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Vanillin derived a carbonate dialdehyde and a carbonate diol: novel platform monomers for sustainable polymers synthesis.

ABSTRACT: Vanillin has been regarded as one of the important biomass-based platform chemicals for aromatic polymers synthesis. Herein, novel symmetric bis(4-formyl-2-methoxyphenyl)carbonate (BFMC) and bis(4-(hydroxymethyl)-2-methoxyphenyl)carbonate (BHMC) polymeric monomers have been synthesized in high yields using vanillin as a raw chemical, which have been submitted for polymer synthesis via well-established polymeric strategies. A new class of poly(carbonate ester)s oligomers with amide moieties in their side chain can be prepared by using the BFMC as one of monomers via the Passerini three compound reaction (3CR). A new class of poly(carbonate ester)s oligomers and poly(carbonate urethane)s can be prepared via reactions between BHMC with dicarboxylic acid chlorides and diisocyanates, respectively. Their structure have been confirmed by ¹H NMR, ¹³C NMR and FTIR, and the gel permeation chromatograph (GPC) analysis shows that the Mn of poly(carbonate ester)s oligomers ranges from 3100 to 7900 with PDI between 1.31 and 1.65, and the Mn of poly(carbonate urethane)s ranges from 16 400 to 24 400 with PDI ranging from 1.36 to 2.17. The DSC analysis shows that the poly(carbonate ester)s oligomers have relative low T _g ranging from 37.4 to 74.1 °C, and the poly(carbonate urethane)s have T _g ranging from 97.3 to 138.3 °C, mainly correlating to the structure of dicarboxylic acid chlorides and diisocyanates used.

SUBMITTER: Bai

PROVIDER: S-EPMC9087012 | biostudies-literature | 2018 Oct

REPOSITORIES: biostudies-literature

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Vanillin derived a carbonate dialdehyde and a carbonate diol: novel platform monomers for sustainable polymers synthesis.

Bai De Chen Qin Q Chai Yang Y Ren Tianhua T Huang Caijuan C Ingram Ian D V IDV North Michael M Zheng Qiang Q Xie Haibo H

RSC advances 20181005 60

Vanillin has been regarded as one of the important biomass-based platform chemicals for aromatic polymers synthesis. Herein, novel symmetric bis(4-formyl-2-methoxyphenyl)carbonate (BFMC) and bis(4-(hydroxymethyl)-2-methoxyphenyl)carbonate (BHMC) polymeric monomers have been synthesized in high yields using vanillin as a raw chemical, which have been submitted for polymer synthesis <i>via</i> well-established polymeric strategies. A new class of poly(carbonate ester)s oligomers with amide moietie ...[more]

PMID: 35548608

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Project description:Advances in technology have led to the production of sustainable antioxidants and natural monomers for food packaging and targeted drug delivery applications. Of particular importance is the synthesis of lignin polymers, and graft polymers, dopamine, and polydopamine, inulin, quercetin, limonene, and vitamins, due to their free radical scavenging ability, chemical potency, ideal functional groups for polymerization, abundance in the natural environment, ease of production, and activation of biological mechanisms such as the inhibition of the cellular activation of various signaling pathways, including NF-κB and MAPK. The radical oxygen species are responsible for oxidative damage and increased susceptibility to cancer, cardiovascular, degenerative musculoskeletal, and neurodegenerative conditions and diabetes; such biological mechanisms are inhibited by both synthetic and naturally occurring antioxidants. The orientation of macromolecules in the presence of the plasticizing agent increases the suitability of quercetin in food packaging, while the commercial viability of terpenes in the replacement of existing non-renewable polymers is reinforced by the recyclability of the precursors (thyme, cannabis, and lemon, orange, mandarin) and marginal ecological effect and antioxidant properties. Emerging antioxidant nanoparticle polymers have a broad range of applications in tumor-targeted drug delivery, food fortification, biodegradation of synthetic polymers, and antimicrobial treatment and corrosion inhibition. The aim of the review is to present state-of-the-art polymers with intrinsic antioxidant properties, including synthesis scavenging activity, potential applications, and future directions. This review is distinct from other works given that it integrates different advances in antioxidant polymer synthesis and applications such as inulin, quercetin polymers, their conjugates, antioxidant-graft-polysaccharides, and polymerization vitamins and essential oils. One of the most comprehensive reviews of antioxidant polymers was published by Cirillo and Iemma in 2012. Since then, significant progress has been made in improving the synthesis, techniques, properties, and applications. The review builds upon existing research by presenting new findings that were excluded from previous reviews.

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Vanillin derived a carbonate dialdehyde and a carbonate diol: novel platform monomers for sustainable polymers synthesis.

Publications

Vanillin derived a carbonate dialdehyde and a carbonate diol: novel platform monomers for sustainable polymers synthesis.

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