Acid functional and epoxy functional polyester resins

• US 5,739,213 A
• Filed: 01/04/1996
• Issued: 04/14/1998
• Est. Priority Date: 01/06/1995
• Status: Expired due to Fees

• Current Assignee: Resolution Performance Products LLC (Bakelite UK TopCo Ltd.)
• Original Assignee: Shell Oil Company (Shell Plc)
• Inventors: Walravens, Marianne Angele, Kooijmans, Petrus Gerardus, Rosenbrand, Gerrit Gerardus, Freriks, Jan
• Primary Examiner(s): Acquah, Samuel A.
• Application Number:
  US08/582,855
• Time in Patent Office: 831 Days
• Field of Search: 528/271, 528/272, 528/300, 528/301, 528/302, 528/307, 528/308, 528/308.6, 528/361, 525/437, 525/438, 525/450
• US Class Current: 525/438
• CPC Class Codes: C08G 59/12 of polycarboxylic acids with epihalohydrins or precursors thereof
• CPC Class Codes: C08G 63/60 derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds
• CPC Class Codes: C08L 2666/18 Polyesters or polycarbonates according to C08L67/00 - C08L69/00; Derivatives thereof
• CPC Class Codes: C09D 163/00 Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
• CPC Class Codes: C09D 167/00 Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain based on polyester-amides C09D177/12; based on polyester-imides C09D179/08; Coating compositions based on derivatives of such polymers
• CPC Class Codes: Y10T 428/31786 Of polyester [e.g., alkyd, etc.]
• CPC Class Codes: Y10T 428/31794 Of cross-linked polyester

Abstract

Linear, tertiary carboxyl functional polyester resins suitable for the production of coatings having excellent outdoor durable properties, the polyester resins obtainable by reaction of

a) at least one aromatic and/or cycloaliphatic carboxylic acid compound A comprising two aromatic- and/or secondary aliphatic carboxyl groups or the anhydride thereof,

b) at least one hydroxyl compound B comprising two aliphatic hydroxyl groups, which groups each independently may be primary or secondary hydroxyl groups,

c) at least one hydroxyl substituted carboxylic acid compound C comprising at least one tertiary aliphatic carboxyl group and two aliphatic hydroxyl groups, which groups each independently may be primary or secondary hydroxyl groups, and

d) optionally one carboxylic acid compound D comprising one carboxyl group, the molar ratio of compounds A:B:C:D being (X+Y-1):X:Y:Z,

wherein X ranges from 2 to 8, Y ranges from 2 to 8, and Z ranges from 0 to 2.

These polyester resins may be used together with a suitable curing agent for the production of powder coatings, or may be converted into the corresponding glycidylesters, which in combination with a suitable curing agent can be used for the production of powder coatings.

Claims

1. A linear, tertiary carboxyl functional polyester resin produced by reacting

a) at least one aromatic and/or cycloaliphatic carboxylic acid compound A comprising two aromatic- and/or secondary aliphatic carboxyl groups or the anhydride thereof,

b) at least one hydroxyl compound B comprising two aliphatic hydroxyl groups,

c) at least one hydroxyl substituted carboxylic acid compound C comprising at least one tertiary aliphatic carboxyl group and two aliphatic hydroxyl groups, and

d) one carboxylic acid compound D comprising one carboxyl group, the molar ratio of compounds A:

B;

C;

D being (X+Y-1);

X;

Y;

Z,

wherein X ranges from 2 to 8, Y ranges from 2 to 8, and Z ranges from 1 to 2.

2. The linear, tertiary carboxyl functional polyester resin of claim 1 in which compound A is a cycloaliphatic dicarboxylic acid comprising two secondary aliphatic carboxyl groups or the anhydride thereof.

3. The linear, tertiary carboxyl functional polyester resin of claim 2 in which compound A is hexahydrophthalic acid or the anhydride thereof.

4. The linear, tertiary carboxyl functional polyester resin of claim 1 in which compound B comprises two secondary aliphatic hydroxyl groups.

5. The linear, tertiary carboxyl functional polyester resin of claim 4 in which compound B comprises one or more cyclohexane rings, the compound being substituted by two secondary hydroxyl groups.

6. The linear, tertiary carboxyl functional polyester resin of claim 5 in which compound B is hydrogenated diphenylol propane.

7. The linear, tertiary carboxyl functional polyester resin of claim 1 in which compound C comprises a tertiary aliphatic carboxyl group and two primary hydroxyl groups.

8. The linear, tertiary carboxyl functional polyester resin of claim 7 in which compound C is dimethylolpropionic acid.

9. The linear, tertiary carboxyl functional polyester resin of claim 1 in which compound D is cyclohexane carboxylic acid.

10. The linear, tertiary carboxyl functional polyester resin of claim 1 in which X ranges from 5 to 7.

11. The linear, tertiary carboxyl functional polyester resin of claim 1 in which Y ranges from 3 to 5.

17. The polyglycidylester resin prepared by reacting a linear, tertiary carboxyl functional polyester resin claim 1 with epihalohydrin in the presence of a base.

18. The polyglycidylester resin of claim 17 wherein the epihalohydrin used is epichlorohydrin.

19. A powder coating composition comprising a polyglycidylester resin of claim 17 and a cross-linking agent.

20. A powder coating composition comprising a linear tertiary aliphatic carboxyl functional polyester resin as claimed in claim 1 and a cross-linking agent.

21. A product coated with the powder coating composition of claim 20.

22. The polyglycidylester resin prepared by reacting a linear, tertiary carboxyl functional polyester resin of claim 4 with epihalohydrin in the presence of a base.

23. The polyglycidylester resin prepared by reacting a linear, tertiary carboxyl functional polyester resin of claim 7 with epihalohydrin in the presence of a base.

24. The polyglycidylester resin prepared by glycidating a linear, tertiary carboxyl functional polyester resin of claim 1.

12. A process for the preparation of the linear, tertiary carboxyl functional polyester resins comprising reacting, in a reactor,

a) at least one aromatic and/or cycloaliphatic carboxylic acid compound A comprising two aromatic- and/or secondary aliphatic carboxyl groups or the anhydride thereof,

b) at least one hydroxyl compound B comprising two aliphatic hydroxyl groups,

c) at least one hydroxyl substituted carboxylic acid compound C comprising at least one tertiary aliphatic carboxyl group and two aliphatic hydroxyl groups, and

d) one carboxylic acid compound D comprising one carboxyl group, the molar ratio of compounds A:

B;

C;

D being (X+Y-1);

X;

Y;

Z,

wherein X ranges from 2 to 8, Y ranges from 2 to 8, and Z ranges from 1 to 2.

13. The process of claim 12 which reaction is carried out at a temperature within the range of about 100°

to about 230°

C., until essentially all the non-tertiary carboxyl groups as initially present in the reaction mixture have reacted.

14. The process of claim 12 wherein compounds A to C and compound D are charged to the reactor, followed by reaction at a temperature within the range of about 120°

to about 230°

C., and the reaction is continued until the non-tertiary carboxyl groups as initially present in the reaction mixture have reacted.

15. The process of claim 12 wherein first compounds A and C are charged to the reactor followed by reaction within the range of about 100°

to about 220°

C., whereafter compound B and optionally compound D is added to the reaction mixture, followed by reaction at a temperature within the range of about 120°

to about 230°

C.

16. The process of claim 12 in which the compounds A to C are reacted in the presence of an esterification catalyst.