Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing
Patent
1992-09-02
1994-07-12
Dean, Ralph H.
Organic compounds -- part of the class 532-570 series
Organic compounds
Silicon containing
528 32, C08F 708
Patent
active
053290364
ABSTRACT:
Novel acetylene-terminated silicone monomers with (a) silane (Si--H) functionalities, (b) silanol (Si--OH) functionalities, or (c) (alpha,omega)phenylethynyl terminated siloxanes, and a novel synthetic route. The (alpha,omega)phenylethynyl-terminated siloxane monomers are prepared, starting with 1,3-bromobenzene, which is converted to 3-TMS-ethynylbromobenzene, where TMS represents the trimethylsilyl group, by reacting 1,3-dibromobenzene with trimethylsilylacetylene and triethylamine in the presence of a palladium catalyst. The 3-bromo-TMS protected phenyl acetylene is then reacted with an alkyllithium compound, such as n-butyllithium, or with magnesium to form the corresponding lithio or Grignard compound, respectively, followed by reaction with a halogenated compound, such as chlorodimethylsilane, to form 3-trimethylsilyl-ethynylphenyldimethyl silane. Next, the TMS protected ethynylphenyl silane is subjected to deprotection and methanolysis of the Si--H bond to form 3-ethynylphenyldimethyl methoxy silane, employing methanol. This silane is then hydrolyzed to form the corresponding silanol. Finally, the silanol is then condensed by known methods to form the disiloxane. The disiloxane monomer can be reacted with a cyclic siloxane, having .gtoreq.3 silicon atoms, each independently substituted with hydrogen, C.sub.1 to C.sub.6 alkyl, phenyl, or phenyl substituted with one or more alkyl or halogen groups, to form oligomers. Both monomers and oligomers form thermoset polymers by heating to a temperature of at least about 250.degree. C.
REFERENCES:
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Mantecon et al "Diethynyl terminated siloxane bases" (bisazomethine schiff base), Polymer Bulletin, vol. 23, 1990, pp. 439-445.
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Y. Nagase et al, "Chemical Modification of Poly(substitued-acetylene). I. Syntheis and Gas Permeability of Poly(1-trimethylsilyl-1-propyne)/Poly(dimethylsiloxane) Graft Copolymer", in Journal of Polymer Science, Part B: Polymer Physics, vol. 29, pp. 171-179 (1991).
Dougherty Thomas K.
Elias William E.
Dean Ralph H.
Denson-Low W. K.
Hughes Aircraft Company
Lachman M. E.
Sales M. W.
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