Cationic poly alpha-1,3-glucan ethers

Patent metadata

Field	Value
Publication number	US-9957334-B2
Application number	US-201415103682-A
Country	US
Kind code	B2
Filing date	Dec 17, 2014
Priority date	Dec 18, 2013
Publication date	May 1, 2018
Grant date	May 1, 2018

Abstract

Poly alpha-1,3-glucan ether compounds are disclosed herein comprising positively charged organic groups. The degree of substitution of the ether compounds is about 0.05 to about 3.0. Also disclosed are methods of producing poly alpha-1,3-glucan ether compounds having positively charged organic groups, as well as methods of using these ether compounds for increasing the viscosity of a aqueous compositions. Hydrocolloids and aqueous solutions comprising the ether compounds are also disclosed.

First claim

What is claimed is:

1. A composition comprising a poly alpha-1,3-glucan ether compound represented by the structure:

wherein
(i) n is at least 6,
(ii) each R is independently an H or a positively charged organic group, and
(iii) the compound has a degree of substitution of about 0.05 to about 3.0.

2. The composition of claim 1 , wherein at least one positively charged organic group comprises a substituted ammonium group.

3. The composition of claim 2 , wherein the positively charged organic group comprises a trimethylammonium group.

4. The composition of claim 2 , wherein the positively charged organic group is a quaternary ammonium group.

5. The composition of claim 1 , wherein at least one positively charged organic group comprises an alkyl group or hydroxy alkyl group.

6. The composition of claim 5 , wherein at least one positively charged organic group is a quaternary ammonium hydroxypropyl group.

7. A method of producing a poly alpha-1,3-glucan ether compound, the method comprising:
(a) contacting poly alpha-1,3-glucan in a reaction under alkaline conditions with at least one etherification agent comprising a positively charged organic group, wherein at least one positively charged organic group is etherified to the poly alpha-1,3-glucan thereby producing a poly alpha-1,3-glucan ether compound represented by the structure:

wherein
n is at least 6,
(ii) each R is independently an H or the positively charged organic group, and
(iii) the compound has a degree of substitution of about 0.05 to about 3.0; and

(b) optionally, isolating the poly alpha-1,3-glucan ether compound produced in step (a).

8. The method of claim 7 , wherein said alkaline conditions comprise an alkali hydroxide solution.

9. The method of claim 7 , wherein the reaction comprises an organic solvent.

10. The method of claim 9 , wherein the organic solvent is isopropanol.

11. The method of claim 7 , wherein step (a) further comprises:
(i) heating the reaction; and/or
(ii) neutralizing the pH of the reaction.

12. The method of claim 7 , wherein at least one positively charged organic group comprises a substituted ammonium group.

13. The method of claim 12 , wherein at least one positively charged organic group comprises a trimethylammonium group.

14. A hydrocolloid or aqueous solution comprising a poly alpha-1,3-glucan ether compound represented by the structure:

wherein
(i) n is at least 6,
(ii) each R is independently an H or a positively charged organic group,
(iii) the compound has a degree of substitution of about 0.05 to about 3.0, and
(iv) the hydrocolloid or aqueous solution has a viscosity of at least about 10 centipoise.

15. A method for increasing the viscosity of an aqueous composition, the method comprising:
contacting a poly alpha-1,3-glucan ether compound with the aqueous composition, wherein the viscosity of the aqueous composition is increased by said compound,
wherein said compound is represented by the structure:

wherein
(i) n is at least 6,
(ii) each R is independently an H or a positively charged organic group, and
(iii) the compound has a degree of substitution of about 0.05 to about 3.0.

16. A method of treating a material, said method comprising:
contacting a material with an aqueous composition comprising a poly alpha-1,3-glucan ether compound represented by the structure:

wherein
(i) n is at least 6,
(ii) each R is independently an H or a positively charged organic group, and
(iii) the compound has a degree of substitution of about 0.05 to about 3.0.

17. The method of claim 16 , wherein the material comprises fabric.

18. The method of claim 17 , wherein the fabric comprises at least one natural fiber, synthetic fiber, or semi-synthetic fiber.

19. The method of claim 17 , wherein the poly alpha-1,3-glucan ether compound adsorbs to the fabric.

20. The hydrocolloid or aqueous solution of claim 14 , wherein the hydrocolloid or aqueous solution is comprised in a personal care product, pharmaceutical product, food product, household product, or industrial product.

21. The hydrocolloid or aqueous solution of claim 14 , further comprising at least one surfactant.

Assignees

• Du Pont
• Du Pont

Inventors

• Dennes T Joseph
• Perticone Andrea M
• Paullin Jayme L

Classifications

• A61K8/73

  Polysaccharides · CPC title

• A61K2800/48

  Thickener, Thickening system · CPC title

• C11D17/0008

  aqueous liquid non soap compositions (C11D3/0015, C11D3/3947, C11D3/3956 take precedence) · CPC title

• C08L5/00

  Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00 · CPC title

• C08B37/0009 Primary

  alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof · CPC title