Patent GB-956006-A (GB)
Title: Copolymeric compositions
IPC: C08G73/04
Filed: 1960-11-03
Abstract: Poly-1:2-alkylene carbamates of the formula: <FORM:0956006/C2/1> , where R1 is hydrogen or an alkyl radical having from 1 to 4 carbon atoms, n is an integer greater than 1 and R is an n-valent oxa-free residue of a polyhydroxy organic compound from which n hydroxyl groups have been removed are made by reacting a 1:2-alkylene imine with a chlorocarbonate of a polyhydroxy compound.  Specified alkylene imines are ethylene imine, 1:2-propylene imine, 1:2-butylene imine, 1:2-pentylene imine, 1:2-hexylene imine and 1:1-dimethylethylene imine. Specified chlorocarbonates are those of 1:4-butanediol, resorcinol, 1:1-isopropylidene bis(p-cyclohexanol), 1:1-isopropylidene-bis (p-phenol) and 1:4-cyclohexane dimethanol. The Specification describes the preparation of poly-1:2-alkylene carbamates from ethylene imine and the bis-chlorocarbonates of:  (a) 1:4-butanediol and (b) resorcinol.ALSO:A liquid curable composition comprises a polyfunctional amine and a poly-1:2-alkylene carbamate of the formula: <FORM:0956006/C3/1> , where R1 is hydrogen or an alkyl radical having from 1 to 4 carbon atoms, n is an integer greater than 1 and R is an n-valent oxa-free residue of a polyhydroxy organic compound from which n hydroxyl groups have been removed.  Specified amines are polyalkylene polyamines, polyfunctional aliphatic amines derived from low polymers of unsaturated fatty acids, reaction products of polyfunctional amines with polymerized fatty acids and aliphatic, alicyclic and aromatic polyfunctional amines, many being exemplified.  The poly-1:2-alkylene carbamates are made by reacting a 1:2-alkylene imine e.g. ethylene imine, 1:2-propylene imine, 1:2-butylene imine, 1:2-pentylene imine, 1:2-hexylene imine or 1:1-dimethyl ethylene imine with a chlorocarbonate of a polyhydroxy compound e.g. 1:4-butanediol, resorcinol, 1:1-isopropylidene bis (p-cyclohexanol), 1:1-isopropylidene-bis(p-phenol) or 1:4-cyclohexanedimethanol. The preparation of poly-1:2-alkylene carbamates from ethylene imine and the bis-chlorocarbonates of:-[A] 1:4-butanediol and [B] resorcinol is described.  The examples describe the reaction between:-(1) triethylene tetramine and N:N1-bis-1:2-ethylene (1:4-butanediol) carbamate; (2) N:N1-bis-1:2-ethylene (1:1-isopropylidene bis (p-cyclohexanol)) carbamate and a low molecular weight polyamide derived from a polymerized fatty acid; (3) N:N1-bis-1:2-ethylene (1:4-butanediol) carbamate and a low molecular weight polyamide derived from a polymerized fatty acid; (4) m-xylylene diamine and N:N1-bis-1:2-ethylene (1:4-butanediol) carbamate; (5) diaminodiphenylsulphone and N:N1-bis-1:2-ethylene (1:4-butanediol) carbamate; (6) N-(2-aminoethyl) piperazine and N:N1-bis-1:2-ethylene-(1:4-butanediol) carbamate; (7) n-butylamine and N:N1-bis-1:2-ethylene (1:4-butaneiol) carbamate; (8) and (9) aniline and N:N1-) bis-1:2-ethylene (1:4-butanediol) carbamate; (10) n-methylcyclohexylamine and N : N1-bis-1:2-ethylene (1:4-butanediol) carbamate and (11) the N:N1-bis-ethylene carbamate of 1:11-isopropylidene-bis-p-phenol and an aliphatic polyfunctional amine.ALSO:Wood, glass, synthetic resinous and metal surfaces are coated with an interpolymer of a polyfunctional amine and a poly-1 : 2-alkylene carbamate of the formula <FORM:0956006/B1-B2/1> where R1 is hydrogen or an alkyl radical having from 1-4 carbon atoms, n is an integer greater than 1 and n is an n-valent oxa-free residue of a polyhydroxy organic compound from which n hydroxyl groups have been removed.  In the examples: (4) polymethylmethacrylate panels are coated with a mixture of m-xylylene diamine and N : N1-bis-1 : 2-ethylene(1 : 4-butanediol)carbamate; (6) wood panels are coated with a mixture of N-(2-aminoethyl)piperazine and N : N1-bis-1: 2-ethylene(1 : 4-butanediol)carbamate; (7) wood panels are coated with a mixture of n-butylamine and N:N1-bis-1:2-ethylene(1:4-butanediol)carbamate; (8) wood panels are coated with a mixture of aniline and N : N1-bis-1 : 2-ethylene(1 : 4-butanediol)carbamate; and (11) aluminium and glass are coated with a solution in benzene of an aliphatic polyfunctional amine and the N : N1-bis-ethylenecarbamate of 1 : 1-isopropylidene-bis-p-phenol; the coatings being cured by the application of heat.ALSO:In Example 11, cotton cloth is impregnated with a solution in benzene of the N:N1-bisethylene carbamate of 1:11-isopropylidene-bis-phenol and an aliphatic polyfunctional amine and cured by heating at 120 DEG C. to improve the water repellancy of the cloth.