Polymeric material including a uretdione-containing material and a thermally activatable amine, two-part compositions, and methods

Patent metadata

Field	Value
Publication number	US-12018114-B2
Application number	US-201917265049-A
Country	US
Kind code	B2
Filing date	Sep 19, 2019
Priority date	Sep 25, 2018
Publication date	Jun 25, 2024
Grant date	Jun 25, 2024

Abstract

The present disclosure provides a polymeric material including a polymerized reaction product of a polymerizable composition including components, and a thermally activatable amine curative, and has a solids content of 90% or greater. 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 first hydroxyl-containing compound has more than one OH group and the optional second hydroxyl-containing compound is a primary alcohol or a secondary alcohol. The present disclosure also provides a two-part composition, in which a polymeric material is included in the first part and the second part includes at least one liquid amine. 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 polymeric material and a method of curing a two-part composition. Advantageously, two-part compositions according to the present disclosure can be used as coatings and adhesive systems having a two-step cure 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 polymeric material comprising:
a polymerized reaction product of a polymerizable composition comprising components, the components comprising:
(a) a uretdione-containing material comprising a reaction product of a diisocyanate reacted with itself;
(b) a first hydroxyl-containing compound having more than one OH group; and
(c) 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

a thermally activatable amine curative, at least one molecule of the thermally activatable amine curative having an average amine functionality of 2.0 or greater;
wherein the polymeric material has an average uretdione ring functionality of at least 1.2, wherein the polymeric material is in the form of a liquid at 24 degrees Celsius, wherein the polymeric material contains 2% by weight or less of isocyanate groups, and wherein the polymeric material comprises a solids content of 90% or greater.

2. The polymeric material of claim 1 , further comprising an acidic stabilizer.

3. The polymeric material of claim 1 , further comprising an accelerator comprising a catalyst for reacting the uretdione-containing material with the first-hydroxyl-containing compound and, if present, with the second hydroxyl-containing compound.

4. The polymeric material of claim 1 , further comprising an epoxy component.

5. 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) an optional thermally activatable amine curative;

wherein the polymeric material has an average uretdione ring functionality of at least 1.2, wherein the polymeric material contains 2% by weight or less of isocyanate groups, and wherein the polymeric material comprises a solids content of 90% or greater and
(2) a second part comprising:
(a) at least one liquid amine, at least one molecule of the at least one liquid amine having an average amine functionality of 2.0 or greater, wherein each amine of the at least one liquid amine comprises a primary amine or a secondary amine; and
(b) an optional thermally activatable amine curative;
wherein the thermally activatable amine curative is present in at least one of the first part or the second part and wherein at least one molecule of the thermally activatable amine curative has an average amine functionality of 2.0 or greater.

6. The two-part composition of claim 5 , wherein at least one amine of the at least one liquid amine comprises a primary amine.

7. The two-part composition of claim 5 , wherein at least one of the first part or the second part further comprises an accelerator comprising a catalyst.

8. The two-part composition of claim 7 , wherein the accelerator is present in the first part and comprises a catalyst for reacting the uretdione-containing material with the first-hydroxyl-containing compound and, if present, with the second hydroxyl-containing compound.

9. The two-part composition of claim 5 , wherein the uretdione-containing material is present in an amount of 10% by weight or greater, 20% by weight or greater, 30% by weight or greater, 40% by weight or greater, or 50% by weight or greater, based on the total weight of the polymeric material.

10. The two-part composition of claim 5 , wherein the thermally activatable amine curative is present in the first part in an amount of 0.5 to 30% by weight, based on the total weight of the polymeric material.

11. The two-part composition of claim 5 , wherein the first part further comprises an epoxy component.

12. The two-part composition of claim 5 , wherein the first part is in the form of a liquid.

13. A polymerized product of the two-part composition of claim 5 .

14. The polymerized product of claim 13 , wherein the polymerized product coats at least a portion of a substrate.

15. A method of adhering two substrates together, the method comprising:
(a) obtaining the two-part composition of claim 5 ;
(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.

16. A method of curing a two-part composition comprising:
(a) obtaining the two-part composition of claim 5 ;
(b) combining at least a portion of the first part with at least a portion of the second part to form a mixture; and
(c) subjecting the mixture to a temperature of 45° C. or higher to provide a polymerized reaction product of the mixture.

Assignees

• 3M Innovative Properties Company

Inventors

• White Kolby L
• Kryger Matthew J
• Rule Joseph D
• Kropp Michael A
• Jung Adrian T

Classifications

• C09J175/12

  from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group · CPC title

• C09D175/12

  from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group · CPC title

• C08G2190/00

  Compositions for sealing or packing joints · CPC title

• C08G59/5013

  containing more than seven carbon atoms, e.g. fatty amines · CPC title

• C08G59/4021

  Ureas; Thioureas; Guanidines; Dicyandiamides · CPC title