Patent GB-778204-A (GB)
Title: Manufacture and use of hardenable ternary condensation products from a compound of the aminotriazine group
IPC: C08G12/40
Filed: 1953-12-23
Abstract: Hardenable ternary condensation products containing COOH or SO3H groups are prepared by reacting one mol. of (a) an aminotriazineformaldehyde condensate or an ether thereof with an alcohol having not more than 4 carbon atoms, with 1-3 mols. of (b) an aliphatic acid, alcohol, mercaptan, partial ester or ether of a polyhydric alcohol, amide, urethane or N-methylol amide or urethane, said aliphatic compound containing a carbon chain of at least 7 carbon atoms, and them reacting the product with 1-2 mols. of (c) an aliphatic monohydroxy- or monomercapto-monocarboxylic or -monosulphonic acid.  Preferred aminotriazine-formaldehyde condensates are methylol melamines or ethers thereof with alcohols such as methyl or butyl alcohol. Other aminotriazines mentioned are melem, melem, ammeline, ammelide, 2 - chloro - 4,6 - diamino - 1,3,5 - triazine, and benzo-, aceto- or formo-guanamine.  As compound (b) above are mentioned, capric, lauric stearic, behenic, oleic, ricinoleic and montanic acid; dodecyl, miricyl, ceryl, oleyl, linoleyl, linolenyl, cetyl and octadecyl alcohol and 2-butyloctanol; dodecyl- and octadecyl-mercaptan, and an ester, e.g. of thioglycollic acid, with a long-chain alcohol; amides from ammonia, methylamine, ethylamine, dodecylamine or octadecylamine and acetic, chloracetic, butyric, capric, lauric, stearic, behenic or oleic acid, dilauric acid amide, and methylene distearic acid amide; octadecyl urethane; a partial ester from glycerol and two mols. of stearic acid; a partial ether from glycerol and two mols. of octadecyl alcohol; N-methylol amides of capric, lauric or oleic acid; N-methylol-dodecyl-, hexadecyl-, or octadecyl-urethane. Suitable acids as component (c) are glycollic acid, oxy-ethane sulphonic acid and thioglycollic acid. Each reaction constituent (a), (b) and (c) may consist of a mixture of two or more appropriate substances.  The reaction between components (a) and (b) may be effected at 50-100 DEG  C. in presence of a condensing agent, e.g. boric or other acid, volatile materials being removed by distillation at reduced pressure or with an entrainer, e.g. benzene or toluene.  The product is preferably reacted with (c) at about 100 DEG  C., if desired in presence of an inert solvent, and under reduced pressure or in an inert atmosphere. The products are wax-like and water-insoluble. Water-soluble salts may be formed with ammonia, alkalies or primary amines.  They may be used for treating textiles, leather or paper for water-repellency, crease and shrink resistance or for softening.  In the examples, condensates are prepared from (1) and (10) methylol melamine methyl ether, N-methylol octadecyl urethane and thioglycollic acid; (2) methylol melamine methyl ether, stearic acid N-methylolamide and thioglycollic acid; (3) an ether-ester from methylated methylol melamine and stearic acid, a stearic acid diglyceride and thioglycollic acid; (4) an ether-ester from methylated methylol melamine and stearic acid; and thioglycollic acid; (5) methylol melamine methyl ether, stearic acid and glycollic acid; (6) methylated methylol melamine, stearic acid diglyceride, N-methylol octadecyl urethane and thioglycollic acid; (7) methylol melamine methyl ether, stearin alcohol and thioglycollic acid; (8) and (9) an ether-ester from methylated methylol melamine and stearic acid, stearic acid diglyceride and thioglycollic acid; (11) an etherester from methylated methylol melamine and stearic acid, and hydroxy ethane sulphonic acid.ALSO:Hardenable ternary condensates (see Group IV(a)) containing COOH or SO3H groups and prepared from (a) an aminotrizine-formaldehyde condensate or ether thereof, (b) an aliphatic acid, alcohol, mercaptan, hydroxy ester, hydroxy ether, amide, urethane, N-methylol amide or N-methylol urethane, said compound containing a carbon chain of at least 7 atoms, and (c) an aliphatic monohydroxy - or monomercapto-monocarboxylic or monosulphonic acid, are used for reducing creasing or shrinking or for softening textiles.  The products are preferably applied in aqueous solution and the dried material heated.  Other materials which may be used with the products include salts, e.g. sodium or aluminium acetate; hydrocarbons, e.g. paraffin wax; solvents, methylolamides and methylolureas.  Products particularly useful for softening are those derived from a methylol melamine ether, an N - methylol urethane of an alcohol with 16-18 carbon atoms, and thioglycollic acid.  Dispersing agents, e.g. the sodium salt of 2 - heptadecyl - N - benzylbenzimidazole disulphonic acid may be added, and such a mixture is used in Example 1 as a softening agent for textile fibres, e.g. viscose artificial silk.  The addition of ammonium chloride to the impregnating liquor gives a soft effect resistant to washing.  In Example 12, viscose artificial silk is treated at 20-30 DEG C. in a bath containing hard water, the disodium salt of N - benzyl - 2 - heptadecyl - benzimidazole disulphonic acid, ammonium chloride and the salt obtained by condensation of methylol melamine methyl ether, N - methylol - octadecylurethane and thioglycollic acid.  The material is dried at 70 DEG C. and heated at 100 DEG C.  It has a soft feel not removed by washing.