High-performance aromatic thermosetting resins with hydroxyl and ethynyl groups

A novel hydroxyl-ethynyl-arene (HEA) resin was synthesized via Aldol condensation and Sonogashira reaction. The structure of the obtained resin was confirmed by the techniques of mass spectroscopy (MS), gel permeation chromatography (GPC), proton nuclear magnetic resonance spectroscopy (H-1-NMR), Fourier transform infrared spectroscopy, (FT-IR) and elemental analysis (EA). Differential scanning calorimetry (DSC) results showed an exotherm at the temperature range of 187 degrees C-245 degrees C, attributable to crosslinking reaction of the acetylene groups. After thermal cure, the obtained cured resin possessed excellent thermal stability. Thermal gravimetric analysis (TGA) in nitrogen showed the Td(5) (temperature of 5% weight loss) was about 400 degrees C, and the char yield in nitrogen was about 78% at 900 degrees C. The laminate composite of HEA resin was prepared and its mechanical and thermal properties were determined. The usefulness of the HEA resin as matrix for ablative composite was evaluated. Copyright (C) 2010 John Wiley & Sons, Ltd.

[1]  T. Zhao,et al.  Polyarylacetylene blends with improved processability and high thermal stability , 2007 .

[2]  Kuang-Ting Hsiao,et al.  A study of direct cure kinetics characterization during liquid composite molding , 2006 .

[3]  C. R. Nair,et al.  Addition curable phenolic resins based on ethynyl phenyl azo functional novolac , 2002 .

[4]  S. Ando,et al.  Thermal analysis and solid-state 13C NMR study of crosslink in polyimides containing acetylene groups in the main chain , 2001 .

[5]  Stephen G. Kuzak,et al.  Dynamic mechanical analysis of fiber-reinforced phenolics , 1999 .

[6]  P. Grenier,et al.  Thermal polymerization of arylacetylenes: 1. Study of a monofunctional model compound , 1997 .

[7]  M. Guigon,et al.  The interface and interphase in carbon fibre-reinforced composites , 1994 .

[8]  S. Swanson,et al.  Acetylene-terminated polyimide cure studies using carbon-13 magic-angle spinning NMR on isotopically labeled samples , 1992 .

[9]  Keith Smith,et al.  The direct production of tri- and hexa-substituted benzenes from ketones under mild conditions , 1991 .

[10]  D. R. Rutherford,et al.  Poly(ethynylene-2,5-thiophenediylethynylenes). Processable, reactive polymers that thermally cross-link , 1988 .

[11]  C. Marvel,et al.  Polymerization using palladium (II) salts: Homopolymers and copolymers from phenylethynyl compounds and aromatic bromides , 1986 .

[12]  F. Villani,et al.  A general synthesis of terminal and internal arylalkynes by the palladium-catalyzed reaction of alkynylzinc reagents with aryl halides , 2002 .