Patent GB-1536468-A (GB)
Title: Organosilicon compounds
IPC: C07F7/18
Filed: 1976-02-26
Abstract: 1536468 Unsaturated polysulphide-containing silanes and siloxanes DYNAMIT NOBEL AG 26 Feb 1976 [1 March 1975] 07725/76 Headings C3P C3S and C3T Organosilicone compounds having the general formula wherein R represents an alkyl radical, a cycloalkyl radical, an alkoxy alkyl radical, or a phenyl radical, R<SP>1</SP> represents an optionally branched alkylene radical, a cycloalkylene radical, a phenylene or a benzylene radical, R<SP>11</SP> represents an oxygen or a sulphur atom, R<SP>111</SP> represents a hydrogen atom or a methyl radical, n is 1 or 2 and x is 1 or 2 may be produced by a process which comprises reacting a mercapto compound having the general formula in which R, R<SP>1</SP>, n and x have the same meanings as in Formula 1 with an acrylic compound having the general formula (3) wherein R<SP>1</SP> and R<SP>11</SP> are as defined above and X represents a substituent which is reactable with the mercapto hydrogen of the mercapto compound. Suitable mercapto compounds are γ-mercaptopropyl trimethoxy silane, #-mercaptoethyl triethoxy silane and suitable acrylic compounds are methacrylic, acrylic and thiomethacrylic acid chlorides. These compounds may be reacted in the presence of a solvent e.g. xylene, a tertiary amine, e.g. triethylamine and a polymerization inhibitor, e.g. hydroquinone or di-tert-butylcresol, at a temperature of - 10‹ to +5‹ C. Other suitable mercaptocompounds are #-mercapto butyl or hexyl trimethoxy or triethoxy silanes which may be reacted with the acrylic compounds in the presence of a transesterification catalyst, e.g. a titanium ester and a polymerization inhibitor at a temperature of from 40‹ to 60‹ C. Alternatively compounds of Formula 1 may be produced by a process which comprises reacting a compound of the general formula wherein x, R<SP>II</SP> and R<SP>III</SP> are as previously defined and R<SP>IV</SP> and R<SP>V</SP> independently represents a hydrogen atom or an alkyl radical or represents a divalent radical or a phenylene radical, a is 0, 1, 2, 3 or 4, and R<SP>VI</SP> represents a hydrogen atom or an alkyl group, with an alkoxy hydrogen silane having the general formula (RO) 4-n -SiH n  where R and n are as defined above, in the presence of a platinum compound, e.g. H 2 PtCl 6  as catalyst, a solvent and a polymerization inhibitor. In an example allyl thiomethacrylate is reacted with trimethoxy silane. Organo-silicon compounds of formula 1 or hydrclysates thereof may be used to pretreat resin fillers and reinforcing materials, e.g. glass fibres, asbestos, quartz or metal oxides in order to promote adhesion between the inorganic media and the resin. In an example an organosilicon compound, e.g. α-methacryl thiopropyl trimethoxyl silane in ethanol is used to treat glass fibres which are subsequently used to reinforce an unsaturated polyester resin. The addition of small amounts, e.g. 1% by weight of the organo-silicon compounds to monomers, e.g. vinyl chloride, styrene and methyl methacrylate used to coat metal or glass surfaces promotes adhesion between the surface and the resin coating obtained when the monomer is polymerized.