Methods of preparing compositions for containers and other articles and methods of using same

• US 10,113,027 B2
• Filed: 10/11/2016
• Issued: 10/30/2018
• Est. Priority Date: 04/14/2014
• Status: Active Grant

• Current Assignee: Swimc, LLC (Sherwin-Williams Company)
• Original Assignee: Swimc, LLC (Sherwin-Williams Company)
• Inventors: Niederst, Jeffrey, O'Brien, Robert M., Romagnoli, Kevin, Von Maier, Mark S., Deng, Lan, Evans, Richard H, Santure, David J., Prouvost, Benoit
• Primary Examiner(s): Fang, Shane
• Application Number:
  US15/290,765
• Publication Number:
  US 20170096521A1
• Time in Patent Office: 749 Days
• CPC Class Codes: B65D 1/12 Cans, casks, barrels, or drums
• CPC Class Codes: B65D 25/14 Linings or internal coatings of containers made by folding or erecting blanks made of paper B65D5/56 ; linings for domestic water storage heaters F24H1/183
• CPC Class Codes: C08F 212/08 Styrene
• CPC Class Codes: C08F 220/06 Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
• CPC Class Codes: C08F 220/14 Methyl esters , e.g. methyl (meth)acrylate
• CPC Class Codes: C08F 220/1802 C2-(meth)acrylate, e.g. ethyl (meth)acrylate
• CPC Class Codes: C08F 283/10 on to polymers containing more than one epoxy radical per molecule C08F283/004 takes precedence
• CPC Class Codes: C08F 4/04 Azo-compounds
• CPC Class Codes: C08G 2150/90 Compositions for anticorrosive coatings
• CPC Class Codes: C08G 2390/40 Inner coatings for containers
• CPC Class Codes: C08G 2650/56 Polyhydroxyethers, e.g. phenoxy resins
• CPC Class Codes: C08G 59/063 with epihalohydrins
• CPC Class Codes: C08G 59/245 aromatic
• CPC Class Codes: C08G 59/621 Phenols
• CPC Class Codes: C08G 59/686 containing nitrogen
• CPC Class Codes: C08L 71/00 Compositions of polyethers obtained by reactions forming an ether link in the main chain of polyacetals C08L59/00; of epoxy resins C08L63/00; of polythioether-ethers C08L81/02; of polyether-sulfones C08L81/06; Compositions of derivatives of such polymers
• CPC Class Codes: C09D 163/00 Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
• CPC Class Codes: C09D 171/00 Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain based on polyacetals C09D159/00; based on epoxy resins C09D163/00; based on polythioether-ethers C09D181/02; based on polyethersulfones C09D181/06; Coating compositions based on derivatives of such polymers
• CPC Class Codes: C09D 5/08 Anti-corrosive paints

Abstract

This invention provides a polymer, which is preferably a polyether polymer. The polymer may be uses in coating compositions. Containers and other articles comprising the polymer and methods of making such containers and other articles are also provided. The invention further provides compositions including the polymer (e.g., powder coatings), which have utility in a variety of coating end uses, including, for example, valve and pipe coatings.

Claims

1. A method of making a high molecular weight polyether polymer, comprising the step of reacting ingredients including:

(i) a nitrogen-containing catalyst having at least one bridgehead Nitrogen atom;

(ii) a diepoxide compound; and

(iii) a hindered polyhydric phenol compound having an atom or group with an atomic weight of at least 15 Daltons in an ortho position relative to an oxygen atom on a phenol ring;

wherein the polyether polymer;

(a) includes at least 25% by weight of aryl or heteroaryl groups and (b) is substantially free of bound bisphenol A, bisphenol F, bisphenol S, polyhydric phenols having estrogenic activity greater than or equal to that of bisphenol S, and epoxides thereof.

2. The method of claim 1, wherein the phenol compound has the below Formula (III):

3. The method of claim 2, wherein the catalyst has a pka of at least 9.

4. The method of claim 2, wherein the catalyst comprises a polycyclic amidine base catalysts or an azabicycloalkane or mixtures thereof.

5. The method of claim 4, wherein the catalyst is selected from the group consisting of 1,5,7-Triazabicyclo(4.4.0)dec-5-ene;

7-Methyl-1,5,7-triazabicyclo(4.4.0)dec-5-ene;

1,8-diazabicyclo[5.4.0]undec-7-ene;

1,5-diazabicyclo[4.3.0]non-5-ene;

1-Azabicyclo[2.2.2]octane; and

similar compounds.

6. The method of claim 2, wherein the catalyst is present in an amount of from 0.01 to 1% by weight, based on the total polymer weight.

7. The method of claim 2, wherein the reaction is carried out at a temperature between 120 and 200°

C. for less than 24 hours.

8. The method of claim 2, wherein the polyether polymer includes at least 45% by weight of phenylene groups and has a glass transition temperature of at least 60°

C.

9. The method of claim 2, wherein the phenol compound comprises a phenol of Formula (III), and wherein t and n are each 1 and R² is an organic group having 8 or more carbon atoms.

10. The method of claim 2, wherein the phenol compound comprises a phenol of Formula (III), and wherein t and n are each 1 and each depicted hydroxyl group in Formula (III) is located at a para position relative to R².

11. The method of claim 2, wherein the phenol compound comprises a phenol of Formula (III), and wherein the phenol of Formula (III) has an atomic weight of less than 600 Daltons and constitutes at least 30% by weight of the polyether polymer.

12. The method of claim 2, wherein the diepoxide compound is non-genotoxic and is derived from a dihydric phenol that that exhibits a log Relative Proliferative Effect value in the MCF-7 cell proliferation assay of less than −

3.

13. The method of claim 2 wherein each phenylene group depicted in Formula (III) includes R¹ groups attached to the phenol ring at both ortho positions relative to the depicted oxygen atom on the phenol ring.

14. The method of claim 1 wherein the hindered polyhydric phenol compound comprises 4,4′

-methylenebis(2,6-dimethylphenol).