Carboxyl functional curable polyesters containing tetra-alkyl cyclobutanediol

Patent metadata

Field	Value
Publication number	US-2016115274-A1
Application number	US-201414524509-A
Country	US
Kind code	A1
Filing date	Oct 27, 2014
Priority date	Oct 27, 2014
Publication date	Apr 28, 2016
Grant date	—

Abstract

A curable polyester resin composition containing residues of:
a) polyhydroxyl compounds that include:
(i) 2,2,4,4-tetraalkylcyclobutane-1,3-diol (TACD) compounds, and (ii) polyhydroxyl compounds other than TACD, and
(b) polycarboxylic acid compounds that include:
(i) polycarboxylic acid compounds, a derivative of polycarboxylic acid compound other than (bii), or a combination thereof, and (ii) a polycarboxylic anhydride compound;

wherein the curable polyester resin has an acid number ranging from about 20 to about 120 mg KOH/g, a hydroxyl number ranging from greater than 0 to about 100 mg KOH/g, and an acid number:hydroxyl (AN:OH) number ratio of at least 0.5:1. The curable polyester resin can be dispersed in water or a solvent and is suitable for waterborne or solventborne coating compositions and powder coating applications. Phenolic based crosslinking coating compositions that contain these curable polyester resins are curable at elevated temperatures.

First claim

1 . A composition comprising a curable polyester resin, said polyester resin comprising the residues of:
a) polyhydroxyl compounds comprising:
(i) a 2,2,4,4-tetraalkylcyclobutane-1,3-diol (TACD) compound, and
(ii) a polyhydroxyl compound other than TACD, and
b) polycarboxyl compounds comprising:
(i) a polycarboxylic acid compound, a derivative of polycarboxylic acid compound other than (bii), or a combination thereof, and
(ii) a polycarboxylic anhydride compound;
wherein said curable polyester resin has an acid number ranging from about 20 to about 120 mg KOH/g, a hydroxyl number ranging from greater than 0 to about 100 mg KOH/g, and an acid number:hydroxyl number ratio (AN:OH) of at least 0.5:1.

2 . The composition of claim 1 , wherein the TACD compound comprises 2,2,4,4-tetramethylcyclobutane-1,3-diol.

3 . The composition of claim 1 , wherein the polyhydroxyl compound (a)(ii) comprises 2,2-dimethyl-1,3-propanediol (neopentyl glycol), 1,4-cyclohexanedimethanol, or 1,1,1-trimethylol propane, or mixtures thereof.

4 . The composition of claim 1 , wherein the polycarboxylic acid (b)(i) comprises isophthalic acid, dimethyl isophthalate, terephthalic acid, dimethyl terephthalate, 1,4-cyclohexanedicarboxylic acid, adipic acid, or mixtures thereof.

5 . The composition of claim 1 , wherein the polycarboxylic acid (b)(i) comprises:
a) (isophthalic acid or dimethyl isophthalate) and (1,4-cyclohexanedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid, or mixtures thereof); or b) (isophthalic acid or dimethyl isophthalate), and (dodecanedioic acid, sebacic acid, azelaic acid, maleic acid, fumaric acid, succinic acid, adipic acid, glutaric acid, itatonic acid, diglycolic acid; or mixtures thereof); or c) isophthalic acid or dimethyl isophthalate; or d) (1,4-cyclohexanedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid, or mixtures thereof) and (dodecanedioic acid, sebacic acid, azelaic acid, maleic acid, fumaric acid, succinic acid, adipic acid, glutaric acid, itatonic acid, diglycolic acid, or mixtures thereof), or e) 1,4-cyclohexanedicarboxylic acid.

6 . The composition of claim 1 , wherein terephthalic acid or derivatives thereof are not present as polycarboxylic acids (b).

7 . The composition of claim 1 , wherein the polycarboxylic anhydride compound (b)(ii) comprises isobutyric anhydride, acetic anhydride, 2-ethyl hexanoic anhydride, phthalic anhydride, maleic anhydride, or trimellitic anhydride, or mixtures thereof.

8 . The composition of claim 1 , wherein the molar quantity of the TACD compound (ai) exceeds the molar quantity of any other polyhydroxyl compound, based on the total moles of polyhydroxyl compounds (a).

9 . The composition of claim 1 , wherein the quantity of the TACD compound is more than 50 mole % and up to 90 mole %, based on the total moles of polyhydroxyl compounds (a).

10 . The composition of claim 1 , wherein the curable polyester resin contains TACD residues in an amount of 25-47 mole %, based on the total moles of all components of the curable polyester resin.

11 . The composition of claim 1 , wherein the molar quantity of the polycarboxylic anhydride compound (bii) is in a range of 8-30 mole %, based on the total moles of polycarboxylic acid (b).

12 . The composition of claim 1 , wherein the molar quantity of the polycaroxylic anhydride compound (b)(ii) is in a range of 3-15 mole % based on the total moles of all components of the curable polyester resins.

13 . The composition of claim 1 , wherein the acid number is in a range from 50 to 120.

14 . The composition of claim 1 , wherein the hydroxyl number is in a range from 20 to 100.

15 . The composition of claim 1 , wherein the AN:OH ratio is least 0.8:1 and up to 20:1.

16 . The composition of claim 1 , wherein the curable polyester resin has an acid number, a hydroxyl number, and an AN:OH ratio that is within the range of any one box designated with an “x” in Table 3:

TABLE 3

Acid #

OH#
50-100
50-90
60-120
65-100
70-100
45-90
50-85
60-90
65-90
30-90

15-90

x
x
x
x

x
x
x

15-75

x
x
x
x

x
x
x

20-70
x

x

x

x
x

20-65
x

x

x

x
x

20-60
x

x

x

x
x

20-50

x

x

x
x

15-45
x
x
x
x
x

x
x
x

10-40
x
x
x
x
x
x
x
x
x
x

 40-100

x

 50-100

x

 60-100

x

AN:OH
0.8:1-5:1
1.5:1-5:1
0.5:1-2:1
1:1-6:1
0.5:1-4:1
1.3:1-6:1
2:1-4:1
0.5:1-3:1
1.5:1-5:1
1:1-8:1

Ratio

Assignees

• Eastman Chem Co

Inventors

• Kuo Thauming
• Liu Junjia
• Hall Phillip Bryan

Classifications

• C09D167/02

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

• C08K5/17

  Amines; Quaternary ammonium compounds · CPC title

• C08G63/199 Primary

  Acids or hydroxy compounds containing cycloaliphatic rings · CPC title

• C08G63/78

  Preparation processes · CPC title