COATING COMPOSITIONS

• US 20130143982A1
• Filed: 09/13/2011
• Published: 06/06/2013
• Est. Priority Date: 09/30/2010
• Status: Active Grant

• Current Assignee: Blue Cube IP LLC (OLIN Corporation)
• Original Assignee: Dow Global Technologies LLC (Dow, Inc.)
• Inventors: Jin, Xin, Drumright, Ray E., White, Jerry E., Hefner, Robert E., Kainz, Bernhard
• Granted Patent: US 9,080,059 B2
• Time in Patent Office: Days
• US Class Current: 523/400
• CPC Class Codes: C08G 59/066 with chain extension or advancing agents
• CPC Class Codes: C08L 2205/05 containing polymer components which can react with one another
• CPC Class Codes: C08L 33/02 Homopolymers or copolymers of acids; Metal or ammonium salts thereof
• CPC Class Codes: C08L 67/00 Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain of polyester-amides C08L77/12; of polyester-imides C08L79/08; Compositions of derivatives of such polymers
• CPC Class Codes: C09D 163/00 Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
• CPC Class Codes: C09D 5/00 Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced electrically insulating plastics, resins or waxes H01B3/30; Filling pastes

Abstract

A coating composition comprising an advanced epoxy resin polymeric composition having the following chemical structure:(formula) I where n is a number from 1 to about 3000; each m independently has a value of 0 or 1; each R0 is independently —H or —CH₃; each R¹ is independently —H or a C₁ to C₆ alkylene radical (saturated divalent aliphatic hydrocarbon radical); R′₁—R′₄ are independently hydrogen, an alkyl, cycloalkyl, an aryl or an aralkyl group or other substituent, for example, a nitro, an isocyanate, or an alkyloxy group; additionally, any two of R′₁-R′₄ may form fused ring independently; and X is cycloalkylene group, including substituted cycloalkylene group, where the substituent groups include an alkyl, cycloalkyl, an aryl or an aralkyl group or other substituent group, for example, a halide, a cyano, a nitro, a blocked isocyanate, or an alkyloxy group; the combination of cycloalkylene and alkylene groups and the combination of alkylene and cycloalkylene group with a bridging moiety in between.

Claims

1. A curable coating composition comprising an epoxy resin polymeric composition having the following chemical structure:

2. The curable coating composition of claim 1, including a curing agent.

3. The curable coating composition of claim 1, wherein the epoxy resin polymeric composition comprises a reaction product of (a) at least one cycloaliphatic diglycidyl ether compound, and (b) at least one aromatic diol.

4. The curable coating composition of claim 3, wherein the at least one cycloaliphatic diglycidyl ether compound comprises diglycidyl ethers of cyclohexanedimethanol.

5. The curable coating composition of claim 3, wherein the at least one cycloaliphatic diglycidyl ether compound comprises a diglycidyl ether of cis-1,3-cyclohexanedimethanol and/or a diglycidyl ether of trans-1,3-cyclohexanedimethanol.

6. The curable coating composition of claim 3, wherein at least one cycloaliphatic diglycidyl ether compound comprises a diglycidyl ether of cis-1,4-cyclohexanedimethanol and/or a diglycidyl ether of trans-1,4-cyclohexanedimethanol

7. The curable coating composition of claim 3, wherein the at least one cycloaliphatic diglycidyl ether compound comprises a diglycidyl ether of cis-1,3-cyclohexanedimethanol, a diglycidyl ether of trans-1,3-cyclohexanedimethanol, a diglycidyl ether of cis-1,4-cyclohexanedimethanol, and/or a diglycidyl ether of trans-1,4-cyclohexanedimethanol.

8. The curable coating composition of claim 3, wherein the at least one cycloaliphatic diglycidyl ether compound comprises a diglycidyl ether of 1, 1′

-cyclohexanedimethanol.

9. The curable coating composition of claim 3, wherein the at least one aromatic diol comprises at least one aromatic diol having the following general chemical structure:

10. The curable coating composition of claim 3, wherein the at least one aromatic diol comprises catechol.

11. The curable coating composition of claim 1, wherein the epoxy resin polymeric composition has a weight average molecular weight of from about 300 to about 1,000,000.

12. The curable coating composition of claim 1, wherein the epoxy resin polymeric composition has an elongation to break at about 21°

C. of from about 4 percent to about 10000 percent as measured by the method ASTM D1708.

13. The curable coating composition of claim 1, wherein the epoxy resin polymeric composition has a tensile toughness at about 21°

C. of from about 0.05 MPa to about 500 Mpa as measured by the method ASTM D1708.

14. The curable coating composition of claim 1, wherein the epoxy resin polymeric composition has a glass transition temperature of from about −

50°

C. to about 200°

C.

15. The curable coating composition of claim 1, wherein the epoxy resin polymeric composition is water-dispersible.

16. The curable coating composition of claim 15, wherein the epoxy resin polymeric composition is made water-dispersible by (i) reaction with a water-dispersible acrylic;

(ii) reaction with a water-dispersible polyester resin;

(iii) grafting with at least one acid monomer which contain a double bond which is polymerizable by free radical mechanism;

(iv) grafting with at least one acid monomer which contain a double bond which is polymerizable by free radical mechanism and a vinylic monomer not containing an acid group;

or (v) reacting the advanced epoxy resin polymeric composition with a phosphoric and water and with (vi) at least partial neutralization with a base of the reaction product of (i) to (v)

17. The curable coating composition of claim 1, including at least one crosslinking reagent, at least one curing catalyst, at least one solvent, or mixtures thereof.

18. The curable coating composition of claim 1, including at least one crosslinking reagent, curing catalyst, or mixtures thereof.

19. A cured coating comprising the cured coating composition of claim 1.

20. The coating of claim 19 used in metal packaging.

21. The coating of claim 19 used for internal or external protective coatings for cans.

22. A process for preparing a coated article comprising the steps of (a) providing the composition of claim 1;

(b) applying the composition of claim 1 to a metal substrate; and

(c) heat curing the composition and substrate at a temperature of from about 0°

C. to about 300°

C.

23. An article made from the composition of claim 1.