Post-polymerisation modification of bio-derived unsaturated polyester resins via Michael additions of 1,3-dicarbonyls

Farmer, Thomas J.; Clark, James H.; Macquarrie, Duncan J.; Ogunjobi, Joseph K.; Castle, Rachael L.

doi:10.1039/c5py01729g

Cited by 34 publications

(49 citation statements)

References 37 publications

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“…The ‫ܯ‬ തതതത was found to be 1254 g mol -1 while weight average molar mass ‫ܯ(‬ ௪ തതതതത ) was 3234 g mol -1 . These values were expected and in accordance with literature data 18,22 . Although, Tang et al claimed that addition of even low amounts of hydroquinone omitted gelation of IA 4 , in this research we found out that gelation still occurs at lower acid value (AV below 50) when performing polycondensation at elevated temperatures (180-220°C).…”

supporting

confidence: 93%

“…Hence, poly(alkyl itaconate) chains were more susceptible to physical entanglement and self-assembling of nanosized phase separations. These aggregations acted as topological constraints and inevitably lead polyester backbone chain closer, namely, the matrix networks stack up more closely 18 . Therefore, much closer networks of the system can demonstrate higher storage modulus at a room temperature.…”

Section: Cured Uprs Characterizationmentioning

confidence: 99%

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Simple One-Pot Synthesis of Fully Biobased Unsaturated Polyester Resins Based on Itaconic Acid

et al. 2017

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For the preparation of fully biobased unsaturated polyester resins (UPRs), the replacement of styrene with alternate nonpetroleum-based monomers turned out to be one of the most challenging tasks. Its complexity lies in the fact that reactive diluents (RD) have to have low viscosity and volatility, good compatibility with prepolymer, and capability to homopolymerize and copolymerize with its unsaturations. In this context, we directed our efforts to develop fully biobased UPRs using the dialkyl itaconates as an alternative to styrene. Therefore, a series of 100% biobased UPRs were prepared from itaconic acid and 1,2-propandiol and diluted by dialkyl itaconates. The resins were characterized by Fourier transform infrared spectroscopy, NMR, volatility, and viscosity measurements, while the cured samples were characterized by dynamic mechanical properties, thermomechanical analysis, thermogravimetric analysis data, and tensile tests. The influence of RD structure on the properties of cured samples was discussed in detail. It was shown that the prepared resins had evaporation rates of dialkyl itaconates of several orders of magnitude less compared to styrene. The cured resins with dimethyl itaconate showed comparable or even better thermal and mechanical properties compared to the one with styrene. This investigation showed that itaconic acid and dialkyl itaconates are promising bioresources for the preparation of fully biobased UPRs for mass consumption.

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confidence: 93%

Section: Cured Uprs Characterizationmentioning

confidence: 99%

Simple One-Pot Synthesis of Fully Biobased Unsaturated Polyester Resins Based on Itaconic Acid

et al. 2017

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“…These have been used as reactive binder resins for coatings, shape-memory materials, printing inks, etc [21][22][23][24][25]. In addition, these polyesters have been exploited in post-polymerization modification reactions to obtain new polymeric structures [26][27][28][29]. However, to date, no examples of unsaturated poly(ester amide)s based on itaconic acid have been reported.…”

Section: Introductionmentioning

confidence: 99%

First Example of Unsaturated Poly(Ester Amide)s Derived From Itaconic Acid and Their Application as Bio-Based UV-Curing Polymers

et al. 2020

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Recently, itaconic acid has drawn considerable attention as a novel radical-curing building block for polyester resins. These bio-based materials have been used in thermal, as well as ultra violet (UV) curing applications, such as printing inks or coatings. Poly(ester amide)s from itaconic acid could be very interesting, as the amide group could alter the properties of the resins as well as cured materials. However, standard polycondensation reactions with diamines are not possible with itaconic acid as the amines preferably react via an aza-Michael addition at the α,β-unsaturated double bond. Therefore, alternative and more elaborate synthetic strategies have to be developed. Herein, we present two different synthetic strategies to poly(ester amide)s from itaconic acid that circumvent the addition reaction of the amines. This is in both cases done by a pre-reaction to form stable amide building blocks that are then reacted with itaconic acid or polyesters derived thereof. The structural composition and the properties of the resin are characterized, and the UV-curing reactivity is examined. All properties are compared to corresponding polyesters from itaconic acid.

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“…12,13 Poly(alkyl)itaconates, and their copolymers, derived from esters of itaconic acid, 14,15 and prepared by conventional radical polymerisations, 16,17,18,19 are well established in the literature as are polyesters derived from itaconic acid and a diol. 20 However, simple poly(alkyl)itaconates invariably have a glass transition temperature (T g ) well below room temperature, resulting in gum-like materials. This restricts the uses of these polymers and excludes them from applications in engineering materials or packaging as substitutes for the ubiquitous and versatile polyacrylates and similar materials for which they might at first appear to be useful biobased replacements.…”

Section: Introductionmentioning

confidence: 99%

Wholly biomass derivable sustainable polymers by ring-opening metathesis polymerisation of monomers obtained from furfuryl alcohol and itaconic anhydride

et al. 2017

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Post-polymerisation modification of bio-derived unsaturated polyester resins via Michael additions of 1,3-dicarbonyls

Abstract: A rapid (5 min), solventless and heterogeneously catalysed methodology is demonstrated for the first time for the Michael addition of 1,3-dicarbonyls to biomass derived unsaturated polyesters.

Cited by 34 publications

References 37 publications

Simple One-Pot Synthesis of Fully Biobased Unsaturated Polyester Resins Based on Itaconic Acid

Simple One-Pot Synthesis of Fully Biobased Unsaturated Polyester Resins Based on Itaconic Acid

First Example of Unsaturated Poly(Ester Amide)s Derived From Itaconic Acid and Their Application as Bio-Based UV-Curing Polymers

Wholly biomass derivable sustainable polymers by ring-opening metathesis polymerisation of monomers obtained from furfuryl alcohol and itaconic anhydride

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