# US 12,215,182 B2 · Urethane prepolymer, adhesive, skin patch material, adhesive tape, wearable device, and wearable device kit > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,215,182 B2 - Document ID: US12215182B2 - Status: Granted - Kind: B2 - Application number: 17/399,512 - Filed: 2021-08-11 - Published: 2021-12-02 - Granted: 2025-02-04 - Earliest claimed: 2019-02-28 - Assignees: AGC Inc. - Applicants: AGC Inc. - Inventors: Makito Nakamura; Haru Kawasaki; Hitoshi Shimoma; Chitoshi Suzuki; Hiroshi Wada - Web page: https://patentgrep.com/patent/US12215182B2 ## CPC - C08G 18/12: using two or more compounds having active hydrogen in the first polymerisation step - C08G 18/246: {containing also tin-carbon bonds} - A61B 5/6833: {Adhesive patches} - A61F 13/0253: {characterized by the adhesive material} - C08G 18/10: Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step - C08G 18/283: {Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds} - C08G 18/4812: {Mixtures of polyetherdiols with polyetherpolyols having at least three hydroxy groups} - C08G 18/4825: {Polyethers containing two hydroxy groups (C08G18/4833 - C08G18/5096 take precedence)} - C08G 18/4829: {Polyethers containing at least three hydroxy groups (C08G18/4833 - C08G18/5096 take precedence)} - C08G 18/4833: {Polyethers containing oxyethylene units} - C08G 18/4837: {and other oxyalkylene units} - C08G 18/73: acyclic - C09J 7/38: Pressure-sensitive adhesives [PSA] - C09J 175/08: from polyethers - C08G 2170/40: Compositions for pressure-sensitive adhesives - C09J 2301/122: the adhesive layer being present only on one side of the carrier, e.g. single-sided adhesive tape - C09J 2475/00: Presence of polyurethane - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - A61B: DIAGNOSIS; SURGERY; IDENTIFICATION (usefulness limited to only animals A61D) - A61F: FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS (dental prosthetics A61C) - 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) ## Abstract Provided are a urethane prepolymer from which is obtained an adhesive which has excellent moisture permeability and which attains both low adhesion to skin and high adhesion to a base material, an adhesive, a skin patch material, an adhesive tape, a wearable device, and a wearable device kit. The urethane prepolymer is a hydroxyl-group-terminated urethane prepolymer obtained by reacting an oxyalkylene polymer A having an average number of hydroxyl groups per molecule of 2.1 to 3, an oxyalkylene polymer B in which the number of hydroxyl groups per molecule is 1, and a diisocyanate compound, the number-average molecular weight of the oxyalkylene polymer B being 5000 or greater, and the content of ethylene oxide units in the hydroxyl-group-terminated urethane prepolymer being more than 10 mass %. ## Claims ### Claim 1 A pressure-sensitive adhesive, obtained by a process comprising: reacting an oxyalkylene polymer A having an average number of hydroxy groups per molecule of from 2.1 to 3, an oxyalkylene polymer B having one hydroxy group per molecule, and a polyisocyanate compound, wherein the pressure-sensitive adhesive has a difference between adhesion to a phenol resin and adhesion to human skin of at least 2 N/15 mm, the oxyalkylene polymer B has a number average molecular weight of at least 5,000, the oxyalkylene polymer B has a molecular weight distribution Mw/Mn of less than 1.20 where Mw is a mass average molecular weight and Mn is a number average molecular weight, the oxyalkylene polymer B has a degree of unsaturation of at most 0.015 meq/g, and the pressure-sensitive adhesive has a content of ethylene oxide units of at least 10 mass %. ### Claim 2 (depends on 1) The pressure-sensitive adhesive of claim 1, wherein the number average molecular weight of the oxyalkylene polymer B is more than 5,000. ### Claim 3 (depends on 1) The pressure-sensitive adhesive of claim 1, wherein the oxyalkylene polymer A includes an oxyalkylene polymer a having three hydroxy groups per molecule and an oxyalkylene polymer b having two hydroxy groups per molecule. ### Claim 4 (depends on 3) The pressure-sensitive adhesive of claim 3, wherein the content of ethylene oxide units in the oxyalkylene polymer a is at least 15 mass %. ### Claim 5 (depends on 1) The pressure-sensitive adhesive of claim 1, wherein the content of ethylene oxide units in the pressure-sensitive adhesive is from 12 to 50 mass %. ### Claim 6 (depends on 1) The pressure-sensitive adhesive of claim 1, wherein the pressure-sensitive adhesive has a storage elastic modulus at 80° C. of at most 4.0×105 Pa. ### Claim 7 (depends on 1) The pressure-sensitive adhesive of claim 1, wherein the pressure-sensitive adhesive has a moisture permeability of at least 3,000 g/m2·day. ### Claim 8 (depends on 1) The pressure-sensitive adhesive of claim 1, wherein the pressure-sensitive adhesive has an adhesion to human skin, of from 0.2 to 1 N/15 mm. ### Claim 9 (depends on 1) An adhesive skin patch, comprising: a substrate; and a pressure-sensitive adhesive layer formed on a surface of the substrate and comprising the pressure-sensitive adhesive of claim 1. ### Claim 10 (depends on 1) A pressure-sensitive adhesive tape, comprising: a substrate; and a pressure-sensitive adhesive layer formed on at least one surface of the substrate and comprising the pressure-sensitive adhesive of claim 1. ### Claim 11 (depends on 1) A wearable device, comprising: a wearable device body; and a pressure-sensitive adhesive layer formed on at least a part of an adherend surface of the wearable device body and comprising the pressure-sensitive adhesive of claim 1. ### Claim 12 (depends on 1) A wearable device kit, comprising: a wearable device body; and the pressure-sensitive adhesive of claim 1 for attaching the wearable device body to skin. ### Claim 13 (depends on 9) A wearable device kit, comprising: a wearable device body; and the adhesive skin patch of claim 9 for attaching the wearable device body to skin. ### Claim 14 (depends on 10) A wearable device kit, comprising: a wearable device body; and the pressure-sensitive adhesive tape of claim 10 for attaching the wearable device body to skin. ### Claim 15 (depends on 2) The pressure-sensitive adhesive of claim 2, wherein the oxyalkylene polymer A includes an oxyalkylene polymer a having three hydroxy groups per molecule and an oxyalkylene polymer b having two hydroxy groups per molecule. ### Claim 16 (depends on 15) The pressure-sensitive adhesive of claim 15, wherein the content of ethylene oxide units in the oxyalkylene polymer a is at least 15 mass %. ### Claim 17 (depends on 2) The pressure-sensitive adhesive of claim 2, wherein the content of ethylene oxide units in the pressure-sensitive adhesive is from 12 to 50 mass %. ### Claim 18 (depends on 2) The pressure-sensitive adhesive of claim 2, wherein the pressure-sensitive adhesive has a storage elastic modulus at 80° C. of at most 4.0×105 Pa. ### Claim 19 (depends on 2) The pressure-sensitive adhesive of claim 2, wherein the pressure-sensitive adhesive has a moisture permeability of at least 3,000 g/m2·day. ### Claim 20 (depends on 2) The pressure-sensitive adhesive of claim 2, wherein the pressure-sensitive adhesive has an adhesion to human skin, of from 0.2 to 1 N/15 mm. ### Claim 21 (depends on 3) The pressure-sensitive adhesive of claim 3, wherein the content of ethylene oxide units in the pressure-sensitive adhesive is from 12 to 50 mass %. ### Claim 22 (depends on 3) The pressure-sensitive adhesive of claim 3, wherein the pressure-sensitive adhesive has a storage elastic modulus at 80° C. of at most 4.0×105 Pa. ### Claim 23 (depends on 1) The pressure-sensitive adhesive of claim 1, wherein the oxyalkylene polymer B has an ethylene oxide content of 5 to 80%.