Monothiolactide, a New Monomer for the Synthesis of Recyclable, Alternating Ester-Thioester Polymers

被引：0

作者：

Narmon, An Sofie ^{[1
,2
]}

Jenisch, Lilliana M. ^{[1
]}

Rey, Jerome ^{[3
]}

Khalil, Ibrahim ^{[1
]}

Badawi, Michael ^{[1
]}

Dusselier, Michiel ^{[1
]}

机构：

[1] Katholieke Univ Leuven, Ctr Sustainable Catalysis & Engn CSCE, Dept Microbial & Mol Syst, Celestijnenlaan 200F, B-3001 Leuven, Belgium

[2] B4Plast BV, IQ Parklaan 2 A, B-3650 Dilsen Stokkem, Belgium

[3] Univ Lorraine, CNRS, Lab Lorrain Chim Mol, F-57000 Metz, France

来源：

CHEMSUSCHEM | 2024年 / 17卷 / 23期

基金：

欧洲研究理事会;

关键词：

Br & oslash; nsted acid catalysis; ring-opening polymerization; (thio)lactone; poly(thio)ester; chemical recycling; MATRIX PHOTOCHEMISTRY;

D O I：

10.1002/cssc.202400134

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Aliphatic polyesters and polythioesters are very interesting alternatives for current fossil-based and degradation-resistant plastics, due to their high (bio)degradability and (chemical) recyclability potential. Two important examples include polylactide (PLD), currently leading the synthetic bioplastics market, and its sulfur analog polythiolactide (PTLD). Both polymers can be made by ring-opening polymerization (ROP) of their corresponding (thio)dilactones, lactide (LD) and thiolactide (TLD) respectively. In this work, the benefits of esters and thioesters were combined in one material by the successful catalytic synthesis and ROP of monothiolactide (MTL), an unprecedented monomer containing half a LD and half a TLD structural unit. MTL can be obtained by a simple direct condensation of biobased lactic acid and thiolactic acid aided by Br & oslash;nsted acid catalysis. The novel, but simple monomer showed to be easily polymerized with triethylamine to materials containing alternating lactic and thiolactic ester units with a very high molar mass. The lower stability of MTL (vs. TLD) resulted in improved ROP thermodynamics, while also fast and controllable polymerization kinetics were observed. The new polymers feature a good chemical recycling and hydrolytic degradation potential with important improvements compared to PTLD and PLD. Finally, a successful co-polymerization with commercial LD was shown, paving the way towards industrialization. Aliphatic poly(thio)esters are interesting alternatives for current degradation-resistant plastics, due to their (bio)degradability and chemical recyclability. Here, the benefits of (poly)lactide ((P)LD) and (poly)thiolactide ((P)TLD) were combined by synthesizing and polymerizing a novel monomer, i. e. monothiolactide, composed of half a LD and half a TLD unit. The new plastic showed improvements regarding polymerization and chemical recycling, combining the best of both polyester and polythioester worlds. image

引用

页数：9