Granted Patent B2

US 12,240,990 · App. 17/250,990 · Granted Mar 4, 2025

Inventors: Stacey James Marsh (Church Hill, TN); Philip Jerome Geiger (Kingsport, TN); John Evan Boisseau (Kingsport, TN)

Assignee: Eastman Chemical Company

C09D167/02C09D7/20

Abstract

Claims (33)

1. A coating comprising:

A. about 2 to about 50 weight percent, based on the total weight of (A), (B) and (C) of a curable, aliphatic polyester resin comprising:

i. diacid residues, comprising at least 90 mole percent, based on the total moles of diacid residues, of the residues of at least one aliphatic diacid, wherein 0 to 40 mole percent of the at least one aliphatic diacid is an alicyclic diacid and 60 to 100 mole percent of the at least one aliphatic diacid is a linear diacid having between 4 and 12 carbons;

ii. diol residues, comprising a) about 25 to 100 mole percent, based on the total moles of diol residues, of the residues of a diol having the structure:

wherein R1, R2, R3, and R4 each independently represent an alkyl radical, and b) 0 to 75 mole percent based on the total moles of diol residues, of a C2-C20 diol selected from the group consisting of 2,2-dimethyl-1,3-propanediol, 1,2 cyclohexanedimethanol, 1,3-cyclohexanedimethanol, 1,4 cyclohexanedimethanol, 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, polyethylene glycol, and 2,2-bis(hydroxymethyl)propionic acid;

iii. about 5 to about 80 mole percent of the residues of at least one polyol, based on the total moles of diol and polyol residues;

B. about 15 to about 85 weight percent, based on the total weight of (A), (B), and (C) of at least one acrylic copolymer of ethylenically unsaturated monomers containing carbamate and/or hydroxy functional groups;

C. about 10 to about 50 weight percent, based on the total weight of (A), (B), and (C), of at least one crosslinker comprising at least one compound reactive with a carbamate and/or hydroxyl group; and

D. about 10 to about 60 weight percent, based on the total weight of (A), (B), (C), and (D) of at least one non-aqueous solvent.

2. The coating of claim 1 wherein the alicyclic diacid is a cyclic aliphatic dicarboxylic acid compound, its diester derivative, its anhydride, or a combination thereof.

3. The coating of claim 2 wherein the alicyclic diacid is selected from the group consisting of 1,4 cyclohexanedicarboxylic acid, 1,3 cyclohexanedicarboxylic acid, hexahydrophthalic anhydride, methyl hexahydrophthalic anhydride, tetrahydrophthalic anhydride, tetrachlorophthalic anhydride, 5-norbornene-2,3-dicarboxylic anhydride, 5-norbornene-2,3-dicarboxylic acid, 2,3-norbornanedicarboxylic acid, 2,3-norbornanedicarboxylic acid anhydride, and mixtures thereof.

4. The coating of claim 1 wherein said linear diacid is an open-chain aliphatic dicarboxylic acid compound, its diester derivative, its anhydride, or a combination thereof.

5. The coating of claim 4 wherein said linear diacid is selected from the group consiting of succinic acid, glutaric acid, adipic acid, itaconic anhydride, itaconic acid, citraconic anhydride, citraconic acid, pimelic acid, suberic acid, dodecanedioic acid, sebacic acid, azelaic acid, and combinations thereof.

6. The coating of claim 1 wherein said diol ii a) 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.

7. The coating of claim 1 , wherein said polyol iii) is a saturated or unsaturated, aliphatic or cycloaliphatic C2-C20 compound.

8. The coating of claim 7 wherein said polyol is selected from the group consisting of 1,1,1-trimethylolpropane, 1,1,1-trimethylolethane, glycerin, pentaerythritol, erythritol, threitol, di-pentaerythritol, sorbitol, and mixtures thereof.

9. The coating of claim 1 wherein said crosslinker comprises at least one melamine compound chosen from hexamethoxymethyl melamine, tetramethoxymethyl benzoguanamine, tetramethoxymethyl urea, and mixed butoxy/methoxy substituted melamines.

10. A coating comprising:

A. about 2 to about 50 weight percent, based on the total weight of (A), (B) and (C) of a curable, aliphatic polyester resin, comprising:

i. diacid residues, comprising at least 90 mole percent, based on the total moles of diacid residues, of the residues of 0 to 40 mole percent hexahydrophthalic anhydride and 60 to 100 mole percent is adipic acid;

ii. diol residues, comprising a) about 25 to 100 mole percent, based on the total moles of diol residues, of the residues of 2,2,4,4-tetramethyl-1,3-cyclobutanediol, based on the total moles of diol residues and b) 0 to 75 mole percent based on the total moles of diol residues of neopentyl glycol; and

iii. about 5 to about 80 mole percent of the residues of trimethylolpropane, based on the total moles of diol and polyol residues;

B. about 15 to about 85 weight percent, based on the total weight of (A), (B), and (C) of at least one acrylic copolymer of ethylenically unsaturated monomers containing carbamate and/or hydroxy functional groups;

C. about 10 to about 50 weight percent, based on the total weight of (A), (B), and (C), of at least one crosslinker comprising at least one compound reactive with a carbamate and/or hydroxyl group; and

D. about 10 to about 60 weight percent, based on the total weight of (A), (B), (C), and (D) of at least one non-aqueous solvent.

11. A coating comprising:

A. about 2 to about 50 weight percent, based on the total weight of (A), (B) and (C) of a curable, aliphatic polyester resin, comprising:

i. diacid residues, comprising at least 90 mole percent, based on the total moles of diacid residues, of the residues of at least one aliphatic diacid where 0 to 40 mole percent is an alicyclic diacid and 60 to 100 mole percent is a linear diacid containing between 4 and 12 carbons;

ii. diol residues, comprising a) 25 to 100 mole percent, based on the total moles of diol residues, of the residues of 2,2,4,4-tetramethyl-1,3-cyclobutanediol, based on the total moles of diol residues; and b) 0 to 75 mole percent based on the total moles of diol residues, of a C2-C20 diol selected from the group consisting of 2,2-dimethyl-1,3-propanediol, 1,2 cyclohexanedimethanol, 1,3-cyclohexanedimethanol, 1,4 cyclohexanedimethanol, 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, polyethylene glycol, and 2,2-bis(hydroxymethyl)propionic acid; and

iii. about 5 to about 80 mole percent of the residues of at least one polyol selected from the group consisting of trimethylolpropane, pentaerythritol, trimethylolethane, erythritol, threitol, dipentaerythritol, sorbitol, and glycerine, based on the total moles of diol and polyol residues;

B. about 15 to about 85 weight percent, based on the total weight of (A), (B), and (C) of at least one acrylic copolymer of ethylenically unsaturated monomers containing carbamate and/or hydroxy functional groups;

C. about 10 to about 50 weight percent, based on the total weight of (A), (B), and (C), of at least one crosslinker comprising at least one compound reactive with a carbamate and/or hydroxyl group; and

D. about 10 to about 60 weight percent, based on the total weight of (A), (B), (C), and (D) of at least one non-aqueous solvent.

Assignments (1)

Continuity (2)

References Cited (37)