Compositions and articles comprising polymerizable ionic liquid mixture, and methods of curing

• US 8,816,029 B2
• Filed: 08/26/2010
• Issued: 08/26/2014
• 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: Wang, Yizhong, Oxman, Joel D., Krepski, Larry R., Zhu, Peiwang, Lewandowski, Kevin M., Holmes, Brian N., Severance, Richard L., Rule, Joseph D., Klun, Thomas P.
• Primary Examiner(s): BERNSHTEYN, MICHAEL
• Application Number:
  US13/380,267
• Publication Number:
  US 20120101184A1
• Time in Patent Office: 1,461 Days
• Field of Search: 526/263, 526/287, 526/312, 526/319, 523/118, 522/167, 522/173
• US Class Current: 526/263
• CPC Class Codes: A61K 6/887 Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: C07D 233/58 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
• CPC Class Codes: C07D 233/60 with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
• CPC Class Codes: C07D 233/61 with hydrocarbon radicals, substituted by nitrogen atoms not forming part of a nitro radical, attached to ring nitrogen atoms
• CPC Class Codes: C08F 22/22 Esters containing nitrogen
• CPC Class Codes: C08F 26/02 by a single or double bond to nitrogen
• CPC Class Codes: C08F 28/02 by a bond to sulfur
• CPC Class Codes: C08K 5/3445 Five-membered rings
• CPC Class Codes: C09D 133/066 containing -OH groups
• CPC Class Codes: C09D 139/00 Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Coating compositions based on derivatives of such polymers
• CPC Class Codes: C09D 141/00 Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur; Coating compositions based on derivatives of such polymers
• CPC Class Codes: C09D 4/06 Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
• CPC Class Codes: Y10T 428/31725 Of polyamide
• CPC Class Codes: Y10T 428/31786 Of polyester [e.g., alkyd, etc.]
• CPC Class Codes: Y10T 428/31935 Ester, halide or nitrile of addition polymer

Abstract

Presently described are curable compositions comprising a mixture of at least one (e.g. free-radically) polymerizable ionic liquid and at least one other ethylenically unsaturated monomer, oligomer, or polymer. The polymerizable ionic liquid is characterized as having an air to nitrogen curing exotherm ratio of at least 0.70. Also described are articles and methods of making articles from such curable compositions. A monofunctional polymerizable ionic liquid is also described comprising a non-polymerizable substituted imidazolium cationic group and a polymerizable sulfonate anion.

Claims

1. A curable composition comprising a polymerizable organic composition comprising

I) at least one multifunctional polymerizable ionic liquid comprising a cation and an anion, and at least two free-radically polymerizable groups selected from (meth)acrylamide, (meth)acrylate, or vinyl ether, the multifunctional polymerizable ionic liquid having an air to nitrogen curing exotherm ratio of at least 0.70;

and ii) at least one other ethylenically unsaturated monomer, oligomer, or polymer.

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

3. The curable composition of claim 1 wherein the other ethylenically unsaturated monomer(s), oligomer(s), or polymer(s) has an air to nitrogen curing exotherm ratio of no greater than 0.50.

4. The curable composition of claim 1 wherein the curable composition comprises a photoinitiator.

5. The curable composition of claim 1 wherein the multifunctional polymerizable ionic liquid comprises an organic anion.

6. The curable composition of claim 1 wherein the multifunctional polymerizable ionic liquid comprises an aromatic carboxylate anion.

7. An article comprising the cured composition of previous claim 1.

8. An article comprising a substrate and the cured coating composition of claim 1 disposed on a surface of the substrate.

9. The curable composition of claim 1 wherein the multifunctional polymerizable ionic liquid has the formula

10. The curable composition of claim 9 wherein the multifunctional polymerizable ionic liquid is

11. The curable composition of claim 1 wherein the multifunctional polymerizable ionic liquid has the formula

12. The curable composition of claim 1 wherein the multifunctional polymerizable ionic liquid has the formula

13. The curable composition of claim 1 wherein the polymerizable organic composition comprises at least 50 wt-% of multifunctional polymerizable ionic liquid.

14. The curable composition of claim 1 wherein curable composition comprises at least 40 wt-% of inorganic filler.

15. The curable composition of claim 1 wherein the filler comprises silica, zirconia, or mixtures thereof.

16. The curable composition of claim 1 wherein the filler has an average primary partilce size of less than 0.100 micrometers.

17. The curable composition of claim 1 wherein the ethylenically unsaturated monomer, oligomer, or polymer is selected from poly(meth)acryl monomers, mono(meth)acryl compounds, and oligomeric (meth)acryl compounds.

18. The curable composition of claim 1 wherein the curable composition can be completely cured in air.

19. A coated substrate comprising a substrate and the curable composition of claim 1 cured on a surface of the substrate.