# US 10,767,088 B2 · Photoreversible adhesive agent > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,767,088 B2 - Document ID: US10767088B2 - Status: Granted - Kind: B2 - Application number: 16/068,570 - Filed: 2017-01-04 - Published: 2019-01-17 - Granted: 2020-09-08 - Earliest claimed: 2016-01-07 - Assignees: National Institute of Advanced Industrial Science and Technology - Applicants: National Institute of Advanced Industrial Science and Technology - Inventors: Haruhisa Akiyama; Hideyuki Kihara; Aishi Yamashita - Web page: https://patentgrep.com/patent/US10767088B2 ## CPC - C08F 293/005: {using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent} - C09J 153/00: Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers - B32B 38/10: Removing layers, or parts of layers, mechanically or chemically - B32B 43/006: {Delaminating} - C08F 293/00: Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule (on to polymers modified by introduction of unsaturated end groups C08F290/02) - C09J 5/00: Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers - C09J 7/387: {Block-copolymers} - B32B 2310/0806: using electromagnetic radiation - B32B 2310/0831: using UV radiation - C08F 2438/01: Atom Transfer Radical Polymerization [ATRP] or reverse ATRP - C09J 107/00: Adhesives based on natural rubber - C09J 133/04: Homopolymers or copolymers of esters {(C09J143/04 takes precedence)} - C09J 2203/318: for the production of liquid crystal displays - C09J 2301/416: use of irradiation - C09J 2301/502: process for debonding adherents - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - 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) - B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM ## Abstract When conventional photo-reactive compounds are to be liquefied with the application of light, liquefaction thereof is time-consuming due to poor sensitivity to ultraviolet light. In the case of conventional photo-reactive compounds, disadvantageously, light does not penetrate through layers to be adhered to each other when such layers are thick. Thus, peeling is not sufficiently performed. Accordingly, it is an object of the present invention to overcome such drawbacks of conventional photo-reactive compounds and provide a photo-reactive adhesive agent exhibiting high sensitivity to light for fluidization and capable of easy peeling. This invention provides a photo-reactive pressure-sensitive adhesive agent comprising, as a main component, a polymeric compound with a weight average molecular weight of 3,000 to 800,000 represented by General Formula (1): wherein A represents a block polymer of monomers represented by Formula (2) below with a molecular weight of 1,000 to 100,000; and B represents a block polymer with a molecular weight of 1,000 to 400,000 having a glass transition point and a melting point of 20° C. or lower, which is liquid or plastically deformable at room temperature, provided that B does not absorb light of a wavelength range of 350 to 600 nm by itself: wherein R1 represents a group having an azobenzene structure represented by Formula (3) below; n is an integer of 2 to 18; m is an integer of 0 to 16; and R2 represents hydrogen or a methyl group. ## Claims ### Claim 1 A photo-reactive pressure-sensitive adhesive agent comprising, as a main component, a polymeric compound with a weight average molecular weight of 3,000 to 800,000 represented by General Formula (1): wherein A represents a block polymer of monomers represented by Formula (2) below with a molecular weight of 1,000 to 100,000; and B represents a block polymer with a molecular weight of 1,000 to 400,000 having a glass transition point and a melting point of 20° C. or lower, which is liquid or plastically deformable at room temperature, wherein B does not absorb light of a wavelength range of 350 to 600 nm: wherein R1 represents a group having an azobenzene structure represented by Formula (3) below; n is an integer of 2 to 18; m is an integer of 0 to 16; and R2 represents hydrogen or a methyl group. ### Claim 2 (depends on 1) The photo-reactive pressure-sensitive adhesive agent according to claim 1, which can be fluidized and peeled from an object to which it is adhered with an application of light. ### Claim 3 (depends on 2) The photo-reactive pressure-sensitive adhesive agent according to claim 2, which can be fluidized and peeled from the object to which it is adhered with an application of ultraviolet light in a wavelength range of 350 to 390 nm at a light exposure dose of 0.05 to 10 J/cm2. ### Claim 4 (depends on 1) The photo-reactive pressure-sensitive adhesive agent according to claim 1, which can be non-fluidized with an application of light in a wavelength range different from that of light used for fluidization to adhere objects to each other. ### Claim 5 (depends on 4) The photo-reactive pressure-sensitive adhesive agent according to claim 4, which can be non-fluidized with an application of light in a wavelength range of 420 to 600 nm. ### Claim 6 (depends on 1) The photo-reactive pressure-sensitive adhesive agent according to claim 1, which can be repeatedly adhered to and peeled from an object via reversible non-fluidization and fluidization with applications of light in different wavelength ranges. ### Claim 7 (depends on 1) A method of adhering the photo-reactive pressure-sensitive adhesive agent according to claim 1 to an object and peeling the adhesive agent from the object comprising: reversible non-fluidization and fluidization with applications of light in different wavelength ranges. ### Claim 8 (depends on 7) The method according to claim 7, wherein the adhesive agent is fluidized with an application of ultraviolet light in a wavelength range of 350 to 390 nm at a light exposure dose of 0.05 to 10 J/cm2. ### Claim 9 (depends on 7) The method according to claim 7, wherein the adhesive agent is non-fluidized with an application of light in a wavelength range of 420 to 600 nm. ### Claim 10 (depends on 7) The method according to claim 7, wherein the adhesive agent can be repeatedly adhered to and peeled from the object via reversible non-fluidization and fluidization with applications of light in different wavelength ranges.