Polymerizable ionic liquid comprising multifunctional cation and antistatic coatings

Patent metadata

Field	Value
Publication number	US-9458327-B2
Application number	US-201414243049-A
Country	US
Kind code	B2
Filing date	Apr 2, 2014
Priority date	Aug 28, 2009
Publication date	Oct 4, 2016
Grant date	Oct 4, 2016

Abstract

A multifunctional polymerizable ionic liquid is described comprising an anion and a cationic group having at least two ethylenically unsaturated polymerizable groups, each bonded to the cationic group via a divalent non-alkyl linking group. The multifunctional linking groups independently comprise a heteroatom such as oxygen or nitrogen. The linking groups may independently comprise one or more linkages such as an amide, urea, and more typically a urethane or ester linkage. The ethylenically unsaturated polymerizable groups are typically (meth)acrylate groups. Coatings and coated articles are also described.

First claim

What is claimed is:

1. A multifunctional polymerizable ionic liquid having the formula

wherein:
Q is nitrogen or phosphorous;
R 1 is independently hydrogen, alkyl, aryl, alkaryl, or a combination thereof;
R 2 is independently an ethylenically unsaturated group selected from (meth)acryl or vinyl ether;
L 1 is the divalent linking group independently comprising one or more linkages selected from amide, urethane, urea, or ester;
m is an integer of 2 to 4;
n is an integer of 0 to 2; and
m+n=4;
X is an anion, wherein when n is 2, X is an organic anion.

2. The multifunctional polymerizable ionic liquid of claim 1 wherein n is at least 1 and R 1 is a lower alkyl of 1 to 4 carbon atoms.

3. The multifunctional polymerizable ionic liquid of claim 1 wherein R 2 is (meth)acrylate.

4. The multifunctional polymerizable ionic liquid of claim 1 wherein the polymerizable ionic liquid has the formula

5. A multifunctional polymerizable ionic liquid wherein the multifunctional polymerizable ionic liquid has the formula

wherein:
R 1 is independently comprises hydrogen, alkyl, aryl, alkaryl, or a combination thereof;
R 2 is independently an ethylenically unsaturated group selected from (meth)acryl or vinyl ether;
L 1 is the divalent linking group independently comprising one or more linkages selected from amide, urethane, urea, or ester;
d is an integer of 0 to 3;
X is an anion.

6. The multifunctional polymerizable ionic liquid of claim 1 wherein the polymerizable ionic liquid has an air to nitrogen curing exotherm ratio of at least 0.90.

7. A coating comprising the multifunctional polymerizable ionic liquid of claim 1 .

8. The coating of claim 7 wherein the coating further comprises at least one polymerizable monomer, oligomer, or polymer.

9. The coating of claim 8 wherein the polymerizable monomer, oligomer, or polymer is selected from poly(meth)acryl monomers, mono(meth)acryl compounds, and oligomeric (meth)acryl compounds.

10. The coating of claim 7 wherein the coating can be completely cured in air.

11. A coated substrate comprising a substrate and the coating claim 1 cured on a surface of the substrate.

12. The multifunctional polymerizable ionic liquid of claim 5 wherein the anion is a sulfonate or fluororganic anion.

13. The coating composition of claim 7 wherein the coating further comprises a monofunctional polymerizable ionic liquid.

14. The coating of claim 13 wherein the monofunctional polymerizable ionic liquid has the formula:
(R 1 ) a-b G + [(CH 2 ) q DR 2 ]X −

wherein
each R 1 comprises independently a hydrogen, alkyl, aryl, alkaryl, or a combination thereof;
G is nitrogen, sulfur or phosphorous;
a is 3 where G is sulfur and a is 4 where G is nitrogen or phosphorous;
q is an integer from 1 to 4;
D is oxygen, sulfur, or NR wherein R is H or a lower alkyl of 1 to 4 carbon atoms;
R 2 is a (meth)acryl; and
X− is an anion.

15. The coating of claim 14 wherein G is nitrogen of an ammonium cation.

16. The coating of claim 14 wherein G is included in the cycle of an imidazolium cation and the monofunctional polymerizable liquid has the formula:

17. The multifunctional polymerizable ionic liquid of claim 5 wherein the polymerizable ionic liquid has an air to nitrogen curing exotherm ratio of at least 0.90.

18. A coating comprising the multifunctional polymerizable ionic liquid of claim 5 .

19. The coating of claim 18 wherein the coating further comprises at least one polymerizable monomer, oligomer, or polymer.

20. The coating of claim 19 wherein the polymerizable monomer, oligomer, or polymer is selected from poly(meth)acryl monomers, mono(meth)acryl compounds, and oligomeric (meth)acryl compounds.

21. The coating of claim 18 wherein the coating can be completely cured in air.

22. A coated substrate comprising a substrate and the coating claim 5 cured on a surface of the substrate.

23. The coating composition of claim 18 wherein the coating further comprises a monofunctional polymerizable ionic liquid.

24. The coating of claim 23 wherein the monofunctional polymerizable ionic liquid has the formula:
(R 1 ) a-b G + [(CH 2 ) q DR 2 ]X −

wherein
each R 1 comprises independently a hydrogen, alkyl, aryl, alkaryl, or a combination thereof;
G is nitrogen, sulfur or phosphorous;
a is 3 where G is sulfur and a is 4 where G is nitrogen or phosphorous;
q is an integer from 1 to 4;
D is oxygen, sulfur, or NR wherein R is H or a lower alkyl of 1 to 4 carbon atoms;
R 2 is a (meth)acryl; and
X− is an anion.

25. The coating of claim 24 wherein G is nitrogen of an ammonium cation.

26. The coating of claim 24 wherein G is included in the cycle of an imidazolium cation and the monofunctional polymerizable liquid has the formula:

Assignees

• 3M Innovative Properties Co

Inventors

• Lewandowski Kevin M
• Krepski Larry R
• Wang Yizhong
• Oxman Joel D
• Zhu Peiwang
• Holmes Brian N
• Klun Thomas P
• Hunt Bryan V

Classifications

• C08F22/22

  Esters containing nitrogen · CPC title

• C08F222/1006

  of polyhydric alcohols or polyhydric phenols · CPC title

• C07C271/16

  to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms · CPC title

• C07C229/16

  to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids · CPC title

• C08F222/22 Primary

  Esters containing nitrogen · CPC title