Patent GB-662548-A (GB)
Title: Process for the manufacture of condensation products derived from aminotriazines andmethylolamide compounds
IPC: C07C51/09
Filed: 1949-03-03
Abstract: Textile finishing and proofing agents comprise aminotriazine derivatives made by reacting a methylol compound of an aminotriazine or an ether thereof with a methylol amide compound containing the group -CO-N-CH2OH, and wherein at least one of the two residues to which this group is bound contains at least one carbon atom, the reaction being carried out in an organic solvent and if desired in presence of a condensing agent, and at temperatures of 50-100 DEG C., at which the water and alcoholic compounds formed during the reaction are removed. Condensing agents specified are boric acid or HCl, and toluene, benzene, &c. aromatic hydrocarbons are suitable solvents. Methylol derivatives of melamine, melam, melem, ammeline, ammelide, or halogen substituted aminotriazine and methylol ethers with monohydric alcohols containing not more than 4 carbon atoms are specified.  Methylolamide compounds specified are stearoylamide and amides of ammonia and primary amines or aniline with carboxylic acids such as acetic, chloracetic, butyric, oleic, capric, lauric, behenic, a -bromo-lauric, naphthenic and resinic acids; urethanes, N : N1-diacylated alkylene or arylene diamines.  The textiles &c. are preferably treated with the condensate in the form of a salt of an acid, e.g. salts of acetic or formic acid, water-soluble aluminium or zirconium salts, zirconium dioxide brine, or a dispersion of paraffin wax; hydrotropic substances, e.g. urea or thiourea, may be added.  In examples: (1) 200 parts methylolated hexamethylol melamine and 150 parts benzene are distilled under reflux with separation of water and return of benzene to the reaction vessel; 162 parts stearic acid N-methylolamide are added and the bath heated to 80-85 DEG  C. at 510 mm. pressure for 4 hours with removal of 10 parts water.  The distillation is continued under reduced pressure until the mass sets. 180 parts of the product are melted and dissolved in 72 parts water and further diluted with 108 parts water, whereupon on addition of formic acid an opalescent solution is obtained.  Wool is impregnated with the solution containing monochloracetic acid, squeezed, dried and heated to 80 DEG  C. for 2 hours.  The wool has a soft feel and shrinks less on washing.  Cotton is rendered water-repellent by similar treatment. Samples furnished describe similar condensation products obtained from methoxy methylol melamines and (1) octadecyl-methylol urethane; (2) coconut fatty acid-N-methylol amide.ALSO:Textile finishing and proofing agents comprise amino-triazine derivatives made by reacting a methylol compound of an aminotriazine or an ether thereof with a methylol amide compound containing the group -CO-N-CH2OH, and wherein at least one of the two residues to which this group is bound contains at least one carbon atom, the reaction being carried out in an organic solvent and if desired in presence of a condensing agent, and at temperatures of 50-100 DEG  C., at which the water and alcoholic compounds formed during the reaction are removed. Condensing agents specified are boric acid or HCl and toluene, benzene &c. aromatic hydrocarbons are suitable solvents.  Methylol derivatives of melamine, melam, melem, ammeline, ammelide, or halogen-substituted aminotriazines and methylol ethers with monohydric alcohols containing not more than 4 C atoms are specified.  Methylolamide compounds specified are stearoylamide and amides of ammonia and primary amines or aniline with carboxylic acids such as acetic, chloracetic, butyric, oleic, capric, lauric, behenic, a -bromolauric, naphthenic and resinic acids; urethanes, N : N1-diacylated alkylene or arylene diamines. 200 parts methylolated hexamethylol melamine and 150 parts benzene are distilled under reflux with separation of water and return of benzene to the reaction vessel, 162 parts stearic acid N-methylolamide are added and the bath heated to 80-85 DEG  C. at 510 mm. pressure for 4 hours with removal of 10 parts water. The distillation is continued under reduced pressure until the mass sets. 180 parts of the product are melted and dissolved in 72 parts water and further diluted with 108 parts water, whereupon on addition of formic acid an opalescent solution is obtained. Samples furnished describe similar condensation products obtained from methoxy methylol melamines and (1) octadecyl-methylol urethane, (2) coconut fatty acid-N-methylol amide.ALSO:Textile finishing and shrinkproofing agents comprise amino-triazine derivatives made by reacting a methylol compound of an aminotriazine or an ether thereof with a methylol amide compound containing the group -CO-N-CH2OH and wherein at least one of the two residues to which this group is bound contains at least one carbon atom (see Group IV (b)).  Methylol derivatives of melamine, melam, melem, ammeline, ammelide, or halogen substituted aminotriazines and methylol ethers with monohydric alcohols containing not more than 4 carbon atoms are specified. Methylolamide compounds specified are stearoylamide and amides of ammonia and primary amines or aniline with carboxylic acids such as acetic, chloracetic, butyric, oleic, capric, lauric, behenic, a -bromo-lauric, naphthenic and resinic acids; urethanes, N : N1-diacylated alkylene or arylene diamines.  The textiles are preferably treated with the condensate in the form of a salt of an acid, e.g. salts of acetic or formic acid; water-soluble aluminium or zirconium salts, zirconium dioxide brine, or a dispersion of paraffin wax; hydrotropic substances, e.g. urea or thiourea may be added.  In examples: (1) 200 parts methylolated hexamethylol melamine and 150 parts benzene are distilled under reflux with separation of water and return of benzene to the reaction vessel; 162 parts stearic acid N-methylolamide are added and the bath heated to 80-85 DEG  C. at 510 mm. pressure for 4 hours with removal of 10 parts water.  The distillation is continued under reduced pressure until the mass sets. 180 parts of the product are melted and dissolved in 72 parts water and further diluted with 108 parts water whereupon on addition of formic acid an opalescent solution is obtained.  Wool is impregnated with the solution containing monochloracetic acid, squeezed, dried and heated to 80 DEG  C. for 2 hours.  The wool has a soft feel and shrinks less on washing.  Cotton is rendered water repellent by similar treatment.  Samples furnished describe similar condensation products obtained from methoxy methylol melamines and (1) octadecyl-methylol urethane; (2) coconut fatty acid-N-methylol amide.