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Synthesis, life cycle assessment, and polymerization of a vanillin-based spirocyclic diol toward polyesters with increased glass transition temperature

Mankar, Smita LU ; Garcia Gonzalez, Nelly LU ; Warlin, Niklas LU ; Valsange, Nitin LU ; Rehnberg, Nicola LU ; Lundmark, Stefan ; Jannasch, Patric LU and Zhang, Baozhong LU (2019) In ACS Sustainable Chemistry & Engineering 7(23). p.19090-19103
Abstract
Bio-based rigid diols are key building blocks in the development and preparation of high performance bioplastics with improved thermal and dimensional stability. Here, we report on the straightforward two-step synthesis of a diol with a spirocyclic acetal structure, starting from bio-based vanillin and pentaerythritol. According to a preliminary life cycle assessment (LCA), the greenhouse gas emissions of this bio-based diol are significantly lower than that of bio-based 1,3-propanediol. Copolymerization of the rigid spiro-diol with 1,6-hexanediol and dimethyl terephthalate by melt polymerization yielded a series of copolyesters, which showed improved glass transition temperature and thermal stability upon the incorporation of the... (More)
Bio-based rigid diols are key building blocks in the development and preparation of high performance bioplastics with improved thermal and dimensional stability. Here, we report on the straightforward two-step synthesis of a diol with a spirocyclic acetal structure, starting from bio-based vanillin and pentaerythritol. According to a preliminary life cycle assessment (LCA), the greenhouse gas emissions of this bio-based diol are significantly lower than that of bio-based 1,3-propanediol. Copolymerization of the rigid spiro-diol with 1,6-hexanediol and dimethyl terephthalate by melt polymerization yielded a series of copolyesters, which showed improved glass transition temperature and thermal stability upon the incorporation of the spiro-acetal units. The crystallinity and melting point of copolyesters decreased with increasing content of the spirocyclic backbone structures. The copolyesters containing 10% of the new diol was semicrystalline while those with 20 and 30% spiro-diol incorporated were completely amorphous. Moreover, dynamic mechanical analysis indicated that the copolyesters showed comparable storage moduli as AkestraTM, a commercial fossil-based high-performance polyester. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
ACS Sustainable Chemistry & Engineering
volume
7
issue
23
pages
13 pages
publisher
The American Chemical Society (ACS)
ISSN
2168-0485
DOI
10.1021/acssuschemeng.9b04930
language
English
LU publication?
yes
id
80b8d872-b5b8-4756-8970-9e9cfad1b8e9
date added to LUP
2019-11-04 23:01:50
date last changed
2019-11-25 21:13:45
@article{80b8d872-b5b8-4756-8970-9e9cfad1b8e9,
  abstract     = {Bio-based rigid diols are key building blocks in the development and preparation of high performance bioplastics with improved thermal and dimensional stability. Here, we report on the straightforward two-step synthesis of a diol with a spirocyclic acetal structure, starting from bio-based vanillin and pentaerythritol. According to a preliminary life cycle assessment (LCA), the greenhouse gas emissions of this bio-based diol are significantly lower than that of bio-based 1,3-propanediol. Copolymerization of the rigid spiro-diol with 1,6-hexanediol and dimethyl terephthalate by melt polymerization yielded a series of copolyesters, which showed improved glass transition temperature and thermal stability upon the incorporation of the spiro-acetal units. The crystallinity and melting point of copolyesters decreased with increasing content of the spirocyclic backbone structures. The copolyesters containing 10% of the new diol was semicrystalline while those with 20 and 30% spiro-diol incorporated were completely amorphous. Moreover, dynamic mechanical analysis indicated that the copolyesters showed comparable storage moduli as AkestraTM, a commercial fossil-based high-performance polyester. },
  author       = {Mankar, Smita and Garcia Gonzalez, Nelly and Warlin, Niklas and Valsange, Nitin and Rehnberg, Nicola and Lundmark, Stefan and Jannasch, Patric and Zhang, Baozhong},
  issn         = {2168-0485},
  language     = {eng},
  number       = {23},
  pages        = {19090--19103},
  publisher    = {The American Chemical Society (ACS)},
  series       = {ACS Sustainable Chemistry & Engineering},
  title        = {Synthesis, life cycle assessment, and polymerization of a vanillin-based spirocyclic diol toward polyesters with increased glass transition temperature},
  url          = {http://dx.doi.org/10.1021/acssuschemeng.9b04930},
  doi          = {10.1021/acssuschemeng.9b04930},
  volume       = {7},
  year         = {2019},
}