Patent GB-1001955-A (GB)
Title: Organosilicon compounds
IPC: C08G12/40
Filed: 1963-05-30
Abstract: The invention comprises silanes of the formula <FORM:1001955/C3/1> wherein R1 is a hydrocrabon or halohydrocarbon radical of fewer than 7 C atoms, y is 0, 1, 2 or 3, R11 is an alkyl, acyl, haloalkyl, or haloacyl group of fewer than 5 C atoms, or a group -(CH2CH2O)1 or 2R111 is an alkyl group of fewer than 5 C atoms), R is a divalent hydrocarbon group free of aliphatic unsaturation, and attached to the nitrogen of the urea ring by a non-aromatic C atom, Y is hydrogen or an alkyl group of fewer than 7 C atoms, and Z is a group -CHD.CHD- or -CHD.CHD. CHD-, where D is hydrogen or a lower alkyl group, and the corresponding siloxanes and copolymers thereof, and compositions containing these.  The silanes are prepared by the reaction of silanes R1y(R11O)3- ySi-R-NH-Z-NHY with urea.  The siloxanes and copolymeric siloxanes may be prepared in an analogous manner from diamino siloxanes or by hydrolysis (or cohydrolysis with other silanes or siloxanes) of the silanes. Copolymers containing 2-50% of units of this invention, the remainder being dimethylsiloxane units, are of particular use in water-proofing cotton fabrics.  The copolymers are best used in conjunction with a methyl- and hydrogen-substituted polysiloxane, and a conventional crease-resisting resin.  Suitable creaseresistant resins are aminoplast resins, e.g. ureaformaldehyde, alkyleneurea-formaldehyde triazineformaldehyde, or triazoneformaldehyde, and epoxy resins, e.g. the glycidyl ethers of glycerol, ethylene glycol or diethylene or dipropylene glycol.  These resins may be monomeric or polymeric, and may be mixed with or reacted with the cyclic urea organosilicon compound. In examples are described the preparation of many cyclic urea organolilicon compounds, including <FORM:1001955/C3/2> and <FORM:1001955/C3/3> and <FORM:1001955/C3/4> and <FORM:1001955/C3/5> and copolymers of these with polydimethylsiloxanes. Other examples describe compositions comprising a copolymer of <FORM:1001955/C3/6> and dimethylsiloxane units, and a polydimethylsiloxane, polymethylhydrogensiloxane, polytrifluoropropylmethylsiloxane or polypropylmethylsiloxane, a polyvinyl alcohol emulsifier or tridecyl alcohol ether of ethylene oxide, toluene and tetrachloro-ethylene, emulsified in water with an ethyleneurea-formaldehyde or melamine-formaldehyde resin or diglycidyl ethylene glycol diether, and catalysts.  Other uses: sizing agents for silicous surfaces, coupling and bonding agents in adhesives, coatings and laminates.ALSO:Water-proofing compositions for cellulosic fabrics comprise silanes or siloxanes or copolymers thereof containing pyrimidone or imidazolone rings attached through a hydrocarbon group to silicon (see Div. C3).  The preferred materials are copolymers containing 2-50% of the units of the invention, the remainder being polydimethylsiloxane units.  These are best used in conjunction with a polysiloxane containing hydrogen and methyl groups attached to silicon, and a crease-resistant resin, e.g. urea-formaldehyde, triazine-formaldehyde, etc., or an epoxy resin.  Example 8 describes the preparation and use of an emulsion containing a 60: 40 mixture of a trimethylsilyl-terminated methyl hydrogen polysiloxane, (A), and a copolymer containing 8.3% by weight of units <FORM:1001955/D1-D2/1> (B), and the rest dimethylsiloxane units, together with an ethylene-urea-formaldehyde resin, (C), a polyvinyl alcohol emulsifier, zinc nitrate, dibutyl tin diacetate, zinc octoate, and water.  Examples 9-15 describe variations of this composition, in which A may be a hydroxy-terminated polydimethylsiloxane or polymethyl-trifluoro-propylsiloxane or a trimethylsilyl-terminated polymethylpropylsiloxane, and the percentage of B in the copolymer, and the amount and nature of the crease-resistant resin (C), and the order of mixing is varied. Tables show the effects of these and other materials on water- and creaseresistance of a cotton fabric.  The solutions or emulsions may be applied by dipping, spraying, or padding.