Synthesis and Property of Eugenol-based Bisphenols and Poly(thioether carbonate)s

Cai-juan Huang; Meng-qian Huang; Qin Chen; Zhu Luo; Hai-bo Xie

doi:10.11777/j.issn1000-3304.2022.22095

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Synthesis and Property of Eugenol-based Bisphenols and Poly(thioether carbonate)s

Research Article | 更新时间：2024-10-08

- Synthesis and Property of Eugenol-based Bisphenols and Poly(thioether carbonate)s
- ACTA POLYMERICA SINICA Vol. 53, Issue 9, Pages: 1095-1103(2022)
- 作者机构：
  
  贵州大学材料与冶金学院高分子材料与工程系贵阳 550025
- 作者简介：
  
  Hai-bo Xie, E-mail: hbxie@gzu.edu.cn
- 基金信息：
- DOI：10.11777/j.issn1000-3304.2022.22095
  CLC：
- Published：20 September 2022，
  
  Published Online：20 July 2022，
  
  Received：25 March 2022，
  
  Accepted：07 May 2022
- 稿件说明：
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黄彩娟,黄梦倩,陈沁等.丁香酚基双酚及聚硫醚碳酸酯的制备及性质研究[J].高分子学报,2022,53(09):1095-1103.

Huang Cai-juan,Huang Meng-qian,Chen Qin,et al.Synthesis and Property of Eugenol-based Bisphenols and Poly(thioether carbonate)s[J].ACTA POLYMERICA SINICA,2022,53(09):1095-1103.
黄彩娟,黄梦倩,陈沁等.丁香酚基双酚及聚硫醚碳酸酯的制备及性质研究[J].高分子学报,2022,53(09):1095-1103. DOI： 10.11777/j.issn1000-3304.2022.22095.

Huang Cai-juan,Huang Meng-qian,Chen Qin,et al.Synthesis and Property of Eugenol-based Bisphenols and Poly(thioether carbonate)s[J].ACTA POLYMERICA SINICA,2022,53(09):1095-1103. DOI： 10.11777/j.issn1000-3304.2022.22095.

摘要

以丁香酚和不同碳链长度的二硫醇为原料，通过紫外光引发的硫醇-烯点击反应，合成了丁香酚基含硫醚结构的双酚单体；之后与三光气反应制备了丁香酚基聚硫醚碳酸酯，并通过硫醚的氧化实现后氧化改性获得聚砜碳酸酯. 采用核磁氢谱、核磁碳谱、红外研究丁香酚基双酚单体及其聚碳酸酯的结构，采用凝胶渗透色谱测定其分子量及分布，通过热重分析仪及示差扫描量热仪对丁香酚基聚碳酸酯的热性能进行研究，结果表明丁香酚基聚碳酸酯分子量在3.27×10

~6.05×10

g/mol之间，热失重5%的温度大于340 ℃，玻璃化转变温度在12.2~24.4 ℃之间，表现出良好的热稳定性，后氧化改性后热稳定性和玻璃化转变温度有所下降.

Abstract

Polycarbonate is one of the most important polymeric materials in human society

which has found wide application in various areas owning to its excellent properties. However

traditional polycarbonates are derived from non-renewable petroleum-based chemicals

some of which are highly toxic. Therefore

the search for renewable resources

such as biomass and carbon dioxide

to replace petroleum-based chemicals for polymer synthesis has received great

attention in recent years. In this work

thioether-containing bisphenols were synthesized from bio-based eugenol and dithiols with different lengths of carbon chain

via

thiol-ene click reaction initiated by UV light. The structures of eugenol-based bisphenols were confirmed by 1H- nuclear magnetic resonance (

H-NMR)

13C- nuclear magnetic resonance (

C-NMR) and Fourier-transform infrared spectroscopy (FTIR)

and the yield reached 76.2%. The obtained bisphenols were polymerized with triphosgene under mild conditions to prepare eugenol-based poly(thioether carbonate)s with satisfying yields. The structures of eugenol-based poly(thioether carbonate)s were illustrated by

NMR

C-NMR and FTIR

which demonstrated the successful preparation of poly(thioether carbonate)s. Gel permeation chromatography (GPC) analysis revealed that the molecular weight of those eugenol-based poly(thioether carbonate)s was in the range from 3.27×10

g/mol to 5.72×10

g/mol with polydispersity index between 1.1 and 1.9. The results of the thermal gravimetric analysis revealed that all the eugenol-based poly(thioether carbonate)s exhibited a one-step degradation pattern with a weight loss of 5% in the range of 343-359 ℃

and maximum degradation rates were found between 379 and 395 ℃

indicating the good thermostability of the as-prepared eugenol-based poly(thioether carbonate)s. The glass transition temperature of eugenol-based poly(thioether carbonate)s decreased from 24.4 ℃ to 12.2 ℃ as the lengths of the carbon chain of dithiols increased. Finally

one eugenol-based poly(thioether carbonate) was post-oxidized with m-chloroperbenzoic acid to obtain poly(sulfone carbonate)

which was confirmed by

NMR

C-NMR and FTIR. After post-oxidation

the obtained poly(sulfone carbonate) exhibited decreased thermal stability and glass transformation temperature.

关键词

丁香酚聚碳酸酯硫醇-烯点击反应后氧化改性

Keywords

EugenolPolycarbonateThiol-ene click reactionPost-oxidation

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