ReviewMarch 21, 2026

Itaconic Acid–Based Compounds Fulfilling the Role of Biotechnologically Produced Alternatives to Fossil-Based Precursors for Material Applications
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Vojtěch Jašek*
Vojtěch Jašek
Institute of Materials Chemistry, Faculty of Chemistry, Brno University of Technology, 61200 Brno, Czech Republic
*Email: [email protected]
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https://orcid.org/0000-0002-8020-4948
Silvestr Figalla
Silvestr Figalla
Institute of Materials Chemistry, Faculty of Chemistry, Brno University of Technology, 61200 Brno, Czech Republic
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Radek Přikryl
Radek Přikryl
Institute of Materials Chemistry, Faculty of Chemistry, Brno University of Technology, 61200 Brno, Czech Republic
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ACS Engineering Au

Cite this: ACS Eng. Au 2026, XXXX, XXX, XXX-XXX

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https://doi.org/10.1021/acsengineeringau.5c00116

Published March 21, 2026

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Abstract

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Itaconic acid (IA) attracts significant attention in several application fields, including the materials industry, due to its solid-state form, which is associated with lower volatility and toxicity, and its exceptional potential for chemical functionalization. This debate presents numerous positive aspects of itaconate-based materials for specific applications, such as additive manufacturing, composite fabrication, coating production, adhesive synthesis, textile additives incorporation, and particular engineering for hydrogels. We evaluate many of the efficient viewpoints and advantages itaconic acid offers for the currently engineered systems that use fossil-based compounds and precursors. Unlike similar functional molecules and species, such as acrylates, methacrylates, or vinyl esters, itaconic acid’s liquid derivatives exhibit negligible volatility, thereby reducing potential health hazards and VOC emissions. Moreover, countless derivatives can be proposed and synthesized when appropriate nucleophiles are selected (e.g., alcohols, amines, and others). Due to the two vacant carboxyl acid groups (−COOH), itaconic acid can be incorporated into multicomponent polyesters, polyethers, polyamides, or other functional systems to enhance their performance, improve processability, or ensure degradability. Finally, itaconates provide a route to biocompatible and degradable/biodegradable systems that can develop into new, unique compounds suitable for specific materials.

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1. Introduction

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Modern society focuses on a sustainable future involving biobased materials, renewable products, or partially or fully recycled or upcycled waste. The motivation to use these entering substances arises not only from the goal of reducing our dependence on fossil-based molecules. The valorization of waste, whether recycled or biotechnologically utilized, may decrease total costs across several material industries. (1−3) From a technological perspective, the petroleum-based approaches offer a straightforward route to the final materials, since no modifications of the entering compounds are required (such as cleaning, grinding, or selection). However, oil is a traded commodity whose value is influenced by global geopolitical conditions. China, as one of the largest oil processors, increased its oil consumption from 24.959 million tons in 2000 to 59.52 million tons in 2017. (4) Oil’s price in the global market plays a critical role for several industries. According to recent sources, the price increased from around 40 USD (calculated in 2021 US dollars) in 2000 to nearly 110 USD in 2023 (the global market experienced several price fluctuations, such as the 2008 global economic crisis and the 2014–2015 global oil oversupply). (5) From the sustainability approach standpoint, the systems targeted for chemical recycling or upcycling must be preconditioned via additional processes, such as purification or grinding. Then, they can represent potential added-value systems that can be transformed into a new functional product. (6−8) This approach takes advantage of their high availability (several entering materials are nontraded waste) while reducing processing and disposal costs. (9−12) The partially and fully biobased materials are processed from several natural resources, such as plant-based building systems (cellulose, lignin, or carbohydrates and their derivatives), (10) vegetable triacylglycerides, (11) or the unsaturated terpenes. (12) The entering compounds are modified via particular petroleum-derived molecules to produce partially biobased products–the modified natural substances fulfilling their application purpose with the help of fossil-based derivatives. (13) The material precursors produced from renewable sources do not contain petroleum-based weight content in their molecular structure.

Two main approaches lead to fully biobased alternatives to the currently used substances. Sustainable chemical synthesis represents an alternative to the production approaches presently in use. (14) The widely used epoxy resins are usually produced from Bisphenol A and epichlorohydrin. (15) Also, the unsaturated structures can be transformed into the epoxy derivatives by the fossil-based 3-chloroperbenzoic acid (MCPBA) and serve the same material purposes. (16) Both approaches produce the epoxy precursors used for numerous coatings and adhesives, the high-performing composite production, or electrical applications (insulators). (17,18) The unsustainable approach may be substituted with naturally derived entering compounds, such as the unsaturated vegetable oils, lignin derivatives, (19) or particular terpenes such as limonene, α/β-pinene, or 3-carene. (20) The epoxidation process can involve the enzymatic catalysis; however, this approach is limited from the upscale and industrial viewpoint. (21) The hydrogen peroxide (H₂O₂) is an ideal candidate to transform the epoxidation into a fully sustainable process. Generally, H₂O₂ is produced from molecular hydrogen and oxygen using the anthraquinone process. (22) The sustainable epoxidation was investigated in numerous studies. Typically, H₂O₂-driven epoxidization requires a catalyst to provide optimal reaction conditions. The particular experimentally tested catalysts were formic acid, (23) acetic acid (in a combination with a strong inorganic acid), (23) Amberlite-supported tungsten, (24) or iron-based multicomponent catalysts. (25) Eventually, several sustainable compounds and systems can be produced using the natural entering materials, such as epoxidized vegetable oils, (26) epoxidized fatty acid monoesters, (26) limonene mono and di epoxide, (20) or the epoxidized geraniol. (27) The synthesized bioepoxides produced via the sustainable approach are used as plasticizers, adhesives, or epoxy resin precursors. (28)

Itaconic acid exemplifies a structurally unique, renewable-source-based, and promising molecular alternative to the previously mentioned compounds. The biotechnological route to fossil-based molecular alternatives offers a greener, more sustainable, and less hazardous approach to prospective systems for material applications, promising a clearer future for manufacturing. (29) Itaconic acid is a unique representative of a biotechnologically produced compound due to its molecular structure possessing significant functional groups (see Figure 1). (30,31) Primarily, this C5 dicarboxylic acid contains a terminal alkene, which can represent a direct substitute for numerous petroleum-based unsaturated monomers. They find their purpose in various material applications, (32) such as acrylates, methacrylates, vinyl esters, allyl alcohol derivatives, or maleic polyesters. (33) The unsaturated double bonds inside the molecular structures undergo radical polymerization, usually initiated by thermal-initiator or photoinitiator. (34) The formed hydrocarbon backbone connects the polymerized structure and typically exhibits high chemical and thermal stability. (35) Such structures are significant for material applications, namely photocurable resins for additive manufacturing, polymerizable precursors for composite fabrication, or phototriggered coatings or adhesives. (36,37) The two carboxylic functional groups in itaconic acid’s structure represent strongly hydrophilic reactive centers that pH stimuli can also trigger. These unmodified centers have the potential to form hydrogel structures or serve as pH-active additives. (38) Naturally, the carboxylic functional group can undergo numerous reactions due to the resonance of its delocalized electrons. (39) Therefore, several nonacidic itaconic acid derivatives can be synthesized, such as esters, amides, anhydrides, thioesters, or nitriles. (40,41)

Figure 1. Graphical illustration of the itaconic acid’s molecular structure contains two carboxylic functional groups exhibiting the reactive delocalized electrons in resonance, a radically polymerizable terminal alkene functional group, and the schematic potential functional derivatives, such as amides (derived from amines and acids), esters (derived from alcohols and acids), and anhydride (derived from two acids).

In addition to the specific applications mentioned, itaconic acid may serve as a promising starting compound for the precise engineering of vitrimeric systems. Vitrimers are usually systems that form 3D molecular polymer sites, but unlike conventional thermosets, the formed resins are reprocessable into new products and resins (thermosets represent permanent polymer structures that cannot be dissolved, melted, or recycled). The processability of vitrimers offers a promising approach to circularity and sustainable systems and materials, as vitrimeric resins can be used and reapplied multiple times (typically under specific conditions, such as elevated temperature and pressure). The reprocessability of such systems lies in their dynamic covalent bonds, usually comprising specific functional groups (epoxy groups (−CH₂(O)CH₂−), free hydroxyls (−OH), imine bonds (C═N), or disulfide bonds (−S–S−)). These bonds form a cross-linked structure that may undergo bond cleavage, releasing the 3D molecular site resin structure. (164,165) The released carbon structure can form another polymer site. Several experimental investigations have been reported in the available literature. The particular itaconic acid–based vitrimers were synthesized from 1,1,1-tris (hydroxymethyl) propane, (166) 1,5,7-triazabicyclo[4.4.0]dec-5-ene together with thioctic acid, (167) 4,4′-dithiodianiline together with dicyclohexylmethane-4,4′-diisocyanate, (168) or epoxidized castor oil. (169) Although vitrimer structures exemplify interesting and potentially circular structures, their carbon backbones often contain several expensive and potentially environmentally hazardous compounds.

Itaconic acid derivatives and products exemplify two different applications that affect the potential materials industry differently. The systems may be partly or fully produced from itaconic acid and other biobased compounds (which would represent sustainable materials from renewable sources) (100) or petroleum-based molecules (which would represent biobased materials containing specific renewable content). (118) Both complete systems functionally derived from itaconic acid represent an innovative and promising alternative to the currently used precursors. However, the functional properties, along with the final costs, determine the applicability in the materials industry. This approach is promising for entirely biobased composites (reinforced by natural fibers) (100) or 3D printing (due to the lower toxicity and volatility of itaconic acid and most of its derivatives, along with the potential for biodegradability or compatibility). (76) The applicability of the directly functional itaconic acid–based additives is another alternative for the potential use of renewable compounds in the materials industry. Itaconate derivatives can serve as efficient viscosity modifiers, biobased fillers, or curing centers. (59,119) Therefore, their presence would decrease the environmental damage while maintaining the functional properties. From an industrial applicability standpoint, substituting functional additives with itaconate derivatives represents a more straightforward option for increasing sustainability. Nevertheless, this work presents all the investigated opportunities for incorporating itaconic acid and its derivatives into various materials.

This review aims to present particular, experimentally investigated, and professionally evaluated compounds and multicomponent systems derived from itaconic acid, serving the following applications connected to the material chemistry:

1.	Reactive Precursors for Additive Manufacturing (3D printing);
2.	Curable Matrixes for Composite Fabrication;
3.	Entering Compounds for the Functional Polymeric Coatings;
4.	Molecular Substances for Adhesives;
5.	Initial Representatives for Textile Additives;
6.	Assisting Monomers for Hydrogel Fabrication.

2. Precursors for 3D Printing

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The reactive alkene functional group is essential for the potential application of itaconic derivatives in additive manufacturing. (42) Commonly, the particular photoreactive compound or designed system, such as acrylate or methacrylate resin, is homogenized with selected photoinitiator (2,2-dimethoxy-1,2-diphenylethan-1-one (Irgacure 651), phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide (BAPO), or diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide (TPO)), (43,44) and the activated photocurable solution is processed by particular additive manufacturing technology and instrumentation (stereolithography (SLA), masked stereolithography (mSLA), or digital light processing (DLP)). (45) The targeted photoreactivity and its rheological profile are two of the most essential characteristics of the precursor system for 3D printing. (46,47) The reactivity is crucial for optimizing the printing irradiation times. Typically, 3D printers use dual irradiation times. (48) The first step is to print the initial layer that holds onto the processing platform. This first layer is typically printed for an excessively long time to ensure optimal adhesion on the platform. The rest of the printed layers usually follow the previously photocured characteristics, allowing determination of their exact curing time to limit the total printing time. (48) In the literature, Jacob’s working curve serves for the determination of the optimal printing time from the particular irradiation source exhibiting set irradiation power, the source wavelength value, and the exposure time. (49) The used working curve’s mathematical equation stands as follows (1) (49)

C_{d} = D_{p} \cdot \ln (\frac{I_{0} t}{E_{c}})

(1)

where C_d stands for the curing depth (m), the slope (D_p) determines the penetration depth (m), I₀ is the irradiation source intensity (W/m²), t stands for the exposure time (s), and E_c represents the critical curing energy (J/m²). This working curve shows the dependence of the cure depth C_p measured after printing on the incident radiant energy (E₀ = I₀·t) used to extract the critical energy, which is then compared to the reactivity values of the resins for additive manufacturing. Furthermore, this working curve provides information on the minimum required exposure time to achieve the desired curing depth. Since the curing layer is determined by the 3D printer (modifiable in the settings), the working exposure time can be identical to the investigated required incident radiant energy. (49,50) The acrylate and methacrylate compounds used for 3D printing were numerously investigated using Jacob’s working curve to reveal their application potential. (51) There are only reports describing itaconates’ reactivity from the indirect standpoint regarding additive manufacturing using photo-DSC to provide the curing characteristics, involving a photoinitiator activity. (52) Reactivity, along with the achievable degree of cure, is the Achilles’ heel of itaconate resins. The chemical structure of itaconic acid determines its lower polymerization rates and the nonquantitative conversion of the methylidene functional group (═CH₂). The published study found that the acrylic acid-containing curable vegetable oil achieved considerably higher double-bond conversion (73%) than several itaconic acid–based curable precursors (the lowest reached 54% conversion). (170) Moreover, the itaconic acid derivatives required multiple curing runs for a 75 μm layer (3–5 runs) compared to the acrylic acid–based precursor (completed in 1 run). (170) Therefore, itaconates typically require longer curing times, and their final conversion is lower compared to the petroleum-based curable precursors. However, the limitation may be solved by longer irradiation exposure times or sufficient dilution with reactive monomers (such as methyl itaconate, which generally achieves higher double bond conversions). (170)

The diluting properties are essential for the 3D printing applications (see the experimental results in Figure 2d). The earlier-mentioned thermoset-producing additive manufacturing instruments rely enormously on the optimal rheological profile of the printed resin due to the functional factors. (53) Typically, the literature reports that the maximum efficient apparent viscosity of the radically polymerized precursor should not exceed 5 Pa·s due to the inefficient resin’s flow during the printing process. (45) When the curable system exhibits a higher viscosity, the instrumentation is unable to provide enough time for the precursor to take a place above the irradiation exposure display. (45) Naturally, the apparent viscosity follows the Arrhenius law describing the flow characteristics’ dependence on the increasing temperature. (54) The particular equation reveals that the higher the working temperature, the lower the actual apparent viscosity, as displayed in eq 2 (54)

\ln η = \frac{E_{η}}{R} \cdot \frac{1}{T} + \ln η_{\infty}

(2)

where η stands for the apparent viscosity (Pa·s), E_η represents the flow activation energy (J/mol), R is the universal gas constant (J·mol^–1·K^–1), T expresses the actual temperature (K), and η_∞ stands for the infinite-temperature viscosity (also known as the pre-exponential factor) (Pa·s). Since the 3D printers for stereolithography usually do not provide the option to operate at elevated temperatures (mainly due to the potential for spontaneous polymerization at higher temperatures), additive manufacturing techniques use reactive diluents (RD) to modify flow properties. (55) RDs are usually low-molecular-weight, reactive compounds with considerably low viscosities (ranging from 1 to 100 mPa·s). (56) There are several invented, commercially available, and widely used RDs exhibiting extremely low apparent viscosity values (isobornyl acrylate (IBOA), isobornyl methacrylate (IBOMA), styrene, ethylene glycol diacrylate (EGDA), ethylene glycol dimethacrylate (EGDMA), methyl acrylate (MA), or methyl methacrylate (MMA)), (57) and several compounds reach higher values in tens of mPa·s (tripropylene glycol diacrylate (TPGDA), 1,6-hexanediol diacrylate (HDDA), or isosorbide dimethacrylate (ISDMA)). (58) The itaconic acid derivatives can represent high-molecular polymerizable compounds triggered by irradiation with photoinitiator assistance. At the same time, low-molecular itaconates might serve as reactive diluents, modifying the rheological profile of the printed thermoset-forming precursors. (59) Such systems could represent novel and innovative biotechnologically produced alternatives to the petrochemical molecules while maintaining the concept of the radically polymerizable systems crucial for 3D printing (see the illustration graphic in Figure 2).

Figure 2. Primary parameters influencing the stereolithography 3D printing. (a) Irradiation source type (the characteristics wavelength and power value), (b) the specific reactivity of the precursor (determined by Jacob’s working curve or differential scanning calorimetry (DSC)), (c) the rheological profile of the resin-forming systems (dependent on the temperature by the Arrhenius law and affected by the reactive diluent’s content) (d) the published diluting properties of the experimentally applied itaconate derivaties. (84) Reproduced from ref (84). Copyright [2017] American Chemical Society.

2.1. Itaconic Acid-Derived Polyester Resins

Itaconic acid, as a compound containing two carboxyl acid groups (−COOH), is ideal for the synthesis of oligopolyesters involving photocurable double bonds, while composed mainly of biobased content (see Figure 3). Usually, the combination of other diacids (such as succinic acid or maleic acid) together with diols (ethylene glycol, propylene glycol, butanediol, hexanediol, or selected poly(ethylene glycol) (PEG)) forms a perspective medium-molecular ester system with sufficient rheological profile and maintained reactivity to fulfill the role of a highly viscous primary precursor for thermoset fabrication. (60−67) Several oligomer itaconic acid-containing polyesters were investigated in the published articles. Papadopoulos et al. (60) synthesized five different polyester systems (see Figure 3a). All produced systems contained itaconic acid and 1,3-propylene glycol to form the polyester oligomers. Additionally, five differing dicarboxylic acids or derivatives (sebacic acid (SebA), succinic acid (SA), 2,5-furandicarboxylic acid (FDCA), isophthalic acid (IsA), and phthalic anhydride (PhA)) were introduced into the oligomer structure to modify the rheological profile, total biobased content, the overall thermo-mechanical properties, and the thermal stability. The authors performed Fischer esterification via azeotropic water removal using toluene as a supporting solvent. All the synthesized ester structures exhibited practically similar thermo-mechanical, thermal, and rheological properties. The produced oligomers were fabricated by stereolithography only after the viscosity was modified with a fossil-based RD, 4-acryloyl morpholine (ACMO), at 27, 37, and 47 wt %. Excessively high viscosity is critical for most oligomer structures. Their relatively high molecular weight, combined with polar functional groups such as hydroxyl (−OH) or ester groups (−COOR′), generates intermolecular forces that negatively affect rheological properties in additive manufacturing. Another scientific paper from Papadopoulos et al. (61) studied the same structures using isobornyl acrylate (IBOA) as an RD. Their findings confirm that such viscous itaconic-based curable polyesters are unable to form a resin precursor for stereolithography without the flow modifications.

Figure 3. (a) Itaconic acid–based polyester used in combination with 4-acryloyl morpholine (ACMO) as a reactive diluent, (60) Reproduced from ref (60). Copyright [2023] American Chemical Society (b) oligomer itaconate precursor systems containing biobased reactive diluents derived from furfuryl, tetrahydrofurfuryl, solketal, and diacetone glucose reactive derivatives, (63) Reproduced from ref (63). Copyright [2025] American Chemical Society (c) Polylactone/itaconate elastomer resins processed by reversible addition–fragmentation chain transfer (RAFT) mediated 3D-printing with polypeptide surface functionalization, (67) Reproduced from ref (67). Copyright [2023] American Chemical Society (d) modified grapheme oxide (GO) nanoparticles incorporated into a itaconate-based 3D printing resin for the enhancement of the material properties while maintaining the advanced functional properties ensured by GO’s the conjugated π-electron system. (66) Reproduced from ref (66). Copyright [2025] American Chemical Society.

Cazin et al. (62) used the same components for oligomer production as the previous authors. They added additional alcohols (cyclohexanedimethanol (CHDM) and isosorbide (IS)) and an acid (acrylic acid (AA)) to modify their systems further. Their main goal was to fabricate the most biobased 3D-printable resin. As the authors conclude, their best result, containing isosorbide, 1,3-propanediol, sebacic acid, succinic acid, phthalic anhydride (potentially biobased), and itaconic acid, reached 95 wt % of biobased content (according to the authors). Most of the presented experimental results were conducted with three systems containing 0, 40, and 60 wt % biobased content. Most importantly, the 3D-printed systems fabricated under standard room-temperature conditions included AA as the radical-polymerizable functional group. The most biobased polyester with itaconic acid had to be heated to 50 °C and printed at inefficient printing times (50, 75, and 100 s per layer). Similar to the previously described systems, the reported ester oligomer structures involving itaconic acid struggled in additive manufacturing under usual conditions.

Bösche et al. (63) synthesized a polyester system involving itaconic acid from several components: itaconic acid, sebacic acid, 1,3-propanediol, and Velvetol H2000 (1,3-polypropanediol) (see Figure 3b). To formulate 3D-printable resins, the authors investigated the applicability of additional biobased (nonitaconic acid-containing) RDs and compared their rheology-modifying properties. The synthesized RDs from renewable sources were furfuryl methacrylate (FMA), tetrahydrofurfuryl methacrylate (THFMA), tetrahydrofurfuryl acrylate (THFA), solketal methacrylate (SMA), and diacetone glucose methacrylate (DAGMA). The authors summarized that DAGMA-containing systems exhibited the most promising properties and results when UV-cured, for the first time in the available literature. The mentioned systems also contained a high level of biobased content (76–84%). Nevertheless, the studied itaconic acid–based polyester oligomer required modification for potential additive manufacturing applications.

Gao et al. (64) chose a different material approach to obtain an itaconic acid-containing polyester structure processed by additive manufacturing. The authors used two diols (2,3-butanediol and 1,4-butanediol) and two diacids (succinic acid and itaconic acid) to prepare an ester oligomer. Then, the formed itaconic acid polyester was mixed with PLA polymer to obtain a thermoplastic vulcanizate (TPV). Eventually, the prepared PLA/itaconic oligomer mixture was processed by FDM 3D printing. This approach differs from the previously described one, as Gao’s team chose a 3D printing approach to process solid-phase thermoplastic vulcanizate. The main goal was to introduce a novel itaconic acid-containing FDM-printable system with enhanced elastic properties of the commercially used PLA. The produced poly(1,4-butanediol/2,3-butanediol/succinic acid/itaconate) (PBBSI) exhibited 20,000–40,000 g/mol number-average molecular weight and 3.2–5.0 dispersity (PDI).

Carmenini and the team investigated an interesting approach to incorporating itaconic acid into a 3D-printable polyester precursor. (65) The authors used the postconsumer poly(ethylene terephthalate) (PET). They transformed it into a photocurable liquid copolyester by incorporating itaconic acid and additional polyol into the PET’s structure in a one-pot process. The process involved postconsumer PET (rPET) that was depolymerized via transesterification using multiple diols (1,4-butanediol, 1,6-hexanediol, and 1,12-dodecanediol) and primarily dimethyl itaconate (DMI). Many different reaction mixtures were prepared from these entering reactants yielding to six systems suitable for 3D printing. The authors decided to involve three RDs in the precursor resins (2-hydroxyethyl methacrylate) (HEMA), 1,6-hexanediol diacrylate (HDDA), and ethylene glycol phenol ether acrylate (EGPEA) primarily to modify the flow characteristics. The eventual printed prototypes ranked in the top 15% of approximately 160 previously assessed formulations, as evaluated by the Sustainable Formulation Score (SFS). The presented approach also demonstrated a promising way to implement an upcycling strategy using postconsumer polymer across different applications.

Maturi et al. (66) used an itaconic acid–based reactive precursor to fabricate graphene oxide (GO) nanoparticles via a 3D printing approach (see Figure 3d). The authors grafted a sustainable photocurable polyester resin, synthesized from dimethyl itaconate, 1,4-butanediol, and dimethyl adipate, to form poly(butylene itaconate-co-adipate) on the GO surface. The main goal was to modify the GO particles to be more compatible with reactive resins for additive manufacturing. The investigation resulted in outstanding results. According to the authors, the modified GO at 0.05 wt % loading led to a considerable increase in the elastic modulus (42%) and tensile strength (40%) compared to the pure photocured resin. Also, the surface modification effectively enhanced the processability of the dispersion, resulting in the system uniformity (due to the better stability) and enhanced deformability. Furthermore, the chemical modification of the used GO did not negatively affect the conjugated π-electron system, which is essential for multifunctional purposes.

Many published articles also focused on incorporating lactones into the complex photocurable reactive precursor systems for 3D printing. Torres et al. (67) investigated itaconic acid–based curable systems incorporating lactones for reversible addition–fragmentation chain transfer (RAFT) polymerization to functionalize polypeptide surfaces (see Figure 3c). The researchers synthesized poly(caprolactone-co-valerolactone) itaconate (poly(CL-co-VL)-IA) oligomer structure modified by pentaerythritol (to ensure the cross-linking properties). Additionally, the 3D printed curable precursor contained 4-Cyano-4-[(dodecylsulfanylthiocarbonyl)sulfanyl]pentanoic acid (CDTPA) that reacted with the used reactive diluents, hydroxyethyl acrylate (HEA), dimethyl itaconate (DMI), or dibutyl itaconate (DBI), through the addition mechanism initiated by diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide (TPO). This engineered, curable, multicomponent system was processed by DLP 3D printing to demonstrate RAFT-mediated additive manufacturing. The use of HEA enhanced the poor reactivity of itaconates in photocurable applications. According to the authors, the eventual DPL-printed prototypes contained approximately 50% renewable content due to the incorporation of itaconic derivatives.

The available literature involves many other itaconic acid–based photocurable precursors incorporated in the polyester structure for 3D printable resins. The published works focused on the incorporation of itaconic acid into a polycaprolactone-based resin for environmentally friendly 3D printing, (162) or on different research investigating itaconic acid-containing terpene-derived systems for photocurable applications. (163) This subsection reports the most recent approaches and various potential applications to provide a comprehensive perspective on the renewable systems for sustainable additive manufacturing. Table 1 summarizes the list of evaluated polyester compounds derived from itaconic acid applied to additive technologies. According to the authors, two of the summarized 3D printing itaconic acid-containing resins (the hydrolyzable sustainable resin and vat polymerization precursor) can contain nearly quantitative biobased content (the photoinitiator in both applications is fossil-based; therefore, the total composition is not fully biobased). (69,70) The rest of the listed systems and products in Table 1 contain considerable content from renewable sources, which may connect the sustainable aspect of itaconic acid in its chemical structure with the high-performing properties ensured by the fossil-based additives and components. (69,71−74) In most of the summarized cases, the reactive diluent was used to improve processability for 3D printing, which is typical for highly viscous itaconate derivatives. The incorporation of a suitable main resin and a reactive diluent would definitely increase the applicability of the resulting 3D printing commercial resin or reprocessable printing systems from renewable sources.

Table 1. List of the Investigated Polyester Precursors Based on Itaconic Acid

polyester itaconate-based precursors
application	carboxyl acids (derivative)	polyol (derivative)	renewable content	additive for 3D printing	refs
3D Printed Nanocomposite	Itaconic Acid, Sebacic Acid	1,3-Propanediol	50 wt %	Reactive Diluent (ACMO)	(68)
Hydrolyzable Sustainable Resin	Itaconic Acid, 1,12-Dodecanedioic Acid	1,3-Propanediol	≈99 wt %	Processed Without 3D Printing	(69)
Vat Polymerization	Monomethyl Itaconoyl Chloride, Caprolactone	Sorbitol	29–97 wt %	(Meth)acrylate Reactive Diluents	(70)
3D Printing Resin	Itaconic Acid, Succinic Acid	1,2-Propanediol, 1,4-Butanediol, 1,8-Octanediol	50 wt %	Reactive Diluent (TEGDMA)	(71)
Extrusion-Based 3D Printing	Itaconic Acid, Succinic Anhydride	1,8-Octanediol	Not Available	Processed Without 3D Printing	(72)
Phosphorescent 3D Printing Resin	Itaconic Acid, Vanillic Acid	Glycerol, 1,3-Propanediol	48.5 wt %	Reactive Diluent (THC, BHI)	(73)
3D Printing Resin	Itaconic Acid, Dimethyl Terephthalate	Ethylene Glycol, 1,3-Propanediol, 1,4-Butanediol, 1,5-Pentanediol, 1,2-Propanediol, 2-Methyl-1,3-Propanediol, 1,3-Butanediol, 3-Methyl-1,5-Pentanediol	48–57 wt %	Reactive Diluent (Styrene)	(74)

2.2. Other Curable Itaconate Resins

Itaconic acid, as a molecule containing two acidic functional groups (−COOH), is primarily used for ester and polyester-involving compounds and systems. However, biobased 3D printing resin precursors can incorporate itaconates in different chemical forms. Carmenini et al. (75) published an investigation focused on isocyanate-free urethanediol itaconates used for additive manufacturing. The authors reported the reaction of 1,4-diaminobutane with ethylene/propylene carbonate to yield urethane structures bearing vacant hydroxyl groups (−OH) (bis(hydroxyethyl)butane-1,4-diyl dicarbamate and bis(hydroxypropyl)butane-1,4-diyl dicarbamate). The formed urethanes were modified by monomethyl itaconoyl chloride, forming the photocurable urethane itaconates ([bis(hydroxyethyl)butane-1,4-diyl dicarbamate] bis(methylitaconate)) and ([bis(hydroxypropyl)butane-1,4-diyl dicarbamate] bis(methylitaconate)). Similarly, as oligomer ester itaconate structures, the urethane itaconates exhibit many intermolecular interactions; therefore, the rheological profile of such compounds complicates the 3D printing process. The authors performed photocuring via additive manufacturing using glycerol-based monomers (not specified) and 1,4-butanediol bis(methyl itaconate) (total RD content: 50 wt %). Eventually, the authors reported that their photocurable resins processed by 3D printing contained 75–90 wt % of biobased content, while their observed tensile strength reached around 1 GPa. The primary goal was to introduce an alternative to polyester itaconate structures used in additive manufacturing, since the authors state that, at present, no fully biobased resin can surpass acrylate and methacrylate precursors for 3D printing in terms of printability and mechanical properties.

Amides are thermodynamically more stable functional derivatives of the carboxylic acids. Therefore, amide synthesis can be performed under mild conditions, without a catalyst, due to the eventual stability of the product. Buratti et al. (76) focused on the combination of caprolactone and 1,4-butanediamine to obtain an oligomer amide structure, terminated by hydroxyl (−OH) functional groups. This intermediate was condensed with vanillic acid and itaconic acid to obtain poly(diamidodiyl itaconate-co-vanillate). This complex ester–amide structure was mixed with numerous additives (bis(2-(methacryloyloxyethyl) itaconate)) (BHI), tris(2-(methacryloyloxyethyl) citrate (THC), 2-hydroxyethyl methacrylate (HEMA), lauric acid (LA), and photoinitiator combination MAPO, BAPO, and DEAP). The authors studied the successfully 3D-printed objects to determine the mechanical properties of the eventual resins. Additionally, the produced system was assessed for potential cytotoxicity, which was excluded based on the observed cellular viability results. A similar poly(ester–amide) synthesis approach was reported in other published articles (see the scheme in Figure 4). (77)

Figure 4. Poly(ester amide) structure incorporating itaconic acid as a reactive polymerizable precursor suitable for stereolithography 3D printing. (76) Reproduced from ref (76). Copyright [2022] American Chemical Society.

Other researchers investigated the incorporation of amide functional bonding into the oligoester structure with different entering compounds. Ouhichi et al. (78) combined the reliable, known itaconate ester structure with thermodynamically stable amide bonding in their produced curable resins. First, they synthesized the biobased oligoester from itaconic acid and 1,6-hexanediol. This condensation reaction was performed using a Dean–Stark apparatus and toluene as the supporting solvent. The amidation involved additional entering substances–adipic acid, ethylene glycol, and hexamethylene diamine. In the first step, amide formation occurred in the absence of a catalyst at 190 °C under nitrogen. Eventually, the entire system was transesterified with the initially synthesized biobased oligoester. The produced systems exhibited polymerizable potential due to the presence of itaconic acid in their structures. Their viscosities ranged from 5000 to 22,000 mPa·s. Eventually, the authors presented a successfully cured prototype to demonstrate the material’s potential.

Kumar et al. investigated an interesting approach to obtain a polymerizable itaconate-derived precursor. (79) The research team proposed a multistep modification of biobased itaconic acid to obtain a three-functional epoxidized reactive compound suitable for thermoset production. In the first step, itaconic acid is modified by allyl bromide via the allylation route. Second, the obtained diallyl itaconate (DAI) was epoxidized with a commercially available epoxidizing agent, meta-chloroperoxybenzoic acid (mCPBA). The obtained product, triepoxidized diallyl itaconate (TEIA), was polymerized and compared to the bisphenol A resin and the cross-linked epoxidized soybean oil system, which represents a biobased system suitable for 3D printing. The obtained TEIA performed similarly to the bisphenol A fossil-based resin commonly used in the industry. Additionally, TEIA thermoset outperformed the epoxidized soybean oil systems in terms of rheology and mechanics, and also exhibited higher thermal stability.

2.3. Itaconate-Based Reactive Diluents

Reactive diluents are essential for most fossil- or biobased systems targeted for 3D printing. Several high-performing systems exhibit high viscosity due to their oligomeric chemical structure, (80) the cumulative polar and hydrogen-bond-forming functional groups (such as carboxyl (−COOH), hydroxyl (−OH), and ester (−COOR′) as a hydrogen bonding acceptor), (81) or highly branched carbon backbones. (82) Reactive diluents contain reactive functional groups (primarily radically polymerizable for stereolithography 3D printing) and possess low molecular weight and various functional groups in their structure to fulfill the required properties for the target application. (83) The fossil and biobased reactive diluents were introduced and described earlier in the chapter. This subsection focuses on the introduction of itaconate-based RDs.

Panic et al. (84) proposed the one-pot synthesis of a fully biobased polyester resin, combined with itaconic acid-derived low-molecular diesters serving as polymerizable diluents. Their strategy involved the synthesis of polyester itanonate structure with 1,2-propylene glycol. The synthesized polyester chain exhibited excessive viscosity (10,000 mPa·s); therefore, five different RDs were incorporated into the precursor system to observe the resulting rheological changes. In total, four itaconic acid symmetric diester derivatives (dimethyl itaconate (DMI), ethyl itaconate (DEI), diisopropyl itaconate (DiPI), and di-n-butyl itaconate (DBI)) were mixed with the synthesized polyester structure and compared to the styrene-diluted precursor. The measured viscosity decreased from the ten thousands mPa·s to 2000–6000 mPa·s (DiPI and DBI fulfilled the RD’s role similarly to the reference styrene). All the biobased itaconate RDs exhibited notably lower volatility over 15 h than styrene. Therefore, their positive role was confirmed based on the released VOCs. The mechanical and thermo-mechanical investigations revealed that DMI achieved the same, or better, values and properties among the biobased RDs. However, styrene outperformed all other biobased RDs due to its high reactivity and aromatic chemical structure, resulting in exceptional rigidity and performance in cured thermosets.

Arnaud et al. (59) conducted a comprehensive study on the synthesis of symmetric and asymmetric itaconic acid–based diesters for dilutingand additive manufacturing applications. Their production approach involved three distinct chemical reactions to produce the RDs. The symmetric itaconic acid diesters derived from nonvolatile alcohols with one free hydroxyl group (−OH) were synthesized via Fischer esterification in the presence of an acidic catalyst (MSA), the spontaneous polymerization inhibitor (BHT), and the supporting solvent (toluene) to facilitate azeotrope water separation. The asymmetric itaconate diesters were synthesized in a three-step process. Initially, they synthesized itaconic anhydride from acetic anhydride under acidic conditions. Next, the formed itaconic anhydride was mixed with both volatile and nonvolatile monofunctional alcohols, resulting in the formation of mono itaconate esters. Eventually, the itaconic acid monoester was modified by a particular epoxy derivative to obtain the final itaconic diester via a nucleophilic substitution mechanism. The third chemical approach led to the synthesis of highly viscous symmetric itaconate diesters derived from pure itaconic acid and an equimolar amount of epoxy compound. The last synthesis was a one-step nucleophilic substitution. All the synthesized reactive diluents produced via the introduced approaches are summarized in Figure 5.

Figure 5. Complex synthetic scheme composed of reactions described and evaluated in the investigation provided by Arnaud and the team. (59) The scheme describes three different chemical approaches leading to the symmetric esters produced via Fischer esterification, asymmetric esters combining anhydride and epoxide compounds, and symmetric esters derived from epoxy entering compounds. Reproduced from ref (59). Copyright [2021] American Chemical Society.

Following the investigation of reactive diluents, Arnaud’s team selected four specific synthesized RDs (DE-1, HE-2, HE-6, and DHE-1: see structures in Figure 5) and used them to modify an oligomer ester derived from itaconic acid and 1,3-propanediol. The excessive viscosity of the polyester structure (25,900 mPa·s) was decreased tremendously down to 1200–11,000 mPa·s (depending on the selected RD), which confirmed the functional character of the chosen compounds. In addition to the rheological investigation, the authors used two systems–polyester itaconic resin with 70–72 wt % of DE-1 and DHE-1, respectively, to fabricate DMA testing specimens via additive manufacturing. Therefore, the printability and sufficient reactivity were also verified. The final two selected diluted precursors exhibited viscosities of 2580 mPa·s for DE-1 and 3450 mPa·s for DHE-1, which are sufficient for manufacturing via 3D printing (as stated in the chapter’s introduction). The 3D printed DMA specimens are illustrated in Figure 6. (59)

Figure 6. Illustrated polyester itaconic acid–based cured resins, modified with selected itaconate-reactive diluents, fabricated through 3D printing. (a) 3D-printed DMA specimen containing dicyclohexyl itaconate (DE-1), (b) 3D-printed DMA specimen containing bis(2-hydroxybutyl) itaconate (DHE-1). (59) Reproduced from ref (59). Copyright [2021] American Chemical Society.

This section describes a potential role for itaconic acid and its derivatives in additive manufacturing as the primary resin alternative to entirely petroleum-based precursors and as a functional additive to enhance specific properties (primarily viscosity). In summary, this material sector exemplifies the following challenges to be overcome for any potential industrial or commercial application:

The significantly lower reactivity of itaconates represents an obstacle to efficient 3D printing at a commercially attractive rate. Low-molecular-weight itaconate derivatives can solve this issue;
The lower degrees of cure of the itaconate polymers often result in decreases in several mechanical properties. Structural engineering of the precursor may lead to an efficient solution;
The rheology levels of itaconate oligomers complicate the 3D printing process. Their adjustment has to be considered.

3. Matrix for Composites

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The itaconic acid-containing partially or fully biobased precursors are sufficiently reactive to serve as matrices for multicomponent systems and composites. Previously, we discussed the importance of rheological character and nominal viscosity levels in the 3D printing process. Speaking of composite production, this factor is covered in the specific fabrication of multicomponent systems, given their different production approaches. Typically, thermal radical initiators are applied to trigger reactive molecules that eventually form the final thermoset structure, in combination with the solid-phase filler. (85) Since most thermally initiated precursors are fabricated at elevated temperatures to ensure the entire decomposition of the initiator, the higher temperatures set during the process typically overcome the potential issues connected to the nonoptimal viscosity levels at room temperature. (86,87) Unlike in additive manufacturing, where the working temperature is usually mild (laboratory temperature), the composite fabrication process temperatures range, which provides much more efficient material production. (85−87)

The thermal initiation kinetics are critical for most of the composite production engineering. (88,89) The elevated temperatures must be set to the values that match the polymerization initiation, and should be the lowest required so the process is rentable and efficient. The Kissinger and Ozawa theories are widely used to calculate the reaction kinetics parameters. Typically, these models are applied to predict the optimal curing conditions and to describe precursors’ behavior at elevated temperatures in the presence of specific thermal initiators. The Kissinger theory equation is displayed in eq 3 (90,91)

\ln (\frac{β}{{T_{p}}^{2}}) = \ln (\frac{AR}{E_{a}}) - \frac{E_{a}}{R} \cdot \frac{1}{T_{p}}

(3)

where β is the heating rate (°C/min); T_p is the exothermic peak temperature (°C); A is the pre-exponential factor (−); E_a is activation energy of the reaction (J/mol) and R is the gas constant (J/(mol·K)). Ozawa’s model is illustrated in eq 4 (92−94)

\ln β = - 1.052 \cdot (\frac{E_{a}}{R \cdot T_{p}})

(4)

where all the representing parameters are similar to those in eq 3. Typically, these two kinetic theories provide the information regarding the polymerization activation energy. This parameter is used for comparison purposes to determine the most and least reactive thermoset precursors. Naturally, the thermal initiator used and the DSC conditions must be constant to obtain polymerization activation energy values suitable for comparison. Several published articles investigated the polymerization kinetics to describe the fabrication in detail. This section summarizes numerous composites with itaconate-derived resin and various solid-phase fillers ranging from high-performing carbon filaments to fully biobased natural systems.

3.1. Carbon Fiber Composites

The itaconic acid–based reactive precursor was used to fabricate different multicomponent systems involving high-performing ultralight carbon fibers as a solid-phase composite filler. These materials do not fully meet the criteria for sustainability due to the components used; however, the resulting systems exhibit many attractive properties suitable for several utilities. Wang et al. (95) incorporated itaconic acid–based epoxide with a sulfur filler into complex carbon fiber composites. The liquid matrix was synthesized from itaconic acid and epichlorohydrine, yielding a polyester oligomer terminated with unreacted oxirane rings. The produced structure was mixed with sulfur powder to obtain a carbon-itaconic structure connected by disulfide bonds. The cross-linking required for the composite production is provided by the unsaturated alkene group (═CH₂) within the itaconic acid structure. The sulfur powder reacts with itaconates via an addition mechanism, forming a disulfide bond. The prepared itaconic-based matrix was fabricated with carbon fibers (CF) at 160 °C for 4 h to produce the final composite. Additionally, the authors performed a material recycling route using the dynamic ester exchanges formed in the used matrix. The authors declare that carbon fiber composites can be fully recycled.

Xiao et al. (96) developed an alternative matrix for composite fabrication using itaconic acid as a biobased, functional starting compound. The authors prepared a multicomponent liquid system, involving itaconic acid epoxy resin (EIA, epoxy value of 0.52), diglycidyl ether bisphenol A (DGEBA, epoxy value of 0.51), and Dicyandiamide (DICY). This reactive matrix was studied as a cured thermoset and also incorporated into carbon fiber composite laminates (CFRP). The produced laminates were heated from room temperature to 70 °C at a rate of 3 °C/min. Eventually, the product was fully cured at 130 °C for 120 min. The whole process was conducted at a pressure below 3 MPa. The density of the produced composites was 1.55 g/cm³, and the fiber volume filling was 60 vol %. The produced itanocate-based CFRP exhibited exceptional hydrothermal stability and durability. This outcome was achieved due to a highly cross-linked matrix structure, and a strong hydrophobic character of the used entering components.

Itaconic acid is usually modified to form nonacidic oligomers or functional reactive compounds that serve as matrices in composite fabrication. Shang et al. (97) investigated an approach that takes the acidic character of this dicarboxylic acid into account and uses it for the composite filler’s surface modification. The authors modified their carbon fibers through a multistep process. Initially, the fiber’s surface was exposed to oxidizing conditions (provided by nitric acid) to obtain carboxylic functional groups (−COOH). Next, the reduction agent, lithium aluminum hydride (LiAlH₄), was used to convert carboxyl groups (−COOH) to hydroxyl groups (−OH). Itaconic acid was esterified onto the premodified surface in a reaction mixture containing catalysts dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP). Eventually, the itaconic acid-branched carbon fibers were mixed with ethylenediamine (EDA) to form amide functional groups (−NH−) terminated by free amines (−NH₂). The modified carbon fibers were fabricated into a composite using epoxy resin DGEBA via vacuum-assisted matrix infusion. The filling volume percentage was 60 ± 1 vol %, and the curing conditions were: 100 °C for 1 h, 120 °C for 3 h, and 150 °C for 3 h. The authors confirm that poly(itaconic acid) treatments improved the carbon fiber’s surface healing, promoting improved interfacial shear strength. Additionally, the grafted amine groups (−NH₂) maintained the mechanical properties while increasing the surface polarity and reactivity with the DGEGA matrix during the composite fabrication.

3.2. Natural Itaconate Composites

The sustainable composite based on itaconic acid requires sustainable solid-phase filling. Both the matrix and the solid phase should be modified using sustainable reactants or exhibit at least a major biobased content. Kocaman et al. (98) investigated the synergy of itaconic acid-derived matrix with natural waste olive pomace (OP). Similar to the previously described syntheses, the authors produced an itaconate epoxy resin derived from itaconic acid and epichlorohydrin, resulting in an oligomeric, trifunctional epoxy compound. The OP was modified by alkalization in a 5 wt % solution of sodium hydroxide. Then, meticulous water-washing and drying of alkalized OP followed. The composited fabrication involved mixing the matrix and alkalized OP, then adding the curing agent (m-xylene diamine (MXDA)). The filled molds were maintained at 40 °C for 30 min to degas the system. The curing process was performed at 40 °C for 24 h, followed by an additional 24 h at 80 °C. The authors successfully produced a highly biobased itaconate composite from natural heterogeneous filling. The alkali-treated OP-composited exhibited enhancements in tensile strength and thermal properties compared to the pure cured matrix. Also, the positive effect was observed from the conducted surface energy investigations and DMA measurements.

Since itaconic acid possesses a reactive alkene group (═CH₂) and two vacant carboxyl acid groups (−COOH), a sustainable composite structure incorporating natural solid-phase fillers may be fabricated. Ghosh et al. (99) achieved the production of a natural composite containing lignin-functionalized poly(itaconic acid) dispersed in a poly(vinyl acetate) matrix. The production process involved the separate functionalization of poly(itaconic acid) and the blending of the resulting liquid–solid phase composite. First, lignin was ultrasonicated in a water solution for 30 min. Then, the 40% neutralized solution of itaconic acid was added to the water-lignin mixture, followed by the addition of 3 wt % of ammonium persulfate (APS). The water solution was heated up to 80 °C for 4 h under a nitrogen atmosphere. Eventually, the final solid product was filtered and washed to remove the free poly(itaconic acid) and unreacted monomers. Since the lignin particles contain free hydroxyl groups (−OH) and the poly(itaconic acid) possesses vacant carboxyl acid groups (−COOH), the blending with poly(vinylacetate) (PVAc) leads to the intermolecular hydrogen bonding formation. The ester functional groups of PVAc (−COOR′) do not contain free hydrogen atoms to serve as hydrogen-bonding donors. Still, their bonded oxygen atoms with vacant electron pairs serve as hydrogen-bond acceptors, enhancing the eventual composite’s properties and characteristics. The poly(itaconic acid)-functionalized lignin was meticulously characterized by zeta potential, FTIR, NMR, FESEM, and TGA. The eventual composite system should exhibit improved adhesive strength compared to a pure PVAc resin.

The fusion of a polymerizable itaconate matrix with the natural solid-phase filler was investigated by Dai and team (see the schematic in Figure 7). (100) The proposed fully biobased matrix was synthesized via polycondensation of ethylene glycol, oxalic acid, and itaconic acid. The authors varied the molar amounts of the dicarboxylic acids, leading to an increase in molecular weight with the increasing itaconic acid content. The polyester structure exhibited excessive viscosity levels (similarly to the polyester precursors described in Section 2.1), ranging from 50,000 to 60,000 mPa·s; therefore, the biobased reactive diluent, dimethyl itaconate, was used as a rheology modifier. The composite consisted of a synthesized unsaturated polyester resin (UPE) and cotton fabric as the solid-phase natural filler. The authors used tert-butyl peroxybenzoate (TBPT) as a thermal initiator. The composites’ curing process lasted 3 h at 110 °C and 15 MPa. The eventually produced composites reinforced with cotton fabrics exhibited sufficient compatibility with the used rheology modifier (dimethyl itaconate). The natural composites achieved a similar glass transition temperature (T_g of 100–120 °C) to that of commercial resins used in the composite industry. (169) The UPS matrices with dimethyl itaconate exhibited competitive thermomechanical and mechanical properties with acrylated epoxidized soybean oil and styrene-based thermosets. According to the authors’ declaration, the synthesized fully biobased composites could replace fossil-based matrices.

Figure 7. Schematic illustration of the proposed fully biobased composite from itaconate resin and cotton fabrics as the solid-phase filler along with thermo-mechanical properties measured by the DMA analysis. (a–e) SEM pictures of the obtained composite prototype, (f) the photo of the fabricated composite. (100) Reproduced from ref (100). Copyright [2018] American Chemical Society.

This section focuses on the application of itaconate derivatives in the composite industry as binding resins (matrices). The following challenges have to be considered before a potential application:

The polymerization reactivity of itaconates. A suitable cross-linker or reactivity can solve this issue;
The reinforcement-matrix compatibility from the chemical structure standpoint. The itaconic acid–based system must be engineered to address this potential problem;
Suitable surface modification of the natural fibers before material fabrication. The compatibility of any resin (including the itaconate) may be problematic.

4. Functional Coatings

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The polymeric coatings and thin layers serve several functional purposes, such as mechanical protection, (103) irradiation protection (UV barrier), (103) decorative role, (103) functional responsive membranes, (104) electronic components, (104) heat insulation, (105) or corrosion resistance. (106) Since every application demands different essential properties to fulfill its application role, a broad spectrum of various parameters is taken into account regarding the engineering and suggestions of each function coating. In connection with all named application field, numerous analyses and measurements provide necessary information regarding the required performance, such as layer thickness monitoring, adhesion levels, pencil hardness, flexibility performance, water absorption, thermal resistivity, microbial/antimicrobial activity, healing properties, thermal stability, rheological profile, surface tension and energy levels, solubility characterization, or UV-absorption for barrier properties. (101−106) The summarizing illustration in Figure 8 displays many of the mentioned properties and characteristics listed above. This section provides a comprehensive review of various itaconate-containing compositions, the factors involved, and the measured performance of the prepared and studied functional thin layers.

Figure 8. Schematic list of potential and investigated application fields for itaconic acid–based polymeric coatings for material applications. The illustrated reaction scheme describes the modification of epoxidized soybean oil (ESO) with itaconic acid monoester, yielding itaconated epoxidized soybean oil (IESO), which represents a green alternative to the commercially used acrylated epoxidized soybean oil (AESO) for general coating applications. (101,102) Reproduced from ref (101) Copyright [2016] American Chemical Society and from ref (101) Copyright [2019] American Chemical Society.

4.1. Bio-Based Alternative Itaconate Coatings

Many published investigations and studies have focused on the development of biobased itaconate-based coating alternatives to the commercial, fossil-based materials. Paraskar et al. (107) proposed an air-cured polyurethane coating composed of vegetable oils and modified with itaconic acid. The synthesis approach involved aminolysis of triacylglycerides with diethanolamine in the presence of a strongly basic catalyst, sodium methoxide. This first step produced fatty acid amides, containing two free hydroxyl groups (−OH) from diethanolamine’s structure, and glycerol represented the reaction byproduct. The second production step comprised an esterification reaction between fatty acid diethanolamides and itaconic acid, forming poly(esteramide) polyol terminated by hydroxyl groups (−OH). Finally, the pre synthesized polyol, containing itaconic acid in the carbon backbone was homogenized with hexamethylene diisocyanate (HDI-biuret and HDI-trimer) at room temperature to form a polyurethane resin. The authors used different types of vegetable oils to characterize changes in the thermoset coatings formed. According to the published results, the castor oil-based polyurethane exhibited a higher cross-linking density and better thermal stability, owing to its higher hydroxyl functionality. On the other hand, the HDI-biuret coatings, containing linseed and karanja oils (with lower hydroxyl content), showed reduced thermal, mechanical, and anticorrosive properties.

Since itaconic acid contains the polymerizable methylidene functional group (═CH₂), the cured thermosets can be applied in coatings. Dong et al. (108) published work focused on the preparation and properties of UV-curable waterborne polyurethane coatings containing itaconic acid in the structure. The study proposed the synthesis of an itaconate-based cross-linking agent formed from itaconic acid and hydroxyethyl acrylate (HEA). The three-functional cross-linking agent, abbreviated “IHA”, was synthesized via Fischer esterification, yielding 93% of the product. The authors proposed a waterborne polyurethane (WPU) composed of poly(butylene adipate) (PBA) as the polyol and isophorone diisocyanate (IPDI) as the −NCO provider. WPU was synthesized through a four-step process, incorporating numerous additional compounds, such as 2,2-dihydroxymethylpropionic acid (DMPA, polyol cross-linker), 1,4-butanediol (BDO, chain extender), and the supportive HEA (−NCO groups terminator). Eventually, the WPU-IHA emulsion was formed, and the coated substrates, containing the prepared polymerizable prepolymers, were UV-cured. The team of researchers provided an exceptional number of analyses, including structural analyses (NMR, FTIR), emulsion stability measurements (zeta potential, particle size monitoring), rheological investigations and mechanical, thermal, and morphological descriptions of the produced thin layers. The results uncovered that the synthesized IHA enhanced the mechanical strength and the adhesion performance of the formed coatings. The waterborne characteristics include water absorption (8.37%) and contact angle (97.2°). The authors proposed the potential applications in antibacterial, self-cleaning, and self-healing utilities.

Several nonpolyurethane thermoset coatings, containing itaconate derivatives, were investigated in the published literature. Huang et al. (109) designed a self-healing, high-performance UV-curable coating fabricated from rubber seed oil and modified with itaconic acid. Their approach comprised itaconic acid modification by glycidyl methacrylate (GMA), forming glycidyl methacrylate precursor (GI). The resulting GI’s structure contains two polymerizable methylidene groups (═CH₂), one vacant hydroxyl, and one unoccupied carboxyl. The following step involved a nucleophilic substitution reaction between GI and epoxidized rubber seed oil (ERSO), resulting in a curable triacylglyceride-modified molecule (GIERSO). The study involved a polymerization kinetics analysis using FTIR and complex thermo-mechanical and thermal characterization via DMA and TGA analyses. Eventually, the tensile measurements and coating performance were provided, along with the studies of the shape memory and self-healing properties. The authors declare that the eventual biobased content reached 84.5%, due to the triacylglyceride and itaconic acid content. Additionally, the self-healing properties were evaluated as outstanding (86–100%), the mechanical strength reached 22.4 MPa, and the glass-transition temperature achieved 119.2 °C.

Optimal rheological characterization is crucial for coating technologies, as it primarily determines the applicable low thickness of the coated layer. When systems exhibit high viscosity, their formation into surface layers becomes much more complicated, or even impossible. The reactive diluents, as discussed earlier, to provide optimal modifications for 3D printing precursors, offer an appropriate opportunity to regulate the flow characteristics of coating technologies. Mehta et al. (110) investigated biobased reactive diluents for rheological modification of highly viscous itaconate-containing polyester systems. The researchers prepared four unsaturated polyesters (UPs) in total, which were modified with different reactive diluents from renewable and nonrenewable sources, and the findings were compared with styrene-based curable systems. Every synthesized UP contained itaconic acid and a second dicarboxylic acid–sebacic acid (C10) or succinic acid (C4). The entering polyols were three in total: 1,4-butanediol, 1,6-hexanediol, and glycerol. Each UP was synthesized via a two-step condensation, reaction involving the selected dicarboxylic acid and the polyol. Next, itaconic acid was introduced into each prepolymerized solution. The measured apparent viscosities exhibited non-Newtonian behavior (particularly pseudoplastic–the viscosity decreased with the increasing shear rate), and the observed viscosity levels ranged from 10 to 10,000 Pa·s at 1 s^–1 shear rate. The influence of the following reactive diluents was investigated: styrene (STY), methyl methacrylate (MMA), 2-hydroxyethyl methacrylate (HEMA), and isobornyl methacrylate (IBOMA). According to the results, the diluting properties of HEMA were comparable to those of the commercially used STY. On the other hand, the MMA and IBOMA-containing UPs exhibited deviation from the STY-involving reference. The reactivity measurements, thermal stability investigations, and volatility studies confirmed that HEMA is the most suitable reactive diluting alternative to styrene for highly biobased itaconate UPs.

Biobased alternatives for coating applications appear in many other sources in the literature. We summarized additional itaconate-involving precursors for thin-layer fabrication in Table 2. Most of the reported studies in the available literature investigated polyester structures, with two systems achieving nearly quantitative biobased content. (111,113,115) The polyester systems are often reported, investigated, and evaluated due to the optimal chemical structure of itaconic acid for polyester synthesis. Also, this compound uses environmentally friendly, often highly safe, and inexpensive starting materials, along with the formed water as a secondary product, thereby reducing risk during synthesis. Other two listed system possess epoxy- and polyurethane-containing chemical structures, which generally increase the potential reprocessability (due to the potential vitrimeric structure), and also ensures different performance, typically better, than polyester resins in terms of coating materials due to the higher content of the polar and bonding-forming functional groups, such as carbamate group (−NH–C(═O)–O−) and the formed hydroxyl group (−OH) usually from the epoxy “ring opening” reaction. (112,114)

Table 2. Summarized Itaconic Acid-Involving Precursors for Polymeric Coatings

itaconate coating precursors
type of the system	itaconic acid function	renewable content	suggested application	refs
Polyester	Cross-linker and Group Modifier	Unspecified	Encapsulation Resin	(111)
Epoxy Resin	Main Carbon Backbone	40–60 wt %	Wood Protective Coating	(112)
Polyester	Carbon Backbone	95–98 wt %	Bio-Based Coating Alternative	(113)
Polyurethane	Polyol Component	30–45 wt %	Bio-Based Coating Alternative	(114)
Polyester	Cross-linker	67–95 wt %	UV-Curable Biobased Coating	(115)

4.2. Functional Itaconate Coatings

The added value of itaconic acid in the coating systems and precursors lies primarily in its renewable character and polymerizable reactivity. Such systems can be suggested and synthesized similarly to their fossil-based analogues (acrylates, methacrylates, vinyl esters, unsaturated polyesters), but represent an opportunity to decrease the potential carbon footprint. In addition to their biobased character, several proposed and studied itaconate coating precursors serve added-value purposes, increasing their utility in the application and materials fields. Dixit et al. (116) reported their synthesis of two-pack polyurethane coatings containing citric and itaconic acids for antimicrobial purposes. Such properties protect the target substrate from weathering, abrasion, microbial colonization, and many other deteriorating processes. First, the authors synthesized propanetriol citrate polyol (PCE) from citric acid and epichlorohydrin. This prepared polyol was used in one case for the production of polyurethane with hexamethylene diisocyanate (HDI) and toluene diisocyanate (TDI). Other proposed material included an extra step: PCE was esterified with itaconic acid via Fisher esterification, assisted by azeotrope distillation. The modified PCE system, involving itaconic acid and poly(1,2,3-propanetriol citrate-co-1,2,3-propanetriol itaconate) (PPCI), was incorporated into a polyurethane using HDI. The organisms used for antimicrobial activity were Bacillus subtilis, Staphylococcus aureus, Escherichia coli, and Candida albicans. The investigations revealed that the PCE-HTDI (nonitaconate polyurethane) exhibited better gloss, adhesion, pencil hardness, and glass transition temperature than the PPCI-HDI coating (itaconic-involving). Both systems demonstrated good solvent resistance and exhibited sufficient antimicrobial activity against the above-listed organisms. The authors declare that their findings imply significant potential for the described coatings in biomedicinal applications.

The combination of sustainable approaches, itaconic acid-reactive structures, and nonisocyanate polyurethanes (NIPU) yielded additional value-added functional materials. Chen et al. (117) introduced a multicomponent NIPU-ester biobased structure exhibiting excellent heat-insulating and corrosive resistance properties. Their approach involved a two-step synthesis. First, they synthesized the NIPU structure from propylene carbonate and 1,10-diaminodecane, possessing two terminal vacant hydroxyl groups (−OH). Subsequently, the researchers esterified their NIPU with itaconic acid via precondensation (catalyzed by p-toluenesulfonic acid (pTSA)), followed by condensation (catalyzed by Tin(II) 2-ethylhexanoate). The product, which is solid at room temperature, was dissolved in an assisting solvent (anhydrous ethanol) and stirred for 1 h at 40 °C to form a homogeneous solution. Eventually, the NIPU emulsion (30% concentration) was formed and coated onto the target substrate. After the curing time (7 days), the layer properties were investigated. The authors found that their five tested entering reactant ratios (leading to the harder and softer materials) exhibited practically identical thermal stabilities. Their best-performing system contained a reactants’ molar ratio of 1:1.1 (NIPU precursor/itaconic acid). This system possessed the lowest thermal conductivity and the highest water contact angle. The uncovered outcome was caused by the optical cross-linking density, ensuring the best heat-insulating and anticorrosion properties.

Most of the described itaconate systems are composed of the functional derivatives of itaconic acid (modified acidic carboxyl functional groups (−COOH) within the diacid’s structure). Since the methylidene group (═CH₂) in the itaconic acid’s structure may be heteropolymerized (with different reactive monomers), interesting functional polymers can be fabricated. Schneider-Chaabane et al. (118) proposed a polyzwitterionic stimulus-responsive structure containing dissociable itaconic acid (see Figure 9). Their suggested coatings were investigated for the self-triggered antimicrobial activity, protein repellency, and cell compatibility. Since the introduced polymers possess a zwitterionic structure, itaconic acid in the carbon backbone (anionic monomer) must be combined with other polymerizable monomers that provide cationic centers must be involved. The authors used itaconic anhydride as an entering compound, which reacted with N-Boc-ethylenediamine to form a monoamide polymerizable monomer, 4-N-Boc-2′-Aminoethyl Itaconic Amide. Then, copolymerization with the polymerizable N,N-dimethylacrylamide and 4-methacryloyloxy benzophenone monomers followed. Finally, the functional deprotection on the cationic center (N-Boc-ethylenediamide) ensured the presence of both anionic monomer (itaconic acid) and cationic monomer (N-ethyleneamine). The authors evaluated the successful synthesis of a zwitterionic copolymer from a biobased building block, which exhibited sufficiently high smoothness and thickness, near-quantitative protein repellency, and substantial antimicrobial activity (against E. coli and S. aureus).

Figure 9. Synthesis of the deprotected zwitterionic itaconic acid involving copolymer (IA-BP-PZI) and the coating strategy ensuring the antimicrobial activity, protein repellency, and cell compatibility investigated by Schneider-Chaabane et al. (118) Reproduced from ref (118). Copyright [2019] American Chemical Society.

In the coating industry, itaconate systems primarily serve as a direct, biobased alternative to fossil-based precursors. Any significant functional properties are engineered selectively with a specific precursor. The following aspects have to be taken into account:

High viscosity levels of itaconate derivatives. The coating industry relies heavily on precisely defined rheological behavior;
The reactivity and degree of cure must be considered and affected by a specific itaconic acid derivative or other suitable additive.

5. Adhesive Precursors

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Adhesives connect various types of substrates by an invasive approach that does not involve the incorporation of connecting materials, such as screws, nuts, bolts, and rivets. Since adhesives do not provide a mechanical connection (provided by the connecting material or welds), their function depends on many combined factors. The compatibility of the target substrate and the adhesive is essential for strong adhesion. The efficient and strong connection between the adhesive and the adherent is affected by the substrate’s surface character (the surface morphology and preconditioning), (123) as well as by the chemical nature of both systems. (124) The physical factor (surface morphology) is usually easily modifiable–the optimal connected surface must be cleaned from small particles (such as dust, impurities), (125) and specifically preconditioned (highly smooth surfaces do not provide sufficient area to provide an optimal number of centers for the dispersion forces formation). (126) Second, the chemical compatibility of the adhesive and adherent is a key parameter for a successful adhesive performance (see schematic illustration in Figure 10) since these characteristics lead to the noncovalent intermolecular interactions (electrostatic and quantum-mechanical). (127,128) Every substrate and cured/polymerized system that forms the connecting matrix exerts dispersion forces that account for the majority of intermolecular interactions in adhesion. Dispersion forces (also known as London forces) are induced dipole–induced dipole interactions that find their foundation in the quantum mechanics description of atoms and molecules. (129,130) All solo or bonded atoms are composed of core particles (protons and neutrons) and the surrounding electrons. (129,130) According to quantum theory, electrons are these negatively charged particles that orbit the atomic core. Apparently, the atom/molecule appears to behave electro-neutral, but the real-time position of electrons and protons varies; therefore, the “induced dipole” is formed when a specific electron–proton position is reached. (129,130)

Figure 10. Schematic interpretation of itaconate-based photocurable adhesive investigated by Jamaludin et al., (119) and an illustration of the forming (and potential) noncovalent molecular interactions, such as hydrogen bonding, dispersion forces, and π–π stacking. (120−122) Reproduced from ref (119) Copyright [2022] American Chemical Society, from ref (120) Copyright [2023] American Chemical Society, from ref (121) Copyright [2023] American Chemical Society, and from ref (122) Copyright [2016] American Chemical Society.

Next to the dispersion forces (which are a part of van der Waals interactions), several more intermolecular connections are formed (see also Figure 10). The induced dipole–dipole interactions (Debye) and the dipole–dipole interactions (Keesom) complete the group of short-range attractive forces. (131) The long-range interactions are composed of ion–ion and ion-dipole noncovalent bonding. (132) The hydrogen bonding is one of the most well-known and essential noncovalent molecular interactions projected in numerous biological and artificial systems. (133) This type of force is explained either by electrostatic theory (the bonded hydrogen atom provide its electron to form bonded elector pair and the core positive charge of proton is attracted by another vacant electron pair of the hydrogen bonding acceptor), (134) or the transfer theory (the molecular covalent bonding leads to the generation of the vacant antibonding electron orbital (which is an acceptor of the vacant electron pair of the hydrogen bonding acceptor atom) and the occupied bonding electron orbital that contains the covalently bonded electrons of two atoms). (134) Other noncovalent interactions include the entropically driven hydrophobic effect (determined by the optical entropy of small, overwhelming molecules, such as liquid solvent) (135) and π-π interactions (representing multipole interactions typically in aromatic structures). (136)

When the itaconic acid structure is considered in the context of adhesion performance, the methylidene function group (═CH₂) is key for the photocured adhesives due to its polymerization activity. Adhesives that combine intermolecular bond formation with a 3D molecular-cured structure outperform standard adhesives lacking reactive groups. (33) Itaconic acid is compared to other structural alternatives (dicarboxylic acids); several compounds, such as citric acid, malic acid, or tartaric acid, possess a significant benefit over itaconic acid due to the presence of a free hydroxyl group (−OH), which generally improves the adhesion performance. This phenomenon has been observed numerous times in published investigations and studies. (156−158) However, if we overlook the linear polyester structures (containing itaconic acid or other dicarboxylic acid), the polymerizable methylene group (═CH₂) makes a critical difference in pressure-sensitive adhesives (PSA). Since itaconic acid is radically polymerizable, it can form linear long chains variously modified through the free carboxylic acid functional groups (−COOH). (159) This aspect provides a significant advantage over similar polymerizable monomers, such as acrylic or methacrylic acid. The published study demonstrated that the itaconic acid-involved curable oil system had lower overall volatility, enhanced T_g (increase of 10–20 °C), and a higher dynamic storage modulus (increase of hundreds of MPa). (101) These two carboxylic acids have a modifiable carboxyl acid functional group (−COOH), but only one instead of two in the case of itaconic acid. This structural composition gives itaconic acid the opportunity for both homogeneous and heterogeneous functionalization, which opens numerous options for specific adhesive applications. (160) Ester, amide, polyurethane functional bonding varies the adhesion performance and highlights itaconic acid and its derivatives’ unique position among the fossil-based alternatives. (161)

Bonding strength is the most essential characteristic of adhesives. This parameter is primarily influenced by the chemical composition of the adhesive and the adherent (as we described earlier) and by the surface area covered by the adhesive. Since the adhesive connection is primarily determined by the dominant surface area rather than the applied adhesive volume, the measured adhesive (lap shear) strength accounts for surface area. The mathematical calculation of the adhesive strength stands as follows (5) (137,146)

σ_{Adhesion} = \frac{F_{MAX}}{A}

(5)

where σ_Adhesion is the adhesion strength (MPa), F_MAX represents the maximum force at adhesion break (N), and A stands for the adhesion area of the specimen (mm²). The following subsections provide a comprehensive review of the itaconate adhesives engineered through different approaches. The targeted sustainable-increasing goal connects all the introduced adhesive systems.

5.1. (Photo)Curable Thermoset Adhesives

Polyurethane chemical structures are among the most well-known and commercially used adhesives, and their molecular composition is highly diverse due to the wide range of polyols and isocyanates. Li et al. (138) used itaconic acid to synthesize an ester derivative capable of reacting with the chosen isocyanate (−NCO source) and of providing an addition reaction with thiocompounds. Initially, the itaconate polyol (IAOH) was synthesized from itaconic acid and 1,6-hexanediol via Fisher esterification. Then, the polyurethane-sulfide vitrimer was produced from the prepared IAOH, toluene diisocyanate (TDI), 1-thioglycerol, 1,3-propanedithiol, and 1,4-phenylenediboronic acid. Since the sulfide-forming components (thiol and methylidene functional groups (═CH₂)) can be unbonded (at high temperatures) and then rebonded, the self-healing character of the thermoset adhesive was investigated. The authors uncovered that their itaconic acid–based polyurethane network with the dynamic boronic ester bonds achieved excellent adhesion strength (8.9 MPa for wood substrate), and the self-healing properties were confirmed by the initial tensile test (reaching 15.6 MPa strength) compared to the recycled thermoset (at 120 °C for 20 min), achieving maintained tensile properties (15.1 MPa of the tensile strength).

Epoxy-based adhesives are also commonly used across numerous material applications, but their molecular structure is largely fossil-based, mainly consisting of bisphenol A derivatives. Kim et al. (139) incorporated itaconic acid into the bisphenol A diglycidyl ether structure to obtain bisphenol A diglycidyl itaconate. The authors used a dual-curing approach: thermally initiated polymerization (1-methylimidazole as the thermal initiator) and photoinitiated polymerization (2,2-dimethoxy-2-phenylacetophenone (DMPA) as the photoinitiator). They concluded that the adhesive characteristics were similar to or superior to those of conventional epoxy acrylate oligomer adhesives (EAOs). Additionally, they increased sustainability by incorporating biobased itaconic acid into the epoxy precursor.

Phototriggered thermoset-forming adhesives have strong potential as efficient, fast-performing, and universal curable adhesives that require only a negligible amount of photoinitiator and an appropriate irradiation source. However, their Achilles heel lies in their exclusive application to fully transparent substrates (or at least one substrate must consist of such material) that allow the irradiation penetration, such as poly(methyl methacrylate) (PMMA), glass, or polypropylene. Jamaludin et al. (119) introduced sustainable itaconate-based polyester structures suitable for photocuring adhesives. Their systems comprised three multifunctional carboxyl acids (itaconic, 1,12-dodecanedioic, and citric acid), which were condensed with a selected polyol (1,3-propanediol). The authors synthesized one particular polyester structure, and their tested specimens varied by the irradiation exposition time (1, 3, 5, 10, 15, and 30 min) (see Figure 11). In total, five substrates were investigated (PMMA, wood, glass, stainless steel, and PTFE), and PMMA served as the transparent substrate required for all experiments. The results reveal a successful synthesis via catalyst-free polycondensation. Irradiation exposure time improved adhesive properties, and the longest-cured systems possessed high hydrophobicity due to high cross-linking density and molecular weight.

Figure 11. Photocurable polyester itaconate sustainable adhesive applied on five different adherents: poly(methyl methacrylate) PMMA, wood, glass, stainless steel, and poly(tetrafluoroethylene) (PTFE). (119) Reproduced from ref (119). Copyright [2022] American Chemical Society.

5.2. Pressure-Sensitive Adhesives (PSA)

Pressure-sensitive adhesives (PSA) are widely used, specifically engineered systems (usually a polymer or oligomer) that form an adhesive bond with the target adherent when light pressure is applied (see schematic in Figure 12). (140) The provided force on the area with particular PSA leads to the system’s directed flow toward the substrate, and the adhesive distributes onto the connected surface. During this process, the short-range van der Waals forces (mainly) are formed, ensuring the connection between adhesive and adherent. (140) PSAs are used in glue tapes, medical devices, automotive, and electronic applications. (141,142) Since itaconic acid is polymerizable, the radically polymerized structure may serve as a biobased alternative to the commonly used PSAs, such as acrylics, rubbers, or silicones. (140−142) Fang et al. (143) investigated the influence of monobutyl itaconate and other comonomers on acrylic latex PSAs. The researchers used monobutyl itaconate, β-carboxyethyl acrylate, and methacrylic acid to produce pressure-sensitive adhesives composed primarily of butyl acrylate (around 90 wt %). The authors investigated numerous measurable parameters of the formed PSAs and revealed that the size of the formed latex particles decreased with increasing amounts. Also, since the added carboxyl acids are hydrophilic, the overall water absorption of fabricated PSAs increased (monobutyl itaconate PSA water absorption 7.6%, methacrylic acid 9.8%, and β-carboxyethyl acrylate 11.3%). In the same trend, the water contact angle decreased, confirming the increasing hydrophilic character. The conclusion revealed that the presence of monobutyl itaconate in PSA improves its cohesive strength.

Figure 12. (a) Highly crosslinked itaconic acid derivative for PSA, (b) itaconic acid ester system enhanced with acrylic derivatives for PSA. Investigated pressure-sensitive adhesives (PSA) containing itaconic acid and its derivatives. (147) Copyright (2024), American Chemical Society. The multicomponent cross-linkable PSA synthesized from sustainable sources is illustrated in the bottom-left corner, (145) while the underwater-performing PSAs for potential wound treatment are displayed in the right half. (146) Reproduced from ref (145) copyright [2025] American Chemical Society and from ref (146) copyright [2024] American Chemical Society.

Unlike the previous study that investigated the impact of an itaconate additive, Casas-Soto et al. (144) studied PSAs composed primarily of itaconic acid derivatives. The researchers engineered five copolymer structures with varying amounts of dibutyl itaconate (DBI) and lauryl methacrylate (LMA), with a constant 1 wt % of itaconic acid in each system. The copolymer was initiated by potassium persulfate (KPS) and stabilized via hydroquinone (HQ). The formed PSA oligomers were investigated structurally (FTIR, NMR), and their molecular weight, gel content, particle size, and conversion were determined. Their functional thermal, viscoelastic, and adhesive properties were also described. In conclusion, the LMA increased the gel content and the molecular weight of the prepared copolymers. The best-performing system, suitable for a PSA-type of adhesive, contained 24 wt % dibutyl itaconate, 75 wt % lauryl methacrylate, and 1 wt % itaconic acid.

Xue and the team synthesized the multicomponent itaconic acid derivatives involving PSAs (see Figure 12a). (145) The proposed copolymer adhesives comprised dibutyl itaconate (initially synthesized from itaconic acid and n-butanol via esterification), acrylic acid, butyl acrylate, and glycidyl methacrylate. The copolymerization was initiated with ammonium persulfate (APS), and the authors produced a total of 5 oligomer structures for potential application as PSAs. Since the proposed copolymers contained vacant carboxyl groups (−COOH, acrylic acid), and reactive epoxy functional groups (−CH(O)CH–, glycidyl methacrylate), the suggested structures underwent intermolecular cross-linking during the emulsion polymerization. The reported viscosities of prepared latexes ranged from 94 to 116 mPa·s, the synthesis yields ranged from 96.3 to 98.6%, and the biobased content ranged from 30.7 to 51.3 wt %. As the authors conclude, their biobased itaconate PSA (containing 30 wt % of dibutyl itaconate) achieved significantly higher holding power and peel strength on polar adherent than the commercial reference acrylic PSA. PSAs with higher itaconate content (50 wt %) showed superior holding power and peel strength on polar substrates but performed poorly on nonpolar substrates.

Several applications require high-performing PSAs capable of operating underwater in wet conditions, especially for biomedical applications. Zeng et al. (146) published a study focused on the engineering of itaconic acid–based adhesives, experimentally tested for potential toxicity, antimicrobial activity, and degradability, suitable for promoting hemostasis of skin wounds (see Figure 12b). The prepared PSAs are composed of the synthesized unsaturated poly(1,2-butylene oxide) (UPBO), which was produced initially from 1,2-butylene oxide, itaconic acid, and a suitable catalyst. Next to the synthesized UPBO, the directly available pentaerythritol acrylate (PETA) and itaconic acid (IA) were mixed with UPBO and UV-initially polymerized (2,2-dimethoxy-2-phenylacetophenone (DMPA) served as an initiator). The conclusion revealed that the hydrophobic segments of poly(1,2-butylene oxide) (PBO) play a key role in removing the hydration layer between adhesive and adherent. This process provides the formation of noncovalent interactions with the adhesive. The authors reported that the prepared PSA exhibits substrate-independent underwater adhesion to both hydrophobic (glass, wood, stainless steel) and hydrophobic (PET, PMMA, and PTFE) surfaces. Additionally, the adhesion strength reached >100 kPa after 30 uses and 20 days of storage underwater.

5.3. Starch-Itaconate-Based Adhesives

Starch-based adhesives are highly hydrophilic and highly sustainable. Therefore, their appropriate combination with itaconic acid can be outstanding for strongly polar substrates, such as wood, paper, or glass. The reactive itaconates may enhance the adhesion performance of starch-based multicomponent systems. Jin et al. (148) investigated an adhesive composed of corn starch, N-hydroxyethyl acrylamide (HEAA), and itaconic acid (IA), copolymerized with initiator ammonium persulfate (APS). The authors aimed to reduce the excessive hydrophilicity of the starch. Their prepared adhesive swelled by 10% after water soaking at 20 °C for 2 h, confirming the decreased polar character and verifying the improved water resistance. The structural analyses confirmed a cross-linked multicomponent structure during the performed hot-pressing.

The regulation of the excessively polar character of starch, resulting in low adhesion strength performance in humid environments, was investigated by Shao and the team. (171) The researchers performed a six-step process leading to the starch adhesives modified by itaconic acid and silicone to increase the wet bonding strength on wood substrates. In the first step, the highly polar corn starch was oxidized using sodium hypochlorite (NaClO). The next step involved homogenizing sodium dodecyl sulfate (SDS) and polyoxyethylene octylphenol ether-10 (OP-10). Then, the specific molar ratios of itaconic acid (IA), 3-methacryloxypropyltrimethoxysilane (MEMO), and 1,2-bis(triethoxysilyl)ethane (BTESE) were prepared for the silanization. Subsequently, the emulsifier (prepared in step two) was mixed with the silanization solution (prepared in step three). Then, the polymerization initiator, ammonium persulfate (APS), was added to into the complex reactive solution to initiate copolymerization. Eventually, the preoxidized corn starch was homogenized with the emulsified silanization solution, initiated by APS to form the final product. The authors determined the optimal conditions for maximizing the wet-bond strength of their prepared adhesive: 60 wt % of starch, the copolymerization initiated by 7.5 wt % of APS (calculated to IA), emulsifier (SDS) content 1.8 wt % (calculated to the silanization solution), and 1.2 wt % of polyoxy-ethylene octylphenol ether-10 (calculated to the silanization solution), reaction temperature of 70 °C, the reaction time 17 h.

Adhesives usually address similar issues and problems to polymeric coatings, since both applications depend heavily on the rheological profile of the reactive precursor. Besides the previously mentioned challenges (at the end of Section 4), the adhesive material sector using itaconic acid deals with the following aspects:

A sufficient linear polymerization stage must be achieved to achieve the required adhesive performance. Also, the precisely engineered itaconate structure contributes to the overall functional performance;
The optical properties of the used precursors must be taken into account, as photocuring applications often require highly transparent precursors, which can be challenging to achieve in biobased systems.

6. Functional Textile Additives

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The molecular composition of itaconic acid is optimal for several modifying purposes due to its two reactive carboxyl acid groups (−COOH), which can react together to form the cyclic itaconic anhydride, which tends to react even more spontaneously. The chemical structure of this dicarboxylic acid can alter the surface tension and energy of the targeted modified material. (151) Textile fibers are a suitable candidate for the functionalization due to their high free hydroxyl group content (−OH), which can be esterified by carboxylic acid (−COOH) or anhydride (R–CO–O–OC–R′) (see Figure 13). The positive outcomes associated with itaconic acid content in several fibers are described in the literature. Sharif et al. (149) focused on the increase in water repellency of cotton fabrics induced by the nontoxic, biobased carboxylic acid combination of stearic acid, succinic acid, and itaconic acid. Stearic acid is a long-chain fatty acid (C18) with exceptional hydrophobic character. The used dicarboxylic acids (succinic and itaconic) served as cross-linkers in the proposed approach. The authors used different amounts of stearic acid (11–50 wt %), tested at temperatures between 160 and 200 °C, and a reaction time of 3 h. In addition to the water repellency investigation, the researchers provided a comprehensive structural characterization of their modified cotton fabrics (using EDX, FTIR, SEM, XRD, and ¹H NMR), and antimicrobial resistance was also observed. The conclusion identified two optimal component recipes for optimal performance. The first modifying solution consisted of 16 wt % stearic acid, 7 wt % sodium hypophosphite, 7 wt % triethanolamine, and 7 wt % succinic acid, heated to 200 °C for 3 h under vacuum (all applied to the cotton fabrics). The second well-performing recipe contained 16 wt % stearic acid, 7 wt % sodium hypophosphite, 7 wt % triethanolamine, and 7 wt % of itaconic acid at 160 °C for 3 h under vacuum. Both of the determined systems reached a water repellency level of 4.

Figure 13. Cellulose fabrics modifications with itaconic acid and its reactive cyclic anhydride intermediates, achieving high durable-press performance and a significant increase in strength retention. (151) Reproduced from ref (151). Copyright [2012] American Chemical Society.

Boondaeng and the team performed another modification of the natural fibers (particularly cellulosic fibers). (150) The goal was to provide an anticrease finish on the tested fabric using itaconic acid and the presynthesized itaconic anhydride. The study also incorporated the biotechnological production of itaconic acid, using Aspergillus terreus K17. The yields obtained were 0.39 g/g and 0.4 g/(L·h) after 72 h of cultivation. After the used acid was produced, analyzed, isolated, and purified, the authors continued engineering the anticrease finish on the selected cotton fiber, which involved several steps, including determining the optimal sodium hypophosphite concentration (NaH₂PO₂, SHP) and setting the optimal process temperature. Naturally, the commercial anticrease finish was used as a reference. In addition to the structural identification methods (FTIR and SEM), the researchers studied the wrinkle recovery angle, breaking force, tearing strength, whiteness and yellowness indexes, and the water contact angle for the experimental and reference anticrease finishes. The conclusion revealed that itaconic acid incorporation improved wrinkle resistance. At the same time, the cotton fabrics remained functionally unchanged, which reflected in the maintainance or improvement of mechanical characteristics compared to the fibers treated with the commercial anticrease mixture. The adverse effects were observed in connection with the fabric coloring–the biotechnologically produced itaconic acid contained residual glucose from the fermentation process, which triggered a Maillard reaction, turning the fabrics yellow.

The textile additives based on intaconic acid represent a promising application field due to the highly biobased material substrate. The itaconate derivatives serve as performance molecules derived from renewable sources, so in this application, the analytical approach is the most critical aspect. The modifications provided by itaconic acid must be observable and demonstrated using suitable analytical instrumentation and approaches.

7. Assisting Monomer for Hydrogels

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Itaconic acid is an ideal assisting monomer or even a reactive substitute for acrylic, methacrylic, and other possible fossil-based compounds due to its renewable origin, multiple functionalities, nonvolatility character, and its unique ability to form the cyclic itaconic anhydride. The two carboxyl acid groups (−COOH) can be esterified to form currently used poly(ethylene oxide) (PEO) or poly(propylene oxide) (PPO) ether structures, providing elevated hydrophobicity due to the unsaturated carbon backbone (see Figure 14b). (153) When the selected reacting polyols possess shorter molecular length and contain more vacant hydroxyl and polar ether/ester bonds, the hydrogel is naturally more hydrophilic, while maintaining the required properties provided by the incorporated itaconic acid, such as antimicrobial ability, anti-inflammation, or self-healing potential. (152−154) The incorporation of presynthesized, specific itaconate (particular functionalized monoesters) represents another hydrogel engineering approach (see Figure 14a). The two functional carboxyl acid groups (−COOH) of itaconic acid can be monoesterified with many different alcohols, ensuring a specific targeted final property. (154) Several itaconate-modified hydrogels are functionalized to ensure their injectability. When the itaconic structure is not incorporated directly into the hydrogel carbon backbone, it can serve as a low-molecular-weight cross-linking agent, affecting the functional hydrogels. The carboxyl acid functional groups (−COOH) can be modified in the monoacid form, forming a monomer derivative with specific physical-chemical properties and polymerizable functionality, which determines its role in the multicomponent systems. (155)

Figure 14. Two particular approaches for incorporating sustainable itaconic acid into the hydrogel structures. (a) The presynthesized itaconic monoesters serve as reactive molecules that can modify the structure of the primary hydrogel site. (154) Reproduced from ref (154). Copyright [2024] American Chemical Society. (b) Pure itaconic acid can be esterified onto the main polymer chain, providing the required properties. (153) Reproduced from ref (153). Copyright [2023] American Chemical Society.

The incorporation into a hydrogel structure via ester bonding enables stimuli-responsive behavior, potentially triggered by pH or salt concentration. Sakthivel et al. (152) investigated pH/salt-responsive polymeric hydrogels exhibiting biocompatible, antimicrobial, and biodegradable characteristics. The proposed multicomponent systems were synthesized through a three-step process. Initially, the condensation of itaconic acid and diethylene glycol took place, producing the ester prepolymer. Subsequently, chain growth was initiated by potassium persulfate, generating prepolymer radicals. Eventually, the polymerization propagation was mediated using acrylic acid and N,N′-Methylenebis(acrylamide) as additional comonomers. The final polymerized structure contained acidic functional groups ((−COOH), represented by acrylic acid) and basic groups ((−NH−), provided by the copolymerized N,N′-Methylenebis(acrylamide)). Structural confirmation was provided by FTIR, MALDI-TOF-MS, SEM, and XRD. Several conclusions were drawn, including the determined maximum swelling extent of the hydrogel at pH 7.4–10, indicating the overwhelming influence of carboxylate anions over protonated amines. Additionally, monovalent cations, such as NaCl, showed greater salt responsiveness due to charge screening. The antibacterial effect was efficient toward (gram + ve) pathogens, and the systems with three itaconic acid monomer units exhibited 80% cell viability index. The determined degradation reached 88%. The authors declare a high utility potential for biomedical applications.

Ma and the team demonstrated another itaconate hydrogel product with high medical potential for wound repair applications. (153) The researchers reported an efficient synthetic approach to obtain polyester, a one-component itaconate hydrogel, produced via simple one-step esterification. This simple engineering approach simplifies the chemical production, thereby increasing its applicability potential. The authors esterified Pluronic (also known as poloxamer/F127), a structurally defined a copolymer of poly(ethylene oxide) (PEO) and poly(propylene oxide) (PPO), with itaconic acid to terminate the free hydroxyl groups (−OH). The formed structure became a slightly acidic, hydrophilic system due to the free carboxyl acid group (−COOH) at the compound’s ends. After several structural and functional investigations, the authors described the efficiently produced itanocate hydrogel as a multifunctional bioactive hydrogel with temperature-sensitive gelation, self-healing, exceptional injectability, and excellent rheological behavior. The main goals, including antibacterial activity, anti-inflammation, and regulation of macrophage polarization, were achieved with the produced hydrogel, and the proposed product could significantly promote the repair of MRSA-infected wounds (MRSA stands for methicillin-resistant Staphylococcus aureus). Generally, the produced itaconate hydrogel shows excellent potential for wound healing and tissue regeneration.

The direct incorporation of a diacid structure into polyester compounds requires both carboxyl acid groups (−COOH) to be in unmodified form. The other engineering approach, targeting specific properties of the eventual hydrogels, uses prefunctionalized itaconates with specific physical-chemical characteristics, thereby the hydrogel-forming molecular system to meet direct requirements. Zhou et al. (154) demonstrated this principle in their work on the injectability of a chitosan-octyl itaconate hydrogel with anti-inflammatory properties. The presented production path involved the functionalization of chitosan with 4-octyl itaconate, forming amide side chains on the chitosan polymer. The authors used the EDC/NHS carbodiimide synthetic pathway, creating a bond between free amine groups (−NH₂) and carboxyl groups (−COOH) (EDC stands for 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimid and NHS represents N-hydroxysuccinimide). The whole functionalization solution comprised chitosan (CS), 4-octyl itaconate (OI), EDC, and NHS, in the following molar ratio (CS/OI/EDC/NHS): 50:1:10:5 (the reaction was performed in a water/ethanol solvent mixture 1:1 (v/v)). After the successful chitosan modification, the injectability, biocompatibility, anti-inflammatory, and antioxidant properties were investigated. The proposed functional modification of chitosan enhanced the hydrogel’s anti-inflammatory properties, suggesting potential biomedical applications.

Next to the direct difunctional linkage in several polyester structures, or the direct and specific modification of suitable hydrogel-forming compounds, itaconic acid represents a low-molecular modifier that is not covalently bonded to the functional systems but provides the required enhancing role in multicomponent materials. Naderi et al. (155) published an investigation focused on itaconate-based external cross-linkers for hydrogels. The authors introduced two itaconate reactive cross-linkers. The IA-GMA monomer was synthesized from itaconic acid (IA) and glycidyl methacrylate (GMA) through the epoxy-opening approach. This monomer contained methylidene reactive groups (═CH₂) suitable for radical polymerization. The second monomer, IA-ECH, was produced from itaconic acid (IA) and epichlorohydrin (ECH) via nucleophilic substitution. IA-ECH is terminated with epoxy functional groups (−CH₂(O)CH₂−) and is suitable for amine-catalyzed systems or ionic-polymerized thermosets. The main conclusions of the study revealed that IG-GMA possessed high water absorbency under load (AUL) due to its polar structure (containing free hydroxyl groups (−OH)). According to the authors, IA-ECH could be fully biobased (they declare that ECH can be synthesized from glycerol). This cross-linker contains both reactive epoxy functional groups (−CH₂(O)CH₂−) and free hydroxyls (−OH, produced from the IA-ECH hydrolysis), which offer potential for complex internal and external cross-linking. However, its reactivity regulation is complicated due to numerous potential products.

Hydrogels exemplify a material sector that could serve in medicinal applications. Sustainability, particularly the biocompatibility and nontoxicity of systems for hydrogel fabrication, is a key parameter for this application segment. The following challenges have to be considered for hydrogel materials:

The suitable substitution of another dicarboxylic acid with itaconic acid must be compatible with the hydrogel substrates (if the specific hydrogel requires it);
The viscoelastic properties of the produced hydrogels must meet the required levels. Itaconic acid may influence the reactivity and, in particular, the rheological profile of the produced hydrogel.

8. Conclusion and Future Outlook

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Itaconic acid is a promising, fully biobased reactive compound, synthesized via the biotechnological process. Several target applications were investigated in the available literature, such as additive manufacturing, composite fabrication, coatings, adhesives, functional textile additives, and medicinal hydrogels. Since itaconic acid has a unique polymerizable chemical structure, that can entirely replace the currently used radical-polymerized compounds, such as acrylates, methacrylates, vinyl esters, or styrene, moreover, this molecule contains two carboxyl acid functional groups (−COOH), which lead to several functional derivatives (anhydrides, esters, or amides). Therefore, itaconic acid may be incorporated into numerous working systems (polyesters, polyamides, or polyethers), thereby modifying their final processability, appearance, or functionality. The specific carbon backbone of itaconic acid offers particular advantages essential to the materials industry.

Sustainability is one of the most evident and substantial advantages itaconic acid offers to numerous material industries. The carbon structure from renewable sources promises the future substitution of fossil-based systems, which complicate the processes from the carbon footprint and disposability standpoints. The biotechnological production of itaconic acid could potentially reduce CO₂ emissions due to the photosynthesis, thereby increasing CO₂ accumulation in biomass. The disposability issue can be overcome in many of the mentioned applications due to the possible degradability of the itaconate-involved systems. In addition to the positive aspects of production and disposability, the biocompatibility of itaconic acid systems and derivatives is an irreplaceable property for several tissue-involving applications. Itaconic acid is suitable for textile modifications in clothing and other wearing materials. Regarding tissue regeneration and functional hydrogels, the itaconate structures represent ideal building and assisting monomers for the synthesis of the main polymer chain or for modifying existing working systems.

The processing factors associated with itaconic acid incorporation improve efficiency and health safety, while the toxicity factors and volatility levels are minimized. Itaconic acid represents an ideal entering reactant due to its nonvolatile, solid-phase appearance. Compared to acrylates, methacrylates, or vinyl esters, itaconic acid is much safer from a respiratory and handling standpoint. Moreover, itaconic acid can be modified to mono- or difunctional derivatives, which after its physical-chemical properties. Therefore, itaconate sustainable alternatives may be functionalized to meet specific requirements, while minimizing handling and toxicity. All the summarized descriptions, characteristics, and functions highligh itaconic acid’s exceptional potential across numerous application fields, advancing toward more sustainable, safe, and efficient generation.

Author Information

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Corresponding Author
- Vojtěch Jašek - Institute of Materials Chemistry, Faculty of Chemistry, Brno University of Technology, 61200 Brno, Czech Republic; https://orcid.org/0000-0002-8020-4948; Email: [email protected]
Authors
- Silvestr Figalla - Institute of Materials Chemistry, Faculty of Chemistry, Brno University of Technology, 61200 Brno, Czech Republic
- Radek Přikryl - Institute of Materials Chemistry, Faculty of Chemistry, Brno University of Technology, 61200 Brno, Czech Republic
Author Contributions
CRediT: Vojtech Jasek conceptualization, visualization, writing - original draft, writing - review & editing; Silvestr Figalla resources, supervision, validation; Radek Přikryl resources, supervision, validation.
Notes
The authors declare no competing financial interest.

Acknowledgments

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V.J. acknowledges the financial support from the Ministry of Education, Youth and Sport of the Czech Republic (project No. FCH-S-26-9028).

References

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Abstract
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Figure 1
Figure 1. Graphical illustration of the itaconic acid’s molecular structure contains two carboxylic functional groups exhibiting the reactive delocalized electrons in resonance, a radically polymerizable terminal alkene functional group, and the schematic potential functional derivatives, such as amides (derived from amines and acids), esters (derived from alcohols and acids), and anhydride (derived from two acids).
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Figure 2
Figure 2. Primary parameters influencing the stereolithography 3D printing. (a) Irradiation source type (the characteristics wavelength and power value), (b) the specific reactivity of the precursor (determined by Jacob’s working curve or differential scanning calorimetry (DSC)), (c) the rheological profile of the resin-forming systems (dependent on the temperature by the Arrhenius law and affected by the reactive diluent’s content) (d) the published diluting properties of the experimentally applied itaconate derivaties. (84) Reproduced from ref (84). Copyright [2017] American Chemical Society.
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Figure 3
Figure 3. (a) Itaconic acid–based polyester used in combination with 4-acryloyl morpholine (ACMO) as a reactive diluent, (60) Reproduced from ref (60). Copyright [2023] American Chemical Society (b) oligomer itaconate precursor systems containing biobased reactive diluents derived from furfuryl, tetrahydrofurfuryl, solketal, and diacetone glucose reactive derivatives, (63) Reproduced from ref (63). Copyright [2025] American Chemical Society (c) Polylactone/itaconate elastomer resins processed by reversible addition–fragmentation chain transfer (RAFT) mediated 3D-printing with polypeptide surface functionalization, (67) Reproduced from ref (67). Copyright [2023] American Chemical Society (d) modified grapheme oxide (GO) nanoparticles incorporated into a itaconate-based 3D printing resin for the enhancement of the material properties while maintaining the advanced functional properties ensured by GO’s the conjugated π-electron system. (66) Reproduced from ref (66). Copyright [2025] American Chemical Society.
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Figure 4
Figure 4. Poly(ester amide) structure incorporating itaconic acid as a reactive polymerizable precursor suitable for stereolithography 3D printing. (76) Reproduced from ref (76). Copyright [2022] American Chemical Society.
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Figure 5
Figure 5. Complex synthetic scheme composed of reactions described and evaluated in the investigation provided by Arnaud and the team. (59) The scheme describes three different chemical approaches leading to the symmetric esters produced via Fischer esterification, asymmetric esters combining anhydride and epoxide compounds, and symmetric esters derived from epoxy entering compounds. Reproduced from ref (59). Copyright [2021] American Chemical Society.
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Figure 6
Figure 6. Illustrated polyester itaconic acid–based cured resins, modified with selected itaconate-reactive diluents, fabricated through 3D printing. (a) 3D-printed DMA specimen containing dicyclohexyl itaconate (DE-1), (b) 3D-printed DMA specimen containing bis(2-hydroxybutyl) itaconate (DHE-1). (59) Reproduced from ref (59). Copyright [2021] American Chemical Society.
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Figure 7
Figure 7. Schematic illustration of the proposed fully biobased composite from itaconate resin and cotton fabrics as the solid-phase filler along with thermo-mechanical properties measured by the DMA analysis. (a–e) SEM pictures of the obtained composite prototype, (f) the photo of the fabricated composite. (100) Reproduced from ref (100). Copyright [2018] American Chemical Society.
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Figure 8
Figure 8. Schematic list of potential and investigated application fields for itaconic acid–based polymeric coatings for material applications. The illustrated reaction scheme describes the modification of epoxidized soybean oil (ESO) with itaconic acid monoester, yielding itaconated epoxidized soybean oil (IESO), which represents a green alternative to the commercially used acrylated epoxidized soybean oil (AESO) for general coating applications. (101,102) Reproduced from ref (101) Copyright [2016] American Chemical Society and from ref (101) Copyright [2019] American Chemical Society.
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Figure 9
Figure 9. Synthesis of the deprotected zwitterionic itaconic acid involving copolymer (IA-BP-PZI) and the coating strategy ensuring the antimicrobial activity, protein repellency, and cell compatibility investigated by Schneider-Chaabane et al. (118) Reproduced from ref (118). Copyright [2019] American Chemical Society.
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Figure 10
Figure 10. Schematic interpretation of itaconate-based photocurable adhesive investigated by Jamaludin et al., (119) and an illustration of the forming (and potential) noncovalent molecular interactions, such as hydrogen bonding, dispersion forces, and π–π stacking. (120−122) Reproduced from ref (119) Copyright [2022] American Chemical Society, from ref (120) Copyright [2023] American Chemical Society, from ref (121) Copyright [2023] American Chemical Society, and from ref (122) Copyright [2016] American Chemical Society.
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Figure 11
Figure 11. Photocurable polyester itaconate sustainable adhesive applied on five different adherents: poly(methyl methacrylate) PMMA, wood, glass, stainless steel, and poly(tetrafluoroethylene) (PTFE). (119) Reproduced from ref (119). Copyright [2022] American Chemical Society.
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Figure 12
Figure 12. (a) Highly crosslinked itaconic acid derivative for PSA, (b) itaconic acid ester system enhanced with acrylic derivatives for PSA. Investigated pressure-sensitive adhesives (PSA) containing itaconic acid and its derivatives. (147) Copyright (2024), American Chemical Society. The multicomponent cross-linkable PSA synthesized from sustainable sources is illustrated in the bottom-left corner, (145) while the underwater-performing PSAs for potential wound treatment are displayed in the right half. (146) Reproduced from ref (145) copyright [2025] American Chemical Society and from ref (146) copyright [2024] American Chemical Society.
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Figure 13
Figure 13. Cellulose fabrics modifications with itaconic acid and its reactive cyclic anhydride intermediates, achieving high durable-press performance and a significant increase in strength retention. (151) Reproduced from ref (151). Copyright [2012] American Chemical Society.
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Figure 14
Figure 14. Two particular approaches for incorporating sustainable itaconic acid into the hydrogel structures. (a) The presynthesized itaconic monoesters serve as reactive molecules that can modify the structure of the primary hydrogel site. (154) Reproduced from ref (154). Copyright [2024] American Chemical Society. (b) Pure itaconic acid can be esterified onto the main polymer chain, providing the required properties. (153) Reproduced from ref (153). Copyright [2023] American Chemical Society.
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Itaconic Acid–Based Compounds Fulfilling the Role of Biotechnologically Produced Alternatives to Fossil-Based Precursors for Material ApplicationsClick to copy article linkArticle link copied!

ACS Engineering Au

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1. Introduction

Figure 1

2. Precursors for 3D Printing

Figure 2

2.1. Itaconic Acid-Derived Polyester Resins

Figure 3

2.2. Other Curable Itaconate Resins

Figure 4

2.3. Itaconate-Based Reactive Diluents

Figure 5

Figure 6

3. Matrix for Composites

3.1. Carbon Fiber Composites

3.2. Natural Itaconate Composites

Figure 7

4. Functional Coatings

Figure 8

4.1. Bio-Based Alternative Itaconate Coatings

4.2. Functional Itaconate Coatings

Figure 9

5. Adhesive Precursors

Figure 10

5.1. (Photo)Curable Thermoset Adhesives

Figure 11

5.2. Pressure-Sensitive Adhesives (PSA)

Figure 12

5.3. Starch-Itaconate-Based Adhesives

6. Functional Textile Additives

Figure 13

7. Assisting Monomer for Hydrogels

Figure 14

8. Conclusion and Future Outlook

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Acknowledgments

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Itaconic Acid–Based Compounds Fulfilling the Role of Biotechnologically Produced Alternatives to Fossil-Based Precursors for Material Applications
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