Waterborne coating compositions based on polyesters containing dmpoa

Patent metadata

Field	Value
Publication number	US-2025011617-A1
Application number	US-202218577747-A
Country	US
Kind code	A1
Filing date	Jul 13, 2022
Priority date	Jul 14, 2021
Publication date	Jan 9, 2025
Grant date	—

Abstract

Disclosed are novel curable polyesters comprising the reaction product of 2,2,4,4-tetramethyl-1,3-cyclobutanediol (TMCD) and dimethylolpropionic acid. The curable polyesters have particular utility in waterborne coating compositions. Such waterborne coating compositions provide a good balance of desirable coating properties for metal packaging applications.

First claim

We claim:

1 . A waterborne coating composition comprising:
a. a polyester, which is the reaction product of the monomers comprising:
i. 2,2,4,4-tetramethyl-1,3-cyclobutanediol (TMCD) in an amount of 30 to 60 mole %, based on the total moles of i-iv,
ii. a diol other than TMCD in an amount of 20 to 69 mole %, based on the total moles of i-iv,
iii. a triol in an amount of 0 to 8 mole %, based on the total moles of i-iv,
iv. dimethylolpropionic acid (DMPOA) in an amount of 15 to 30 mole %, based on the total moles of i-iv,
v. an α,β-unsaturated diacid or anhydride in an amount of 0 to 20 mole %, based on the total moles of v-vii,
vi. an aromatic diacid in an amount of 80 to 100 mole %, based on the total moles of v-vii, and
vii. an aliphatic diacid in an amount of 0 to 20 mole %, based on the total moles of v-vii, and
b. a crosslinker, wherein said polyester has an acid number of 30 to 100 mgKOH/g, hydroxyl number of 6 to 30 mgKOH/g, number average molecular weight of 4,000 to 25,000 g/mole, and weight average molecular weight of 13,000 to 200,000 g/mole.

2 . The waterborne coating composition of claim 1 , wherein said 2,2,4,4-tetramethyl-1,3-cyclobutanediol (TMCD) (i) is in an amount of 35-55 mole %, said diol other than TMCD (ii) in an amount of 30 to 62 mole %, said triol (iii) in an amount of 0 to 5 mole %, said DMPOA (iv) in an amount of 15-25 mole %, said α,β-unsaturated diacid or anhydride (v) in an amount of 0 to 18 mole, said aromatic diacid (vi) in an amount of 67 to 95 mole %, and said aliphatic diacid (vii) in an amount of 0 to 15 mole %.

3 . The waterborne coating composition of claim 1 , wherein said 2,2,4,4-tetramethyl-1,3-cyclobutanediol (TMCD) (i) is in an amount of 40-50 mole %, said diol other than TMCD (ii) in an amount of 40 to 55 mole %, said triol (iii) in an amount of 0 to 3 mole %, said DMPOA (iv) in an amount of 15-20 mole %, said α,β-unsaturated diacid or anhydride (v) in an amount of 0 to 15 mole, said aromatic diacid (vi) in an amount of 5 to 93 mole %, and said aliphatic diacid (vii) in an amount of 0 to 10 mole %.

4 . The waterborne coating composition of any of the preceding claims , wherein said diol other than TMCD (ii) is one or more selected from 1,4-cyclohexanedimethanol, 1,3-cyclohexanedimethanol, 1,6-hexanediol, 2-methyl-1,3-propanediol, neopentyl glycol, and 2,2,4-trimethyl-1,3-pentanediol.

5 . The waterborne coating composition of any of the preceding claims , wherein said triol (iii) is trimethylolpropane.

6 . The waterborne coating composition of any of the preceding claims , wherein said α,β-unsaturated diacid or anhydride (v) is one or more selected from the group comprising maleic anhydride, maleic acid, fumaric acid, itaconic anhydride, and itaconic acid.

7 . The waterborne coating composition of any of the preceding claims , wherein said aromatic diacid (vi) is one or more selected from isophthalic acid and its esters, and terephthalic acid and its esters.

8 . The waterborne coating composition of any of the preceding claims , wherein said aliphatic diacid (vii) is one or more selected from succinic acid, adipic acid, sebacic acid, 1,4-cyclohexane dicarboxylic acid, and 1,3-cyclohexane dicarboxylic acid.

9 . The waterborne coating composition of any of the preceding claims , wherein said aliphatic diacid (vi) is sebacic acid, adipic acid, or a mixture thereof.

10 . The waterborne coating composition of any of the preceding claims , wherein said polyester (a) has a hydroxyl number of 6-25 mgKOH/g.

11 . The waterborne coating composition of any of the preceding claims , wherein said polyester (a) has an acid number of 50-100 mgKOH/g.

12 . The waterborne coating composition of any of the preceding claims , wherein said polyester (a) has a Tg of 40-110° C.

13 . The waterborne coating composition of any of the preceding claims , wherein said polyester (a) is made by using a titanium catalyst.

14 . The waterborne coating composition of any of the preceding claims , wherein said polyester has an acid number of 30-100 mgKOH/g and hydroxyl number of 6-30 mgKOH/g,

15 . The waterborne coating composition of any of the preceding claims , wherein said waterborne coating composition further comprises a neutralizing agent and water.

16 . The waterborne coating composition of any of the preceding claims , wherein said waterborne coating composition further comprises an organic co-solvent.

17 . The waterborne coating composition of any of the preceding claims , wherein said crosslinker is one or more selected from isocyanate, amino resin, and phenolic resin crosslinkers.

18 . The waterborne coating composition of any of the preceding claims , wherein said polyester (a) is in an amount of 50-90 weight % and said crosslinker (b) in an amount of 10-50 weight %, based on the total weight of (a) and (b).

19 . An article, of which at least a portion is coated with the waterborne coating composition of any of the preceding claims .

Assignees

• Houston Katelyn Rose
• He Hongkun
• Marsh Stacey James
• Kuo Thauming
• Eastman Chem Co

Inventors

• Houston Katelyn Rose
• He Hongkun
• Marsh Stacey James
• Kuo Thauming

Classifications

• C08G63/85

  Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof {(C08G63/823 takes precedence)} · CPC title

• C08G63/06

  derived from hydroxycarboxylic acids · CPC title

• C09D7/20

  Diluents or solvents · CPC title

• B65D25/14

  Linings or internal coatings (of containers made by folding or erecting blanks made of paper B65D5/56 {; linings for domestic water storage heaters F24H1/183}) · CPC title

• C08G63/52

  Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation · CPC title