Synthesis, life cycle assessment, and polymerization of a vanillin-based spirocyclic diol toward polyesters with increased glass transition temperature
(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)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/80b8d872-b5b8-4756-8970-9e9cfad1b8e9
- author
- 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
- organization
- publishing date
- 2019-12-02
- 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)
- external identifiers
-
- scopus:85075621472
- 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
- 2022-04-18 18:30:08
@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}}, month = {{12}}, 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}}, }