# US 11,111,417 B2 · Adhesives for assembling components of inert material > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,111,417 B2 - Document ID: US11111417B2 - Status: Granted - Kind: B2 - Application number: 16/303,048 - Filed: 2017-05-19 - Published: 2019-10-03 - Granted: 2021-09-07 - Earliest claimed: 2016-05-19 - Assignees: Sicpa Holding SA - Applicants: Sicpa Holding SA - Inventors: Davide Ciampini - Web page: https://patentgrep.com/patent/US11111417B2 ## CPC - C09J 4/06: {Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond} in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00 - C08G 59/22: Di-epoxy compounds - C08G 65/2603: {the other compounds containing oxygen} - C08K 5/01: Hydrocarbons {(C08K5/0091 takes precedence)} - C08K 5/07: Aldehydes; Ketones - C08K 5/09: Carboxylic acids; Metal salts thereof; Anhydrides thereof - C08K 5/375: containing six-membered aromatic rings {(C08K5/3725 takes precedence)} - C08K 5/5435: containing oxygen in a ring - C08K 5/56: Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond - C09J 5/06: involving heating of the applied adhesive - C09J 163/00: Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins - C09J 2301/416: use of irradiation - 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) - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) ## Abstract The present invention relates to adhesive formulations for bonding materials, comprising 40 to 80 wt.-% of an epoxy monomer, and 15 to 30 wt.-% of an oxetane monomer, and 0.1 to 10 wt.-% of an adhesion promotor, and 0.1 to 5 wt.-% of a sensitizer, and 1 to 10 wt.-% of a radiation and temperature activable photoinitiator or a mixture of a photoinitiator and a thermal initiator. Further, the present invention relates to a method for bonding at least two parts of which one is at least an inert material, comprising the steps applying to one part an adhesive formulation as described, placing another part to be bond on the one part, exposing the parts to UV light radiation and heat treating of the part. ## Claims ### Claim 1 An adhesive formulation for bonding two materials at least one of which being an impregnated or impermeabilized material, comprising 40 to 80 wt.-% of an epoxy monomer; and 15 to 30 wt.-% of an oxetane monomer; and 0.1 to 10 wt.-% of an adhesion promotor; and 0.1 to 5 wt.-% of a sensitizer; and 1 to 10 wt.-% of a radiation and temperature activatable photoinitiator or a mixture of a photoinitiator and a thermal initiator, and further comprising a fluorurated epoxy monomer being 3-Perfluorooctyl-1,2-propenoxide. ### Claim 2 (depends on 1) The formulation according to claim 1, wherein the epoxy monomer is selected from the group consisting of an epoxy cresol novolac, (3′,4′-epoxycyclohexane)methyl 3,4-epoxycyclohexylcarboxylate 3,4-Epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate; Diglycidyl 1,2-cyclohexanedicarboxylate; Cyclohexene oxide; 1,2,5,6-Diepoxycyclooctane and Poly[(phenyl glycidyl ether)-co-formaldehyde]. ### Claim 3 (depends on 1) The formulation according to claim 1, wherein the oxetane monomer is selected from the group consisting of bis[1-ethyl(3-oxetanyl)]methyl ether, 3-Ethyl-3-oxetanemethanol; 3,3-Dimethyloxetane and 3-ethyl-3-[(2-ethylhexyloxy)methyl]oxetane. ### Claim 4 (depends on 1) The formulation according to claim 1, wherein the adhesion promotor is a silane-epoxy adhesion promoter. ### Claim 5 (depends on 1) The formulation according to claim 1, wherein the sensitizer is a UV-Vis sensitizer. ### Claim 6 (depends on 1) The formulation according to claim 1, wherein the radiation and temperature activatable photoinitiator is a cationic photoinitiator. ### Claim 7 (depends on 1) The formulation according to claim 1, wherein in the mixture of photoinitiator and thermal initiator the thermal initiator is an anhydride and the photoinitiator is a cationic photoinitiator. ### Claim 8 (depends on 1) The formulation according to claim 1, wherein the adhesion promotor is selected from the group consisting of gamma-glycidoxypropyltrimethoxysilane, (3-Glycidyloxypropyl)triethoxysilane; (3-Glycidyloxypropyl)trimethoxysilane and Trimethoxy[2-(7-oxabicyclo[4.1.0] kept-3-yl)ethyl] silane. ### Claim 9 (depends on 1) The formulation according to claim 1, wherein the sensitizer is selected from the group consisting of anthracene; 9-Fluorenone; perylene and 9,10-diethoxyanthracene. ### Claim 10 (depends on 1) The formulation according to claim 1, wherein in the mixture of photoinitiator and thermal initiator the thermal initiator is selected from the group consisting of Phtalic anhydride; Maleic anhydride; Cyclobutane-1,2,3,4-tetracarboxylic dianhydride; Benzoic anhydride and Oleic anhydride, and the photoinitiator is selected from the group consisting of Diphenyliodonium hexafluorophosphate, diphenyliodonium hexafluoroantimonate, Triarylsulfonium hexafluorophosphate salts and Triphenylsulfonium triflate. ### Claim 11 (depends on 1) The formulation according to claim 1, wherein the adhesion promotor is gamma-glycidoxypropyltrimethoxysilane. ### Claim 12 (depends on 1) The formulation according to claim 1, wherein the two materials are an impregnated graphite material and a silicon material. ### Claim 13 A method for bonding at least two parts of which one is at least an impregnated or impermeabilized material, comprising the following steps: applying to one part an adhesive formulation for bonding two materials at least one of which being an impregnated or impermeabilized material, comprising 40 to 80 wt.-% of an epoxy monomer; and 15 to 30 wt.-% of an oxetane monomer; and 0.1 to 10 wt.-% of an adhesion promotor; and 0.1 to 5 wt.-% of a sensitizer; and 1 to 10 wt.-% of a radiation and temperature activatable photoinitiator or a mixture of a photoinitiator and a thermal initiator, and further comprising a fluorurated epoxy monomer being 3-Perfluorooctyl-1,2-propenoxide; placing another part to be bond on the one part; exposing the parts to UV light radiation; and heat treating of the part.