# US 9,518,202 B2 · Self-adhesive of renewable origin with temperature-stable adhesive power > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,518,202 B2 - Document ID: US9518202B2 - Status: Granted - Kind: B2 - Application number: 14/522,880 - Filed: 2014-10-24 - Published: 2015-04-30 - Granted: 2016-12-13 - Earliest claimed: 2013-10-24 - Assignees: Bostik SA - Applicants: Bostik S.A. - Inventors: Olivier Laferte; Stéphane Fouquay - Web page: https://patentgrep.com/patent/US9518202B2 ## CPC - C09J 175/06: from polyesters - C08G 18/10: Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step - C08G 18/227: {of antimony, bismuth or arsenic} - C08G 18/4233: {derived from polymerised higher fatty acids or alcohols} - C08G 18/755: {and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate} - C08G 65/33348: {containing isocyanate group} - C08G 65/336: containing silicon - C09J 7/20: characterised by their carriers - C09J 7/35: Heat-activated - C09J 7/38: Pressure-sensitive adhesives [PSA] - C09J 171/00: Adhesives based on polyethers obtained by reactions forming an ether link in the main chain (based on polyacetals C09J159/00; based on epoxy resins C09J163/00; based on polythioether-ethers C09J181/02; based on polyethersulfones C09J181/06); Adhesives based on derivatives of such polymers - C09J 175/04: Polyurethanes - C09J 193/04: Rosin - C08G 2170/20: Compositions for hot melt adhesives - C08G 2170/40: Compositions for pressure-sensitive adhesives - C09J 2203/334: as a label - C09J 2471/00: Presence of polyether - C09J 2475/00: Presence of polyurethane - Y10T 428/2896: including nitrogen containing condensation polymer [e.g., polyurethane, polyisocyanate, etc.] - 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 - Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION ## Abstract Heat-curable adhesive composition: 47-60% of polyether/polyurethane bearing alkoxysilane end groups and polyurethanes bearing alkoxysilane end groups of formula (II): in which: R6 is a divalent C5-C15 hydrocarbon-based radical; R7 is a divalent C1-C3 alkylene radical; R8 and R9 are a C1-C4 alkyl; q is 0, 1 or 2; r is such that the number-average molar mass of the polymers of formula (II) is between 900 Da and 11 kDa; R10 is a divalent polyester block with a hydroxyl number IOH of between 40 and 60 mg KOH/g; 37-50% of a compatible tackifying resin; and 0.01-3% of a crosslinking catalyst. ## Claims ### Claim 1 A heat-curable adhesive composition comprising: (α) from 47% to 60% weight/weight of a composition (A) comprising polymers bearing hydrolyzable alkoxysilane end groups which composition (A) is: from 10% to 50% weight/weight of a polymer (A1) of formula (I): in which: R1 represents a divalent hydrocarbon-based radical comprising from 5 to 15 carbon atoms, which may be aromatic or aliphatic, and linear, branched or cyclic; R2 represents a linear or branched divalent alkylene radical comprising from 1 to 4 carbon atoms; R3 represents a linear divalent alkylene radical comprising from 1 to 3 carbon atoms; R4 and R5, which may be identical or different, each represent a linear or branched alkyl radical of 1 to 4 carbon atoms; n is an integer such that the number-average molar mass of the polyether block of formula —[OR2]n— is between 300 Da and 30 kDa; m is either equal to 0 or a non-zero integer such that the number-average molar mass of the polymer of formula (I) is between 600 Da and 60 kDa; p is an integer equal to 0, 1 or 2; and from 50% to 90% weight/weight of a composition (A2) comprising at least 85% weight/weight of polyurethanes bearing hydrolysable alkoxysilane end groups of formula (II): in which: R6 represents a divalent hydrocarbon-based radical comprising from 5 to 15 carbon atoms, which may be aromatic or aliphatic, and linear, branched or cyclic; R7 represents a linear divalent alkylene radical comprising from 1 to 3 carbon atoms; R8 and R9, which may be identical or different, each represent a linear or branched alkyl radical of 1 to 4 carbon atoms; q is an integer equal to 0, 1 or 2; r is a number such that the number-average molar mass of the polymers of formula (II) is between 900 Da and 11 kDa; R10 represents a divalent polyester block of formula (III): in which: R11 represents a divalent hydrocarbon-based radical which is derived from a dimerized fatty alcohol by replacement of each of the two hydroxyl groups with a free valency, the said alcohol having a hydroxyl number IOH of between 200 and 220 mg KOH/g; R12 represents a divalent hydrocarbon-based radical which is derived from a dimerized fatty acid by replacement of each of the two carboxyl groups —COOH with a free valency, the said acid having an acid number IA of between 190 and 200 mg KOH/g; s is a number such that the polyester diol of formula IV: OH—R10—OH (IV) has a hydroxyl number IOH of between 40 and 60 mg KOH/g; (β) from 37% to 50% weight/weight of a compatible tackifying resin (B) with a number-average molar mass of between 200 Da and 10 kDa; and (γ) from 0.01% to 3% weight/weight of a crosslinking catalyst (C). ### Claim 2 (depends on 1) The heat-curable adhesive composition according to claim 1, wherein polymer (A1) is a polyether, corresponding to formula (I) in which m equals 0. ### Claim 3 (depends on 1) The heat-curable adhesive composition according to claim 1, wherein in polymer (A1): R4 and R5, which may be identical or different, each represent a methyl or ethyl radical; R2 is ethylene, isopropylene, n-propylene, n-butylene, or ethylethylene. ### Claim 4 (depends on 1) The heat-curable adhesive composition according to claim 1, wherein in the polymers of formula (II) the hydroxyl number IOH of the polyester diol of formula (IV) corresponding to the divalent polyester radical R10 varies within a range from 45 to 55 mg KOH/g. ### Claim 5 (depends on 1) The heat-curable adhesive composition according to claim 1, wherein in the polymers of formula (II) the dimerized fatty acid from which the radical R12 is derived has an acid number IA of between 194 and 198 mg KOH/g. ### Claim 6 (depends on 1) The heat-curable adhesive composition according to claim 1, wherein in the polymers of formula (II) the dimerized fatty alcohol from which the radical R11 is derived has a hydroxyl number IOH of between 202 and 212 mg KOH/g. ### Claim 7 (depends on 1) The heat-curable adhesive composition according to claim 1, wherein in the polymers of formula (II) the radical R6 is one of the following divalent radicals for which the formulae below reveal the two free valencies: a) a divalent radical derived from isophorone: ### Claim 8 (depends on 1) The heat-curable adhesive composition according to claim 1, wherein in the polymers of formula (II) the radical R6 is a divalent radical derived from isophorone. ### Claim 9 (depends on 1) The heat-curable adhesive composition according to claim 1, wherein in the polymers of formula (II): R7 is a divalent methylene or n-propylene radical; R8 and R9 each represent a methyl or ethyl radical; and/or q equals 0 or 1. ### Claim 10 (depends on 1) The heat-curable adhesive composition according to claim 1, wherein composition (A) is from 10% to 30% weight/weight of polymer (A1) and from 70% to 90% weight/weight of composition (A2). ### Claim 11 (depends on 1) The heat-curable adhesive composition according to claim 1, wherein the tackifying resin (B) is: (iii) rosins of natural or modified origin, or (v) terpenic resins, resulting from the polymerization of terpenic hydrocarbons. ### Claim 12 (depends on 1) The heat-curable adhesive composition according to claim 1, comprising: (α) from 50% to 55% weight/weight of composition (A) of polymers bearing hydrolysable alkoxysilane end groups, (β) from 43% to 48% weight/weight of tackifying resin (B), and (γ) from 0.45% to 2.5% weight/weight of crosslinking catalyst (C). ### Claim 13 (depends on 1) The heat-curable adhesive composition according to claim 1, having a Brookfield viscosity measured at 100° C. between 10 and 100 Pa·s. ### Claim 14 (depends on 1) A self-adhesive support obtained via the process comprising: (a) preheating to a temperature of between 50 and 130° C. the adhesive composition as defined in claim 1, and then (b) coating it onto a support layer, and then (c) curing it, by heating the support thus coated to a temperature of between 50 and 150° C. ### Claim 15 (depends on 14) One-sided or two-sided self-adhesive labels or tapes, comprising in said labels or tapes the self-adhesive support as defined in claim 14. ### Claim 16 (depends on 11) The heat-curable adhesive composition according to claim 11, wherein the tackifying resin (B) is rosin extracted from pine gum, wood rosin extracted from tree roots or hydrogenated, dimerized or polymerized derivatives thereof or derivatives esterified with monoalcohols or polyols. ### Claim 17 (depends on 16) The heat-curable adhesive composition according to claim 16, wherein (B) is glycerol. ### Claim 18 (depends on 11) The heat-curable adhesive composition according to claim 11, wherein (B) is a terpenic resin resulting from the polymerization of monoterpene in the presence of a Friedel-Craft catalyst.