Copolymer comprising a lignin or lignin derivative and a poly(alkylene oxide) alkyl ether (meth)acrylate, and a hydrogel comprising the copolymer

Patent metadata

Field	Value
Publication number	US-10683382-B2
Application number	US-201615552262-A
Country	US
Kind code	B2
Filing date	Feb 18, 2016
Priority date	Feb 18, 2015
Publication date	Jun 16, 2020
Grant date	Jun 16, 2020

Abstract

A copolymer comprising an oxygenated polyaromatic alcohol and a poly (alkylene oxide) alkyl ether (meth)acrylate is disclosed, wherein the oxygenated polyaromatic alcohol is preferably lignin or lignin derivative. A hydrogel comprising the copolymer and a cyclic oligosaccharide such as α-cyclodextrin is also disclosed, which can be used in biomedical or personal care industries, for example as a carrier for an active agent.

First claim

The invention claimed is:

1. A hydrogel comprising:
1 wt % to 4 wt % of a copolymer comprising an oxygenated polyaromatic alcohol and a poly (alkylene oxide) alkyl ether (meth)acrylate; and
6 wt % to 14 wt % of a cyclic oligosaccharide.

2. The hydrogel of claim 1 , wherein said copolymer has a molecular weight in the range of 5,000 g/mol to 500,000 g/mol.

3. The hydrogel of claim 1 , wherein said copolymer has a polydispersity of at least 1.

4. The hydrogel of claim 1 , wherein said copolymer has a melting temperature in the range of 32° C. to 36° C.

5. The hydrogel of claim 1 , wherein said copolymer has a degradation temperature in the range of 350° C. to 370° C.

6. The hydrogel of claim 1 , wherein said copolymer has 5 to 1,000 molecules of poly (alkylene oxide) alkyl ether (meth)acrylate bound to each molecule of the oxygenated polyaromatic alcohol.

7. The hydrogel of claim 1 , wherein said oxygenated polyaromatic alcohol is a lignin or a lignin derivative,
wherein said lignin is selected from the group consisting of lignin, steam explosion lignin, acid hydrolysis lignin, lignosulfonate, soda lignin and organosolv lignin or
wherein said lignin derivative is selected from the group consisting of lignin esters, lignin ethers, carboxy lignins, hydroxyalkylated lignin, acylated lignin and hydroxyalkoxy lignins or is further selected from the group consisting of lignin acetate, lignin propionate, lignin butyrate, lignin ethyl ether, lignin methyl ether, carboxymethyl lignin, (hydroxyethoxy) lignin, and (hydroxypropoxy) lignin.

8. The hydrogel of claim 1 , wherein said oxygenated polyaromatic alcohol is contained in said copolymer at a weight percentage in the range of 0.5% to 90%.

9. The hydrogel of claim 1 , wherein said poly (alkylene oxide) alkyl ether (meth)acrylate is selected from the group consisting of poly (ethylene glycol) methyl ether (meth)acrylate, poly (ethylene glycol) ethyl ether (meth)acrylate, poly (propylene glycol) methyl ether (meth)acrylate, poly (propylene glycol) ethyl ether (meth)acrylate, and mixtures thereof.

10. The hydrogel of claim 1 , wherein said poly (alkylene oxide) alkyl ether (meth)acrylate is a grafted polymer, a block copolymer, a star polymer, a brush polymer or a hyperbranched polymer.

11. The hydrogel of claim 1 , wherein said poly (alkylene oxide) alkyl ether (meth) acrylate contains an average number of alkylene oxide groups in the range of from 2 to 460.

12. The hydrogel of claim 1 , wherein said poly (alkylene oxide) alkyl ether (meth)acrylate has a molecular weight in the range of 200 g/mol to 20,000 g/mol.

13. The hydrogel of claim 1 , further comprising a polymer selected from the group consisting of polyester, polyurethane, polyamide, polyether, polysaccharide, poly(amino acid)s, polypeptides and proteins.

14. The hydrogel of claim 1 wherein the cyclic oligosaccharide is selected from the group consisting of α-cyclodextrin, β-cyclodextrin, γ-cyclodextrin and methyl-β-cyclodextrin.

15. The hydrogel of claim 1 , having a storage modulus in the range of 0.01 Pa to 100 GPa.

16. A method for forming a hydrogel comprising adding a cyclic oligosaccharide to a copolymer to form a mixture that undergoes gelation to form the hydrogel, wherein said copolymer comprises an oxygenated polyaromatic alcohol and a poly (alkylene oxide) alkyl ether (meth)acrylate, and wherein the formed hydrogel comprises about 1 wt % to about 4 wt % of said copolymer and about 6 wt % to about 14 wt % of said cyclic oligosaccharide.

17. The method of claim 16 , wherein said mixture is 1) a copolymer aqueous solution mixed with a cyclic oligosaccharide aqueous solution, or 2) the cyclic oligosaccharide in powder form added to a copolymer aqueous solution.

18. The method of claim 17 , wherein said copolymer aqueous solution comprises 0.1 wt % to 80 wt % of said copolymer, based on the weight of the mixture.

19. The method of claim 16 , wherein the mixture contains 1 wt % to 50 wt % of the cyclic oligosaccharide, based on the weight of the mixture.

Assignees

• Agency Science Tech & Res

Inventors

• Kai Dan
• Loh Xian Jun

Classifications

• C08G83/003

  Dendrimers · CPC title

• C08F220/286

  and containing polyethylene oxide in the alcohol moiety, e.g. methoxy polyethylene glycol (meth)acrylate · CPC title

• C08G83/005

  Hyperbranched macromolecules · CPC title

• A61L27/18

  obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• C08L2203/02

  for biomedical use · CPC title