(alpha, omega)phenylethynyl siloxane monomers, oligomers, and polymers thereof
US5329036A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Sep 2, 1992 |
| Grant date | Jul 12, 1994 |
| Priority date | — |
| Expiry date | Sep 2, 2012 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC08G77/455
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
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 disilox…
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