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    • 9. 发明授权
    • (alpha, omega)phenylethynyl siloxane monomers, oligomers, and polymers
thereof
    • (α,ω)苯乙炔基硅氧烷单体,低聚物及其聚合物
    • US5329036A
    • 1994-07-12
    • US939326
    • 1992-09-02
    • Thomas K. DoughertyWilliam E. Elias
    • Thomas K. DoughertyWilliam E. Elias
    • C07F7/08C07F7/18C08F38/00C08F290/00C08F299/08C08G77/04C08G77/20C08G77/22C08G77/455C08F7/08
    • C07F7/0896C07F7/0836C07F7/0847C07F7/1844C08G77/045C08G77/20C08G77/455
    • 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.
    • 具有(a)硅烷(Si-H)官能团,(b)硅烷醇(Si-OH)官能团或(c)(α,ω))苯基乙炔基封端的硅氧烷的新型乙炔封端的有机硅单体和新的合成路线。 制备(α,ω)苯基乙炔基封端的硅氧烷单体,通过1,3-二溴苯与三甲基甲硅烷基乙炔和三乙胺反应,由1,3-溴苯转化成3-TMS-乙炔基溴苯,其中TMS代表三甲基甲硅烷基 在钯催化剂存在下。 然后将3-溴-TT保护的苯基乙炔与烷基锂化合物如正丁基锂或与镁反应,分别形成相应的锂或格利雅化合物,随后与卤代化合物如氯二甲基硅烷反应, 形成3-三甲基甲硅烷基 - 乙炔基苯基二甲基硅烷。 接着,使用甲醇对TMS保护的乙炔基苯基硅烷进行Si-H键的去保护和甲醇分解以形成3-乙炔基苯基二甲基甲氧基硅烷。 然后将该硅烷水解形成相应的硅烷醇。 最后,通过已知的方法使硅烷醇缩合形成二硅氧烷。 二硅氧烷单体可与具有大于或等于3个硅原子的环状硅氧烷,各自独立地被氢取代,C1至C6烷基,苯基或被一个或多个烷基或卤素基团取代的苯基,以形成低聚物。 单体和低聚物通过加热至至少约250℃的温度形成热固性聚合物