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

Patent metadata

Field	Value
Publication number	US-11292870-B2
Application number	US-201816632679-A
Country	US
Kind code	B2
Filing date	Aug 20, 2018
Priority date	Sep 7, 2017
Publication date	Apr 5, 2022
Grant date	Apr 5, 2022

Abstract

The present disclosure provides a polymeric material including a reaction product of a polymerizable composition and having a solids content of 90% or greater. The polymerizable composition includes a uretdione-containing material including a reaction product of a diisocyanate reacted with itself, a first hydroxyl-containing compound having a single OH group, and a second hydroxyl-containing compound having more than one OH group. The first hydroxyl-containing compound is a primary alcohol or a secondary alcohol, plus the second hydroxyl-containing compound is a diol and the reaction product contains 0.2 to 0.5, inclusive, of diol equivalents relative to isocyanate equivalents. 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 reaction product of a polymerizable composition, the polymerizable composition comprising:
a. a uretdione-containing material comprising a reaction product of a diisocyanate reacted with itself;
b. a first hydroxyl-containing compound having a single OH group, wherein the first hydroxyl-containing compound is a primary alcohol or a secondary alcohol; and
c. a second hydroxyl-containing compound having more than one OH group, wherein the second hydroxyl-containing compound is a diol and the polymerizable composition comprises 0.2 to 0.5, inclusive, of OH equivalents from the diol relative to isocyanate equivalents;
wherein the polymeric material comprises a solids content of 90% or greater, wherein the polymeric material comprises an average of 1.3 to 2.5, inclusive, of a uretdione functional group in a backbone of the polymeric material, and wherein the polymeric material comprises a dynamic viscosity of 10 Poise (P) to 10,000 P, inclusive, as determined using a Brookfield viscometer at 24 degrees Celsius.

2. The polymeric material of claim 1 , wherein the first hydroxyl-containing compound is an alkyl alcohol, a polyester alcohol, or a polyether alcohol.

3. The polymeric material of claim 1 , wherein the second hydroxyl-containing compound is an alkylene diol, a polyester diol, or a polyether diol.

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

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

5. The polymeric material of claim 1 , wherein the first hydroxyl-containing compound is of Formula II:
R 2 —OH  II

wherein R 2 is selected from R 3 , R 4 , and a C 1 to C 50 alkyl;
wherein R 3 is of Formula III:

wherein m=1 to 20, R 5 is an alkyl, and R 6 is an alkylene;

wherein R 4 is of Formula IV:

wherein n=1 to 20, R 7 is an alkyl, and R 8 is an alkylene.

6. The polymeric material of claim 1 , wherein the second hydroxyl-containing compound is of Formula V:
HO—R 9 —OH  V

wherein R 9 is selected from R 10 , and an alkylene wherein R 10 is of Formula VI or Formula VII:

wherein each of R 11 , R 12 , R 13 , R 14 , and R 15 is independently selected from an alkylene, wherein each of v and y is independently selected from 1 to 40, and wherein x is selected from 0 to 40.

7. The polymeric material of claim 1 , comprising an average of 1.5 to 1.8, 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 diisocyanate comprises hexamethylene diisocyanate.

10. The polymeric material of claim 1 , wherein the polymeric material comprises an average of 1.3 or fewer isocyanurate units per molecule of the polymeric material.

11. The polymeric material of claim 1 , wherein a sum of the OH equivalents of the first hydroxyl-containing compound and the second hydroxyl-containing compound is equal to or greater than the isocyanate equivalents of the polymeric material.

12. A two-part composition comprising:
a. a first part comprising a polymeric material comprising a reaction product of a polymerizable composition, the polymerizable composition comprising:
i. a uretdione-containing material comprising a reaction product of a diisocyanate reacted with itself;
ii. a first hydroxyl-containing compound having a single OH group, wherein the first hydroxyl-containing compound is a primary alcohol or a secondary alcohol; and
iii. a second hydroxyl-containing compound having more than one OH group wherein the second hydroxyl-containing compound is a diol and the polymerizable composition comprises 0.2 to 0.5, inclusive, of OH equivalents from the diol relative to isocyanate equivalents;
wherein the polymeric material comprises an average of 1.3 to 2.5, inclusive, 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 wherein the polymeric material comprises a dynamic viscosity of 10 Poise (P) to 10,000 P, inclusive, as determined using a Brookfield viscometer at 24 degrees Celsius; and

b. a second part comprising at least one amine, 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.

13. The two-part composition of claim 12 , wherein the at least one amine comprises a molecular weight of 2,000 grams per mole or less.

14. A polymerized product of the two-part composition of claim 12 .

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

16. The polymerized product of claim 14 , wherein the polymerized product is disposed between two substrates.

17. The polymerized product of claim 15 , wherein at least one substrate comprises a moisture impermeable material.

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 comprising a polymeric material comprising a reaction product of a polymerizable composition, the polymerizable composition comprising:
1. a uretdione-containing material comprising a reaction product of a diisocyanate reacted with itself;
2. a first hydroxyl-containing compound having a single OH group, wherein the first hydroxyl-containing compound is a primary alcohol or a secondary alcohol; and
3. a second hydroxyl-containing compound having more than one OH group wherein the second hydroxyl-containing compound is a diol and the polymerizable composition comprises 0.2 to 0.5, inclusive, of OH equivalents from the diol relative to isocyanate equivalents;

wherein the polymeric material comprises an average of 1.3 to 2.5, inclusive, 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 wherein the polymeric material comprises a dynamic viscosity of 10 Poise (P) to 10,000 P, inclusive, as determined using a Brookfield viscometer at 24 degrees Celsius; and
ii. a second part comprising at least one amine, 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 comprising

Assignees

• 3M Innovative Properties Co

Inventors

• Rule Joseph D
• Thompson Zachary J
• Kropp Michael A
• White Kolby L

Classifications

• C08G18/3228

  acyclic · CPC title

• C08G18/48

  Polyethers · CPC title

• C08G18/329

  containing aromatic groups · CPC title

• C08G18/2825

  having at least 6 carbon atoms · CPC title

• C08G18/5024

  containing primary and/or secondary amino groups · CPC title