WO2008038864A1 - Film biocompatible à faible toxicité utilisant du chitosane et du polyéthylène glycol - Google Patents

Film biocompatible à faible toxicité utilisant du chitosane et du polyéthylène glycol Download PDF

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Publication number
WO2008038864A1
WO2008038864A1 PCT/KR2007/000247 KR2007000247W WO2008038864A1 WO 2008038864 A1 WO2008038864 A1 WO 2008038864A1 KR 2007000247 W KR2007000247 W KR 2007000247W WO 2008038864 A1 WO2008038864 A1 WO 2008038864A1
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WIPO (PCT)
Prior art keywords
polyethylene glycol
chitosan
film
weight
agent
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Application number
PCT/KR2007/000247
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English (en)
Inventor
Hyun-Oh Yoo
Tae-Won Son
Byung-Giu Kim
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Genic Co., Ltd.
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Application filed by Genic Co., Ltd. filed Critical Genic Co., Ltd.
Publication of WO2008038864A1 publication Critical patent/WO2008038864A1/fr

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    • 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
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
    • C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
    • C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
    • 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
    • A61K8/0216—Solid or semisolid forms
    • 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
    • A61K8/736—Chitin; Chitosan; Derivatives thereof
    • 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
    • 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
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
    • C08L5/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
    • 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
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/594—Mixtures of polymers

Definitions

  • the present invention relates to a low toxic, biocompatible film. More specifically, the present invention relates to a low-toxic, biocompatible film which is prepared using chitosan and polyethylene glycol, and is useful for medical or cosmetic applications due to non- or low-toxicity and irritation to the skin.
  • Chitosan is abundant in nature and is widely available in the form of various products. Chitosan is a kind of an aminopoly saccharide found in nature, and is a natural material obtained by deacetylation of chitin which is contained in exoskeletons and shells of crustaceans such as crabs, prawns and shrimps, cuttlefish bones, and cell walls of microorganisms such as fungi, mushrooms and bacteria.
  • Chitosan is a biocompatible material having non-toxicity and biodegradability, and is known to have various functions including biological applicability for use in, for example, cell fusion, in vivo tissue culture and hemorrhage stopping, biological properties such as antibacterial activity and biocompatibility, and physiological activities such as lowering of a blood cholesterol level, facilitation of intestinal metabolism, an anti-cancer activity by immune enhancement, improvement of liver functions, a hypoglycemic activity and a heavy metal-detoxifying activity.
  • Chitosan is represented by Formula I below:
  • Chitin is found abundantly in hard epidermis, shells or exoskeletons of crustaceans and insects and in cell walls of fungi such as molds, yeasts and mushrooms, and along with potassium carbonate, ashes, proteins, lipids and pigments, serves to support the main structure of the shells and exoskeletons of various animals.
  • US Patent No. 3533940 discloses a method for preparing chitosan from chitin, along with its application to fibers and films.
  • the prepared chitosan is dissolved in an aqueous solution of an organic acid such as acetic acid to thereby prepare a solution for formation of fibers and films.
  • an organic acid such as acetic acid
  • chitin is dissolved in polar organic solvents such as dimethy- lacetamide containing lithium chloride to produce chitin fibers.
  • polar organic solvents such as dimethy- lacetamide containing lithium chloride
  • 4996307 proposes a method for preparing a water- soluble, high molecular weight acylated chitosan having a degree of acylation of 35 to 65%, which can be achieved within a short period of time and at a high yield in the same system.
  • US Patent No. 5900479 discloses the production of water-insoluble chitin films and fibers using an aqueous organic acid solution of chitosan. Further, US Patent No.
  • 4286087 discloses a process of making a chitin powder which comprises adding chitin to a solution of phosphoric acid dissolved in an aliphatic alcohol, heating the solution until homogeneous dispersion is achieved, stirring the dispersion to hydrolyze the chitin, separating the hydrolyzed chitin from the dispersion, drying the separated chitin and grinding the dried chitin to a desired particle size.
  • US Patent 5836970 has proposed a technique of applying a blend or mixture consisting of chitosan and alginate in a suitable ratio as a wound dressing in the form of a powder, film or gel, and has asserted that the application of such a wound dressing exhibits wound-healing promoting effects.
  • US Patent Nos. 3632754 and 3914413 teach that chitin has therapeutic effects of facilitating wound healing and can be physiologically solubilized by virtue of its hydrolysis by the action of lysozyme.
  • European Patent No. 0089152 and Japanese Patent No. 86141373 there is disclosed a method of preparing a wound protective dressing using a composite film of chitosan and keratin or collagen.
  • Kenji Okuyama et al Macromolecular Vol. 30, 5849, 1997) have suggested a theoretical basis that hydrated chitosan molecules can form a two-dimensional conformation during a crystallization process, and Sonja Salmon et al (Journal of Polymer Sci. Part B: Polymer Physics, Vol. 33, 1007, 1995) have reported that it is only possible to prepare one-dimensional fibride using chitosan.
  • a polyethylene glycol which is a water-soluble polymer prepared by the reaction of a hydrocarbon glycol as a monomer with a hydrocarbon oxide as a monomer in the presence of water, has various molecular weights ranging from several hundreds to several tens of thousands and shows different conformations depending upon a molecular weight thereof.
  • the polyethylene glycol is represented by Formula II below: [18]
  • the polyethylene glycol has a molecular weight of 200 to 400, it is present as a liquid state.
  • the polyethylene glycol having a molecular weight of about 600 exists as a semi-solid state.
  • the polyethylene glycol having a molecular weight of about 1000 is in a soft wax state and the polyethylene glycol having a molecular weight of more than about 3000 is in a hard wax state. Since the polyethylene glycol is water-soluble due to high hygroscopicity and hydrophilicity thereof, the polyethylene glycol is widely used in various processing by grafting or post-treatment of fibers, in order to improve absorptiveness, antistaticity and decontamination capability of the fibers.
  • the polyethylene glycol exhibits superior compatibility and no toxicity/irritation to the skin, and has diverse applications and uses as medicines, cosmetics, and lubricants for various processing.
  • the polyethylene glycol is used as a non-ionic surfactant primarily for fatty acids and esters, and is also used as an emulsifying agent, a dispersant, a detergent or the like.
  • the polyethylene glycol is used for various applications such as rubber molding, spinning, ceramics, lubricants upon metal processing, adhesives, cellophane, wetting agents, abrasives, water-based paints, printing inks and the like.
  • Tatsuro In order to improve the solubility of chitosan in water or organic solvents, Tatsuro
  • Ouchi et al (Polymer. Vol. 39, No. 21, 5171-5175, 1998) have achieved grafting of the polyethylene glycol into chitosan by preparing triphenylmethylene chitosan and subjecting the prepared triphenylmethylene chitosan to a coupling reaction with methoxy polyethylene glycolic acid in the presence of dimethylformamide, using a water-soluble carbodiimide method.
  • chitosan can be used as a medical material by dissolving chitosan in a 2% acetic acid solution to prepare a 4% chitosan solution, mixing the chitosan solution with a 4% polyethylene glycol solution and a 1% glu- taraldehyde solution, and maintaining the mixed solution at 37°C for 24 hours to thereby prepare a chitosan-polyethylene glycol hydrogel.
  • a low-toxicity film of the present invention prepared using chitosan and polyethylene glycol monosuccinate, may be used as a high-grade medical material having excellent biocompatibility, and is applicable to various fields including cosmetic and medical materials having non-toxicity and irritation to the skin.
  • the present invention has been made in view of the above problems, and it is an object of the present invention to provide a low-toxic, biocompatible film which is highly biocompatible and is useful for medical or cosmetic applications due to non- or low-toxicity and irritation to the skin, via the use of chitosan and polyethylene glycol.
  • FlG. 1 is a cross-sectional SEM of a low-toxic, biocompatible film prepared according to the present invention, using chitosan and polyethylene glycol.
  • a low-toxic, biocompatible film comprising a water-soluble organic salt of chitosan and polyethylene glycol monosuccinate which is obtained by mixing 0.3 to 99% by weight of a polyethylene glycol monosuccinate obtained from esterification of a mixture of a polyethylene glycol having a number ave rage molecular weight of 200 to 20,000 g/mol and a succinic anhydride in a molar equivalent ratio; 0.1 to 30% by weight of chitosan having a number average molecular weight of 1,000 to 1,000,000 g/mol, a deacetylation degree of 60 to 99% and a viscosity of 1 to 100,000 cps; and 0.1 to 96% by weight of water.
  • a method for preparing a low-toxic, biocompatible film using chitosan and a polyethylene glycol comprising subjecting a mixture of a polyethylene glycol having a number average molecular weight of 200 to 20,000 g/mol and a succinic anhydride in a molar equivalent ratio to esterification to thereby prepare a polyethylene glycol monosuccinate; adding 0.1 to 30% by weight of chitosan having a number average molecular weight of 1,000 to 1,000,000 g/mol, a deacetylation degree of 60 to 99% and a viscosity of 1 to 100,000 cps and 0.1 to 96% by weight of water to the polyethylene glycol monosuccinate, thereby preparing a water-soluble organic salt of chitosan and polyethylene glycol monosuccinate; and casting the resulting organic salt on a glass plate or Teflon film using a film casting machine, thereby forming a
  • a biocompatible film which is produced using polyethylene glycol monosuccinate and chitosan.
  • the film of the present invention is obtained by adding high-purity chitosan in a certain ratio to a polyethylene glycol monosuccinate obtained from esterification of a mixture of a polyethylene glycol having a number average molecular weight of 200 to 20,000 g/mol and a succinic anhydride in a molar equivalent ratio to thereby prepare a water-soluble organic salt of chitosan and polyethylene glycol monosuccinate and casting the resulting organic salt, and has characteristics such as an excellent biocompatibility and non- or low-toxicity and irritation to the skin.
  • the chitosan used in the present invention is a deacetylation product of chitin, and has a number average molecular weight of 1,000 g/mol to 1,000,000 g/mol and a deacetylation degree of 60 to 99%. More preferably, the chitosan has a number average molecular weight of 10,000 g/mol to 500,000 g/mol and a deacetylation degree of 70 to 96%. Generally, chitosan should have a deacetylation degree of more than 50%, in order to achieve conversion of chitin into chitosan, and it is very difficult to obtain the chitosan having a deacetylation degree of more than 99%.
  • the chitosan has a molecular weight of less than 1,000 g/mol, this may lead to deterioration in characteristics of the chitosan as a polymer oligosaccharide. If the chitosan has an excessively high molecular weight of more than 1,000,000 g/mol, it is difficult to form a salt compound of the chitosan and polyethylene glycol monosuccinate.
  • the polyethylene glycol used in the present invention has a number average molecular weight of 200 g/mol to 20,000 g/mol, preferably of 200 g/mol to 1,000 g/ mol. Where the polyethylene glycol having such a molecular weight range is used, it is easy to form a salt compound of the chitosan and polyethylene glycol monosuccinate.
  • the film of the present invention may contain one or more additives selected from medicines, solvents, nutrients, hygroscopic agents, coloring agents, lubricants, organic acids, surfactants, humectants, excipients, emulsifying agents, coating agents, adhesives, fillers, plasticizers, curing agents, rubbers, fats including natural fats, oil including natural oil, wax, plant extracts, hydrocarbon such as liquid paraffin, squalene, squalane, mineral oil, fatty acids, unsaturated fatty acids, aliphatic polyesters, fish oil, lipids, vitamins, UV blocking agents, retinol and antibacterial agents, depending upon desired applications.
  • additives selected from medicines, solvents, nutrients, hygroscopic agents, coloring agents, lubricants, organic acids, surfactants, humectants, excipients, emulsifying agents, coating agents, adhesives, fillers, plasticizers, curing agents, rubbers, fats including natural fats, oil including
  • a mixture of a polyethylene glycol and a succinic anhydride in a molar equivalent ratio is subjected to esterification reaction to thereby prepare a polyethylene glycol monosuccinate.
  • the polyethylene glycol monosuccinate is represented by Formula in below.
  • the polyethylene glycol preferably has a number average molecular weight of 200 to 20,000 g/mol, as mentioned above.
  • the polyethylene glycol and succinic anhydride are preferably mixed in a molar equivalent ratio of about 1:1. More preferably, the molar equivalent ratio of the polyethylene glycol and succinic anhydride is in a range of about 1 :0.4 to 1 : 1.5, but is not limited thereto.
  • a reaction temperature is in a range of 0 to 100°C.
  • the organic salt prepared through Sections (1) and (2) is cast to thereby prepare a film. Formation of the film may be carried out by a film casting method conventionally known in the art.
  • the organic salt can be formed into the film by casting the salt on a glass plate or Teflon film using a film casting machine.
  • the thus-prepared film of the present invention preferably has a pH of 4 to 7, and a thickness of 2 to 2,000 D without particular limitation.
  • At least one additive selected from the group consisting of a softener, a surfactant, a hygroscopic agent, a humectant, a stabilizer, an excipient, a medicine, a solvent, a plasticizer, a curing agent, an absorbent, a filler, a reinforcing agent, a coloring agent, an organic acid, silicone oil, a rubber, a fat including natural fat, oil including natural oil, wax, a plant extract, liquid paraffin, squalene, squalane, mineral oil, a fatty acid, an unsaturated fatty acid, an aliphatic polyester, fish oil, lipid, a vitamin, a UV blocking agent, retinol and an antibacterial agent, may be further added to the organic salt.
  • a softener a surfactant, a hygroscopic agent, a humectant, a stabilizer, an excipient, a medicine, a solvent, a plasticizer, a cu
  • the film of the present invention has various functionalities such as biodegradability, antibacterial activity, hemostatic activity, biocompatibility, cell capture capability, in vivo tissue culture ability, anti-odor effects, cell fusion capability, moisturizing properties, absorptiveness, and heat storage and release characteristics. It is expected that the film of the present invention may be used as cosmetics or medical materials such as skin patches, gauze and wound dressings, via addition of an appropriate additive depending upon desired applications, or may be used as various processed materials such as wet coating films, bioadhesive tapes, antibacterial films and the like.
  • FIG. 1 shows a cross-sectional SEM of the thus-prepared film.
  • Example 2 Each 5 g of chitosan having a deacetylation degree of 96% and a viscosity of 2.8 cps, 12.6 cps, 105 cps and 1440 cps and 100 g of water were added to 10 g of polyethylene glycol monosuccinate prepared as in Example 1, thereby obtaining an organic salt of chitosan and polyethylene glycol monosuccinate which was then formed into a film.
  • Example 3 [80] 400 g of a polyethylene glycol having a molecular weight of 400 and 100 g of a succinic anhydride having a purity of 99% were reacted in a molar equivalent ratio as in Example 1, thereby preparing a polyethylene glycol monosuccinate. Chitosan having a viscosity of 12.6 cps and water were added to the polyethylene glycol monosuccinate in a ratio as given in Table 1 below, thereby preparing an aqueous organic salt solution of the chitosan and polyethylene glycol monosuccinate. The thus-prepared organic salt solution was cast into a film on a glass plate.
  • the film according to the present invention composed of the water-soluble organic salt of chitosan and polyethylene glycol monosuccinate, has exhibited the cell viability of about 70 to 80% in the cytotoxic test.
  • the film according to the present invention exhibits non- or low-toxicity and irritation to the skin and therefore can be usefully used for medical or cosmetic applications.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Materials Engineering (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Dermatology (AREA)
  • Medicinal Preparation (AREA)
  • Cosmetics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Materials For Medical Uses (AREA)

Abstract

Cette invention concerne un film biocompatible à faible toxicité utilisant du chitosane et un polyéthylène glycol. Plus particulièrement, cette invention concerne un film biocompatible à faible toxicité comprenant un sel organique hydrosoluble de chitosane et de monosuccinate de polyéthylène glycol obtenu par mélange de 0,3 à 99% en poids d'un monosuccinate de polyéthylène glycol obtenu par estérification d'un mélange de polyéthylène glycol présentant un poids moléculaire moyen compris entre 200 et 20 000 g/mol et un anhydride succinique à un rapport équivalent molaire; de 0,1 à 30% en poids de chitosane présentant un poids moléculaire moyen compris entre 1000 à 1 000 000 g/mol, un degré de désacétylation de 60 à 99% et une viscosité de 1 à 100 000 cps; et de 0,1 à 96% en poids d'eau; ainsi qu'un procédé de préparation correspondant. Le film décrit dans cette invention présente une toxicité faible voire inexistante et il est peu irritant pour la peau, ce qui permet de l'utiliser pour des applications cosmétiques ou médicales.
PCT/KR2007/000247 2006-09-27 2007-01-15 Film biocompatible à faible toxicité utilisant du chitosane et du polyéthylène glycol WO2008038864A1 (fr)

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KR10-2006-0094393 2006-09-27
KR1020060094393A KR100812824B1 (ko) 2006-09-27 2006-09-27 키토산과 폴리에틸렌글리콜을 이용한 생체친화성 저독성필름

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012136082A1 (fr) * 2011-04-02 2012-10-11 佛山市优特医疗科技有限公司 Pansement pour plaies à base de chitosane et son procédé de fabrication
CN109485747A (zh) * 2017-09-12 2019-03-19 中国科学院理化技术研究所 一种水溶性壳聚糖抗菌衍生物及其制备方法
IT202000007237A1 (it) * 2020-04-06 2021-10-06 Agrilaete S R L Composizione a base di chitosano rapidamente solubile in acqua e metodo per ottenerla
CN114848890A (zh) * 2022-03-11 2022-08-05 安徽农业大学 一种可按需溶解的抗菌敷料及其制备方法

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101038699B1 (ko) * 2009-02-09 2011-06-02 연세대학교 산학협력단 생체 친화성 산화막 필름 및 그의 제조 방법
KR101357899B1 (ko) 2011-02-25 2014-02-03 서울대학교산학협력단 간세포 표적 유전자 전달체로서 갈락토실화 폴리에틸렌글리콜-키토산-그라프트-스페르민 공중합체 및 이를 이용한 유전자 치료
CN113797385B (zh) * 2021-08-18 2022-05-24 山东大学 一种壳聚糖/聚乙二醇水凝胶及其制备方法与应用

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US3533940A (en) * 1967-06-02 1970-10-13 Quintin P Peniston Method for treating an aqueous medium with chitosan and derivatives of chitin to remove an impurity
US5900479A (en) * 1995-05-05 1999-05-04 Virginia Tech Intellectual Properties, Inc. Chitin-based coatings
KR20010016482A (ko) * 2000-12-14 2001-03-05 손태원 키토산과 젤라틴으로 조성된 연질 겔
KR20030011358A (ko) * 2001-05-22 2003-02-07 다이셀 가가꾸 고교 가부시끼가이샤 생분해속도가 제어된 생분해성 수지 조성물, 필름 및농업용 멀티필름
KR20050042305A (ko) * 2003-11-01 2005-05-09 학교법인 영남학원 키토산과 폴리에틸렌 글리콜 모노숙시네이트의 수용성유기염 화합물

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AU8184601A (en) 2000-06-27 2002-01-08 Hoffmann La Roche Method for preparing a composition

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US3533940A (en) * 1967-06-02 1970-10-13 Quintin P Peniston Method for treating an aqueous medium with chitosan and derivatives of chitin to remove an impurity
US5900479A (en) * 1995-05-05 1999-05-04 Virginia Tech Intellectual Properties, Inc. Chitin-based coatings
KR20010016482A (ko) * 2000-12-14 2001-03-05 손태원 키토산과 젤라틴으로 조성된 연질 겔
KR20030011358A (ko) * 2001-05-22 2003-02-07 다이셀 가가꾸 고교 가부시끼가이샤 생분해속도가 제어된 생분해성 수지 조성물, 필름 및농업용 멀티필름
KR20050042305A (ko) * 2003-11-01 2005-05-09 학교법인 영남학원 키토산과 폴리에틸렌 글리콜 모노숙시네이트의 수용성유기염 화합물

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012136082A1 (fr) * 2011-04-02 2012-10-11 佛山市优特医疗科技有限公司 Pansement pour plaies à base de chitosane et son procédé de fabrication
CN102727925A (zh) * 2011-04-02 2012-10-17 佛山市优特医疗科技有限公司 酰化壳聚糖伤口敷料、其制备方法及其应用
CN102727925B (zh) * 2011-04-02 2014-09-17 佛山市优特医疗科技有限公司 酰化壳聚糖伤口敷料、其制备方法及其应用
CN109485747A (zh) * 2017-09-12 2019-03-19 中国科学院理化技术研究所 一种水溶性壳聚糖抗菌衍生物及其制备方法
IT202000007237A1 (it) * 2020-04-06 2021-10-06 Agrilaete S R L Composizione a base di chitosano rapidamente solubile in acqua e metodo per ottenerla
EP3892675A1 (fr) * 2020-04-06 2021-10-13 Agrilaete S.r.l. Composition à base de chitosan rapidement soluble dans l'eau et méthode d'obtention de cette composition
CN114848890A (zh) * 2022-03-11 2022-08-05 安徽农业大学 一种可按需溶解的抗菌敷料及其制备方法

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