IP Library › Granted Patent US 11,401,372
Granted Patent B2
US 11,401,372 · App. 16/063,387 · Granted Aug 2, 2022

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

Inventors: Jong-ki Sim (Gunpo-si, KR); Soon-Ki Kim (Suwon-si, KR)
Assignee: SK CHEMICALS CO., LTD.
C08G63/668C08G63/02C08G63/66C08G63/672C09D7/00C09D7/20C09D7/40C09D167/02C09D167/025
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Quick Facts
Patent No.
US 11,401,372
App. No.
16/063,387
Granted
Aug 2, 2022
Kind
B2
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 C 7-14 alkane. A coating formed from a coating composition containing the polyester shows excellent heat resistance, hardness, chemical resistance, pollution resistance, and hydrolysis resistance.

Claims (31)

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.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 18, 2018
From: SIM, JONG-KI; KIM, SOON-KI
To: SK CHEMICALS CO., LTD.
Reel/Frame 046120/0772 →
Priority Claims (1)
KR 10-2016-0014425 · Feb 4, 2016 · national
Continuity (1)
Related Publication 20190077908A1 · Mar 14, 2019