Polysaccharide derivatives and cross-metathesis processes for preparing them

Patent metadata

Field	Value
Publication number	US-10851179-B2
Application number	US-201515125787-A
Country	US
Kind code	B2
Filing date	Mar 16, 2015
Priority date	Mar 14, 2014
Publication date	Dec 1, 2020
Grant date	Dec 1, 2020

Abstract

Methods for the cross-metathesis of polysaccharides with one or more olefin-terminated side chains and cross-metathesized products are described. In an exemplary embodiment, a method for the synthesis of cellulose ω-carboxyesters via olefin cross-metathesis with acrylates is described. Conditions of the reactions were relatively mild and the olefin-substituted polysaccharides and the appropriate acrylate partners appear to follow Grubbs rules as summarized herein. Additionally, a method of hydrogenation of the cross-metathesized product is described. The compounds and methods may be useful for waterborne coating applications, adhesives, lubricants, or any product in need of dispersion in an aqueous media.

First claim

The invention claimed is:

1. A compound having the formula:

wherein:
R is H, methyl, ethyl, acetyl, propionyl, or butyryl;
n=10-10,000; and

2. The compound of claim 1 , wherein:
m=8 and

3. The compound of claim 2 , wherein R═H.

4. The compound of claim 2 , wherein R=acetyl.

5. The compound of claim 1 , wherein:
m=8 and

 wherein a=1-3.

6. The compound of claim 5 , wherein R═H.

7. The compound of claim 5 , wherein R=acetyl.

8. The compound of claim 1 , wherein:
m=8 and

9. The compound of claim 8 , wherein R═H.

10. The compound of claim 8 , wherein R=acetyl.

11. The compound of claim 1 , wherein:
m=2 and

12. The compound of claim 11 , wherein R═H.

13. The compound of claim 11 , wherein R=acetyl.

14. The compound of claim 1 , wherein:
m=2 and

 wherein a=1-3.

15. The compound of claim 14 , wherein R═H.

16. The compound of claim 14 , wherein R=acetyl.

17. The compound of claim 1 , wherein the compound is amphiphilic.

18. A composition comprising:
an aqueous solution, suspension, or colloid of a compound having the formula:

wherein:
R is H, methyl, ethyl, acetyl, propionyl, or butyryl;
n=10-10,000; and
m=b and

 or
m=8 and

 wherein a=1-3; or

 wherein a=1-3.

19. A composition comprising:
a compound having the formula:

wherein:
R is H, methyl, ethyl, acetyl, propionyl, or butyryl;
n=10-10,000; and

 wherein a=1-3;

wherein the composition is in the form of a coating, adhesive, and/or lubricant.

20. The composition of claim 19 , wherein the compound is amphiphilic and dispersible in water.

Assignees

• Edgar Kevin J
• Meng Xiangtao
• Dong Yifan
• Virginia Tech Intellectual Properties Inc

Inventors

• Edgar Kevin J
• Meng Xiangtao
• Dong Yifan

Classifications

• C08L33/02 Primary

  Homopolymers or copolymers of acids; Metal or ammonium salts thereof · CPC title

• C08B11/193

  Mixed ethers, i.e. ethers with two or more different etherifying groups · CPC title

• C08B11/20

  Post-etherification treatments of chemical or physical type, {e.g. mixed etherification in two steps}, including purification · CPC title

• C08F290/10

  Polymers provided for in subclass C08B · CPC title

• C08B37/00

  Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof (cellulose D21; {microbiological processes C12P}) · CPC title