Effect of unsymmetrical spiro dianhydride structure on properties of fully aliphatic polyimides

Hwan Chul Yu, S. Vijay Kumar, Jiyoung Choi, Kazuaki Kudo, Yong Hoon Jang, Chan Moon Chung

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Structure-property relationship was studied for fully aliphatic polyimides containing alicyclic dianhydride and diamine units. Rel-(1′R,3S,5′S) -spiro[furan-3(2H),6′-[3]oxabicyclo[3.2.1]octane]-2,2′,4′, 5(4H)-tetrone (DAn) was used as an unsymmetrical spiro dianhydride, and 1,2,3,4-cyclopentanetetracarboxylic dianhydride (CPDA) and bicyclo[2.2.2]oct-7- ene-2,3,5,6-tetracarboxylic dianhydride (BOCA) were used as symmetrical non-spiro dianhydrides. 4,4′-Methylenebis(2-methylcyclohexylamine) (MMCA) and 5-amino-1,3,3-trimethylcyclohexanemethylamine (AMCH) were N-silylated, and reacted with the dianhydrides to prepare the fully alicyclic polyimides. The formation of the polyimides was confirmed by Fourier transform infrared spectroscopy. DAn-based polyimides showed higher solubility than the polyimides derived from CPDA or BOCA. This was explained based on the results of wide-angle X-ray diffraction (WAXD) analysis of the polyimides. The WAXD study showed that DAn-based polyimides have greater full width at half maximum (FWHM) and d-spacing values than the other polyimides. This indicates that DAn-containing polyimides have lower intermolecular order, decreased intermolecular interaction, and less close chain packing compared to the other polyimides. It is considered that the morphology of DAn polyimides is attributable to the unsymmetrical spiro structure of DAn that leads to bulkiness, irregularity, and non-linearity of the polyimide chains. Decomposition temperatures of the polyimides were investigated by thermogravimetric analysis (TGA) and UV-visible spectroscopy was performed to evaluate the optical transparency of the polyimides.

Original languageEnglish
Pages (from-to)418-424
Number of pages7
JournalHigh Performance Polymers
Volume24
Issue number5
DOIs
Publication statusPublished - 2012 Aug 1

Fingerprint

Polyimides
Diamines
Full width at half maximum
Transparency
X ray diffraction analysis
Fourier transform infrared spectroscopy
Thermogravimetric analysis
Solubility
Spectroscopy

All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Polymers and Plastics
  • Materials Chemistry

Cite this

Yu, Hwan Chul ; Kumar, S. Vijay ; Choi, Jiyoung ; Kudo, Kazuaki ; Jang, Yong Hoon ; Chung, Chan Moon. / Effect of unsymmetrical spiro dianhydride structure on properties of fully aliphatic polyimides. In: High Performance Polymers. 2012 ; Vol. 24, No. 5. pp. 418-424.
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abstract = "Structure-property relationship was studied for fully aliphatic polyimides containing alicyclic dianhydride and diamine units. Rel-(1′R,3S,5′S) -spiro[furan-3(2H),6′-[3]oxabicyclo[3.2.1]octane]-2,2′,4′, 5(4H)-tetrone (DAn) was used as an unsymmetrical spiro dianhydride, and 1,2,3,4-cyclopentanetetracarboxylic dianhydride (CPDA) and bicyclo[2.2.2]oct-7- ene-2,3,5,6-tetracarboxylic dianhydride (BOCA) were used as symmetrical non-spiro dianhydrides. 4,4′-Methylenebis(2-methylcyclohexylamine) (MMCA) and 5-amino-1,3,3-trimethylcyclohexanemethylamine (AMCH) were N-silylated, and reacted with the dianhydrides to prepare the fully alicyclic polyimides. The formation of the polyimides was confirmed by Fourier transform infrared spectroscopy. DAn-based polyimides showed higher solubility than the polyimides derived from CPDA or BOCA. This was explained based on the results of wide-angle X-ray diffraction (WAXD) analysis of the polyimides. The WAXD study showed that DAn-based polyimides have greater full width at half maximum (FWHM) and d-spacing values than the other polyimides. This indicates that DAn-containing polyimides have lower intermolecular order, decreased intermolecular interaction, and less close chain packing compared to the other polyimides. It is considered that the morphology of DAn polyimides is attributable to the unsymmetrical spiro structure of DAn that leads to bulkiness, irregularity, and non-linearity of the polyimide chains. Decomposition temperatures of the polyimides were investigated by thermogravimetric analysis (TGA) and UV-visible spectroscopy was performed to evaluate the optical transparency of the polyimides.",
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Effect of unsymmetrical spiro dianhydride structure on properties of fully aliphatic polyimides. / Yu, Hwan Chul; Kumar, S. Vijay; Choi, Jiyoung; Kudo, Kazuaki; Jang, Yong Hoon; Chung, Chan Moon.

In: High Performance Polymers, Vol. 24, No. 5, 01.08.2012, p. 418-424.

Research output: Contribution to journalArticle

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T1 - Effect of unsymmetrical spiro dianhydride structure on properties of fully aliphatic polyimides

AU - Yu, Hwan Chul

AU - Kumar, S. Vijay

AU - Choi, Jiyoung

AU - Kudo, Kazuaki

AU - Jang, Yong Hoon

AU - Chung, Chan Moon

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N2 - Structure-property relationship was studied for fully aliphatic polyimides containing alicyclic dianhydride and diamine units. Rel-(1′R,3S,5′S) -spiro[furan-3(2H),6′-[3]oxabicyclo[3.2.1]octane]-2,2′,4′, 5(4H)-tetrone (DAn) was used as an unsymmetrical spiro dianhydride, and 1,2,3,4-cyclopentanetetracarboxylic dianhydride (CPDA) and bicyclo[2.2.2]oct-7- ene-2,3,5,6-tetracarboxylic dianhydride (BOCA) were used as symmetrical non-spiro dianhydrides. 4,4′-Methylenebis(2-methylcyclohexylamine) (MMCA) and 5-amino-1,3,3-trimethylcyclohexanemethylamine (AMCH) were N-silylated, and reacted with the dianhydrides to prepare the fully alicyclic polyimides. The formation of the polyimides was confirmed by Fourier transform infrared spectroscopy. DAn-based polyimides showed higher solubility than the polyimides derived from CPDA or BOCA. This was explained based on the results of wide-angle X-ray diffraction (WAXD) analysis of the polyimides. The WAXD study showed that DAn-based polyimides have greater full width at half maximum (FWHM) and d-spacing values than the other polyimides. This indicates that DAn-containing polyimides have lower intermolecular order, decreased intermolecular interaction, and less close chain packing compared to the other polyimides. It is considered that the morphology of DAn polyimides is attributable to the unsymmetrical spiro structure of DAn that leads to bulkiness, irregularity, and non-linearity of the polyimide chains. Decomposition temperatures of the polyimides were investigated by thermogravimetric analysis (TGA) and UV-visible spectroscopy was performed to evaluate the optical transparency of the polyimides.

AB - Structure-property relationship was studied for fully aliphatic polyimides containing alicyclic dianhydride and diamine units. Rel-(1′R,3S,5′S) -spiro[furan-3(2H),6′-[3]oxabicyclo[3.2.1]octane]-2,2′,4′, 5(4H)-tetrone (DAn) was used as an unsymmetrical spiro dianhydride, and 1,2,3,4-cyclopentanetetracarboxylic dianhydride (CPDA) and bicyclo[2.2.2]oct-7- ene-2,3,5,6-tetracarboxylic dianhydride (BOCA) were used as symmetrical non-spiro dianhydrides. 4,4′-Methylenebis(2-methylcyclohexylamine) (MMCA) and 5-amino-1,3,3-trimethylcyclohexanemethylamine (AMCH) were N-silylated, and reacted with the dianhydrides to prepare the fully alicyclic polyimides. The formation of the polyimides was confirmed by Fourier transform infrared spectroscopy. DAn-based polyimides showed higher solubility than the polyimides derived from CPDA or BOCA. This was explained based on the results of wide-angle X-ray diffraction (WAXD) analysis of the polyimides. The WAXD study showed that DAn-based polyimides have greater full width at half maximum (FWHM) and d-spacing values than the other polyimides. This indicates that DAn-containing polyimides have lower intermolecular order, decreased intermolecular interaction, and less close chain packing compared to the other polyimides. It is considered that the morphology of DAn polyimides is attributable to the unsymmetrical spiro structure of DAn that leads to bulkiness, irregularity, and non-linearity of the polyimide chains. Decomposition temperatures of the polyimides were investigated by thermogravimetric analysis (TGA) and UV-visible spectroscopy was performed to evaluate the optical transparency of the polyimides.

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