Polyester resin having excellent heat resistance and solubility in solvents, and coating composition containing same

Patent metadata

Field	Value
Publication number	US-11401372-B2
Application number	US-201716063387-A
Country	US
Kind code	B2
Filing date	Jan 5, 2017
Priority date	Feb 4, 2016
Publication date	Aug 2, 2022
Grant date	Aug 2, 2022

Abstract

A polyester resin and a coating composition containing the polyester resin are disclosed. The polyester resin includes a repeating unit obtained by copolymerizing (a) a divalent acid component and (b) a diol component containing (b-1) an isosorbide and (b-2) a cycloaliphatic diol, and has excellent heat resistance and solubility in a solvent. The cycloaliphatic diol may be one or more diol derivatives of a tricycle C7-14 alkane. A coating formed from a coating composition containing the polyester shows excellent heat resistance, hardness, chemical resistance, pollution resistance, and hydrolysis resistance.

First claim

The invention claimed is:

1. A polyester resin comprising a repeating unit obtained by copolymerizing the following (a) and (b):
(a) a divalent acid component;
(b) a diol component comprising (b-1) an isosorbide, (b-2) a cycloaliphatic diol, and (b-3) neopentyl glycol,
wherein the cycloaliphatic diol (b-2) is one or more diol derivatives of a tricycle C7-14 alkane;
wherein a molar ratio of a sum of the isosorbide (b-1) and the cycloaliphatic diol (b-2) to the neopentyl glycol (b-3) is 0.5 to 2.5:1;
wherein the diol component (b) comprises 1 to 50 mol % of the isosorbide (b-1) and 1 to 80 mol % of the cycloaliphatic diol (b-2) based on a total number of moles of the diol component;
wherein an amount of the neopentyl glycol (b-3) employed for the copolymerization is 23 mol % to 52.3 mol % based on a total number of moles of the diol component (b) employed in the copolymerization; and wherein the polyester resin has a glass transition temperature of 80° C. or higher.

2. The polyester resin of claim 1 , wherein the cycloaliphatic diol (b-2) is a diol derivative of a compound selected from the group consisting of tricyclo[3.2.1.0 2,6 ]octane, tricyclo[4.2.1.0 2,6 ]nonane, tricyclo[5.2.1.0 2,6 ]decane, tricyclo[6.2.1.0 2,6 ]undecane, tricyclo[7.2.1.0 2,6 ]dodecane, tricyclo[4.2.1.1 2,5 ]decane, tricyclo[4.3.1.1 2,5 ]decane, tricyclo[4.4.1.1 2,5 ]decane, tricyclo[2.2.1.0 2,6 ]heptane, tricyclo[2.2.2.0 2,6 ]octane, tricyclo[3.2.2.0 2,6 ]nonane, tricyclo[3.3.1.1 3,6 ]decane, tricyclo[3.2.1.1 3,7 ]nonane, tricyclo[4.2.2.2 2,5 ]dodecane, tricyclo[4.3.2.2 2,5 ]tridecane, tricyclo[4.4.2.2 2,5 ]tetradecane, tricyclo[4.2.1.0 3,7 ]nonane, tricyclo[4.4.1.1 1,5 ]dodecane, tricyclo[6.2.1.0 2,7 ]undecane, tricyclo[5.2.2.0 2,6 ]undecane, tricyclo[6.2.2.0 2,7 ]dodecane, tricyclo[4.3.2.0 2,5 ]undecane, tricyclo[4.2.2.0 2,5 ]decane and tricyclo[5.5.1.0 3,11 ]tridecane, or a mixture thereof.

3. The polyester resin of claim 1 , wherein the divalent acid component (a) comprises one or more C 8 -C 14 aromatic dicarboxylic acids.

4. The polyester resin of claim 1 , wherein the divalent acid component (a) comprises a compound selected from the group consisting of terephthalic acid, isophthalic acid, naphthalene dicarboxylic acid, diphenyl dicarboxylic acid, a derivative thereof, and a mixture thereof.

5. The polyester resin of claim 4 , wherein the divalent acid component (a) comprises the terephthalic acid, the isophthalic acid, or a mixture thereof in an amount of 1 to 100 mol % based on a total number of moles of the divalent acid component (a).

6. The polyester resin of claim 1 , wherein the polyester resin has a number average molecular weight of 2,000 to 20,000, a hydroxyl value of 2 to 60 mgKOH/g, and an acid value of 0.1 to 20 mgKOH/g.

7. The polyester resin of claim 1 , wherein the polyester resin has a glass transition temperature of 80 to 150° C.

8. A coating composition, comprising:
a polyester resin; and
an organic solvent,
wherein the polyester resin comprises a repeating unit obtained by copolymerizing the following (a) and (b):
(a) a divalent acid component;
(b) a diol component comprising (b-1) an isosorbide, (b-2) a cycloaliphatic diol, and (b-3) neopentyl glycol,
wherein the cycloaliphatic diol (b-2) is one or more diol derivatives of a tricycle C7-14 alkane;
wherein a molar ratio of a sum of the isosorbide (b-1) and the cycloaliphatic diol (b-2) to the neopentyl glycol (b-3) is 0.5 to 2.5:1;
wherein the diol component (b) comprises 1 to 50 mol % of the isosorbide (b-1) and 1 to 80 mol % of the cycloaliphatic diol (b-2) based on a total number of moles of the diol component;
wherein an amount of the neopentyl glycol (b-3) employed for the copolymerization is 23 mol % to 52.3 mol % based on a total number of moles of the diol component (b) employed in the copolymerization; and wherein the polyester resin has a glass transition temperature of 80° C. or higher.

9. The coating composition of claim 8 , wherein the organic solvent is selected from the group consisting of an aromatic hydrocarbon solvent, a glycol ester solvent, a glycol ether solvent, a ketone solvent, an alcohol solvent, and a mixture thereof.

10. The coating composition of claim 8 , wherein the coating composition comprises 10 to 40 wt % of the polyester resin and 60 to 90 wt % of the organic solvent.

11. The coating composition of claim 8 , wherein the coating composition further comprises a component selected from the group consisting of a cross-linking agent, a curing catalyst, an additive for slip property, a smoothening agent, a defoaming agent, a pigment, a leveling agent, and a mixture thereof.

12. The coating composition of claim 8 , wherein the cycloaliphatic diol (b-2) is a diol derivative of a compound selected from the group consisting of tricyclo[3.2.1.0 2,6 ]octane, tricyclo[4.2.1.0 2,6 ]nonane, tricyclo[5.2.1.0 2,6 ]decane, tricyclo[6.2.1.0 2,6 ]undecane, tricyclo[7.2.1.0 2,6 ]dodecane, tricyclo[4.2.1.1 2,5 ]decane, tricyclo[4.3.1.1 2,5 ]decane, tricyclo[4.4.1.1 2,5 ]decane, tricyclo[2.2.1.0 2,6 ]heptane, tricyclo[2.2.2.0 2,6 ]octane, tricyclo[3.2.2.0 2,6 ]nonane, tricyclo[3.3.1.1 3,6 ]decane, tricyclo[3.2.1.1 3,7 ]nonane, tricyclo[4.2.2.2 2,5 ]dodecane, tricyclo[4.3.2.2 2,5 ]tridecane, tricyclo[4.4.2.2 2,5 ]tetradecane, tricyclo[4.2.1.0 3,7 ]nonane, tricyclo[4.4.1.1 1,5 ]dodecane, tricyclo[6.2.1.0 2,7 ]undecane, tricyclo[5.2.2.0 2,6 ]undecane, tricyclo[6.2.2.0 2,7 ]dodecane, tricyclo[4.3.2.0 2,5 ]undecane, tricyclo[4.2.2.0 2,5 ]decane and tricyclo[5.5.1.0 3,11 ]tridecane, or a mixture thereof.

13. The coating composition of claim 8 , wherein the divalent acid component (a) comprises one or more C 8 -C 14 aromatic dicarboxylic acids.

14. The coating composition of claim 8 , wherein the divalent acid component (a) comprises a compound selected from the group consisting of terephthalic acid, isophthalic acid, naphthalene dicarboxylic acid, diphenyl dicarboxylic acid, a derivative thereof, and a mixture thereof.

15. The coating composition of claim 8 , wherein the divalent acid component (a) comprises the terephthalic acid, the isophthalic acid, or a mixture thereof in an amount of 1 to 100 mol % based on a total number of moles of the divalent acid component (a).

16. The coating composition of claim 8 , wherein the polyester resin has a number average molecular weight of 2,000 to 20,000, a hydroxyl value of 2 to 60 mgKOH/g, and an acid value of 0.1 to 20 mgKOH/g.

Assignees

• Sk Chemicals Co Ltd

Inventors

• Sim Jong-Ki
• Kim Soon-Ki

Classifications

• C08G63/672 Primary

  Dicarboxylic acids and dihydroxy compounds · CPC title

• C09D167/025

  containing polyether sequences · CPC title

• C09D7/00

  Features of coating compositions, not provided for in group C09D5/00 (driers C09F9/00); Processes for incorporating ingredients in coating compositions · CPC title

• C09D167/02

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

• C08G63/02

  Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds · CPC title