Glycidyl esters of α, α branched acids from renewable sources and formulations thereof
AssigneeHexion Inc.
InventorsCédric Le Fevere De Ten Hove, Christophe Steinbrecher, Robert Van't Sand, Denis Heymans, Jimmy Antonius Van Rijn, Robin Christiaan Martens
Life of this patent
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Abstract
The invention relates to compositions of α,α-branched alkane carboxylic acids glycidyl esters which derived from rosin and or hydrogenated rosin reacted with an epihalohydrin. The above glycidyl esters compositions can be used for example, as monomer in binder compositions for paints or adhesives, as reactive diluent or as acid scavenger. This invention is also about the uses of rosin and or hydrogenated rosin glycidyl ester in combinations with polyester polyols, or acrylic polyols, or polyether polyols.
Claims14
A process for the manufacture of glycidyl esters of rosin and/or hydrogenated rosin, comprising
- (a) reacting a rosin acid with a epoxyalkyl halide in a 1.01-20 molar excess, in the presence of water and a water-miscible solvent, and in the presence of a catalyst, in an amount of at most 45 mol % of the molar amount of the rosin acid, at a temperature in the range of from 30 to 110° C. during a period of time in the range of from 0.5 to 2.5 hr,
- (b) adding an alkali metal hydroxide or alkali metal alkanolate up to a molar ratio in the range of from 0.9:1 to 1.2:1 as to the rosin acid and reacting at a temperature of from 0 to 80° C. to prepare a reaction mixture,
- (c) distilling the reaction mixture to remove the excess epoxyalkyl halide solvent and water formed, and
- (d) removing an alkali metal halide salt by washing the obtained glycidyl ester with water to complete the dehydrohalogenation.
A process for the manufacture of glycidyl esters of rosin and/or hydrogenated rosin, comprising
- (a) reacting a rosin acid with an epoxyalkyl halide in a 1.01-20 molar excess, in the presence of water, and in the presence of a catalyst, in an amount of at most 45 mol % of the molar amount of the rosin acid, at a temperature in the range of from 30 to 110° C. during a period of time about 7 hr,
- (b) adding an alkali metal hydroxide or alkali metal alkanolate up to a molar ratio of about 1.24:1 as to the rosin acid and reacting at a temperature of from 0 to 80° C. to prepare a reaction mixture,
- and
- (c) removing an alkali metal halide salt by washing the obtained glycidyl ester with water to complete the dehydrohalogenation.
Dependencies are inferred from the claim text.