Patent GB-789950-A (GB)
Title: Improvements in or relating to organo-silicon compounds
IPC: C07F7/18
Filed: 1956-05-22
Abstract: Fibres of glass, cotton, wool, nylon, rayon and polyacrylonitrile are treated, e.g. for sizing, with an aqueous solution of a silane of the general formula: RnSi(OCHR11CH2NR12.HY)4-n or a partial condensate thereof, in which at least one of the R groups is a hydrocarbonoxy, other than alkoxy, radical attached to the silicon through at least one oxygen atom, the remainder being hydrocarbon or alkoxy radicals or hydrogen, n is from 1 to 3, R11 is hydrogen or methyl, R1 is a hydrocarbon radical containing less than 11 carbon atoms or hydrogen or a hydroxyalkyl radical containing 2 or 3 carbon atoms, and Y is chlorine or an acyloxy radical containing less than 4 carbon atoms (see Group IV (a)).  The compounds may be monomeric or polymeric silanes or polysiloxanes.  Concentrations of 0.05 to 1 per cent are generally employed.  The solutions may be stabilized by a weak acid, e.g. acetic acid, to a pH of about 4-6.ALSO:Glass and other surfaces such as masonry, paper, wood, metal and organic plastics, may be coated with a silane of the general formula: RnSi(OCHR11CH2NR12.HY)4-n or a partial condensate thereof, in which at least one of the R groups is a hydrocarboxy, other than alkoxy, radical attached to the silicon through at least one oxygen atom, the remainder being hydrocarbon or alkoxy radicals or hydrogen, n is from 1 to 3, R11 is hydrogen or methyl, R1 is a hydrocarbon radical containing less than, 11 carbon atoms, or hydrogen, or a hydroxy alkyl radical containing 2 or 3 carbon atoms, and Y is chlorine or an acyloxy radical containing less than 4 carbon atoms, (see Group IV (a)).  The compounds, which may be monomeric or polymeric silanes or polysiloxanes, may be applied undiluted or in organic solvents, but are generally in the form of aqueous solutions. Concentrations of 1 to 10 per cent for masonry and 0.05 to 1 per cent for glass are employed.  The aqueous solutions may be stabilized by a weak acid, e.g. acetic, to a pH of about 4 to 6. In an example, glass is lubricated by applying an aqueous solution of a product containing 1 stearyl group and an average of 1.4 OCH2CH2NEt.HCl groups per Si atom, the remaining valencies being attached to polyethylene oxide residues.  Labels coated with a water base glue could be readily adhered to the treated glass.ALSO:The invention comprises silanes of the general formula RnSi(OCHR11CH2NR12.HY)4-n, and partial condensates thereof, in which at least one of the R groups is a hydrocarbonoxy, other than alkoxy, radical attached to the silicon through at least one oxygen atom, the remainder being hydrocarbon or alkoxy radicals or hydrogen, n is from 1 to 3, R11 is hydrogen or methyl, R1 is a hydrocarbon radical containing less than 11 carbon atoms, or hydrogen, or a hydroxyalkyl radical containing 2 or 3 carbon atoms, and Y is chlorine or an acyloxy radical containing less than 4 carbon atoms.  The compounds can be monomeric or polymeric silanes or polysiloxanes.  The polymeric silanes are formed when some of the R groups are derived from polyhydric alcohols.  The compounds are best prepared by reacting silanes of the formula RnSiY4-n with amines of the formula R12NCH2CHR11OH.  A solvent such as benzene, toluene, petroleum ether, methylene chloride or tert.-butanol, may be present.  The condensates may be prepared by partially hydrolysing the silanes or by reacting the amino alcohols with halo- or acyloxy-siloxanes.  The hydrocarbonoxy radicals (other than alkoxy) may be alkenyloxy; aryloxy; hydroxylated radicals such as hydroxyalkoxy and glyceryl; radicals of the formula O(CH2)xOA, where A is a hydrocarbon radical such as a lower alkyl; radicals of the formula -OB, where B is a polyalkylene oxide residue such as (CH2CH2O)xH, (CH(CH3)CH2O)xH, (CH2CH2-O)xCH3 and (CH2CH2O)xC2H5\t and (CH2CH2O)x.  The remaining groups in the compounds may be the same as in the parent Specification.  The compounds are useful for rendering surfaces water-repellent and for sizing glass and other fibres.  They may be applied per se or in aqueous or organic solution in concentrations of up to 10 per cent.  Aqueous solutions may be stabilized by adding about 0.2 per cent of a weak acid, e.g. acetic, to a pH of about 4-6.  In the examples: (1) C17H35SiCl3 is heated with a polyethylene oxide glycol having an average molecular weight of 600 and the product is reacted with diethylethanolamine in tert.-butanol.  The final product has 1 stearyl group and an average of 1.4 OCH2CH2NEt2.HCl groups per Si atom, the remaining valencies being attached to the polyethylene oxide residue.  (2) A monomethyl ether of a polyethylene oxide glycol is reacted with C17H35SiCl3\t and the reaction continued as in (1) to give <FORM:0789950/IV (a)/1> (3) The reaction product of resorcinol, allyl trichlorosilane and vinyl trichlorosilane was added to dimethylethanolamine in methylene chloride to give a mixture of substances in which one allyl or one vinyl group was attached to each Si atom, the remaining valencies of which were satisfied by resorcinoxy and (OCH2CH2NMe2.HCl) radicals.