Skip to main content
U.S. Department of Energy
Office of Scientific and Technical Information

Terephthalic Acid Copolyesters Containing Tetramethylcyclobutanediol for High‐Performance Plastics

Journal Article · · ChemistryOpen
 [1];  [2];  [3];  [4]
  1. Biosciences Division Oak Ridge National Laboratory Oak Ridge Tennessee 37831 USA
  2. Department of Mechanical Engineering University of Vermont Burlington Vermont 05405 USA
  3. Manufacturing Science Division Oak Ridge National Laboratory Oak Ridge Tennessee37831 USA
  4. Department of Chemical and Biomolecular Engineering University of Tennessee Knoxville Tennessee 37996 USA, Joint Institute of Biological Sciences Biosciences Division Oak Ridge National Laboratory Oak Ridge Tennessee 37831 USA, Center for Renewable Carbon Department of Forestry Wildlife and Fisheries University of Tennessee Institute of Agriculture Knoxville Tennessee 37996 USA

Abstract

There is a need for high‐performance applications for terephthalic acid (TPA) polyesters with high heat resistance, impact toughness, and optical clarity. Bisphenol A (BPA) based polycarbonates and polyarylates have such properties, but BPA is an endocrine disruptor. Therefore, new TPA polyesters that are less hazardous to health and the environment are becoming popular. Tetramethylcyclobutanediol (TMCD) is a difunctional monomer that can be polymerized with TPA and other diols to yield copolyesters with superior properties to conventional TPA polyesters. It has a cyclobutyl ring that makes it more rigid than cyclohexanedimethanol (CHDM) and EG. Thus, TMCD containing TPA copolyesters can have high heat resistance and impact strength. TPA can be made from abundantly available upcycled polyethylene terephthalate (PET). Therefore, this review discusses the synthesis of monomers and copolyesters, the impact of diol composition on material properties, molecular weight, effects of photodegradation, health safety, and substitution of cyclobutane diols for future polyesters.

Sponsoring Organization:
USDOE
OSTI ID:
1813641
Alternate ID(s):
OSTI ID: 1813642
OSTI ID: 1824974
Journal Information:
ChemistryOpen, Journal Name: ChemistryOpen Journal Issue: 8 Vol. 10; ISSN 2191-1363
Publisher:
Wiley Blackwell (John Wiley & Sons)Copyright Statement
Country of Publication:
Germany
Language:
English

References (39)

A disulfide bridge in the calcium binding site of a polyester hydrolase increases its thermal stability and activity against polyethylene terephthalate journal April 2016
Influence of UV stabilizers on the weathering of PETG and PCTT films journal July 2019
Structure–property relationship of poly(cyclohexane 1,4‐dimethylene terephthalate) modified with high trans‐1,4‐cyclohexanedimethanol and 2,6‐naphthalene dicarboxylicacid journal January 2020
Ueber Ketene. Zweite Mittheilung: Dimethylketen journal January 1906
RIS Models and Unperturbed Chain Properties of Polyesters Containing 1,3-Cyclobutylene and 1,4-Cyclohexylene Linkages journal February 2003
Interfacial polycondensation. X. Polyphenyl esters journal November 1959
Development of amorphous copolyesters based on 1,4-cyclohexanedimethanol journal January 2004
Study of the structure–property relationships in a high impact and shape memory polyester by the stereoisomer selection of the cyclobutane diol monomer journal August 2013
RMMC simulations of the chain properties of polyester homopolymers from 1,4-cyclohexanedimethanol and 2,2,4,4-tetramethyl-1,3-cyclobutanediol journal January 2002
Bisphenol A and its substitutes regulate human B cell survival via Nrf2 expression journal April 2020
Identification of non-volatile migrants from baby bottles by UPLC-Q-TOF-MS journal September 2019
Real-time ageing of polyesters with varying diols journal March 2021
Copolyterephthalates containing tetramethylcyclobutane with impact and ballistic properties greater than bisphenol A polycarbonate journal August 2006
Chain mobility, secondary relaxation, and oxygen transport in terephthalate copolyesters with rigid and flexible cyclic diols journal October 2017
Comparative techniques for molecular weight evaluation of poly (ethylene terephthalate) (PET) journal September 2005
A tiered high-throughput screening approach for evaluation of estrogen and androgen receptor modulation by environmentally relevant bisphenol A substitutes journal May 2020
Estrogenic Activity Data Extraction and in Silico Prediction Show the Endocrine Disruption Potential of Bisphenol A Replacement Compounds journal September 2015
Influence of Bibenzoate Regioisomers on Cyclohexanedimethanol-Based (Co)polyester Structure–Property Relationships journal January 2019
Biodegradation of PET: Current Status and Application Aspects journal April 2019
Renewable Cyclobutane-1,3-dicarboxylic Acid (CBDA) Building Block Synthesized from Furfural via Photocyclization journal May 2020
Biobased Poly(ethylene 2,5-furancoate): No Longer an Alternative, but an Irreplaceable Polyester in the Polymer Industry journal May 2020
Novel Biobased Furanic Diols as Potential Alternatives to BPA: Synthesis and Endocrine Activity Screening journal December 2020
Liquid-phase catalytic oxidation of p-xylene journal February 1992
Chemical Recycling of Poly(ethylene terephthalate) journal April 1997
Chemistry of Dimethylketene Dimer. I. Catalytic Hydrogenation and Ring Cleavage by Alcohols journal March 1961
Ketene-Based Route to rigid Cyclobutanediol Monomers for the Replacement of BPA in High Performance Polyesters journal October 2012
Ror2 signaling regulates Golgi structure and transport through IFT20 for tumor invasiveness journal January 2017
New bio-based monomers: tuneable polyester properties using branched diols from biomass journal January 2017
Accelerated physical ageing of poly(1,4-cyclohexylenedimethylene- co -2,2,4,4-tetramethyl-1,3-cyclobutanediol terephthalate) journal January 2019
Synthesis and characterization of BPA-free polyesters by incorporating a semi-rigid cyclobutanediol monomer journal January 2020
Planar cyclobutanes: structure of 2,2,4,4-tetramethyl-cyclobutane-trans-1,3-diol journal January 1969
Property Modification via Crosslinking in CBDO-Based Copolyterephthalates journal June 2008
Linear and cyclic oligomers in PET, glycol-modified PET and Tritan™ used for food contact materials journal November 2020
The Estrogen Receptor Relative Binding Affinities of 188 Natural and Xenochemicals: Structural Diversity of Ligands journal March 2000
The crystal and molecular structure of cis -2,2,4,4-tetramethyl-1,3-cyclobutanediol journal June 1976
Synthesis and characterization of aliphatic-aromatic copolyesters based on Cis-1,3-indanediol journal May 2013
Chemicals having estrogenic activity can be released from some bisphenol a-free, hard and clear, thermoplastic resins journal December 2014
Estrogenic chemicals often leach from BPA-free plastic products that are replacements for BPA-containing polycarbonate products journal May 2014
Using a marine microalga as a chassis for polyethylene terephthalate (PET) degradation journal October 2019

Similar Records

3D printing of a recycled copolyester of terephthalic acid, cyclohexanedimethanol and tetramethylcyclobutanediol
Journal Article · Sun Dec 25 23:00:00 EST 2022 · Polymer Testing · OSTI ID:1922311

Related Subjects