Patent GB-742055-A (GB)
Title: N-carboxymethyl substituted alkylene and polyalkylene polyamines
Filed: 1952-06-17
Abstract: The invention relates to N-carboxymethylated polyamines having the general formula <FORM:0742055/IV(a)/1> in which X is a keryl group derived from a monochloro kerosene, R is an alkylene group containing 2 or 3 carbon atoms, n is 0, 1 or 2 and Z is a hydrogen atom or the group -CH2.COOM where M is hydrogen, an alkali metal or the ammonium group, at least one Z having the formula -CH2.COOM.  They may be prepared from N-keryl polyamines of the formula X-NH-R(NH-R)n-NH2 by reacting the amine with one to five mols. of mono-chloracetic acid or an alkali metal or ammonium salt thereof, or with formaldehyde and an alkali-metal or ammonium cyanide in aqueous medium.  The salts obtained may be converted into the corresponding free acids by acidification. The products have detersive, wetting-out, lathering and calcium-ion sequestering properties.  They may be used in the textile, pulp and leather industries and are useful generally in stabilizing aqueous solutions of materials which form water-insoluble salts, e.g. soaps (see Group III) and certain germicides (see Group VI).  Examples describe the production of (1) trisodium tris (N-carboxymethyl)-N-keryl diethylene triamine by the alternate portionwise addition of aqueous formaldehyde and sodium cyanide to an aqueous solution of the N-kerylated amine and sodium hydroxide refluxing under reduced pressure; (2) a mixture of the salt of (1) and tetra-sodium tetrakis (N-carboxymethyl) N-keryl diethylene triamine is prepared similarly using a higher temperature.  Reference is also made to products derived from N-kerylated ethylene diamine, propylene diamine, trimethylene diamine, triethylene tetramine and dipropylene triamine.  Other alkali metal salts mentioned are the potassium and lithium salts. The N-keryl polyamines are prepared by condensing the unsubstituted polyamine with a substantially monochlorinated kerosene at between 100 DEG  and 200 DEG  C. Reference has been directed by the Comptroller to Specification 600,629.ALSO:N-keryl-N-carboxymethyl substituted alkylene polyamines having the general formula <FORM:0742055/III/1> in which X represents a keryl group derived from a monochlorokerosene, R is an alkylene group having 2 or 3 carbon atoms, n, is 0, 1 or 2 and Z is a hydrogen atom or the group -CH2COOM, wherein M represents a hydrogen atom, an alkali metal atom or the ammonium group, and at least one Z has the formula -CH2COOM (see Group IV(b)) are added to soaps and other detergents to prevent the formation of curds and scums during washing operations.  Liquid soaps are thereby stabilized against cloud-formation.  The usual fillers and builders may be present. Reference has been directed by the Comptroller to Specification 600,629 [Group IV(b)].ALSO:Quaternary ammonium type germicides are prevented from precipitating in hard waters by means of N-keryl-N-carboxymethylated polyamines having the general formula <FORM:0742055/VI/1> in which X is a keryl group derived from a monochlorokerosene, R is an alkylene group containing 2 or 3 carbon atoms, n is 0, 1 or 2 and Z is a hydrogen atom or the group -CH2. COOM where M is hydrogen, an alkali metal of the ammonium group, at least one Z having the formula -CH2.COOM (see Group IV(b)). Reference has been directed by the Comptroller to Specification 600,629, [Group IV(b)].