Thermal polymerization of arylacetylenes: 1. Study of a monofunctional model compound

Gandon, S.; Mison, P.; Bartholin, M.; Merçier, Régis; Sillion, Bernard; Geneve, E.; Greniér, Philippe; Grenier‐Loustalot, Marie‐Florence

doi:10.1016/s0032-3861(96)00658-1

Cited by 22 publications

(17 citation statements)

References 19 publications

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“…Although acetylene‐containing resins have been researched for decades, the literature data do not allow a complete understanding of such unusual radical polymerization and many questions are still without answer 11. Many previous studies, based on the analysis of compounds formed during thermal polymerization of monofuctional model compounds confirmed that low‐molar mass are formed initially by ways of Strauss coupling, Glaser coupling, and diene‐diene dimmers.…”

Section: Resultsmentioning

confidence: 99%

High‐performance aromatic thermosetting resins with hydroxyl and ethynyl groups

Yang

Shi

Wang

et al. 2011

Polymers for Advanced Techs

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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 (1H‐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°C–245°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 Td5 (temperature of 5% weight loss) was about 400°C, and the char yield in nitrogen was about 78% at 900°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 © 2010 John Wiley & Sons, Ltd.

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Section: Resultsmentioning

confidence: 99%

High‐performance aromatic thermosetting resins with hydroxyl and ethynyl groups

Yang

Shi

Wang

et al. 2011

Polymers for Advanced Techs

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“…According to literature acetylene can react under cationic, coordination, free radical, photolytic. Thermal polymerization of model diethynyl compounds in the literature showed reaction paths forming Strauss coupling, Diels‐Alder products, trimers, tetramers, naphthalenes, and conjugated polymers 27. One study of acetylene terminated imide reported 30% of the acetylenic groups underwent cyclotrimerization while the remainder was consumed by other reactions 28.…”

Section: Resultsmentioning

confidence: 99%

Preparation and characterization of high char yield polybenzoxazine/polyarylacetylene blends for resin‐transfer molding

Pan

Luo

et al. 2009

J of Applied Polymer Sci

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Benzoxazine precursors (BOZP), 6,6′‐bis(2,3‐dihydro‐3‐(3‐ethynylphenyl)‐4H‐1,3‐ benzoxazinyl)ketone and 6,6′‐bis(2,3‐dihydro‐3‐(3‐ethynylphenyl)‐4H‐1,3‐benzoxazinyl)ether were synthesized and characterized by Proton nuclear magnetic resonace (1H‐NMR) and Fourier transform infrared spectroscopy (FTIR). The polyarylacetylene (PAA) was synthesized through thermal polymerization of diethynylbenzene, and characterized by 1H‐NMR, FTIR, and Differential Scanning Calorimetry (DSC). The BOZP/PAA blends were prepared with different contents of PAA, and their viscosity was measured using NDJ‐79 rotating visometer. The curing behavior of BOZP/PAA blends was characterized by DSC. The thermal stability of cured BOZP/PAA blends was studied using Thermogravimetric Analysis, the results show char yield at 800°C was in the range of 78–84%. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2009

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“…3,5-Dibromo-1-(3-hydroxyl-3-methylbutynyl)benzene was synthesized as previously described [7]. [8], 3,5-dihexyloxybenzyl alcohol [9], 3,5-didodecyloxybenzyl alcohol [10], 3,5bis(3,5-dihexyloxybenzyloxy)benzyl alcohol [11], and (4hexyloxyphenyl)acetylene (Hex0H) [12] were synthesized according to the literature procedures. (Bicyclo [2.2.1]hepta-2,5-diene)chlororhodium(I) dimer catalyst ([Rh(nbd)Cl] 2 ) (Aldrich Co.), bis(triphenylphosphine)palladium(II) chloride (Aldrich Co.), and n-butyllithium (Kanto Chemical Co., Inc., 1.6 M in hexane) were used without further purification.…”

Section: Methodsmentioning

confidence: 99%

Polymerization of Phenylacetylene-Based Monodendrons with Alkoxy Peripheral Groups and Oxygen/Nitrogen Permeation Behavior of Their Membranes

Kaneko

Sato

Uchiya

et al. 2012

International Journal of Polymer Science

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Monodendron monomers with alkoxy peripheral groups were synthesized, and the focal point of monodendrons, terminal acetylene, was polymerized with rhodium catalyst to yield corresponding polydendrons with a high molecular weight. The polydendrons were soluble in common organic solvents and readily formed membranes. Oxygen permselectivity was improved in the polydendrons with a space-persistent dendritic crowd. It was found that the well-defined dendritic and rod-like structure of the polydendrons was useful for permselective membrane.

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Thermal polymerization of arylacetylenes: 1. Study of a monofunctional model compound

Cited by 22 publications

References 19 publications

High‐performance aromatic thermosetting resins with hydroxyl and ethynyl groups

High‐performance aromatic thermosetting resins with hydroxyl and ethynyl groups

Preparation and characterization of high char yield polybenzoxazine/polyarylacetylene blends for resin‐transfer molding

Polymerization of Phenylacetylene-Based Monodendrons with Alkoxy Peripheral Groups and Oxygen/Nitrogen Permeation Behavior of Their Membranes

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