Cationic poly alpha-1,3-glucan ethers
View Patent ↗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.
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,
(iii) the compound has a degree of substitution up to about 3.0, and
(iv) at least 80% of the glycosidic linkages of the poly alpha-1,3-glucan ether compound are alpha-1,3 glycosidic linkages,
and wherein at least one positivity charged organic group is a quaternary ammonium hydroxpropyl group.
2. The composition of claim 1 , wherein the quaternary ammonium hydroxypropyl group comprises trialkylammonium.
3. The composition of claim 2 , wherein the trialkylammonium is trimethylammonium.
4. The composition of claim 1 , wherein the poly alpha-1,3-glucan ether compound has one or more of the same positively charged organic group.
5. The composition of claim 1 , wherein the poly alpha-1,3-glucan ether compound has two or more different positively charged organic groups.
6. The composition of claim 1 , wherein the poly alpha-1,3-glucan ether compound further comprises at least one nonionic organic group.
7. The composition of claim 1 , wherein at least 90% of the glycosidic linkages of the poly alpha-1,3-glucan ether compound are alpha-1,3 glycosidic linkages.
8. The composition of claim 7 , wherein at least 95% of the glycosidic linkages of the poly alpha-1,3-glucan ether compound are alpha-1,3 glycosidic linkages.
9. The composition of claim 1 , wherein the composition is a personal care product, household product, industrial product, pharmaceutical product, or food product.
10. The composition of claim 1 , wherein the composition is a fabric care product.
11. The composition of claim 1 , wherein the composition comprises at least one surfactant.
12. The composition of claim 1 , wherein the composition comprises at least one enzyme.
13. The composition of claim 1 , wherein the composition is an aqueous composition.
14. The composition of claim 1 , wherein the composition comprises fiber and said poly alpha-1,3-glucan ether compound.
15. The composition of claim 14 , wherein said poly alpha-1,3-glucan ether compound is on the surface of the composition.
16. The composition of claim 14 , wherein the fiber is a natural fiber.
17. The composition of claim 16 , wherein natural fiber comprises cellulosic fiber.
18. The composition of claim 14 , wherein the fiber is a synthetic fiber.
19. The composition of claim 18 , wherein the synthetic fiber comprises polyester.
20. The composition of claim 14 , wherein the fiber is a semi-synthetic fiber, optionally wherein the semi-synthetic fiber comprises rayon.
21. The composition of claim 14 , wherein the composition is fabric.
22. The composition of claim 14 , wherein the composition is non-woven fabric, padding, or foam.
23. The composition of claim 14 , wherein the composition is paper.
24. 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
(i) n is at least 6,
(ii) each R is independently an H or the positively charged organic group,
(iii) the compound has a degree of substitution up to about 3.0, and
(iv) at least 80% of the glycosidic linkages of the poly alpha-1,3-glucan ether compound are alpha-1,3 glycosidic linkages, and
wherein the etherification agent is 3-chloro-2-hydroxypropyl trimethyl ammonium chloride; and
(b) optionally, isolating the poly alpha-1,3-glucan ether compound produced in step (a).
25. 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 the positively charged organic group,
(iii) the compound has a degree of substitution up to about 3.0, and
(iv) at least 80% of the glycosidic linkages of the poly alpha-1,3-glucan ether compound are alpha-1,3 glycosidic linkages,
and wherein at least one positively charged organic group is a quaternary ammonium hydroxypropyl group.
26. 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 the positively charged organic group,
(iii) the compound has a degree of substitution up to about 3.0, and
(iv) at least 80% of the glycosidic linkages of the poly alpha-1,3-glucan ether compound are alpha-1,3 glycosidic linkages,
and wherein at least one positivity charged organic group is a quaternary ammonium hydroxypropyl group.
27. The method of claim 26 , wherein the material comprises fabric.
28. 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,
(iii) the compound has a degree of substitution up to about 3.0, and
(iv) at least 80% of the glycosidic linkages of the poly alpha-1,3-glucan ether compound are alpha-1,3 glycosidic linkages,
and wherein the poly alpha-1,3-glucan ether compound has two or more different positively charged organic groups.
29. A composition comprising at least one surfactant and 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 up to about 3.0, and
(iv) at least 80% of the glycosidic linkages of the poly alpha-1,3-glucan ether compound are alpha-1,3 glycosidic linkages.
30. The composition of claim 29 , wherein at least one positively charged organic group comprises a substituted ammonium group.
31. The composition of claim 30 , wherein the positively charged organic group comprises trialkylammonium.
32. The composition of claim 31 , wherein the trialkylammonium is trimethylammonium.
33. The composition of claim 29 , wherein at least one positively charged organic group comprises an alkyl group or hydroxy alkyl group.
34. The composition of claim 33 , wherein at least one positively charged organic group is a quaternary ammonium hydroxypropyl group.
35. The composition of claim 29 , wherein the poly alpha-1,3-glucan ether compound further comprises at least one nonionic organic group.
36. The composition of claim 29 , wherein at least 90% of the glycosidic linkages of the poly alpha-1,3-glucan ether compound are alpha-1,3 glycosidic linkages.
37. The composition of claim 36 , wherein at least 95% of the glycosidic linkages of the poly alpha-1,3-glucan ether compound are alpha-1,3 glycosidic linkages.
38. The composition of claim 29 , wherein the composition is a personal care product, household product, industrial product, pharmaceutical product, or food product.
39. The composition of claim 29 , wherein the composition is a fabric care product.
40. The composition of claim 29 , wherein the composition comprises at least one enzyme.
41. A composition comprising at least one enzyme and 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 up to about 3.0, and
(iv) at least 80% of the glycosidic linkages of the poly alpha-1,3-glucan ether compound are alpha-1,3 glycosidic linkages.
42. The composition of claim 41 , wherein at least one positively charged organic group comprises a substituted ammonium group.
43. The composition of claim 42 , wherein the positively charged organic group comprises trialkylammonium.
44. The composition of claim 43 , wherein the trialkylammonium is trimethylammonium.
45. The composition of claim 41 , wherein at least one positively charged organic group comprises an alkyl group or hydroxy alkyl group.
46. The composition of claim 45 , wherein at least one positively charged organic group is a quaternary ammonium hydroxypropyl group.
47. The composition of claim 41 , wherein at least 90% of the glycosidic linkages of the poly alpha-1,3-glucan ether compound are alpha-1,3 glycosidic linkages.
48. The composition of claim 41 , wherein the composition is a personal care product, household product, industrial product, pharmaceutical product, or food product.
49. The composition of claim 41 , wherein the composition is a fabric care product.
50. The composition of claim 41 , wherein the composition comprises at least one surfactant.
51. A composition comprising fiber and 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 up to about 3.0, and
(iv) at least 80% of the glycosidic linkages of the poly alpha-1,3-glucan ether compound are alpha-1,3 glycosidic linkages.
52. The composition of claim 51 , wherein at least one positively charged organic group comprises a substituted ammonium group.
53. The composition of claim 52 , wherein the positively charged organic group comprises trialkylammonium.
54. The composition of claim 53 , wherein the trialkylammonium is trimethylammonium.
55. The composition of claim 51 , wherein at least one positively charged organic group comprises an alkyl group or hydroxy alkyl group.
56. The composition of claim 55 , wherein at least one positively charged organic group is a quaternary ammonium hydroxypropyl group.
57. The composition of claim 51 , wherein at least 90% of the glycosidic linkages of the poly alpha-1,3-glucan ether compound are alpha-1,3 glycosidic linkages.
58. The composition of claim 51 , wherein said poly alpha-1,3-glucan ether compound is on the surface of the composition.
59. The composition of claim 51 , wherein the fiber is a natural fiber.
60. The composition of claim 59 , wherein natural fiber comprises cellulosic fiber.
61. The composition of claim 51 , wherein the fiber is a synthetic fiber.
62. The composition of claim 61 , wherein the synthetic fiber comprises polyester.
63. The composition of claim 51 , wherein the fiber is a semi-synthetic fiber, optionally wherein the semi-synthetic fiber comprises rayon.
64. The composition of claim 51 , wherein the composition is fabric.
65. The composition of claim 51 , wherein the composition is non-woven fabric, padding, or foam.
66. The composition of claim 51 , wherein the composition is paper.
67. A method of treating a material that comprises fabric, said method comprising:
contacting said 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 the positively charged organic group,
(iii) the compound has a degree of substitution up to about 3.0, and
(iv) at least 80% of the glycosidic linkages of the poly alpha-1,3-glucan ether compound are alpha-1,3 glycosidic linkages.