Toward replacement of styrene by bio-based methacrylates in unsaturated polyester resins

Cousinet, Sylvain; Ghadban, Ali; Fleury, Étienne; Lortie, Frédéric; Pascault, Jean‐Pierre; Portinha, Daniel

doi:10.1016/j.eurpolymj.2015.02.016

Cited by 90 publications

(84 citation statements)

References 27 publications

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“…To determine the volatility of MVA and to compare it to that of styrene, the mass loss of MVA and styrene over time was measured using TGA ( Figure ). The results confirmed that styrene was highly volatile, as it completely evaporated (only 0.3% remained) in about 65 min at 30 °C, which was in agreement with Sylvain, Cousinet et al, who worked on replacing styrene with bio‐based methacrylates for UPR . In contrast, MVA exhibited significantly lower HAP/VOC emissions with a weight loss of less than 5% after isothermal for 9 h at 30 °C, confirming that the synthesized MVA is a promising comonomer monomer with low VOC.…”

Section: Resultssupporting

confidence: 87%

Soybean‐Oil‐Based Thermosetting Resins with Methacrylated Vanillyl Alcohol as Bio‐Based, Low‐Viscosity Comonomer

Zhang

Thakur

et al. 2017

Macro Materials & Eng

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A novel, bio‐based, aromatic monomer (methacrylated vanillyl alcohol, MVA) is synthesized using vanillyl alcohol and methacrylic anhydride in the absence of solvents. The resulting MVA is used as a sustainable comonomer to replace styrene in a maleinated acrylated epoxidized soybean‐oil (MAESO) resin to produce novel thermosets via free radical polymerization. The influence of MVA loading on the viscosity, gelation time, curing extent, thermomechanical properties, and tensile properties of the MAESO–MVA thermoset is investigated. The synthesized MVA exhibits very low volatility, which is beneficial for the development of construction material with low or zero emission. The viscosity of the MAESO–MVA system can be tailored to meet the commercial requirements. Increasing the MVA content accelerates the crosslinking reaction rate and improves thermal and mechanical properties of the MAESO–MVA system. The glass transition temperature increases with increasing MVA content. Soxhlet extraction experiments show that more than 90% of the components are incorporated into the crosslinking network. Overall, the developed MVA monomer shows promising properties to be used as an effective, green comonomer to replace styrene.

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Section: Resultssupporting

confidence: 87%

Soybean‐Oil‐Based Thermosetting Resins with Methacrylated Vanillyl Alcohol as Bio‐Based, Low‐Viscosity Comonomer

Zhang

Thakur

et al. 2017

Macro Materials & Eng

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“…This finding could be related to the presence of two distinct mechanical relaxations, therefore showing the presence of two distinguished phases in the polymer blend. A study conducted by Cousinet et al [15] highlighted the presence of two peaks on tan (d) spectrum at 70°C and 165°C, on UP resins dissolved in methacrylate compounds such as BDDMA and IBOMA (isobornyl methacrylate). The first peak at about 70°C is from the UP-BDDMA part and is more specifically the phase rich in polyester resin.…”

Section: Mechanical Spectroscopy Resultsmentioning

confidence: 99%

“…In addition, processed polymers are usually in a nonequilibrium state at the end of the shaping process; thus, heating occurs during measurements operates as an annealing that allows the network tending toward an equilibrium state with a structural recovery [27]. The macroscopic properties of the thermosets depend on the cross-link density [15]. The heating increases the average number of cross-links and reduces the average length between them, thus increasing the polymer density.…”

Section: Post-cross-linking Effects On Dielectric Propertiesmentioning

confidence: 99%

Mechanical, dielectric, and physicochemical properties of impregnating resin based on unsaturated polyesterimides

Fetouhi

Petitgas²,

Dantras

et al. 2017

Eur. Phys. J. Appl. Phys.

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Abstract. This work aims to characterize the dielectric and the mechanical properties of a resin based on an unsaturated polyesterimide diluted in methacrylate reactive diluents used in the impregnation of rotating machines. The broadband dielectric spectrometry and the dynamic mechanical analysis were used to quantify the changes in dielectric and mechanical properties of the network PEI resin, as a function of temperature and frequency. The network characterizations highlight the presence of two main relaxations, a and a 0 , confirmed by the differential scanning calorimetry analysis, showing the complexity of the chemical composition of this resin. The dielectric spectroscopy shows a significant increase in the dielectric values due to an increase of the material conductivity, while the mechanical spectroscopy shows an important decrease of the polymer rigidity and viscosity expressed by an important decrease in the storage modulus. The PEI resin shows a high reactivity when it is submitted in successive heating ramps, which involves in a post-cross-linking reaction.

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“…In recent years, a series of bio-based vinyl monomers, mainly acrylates and methacrylates, have been developed to replace styrene as reactive diluents for vinyl ester resins and unsaturated polyester resins, 23 such as methacrylated fatty acid (methacrylated lauric acid, methacrylated hexanol, and methacrylated oatanoil acid), [24][25][26][27] 35 and methacrylated rosin derivatives. 36 However, these reported bio-based reactive diluents have some drawbacks: (1) the availability of some renewable resources is not industrially mass-produced.…”

Section: Introductionmentioning

confidence: 99%

Bio-based reactive diluents as sustainable replacements for styrene in MAESO resin

Zhang

Thakur

et al. 2018

RSC Adv.

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Four different biorenewable methacrylated/acrylated monomers, namely, methacrylated fatty acid (MFA), methacrylated eugenol (ME), isobornyl methacrylate (IM), and isobornyl acrylate (IA) were employed as reactive diluents (RDs) to replace styrene (St) in a maleinated acrylated epoxidized soybean oil (MAESO) resin to produce bio-based thermosetting resins using free radical polymerization. The curing kinetics, gelation times, double bond conversions, thermal-mechanical properties, and thermal stabilities of MAESO-RD resin systems were characterized using DSC, rheometer, FT-IR, DMA, and TGA. The results indicate that all four RD monomers possess high bio-based carbon content (BBC) ranging from 63.2 to 76.9% and low volatilities (less than 7 wt% loss after being held isothermally at 30 C for 5 h). Moreover, the viscosity of the MAESO-RD systems can be tailored to acceptable levels to fit the requirements for liquid molding techniques. Because of the introduction of RDs to the MAESO resin, the reaction mixtures showed an improved reactivity and an accelerated reaction rate. FT-IR results showed that almost all the C]C double bonds within MAESO-RD systems were converted. The glass transition temperatures (T g ) of the MAESO-RDs ranged from 44.8 to 100.8 C, thus extending the range of application. More importantly, the T g of MAESO-ME resin (98.1 C) was comparable to that of MAESO-St resin (100.8 C).Overall, this work provided four potential RDs candidates to completely replace styrene in the MAESO resin, with the ME monomer being the most promising one.

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Toward replacement of styrene by bio-based methacrylates in unsaturated polyester resins

Cited by 90 publications

References 27 publications

Soybean‐Oil‐Based Thermosetting Resins with Methacrylated Vanillyl Alcohol as Bio‐Based, Low‐Viscosity Comonomer

Soybean‐Oil‐Based Thermosetting Resins with Methacrylated Vanillyl Alcohol as Bio‐Based, Low‐Viscosity Comonomer

Mechanical, dielectric, and physicochemical properties of impregnating resin based on unsaturated polyesterimides

Bio-based reactive diluents as sustainable replacements for styrene in MAESO resin

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