Thermogelling polymers composed of poly(cyclohexylenedimethylene adipate) and poly(ethylene glycol)

Yuhsin Tsai, Li Cheng Jheng, Lien-Chung Hsu

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Block copolymers composed of hydrophilic poly(ethylene glycol) (PEG) and hydrophobic biodegradable polyesters have been reported as thermogelling polymers, because they feature temperature-dependent sol-to-gel or gel-to-sol transitions in aqueous solutions. In this study, a series of thermogelling poly(ethylene glycol methyl ether)-block-poly(cyclohexylenedimethylene adipate)-block-poly(ethylene glycol methyl ether) triblock copolymers and PEG-block-poly(cyclohexylenedimethylene adipate) multiblock copolymers was synthesized by reacting hydroxyl-terminated poly(cyclohexylenedimethylene adipate) (PCA) with poly(ethylene glycol methyl ether) and PEG, respectively, using 1,6-diisocyanatohexane as the coupling agent. Two hydroxyl-terminated PCAs, i.e., poly(1,4-cyclohexylenedimethylene adipate) and poly(1,3/1,4- cyclohexylenedimethylene adipate), were synthesized by the condensation reaction of adipic acid (AA) with 1,4-cyclohexanedimethanol (CHDM) and 1,3/1,4-CHDM, respectively, and used as the hydrophobic polyester blocks of these thermogelling copolymers to compare the effect of crystallinity on the sol-to-gel transition behavior. The polymers were characterized using proton nuclear magnetic resonance, Fourier transform infrared spectroscopy, gel permeation chromatography, differential scanning calorimetry, solubility testing, and rheological analysis. Experimental results revealed that the structure of the PCA block (crystalline vs. amorphous), the molecular weights of the hydrophobic PCA and hydrophilic PEG blocks, and the type of thermogelling polymer (triblock vs. multiblock) influenced the solubility, polymer micelle packing characteristics, maximum storage modulus, and sol-to-gel temperature of the polymers. Among all the samples at 40 wt.% aqueous solutions, triblock copolymer TB3 showed sol-to-gel temperature at 22°C, and had the highest maximum storage modulus about 170 Pa.

Original languageEnglish
Pages (from-to)541-548
Number of pages8
JournalEuropean Polymer Journal
Volume48
Issue number3
DOIs
Publication statusPublished - 2012 Mar 1

Fingerprint

Polyethylene glycols
glycols
Polymers
ethylene
gels
Polymethyl Methacrylate
copolymers
Sols
polymers
ethers
Gels
Methyl Ethers
polyesters
Block copolymers
Ethers
solubility
Polyesters
aqueous solutions
gel chromatography
Hydroxyl Radical

All Science Journal Classification (ASJC) codes

  • Physics and Astronomy(all)
  • Polymers and Plastics
  • Organic Chemistry

Cite this

@article{68c4e2330b9247aca52c2207b53543cd,
title = "Thermogelling polymers composed of poly(cyclohexylenedimethylene adipate) and poly(ethylene glycol)",
abstract = "Block copolymers composed of hydrophilic poly(ethylene glycol) (PEG) and hydrophobic biodegradable polyesters have been reported as thermogelling polymers, because they feature temperature-dependent sol-to-gel or gel-to-sol transitions in aqueous solutions. In this study, a series of thermogelling poly(ethylene glycol methyl ether)-block-poly(cyclohexylenedimethylene adipate)-block-poly(ethylene glycol methyl ether) triblock copolymers and PEG-block-poly(cyclohexylenedimethylene adipate) multiblock copolymers was synthesized by reacting hydroxyl-terminated poly(cyclohexylenedimethylene adipate) (PCA) with poly(ethylene glycol methyl ether) and PEG, respectively, using 1,6-diisocyanatohexane as the coupling agent. Two hydroxyl-terminated PCAs, i.e., poly(1,4-cyclohexylenedimethylene adipate) and poly(1,3/1,4- cyclohexylenedimethylene adipate), were synthesized by the condensation reaction of adipic acid (AA) with 1,4-cyclohexanedimethanol (CHDM) and 1,3/1,4-CHDM, respectively, and used as the hydrophobic polyester blocks of these thermogelling copolymers to compare the effect of crystallinity on the sol-to-gel transition behavior. The polymers were characterized using proton nuclear magnetic resonance, Fourier transform infrared spectroscopy, gel permeation chromatography, differential scanning calorimetry, solubility testing, and rheological analysis. Experimental results revealed that the structure of the PCA block (crystalline vs. amorphous), the molecular weights of the hydrophobic PCA and hydrophilic PEG blocks, and the type of thermogelling polymer (triblock vs. multiblock) influenced the solubility, polymer micelle packing characteristics, maximum storage modulus, and sol-to-gel temperature of the polymers. Among all the samples at 40 wt.{\%} aqueous solutions, triblock copolymer TB3 showed sol-to-gel temperature at 22°C, and had the highest maximum storage modulus about 170 Pa.",
author = "Yuhsin Tsai and Jheng, {Li Cheng} and Lien-Chung Hsu",
year = "2012",
month = "3",
day = "1",
doi = "10.1016/j.eurpolymj.2011.12.007",
language = "English",
volume = "48",
pages = "541--548",
journal = "European Polymer Journal",
issn = "0014-3057",
publisher = "Elsevier Limited",
number = "3",

}

Thermogelling polymers composed of poly(cyclohexylenedimethylene adipate) and poly(ethylene glycol). / Tsai, Yuhsin; Jheng, Li Cheng; Hsu, Lien-Chung.

In: European Polymer Journal, Vol. 48, No. 3, 01.03.2012, p. 541-548.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Thermogelling polymers composed of poly(cyclohexylenedimethylene adipate) and poly(ethylene glycol)

AU - Tsai, Yuhsin

AU - Jheng, Li Cheng

AU - Hsu, Lien-Chung

PY - 2012/3/1

Y1 - 2012/3/1

N2 - Block copolymers composed of hydrophilic poly(ethylene glycol) (PEG) and hydrophobic biodegradable polyesters have been reported as thermogelling polymers, because they feature temperature-dependent sol-to-gel or gel-to-sol transitions in aqueous solutions. In this study, a series of thermogelling poly(ethylene glycol methyl ether)-block-poly(cyclohexylenedimethylene adipate)-block-poly(ethylene glycol methyl ether) triblock copolymers and PEG-block-poly(cyclohexylenedimethylene adipate) multiblock copolymers was synthesized by reacting hydroxyl-terminated poly(cyclohexylenedimethylene adipate) (PCA) with poly(ethylene glycol methyl ether) and PEG, respectively, using 1,6-diisocyanatohexane as the coupling agent. Two hydroxyl-terminated PCAs, i.e., poly(1,4-cyclohexylenedimethylene adipate) and poly(1,3/1,4- cyclohexylenedimethylene adipate), were synthesized by the condensation reaction of adipic acid (AA) with 1,4-cyclohexanedimethanol (CHDM) and 1,3/1,4-CHDM, respectively, and used as the hydrophobic polyester blocks of these thermogelling copolymers to compare the effect of crystallinity on the sol-to-gel transition behavior. The polymers were characterized using proton nuclear magnetic resonance, Fourier transform infrared spectroscopy, gel permeation chromatography, differential scanning calorimetry, solubility testing, and rheological analysis. Experimental results revealed that the structure of the PCA block (crystalline vs. amorphous), the molecular weights of the hydrophobic PCA and hydrophilic PEG blocks, and the type of thermogelling polymer (triblock vs. multiblock) influenced the solubility, polymer micelle packing characteristics, maximum storage modulus, and sol-to-gel temperature of the polymers. Among all the samples at 40 wt.% aqueous solutions, triblock copolymer TB3 showed sol-to-gel temperature at 22°C, and had the highest maximum storage modulus about 170 Pa.

AB - Block copolymers composed of hydrophilic poly(ethylene glycol) (PEG) and hydrophobic biodegradable polyesters have been reported as thermogelling polymers, because they feature temperature-dependent sol-to-gel or gel-to-sol transitions in aqueous solutions. In this study, a series of thermogelling poly(ethylene glycol methyl ether)-block-poly(cyclohexylenedimethylene adipate)-block-poly(ethylene glycol methyl ether) triblock copolymers and PEG-block-poly(cyclohexylenedimethylene adipate) multiblock copolymers was synthesized by reacting hydroxyl-terminated poly(cyclohexylenedimethylene adipate) (PCA) with poly(ethylene glycol methyl ether) and PEG, respectively, using 1,6-diisocyanatohexane as the coupling agent. Two hydroxyl-terminated PCAs, i.e., poly(1,4-cyclohexylenedimethylene adipate) and poly(1,3/1,4- cyclohexylenedimethylene adipate), were synthesized by the condensation reaction of adipic acid (AA) with 1,4-cyclohexanedimethanol (CHDM) and 1,3/1,4-CHDM, respectively, and used as the hydrophobic polyester blocks of these thermogelling copolymers to compare the effect of crystallinity on the sol-to-gel transition behavior. The polymers were characterized using proton nuclear magnetic resonance, Fourier transform infrared spectroscopy, gel permeation chromatography, differential scanning calorimetry, solubility testing, and rheological analysis. Experimental results revealed that the structure of the PCA block (crystalline vs. amorphous), the molecular weights of the hydrophobic PCA and hydrophilic PEG blocks, and the type of thermogelling polymer (triblock vs. multiblock) influenced the solubility, polymer micelle packing characteristics, maximum storage modulus, and sol-to-gel temperature of the polymers. Among all the samples at 40 wt.% aqueous solutions, triblock copolymer TB3 showed sol-to-gel temperature at 22°C, and had the highest maximum storage modulus about 170 Pa.

UR - http://www.scopus.com/inward/record.url?scp=84857053088&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84857053088&partnerID=8YFLogxK

U2 - 10.1016/j.eurpolymj.2011.12.007

DO - 10.1016/j.eurpolymj.2011.12.007

M3 - Article

VL - 48

SP - 541

EP - 548

JO - European Polymer Journal

JF - European Polymer Journal

SN - 0014-3057

IS - 3

ER -