Patent GB-771635-A (GB)
Title: Amphoteric surface-active organic compounds and process of preparing same
Filed: 1955-05-19
Abstract: The invention comprises amphoteric surface-active agents which yield soluble surface-active salts in presence of acids and bases of the formula <FORM:0771635/IV(b)/1> wherein xis an integer from 1 to 3, y ranges from 0 to 3, but x+y is not greater than 5, R1 is alkyl or alkaryl of 8-18 carbon atoms, A is a divalent group of formula: -NR3-, -NR3-(C2H4NH)z-, or -NR3-(C3H6NH)z (Z being 1 to 3, R3 representing H or alkyl of 8-18 carbon atoms), R2 is methyl, ethyl, propyl, halogen, carboxyl, or the group <FORM:0771635/IV(b)/2> They are bactericides (see Group VI) and are made by reacting at elevated temperatures an amine of formula R1-A-H with formaldehyde and with a phenol of the formula <FORM:0771635/IV(b)/3> the molecular proportions of amine and formaldehyde being about 1 : 1, while the molecular proportions of amine to phenol are from about 1 : 1 to 3 : 1 according to the number of R1-A-CH2- groups in the compound to be produced. In examples: formaldehyde is reacted with (1) octylamine and phenol to give o- and p-octylaminomethylphenol, (2) dodecyl-diethylene triamine and phenol to give o- and p-dodecyl-diethylene-triamine-methylphenol; (3) dodecyl-diethylenetriamine and p-chloro-m-cresol to give o - dodecyl - diethylenetriaminomethyl - p - chloro - m - cresol; (4) octyl - diethylenetriamine and p-cresol to give o-octyldiethylene-triamino - methyl - p - cresol; (5) octyl - diethylene-triamine and p-chloro-m-xylenol to give o - octyl - diethylenetriamine - methyl - p - chloro - m - xylenol; (6) p - dodecylbenzyl-triethylene-tetramine and phenol to give p-dodecylbenzyl - triethylenetetramino - methyl - o-or -p-hydroxybenzene; (7) tetradecylamine and phenol to give bis-tetradecylaminomethyl-phenol; (8) octyldiethylenetriamine and p-cresol to give bis-(o-octyl-diethylenetriaminomethyl)-p-cresol; (9) dodecyldiethylenetriamine and p-chloro-m-cresol to give bis-(o-dodecyl-diethylenetriamino-methyl)-p-chloro-m-cresol; (10) dodecyl - diethylenetriamine and salicylic acid or p-hydroxy-benzoic acid to give 3,5-bis-(dodecyl - diethylenetriaminomethyl) - salicylic acid or p-hydroxy-benzoic acid; (11) dodecyl-diethylenetriamine and 2,2-bis-(4,4-dioxy-diphenyl)-propane to give 2,2-bis-(p-hydroxy-m,m - di - (dodecyldiethylene - triaminomethyl)-phenyl)-propane.ALSO:Bactericidal compositions comprise aqueous solutions of acid salts (e.g. formic, acetic, or lactic salts) of compounds of the formula:-  <FORM:0771635/VI/1> where in x is an integer from 1 to 3, y ranges from 0 to 3, but x + y is not greater than 5, R1 is alkyl or alkaryl of 8-18 carbon atoms, A is a divalent group of formula:-NR3-, -NR3-(C2 H4 NH)z, or -NR3-(C3 H6 NH) z - (z being 1 to 3, and R3 representing H or alkyl of 8-18 carbon atoms), R2 is methyl, ethyl, propyl, halogen, carboxyl, or the group:-  <FORM:0771635/VI/2> The concentration of the salt may be 5-25 per cent.  Compounds of the above formula which are specified include o- and p-octylaminomethylphenol, o- and p-dodecyldiethylenetriamino - methylphenol, o - dodecyldiethylenetriamino - methyl - p - chloro -m-cresol, o - octyldiethylenetriamino - methyl - p - cresol, o - octyl - diethylenetriamino - methyl - p - chloro - m - xylenol Others are listed.