Anionic glycasuccinamide sufactants and a process for their manufacture

A process for making an alkyl or alkenyl glycasuccinamide compound having the formulas:

• ##STR134## wherein A is selected from the group consisting of the following structures which are attached to the succinate ring via the nitrogen (N) atom on said structures:
• ##STR135## wherein A.sub.1 is hydrogen (H), an alkali metal, alkaline earth metal, basic amino acid, ammonium, alkyl substituted ammonium or mono-, di-, trialkanolammonium group having about 1 to about 6 carbon atoms or mixtures thereof;
• wherein G is selected from the group consisting of hydrogen (H), a SO.sub.3 M, PO.sub.3 M.sub.2, (CH.sub.2 CH.sub.2 O).sub.a H or (CH.sub.2 CHCH.sub.3 O).sub.b H group, a mono-, disaccharide or mixtures thereof;
• wherein M is selected from the group consisting of hydrogen (H), an alkali metal, alkaline earth metal, ammonium, alkyl substituted ammonium or mono-, di-, trialkanolammonium group having about 1 to about 5 carbon atoms or mixtures thereof;
• wherein W is a CH.sub.2 group, oxygen atom (O) or mixtures thereof;
• wherein X is hydrogen (H), an alkyl group having about 1 to about 4 carbon atoms or mixtures thereof;
• wherein Y is a NR.sub.10, .sup.+ N(R.sub.10).sub.2, O, S, SO, SO.sub.2, COO, OOC, CONR.sub.10, NR.sub.10 CO group or mixtures thereof;
• wherein Z is a CH.dbd.CH or CH.sub.2 CH.sub.2 group;
• wherein R.sub.9 is a straight or branched chain saturated or unsaturated hydrocarbon which may be unsubstituted or substituted with an aromatic, cycloaliphatic or mixed aromatic radical having about 1 to about 31 carbon atoms;
• wherein R.sub.10 is hydrogen (H), a hydroxylalkyl group having about 1 to about 6 carbon atoms, a straight or branched chain, saturated or unsaturated hydrocarbon which may be unsubstituted or substituted with an aromatic, cycloaliphatic or mixed aromatic aliphatic radical having about 1 to about 8 carbon atoms;
• wherein R.sub.11 is hydrogen (H), or an alkyl, alkenyl or hydroxyalkyl group having about 1 to about 6 carbon atoms;
• wherein R.sub.12 is hydrogen (H), or an alkyl, alkenyl or hydroxyalkyl group having about 1 to about 6 carbon atoms;
• wherein R.sub.13 is hydrogen (H), a straight or branched chain saturated or unsaturated hydrocarbon which may be unsubstituted or substituted with a hydroxyl, polyhydroxyl, aromatic, cycloaliphatic or mixed aromatic radical having about 1 to about 31 carbon atoms;
• wherein a=0-35;
• b=0-35;
• c=1-3;
• d=1-5;
• e=0-35;
• m=0-8;
• n=1-6;
• o=0-2;
• p=0-4;
• q=0-3;
• r=0-3;
• and s=0-1;
• wherein structures (1) and (2) are disaccharide and structures (3) to (9) are mono or disaccharides;
• which process comprises reacting a glycamine with a second reactant selected from the group consisting of alkyl- or alkenyl succinic or glutaric anhydride, alkyl- or alkenyl dicarboxylic acid, alkyl- or alkenyl dicarboxylic acid ester or mixtures thereof in the presence or absence of a base catalyst.

A process for making an alkyl- or alkenyl glycasuccinamide compound having the formulas:

• ##STR140## wherein A.sub.1 is hydrogen (H), an alkali metal, alkaline earth metal, basic amino acid, ammonium, alkyl substituted ammonium or mono-, di-, trialkanolammonium group having about 1 to about 5 carbon atoms;
• wherein W is a CH.sub.2 group, an oxygen atom (O);
• wherein X is hydrogen (H), or an alkyl group having about 1 to about 2 carbon atoms;
• wherein Y is a NR.sub.10, +N(R.sub.10).sub.2, O, COO, OOC group or mixtures thereof;
• wherein Z is a CH.sub.2 CH.sub.2 or CH.dbd.CH group;
• wherein R.sub.9 is a straight chain saturated hydrocarbon which is un-substituted or substituted with an aromatic, cycloaliphatic or mixed aromatic radical comprising from about 2 to about 25 carbon atoms;
• wherein R.sub.10 is a straight or branched chain, saturated or unsaturated hydrocarbon radical having about 1 to about 5 carbon atoms;
• wherein R.sub.13 is hydrogen (H), a straight or branched chain saturated or unsaturated hydrocarbon which may be unsubstituted or substituted with a hydroxyl, polyhydroxyl radical having about 1 to about 16 carbon atoms;
• wherein c=1-3;
• d=1-4;
• and e=0-25;
• which process comprises reacting a glycamine with a second reactant selected from the group consisting of alkyl- or alkenyl succinic or glutaric anhydride, alkyl- or alkenyl dicarboxylic acid, alkyl- or alkenyl dicarboxylic acid ester or mixtures thereof in the presence or absence of a base catalyst.