Radiation curable water based cationic inks and coatings

• US 6,232,361 B1
• Filed: 12/11/1998
• Issued: 05/15/2001
• Est. Priority Date: 12/11/1998
• Status: Expired due to Term

• Current Assignee: Sun Chemical Corporation
• Original Assignee: Sun Chemical Corporation
• Inventors: Rose, Bruce, Turgis, Jean Dominique, Chatterjeee, Subhankar, Laksin, Mikhail
• Primary Examiner(s): Seidleck, James J.
• Assistant Examiner(s): McClendon, Sanza L
• Application Number:
  US09/209,227
• Time in Patent Office: 886 Days
• Field of Search: 522/100, 522/168, 522/170, 522/84, 522/81, 522/75, 522/86, 522/182, 523/160, 106/31.28, 106/31.13, 106/31.6, 106/31.85, 428/413, 428/500
• US Class Current: 522/84
• CPC Class Codes: C08G 59/24 carbocyclic
• CPC Class Codes: C08G 59/68 characterised by the catalysts used
• CPC Class Codes: C08G 65/18 Oxetanes
• CPC Class Codes: C08G 65/20 Tetrahydrofuran
• CPC Class Codes: C08G 65/22 Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
• CPC Class Codes: C09D 11/101 Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
• CPC Class Codes: C09D 11/30 Inkjet printing inks
• CPC Class Codes: G03F 7/038 Macromolecular compounds which are rendered insoluble or differentially wettable G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021
• CPC Class Codes: Y10T 428/31511 Of epoxy ether
• CPC Class Codes: Y10T 428/31855 Of addition polymer from unsaturated monomers

Abstract

An actinic radiation curable, cationic polymerizable, ink and coating composition having greatly enhanced reactivity, and reduced viscosity and are low in odor comprised of an aqueous solution containing a cationic polymerizable compound such as an cycloaliphatic epoxy compound, a water compatible hydroxy functional cyclic ether compound, particularly, an epoxy or oxetane compound, and water.

Claims

1. An actinic radiation curable, cationic polymerizable, composition comprising an aqueous solution of:

(a) a cationic polymerizable compound having two or more epoxy groups, oxetane groups, or a combination thereof;

(b) a hydroxy alkyl cyclic ether selected from the group consisting of a hydroxyalkyl oxetane compound, a hydroxyalkyl epoxy compound, and a combination thereof;

(c) water; and

(d) a cationic initiator.

2. The composition of claim 1 wherein the cationic polymerizable compound is a cycloaliphatic epoxy compound.

3. The composition of claim 2 wherein the cycloaliphatic epoxy compound is 3,4-epoxycyclohexylmethyl -3′

,4′

-epoxycyclohexylcarboxylate.

4. The composition of claim 1 wherein the cationic polymerizable compound is selected from the group consisting of a diglycidyl ether of bisphenol A;

diglycidyl ether of alkoxylated bisphenol A;

a triglycidyl ether of alkoxylated bisphenol A;

novalac epoxy; and

combinations thereof.

5. The composition of claim 1 wherein the hydroxy alkyl cyclic ether is the hydroxyalkyl oxetane.

6. The composition of claim 5 wherein the hydroxyalkyl oxetane has the structure:

wherein R₁ is an alkenyl group having 1 to 2 carbon atoms, and R₂ is hydrogen or an alkyl group having 1 to 6 carbon atoms.

7. The composition of claim 6 wherein the hydroxyalkyl oxetane is 3-ethyl-3-hydroxymethyl-oxetane.

8. The composition of claim 1 wherein the hydroxy alkyl cyclic ether is the hydroxyalkyl epoxy compound.

9. The composition of claim 8 wherein the hydroxyalkyl epoxy compound has the structure:

wherein R₃ is an alkenyl group having 1 to 2 carbon atoms, and R₄ is hydrogen or an alkyl group having 1 to 6 carbon atoms.

10. The composition of claim 9 wherein the hydroxyalkyl epoxy compound is 4-hydroxymethyl-1,2-epoxycyclohexane.

11. The composition of claim 1 wherein the hydroxy alkyl cyclic ether is the combination of the hydroxyalkyl oxetane and the hydroxyalkyl epoxy.

12. The composition of claim 11 wherein the hydroxyalkyl oxetane is 3-ethyl-3-hydroxymethyl-oxetane and the hydroxyalkyl epoxy is 4-hydroxymethyl-1,2-epoxycyclohexane.

13. The composition of claim 1 wherein the actinic radiation is ultraviolet radiation.

14. The composition of claim 1 wherein the actinic radiation is an electron beam.

15. The composition of claim 1 wherein the coating composition further comprises a colorant.

16. The composition of claim 15 wherein the colorant is a dye.

17. The composition of claim 15 wherein the colorant is a pigment dispersed in the aqueous solution.

18. The composition of claim 1 wherein the coating composition further comprises a vinyl ether.

19. The composition of claim 1 further comprising less than 35 wt. % based on the weight of the coating composition of a free radical, addition polymerizable composition.

20. The composition of claim 19 wherein the free radical, addition polymerizable composition comprises:

(1) an oligomer, a polymer or a combination thereof,

(2) an ethylenically unsaturated monomeric diluent; and

(3) a free radical photoinitiation system activated by the actinic radiation.

21. An actinic radiation curable, cationic polymerizable, composition comprised of

an aqueous solution of components:

(a) a cationic polymerizable compound having two or more epoxy groups, oxetane groups, or a combination thereof;

(b) a hydroxy alkyl cyclic ether selected from the group consisting of a hydroxyalkyl oxetane compound, a hydroxyalkyl epoxy compound, and a combination thereof;

(c) water; and

(d) a cationic initiator;

having physical properties characterized by a three component phase diagram;

wherein the vertices of said diagram represent 100 wt. % concentration of each component (a), (b) and (c); and

wherein the binary concentrations of the cationic polymerizable compound and water are plotted along a first binary axis;

the binary concentrations of the hydroxy alkyl cyclic ether and cationic polymerizable compound are plotted along a second binary axis; and

the binary concentrations of the water and cyclic ether are plotted along a third binary axis; and

wherein a cloud point curve within said diagram separates the single phase concentration region from the two-phase concentration region for the ternary mixture of components (a), (b) and (c).

22. The composition of claim 21 wherein the single phase region is bound by the cloud point curve and the second binary axis.

23. The composition of claim 22 represented by a region bound by the cloud point curve, second binary axis and a portion of the third binary axis wherein the water concentration ranges from 0 to 45 wt. %.

24. A printing ink prepared from the actinic radiation curable, cationic polymerizable, composition of claim 21.

25. A coating prepared from the actinic radiation curable, cationic polymerizable, composition of claim 21.