WO2012167936A2 - Combinaisons de principes actifs comprenant de l'є-polylysine (epsilon-polylysine) et un ou plusieurs terpènes - Google Patents

Combinaisons de principes actifs comprenant de l'є-polylysine (epsilon-polylysine) et un ou plusieurs terpènes Download PDF

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Publication number
WO2012167936A2
WO2012167936A2 PCT/EP2012/002425 EP2012002425W WO2012167936A2 WO 2012167936 A2 WO2012167936 A2 WO 2012167936A2 EP 2012002425 W EP2012002425 W EP 2012002425W WO 2012167936 A2 WO2012167936 A2 WO 2012167936A2
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WO
WIPO (PCT)
Prior art keywords
polylysine
terpenes
cosmetic
skin
preparations
Prior art date
Application number
PCT/EP2012/002425
Other languages
German (de)
English (en)
Other versions
WO2012167936A3 (fr
Inventor
Bernd Traupe
Laura PRIEBE
Michael WÖHRMANN
Christian Dingler
Original Assignee
Beiersdorf Ag
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
Priority claimed from DE201110077070 external-priority patent/DE102011077070A1/de
Priority claimed from DE201110077077 external-priority patent/DE102011077077A1/de
Application filed by Beiersdorf Ag filed Critical Beiersdorf Ag
Priority to EP12728396.8A priority Critical patent/EP2717838A2/fr
Priority to BR112013027487A priority patent/BR112013027487A2/pt
Publication of WO2012167936A2 publication Critical patent/WO2012167936A2/fr
Publication of WO2012167936A3 publication Critical patent/WO2012167936A3/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • 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
    • A61K8/88—Polyamides
    • 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
    • A61Q19/008—Preparations for oily skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/006—Antidandruff preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • 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
    • A61K2800/52—Stabilizers
    • A61K2800/522—Antioxidants; Radical scavengers

Definitions

  • the present invention relates to drug combinations of ⁇ -polylysine (epsilon-polylysine) and one or more terpenes, as well as cosmetic or dermatological preparations containing such drug combinations and their use as against
  • Bacteria, mycota and viruses are effective substances.
  • the healthy warm-blooded organism especially the healthy human skin, is populated with a variety of non-pathogenic microorganisms.
  • This so-called microflora of the skin is not only harmless, it represents an important protection against opportunistic or pathogenic germs.
  • Bacteria belong to the prokaryotic ones. They can roughly fit their shape (sphere, cylinder, curved cylinder) as well as the structure of their cell wall (gram-positive,
  • antibiotics for example, which is not applicable to all antimicrobial substances, can be dated to the year 1941, although the first findings on penicillin were already found in 1929. Antibiotics in the modern sense are not for all medical, already not suitable for cosmetic applications, as often the warm-blooded
  • Organism such as the diseased patient, is impaired in any way in its metabolic functions when used.
  • An object of the present invention was therefore to enrich the state of the art in this direction, in particular therefore to provide substances which are available against
  • Gram-positive and / or Gram-negative bacteria are effective, without the use of the substances would be an unacceptable impairment of the health of the user would be connected.
  • Gram-negative bacteria are, for example, Escherichia coli, Pseudomonas species and
  • Enterobacteriaceae such as Citrobacter.
  • Gram-positive bacteria also play a role in cosmetics and dermatology.
  • bacterial secondary infections of etiological importance are, among other influences.
  • One of the most important microorganisms associated with impure skin is Propionibacterium acnes.
  • Impure skin and / or comedones affect the well-being of those affected but even in mild cases. Since virtually every adolescent or person is affected by blemished skin of some kind, many people need to remedy this condition.
  • a particular object of the present invention was therefore to find a substance or combination of substances which is effective against impure skin or Propionibacterium acnes.
  • the present invention relates to cosmetic deodorants.
  • Such formulations serve to eliminate body odor, which arises when the per se odorless fresh sweat is decomposed by especially gram-positive microorganisms.
  • the usual cosmetic deodorants are based on different active principles.
  • liquid deodorants for example aerosol sprays, roll-ons and the like, as well as solid preparations, for example deodorant sticks ("sticks"), powders, powder sprays, intimate cleaners, etc.
  • antiperspirants can be prevented by astringents - mainly aluminum salts such as aluminum hydroxychloride (Aluchlorhydrat) - the formation of sweat.
  • Aluchlorhydrat aluminum hydroxychloride
  • the bacterial flora on the skin can be reduced.
  • only the odor causing microorganisms should be effectively reduced. In practice, however, it has been found that the entire microflora of the skin can be affected.
  • the sweat flow itself is not affected by this, in the ideal case, only the microbial decomposition of the sweat is temporarily stopped.
  • body odor can also be masked by fragrances, a method that is least in line with the consumer's aesthetic needs, as the mixture of body odor and perfume smells rather unpleasant.
  • Deodorants should fulfill the following conditions:
  • Another object of the present invention was therefore to develop cosmetic deodorants which do not have the disadvantages of the prior art.
  • the deodorants should protect the microflora of the skin largely, but selectively reduce the number of microorganisms that are responsible for the body odor.
  • a further object was to develop cosmetic deodorants which harmonize with the widest possible variety of customary cosmetic auxiliaries and additives, in particular with the perfume ingredients which are especially important in deodorizing or antiperspirant formulations.
  • Yet another object of the invention was to provide cosmetic deodorants which are effective over a prolonged period, on the order of at least half a day, without noticeably reducing their effect.
  • Mushrooms also called fungi, mycota or mycobionts, count as eucaryotes in contrast to the bacteria. Eucaryotes are living beings, whose cells (Eucyten), in contrast to those of the so-called Procaryonten (Procyten) over one by nuclear envelope and nuclear membrane have the nucleus delimited from the rest of the cytoplasm. The nucleus contains the genetic information stored in chromosomes.
  • mycobionts include, for example, yeasts (Protoascomycetes), molds (Plectomycetes), mildew (Pyrenomycetes), downy mildew (Phycomycetes) and wild mushrooms (Basidiomycetes).
  • Fungi are not plant organisms, but like these they have a cell wall, cell-filled vacuoles, and a microscopically visible plasma flow. They contain no photosynthetic pigments and are C-heterotrophic. They grow under aerobic conditions and gain energy through oxidation of organic substances. However, some representatives, such as yeasts, are facultative anaerobes and capable of producing energy through fermentation processes.
  • Dermatomycoses are diseases in which certain types of fungi, especially dermatophytes, invade the skin and hair follicles.
  • the symptoms of dermatomycoses include blisters, exfoliation, rhagades and erosion, usually associated with itching or allergic eczema.
  • Dermatomycoses can be subdivided essentially into the following four groups: dermatophytic (for example, epidermophytic, favus, microspore, trichophytic), yeast mycoses (e.g.
  • Pityriasis and other pityrosporum-related mycoses candidal infections, blastomycosis, Buschke's disease, torulosis, piedra alba, torulopsidosis, trichosporosis
  • Mold mycoses e.g., aspergillosis, cephalosporidosis, phycomycosis and scopolular isopidosis
  • systemic mycoses e.g., chromomycosis, coccidiomycosis, histoplasmosis
  • the pathogenic and facultative pathogens include, for example, Candida species (e.g., Candida albicans) and those of the family Pityrosporum from the group of yeasts.
  • topically administered antibiotics have the disadvantage that they free the skin flora not only from the secondary pathogen, but also the inherently physiological skin flora strong
  • the object of the present invention was to eliminate the disadvantages of the prior art and to provide substances and preparations containing such substances, which in the broadest sense prevent, combat or avert microbial infestation.
  • Active substance combinations comprising: a) ⁇ -polylysine (epsilon-polylysine)
  • one or more terpenes for example esters with terpene structure have synergistic antimicrobial action and remedy the disadvantages of the prior art.
  • ⁇ -Polylysine represents a polymer in which the ⁇ -terminal amino group of a lysine molecule is linked to the acid function of another lysine molecule
  • the index "n" (more precisely, the value n / 2) defines the degree of polymerization of the polylysine.
  • the INCI name is poly [imino [(2S) -2-amino-1-oxo-1,6-hexanediyl]], it has the CAS no. 28211-04-3
  • the homopolymer ⁇ -polylysine is known to be described and used as an antimicrobial agent against yeasts, fungi and gram-positive and gram-negative bacteria. Currently it is used as a preservative, especially in Japan, Korea and the US.
  • the homopolymer ⁇ -polylysine is known to be described and used as an antimicrobial agent against yeasts, fungi and gram-positive and gram-negative bacteria. Currently it is used as a preservative, especially in Japan, Korea and the US.
  • Production of the ⁇ -polylysine takes place via a natural fermentative process.
  • ⁇ -polylysines which have a degree of polymerization n / 2 of from 2 to 200, preferably from 10 to 100, particularly preferably from 23 to 35.
  • ⁇ -polylysine is preferably used in cosmetic or dermatological compositions in a content of 0.0005-50.0% by weight, in particular 0.01-20.0% by weight, based on the total weight of the composition.
  • compositions advantageously contain 0.02-10.0% by weight, more preferably 0.02-5.0% by weight, of ⁇ -polylysine, very particularly preferably 0.05-0.5% by weight, in each case based on the total weight of the composition.
  • ⁇ -Polylysine is readily incorporated into common cosmetic or dermatological formulations, advantageously in pump sprays, aerosol sprays, creams, ointments, tinctures, lotions, nail care products (e.g., nail polishes, nail polish removers, nail balms) and the like.
  • Terpenes are a highly heterogeneous and very large group of chemical compounds that naturally occur as secondary ingredients in organisms. They are formally derived from isoprene and are characterized by a large variety of carbon skeletons and low number of functional groups. There are over 8,000 terpenes and over 30,000 closely related terpenoids known. Most terpenes are natural products, mainly of plant and rare animal origin. In nature come predominantly
  • the terpenes are the main component of the essential oils produced in plants.
  • terpenes The original classification of terpenes is based on the observation that they can often be formally described as a series of isoprene units.
  • Isoprene units a diterpene and so on.
  • the terpene are selected from the group of mono-, sesqui- and diterpenes.
  • terpenes Menthol, citronellol, geraniol, nero, linalool and terpineol, bomeol, thujol, sabinol, myrtenol, thymol, verbenol, fenchol, piperitol, (perillaaldehyde, phellandral, citronellal, citral, myrtenal, menthone, piperone, pulegone, carvone, thujone, umbellulone , Verbenone, chrysanthenone, fenchone, camphor) cineole, menthofuran, linalooloxide, rose oxide, or peroxides such as ascaridol or qinghaosu (artemisinin).
  • the or the terpenes are selected from the group of mono-, sesqui- and diterpenes which have one or more hydroxyl functions.
  • ester with terpene structure is particularly preferred according to the invention:
  • Terpene structure preferably used in cosmetic or dermatological compositions a content of 0.0005 - 50.0 wt .-%, in particular 0.001 - 20.0 wt .-%, based on the total weight of the composition are preferred.
  • the compositions advantageously contain 0.02-10.0% by weight, more preferably 0.001-5.0% by weight, of the terpenes used according to the invention, very particularly preferably 0.001-2.5% by weight, based in each case on the Total weight of the composition.
  • the total of one or more terpenes on the other hand, of 10: 1 to 1; 100, advantageously from 5: 1 to 1 to 20, in particular advantageously selected from 1: 1 to 1: 0.
  • the active compound combinations used according to the invention are particularly suitable for use as a deodorizing active ingredient in cosmetic deodorants as well as against impure skin and mild forms of acne.
  • Active substance combinations can prevent spoilage of organic substances, in particular cosmetic and dermatological preparations, by infestation with Gram-positive and Gram-negative bacteria, cyanoids and viruses when added to these preparations.
  • the individual active ingredients used according to the invention can be incorporated without difficulty into customary cosmetic or dermatological formulations, advantageously in pump sprays, aerosol sprays, creams, ointments, tinctures, lotions, nail care products (e.g.
  • the individual active ingredients used according to the invention are advantageously in the form of antidandruff shampoos.
  • a pH range of 3.5 to 7.5 is advantageous. It is particularly favorable to choose the pH in a range of 4.0-6.5.
  • the cosmetic and / or dermatological formulations according to the invention may be composed as usual and used for the treatment of the skin and / or the hair in the sense of a dermatological treatment or a treatment in the sense of nourishing cosmetics. But they can also be used in make-up products in decorative cosmetics.
  • the cosmetic and / or dermatological formulations according to the invention are applied to the skin and / or the hair in a sufficient amount in the manner customary for cosmetics and dermatological agents.
  • cosmetic and dermatological preparations that are in the form of a sunscreen.
  • these additionally contain at least one UVA filter and / or at least one UVB filter and / or at least one inorganic pigment.
  • Cosmetic preparations according to the invention for protecting the skin from UV rays may be in various forms, such as e.g. Usually used for this type of preparations. So they can e.g. a solution, a water-in-oil (W / O) or oil-in-water (O / W) type emulsion, or a multiple emulsions, such as water-in-oil-in-water (W / O / W), a gel, a hydrodispersion, a solid stick or even an aerosol.
  • W / O water-in-oil
  • O / W oil-in-water
  • the cosmetic preparations according to the invention may contain cosmetic adjuvants such as are commonly used in such preparations, e.g. Antioxidants, perfumes, antifoaming agents, colorants, pigments which have a coloring effect, thickeners, surface-active substances, emulsifiers,
  • cosmetic adjuvants such as are commonly used in such preparations, e.g. Antioxidants, perfumes, antifoaming agents, colorants, pigments which have a coloring effect, thickeners, surface-active substances, emulsifiers,
  • softening substances moisturizing and / or moisturizing substances, fats, oils, waxes or other customary constituents of a cosmetic formulation, such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.
  • Emulsions are advantageous according to the invention and contain e.g. the said fats, oils, waxes and other fatty substances, as well as water and an emulsifier, as commonly used for such a type of formulation.
  • Gels according to the invention usually contain low C number alcohols, e.g. Ethanol, isopropanol, 1, 2-propanediol, glycerol and water or an above-mentioned oil in
  • a thickening agent which in oily-alcoholic gels preferably silica or an aluminum silicate, in aqueous-alcoholic or alcoholic gels
  • Solid sticks according to the invention contain, for example, natural or synthetic waxes, fatty alcohols or fatty acid esters. Preference is given to lip balms and deodorant sticks ("deodorant sticks").
  • Suitable propellants for cosmetic or dermatological preparations which can be sprayed from aerosol containers according to the invention are the customary known highly volatile, liquefied propellants, e.g. Hydrocarbons (propane, butane, isobutane) suitable, which can be used alone or in combination with each other. Also, compressed air is advantageous to use.
  • Hydrocarbons propane, butane, isobutane
  • the preparations according to the invention may also contain substances which absorb UV radiation in the UVB range, the total amount of the filter substances being e.g. 0.1 wt .-% to 30 wt .-%, preferably 0.5 to 10 wt .-%, in particular 1 to 6 wt .-%, based on the total weight of the preparation to provide cosmetic preparations, which protect the skin from the entire range of ultraviolet radiation.
  • the total amount of the filter substances being e.g. 0.1 wt .-% to 30 wt .-%, preferably 0.5 to 10 wt .-%, in particular 1 to 6 wt .-%, based on the total weight of the preparation to provide cosmetic preparations, which protect the skin from the entire range of ultraviolet radiation.
  • Cosmetic preparations for the care of the hair are, for example, shampooing agents, preparations which rinse the hair before or after the hair
  • Shampooing, before or after the permanent wave treatment, before or after the coloring or discoloration of the hair are applied to preparations for blowing or inserting the hair, preparations for dyeing or decolorizing, a hairdressing and treatment lotion, a hair dye or perming agent.
  • the cosmetic preparations contain active ingredients and adjuvants such as are commonly used for this type of preparations for hair care and hair treatment.
  • auxiliaries are preservatives, surface-active substances, substances for preventing foaming, emulsifiers, thickeners, fats, oils, waxes, organic solvents, bactericides, perfumes, dyes or pigments, whose job is to dye the hair or the preparation itself, electrolytes , Preparations against the greasing of the hair.
  • Cosmetic preparations which are a shampoo or a washing, shower or bath preparation preferably comprise at least one anionic, nonionic or amphoteric surfactant or mixtures thereof, at least one dialkyl substituted carboxylic acid in the aqueous medium and adjuvants conventionally used therefor.
  • Corynebacterium. jeikeium (DSM 7171) was streaked from a cryovial (EN 12353) on an agar plate (C + T agar) and incubated at 30 ° C for 48 h. Then a second passage was created.
  • the raw materials were heated at 80 ° C in a water bath and then proportionally mixed with PE water to produce the raw material / water solutions.
  • solid ⁇ -polylysine was dissolved in the emulsifier / water mixture.
  • a sample was prepared solely with ⁇ -polylysine in water.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)
  • Polyamides (AREA)

Abstract

L'invention concerne des combinaisons de principes actifs comprenant : a) de l'ε-polylysine (epsilon-polylysine), b) un ou plusieurs terpènes, par exemple, les esters présentant une structure de terpène.
PCT/EP2012/002425 2011-06-07 2012-06-07 Combinaisons de principes actifs comprenant de l'є-polylysine (epsilon-polylysine) et un ou plusieurs terpènes WO2012167936A2 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP12728396.8A EP2717838A2 (fr) 2011-06-07 2012-06-07 Combinaisons de principes actifs comprenant de l' e-polylysine (epsilon-polylysine) et un ou plusieurs terpènes
BR112013027487A BR112013027487A2 (pt) 2011-06-07 2012-06-07 Combinações de substâncias ativas e formulações cosméticas

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE102011077070.4 2011-06-07
DE102011077077.1 2011-06-07
DE201110077070 DE102011077070A1 (de) 2011-06-07 2011-06-07 Wirkstoffkombinationen aus Epsilon-Polylysin und einem oder mehreren Estern mit Terpenstruktur
DE201110077077 DE102011077077A1 (de) 2011-06-07 2011-06-07 Wirkstoffkombinationen aus Epsilon-Polylysin und einem odermehreren Terpenen

Publications (2)

Publication Number Publication Date
WO2012167936A2 true WO2012167936A2 (fr) 2012-12-13
WO2012167936A3 WO2012167936A3 (fr) 2013-11-21

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PCT/EP2012/002425 WO2012167936A2 (fr) 2011-06-07 2012-06-07 Combinaisons de principes actifs comprenant de l'є-polylysine (epsilon-polylysine) et un ou plusieurs terpènes

Country Status (3)

Country Link
EP (1) EP2717838A2 (fr)
BR (1) BR112013027487A2 (fr)
WO (1) WO2012167936A2 (fr)

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CN108125804A (zh) * 2018-01-29 2018-06-08 南阳师范学院 一种抑菌清爽型洗头膏及其制备方法
US10470459B2 (en) 2014-05-28 2019-11-12 Ipabc Ltd Antimicrobial preparations, methods for preparing the same and uses thereof to combat microorganisms

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HIRAKI, J. ET AL.: "Use of ADME studies to confirm the safety of ?-polylysine as a preservative in food", REGULATORY TOXICOLOGY AND PHARMACOLOGY, vol. 37, no. 2, 2003, pages 328 - 340, XP055287730, DOI: doi:10.1016/S0273-2300(03)00029-1
HIRAKI, J.: "Basic and applied studies on E-polylysine", JOURNAL OF ANTIBACTERIAL ANTIFUNGAL AGENTS, vol. 23, 1995, pages 349 - 354
See also references of EP2717838A2
SHIMA, S. ET AL.: "Antimicrobial action of ?-poly-L-lysine", JOURNAL OF ANTIBIOTICS, vol. 37, no. 11, 1984, pages 1449 - 1455, XP009079625
SHIMA, S.; SAKAI H.: "Polylysine produced by Streptomyces", AGRICULTURAL AND BIOLOGICAL CHEMISTRY, vol. 41, 1977, pages 1807 - 1809

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10470459B2 (en) 2014-05-28 2019-11-12 Ipabc Ltd Antimicrobial preparations, methods for preparing the same and uses thereof to combat microorganisms
CN108125804A (zh) * 2018-01-29 2018-06-08 南阳师范学院 一种抑菌清爽型洗头膏及其制备方法

Also Published As

Publication number Publication date
BR112013027487A2 (pt) 2017-09-12
EP2717838A2 (fr) 2014-04-16
WO2012167936A3 (fr) 2013-11-21

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