Advanced Polymers from Simple Benzoxazines and Phenols by Ring-Opening Addition Reactions

Zeynep Deliballi; Baris Kiskan; Yusuf Yagci

doi:10.1021/acs.macromol.0c00225

Advanced Polymers from Simple Benzoxazines and Phenols by Ring-Opening Addition Reactions

Zeynep Deliballi, Baris Kiskan^*, Yusuf Yagci

^*Corresponding author for this work

Department of Chemistry

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

37 Citations (Scopus)

Abstract

Simple benzoxazines were mixed and reacted with various phenolics such as phenol, p-nitrophenol, p-cresol, 1,3-dihyroxybenzene (resorcinol), 1,3,5-trihydroxybenzene (phloroglucinol), and N-(2-hydroxyphenyl)benzamide. The influence of these phenolic compounds on ring-opening polymerization temperature of benzoxazines was examined by DSC analysis. The cresol-based benzoxazine (C-a) and phenolics yielded polymers with molecular weight of around 1500 Da. Interestingly, for C-a/resorcinol-and C-a/phloroglucinol-based polymers, a second GPC trace was observed that corresponds to a few million daltons for mixing ratios of 4:1 and 5:1. Moreover, the mixtures of C-a and N-(2-hydroxyphenyl)benzamide gave poly(benzoxazine-benzoxazole)s through a new methodology eliminating the need of synthesis of ortho-amide benzoxazines. The obtained polymers were soluble and characterized in detail by ¹H NMR, ¹³C NMR, GPC, DSC, and TGA analyses.

Original language	English
Pages (from-to)	2354-2361
Number of pages	8
Journal	Macromolecules
Volume	53
Issue number	7
DOIs	https://doi.org/10.1021/acs.macromol.0c00225
Publication status	Published - 14 Apr 2020

Bibliographical note

Publisher Copyright:
© 2020 American Chemical Society.

Funding

The authors thank the Istanbul Technical University Research Fund for financial support, and Z.D also thanks the Council of Higher Education (YOK) for financial support.

Funders	Funder number
Istanbul Technical University Research Fund
YOK
Yükseköğretim Kurulu

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abstract = "Simple benzoxazines were mixed and reacted with various phenolics such as phenol, p-nitrophenol, p-cresol, 1,3-dihyroxybenzene (resorcinol), 1,3,5-trihydroxybenzene (phloroglucinol), and N-(2-hydroxyphenyl)benzamide. The influence of these phenolic compounds on ring-opening polymerization temperature of benzoxazines was examined by DSC analysis. The cresol-based benzoxazine (C-a) and phenolics yielded polymers with molecular weight of around 1500 Da. Interestingly, for C-a/resorcinol-and C-a/phloroglucinol-based polymers, a second GPC trace was observed that corresponds to a few million daltons for mixing ratios of 4:1 and 5:1. Moreover, the mixtures of C-a and N-(2-hydroxyphenyl)benzamide gave poly(benzoxazine-benzoxazole)s through a new methodology eliminating the need of synthesis of ortho-amide benzoxazines. The obtained polymers were soluble and characterized in detail by 1H NMR, 13C NMR, GPC, DSC, and TGA analyses.",

author = "Zeynep Deliballi and Baris Kiskan and Yusuf Yagci",

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AU - Kiskan, Baris

AU - Yagci, Yusuf

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AB - Simple benzoxazines were mixed and reacted with various phenolics such as phenol, p-nitrophenol, p-cresol, 1,3-dihyroxybenzene (resorcinol), 1,3,5-trihydroxybenzene (phloroglucinol), and N-(2-hydroxyphenyl)benzamide. The influence of these phenolic compounds on ring-opening polymerization temperature of benzoxazines was examined by DSC analysis. The cresol-based benzoxazine (C-a) and phenolics yielded polymers with molecular weight of around 1500 Da. Interestingly, for C-a/resorcinol-and C-a/phloroglucinol-based polymers, a second GPC trace was observed that corresponds to a few million daltons for mixing ratios of 4:1 and 5:1. Moreover, the mixtures of C-a and N-(2-hydroxyphenyl)benzamide gave poly(benzoxazine-benzoxazole)s through a new methodology eliminating the need of synthesis of ortho-amide benzoxazines. The obtained polymers were soluble and characterized in detail by 1H NMR, 13C NMR, GPC, DSC, and TGA analyses.

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Advanced Polymers from Simple Benzoxazines and Phenols by Ring-Opening Addition Reactions

Abstract

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