Chain Extension of Poly(butylene adipate) with 2,2’-(1,4- Phenylene)-bis(2-oxazoline)

Luo, Si Yang; Zhao, Jing

doi:10.4028/www.scientific.net/amr.11-12.387

Cited by 3 publications

(6 citation statements)

References 5 publications

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“…The chain-extension procedure can be performed by using phosgene, [152] dicarbonate, [153] diisocyanate, [154] bis(2-oxazoline), [155] or bis(caprolactamate). To circumvent this issue and to synthesize high molar mass polyesters, chain extension can be performed on the a,w-dihydroxyl-terminated oligomers.…”

Section: Chain Extensionmentioning

confidence: 99%

“…Contraryt ot he process with phosgene, which is carriedo ut in solution,c hain extension with diisocyanate is performed without solvent, which is ag reat advantage.T his process has been industrially used for 20 years by Showa Denko, for example, for the synthesis of high molar mass chain-extended PBS by using 1,6-hexamethylene diisocyanate. [154] In addition to these two main techniques, bis(2-oxazoline) [154] or bis(caprolactamate) molecules [155] have been more recently used as coupling agents ( Figure 11). Two strategies were studied.…”

Section: Reviewsmentioning

confidence: 99%

“…To circumvent this issue and to synthesize high molar mass polyesters, chain extension can be performed on the a,w-dihydroxyl-terminated oligomers. The chain-extension procedure can be performed by using phosgene, [152] dicarbonate, [153] diisocyanate, [154] bis(2-oxazoline), [155] or bis(caprolactamate). [155] The chain extension of a,w-dihydroxyl-terminated polyester oligomers (M n % 1000-3000 gmol À1 )w ith phosgenei sp erformed in solution (mostly in chloroform) at low temperature (0-5 8C) by using N-ethyl-N,N-diisopropylamine (EDIPA) and 4dimethylaminopyridine (DMAP) as acid acceptora nd acylation catalyst, respectively ( Figure 10).…”

Section: Chain Extensionmentioning

confidence: 99%

“…The chain-extension procedure can be performed by using phosgene, [152] dicarbonate, [153] diisocyanate, [154] bis(2-oxazoline), [155] or bis(caprolactamate). [155] The chain extension of a,w-dihydroxyl-terminated polyester oligomers (M n % 1000-3000 gmol À1 )w ith phosgenei sp erformed in solution (mostly in chloroform) at low temperature (0-5 8C) by using N-ethyl-N,N-diisopropylamine (EDIPA) and 4dimethylaminopyridine (DMAP) as acid acceptora nd acylation catalyst, respectively ( Figure 10). For this, EDIPAa sa na cid acceptor is ab etter choice than the more usual trimethylamine, since EDIPAi sl ess prone to undergo side reactions with acylating agents, due to its larger steric hindrance.…”

Section: Chain Extensionmentioning

confidence: 99%

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Biotic and Abiotic Synthesis of Renewable Aliphatic Polyesters from Short Building Blocks Obtained from Biotechnology

2018

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Biobased polymers have seen their attractiveness increase in recent decades thanks to the significant development of biorefineries to allow access to a wide variety of biobased building blocks. Polyesters are one of the best examples of the development of biobased polymers because most of them now have their monomers produced from renewable resources and are biodegradable. Currently, these polyesters are mainly produced by using traditional chemical catalysts and harsh conditions, but recently greener pathways with nontoxic enzymes as biocatalysts and mild conditions have shown great potential. Bacterial polyesters, such as poly(hydroxyalkanoate)s (PHA), are the best example of the biotic production of high molar mass polymers. PHAs display a wide variety of macromolecular architectures, which allow a large range of applications. The present contribution aims to provide an overview of recent progress in studies on biobased polyesters, especially those made from short building blocks, synthesized through step-growth polymerization. In addition, some important technical aspects of their syntheses through biotic or abiotic pathways have been detailed.

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Section: Chain Extensionmentioning

confidence: 99%

Section: Reviewsmentioning

confidence: 99%

Section: Chain Extensionmentioning

confidence: 99%

Section: Chain Extensionmentioning

confidence: 99%

See 2 more Smart Citations

Biotic and Abiotic Synthesis of Renewable Aliphatic Polyesters from Short Building Blocks Obtained from Biotechnology

2018

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“…18 However, the chain-extending efficiency of this noncatalyzed chain extension was not good. The reproducibility of the noncatalyzed chain extension was poor, and high-molecular-weight polyesters were seldom obtained.…”

Section: Introductionmentioning

confidence: 97%

Catalyzed chain extension of poly(butylene adipate) and poly(butylene succinate) with 2,2′‐(1,4‐phenylene)‐bis(2‐oxazoline)

Huang

Luo

et al. 2009

J of Applied Polymer Sci

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Low-molecular-weight HOOC-terminated poly(butylene adipate) prepolymer (PrePBA) and poly(butylene succinate) prepolymer (PrePBS) were synthesized through melt-condensation polymerization from adipic acid or succinic acid with butanediol. The catalyzed chain extension of these prepolymers was carried out at 180-220 C with 2,2 0 -(1,4-phenylene)-bis(2-oxazoline) as a chain extender and p-toluenesulfonic acid (p-TSA) as a catalyst. Higher molecular weight polyesters were obtained from the catalyzed chain extension than from the noncatalyzed one. However, an improperly high amount of p-TSA and a high temperature caused branching or a crosslinking reaction. Under optimal conditions, chain-extended poly (butylene adipate) (PBA) with a number-average molecular weight up to 29,600 and poly(butylene succinate) (PBS) with an intrinsic viscosity of 0.82 dL/g were synthesized. The chain-extended polyesters were characterized by IR spectroscopy, 1 H-NMR spectroscopy, differential scanning calorimetry (DSC), thermogravimetric analysis, wide-angle X-ray scattering, and tensile testing. DSC, wide-angle X-ray scattering, and thermogravimetric analysis characterization showed that the chain-extended PBA and PBS had lower melting temperatures and crystallinities and slower crystallization rates and were less thermally stable than PrePBA and PrePBS. This deterioration of their properties was not harmful enough to impair their thermal processing properties and should not prevent them from being used as biodegradable thermoplastics. The tensile strength of the chain-extended PBS was about 31.05 MPa. V C 2009 Wiley Periodicals, Inc. J Appl Polym

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Chain extension of adipic acid and (or) succinic acid/butanediol polyesters with 2,2′‐(1,4‐phenylene)‐bis(2‐oxazoline) and adipoylbiscaprolactamate combined chain extenders

Shi

Zhao

et al. 2011

Polymers for Advanced Techs

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This paper provided an easy and flexible method to synthesize high molecular weight polyesters by polycondensation and chain extension. Low molecular weight polybutylene adipate, polybutylene succinate, and poly(butylene succinate‐co‐butylene adipate) (PBSA) were synthesized through melt condensation polymerization from adipic acid and/or succinic acid with butanediol. The prepolyesters obtained had different amount of COOH and OH terminal groups. Chain extension of them was carried out at 180–240°C using 2,2′‐(1,4‐phenylene)‐bis(2‐oxazoline) and adipoyl biscaprolactamate as combined chain extenders. The influencing factors of the chain extension were studied. At the optimal conditions, chain‐extended polybutylene adipate with Mn up to 39,100, polybutylene succinate with intrinsic viscosity of 0.99 dl/g, and PBSA with intrinsic viscosity from 0.73 to 0.81 dl/g were synthesized. The chain‐extended polyesters were characterized by IR spectrum, 1H NMR spectrum, differential scanning calorimetry, thermogravimetric analysis (TGA), wide angle X‐ray scattering, and tensile test. The thermal analysis showed that chain extension often led to slight decrease of the regularity, the crystallinity, and the melting point. This deterioration of the properties is not harmful enough to impair their thermal properties and obstruct them from being used as biodegradable thermoplastics. The TGA showed that the chain‐extended polyesters were stable with initial decomposition temperature over 354.7°C. The tensile strength of the chain extended PBS and PBSAs with butylene adipate units less than 20 mol% was in the range of 18.95–31.22 MPa. Copyright © 2010 John Wiley & Sons, Ltd.

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Chain Extension of Poly(butylene adipate) with 2,2’-(1,4- Phenylene)-bis(2-oxazoline)

Cited by 3 publications

References 5 publications

Biotic and Abiotic Synthesis of Renewable Aliphatic Polyesters from Short Building Blocks Obtained from Biotechnology

Biotic and Abiotic Synthesis of Renewable Aliphatic Polyesters from Short Building Blocks Obtained from Biotechnology

Catalyzed chain extension of poly(butylene adipate) and poly(butylene succinate) with 2,2′‐(1,4‐phenylene)‐bis(2‐oxazoline)

Chain extension of adipic acid and (or) succinic acid/butanediol polyesters with 2,2′‐(1,4‐phenylene)‐bis(2‐oxazoline) and adipoylbiscaprolactamate combined chain extenders

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