ADVANCED POLY EPOXY ESTER RESIN COMPOSITIONS

• US 20130178591A1
• Filed: 09/22/2011
• Published: 07/11/2013
• Est. Priority Date: 09/30/2010
• Status: Abandoned Application

• Current Assignee: Blue Cube IP LLC (OLIN Corporation)
• Original Assignee: Dow Global Technologies LLC (Dow, Inc.)
• Inventors: Jin, Xin, Drumright, Ray E., Kainz, Bernhard, White, Jerry E., Hefner, Robert E. Jr.
• Application Number:
  US13/814,807
• Publication Number:
  US 20130178591A1
• Time in Patent Office: Days
• US Class Current: 525/437
• CPC Class Codes: C08G 59/066 with chain extension or advancing agents
• CPC Class Codes: C08G 59/186 with acids
• CPC Class Codes: C08G 63/181 Acids containing aromatic rings
• CPC Class Codes: C08G 63/672 Dicarboxylic acids and dihydroxy compounds
• CPC Class Codes: C08L 2205/05 containing polymer components which can react with one another
• CPC Class Codes: C08L 33/04 Homopolymers or copolymers of esters C08L43/04 takes precedence
• CPC Class Codes: C08L 63/00 Compositions of epoxy resins; Compositions of derivatives of epoxy resins
• 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

Abstract

A poly epoxy ester resin composition of the following chemical structure: where n is a number from 2 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), Ar is a divalent aryl group or heteroarylene group;_and X is cycloalkylene group, including substituted cycloalkylene group, where the substitute group include an alkyl, cycloalkyl, an aryl or an aralkyl group or other substitute group, for example, a halogen, 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 poly epoxy ester resin composition comprising the following chemical structure:

2. The composition of claim 1, wherein the advanced poly epoxy ester resin polymeric composition comprises a reaction product of (a) at least one cycloaliphatic diglycidyl ether compound, and (b) at least one aromatic dicarboxylic acid compound.

3. The composition of claim 2, wherein the at least one cycloaliphatic diglycidyl ether compound comprises a diglycidyl ether of cyclohexanedimethanol.

4. The composition of claim 2, 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.

5. The composition of claim 2, 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.

6. The composition of claim 2, 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-cycloexanedimethanol, and/or a diglycidyl ether of trans-1,4-cyclohexanedimethanol.

7. The composition of claim 2, wherein the at least one cycloaliphatic diglycidyl ether compound comprises a diglycidyl ether of 1,1-cyclohexanedimethanol.

8. The composition of claim 2, wherein the at least one aromatic dicarboxylic acid compound comprises any aromatic compound with dicarboxylic acid structures and mixtures thereof.

9. The composition of claim 2, wherein the at least one aromatic dicarboxylic acid compound comprises a naphthalene dicarboxylic acid with the two —

COOH group at any substitute positions, and mixtures thereof and the like.

10. The composition of claim 1, wherein the weight average molecular weight of the advanced poly epoxy ester resin polymeric composition is from about 300 to about 1,000,000.

11. The composition of claim 1, wherein the elongation to break at about 21°

C. of the advanced poly epoxy ester resin polymeric composition is from about 5 percent to about 2000 percent as measured by the method ASTM D1708.

12. The composition of claim 1, wherein the tensile toughness at about 21°

C. of the advanced poly epoxy ester resin polymeric composition is from about 0.05 MPa to about 500 MPa as measured by the method ASTM D1708.

13. The composition of claim 1, wherein the glass transition temperature of the advanced poly epoxy ester resin polymeric composition is from about −

50°

C. to about 200°

C.

14. The composition of claim 1, wherein the advanced poly epoxy ester resin composition is made water-dispersible by (i) reacting the advanced poly epoxy ester resin polymeric composition with a water-dispersible acrylic;

(ii) reacting the advanced poly epoxy ester resin polymeric composition with a water-dispersible polyester resin;

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

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

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

15. The composition of claim 1, wherein the advanced poly epoxy ester resin composition is made water-dispersible by incorporating a dicarboxylic acid with a double bond which is polymerizable by free radical mechanism into the backbone and grafting with at least one acid monomer with a double bond which is polymerizable by free radical mechanism and a vinylic monomer not containing an acid group and at least partial neutralizating with a base.

16. A curable poly epoxy ester resin composition comprising (a) the poly epoxy ester resin composition of claim 1;

and (b) at least one curing agent.

17. A cured resin prepared from the curable poly epoxy ester resin composition of claim 16.

18. A process for preparing the poly epoxy ester resin composition of claim 1 comprising preparing an advanced poly epoxy ester resin polymeric composition by reacting (a) at least one cycloaliphatic diglycidyl ether compound, and (b) at least one aromatic dicarboxylic acid compound.