Patent GB-872138-A (GB)
Title: Improvements in or relating to substituted organosilicon compounds
IPC: C08G77/00
Filed: 1959-07-30
Abstract: The invention comprises polyaminoalkyl substituted organosilicon compounds which can be made by intimately mixing with water (1) at least one silane of the formula R11 (ZnR1)Si(OR)2, with or without (2) at least one silane of the formula R111ySi(OR)4-y, where each R is preferably an alkyl radical of 1-3 C atoms, R1 is an aliphatic hydro-carbon radical of 1 or more than 2 C atoms and having a valency of n+1 where n is 1, 2 or 3, Z is a monovalent radical attached to R1 by a carbon-nitrogen bond and is composed of C, N and H atoms in which all the N atoms are present as amino groups and which contains at least 2 amino groups, the ratio of C atoms to N atoms in the group -R1Zn being less than 6 : 1, R11 is a monovalent hydrocarbon radical free from aliphatic unsaturation, y is 0, 1, 2 or 3 and R111 is a monovalent saturated or unsaturated hydrocarbon or halogenated aryl radical, the amount of any silane (2) present in which y is 2 being less than 50 molar per cent of the total silanes.  The amount of water used with silanes (1) and (2) is at least equivalent to 50 molar per cent of the total OR groups present.  Water-miscible organic solvents, e.g. lower aliphatic alcohols, dioxane, and tetrahydrofuran are incorporated in the silanes and/or in the hydrolysis water, particularly when the content of silane (2) is sufficiently high to form insoluble hydrolysates.  The hydrolysis is best effected by heating the mixture of silanes (1) and (2) to at least 50 DEG C. while the water is being added thereto in increments. The reaction products are mixtures of siloxanes, silanols, unreacted silanes and compounds containing siloxane linkages, ­SiOH groups and -OR radicals, and are often used as solutions in water.  When the aqueous reaction product is exposed to air and dried, or distilled free from alcohol and water or otherwise completely hydrolysed and condensed, the products are polymers or copolymers composed of siloxane units derived from the above silanes.  Salts are obtained by contacting the products with any acid.  In a typical Example (1) (MeO)2MeSi (CH2)3NH,CH2,CH2NH2 was mixed with water at room temperature to give a solution which, when freed of water, yielded a liquid containing the disiloxane diol <FORM:0872138/IV (a)/1> and a small amount of a polyaminoalkylmethylsiloxane polymer.  Uses: To improve the wettability of and adhesion of resins and dyes to glass; as intermediates for modified resins; and as curing agents for epoxy resins.  The polyaminoalkylsilanes can be made by reacting a polyamine, e.g. ethylenediamine, diethylenetriamine, 1, 6-hexanediamine, 3-aminoethyl-1, 6-diaminohexane, N, N1-dimethylhexamethylenediamine, cadaverine, piperazine, di-1, 2-propanediamine, methylhydrazine, 1-aminoguanidine, 2-pyrazoline, benzenetriamine, benzenepentamine, benzylhydrazine, N-methyl-p-phenylenediamine, N, N1-dimethyl-p-phenylenediamine and 3-o-tolylenediamine, with a halohydrocarbon-substituted hydrocarbon dialkoxysilane, where each halogen atom is on a C atom which is either a  to the Si atom or as far removed as the g  position, under anhydrous conditions at 50 DEG -200 DEG C., using a molar excess of the polyamine. The halohydrocarbon silanes can be made (1) by reacting the corresponding aliphatic hydrocarbon containing at least one unsaturated linkage with R11SiCl2 in the presence of a Pt catalyst, with subsequent alkoxylation of the reaction product, or (2) by halogenating CH3Si Cl3 to form, e.g. Cl,CH2SiCl3 or BrCH2SiCl3, and reacting the product with the appropriate Grignard reagent to produce Cl,CH2,R11SiCl2 and alkoxylating the resulting silane to yield the desired silane.