Photoactive polyesters containing o-nitro benzyl ester functionality for photodeactivatable adhesion

Stephen M. June; Takeo Suga; William H. Heath; Qin Lin; Rama Puligadda; Lei Yan; David Dillard; Timothy E. Long

doi:10.1080/00218464.2013.768112

Photoactive polyesters containing o-nitro benzyl ester functionality for photodeactivatable adhesion

Stephen M. June, Takeo Suga, William H. Heath, Qin Lin, Rama Puligadda, Lei Yan, David Dillard, Timothy E. Long

Research output: Contribution to journal › Article › peer-review

17 Scopus citations

Abstract

The fabrication of modern microelectronic silicon devices mechanically challenges these thin silicon substrates during manufacturing operations. Melt and solution polyesterification enabled the synthesis of polyesters containing photoreactive o-nitro benzyl ester units for use as a potential photocleavable adhesive. Melt transesterification provided a solvent-free method for synthesis of 2-nitro-p-xylylene glycol (NXG)-containing polyesters of controlled molecular weights. ¹H NMR spectroscopy confirmed the chemical composition of the photoactive polyesters. Size exclusion chromatography (SEC) determined the number-average molecular weights (Mn) of the polyesters synthesized in the range of 6000 to 12000 g/mol. ¹H NMR spectroscopy confirmed increasing levels of photocleavage of the o-nitro benzyl ester functionality with increasing exposure to broad wavelength UV irradiation, and exposure levels ranged from 0-187 J/cm² UVA. Photocleaveage of approximately 90% of the o-nitro benzyl ester (ONB) units within the backbone of the polymer occurred at maximum dosage. Wedge fracture testing revealed approximately a two-fold decrease in fracture energy upon UV irradiation, suggesting that these structural adhesives offer potential for commercial "flip bonding" applications.

Original language	English (US)
Pages (from-to)	548-558
Number of pages	11
Journal	Journal of Adhesion
Volume	89
Issue number	7
DOIs	https://doi.org/10.1080/00218464.2013.768112
State	Published - Jul 3 2013
Externally published	Yes

Keywords

Melt transesterification
Micro-fabrication processes
Photoreactive
Polyester
Reversible adhesives
Structural adhesives
Temporary bonding

ASJC Scopus subject areas

General Chemistry
Mechanics of Materials
Surfaces and Interfaces
Surfaces, Coatings and Films
Materials Chemistry

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10.1080/00218464.2013.768112

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title = "Photoactive polyesters containing o-nitro benzyl ester functionality for photodeactivatable adhesion",

abstract = "The fabrication of modern microelectronic silicon devices mechanically challenges these thin silicon substrates during manufacturing operations. Melt and solution polyesterification enabled the synthesis of polyesters containing photoreactive o-nitro benzyl ester units for use as a potential photocleavable adhesive. Melt transesterification provided a solvent-free method for synthesis of 2-nitro-p-xylylene glycol (NXG)-containing polyesters of controlled molecular weights. 1H NMR spectroscopy confirmed the chemical composition of the photoactive polyesters. Size exclusion chromatography (SEC) determined the number-average molecular weights (Mn) of the polyesters synthesized in the range of 6000 to 12000 g/mol. 1H NMR spectroscopy confirmed increasing levels of photocleavage of the o-nitro benzyl ester functionality with increasing exposure to broad wavelength UV irradiation, and exposure levels ranged from 0-187 J/cm2 UVA. Photocleaveage of approximately 90% of the o-nitro benzyl ester (ONB) units within the backbone of the polymer occurred at maximum dosage. Wedge fracture testing revealed approximately a two-fold decrease in fracture energy upon UV irradiation, suggesting that these structural adhesives offer potential for commercial {"}flip bonding{"} applications.",

keywords = "Melt transesterification, Micro-fabrication processes, Photoreactive, Polyester, Reversible adhesives, Structural adhesives, Temporary bonding",

author = "June, {Stephen M.} and Takeo Suga and Heath, {William H.} and Qin Lin and Rama Puligadda and Lei Yan and David Dillard and Long, {Timothy E.}",

note = "Funding Information: This research was supported by Brewer Science, Inc. under contract #N00014-07-C-0797.",

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AU - June, Stephen M.

AU - Suga, Takeo

AU - Heath, William H.

AU - Lin, Qin

AU - Puligadda, Rama

AU - Yan, Lei

AU - Dillard, David

AU - Long, Timothy E.

N1 - Funding Information: This research was supported by Brewer Science, Inc. under contract #N00014-07-C-0797.

PY - 2013/7/3

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N2 - The fabrication of modern microelectronic silicon devices mechanically challenges these thin silicon substrates during manufacturing operations. Melt and solution polyesterification enabled the synthesis of polyesters containing photoreactive o-nitro benzyl ester units for use as a potential photocleavable adhesive. Melt transesterification provided a solvent-free method for synthesis of 2-nitro-p-xylylene glycol (NXG)-containing polyesters of controlled molecular weights. 1H NMR spectroscopy confirmed the chemical composition of the photoactive polyesters. Size exclusion chromatography (SEC) determined the number-average molecular weights (Mn) of the polyesters synthesized in the range of 6000 to 12000 g/mol. 1H NMR spectroscopy confirmed increasing levels of photocleavage of the o-nitro benzyl ester functionality with increasing exposure to broad wavelength UV irradiation, and exposure levels ranged from 0-187 J/cm2 UVA. Photocleaveage of approximately 90% of the o-nitro benzyl ester (ONB) units within the backbone of the polymer occurred at maximum dosage. Wedge fracture testing revealed approximately a two-fold decrease in fracture energy upon UV irradiation, suggesting that these structural adhesives offer potential for commercial "flip bonding" applications.

AB - The fabrication of modern microelectronic silicon devices mechanically challenges these thin silicon substrates during manufacturing operations. Melt and solution polyesterification enabled the synthesis of polyesters containing photoreactive o-nitro benzyl ester units for use as a potential photocleavable adhesive. Melt transesterification provided a solvent-free method for synthesis of 2-nitro-p-xylylene glycol (NXG)-containing polyesters of controlled molecular weights. 1H NMR spectroscopy confirmed the chemical composition of the photoactive polyesters. Size exclusion chromatography (SEC) determined the number-average molecular weights (Mn) of the polyesters synthesized in the range of 6000 to 12000 g/mol. 1H NMR spectroscopy confirmed increasing levels of photocleavage of the o-nitro benzyl ester functionality with increasing exposure to broad wavelength UV irradiation, and exposure levels ranged from 0-187 J/cm2 UVA. Photocleaveage of approximately 90% of the o-nitro benzyl ester (ONB) units within the backbone of the polymer occurred at maximum dosage. Wedge fracture testing revealed approximately a two-fold decrease in fracture energy upon UV irradiation, suggesting that these structural adhesives offer potential for commercial "flip bonding" applications.

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KW - Structural adhesives

KW - Temporary bonding

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Photoactive polyesters containing o-nitro benzyl ester functionality for photodeactivatable adhesion

Abstract

Keywords

ASJC Scopus subject areas

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