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

Patent metadata

Field	Value
Publication number	US-9718989-B1
Application number	US-201715410003-A
Country	US
Kind code	B1
Filing date	Jan 19, 2017
Priority date	Jun 3, 2016
Publication date	Aug 1, 2017
Grant date	Aug 1, 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) 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 ore 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 wherein a portion of or all of the polyester macromers are crosslinked by Michael Addition of the Michael Addition Donors pendant from the polymers to the 1-alkene groups of the polyester macromers
wherein the crosslinks by Michael Addition of the Michael Addition Donors pendant from the polymers to the 1-alkene groups of the polyester macromer correspond to the formula

wherein X is the residue of a Michael Addition Donor; and
R x is the polymer or the substrate to which the residue of the Michael Addition Donor is bonded.

2. A composition according to claim 1 wherein X is independently in each occurrence O, NR y , or S;
R x is independently in each occurrence a polymer comprising an acrylic polyol, amine modified acrylic polyol, polycarbonate polyol, modified acrylic copolymer poly, polyester polyol, polyether polyol or siloxane polyol or a substrate; and,
R y is independently in each occurrence H or a hydrocarbyl group.

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

4. A composition according to claim 1 wherein the pendant Michael Addition donor groups comprise amines, hydroxyl, thiol, or mixtures thereof.

5. 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.

6. 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.

7. A composition according to claim 1 wherein the polyester macromer exhibits a number average molecular weight of about 400 to about 3000.

8. A composition comprising
i) a plurality of 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 dole 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 morn diols;
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;
iii) one or more 1,1-diester-1-alkenes; and
iv) one or more polymers having pendant Michael Addition donor groups;
wherein a portion of or all of the polyester macromers are crosslinked through the 1,1-alkene groups by Michael Addition of the Michael Addition Donors pendant from the polymers;
wherein the crosslinks by Michael Addition of the Michael Addition Donors pendant from the polyols to the 1-alkene groups of the polyester macromer correspond to the formula

wherein X is the residue of a Michael Addition Donor; and
R x is the polymer or the substrate to which the residue of the Michael Addition Donor is bonded.

9. A composition according to claim 8 wherein the pendant Michael Addition donor groups comprise functional groups containing active hydrogen atoms.

10. A composition according to claim 8 wherein the pendant Michael Addition donor groups comprise amines, hydroxyl, thiol, or mixtures thereof.

11. A composition according to claim 8 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.

12. A composition according to claim 8 wherein the one or more polymers having pendant Michael Addition donor groups comprise one or more acrylic polyols or amine modified acrylic polyols.

13. A composition according to claim 8 wherein X is independently in each occurrence O, NR y , or S; and
R x is independently in each occurrence a polymer comprising an acrylic polyol, amine modified acrylic polyol, polycarbonate polyol, modified acrylic copolymer polyol, polyester polyol, polyether polyol or silane polyol or a substrate; and,
R y is H or a hydrocarbyl group.

14. A composition according to claim 8 wherein a portion of the polyester macromers are crosslinked through some of the 1,1-alkene groups wherein the crosslinks between chains are represented by formula 17:

wherein F is separately in each occurrence a direct bond or the residue of a compound that polymerizes with an unsaturated group by anionic polymerization or free radical polymerization.

15. A composition according to claim 14 wherein F is separately in each occurrence a direct bond or the residue of a 1,1-diester-1-alkene or a multifunctional monomer.

16. A composition according to claim 8 wherein the polyester macromer exhibits a number average molecular weight of about 400 to about 3000.

17. A composition according to claim 1 wherein a portion of the polyester macromers are crosslinked through some of the 1,1-alkene groups wherein the crosslinks between chains are represented by formula 17:

wherein F is separately in each occurrence a direct bond or the residue of a compound that polymerizes with an unsaturated group by anionic polymerization or free radical polymerization.

18. A composition according to claim 17 wherein F is separately in each occurrence a direct bond or the residue of a 1,1-diester-1-alkene or a multifunctional monomer.

Assignees

• Sirrus Inc

Inventors

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

Classifications

• C08L83/04

  Polysiloxanes · CPC title

• C08G63/78

  Preparation processes · CPC title

• C08L79/08

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

• C08L67/06

  Unsaturated polyesters · CPC title

• C08L79/02

  Polyamines · CPC title