High Molecular Weight Soybean Oil-based Polyesters through Carboxyl-ester Transesterification

Qiu-quan Cai; Hong-jie Zhang; Xu-xia Yao; Wei-pu Zhu

doi:10.11777/j.issn1000-3304.2020.20260

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High Molecular Weight Soybean Oil-based Polyesters through Carboxyl-ester Transesterification

Research Article | 更新时间：2021-05-07

- High Molecular Weight Soybean Oil-based Polyesters through Carboxyl-ester Transesterification
- Acta Polymerica Sinica Vol. 52, Issue 5, Pages: 489-498(2021)
- 作者机构：
  
  1.高分子合成与功能构造教育部重点实验室浙江大学高分子科学与工程学系
  2.浙江大学材料科学与工程学院
  3.浙江省吸附分离材料与应用技术重点实验室　杭州 310027
- 作者简介：
- 基金信息：
- DOI：10.11777/j.issn1000-3304.2020.20260
  CLC：
- Published：3 May 2021，
  
  Published Online：25 January 2021，
  
  Received：30 November 2020，
  
  Revised：19 December 2020，
扫描看全文
Qiu-quan Cai, Hong-jie Zhang, Xu-xia Yao, Wei-pu Zhu. High Molecular Weight Soybean Oil-based Polyesters through Carboxyl-ester Transesterification. [J]. Acta Polymerica Sinica 52(5):489-498(2021)
DOI：

Qiu-quan Cai, Hong-jie Zhang, Xu-xia Yao, Wei-pu Zhu. High Molecular Weight Soybean Oil-based Polyesters through Carboxyl-ester Transesterification. [J]. Acta Polymerica Sinica 52(5):489-498(2021) DOI： 10.11777/j.issn1000-3304.2020.20260.

摘要

以大豆油为原料可高效合成大豆油基二元醇(SOD)，通过与二元酸的熔融缩聚获得大豆油基聚酯. 然而传统的酯化和酯交换机理无法获得高分子量的聚酯产物，其原因在于反应过程中醇酸单元摩尔比偏离达到高分子量所需的等摩尔比条件. 本研究采用一种新型的端羧基酯交换(CET)机理成功合成了高分子量的大豆油基聚酯，首先以过量的可升华二元酸与SOD酯化生成羧基封端预聚物，再通过CET在高真空下脱除过量的二元酸，动态地逼近醇酸等摩尔比条件，从而获得了黏均分子量可达123 kDa的高分子量大豆油基聚酯. 该聚酯具有良好的热稳定性和高透明性，其黏附性能可达压敏胶黏剂的商用标准. 这种含不饱和脂肪族侧链的聚酯还可通过巯-烯“点击”反应引入季铵盐基团，获得抗菌型大豆油基聚酯.

Abstract

Soybean oil-based diols (SOD) can be synthesized from soybean oil and polymerized with diacids to give soybean oil-based polyesters. However

the conventional esterification and transesterification mechanisms of polycondensation are incapable of obtaining high molecular weight (HMW) soybean oil-based polyesters due to the kinetic deviation of diol/diacid unit ratio from 1∶1

which is required for producing HMW polyesters. Here we introduce a novel carboxyl-ester transesterification (CET) mechanism to synthesize HMW soybean oil-based polyesters through melt polycondensation. Using excess diacids to esterify with SOD

a carboxyl-terminated prepolymer was first afforded. Then the excess diacids were regenerated

via

CET and removed through sublimation

thus dynamically approaching the stoichiometric condition of the diol/diacid unit

through which a series of HMW soybean oil-based polyesters with viscosity-average molecular weights up to 123 kDa were obtained. The resultant polyesters exhibit good thermal stability and high transparency

and their adhesive performances are comparable to those of commercial pressure-sensitive adhesives. Furthermore

antibacterial soybean oil-based polyesters were achieved

via

thiol-ene “click” reaction of the alkene groups in the aliphatic side chain of polyesters with a thiolated quaternary ammonium salt.

关键词

端羧基酯交换熔融缩聚植物油高分子量聚酯压敏胶黏剂

Keywords

Carboxyl-ester transesterificationMelt polycondensationVegetable oilHigh molecular weight polyesterPressure-sensitive adhesive

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