High performance benzoxazine monomers and polymers containing furan groups

Abstract

Furan-containing benzoxazine monomers, 3-furfuryl-3,4-dihydro-2H-1,3benzoxazine (P-FBz) and bis(3-furfuryl-3,4-dihydro-2H-1,3-benzoxazinyl)isopropane (BPA-FBz), were prepared using furfurylamine as a raw material. The chemical structures of P-FBz and BPA-FBz were characterized with FTIR, 1 H NMR, elemental analysis, and mass spectrometry. Formation of furfurylamine Mannich bridge networks in the polymerizations of P-FBz and BPA-FBz increased the cross-linking densities and thermal stability of the resulting polybenzoxazines. P-FBz-and BPA-FBzbased polymers also exhibited high glass transition temperatures above 300 8C, high char yields, and low flammability with limited oxygen index values of 31. The dielectric (D k ¼ 3.21-3.39) and mechanical properties (high storage modulus of 3.0-3.9 GPa and low coefficient of thermal expansion of 37.7 -45.4 ppm) of the P-FBzand BPA-FBz-based polymers were superior or comparable to other polybenzoxazines.

Facile approach to functionalizing polymers with specific chemical groups by an ozone treatment: Preparation of crosslinkable poly(vinylidene fluoride) possessing benzoxazine pendent groups

“…The crosslinking density obtained for crosslinked PVDF was lower than that observed for thermosetting resins. 23 However, they provided evidence for the performance of the crosslinking behavior of PVDF-Bz. The crosslinking behavior of PVDF-Bz was also observed with the changes in the mechanical properties of the PVDF polymers.…”

“…[18][19][20][21][22] Crosslinkable sites on PVDF can be formed through dehydrofluorination on PVDF [18][19][20] or be introduced onto PVDF chains with functional comonomers in PVDF preparation. 21,22 As PVDF-BQ possesses phenol pendent groups, in this work, benzoxazine groups, which can perform a ring-opening addition reaction under heat, [23][24][25][26] are incorporated into PVDF by the reaction of PVDF-BQ with formaldehyde and aniline. This reaction demonstrates the reactivity and chemical versatility of PVDF-BQ chains and provides a convenient approach for preparing crosslinkable PVDF.…”

Comparison of two bisbenzoxazines containing carboxylic groups and their thermal polymerization

“…Thus, many studies on performance enhancement of polybenzoxazine mainly include copolymer, polymer alloys, fiber-reinforced composites, nanocomposite, etc. [7][8][9][10][11]. Another effective approach is preparation of monomers with additional functionality [12,13].…”

Development and application of novel ring‐opening polymerizations to functional networked polymers

“…11 Thanking to the structural diversity of these starting materials, a wide range of benzoxazine-type monomers involving curable multifunctional ones and intriguing structures have been developed. [12][13][14][15][16][17][18][19][20][21][22] In Scheme 1, the synthesis of a bifunctional benzoxazine from bisphenol-A and aniline and its polymerization are shown as typical examples. The resulting main chain has phenolic moiety bridged by Mannich-type linkage (ACH 2 ANRACH 2 A).…”