# US 10,370,481 B2 · Non-hot-melt 2,4-TDI-based polyurethane composition bearing NCO end groups and having a low content of TDI monomer, comprising at least one isocyanate compound of particular molar volume > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,370,481 B2 - Document ID: US10370481B2 - Status: Granted - Kind: B2 - Application number: 14/722,731 - Filed: 2015-05-27 - Published: 2015-12-03 - Granted: 2019-08-06 - Earliest claimed: 2014-05-28 - Assignees: Bostik SA - Applicants: Bostik SA - Inventors: Federico Sanz; Guillaume Michaud - Web page: https://patentgrep.com/patent/US10370481B2 ## CPC - C08G 18/7642: {containing at least two isocyanate or isothiocyanate groups linked to the aromatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate groups, e.g. xylylene diisocyanate or homologues substituted on the aromatic ring} - C08G 18/10: Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step - C08G 18/307: {Atmospheric humidity} - C08G 18/4829: {Polyethers containing at least three hydroxy groups (C08G18/4833 - C08G18/5096 take precedence)} - C08G 18/4845: {containing oxypropylene or higher oxyalkylene end groups} - C08G 18/7614: {containing only one aromatic ring} - C08G 18/7621: {being toluene diisocyanate including isomer mixtures} - C09J 175/08: from polyethers - C08G 2170/40: Compositions for pressure-sensitive 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 1) Polyurethane composition comprising: a) at least 98% by weight of at least one non-hot-melt polyurethane bearing NCO end groups based on 2,4-toluene diisocyanate, b) a TDI monomer content of less than 0.1% by weight, c) at least one particular isocyanate compound with a molar volume of less than or equal to 300 milliliters per mole. 2) Process for preparing a polyurethane composition as defined previously, and an adhesive composition formulated from such a polyurethane composition. ## Claims ### Claim 1 A polyurethane composition comprising: a) at least 98% by weight of at least one polyurethane bearing NCO end groups based on 2,4-toluene diisocyanate (2,4-TDI), which is not solid at a temperature ranging from 5 to 35° C., b) a TDI monomer content of less than 0.1% by weight, c) at least one isocyanate compound with a molar volume of less than or equal to 300 milliliters per mole (mL/mol) (noted compound A), in which the isocyanate group(s) are not linked to a carbon atom of an aromatic hydrocarbon-based ring, the weight percentages being expressed relative to the total weight of said composition. ### Claim 2 (depends on 1) The composition according to claim 1, wherein the compound(s) (A) are monoisocyanates or diisocyanates. ### Claim 3 (depends on 1) The composition according to claim 1, compound (A) is XDI. ### Claim 4 (depends on 1) The composition according to claim 1, comprising a total content of compound(s) (A) which is non-zero and less than 0.5% by weight relative to the weight of said composition. ### Claim 5 (depends on 1) The composition according to claim 1, wherein the non-hot-melt polyurethane(s) bearing NCO end groups based on 2,4-TDI may be obtained via a polyaddition reaction of a polyisocyanate composition consisting of TDI at 95% by weight at least of 2,4-TDI relative to the weight of TDI, and of a composition comprising polyol(s), at a temperature of less than 95° C., under anhydrous conditions, in amounts of polyisocyanate(s) and of polyol(s) leading to an NCO/OH ratio noted r1 ranging from 1.60 to 1.90. ### Claim 6 (depends on 5) The composition according to claim 5, wherein the temperature ranges from 70 to 80° C. and the NCO/OH ratio noted r1 ranges from 1.65 to 1.80. ### Claim 7 (depends on 5) The composition according to claim 5, wherein the composition comprising polyol(s) comprises at least one polyether polyol. ### Claim 8 (depends on 1) An adhesive composition, comprising: at least 50% by weight of a polyurethane composition as defined in claim 1, from 0 to 1% by weight of at least one crosslinking catalyst, from 0 to 20% by weight of at least one filler, from 0 to 20% by weight of at least one plasticizer, from 0 to 10% by weight of at least one rheology agent, from 0 to 50% by weight of at least one tackifying resin, from 0 to 10% by weight of at least one adjuvant comprising adhesion promoters, UV stabilizers (or antioxidants), pigments, colorants, or a mixture thereof, said weight percentages being expressed relative to the total weight of the adhesive composition. ### Claim 9 (depends on 1) A process for preparing a composition as defined in claim 1, comprising a step in which the compound(s) (A), and the other ingredient(s) optionally present in said composition, are mixed with a polyurethane composition comprising at least one polyurethane bearing NCO end groups based on 2,4-TDI, which is not solid at a temperature ranging from 5 to 35° C., and a TDI content of less than 0.1% by weight relative to the weight of said composition, at a temperature of less than or equal to 95° C., under anhydrous conditions in post-synthesis of said 2,4-TDI-based polyurethane bearing NCO end groups. ### Claim 10 (depends on 9) The process according to claim 9 for preparing a composition, wherein the compound(s) (A) are mixed with said composition: either directly after the end of the reaction for the synthesis of the polyurethane bearing NCO end groups based on 2,4-TDI, or after one, several or all of the other ingredients of the composition have been mixed with the polyurethane bearing NCO end groups based on 2,4-TDI. ### Claim 11 A method for stabilizing the viscosity of a composition comprising at least 98% by weight of at least one polyurethane based on 2,4-TDI bearing NCO end groups, which is not solid at a temperature ranging from 5 to 35° C., and a TDI content of less than 0.1% by weight relative to the weight of said composition, comprising adding to said composition at least one isocyanate compound with a molar volume of less than or equal to 300 milliliters per mole other than TDI, which isocyanate compound does not have isocyanate groups linked to a carbon atom of an aromatic hydrocarbon ring.