Catechol-containing adhesive hydrogel, composition for preparing adhesive hydrogel, and compositions each including said adhesive hydrogel

Patent metadata

Field	Value
Publication number	US-11078381-B2
Application number	US-202016801309-A
Country	US
Kind code	B2
Filing date	Feb 26, 2020
Priority date	May 26, 2015
Publication date	Aug 3, 2021
Grant date	Aug 3, 2021

Abstract

A hydrogel that adheres to the surface of materials is provided by using as constituent elements a water-soluble main chain monomer, crosslinking agent, polymerization initiator, and adhesive monomer having at least a catechol group in a side chain.

First claim

What is claimed is:

1. A composition for preparing adhesive hydrogel including a water-soluble main chain monomer, a crosslinking agent, a polymerization initiator, an adhesive monomer having a catechol group in a side chain, and water, provided that any inorganic nano-silicate in not included.

2. The composition for preparing adhesive hydrogel according to claim 1 , wherein the adhesive monomer is added in a proportion of 8% or more to the total number of mol of the main chain monomer and the adhesive monomer.

3. The composition for preparing adhesive hydrogel according to claim 1 , wherein the catechol group is derived from DOPA or a derivative thereof.

4. The composition for preparing adhesive hydrogel according to claim 1 , wherein the water-soluble main chain monomer is a vinyl group-containing monomer.

5. The composition for preparing adhesive hydrogel according to claim 1 , further comprising an electrolyte and/or a polar solvent.

6. The composition for preparing adhesive hydrogel according to claim 1 , wherein the crosslinking agent is a crosslinking agent capable of introducing a three-dimensional crosslinked structure by polymerizable double bonds.

7. A method of applying an amount of the composition of claim 1 onto a ship bottom effective to antifoul paint.

8. A method of coating a base material with an amount of the composition of claim 1 effective to lubricate the top of the base material.

9. A method of applying an amount of the composition of claim 1 onto a base material effective to antifoul the base material.

10. A method for synthesizing an adhesive hydrogel including (i) a step of preparing a prepolymer aqueous solution containing a composition of claim 1 , and (ii) a polymerization initiation step for conducting a polymerization initiation reaction in the prepolymer aqueous solution.

11. The composition for preparing adhesive hydrogel according to claim 1 , substantially composed of a water-soluble main chain monomer, a crosslinking agent, a polymerization initiator, an adhesive monomer having a catechol group in a side chain, agents which are used to make buffer action in the adhesive hydrogel and water, and wherein the adhesive monomer is added in a proportion of 5% or more to the total number of mol of the main chain monomer and the adhesive monomer.

12. The composition for preparing adhesive hydrogel according to claim 11 , wherein the adhesive monomer is added in a proportion of 8% or more to the total number of mol of the main chain monomer and the adhesive monomer.

13. The composition for preparing adhesive hydrogel according to claim 11 , wherein the catechol group is derived from DOPA or a derivative thereof.

14. The composition for preparing adhesive hydrogel according to claim 11 , wherein the water-soluble main chain monomer is a vinyl group-containing monomer.

15. The composition for preparing adhesive hydrogel according to claim 11 , further comprising an electrolyte and/or a polar solvent.

16. The composition for preparing adhesive hydrogel according to claim 11 , wherein the crosslinking agent is a crosslinking agent capable of introducing a three-dimensional crosslinked structure by polymerizable double bonds.

17. A method of applying an amount of the composition of claim 11 onto a ship bottom effective to antifoul paint.

18. A method of coating a base material with an amount of the composition of claim 11 effective to lubricate the top of the base material.

19. A method of applying an amount of the composition of claim 11 onto a base material effective to antifoul the base material.

20. A method for synthesizing an adhesive hydrogel including (i) a step of preparing a prepolymer aqueous solution containing a composition of claim 11 , and (ii) a polymerization initiation step for conducting a polymerization initiation reaction in the prepolymer aqueous solution.

21. A method of (i) adhering bone, teeth, or soft tissues, or (ii) of adhering bone, teeth, or soft tissue and a medical member, with an adhesive in a medical field,
the adhesive comprising a composition for preparing adhesive hydrogel including:

a water-soluble main chain monomer,
a crosslinking agent,
a polymerization initiator,
an adhesive monomer having a catechol group in a side chain, and
water,
wherein the adhesive monomer is added in a proportion of 5% or more to the total number of mol of the main chain monomer and the adhesive monomer,
and wherein all of the catechol groups of the adhesive monomer can participate in adhesion to a substrate and the hydrogel has a structure in which the catechol groups are present in the polymer in a free state.

22. The method of adhering according to claim 21 , wherein the medical member is a sensor electrode, a stimulation electrode, or an implant.

Assignees

• Japan Science & Tech Agency

Inventors

• Yabu Hiroshi
• Nishizawa Matsuhiko
• Nagamine Kuniaki
• Saito Yuta
• Kamei Jun
• Shimazaki Tatsuaki
• CHIHARA Shun

Classifications

• C08F220/58 Primary

  containing oxygen in addition to the carbonamido oxygen {, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine} · CPC title

• C09J11/06

  organic · CPC title

• A61L26/0014

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

• C09D7/40

  Additives · CPC title

• C10M107/24

  containing monomers having an unsaturated radical bound to an alcohol, aldehyde, ketonic, ether, ketal or acetal radical · CPC title