# US 10,479,916 B2 · Latent two-part polyurethane adhesives curable with infrared radiation > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,479,916 B2 - Document ID: US10479916B2 - Status: Granted - Kind: B2 - Application number: 15/579,738 - Filed: 2016-06-14 - Published: 2018-06-28 - Granted: 2019-11-19 - Earliest claimed: 2015-06-18 - Assignees: Dow Global Technologies LLC - Applicants: Dow Global Technologies LLC - Inventors: Stefan Schmatloch; Joel Kunz; Sergio Grunder - Web page: https://patentgrep.com/patent/US10479916B2 ## CPC - B29B 7/726: {Measuring properties of mixture, e.g. temperature or density (B29B7/724 takes precedence)} - C09J 175/08: from polyethers - B32B 37/12: characterised by using adhesives - C08G 18/165: {covered by C08G18/18 and C08G18/24} - C08G 18/2063: {having two nitrogen atoms in the condensed ring system} - C08G 18/242: {organometallic compounds containing tin-carbon bonds} - C08G 18/244: {tin salts of carboxylic acids} - C08G 18/4812: {Mixtures of polyetherdiols with polyetherpolyols having at least three hydroxy groups} - C08G 18/482: {Mixtures of polyethers containing at least one polyether containing nitrogen} - C08G 18/4837: {and other oxyalkylene units} - C08G 18/5024: {containing primary and/or secondary amino groups} - C08G 18/6674: {with compounds of group C08G18/3203} - C08G 18/798: {containing urethdione groups} - C08J 3/24: Crosslinking, e.g. vulcanising, of macromolecules (mechanical aspects B29C35/00; crosslinking agents C08K) - C08J 3/244: {Stepwise homogeneous crosslinking of one polymer with one crosslinking system, e.g. partial curing} - C08J 3/28: Treatment by wave energy or particle radiation - C09J 5/06: involving heating of the applied adhesive - C09J 11/04: inorganic - C09J 175/04: Polyurethanes - B32B 7/12: using interposed adhesives or interposed materials with bonding properties - B32B 2037/1253: {curable adhesive} - C08J 2375/04: Polyurethanes - C08K 3/04: Carbon - C08K 3/346: {Clay} - C08K 3/36: Silica - C08K 9/00: Use of pretreated ingredients - C09J 2301/416: use of irradiation - C09J 2400/226: in the substrate - C09J 2475/00: Presence of polyurethane - B29B: PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS - 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 - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29) - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) ## Abstract Disclosed are latent two-part polyurethane adhesives that rapidly develop adhesive strength when cured by application of infrared radiation containing a polyol component which includes; one or more polyols having a hydroxyl equivalent weight of 400 to 2000 and a nominal hydroxyl functionality of 2 to 4; one or more aliphatic diol chain extenders; and one or more latent room temperature organometallic catalysts; b) a polyisocyanate component containing one or more polyisocyanate compounds; and v) a carboxylic acid-blocked cyclic amidine compound and vi) a phenol-blocked cyclic amidine compound which each may be located in the polyol component or the isocyanate component. Further disclosed are methods of bonding structures together using the latent two-part polyurethane adhesives. ## Claims ### Claim 1 A composition comprising a polyol component and an isocyanate component, wherein: a) the polyol component includes; i) one or more polyols having a hydroxyl equivalent weight of 400 to 2000 and a nominal hydroxyl functionality of 2 to 4; ii) one or more aliphatic diol chain extenders; and iii) one or more latent room temperature organometallic catalysts; b) the polyisocyanate component includes: iv) one or more polyisocyanate compounds; wherein the polyisocyanate component includes isocyanate groups and the polyol component isocyanate-reactive groups wherein a ratio of a number of the isocyanate groups in the polyisocyanate component to a number of the isocyanate-reactive groups in the polyol component is about 1.0 to about 1.8; and v) one or more carboxylic acid-blocked cyclic amidine compounds and vi) one or more phenol-blocked cyclic amidine compounds are located in the polyol component or the isocyanate component and the composition is useful as a two-component polyurethane adhesive composition. ### Claim 2 (depends on 1) A composition according to claim 1 wherein the one or more latent room temperature organometallic catalysts contain tin, zinc or bismuth. ### Claim 3 (depends on 1) A composition according to claim 1 wherein the one or more latent room temperature organometallic catalysts are zinc alkanoates, bismuth alkanoates, dialkyltin alkanoates, dialkyl tin mercaptides, dialkyl tin bis(alkylmercaptoacetates), dialkyltin thioglycolates or mixtures thereof. ### Claim 4 (depends on 1) A composition according to claim 1 wherein the one or more latent room temperature organometallic catalysts are dialkyl tin mercaptides, dialkyl tin bis(alkylmercaptoacetates), dialkyltin thioglycolates or mixtures thereof. ### Claim 5 (depends on 1) A composition according to claim 1 wherein the one or more carboxylic acid-blocked cyclic amidine compounds and the one or more phenol-blocked cyclic amidine compounds comprise at least one of a carboxylic acid-blocked 1,8-Diazabicyclo[5.4.0]undec-7-ene) or 1,5-Diazabicyclo[4.3.0]non-5-ene or a phenol-blocked 1,8-Diazabicyclo[5.4.0]undec-7-ene) or 1,5-Diazabicyclo[4.3.0]non-5-ene. ### Claim 6 (depends on 1) A composition according to claim 1 wherein the one or more latent room temperature organometallic catalysts are present in an amount of about 0.005 to about 1.0 percent by weight based on the weight of the polyol component, the phenol blocked cyclic amidine compounds are present in an amount of about 0.01 to about 2.0 percent by weight based on the weight of the polyol or polyisocyanate component; and the carboxylic acid blocked cyclic amidine compounds are present in an amount of about 0.01 to about 2.0 percent by weight based on the weight of the polyol or polyisocyanate component. ### Claim 7 (depends on 1) A composition according claim 1 wherein the polyol component contains one or more particulate fillers. ### Claim 8 (depends on 1) A composition according to claim 1 wherein the polyisocyanate component contains one or more particulate fillers. ### Claim 9 (depends on 6) A composition according to claim 6 wherein: the one or more polyols having a hydroxyl equivalent weight of 400 to 2000 and a nominal hydroxyl functionality of 2 to 4 are present in an amount of about 35 to about 80 percent by weight of the polyol component; the one or more chain extenders are present in an amount of about 1 to about 10 percent by weight of the polyol component; and the polyisocyanate compound is present in an amount of about 20 to about 65 percent by weight of the polyisocyanate component. ### Claim 10 (depends on 1) A composition according to claim 1 wherein the one or more latent room temperature organometallic catalysts are present in an amount of about 0.020 to about 0.050 percent by weight based on the weight of the polyol component, the phenol-blocked cyclic amidine compounds are present in an amount of about 0.01 to about 1.0 percent by weight based on the weight of the polyol or polyisocyanate component; and the carboxylic acid-blocked cyclic amidine compounds are present in an amount of about 0.01 to about 1.0 percent by weight based on the weight of the polyol or polyisocyanate component. ### Claim 11 (depends on 1) A composition according to claim 1 wherein the carboxylic acid-blocked cyclic amidine compound includes a cyclic amidine compound blocked with an aliphatic carboxylic acid having 1 to 24 carbon atoms or a mixture of two or more thereof. ### Claim 12 (depends on 1) A composition according to claim 1 wherein the phenol-blocked cyclic amidine compound includes a cyclic amidine compound blocked with a phenol, a substituted phenol, or a mixture of two or more thereof. ### Claim 13 (depends on 1) A composition according to claim 1 wherein the polyisocyanate component includes both aliphatic and aromatic isocyanates. ### Claim 14 (depends on 1) A composition according to claim 1 wherein the particulate filler constitutes about 10 to about 50 percent of the weight of the polyisocyanate component. ### Claim 15 (depends on 1) A composition according to claim 1 wherein the particulate filler constitutes about 25 to about 60 percent of the weight of the polyol component. ### Claim 16 (depends on 1) A method comprising a) contacting the polyol component and the isocyanate component according to claim 1 and mixing to form a homogeneous mixture; b) applying the mixture to a first substrate; c) contacting a second substrate with the first substrate with the mixture of part a disposed between the first and second substrate; and d) exposing a portion of the mixture to heat under conditions such that the mixture partially cures sufficiently such that the first and second substrate are bonded such that the substrates can be moved. ### Claim 17 (depends on 16) A method according to claim 16 which includes e) heating the two substrates at a temperature for a time to fully cure the mixture to bond the two substrates together. ### Claim 18 (depends on 16) A method according to claim 16 wherein the heat is applied in step d by infrared heating. ### Claim 19 (depends on 17) A method according to claim 17 wherein: the time frame between steps d and e is about 24 hours or more; or at least one of the substrates is a fiber reinforced plastic. ### Claim 20 A composition comprising a polyol component and an isocyanate component, wherein: a) the polyol component includes; i) one or more polyols having a hydroxyl equivalent weight of 400 to 2000 and a nominal hydroxyl functionality of 2 to 4; ii) one or more aliphatic diol chain extenders; and iii) one or more latent room temperature organometallic catalysts; b) the polyisocyanate component includes: iv) one or more polyisocyanate compounds; wherein v) one or more carboxylic acid-blocked cyclic amidine compounds and vi) one or more phenol-blocked cyclic amidine compounds are located in the polyol component or the isocyanate component and the composition is useful as a two-component polyurethane adhesive composition.