Coatings containing polyester macromers containing 1,1-dicarbonyl-substituted 1 alkenes

Patent metadata

Field	Value
Publication number	US-9567475-B1
Application number	US-201615298637-A
Country	US
Kind code	B1
Filing date	Oct 20, 2016
Priority date	Jun 3, 2016
Publication date	Feb 14, 2017
Grant date	Feb 14, 2017

Abstract

Compositions comprising a) one or more polyester macromers containing one or more chains of the residue of one or more diols and one or more diesters wherein the residue of the one or more diols and the one or more diesters alternate along the chain and a portion of the diesters are 1,1-diester-1-alkenes and at least one terminal end comprises the residue of one of the 1,1-diester-1 alkenes and wherein one or more terminal ends may comprise the residue of one or more diols; and b) one or more polymers having pendant Michael Addition donor groups. Disclosed are coating prepared from these compositions.

First claim

The invention claimed is:

1. A composition comprising a) a polyester macromer composition comprising one or more polyester macromers containing one or more chains of the residue of one or more diols and one or more diesters wherein the residue of the one or more diols and the one or more diesters alternate along the chain and a portion of the diesters are 1,1-diester-1-alkenes and at least one terminal end comprises the residue of one of the 1,1-diester-1 alkenes and wherein one or more terminal ends may comprise the residue of one or more diols; and b) one or more polymers having pendant Michael Addition donor groups.

2. A composition according to claim 1 wherein the pendant Michael Addition donor groups comprise functional groups containing active hydrogen atoms.

3. A composition according to claim 2 wherein the pendant Michael Addition donor groups comprise amines, hydroxyl, thiol, or mixtures thereof.

4. A composition according to claim 1 wherein the one or more polymers having pendant Michael Addition donor groups comprise one or more of acrylic polyols, amine modified acrylic polyols, polycarbonate polyols, modified acrylic copolymer polyols, polyester polyols, polyether polyols and siloxane polyols.

5. A composition according to claim 1 wherein the one or more polymers having pendant Michael Addition donor groups comprise one or more acrylic polyols or amine modified acrylic polyols.

6. A composition according to claim 1 which comprises from about 40 to about 90 percent by weight of the one or more polyester macromers and from about 10 to 60 percent by weight of the one or more one or more polymers having pendant Michael Addition donor groups wherein the amounts are based on the weight of the composition.

7. A composition according to claim 6 which contains a solvent which comprises one or more polar aprotic solvents.

8. A composition according to claim 1 wherein the polyester macromer exhibits a number average molecular weight of about 700 to about 3000.

9. A composition according to claim 1 wherein the polyester macromer composition comprises:
i) a plurality of polyester macromers;
ii) one or more multifunctional monomers containing the residue of one or more polyols and one or more 1,1-diester-1-alkenes, wherein the multifunctional monomers have substantially all of the hydroxyl groups of the polyols replaced with the 1,1-diester-1-alkenes; and
iii) one or more 1,1-diester-1-alkenes.

10. A composition according to claim 9 wherein the polyester macromer composition comprises
i) from about 10 to about 90 percent by weight of the plurality of polyester macromers;
ii) from about 1 to about 50 percent by weight of the one or more multifunctional monomers; and
iii) from about 1 to about 30 percent by weight of the one or more 1,1-diester-1-alkenes wherein the percentages are based on the amounts of the ingredients listed.

11. A composition according to claim 1 wherein the polymers having pendant Michael Addition donor groups exhibit a hydroxyl number of about 50 to about 200.

12. A coating obtained by curing a composition according to claim 1 .

13. The coating according to claim 12 having a thickness of about 2 to about 160 microns.

14. The coating according to claim 12 wherein the polyester macromers are crosslinked through the 1,1-alkene groups and/or by Michael Addition of the Michael Addition donor groups pendant from the polymers having pendant Michael Addition Donor groups to the 1-alkene groups.

15. The coating according to claim 12 wherein the cured coating exhibits one or more of the following properties of a gloss according to ASTM D523-08 at 20°, or 60°, or 85° of 40 GU or greater; a pencil hardness according to ASTM D3363-00 of 3H or greater; a solvent resistance according to ASTM D5402-93 to 80 rubs of methyl ethyl ketone or greater; mandrel flexibility according to ASTM D522-93 of 80 percent or greater; cross hatch adhesion of 4B or higher and 100 percent according to ASTM D3359-09 and acid resistance up to 70° C. and base resistance at greater than 70° C. according to GMW 14701.

16. A method comprising contacting a composition according to claim 1 with a surface of a substrate wherein the surface is at least mildly nucleophilic and forming a coating on the surface of the substrate comprising the composition containing the one or more polyester macromers.

17. A method according to claim 16 wherein the substrate has a pigmented coating deposited on its surface wherein the pigmented coating is mildly basic or nucleophilic.

18. A method according to claim 16 which includes exposing the substrate with the composition containing one or more polyester macromers deposited on the substrate to a temperature of about 20° C. to about 150° C. for about 10 minutes to about 120 minutes under conditions such that the coating containing one or more polyester macromers disposed on the surface of the substrate is crosslinked.

19. A method according to claim 16 wherein the coating or the surface of the substrate contains a catalyst for Michael Addition.

20. A method according to claim 16 wherein the coating on the surface of the substrate contains an initiator for anionic polymerization.

Assignees

• Sirrus Inc

Inventors

• Palsule Aniruddha S
• Sullivan Jeffrey M
• Vanderpool Katherine E
• Holzer Alexander R
• Deshpande Anushree
• Klier John

Classifications

• C08L67/06

  Unsaturated polyesters · CPC title

• C08L71/02

  Polyalkylene oxides · CPC title

• C08G63/78

  Preparation processes · CPC title

• C08L83/04

  Polysiloxanes · CPC title

• C08L79/08

  Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors · CPC title