POLY(OLIGOETHYLENE GLYCOL METHACRYLATE) HYDROGEL COMPOSITIONS, AND METHODS OF USE THEREOF

• US 20190321512A1
• Filed: 06/24/2019
• Published: 10/24/2019
• Est. Priority Date: 11/04/2014
• Status: Active Application

• Current Assignee: Mcmaster University
• Original Assignee: Mcmaster University
• Inventors: Hoare, Todd, Bakaic, Emilia, Smeets, Niels M.B., Deng, Xudong
• Application Number:
  US16/450,151
• Publication Number:
  US 20190321512A1
• Time in Patent Office: Days
• CPC Class Codes: A61L 24/0031 Hydrogels or hydrocolloids
• CPC Class Codes: A61L 24/043 Mixtures of macromolecular materials
• CPC Class Codes: A61L 26/0052 Mixtures of macromolecular compounds
• CPC Class Codes: A61L 26/008 Hydrogels or hydrocolloids
• CPC Class Codes: A61L 27/26 Mixtures of macromolecular compounds
• CPC Class Codes: A61L 27/52 Hydrogels or hydrocolloids
• CPC Class Codes: A61M 5/19 having more than one chamber , e.g. including a manifold coupling two parallelly aligned syringes through separate channels to a common discharge assembly surgical glue applicators A61B17/00491
• CPC Class Codes: C08L 71/02 Polyalkylene oxides

Abstract

The present application relates to hydrogel compositions comprising first and second precursor polymers, wherein the precursor polymers are modified poly(oligoethylene glycol methacrylate) copolymers that are crosslinked through electrophile-nucleophile reactions.

Claims

1. A nucleophile-functionalized poly(oligoethylene glycol methacrylate) polymer which comprises a nucleophilic moiety which is a hydrazide or amine derivative, a carbonyl hydrate, an alcohol, cyanohydrin or cyanohydrin derivative, a thiol or thiol derivative, or a phosphorus ylide or derivatives thereof.

2. The polymer of claim 1, wherein the nucleophilic moiety is a hydrazide moiety.

3. The polymer of claim 1, wherein the polymer comprises monomeric units of:

a. a first monomer which is oligoethylene glycol methacrylate, or a derivative thereof; and

b. at least a second polymerizable monomer which is functionalized or is capable of being functionalized with a hydrazide moiety.

4. The polymer of claim 3, wherein the first monomer has the structure of the formula (I)

5. The hydrogel composition of claim 4, wherein

R¹ is H or (C₁-C₄)alkyl, and

R² is H, (C₁-C₄)alkyl, -(C₀-C₂)-alkylene-phenyl, or —

C(O)O—

R′

, wherein R′

is H or (C₁-C₄)alkyl.

6. The polymer of claim 3, wherein the second polymerizable monomer has a carboxylic acid moiety.

7. The polymer of claim 6, wherein the second polymerizable monomer is acrylic acid or a derivative thereof, methacrylic acid, itaconic acid, fumaric acid, maleic acid, or vinylacetic acid.

8. The polymer of claim 3, further comprising one or more monomers which are methacrylic acid, itaconic acid, fumaric acid, maleic acid, vinylacetic acid or tert-butyl-2-acryloylhydrazinecarboxylate (BAHC), 2-dimethylaminoethylmethacrylate (DMAEMA), 2-dimethylaminoethyacrylate (DMAEA), aminoethyl methacrylate (AEMA), allylamine, or derivatives of any of the above, or which has the structure of the formula (II)

9. A method for coating a porous substrate, the method comprising adsorbing or reacting a compound with the porous substrate, wherein the compound comprises a nucleophile-functionalized poly(oligoethylene glycol methacrylate) polymer as defined in claim 1.

10. The method of claim 9 wherein the compound comprises a nucleophilic moiety which is a hydrazide or amine derivative, carbonyl hydrate, an alcohol, cyanohydrin or cyanohydrin derivative, a thiol or thiol derivative, or a phosphorus ylide or derivatives thereof.

11. The method of claim 10, wherein the nucleophilic moiety is a hydrazide or amine, or derivative thereof.

12. The method of claim 11, wherein the nucleophilic moiety is a hydrazide or hydrazide derivative.

13. The method of claim 9, wherein the porous substrate is a membrane or filter.

14. The method of claim 9, wherein the porous substrate comprises cellulose.

15. The method of claim 9, further comprising reacting the compound with an electrophile-functionalized poly(oligoethylene glycol methacrylate) second polymer, wherein the compound and second polymer are crosslinked through covalent bonds by reaction of the nucleophilic and electrophilic moieties.

16. The method of claim 15, wherein a hydrogel is formed on the substrate.

17. A coated porous substrate comprising a porous substrate and a compound adsorbed or reacted with the porous substrate, wherein the compound comprises a nucleophile-functionalized poly(oligoethylene glycol methacrylate) polymer as defined in claim 1.

18. The coated porous substrate of claim 17, wherein the compound comprises a nucleophilic moiety which is a hydrazide or amine derivative, carbonyl hydrate, an alcohol, cyanohydrin or cyanohydrin derivative, a thiol or thiol derivative, or a phosphorus ylide or derivatives thereof.

19. The coated porous substrate of claim 18 wherein the compound is a hydrazide or amine derivative.

20. The coated porous substrate of claim 17, wherein the porous substrate is a membrane or filter