WATER-BASED HYDROGEL, AND REACTION PRODUCT OF ISOSORBIDE EPOXIDE AND AMINES

Abstract

The invention relates to a hydrogel based on water, on hydrosoluble monomeric or polymeric isosorbide epoxide and on hydrosoluble amine, to the method for preparing same and to the use thereof.

Claims

1-9. (canceled)

10. A hydrogel based on water and on the reaction product of hydrosoluble monomeric or polymeric isosorbide epoxide and of hydrosoluble amine selected from a hydrosoluble diamine, triamine or polyamine.

11. The hydrogel according to claim 10, wherein the hydrosoluble monomeric or polymeric isosorbide epoxide has the following formula (I): ##STR00002## Where n is an integer from 0 to 300, preferably from 0 to 10, and more preferentially from 0 to 5.

12. The hydrogel according to claim 10, wherein the hydrosoluble diamine, triamine or polyamine is selected from lysine, arginine, asparagine, glutamine, isophorone diamine, diaminodiphenylsulfone, hexamethylene diamine, m-xylenediamine and polyetheramines such as Jeffamine D-230, Jeffamine T-403 and mixtures thereof.

13. The hydrogel according to claim 10, wherein the ratio of hydrosoluble monomeric or polymeric isosorbide epoxide equivalents to the number of N—H functions of the hydrosoluble amine is between 1:5 and 5:1, preferably between 1:2 and 2:1, and more preferentially 1:1.

14. The hydrogel according to claim 10, having a moisture content of 50 to 99%.

15. The hydrogel according to claim 10, further comprising a water-soluble active ingredient, preferably an odorizing molecule, a cosmetic active ingredient or a hydrosoluble pharmaceutical active ingredient and more preferentially isosorbide.

16. A method for preparing a hydrogel as defined in claim 10, comprising the following steps: 1) Mixing the hydrosoluble monomeric or polymeric isosorbide epoxide with a hydrosoluble amine, 2) Adding water to the previous mixture, 3) Mixing until a translucent liquid is obtained, and 4) Leaving to react.

17. The method for preparing a hydrogel according to claim 16, wherein step 2) comprises adding an active ingredient.

18. A use of a hydrogel as defined in claim 10 in the medical, cosmetics, agricultural or optical fields, in the field of water treatment, hygiene products, in separation technology or in the energy sector.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

[0058] Other features, details and advantages of the invention will appear from reading the following detailed description, and by analyzing the appended drawings, in which:

[0059] FIG. 1

[0060] FIG. 1 is a diagram showing the kinetics of the concentration of isosorbide salted out into water from the preparation of example 2.

EXAMPLES

[0061] Reagents:

Isosorbide epoxide: Roquette.

Lysine: Ajinomoto.

[0062] Isosorbide as active ingredient: Roquette.
Water: Demineralized water.

Example 1: Preparation of a Hydrogel Containing 50% by Weight of Water

[0063] 5 g of isosorbide epoxide (EEW=180 g/eq) (i.e. the product of formula (I) with R═H and n=0) are mixed with 1.03 g of lysine. 6.03 g of demineralized water are then added. Mixing is finally carried out in order to obtain a homogeneous preparation. The mixture is poured into a mold, then left to react at ambient temperature. The hydrogel is obtained after 72 h. The hydrogel thus obtained is removed from the mold.

Example 2: Preparation of a Hydrogel Containing 50% by Weight of Water, Further Comprising Isosorbide as Active Ingredient

[0064] 5 g of isosorbide epoxide (EEW=180 g/eq) are mixed with 1.03 g of lysine. 6.03 g of a 20% by weight aqueous solution of isosorbide are then added. Mixing is finally carried out in order to obtain a homogeneous preparation. The mixture is poured into a mold, then left to react at ambient temperature. The hydrogel is obtained after 72 h. The hydrogel containing the active ingredient thus obtained is removed from the mold.

Example 3: Salting-Out Test of the Preparation of Example 2

[0065] The hydrogel containing the isosorbide obtained according to example 2 is subsequently submerged in a given volume of water. The content of isosorbide salted out is determined by gas chromatography in the form of trimethylsilyl derivatives and quantified by the internal calibration method as described below:

[0066] Name of apparatus: CPG, type Varian 3800 or Bruker 450 equipped with a split-splitless injector; a FID detector; a DB1 capillary column (J&W scientific ref 123-1033; 30 m in length; 0.32 mm in internal diameter; 1 micron film thickness.

[0067] Analysis conditions:

Column temperature: temperature program starting from injection, from 140° to 250° C. at a rate of 3° C./minute, then up to 300° C. at a rate of 10° C./min.
Injector temperature: 300° C.
Detector temperature: 300° C.

Pressure: 10 psi

Vector gas: Helium

[0068] Injection mode: split, with imperative “liner split”
Flow rate of split: 80 ml/minute
Hydrogen flow rate: 30 ml/minute
Air flow rate: 400 ml/minute
Volume injected: 1 microliter
Approximately precisely 1 g of product and 50 mg of internal standard (α-methyl-D-glucopyranoside) are weighed into a 100 ml beaker. Approximately 50 ml of pyridine (4-1) are added. This is left under magnetic stirring until complete dissolution is achieved.
1 ml of the solution, 1 ml of pyridine and 0.3 ml of BSTFA are deposited in a 2 ml dish with screw-on lid. The lid is closed. The container is agitated. It is left in a dry bath temperature controlled to 70° C. for 30 minutes, before injecting 1 microliter.

[0069] The kinetics of concentration of isosorbide salted-out into water is given in FIG. 1, for which the threshold of 2.5% corresponds to the maximum concentration which can be implemented in this test in light of the amount of isosorbide introduced and the known volume of water used for the salting out step.

[0070] This test shows that the hydrogel formed has a capacity for salting out isosorbide. The latter is completely salted out after 4 h.

[0071] As a result, the inventors have discovered that the hydrogel according to the invention makes it possible to salt out active ingredients, with this salting out time being adjustable based on the formulation of the hydrogel.

[0072] The hydrogel according to the invention, obtained according to a simple preparation method, is a good alternative to hydrogels based on polymers of fossil origin. Said hydrogel according to the invention has good water absorption, making it possible to advantageously salt out the active ingredient it contains. Due to these properties, the hydrogel according to the invention can therefore be used in various applications, particularly in the medical, cosmetics, agricultural or optical fields, in the field of water treatment, hygiene products, in separation technology or in the energy sector.