IP Library Granted Patent US 12,460,106
Granted Patent B2
US 12,460,106 · App. 18/576,825 · Granted Nov 4, 2025

One-component moisture-curable adhesive composition

Inventors: Shahin Akhlaghi (Amsterdam, NL); Hendrica Petronella Maria Verlaan-Hooft (Amsterdam, NL)
Assignee: Akzo Nobel Coatings International B.V.
C09J7/10C09J4/00C09J175/08C09J2301/312C09J2301/408C09J2301/50C09J2400/303
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Quick Facts
Patent No.
US 12,460,106
App. No.
18/576,825
Granted
Nov 4, 2025
Kind
B2
Abstract

A one-component moisture-curing polyurethane adhesive composition is provided, comprising an isocyanate-functional prepolymer obtainable by reacting (a) one or more polyisocyanates comprising methyl diphenyl diisocyanate; and (b) a polyol mixture comprising (b1) a linear butylene oxide-based diol with two primary hydroxyl groups; and (b2) a polyether triol with three secondary hydroxyl groups wherein 55 to 75% of the hydroxyl groups in polyol mixture (b) are hydroxyl groups from butylene oxide-based diol (b1), wherein the equivalent ratio between isocyanate groups in (a) and hydroxyl groups in (b) is in the range of from 3.5 to 7.0, and wherein the content of free isocyanate groups in the adhesive composition is in the range of from 14 to 17 wt %. A method of bonding a first piece of material to a second piece of material using such adhesive composition, and an object made using the method, are also provided.

Claims (22)

1 . A one-component moisture-curable adhesive composition comprising from 80 to 100 wt % of an isocyanate-functional prepolymer obtainable by reacting:

(a) one or more polyisocyanates comprising methyl diphenyl diisocyanate; and

(b) a polyol mixture comprising:

(b1) a linear butylene oxide-based diol with two primary hydroxyl groups; and

(b2) a polyether triol with three secondary hydroxyl groups,

wherein in the range of from 55 to 75% of the hydroxyl groups in polyol mixture (b) are hydroxyl groups from butylene oxide-based diol (b1), wherein the equivalent ratio between isocyanate groups in (a) and hydroxyl groups in (b) is in the range of from 3.5 to 7.0, and wherein the content of free isocyanate groups in the adhesive composition is in the range of from 14 to 17 wt % determined according to ASTM D2572-19.

2 . A one-component moisture-curable adhesive composition according to claim 1 , further comprising a curing catalyst.

3 . A one-component moisture-curable adhesive composition according to claim 2 , wherein the curing catalyst is 2,2′-dimorpholinediethylether.

4 . A one-component moisture-curable adhesive composition according to claim 1 , wherein butylene oxide-based diol (b1) has a number average molecular weight in the range of from 500 to 1,500 g/mol determined by size-exclusion chromatography using polystyrene standards according to ISO 16014-1.

5 . A one-component moisture-curable adhesive composition according to claim 1 , wherein polyether triol (b2) has a number average molecular weight in the range of from 500 to 1,500 g/mol determined by size-exclusion chromatography using polystyrene standards according to ISO 16014-1.

6 . A one-component moisture-curable adhesive composition according to claim 1 , wherein the polyol mixture (b) is substantially free of any polyols other than (b1) and (b2).

7 . A one-component moisture-curable adhesive composition according to claim 1 , wherein in the range of from 60 to 70% of the hydroxyl groups in polyol mixture (b) are hydroxyl groups from butylene oxide-based diol (b1).

8 . A one-component moisture-curable adhesive composition according to claim 1 , wherein the equivalent ratio between isocyanate groups in (a) and hydroxyl groups in (b) is in the range of from 4.0 to 6.5.

9 . A one-component moisture-curable adhesive composition according to claim 1 , wherein the content of free isocyanate groups in the adhesive composition is in the range of from 15.0 to 16.5 wt % determined according to ASTM D2572-19.

10 . A one-component moisture-curable adhesive composition according to claim 1 , wherein the one or more polyisocyanates (a) essentially consists of methyl diphenyl diisocyanate.

11 . A one-component moisture-curable adhesive composition according to claim 1 comprising from 85 to 99.8 wt % of the prepolymer.

12 . A one-component moisture-curable adhesive composition according to claim 1 , further comprising one or more additives.

13 . A one-component moisture-curable adhesive composition according to claim 1 , wherein the equivalent ratio between isocyanate groups in (a) and hydroxyl groups in (b) is in the range of from 4.5 to 6.0.

14 . A one-component moisture-curable adhesive composition according to claim 1 , further comprising a defoaming agent and/or a thickener.

15 . A method of bonding a first piece of material to a second piece of material, comprising contacting a surface of the first material with a surface of the second material, wherein at least one of the contacted surfaces has the adhesive composition according to claim 1 applied to it prior to the contacting.

16 . An object comprising a first piece of material and a second piece of material bonded with the adhesive composition according to claim 1 .

17 . An object according to claim 16 , wherein the material is wood, and the object is a structural wood product.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 5, 2024
From: AKHLAGHI, SHAHIN; VERLAAN-HOOFT, HENDRICA PETRONELLA MARIA
To: AKZO NOBEL COATINGS INTERNATIONAL B.V.
Reel/Frame 066030/0693 →
Priority Claims (1)
EP 21185297 · Jul 13, 2021 · regional
Continuity (1)
Related Publication 20240309242A1 · Sep 19, 2024
References Cited (35)
US 7253244B2 · Gruenewaelder et al. · 2007 [cited by applicant]
US 10662276B2 · Colson et al. · 2020 [cited by applicant]
US 20040259968A1 · Krebs · 2004 [cited by applicant]
US 20050032972A1 · Gruenewaelder et al. · 2005 [cited by applicant]
US 20050137377A1 · Gruenewaelder et al. · 2005 [cited by applicant]
US 20060283548A1 · Singh et al. · 2006 [cited by applicant]
US 20170321095A1 · Pela et al. · 2017 [cited by applicant]
US 20210024795A1 · Schmatloch et al. · 2021 [cited by applicant]
EP 0244608A1 · 1987 [cited by applicant]
EP 1072620A2 · 2001 [cited by applicant]
EP 1072620B1 · 2005 [cited by examiner]
JP 61141777A · 1984 [cited by applicant]
JP 2009132832 · 2009 [cited by applicant]
JP 2014201635 · 2014 [cited by applicant]
JP 2016507596 · 2016 [cited by applicant]
JP 2021011538 · 2021 [cited by applicant]
WO 9919141A1 · 1999 [cited by applicant]
WO 03016368A1 · 2003 [cited by applicant]
WO 03055929A1 · 2003 [cited by applicant]
WO 2016060977A1 · 2016 [cited by applicant]
WO 2016196258A1 · 2016 [cited by applicant]
WO 2017083380A1 · 2017 [cited by applicant]
WO 2019081598A1 · 2019 [cited by applicant]
WO 2020023696A1 · 2020 [cited by applicant]
WO 2020201419A1 · 2020 [cited by applicant]
WO 2021022470A1 · 2021 [cited by applicant]
“Office Action,” for Japanese Patent Application No. 2024-500178 mailed Aug. 6, 2024 (6 pages) with English translation. [cited by applicant]
International Search Report and Written Opinion of Corresponding International Application No. PCT/EP2022/069450, mailed Oct. 21, 2022. [cited by applicant]
Extended European Search Report of Corresponding EP Application No. 21185297.5, dated Jan. 19, 2022. [cited by applicant]
English Translation of EP0244608A1. [cited by applicant]
English Translation of EP1072620A2. [cited by applicant]
Derwent Abstract of JP1141777A. [cited by applicant]
English Translation of WO03016368A1. [cited by applicant]
English Translation of WO03055929A1. [cited by applicant]
English Translation of WO2020201419A1. [cited by applicant]