Synthesis and characterization of novel acid-sensitive tert-butyl methacrylate and isobutyl methacrylate containing star-shaped polymers

Timothy E. Long; Lars Kilian; Zhen He Wang; Alan R. Esker

doi:10.1117/12.446778

Synthesis and characterization of novel acid-sensitive tert-butyl methacrylate and isobutyl methacrylate containing star-shaped polymers

Timothy E. Long, Lars Kilian, Zhen He Wang, Alan R. Esker

Research output: Contribution to journal › Conference article › peer-review

5 Scopus citations

Abstract

Star-shaped polymers containing poly(isobutyl methacrylate) (iBMA) and poly(tert-butyl methacrylate) (t-BMA) arms coupled to a 2,5-dimethyl-2,5-hexanediol dimethacrylate (DHDMA) core were synthesized using arm-first living anionic polymerization. Gel permeation chromatography (GPC) indicated that coupling efficiencies were high and coupled products exhibited a monomodal molecular weight distribution. The star-shaped polymer number-average molecular weights were 8-10 times higher than the precursor arm molecular weights. The ratio of coupling reagent to living chain end concentration controlled the molecular weight of the star-shaped polymer and the number of coupled arms. The molecular weight distributions of the star-shaped polymers ranged from 1.5-2.0. Due to the labile tertiary-butyl esters contained in the DHDMA cores, these star-shaped polymers were readily hydrolyzed in the presence of acid catalysts. For example, poly(iBMA) star-shaped polymers were hydrolytically stable at 25 °C and hydrolyzed readily at 65 °C in the presence of hydrochloric acid. In addition, the poly(t-BMA) containing star-shaped polymers degraded under similar conditions. The degradation process for the iBMA and t-BMA containing star-shaped polymers was confirmed using ¹H NMR spectroscopy, and poly(iBMA)-block-poly(methacrylic acid) and poly(methacrylic acid) were obtained, respectively.

Original language	English (US)
Pages (from-to)	65-74
Number of pages	10
Journal	Proceedings of SPIE - The International Society for Optical Engineering
Volume	4512
DOIs	https://doi.org/10.1117/12.446778
State	Published - 2001
Externally published	Yes
Event	Complex Adaptive Structures - Hutchinson Island, FL, United States Duration: Jun 4 2001 → Jun 6 2001

Keywords

Anionic polymerization
Coupling
Degradable
Hydrolysis
Methacrylate
Star-shaped polymer
Synthesis

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
Condensed Matter Physics
Computer Science Applications
Applied Mathematics
Electrical and Electronic Engineering

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10.1117/12.446778

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Synthesis and characterization of novel acid-sensitive tert-butyl methacrylate and isobutyl methacrylate containing star-shaped polymers. / Long, Timothy E.; Kilian, Lars; Wang, Zhen He et al.
In: Proceedings of SPIE - The International Society for Optical Engineering, Vol. 4512, 2001, p. 65-74.

Research output: Contribution to journal › Conference article › peer-review

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title = "Synthesis and characterization of novel acid-sensitive tert-butyl methacrylate and isobutyl methacrylate containing star-shaped polymers",

abstract = "Star-shaped polymers containing poly(isobutyl methacrylate) (iBMA) and poly(tert-butyl methacrylate) (t-BMA) arms coupled to a 2,5-dimethyl-2,5-hexanediol dimethacrylate (DHDMA) core were synthesized using arm-first living anionic polymerization. Gel permeation chromatography (GPC) indicated that coupling efficiencies were high and coupled products exhibited a monomodal molecular weight distribution. The star-shaped polymer number-average molecular weights were 8-10 times higher than the precursor arm molecular weights. The ratio of coupling reagent to living chain end concentration controlled the molecular weight of the star-shaped polymer and the number of coupled arms. The molecular weight distributions of the star-shaped polymers ranged from 1.5-2.0. Due to the labile tertiary-butyl esters contained in the DHDMA cores, these star-shaped polymers were readily hydrolyzed in the presence of acid catalysts. For example, poly(iBMA) star-shaped polymers were hydrolytically stable at 25 °C and hydrolyzed readily at 65 °C in the presence of hydrochloric acid. In addition, the poly(t-BMA) containing star-shaped polymers degraded under similar conditions. The degradation process for the iBMA and t-BMA containing star-shaped polymers was confirmed using 1H NMR spectroscopy, and poly(iBMA)-block-poly(methacrylic acid) and poly(methacrylic acid) were obtained, respectively.",

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T1 - Synthesis and characterization of novel acid-sensitive tert-butyl methacrylate and isobutyl methacrylate containing star-shaped polymers

AU - Long, Timothy E.

AU - Kilian, Lars

AU - Wang, Zhen He

AU - Esker, Alan R.

PY - 2001

Y1 - 2001

N2 - Star-shaped polymers containing poly(isobutyl methacrylate) (iBMA) and poly(tert-butyl methacrylate) (t-BMA) arms coupled to a 2,5-dimethyl-2,5-hexanediol dimethacrylate (DHDMA) core were synthesized using arm-first living anionic polymerization. Gel permeation chromatography (GPC) indicated that coupling efficiencies were high and coupled products exhibited a monomodal molecular weight distribution. The star-shaped polymer number-average molecular weights were 8-10 times higher than the precursor arm molecular weights. The ratio of coupling reagent to living chain end concentration controlled the molecular weight of the star-shaped polymer and the number of coupled arms. The molecular weight distributions of the star-shaped polymers ranged from 1.5-2.0. Due to the labile tertiary-butyl esters contained in the DHDMA cores, these star-shaped polymers were readily hydrolyzed in the presence of acid catalysts. For example, poly(iBMA) star-shaped polymers were hydrolytically stable at 25 °C and hydrolyzed readily at 65 °C in the presence of hydrochloric acid. In addition, the poly(t-BMA) containing star-shaped polymers degraded under similar conditions. The degradation process for the iBMA and t-BMA containing star-shaped polymers was confirmed using 1H NMR spectroscopy, and poly(iBMA)-block-poly(methacrylic acid) and poly(methacrylic acid) were obtained, respectively.

AB - Star-shaped polymers containing poly(isobutyl methacrylate) (iBMA) and poly(tert-butyl methacrylate) (t-BMA) arms coupled to a 2,5-dimethyl-2,5-hexanediol dimethacrylate (DHDMA) core were synthesized using arm-first living anionic polymerization. Gel permeation chromatography (GPC) indicated that coupling efficiencies were high and coupled products exhibited a monomodal molecular weight distribution. The star-shaped polymer number-average molecular weights were 8-10 times higher than the precursor arm molecular weights. The ratio of coupling reagent to living chain end concentration controlled the molecular weight of the star-shaped polymer and the number of coupled arms. The molecular weight distributions of the star-shaped polymers ranged from 1.5-2.0. Due to the labile tertiary-butyl esters contained in the DHDMA cores, these star-shaped polymers were readily hydrolyzed in the presence of acid catalysts. For example, poly(iBMA) star-shaped polymers were hydrolytically stable at 25 °C and hydrolyzed readily at 65 °C in the presence of hydrochloric acid. In addition, the poly(t-BMA) containing star-shaped polymers degraded under similar conditions. The degradation process for the iBMA and t-BMA containing star-shaped polymers was confirmed using 1H NMR spectroscopy, and poly(iBMA)-block-poly(methacrylic acid) and poly(methacrylic acid) were obtained, respectively.

KW - Anionic polymerization

KW - Coupling

KW - Degradable

KW - Hydrolysis

KW - Methacrylate

KW - Star-shaped polymer

KW - Synthesis

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Y2 - 4 June 2001 through 6 June 2001

ER -

Synthesis and characterization of novel acid-sensitive tert-butyl methacrylate and isobutyl methacrylate containing star-shaped polymers

Abstract

Keywords

ASJC Scopus subject areas

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