Aliphatic polyester coating compositions containing tetramethyl cyclobutanediol

Patent metadata

Field	Value
Publication number	US-10676565-B2
Application number	US-201715846388-A
Country	US
Kind code	B2
Filing date	Dec 19, 2017
Priority date	May 19, 2015
Publication date	Jun 9, 2020
Grant date	Jun 9, 2020

Abstract

Disclosed are aliphatic polyester resins containing specific molar quantities of 2,2,4,4-tetramethyl-1,3-cyclobutanediol, and solvent borne, thermosetting monocoating compositions prepared therefrom. The aliphatic polyesters exhibit good hardness and flexibility when formulated into thermosetting coatings compositions.

First claim

We claim:

1. A method for applying a thermosetting monocoat coating composition to a substrate comprising:
I. providing a substrate for coating;
II. providing a thermosetting monocoat coating composition comprising:
A. 50 to 90 weight percent, based on the total weight of (A) and (C), of at least one curable, aliphatic polyester, comprising residues of:
i. hydroxyl component, said hydroxyl component comprising the residues of:
a. from 5 to 45 mole %, based on the total moles of (a) and (b), of 2,2,4,4-tetraalkylcyclobutane-1,3-diol (TACD);
b. from 55 to 95 mole % based on the total moles of (a) and (b), of a diol other than TACD; and
c. from 3 to 35 mole %, based on the total moles of (a), (b) and (c), of a polyol;
ii. a diacid component, said diacid component comprising the residues of:
d. from 60 to 90 mole %, based on the total moles of the diacids (d) and (e), of an alicyclic diacid; and
e. from 10 to 40 mole %, based on the total moles of the diacids (d) and (e), of an acyclic aliphatic diacid;

wherein the curable polyester contains diacid residues in an amount of at least 90 mole % of aliphatic diacid residues, based on the total moles of all diacid residues in the curable polyester, and, wherein the curable polyester has a hydroxyl number of 50 to 450 mgKOH/g of polyester, an acid number of 0 to 80 mgKOH/g, and a number average molecular weight of 300 to 10,000 g/mole of polyester;
B. from 10 to 50 weight percent, based on the total weight of the coating composition, of a solvent other than water; and
C. from 10 to 50 weight percent, based on the total weight of (A) and (C), of a crosslinker comprising an aminoplast and/or isocyanate;
III. applying said thermosetting monocoat coating composition to said substrate to produce a coated substrate; and
IV. applying heat to the coated substrate to a predetermined temperature and for a predetermined time to produce a cured coating wherein the cured coating has an impact resistance of greater than 35 in.-lb as determined in accordance with ASTM D 2794, wherein said cured coating has a gloss retention, after abrasion, based on ASTM D 6279, of greater than 50%, and wherein said cured coating has a gloss retention, based on SAE J2527, of greater than 85% after 2000 hours.

2. The method of claim 1 , wherein said TACD is 2,2,4,4-tetramethyl-1,3-cyclobutanediol.

3. The method of claim 1 , wherein said the alicyclic diacid (d) comprises hexahydrophthalic anhydride (HHPA).

4. The method of claim 1 , wherein said polyester in said monocoat coating composition has an acid number of less than 20 mgKOH/g of polyester.

5. The method of claim 1 , wherein said polyester in said monocoat coating has a hydroxyl number of 100 to 200 mgKOH/g of polyester.

6. The method of claim 1 , wherein said cured coating has an König hardness of from 60 to 200 sec, as determined in accordance with ASTM D 4366 (König).

7. The method of claim 1 , wherein said cured coating has a gloss retention, based on SAE J2527, of greater than 85% after 4000 hours.

8. The method of claim 1 , wherein said applying the thermosetting monocoat coating composition to the substrate step comprises brushing, spraying, and roll coating.

9. The method of claim 8 , comprising spraying, wherein said spraying comprises rotational bell spraying.

10. The method of claim 9 , wherein said heating step comprises heating said coated substrate to a temperature of from 60° C. to 200° C. for a period of from 5 seconds to 5 hours.

11. The method of claim 10 , wherein said period is from 10 minutes to 1 hour.

12. The method of claim 1 , wherein said solvent in said thermosetting monocoat coating comprises less than 3 weight % water, based on the weight of the solution.

13. The method of claim 1 , wherein the crosslinker (C) is an aminoplast selected from the group comprising hexamethoxymethylmelamine, tetramethoxymethyin.-lbenzo-guanamine, tetramethoxymethylurea, hexabutoxymethylmelamine, mixed butoxy/methoxy methylmelamines and mixtures thereof.

14. The method of claim 1 wherein the diol (b) is selected from the group consisting of 2,2-dimethyl-1,3-propanediol (neopentyl glycol), 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, 1,4-butanediol, 1,6-hexanediol and mixtures thereof.

15. The method of claim 1 , wherein at least 15 mole % of the diol (b) residues is neopentyl glycol based on the total moles of diol (b).

16. The method of claim 1 , wherein the molar ratio of (b):(a) is from 1.5:1 to 2.0:1.

17. The method of claim 1 , wherein the polyol (c) is one or more selected from the group consisting of 1,1,1-trimethylolpropane (TMP), 1,1,1-trimethylolethane, glycerin, and pentaerythritol.

18. The method of claim 1 , wherein the alicyclic diacid (d) is selected from the group consisting of hexahydrophthalic anhydride (HHPA), 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.

19. The method of claim 1 , wherein the acyclic aliphatic diacid (e) is selected from the group consisting of adipic acid, maleic anhydride, maleic acid, fumaric acid, itaconic anhydride, succinic acid, succinic anhydride, glutaric acid, itaconic acid, citraconic anhydride, citraconic acid, dodecanedioic acid, sebacic acid, azelaic acid, and mixtures thereof.

20. The method of claim 1 , wherein (a) comprises from 30 to 40 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and (b) comprises from 60 to 70 mole % of a 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, 1,4-butanediol, 1,6-hexanediol and mixtures thereof, wherein the mole % is based on the total moles of (a) and (b).

21. The method of claim 1 , wherein the diacid component comprise 60 to 70 mole % of the residues of at least one alicyclic diacid comprising an anhydride and 32 to 38 mole % residues of an acyclic alphatic diacid comprising adipic acid, succinic anhydride, succinic acid, glutaric acid and mixtures thereof, and, wherein the curable polyester is obtained with no or less than 3 mole % acids having a carboxylic acid functionality of greater than 2 based on the total moles of all carboxylic acid compound residues.

Assignees

• Eastman Chem Co

Inventors

• Zhou Jianhui
• Marsh Stacey James

Classifications

• C08G63/16 Primary

  Dicarboxylic acids and dihydroxy compounds · CPC title

• C08G2150/00

  Compositions for coatings · CPC title

• C09D167/06

  Unsaturated polyesters having carbon-to-carbon unsaturation · CPC title

• C09D7/20

  Diluents or solvents · CPC title

• C08G63/12 Primary

  derived from polycarboxylic acids and polyhydroxy compounds · CPC title