Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
  • C08J3/00—Processes of treating or compounding macromolecular substances
  • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
  • C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
  • C08J3/075—Macromolecular gels
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/74—Synthetic polymeric materials
  • A61K31/765—Polymers containing oxygen
  • A61K31/77—Polymers containing oxygen of oxiranes
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
  • A61K8/04—Dispersions; Emulsions
  • A61K8/042—Gels
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
  • A61K8/86—Polyethers
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K9/00—Medicinal preparations characterised by special physical form
  • A61K9/0012—Galenical forms characterised by the site of application
  • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K9/00—Medicinal preparations characterised by special physical form
  • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
  • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
  • C08G59/22—Di-epoxy compounds
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
  • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
  • C08G59/22—Di-epoxy compounds
  • C08G59/26—Di-epoxy compounds heterocyclic
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
  • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
  • C08G59/32—Epoxy compounds containing three or more epoxy groups
  • C08G59/3236—Heterocylic compounds
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
  • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
  • C08G59/50—Amines
  • C08G59/504—Amines containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/10—General cosmetic use
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
  • C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins

Definitions

• the present invention relates to a hydrogel and more particularly to a water-based hydrogel, and to the reaction product of water-soluble monomeric or polymeric isosorbide epoxide and water-soluble amine, its method of preparation and its use.
• Hydrogels are a class of products which consist of a reversible physical or irreversible chemical network in which water can be trapped. These hydrogels are insoluble in water. Hydrogels are highly absorbent polymeric materials and are used in a variety of applications.
• polymer hydrogels in the literature contain polyester, polyurethane or silicone groups.
• Epoxies have been little studied in the manufacture of gels and even less in the manufacture of hydrogels. However, this involves simple and quantitative reactions at low temperatures. In addition, it is very insensitive to the presence of water, oxygen or impurities. Epoxies also exhibit excellent mechanical and thermal properties. Many epoxies and amines are available, but very few are soluble in water.
• WO2008079440A2 describes a process for preparing a superelastic epoxy-based hydrogel by reaction between polyetheramine and a polyglycidyl ether.
• hydrogels are their poor mechanical properties.
• the proportion of rigid monomer or the degree of crosslinking can be increased.
• the material becomes more fragile and has a reduced absorption capacity.
• hydrogels prepared from epoxy polymer of natural and non-fossil origin having improved mechanical properties while being easy to obtain and retaining facilitated water absorption.
• hydrogel based on polymers of natural and non-fossil origin such as isosorbide epoxide polymers or monomers, exhibited such characteristics.
• the rigid bicyclic structure of the isosorbide epoxide makes it possible to improve the mechanical properties of the hydrogels which are prepared with these polymers or monomers of isosorbide epoxide, while keeping very good characteristics. absorption of water thanks to the hydrophilic nature of these compounds.
• thermoset epoxy polymers and, more specifically, thermoset polymers obtained from renewable resources.
• a first object of the present invention relates to a water-based hydrogel, and to the reaction product of isosorbide epoxide monomer or water-soluble polymer and water-soluble amine chosen from a di-, tri-, or polyamine water soluble.
• a second object of the present invention relates to a process for preparing a hydrogel according to the invention comprising the following steps:
• a final object of the present invention relates to the use of the hydrogel according to the invention in the medical, cosmetic, agricultural, optical field, in the field of water treatment, hygiene products, in separation technology or in energy.
• water-based hydrogel and the reaction product of water-soluble monomeric or polymeric isosorbide epoxide and water-soluble amine selected from a water-soluble di-, tri-, or polyamine.
• water-based hydrogel is meant a material consisting of a three-dimensional network obtained by crosslinking of polymer chains in which water or an oil-in-water emulsion can be trapped.
• the three-dimensional cross-linked network, which is insoluble, is referred to in the following as the matrix of the hydrogel.
• the hydrogel matrix is composed of monomeric or polymeric isosorbide epoxide having the following formula (I): formula (I) [0022] where n is an integer from 0 to 300, in particular from 0 to 10, and more particularly from 0 to 5.
• the epoxide according to formula (I) can be manufactured according to the process described in application WO 2015/110758 A1.
• Isosorbide epoxide can be a mixture of different isosorbide epoxides which differ from each other by the R substituent and / or the n index.
• the index n can range from 0 to 300, in particular be equal to 290, 280, 270, 260, 250, 240, 230, 220, 210, 200, 190, 180, 170, 160, 150, 140 , 130, 120, 110, 100, 90, 80, 70, 60, 50, 40, 30, 20, 10, 9, 8, 7, 6, 5, 4, 3, 2, 1.
• the index n can be between 0 and 290, 0 and 280, 0 and 270, 0 and 260, 0 and 250, 0 and 240, 0 and 230, 0 and 220, 0 and 210, 0 and 200, 0 and 190, 0 and 180, 0 and 170, 0 and 160, 0 and 150, 0 and 140, 0 and 130, 0 and 120, 0 and 110, 0 and 100, 0 and 90, 0 and 80, 0 and 70, 0 and 60, 0 and 50, 0 and 40, 0 and 30, 0 and 20, 0 and 10, 0 and 9, 0 and 8, 0 and 7, 0 and 6, 0 and 5.
• the index n can be between 1 and 290, 1 and 280, 1 and 270, 1 and 260, 1 and 250, 1 and 240, 1 and 230, 1 and 220, 1 and 210, 1 and 200,
• the index n can be between 2 and 290, 2 and 280, 2 and 270, 2 and 260, 2 and 250, 2 and 240, 2 and 230, 2 and 220, 2 and 210, 2 and 200,
• the index n can be between 3 and 290, 3 and 280, 3 and 270, 3 and 260, 3 and 250, 3 and 240, 3 and 230, 3 and 220, 3 and 210, 3 and 200,
• the index n can be between 4 and 290, 4 and 280, 4 and 270, 4 and 260, 4 and 250, 4 and 240, 4 and 230, 4 and 220, 4 and 210, 4 and 200,
• the index n can be between 5 and 290, 5 and 280, 5 and 270, 5 and 260, 5 and 250, 5 and 240, 5 and 230, 5 and 220, 5 and 210, 5 and 200,
• the index n can be between 10 and 290, 10 and 280, 10 and 270, 10 and 260, 10 and 250, 10 and 240, 10 and 230, 10 and 220, 10 and 210, 10 and 200, 10 and 190, 10 and 180, 10 and 170, 10 and 160, 10 and 150, 10 and 140, 10 and 130, 10 and 120, 10 and 110, 10 and 100, 10 and 90, 10 and 80, 10 and 70, 10 and 60, 10 and 50, 10 and 40, 10 and 30, 10 and 20.
• the monomeric or polymeric isosorbide epoxide of formula (I) is crosslinked using a crosslinking agent.
• the crosslinking agent is a water soluble amine selected from a water soluble di-, tri-, or polyamine.
• the water-soluble amine is chosen from amino acids such as lysine, arginine, asparagine, glutamine, isophorone diamine, diaminodiphenylsulfone, hexamethylene diamine, m-xylendiamine and polyetheramines such as diaminopolypropylene glycol (Jeffamine® D-230) and trimethylolpropane poly (oxypropylene) triamine (Jeffamine® T-403) as well as mixtures thereof.
• amino acids such as lysine, arginine, asparagine, glutamine, isophorone diamine, diaminodiphenylsulfone, hexamethylene diamine, m-xylendiamine and polyetheramines such as diaminopolypropylene glycol (Jeffamine® D-230) and trimethylolpropane poly (oxypropylene) triamine (Jeffamine® T-403) as well as mixtures thereof.
• the ratio of epoxide equivalent of isosorbide monomer or water-soluble polymer to the number of NH functions of the water-soluble amine is between 1: 5 and 5: 1, preferably between 1: 2 and 2: 1 and more preferably 1: 1, the optimum ratio lying between 2: 1 and 1: 2 with a maximum density for a ratio of 1: 1.
• water demineralized water.
• the hydrogel has a degree of hydration of 50 to 99%.
• the hydration level is measured using the TGA: TG209F1 iris device from NETZSCH, according to the following method:
• a few mg of product are placed in an alumina crucible.
• a heating ramp is carried out from 25 ° C. to 300 ° C. at 10 ° C./min under inert gas (nitrogen with a flow rate of 40 ml / min).
• the hydrogel When the hydrogel is in the presence of a stimulus to which it is sensitive, it swells or contracts. Mention may be made, as type of stimulus, of pH, temperature, enzymes or other biochemical agents. It can also swell or shrink over time, depending on the environment in which it is found.
• the hydrogel according to the invention has the following properties:
• the mechanical properties and the crosslinking density of the hydrogel can be adjusted during the preparation process of the hydrogel.
• the hydrogels can have different physical forms, such as for example:
• the hydrogel is biocompatible.
• the hydrogel further comprises an active. All the characteristics of the hydrogel described above also apply to the hydrogel comprising an active.
• active is meant any body, material, or substance, pure or as a mixture, of a chemical, biochemical or living nature, having a technical effect or function, in a field of industry, in particular medical, cosmetic, agricultural, optical, in the field of water treatment, hygiene products, in separation technology or in energy etc.
• the active ingredient can be a pharmaceutical active principle which would be released under certain conditions.
• the active ingredient can be a skin tightening molecule.
• the active agent can be a molecule released on the surface of the eye when wearing a contact lens.
• the active ingredient can be a decontaminant.
• the active ingredient can be a decontaminant.
• the active ingredient When the hydrogel is water-based, the active ingredient is dissolved in water. The solution is then captured by the meshes of the network and is finally released by syneresis.
• the hydrogel When the hydrogel is based on an oil-in-water emulsion, the active ingredient is dissolved in the oily, discontinuous phase, emulsion. The emulsion is then captured by the meshes of the network and is finally released by syneresis.
• the active agent is a water-soluble active agent, preferably an odorous molecule, a cosmetic active agent or a water-soluble pharmaceutical active agent. This active agent can for example be isosorbide which is known for these healing properties.
• the hydrogel does not include an active ingredient, it makes it possible to subtract solid or particulate elements from a liquid medium containing this hydrogel.
• This hydrogel has utility in the medical, cosmetic, agricultural, optical fields, in the field of water treatment, hygiene products, in separation technology or in energy.
• the hydrogel can remove toxic molecules present in the human body.
• the hydrogel can remove unwanted molecules present on the surface of the skin.
• hydrogel can remove active ingredients from wastewater.
• the hydrogel can subtract the surfaces of an unwanted molecule.
• the hydrogel can subtract the molecule from a solution that one wishes to purify.
• measuring solid or particulate elements from a liquid medium containing this hydrogel means the act of trapping, or capturing, elements present in a liquid medium and then removing them from said medium.
• hydrogel in the medical, cosmetic, agricultural, optical field, in the field of water treatment, hygiene products, in separation technology or in energy.
• the process for preparing a hydrogel according to the invention comprises the following steps:
• an active is included in the hydrogel then it is prepared as above but adding the active during step 2) described above.
• steps 1) and 2) of the process for preparing the hydrogel according to the invention can be carried out successively in this order or vice versa or simultaneously.
• FIG. 1 is a diagram showing the kinetics of the concentration of isosorbide released into water from the preparation of Example 2.
• Isosorbide epoxide Arugula.
• Lysine Ajinomoto.
• Isosorbide as an active ingredient Arugula.
• Example 1 preparation of a hvdroael at 50% by mass of water
• Example 2 preparation of a hvdroael at 50% by mass of water further comprising isosorbide as active ingredient
• Example 3 relaraaae test of the preparation of Example 2
• the hydrogel containing the isosorbide obtained according to Example 2 is then immersed in a given volume of water.
• the released isosorbide content is determined by gas chromatography in the form of trimethylsilyl derivatives and quantified by the internal calibration method as described below
• the hydrogel according to the invention obtained by a simple preparation process, is a good alternative to hydrogels based on a polymer of fossil origin.
• the latter exhibits good water absorption, allowing the active ingredient it contains to be advantageously released. Because of these properties, the hydrogel according to the invention can therefore be used in various applications, in particular in the medical, cosmetic, agricultural, optical fields, water treatment, hygiene products, in technology. of separation or in energy.

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• Health & Medical Sciences (AREA)
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• Life Sciences & Earth Sciences (AREA)
• Medicinal Chemistry (AREA)
• Veterinary Medicine (AREA)
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• General Health & Medical Sciences (AREA)
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• Chemical Kinetics & Catalysis (AREA)
• Polymers & Plastics (AREA)
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• Dispersion Chemistry (AREA)
• Birds (AREA)
• Dermatology (AREA)
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• Cosmetics (AREA)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
• Solid-Sorbent Or Filter-Aiding Compositions (AREA)
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• 2019
  • 2019-11-27 FR FR1913342A patent/FR3103380B1/fr active Active
• 2020
  • 2020-11-26 EP EP20824305.5A patent/EP4065624A1/fr active Pending
  • 2020-11-26 WO PCT/FR2020/052182 patent/WO2021105619A1/fr unknown
  • 2020-11-26 US US17/756,396 patent/US20220403118A1/en active Pending
  • 2020-11-26 JP JP2022531071A patent/JP2023503358A/ja active Pending
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