Carboxylate ester of polysaccharide

Patent metadata

Field	Value
Publication number	US-10167347-B2
Application number	US-201515125220-A
Country	US
Kind code	B2
Filing date	Mar 11, 2015
Priority date	Mar 25, 2014
Publication date	Jan 1, 2019
Grant date	Jan 1, 2019

Abstract

The invention relates to a carboxylate ester of polysaccharide characterized in that it possesses ester bonds with trimellitic anhydride and is soluble in water. The polysaccharide is esterified with trimellitic anhydride and the degree of substitution of the polysaccharide lies in the range of from 0.5 to 3. The invention further relates to methods for the manufacture of these polysaccharides esters in organic solvents, in water or in an extruder or a kneader and to their use in fabric and home care formulations.

First claim

The invention claimed is:

1. A carboxylate ester of polysaccharide, wherein the polysaccharide is esterified with trimellitic anhydride and wherein a degree of substitution of the polysaccharide lies in the range of from 1 to 2.5.

2. The carboxylate ester of polysaccharide according to claim 1 , wherein the polysaccharide is inulin, maltodextrin, xyloglucan, alginate, starch, or a mixture thereof.

3. The carboxylate ester of polysaccharide according to claim 1 , wherein the polysaccharide is inulin and an average chain length of the inulin lies in the range of from 3 to 100 fructose units.

4. The carboxylate ester of polysaccharide according to claim 1 , wherein the polysaccharide is inulin and an average chain length of the inulin lies in the range of from 10 to 40 fructose units.

5. A method of preparing a carboxylate ester of polysaccharide of claim 1 , comprising:
i) mixing a polysaccharide with trimellitic anhydride and a catalyst in an organic solvent, wherein a molar ratio of trimellitic anhydride to monosaccharide unit lies in a range of from 1:2 to 4:1,
ii) stirring the solution obtained in step i) at a temperature lying in a range of from 20 to 100° C. for 1 to 10 hours,
iii) precipitating an esterified polymer obtained in step ii) by adding a mixture of sodium hydroxide and an alcohol to the reaction mixture obtained in step ii).

6. The method according to claim 5 , wherein the solvent is pyridine, dimethylformamide, dimethyl sulfoxide, or a mixture thereof.

7. The method according to claim 5 , wherein the catalyst is 1-methyl-imidazole.

8. A method of preparing a carboxylate ester of polysaccharide of claim 1 , comprising:
i) mixing a polysaccharide with water and with an aqueous alkali solution, which optionally comprises 1-methyl-imidazole,
ii) stirring the solution obtained in step i) with trimellitic anhydride at a temperature lying in a range of from 0° C. to 50° C. for 1 to 10 hours, wherein the reaction is carried out at a pH of from 8 to 9 and wherein the molar ratio of trimellitic anhydride to monosaccharide unit lies in a range of from 1:2 to 4:1,
iii) optionally precipitating the polymer obtained in step ii) by freeze drying, spray drying, or spray granulation.

9. A method for the preparation of a carboxylate ester of polysaccharide of claim 1 , wherein a polysaccharide is reacted with trimellitic anhydride in an extruder or a kneader in the presence of a catalyst and wherein a molar ratio of trimellitic anhydride to monosaccharide unit lies in a range of from 1:2 to 4:1.

10. The method according to claim 9 , wherein the polysaccharide is reacted in the presence of a non-ionic surfactant.

11. The method according to claim 9 , wherein the catalyst is 1-methyl-imidazole.

12. An aqueous solution comprising the carboxylate ester of polysaccharide according to claim 1 .

13. A laundry cleaning composition comprising from 0.1% to about 10% by weight of the carboxylate ester of polysaccharide according to claim 1 and from 1% to about 70% by weight of one or more surfactant.

14. A powder comprising the carboxylate ester of polysaccharide according to claim 1 .

15. An automatic dishwashing detergent composition comprising from 0.1% to about 15% by weight of the carboxylate ester of polysaccharide according to claim 1 , from 0.1% to 30% by weight of a bleach and optionally a bleach activator, and from 1% to about 30% by weight of one or more surfactant.

Assignees

• Basf Se

Inventors

• Shabelina Natalia
• Witteler Helmut
• Detering Juergen
• Schneider Ulrich
• Neumann Jessica

Classifications

• C11D3/39

  Organic or inorganic per-compounds · CPC title

• C11D3/226

  esterified · CPC title

• C08B37/0054 Primary

  Inulin, i.e. beta-2,1-D-fructofuranan; Derivatives thereof · CPC title

• C11D11/0023

  Chemistry & Metallurgy · mapped topic

• C11D11/0017

  Chemistry & Metallurgy · mapped topic