Bifunctional modified biopolymer based polymers and hydrogels obtainable from such bifunctional modified biopolymer based polymers

Patent metadata

Field	Value
Publication number	US-2021198433-A1
Application number	US-201917058368-A
Country	US
Kind code	A1
Filing date	May 29, 2019
Priority date	May 31, 2018
Publication date	Jul 1, 2021
Grant date	—

Abstract

The invention relates to a bifunctional modified biopolymer based polymer, comprising at least one polymer chain comprising n first functional groups and m second functional groups. The first functional groups comprise groups able of being radically cross-linked following a free radical chain- growth polymerisation. The second functional groups comprise groups able to thiol-ene crosslinking. Preferred bifunctional modified biopolymer based polymers comprise bifunctional modified gelatin and bifunctional modified collagen. The invention further relates to a method to prepare such a bifunctional modified biopolymer based polymer and to a method to prepare a hydrogel starting from such bifunctional modified biopolymer based polymer. Furthermore the invention relates to hydrogels obtainable starting from such bifunctional modified biopolymer based polymers and to the use of such hydrogels.

First claim

1 - 15 . (canceled)

16 . A bifunctional modified biopolymer based polymer comprising at least one polymer chain, wherein:
the at least one polymer chain comprises n first functional groups and m second functional groups, with both n and m not being zero; the first functional groups comprise groups that are radically cross-linkable following a free radical chain-growth polymerization; and the second functional groups comprise thiol-ene cross-linkable groups that remain unreacted during free radical chain-growth polymerization of the first functional groups.

17 . The bifunctional modified biopolymer based polymer of claim 16 , wherein the biopolymer based polymer is selected from the group consisting of polypeptides, proteins, polysaccharides, nucleic acids, gelatins, collagens, alginates, dextrans, agarose, glycosaminoglycans, chitosans and carrageenans, derivates thereof, recombinant analogues thereof, and synthetic analogues thereof.

18 . The bifunctional modified biopolymer based polymer of claim 16 , wherein the first functional groups comprise methacrylamide functional groups, acrylamide functional groups, methacrylate functional groups, acrylate functional groups, or combinations thereof.

19 . The bifunctional modified biopolymer based polymer of claim 16 , wherein the second functional groups comprise norbornene functional groups, vinylether functional groups, vinyl ester functional groups, allyl ether functional groups, propenyl ether functional groups, alkene functional groups, N-vinylamide functional groups, or combinations thereof.

20 . The bifunctional modified biopolymer based polymer of claim 16 , wherein:
the first functional groups comprise methacrylamide functional groups, acrylamide functional groups, methacrylate functional groups, acrylate functional groups, or combinations thereof; and the second functional groups comprise norbornene functional groups, vinylether functional groups, vinyl ester functional groups, allyl ether functional groups, propenyl ether functional groups, alkene functional groups, N-vinylamide functional groups, or combinations thereof.

21 . The bifunctional modified biopolymer based polymer of claim 16 , wherein the biopolymer based polymer comprises exactly one polymer chain.

22 . A method to prepare a bifunctional modified biopolymer based polymer according to claim 16 from a biopolymer based polymer comprising at least one polymer chain comprising primary functional groups, the method comprising:
functionalizing a first part of the primary functional groups to introduce n first functional groups, with n not being zero, the first functional groups being radically cross-linkable following a free radical chain-growth polymerization; and
functionalizing a second part of the primary functional groups to introduce m second functional groups, with m not being zero, the second functional groups comprising thiol-ene cross-linkable groups that remain unreacted during free chain-growth polymerization of the primary functional groups,

wherein the functionalizing the first part of the primary functional groups and the functionalizing the second part of the primary functional groups are performed simultaneously or sequentially in any order.

23 . The method of claim 22 , wherein:
the primary functional groups comprise amine functional groups and/or carboxylic acid functional groups and/or hydroxyl functional groups; and functionalizing the first part of the primary functional groups comprises a reaction of the amine functional groups and/or a reaction of the carboxylic acid functional groups and/or a reaction of the hydroxyl functional groups.

24 . The method of claim 22 , wherein:
the primary functional groups comprise amine functional groups and/or carboxylic acid functional groups and/or hydroxyl functional groups; and functionalizing the second part of the primary functional groups comprises a reaction of the amine functional groups and/or a reaction of the carboxylic acid functional groups and/or a reaction of the hydroxyl functional groups.

25 . The method of claim 24 , wherein the reaction of the amine functional groups and/or the reaction with the carboxylic acid functional groups and/or the reaction with the hydroxyl functional groups comprises a carbodiimide coupling reaction.

26 . A method to prepare a hydrogel, the method comprising:
crosslinking a bifunctional modified biopolymer based polymer according to claim 16 by free radical chain-growth polymerization of at least a part of the n first functional groups; and crosslinking and/or functionalizing at least a part of the m second functional groups.

27 . The method of claim 26 , wherein crosslinking and/or functionalizing at least a part of the m second functional groups comprises crosslinking of at least a part of the m second functional groups.

28 . The method of claim 26 , wherein crosslinking and/or functionalizing at least a part of the m second functional groups comprises functionalizing at least part of the m functional groups.

29 . The method of claim 26 , wherein crosslinking and/or functionalizing at least a part of the m second functional groups comprises crosslinking a first part of the m functional groups and functionalizing a second part of the m functional groups.

30 . A hydrogel obtained by the method according to claim 26 .

31 . The hydrogel of claim 30 , adapted as a wound dressing.

Assignees

• Univ Gent
• Univ Brussel Vrije

Inventors

• Van Hoorick Jasper
• Van Vlierberghe Sandra

Classifications

• C08L89/06

  derived from leather or skin {, e.g. gelatin} · CPC title

• A61L27/52

  Hydrogels or hydrocolloids · CPC title

• A61L26/0038

  Gelatin · CPC title

• C08H1/06 Primary

  derived from horn, hoofs, hair, skin or leather · CPC title

• A61L27/222

  Gelatin · CPC title