Adhesion promoter resin compositions and coating compositions having the adhesion promoter resin compositions

• US 9,617,446 B2
• Filed: 12/23/2011
• Issued: 04/11/2017
• Est. Priority Date: 12/29/2010
• Status: Active Grant

• Current Assignee: AKZO Nobel Coatings International BV (Nouryon BV)
• Original Assignee: AKZO Nobel Coatings International BV (Nouryon BV)
• Inventors: Pompignano, Gary, Dyer, David John, Higgs, Stuart
• Primary Examiner(s): Feely, Michael J
• Application Number:
  US13/997,716
• Publication Number:
  US 20130324652A1
• Time in Patent Office: 1,936 Days
• Field of Search: None
• CPC Class Codes: C08G 59/027 obtained by epoxidation of unsaturated precursor, e.g. polymer or monomer
• CPC Class Codes: C08G 59/1422 containing phosphorus
• CPC Class Codes: C08L 63/08 Epoxidised polymerised polyenes
• CPC Class Codes: C09D 147/00 Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Coating compositions based on derivatives of such polymers C09D145/00 takes precedence; based on conjugated diene rubbers C09D109/00 - C09D121/00
• CPC Class Codes: C09D 163/00 Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
• CPC Class Codes: C09D 163/08 Epoxidised polymerised polyenes
• CPC Class Codes: C09D 7/65 macromolecular C09D7/41-C09D7/48 take precedence

Abstract

Coating compositions are disclosed having a non-bisphenol A based film forming resin and an adhesion promoter resin. The coating compositions provide an alternate to epoxy resins that still allow melamine formaldehyde free cure, blush resistance, capability to retort and can withstand hard-to-hold beverages. In some embodiments, the coating compositions are used to coat substrates such as cans and packaging materials for the storage of food and beverages. Substrates can be coated by preparing an adhesion promoter composition by a method including mixing an epoxidized resin and a solvent to form a mixture, adding a phosphoric acid compound to the resulting mixture to form a phosphate ester, adding water to partially hydrolyze the phosphate ester, and adding a neutralizer to form the adhesion promoter resin, followed by blending the adhesion promoter resin with a non-bisphenol A based film forming resin to form a coating composition, and applying the coating composition to the substrate.

Claims

1. A sprayable coating composition for forming a food or beverage contact coating, the coating composition comprising:

a non-bisphenol A based film forming resin;

an adhesion promoter composition present in an amount from about 0.5% to about 10% by weight total solids content, wherein the adhesion promoter composition includes (i) a monophosphate ester hydrolysis product formed from water and a di- or tri-phosphate ester phosphorylation product of an epoxidized resin and a phosphoric acid compound and (ii) a basic neutralizer,

wherein the coating composition is free of bisphenol A.

2. The coating composition of claim 1, wherein the basic neutralizer is present in an amount from about 0.25 to about 1.5 equivalents of the phosphoric acid compound.

3. The coating composition of claim 2, wherein the basic neutralizer is present in an amount from about 0.75 to about 1.0 equivalents of the phosphoric acid compound.

4. The coating composition of claim 1, further comprising a solvent selected from the group consisting of 2-butoxyethanol, butanol, 2-hexoxyethanol, and a combination thereof.

5. The coating composition of claim 1, wherein the basic neutralizer is selected from the group consisting of a tertiary amine, a secondary amine, a primary amine, sodium hydroxide, potassium hydroxide, a carbonate, and a combination thereof.

6. The coating composition of claim 5, wherein the tertiary amine is selected from the group consisting of dimethyl ethanol amine, 2-dimethylamino-2-methylpropanol, tributylamine, and a combination thereof.

7. The coating composition of claim 1, further comprising water.

8. The coating composition of claim 1, wherein the non-bisphenol A based film forming resin is selected from the group consisting of a latex coating composition, a polyester coating composition, a polyolefin coating composition, a polyurethane coating composition, a polyacrylic coating composition, a polycarbonate coating composition, a polyurea coating composition, and a combination thereof.

9. The coating composition of claim 1, wherein the phosphoric acid compound is selected from the group consisting of phosphoric acid, superphosphoric acid, polyphosphoric acid, P₂O₅, and a combination thereof.

10. The coating composition of claim 1, wherein the epoxidized resin is selected from the group consisting of a mono- or a diglycidyl ether of a diol, a mono- or a diglycidyl ester of a diacid, an epoxidized soybean oil, an epoxidized polybutadiene, and a combination thereof.

15. A substrate coated with the coating composition of claim 1.

11. A method of coating a substrate comprising:

a) preparing an adhesion promoter composition including (i) a monophosphate ester hydrolysis product formed from water and a di- or tri-phosphate ester phosphorylation product of an epoxidized resin and a phosphoric acid compound and (ii) a basic neutralizer, by a method comprising;

(1) mixing the epoxidized resin and a solvent to form a mixture;

(2) adding the phosphoric acid compound to the resulting mixture to form the di- or tri-phosphate ester phosphorylation product;

(3) adding water to break up di- or tri-phosphate esters of the di- or tri-phosphate ester phosphorylation product to mono-phosphate esters and to partially hydrolyze the mono-phosphate esters; and

(4) adding the basic neutralizer to form the adhesion promoter composition;

b) blending the adhesion promoter composition with a non-bisphenol A based film forming resin to form a coating composition, wherein the coating composition is free of bisphenol A and wherein the adhesion promoter composition is present in an amount from about 0.5% to about 10% by weight total solids content; and

c) applying the coating composition to the substrate.

12. The method of claim 11, wherein the solvent is selected from the group consisting of 2-butoxyethanol, butanol, 2-hexoxyethanol, and a combination thereof.

13. The method of claim 11, wherein the basic neutralizer is selected from the group consisting of a tertiary amine, a secondary amine, a primary amine, sodium hydroxide, potassium hydroxide, a carbonate, and a combination thereof.

14. The method of claim 13, wherein the tertiary amine is selected from the group consisting of dimethyl ethanol amine, 2-dimethylamino-2-methylpropanol, tributylamine, and a combination thereof.