WO1997016212A1 - Water soluble films - Google Patents

Water soluble films Download PDF

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Publication number
WO1997016212A1
WO1997016212A1 PCT/EP1996/004780 EP9604780W WO9716212A1 WO 1997016212 A1 WO1997016212 A1 WO 1997016212A1 EP 9604780 W EP9604780 W EP 9604780W WO 9716212 A1 WO9716212 A1 WO 9716212A1
Authority
WO
WIPO (PCT)
Prior art keywords
water soluble
film
wound
active substance
soluble polymer
Prior art date
Application number
PCT/EP1996/004780
Other languages
French (fr)
Inventor
Elizabeth Jacques
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 DK96938056T priority Critical patent/DK0861096T3/en
Priority to DE69623801T priority patent/DE69623801T2/en
Priority to AT96938056T priority patent/ATE224208T1/en
Priority to US09/066,400 priority patent/US6175054B1/en
Priority to EP96938056A priority patent/EP0861096B1/en
Priority to AU75628/96A priority patent/AU7562896A/en
Publication of WO1997016212A1 publication Critical patent/WO1997016212A1/en

Links

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
    • A61L15/42—Use of materials characterised by their function or physical properties
    • A61L15/44—Medicaments
    • 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
    • A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
    • A61K9/7007—Drug-containing films, membranes or sheets
    • 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
    • A61L15/24—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds; 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
    • 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
    • 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
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/10—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing inorganic materials
    • A61L2300/102—Metals or metal compounds, e.g. salts such as bicarbonates, carbonates, oxides, zeolites, silicates
    • A61L2300/104—Silver, e.g. silver sulfadiazine
    • 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
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
    • A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
    • 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
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
    • A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
    • A61L2300/406—Antibiotics
    • 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
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
    • A61L2300/428—Vitamins, e.g. tocopherol, riboflavin

Definitions

  • the invention relates to water soluble films and in particular water soluble films used to deliver an active substance to a wound.
  • active substances such as antioxidants, deodorants, perfumes or pharmacologically active substances in hydrocolloid wound dressings.
  • actives as optional ingredients in a composition forming the wound and skin contacting layer of a wound dressing.
  • Such compositions is described in EP-B-0092999, EP-B-130061 or EP-B-190814.
  • the composition comprises a homogeneous blend of hydrocolloid to absord exudate from the wound and an adhesive such as polyisobutylene to stick the dressing to the surrounding skin.
  • an adhesive such as polyisobutylene
  • An alternative wound dressing to a hydrocolloid based dressing is one based on fibres sometimes referred to as super-absorbant fibres.
  • Such fibres are described in WO-A- 93/12275 which describes modified cellulose fibres and in PCT/GB/9400102 which describes reprocessed alginate fibres.
  • active substances it is difficult to incorporate active substances into such fibres because of the processes used in their manufacture.
  • cellulose based fibres are produced according to a method which includes a step in which the fibres are washed with a solution containing a high proportion of industrial alcohol. The use of such a wash on fibres comprising an active substance may cause inactivity or a reduction in activity of the substance.
  • the invention provides a water soluble film having a thickness of from 0.03mm to 0.5mm comprising a water soluble polymer and an active substance.
  • the film thickness is from 0.01mm to 0.1mm.
  • Such a film may predictably and rapidly release active substance into a wound.
  • Such a film may be incorporated into a wound dressing as a separate layer which contacts the wound.
  • the invention provides a wound dressing comprising a water soluble film said film comprising a water soluble polymer and an active substance.
  • Such a film may be integrally formed as an outer layer of a dressing so as to allow rapid delivery of an active substance to the wound from the dressing. This has the advantage that the active is not subjected to the processing regime of the fibre.
  • Water soluble polymers suitable for use in the present invention include sodium carboxymethylcellulose and particularly those sodium carboxymethylcelluloses having a viscosity in the range of 200 to 800 mPas, sodium alginate, hyaluronic acid and in particular the sodium salt, hydroxypropylcellulose, polyvinylalcohol, and hydroxyethylcellulose.
  • the water soluble polymer is present at a level of from 20% to 99.5%, more preferably 30% to 94.5% and most preferably 60% to 90% by weight of the dry film.
  • Active substances suitable for use in the present invention include antibiotics such as polymyxin B and zinc bacitracin, antimicrobials such as metronidizole and silver sulphur diazine, broad spectrum antimicrobials such as PVPI and free radical scavengers such as vitamin A and vitamin E .
  • antibiotics such as polymyxin B and zinc bacitracin
  • antimicrobials such as metronidizole and silver sulphur diazine
  • broad spectrum antimicrobials such as PVPI
  • free radical scavengers such as vitamin A and vitamin E .
  • the active substance is present at a level of from 0.5% to 10%, more preferably 0.5% to 40% and most preferably 0.5% to 5% by weight of the dry film.
  • Films according to the present invention preferably comprise a plasticiser to increase the flexibility of the film.
  • plasticisers suitable for use in films of the present invention include propylene glycol, glycerol, depanthanol, sodium lactate, polyethylene glycol and sorbitol .
  • the plasticiser is preferably present at a level of from 5% to 80%, more preferably 30% to 60% by weight of the dry film.
  • Films according to the present invention preferably comprise a deodorising agent for example chlorophyllin or GrillocinTM.
  • a deodorising agent for example chlorophyllin or GrillocinTM.
  • the deodorising agent is preferably present at a level of from 0.5% to 15%, more preferably 1% to 10% by weight of the dry film.
  • Wound dressings comprising a water soluble film comprising a water soluble polymer and an active substance preferably comprise a substrate made from fibres of cellulose, alginate or hyaluronic acid to which the film is attached or a substrate of hydrocolloid such as that described in EP 92999B to which the film is attached.
  • the solution was allowed to de-aerate either by using a vacuum or with time.
  • the solution was then coated onto a suitable release paper (for example MelinexTM) at a coating thickness of approximately 1mm.
  • a suitable release paper for example MelinexTM
  • Fibrous substrates such as KALTOSTAT 1 " an alginate fibre dressing ex CV Laboratories Ltd and a fibrous dressing made as described in WO 9416746 was then placed on the film solution and caused to dry by placing them in an oven at 40 to 80°C for approximately half an hour to a final film thickness of about 0.1 mm.
  • the resulting dressing was irradiated by an ⁇ source of 25KGy and packaged in a polythene backed foil pouch. The irradiation had no detrimental effects on the dressing.
  • the dressings dissolved readily in water or in saline solution, were opaque and very flexible which allowed them to be cut using scissors.
  • the dressings were also sufficiently robust that they could be torn by hand. For the fibrous dressings without the water soluble film applied this was not possible.
  • Example 1 The method of Example 1 was repeated with the following aqueous solutions to make wound dressings according to the invention.
  • the resulting film had a tacky surface making it readily adhere to the fibrous substrates or dry skin.
  • a hydrocolloid substrate such as GRANUFLEX ex ConvaTec as described in EP92999B

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Hematology (AREA)
  • Materials Engineering (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Materials For Medical Uses (AREA)
  • Laminated Bodies (AREA)
  • Absorbent Articles And Supports Therefor (AREA)
  • Medicinal Preparation (AREA)
  • General Preparation And Processing Of Foods (AREA)
  • Jellies, Jams, And Syrups (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cosmetics (AREA)
  • Wrappers (AREA)

Abstract

A water soluble film having a thickness of from 0.03 mm to 0.5 mm comprising a water soluble polymer and an active substance.

Description

WATER SOLUBLE FILMS
The invention relates to water soluble films and in particular water soluble films used to deliver an active substance to a wound.
It is known to use active substances such as antioxidants, deodorants, perfumes or pharmacologically active substances in hydrocolloid wound dressings. In particular it is known to include actives as optional ingredients in a composition forming the wound and skin contacting layer of a wound dressing. Such compositions is described in EP-B-0092999, EP-B-130061 or EP-B-190814. Typically the composition comprises a homogeneous blend of hydrocolloid to absord exudate from the wound and an adhesive such as polyisobutylene to stick the dressing to the surrounding skin. Generally the delivery of the active substance from such a dressing is unpredictable and slow because the active is distributed throughout the adhesive layer and not concentrated at the wound and skin contacting sur ace.
An alternative wound dressing to a hydrocolloid based dressing is one based on fibres sometimes referred to as super-absorbant fibres. Such fibres are described in WO-A- 93/12275 which describes modified cellulose fibres and in PCT/GB/9400102 which describes reprocessed alginate fibres. In general, it is difficult to incorporate active substances into such fibres because of the processes used in their manufacture. For example in WO 93/12275 cellulose based fibres are produced according to a method which includes a step in which the fibres are washed with a solution containing a high proportion of industrial alcohol. The use of such a wash on fibres comprising an active substance may cause inactivity or a reduction in activity of the substance.
We have now found that it is possible to incorporate active substances into water soluble films that can be used as part of or in addition to a wound dressing to deliver active substances to a wound.
Accordingly the invention provides a water soluble film having a thickness of from 0.03mm to 0.5mm comprising a water soluble polymer and an active substance. Preferably the film thickness is from 0.01mm to 0.1mm.
Because of its thinness such a film may predictably and rapidly release active substance into a wound. Such a film may be incorporated into a wound dressing as a separate layer which contacts the wound.
Accordingly the invention provides a wound dressing comprising a water soluble film said film comprising a water soluble polymer and an active substance.
Such a film may be integrally formed as an outer layer of a dressing so as to allow rapid delivery of an active substance to the wound from the dressing. This has the advantage that the active is not subjected to the processing regime of the fibre.
Water soluble polymers suitable for use in the present invention include sodium carboxymethylcellulose and particularly those sodium carboxymethylcelluloses having a viscosity in the range of 200 to 800 mPas, sodium alginate, hyaluronic acid and in particular the sodium salt, hydroxypropylcellulose, polyvinylalcohol, and hydroxyethylcellulose. Preferably the water soluble polymer is present at a level of from 20% to 99.5%, more preferably 30% to 94.5% and most preferably 60% to 90% by weight of the dry film.
Active substances suitable for use in the present invention include antibiotics such as polymyxin B and zinc bacitracin, antimicrobials such as metronidizole and silver sulphur diazine, broad spectrum antimicrobials such as PVPI and free radical scavengers such as vitamin A and vitamin E . Preferably the active substance is present at a level of from 0.5% to 10%, more preferably 0.5% to 40% and most preferably 0.5% to 5% by weight of the dry film.
Films according to the present invention preferably comprise a plasticiser to increase the flexibility of the film. Examples of plasticisers suitable for use in films of the present invention include propylene glycol, glycerol, depanthanol, sodium lactate, polyethylene glycol and sorbitol . When present the plasticiser is preferably present at a level of from 5% to 80%, more preferably 30% to 60% by weight of the dry film.
Films according to the present invention preferably comprise a deodorising agent for example chlorophyllin or Grillocin™. When present the deodorising agent is preferably present at a level of from 0.5% to 15%, more preferably 1% to 10% by weight of the dry film.
Wound dressings according to the present invention comprising a water soluble film comprising a water soluble polymer and an active substance preferably comprise a substrate made from fibres of cellulose, alginate or hyaluronic acid to which the film is attached or a substrate of hydrocolloid such as that described in EP 92999B to which the film is attached.
The following examples illustrate preferred embodiments of the invention.
Example 1
An aqueous solution of the following components was made by dissolving the components in water:
% by weight
Sodium CMC 6% Propylene Glycol 4%
Silver sulphadiazine 0.1%
Water to 100%
The solution was allowed to de-aerate either by using a vacuum or with time. The solution was then coated onto a suitable release paper (for example Melinex™) at a coating thickness of approximately 1mm. Fibrous substrates such as KALTOSTAT1" an alginate fibre dressing ex CV Laboratories Ltd and a fibrous dressing made as described in WO 9416746 was then placed on the film solution and caused to dry by placing them in an oven at 40 to 80°C for approximately half an hour to a final film thickness of about 0.1 mm.
The resulting dressing was irradiated by an α source of 25KGy and packaged in a polythene backed foil pouch. The irradiation had no detrimental effects on the dressing.
The dressings dissolved readily in water or in saline solution, were opaque and very flexible which allowed them to be cut using scissors. The dressings were also sufficiently robust that they could be torn by hand. For the fibrous dressings without the water soluble film applied this was not possible.
Example 2
The method of Example 1 was repeated with the following aqueous solutions to make wound dressings according to the invention.
Solution 1
% by weight
Sodium CMC 6
Glycerol 14
Sodium silver diazine 0.2 water to 100
The resulting film had a tacky surface making it readily adhere to the fibrous substrates or dry skin.
Solution 2 % by weight
Sodium CMC 6
Propylene glycol 4
Metronidazole 0.08 Water to 100%
Solution 3
% by weight
Sodium CMC 6
Propylene Glycol 4
Zinc bacitracin 0.0079
Polymyxin B 0.0435
Water to 100%
Solution 4
% by weight Hydroxypropylcellulose 20 Zinc bacitracin 0.026
Polymyxin B 0.145 Water to 100%
Solution 5
% by weight Hydroxypropylcellulose 5 Glycerol 1.5
Povidone Iodine 3.25
Water to 100%
Example Using the method of Example 1 the solution of Example 1, solution 2 and solution 5 were coated onto separate release papers and dried. Fibrous dressings were not placed on the films but instead, the resulting films were then placed on the wound contacting surface of a hydrocolloid substrate such as GRANUFLEX ex ConvaTec as described in EP92999B so that only the central portion of the surface of the substrate was covered by the film. This allows the film to contact the wound without affecting the adhesive properties of the substrate on the surrounding skin.

Claims

1. A water soluble film having a thickness of from 0.03mm to 0.5mm comprising a water soluble polymer and an active substance.
2. A water soluble ilm as claimed in claim l wherein the film thickness is from 0.01mm to 0.1mm.
3. A wound dressing comprising a water soluble film said film comprising a water soluble polymer and an active substance.
4. A wound dressing as claimed in any preceding claim wherein the water soluble polymer is selected from the group comprising sodium carboxymethylcellulose and particularly those sodium carboxymethylcelluloses having a viscosity in the range of 200 to 800 mPas, sodium alginate, hyaluronic acid and in particular the sodium salt, hydroxypropylcellulose, polyvinylalcohol , and hydroxyethylcellulose.
5. A wound dressing as claimed in any preceding claim wherein the water soluble polymer is present at a level of from 20% to 99.5% by weight of the dry film.
PCT/EP1996/004780 1995-11-01 1996-10-31 Water soluble films WO1997016212A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
DK96938056T DK0861096T3 (en) 1995-11-01 1996-10-31 Water-soluble films
DE69623801T DE69623801T2 (en) 1995-11-01 1996-10-31 WATER-SOLUBLE FILM
AT96938056T ATE224208T1 (en) 1995-11-01 1996-10-31 WATER SOLUBLE FILM
US09/066,400 US6175054B1 (en) 1995-11-01 1996-10-31 Water soluble films
EP96938056A EP0861096B1 (en) 1995-11-01 1996-10-31 Water soluble films
AU75628/96A AU7562896A (en) 1995-11-01 1996-10-31 Water soluble films

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB9522314.5A GB9522314D0 (en) 1995-11-01 1995-11-01 Water soluble films
GB9522314.5 1995-11-01

Publications (1)

Publication Number Publication Date
WO1997016212A1 true WO1997016212A1 (en) 1997-05-09

Family

ID=10783182

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1996/004780 WO1997016212A1 (en) 1995-11-01 1996-10-31 Water soluble films

Country Status (10)

Country Link
US (1) US6175054B1 (en)
EP (1) EP0861096B1 (en)
AT (1) ATE224208T1 (en)
AU (1) AU7562896A (en)
DE (1) DE69623801T2 (en)
DK (1) DK0861096T3 (en)
ES (1) ES2183013T3 (en)
GB (1) GB9522314D0 (en)
PT (1) PT861096E (en)
WO (1) WO1997016212A1 (en)

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WO1999008691A2 (en) * 1997-08-14 1999-02-25 Periodontix, Inc. Use of locally delivered metal ions for treatment of periodontal disease
EP1057481A1 (en) * 1998-11-18 2000-12-06 Medical Industries Corporation Agents for repairing damaged tissue sites

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US7612248B2 (en) * 2002-12-19 2009-11-03 3M Innovative Properties Company Absorbent medical articles
FR2880262B1 (en) * 2005-01-03 2013-11-08 Oreal COSMETIC OR DERMATOLOGICAL ARTICLE COMPRISING A WATER-SOLUBLE SUPPORT
US20070110792A9 (en) * 2005-01-03 2007-05-17 L'oreal Cosmetic or dermatological article comprising a medium that is soluble in water
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US7935647B2 (en) * 2006-12-15 2011-05-03 E. I. Du Pont De Nemours And Company Laminates of acid polysaccharide films
US8232238B2 (en) 2010-06-03 2012-07-31 The Clorox Company Concentrated film delivery systems
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JP7127135B2 (en) 2018-01-26 2022-08-29 ザ プロクター アンド ギャンブル カンパニー Water soluble products and related processes
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US11053466B2 (en) 2018-01-26 2021-07-06 The Procter & Gamble Company Water-soluble unit dose articles comprising perfume
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US10982176B2 (en) 2018-07-27 2021-04-20 The Procter & Gamble Company Process of laundering fabrics using a water-soluble unit dose article
WO2020159860A1 (en) 2019-01-28 2020-08-06 The Procter & Gamble Company Recycleable, renewable, or biodegradable package
EP3712237A1 (en) 2019-03-19 2020-09-23 The Procter & Gamble Company Fibrous water-soluble unit dose articles comprising water-soluble fibrous structures
US11679066B2 (en) 2019-06-28 2023-06-20 The Procter & Gamble Company Dissolvable solid fibrous articles containing anionic surfactants
MX2023001042A (en) 2020-07-31 2023-02-16 Procter & Gamble Water-soluble fibrous pouch containing prills for hair care.

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EP0386960A2 (en) * 1989-03-07 1990-09-12 American Cyanamid Company Pharmaceutical compositions useful as drug delivery vehicles and/or as wound dressings
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Cited By (5)

* Cited by examiner, † Cited by third party
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WO1999008691A2 (en) * 1997-08-14 1999-02-25 Periodontix, Inc. Use of locally delivered metal ions for treatment of periodontal disease
WO1999008691A3 (en) * 1997-08-14 1999-05-06 Periodintix Inc Use of locally delivered metal ions for treatment of periodontal disease
US6153210A (en) * 1997-08-14 2000-11-28 Periodontix, Inc. Use of locally delivered metal ions for treatment of periodontal disease
EP1057481A1 (en) * 1998-11-18 2000-12-06 Medical Industries Corporation Agents for repairing damaged tissue sites
EP1057481A4 (en) * 1998-11-18 2001-11-07 Medical Ind Corp Agents for repairing damaged tissue sites

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GB9522314D0 (en) 1996-01-03
DE69623801D1 (en) 2002-10-24
US6175054B1 (en) 2001-01-16
ATE224208T1 (en) 2002-10-15
AU7562896A (en) 1997-05-22
DE69623801T2 (en) 2003-08-07
EP0861096A1 (en) 1998-09-02
EP0861096B1 (en) 2002-09-18
ES2183013T3 (en) 2003-03-16
PT861096E (en) 2002-11-29
DK0861096T3 (en) 2002-12-23

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