Patent GB-844421-A (GB)
Title: Organosilicon compounds
IPC: C07F9/02
Filed: 1958-09-01
Abstract: The invention comprises organosilicon compounds having at least one organic radical bonded to Si by a Si-C linkage, the organic radical consisting essentially of a divalent hydrocarbon radical, which may contain ether linkages, containing at least one radical (A) of the general formula <FORM:0844421/IV(a)/1> in which each R is a H atom or a monovalent hydrocarbon radical, each X and each Y is a hydroxy group or radical of the formula <FORM:0844421/IV(a)/2> wherein each R1 is H or a halogen atom or a monovalent hydrocarbon radical, m is 0 or 1, each Z is oxygen or sulphur and n is 0, 1 or 2, and at least one of X and Y in any single radical (A) is a P-containing radical, any remaining valencies of Si atoms in the organosilicon compound being satisfied by hydrocarbon or halogeno-hydrocarbon radicals, hydrocarbonoxy or halohydrocarbonoxy radicals, H atoms or O atoms. Many examples of hydrocarbon radicals, which may be saturated, unsaturated or cycloaliphatic or aromatic, halogeno hydrocarbon radicals, and divalent hydrocarbon radicals are given.  The compounds can be made by reacting organosilicon epoxides, as disclosed in Specification 834,326, with a phosphorus-containing compound having at least one acid H atom, e.g. ortho-, poly-, meta-, ultra-, hypo-, chloro- and pyro-phosphoric acids; phosphorous and hypoand pyro-phosphorous acids; phosphinous, phosphonic and phosphinic acids; acid phosphates and mono-organophosphites, and the corresponding thio and thione compounds of phosphorus.  The silicon compounds containing the phosphorus-containing groups may be silanes or compounds containing Si-O-Si bonds, Si-R11-Si bonds, Si-(R11O)x-Si bonds, Si-R11 (OR11)xSi bonds or Si-O(R11O)x-Si bonds, where R11 is a divalent hydrocarbon or halohydrocarbon radical and x is a whole number, and may also contain Si-bonded H atoms and OH groups.  A phosphorus acid containing more than one active acid H can react with more than one epoxide group thereby connecting 2 Si atoms through a linkage such as SiR11OPOR11Si.  The compounds can be stabilized by dilution with water or an alcohol.  In Typical Examples (1) aqueous H3PO4 was added slowly to an acetone solution of <FORM:0844421/IV(a)/3> to give a clear solution of <FORM:0844421/IV(a)/4> which cured on glass in 16 hours at 120 DEG C. to a clear, tough, water-insoluble film; a portion of the product solution was neutralised with NH4OH to give a salt which cured on glass in 10 minutes at 120 DEG C.; (6).  C6H5P(O)(OH)2 was added to hot (140 DEG C.) <FORM:0844421/IV(a)/5> and the mixture maintained at 140 DEG C. for 1 hour, to give a liquid polymer of unit formula: <FORM:0844421/IV(a)/6> and which was found to be a good curing agent for epoxy resins; (7) a diethyleneglycol-diemthyl ether solution of the product of (6) mixed with a butanol-xylene solution of a urea-formaldehyde resin to give a mixture which cured in 1 hour at 130 DEG C. to a tough, clear, flexible film; (8) a solution of the product of (6) was added to two organic solvent solutions of 2,2-bis(4,41-dihydroxyphenyl)-propane epichlorohydrin condensation products, having molecular weights of 900 and 1400; each mixture cured in 1 hour at 150 DEG C. to give clear films.  Uses: the neutral compounds are good lubricants and have good fire resistance; the acid compounds will cure epoxy, urea-aldehyde and melamine-aldehyde resins, are useful as oxidation stabilisers or colour inhibitions in alkyl resins, and are good primers on steel for improving the adhesion of synthetic resins.