Polymeric material including a uretdione-containing material and an epoxy component, two-part compositions, and methods

Patent metadata

Field	Value
Publication number	US-11655327-B2
Application number	US-201917265023-A
Country	US
Kind code	B2
Filing date	Sep 16, 2019
Priority date	Sep 20, 2018
Publication date	May 23, 2023
Grant date	May 23, 2023

Abstract

The present disclosure provides a polymeric material including a polymerized reaction product of a polymerizable composition including components 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; an optional second hydroxyl-containing compound having a single OH group, wherein; and an epoxy component. 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 the polymeric material is included in the first part and the second part includes at least one 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 making a two-part composition. Advantageously, two-part compositions according to the present disclosure can be used as coatings and adhesive systems 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;
(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
(d) an epoxy component;

wherein the polymeric material comprises a solids content of 90% or greater and exhibits a dynamic viscosity of 10 Poise (P) to 10,000 P, inclusive, as determined using a Brookfield viscometer.

2. The polymeric material of claim 1 , wherein components (a), (b), and, if present, (c), are reacted, and then component (d) is combined with the reaction product of components (a), (b), and, if present, (c).

3. The polymeric material of claim 1 , wherein component (d) is present at the time of reaction of components (a), (b), and, if present, (c).

4. The polymeric material of claim 1 , wherein the second hydroxyl-containing compound is present and is an alkyl alcohol, a polyester alcohol, or a polyether alcohol.

5. The polymeric material of claim 1 , wherein the first hydroxyl-containing compound is an alkylene polyol, a polyester polyol, or a polyether polyol.

6. The polymeric material of claim 1 , wherein the uretdione-containing material comprises a compound of Formula I:

wherein R 1 is independently a C 4 to C 14 alkylene, arylene, and alkaralyene.

7. The polymeric material of claim 1 , comprising an average of 1.3 to 6.0, inclusive, of a uretdione functional group in a backbone of the polymeric material.

8. The polymeric material of claim 1 , wherein the polymeric material is essentially free of isocyanates.

9. The polymeric material of claim 1 , wherein the epoxy component exhibits a Log water octanol partition coefficient according to the Moriguchi method of less than 27.5, less than 18, less than 10, less than 5, or less than 2.3.

10. The polymeric material of claim 1 , wherein the epoxy component comprises at least one multifunctional epoxy.

11. The polymeric material of claim 1 , wherein the epoxy component comprises at least one glycidyl ether group.

12. The polymeric material of claim 1 , wherein the epoxy component comprises an aliphatic epoxy.

13. The polymeric material of claim 1 , wherein the epoxy component is present in an amount of 31% by weight or less, based on the total weight of the polymerizable composition.

14. A two-part composition comprising:
(a) a first part comprising a polymeric material comprising:
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;
(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
(iv) (iv) an epoxy component;
wherein the polymeric material comprises an average of 1.3 or greater of a uretdione functional group in a backbone of the polymeric material and wherein the polymeric material comprises a solids content of 90% or greater and exhibits a dynamic viscosity of 10 Poise (P) to 10,000 P, inclusive, as determined using a Brookfield viscometer; and

(b) a second part comprising at least one amine, at least one molecule of the at least one amine having an average amine functionality of 2.0 or greater, wherein each amine is a primary amine or a secondary amine.

15. The two-part composition of claim 14 , wherein at least one molecule of the at least one amine has an average amine functionality of 3.0 or greater.

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

17. The polymerized product of claim 16 , wherein the polymerized product coats at least a portion of a substrate.

18. A method of adhering two substrates together, the method comprising:
(a) obtaining a two-part composition, the two-part composition comprising:
(i) a first part comprising:
a polymeric material comprising a reaction product of a polymerizable composition comprising components, the components comprising:
(1) a uretdione-containing material comprising a reaction product of a diisocyanate reacted with itself;
(2) a first hydroxyl-containing compound having more than one OH group;
(3) 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
(4) an epoxy component;

wherein the polymeric material comprises an average of 1.3 or greater of a uretdione functional group in a backbone of the polymeric material and wherein the polymeric material comprises a solids content of 90% or greater and exhibits a dynamic viscosity of 10 Poise (P) to 10,000 P, inclusive, as determined using a Brookfield viscometer; and
(ii) a second part comprising at least one amine, at least one molecule of the at least one amine having an average amine functionality of 2.0 or greater wherein each amine is a primary amine or a secondary amine;

(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.

19. The method of claim 18 , wherein the adhesive exhibits a minimum overlap shear on aluminum of 0.3 megaPascals (MPa).

20. A method of making a two-part composition, the method comprising:
(a) providing a first part by forming a polymeric material of claim 1 ; and
(b) providing a second part comprising at least one amine, at least one molecule of the at least one amine having an average amine functionality of 2.0 or greater, wherein each amine is a primary amine or a secondary amine.

Assignees

• 3M Innovative Properties Company

Inventors

• White Kolby L
• Rule Joseph D
• Kropp Michael A
• Kryger Matthew J
• Thompson Zachary J
• Ross Richard B

Classifications

• C08G18/4238

  derived from dicarboxylic acids and dialcohols · CPC title

• B32B5/32

  at least two} layers being foamed {and next to each other · CPC title

• B32B5/18

  characterised by features of a layer {of} foamed material · CPC title

• C08G18/2825 Primary

  having at least 6 carbon atoms · CPC title

• C09J163/00

  Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins · CPC title