Patent GB-686068-A (GB)
Title: Improvements in or relating to organosilylamines
IPC: C07F7/08
Filed: 1951-04-25
Abstract: Catalysts for the setting of organosiloxane resins comprise organo-silicon compounds of the general formula (R3SiCH2)aNR1bH3-a-b wherein a is 1 or 2, b is 0, 1 or 2, the sum of a and b being not greater than 3, R is an alkyl, monocyclic aryl hydrocarbon or alkoxy radical, and R1 is an alkyl, alicyclic hydrocarbon or monocyclic aryl hydrocarbon radical or a hydroxyalkyl radical in which the OH group is at least beta to the nitrogen atom, and salts derived from the above organo-silicon compounds and having the general formula <FORM:0686068/IV (a)/1> wherein a is 1 or 2, b1 is 0, 1, 2 or 3, the sum of a and b1 being not greater than 4, Y is an acid anion, and R and R1 have the significance indicated above.  The organo-silicon compounds of both the above general formul  are used as intermediates in the production of organo-silicon resins.ALSO:The invention comprises organo-silicon compounds of the general formula (R3SiCH2)aNR1bH3-a-b wherein a is 1 or 2, b has a value from 0 to 2 (the sum of a+b being not greater than 3), R is an alkyl, monocyclic aryl hydrocarbon or alkoxy radical, and R1 is an alkyl, alicyclic hydrocarbon or monocyclic aryl hydrocarbon radical or a hydroxyalkyl radical in which the OH group is at least beta to the nitrogen, salts of the above compounds having the general formula [(R3SiCH2)aNR1b1H4-a-b1] wherein a is 1 or 2, b1 has a value from 0 to 3 (the sum of a and b1 being not greater than 4), Y is an acid anion and R and R1 have the above significance, and a process for preparing the above compounds by heating a compound of the general formula R3SiCH2X with a compound of the general formula R11bNH3-b, where X represents chlorine or bromine, and R11 is an alkyl, alicyclic hydrocarbon, monocyclic aryl hydrocarbon or hydroxyalkyl radical in which the hydroxy substituent has been blocked and is beta to the nitrogen, at a temperature of at least 50 DEG  C. Halomethylsilane reactants referred to are trimethyl-, tripropyl-, triphenyl-, phenylisopropoxymethyl-, octadecoxydimethyl- and triethoxy-chloromethylsilane, and phenyldimethyl- and diethoxymethyl-bromomethylsilane.  Amino reactants referred to are ammonia, methylamine, aniline, cyclohexylamine, isopropylamine, dimethylamine, tolylamines, ethanolamine and gamma-propanolamine.  In the examples, the following compounds are prepared: trimethylsilylamine and its hydrochloride and adipate, bis-(trimethylsilylmethyl) amine and its hydrochloride, dimethylethoxysilylmethylamine, bis - (dimethylethoxysilylmethyl)amine, N-(trimethylsilylmethyl)phenylamine and its hydrochloride, dimethylphenylsilylmethylamine and its hydrochloride, bis-(dimethylphenylsilylmethyl) amine and its hydrochloride, (trimethylsilylmethyl) dimethylamine and its hydrochloride and quaternary salt derived from methyl iodide, N-dimethylethoxysilylmethyl) cyclohexylamine, bis-N-(dimethylethoxysilylmethyl)-cyclohexylamine, N-(trimethylsilylmethyl) cyclohexylamine and its hydrochloride, N-(trimethylsilylmethyl) octadecylamine and its hydrochloride, bis-(trimethylsilylmethyl) octadecylamine, N - (trimethylsilylmethyl) methylamine and its hydrochloride, diethoxymethylsilylamine, bis-(diethoxymethylsilylmethyl) amine, N-(trimethylsilylmethyl) isopropylamine and its hydrochloride N-(trimethylsilylmethyl) beta-hydroxyethylamine and its hydrochloride, triethoxysilylmethylamine and bis-(triethoxysilylmethyl) amine.  The silicon-containing azo dye p-NO2C6H4 NNC6H4NH-CH2Si(CH3)3 is prepared by reacting the diazonium salt of p-nitro-aniline with N-(trimethylsilylmethyl) phenylamine. Chloromethyldimethylphenylsilane is prepared by reacting chloromethyldimethylchlorosilane and phenyl magnesium bromide. Bis-(beta-aminoethoxy) dimethylsilane is prepared by heating at a temperature above the boiling-point of ethyl alcohol dimethyldiethoxysilane and ethanolamine.  Chloromethyltriethoxysilane is prepared by chlorinating methyltrichlorosilane in the presence of light to give chloromethyltrichlorosilane which is then reacted with ethyl alcohol.ALSO:A monazo dye is prepared by coupling the diazonium salt of p-nitro-aniline and N-(trimethylsilylmethyl) phenylamine.ALSO:Emulsifying agents comprise organosilicon compounds of the general formula (R3SiCH2)a NR1b H3-a-b, wherein a is 1 or 2, b is 0, 1 or 2, the sum of a and b being not greater than 3, R is an alkyl, monocyclic aryl hydrocarbon or alkoxy radical, and R1 is an alkyl, alicyclic hydrocarbon or monocyclic hydrocarbon radical or a hydroxyalkyl radical in which the OH group is at least beta to the nitrogen, and salts derived from the above organo-silicon compounds said salts being of the general formula [(R3SiCH2)a NR1b1 H4-a-b1]g , wherein a is 1 or 2, b1 is 0, 1, 2 or 3, the sum of a and b1 being not greater than 4, g  is an acid anion, and R and R1 have the significance indicated above.