Water-dilutable polyester, process for the preparation thereof and the use thereof

• US 4,390,688 A
• Filed: 03/12/1982
• Issued: 06/28/1983
• Est. Priority Date: 03/14/1981
• Status: Expired due to Fees

• Current Assignee: Hoechst Aktiengesellschaft (Sanofi )
• Original Assignee: Hoechst Aktiengesellschaft (Sanofi )
• Inventors: Walz, Gerd, Sprenger, Walter, Wirth, Thaddaus
• Primary Examiner(s): Phynes, Lucille M.
• Application Number:
  US06/357,571
• Time in Patent Office: 473 Days
• Field of Search: 528/295.3, 528/296, 528/297, 525/438, 525/443, 525/119, 523/400
• US Class Current: 528/295.3
• CPC Class Codes: C08G 59/4284 together with other curing agents
• CPC Class Codes: C08G 63/42 Cyclic ethers C08G59/00 takes precedence; Cyclic carbonates; Cyclic sulfites; Cyclic orthoesters
• CPC Class Codes: C08G 63/58 Cyclic ethers C08G59/00 takes precedence; Cyclic carbonates; Cyclic sulfites ; Cyclic orthoesters

Abstract

A water dilutable polyester having a good resistance to hydrolysis based on

(A) at least one dicarboxylic acid unit,

(B) at least one polycarboxylic monoanhydride and

(C) at least one alcohol component containing at least dihydric alcohol,

the COOH groups of the polyester being at least partially present in the form of salts with amine, characterized in that the polyester is also derived from

(D) at least one epoxy compound which contains at least two oxiran rings and is selected from the group consisting of epoxidized fatty acids, derivatives thereof and epoxidized aliphatic hydrocarbons or mixtures thereof with up to 30% of monoepoxides, the percentage being based on the epoxy groups, and in that the polycarboxylic monoanhydride (B) is incorporated in the form of a half ester and is other than phthalic anhydride and maleic anhydride.

The invention also relates to a process for the preparation of such polyester, its use in a coating composition and to articles coated with such coating compositions.

Claims

1. A water-dilutable polyester having a good resistance to hydrolysis in which free COOH-groups are at least partially present in the form of ammonium salts, derived from

(A) at least one dicarboxylic acid unit;

(B) at least one polycarboxylic monoanhydride being built-in in the form of a half-ester and different from phthalic anhydride and maleic anhydride;

(C) at least one alcohol component containing an at least dihydric alcohol and

(D) at least one epoxy compound having at least two oxiran rings and being selected from the group consisting of epoxidized fatty acids, derivatives thereof, epoxidizid aliphatic hydrocarbons and mixtures thereof with monoepoxides.

2. A polyester as claimed in claim 1 wherein an amount of at least 50% of the epoxy groups of compound (D) is esterified.

3. A process for the preparation of a polyester as claimed in claim 1 which comprises

(a) reacting in a first step (A) at least one dicarboxylic acid unit with (D) at least one epoxy compound having at least two oxiran rings, selected from the group consisting of epoxidized fatty acids, derivatives thereof, epoxidized aliphatic hydrocarbons and mixtures thereof with monoepoxides and (C) at least one alcohol component comprising an at least dihydric alcohol to form a polyester having an acid number between 2 and 100,

(b) reacting in a second step any polyester obtained in step (a) having an acid number of at least 15 with an epoxy compound selected from the group consisting of a monoepoxide, a polyepoxide and a combination of both, said epoxide containing additionally at least one ester group, to form a polyester having an acid number below 15,

(c) reacting the polyester having an acid number below 15 obtained in step (a) or (b) with (B) at least one polycarboxylic monoanhydride, different from phthalic anhydride and maleic anhydride, between ambient temperature and 170°

C., thus forming a half-ester of the monoanhydride.

(d) converting free COOH--groups of the half-ester obtained in step (c) with an amine to the ammonium salt and

(e) separating the product of step (d) or diluting said product with a suitable solvent.

4. A process as claimed in claim 3 wherein in step (c) the polyester is reacted with component (B) selected from the group consising of trimellitic anhydride, an at least partially hydrogenated anhydride of an aromatic dicarboxylic acid and a combination of both.

5. A process as claimed in claim 3 wherein the polyester condensation in step (a) is performed at a temperature of at least 170°

C.

6. A process as claimed in claim 3 wherein in step (a) a polyester is prepared from the acid component, the alcohol component and such an amount of the epoxide compound (D) in the form of a polyepoxide containing epoxy groups and at least one ester group, alone or in combination with a monoepoxide, to form a polyester having an acid number below 15, and subsequently the reaction is continued in step (b) or, under omission of step (b), in step (c).

7. A coating composition comprising a polyester as claimed in claim 1 alone or in combination with at least one water-dilutable substance selected from the group consisting of an amino resin and an epoxide.

8. A composition as claimed in claim 7 containing the polyester in combination with (α

) at least one water-dilutable epoxide being free from glycidyl ester and ether groups, containing at least one epoxy group and at least one ester group of a monocarboxylic acid and a further ester group being vicinally arranged to said first ester group which second ester group has been formed by reaction of an OH--group with a polycarboxylic monoanhydride, the second COOH--group which has been formed from the anhydride by the partial esterification being at least partially present in the form of a salt of a base of with (β

) a combination of that defined in (α

) with a water-dilutable amino resin.

9. A composition as claimed in claim 8 in combination with a polymer dispersion.

10. An article coated with a coating composition as claimed in claim 7.

11. A polyester as claimed in claim 1 wherein the epoxy compound used is a mixture containing up to 30% of a monoepoxide, the percentage being referred to the total of epoxide groups.