Thermosetting coating compositions

Patent metadata

Field	Value
Publication number	US-9988553-B2
Application number	US-201715435353-A
Country	US
Kind code	B2
Filing date	Feb 17, 2017
Priority date	Feb 22, 2016
Publication date	Jun 5, 2018
Grant date	Jun 5, 2018

Abstract

The present invention provides emulsions comprising curable polyesters and certain surfactants. The emulsions are useful as coatings binders in waterborne thermosetting coating compositions and can be used in conjunction with cross-linking compounds reactive with curable polyesters. Also provided are shaped or formed articles coated with the waterborne thermosetting coating compositions of the invention.

First claim

We claim:

1. An aqueous polyester emulsion comprising:
a) a curable polyester;
b) a non-ionic emulsifier having the structure

wherein each Z is independently a C 1 to C 4 hydrocarbon radical, x is an integer ranging from 1 to 5, Y is a divalent C 1 to C 4 hydrocarbon radical, and n is an integer from 1 to 100; and
c) water.

2. The emulsion of claim 1 , wherein the curable polyester is comprised of residues of:
a) polyhydroxyl compounds comprising:
i. diol compounds in an amount of 50 mole % to 100 mole % and
ii. polyol compounds having 3 or more hydroxyl groups in an amount of 0 to 50 mole %,

wherein the mole % is based on 100% of all moles of polyhydroxyl compounds a); and
b) polycarboxyl compounds comprising:
i. dicarboxylic acid compounds, derivatives of dicarboxylic acid compounds, the anhydrides of dicarboxylic acids, or combinations thereof; and/or
ii. tricarboxylic acid compounds having 3 carboxylic acid groups.

3. The emulsion of claim 2 , wherein the diol compounds are selected from the group consisting of 2,2,4,4-tetraalkylcyclobutane-1,3-diol (TACD), 2,2-dimethyl-1,3-propanediol (neopentyl glycol), 1,2-cyclohexanedimethanol, 1,3-cyclohexanedimethanol, 1,4-cyclohexanedimethanol, isosorbide, 2,2,4-trimethyl-1,3-pentanediol, hydroxypivalyl hydroxypivalate, 2-methyl-1,3-propanediol, 2-butyl-2-ethyl-1,3-propanediol, 2-ethyl-2-isobutyl-1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 2,2,4,4-tetramethyl-1,6-hexanediol, 1,10-decanediol, 1,4-benzenedimethanol, ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tetraethylene glycol, and polyethylene glycol.

4. The emulsion of claim 2 , wherein the diol is selected from the group consisting of 2,2,4,4-tetramethylcyclobutane-1,3-diol (TMCD), 2,2,4,4-tetraethylcyclobutane-1,3-diol, 2,2,4,4-tetra-n-propylcyclobutane-1,3-diol, 2,2,4,4-tetra-n-butylcyclobutane-1,3-diol, 2,2,4,4-tetra-n-pentylcyclobutane-1,3-diol, 2,2,4,4-tetra-n-hexylcyclobutane-1,3-diol, 2,2,4,4-tetra-n-heptylcyclobutane-1,3-diol, 2,2,4,4-tetra-n-octylcyclobutane-1,3-diol, 2,2-dimethyl-4,4-diethylcyclobutane-1,3-diol, 2-ethyl-2,4,4-trimethylcyclobutane-1,3-diol, 2,4-dimethyl-2,4-diethyl-cyclobutane-1,3-diol, 2,4-dimethyl-2,4-di-n-propylcyclobutane-1,3-diol, 2,4-n-dibutyl-2,4-diethylcyclobutane-1,3-diol, 2,4-dimethyl-2,4-diisobutylcyclobutane-1,3-diol, and 2,4-diethyl-2,4-diisoamylcyclobutane-1,3-diol.

5. The emulsion of claim 2 , wherein the polyol compounds are selected from the group consisting of 1,1,1-trimethylol propane, 1,1,1-trimethylolethane, glycerin, pentaerythritol, erythritol, threitol, dipentaerythritol, and sorbitol, and mixtures thereof.

6. The emulsion of claim 2 , wherein the polycarboxylic acid compounds are selected from the group consisting of isophthalic acid (or dimethyl isophthalate), terephthalic acid (or dimethyl terephthalate), phthalic acid, phthalic anhydride, 1,4-cyclohexanedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid, hexahydrophthalic anhydride, tetrahydrophthalic anhydride, tetrachlorophthalic anhydride, dodecanedioic acid, sebacic acid, azelaic acid, succinic anhydride, succinic acid, adipic acid, 2,6-naphthalenedicarboxylic acid, glutaric acid, diglycolic acid; 2,5-norbornanedicarboxylic acid; 1,4-naphthalenedicarboxylic acid; 2,5-naphthalenedicarboxylic acid; diphenic acid; 4,4′-oxydibenzoic acid; 4,4′-sulfonyidibenzoic acid, and mixtures thereof.

7. The emulsion of claim 1 , wherein the curable polyester has a hydroxyl number of from 30 to 200 mg KOH/g; and an acid number of less than 50.

8. The emulsion of claim 1 , wherein the curable polyester has a glass transition temperature (Tg) of from 40° C. to 120° C., as measured by ASTM D3418.

9. A thermosetting coating composition comprising:
a) an aqueous polyester emulsion comprising:
i. a curable polyester;
ii. a non-ionic emulsifier having the structure;

wherein each Z is independently a C 1 to C 4 hydrocarbon radical, x is an integer ranging from 1 to 5, Y is a divalent C 1 to C 4 hydrocarbon radical, and n is an integer from 1 to 100, and
iii. water; and

b) a cross-linker.

10. The thermosetting coating composition of claim 9 , wherein the cross-linker is selected from the group consisting of amino resins, isocyanates, and phenolic resins.

11. The thermosetting coating composition of claim 9 , wherein the curable polyester is comprised of residues of:
a) polyhydroxyl compounds comprising:
i. diol compounds in an amount of 50 mole % to 100 mole % and
ii. polyol compounds having 3 or more hydroxyl groups in an amount of 0 to 50 mole %,

wherein the mole % is based on 100% of all moles of polyhydroxyl compounds a); and
b) polycarboxyl compounds comprising:
i. dicarboxylic acid compounds, derivatives of dicarboxylic acid compounds, the anhydrides of dicarboxylic acids, or combinations thereof; and/or
ii. tricarboxylic acid compounds having 3 carboxylic acid groups.

12. The thermosetting coating composition of claim 11 , wherein the diol compounds are selected from the group consisting of 2,2,4,4-tetraalkylcyclobutane-1,3-diol (TACD), 2,2-dimethyl-1,3-propanediol (neopentyl glycol), 1,2-cyclohexanedimethanol, 1,3-cyclohexanedimethanol, 1,4-cyclohexanedimethanol, isosorbide, 2,2,4-trimethyl-1,3-pentanediol, hydroxypivalyl hydroxypivalate, 2-methyl-1,3-propanediol, 2-butyl-2-ethyl-1,3-propanediol, 2-ethyl-2-isobutyl-1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 2,2,4,4-tetramethyl-1,6-hexanediol, 1,10-decanediol, 1,4-benzenedimethanol, ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tetraethylene glycol, and polyethylene glycol.

13. The thermosetting coating composition of claim 11 , wherein the diol is selected from the group consisting of 2,2,4,4-tetramethylcyclobutane-1,3-diol (TMCD), 2,2,4,4-tetraethylcyclobutane-1,3-diol, 2,2,4,4-tetra-n-propylcyclobutane-1,3-diol, 2,2,4,4-tetra-n-butylcyclobutane-1,3-diol, 2,2,4,4-tetra-n-pentylcyclobutane-1,3-diol, 2,2,4,4-tetra-n-hexylcyclobutane-1,3-diol, 2,2,4,4-tetra-n-heptylcyclobutane-1,3-diol, 2,2,4,4-tetra-n-octylcyclobutane-1,3-diol, 2,2-dimethyl-4,4-diethylcyclobutane-1,3-diol, 2-ethyl-2,4,4-trimethylcyclobutane-1,3-diol, 2,4-dimethyl-2,4-diethyl-cyclobutane-1,3-diol, 2,4-dimethyl-2,4-di-n-propylcyclobutane-1,3-diol, 2,4-n-dibutyl-2,4-diethylcyclobutane-1,3-diol, 2,4-dimethyl-2,4-diisobutylcyclobutane-1,3-diol, and 2,4-diethyl-2,4-diisoamylcyclobutane-1,3-diol.

14. The thermosetting coating composition of claim 9 , wherein the polyol compounds are selected from the group consisting of 1,1,1-trimethylol propane, 1,1,1-trimethylolethane, glycerin, pentaerythritol, erythritol, threitol, dipentaerythritol, and sorbitol, and mixtures thereof.

15. The thermosetting coating composition of claim 9 , wherein the polycarboxylic acid compounds are selected from the group consisting of isophthalic acid (or dimethyl isophthalate), terephthalic acid (or dimethyl terephthalate), phthalic acid, phthalic anhydride, 1,4-cyclohexanedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid, hexahydrophthalic anhydride, tetrahydrophthalic anhydride, tetrachlorophthalic anhydride, dodecanedioic acid, sebacic acid, azelaic acid, succinic anhydride, succinic acid, adipic acid, 2,6-naphthalenedicarboxylic acid, glutaric acid, diglycolic acid; 2,5-norbornanedicarboxylic acid

Assignees

• Eastman Chem Co

Inventors

• Dziczkowski Jamie Sue
• Chaffin Kenneth Douglas

Classifications

• C08L2312/04

  with phenolic resin · CPC title

• C09D167/02 Primary

  Polyesters derived from dicarboxylic acids and dihydroxy compounds (C09D167/06 takes precedence) · CPC title

• C08K5/06

  Ethers; Acetals; Ketals; Ortho-esters · CPC title

• C08L2666/34

  Oxygen-containing compounds, including ammonium and metal salts · CPC title

• C08L67/02

  Polyesters derived from dicarboxylic acids and dihydroxy compounds (C08L67/06 takes precedence) · CPC title