Two-part compositions including a uretdione-containing material and inorganic filler, products, and methods

Patent metadata

Field	Value
Publication number	US-12351673-B2
Application number	US-202017770366-A
Country	US
Kind code	B2
Filing date	Dec 10, 2020
Priority date	Dec 19, 2019
Publication date	Jul 8, 2025
Grant date	Jul 8, 2025

Abstract

The present disclosure provides a two-part composition polymeric material including a first part and a second part. The first part includes an inorganic filler and a polymeric material including a polymerized reaction product of a polymerizable composition including components. The components include a uretdione-containing material including a reaction product of a diisocyanate reacted with itself; a first hydroxyl-containing compound; and an optional second hydroxyl-containing compound having a single OH group. The second part includes a polythiol having an average sulfhydryl group functionality of 2 or greater. Further, a method of adhering two substrates is provided, including obtaining a two-part composition; combining at least a portion of the first part with at least a portion of the second part to form a mixture; disposing at least a portion of the mixture on a first substrate; and contacting a second substrate with the mixture disposed on the first substrate. The disclosure also provides a polymerized product of the two-part composition and a battery module. Advantageously, two-part compositions can be used as coatings and adhesive systems including high loadings of inorganic filler, such as thermally conductive filler, with handling and performance similar to existing two-part urethane systems, but with less sensitivity to water.

First claim

What is claimed is:

1. A two-part composition comprising:
1) a first part comprising a polymeric material comprising:
a) a polymerized reaction product of a polymerizable composition comprising components, the components comprising:
i) a uretdione-containing material comprising a reaction product of a diisocyanate reacted with itself;
ii) a first hydroxyl-containing compound having more than one OH group; and
iii) an optional second hydroxyl-containing compound having a single OH group, wherein the second hydroxyl-containing compound is a primary alcohol or a secondary alcohol; and

b) 40% by weight or greater of an inorganic filler, based on the total weight of the polymeric material;
wherein the polymerized reaction product comprises a uretdione functionality of 1.3 to 2.5 and wherein the polymerized reaction product has a number average molecular weight (Mn) of 1100 grams per mole (g/mol) or greater; and

2) a second part comprising:
a) a polythiol having an average sulfhydryl group functionality of 2 or greater; and
b) 40% by weight or greater of an inorganic filler, based on the total weight of the second part.

2. The two-part composition of claim 1 , wherein the inorganic filler of the first part, the second part, or both, comprises at least one of aluminum oxide, boron nitride, silicon dioxide, alumina trihydrate (ATH), aluminum nitride, silicon carbide, beryllium oxide, zinc oxide, carbon nanotubes, graphene, graphite, aluminum, or copper.

3. The two-part composition of claim 1 , wherein the inorganic filler of the first part is present in an amount of 45% by weight to 95% by weight, based on the total weight of the polymeric material.

4. The two-part composition of claim 1 , wherein the inorganic filler of the first part is present in an amount of 30 % by volume to 70% by volume, based on the total volume of the polymeric material.

5. The two-part composition of claim 1 , wherein the polythiol comprises a primary thiol.

6. The two-part composition of claim 1 , wherein the polythiol comprises a secondary thiol.

7. The two-part composition of claim 1 , wherein the first hydroxyl-containing compound is an alkylene polyol, a polyester polyol, or a polyether polyol.

8. The two-part composition of claim 1 , wherein the first hydroxyl-containing compound is of Formula II:
HO—R 2 —OH  II

wherein R 2 is selected from R 3 , an alkylene, and an alkylene substituted with an OH group, wherein R 3 is of Formula III or Formula IV:

wherein each of R 4 , R 5 , R 6 , R 7 , and R 8 is independently an alkylene, wherein each of v and y is independently 1 to 40, and wherein x is selected from 0 to 40.

9. The two-part composition of claim 1 , wherein the first hydroxyl-containing compound is a polypropylene glycol polyol or a polytetramethylene ether glycol.

10. The two-part composition of claim 9 , wherein the first hydroxyl-containing compound has a number average molecular weight of 500 to 4,000 g/mol.

11. The two-part composition of claim 1 , wherein the polymeric material further comprises at least one epoxy component.

12. The two-part composition of claim 1 , wherein the polymeric material further comprises at least one acrylate component.

13. The two-part composition of claim 1 , wherein the polymeric material exhibits a viscosity of 10,000 centiPoise (cP) to 11,000,000 cP, as determined using a parallel-plate geometry using steady flow mode and a shear rate of 1 1/s at 25° C.

14. A polymerized product of the two-part composition of claim 1 .

15. The polymerized product of claim 14 , exhibiting at least one of an overlap shear to aluminum of 1 MPa or greater at 140° C., a thermal conductivity of 0.5 W/m*K or greater, a tensile peak load of 0.25 or greater, a modulus of 500 MPa or less, or an elongation percent of 5 or greater.

16. A battery module comprising a plurality of battery cells connected to a base plate by a layer of the polymerized product of claim 14 .

17. A method of adhering two substrates together comprising:
A) obtaining a two-part composition, the two-part composition comprising:
1) a first part comprising a polymeric material comprising:
a) a polymerized reaction product of a polymerizable composition comprising components, the components comprising:
i) a uretdione-containing material comprising a reaction product of a diisocyanate reacted with itself;
ii) a first hydroxyl-containing compound having more than one OH group; and
iii) an optional second hydroxyl-containing compound having a single OH group, wherein the second hydroxyl-containing compound is a primary alcohol or a secondary alcohol; and

b) 40% by weight or greater of an inorganic filler, based on the total weight of the polymeric material;
wherein the polymerized reaction product comprises a uretdione functionality of 1.3 to 2.5 and wherein the polymerized reaction product has a number average molecular weight (Mn) of 1100 grams per mole (g/mol) or greater; and

2) a second part comprising:
a) a polythiol having an average sulfhydryl group functionality of 2 or greater; and
b) 40% by weight or greater of an inorganic filler, based on the total weight of the second part;

B) combining at least a portion of the first part with at least a portion of the second part to form a mixture;
C) disposing at least a portion of the mixture on a first major surface of a first substrate; and
D) contacting a first major surface of a second substrate with the mixture disposed on the first substrate.

Assignees

• 3M Innovative Properties Company

Inventors

• White Kolby L
• Yao Li
• Rule Joseph D
• Kryger Matthew J
• Kropp Michael A

Classifications

• Y10T428/2896

  including nitrogen containing condensation polymer [e.g., polyurethane, polyisocyanate, etc.] · CPC title

• C09J2203/33

  for batteries or fuel cells · CPC title

• C09J2203/326

  for bonding electronic components such as wafers, chips or semiconductors · CPC title

• C09J175/08

  from polyethers · CPC title

• C08K2201/001

  Conductive additives · CPC title