Patent GB-586190-A (GB)
Title: Improvements relating to the preparation of quaternary salts of dimethylurea monoethers
IPC: D06M13/432
Filed: 1944-02-09
Abstract: A quaternary compound of a dimethyl urea monoether having the formula ROCH2.NHCONH.CH2.N(tert.)Y where R is the residue of an aliphatic alcohol of 4 or more carbon atoms, N(tert.) represents the molecule of a tertiary nitrogen base and Y a salt-forming anion, is prepared by heating a salt of a tertiary nitrogen base at a temperature of 30 DEG  to 80 DEG  C. with a diether of dimethylol urea of the formula ROCH2.NHCONH.CH2OR1, where R is as above and R1 represents an alkyl radical which does not contain more carbon atoms than R and preferably not more than 6; an alcohol R1OH is liberated.  The diethers, used as starting materials, may be prepared by reacting one mole. of dimethylol urea with two moles (preferably a large excess over two moles.) of an alcohol ROH in the presence of an acid condensing agent, or to obtain a mixed ether, by preparing a diether as above using an alcohol R1OH and reacting the diether with the appropriate quantity of alcohol ROH under acid conditions so replacing one of the first alcohol residues by the second.  Alcohols of the formula ROH include butyl, amyl, n-dodecyl and higher alcohols obtained by the reduction of coconut fatty acids, and branched chain alcohols, such as isobutyl alcohol, 2-, 3- and 4-methyl pentanol-1, 2-ethyl hexanol-1, 5-ethyl nonanol-2, 3 : 9-diethyl tridecanol-6 and mixtures of branched chain alcohols obtained by hydrogenation of higher aliphatic ketones with nickel catalysts or of oxides of carbon with promoted copper-chromium catalysts; commercial mixtures of the former type may contain 2-methyl pentanol-1, di-isopropyl carbinol, 2 : 4-dimethyl pentanol-1, 2 : 4-dimethyl hexanol-3, 4-methyl hexanol-1, 2 : 4-dimethyl-hexanol-1, 4-methyl heptanol-1 and some ketones such as 2 : 4-dimethyl-hexanone-3. Suitable amine salts are those of trimethylamine, triethylamine and pyridine bases including picolines and quinolines, especially the salts of hydrochloric, hydrobromic, hydriodic, nitric and sulphurous acids; salts with acetic and chloroacetic acids may also be used.  The quaternary compounds decompose on heating at above 80 DEG  C. forming water-insoluble resinous polymers.  They may be used, therefore, in the creaseproofing and waterproofing of textile fibres, in producing paper of improved wetstrength and in the treatment of leather (see Group VIII); for the treatment of pigments and as latent accelerators for amino plastics and adhesives.  In examples: (1) stearyl methyl ether of dimethylol urea is reacted with pyridine hydrochloride in ethyl alcohol at 70 DEG  C. and the solution dried at 40-50 DEG  C.; the water-soluble pyridine salt to obtained on heating in the dry state or in aqueous solution looses pyridine and forms a resin; (2) lauryl methyl ether of dimethylol urea is similarly reacted with trimethylamine hydrochloride; (3) as in (1) using the pyridine sulphite as the amine salt; the product yields a foaming solution; (4) dimethylol urea is heated at 80 DEG  C. with n-butanol in the presence of phthalic acid, liberated water is distilled off and the mixture then heated with 2-ethyl hexanol-1 under reduced pressure at 90 DEG  C. to form the butyl octyl ether of dimethylol urea, the liberated butanol being distilled off and the mixed ether reacted with pyridine hydrochloride as above.  The lauryl or stearyl methyl ether of dimethylol urea is prepared by heating, for example n-octadecanol with dimethoxy dimethyl urea in the presence of phthalic acid and distilling off the liberated methanol.  Dimethoxy dimethyl urea is prepared by dissolving dimethylolurea in methanol containing a little oxalic acid, the pH being adjusted to a value of about 8.0 by means of caustic soda; trimethoxy trimethyl melamine is prepared in like manner.