Patent GB-858445-A (GB)
Title: Improvements in or relating to silanes
IPC: C07F7/18
Filed: 1958-12-12
Abstract: The invention comprises aminohydrocarbon trialkoxy silanes of the formula (RO)3SiR1Zn, where R is an alkyl group of 1 to 3 carbon atoms, R1 is an aliphatic hydrocarbon radical of one or more than two carbon atoms and a valency of n + 1, n is at least 1, and Z is a monovalent radical containing at least 2 amine groups attached to R1 through a carbon-nitrogen bond and is composed of carbon, hydrogen and nitrogen atoms, all the nitrogen being present as amine groups, the ratio of carbon to nitrogen atoms in R1Zn being less than 6:1. The radical R1 includes any number and combination of <FORM:0858445/IV(a)/1> vinylene and methylene groups which may contain methyl and vinyl groups.  The amine groups may be primary, secondary or tertiary and include imines.  The compounds may be prepared by reacting a polyamine with a halohydrocarbonyl trialkoxy silane where the halogen is on a carbon atom which is alpha or at least gamma to the silicon atom, preferably at temperatures of 50 DEG to 200 DEG C. under anhydrous conditions.  Suitable polyamines are ethylene diamine, diethylene triamine, 1, 6-hexanediamine, 3-aminoethyl-1, 6-diamino-hexane, N, N1-dimethyl hexamethylene diamine, cadaverine, piperazine, di-1, 2-propane diamine, methyl hydrazine, 1-aminoguanidine, 2-pyrazoline, benzene triamine, benzene pentamine, benzyl hydrazine, N-methyl-p-phenylene diamine, N, Ndimethyl-p-phenylene diamine and 3-o-tolylene diamine.  The products are water-soluble and aqueous solutions are used to provide coatings of siloxanes on glass.  The examples describe the preparation of: (1) and (2) (RO) 3SiCH2CH2CH2 NHCH2CH2NH2, where R is Me, Et, n-Pr and i-Pr; (3)(MeO) 3SiCH2CHMECH2NHCH2CH2 NH2, (MeO) 3SiCH = CH CH2NHCH2CH2 NH2, (MeO) 3SiCH2CH = CHCH2CH2NHCH2 CH2NH2, (MeO) <FORM:0858445/IV(a)/2> and (4) and (5) a number of other compounds such as <FORM:0858445/IV(a)/3> and (MeO) 3SiCH2NHC6H4NMe2. Specification 804,097 is referred to.ALSO:Glass cloth is coated with an organosilicon compound and dyed with any direct acid dye such as is employed on wool, the silicon compound having the formula (RO)3SiR1Zn, where R is an alkyl group of 1 to 3 carbon atoms, R1 is an aliphatic hydrocarbon radical of one or more than two carbon atoms and a valency of n+ 1, n is at least 1, and Z is a monovalent radical containing at least 2 amine groups attached to R1 through a carbon-nitrogen bond, the ratio of carbon to nitrogen atoms in R1Zn being less than 6 : 1 (see Group IV(a)).  In examples (6) heat-cleaned glass cloth is immersed in a 0,5% aqueous solution of (MeO)3Si CH2 CH2 CH2 NH CH2 CH2 NH2, air-dried, and dyed (a) by immersing in a 3% aqueous solution of Brilliant Croceine 3BA containing 4% H2SO4 at a temperature of 95 DEG C. for 1 hour, (b) with Nigrosine ESB Cl 865, and (c) with Pontachrome Brown RH; (7) heat-cleaned glass cloth is immersed in a 1% aqueous solution of (MeO)3 Si CH2 CH2 CH2 NH CH2 CH2 NH2, heated at 110 DEG C. for 10 mins. and dyed with aqueous Brilliant Croceine 3BA.ALSO:Glass is coated with an organosilicon compound of the formula (RO)3SiR1Zn, where R is an alkyl group of 1 to 3 carbon atoms, R1 is an aliphatic hydrocarbon radical of one or more than two carbon atoms and a valency of n+1, n is at least 1, and Z is a monovalent radical containing at least 2 amine groups attached to R1 through a carbon-nitrogen bond and is composed of carbon, hydrogen and nitrogen atoms, all the nitrogen being present as amine groups, the ratio of carbon to nitrogen atoms in R1Zn being less than 6:1 (see Group IV(a)). p  The compounds may be applied as solutions in water or organic solvents, by any common method, e.g. dipping or spraying, preferably as 0.1 to 3% aqueous solutions followed by drying advantageously at a raised temperature.  The result is a glass base coated with a hydrolysis product of the silane, providing improved adhesion of organic resins and wettability by organic solvents, and which may be dyed.