Anionic glycasuccinamide sufactants and a process for their manufacture

• US 5,844,103 A
• Filed: 03/24/1995
• Issued: 12/01/1998
• Est. Priority Date: 03/24/1995
• Status: Expired due to Fees

• Current Assignee: Lever Brothers Company (Unilever PLC)
• Original Assignee: Lever Brothers Company, Division Of Conopco, Inc.
• Inventors: Au, Van, Harichian, Bijan, Vermeer, Robert
• Primary Examiner(s): Knode, Marian C
• Assistant Examiner(s): Lee, Howard C.
• Application Number:
  US08/410,198
• Time in Patent Office: 1,348 Days
• Field of Search: 536/1.11, 536/4.1, 536/18.5, 536/17.2, 536/18.7, 536/123.1, 536/123.13, 424/49, 424/52, 424/54, 568/852, 510/470
• US Class Current: 536/17.2
• CPC Class Codes: C11D 1/528 Carboxylic amides (R1-CO-NR2R3), where at least one of the chains R1, R2 or R3 is interrupted by a functional group, e.g. a -NH-, -NR-, -CO-, or -CON- group ethers C11D1/526

Abstract

The present invention relates to a new class of carbohydrate based nonionic surfactant, i.e., alkyl and alkenyl glycasuccinamide, and a process for their manufacture.

Claims

1. An anionic alkyl- or alkenyl glycasuccinamide surfactant compound having the formulas:

##STR86## wherein A is selected from the group consisting of the following structures (1) to (9) which are attached to the succinate ring via the nitrogen (N) atom;

##STR87## wherein A₁ 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 SO₃ M, PO₃ M₂, (CH₂ CH₂ O)_a H or (CH₂ CHCH₃ O)_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 CH₂ 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 NR₁₀, +N(R₁₀)₂, O, S, SO, SO₂, COO, OOC, CONR₁₀, NR₁₀ CO group or mixtures thereof;

wherein Z is a CH═

CH or CH₂ CH₂ group;

wherein R₉ 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 R₁₀ 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 R₁₁ is hydrogen (H), or an alkyl, alkenyl or hydroxyalkyl group having about 1 to about 6 carbon atoms;

wherein R₁₂ is hydrogen (H), or an alkyl, alkenyl or hydroxyalkyl group having about 1 to about 6 carbon atoms;

wherein R₁₃ 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.

2. A compound according to claim 1,

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:

##STR88## wherein A₁ 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 G is hydrogen (H), a (CH₂ CH₂ O)_a H or (CH₂ CHCH₃ O)_b H group, a mono-, disaccharide or mixtures thereof;

wherein W is a CH₂ group, oxygen atom (O) or mixtures thereof;

wherein X is hydrogen (H), an alkyl group having about 1 to about 3 carbon atoms or mixtures thereof;

wherein Y is a NR₁₀, +N(R₁₀)₂, O, COO, OOC group or mixtures thereof;

wherein Z is a CH═

CH or CH₂ CH₂ group;

wherein R₉ 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 2 to about 25 carbon atoms;

wherein R₁₀ is hydrogen (H), a hydroxylalkyl group having about 1 to about 4 carbon atoms, a straight or branched chain, saturated or unsaturated hydrocarbon radical having about 1 to about 5 carbon atoms;

wherein R₁₁ is hydrogen (H), or an alkyl, alkenyl or hydroxyalkyl group having about 1 to about 5 carbon atoms;

wherein R₁₂ is hydrogen (H), or an alkyl, alkenyl or hydroxyalkyl group having about 1 to about 5 carbon atoms;

wherein R₁₃ 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 16 carbon atoms;

a=0-25;

b=0-25;

c=1-3;

d=1-4;

e=0-25;

m=0-7;

n=1-5;

o=0-2;

p=0-3;

q=0-2;

r=0-2; and

s=0-1.

3. A compound according to claim 1

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;

##STR89## wherein A₁ 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 4 carbon atoms;

wherein G is hydrogen (H), a (CH₂ CH₂ O)_a H or (CH₂ CHCH₃ O)_b H group, a monosaccharide or mixtures thereof;

wherein X is hydrogen (H), an alkyl group having about 1 to about 2 carbon atoms or mixtures thereof;

wherein Y is an oxygen atom (O);

wherein Z is a CH═

CH or CH₂ CH₂ group;

wherein R₉ is a straight or branched chain saturated hydrocarbon radical having about 3 to about 23 carbon atoms;

wherein R₁₂ is hydrogen (H), or an alkyl, alkenyl or hydroxyalkyl group having about 1 to about 4 carbon atoms;

wherein R₁₃ 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 6 carbon atoms;

a=0-15;

b=0-15;

c=1-2;

d=1-4;

e=0-15;

m=0-5;

n=1-5;

o=0-1;

p=0-2; and

q=0-2.

4. A compound according to claim 1

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;

##STR90## wherein A₁ 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 4 carbon atoms;

wherein G is hydrogen (H);

wherein X is hydrogen (H), an alkyl group having about 1 carbon atom;

wherein Y is an oxygen atom (O);

wherein Z is a CH═

CH or CH₂ CH₂ group;

wherein R₉ is a straight or branched chain saturated hydrocarbon radical having about 4 to about 22 carbon atoms;

wherein R₁₂ is hydrogen (H), or an alkyl, alkenyl or hydroxyalkyl group having about 1 to about 4 carbon atoms;

wherein R₁₃ 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 6 carbon atoms;

c=1;

d=1-4;

e=0-5;

m=0;

n=1-4;

o=0-1;

p=0-1; and

q=1.

5. A compound according to claim 1

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;

##STR91## wherein A₁ is hydrogen (H), an alkali metal, alkaline earth metal, basic amino acid, ammonium, alky) substituted ammonium or mono-, di-, trialkanolammonium group having about 1 to about 4 carbon atoms;

wherein X is hydrogen (H), an alkyl group having about 1 carbon atom;

wherein Y is an oxygen atom (O);

wherein Z is a CH═

CH or CH₂ CH₂ group;

wherein R₉ is a straight or branched chain saturated hydrocarbon radical having about 4 to about 22 carbon atoms;

wherein R₁₃ 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 6 carbon atoms;

c=1;

d=1-4; and

e=0-5.

6. A compound according to claim 4 having the structure:

##STR92## wherein;

A= ##STR93## A₁ =sodium (Na);

G=hydrogen (H);

R₉ =C₁₀ H₂₁ ;

R₁₃ =hydrogen (H);

W=oxygen (O);

Z=CH₂ CH₂ ;

c=1;

e=0;

m=0; and

n=4.

7. A compound according to claim 4 having the structure:

##STR94## wherein;

A= ##STR95## A₁ =sodium (Na);

G=hydrogen (H);

R₉ =C₁₂ H₂₅ ;

R₁₃ =hydrogen (H);

W=oxygen (O);

X=hydrogen (H);

Y=oxygen (O);

Z=CH₂ CH₂ ;

c=1;

d=2;

e=3;

m=0; and

n=4.

8. A compound according to claim 3 having the structure:

##STR96## wherein;

A= ##STR97## A₁ =potassium (K);

G=hydrogen (H) or (CH₂ CH₂ O)_a H group;

R₉ =C₉ H₁₉ ;

R₁₃ =hydrogrn (H);

W=CH₂ ;

Z=CH₂ CH₂ ;

a=can vary from about 1 to about 12 for a total average of 6;

c=1;

e=0;

m=0; and

n=4.

9. A compound according to claim 4 having the structure:

##STR98## wherein;

A= ##STR99## A₁ =ammonium (NH₄);

G=hydrogen (H);

R₉ =C₇ H₁₅ ;

R₁₃ =hydrogen (H);

W=CH₂ ;

Z=CH═

CH;

c=1;

e=0;

m=0; and

n=4.

10. A compound according to claim 3 having the structure:

##STR100## wherein;

A= ##STR101## A₁ =triethanolammonium HN(CH₂ CH₂ OH)₃ !;

G=hydrogen (H);

R₉ =C₉ H₁₉ ;

R₁₃ =hydrogen (H);

W=CH₂ ;

Z=CH═

CH;

c=1;

e=0; and

n=4.

11. A compound according to claim 4, having the structure:

##STR102## wherein;

A= ##STR103## A₁ =magnesium (Mg);

G=hydrogen (H);

R₉ =C₇ H₁₅ ;

R₁₃ =hydrogen (H);

W=CH₂ ;

Z=CH═

CH;

c=1;

e=0;

p=1; and

q=1.

12. A compound according to claim 3 having the structure:

##STR104## wherein;

A= ##STR105## A₁ =sodium (Na);

G=hydrogen (H);

R₉ =C₉ H₁₉ ;

R₁₃ =hydrogen (H);

W=CH₂ ;

Z=CH═

CH;

c=1;

e=O;

o=O; and

p=O.

13. A compound according to claim 4 having the structure:

##STR106## wherein;

A= ##STR107## A₁ =sodium (Na);

G=hydrogen (H);

R₉ =C₉ H₁₉ ;

R₁₂ =CH₃ ;

R₁₃ =hydrogen (H);

W=CH₂ ;

Z=CH═

CH;

c=1;

e=O;

o=1; and

p=1.

14. A compound according to claim 4 having the structure:

##STR108## wherein;

A= ##STR109## A₁ =sodium (Na);

G=hydrogen (H);

R₉ =C₁₂ H₂₅ ;

R₁₃ =CH₃ ;

W=oxygen (O);

X=hydrogen (H);

Y=oxygen (O);

Z=CH₂ CH₂ ;

c=1;

d=2;

e=2;

m=0; and

n=4.

15. A compound according to claim 4 having the structure:

##STR110## wherein;

A= ##STR111## A₁ =potassium (K);

G=hydrogen (H);

R₉ =C₁₃ H₂₉ ;

R₁₃ =CH₃ ;

W=CH₂ ;

Z=CH═

CH;

c=1;

e=0;

m=0; and

n=4.

16. A compound according to claim 4, having the structure:

##STR112## wherein;

A= ##STR113## A₁ =methyl D-glucammonium from methyl D-glucamine;

G=hydrogen (H);

R₉ =C₁₁ H₁₉ ;

R₂₃ ;

R₁₃ =CH₃ ;

W=CH₂ ;

Z=CH═

CH;

c=1;

e=0;

m=0; and

n=4.

17. A compound according to claim 4 having the structure:

##STR114## wherein;

A= ##STR115## A₁ =ammoniumglycinate from glycine;

G=hydrogen (H);

R₉ =C₉ H₁₉ ;

R₁₃ =CH₃ ;

W=CH₂ ;

Z=CH═

CH;

c=1;

e=0;

m=0;

n=4;

p=1; and

q-1.

18. A compound according to claim 4, having the structure:

##STR116## wherein;

A= ##STR117## A₁ =monoethanolammonium NH3CH2CH2OH!;

G=hydrogen (H);

R₉ =C₇ H₁₅ ;

R₁₃ ;

=CH₃ ;

W=CH₂ ;

Z=CH═

CH;

c=1;

e=0;

m=0; and

n=4.

19. A compound according to claim 4 having the structure:

##STR118## wherein;

A= ##STR119## A₁ =sodium (Na);

G=hydrogen (H);

R₉ =C₁₁ H₂₃ ;

R₁₃ =CH₂ CH₃ ;

W=CH₂ ;

Z=CH═

CH;

c=1;

e=0;

m=0; and

n=4.

20. A compound according to claim 3 having the structure:

##STR120## wherein;

A= ##STR121## A₁ =ammonium (NH₄);

G=hydrogen (H);

R₉ =C₁₃ H₂₇ ;

R₁₃ =sorbityl;

W=CH₂ ;

Z=CH═

CH;

c=1;

e=0;

m=0; and

n=4.

21. A compound according to claim 4 having the structure:

##STR122## wherein;

A= ##STR123## A₁ =sodium (Na);

G=hydrogen (H);

R₉ =C₁₃ H₂₇ ;

R₁₃ =CH₂ CH₂ OH;

W=CH₂ ;

Z=CH═

CH;

c=1;

e=0;

m=0; and

n=4.

22. A compound according to claim 5 having the structure:

##STR124## wherein;

A= ##STR125## A₁ =hydrogen (H) or galactose;

R₉ =C₁₁ H₂₃ ;

R₁₃ =hydrogen (H);

W=CH₂ ;

Z=CH₂ CH₂ ;

c=1;

e=0;

m=0; and

n=4.

23. A compound according to claim 5 having the structure:

##STR126## wherein;

A= ##STR127## A₁ =potassium (K);

G=hydrogen (H) or galactose;

R₉ =C₁₃ H₂₇ ;

R₁₃ =CH₃ ;

W=CH₂ ;

Z=CH═

CH;

c=1;

e=0;

m=0; and

n=4.

24. A compound according to claim 5 having the structure:

##STR128## wherein;

A= ##STR129## A₁ =ammonium (NH₄);

G=hydrogen (H) or glucose;

R₉ =C₁₁ H₂₃ ;

R₁₃ =CH₃ ;

W=CH₂ ;

Z=CH═

CH;

c=1;

e=0;

m=0; and

n=4.

25. A compound according to claim 5 having the structure:

##STR130## wherein;

A= ##STR131## A₁ =hydrogen (H);

G=hydrogen (H) or glucose;

R₉ =C₉ H₁₉ ;

R₁₃ =CH₃ ;

W=CH₂ ;

Z=CH═

CH;

c=1;

e=0;

m=0;

n=4;

p=1; and

q=1.

26. A compound according to claim 5 having the structure:

##STR132## wherein;

A= ##STR133## A₁ =sodium (Na);

G=hydrogen (H) or glucose;

R₉ =C₉ H₁₉ ;

R₂₃ ;

R₁₃ =CH₃ ;

W =CH₂ ;

Z=CH═

CH;

c=1;

e=0;

m=0; and

n=4.

27. 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 A₁ 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 SO₃ M, PO₃ M₂, (CH₂ CH₂ O)_a H or (CH₂ CHCH₃ O)_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 CH₂ 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 NR₁₀, ⁺ N(R₁₀)₂, O, S, SO, SO₂, COO, OOC, CONR₁₀, NR₁₀ CO group or mixtures thereof;

wherein Z is a CH═

CH or CH₂ CH₂ group;

wherein R₉ 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 R₁₀ 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 R₁₁ is hydrogen (H), or an alkyl, alkenyl or hydroxyalkyl group having about 1 to about 6 carbon atoms;

wherein R₁₂ is hydrogen (H), or an alkyl, alkenyl or hydroxyalkyl group having about 1 to about 6 carbon atoms;

wherein R₁₃ 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.

28. A process for making an alkyl or alkenyl glycasuccinamide compound according to claim 27

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;

##STR136## wherein A₁ 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 G is hydrogen (H), a (CH₂ CH₂ O)_a H or (CH₂ CHCH₃ O)_b H group, a mono-, disaccharide or mixtures thereof;

wherein W is a CH₂ group, oxygen atom (O) or mixtures thereof;

wherein X is hydrogen (H), an alkyl group having about 1 to about 3 carbon atoms or mixtures thereof;

wherein Y is a NR₁₀, ⁺ N(R₁₀)₂, O, COO, OOC group or mixtures thereof;

wherein Z is a CH═

CH or CH₂ CH₂ group;

wherein R₉ 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 2 to about 25 carbon atoms;

wherein R₁₀ is hydrogen (H), a hydroxylalkyl group having about 1 to about 4 carbon atoms, a straight or branched chain, saturated or unsaturated hydrocarbon radical having about 1 to about 5 carbon atoms;

wherein R₁₁ is hydrogen (H), or an alkyl, alkenyl or hydroxyalkyl group having about 1 to about 5 carbon atoms;

wherein R₁₂ is hydrogen (H), or an alkyl, alkenyl or hydroxyalkyl group having about 1 to about 5 carbon atoms;

wherein R₁₃ 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 16 carbon atoms;

a=0-25;

b=0-25;

c=1-3;

d=1-4;

e=0-25;

m=0-7;

n=1-5;

o=0-2;

p=0-3;

q=0-2;

r=0-2; and

s=0-1;

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.

29. A process for making an alkyl or alkenyl glycasuccinamide compound according to claim 27

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;

##STR137## wherein A₁ 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 4 carbon atoms;

wherein G is hydrogen (H), a (CH₂ CH₂ O)_a H or (CH₂ CHCH₃ O)_b H group, a monosaccharide or mixtures thereof;

wherein X is hydrogen (H), an alkyl group having about 1 to about 2 carbon atoms or mixtures thereof;

wherein Y is an oxygen atom (O);

wherein Z is a CH═

CH or CH₂ CH₂ group;

wherein R₉ is a straight or branched chain saturated hydrocarbon radical having about 3 to about 23 carbon atoms;

wherein R₁₂ is hydrogen (H), or an alkyl, alkenyl or hydroxyalkyl group having about 1 to about 4 carbon atoms;

wherein R₁₃ 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 6 carbon atoms;

a=0-15;

b=0-15;

c=1-2;

d=1-4;

e=0-15;

m=0-5;

n=1-5;

o=0-1;

p=0-2; and

q=0-2;

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.

30. A process for making an alkyl or alkenyl glycasuccinamide compound according to claim 27

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;

##STR138## wherein A₁ 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 4 carbon atoms;

wherein G is hydrogen (H);

wherein X is hydrogen (H), an alkyl group having about 1 carbon atom;

wherein Y is an oxygen atom (O);

wherein Z is a CH═

CH or CH₂ CH₂ group;

wherein R₉ is a straight or branched chain saturated hydrocarbon radical having about 4 to about 22 carbon atoms;

wherein R₁₂ is hydrogen (H), or an alkyl, alkenyl or hydroxyalkyl group having about 1 to about 4 carbon atoms;

wherein R₁₃ 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 6 carbon atoms;

c=1;

d=1-4;

e=0.5;

m=0;

n=1-4;

o=0-1;

p=0-1; and

q=1;

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.

31. A process for making an alkyl- or alkenyl glycasuccinamide compound according to claim 27 ##STR139## wherein A₁ 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 4 carbon atoms;

wherein X is hydrogen (H), an alkyl group having about 1 carbon atom;

wherein Y is an oxygen atom (O);

wherein Z is a CH═

CH or CH₂ CH₂ group;

wherein R₉ is a straight or branched chain saturated hydrocarbon radical having about 4 to about 22 carbon atoms;

wherein R₁₃ 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 6 carbon atoms;

c=1;

d=1-4; and

e=0-5;

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.

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

##STR140## wherein A₁ 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 CH₂ 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 NR₁₀, +N(R₁₀)₂, O, COO, OOC group or mixtures thereof;

wherein Z is a CH₂ CH₂ or CH═

CH group;

wherein R₉ 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 R₁₀ is a straight or branched chain, saturated or unsaturated hydrocarbon radical having about 1 to about 5 carbon atoms;

wherein R₁₃ 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.

33. A process for making an alkyl- or alkenyl glycasuccinamide compound having the formula according to claim 32

wherein A₁ 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 4 carbon atoms;

wherein W is a CH₂ group or an oxygen atom (O);

wherein X is hydrogen (H), or an alkyl group having 1 carbon atom;

wherein Y is a oxygen atom (O);

wherein Z is a CH₂ CH₂ or CH═

CH group;

wherein R₉ is a straight chain saturated hydrocarbon which is un-substituted or substituted with an aromatic, cycloaliphatic or mixed aromatic radical comprising from about 3 to about 23 carbon atoms;

wherein R₁₃ 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 6 carbon atoms;

wherein c=1-2;

d=1-4; and

e=0-5;

which process comprises reacting a glycamine with a second reactant selected from the group consisting of alkyl- or alkenyl succinic anhydride, alkyl- or alkenyl dicarboxylic acid, alkyl- or alkenyl dicarboxylic acid ester or mixtures thereof in the presence or absence of a base catalyst.

34. A process according to claim 33, wherein the NR₁₃ -sugar is from the structure:

##STR141## wherein G is hydrogen (H), a (CH₂ CH₂ O)_a H or (CH₂ CHCH₃ O)_b H group, a mono-, disaccharide or mixtures thereof;

wherein R₁₃ 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 6 carbon atoms;

wherein a and b are each from about 0 to about 35 and the sum of a and b are from about 0 to about 35;

wherein n is from about 1 to about 6;

wherein m is from about 0 to about 8 and the sum of n and m are from about 0 to about 10.

35. A process according to claim 33, wherein the NR₁₃ -sugar is from the structure:

##STR142## wherein G is hydrogen (H), a (CH₂ CH₂ O)_a H or (CH₂ CHCH₃ O)_b H group, a mono-, disaccharide or mixtures thereof;

wherein R₁₃ 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 6 carbon atoms;

wherein a and b are each from about 0 to about 35 and the sum of a and b are from about 0 to about 35;

wherein n is from about 1 to about 6;

wherein m is from about 0 to about 8 and the sum of n and m are from about 0 to about 10.

36. A process according to claim 33, wherein the NR₃ -sugar is from the structure:

##STR143## wherein G is hydrogen (H), a (CH₂ CH₂ O)_a H or (CH₂ CHCH₃ O)_b H group, a mono-, disaccharide or mixtures thereof;

wherein R₁₃ 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 6 carbon atoms;

wherein a and b are each from about 0 to about 35 and the sum of a and b are from about 0 to about 35;

wherein o is from about 0 to about 2; and

p is from about 0 to about 4.

37. A process according to claim 33, wherein the NR₁₃ -sugar is from the structure:

##STR144## wherein G is hydrogen (H), a SO₃ M, PO₃ M₂, (CH₂ CH₂ O)_a H or (CH₂ CH-CH₃ O)_b H group, a mono-, disaccharide or mixtures thereof;

wherein M is hydrogen (H), an alkali metal, alkaline earth metal, ammonium, alkyl substituted ammonium or mono-, di-, trialkanolammonium group with about 1 to about 5 carbon atoms;

wherein a and b are each from about 0 to about 35 and the sum of a and b are from about 0 to about 35;

wherein p and q are each from about 0 to about 3;

wherein r is from about 0 to about 4;

wherein s is from about 0 to about 1 and the sum of p, q and r are from about 0 to about 6.

38. A process according to claim 33, wherein the NR₁₃ -sugar is from the structure:

##STR145## wherein G is hydrogen (H), a (CH₂ CH₂ O)_a H or (CH₂ CHCH₃ O)_b H group, a mono-, disaccharide or mixtures thereof;

wherein R₁₃ 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 6 carbon atoms;

wherein a and b are each from about 0 to about 35 and the sum of a and b are from about 0 to about 35;

wherein o is from about 0 to about 2 and p is from about 0 to about 4.

39. A process according to claim 33, wherein the NR₁₃ -sugar is from the structure:

##STR146## wherein G is hydrogen (H), a SO₃ M, PO₃ M₂, (CH₂ CH₂ O)_a H or (CH₂ CH-CH₃ O)_b H group, a mono-, disaccharide or mixtures thereof;

wherein M is hydrogen (H), an alkali metal, alkaline earth metal, ammonium, alkyl substituted ammonium or mono-, di-, trialkanolammonium group with about 1 to about 5 carbon atoms;

wherein R₁₁ is hydrogen (H), or an alkyl, alkenyl or hydroxyalkyl group having about 1 to about 5 carbon atoms;

wherein a and b are each from about 0 to about 35 and the sum of a and b are from about 0 to about 35;

wherein p and q are each from about 0 to about 3;

wherein r is from about 0 to about 4;

wherein s is from about 0 to about 1 and the sum of p, q and r are from about 0 to about 6.

40. A process according to claim 33, wherein the NR₁₃ -sugar is from the structure:

##STR147## wherein G is hydrogen (H), a (CH₂ CH₂ O)_a H or (CH₂ CHCH₃ O)_b H group, a mono-, disaccharide or mixtures thereof;

wherein R₁₂ is hydrogen (H), or an alkyl, alkenyl or hydroxyalkyl group having about 1 to about 5 carbon atoms;

wherein R₁₃ 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 6 carbon atoms;

wherein a and b are each from about 0 to about 35 and the sum of a and b are from about 0 to about 35;

wherein o is from about 0 to about 2;

wherein p is from about 0 to about 4; and

q is from about 0 to about 3.

41. A process according to claim 33 wherein the s NR₁₃ -sugar is from a Z-amino-Z-deoxyketose wherein Z is from about 2 to about 8.

42. A process according to claim 33, wherein the glycamine is selected from the group consisting of glucamine (1-amino-1-deoxyglucitol), methyl glucamine, ethyl glucamine, propyl glucamine, hydroxyethyl glucamine, maltamine, methyl malt-amine ethyl maltamine, propyl maltamine, butyl maltamine, hydroxyethyl maltamine, lactamine, methyl lactamine, ethyl lactamine, propyl lactamine, butyl lactamine, hydroxyethyl lactamine, ethoxylated methyl glucamine, ethoxylated methyl maltamine, ethoxylated methyl lactamine, propoxylated methyl glucamine, propoxylated methyl maltamine, propoxylated methyl lactamine, 3-amino-1,2-propanediol, 3-methylamino-1,2-propanediol, sorbitanamine, methyl sorbitanamine, ethyl sorbitanamine, propyl sorbitanamine, hydroxyethyl sorbitanamine, glucosylamine (1-amino-1-deoxyglucose), methyl glucosyl-amine, ethyl glucosylamine, propyl glucosylamine, hydroxyethyl glucosylamine, maltosylamine (1-amino-1-deoxymaltose) methyl maltosylamine, ethyl maltosylamine, hydroxyethyl maltosylamine, lactosylamine (1-amino-1-deoxylactose), methyl lactosylamine, ethyl lactosylamine, hydroxyethyl lactosylamine, 6-amino-6-deoxyglucose, 6-amino-6-deoxymethylglucoside, 6-amino-6-deoxyethyl-glucoside, 6-methylamino-6-deoxyglucose, 6-ethyl-amino-6-deoxymethyl-glucoside, 6-hydroxyethylamino-6-deoxyethylgluco-side mixtures thereof.

43. A process according to claim 33, wherein the second reactant is an alkyl- or alkenyl succinic anhydride, an alkyl- or alkenyl dicarboxylic acid, an alkyl- or alkenyl dicarboxylic acid ester or mixtures thereof, wherein the alkyl or alkenyl group comprises from about 4 to about 22 hydrocarbon atoms.

44. A process according to claim 33, wherein the second reactant is a heteroatom containing alkyl- or alkenyl succinic anhydride, a heteroatom containing alkyl- or alkenyl dicarboxylic acid, a heteroatom containing alkyl- or alkenyl dicarboxylic acid ester or mixtures thereof, wherein the alkyl or alkenyl group comprises from about 2 to about 22 hydrocarbon atoms and the heteroatom is a oxygen atom (O).

45. A process according to claim 33, wherein the reaction temperature is from about 20°

C. to about 300°

C.

46. A process according to claim 33, wherein the reaction is carried out under an inert gas blanket.

47. A process according to claim 33, wherein the reaction is carried out at or below atmospheric pressure.

48. A process according to claim 33, wherein the reaction additionally comprises an organic or inorganic base.

49. A process according to claim 33, wherein the base is selected from the group consisting of sodium hydroxide, sodium methoxide, sodium ethoxide, sodium carbonate, potassium carbonate, potassium hydroxide, sodium bicarbonate, trisodium citrate, sodium laurate, disodium oxalate, tripropyl-amine, monoethanolamine, diethanolamine, triethanolamine, glucamine, methyl glucamine, hydroxyethyl glucamine, sodium sarcosinate, sodium glycinate and mixtures thereof.

50. A process according to claim 33, wherein the molar ratio of glycamine to base is from about 500:

1 to about 1;

1.

51. A process according to claim 33, wherein the reaction additionally comprises a solvent, wherein said solvent is water, an organic solvent or mixtures thereof.

52. A process according to claim 33, wherein the solvent is selected from the group consisting of methanol, ethanol, propanol isopropanol, propylene glycol, ethylene glycol, diethylene glycol, polyethylene glycol, glycerol and mixtures thereof.

53. A process according to claim 33, wherein the water or organic solvent is used at a level from about 5% to about 95% by weight of the total reaction mixture.

54. A process according to claim 33, wherein there is additionally present an organic or inorganic acid capable of adjusting the pH of the reaction mixture in the range of about 4 to about 9.

55. A process according to claim 33, wherein there is additionally present a color improvement agent, wherein said agent is a bleaching or reducing agent.

56. A process according to claim 33, wherein the color improvement agent is bleaching agent selected from the group consisting of hydrogen peroxide, sodium hypochlorite, sodium perborate, sodium percarbonate, benzoyl peroxide, peroxymonosulfate, peroxylauric acid, peroxybenzoic acid and mixtures thereof.

57. A process according to claim 33, wherein the color improvement agent is reducing agent selected from the group consisting of sodium bisulfite, sodium sulfite, potassium bisulfite, potassium sulfite, sodium borohydride, potassium borohydride, sodium aluminum hydride, sodium hydride and mixtures thereof.

58. A process according to claim 33, wherein the reactant is an alkyl- or alkenyl glycasuccinimide surfactant that is hydrolyzed with water or aqueous solvent in presence of an organic or inorganic acid or base at about 5°

C. to about 70°

C.