# US 4,395,530 A · Catalyst initiated prepolymer systems > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,395,530 A - Document ID: US4395530A - Status: Granted - Kind: A - Application number: 06/325,315 - Filed: 1981-11-27 - Granted: 1983-07-26 - Earliest claimed: 1980-10-24 - Assignees: Colamco, Inc. - Inventors: James A. Hammond - Web page: https://patentgrep.com/patent/US4395530A ## CPC - C08G 18/089: {Reaction retarding agents} - C08G 18/16: Catalysts (catalysts in general B01J) - C09J 175/04: Polyurethanes - C08G 2170/60: Compositions for foaming; Foamed or intumescent adhesives - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON 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) ## Abstract A process for the manufacture of a polyurethane prepolymer adhesive by a catalyst initiated reaction of polyol and isocyanate copolymers is performed under room temperature conditions, and in convenient quantities for application, storage, and transportation purposes. Compounding includes alternatives of catalyst and co-catalyst combinations, and additives, including a reaction inhibitor, plasticizer, delayed reaction catalyst and surfactant. ## Claims ### Claim 1 A process for manufacturing a polyurethane prepolymer adhesive under room temperature conditions comprising the steps of: (a) introducing a predetermined amount of at least one polyol reactant into a reaction vessel; (b) mixing a predetermined amount of least one isocyanate reactant into the reaction vessel to give a uniform resin mixture sufficient to give an excess active isocyanate content in the polyurethane prepolymer adhesive of approximately 5% to 20% by weight; (c) adding a predetermined amount of catalyst to initiate reaction of the reactants in the reaction vessel, with vigorous stirring to give a uniform mixture, said predetermined amount of catalyst being sufficient to allow the reaction to substantially reach completion within 2 to 8 hours; (d) isolating the mixed contents in the reaction vessel from ambient conditions to prevent contamination of the contents by ambient moisture; and (e) mixing the reactants during the reaction in the reaction vessel until the reaction substantially subsides, whereby the polyurethane prepolymer adhesive is formed. ### Claim 2 (depends on 1) The process according to claim 1 further comprising the step of mixing into the polyol-isocyanate mixture a fire retardant. ### Claim 3 (depends on 1) The process according to claim 1 further comprising the step of mixing into the polyurethane prepolymer adhesive a reaction inhibitor. ### Claim 4 (depends on 1) The process according to claim 1 further comprising the step of mixing into the polyurethane prepolymer adhesive a plasticizer. ### Claim 5 (depends on 1) The process according to claim 1 further comprising the step of mixing into the polyol-isocyanate mixture a predetermined amount of a plasticizer, said predetermined amount ranging from 0-50%, by weight. ### Claim 6 (depends on 1) The process according to claim 1 further comprising the step of mixing into the polyurethane prepolymer adhesive a predetermined amount of a plasticizer, said predetermined amount ranging from 0-5%, by weight. ### Claim 7 (depends on 6) The process according to claim 6 wherein the delayed action catalyst is a hydroxylated quaternary ammonium carbonate. ### Claim 8 (depends on 6) The process according to claim 6 further comprising the step of mixing into a polyurethane prepolymer adhesive a predetermined amount of a surfactant, said predetermined amount ranging from 0-10%, by weight. ### Claim 9 (depends on 1) The process according to claim 1 further comprising the step of mixing into the polyurethane prepolymer adhesive a predetermined amount of a surfactant. ### Claim 10 (depends on 8, 9) The process according to claim 8 or claim 9 wherein the surfactant is selected from the group consisting of polysiloxane polyoxyalkylene block copolymer surfactants and polyol derive organic surfactants. ### Claim 11 (depends on 1) The process according to claim 1 wherein the amount of catalyst is predetermined by a method comprising the steps of: (a) removing a 150 gram sample of the unreacted resin mixture from the reaction vessel; (b) adding an estimated amount of catalyst to the sample in a suitable vessel; (c) adjusting the estimated amount of catalyst to cause a temperature rise of the sample of 5 to 10 degrees F. within 5 to 10 minutes from the time of addition of catalyst to the sample; and (d) measuring the added amount of catalyst for the reaction vessel proportional to the amount of the sample which was determined in step (c). ### Claim 12 (depends on 1) The process according to claim 1 further comprising the step of mixing into the polyol reactant a predetermined amount of a co-catalyst, said predetermined amount ranging from 0-10%, by weight. ### Claim 13 (depends on 1) The process according to claim 1 wherein the excess active isocyanate content in the polyurethane prepolymer adhesive is in the range of approximately 5 to 20 percent by weight. ### Claim 14 (depends on 1) The process according to claim 1 wherein the step of isolating the mixed contents in the reaction vessel includes purging the contents of the reaction vessel with dry nonreactive gases. ### Claim 15 (depends on 1) The process according to claim 1 wherein the reaction vessel is a drum, and the step of mixing the reactants during the reaction is performed with a means for continuously rolling the drum. ### Claim 16 (depends on 1) The process according to claim 1 wherein the step of mixing the reactants during the reaction is performed by a means for stirring the reactants. ### Claim 17 (depends on 3) The process according to claim 3 wherein the reaction inhibitor comprises a Lewis acid. ### Claim 18 (depends on 4) The process according to claim 4 wherein the plasticizer comprises a light petroleum oil. ### Claim 19 (depends on 1) The process according to claim 1 wherein the catalyst is an organometallic compound. ### Claim 20 (depends on 1) The process according to claim 1 wherein the excess active isocyanate content in the polyurethane prepolymer adhesive is approximately 8 to 11.5 percent by weight. ### Claim 21 (depends on 3) The process according to claim 3 wherein the reaction inhibitor additive is selected from the group consisting of benzoyl chloride, acetyl chloride, and acetic anhydride. ### Claim 22 (depends on 12) The process according to claim 12 wherein the co-catalyst is treated with a drying agent to withdraw water from the co-catalyst. ### Claim 23 (depends on 1) The process according to claim 1 wherein the catalyst is selected from a group consisting of dibutyl tin dilaurate and di(phenylmercuric) dodecenyl succinate. ### Claim 24 (depends on 1) The process according to claim 1 further comprising the step of adding a predetermined amount of at least one co-catalyst to the polyol reactant, wherein the co-catalyst is a Lewis base selected from the group consisting of triethylenediamine, dimethyl ethanolamine, and N,N,N',N'-tetrakis (2-hydroxypropyl) ethylenediamine. ### Claim 25 (depends on 1) The process according to claim 1 wherein the polyol reactant is selected from the group consisting of dipropylene glycol, polypropylene glycol, polyethylene glycol, polybutadiene glycol, polyethylene triol and polypropylene triol. ### Claim 26 (depends on 1) The process according to claim 1 wherein the isocyanate reactant is selected from the group consisting of diphenylmethane diisocyanate; polymethylene polyphenylisocyanate; 2, 4 toluene diisocyanate; 2, 6 toluene diisocyanate; hexamethylene diisocyanate and isophorone diisocyanate. ### Claim 27 (depends on 17) The process according to claim 17 wherein the Lewis acid reaction inhibitor is selected from a group consisting of benzoyl chloride, acetyl chloride, and acetic anhydride, and the plasticizer comprises a light petroleum aromatic oil. ### Claim 28 (depends on 1) A polyurethane prepolymer adhesive manufactured by the process of claim 1. ### Claim 29 (depends on 6) A polyurethane prepolymer adhesive manufactured by the process of claim 6. ### Claim 30 (depends on 1) The process according to claim 1 wherein said predetermined amount of catalyst is added after said polyol reactant and said isocyanate reactant are mixed to give said uniform resin mixture.