Polyesters for coatings

• US 8,637,581 B2
• Filed: 11/12/2010
• Issued: 01/28/2014
• Est. Priority Date: 11/13/2009
• Status: Active Grant

• Current Assignee: Allnex Belgium SA (Allnex Holding S.a r.l.)
• Original Assignee: Cytec Surface Specialties S.A.
• Inventors: Moens, Luc
• Primary Examiner(s): BOYKIN, TERRESSA M
• Application Number:
  US13/497,600
• Publication Number:
  US 20120220676A1
• Time in Patent Office: 1,173 Days
• Field of Search: 521/48.5
• US Class Current: 521/48.5
• CPC Class Codes: C08G 63/672 Dicarboxylic acids and dihydroxy compounds
• CPC Class Codes: C08G 63/916 Dicarboxylic acids and dihydroxy compounds
• CPC Class Codes: C08J 11/24 containing hydroxyl groups
• CPC Class Codes: C08J 2367/02 Polyesters derived from dicarboxylic acids and dihydroxy compounds; C08J2367/06 takes precedence
• CPC Class Codes: C09D 167/02 Polyesters derived from dicarboxylic acids and dihydroxy compounds C09D167/06 takes precedence
• CPC Class Codes: C09D 167/025 containing polyether sequences
• CPC Class Codes: C09D 167/07 having terminal carbon-to-carbon unsaturated bonds
• CPC Class Codes: Y02P 20/582 Recycling of unreacted starting or intermediate materials
• CPC Class Codes: Y02W 30/62 Plastics recycling; Rubber recycling

Abstract

The present invention relates to polyesters that can be prepared from renewable resources and/or recycled materials and the production process thereof. In particular, hydroxyl-functional or carboxyl-functional polyesters containing moieties of terephthalic acid and/or isophthalic acid, ethylene glycol, a dianhydrohexitol, and of one or more linear chain dicarboxylic acids are provided. Further, the polyesters have a number average molecular weight, as measured by gel permeation chromatography, of from 400 to 15000 daltons, more preferably from 550 to 15000 daltons. The polyesters of the invention can basically be prepared from recycled polyethylene terephthalate and from renewable polyacids and/or polyols. The present invention further provides a process to produce such polyesters via glycolysis of a polyethylene terepthalate and/or a polyethylene isophthalate with a dianhydrohexitol.

Claims

1. A hydroxyl-functional or a carboxyl-functional polyester comprising moieties of

(a) terephthalic acid and/or isophthalic acid,

(b) ethylene glycol,

(c) a dianhydrohexitol, and of

(d) one or more linear chain dicarboxylic acids

wherein the polyester has a number average molecular weight, as measured by gel permeation chromatography, of from 400 to 15000 daltons.

2. The polyester of claim 1 comprising, based on the total weight of the polyester:

(a) from 10% to 80% by weight of moieties of terephthalic acid and/or of isophthalic acid,

(b) from 5% to 35% by weight of moieties of ethylene glycol,

(c) from 5% to 40% by weight of moieties of dianhydrohexitol,

(d) from 5% to 40% by weight of moieties of linear chain dicarboxylic acids, and

(e) from 0% to 40% by weight of moieties of one or more other polyols (e1) and/or of one or more other polyacids (e2 ).

3. The polyester of claim 2, wherein the dianhydrohexitol is isosorbide.

4. A (meth)acryloyl-functional polyester prepared from a polyester of claim 1.

5. A coating composition comprising at least one polyester of claim 1.

6. An article coated, partially or entirely, with a coating composition of claim 5.

17. The polyester of claim 1, wherein the polyester has a number average molecular weight, as measured by gel permeation chromatography, of from 550 to 15000 daltons.

7. A process to produce a polyester comprising a step of

(1) glycolysis of a polyethylene terephthalate and/or a polyethylene isophthalate with a dianhydrohexitol, followed

(2) where needed, by one or more additional steps,

wherein a polyester is produced that is hydroxyl-functional or carboxyl-functional, and that has a number average molecular weight, as measured by gel permeation chromatography, of from 400 to 15000 daltons.

8. The process of claim 7 wherein step (2 ) comprises a step of chain extension and/or carboxylation of a hydroxyl-functional polyester previously obtained.

9. The process of claim 8 wherein for said chain extension and/or said carboxylation one or more linear chain dicarboxylic acids are used.

10. The process of claim 7 wherein the polyethylene terephthalate and/or of a polyethylene isophthalate used in step (1 ) is provided under the form of a material comprising said polyethylene terephthalate and/or said polyethylene isophthalate.

11. The process of claim 10 wherein said material is a recycled material.

12. The process of claim 11 wherein said recycled material is recycled polyethylene terephthalate.

13. The process of claim 7 wherein said dianhydrohexitol is isosorbide obtained from a bio-based feedstock.

14. The process of claim 7 further comprising a step of converting a hydroxylfunctional polyester or a carboxyl-functional polyester thus obtained into a (meth)acryloylfunctional polyester.

15. The process of claim 14 wherein a (meth)acryloyl group end-capped polyester is obtained from the reaction of a diisocyanate with a hydroxylalkyl(meth)acrylate and with the terminal hydroxyl groups of a hydroxyl-functional polyester, or from the reaction of a (meth)acrylic acid with the terminal hydroxyl groups of a hydroxyl-functional polyester.

16. The process of claim 14 wherein a (meth)acryloyl group end-capped polyester is obtained from the reaction of glycidyl(meth)acrylate and the terminal carboxyl groups of a carboxylfunctional polyester.

18. The process of claim 7, wherein a polyester is produced that is hydroxyl-functional or carboxyl-functional, and that has a number average molecular weight, as measured by gel permeation chromatography, of from 550 to 15000 daltons.