# US 12,600,890 B2 · Solventless adhesive compositions and laminate materials prepared therefrom > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,600,890 B2 - Document ID: US12600890B2 - Status: Granted - Kind: B2 - Application number: 18/577,022 - Filed: 2021-07-30 - Published: 2024-09-19 - Granted: 2026-04-14 - Earliest claimed: 2021-07-30 - Assignees: Arkema France - Applicants: Arkema France - Inventors: Chenyan Bai; Thorsten Schmidt - Web page: https://patentgrep.com/patent/US12600890B2 ## CPC - C09J 175/04: Polyurethanes - C09J 175/06: from polyesters - C08G 18/12: using two or more compounds having active hydrogen in the first polymerisation step - C08G 18/4018: {Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48} - C08G 18/758: {containing two or more cycloaliphatic rings} - C08G 18/792: {formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates} - C09J 175/08: from polyethers - B32B 37/12: characterised by using adhesives - Y02E 10/50: Photovoltaic [PV] energy - 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 - B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM - Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION ## Abstract Disclosed is a solventless adhesive composition comprising (A) an isocyanate component obtained by the reaction of reactants comprising at least one monomeric cycloaliphatic isocyanate compound and at least one first polyol; and (B) a polyol component comprising particularly selected polyols. The solventless adhesive composition can be used for the production of laminate materials, e.g. laminate backsheet of a photovoltaic device, which well meets the requirements of various compliance regulations and has superior performance properties such as bond strength, aging resistance, yellowing resistance, delamination resistance, and the like. A method for producing said laminate material and the resultant laminate material are also disclosed. ## Claims ### Claim 1 A solventless adhesive composition, comprising: (A) an isocyanate component comprising a prepolymer which is the reaction product of reactants comprising: (a) at least one monomeric cycloaliphatic isocyanate compound comprising at least one cyclohexyl(ene) group and more than one isocyanate groups, and (b) at least one first polyol selected from the group consisting of a first polyester polyol, a first polycarbonate polyol, a first polyether polyol, and combinations thereof, wherein the prepolymer comprises more than one free isocyanate groups; wherein the first polyol comprises from 10 to 50 wt % of the first polycarbonate polyol, from 40 to 85 wt % of the first polyester polyol, and from 0 to 20 wt % of the first polyether polyol, based on the total weight of the first polyol, (B) a polyol component comprising at least one second polyol selected from the group consisting of a second polycarbonate polyol, a second polyester polyol, a second polyether polyol, a mixture of the second polycarbonate polyol, the second polyester polyol and the second polyether polyol, and any combinations thereof. ### Claim 2 (depends on 1) The solventless adhesive composition of claim 1, wherein the monomeric cycloaliphatic isocyanate compound is selected from the group consisting of isophorone diisocyanate (IPDI), methylene-bis(cyclohexylisocyanate) (HMDI), and a combination thereof; and the monomeric cycloaliphatic isocyanate compound is free of dimer, trimer or oligomer. ### Claim 3 (depends on 1) The solventless adhesive composition of claim 1, wherein the (A) isocyanate component optionally comprises (c) at least one secondary isocyanate compound other than the monomeric cycloaliphatic isocyanate compound, selected from the group consisting of C2-C16 aliphatic diisocyanate, C5-C18 cycloaliphatic diisocyanate, Co-Cis aromatic diisocyanate, carbodiimide modified isocyanate, allophanate modified isocyanate, and a combination thereof; or the (A) isocyanate component is free of any isocyanate compound other than the monomeric cycloaliphatic isocyanate compound. ### Claim 4 (depends on 1) The solventless adhesive composition of claim 1, wherein the solventless adhesive composition is free of any polymerization unit derived from (meth)acrylate, (meth)acrylic acid, polylactone, polyolefin, bis-phenol resin and vinyl acetate. ### Claim 5 (depends on 1) The solventless adhesive composition of claim 1, wherein the content of the (a) monomeric cycloaliphatic isocyanate compound is from 40 to 70 wt %, and the content of the (b) first polyol is 30-60 wt %, based on the total weight of the isocyanate component. ### Claim 6 (depends on 1) The solventless adhesive composition of claim 1, wherein the (B) polyol component comprises from 8 to 50 wt % of the second polycarbonate polyol, from 15 to 70 wt % of the second polyester polyol, and from 10 to 50 wt % of the second polyether polyol, based on the total weight of the (B) polyol component. ### Claim 7 (depends on 1) The solventless adhesive composition of claim 1, wherein the weight ratio of the isocyanate component (A):the polyol component (B) is 100:(30-65). ### Claim 8 (depends on 1) The solventless adhesive composition of claim 1, wherein the first polyester polyol has an average hydroxyl functionality of 1.8 to 3 and a molecular weight from 500 to 5,000, the first polyether polyol has an average hydroxyl functionality of 1.8 to 3 and a molecular weight from 400 to 5,000; the first polycarbonate polyol has an average hydroxyl functionality of 1.8 to 3 and a molecular weight from 500 to 5,000; the second polyester polyol has an average hydroxyl functionality of 1.8 to 3 and a molecular weight from 500 to 5,000, the second polyether polyol has an average hydroxyl functionality of 1.8 to 3 and a molecular weight from 400 to 5,000; and the second polycarbonate polyol has an average hydroxyl functionality of 1.8 to 3 and a molecular weight from 500 to 5,000. ### Claim 9 (depends on 1) A laminate material, comprising at least one first substrate, at least one second substrate, and at least one adhesive layer sandwiched therebetween, wherein the adhesive layer is derived from the solventless adhesive composition according to claim 1, and each of the first and second substrate is independently selected from the group consisting of metal foil, polymer layer, fabric layer, and combinations thereof. ### Claim 10 (depends on 1, 9) A method of producing a laminate material according to claim 9, comprising: (a) providing at least one first substrate and at least one second substrate; and (b) adhering the first substrate and the second substrate together by using the solventless adhesive composition according to claim 1. ### Claim 11 (depends on 1) The solventless adhesive composition of claim 1, wherein the monomeric cycloaliphatic isocyanate compound is selected from the group consisting of isophorone diisocyanate (IPDI), methylene-bis(cyclohexylisocyanate) (HMDI), and a combination thereof; or the monomeric cycloaliphatic isocyanate compound is free of dimer, trimer or oligomer.