IP Library › Granted Patent US 12,545,782
Granted Patent B2
US 12,545,782 · App. 18/007,291 · Granted Feb 10, 2026

Thermally curable compositions, thermally cured compositions, and articles prepared therefrom

Inventor: Christian Heering (Düsseldorf, DE)
Assignee: 3M Innovative Properties Company
C08L63/00C08G59/5033C08G59/686C08K5/17C09J163/00
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Quick Facts
Patent No.
US 12,545,782
App. No.
18/007,291
Granted
Feb 10, 2026
Kind
B2
Abstract

Thermally curable compositions with excellent storage stability are provided that curing system comprising a compound of Formula (I). In Formula (I), L +n is a ulmetal or alkaline earth metal and n is equal to 1 or 2. Groups A and B are each independently an alkyl having 1 to 12 carbon atoms, a cycloalkyl having 3 to 12 carbon atoms, an aryl having 6 to 12 carbon atoms, an aralkyl or alkaryl group having from 7 to 12 carbon atoms, or a group of formula —[(Z)—N(R 1 )(R 2 )] where Z is an alkylene having from 1 to 12 carbon atoms and R 1 and R 2 are each independently an alkyl groups having from 1 to 6 carbon atoms. Cured compositions formed from the thermally curable compositions, articles containing the thermally curable composition, articles containing the cured composition, and methods of bonding with the thermally curable compositions are provided. The thermally curable compositions can be used, for example, in various construction and transportation applications.

Claims (29)

1 . A thermally curable composition comprising:

a) a thermally curable resin; and

b) a thermal curing system comprising a compound of formula (I)

wherein:

L +n is a cation of an alkali metal or alkaline earth metal where n is equal to 1 or 2;

A and B are each independently an alkyl having 1 to 12 carbon atoms, a cycloalkyl having 3 to 12 carbon atoms, an aryl having 6 to 12 carbon atoms, an aralkyl or alkaryl having from 7 to 12 carbon atoms;

Z is an alkylene having from 1 to 12 carbon atoms;

R 1 and R 2 are each independently an alkyl groups having from 1 to 6 carbon atoms; and

the thermally curable composition having a storage stability of at least 30 days when stored at room temperature and 50 percent relative humidity.

2 . The thermally curable composition of claim 1 , wherein A and B are each independently tert-butyl, neopentyl, tert-pentyl, neo-hexyl, or tert-hexyl.

3 . The thermally curable composition of claim 1 , wherein L +n is a cation of sodium, lithium, potassium, calcium, or magnesium.

4 . The thermally curable composition of claim 1 , wherein the compound of Formula (I) is [2,6-di-tert-butyl-4-(dimethylaminomethyl) phenoxy]-lithium, [2,6-di-tert-butyl-4-(dimethylaminomethyl) phenoxy]-sodium, [2,6-di-tert -butyl-4-(dimethylaminomethyl) phenoxy]-potassium, bis [2,6-di-tert-butyl-4-(dimethylaminomethyl) phenoxy]-calcium, bis [2,6-di-tert-butyl-4-(dimethylaminomethyl) phenoxy]-magnesium, or a mixture thereof.

5 . The thermally curable composition of claim 1 , wherein the compound of Formula (I) dissociates at a temperature equal to at least 60 degrees Celsius.

6 . The thermally curable composition of claim 1 , wherein the thermally curable resin comprises a plurality of functional groups selected from the group consisting of an epoxy group, isocyanate group, urethane group, and a mixture thereof.

7 . A cured composition comprising reaction product of the thermally curable composition of claim 1 .

8 . The cured composition of claim 7 , wherein the cured composition is a structural adhesive composition.

9 . A first article comprising:

a first substrate; and

a thermally curable composition of claim 1 , wherein a first surface of the thermally curable composition is positioned adjacent to the first substrate.

10 . The first article of claim 9 , wherein the first article further comprises a second substrate and wherein the second substrate is positioned adjacent to a second surface of the thermally curable composition opposite the first surface of the thermally curable composition.

11 . A second article comprising:

a first substrate;

a second substrate; and

a cured composition of claim 7 , wherein a first surface of the cured composition is positioned adjacent to the first substrate and a second surface of the cured composition is positioned adjacent to the second substrate, the second surface of the cured composition being opposite the first surface of the cured composition, the first substrate being bonded to the second substrate through the cured composition.

12 . A method of bonding two substrates together the method comprising:

providing (a) a first substrate, (b) a second substrate, and (c) a thermally curable composition according to claim 1 ;

positioning a first surface of the thermally curable composition adjacent to the first substrate;

positioning the second substrate adjacent to a second surface of the thermally curable composition opposite the first surface of the thermally curable composition; and

heating the thermally curable composition to form a cured composition that bonds the first substrate to the second substrate.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 27, 2023
From: HEERING, CHRISTIAN
To: 3M INNOVATIVE PROPERTIES COMPANY
Reel/Frame 062517/0935 →
Priority Claims (1)
EP 20193551 · Aug 31, 2020 · regional
Continuity (1)
Related Publication 20230279216A1 · Sep 7, 2023
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