WO1997002845A1 - A film for topical use in the treatment of wounds - Google Patents

A film for topical use in the treatment of wounds Download PDF

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Publication number
WO1997002845A1
WO1997002845A1 PCT/EP1996/003079 EP9603079W WO9702845A1 WO 1997002845 A1 WO1997002845 A1 WO 1997002845A1 EP 9603079 W EP9603079 W EP 9603079W WO 9702845 A1 WO9702845 A1 WO 9702845A1
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WO
WIPO (PCT)
Prior art keywords
film
hyaluronic acid
wounds
films
treatment
Prior art date
Application number
PCT/EP1996/003079
Other languages
French (fr)
Inventor
Derek Hollingsbee
Elizabeth Joan Jacques
Gillian M. Eccleston
Margaret Ellen Louise Courtney
Original Assignee
Bristol-Myers Squibb Company
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bristol-Myers Squibb Company filed Critical Bristol-Myers Squibb Company
Priority to GB9803131A priority Critical patent/GB2319729B/en
Priority to AU66989/96A priority patent/AU6698996A/en
Publication of WO1997002845A1 publication Critical patent/WO1997002845A1/en

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Classifications

    • 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
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
    • A61L15/225—Mixtures of macromolecular compounds
    • 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
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
    • A61L15/28—Polysaccharides or their derivatives
    • 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

Definitions

  • the present invention relates to films for topical use in 10 the treatment of wounds, and in particular to films comprising hyaluronic acid or salts thereof alone or in combination with a hydrocolloid, and a process for making films comprising hyaluronic acid or salts thereof alone or in combination with a hydrocolloid. 15
  • Hyaluronic acid is an acid complex carbohydrate functioning mainly as a binding and protective component in connective tissue. It is known that administration of exogenous hyaluronic acid determines an antiphlogistic and 20 stimulating effect on the granulation tissue, which accelerates cicatrization and re-epi helialization of lesions.
  • compositions are known from European Patent 25 Application No. 0 480 198 which contain the sodium salt of hyaluronic acid and antiseptic substances for topical use. These compositions are however in the form of emulsions or hydrogels. When used in the treatment of wounds these product forms can suffer from the disadvantage that they 30 add liquid to the wound site which adds to the problem of management of wound exudate. In addition these product forms make it difficult to apply a known and uniform dose to the wound. From Japanese Patent Application No. 268765 to Kiburn Foods Inc it is known to make sheets from hyaluronic acid salt, fibrous crystals for use in the treatment of skin lesions. These fibrous crystal sheets suffer from the disadvantage that they are fairly brittle and do not conform readily to the wound site.
  • the present invention which accordingly provides a film for topical use in the treatment of wounds comprising hyaluronic acid and hydrocolloid.
  • the advantages of this film are that because the film is dry, exudate is readily absorbed by both the hyaluronic acid and the hydrocolloid and dosing is uniform and predictable.
  • the topical film of the invention contributes to haemostasis.
  • a further aspect of the invention provides a clear and continuous film for topical use in the treatment of wounds comprising hyaluronic acid.
  • the use of a clear film gives the advantage of wound visualisation without removal of the dressing.
  • the clear film assists in wound healing and haemostasis.
  • a further aspect of the invention provides a process for making a film comprising hyaluronic acid comprising the steps of:
  • the process according to the invention has the advantage of simplicity and aids the easy and controlled addition of other components .
  • the hyaluronic acid is water soluble potentially toxic organic solvents need not be used.
  • Suitable solvents for use in place of or in addition to water are propylene glycol and glycerol .
  • Hyaluronic acid as used in the present invention is found as a naturally occuring substance in the intracellular matrix of connective tissue. Preferably it is used in compositions of the present invention in the form of its acid salt, most preferably the sodium salt. This ensures water solubility to the hyaluronic acid and gives instantaneous dosage to the wound site.
  • Commercially available hyaluronic acid or salts thereof has molecular weights in the range of from 50,000 to 2,000,000. We have found that the molecular weight of the hyaluronic acid used influences the characteristics of the film. Thus hyaluronic acid ⁇ of different molecular weight can be blended to create particularly flexible films or particularly strong films.
  • the salts can be prepared commercially in a bacterial fermentation process or from animal tissues using appropriate extraction techniques. Prokaryotic hyaluronic acid is less expensive than the tissue extracted version, has higher purity and is available in larger quantities.
  • the films of the present invention preferably comprise up to 100% hyaluronic acid, more preferably from 0.1% to 90% of hyaluronic acid when the film further comprises hydrocolloid.
  • Suitable hydrocolloid materials for use in the present invention include sodium, calcium (or other alkali metal or alkaline earth metal salts thereof) carboxymethylcellulose sodium carboxymethyl cellulose being preferred, pectin, gelatin, guar gum, locust bean gum, collagen polyvinylalcohol, hydroxyethyl cellulose, polyvinyl pyrollidone, alginates and salts thereof, chitin, aloe vera, hydroxypropylmethylcellulose and gum karaya.
  • the films of the present invention preferably comprise from 10% to 90% by weight of hydrocolloid.
  • the films of the invention may also comprise various optional ingredients such as antibacterial agents and pharmaceutical agents and/or excipients such as preservatives, humectants and plasticiers.
  • Particularly preferred optional ingredients include silver sulphadiazine, polyvinylpyrrolidone iodine, chlorhexidine and metronidazole .
  • a hyaluronic acid film was prepared by mixing prokaryotic sodium hyaluronate of molecular weight 1,570,000 (Batch No.5021) ex Pronova Biopolymers of Box 8, Alton, Hampshire, GU3 4Y2, United Kingdom in water using an overhead propeller to form a 2% by weight solution.
  • the solution was coated onto Melinex S Film, a polyethylene terephthalate ex ICI Films, at a coating thickness of 2mm and oven dried overnight. The percentage of sodium hyaluronate in the final film was 100%.
  • the following example shows the effect of hyaluronic acid containing films on skin lesions.
  • six wounds 0.5 cm in diameter and extending down to the level of the muscle fascia
  • a gauze dressing was applied to the freshly created wounds on day 0 for a period of 24 hours.
  • the following treatments were applied to the wounds from day 1 post-operatively.
  • Treatment A A film prepared by the method of Example 1 under V5 dressings. Treatment B Control
  • Dressings were changed on days 2,4,7,9 and 11. Evaluation of the healing of the wounds was undertaken by measurement of the contraction rate, laser Doppler evaluation of blood flow and histological evaluation of biopsies including various stainings for identification and analysis .
  • the histological data showed that all the wounds followed a normal progression of wound healing.
  • the Treatment A wounds showed more advanced fibroplasia with development of granulation tissue .
  • Example 1 was repeated by preparing a 2.00% by weight solution of hyaluronic acid extracted from tissue, in this case rooster comb (Pentapharm, Basel, Switzerland) which was then cast onto Melinex S Film in a 2mm layer and dried overnight .
  • rooster comb Pentapharm, Basel, Switzerland
  • Example 1 was repeated by preparing a 2.00% by weight solution of hyaluronic acid extracted from human umbilical cord tissue (Sigma Chemical Co., Poole, Dorset, UK) which was then cast onto Melinex S Film in a 2 mm layer and dried overnight .
  • Films according to the invention were made from separate aqueous solutions of the ingredients as shown in the following table made according to the method of Example 1.
  • the solutions were coated onto Melinex S Film, a polyethylene terephthalate ex ICI Films, at a coating thickness of 2mm and oven dried overnight .
  • the resulting films had a thickness of 0.5mm.
  • Films according to the invention were made from separate aqueous solution ⁇ of the ingredients as shown in the following table made according to the method of Example 1 except that the coating thicknes ⁇ and drying times were varied to give a final film thickness of 0.5mm.
  • PVP powdered PVP direct to ⁇ fully hydrated solution of hyaluronic acid.
  • those films which optionally comprise co-solvents such as propylene glycol or glycerol these components were added as liquids to fully hydrated solutions of the other components .
  • the addition of polyethylene glycol where present was made as a solid or molten solution to fully hydrated solution ⁇ of the other components.
  • the solutions were coated onto a sub ⁇ trate for example metal, glass, acetate,polystyrene or polypropylene and dried to a final thickness of 0.5mm.
  • the films comprising a mixture of hyaluronic acid and a hydrocolloid were found to have the advantage of increased film strength over films containing hydrocolloid alone. This can be seen by comparing the results of Example 15 with those obtained from a film made of hydrocolloid alone - the film of,Example 15 had a Max. Force of 15 N while that of a hydrocolloid alone has a Max. Force of 2.6 N.
  • the addition of hydrocolloids to the films is beneficial because some hydrocolloids are believed to have useful wound healing properties in their own right for example aloe vera and chitin.
  • the films comprising a mixture of PVP and hyaluronic acid were found to be particularly strong.
  • the films comprising glycol, glycerol or polyethylene glycol as co-solvents were found to be very flexible.
  • the maximum force to break 10mm x 50mm x 0.5mm samples of the film and their extension at breaking were measured using a Texture Analyser (ex Stable Micro Systems) at a velocity of O.Smms" 1 .
  • the time taken for one of the samples to dissolve completely in 50 ml of water was measured and noted as the dissolution time.
  • films were prepared from 1 to 2% by weight solutions of hyaluronic acid, and hydrocolloid. Films were prepared from the individual solutions and mixtures of different solutions. The films produced were clear and dis ⁇ olved rapidly (1-2 minutes)
  • This film was prepared from a 1% prokaryotic solution of hyaluronic acid with 0.1% polyethylene glycol. The film was clear and dissolved readily.
  • This film was prepared from a 20% solution of low molecular weight prokaryotic hyaluronic acid and was clear with a yellow to flesh coloured tint.
  • Thi ⁇ film was prepared as example 21 except that the solution additionally contained 0.2% propylene glycol.
  • the film was clear with a flesh coloured tint .
  • These films were prepared from a mixture of hyaluronic acids of different molecular weight ⁇ .
  • the film ⁇ were yellow to clear.
  • a film was prepared from a solution comprising 1% by weight of prokaryotic hyaluronic acid and 0.5% by weight of polyethylene glycol according to the method described above. The resulting film was clear and continuous.
  • the maximum force to break 10mm x 50mm x 0.5mm samples of the film and their extension at breaking were measured using a Texture Analyser (ex Stable Micro Systems) at a velocity of O.Smms "1 .
  • the time taken for one of the samples to dis ⁇ olve completely in 50 ml of water was measured and noted as the dissolution time.

Abstract

A film for topical use in the treatment of wounds comprising hyaluronic acid or salts thereof and hydrocolloid.

Description

≠
I .-A FILM FOR TOPICAL USE IN THE TREATMENT OF WOUNDS
The present invention relates to films for topical use in 10 the treatment of wounds, and in particular to films comprising hyaluronic acid or salts thereof alone or in combination with a hydrocolloid, and a process for making films comprising hyaluronic acid or salts thereof alone or in combination with a hydrocolloid. 15
Hyaluronic acid is an acid complex carbohydrate functioning mainly as a binding and protective component in connective tissue. It is known that administration of exogenous hyaluronic acid determines an antiphlogistic and 20 stimulating effect on the granulation tissue, which accelerates cicatrization and re-epi helialization of lesions.
Pharmaceutical compositions are known from European Patent 25 Application No. 0 480 198 which contain the sodium salt of hyaluronic acid and antiseptic substances for topical use. These compositions are however in the form of emulsions or hydrogels. When used in the treatment of wounds these product forms can suffer from the disadvantage that they 30 add liquid to the wound site which adds to the problem of management of wound exudate. In addition these product forms make it difficult to apply a known and uniform dose to the wound. From Japanese Patent Application No. 268765 to Kiburn Foods Inc it is known to make sheets from hyaluronic acid salt, fibrous crystals for use in the treatment of skin lesions. These fibrous crystal sheets suffer from the disadvantage that they are fairly brittle and do not conform readily to the wound site. In addition, being white and opaque, they do not allow visualisation of the wound without removal. An additional disadvantage which is particularly marked for the intended use is that in the manufacture of the crystals flammable, toxic organic solvents are used which may be left as traces in the dressing and potentially damage the wound.
We have now found that these problems are mitigated by the present invention which accordingly provides a film for topical use in the treatment of wounds comprising hyaluronic acid and hydrocolloid. The advantages of this film are that because the film is dry, exudate is readily absorbed by both the hyaluronic acid and the hydrocolloid and dosing is uniform and predictable. We also believe that the topical film of the invention contributes to haemostasis.
A further aspect of the invention provides a clear and continuous film for topical use in the treatment of wounds comprising hyaluronic acid. The use of a clear film gives the advantage of wound visualisation without removal of the dressing. The clear film assists in wound healing and haemostasis. A further aspect of the invention provides a process for making a film comprising hyaluronic acid comprising the steps of:
(i) mixing the hyaluronic acid or the hyaluronic acid and hydrocolloid in water or a suitable solvent and,
(ii) casting said mixture onto a substrate to form a film.
The process according to the invention has the advantage of simplicity and aids the easy and controlled addition of other components . As the hyaluronic acid is water soluble potentially toxic organic solvents need not be used. Suitable solvents for use in place of or in addition to water are propylene glycol and glycerol .
Hyaluronic acid as used in the present invention is found as a naturally occuring substance in the intracellular matrix of connective tissue. Preferably it is used in compositions of the present invention in the form of its acid salt, most preferably the sodium salt. This ensures water solubility to the hyaluronic acid and gives instantaneous dosage to the wound site. Commercially available hyaluronic acid or salts thereof has molecular weights in the range of from 50,000 to 2,000,000. We have found that the molecular weight of the hyaluronic acid used influences the characteristics of the film. Thus hyaluronic acidε of different molecular weight can be blended to create particularly flexible films or particularly strong films. The salts can be prepared commercially in a bacterial fermentation process or from animal tissues using appropriate extraction techniques. Prokaryotic hyaluronic acid is less expensive than the tissue extracted version, has higher purity and is available in larger quantities. The films of the present invention preferably comprise up to 100% hyaluronic acid, more preferably from 0.1% to 90% of hyaluronic acid when the film further comprises hydrocolloid.
Suitable hydrocolloid materials for use in the present invention include sodium, calcium (or other alkali metal or alkaline earth metal salts thereof) carboxymethylcellulose sodium carboxymethyl cellulose being preferred, pectin, gelatin, guar gum, locust bean gum, collagen polyvinylalcohol, hydroxyethyl cellulose, polyvinyl pyrollidone, alginates and salts thereof, chitin, aloe vera, hydroxypropylmethylcellulose and gum karaya. The films of the present invention preferably comprise from 10% to 90% by weight of hydrocolloid.
The films of the invention may also comprise various optional ingredients such as antibacterial agents and pharmaceutical agents and/or excipients such as preservatives, humectants and plasticiers. Particularly preferred optional ingredients include silver sulphadiazine, polyvinylpyrrolidone iodine, chlorhexidine and metronidazole .
The following are representative exampleε of dressings within the scope of the invention.
Example 1
A hyaluronic acid film was prepared by mixing prokaryotic sodium hyaluronate of molecular weight 1,570,000 (Batch No.5021) ex Pronova Biopolymers of Box 8, Alton, Hampshire, GU3 4Y2, United Kingdom in water using an overhead propeller to form a 2% by weight solution. The solution was coated onto Melinex S Film, a polyethylene terephthalate ex ICI Films, at a coating thickness of 2mm and oven dried overnight. The percentage of sodium hyaluronate in the final film was 100%.
Example 2
The following example shows the effect of hyaluronic acid containing films on skin lesions. In a porcine wound model study six wounds (0.5 cm in diameter and extending down to the level of the muscle fascia) were created on each of the porcine models in the study. A gauze dressing was applied to the freshly created wounds on day 0 for a period of 24 hours. The following treatments were applied to the wounds from day 1 post-operatively.
Treatment A A film prepared by the method of Example 1 under V5 dressings. Treatment B Control
Dressings were changed on days 2,4,7,9 and 11. Evaluation of the healing of the wounds was undertaken by measurement of the contraction rate, laser Doppler evaluation of blood flow and histological evaluation of biopsies including various stainings for identification and analysis .
The results of the measurements of contraction rates of the wounds showed a significant difference between the treatment and control .
Evaluation of the angiogenic response in the wounds showed that on day 4 there was no significant difference in perfusion levels between the treatments. However on day 7 the results showed that the mean perfusion levels in the Treatment A wounds were higher than the control .
The histological data showed that all the wounds followed a normal progression of wound healing. The Treatment A wounds showed more advanced fibroplasia with development of granulation tissue .
Example 3
Example 1 was repeated by preparing a 2.00% by weight solution of hyaluronic acid extracted from tissue, in this case rooster comb (Pentapharm, Basel, Switzerland) which was then cast onto Melinex S Film in a 2mm layer and dried overnight .
Example 4
Example 1 was repeated by preparing a 2.00% by weight solution of hyaluronic acid extracted from human umbilical cord tissue (Sigma Chemical Co., Poole, Dorset, UK) which was then cast onto Melinex S Film in a 2 mm layer and dried overnight .
Examples 5 to 14
Films according to the invention were made from separate aqueous solutions of the ingredients as shown in the following table made according to the method of Example 1.
The solutions were coated onto Melinex S Film, a polyethylene terephthalate ex ICI Films, at a coating thickness of 2mm and oven dried overnight . The resulting films had a thickness of 0.5mm.
Examples 15 to 28
Films according to the invention were made from separate aqueous solutionε of the ingredients as shown in the following table made according to the method of Example 1 except that the coating thicknesε and drying times were varied to give a final film thickness of 0.5mm. In making films comprising PVP it was found possible to add powdered PVP direct to ε fully hydrated solution of hyaluronic acid. In those films which optionally comprise co-solvents such as propylene glycol or glycerol these components were added as liquids to fully hydrated solutions of the other components . The addition of polyethylene glycol where present was made as a solid or molten solution to fully hydrated solutionε of the other components. The solutions were coated onto a subεtrate for example metal, glass, acetate,polystyrene or polypropylene and dried to a final thickness of 0.5mm.
The films comprising a mixture of hyaluronic acid and a hydrocolloid were found to have the advantage of increased film strength over films containing hydrocolloid alone. This can be seen by comparing the results of Example 15 with those obtained from a film made of hydrocolloid alone - the film of,Example 15 had a Max. Force of 15 N while that of a hydrocolloid alone has a Max. Force of 2.6 N. The addition of hydrocolloids to the films is beneficial because some hydrocolloids are believed to have useful wound healing properties in their own right for example aloe vera and chitin. The films comprising a mixture of PVP and hyaluronic acid were found to be particularly strong. The films comprising glycol, glycerol or polyethylene glycol as co-solvents were found to be very flexible. The maximum force to break 10mm x 50mm x 0.5mm samples of the film and their extension at breaking were measured using a Texture Analyser (ex Stable Micro Systems) at a velocity of O.Smms"1. The time taken for one of the samples to dissolve completely in 50 ml of water was measured and noted as the dissolution time.
Examples 15 to 19
These films were prepared from 1 to 2% by weight solutions of hyaluronic acid, and hydrocolloid. Films were prepared from the individual solutions and mixtures of different solutions. The films produced were clear and disεolved rapidly (1-2 minutes)
This film was prepared from a 1% prokaryotic solution of hyaluronic acid with 0.1% polyethylene glycol. The film was clear and dissolved readily.
Example 21
This film was prepared from a 20% solution of low molecular weight prokaryotic hyaluronic acid and was clear with a yellow to flesh coloured tint.
Example 22
Thiε film was prepared as example 21 except that the solution additionally contained 0.2% propylene glycol. The film was clear with a flesh coloured tint .
Examples 23 to 25
These films were prepared from a mixture of hyaluronic acids of different molecular weightε . The filmε were yellow to clear.
Examples 26 and 27
These films were prepared from solutions of high molecular weight prokaryotic hyaluronic acid and poly- vinylpyrollidone. The filmε were very strong with parameters beyond the measuring capabilities of the equipment.
Example 29
A film was prepared from a solution comprising 1% by weight of prokaryotic hyaluronic acid and 0.5% by weight of polyethylene glycol according to the method described above. The resulting film was clear and continuous.
The maximum force to break 10mm x 50mm x 0.5mm samples of the film and their extension at breaking were measured using a Texture Analyser (ex Stable Micro Systems) at a velocity of O.Smms"1. The time taken for one of the samples to disεolve completely in 50 ml of water was measured and noted as the dissolution time.
Disεolution time: 10 minuteε Force to break: 8.8 N Extenεion at break: 20mm
Figure imgf000013_0001
Figure imgf000013_0002
Figure imgf000014_0001
e ui ment. These filmε were howev ticul t

Claims

A film for topical use in the treatment of wounds comprising hyaluronic acid or salts thereof and hydrocolloid.
A clear and continuous film for topical use in the treatment of wounds comprising hyaluronic acid or salts thereof.
3. A clear and continuous film as claimed in claim 2 which further comprises hydrocolloid.
4. A process for making a film comprising hyaluronic acid or salts thereof comprising the steps of: (i) mixing the hyaluronic acid and hydrocolloid in a suitable solvent and, (ii) casting said mixture onto a substrate to form a film.
S. A process for making a film comprising hyaluronic acid or salts thereof comprising the steps of: (i) mixing the hyaluronic acid in a suitable solvent and, (ii) casting said mixture onto a substrate to form a film.
6. A process a claimed in claim 4 or claim 5 wherein the solvent is water.
7. Use of a composition comprising hyaluronic acid or salts thereof and hydrocolloid in the preparation of a medicament for use in the treatment of wounds.
Use as claimed in claim 7 wherein the wounds are chronic wounds.
PCT/EP1996/003079 1995-07-13 1996-07-12 A film for topical use in the treatment of wounds WO1997002845A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB9803131A GB2319729B (en) 1995-07-13 1996-07-12 A film for topical use in the treatment of wounds
AU66989/96A AU6698996A (en) 1995-07-13 1996-07-12 A film for topical use in the treatment of wounds

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB9514361.6A GB9514361D0 (en) 1995-07-13 1995-07-13 A film for topical use in the treatment of wounds
GB9514361.6 1995-07-13

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Cited By (13)

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WO1998017328A1 (en) * 1996-10-22 1998-04-30 Smith & Nephew Plc Absorbent dressing
DE19712699A1 (en) * 1997-03-26 1998-10-01 Thueringisches Inst Textil Rapid dressing for wounds, used to improve environment of wound
WO1999004828A2 (en) * 1997-07-28 1999-02-04 Fidia Advanced Biopolymers, S.R.L. Use of hyaluronic acid derivatives in the preparation of biomaterials
GB2333711A (en) * 1996-10-22 1999-08-04 Smith & Nephew Absorbant dressing
WO2001078692A2 (en) * 2000-04-13 2001-10-25 Color Access, Inc. Membrane delivery system
EP1174463A1 (en) * 1999-02-19 2002-01-23 Denki Kagaku Kogyo Kabushiki Kaisha Hyaluronic acid gel composition, process for producing the same, and medical material containing the same
WO2003059404A2 (en) * 2002-01-18 2003-07-24 Cpn Spol. S R.O. Preparation for wound healing and prevention of bandage adhesion to the wound
GB2370277B (en) * 2000-12-21 2005-01-05 Matang Mfg Sdn Bhd Plant-based emollient-containing glove and method for making same
LT5549B (en) 2007-07-23 2009-02-25 Cpn Spol. S R.O. Preparation for wound healing and prevention of bandage adhesion to the wound
JP2014114355A (en) * 2012-12-07 2014-06-26 Dainichiseika Color & Chem Mfg Co Ltd Method for manufacturing hyaluronic acid film, and hyaluronic acid film
US20200253876A1 (en) * 2017-10-12 2020-08-13 Solyplus Berlin Gmbh Methods of fabrication of concentrated and homogeneously wetted massive polymers and applications thereof
EP3593973A4 (en) * 2017-03-07 2020-10-28 Jinwoo Bio Co., Ltd. Method for manufacturing hyaluronate film, and hyaluronate film manufactured thereby
WO2023229557A1 (en) * 2022-05-23 2023-11-30 Ondokuz Mayis Universitesi Polymer composite film having properties of adhesion and healing on wet surfaces

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Cited By (20)

* Cited by examiner, † Cited by third party
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GB2333711A (en) * 1996-10-22 1999-08-04 Smith & Nephew Absorbant dressing
WO1998017328A1 (en) * 1996-10-22 1998-04-30 Smith & Nephew Plc Absorbent dressing
DE19712699A1 (en) * 1997-03-26 1998-10-01 Thueringisches Inst Textil Rapid dressing for wounds, used to improve environment of wound
DE19712699C2 (en) * 1997-03-26 2000-05-25 Thueringisches Inst Textil Process for the production of wound dressings with wound care active substances
WO1999004828A2 (en) * 1997-07-28 1999-02-04 Fidia Advanced Biopolymers, S.R.L. Use of hyaluronic acid derivatives in the preparation of biomaterials
WO1999004828A3 (en) * 1997-07-28 1999-06-10 Fidia Advanced Biopolymers Srl Use of hyaluronic acid derivatives in the preparation of biomaterials
EP1174463A1 (en) * 1999-02-19 2002-01-23 Denki Kagaku Kogyo Kabushiki Kaisha Hyaluronic acid gel composition, process for producing the same, and medical material containing the same
EP1174463A4 (en) * 1999-02-19 2008-04-16 Denki Kagaku Kogyo Kk Hyaluronic acid gel composition, process for producing the same, and medical material containing the same
WO2001078692A2 (en) * 2000-04-13 2001-10-25 Color Access, Inc. Membrane delivery system
WO2001078692A3 (en) * 2000-04-13 2002-05-23 Color Access Inc Membrane delivery system
US6497887B1 (en) 2000-04-13 2002-12-24 Color Access, Inc. Membrane delivery system
GB2370277B (en) * 2000-12-21 2005-01-05 Matang Mfg Sdn Bhd Plant-based emollient-containing glove and method for making same
WO2003059404A2 (en) * 2002-01-18 2003-07-24 Cpn Spol. S R.O. Preparation for wound healing and prevention of bandage adhesion to the wound
WO2003059404A3 (en) * 2002-01-18 2004-03-18 Cpn Spol Sro Preparation for wound healing and prevention of bandage adhesion to the wound
LT5549B (en) 2007-07-23 2009-02-25 Cpn Spol. S R.O. Preparation for wound healing and prevention of bandage adhesion to the wound
JP2014114355A (en) * 2012-12-07 2014-06-26 Dainichiseika Color & Chem Mfg Co Ltd Method for manufacturing hyaluronic acid film, and hyaluronic acid film
EP3593973A4 (en) * 2017-03-07 2020-10-28 Jinwoo Bio Co., Ltd. Method for manufacturing hyaluronate film, and hyaluronate film manufactured thereby
US11298855B2 (en) 2017-03-07 2022-04-12 Jinwoo Bio Co., Ltd. Method for manufacturing hyaluronate film, and hyaluronate film manufactured thereby
US20200253876A1 (en) * 2017-10-12 2020-08-13 Solyplus Berlin Gmbh Methods of fabrication of concentrated and homogeneously wetted massive polymers and applications thereof
WO2023229557A1 (en) * 2022-05-23 2023-11-30 Ondokuz Mayis Universitesi Polymer composite film having properties of adhesion and healing on wet surfaces

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GB9514361D0 (en) 1995-09-13
GB2319729A (en) 1998-06-03
GB2319729B (en) 1999-07-21
GB9803131D0 (en) 1998-04-08
AU6698996A (en) 1997-02-10

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