Bisphenol-A free polyether resins based on phenol stearic acid and coating compositions formed therefrom

Patent metadata

Field	Value
Publication number	US-9540484-B2
Application number	US-201414776209-A
Country	US
Kind code	B2
Filing date	Mar 14, 2014
Priority date	Mar 15, 2013
Publication date	Jan 10, 2017
Grant date	Jan 10, 2017

Abstract

Coating compositions can be prepared from a polyether resin, wherein the smallest difunctional hydroxyl phenyl segment used to form the polyether resin has a molecular weight greater than about 500, and wherein the smallest difunctional hydroxyl phenyl segment used to form the polyether resin does not comprise two or more non-impaired hydroxyl groups attached to two or more different five-membered or six-membered carbon atom rings in a segment having a molecular weight less than about 500. The polyether resin can be prepared by reacting a dihydroxyl compound and/or a diamine compound with a phenol stearic acid compound to produce a diphenol, and reacting the diphenol with a diglycidyl ether compound to form the polyether resin.

First claim

What is claimed is:

1. A bisphenol A-free polyether resin, wherein the smallest difunctional hydroxyl phenyl segment used to form the polyether resin has a molecular weight greater than 500, wherein the smallest difunctional hydroxyl phenyl segment used to form the polyether resin does not comprise two or more non-impaired hydroxyl groups attached to two or more different five-membered or six-membered carbon atom rings in a segment having a molecular weight less than 500, and wherein the polyether resin is prepared by a method comprising
a) reacting a dihydroxyl compound and/or a diamine compound with a phenol stearic acid compound to produce a diphenol; and
b) reacting the diphenol with a diglycidyl ether compound to form the polyether resin.

2. The bisphenol A-free polyether resin of claim 1 , wherein the phenol stearic acid compound comprises 10-(p-hydroxyphenyl)-octadecanoic acid.

3. A coating composition obtained from neutralization of the bisphenol A-free polyether resin of claim 1 .

4. The bisphenol A-free polyether resin of claim 1 , wherein the reaction mixture comprises a crosslinker.

5. The bisphenol A-free polyether resin of claim 4 , wherein the crosslinker comprises a phenolic resin.

6. The bisphenol A-free polyether resin of claim 1 , wherein the dihydroxyl compound comprises 1,4-cyclohexane dimethanol, butane diol, neopentyl glycol, 1,3-cyclohexane dimethanol, ethylene glycol, propylene glycol, 1,3-propane diol, diethylene glycol, a polyether glycol, a polyester, a polycarbonate, a hydroxyl functional polyolefin, or a mixture thereof.

7. The bisphenol A-free polyether resin of claim 1 , wherein the diamine compound comprises a piperazine compound, ethylene diamine, hexamethylene diamine, a fatty diamine, or a mixture thereof.

8. The bisphenol A-free polyether resin of claim 1 , wherein the diglycidyl ether compound comprises the diglycidyl ether of 1,4-cyclohexane dimethanol, butane diol, neopentyl glycol, cyclohexane dimethanol, ethylene glycol, propylene glycol, 1,3-propane diol, trimethylol propane, diethylene glycol, a polyether glycol, or a mixture thereof.

9. The bisphenol A-free polyether resin of claim 1 , wherein the acid number of the polyether resin is less than 30 mg KOH/resin.

10. The bisphenol A-free polyether resin of claim 1 , wherein the polyether resin is prepared in the presence of a catalyst.

11. The bisphenol A-free polyether resin of claim 10 , wherein the catalyst is an acid catalyst.

12. The bisphenol A-free polyether resin of claim 1 , wherein the phenol stearic acid compound is present in a mole ratio of about 1:1 of the hydroxyl or amine functionality.

13. The bisphenol A-free polyether resin of claim 1 , wherein the polyether resin is prepared in the presence of an initiator comprising t-butyl peroxy benzoate, t-butyl peroctoate, dibenzoyl peroxide, 1,1,3,3-tetramethylbutyl-peroxy-2-ethylhexanoate, or a mixture thereof.

14. A coating composition comprising the bisphenol A-free polyether resin of claim 1 .

15. A method of coating a substrate comprising applying the coating composition of claim 14 to the substrate.

16. The coating composition of claim 14 , further comprising a crosslinker.

17. The coating composition of claim 16 , wherein the crosslinker comprises a phenolic resin.

18. A method for preparing bisphenol A-free polyether comprising the steps of:
a) reacting a dihydroxyl compound and/or a diamine compound with a phenol stearic acid compound to produce a diphenol; and
b) reacting the diphenol with a diglycidyl ether compound to form the polyether resin.

19. The method of claim 18 , wherein the phenol stearic acid compound comprises 10-(p-hydroxyphenyl)-octadecanoic acid.

20. A coating composition comprising a bisphenol A-free polyether resin, wherein the smallest difunctional hydroxyl phenyl segment used to form the polyether resin has a molecular weight greater than 500, wherein the smallest difunctional hydroxyl phenyl segment used to form the polyether resin does not comprise two or more non-impaired hydroxyl groups attached to two or more different five-membered or six-membered carbon atom rings in a segment having a molecular weight less than 500.

21. The coating composition of claim 20 , further comprising a crosslinker.

22. The coating composition of claim 21 , wherein the crosslinker comprises phenolic resin.

23. A method of coating a substrate comprising applying the coating composition of claim 20 to the substrate.

Assignees

• Akzo Nobel Coatings Int Bv
• Si Group Inc

Inventors

• Craun Gary Pierce
• Bode Daniel
• Banach Timothy Edward
• Robideau Gary Joseph
• Howard Leigh Scott

Classifications

• C08G2650/56

  Polyhydroxyethers, e.g. phenoxy resins · CPC title

• C08G59/62

  Alcohols or phenols · CPC title

• C08G59/182

  using pre-adducts of epoxy compounds with curing agents · CPC title

• C08G65/48 Primary

  Polymers modified by chemical after-treatment · CPC title

• C08G59/621

  Phenols · CPC title