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

• US 10,150,886 B2
• Filed: 06/29/2017
• Issued: 12/11/2018
• Est. Priority Date: 06/03/2016
• Status: Expired due to Fees

• Current Assignee: Sirrus, Inc (Nippon Shokubai Company Limited)
• Original Assignee: Sirrus, Inc (Nippon Shokubai Company Limited)
• Inventors: Palsule, Aniruddha S., Sullivan, Jeffrey M., Vanderpool, Katherine E., Holzer, Alexander R., Deshpande, Anushree, Klier, John
• Primary Examiner(s): Nguyen, Vu A
• Application Number:
  US15/638,290
• Publication Number:
  US 20170349781A1
• Time in Patent Office: 530 Days
• Field of Search: None
• CPC Class Codes: C08G 63/00 Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule polyester-amides C08G69/44; polyester-imides C08G73/16
• CPC Class Codes: C08G 63/52 Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
• CPC Class Codes: C08G 63/553 Acids or hydroxy compounds containing cycloaliphatic rings, e.g. Diels-Alder adducts
• CPC Class Codes: C08G 63/676 in which at least one of the two components contains aliphatic unsaturation
• CPC Class Codes: C08G 63/78 Preparation processes
• CPC Class Codes: C08L 33/06 of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
• CPC Class Codes: C08L 67/06 Unsaturated polyesters
• CPC Class Codes: C08L 71/02 Polyalkylene oxides
• CPC Class Codes: C08L 79/02 Polyamines
• CPC Class Codes: C08L 79/08 Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: C09D 133/06 of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
• CPC Class Codes: C09D 167/02 Polyesters derived from dicarboxylic acids and dihydroxy compounds C09D167/06 takes precedence
• CPC Class Codes: C09D 167/06 Unsaturated polyesters having carbon-to-carbon unsaturation
• CPC Class Codes: C12P 7/625 Polyesters of hydroxy carboxylic acids

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.

Claims

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 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;

wherein the diols used to prepare the polyester macromers comprise diols with aliphatic backbones that are branched or diols with cycloaliphatic backbones.

2. A composition according to claim 1 wherein the branched aliphatic chains have at least one branch on the 2 carbon atom.

3. A composition according to claim 2 wherein the diols used to prepare the polyester macromers comprise diols with branched aliphatic chains having at least one branch on the 2 carbon atom and diols with cycloaliphatic backbones.

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

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

6. A composition according to claim 1 wherein the Michael Addition donor groups comprise amines and/or hydroxyl.

7. A composition according to claim 1 wherein the polyester macromers contain one or more alternating chains of the residue of one or more diols and one or more diesters wherein each of the chains are bonded at one end to an oxygen of the residue of a polyol having three or more of the oxygen atoms.

8. 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.

9. 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.

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

11. A composition according to claim 10 which contains a solvent which comprises one or more alkylene glycol ethers, acetate modified alkylene glycol ethers, or ketones, having a boiling point of about 80°

C. to about 200°

C.

12. A composition according claim 11 wherein the solvent is present in an amount of about 5 to about 30 percent by weight wherein the amounts are based on the weight of the composition.

13. A composition according to claim 7 wherein the oxygens from the hydroxyl groups on the diols and polyols of the polyester macromers are bonded to aliphatic carbon atoms.

14. A composition according to claim 1 wherein the one or more chains of the polyester macromers comprise a residue of one or more dihydrocarbyl dicarboxylates.

15. A composition according to claim 14 wherein from about 1 to about 4 dihydrocarbyl dicarboxylates are contained in each chain.

16. A composition according to claim 1 wherein the polyester macromers are present as a composition comprising from about 10 to about 90 percent by weight of a plurality of polyester macromers;

from about 1 to about 50 percent by weight of one or more multifunctional monomers; and

from about 0 to about 30 percent by weight of one or more 1,1-diester-1-alkenes.

17. A composition according to claim 16 wherein the of one or more 1,1-diester-1-alkenes are present in an amount of 0 percent by weight.

18. A composition according to claim 1 which comprises a catalyst for Michael Addition.

19. A composition according to claim 1 which comprises a catalyst for Michael Addition of a hydroxyl group on to an alkene group.

20. A composition according to claim 1 which includes one or more of the following components:

pigments, fillers, reinforcing agents, anti-slip additives, and additves to improve abrasion resistance.