Methods of making new surface active compounds

Claim 1

A method of preparing a compound selected from those of the following formulae: ##STR13## and mixtures of I and II, wherein 1) R is a C 6 to C 30 aliphatic radical, preferably alkyl or alkenyl; 2) X, Y and Z are independently selected from the group consisting of C 1 to C 6 alkyl, C 2 to C 6 alkenyl and (--CH 2 CHR 3 O--) n H groups wherein R 3 is independently selected from hydrogen and C 1 to C 4 alkyl, and n is independently an integer from 1 to 20; 3) R 2 is C 1 to C 18 alkyl, C 2 to C 18 alkenyl, benzyl or phenylethyl; 4) R 1 is hydrogen, C 1 to C 4 alkyl or C 2 to C 6 alkenyl; 5) An is a water-solubilizing anion; 6) q is an integer of 1 to 4 equivalent to the valence of the anion (An); and at least one of X, Y and Z is a (--CH 2 CHR 3 O--) n H group comprising: A. reacting a compound of the formula RNHCH.sub.2 CHR.sub.1 CH.sub.2 NH.sub.2 with at least 3 moles per mole of said latter compound of an alkylating agent which comprises at least one mole per mole of said compound of an alkylene oxide of the formula ##STR14## and then reacting the resulting di-tertiary amine, in either order with B. one mole per mole of said amine of an alkylating agent of the formula R 2 An to quaternize one tertiary atom and with C. an oxidizing agent to oxidize the other tertiary nitrogen atom to an amine oxide.

Claim 2

A method of preparing a compound selected from those of the following formulae: ##STR13## and mixtures of I and II, wherein 1) R is a C 6 to C 30 aliphatic radical, preferably alkyl or alkenyl; 2) X, Y and Z are independently selected from the group consisting of C 1 to C 6 alkyl, C 2 to C 6 alkenyl and (--CH 2 CHR 3 O--) n H groups wherein R 3 is independently selected from hydrogen and C 1 to C 4 alkyl, and n is independently an integer from 1 to 20; 3) R 2 is C 1 to C 18 alkyl, C 2 to C 18 alkenyl, benzyl or phenylethyl; 4) R 1 is hydrogen, C 1 to C 4 alkyl or C 2 to C 6 alkenyl; 5) An is a water-solubilizing anion; 6) q is an integer of 1 to 4 equivalent to the valence of the anion (An); and at least one of X, Y and Z is a (--CH 2 CHR 3 O--) n H group comprising: A. reacting a compound of the formula RNHCH.sub.2 CHR.sub.1 CH.sub.2 NH.sub.2 with at least 3 moles per mole of said latter compound of an alkylating agent which comprises at least one mole per mole of said compound of an alkylene oxide of the formula ##STR14## and then reacting the resulting di-tertiary amine, in either order with B. one mole per mole of said amine of an alkylating agent of the formula R 2 An to quaternize one tertiary atom and with C. an oxidizing agent to oxidize the other tertiary nitrogen atom to an amine oxide.