Aromatic polyethers, polysulfones, and polyketones as laminating resins. V. Polymers containing acetylenic side groups

Samyn, Celest; Marvel, C. S.

doi:10.1002/pol.1975.170130506

Cited by 15 publications

(1 citation statement)

References 11 publications

(5 reference statements)

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“…Acetylene‐ or phenylacetylene‐terminated resins can be thermally cured without giving off volatiles. Acetylene groups have been used as crosslinking reaction sites in aromatic polyimides,1, 2 poly(ether ketone sulfone)s,3, 4 polyphenylquinoxalines,5 poly(phenyl‐ as ‐triazine)s,6 Schiff base polymers,7 poly(perfluoroalkylene ether benzoxazole)s,8 poly(phenylquinozaline)s9 and polyphenylenes 10. Resins terminated with acetylene or phenylacetylene have a long shelf life and their cured products have excellent solvent resistance and favorable combination of physical and mechanical properties at high temperature.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and thermal cure of diphenyl ethers terminated with acetylene and phenylacetylene

Wang

Zhang

et al. 2006

Polymer International

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Two kinds of novel compounds, diphenylacetylene diphenyl ether (DPADPE) and diacetylene diphenyl ether (DADPE), were prepared and polymerized under heating. Raman, DSC and 13 C CP/MAS NMR analyses were used for studying the polymerization reaction. DPADPE and DADPE have melting points at 190 and 79 • C, with exothermic peaks of the DSC curves at 375 and 215 • C for curing, respectively. Raman and 13 C CP/MAS NMR spectra show that DPADPE could be cured at a temperature higher than 300 • C and DADPE at a lower temperature of higher than 150 • C. The kinetic parameters for the thermal crosslinking reactions were obtained by the Ozawa method and the results show that the apparent activation energy is 152 kJ mol −1 for DPADPE and 109 kJ mol −1 for DADPE. An ene-yne Straus product appears in the cured DADPE, whereas this product has not been identified in the cured DPADPE. The cured DPADPE and DADPE demonstrate good thermal and thermo-oxidative stability.

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Section: Introductionmentioning

confidence: 99%

Synthesis and thermal cure of diphenyl ethers terminated with acetylene and phenylacetylene

Wang

Zhang

et al. 2006

Polymer International

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Functional polymers and sequential copolymers by phase transfer catalysis, 2. Synthesis and characterization of aromatic poly(ether‐sulfone)s containing vinylbenzyl and ethynylbenzyl chain ends

Percéc¹,

Auman²

1984

Makromol. Chem.

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A simple method for the synthesis of a,w-bis(vinylbenzy1) aromatic poly(ether-su1fone)s (2) and their transformation into a,w-bis(ethynylbemyl) aromatic poly(ether-su1fone)s (4) is presented. This method involves a fast and quantitative Williamson etherification of the a,w-bis(hydroxypheny1)polysulfone with a mixture of p-and rn-chloromethylstyrenes in the presence of tetrabutylammonium hydrogen sulfate as phase transfer catalyst, a subsequent bromination, and then a dehydrobromination with potassium tert-butoxide. The DSC study of the thermal curing of these a,w-bis(vinylbenzy1)polysulfones and a,w-bis(ethynylbenzy1)polysulfones demonstrates high thermal reactivity for this new class of styrene-terminated oligomers. a) Part I , cf."). b, Publication delayed upon author's request. *) 5-Norbornene-2,3-dicarboximido.

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Functional polymers and sequential copolymers by phase transfer catalysis, 3. Syntheses and characterization of aromatic poly(ether sulfone)s and poly(oxy‐2,6‐dimethyl‐1,4‐phenylene) containing pendant vinyl groups

Percéc

Auman

1984

Makromol. Chem.

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A method for the syntheses of a,w-dibenzyl aromatic poly(ether su1fone)s (PSU) and poly(oxy-2,6-dimethyl-l,4-phenylene) (POP) containing pendant vinyl groups is presented. The first step of the synthetic procedure involves the chloromethylation of PSU and POP to provide polymers with chloromethyl groups. POP, containing bromomethyl groups, was obtained by radical bromination of the methyl groups. Both chloromethylated and bromomethylated starting materials were transformed into their phosphonium salts, and then subjected to a phase transfer catalyzed Wittig reaction to provide polymers with pendant vinyl groups. A PSU, containing pendant ethynyl groups, was prepared by bromination of the PSU, containing pendant vinyl groups, followed by a phase transfer catalyzed dehydrobromination. Differential scanning calorimetry of the thermal curing of the polymers containing pendant vinyl and ethynyl groups showed that the curing reaction is much faster for the polymers containing vinyl groups. The resulting network polymers are flexible when the starting polymer contains pendant vinyl groups, and very rigid when it contains pendant ethynyl groups. Scheme I : 1 3 4 TBAH. IH,CICH~I,IBHSO: Functional polymers and sequential copolymers by phase transfer catalysis, 3 2321An aromatic PSU containing pendant ethynyl groups was prepared by bromination of the vinyl groups of a PSU sample, followed by dehydrobromination with NaOH in the presence of tetrabutylammonium hydrogen sulfate (TBAH) as phase transfer catalyst (Scheme 1 ) . Scheme 2:The thermal curing of both PSU and POP containing pendant vinyl and ethynyl groups was studied by DSC, and demonstrated a very high thermal reactivity for this new class of thermally reactive polymers. Experimental partMaterials: Bisphenol-A (BPA) (4,4 '4sopropylidenediphenol) (from Aldrich) was recrystallized from aqueous methanol. 4,4'-Dichlorodiphenyl sulfone (DCPS) (from Aldrich) was recrystallized twice from toluene. Tetrabutylammonium hydrogen sulfate (TBAH), benzylchloride, 1,1,2,2-tetrachloroethane (TCE), triphenylphosphine (PPh, ), 1,4-dioxane, toluene, bromine, potassium tert-butoxide (K-t-Bu), formaldehyde (37 wt.-% aqueous solution) (all from Aldrich) were used as received.

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Aromatic polyethers, polysulfones, and polyketones as laminating resins. V. Polymers containing acetylenic side groups

Cited by 15 publications

References 11 publications

Synthesis and thermal cure of diphenyl ethers terminated with acetylene and phenylacetylene

Synthesis and thermal cure of diphenyl ethers terminated with acetylene and phenylacetylene

Functional polymers and sequential copolymers by phase transfer catalysis, 2. Synthesis and characterization of aromatic poly(ether‐sulfone)s containing vinylbenzyl and ethynylbenzyl chain ends

Functional polymers and sequential copolymers by phase transfer catalysis, 3. Syntheses and characterization of aromatic poly(ether sulfone)s and poly(oxy‐2,6‐dimethyl‐1,4‐phenylene) containing pendant vinyl groups

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