Patent GB-763323-A (GB)
Title: Improvements in or relating to methylolated quaternary ammonium guanamines
IPC: C08J5/22
Filed: 1954-11-17
Abstract: The invention comprises compounds of the general formula <FORM:0763323/IV(b)/1> where R may be hydrogen or an alkyl group of 1-4 carbon atoms, R0 is hydrogen or a group RO-CH2-, R1 and R2 may be alkyl groups or may together form a saturated, divalent aliphatic chain which together with the nitrogen atom forms a 5 or 6 membered hererocyclic ring such a morpholine, thiamorpholine, 3 : 5-dimethyl morpholine, pyrrolidine, piperidine or N-methylpiperazine, R3 is an alkyl, aralkyl or alkenyl group and X is an anion or R3 and X may together be a propiobetaine radical.  Preferably R1 and R2 are methyl groups, R is hydrogen or a methyl group and R0 is a methylol or methoxymethyl group.  The compounds are made by treating an aminoacetoguanamine of the general formula <FORM:0763323/IV(b)/2> with an alkylating agent or an alkenylating or aralkylating agent such as an alkyl, alkenyl or aralkyl bromide or chloride, or with b -propiolactone, and treating the resulting quaternary salt with formaldehyde, preferably at a temperature of 40 DEG  to 100 DEG  C. and at a pH between 7 and 10 to give a mono or dimethylol derivative of the formula I which may be etherified if desired by heating with an alcohol under acidic conditions giving a product of the formula I in which R is an alkyl group.  In examples dimethylaminoacetoguanamine is reacted with (1) benzyl chloride; (2) dodecenyl chloride; (3) dodecyl bromide; (4) methyldodecylbenzyl chloride; (5) n-octadecyl bromide; and (6) b -propiolactone; the resulting quaternary compounds or, in the latter case betaine, are treated with formaldehyde to give mono or dimethylol derivatives; corresponding alkoxy derivatives may be formed, e.g. the quaternary compound of (1) and the betaine of (4) are treated with methyl hemiformal and methanolic formaldehyde respectively to give methoxymethyl derivatives, and the methylol derivative obtained from (3) is converted to the methoxymethyl derivative by treatment with methanol; also, Example (7) morpholinoacetoguanamine is quaternated with methyl iodide and the resulting quaternary salt is treated with formaldehyde to give the methylol derivative; in the processes of (1) and (7) the specified guanamine starting materials may be replaced by diethylaminoacetoguanidine and pyrrolidinoacetoguanamine respectively.  Starting materials.  Tertiary aminoacetoguanamines of the formula II, such as dimethylaminoacetoguanamine, diethylaminoacetoguanamine, morpholinoacetoguanamine and pyrrolidinoacetoguanamine are made by reaction between dicyandiamide and an aminoacetonitrile of the formula R1(R2)N.CH2.CN in the presence of an alkali.ALSO:Anti-static agents for the treatment of textiles comprise guanamines of the formula <FORM:0763323/IV(b)/1> (see Group IV(b)) wherein R is hydrogen or an alkyl group of 1-4 carbon atoms, R0 is hydrogen or a group RO-CH2-, R1 and R2 are alkyl groups or together with the nitrogen atom form a 5 or 6 membered heterocyclic radical such as morpholine, thiamorpholine, 3:5-dimethylmorpholine, pyrrolidine, piperidine or N-methylpiperazine and R3 is an alkyl, aralkyl or alkenyl radical and X is an anion or R3 and X together may be a propiobetaine radical.  The compounds are suitable for application to fibres of cellulose acetate, nylon, polyester condensates and polyacrylonitrile.  In examples (1) nylon is treated with a solution of [2:4-bis (methoxymethylamino)-triazinyl-(6)-methyl] dimethyl benzyl ammonium chloride; (6) [2:4-bis (methoxymethylamino)-triazinyl-(6)-methyl] dimethyl b -carboxyethyl-amine betaine is used to treat a polyacrylonitrile fabric to give an anti-static finish, a similar compound is used for the treatment of rayon.  Other specified anti-static agents include compounds substituted by hydroxymethylamino groups in the 2:4 positions of the triazine ring and compounds wherein R3 is a dodecyl, dodecenyl, methyldodecylbenzyl or octadecyl group.