Epoxy monomers from sucrose
AssigneeHawaiian Sugar Planters' Association
InventorsNavzer D. Sachinvala, Morton H. Litt
Life of this patent
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Abstract
A method for producing sucrose-based epoxy monomers having one to eight epoxy groups per molecule of sucrose, which comprises reacting a mixture comprising: a sucrose monomer having an allyl-containing group on at least one of the hydroxyl groups, and a reagent or catalyst selected from molybdenum, tungsten, vanadium, titanium and peracid, in the presence of hydrogen peroxide or a derivative thereof, in relative amounts sufficient to produce a sucrose-based epoxy monomer. Monomers thus produced are also provided. The sucrose-based epoxy monomers can be cured to produce a sucrose-based epoxy resin. Such resins are useful, for example, as adhesives, composites and coatings.
Claims23
A method for producing a saccharide-based epoxy monomer having one to eight epoxy groups per molecule of saccharide, which comprises reacting a mixture comprising:
- (a) a monomer comprising an allyl-containing group which is bonded to at least one primary or secondary hydroxyl group on a saccharide, and
- (b) an acidic or metallic catalyst in the presence of an oxidizing agent,
- in relative amounts sufficient to produce a saccharide-based epoxy monomer having one to seven epoxy groups per molecule of saccharide.
A method for producing sucrose-based epoxy monomers having one to eight epoxy groups per molecule of sucrose, which comprises reacting a mixture comprising:
- (a) a sucrose monomer having an allyl-containing group on at least one of the hydroxyl groups;
- and
- (b) an acidic or metallic catalyst in the presence of an oxidizing agent,
- in relative amounts sufficient to produce a sucrose-based epoxy monomer.
A method for preparing an epoxy-allylsucrose or epoxy-crotylsucrose monomer comprising:
- (a) treating sucrose with a suspension of dimethylsulfoxide and sodium hydride at a temperature of between about 0.degree. and about 10.degree. C. to obtain a sucrose mixture;
- (b) stirring the sucrose mixture for between about 30 and about 80 minutes while allowing the temperature to attain between about 35.degree. to about 40.degree. C.;
- (c) cooling the sucrose mixture to between about 0.degree. and about 10.degree. C.;
- (d) treating the sucrose mixture with allyl or crotyl chloride;
- (e) stirring the mixture from (d) for a time sufficient for the sucrose to react with the allyl or crotyl chloride;
- (f) recovering octa-O-allylsucrose or octa-O-crotylsucrose;
- (g) adding an acidic or metallic catalyst in the presence of an oxidizing agent to the octa-O-allylsucrose or octa-O-crotylsucrose in relative amounts sufficient to produce an epoxy-allylsucrose or epoxy-crotylsucrose monomer;
- and
- (h) recovering the epoxy-allylsucrose or epoxy-crotylsucrose monomer.
Dependencies are inferred from the claim text.