CA2416504A1 - Crosslinking of polysaccharide(s), preparation of hydrogel(s), polysaccharide(s) and hydrogels(s) obtained and their uses - Google Patents

Crosslinking of polysaccharide(s), preparation of hydrogel(s), polysaccharide(s) and hydrogels(s) obtained and their uses Download PDF

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Publication number
CA2416504A1
CA2416504A1 CA002416504A CA2416504A CA2416504A1 CA 2416504 A1 CA2416504 A1 CA 2416504A1 CA 002416504 A CA002416504 A CA 002416504A CA 2416504 A CA2416504 A CA 2416504A CA 2416504 A1 CA2416504 A1 CA 2416504A1
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CA
Canada
Prior art keywords
polymer
crosslinking
process according
crosslinking agent
hydrogel
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002416504A
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French (fr)
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CA2416504C (en
Inventor
Estelle Piron
Raymonde Tholin
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Allergan Industrie SAS
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Individual
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Application filed by Individual filed Critical Individual
Publication of CA2416504A1 publication Critical patent/CA2416504A1/en
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Publication of CA2416504C publication Critical patent/CA2416504C/en
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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
    • 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
    • A61K8/73—Polysaccharides
    • A61K8/735—Mucopolysaccharides, e.g. hyaluronic acid; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/14—Macromolecular materials
    • A61L27/20—Polysaccharides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L27/52—Hydrogels or hydrocolloids
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
    • C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
    • C08B37/0072—Hyaluronic acid, i.e. HA or hyaluronan; Derivatives thereof, e.g. crosslinked hyaluronic acid (hylan) or hyaluronates
    • 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
    • C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
    • 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
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/91—Injection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2400/00—Materials characterised by their function or physical properties
    • A61L2400/06—Flowable or injectable implant compositions
    • 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
    • C08J2305/00—Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2301/00 or C08J2303/00
    • C08J2305/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof

Abstract

The invention relates to a process for the crosslinking of polysaccharides.
The process of the invention is a process for the crosslinking of at least one polymer selected from polysaccharides and their derivatives, under the action of at least one polyfunctional crosslinking agent, characterized in that said polyfunctional crosslinking agent is reacted with said polymer, in the solid state, during hydration. The invention is applied to the manufacture of hydrogels and gels that can be used, in particular, in plastic or cosmetic surgery.

Claims (12)

1. A process for the crosslinking of at least one polymer selected from poly-saccharides and their derivatives, under the action of at least one polyfunctional crosslinking agent, characterized in that said polyfunctional crosslinking agent is reacted with said polymer, in the solid state, during hydration.
2. The crosslinking process according to claim 1, characterized in that said polyfunctional crosslinking agent reacts with said solid polymer in basic solution.
3. The crosslinking process according to claim 1 or 2, characterized in that said polyfunctional crosslinking agent is an epoxide advantageously selected from 1,4-butanediol diglycidyl ether, 1,2-bis(2,3-epoxypropoxy)ethylene and 1-(2,3-epoxypropyl)-2,3-epoxycyclohexane.
4. The crosslinking process according to claim 3, characterized in that said polyfunctional crosslinking agent consists of 1,4-butanediol diglycidyl ether.
5. The crosslinking process according to any one of claims 1 to 4, characterized in that said polymer is selected from hyaluronic acid, its salts and their mixtures, and in that said polymer advantageously consists of sodium hyaluronate.
6. The crosslinking process according to claim 5, characterized in that said polymer is crosslinked, via its hydroxyl groups, by means of said crosslinking agent to a degree of crosslinking defined by a ratio Total number of reactive groups in said crosslinking agent R=
Total number of disaccharide units in the hyaluronic acid molecules of between 0.10 and 0.50.
7. A process for the preparation of an injectable hydrogel of at least one cross-linked polymer selected from polysaccharides and their derivatives, characterized in that it comprises the crosslinking of said polymer according to any one of claims 1 to 6, followed by the swelling of said crosslinked polymer by hydration.
8. The preparative process according to claim 7, characterized in that it comprises:
- the crosslinking of said polymer according to any one of claims 1 to 6;
- the swelling of said crosslinked polymer;
- the purification of said swollen crosslinked polymer; and - the sterilization, if necessary, of said purified swollen crosslinked polymer.
9. A crosslinked polymer obtainable by carrying out a crosslinking process according to any one of claims 1 to 6.
10. An injectable hydrogel obtainable by carrying out a preparative process according to claim 7 or 8.
11. A filling gel useful in plastic or cosmetic surgery, characterized in that it is based on a charged or uncharged hydrogel according to claim 10.
12. The filling gel according to claim 11, characterized in that it consists of a monophase hydrogel according to claim 10.
CA002416504A 2000-07-19 2001-07-16 Crosslinking of polysaccharide(s), preparation of hydrogel(s), polysaccharide(s) and hydrogels(s) obtained and their uses Expired - Lifetime CA2416504C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR00/09497 2000-07-19
FR0009497A FR2811996B1 (en) 2000-07-19 2000-07-19 CROSS-LINKING OF POLYSACCHARIDE (S), PREPARATION OF HYDROGEL (S); POLYSACCHARIDE (S) AND HYDROGEL (S) OBTAINED, THEIR USES
PCT/FR2001/002300 WO2002006350A1 (en) 2000-07-19 2001-07-16 Polysaccharide crosslinking, hydrogel preparation, resulting polysaccharide(s) and hydrogel(s), uses thereof

Publications (2)

Publication Number Publication Date
CA2416504A1 true CA2416504A1 (en) 2002-01-24
CA2416504C CA2416504C (en) 2009-11-24

Family

ID=8852712

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002416504A Expired - Lifetime CA2416504C (en) 2000-07-19 2001-07-16 Crosslinking of polysaccharide(s), preparation of hydrogel(s), polysaccharide(s) and hydrogels(s) obtained and their uses

Country Status (7)

Country Link
US (1) US6921819B2 (en)
EP (1) EP1303542B3 (en)
CA (1) CA2416504C (en)
DE (1) DE60113121T3 (en)
ES (1) ES2250441T7 (en)
FR (1) FR2811996B1 (en)
WO (1) WO2002006350A1 (en)

Cited By (2)

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US10328180B2 (en) 2008-08-04 2019-06-25 Allergan Industrie, S.A.S. Hyaluronic acid-based gels including lidocaine

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