Patent GB-1382090-A (GB)
Title: Silyl-substituted urea derivatives and a process for their preparation
IPC: C07F7/18
Filed: 1972-11-06
Abstract: 1382090 Silyl-substituted urea derivatives BAYER AG 6 Nov 1972 [6 Nov 1971] 50998/72 Headings C3R C3T and C3P  A silyl-substituted urea derivative of the Formula (I) in which R represents an alkyl, cycloalkyl, phenyl or benzyl radical, R<SP>1</SP> represents an alkyl, cycloalkyl or aryl radical which may be halogenated or cyano-substituted, B<SP>11</SP> represents a hydrogen atom or a methyl or phenyl radical, R<SP>111</SP> represents a hydrogen atom or R<SP>1</SP> radical, Q<SP>1</SP> represents an alkyl, cycloalkyl, arylalkyl aryl or alkyl-aryl radical of valency (b + 1), Q represents a c valent radical obtained by the removal of cHX groups from a compound, preferably with a molecular weight of 200-150,000, containing ester, amide, urethane, thioester, acetal, urea, hydroazodicarbonamide, hydrazide and/or carbonate groups and may also contain additional ether groups; a=0, 1 or 2; b=1 to 7; c=1-8; X represents O, S, -NH or -NY where Y represents an alkyl, cycloalkyl or phenyl radical. The derivatives are prepared by reacting an aminoalkyl silane derivative of the formula with an isocyanate-containing compound of the formula preferably at -20-150 C in the presence of a solvent. The isocyanate-containing compound may be obtained by reacting a polyisocyanate of the formula Q<SP>1</SP>(NCO) b+1  with a compound of the formula (HX) c Q. Preferred compounds (HX) c Q are polyaddition products of a polyisocyanate with polyesters containing at least 2-OH groups, polyethers, polythioethers or with polycarbonates containing at least 2-OH groups. The reaction may be carried out in the presence of chain lengthening diamines. The solvent preferably consists at least partially of secondary or tertiary alcohols, halogenated hydrocarbons or acid amides to prevent premature gelling, cross-linking or sedimentation of the reaction product. The derivatives of Formula (I) can be cross-linked with the formtion of polysiloxane bonds on exposure to atmospheric moisture. Acid anhydrides, acids or compounds which split off acids can be added to the resulting solution of the derivative (I) to enhance the stabilizing effect of the above solvents during storage and to activate the cross-linking. In Example 1, a polyesterpolyurethane-polyurea with triethoxysilane urea end groups which is cross-linked on exposure to moisture is prepared by reacting a polyester of adipic acid and ethylene glycol with 1-isocyanato - 3,3,5 - trimethyl - 5 - isocyanatomethyl-cyclohexane and reacting the resulting NCO-terminated prepolymer in a toluene/t.- butanol solvent mixture with isophorone diamine and then with N-cyclohexyl (aminomethyl) triethoxy silane. In Example 2, the polyester of Example 1 is replaced with polypropylene glycol polyether. In Example 3, the diisocyanate of Example (1) is replaced by others such as (a) hexamethylene diisocyanates, (b) m-xylylene diisocyanate; (c) trimethyl hexamethylene diisocyanate; (d) a mixture of hexamethylene diisocyanate and the diisocyanate of Example 1: (e) an isocyanate telomer of hexamethylene diisocyanate and vinyl acetate. In Example 4, the polyester of Example (1) is replaced by (a) a polyester of adipic acid and butane-1,4-diol; (b) a polyester of adipic acid, hexanediol and neopentyl glycol; (c) a polythioether of thiodiglycol and triethylene glycol; (d) polybutylene glycol polyether. In Example 6, the NCO-terminated prepolymer of Example 1 is reacted with further diisocyanate before the subsequent reaction with isophorone diamine and the ethoxy silane. Excess ethoxy silane is added as a chain cross-linker, and acetic acid anhydride is added as stabilizer. In Example 6, a polyurethane foam is soaked in the polyurethanepolyurea of Example 1, and dried to produce a light stable, non-sticky soft, open-celled, elastic foam. In Example 7, the following toluene solutions of polyisocyanates are reacted with N-cyclohexyl-(aminomethyl)triethoxysilane; (a) a copolymer of styrene, butyl acrylate and beta-isocyanatoethyl methacrylate; (b) a telomer of the polyisocyanate of the formula C 2 H 5 -C-(CH 2 OCONH-R-NCO) 3  in which R represents and 30% wt. of grafted polystyrene segments; (c) an α-#-diisocyanato prepolymer of hexamethylene diisocyanate and propylene glycol polyether which has been grafted with vinyl acetate. In Example 9, the ethoxy-silane of example 1 is replaced by (a) Solutions of any of the polymers in Examples 1-9 undergo cross-linking in the presence of moisture to form films. In Example 10, the polyester polyurethane polyurea of Example 1 is condensed with the polyether-poly-urethane polyurea of Example 2 to form homogeneous films.