Modified Lignin Biopolymer Useful in Cleaning Compositions

• US 20100075878A1
• Filed: 09/18/2009
• Published: 03/25/2010
• Est. Priority Date: 09/19/2008
• Status: Active Grant

• Current Assignee: The Procter & Gamble Company
• Original Assignee: The Procter & Gamble Company
• Inventors: Hubesch, Bruno Albert Jean, Wang, Xiaoru Jenny, Gizaw, Yonas, Zannoni, Luke Andrew, Dupont, Jeffrey Scott
• Granted Patent: US 8,075,637 B2
• Time in Patent Office: Days
• US Class Current: 510/119
• CPC Class Codes: A61K 8/9794 Liliopsida [monocotyledons]
• CPC Class Codes: A61Q 5/02 Preparations for cleaning the hair
• CPC Class Codes: C08H 6/00 Macromolecular compounds derived from lignin, e.g. tannins, humic acids
• CPC Class Codes: C11D 3/3707 Polyethers, e.g. polyalkyleneoxides
• CPC Class Codes: C11D 3/382 Vegetable products, e.g. soya meal, wood flour, sawdust

Abstract

Novel modified lignin polymers containing anionic, cationic, and/or alkoxy substitution are disclosed. Further, new cleaning compositions including the novel substituted lignin polymers are disclosed. Methods of forming the modified lignin polymers and cleaning compositions are disclosed.

Claims

1. A modified lignin polymer comprising:

a randomly substituted lignin backbone comprising substituted lignin monomer residues and unsubstituted lignin monomer residues, wherein at least two or more of the hydroxyl groups on the randomly substituted lignin backbone have been substituted with R substituent groups,

wherein each R substituent group is independently an R substituent type selected from the group consisting of nitrogen containing substituents R¹ with a substitution weight percentage ranging from 0% to 75%, anionic substituents R² with a substitution weight percentage ranging from 0% to 90%, alkoxy substituents R³ with a substitution weight percentage ranging from 0% to 90%, and combinations of any thereof, provided that the randomly substituted lignin backbone comprises at least two different R substituent types.

2. The modified lignin polymer of claim 1, wherein the modified lignin polymer has a weight average molecular weight ranging from 2,000 Daltons to 300,000 Daltons.

3. The modified lignin polymer of claim 1, wherein the modified lignin polymer comprises substituted lignin monomer residues and unsubstituted lignin monomer residues selected from the group consisting of substituted and unsubstituted residues of p-coumaryl alcohol, coniferyl alcohol, sinapyl alcohol, derivatives thereof, and mixtures thereof.

4. The modified lignin polymer of claim 1, wherein the modified lignin polymer is incorporated into a cleaning composition, a fabric care composition, a dish cleaning composition, a home care composition, or a personal care composition.

5. The modified lignin polymer of claim 1, wherein the each R substituent is attached to the lignin backbone at an oxygen on the lignin backbone.

6. The modified lignin polymer of claim 1, wherein each nitrogen containing substituent R¹ independently has a structure according to Formula II:

where each R⁴ is selected from the group consisting of a lone pair of electrons, H, CH₃, and linear or branched, saturated or unsaturated C₂-C₁₈ alkyl, provided that at least two of the R⁴ groups are not a lone pair of electrons;

R⁵ is a linear or branched, saturated or unsaturated C₂-C₁₈ alkyl chain or a linear or branched, saturated or unsaturated secondary hydroxy(C₂-C₁₈)alkyl chain;

L is a linking group selected from the group consisting of —

O—

, —

C(O)O—

, —

NR⁶—

, —

C(O)NR⁶—

, and —

NR⁶C(O)NR⁶—

, where R⁶ is H or C₁-C₆ alkyl;

y has a value of 0 or 1;

and z has a value of 0 or 1.

7. The modified lignin polymer of claim 1, wherein each anionic substituent R² independently has a structure according to Formula III:

wherein R⁷ is an anionic group selected from the group consisting of carboxylate, carboxymethyl, succinate, sulfate, sulfonate, arylsulfonate, phosphate, phosphonate, dicarboxylate, and polycarboxylate;

L'"'"' is a linking group selected from the group consisting of —

O—

, —

C(O)O—

, —

NR⁸—

, —

C(O)NR⁸—

, and —

NR⁸C(O)NR⁸—

, where R⁸ is H or C₁-C₆ alkyl;

a has a value of 0 or 1; and

b is an integer from 0 to 18.

8. The modified lignin polymer of claim 1, wherein each alkoxy substituent R³ independently has a structure according to Formula IV:

wherein e has a value of 0 or 1;

f is an integer from 0 to 8;

g is an integer from 0 to 50;

L″

is a linking group selected from the group consisting of —

O—

, —

C(O)O—

, —

NR¹¹—

, —

C(O)NR¹¹—

, and —

NR¹¹C(O)NR¹¹—

, where R¹¹ is H or C₁-C₆ alkyl;

each R⁹ is the group ethylene, propylene, butylene, or mixtures thereof; and

R¹⁰ is an end group selected from the group consisting of hydrogen, C₁-C₂₀ alkyl, hydroxy, —

OR¹ and —

OR².

9. The modified lignin polymer of claim 8, wherein R⁹ has a structure —

CH(R¹²)CH₂—

where R¹² is hydrogen, methyl, or ethyl.

10. The modified lignin polymer of claim 1, further comprising one or more hydrophobic substituents R¹³ attached to the lignin backbone at an oxygen, with a substitution weight percentage ranging from 0.1% to 50%, wherein each hydrophobic substituent R¹³ independently has a structure selected from a linear or branched, saturated or unsaturated C₁-C₁₈ alkyl, a linear or branched, saturated or unsaturated C₇-C₁₈ alkylaryl, a linear or branched, saturated or unsaturated secondary hydroxy(C₂-C₁₈)alkyl, or a hydrophobic polymer graft.

11. The modified lignin polymer of claim 1, wherein the randomly substituted lignin backbone is derived from a lignin selected from the group consisting of lignin sulfonates, Kraft lignins, soda lignins, organosolv lignins, softwood lignin, hardwood lignin, cellulosic grasses lignins, corn stover lignins, steam explosion lignins and combinations of any thereof.

12. The modified lignin polymer of claim 1, wherein the modified lignin polymer is not a modified lignin phenol.

13. A modified lignin polymer comprising:

a randomly substituted lignin backbone having a structure

comprising substituted lignin monomer residues and unsubstituted lignin monomer residues selected from the group consisting of substituted and unsubstituted residues of p-coumaryl alcohol, coniferyl alcohol, sinapyl alcohol, derivatives thereof, and mixtures thereof, wherein at least two or more of the hydroxyl groups on the randomly substituted lignin backbone have been substituted with R substituent groups,

where p is an integer from 1 to 3, and each R substituent group is independently R substituent types selected from the group consisting of;

nitrogen containing substituents R¹ with a substitution weight percentage ranging from 0% to 75%, each R¹ independently having a structure according to Formula II;

where each R⁴ is selected from the group consisting of a lone pair of electrons, H, CH₃, and linear or branched, saturated or unsaturated C₂-C₁₈ alkyl, provided that at least two of the R⁴ groups are not a lone pair of electrons;

R⁵ is a linear or branched, saturated or unsaturated C₂-C₁₈ alkyl chain or a linear or branched, saturated or unsaturated secondary hydroxy(C₂-C₁₈)alkyl chain;

L is a linking group selected from the group consisting of —

O—

, —

C(O)O—

, —

NR⁶—

, —

C(O)NR⁶—

, and —

NR⁶C(O)NR⁶—

, where R⁶ is H or C₁-C₆ alkyl;

y has a value of 0 or 1; and

z has a value of 0 or 1;

anionic substituents R² with a substitution weight percentage ranging from 0% to 90%, each R² independently having a structure according to Formula III;

wherein R⁷ is an anionic group selected from the group consisting of carboxylate, carboxymethyl, succinate, sulfate, sulfonate, arylsulfonate, phosphate, phosphonate, dicarboxylate, and polycarboxylate;

L′

is a linking group selected from the group consisting of —

O—

, —

C(O)O—

, —

NR⁸—

, —

C(O)NR⁸—

, and —

NR⁸C(O)NR⁸—

, where R⁸ is H or C₁-C₆ alkyl;

a has a value of 0 or 1; and

b is an integer from 0 to 18;

alkoxy substituents R³ with a substitution weight percentage ranging from 0% to 90%, each R³ independently having a structure according to Formula IV;

wherein e has a value of 0 or 1;

f is an integer from 0 to 8;

g is an integer from 0 to 50;

L″

is a linking group selected from the group consisting of —

O—

, —

C(O)O—

, —

NR¹¹—

, —

C(O)NR¹¹—

, and —

NR¹¹C(O)NR¹¹—

, where R¹¹ is H or C₁-C₆ alkyl;

each R⁹ is the group ethylene, propylene, butylene, or mixtures thereof; and

R¹⁰ is an end group selected from the group consisting of hydrogen, C₁-C₂₀ alkyl, hydroxy, —

OR¹ and —

OR²; and

combinations of any thereof,

provided that the randomly substituted lignin backbone comprises at least two different R substituent types.

14. The modified lignin polymer of claim 13, wherein the modified lignin polymer has a weight average molecular weight ranging from 2,000 Daltons to 300,000 Daltons.

21. A method of treating a fabric comprising:

contacting the fabric with an effective amount of a fabric care composition comprising the modified lignin polymer according to claim 13.

15. A cleaning composition comprising a modified lignin polymer having a randomly substituted lignin backbone comprising:

substituted lignin monomer residues and unsubstituted lignin monomer residues, wherein at least two or more of the hydroxyl groups on the randomly substituted lignin backbone have been substituted with R substituent groups,

wherein each R substituent group is independently an R substituent type selected from the group consisting of nitrogen containing substituents R¹ with a substitution weight percentage ranging from 0% to 75%, anionic substituents R² with a substitution weight percentage ranging from 0% to 90%, alkoxy substituents R³ with a substitution weight percentage ranging from 0% to 90%, and combinations of any thereof, provided that the randomly substituted lignin backbone comprises at least two different R substituent types.

16. The cleaning composition of claim 15, further comprising at least one or more adjuncts selected from the group consisting of bleach activators, surfactants, builders, chelating agents, dye transfer inhibiting agents, dispersants, enzymes, enzyme stabilizers, catalytic metal complexes, polymeric dispersing agents, clay and soil removal/anti-redeposition agents, brighteners, suds suppressors, dyes, perfumes, perfume delivery systems, structure elasticizing agents, fabric softeners, carriers, hydrotropes, processing aids, and pigments.

17. The cleaning composition of claim 15, wherein the cleaning composition is a product selected from the group consisting of liquid laundry detergents, solid laundry detergents, laundry soap products, laundry spray treatment products, laundry pre-treatment products, hand dish washing detergents, automatic dishwashing detergents, a beauty care detergent, hard surface cleaning detergents, carpet cleaning detergents, a shampoo, and a household cleaning detergent.

18. A method for making a cleaning composition comprising:

adding a modified lignin polymer to the cleaning composition,

wherein the modified lignin polymer has a randomly substituted lignin backbone comprising;

substituted lignin monomer residues and unsubstituted lignin monomer residues, wherein at least two or more of the hydroxyl groups on the randomly substituted lignin backbone have been substituted with R substituent groups,

wherein each R substituent group is independently an R substituent type selected from the group consisting of nitrogen containing substituents R¹ with a substitution weight percentage ranging from 0% to 75%, anionic substituents R² with a substitution weight percentage ranging from 0% to 90%, alkoxy substituents R³ with a substitution weight percentage ranging from 0% to 90%, and combinations of any thereof, provided that the randomly substituted lignin backbone comprises at least two different R substituent types.

19. The method of claim 18, further comprising:

adding at least one or more adjuncts selected from the group consisting of bleach activators, surfactants, builders, chelating agents, dye transfer inhibiting agents, dispersants, enzymes, enzyme stabilizers, catalytic metal complexes, polymeric dispersing agents, clay and soil removal/anti-redeposition agents, brighteners, suds suppressors, dyes, perfumes, perfume delivery systems, structure elasticizing agents, fabric softeners, carriers, hydrotropes, processing aids, and pigments to the cleaning composition.

20. The method of claim 18, further comprising:

modifying a lignin polymer by substituting at least two hydroxyl groups on a lignin polymer backbone with at least two R substituent groups.