Patent GB-586429-A (GB)
Title: Improvements in or relating to the finishing of textiles
IPC: D06M15/423
Filed: 1942-08-06
Abstract: A finishing composition for textiles, e.g. of cotton, linen, wool, viscose, cellulose acetate, rayon and silk, comprises a guanamine of the formula <FORM:0586429/IV/1> in which (a) R is an aliphatic or cyclo-aliphatic group containing at least seven carbon atoms and X, A and B are hydrogen or monovalent aliphatic groups, or (b) in which at least one of A, B and X is a monovalent aliphatic, cyclo-aliphatic or aromatic group and R is hydrogen, an aliphatic, cyclo-aliphatic or aromatic group and A, B, X and R contain a total of at least seven carbon atoms, or a formaldehyde condensation product thereof, and a urea-, thiourea-or melamine - aldehyde resin.  Guanamines specified are octano-, decano-, lauro-, myristo-, palmito-, stearo-, oleo- and linoleo-guanamine and the guanamines obtained by reacting biguanide or substituted biguanides with vegetable and animal oils, e.g. olive, coconut, tea-seed, peanut or hydrogenated cotton-seed oils, the fatty acids thereof or their methyl esters; methyl - isoamyl - acetoguanamine, N - acyl - acetoguanamines, b ,b  - di - n - propyl - propionoguanidine, di-isobutyl-acetoguanamine, n-amyl-n-heptyl-acetoguanamine, di-n-heptyl-aceto-, di-n-octyl-aceto-, ethyl-n-butyl-aceto-, ethyl-isoamyl-aceto-, di-n-butyl-aceto-, di-n-propyl - aceto-, 41 - ethyl - 2 - octanoguanamine, o - carboxy - endomethylene - tetrahydro - benzo - guanamine obtained by condensing cis-endomethylene-3.6-D 4-tetrahydrophthalic acid with biguanide, and the cyclo-aliphatic derivative obtained by condensing biguanide with naphthenic acid or with maleic-tung oil or terpene condensation products; a ,a 1-dichloro-stearo-, 9, 10 - dibromo - stearo -, 10 - bromo - decano - guanamine and alkali metal salts of 10-sulphodecano - guanamine; b  - octadecylamino - propiono-, stearoylamino - aceto-, b  - octadecoxy - propiono-, b -amyloxy-propiono-, glucono-, O -carboxy-, O  - carbomethoxy-, and O  - carbobutoxy - pelargono-, b  - N - dibutylcarbamyl - propiono-, a  - methoxy - b  - N - octylcarbamyl - propiono-, b  - carboxy - b  - amyloxy - propiono - and O -acetyl-undecano-guanamines; 4-N-phenyllauro-, -octano-, -hexano-, -butyro- and -aceto-guanamines, 4 - N - phenyl - (21-ethyl) - hexano-, 4 - N - phenyl - (21 - methoxy) - propiono-, 4 - N - hydroxyphenyl - butyro-, 4 - N - m - aminophenyl-butyro-, 4 - N - cyclohexyl - (21 - ethyl) - hexano-, 4 - N - lauroyl - lauro- and 4 - N - octanoyl - octano-guanamines; 4 - N - p - tertiary - amylphenyl- and 4 - N - butyl - 4 - N - phenyl - formoguanidines, 4 - N - phenyl-, 4 - N - cyclohexyl-, 4 - N - butyl - benzo - guanamines; 4,6 - N,N1 - dibutyl - benzo-, 4,6-N,N1-dimethyl - hexano-, 4,6 - N,N1 - diethanol - lauro- and 4 - N - phenyl - N - myristoyl myristo - guanamines.  The compositions are preferably prepared by dispersing a solution of the guanamine or condensation product in methanol, ethanol, isopropanol or ethylene glycol ethyl ether in an aqueous solution or dispersion of the resin with the aid of sodium isopropyl naphthalene p  sulphonate, sodium lauryl sulphate, sulphite cellulose liquor and sodium, ammonium or ethanolamine stearates and oleates. Gum tragacanth, gum ghatti, gum arabic, hydrogenated ester gum, fillers, and curing accelerators, e.g. hexamethylene tetramine and diammonium phosphate, may be added.  The fabric is immersed in the dispersion, squeezed, dried at 250 DEG  F. and further heated to cure the resin and provide a laundry-resistant waterproof finish.  The guanamine condensation products are prepared by heating with aqueous formaldehyde, paraformaldehyde or trioxymethylene.  If the resulting emulsion is heated under reduced pressure, a paste is formed which hardens on cooling and further dehydration to a soft resin.  The urea-, thiourea- or melamine-aldehyde resins are preferably used in water-soluble or water-dispersible form.  Methylolmelamines alkylated with methanol or a polyethylene glycol may be used.  Stearoguanamine is prepared by mixing biguanide and methyl stearate with a solution of sodium in methanol and ethanol and allowing to stand.  The precipitate is recrystallized from methyl ethyl ketone. Decanoguanamine, n-octanoguanamine, 21-ethylhexanoguanamine, lauroguanamine, and myristoguanamine are similarly prepared.  O  - Carboxypelargono - guanamine is prepared by allowing a mixture of biguanide and sodium butyl sebacate dispersed in methanol to stand. The precipitate of sodium salt is extracted with hot water and precipitated with acid.  O -Carboxypropiono-guanamine is similarly prepared from sodium methyl succinate, 2 - carboxy - 3 - isopropyl - 6 - methyl - endomethylene - tetrahydrobenzo - guanamine is prepared by refluxing a methanol solution of 3 - methyl - 6 - isopropyl - endomethylene-tetrahydrophthalic anhydride and adding sodium dissolved in methanol, ethylene glycol methyl ether, and biguanide. The methanol is evaporated, the product dissolved in water, acidified, extracted with carbon tetrachloride and neutralized with ammonium hydroxide.  O  - Carboxy - endomethylene - tetrahydrobenzo - guanamine is similarly prepared from sodium methyl endomethylene tetrahydrophthalate.  The N-substituted guanamines may be prepared by fusion with amine salts, preferably in the presence of phenol and zinc chloride as catalyst.  N-acyl guanamines may be prepared by heating with acid anhydrides or acid chlorides, preferably in the presence of a trialkylamine.