Branched polyester-urethane resins and coatings comprising the same

Patent metadata

Field	Value
Publication number	US-10035872-B2
Application number	US-201514967763-A
Country	US
Kind code	B2
Filing date	Dec 14, 2015
Priority date	Apr 1, 2010
Publication date	Jul 31, 2018
Grant date	Jul 31, 2018

Abstract

An uncured branched polyester-urethane resin prepared by free radical polymerization of an unsaturated polyester prepolymer having a polyol segment, an unsaturated polycarboxylic acid and/or an anhydride and/or ester thereof, and a urethane segment, wherein the polymerization occurs primarily by reaction of the unsaturation is disclosed. Coatings comprising the same are also disclosed, as are substrates coated at least in part with such coatings.

First claim

What is claimed is:

1. An uncured branched polyester-urethane resin prepared by free radical polymerization of double bonds in an unsaturated polyester-urethane prepolymer, wherein the unsaturated polyester-urethane prepolymer is prepared by reacting:
a) one or more polyols;
b) one or more unsaturated polycarboxylic acids and/or anhydrides and/or esters thereof; and
c) one or more isocyanates; wherein the branched polyester-urethane resin is not prepared from unsaturated monomers other than the unsaturated polycarboxylic acids and/or anhydrides and/or esters thereof of b), and wherein the branched polyester-urethane resin is not a graft copolymer.

2. The polyester-urethane resin of claim 1 , wherein the polyol comprises neopentyl glycol, and the unsaturated polycarboxylic acid, anhydride and/or ester thereof comprises maleic acid, maleic anhydride and/or an ester of maleic acid.

3. The polyester-urethane resin of claim 1 , wherein the polyester-urethane prepolymer is reacted with a carboxylic acid, anhydride or ester and neutralized with an amine prior to free radical polymerization.

4. The polyester-urethane resin of claim 3 , wherein the carboxylic acid comprises 2,2-dimethylolpropionic acid and the amine comprises triethylamine.

5. The polyester-urethane resin of claim 1 , wherein a urethane segment is formed on the polyester-urethane resin by reaction of an isocyanate with a hydroxyl group from the polyol.

6. The polyester-urethane resin of claim 1 , wherein the isocyanate comprises isophorone diisocyanate.

7. The polyester-urethane resin of claim 1 , wherein the free radical polymerization occurs in an aqueous solution.

8. The polyester-urethane resin of claim 1 , wherein the M w of the polyester-urethane resin is 30,000 or greater as determined by gel permeation chromatography using a polystyrene standard for calibration.

9. The polyester-urethane resin of claim 1 , wherein the Mw of the polyester-urethane prepolymer is 2,500 or greater as determined by gel permeation chromatography using a polystyrene standard for calibration.

10. A coating composition comprising the polyester-urethane resin of claim 1 and a crosslinker therefor.

11. The coating composition of claim 10 , having a chip resistance lower than 2 as measured with an Erichsen stone hammer blow testing instrument model 508 operated at 2 bar and 25° C.

12. The coating composition of claim 10 , wherein the polyol comprises neopentyl glycol, and the unsaturated polycarboxylic acid, anhydride and/or ester thereof comprises maleic acid, maleic anhydride and/or an ester of maleic acid.

13. The coating of claim 10 , wherein the coating is a basecoat.

14. A substrate coated at least in part with the coating of claim 10 .

15. The substrate of claim 14 , wherein the substrate is part of a vehicle.

16. A process for forming a multilayer coating system on a substrate, the process comprising:
forming a first basecoat layer over at least a portion of a substrate by depositing a first basecoat composition over at least a portion of the substrate;
optionally, drying or curing the first basecoat layer;
forming a second basecoat layer on at least a portion of the first basecoat layer by depositing a second basecoat composition, which is the same or different from the first basecoat composition, directly onto at least a portion of the first basecoat layer;
optionally, drying or curing the second basecoat layer; and
curing any uncured coating layer,

wherein at least one of the first basecoat composition and the second basecoat composition comprises a coating composition of claim 10 .

17. The process of claim 16 , further comprising forming a clearcoat composition on at least a portion of the second basecoat layer by depositing a clearcoat composition over at least a portion of the second basecoat layer.

18. The process of claim 16 , further comprising forming an electrodeposition coating layer by electrodepositing a electrodepositable coating composition on at least a portion of the substrate prior to the step of forming the first basecoat layer.

19. The process of claim 16 , wherein the second basecoat composition is different from the first basecoat composition.

20. The process of claim 16 , wherein the second basecoat composition comprises the coating composition of claim 10 .

21. An uncured branched polyester-urethane resin prepared by:
a) free radical polymerization of double bonds of at least one unsaturated polyester prepolymer having hydroxyl functionality to form a polyester polymer and
b) reaction of the polyester polymer formed in step a) with an isocyanate,
wherein the polyester prepolymer is prepared by reacting:
i) one or more polyols; and
ii) one or more unsaturated polycarboxylic acids and/or anhydrides and/or esters thereof; and wherein the branched polyester-urethane resin is not prepared from unsaturated monomers other than the unsaturated polycarboxylic acids and/or anhydrides and/or esters thereof of ii), such that the branched polyester-urethane resin is not a graft copolymer.

22. The polyester-urethane resin of claim 21 , wherein the reaction product of step b) is reacted with a carboxylic acid and neutralized with an amine and dispersed in water.

23. The polyester-urethane resin of claim 21 , wherein the isocyanate comprises isophorone diisocyanate.

24. An uncured branched polyester-urethane resin prepared by free radical polymerization of a double bond of a first unsaturated polyester prepolymer and a double bond of a second unsaturated polyester prepolymer, wherein each prepolymer is independently prepared by reacting:
a) one or more polyols; and
b) one or more unsaturated polycarboxylic acids and/or anhydrides and/or esters thereof; and wherein at least one of the unsaturated polyester prepolymers comprises a urethane segment, and wherein the prepolymers are the same or different, and wherein the branched polyester-urethane resin is not prepared from unsaturated monomers other than the unsaturated polycarboxylic acids and/or anhydrides and/or esters thereof of b), such that the branched polyester-urethane resin is not a craft copolymer.

Assignees

• Ppg Ind Ohio Inc

Inventors

• Ciaccio Francesco
• Antonaci Annamaria
• Bonello Eddy
• Schoch Stephane
• Klaeger Wolfgang
• Seiler Beate
• Camerano José
• Singer Debra L
• Schwendeman John E
• Swarup Shanti

Classifications

• C09D175/06 Primary

  from polyesters · CPC title

• C08G18/0823

  containing carboxylate salt groups or groups forming them · CPC title

• C08G18/10

  Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step · CPC title

• Y10T428/1355

  Elemental metal containing [e.g., substrate, foil, film, coating, etc.] · CPC title

• C08G18/68

  Unsaturated polyesters · CPC title