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