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

• US 9,127,101 B2
• Filed: 07/15/2014
• Issued: 09/08/2015
• 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:
  US14/331,499
• Publication Number:
  US 20140322550A1
• Time in Patent Office: 420 Days
• Field of Search: 526/263, 526/287, 526/312, 526/319, 523/118, 522/167, 522/173
• US Class Current: 1/1
• 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 30 wt-% of a multifunctional polymerizable ionic liquid comprising an anion and a cationic group having at least two free-radically polymerizable groups each bonded to the cationic group via a divalent linking group wherein the linking group independently comprises one or more linkages selected from amide, urethane, or ester and the multifunctional polymerizable ionic liquid has 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 polymerizable organic composition further comprises is a monofunctional polymerizable ionic liquid.

3. 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.

4. 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.

5. The curable composition of claim 4 wherein the other ethylenically unsaturated monomer, oligomer, or polymer having an air to nitrogen curing exotherm ratio of no greater than 0.50 is present an amount of at least 25 wt-% of the total polymerizable organic composition.

6. The curable composition of claim 1 wherein the multifunctional polymerizable ionic liquid is present in an amount up to about 50 wt-% of the curable composition.

7. The curable composition of claim 1 wherein the curable composition is free of filler.

8. The curable composition of claim 1 wherein the curable composition comprises filler.

9. The curable composition of claim 8 wherein the curable composition comprises inorganic nanoparticles.

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

11. The curable composition of claim 1 wherein the cation is a substituted ammonium, phosphonium, or imidazolium cation.

12. The curable composition of claim 1 wherein the anion is an organic anion.

13. The curable composition of claim 1 wherein the anion is a sulfonate anion.

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

15. An article comprising the cured composition of claim 1.

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

17. A method of making an article comprising:

providing the curable composition of claim 1;

casting the curable composition in contact with a mold; and

curing the composition.

18. A method of coating a curable composition comprising:

providing the curable composition of claim 1;

applying the composition to a substrate; and

curing the composition.

19. The method of claim 17 wherein the composition is cured in air.

20. The method of claim 18 wherein the composition is cured in air.