Patent GB-619536-A (GB)
Title: Manufacture and application of new textile treatment agents
IPC: D06M15/423
Filed: 1946-08-14
Abstract: Compounds R(OCONH-CH2-OR1)3, wherein R is an aliphatic radicle, substituted or not, and R1 is hydrogen or an alkyl radicle are prepared from triscarbamates R(OCONH2)3 either by treatment with formaldehyde or a polymer thereof optionally in the presence of an inert solvent under alkaline conditions to obtain compounds in which R1 is hydrogen or under acid conditions in the presence of an aliphatic alcohol to obtain compounds in which R1 is alkyl.  The compounds may also be obtained on treating the halogeno-methyl derivatives of the triscarbamates, obtained by treatment of the latter with formaldehyde and a hydrogen halide, with an aliphatic alcohol or from the hydroxy-methyl derivatives of the triscarbamates on treatment with an aliphatic alcohol under acid conditions. Slightly elevated temperatures, e.g. 40-60 DEG  C., are preferred for the above processes.  Triscarbamates, e.g. triolein - 11 : 111 : 1111 - triol and tristearin - 11 : 111 : 1111-triol triscarbamates, are prepared by treating a compound R(OH)3, e.g. glycerol, or derivatives thereof, e.g. castor and hydrogenated castor oils, with phosgene and ammonia.  Alcohols specified are methyl, ethyl, propyl and n-butyl alcohols, glycol and glycollic acid.  The compounds are soluble or dispersible in water with e.g. the condensation product of cetyl alcohol with 17 molecular proportions of ethylene oxide, and soluble in such organic solvents as alcohols, acetone, benzene, toluene, chloroform, ethylene dichloride and dioxan. Heated above 100 DEG  C. under acid conditions water-insoluble resins are formed.  Textile materials of animal or vegetable origin or composed of regenerated cellulose or of cellulose esters or ethers are rendered shrink-resistant on impregnation with a solution or dispersion of the compound or compounds in water or an organic solvent followed by drying and heat treatment under acid conditions obtained directly by acids or from salts of bases which liberate acids on heating, e.g. pyridine hydrochloride or hydrobromide or decomposable quaternary compounds, e.g. cetoxy- and stearamido-methylpyridinium chloride. Other textile agents such as polyvalent metal salts, e.g. aluminium acetate may be added to the impregnating fluid (see Group VIII) and when condensation products of formaldehyde with phenols or urea or urea derivatives are added the textiles become crease - resistant. In examples, the triscarbamate of (1) hydrogenated castor oil, essentially tristearin-11 : 111 : 1111-triol triscarbamate, and (2) castor oil, essentially triolein-11 : 111 : 1111-triol triscarbamate, are converted to their methylol derivatives by treatment in benzene solution with paraformaldehyde and anhydrous potassium carbonate and the product of (1) is ethylated in (5) with ethanol and hydrogen chloride and methylated in (8) with methanol and hydrogen chloride, in (6) and (7) the chloromethyl derivatives of the triscarbamate of castor oil, obtained by the action of formaldehyde and hydrogen chloride on the triscarbamate, are treated with n-butyl and ethyl alcohols respectively to give the corresponding ethers, and in (3) and (4) wool flannel is rendered shrink resistant by treatment with an aqueous hydrochloric acid dispersion containing the condensation product of cetyl alcohol with 17 molecular proportions of ethylene oxide together with the products of (1) and (2) respectively followed by drying and baking.ALSO:Compounds R (OCONHCH2OR1)3, wherein R is an aliphatic radicle, substituted or not, and R1 is hydrogen or an alkyl radicle are prepared from triscarbamates R(OCONH2)3 either by treatment with formaldehyde or a polymer thereof optionally in the presence of an inert solvent under alkaline conditions to obtain compounds in which R1 is hydrogen or under acid conditions in the presence of an aliphatic alcohol to obtain compounds in which R1 is alkyl.  The compounds may also be obtained on treating the halogeno-methyl derivatives of the triscarbamates, obtained by treatment of the latter with formaldehyde and a hydrogen halide, with an aliphatic alcohol or from the hydroxy-methyl derivatives of the triscarbamates on treatment with an aliphatic alcohol under acid conditions.  Slightly elevated temperates, e.g. 40-60 DEG  C. are preferred for the above processes.  Triscarbamates, e.g. triolein-11 : 111 : 1111-triol and t tristearin-11 : 111 : 1111-triol triscarbamates are prepared by treating a compound R(OH)3, e.g. glycerol, or derivatives thereof, e.g. castor and hydrogenated castor oils, with phosgene and ammonia.  Alcohols specified are methyl, ethyl, propyl and n-butyl alcohols, glycol and glycollic acid.  The compounds are soluble or dispersible in water with e.g. the condensation product of cetyl alcohol with 17 molecular proportions of ethylene oxide, and soluble in such organic solvents as alcohols, acetone, benzene, toluene, chloroform, ethylene dichloride and dioxan. Heated above 100 DEG  C. under acid conditions water-insoluble resins are formed.  Textile materials of animal or vegetable origin or composed of regenerated cellulose or of cellulose esters or ethers are rendered shrink-resistant on impregnation with a solution or dispersion of the compound or compounds in water or an organic solvent followed by drying and heat treatment under acid conditions obtained directly by acids or from salts of bases which liberate acids on heating, e.g. pyridine hydrochloride or hydrobromide or decomposable quaternary compounds, e.g. cetoxy- and stearamido-methyl-pyridinium chloride.  Other textile agents such as polyvalent metal salts, e.g. aluminium acetate may be added to the impregnating fluid (see Group VIII) and when condensation products of formaldehyde with phenols or urea or urea derivatives are added the textiles become crease-resistant.  In examples, the triscarbamate of (1) hydrogenated castor oil, essentially tristearin-11 : 111 : 1111-triol triscarbamate and (2) castor oil, essentially triolein-11 : 111 : 1111-triol triscarbamate, are converted to their methylol derivatives by treatment in benzene solution with paraformaldehyde and anhydrous potassium carbonate and the product of (1) is ethylated in (5) with ethanol and hydrogen chloride and methylated in (8) with methanol and hydrogen chloride, in (6) and (7) the chloromethyl derivatives of the triscarbamate of castor oil, obtained by the action of formaldehyde and hydrogen chloride on the triscarbamate, are treated with n-butyl and ethyl alcohols respectively to give the corresponding ethers, and in (3) and (4) wool flannel is rendered shrink resistant by treatment with an aqueous hydrochloric acid dispersion containing the condensation product of cetyl alcohol with 17 molecular proportions of ethylene oxide together with the products of (1) and (2) respectively followed by drying and baking.ALSO:Compounds R(OCONH CH2 OR1)3, wherein R is an aliphatic radicle, substituted or not, and R1 is hydrogen or an alkyl radicle are prepared from triscarbamates R(OCONH2)3 either by treatment with formaldehyde or a polymer thereof optionally in the presence of an inert solvent under alkaline conditions to obtain compounds in which R1 is hydrogen or under acid conditions in the presence of an aliphatic alcohol to obtain compounds in which R1 is alkyl.  The compounds may also be obtained on treating the halogeno-methyl derivatives of the triscarbamates, obtained by treatment of the latter with formaldehyde and a hydrogen halide, with an aliphatic alcohol or from the hydroxy-methyl derivatives of the triscarbamates on treatment with an aliphatic alcohol under acid conditions. Slightly elevated temperatures, e.g. 40-60 DEG  C. are preferred for the above processes.  Triscarbamates, e.g. triolein - 11 : 111 : 1111 - triol and tristearin - 11 : 111 : 1111-triol triscarbamates are prepared by treating a compound R(OH)3, e.g. glycerol, or derivatives thereof, e.g. castor and hydrogenated castor oils, with phosgene and ammonia.  Alcohols specified are methyl, ethyl, propyl and n-butyl alcohols, glycol and glycollic acid.  The compounds are soluble or dispersible in water with e.g. the condensation product of cetyl alcohol with 17 molecular proportions of ethylene oxide, and soluble in such organic solvents as alcohols, acetone, benzene, toluene, chloroform, ethylene dichloride and dioxan. Heated above 100 DEG  C. under acid conditions water-insoluble resins are formed.  Textile materials of animal or vegetable origin or composed of regenerated cellulose or of cellulose esters or ethers are rendered shrink-resistant on impregnation with a solution or dispersion of the compound or compounds in water or an organic solvent followed by drying and heat treatment under acid conditions obtained directly by acids or from salts of bases which liberate acids on heating, e.g. pyridine hydrochloride or hydrobromide or decomposable quaternary compounds, e.g. cetoxy- and stearamido-methylpyridinium chloride. Other textile agents such as polyvalent metal salts, e.g. aluminium acetate may +  be added to the impregnating fluid (see Group VIII) and when condensation products of formaldehyde with phenols or urea or urea derivatives are added the textiles become crease - resistant. In examples the triscarbamate of (1) hydrogenated castor oil, essentially tristearin-11 : 111 : 1111-triol triscarbamate, and (2) castor oil, essentially triolein-11 : 111 : 1111-triol triscarbamate, are converted to their methylol derivatives by treatment in benzene solution with paraformaldehyde and anhydrous potassium carbonate and the product of (1) is ethylated in (5) with ethanol and hydrogen chloride and methylated in (8) with methanol and hydrogen chloride, in (6) and (7) the chloromethyl derivatives of the triscarbamate of castor oil, obtained by the action of formaldehyde and hydrogen chloride on the triscarbamate, are treated with n-butyl and ethyl alcohols respectively to give the co