Cationic poly alpha-1,3-glucan ethers

• US 9,957,334 B2
• Filed: 12/17/2014
• Issued: 05/01/2018
• Est. Priority Date: 12/18/2013
• Status: Active Grant

• Current Assignee: Nutrition & Biosciences USA 4, Inc. (International Flavors & Fragrances Incorporated)
• Original Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Inventors: Dennes, T. Joseph, Perticone, Andrea M., Paullin, Jayme L.
• Primary Examiner(s): Mruk, Brian P
• Application Number:
  US15/103,682
• Publication Number:
  US 20160311935A1
• Time in Patent Office: 1,231 Days
• CPC Class Codes: A61K 2800/48 Thickener, Thickening system
• CPC Class Codes: A61K 2800/5426 cationic
• CPC Class Codes: A61K 8/73 Polysaccharides
• CPC Class Codes: A61Q 11/00 Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
• CPC Class Codes: C08B 37/0009 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 Class Codes: C08L 5/00 Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
• CPC Class Codes: C11D 17/0008 aqueous liquid non soap compositions C11D3/0015, C11D3/3947, C11D3/3956 take precedence
• CPC Class Codes: C11D 17/003 Colloidal solutions, e.g. gels; Thixotropic solutions or pastes
• CPC Class Codes: C11D 3/227 with nitrogen-containing groups

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.

Claims

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

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;

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:

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.

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;

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;

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.