Thermally curable benzoxazine monomer with a photodimerizable coumarin group

Baris Kiskan; Yusuf Yagci

doi:10.1002/pola.21934

Thermally curable benzoxazine monomer with a photodimerizable coumarin group

Baris Kiskan, Yusuf Yagci^*

^*Corresponding author for this work

Department of Chemistry

Istanbul Technical University

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

150 Citations (Scopus)

Abstract

A new monomer, 4-methyl-9-p-tolyl-9,10-dihydrochromeno[8,7-e][1,3]oxazin- 2(8H)-one, possessing both benzoxazine and coumarin rings in its structure was synthesized by the reaction of 4-methyl-7-hydroxycoumarin, paraformaldehyde, and p-toluidine in methanol at 40°C and characterized with spectral analysis. Upon photolysis around 300 nm, this monomer underwent dimerization via the [2πs+2πs] cycloaddition reaction. Photodimerization reactions were investigated with UV and ¹H NMR spectroscopy measurements. The thermal ring-opening reaction of the benzoxazine ring was demonstrated with differential scanning calorimetry measurements. The thermal behavior of the cured product was also investigated with thermogravimetric analysis.

Original language	English
Pages (from-to)	1670-1676
Number of pages	7
Journal	Journal of Polymer Science, Part A: Polymer Chemistry
Volume	45
Issue number	9
DOIs	https://doi.org/10.1002/pola.21934
Publication status	Published - 1 May 2007

Keywords

Benzoxazine
Coumarin
Crosslinking
Photodimerization
Thermal ring-opening polymerization
Thermosets

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10.1002/pola.21934

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title = "Thermally curable benzoxazine monomer with a photodimerizable coumarin group",

abstract = "A new monomer, 4-methyl-9-p-tolyl-9,10-dihydrochromeno[8,7-e][1,3]oxazin- 2(8H)-one, possessing both benzoxazine and coumarin rings in its structure was synthesized by the reaction of 4-methyl-7-hydroxycoumarin, paraformaldehyde, and p-toluidine in methanol at 40°C and characterized with spectral analysis. Upon photolysis around 300 nm, this monomer underwent dimerization via the [2πs+2πs] cycloaddition reaction. Photodimerization reactions were investigated with UV and 1H NMR spectroscopy measurements. The thermal ring-opening reaction of the benzoxazine ring was demonstrated with differential scanning calorimetry measurements. The thermal behavior of the cured product was also investigated with thermogravimetric analysis.",

keywords = "Benzoxazine, Coumarin, Crosslinking, Photodimerization, Thermal ring-opening polymerization, Thermosets",

author = "Baris Kiskan and Yusuf Yagci",

year = "2007",

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day = "1",

doi = "10.1002/pola.21934",

language = "English",

volume = "45",

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journal = "Journal of Polymer Science, Part A: Polymer Chemistry",

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publisher = "John Wiley \& Sons Inc.",

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TY - JOUR

T1 - Thermally curable benzoxazine monomer with a photodimerizable coumarin group

AU - Kiskan, Baris

AU - Yagci, Yusuf

PY - 2007/5/1

Y1 - 2007/5/1

N2 - A new monomer, 4-methyl-9-p-tolyl-9,10-dihydrochromeno[8,7-e][1,3]oxazin- 2(8H)-one, possessing both benzoxazine and coumarin rings in its structure was synthesized by the reaction of 4-methyl-7-hydroxycoumarin, paraformaldehyde, and p-toluidine in methanol at 40°C and characterized with spectral analysis. Upon photolysis around 300 nm, this monomer underwent dimerization via the [2πs+2πs] cycloaddition reaction. Photodimerization reactions were investigated with UV and 1H NMR spectroscopy measurements. The thermal ring-opening reaction of the benzoxazine ring was demonstrated with differential scanning calorimetry measurements. The thermal behavior of the cured product was also investigated with thermogravimetric analysis.

AB - A new monomer, 4-methyl-9-p-tolyl-9,10-dihydrochromeno[8,7-e][1,3]oxazin- 2(8H)-one, possessing both benzoxazine and coumarin rings in its structure was synthesized by the reaction of 4-methyl-7-hydroxycoumarin, paraformaldehyde, and p-toluidine in methanol at 40°C and characterized with spectral analysis. Upon photolysis around 300 nm, this monomer underwent dimerization via the [2πs+2πs] cycloaddition reaction. Photodimerization reactions were investigated with UV and 1H NMR spectroscopy measurements. The thermal ring-opening reaction of the benzoxazine ring was demonstrated with differential scanning calorimetry measurements. The thermal behavior of the cured product was also investigated with thermogravimetric analysis.

KW - Benzoxazine

KW - Coumarin

KW - Crosslinking

KW - Photodimerization

KW - Thermal ring-opening polymerization

KW - Thermosets

UR - https://www.scopus.com/pages/publications/34248147619

U2 - 10.1002/pola.21934

DO - 10.1002/pola.21934

M3 - Article

AN - SCOPUS:34248147619

SN - 0887-624X

VL - 45

SP - 1670

EP - 1676

JO - Journal of Polymer Science, Part A: Polymer Chemistry

JF - Journal of Polymer Science, Part A: Polymer Chemistry

IS - 9

ER -

Thermally curable benzoxazine monomer with a photodimerizable coumarin group

Abstract

Keywords

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