# US 11,078,381 B2 · Catechol-containing adhesive hydrogel, composition for preparing adhesive hydrogel, and compositions each including said adhesive hydrogel > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,078,381 B2 - Document ID: US11078381B2 - Status: Granted - Kind: B2 - Application number: 16/801,309 - Filed: 2020-02-26 - Published: 2020-06-18 - Granted: 2021-08-03 - Earliest claimed: 2015-05-26 - Assignees: Japan Science and Technology Agency - Applicants: Japan Science and Technology Agency - Inventors: Hiroshi Yabu; Matsuhiko Nishizawa; Kuniaki Nagamine; Yuta Saito; Jun Kamei; Tatsuaki Shimazaki; Shun Chihara - Web page: https://patentgrep.com/patent/US11078381B2 ## CPC - C09J 4/00: Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16} - A61K 6/30: Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives - A61L 24/0031: {Hydrogels or hydrocolloids} - A61L 24/06: obtained by reactions only involving carbon-to-carbon unsaturated bonds {(A61L24/043, A61L24/046 take precedence)} - A61L 26/00: Chemical aspects of, or use of materials for, {wound dressings or} bandages {in liquid, gel or powder form} - A61L 26/0014: {obtained by reactions only involving carbon-to-carbon unsaturated bonds} - A61L 26/008: {Hydrogels or hydrocolloids} - C08F 220/58: containing oxygen in addition to the carbonamido oxygen {, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine} - C09D 4/00: Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16} - C09D 5/16: Antifouling paints; Underwater paints - C09D 7/40: Additives - C09J 11/06: organic - C10M 107/22: Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds - C10M 107/24: containing monomers having an unsaturated radical bound to an alcohol, aldehyde, ketonic, ether, ketal or acetal radical - C10M 173/02: not containing mineral or fatty oils - C10M 2217/024: containing monomers having an unsaturated radical bound to an amido or imido group - C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H) - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) - A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K) - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D) - C10M: LUBRICATING COMPOSITIONS (well drilling compositions C09K8/02); USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION (mould release, i.e. separating, agents for metals B22C3/00, for plastics or substances in a plastic state, in general B29C33/56, for glass C03B40/02; textile lubricating compositions D06M11/00, D06M13/00, D06M15/00; immersion oils for microscopy G02B21/33) ## 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. ## Claims ### Claim 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. ### Claim 2 (depends on 1) 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. ### Claim 3 (depends on 1) The composition for preparing adhesive hydrogel according to claim 1, wherein the catechol group is derived from DOPA or a derivative thereof. ### Claim 4 (depends on 1) The composition for preparing adhesive hydrogel according to claim 1, wherein the water-soluble main chain monomer is a vinyl group-containing monomer. ### Claim 5 (depends on 1) The composition for preparing adhesive hydrogel according to claim 1, further comprising an electrolyte and/or a polar solvent. ### Claim 6 (depends on 1) 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. ### Claim 7 (depends on 1) A method of applying an amount of the composition of claim 1 onto a ship bottom effective to antifoul paint. ### Claim 8 (depends on 1) 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. ### Claim 9 (depends on 1) A method of applying an amount of the composition of claim 1 onto a base material effective to antifoul the base material. ### Claim 10 (depends on 1) 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. ### Claim 11 (depends on 1) 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. ### Claim 12 (depends on 11) 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. ### Claim 13 (depends on 11) The composition for preparing adhesive hydrogel according to claim 11, wherein the catechol group is derived from DOPA or a derivative thereof. ### Claim 14 (depends on 11) The composition for preparing adhesive hydrogel according to claim 11, wherein the water-soluble main chain monomer is a vinyl group-containing monomer. ### Claim 15 (depends on 11) The composition for preparing adhesive hydrogel according to claim 11, further comprising an electrolyte and/or a polar solvent. ### Claim 16 (depends on 11) 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. ### Claim 17 (depends on 11) A method of applying an amount of the composition of claim 11 onto a ship bottom effective to antifoul paint. ### Claim 18 (depends on 11) 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. ### Claim 19 (depends on 11) A method of applying an amount of the composition of claim 11 onto a base material effective to antifoul the base material. ### Claim 20 (depends on 11) 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. ### Claim 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. ### Claim 22 (depends on 21) The method of adhering according to claim 21, wherein the medical member is a sensor electrode, a stimulation electrode, or an implant.