Acrylic polyol resins compositions
View Patent ↗The invention relates to compositions of hydroxyl functional acrylic resins (acrylic polyols) comprising a mixture of α,α-branched alkane carboxylic glycidyl esters derived from butene oligomers characterized in that the sum of the concentration of the blocked and of the highly branched isomers is at least 50%, preferably above 60% and most preferably above 75% on total composition.
1. A hydroxyl functional acrylic resin composition prepared from a mixture of α,α-branched alkane carboxylic glycidyl esters wherein a sum of the concentration of blocked and of highly branched isomers is at least 50 wt % based on the total weight of the mixture and wherein the mixture of α,α-branched alkane carboxylic glycidyl esters is selected from the group consisting of 2,2-dimethyl 3,3-dimethyl pentanoic acid glycidyl ester, 2-methyl 2-isopropyl 3-methyl butanoic acid glycidyl ester, 2-methyl 2-ethyl 3,3-dimethyl butanoic acid glycidyl ester, 2,2-dimethyl 3-methyl 4-methyl pentanoic acid glycidyl ester, 2,2-dimethyl 4,4-dimethyl pentanoic acid glycidyl ester, and combinations of any two or more thereof.
2. The composition of claim 1 wherein the mixture of α,α-branched alkane carboxylic glycidyl esters is based on a neononanoic (C9) acid mixture wherein the sum of the concentration of the blocked and of the highly branched isomers is at least 50 wt % based on the total weight of the mixture.
3. The composition of claim 1 wherein the mixture of α,α-branched alkane carboxylic glycidyl esters comprises 2,2-dimethyl 3,3-dimethyl pentanoic acid glycidyl ester, 2-methyl 2-isopropyl 3-methyl butanoic acid glycidyl ester and 2-methyl 2-ethyl 3,3-dimethyl butanoic acid glycidyl ester in an amount above 10 wt % based on the weight of the mixture.
4. The composition of claim 3 wherein the mixture of α,α-branched alkane carboxylic glycidyl esters comprises 2,2-dimethyl 3,3-dimethyl pentanoic acid glycidyl ester, 2-methyl 2-isopropyl 3-methyl butanoic acid glycidyl ester and 2-methyl 2-ethyl 3,3-dimethyl butanoic acid glycidyl ester in an amount above 15 wt % based on the total weight of the mixture.
5. The composition of claim 3 wherein the mixture of α,α-branched alkane carboxylic glycidyl esters comprises 2,2-dimethyl 3,3-dimethyl pentanoic acid glycidyl ester, 2-methyl 2-isopropyl 3-methyl butanoic acid glycidyl ester and 2-methyl 2-ethyl 3,3-dimethyl butanoic acid glycidyl ester in an amount above 25 wt % based on the total weight of the mixture.
6. The composition of claim 2 wherein the sum of the concentration of the blocked isomers and of the highly branched isomers is above 60 wt % based on the total weight of the mixture.
7. The composition of claim 2 wherein the sum of the concentration of the blocked isomers and of the highly branched isomers is above 75 wt % based on the total weight of the mixture.
8. The composition of claim 1 wherein the mixture of α,α-branched alkane carboxylic glycidyl esters comprises 2,2-dimethyl 3,3-dimethyl pentanoic acid glycidyl ester, 2-methyl 2-isopropyl 3-methyl butanoic acid glycidyl ester, 2-methyl 2-ethyl 3,3-dimethyl butanoic acid glycidyl ester, 2,2-dimethyl 3-methyl 4-methyl pentanoic acid glycidyl ester and 2,2-dimethyl 4,4-dimethyl pentanoic acid glycidyl ester in an amount above 40 wt % based on the weight of the mixture.
9. The composition of claim 8 wherein the mixture of α,α-branched alkane carboxylic glycidyl esters 2,2-dimethyl 3,3-dimethyl pentanoic acid glycidyl ester, 2-methyl 2-isopropyl 3-methyl butanoic acid glycidyl ester, 2-methyl 2-ethyl 3,3-dimethyl butanoic acid glycidyl ester, 2,2-dimethyl 3-methyl 4-methyl pentanoic acid glycidyl ester and 2,2-dimethyl 4,4-dimethyl pentanoic acid glycidyl ester in an amount above 50w t % based on the weight of the mixture.
10. The composition of claim 8 wherein the mixture of α,α-branched alkane carboxylic glycidyl esters 2,2-dimethyl 3,3-dimethyl pentanoic acid glycidyl ester, 2-methyl 2-isopropyl 3-methyl butanoic acid glycidyl ester, 2-methyl 2-ethyl 3,3-dimethyl butanoic acid glycidyl ester, 2,2-dimethyl 3-methyl 4-methyl pentanoic acid glycidyl ester and 2,2-dimethyl 4,4-dimethyl pentanoic acid glycidyl ester in an amount above 60 wt % based on the weight of the mixture.
11. The composition of claim 1 wherein the mixture of α,α-branched alkane carboxylic glycidyl esters comprises 2-methyl 2-ethyl hexanoic acid glycidyl ester in an amount of below 40 wt % based on the weight of the mixture.
12. The composition of claim 11 wherein the mixture of α,α-branched alkane carboxylic glycidyl esters comprises 2-methyl 2-ethyl hexanoic acid glycidyl ester in an amount of below 30 wt % based on the weight of the mixture.
13. The composition of claim 11 wherein the mixture of α,α-branched alkane carboxylic glycidyl esters comprises 2-methyl 2-ethyl hexanoic acid glycidyl ester in an amount of below 20 wt % based on the weight of the mixture.
14. A process to prepare the hydroxyl functional acrylic resin composition of claim 1 comprising incorporating the mixture of α,α-branched alkane carboxylic glycidyl esters comprising epoxy groups into a hydroxyl functional acrylic resins by the reaction of the epoxy group with a carboxylic acid group of ethylene carboxylic acid compounds from hydroxyl ethylene carboxylate ester monomers which are then reacted with one or more unsaturated monomers via a radical polymerization reaction, in one step or more.
15. The composition of claim 1 having a calculated hydroxyl value between 50 and 180 mgKOH/g on solids, or a number average molecular weight (Mn) between 2500 and 50000 Dalton measured according to polystyrene standard.
16. A binder composition useful for a coating composition comprising the hydroxyl functional acrylic resin composition of claim 1 .
17. A metal or plastic substrate coated with a coating composition comprising the binder composition of the claim 16 .
18. The hydroxyl functional acrylic resin composition of claim 1 prepared in presence of a polyester polyol.
19. The composition of claim 1 wherein the sum of the concentration of the blocked isomers and of the highly branched isomers is above 60 wt % based on the total weight of the mixture.
20. The composition of claim 1 wherein the sum of the concentration of the blocked isomers and of the highly branched isomers is above 75 wt % based on the weight of the mixture.
21. The composition of claim 1 wherein the mixture of α,α-branched alkane carboxylic glycidyl esters is derived from butene oligomers.