Synthesis and application of cinnamate-functionalized rubber for the preparation of UV-curable films

Wu, Wei; Karamdoust, Solmaz; Turowec, Bethany A.; Gillies, Elizabeth R.

doi:10.1016/j.eurpolymj.2013.10.003

Cited by 8 publications

(7 citation statements)

References 35 publications

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“…These photocrosslinkable cinnamoyl-conjugated bio-based polymers are widely prepared by condensing the carboxylic acid of cinnamic acid with hydroxyl or amino groups of bio-based building blocks [451]. Cinnamoyl moieties were therefore associated with biodegradable polyesters such as poly(lactic acid) and poly(-caprolactone) [452], gelatin [453][454][455], hyaluronic acid [456][457][458], alginate [459,460] and hydroxylpropyl cellulose [460], but also benzoxazines, lithocholic acid [461], oil-based ricinoleic acid [462], acrylate monomers [463] and butyl rubber derivatives [464]. Polymers containing cinnamoyl moieties have been used in a wide of applications to produce photo-crosslinked polymer materials [465][466][467][468][469][470], photo-crosslinked hydrogels [471][472][473], materials for photoinduced alignment of liquid crystals [474][475][476][477][478], in advanced microelectronics [479], in photolithography [480], in non-linear-optical materials [481], and for the synthesis of photocurable coatings [482].…”

Section: From Cinnamate Derivativesmentioning

confidence: 99%

Bio-sourced monomers and cationic photopolymerization–The green combination towards eco-friendly and non-toxic materials

Pierau

Elian

Akimoto

et al. 2022

Progress in Polymer Science

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Section: From Cinnamate Derivativesmentioning

confidence: 99%

Bio-sourced monomers and cationic photopolymerization–The green combination towards eco-friendly and non-toxic materials

Pierau

Elian

Akimoto

et al. 2022

Progress in Polymer Science

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“…14 This allylic alcohol functionality has been used to graft PEO with high efficiency 15 and also to install cinnamate moieties for UV-curing of rubber films. 35 Herein we report the clean conversion of the exo-allylic alcohol functionality to an exo-conjugated diene and application of this diene in Diels−Alder [4 + 2] cycloaddition chemistry a strategic "click" method for the functionalization of polymers. 19 In previous work, dehydrohalogenation of brominated RB has been used to prepare diene functionalized rubber.…”

Section: ■ Introductionmentioning

confidence: 99%

Rubber Functionalization by Diels–Alder Chemistry: From Cross-Linking to Multifunctional Graft Copolymer Synthesis

Moustafa

Gillies

2013

Macromolecules

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The functionalization of polyisobutylene-co-isoprene, commonly referred to as butyl rubber, was investigated with the aim of preparing multifunctional materials. First, the acid catalyzed ring-opening of epoxidized butyl rubber was investigated. Ring-opening followed by elimination resulted in the formation of different dienes depending on the reaction conditions. It was possible to cleanly isolate the exo-diene, which readily undergoes Diels–Alder [4 + 2] cycloaddition reactions and it was demonstrated that this chemistry could be used to prepare multifunctional graft copolymers. For example, poly(ethylene oxide) (PEO) or polystyrene (PS) could be grafted while at the same time introducing carboxylic acid moieties along the polymer backbone, and both polymers could be simultaneously grafted to form mixed graft copolymers with tunable tensile properties. Furthermore, it was demonstrated that reaction with a dimaleimide led to efficient cross-linking of the rubber and this cross-linking could be reversed upon heating due to the thermoreversible nature of the Diels–Alder reaction. Thus, this chemistry allows for clean and facile synthesis of new rubber derivatives, opening possibilities for new rubber applications.

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“…The unirradiated poly(HEMA-co-CEMA) had a main absorption peak at 283 nm attributed to the ethenylbenzene unit of cinnamoyl groups. This absorption decreased in the time course of UV irradiation, suggesting the occurrence of photo-dimerization [13][14][15]17,29,30,33,34,38,44]. The rate of this absorption decline of P(H60/C40) was higher than that of P(H25/C75) and that of P(H0/C100).…”

Section: Photocrosslinking Of Poly(hema-co-cema)mentioning

confidence: 95%

“…Except for our original reports [27,28], however, there are only few reports regarding the cell proliferation assays carried out on photocrosslinked materials carrying cinnamoyl groups at high density. Wu et al [29] carried out the in vitro cell adhesion and growth assay of butyl rubber derivatives that were prepared from hydroxyl-functionalized butyl rubber and cinnamoyl chloride, cured by UV-light exposure. They showed that no toxic compound leaches from these cinnamoyl-functionalized butyl rubber derivatives, but myoblast cell adhesion was low on the crosslinked films.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Photocrosslinkable Copolymers of Cinnamoyl Group-modified Methacrylate and 2-Hydroxyethyl Methacrylate, and Fibroblast Cell Growth on Their Thin Films

Yano

Iwase

Shibata

et al. 2020

J. Photopol. Sci. Technol.

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Cinnamoyl-modified methacrylate, 2-cinnamoyloxyethyl methacrylate (CEMA), was synthesized from 2-hydroxyethyl methacrylate (HEMA) and cinnamoyl chloride. Copolymers with various cinnamoyl contents were synthesized by random copolymerization of HEMA and CEMA at different feed ratios. Thus three copolymers with different CEMA contents were synthesized, and the monomer composition ([HEMA]:[CEMA]) in the copolymers ranged from 75:25 to 0:100. The coating films of copolymers on glass plates were prepared by the dip-coating method. Photo-induced dimerization of the cinnamoyl groups in the copolymers was confirmed by the ultraviolet-visible (UV-Vis) spectral changes. The cell proliferation on the photocrosslinked copolymers was tested using 3T3 Swiss albino mouse embryo fibroblasts. The results of the cell proliferation assay revealed that the photocrosslinked copolymers carrying more cinnamoyl groups promoted the cell proliferation compared with the photocrosslinked copolymers carrying less cinnamoyl groups. According to the results in the present study and our previous studies on cinnamoyl-modified trehalose and cinnamoyl-modified hydroxypropyl cellulose, it is presumable that the photodimerized cinnamoyl groups existing on the surface of materials at high density have some preferable effect on promoting fibroblast cell adhesion.

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Synthesis and application of cinnamate-functionalized rubber for the preparation of UV-curable films

Cited by 8 publications

References 35 publications

Bio-sourced monomers and cationic photopolymerization–The green combination towards eco-friendly and non-toxic materials

Bio-sourced monomers and cationic photopolymerization–The green combination towards eco-friendly and non-toxic materials

Rubber Functionalization by Diels–Alder Chemistry: From Cross-Linking to Multifunctional Graft Copolymer Synthesis

Synthesis of Photocrosslinkable Copolymers of Cinnamoyl Group-modified Methacrylate and 2-Hydroxyethyl Methacrylate, and Fibroblast Cell Growth on Their Thin Films

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