IP Library Granted Patent US 12686766
Granted Patent B2
US 12686766 · App. 17/593,250 · Granted Jul 21, 2026

Curable compositions, articles therefrom, and methods of making and using same

Inventors: Lingjie Tong (Shanghai, CN); Yuan Zhao (Shanghai, CN); Li Yao (Woodbury, MN); Shuang Wu (Shanghai, CN); Xiaohai Sheng (Shanghai, CN); Xinxin Sun (Shanghai, CN); Ahmad Shaaban (Cologne, DE); Menghuang Feng (Tianjin, CN)
Assignee: 3M Innovative Properties Company
C08L63/00C08G59/245C08G59/66C08G59/686C08K3/013C08K3/22C08K5/37C08K7/18C08K9/06C09J163/00H01M10/653H01M50/209H01M50/233C08K2003/2227H01M50/264H01M2220/20
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Quick Facts
Patent No.
US 12686766
App. No.
17/593,250
Granted
Jul 21, 2026
Kind
B2
Abstract

A curable composition includes a first part comprising an epoxy resin; and a second part comprising a multifunctional, functional thiol containing compound. The curable composition further includes an inorganic filler present in an amount of at least 40 weight %, based on the total weight of the curable composition. The multifunctional, functional thiol containing compound comprises ether in the backbone thereof.

Claims (30)

1 . A curable composition comprising:

a first part comprising an epoxy resin; and

a second part comprising a multifunctional, functional thiol containing compound; and

an inorganic filler present in an amount of at least 40 weight %, based on the total weight of the curable composition,

wherein the

multifunctional, functional thiol containing compound is represented by the following formula:

wherein, independently,

R 3 being R 1 O(CH 2 CHR 2 O) n R 1 ;

each R 1 independently represents an alkylene group having from 2 to 12 carbon atoms;

R 4 being a branched aliphatic chain containing 2 to 18 sulfur or nitrogen junctions and a being 2 to 10; or R 4 being HSR 1 O(CH 2 CHR 2 O)R 1 S, and a being 1;

each R 2 independently represents H or CH 3 ;

n represents an integer from 1 to 20;

R 5 being bisphenol A, or bisphenol F, or bisphenol S, or biphenyl, or halogenated bisphenol or aliphatic chain having from 1 to 18 carbon atoms; and

m being 0 to 18.

2 . The curable composition of claim 1 , wherein the epoxy resin of the first part comprises an internally flexible bisphenol epoxy resin of formula

where Ar is bisphenol A, bisphenol F, bisphenol Z, or a mixture thereof.

3 . The curable composition of claim 1 , wherein the epoxy resin of the first part comprises a phosphonic acid group in the backbone thereof.

4 . The curable composition of claim 1 , wherein the epoxy resin of the first part further comprises a rigid bisphenol epoxy resin, wherein the rigid bisphenol epoxy resin is present in the curable composition in an amount of less than 50 wt. %, based on the total weight of epoxy resin.

5 . The curable composition according to claim 1 , further comprising an amine terminated silane coupling agent, a mercaptan terminated silane coupling agent, or an epoxy terminated silane coupling agent.

6 . The curable composition according to claim 1 , further comprising a catalyst.

7 . The curable composition according to claim 1 , wherein epoxy resin is present in the curable composition in an amount of at least 20 wt. %, based on the total weight of the unfilled curable composition.

8 . The curable composition according to claim 1 , wherein multifunctional, functional thiol containing compounds are present in the curable composition in an amount of 4.9-20 wt. %, based on the total weight of the unfilled curable composition.

9 . The curable composition according to claim 1 , further comprising a multifunctional amine.

10 . The curable composition according to claim 1 , wherein the inorganic filler present in an amount of at least 50 wt. %, based on the total weight of the curable composition.

11 . An article comprising a cured composition, wherein the cured composition is the reaction product of the curable composition according to claim 1 .

12 . The article of claim 11 , wherein the cured composition has a thickness between from 5 microns to 10000 microns.

13 . The article of claim 11 , further comprising a metal substrate having a surface, wherein the cured composition is disposed on the surface of the substrate.

14 . The article of claim 11 comprising a first substrate, a second substrate and the cured composition disposed between and adhering the first substrate to the second substrate.

15 . The article of claim 11 , wherein the article is a battery module comprising a plurality of battery cells connected to a first base plate by a first layer of the reaction product of the curable composition.

16 . A method of making a battery module comprising: applying a first layer of a curable composition according to claim 1 to a first surface of a first base plate, attaching a plurality of battery cells to the first layer to connect the battery cells to the first base plate, and curing the curable composition.