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WO-2026096472-A1 - METHODS FOR PRODUCING CATIONIC 1,3-ALPHA-GLUCAN

WO2026096472A1WO 2026096472 A1WO2026096472 A1WO 2026096472A1WO-2026096472-A1

Abstract

Cationic α-1,3-glucans and methods for producing cationic α-1,3-glucans, and compositions that include cationic α-1,3-glucans, which may be used as a polyelectrolyte, a flocculant, etc. The methods may include contacting a α-1,3-glucan and a haloacyl halide to produce a haloacylated α-1,3-glucan, and contacting the haloacylated α-1,3-glucan and the amine to produce the cationic α-1,3-glucan. The methods may include forming one or more suspensions in which α-1,3-glucan is dispersed.

Inventors

  • METSÄLÄ, Erkki Johannes

Assignees

  • KEMIRA OYJ
  • KEMIRA WATER SOLUTIONS INC.

Dates

Publication Date
20260507
Application Date
20251028
Priority Date
20241210

Claims (20)

  1. Claims -
  2. 1. A method for producing a cationic polysaccharide, the method comprising:
  3. contacting a-l,3-glucan and a haloacyl halide to produce a haloacylated a-1,3- glucan; and
  4. contacting the haloacylated a-l,3-glucan and an amine to produce a cationic a- 1,3 -glucan;
  5. wherein the contacting of the a-l,3-glucan and the haloacyl halide comprises - contacting the a-l,3-glucan and a first liquid to form a first mixture, wherein the a-l,3-glucan is insoluble, or partially soluble in the first liquid, and the first mixture is a suspension in which the a-l,3-glucan is dispersed; and
  6. disposing the haloacyl halide in the first mixture.
  7. 2. The method of claim 1, wherein the first liquid comprises a polar organic liquid.
  8. 3. The method of claim 2, wherein the polar organic liquid comprises dimethylformamide (DMF).
  9. 4. The method of claim 1, wherein the haloacylated a-1,3-glucan is soluble in the first liquid.
  10. 5. The method of claim 1, further comprising:
  11. disposing the haloacylated a- 1,3 -glucan in a second liquid to form a second mixture;
  12. wherein the contacting of the contacting the haloacylated a-l,3-glucan and the amine comprises disposing the amine in the second liquid.
  13. 6. The method of claim 5, wherein the second liquid is a solvent in which the haloacylated a-l,3-glucan is soluble, and wherein the second mixture is a homogeneous mixture.
  14. 7. The method of claim 5, wherein the second liquid comprises a polar organic liquid. 8. The method of claim 7. wherein the polar organic liquid comprises acetonitrile, dimethyl sulfoxide, or a combination thereof.
  15. 9. The method of claim 1, wherein (i) the contacting of the a-l,3-glucan and the haloacyl halide, and (ii) the contacting of the haloacylated a-l,3-glucan and the amine are performed in anhydrous conditions.
  16. 10. The method of claim 1, wherein the haloacyl halide comprises chloroacetyl chloride.
  17. 11. The method of claim 1, wherein the haloacyl halide comprises a compound of the following formula:
  18. wherein R is a divalent Ci-Ce hydrocarbyl; and
  19. wherein X 1 and X 2 are independently selected from a halogen.
  20. 12. The method of claim 1, wherein the amine is a tertiary (3°) amine.

Description

METHODS FOR PRODUCING CATIONIC 1,3-ALPHA-GLUCAN Cross-reference to Related Applications [0001] This application claims priority to Finnish Patent Application No. 20246442, filed December 10, 2024, and U. S. Provisional Patent Application No. 63/713,415, filed October 29, 2024, which are incorporated by reference herein. Background [0002] Cationic polysaccharides are useful in a number of processes, compositions, etc. (e g., WO2023287684). For example, cationic polysaccharides or compositions that include cationic polysaccharides may be used as polyelectrolytes, flocculants, etc. [0003] There remains a need for cationic polysaccharides and methods for producing cationic polysaccharides, such as betainate substituted a-1.3-glucans. There also remains a need for cationic polysaccharides that are hydrolysable, including those that are hydrolysable and capable of maintaining cationicity for a time effective to serve one or more purposes or roles, such as to serve as a flocculant. There also remains a need for cationic polysaccharides that are biodegradable, including those that biodegrade into one or more environmentally benign decomposition products. Brief Summary [0004] Provided herein are cationic a- 1,3 -glucans, methods of producing cationic a-1,3-glucans, and compositions that address one or more of the foregoing needs. [0005] In one aspect, methods for producing cationic polysaccharides, such as cationic a-l,3-glucans are provided. In some embodiments, the methods include contacting a-l,3-glucan, ahaloacyl halide, and an amine, such as a tertiary amine, to produce a cationic a-l,3-glucan. In some embodiments, the methods include contacting a-l,3-glucan, a haloacyl halide, an amine, such as a primary or secondary' amine, and a quaternizing agent to produce a cationic a-l,3-glucan. The contacting of the a-l,3-glucan, the haloacyl halide, and the amine may include contacting the a-l,3-glucan and the haloacyl halide to produce a haloacylated a-l,3-glucan; and contacting the haloacylated a-l,3-glucan and the amine (or the amine and the quaternizing agent) to produce the cationic a- 1,3 -glucan. [0006] In another aspect, cationic a-l,3-glucans and compositions that include cationic a-l,3-glucans are provided. The cationic a-l,3-glucans or the compositions that include the cationic a-1,3-glucans may be used as a flocculant or a polyelectrolyte. [0007] Additional aspects will be set forth in part in the description which follows, and in part will be obvious from the description, or may be learned by practice of the aspects described herein. The advantages described herein may be realized and attained by means of the elements and combinations particularly pointed out in the appended claims. It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are not restrictive. Detailed Description [0008] Provided herein are methods for producing cationic polysaccharides, such as cationic a- 1,3 -glucans. The methods generally may include (i) contacting a-l,3-glucan, a haloacyl halide, and an amine, such as a tertiary amine, to produce a cationic a-l,3-glucan; or (ii) contacting a-l,3-glucan, a haloacyl halide, an amine, such as a primary or a secondary amine, and a quaternizing agent to produce a cationic a-l,3-glucan. [0009] The contacting of the a-l,3-glucan, the haloacyl halide, and the amine (or the amine and the quaternizing agent) may be achieved using any known technique and any known apparatuses. The starting materials also may be contacted in any order or in any manner. Any combination of temperature and pressure may be used to effect any of the chemical reactions among the starting materials, intermediate products, etc. [0010] The contacting of the a-l,3-glucan, the haloacyl halide, and the amine may include contacting the a-1.3-glucan and the haloacyl halide to produce a haloacylated a-1,3-glucan; and contacting the haloacylated a-1,3-glucan and the amine (or the amine and the quaternizing agent) to produce the cationic a-l,3-glucan. [0011] The a-l,3-glucan used as a starting material in the methods described herein may be obtained from any source. The a-l,3-glucan may be made according to known methods, such as those disclosed in U. S. Patent No. 8,642,757, U. S. Patent No. 9,139,718, U. S. Patent No. 9,169,506, U. S. Patent No. 10,472,657, and U. S. Patent No. 10,774,352. For example, poly a-l,3-glucan can be enzymatically produced from sucrose using one or more glucosyltransferase (gtf) enzymes (e.g., gtfJ), such as those disclosed in U. S. Patent No. 7,000,000, U. S. Patent Application Publication No. 2013/0244288 and U. S. Patent Application Publication No. 2013/0244287. [0012] Generally, a a-l,3-glucan may be contacted with any amount of a haloacyl halide. Similarly, a haloacylated a-l,3-glucan may be contacted with any amount of an amine (or amine and quaternizing agent). In some embodiments, a mole ratio of the a-1