Polymerizable ionic liquid comprising multifunctional cation and antistatic coatings

• US 9,458,327 B2
• Filed: 04/02/2014
• Issued: 10/04/2016
• Est. Priority Date: 08/28/2009
• Status: Active Grant

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Lewandowski, Kevin M., Krepski, Larry R., Wang, Yizhong, Oxman, Joel D., Zhu, Peiwang, Holmes, Brian N., Klun, Thomas P., Hunt, Bryan V.
• Primary Examiner(s): MCCLENDON, SANZA L
• Application Number:
  US14/243,049
• Publication Number:
  US 20140213726A1
• Time in Patent Office: 916 Days
• US Class Current: 1/1
• CPC Class Codes: C07C 219/06 having the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton
• CPC Class Codes: C07C 229/16 to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids
• CPC Class Codes: C07C 271/16 to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
• CPC Class Codes: C07D 233/60 with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
• CPC Class Codes: C08F 22/22 Esters containing nitrogen
• CPC Class Codes: C08F 222/102 of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
• CPC Class Codes: C08F 222/22 Esters containing nitrogen
• CPC Class Codes: C09D 4/00 Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16

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.

Claims

1. A multifunctional polymerizable ionic liquid having the formula

2. The multifunctional polymerizable ionic liquid of claim 1 wherein n is at least 1 and R¹ is a lower alkyl of 1 to 4 carbon atoms.

3. The multifunctional polymerizable ionic liquid of claim 1 wherein R² is (meth)acrylate.

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

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.

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:

(R¹)_a-bG⁺[(CH₂)_qDR²]X⁻

wherein

each R¹ 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;

R² 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:

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

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

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:

(R¹)_a-bG⁺[(CH₂)_qDR²]X⁻

wherein

each R¹ 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;

R₂ 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: