Process for producing isohexide glycidyl ethers, products thus obtained, and uses thereof

Patent metadata

Field	Value
Publication number	US-10174152-B2
Application number	US-201515113078-A
Country	US
Kind code	B2
Filing date	Jan 21, 2015
Priority date	Jan 21, 2014
Publication date	Jan 8, 2019
Grant date	Jan 8, 2019

Abstract

A process for producing bis-anhydrohexitol ether compositions and in particular isohexide glycidyl ether compositions, one of the originalities of which is azeotropic distillation carried out under reduced pressure. Such compositions are used to produce epoxy resins, the function thereof being to form a three-dimensional macromolecular network. The compositions obtained according to the process are rich in diepoxy derivatives of isosorbide to the detriment of monoepoxy derivatives, only the first participating in the formation of the three-dimensional network. The crosslinking density is therefore increased, thereby making it possible to obtain a material which is more chemically resistant and mechanically stronger and which has a higher glass transition temperature (Tg), compared with the same materials obtained with bis-anhydrohexitol ether compositions according to the prior art.

First claim

The invention claimed is:

1. A process for producing bis-anhydrohexitol ether compositions, comprising the following steps:
a) bringing a dianhydrohexitol into contact with an organic halide,
b) placing the resulting mixture of dianhydrohexitol and organic halide under vacuum so as to obtain a negative pressure of between 100 mbar and 1000 mbar,
c) heating the mixture under vacuum at a temperature of between 50° C. and 120° C. and thus carrying out an azeotropic distillation,
d) then adding to said mixture a basic reagent for a period of between 1 hour and 10 hours and then continuing the azeotropic distillation,
e) recovering the bis-anhydrohexitol ether composition after a filtration step, concentration of the filtering and optionally a purification step.

2. The process as claimed in claim 1 , wherein the dianhydrohexitol comprises one of isosorbide, isomannide and isoidide.

3. The process as claimed in claim 1 , wherein the organic halide is chosen from epibromohydrin, epifluorohydrin, epiiodohydrin and epichlorohydrin.

4. The process as claimed in claim 1 , wherein the basic reagent is chosen from lithium hydroxide, potassium hydroxide, calcium hydroxide and sodium hydroxide optionally in the form of an aqueous solution.

5. The process as claimed in claim 1 , wherein a phase-transfer catalyst is added during step a).

6. The process as claimed in claim 5 , wherein the phase-transfer catalyst is chosen from tetrabutylammonium halides or sulfates.

7. The process as claimed in claim 5 , wherein the amount of phase-transfer catalyst is between 0.01% and 5% by weight relative to the dianhydrohexitol.

8. A bis-anhydrohexitol ether composition obtained according to the process of claim 1 .

9. The process as claimed in claim 5 , wherein the phase-transfer catalyst is hydrogen sulfate.

Assignees

• Roquette Freres

Inventors

• Buffe Clothilde
• Dolenec Amelie
• Ibert Mathias

Classifications

• C07D493/04 Primary

  Ortho-condensed systems · CPC title

• C09J4/00

  Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16} · CPC title

• C08G59/5026

  cycloaliphatic · CPC title

• C07D407/14

  containing three or more hetero rings · CPC title

• C08G59/26 Primary

  heterocyclic · CPC title