US20160106879A1 - Antiseptic wound dressing - Google Patents

Antiseptic wound dressing Download PDF

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Publication number
US20160106879A1
US20160106879A1 US14/888,259 US201314888259A US2016106879A1 US 20160106879 A1 US20160106879 A1 US 20160106879A1 US 201314888259 A US201314888259 A US 201314888259A US 2016106879 A1 US2016106879 A1 US 2016106879A1
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US
United States
Prior art keywords
antiseptic
cyclodextrin
material according
carrier material
betaine
Prior art date
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Abandoned
Application number
US14/888,259
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English (en)
Inventor
Harald K. Horchler
Hans-Jürgen Buschmann
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Hawest Research AG
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Hawest Research AG
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Assigned to Hawest Research AG reassignment Hawest Research AG ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HORCHLER, HARALD K., BUSCHMANN, Hans-Jürgen
Publication of US20160106879A1 publication Critical patent/US20160106879A1/en
Abandoned legal-status Critical Current

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    • 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
    • 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
    • A61L15/20—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing organic materials
    • 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
    • A61L15/425—Porous materials, e.g. foams or sponges
    • 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
    • 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
    • A61L15/46—Deodorants or malodour counteractants, e.g. to inhibit the formation of ammonia or bacteria
    • 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
    • A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
    • A61L2300/204—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials with nitrogen-containing functional groups, e.g. aminoxides, nitriles, guanidines
    • A61L2300/206—Biguanides, e.g. chlorohexidine
    • 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
    • A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
    • A61L2300/23—Carbohydrates
    • 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
    • A61L2300/80—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special chemical form
    • A61L2300/802—Additives, excipients, e.g. cyclodextrins, fatty acids, surfactants

Definitions

  • the invention relates to an antiseptic material, which in particular can also be used for wound dressings. It contains a carrier material and one or more antiseptics and a surfactant.
  • Antiseptically finished materials for the clinical area, especially for wound care, but also for cosmetic and other purposes, are widely known and in use. Such materials consist as a rule of a carrier material, which is finished with one or more antiseptics. Both textile materials and non-textile materials, such as polymer films and foams, come into question as carrier material.
  • chlorhexidine polyethylenimine (Lupasol®), spermine, triethylenetetramine or also polyhexanide (PHMB, poly(hexamethylene biguanide) hydrochloride
  • PHMB poly(hexamethylene biguanide) hydrochloride
  • an antiseptic finish of textiles for the health care or the infection protection in which the finish remains active over longer time, would also be desirable.
  • the task of the invention is the provision of an antiseptic material which retains its effectiveness over longer time but simultaneously acts less toxically on human and animal cells, is simple to manufacture and simple to handle.
  • This task is accomplished with an antiseptic material of the type mentioned initially, in which the carrier material is finished with a cyclodextrin or cyclodextrin derivative, which is loaded with the antiseptic or with several antiseptics.
  • any material that is finished antiseptically in the described way is understood as antiseptic material.
  • a material respectively has a carrier material, which contains an antiseptic and a surfactant.
  • Textile materials in particular come into question as carrier material, wherein they may be woven textile fabrics or nonwovens.
  • Plastics also come into question as carrier material, especially porous plastic foams, as find application in the medicine in the wound treatment, especially open-porous polyurethanes, which qualify as eminently body-friendly.
  • textile materials includes all types and forms of natural and synthetic fibers and textiles produced from them. Woven and nonwoven fabrics of cotton and polyester can be mentioned in particular.
  • the carrier materials used according to the invention are finished with a cyclodextrin or cyclodextrin derivative.
  • the known ⁇ -, ⁇ - and ⁇ -cyclodextrin forms are understood as cyclodextrins, wherein they are cyclic sugar molecules with 6, 7 or 8 ⁇ -D-glucose units.
  • These cyclodextrins may be derivatized in the usual way.
  • they may be provided with anchor groups known in and for themselves, via which a binding to a carrier material takes place. This binding may take place in chemical way, in physical way via interactions or else purely mechanically via so-called anchor groups, which interlock with the carrier material.
  • a physical binding takes place, for example, via electrostatic interactions or via chemical interactions between the molecule or its derivative, for example hydrophilic/hydrophobic interactions of the cyclodextrin with the surroundings and the surface of the carrier material. All of these methods are adequately described in the literature.
  • cyclodextrin derivatives derivatives of the ⁇ -, ⁇ - and ⁇ -cyclodextrins are known that in addition to an anchor group have a further functionalization in order to achieve desired effects. Such derivatives are to be selected such that they exert not any negative but if necessary a positive influence on the complex formation of the cyclodextrin with the antiseptic.
  • surfactants come into question as surfactants, but especially betaines. Especially undecylenic amidopropyl betaine and trimethylammonium acetate would have to be mentioned here. As a rule the surfactants are bound not to the cyclodextrin but instead via electrostatic interactions to the carrier material.
  • the carrier material coming into use according to the invention as a rule contains 1 to 5 wt % cyclodextrin or derivative thereof, especially 3 wt %, relative to the weight of the carrier material. Investigations have shown that, with proper process control, almost all cyclodextrin units are loaded in the usual case with one molecule of the antiseptic, i.e. the ratio of the cyclodextrin molecules to the molecules of the antiseptic lies in the range of 0.1 to 1.0. Where the surfactant or betaine is concerned, as a rule it is contained in the antiseptic material approximately in the same amount as the antiseptic.
  • the antiseptic material according to the invention has a high bactericidal activity and in addition is antivirally and fungicidally active.
  • the fungicidal activity is obtained above all by the addition of the betaine, which is capable of detaching biofilms from wound surfaces and of promoting the penetration of the antiseptic into the wound. It exerts a kind of entrainment effect.
  • Tests with pathogenic germs, especially of S. aureus, E. coli and C. albicans have achieved a practically 100% inhibition of the microorganism in a short time.
  • cyclodextrins are suitable for assimilating protein substances and other decomposition products of body cells and of removing them from the surroundings. A healing-promoting and simultaneously also odor-reducing effect is derived from this. The wound is kept cleaner on the whole. Associated with the assimilation of such decomposition products is the release of antiseptics, which are contained in the cyclodextrin and which in this way are delivered gradually into the wound region. This is responsible for the lasting effect of the antiseptic materials according to the invention.
  • the antiseptic materials according to the invention may be used for a multiplicity of purposes. This is especially the use in conjunction with the wound care as wound dressing, bandage material or plasters. Foams may be used for the filling of wounds in the course of a vacuum therapy. Furthermore, in the clinical area, everyday textiles for health care, such as bed linens, gowns, patient clothing and the like, may be finished accordingly. A further application is that in cosmetic patches, and also for work garments outside hospitals in areas in which contamination with microorganisms cannot be ruled out. Finally, such a finish may also be used for the surface treatment of garments that are used for the protection of the transmission of bacteria and viruses and, for example, is specified for Mecca mits. Everyday textiles may be reloaded after the laundering.
  • Particularly preferred antiseptic materials have a carrier material that is finished with ⁇ -cyclodextrin that is loaded with polyhexanide.
  • Undecylenic amidopropyl betaine is present as the betaine.
  • This cyclodextrin is bound via an anchor group to a polysaccharide, which will be applied onto the carrier material.
  • common gel-forming polysaccharides come into question as the polysaccharide, such as carrageenan, tragacanth, guar, fucoidan or alginate.
  • the binding of the cyclodextrin takes place by reaction of monochlorotriazenyl- ⁇ -cyclodextrin in water at an elevated temperature (90° C.) in the presence of sodium hydroxide solution at a pH of 11 to 12.
  • the product so obtained, in which the ⁇ -cyclodextrin is bound to the polysaccharide, may be applied durably onto the carrier material by spraying or padding. It remains there even after several launderings.
  • the loading of the cyclodextrin with the antiseptic takes place by immersing the carrier material in a solution of the antiseptic, by spraying the antiseptic or by reacting the monochlorotriazenyl- ⁇ -cyclodextrin with the polysaccharide in the presence of the antiseptic manufactured. In the latter case, it must be ensured that undesired side reactions do not occur.
  • a further preferred form of the binding of the cyclodextrin to the carrier material may be achieved via polyvinylamine or polyethylenimine.
  • ⁇ -Cyclodextrin-substituted polyvinylamine or polyethylenimine adheres excellently to the surface of textiles, but also of polyurethane foams, which is why correspondingly finished carrier material is also suitable in particular for wound treatment, but also for garments.
  • the invention also relates to an aqueous solution, which contains a cyclodextrin bound to a polyvinylamine or polyethylenimine, which is loaded with polyhexamide and additionally contains undecylenic amidopropyl betaine.
  • PHMB/betaine complex or complex a carrier material that is finished with 3% polyvinylamine- ⁇ -cyclodextrin and is loaded with approximately equal amounts of PHMB and undecylenic amidopropyl betaine, hereinafter referred to as the PHMB/betaine complex or complex, has a series of advantageous properties:
  • solutions prepared in the following examples are suitable for the spraying of textile materials, foams, etc. of the most diverse materials, such as, for example, polyester, cotton, polyacrylonitrile, glass fibers, polyurethane, etc.
  • the fixation of the cyclodextrin derivatives takes place by electrostatic and hydrophobic interactions with the respective surface.
  • the cyclodextrin derivatives synthesized in this example do not have any kind of biostatic effects.
  • the biostatic action of the finish can be determined by means of the formazan test (F. P. Altman, Progr. Histochem. Cytochem. 9 (1976); W. Oppermann, R. Gutmann, S. Schmitt, E. Held-Föhn, Textilveredelung 37, 19 (2003)).
  • Suitable cyclodextrin derivatives are described in the corresponding patent literature.
  • the preparation of monochlorotriazine-substituted ⁇ -cyclodextrin is known from DE 44 29 229 and of further cyclodextrin derivatives with one or more reactive anchor groups from DE 101 55 781.
  • a binding of cyclodextrin to fibrous materials is also possible by the use of bifunctional or polyfunctional reagents, such as via diisocyanates and the like (W. Volz, Anti-Smell Finishes in Textile Processing, Textilveredelung 38, 17 (2003)), or by the use of dimethylureas and similar compounds, such as are also used for crease-resistant finishing of cellulosic materials (H.-J. Burschmann, D. Knittel, E. Schollmeyer: Crease-resistant finishing of cotton in the presence of cyclodextrins for incorporation of fragrances, Melliand Textilbiler. 72, 198 (1991)).
  • chlorhexidine and polyhexanide in aqueous solution are used as antiseptics.
  • A) The textile material or the foam is finished with cyclodextrins.
  • an aqueous solution of a cyclodextrin derivative (see above) or an aqueous solution of a cyclodextrin substituted with polyvinylamine or polyethylenimine (approx. 3% cyclodextrin content) is sprayed onto the material to be finished.
  • An aqueous solution of the antiseptic (0.08 to 0.22% PHMB; 0.1 to 0.15% betaine) is sprayed simultaneously, wherein both solutions must have a pH of 5 to 7, since otherwise the formation of a precipitate takes place.
  • the textile material or the foam is finished with cyclodextrins.
  • cyclodextrins For this purpose, an aqueous solution of a cyclodextrin derivative (see above) or an aqueous solution of a cyclodextrin substituted with polyvinylamine or polyethylenimine (approx. 3% cyclodextrin content) with a pH of 5 to 7 is sprayed onto the material to be finished and dried. Then an aqueous solution of the antiseptic (0.1% PHMB; 0.1% betaine) is sprayed. The application of both solutions may also be performed by means of a padding machine.
  • a mixture of the cyclodextrin derivative (see above) or of a cyclodextrin substituted with polyvinylamine or polyethylenimine and of the antiseptic is prepared in aqueous solution by mixing both components (equimolar, preferably 0.001 to 0.01 mol/L), wherein the aqueous phase must have a pH of 5 to 7, in order to prevent the formation of an insoluble precipitate.
  • the resulting aqueous solution is sprayed onto the textile material or is applied onto the textile material or the foam by an application by means of a padding machine.
  • a woven cotton fabric is immersed in an aqueous solution of monochlorotriazinyl- ⁇ -cyclodextrin (sodium salt, 20-100 g/L) (Cavasol® W7 MCT, Wacker-Chemie GmbH), which has been adjusted to a pH of 4 to 6 with acetic acid (60%). Then the fabric is quetched on a padding machine (liquor uptake approx. 70%). Thereafter the fabric is predried at 80° C. for 10 minutes and then fixed at 160° C. for 7 minutes. Then an aqueous solution of the antiseptic (0.1% PHMB) is sprayed on or applied by an application by means of a padding machine. At the same time or subsequently, the betaine is applied from aqueous solution (0.1% betaine).
  • monochlorotriazinyl- ⁇ -cyclodextrin sodium salt, 20-100 g/L
  • acetic acid 60%
  • the fabric is quetched on a padding machine (li
  • the FIGURE schematically shows a cyclodextrin molecule with polyhexamide loading and an anchor group, which mechanically anchors the cyclodextrin onto a textile fiber.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Epidemiology (AREA)
  • Hematology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dispersion Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Medicinal Preparation (AREA)
US14/888,259 2012-03-02 2013-03-01 Antiseptic wound dressing Abandoned US20160106879A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE102012004024.5 2012-03-02
DE102012004024A DE102012004024A1 (de) 2012-03-02 2012-03-02 Wundauflage
PCT/EP2013/054132 WO2013127983A1 (de) 2012-03-02 2013-03-01 Antiseptische wundauflage

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2013/054132 A-371-Of-International WO2013127983A1 (de) 2012-03-02 2013-03-01 Antiseptische wundauflage

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US18/062,678 Continuation US20230096579A1 (en) 2012-03-02 2022-12-07 Antiseptic wound dressing

Publications (1)

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US20160106879A1 true US20160106879A1 (en) 2016-04-21

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Application Number Title Priority Date Filing Date
US14/888,259 Abandoned US20160106879A1 (en) 2012-03-02 2013-03-01 Antiseptic wound dressing
US18/062,678 Pending US20230096579A1 (en) 2012-03-02 2022-12-07 Antiseptic wound dressing

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Application Number Title Priority Date Filing Date
US18/062,678 Pending US20230096579A1 (en) 2012-03-02 2022-12-07 Antiseptic wound dressing

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US (2) US20160106879A1 (da)
EP (1) EP2819711B1 (da)
DE (1) DE102012004024A1 (da)
DK (1) DK2819711T3 (da)
WO (1) WO2013127983A1 (da)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109329588A (zh) * 2018-10-24 2019-02-15 浙江海洋大学 深水网箱养殖用的海水鱼配合饲料

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106963974A (zh) * 2017-05-26 2017-07-21 江苏耐雀生物工程技术有限公司 一种含紫草素的创可贴及其制备方法
BR112020026571A2 (pt) * 2018-07-04 2021-03-23 Coloplast A/S Curativo de ferida fibroso, e, método para fabricar um curativo de ferida fibroso.
CN112334162A (zh) * 2018-07-04 2021-02-05 科洛普拉斯特公司 包括抗菌剂的泡沫伤口敷料

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Publication number Priority date Publication date Assignee Title
US20040031107A1 (en) * 2000-10-17 2004-02-19 Ulrich Pegelow Cleaning material
DE102004008913A1 (de) * 2004-02-24 2005-09-08 Henkel Kgaa Cyclodextrinderivat mit einem Ionen
US7604816B2 (en) * 2004-05-07 2009-10-20 Resorba Wundversorgung Gmbh & Co. Kg Bio-absorbable collagen-based wound dressing

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Publication number Priority date Publication date Assignee Title
DE4429229A1 (de) 1994-08-18 1996-02-22 Consortium Elektrochem Ind Cyclodextrinderivate mit mindestens einem stickstoffhaltigen Heterozyklus, ihre Herstellung und Verwendung
DE10155781A1 (de) 2001-11-14 2003-05-22 Deutsches Textilforschzentrum Verfahren zur Herstellung von reaktiven Cyclodextrinen, ein damit ausgerüstetes textiles Material und deren Verwendung
CA2637720A1 (en) * 2006-02-28 2007-09-07 Tyco Healthcare Group Lp Antimicrobial medical devices

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040031107A1 (en) * 2000-10-17 2004-02-19 Ulrich Pegelow Cleaning material
DE102004008913A1 (de) * 2004-02-24 2005-09-08 Henkel Kgaa Cyclodextrinderivat mit einem Ionen
US7604816B2 (en) * 2004-05-07 2009-10-20 Resorba Wundversorgung Gmbh & Co. Kg Bio-absorbable collagen-based wound dressing

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109329588A (zh) * 2018-10-24 2019-02-15 浙江海洋大学 深水网箱养殖用的海水鱼配合饲料

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Publication number Publication date
EP2819711B1 (de) 2020-11-11
DE102012004024A1 (de) 2013-09-05
WO2013127983A1 (de) 2013-09-06
US20230096579A1 (en) 2023-03-30
EP2819711A1 (de) 2015-01-07
DK2819711T3 (da) 2021-02-15

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