Synthesis and crosslinking reaction of a novel polymer containing benzoxazine and phenyleneethynylene moieties in the main chain. Issue 24 (4th November 2019)

• Record Type: Journal Article
• Authors: Kobayashi, Takumi; Goto, Masahide; Minami, Masaki; Sanda, Fumio
• Is Part Of: Journal of polymer science. Volume 57:Issue 24(2019)
• Page Start: 2581
• Page End: 2589
• Publication Date: 2019-11-04
• Subjects: benzoxazine -- IR spectroscopy, NMR spectroscopy -- phenyleneethynylene -- polymers -- ring‐opening polymerization -- Sonogashira–Hagihara coupling polymerization -- thermal stability; 547
• DOI: 10.1002/pola.29536
• Languages: English
• ISSNs: 0887-624X

Abstract

ABSTRACT: A novel polymer, poly(1 ) containing benzoxazine and phenyleneethynylene moieties in the main chain with number‐average molecular weights ranging from 1400 to 9800 was obtained quantitatively by the Sonogashira–Hagihara coupling polymerization of the corresponding iodophenyl‐ and ethynylphenyl‐substituted monomer 1 . Poly(1 ) was heated at 200 °C under N2 for 2 h to obtain the cured polymer, poly(1 )′ via the ring‐opening polymerization of the benzoxazine moieties. The structures of the polymer before and after curing were confirmed by 1 H‐NMR, IR, and UV–vis absorption and reflectance spectroscopies. Poly(1 )′ was thermally more stable than monomer 1 and poly(1 ). A specimen was prepared from a mixture of poly(1 ) and phenol‐diaminodiphenylmethane type benzoxazine 2 by heating at 200 °C for 2 h under N2 . The poly(1 )/2 resin was thermally stable than bisphenol‐A type benzoxazine resin 3 . Poly(1 ) exhibited XRD peaks corresponding to the d ‐spacings of 1.26–0.98 and 0.40 nm, assignable to the repeating monomer unit and alignment of polymer molecules, respectively. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 2581–2589 Abstract : A novel polymer containing benzoxazine and phenyleneethynylene moieties in the main chain was obtained by the Sonogashira–Hagihara coupling polymerization. The polymer was crosslinked by the ring‐opening polymerization of the benzoxazine moieties at 200 °C keeping the phenyleneethynylene backbone intact. The cured resin was thermally stable as evidenced by thermogravimetric analysis.