EP3389619A1 - Préparations contenant des carnosines - Google Patents

Préparations contenant des carnosines

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Publication number
EP3389619A1
EP3389619A1 EP15813021.1A EP15813021A EP3389619A1 EP 3389619 A1 EP3389619 A1 EP 3389619A1 EP 15813021 A EP15813021 A EP 15813021A EP 3389619 A1 EP3389619 A1 EP 3389619A1
Authority
EP
European Patent Office
Prior art keywords
acid
derivatives
skin
salts
esters
Prior art date
Legal status (The legal status 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 status listed.)
Pending
Application number
EP15813021.1A
Other languages
German (de)
English (en)
Inventor
Gabriele Vielhaber
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Symrise AG
Original Assignee
Symrise 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
Application filed by Symrise AG filed Critical Symrise AG
Publication of EP3389619A1 publication Critical patent/EP3389619A1/fr
Pending legal-status Critical Current

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Classifications

    • 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
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/068—Microemulsions
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/27—Zinc; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/29—Titanium; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—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
    • A61K8/35—Ketones, e.g. benzophenone
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • 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
    • A61Q19/08—Anti-ageing preparations
    • 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
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/21—Emulsions characterized by droplet sizes below 1 micron
    • 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
    • A61K2800/42—Colour properties
    • A61K2800/43—Pigments; Dyes

Definitions

  • the invention is in the field of cosmetics or pharmacy and relates to the use of preparations containing carnosine and carnosine derivatives.
  • ROS reactive oxygen species
  • Carnosine according to a report by Babizhayev et al., moreover, intercept alpha-beta-unsaturated aldehydes released in the peroxidation of fatty acids of the cell membrane under oxidative stress [Membran & Cell Biol. 12 (1), pp. 89-99 (1998)].
  • compositions which contain an antioxidant that protect the skin from IR radiation.
  • an antioxidant that protect the skin from IR radiation.
  • carnosine and arsenic are also mentioned.
  • the topically applied compositions comprise one or more inorganic and / or organic UV filters.
  • EP 2545898 A1 discloses preparations which protect the skin from damage by I R rays and thereby contain plant extracts, vitamins, ruby powder, mica and titanium dioxide.
  • carnosine is also mentioned as a further suitable excipient, but as radical scavenger.
  • EP 2181697 A2 sunscreen in O / W form, which are characterized by a special cocktail of emulsifiers and sunscreen filters.
  • Table 3-3 discloses two compositions (Examples 22 and 23) containing the combination of carnosine with UV filters.
  • WO 2010 124817 A2 relates to conditioning agents based on, inter alia, dipeptides such as carnosine for hair.
  • dipeptides such as carnosine for hair.
  • EP 1310238 A2 discloses cosmetic or dermatological light stabilizer formulations which comprise at least one cholesteric liquid-crystalline component reflecting in the infrared wavelength range from 750 nm to 2500 nm, at least one filter substance protecting against radiation in the ultraviolet radiation range from 280 nm to 449 nm, and contain at least one cosmetically acceptable carrier and their use.
  • antioxidants e.g. Carnosine be present.
  • the object of the present invention was therefore to find a substance or a substance class which is particularly suitable for the prevention and treatment of degeneration phenomena, in particular aging phenomena of the skin, which are not or at least not exclusively due to the action of UV or IR radiation. Radiation can be caused.
  • substances that stimulate the cellular repair functions and counteract damage to the skin caused by air pollution and aging are not or at least not exclusively due to the action of UV or IR radiation.
  • a first subject of the invention relates to a preparation containing at least
  • R 1 is H or CH 3 and R 2 is H or COOH or salts thereof for use as a medicament for the prevention and / or treatment of degeneration and aging of the skin, which are not or not exclusively caused by the action of light ,
  • Another object of the invention relates to a preparation containing
  • Rl is H or CH3 and R2 is H or COOH, or their salts
  • carnosines of which hitherto only an anti-oxidative effect with regard to the trapping of oxygen radicals was known, are also capable of other processes which take place on the skin surface or in the subcutaneous layer to influence positively. These include, in particular, the stimulation of the formation of the enzyme G6PDH and, consequently, the increase in the production of intracellular DNA, both important parameters for cell protection and skin renewal. It was particularly surprising that the activity was increased by the addition of UV light protection filters could be increased even though these substances alone show no activity.
  • the active ingredients which make up the formula (I) there are basically known compounds which are accessible by the usual methods of organic chemistry.
  • this is a group of substances which is formed by carnosine, L-carnosine, D-carnosine, D / L-carnosine, carnicin, carnicin * HCI, anserine, D-anserine, L-anserine and L-anserine * HN0 3 and their mixtures.
  • Salts of the compounds of the formula (I) are preferably understood according to the invention as salts of the compounds of the formula (I) with mineral acids, and particular preference is given to salts of the formula (I):
  • n 1,2 or 3 and A is HCl or HNO 3 and R 1 is H or CH 3 and R 2 is H or COOH.
  • the revitalizing and reactivating activity of carnosine increases, as mentioned above, in particular the activity of G6PDH production and counteracts apoptosis.
  • the use of the substances as protective and restorative medicaments or care agents is possible in principle for all preparations which are used for the prevention of damage or damage to the skin and thus in skin care and prophylaxis.
  • Another use in this field is the application of sensitive, damaged by allergy or other causes skin.
  • the damage to the skin can have a variety of causes.
  • UV sun protection factors may be UV-A filters, UV-B filters, pigments or mixtures thereof, which are further explained below.
  • UV-A and UV-B light protection filters UV-A and UV-B light protection filters
  • UV sunscreen factors for example, at room temperature, liquid or crystalline organic substances (sunscreen) to understand that are able to absorb ultraviolet rays and the absorbed energy in the form of long-wave radiation, e.g. Heat again.
  • the UV sunscreen factors are present in amounts of 0.1 to 5 and preferably 0.2 to 1 wt .-%.
  • UVB filters can be oil-soluble or water-soluble. As oil-soluble substances are e.g. to call:
  • 4-aminobenzoic acid derivatives preferably 2-ethylhexyl 4- (dimethylamino) benzoate, 2-octyl 4- (dimethylamino) benzoate and 4- (dimethylamino) benzoic acid amyl ester;
  • esters of cinnamic acid preferably 4-methoxycinnamic acid 2-ethylhexyl ester, propyl 4-methoxycinnamate, isoamyl 4-methoxycinnamate 2-ethylhexyl 2-cyano-3,3-phenylcinnamate (octocrylene);
  • Esters of salicylic acid preferably 2-ethylhexyl salicylate, 4-isopropylbenzyl salicylate, homomenthyl salicylate;
  • benzophenone preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone;
  • Esters of benzalmalonic acid preferably di-2-ethylhexyl 4-methoxybenzmalonate
  • Triazine derivatives e.g. 2,4,6-trianilino (p-carbo-2'-ethyl-1-hexyloxy) -l, 3,5-triazine and octyl triazone or dioctyl butamido triazone (Uvasorb® HEB);
  • Propane 1,3-diones e.g. 1- (4-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1,3-dione;
  • Suitable water-soluble substances are:
  • Sulfonic acid derivatives of benzophenones preferably 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and its salts;
  • Sulfonic acid derivatives of 3-Benzylidencamphers such as 4- (2-oxo-3-bornylidenme- thyl) benzenesulfonic acid and 2-methyl-5- (2-oxo-3-bomylidene) sulfonic acid and salts thereof.
  • UV-A filter in particular derivatives of benzoylmethane in question, such as L- (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-l, 3-dione, 4-tert .- Butyl 4'-methoxy-dibenzoylmethane (Parsol® 1789), 2- (4-diethylamino-2-hydroxybenzoyl) -benzoic acid hexyl ester (Uvinul® A Plus), 1-phenyl-3- (4'-isopropylphenyl) -propane-1, 3-dione and enamine compounds.
  • the UV-A and UV-B filters can also be used in mixtures.
  • Particularly favorable combinations consist of the derivatives of benzoylmethane, for example 4-tert-butyl-4'-methoxydibenzoylmethane (Parsol® 1789) and 2-cyano-3,3-phenylcinnamic acid 2-ethylhexyl ester (octocrylene) in combination with ester cinnamic acid, preferably 4-methoxycinnamic acid 2-ethylhexyl ester and / or 4-methoxycinnamic acid propyl ester and / or 4-methoxycinnamic acid isoamyl ester.
  • benzoylmethane for example 4-tert-butyl-4'-methoxydibenzoylmethane (Parsol® 1789) and 2-cyano-3,3-phenylcinnamic acid 2-ethylhexyl ester (octocrylene) in combination with ester cinnamic acid, preferably 4-
  • insoluble photoprotective pigments namely finely dispersed metal oxides or salts
  • suitable metal oxides are in particular zinc oxide and titanium dioxide and, in addition, oxides of iron, zirconium, silicon, manganese, aluminum and cerium and mixtures thereof.
  • salts silicates (talc), barium sulfate or zinc stearate can be used.
  • the oxides and salts are used in the form of the pigments for skin-care and skin-protecting emulsions and decorative cosmetics.
  • the particles should have an average diameter of less than 100 nm, preferably between 5 and 50 nm and in particular between 15 and 30 nm.
  • the pigments can have a spherical shape, but it is also possible to use those particles which have an ellipsoidal or otherwise deviating shape from the spherical shape.
  • the pigments can also be surface-treated, ie hydrophilized or hydrophobized. Typical examples are coated titanium dioxides, for example Titandioxid T 805 (Degussa) or Eusolex ® T2000, Eusolex ® T, Eusolex ® T-ECO, Eusolex ® TS, Eusolex ® T-Aqua, Eusolex ® T-45D (all Merck), Uvinul TiO 2 (BASF).
  • Suitable hydrophobic coating agents are in particular silicones and in particular trialkoxyoctylsilanes or simethicones.
  • I n sunscreen agents are preferably used so-called micro- or nanopigments.
  • micronized zinc oxide such as Z-COTE ® or Z-COTE HP1 ® is used.
  • Both the medicaments and the cosmetic preparations described below may contain as component (c) carriers or solvents which are selected from the group formed by water, alcohols, esters, butylene glycol, dipropylene glycol, ethanol, ethoxydiglycol , Ethyl acetate, glycerol, propanol, isopropanol, macrogols, propylpropylene glycol (2) methyl ether, propylpropyl-glycol (3) methyl ether, propylene carbonate, propylene glycol, triethylene glycol, isoparaffin, amyl acetate, amyl benzoate, benzyl acetate, butyl acetate, butylene glycol, butyl lactate, butooctyl benzoate, butooctyl salicylate , C10-C13 alkanes, C14-C17 alkanes, C11-C15 cycloalkanes, caprylyl butyrate, isoparaffin
  • the medicaments according to the invention contain components (a) and (b) preferably in a weight ratio of from about 1:99 to about 99: 1, in particular from about 5:95 to about 20:80 and most preferably from about 10:90 until about 15:85.
  • the synergy is most pronounced when the two components are used approximately in the weight ratio 1: 5.
  • a preferred medicament has the following composition:
  • Another object of the present invention relates to cosmetic compositions for the treatment of degeneration and especially aging of the skin, which are not or not exclusively based on the influence of light, containing
  • Rl is H or CH3 and R2 is H or COOH, or their salts
  • the preparations according to the invention are preferably in the form of creams, lotions, gels, pastes or capsules and in particular are anti-aging agents. Further preferred is that the component (a) based on the total composition in amounts of from 0.001 to about 5 wt .-%, preferably about 0.01 to about 1 wt .-%, more preferably about 0.05 to 0.5 wt .-% and in particular 0.1 to 0.25 wt .-% is present. The proportion of component (b) may exceed that of component (a) by a factor of about 2 to about 20, in particular about 5 to about 15 and in particular about 8 to about 10.
  • compositions according to the invention may contain further typical auxiliaries and additives, such as, for example, mild surfactants, oil particles, emulsifiers, pearlescent waxes, bodying agents, thickeners, superfatting agents, stabilizers, polymers, silicone compounds, fats, waxes, lecithins, phospholipids, humectants, biogenic agents, antioxidants, deodorants, antiperspirants, self-tanning agents, tyrosine inhibitors (depigmentation agents), hydrotropes, solubilizers, preservatives, perfume oils, dyes and the like.
  • mild surfactants such as, for example, mild surfactants, oil particles, emulsifiers, pearlescent waxes, bodying agents, thickeners, superfatting agents, stabilizers, polymers, silicone compounds, fats, waxes, lecithins, phospholipids, humectants, biogenic agents, antioxidants, deodorants, antiperspirants, self-t
  • anionic, nonionic, cationic and / or amphoteric or zwitterionic surfactants may be included, the proportion of the means usually at about 1 to 70, preferably 5 to 50 and especially 10 to 30 wt .-% is.
  • anionic surfactants are soaps, alkylbenzenesulfonates, alkanesulfonates, olefinsulfonates, alkyl ether sulfonates, glycerol ether sulfonates, cc-methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, alkyl ether sulfates, glycerol ether sulfates, fatty acid ether sulfates, hydroxy mixed ether sulfates, monoglyceride (ether) sulfates, fatty acid amide (ether) sulfates, mono- and dialkylsulfosuccinates, mono- and dialkylsulfosuccinamates, sulfotriglycerides, amide soaps, ethercarboxylic acids and their salts, fatty acid isethionates, fatty acid sarcosates,
  • anionic surfactants contain polyglycol ether chains, these may have a conventional, but preferably a narrow homolog distribution.
  • Typical examples of nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol ethers, fatty amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers, optionally partially oxidized alk (en) yloligoglycosides or glucuronic acid derivatives, fatty acid N-alkylglucamides, protein hydrolysates (in particular wheat-based vegetable products ), Polyol fatty acid esters, sugar esters, sorbitan esters, polysorbates and amine oxides.
  • nonionic surfactants contain polyglycol ether chains, these may have a conventional, but preferably a narrow homolog distribution.
  • cationic surfactants are quaternary ammonium compounds, such as dimethyl distearyl ammonium chloride, and ester quats, especially quaternized fatty acid trialkanolamine ester salts.
  • amphoteric or zwitterionic surfactants are alkylbetaines, alkylamidobetaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines. The surfactants mentioned are exclusively known compounds.
  • Typical examples of particularly suitable mild, ie particularly skin-compatible, surfactants are fatty alcohol polyglycol ether sulfates, monoglyceride sulfates, mono- and / or dialkyl sulfosuccinates, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, fatty acid tamates, ⁇ -olefinsulfonates, ethercarboxylic acids, alkyl oligoglucosides, fatty acid glucamides, alkylamidobetaines, amphoacetals and / or protein fatty acid condensates, the latter preferably based on wheat proteins.
  • Guerbet alcohols based on fatty alcohols having 6 to 18, preferably 8 to 10, carbon atoms, esters of linear C 6 -C 22 fatty acids with linear or branched C 6 -C 2 2 fatty alcohols or esters of branched alcohols are used as the oil body C 6 -C 3 -carboxylic acids with linear or branched C 6 -C 22 fatty alcohols, such as, for example, myristyl myristate, myristyl palmitate, myristyl stearate, myristyl isostearate, myristyl oleate, myristyl behenate, myristyl erucate, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl isostearate, cetyl oleate, cetyl behenate, cetyl erucate , Stearylmyristat, stearyl palmitate, stearyl stearate, Ste
  • esters of linear C 6 -C 22 fatty acids with branched alcohols are esters of linear and / or branched fatty acids with polyhydric alcohols (for example propylene glycol, dimer diol or trimer triol) and / or Guerbet alcohols, triglycerides based on C 6 -C 0 fatty, liquid mono- / di- / triglyceride mixtures based on C 6 -C 8 - fatty acids, esters of C 6 -C 22 fatty alcohols and / or Guerbet alcohols with aromatic carboxylic acids, in particular benzoic acid, esters of C 2 -C 2 dicarboxylic acids with linear or branched alcohols having 1 to 22 carbon atoms
  • Suitable emulsifiers are, for example, nonionic surfactants from at least one of the following groups:
  • alkyl and / or alkenyl oligoglycosides having 8 to 22 carbon atoms in the alk (en) yl radical and their ethoxylated analogs;
  • Adducts of 15 to 60 moles of ethylene oxide with castor oil and / or hydrogenated castor oil Adducts of 15 to 60 moles of ethylene oxide with castor oil and / or hydrogenated castor oil;
  • Partial esters of polyglycerol (average intrinsic condensation degree 2 to 8), polyethylene glycol (molecular weight 400 to 5000), trimethylolpropane, pentaerythritol, sugar alcohols (eg sorbitol), alkylglucosides (eg methylglucoside, butylglucoside, laurylglucoside) and polyglucosides (eg cellulose) saturated and / or unsaturated, linear or branched fatty acids having 12 to 22 carbon atoms and / or hydroxycarboxylic acids having 3 to 18 carbon atoms and their adducts with 1 to 30 moles of ethylene oxide;
  • Block copolymers e.g. Polyethylene glycol-30 dipolyhydroxystearates
  • polymeric emulsifiers such as Pemulen grades (TR-L, TR-2) from Goodrich or Cosmedia SP ® Cognis;
  • Alkoxylates The addition products of ethylene oxide and / or of propylene oxide with fatty alcohols, alkylphenols or castor oil are known, commercially available products. These are mixtures of homologs whose average alkoxylation degree is the ratio of the molar amounts of ethylene oxide and / or Propylene oxide and substrate, with which the addition reaction is carried out, corresponds. 2 Ci / i 8 - fatty acid mono- and diesters of addition products of ethylene oxide onto glycerol are known as refatting agents for cosmetic preparations. Alkyl and / or alkenyl oligoglycoside. Alkyl and / or alkenyl oligoglycosides, their preparation and their use are known from the prior art.
  • glycoside radical both monoglycosides in which a cyclic sugar residue is glycosidically linked to the fatty alcohol and oligomeric glycosides having a degree of oligomerization of preferably approximately 8 are suitable.
  • the degree of oligomerization is a statistical mean, which is based on a homolog distribution typical for such technical products.
  • Partial glycerides Typical examples of suitable partial glycerides are Hydroxystea- rinkladremonoglycerid, hydroxystearic acid diglyceride, isostearic acid, Isostea- rinklarediglycerid, klarediglycerid oleic acid monoglyceride, oleic acid diglyceride, Ricinolklaremoglycerid, ricinoleic, Linolklaremonoglycerid, Linolklarediglycerid, Linolenkladoglycerid, Linolenklad, Erucaklaklamonoglycerid, Erucaklarediglycerid, Weinklaremonogly- cerid, Weinklarediglycerid, Citronenklamonoglycerid, Citronendiglycerid, Citronendiglycerid, Malic acid monoglyceride, malic acid diglyceride and their technical mixtures which, subordinated to the production process,
  • Sorbitan esters As sorbitan esters sorbitan, sorbitan sesquiisostearat, sorbitan diisostearate, sorbitan triisostearate, sorbitan, sorbitan sesquioleate, sorbitan dioleate, trioleate, Sorbitanmonoerucat, Sorbitansesquierucat, Sorbitandierucat, Sorbitantrierucat, Sorbitanmonoricinoleat, Sorbitansesquiricinoleat, bitandiricinoleat sorting, Sorbitantriricinoleat, Sorbitanmonohydroxystearat, sorbitan sesquihydroxystearat , Sorbitan dihydroxystearate, sorbitan trihydroxystearate, sorbitan mono- tartrate, sorbitan sesquivar tartrate, sorbitan dandristrate, sorbitan tri- tartrate, sorbitan monocitrate, sorbitan sicci
  • polyglycerol esters are polyglyceryl-2 dipolyhydroxystearates (Dehymuls® PGPH), polyglycerol-3-diisostearates (Lameform® TGI), polyglyceryl-4 isostearates (Isolan® Gl 34), polyglyceryl-3 oleates, diisostearoyl polyglyceryl-3 diisostearates (Isolan® PDI), Polyglyceryl-3 Methylglucose Distearate (Tego Care® 450), Polyglyceryl-3 Beeswax (Cera Bellina®), Polyglyceryl-4 Caprate (Polyglycerol Caprate T2010 / 90), Polyglyceryl-3 Cetyl Ether (Chimexane® NL) , Polyglyceryl-3 Distearate (Cromophor® GS 32) and Polyglyceryl Polyricinoleate (Admul® WOL 140
  • polystyrene resin examples include the mono-, di- and triesters of trimethylolpropane or pentaerythritol reacted with 1 to 30 mol of ethylene oxide with lauric acid, coconut fatty acid, tallow fatty acid, palmitic acid, stearic acid, oleic acid, behenic acid and the like.
  • Anionic emulsifiers are aliphatic fatty acids having 12 to 22 carbon atoms, such as palmitic acid, stearic acid or behenic acid, and dicarboxylic acids having 12 to 22 carbon atoms, such as azelaic acid or sebacic acid. Amphoteric and cationic emulsifiers. Furthermore, zwitterionic surfactants can be used as emulsifiers. Zwitterionic surfactants are those surface-active compounds which carry at least one quaternary ammonium group and at least one carboxylate and one sulfonate group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammoniumglycinate, for example Kokosalkyldimethylammoniumglycinat, N-acylaminopropyl-N, N-dimethylammoniumglycinate, for example Kokosacyl- aminopropyldimethyl-ammoniumglycinat, and 2-alkyl-3-carboxylmethyl 3-hydroxyethylimidazolines having in each case 8 to 18 C atoms in the alkyl or acyl group, and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • betaines such as the N-alkyl-N, N-dimethylammoniumglycinate, for example Kokosalkyldimethylammoniumglycinat, N-acylaminopropyl-N, N-dimethylammoniumglycinate, for example Kokos
  • fatty acid amide derivative known by the CTFA name Cocamidopropyl Betaine.
  • emulsifiers are ampholytic surfactants.
  • Ampholytic surfactants are surface-active compounds which, in addition to a C8 / i 8 alkyl or acyl group, contain at least one free amino group and at least one -COOH or -S0 3 H group and capable of forming inner salts.
  • phytochemical surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids each having about 8 up to 18 carbon atoms in the alkyl group.
  • pholytic surfactants are N-cocoalkylaminopropionate, Kokosacylaminoethylaminopropionat and the Ci 2 / i 8 acylsarcosine.
  • cationic surfactants may also be used as emulsifiers, particular preference being given to those of the esterquat type, preferably methyl-quaternized difatty acid diethanolamine ester salts. Fats and waxes
  • Typical examples of fats are glycerides, ie solid or liquid vegetable or animal products, which consist essentially of mixed glycerol esters of higher fatty acids
  • waxes include natural waxes, such as candelilla wax, carnauba wax, Japan wax, esparto wax, cork wax, Guaruma wax, rice germ oil wax, sugar cane wax, ouricury wax, montan wax, beeswax, shellac wax, spermaceti, lanolin (wool wax), crepe fat, ceresin, ozokerite (groundwax), petrolatum, paraffin waxes, microwaxes; chemically modified waxes (hard waxes), such as montan ester waxes, Sasol waxes, hydrogenated jojoba waxes and synthetic waxes, such as polyalkylene waxes and polyethylene glycol waxes in question.
  • natural waxes such as candelilla wax, carnauba wax, Japan wax,
  • lecithins In addition to the fats come as additives and fat-like substances such as lecithins and phospholipids in question.
  • lecithin those skilled in the art will understand those glycerophospholipids which are formed from fatty acids, glycerol, phosphoric acid and choline by esterification.
  • Lecithins are therefore often referred to in the art as Phosphatidylcholine (PC).
  • PC Phosphatidylcholine
  • Examples of natural lecithins include the cephalins, which are also referred to as phosphatidic acids and represent derivatives of l, 2-diacyl-sn-glycerol-3-phosphoric acids.
  • phospholipids are usually understood as meaning mono- and preferably diesters of phosphoric acid with glycerol (glycerol phosphates), which are generally regarded as fats.
  • glycerol phosphates glycerol phosphates
  • sphingosines or sphingolipids are also suitable.
  • suitable pearlescent waxes are: alkylene glycol esters, especially ethylene glycol distearate; Fatty acid alkanolamides, especially coconut fatty acid diethanolamide; Partial glycerides, especially stearic acid monoglyceride; Esters of polybasic, optionally hydroxy-substituted carboxylic acids with fatty alcohols having 6 to 22 carbon atoms, especially long-chain esters of tartaric acid; Fatty substances, such as, for example, fatty alcohols, fatty ketones, fatty aldehydes, fatty ethers and fatty carbonates, which in total have at least 24 carbon atoms, especially laurone and distearyl ether; Fatty acids such as stearic acid, hydroxystearic acid or behenic acid, ring-opening products of olefin epoxides having 12 to 22 carbon atoms with fatty alcohols having 12 to 22 carbon atoms and / or polyols having 2 to 15 carbon atoms
  • Coolants are compounds that produce a feeling of coldness on the skin.
  • these are menthol compounds which - in addition to the parent menthol itself - for example selected from the group formed by menthol methyl ether, menthone glyceryl acetal (FEMA GRAS 1 3807), menthone glyceryl ketal (FEMA GRAS 3808) , Menthyl Lactate (FEMA GRAS 3748), Menthol Ethylene Glycol Carbonate (FEMA GRAS 3805), Menthol Propylene Glycol Carbonate (FEMA GRAS 3806), Menthyl N-Ethyloxamate, Monomethyl Succinate (FEMA GRAS 3810), Monomenthyl Glutamate (FEMA GRAS 4006) , Menthoxy-1,2-propanediol (FEMA GRAS 3784), menthoxy-2-methyl-1,2-propanediol (FEMA GRAS 3849) and the menthane carboxylic acid esters and amide
  • FEMA GRAS 3810 A first important representative of these substances is the monomenthyl succinate (FEMA GRAS 3810). Both the succinate and the analogous monomenthyl glutarate (FEMA GRAS 4006) are important representatives of monomenthyl esters based on di- and polycarboxylic acids:
  • FEMA Frute and Extracts Manufacturers Association
  • GRAS is defined as "Generally Regarded ⁇ s Safe”
  • a FEMA GRAS designation means that the substance identified in this way is tested according to the standard method and considered to be toxicologically harmless. Examples of applications of these substances can be found for example in the publications WO 2003 043431 (Unilever) or EP 1332772 AI (IFF).
  • polyols such as glycols, glycerol, or carbohydrates
  • FEMA GRAS 3805 Frescolat ® MGC
  • menthol 2-methyl-l, 2-propanediol carbonates FEMA GRAS 3849
  • FEMA GRAS 3748 Frescolat ® ML
  • FEMA GRAS 3807 Menthone glyceryl acetal
  • FEMA GRAS 3808 Menthone glyceryl ketal
  • menthones glyceryl acetal / ketal and the Menthyl Lactate and Menthol Ethylene Glycol carbonates or menthol Propylene Glycol Carbonatw have proven that the Applicant under the names Frescolat ® MGA, Frescolat ® ML, Frecolat ® MGC and Frescolat ® M PC distributes.
  • menthol compounds were first developed which have a C-C bond in the 3-position and from which a number of representatives can likewise be used. These substances are generally referred to as WS types.
  • Base is a menthol derivative in which the hydroxyl is replaced by a carboxyl group (WS-1). From this structure, all other types of WS are derived, such as the preferred species WS-3, WS-4, WS-5, WS-12, WS-14 and WS-30.
  • fatty alcohols or hydroxy fatty alcohols having 12 to 22 and preferably 16 to 18 carbon atoms and in addition partial glycerides, fatty acids or hydroxy fatty acids into consideration. Preference is given to a combination of these substances with alkyl oligoglucosides and / or fatty acid N-methylglucamides of the same chain length and / or polyglycerol poly-12-hydroxystearates.
  • Suitable thickening agents are, for example, Aerosil types (hydrophilic silicas), polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and Tylose, carboxymethylcellulose and hydroxyethyl and hydroxypropylcellulose, and also higher molecular weight polyethylene glycol mono- and diesters fatty acids, polyacrylates, (eg Carbopole® and Pemulen types from Goodrich, Synthalene® from Sigma, Keltrol types from Kelco, sepiolite types from Seppic, Salcare types from Allied Colloids), polyacrylamides, polymers, polyvinyl alcohol and polyvinylpyrrolidone.
  • Aerosil types hydrophilic silicas
  • polysaccharides in particular xanthan gum, guar guar, agar agar, alginates and Tylose, carboxymethylcellulose and hydroxyethyl and hydroxypropylcellulose, and also higher molecular weight polyethylene
  • bentonites such as Bentone ® Gel VS-5PC (Rheox) have shown which is torit to a mixture of cyclopentasiloxane, disteardimonium HEC and is propylene carbonate.
  • surfactants such as, for example, ethoxylated fatty acid glycerides, esters of fatty acids with polyols, such as pentaerythritol or trimethylolpropane, fatty alcohol ethoxylates with narrow homolog distribution or alkyl oligoglucosides, and electrolytes, such as common salt and ammonium chloride.
  • superfatting agents and stabilizers such as Bentone ® Gel VS-5PC (Rheox) have shown which is torit to a mixture of cyclopentasiloxane, disteardimonium HEC and is propylene carbonate.
  • surfactants such as, for example, ethoxylated fatty acid glycerides, esters of
  • Superfatting agents which can be used are substances such as, for example, lanolin and lecithin, as well as polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides, the latter simultaneously serving as foam stabilizers.
  • metal salts of fatty acids e.g. Magnesium, aluminum and / or zinc stearate or ricinoleate can be used.
  • Suitable cationic polymers are, for example, cationic cellulose derivatives, e.g. a quaternized hydroxyethylcellulose available under the name Polymer JR 400® from Amerchol, cationic starch, copolymers of diallylammonium salts and acrylamides, quaternized vinylpyrrolidone / vinylimidazole polymers, e.g.
  • Lucvivat® (BASF), condensation products of polyglycols and amines, quaternized collagen polypeptides, such as lauryldimonium hydroxypropyl hydrolyzed collagen (Lamequat®L / Grünau), quaternized wheat polypeptides, polyethylenimine, cationic silicone polymers, e.g.
  • Amodimethicones, copolymers of adipic acid and dimethylaminohydroxypropyldiethylenetriamine (Cartaretine® / Sandoz), copolymers of acrylic acid with dimethyldiallylammonium chloride (Merquat® 550 / Chemviron), polyamino-polyamides and their crosslinked water-soluble polymers, cationic chitin derivatives such as quaternized chitosan, optionally microcrystalline, condensation products from dihaloalkylene, such as Dibromobutane with bis-dialkylamines, e.g. Bis-dimethylamino-1,3-propane, cationic guar gum, e.g. Jaguar® CBS, Jaguar® C-17, Jaguar® C-16 from Celanese, quaternized ammonium salt polymers, e.g. Mirapol® A-15, Mirapol® AD-1, Mirapol® AZ-1 from Miranol.
  • Suitable anionic, zwitterionic, amphoteric and nonionic polymers are, for example, vinyl acetate / crotonic acid copolymers, vinylpyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate / isobornyl acrylate copolymers, methyl vinyl ether / maleic anhydride copolymers and their esters, uncrosslinked and polyols crosslinked polyacrylic acids, acrylamidopropyltrimethylammonium chloride / acrylate copolymers, octylacrylamide / methyl methacrylate / tert.butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate copolymers, polyvinylpyrrolidone, vinylpyrrolidone / vinyl acetate copolymers, vinylpyrrolidone / dimethylaminoethyl methacrylate / vinylcaprolactam Terpol
  • Suitable silicone compounds are, for example, dimethylpolysiloxanes, methylphenylpolysiloxanes, cyclic silicones and amino, fatty acid, alcohol, polyether, epoxy, fluorine, glycoside and / or alkyl-modified silicone compounds which are both liquid and resin-form at room temperature may be present.
  • simethicones which are mixtures of dimethicones having an average chain length of from 200 to 300 dimethylsiloxane units and hydrogenated silicates.
  • Humectants serve to further optimize the sensory properties of the composition and to regulate the moisture of the skin. At the same time, the low-temperature stability of the preparations according to the invention, in particular in the case of emulsions, is increased.
  • the humectants are usually contained in an amount of 0.1 to 15% by weight, preferably 1 to 10% by weight, and more preferably 5 to 10% by weight.
  • u.a. Amino acids, pyrrolidonecarboxylic acid, lactic acid and its salts, lactitol, urea and urea derivatives, uric acid, glucosamine, creatinine, cleavage products of collagen, chitosan or chitosan salts / derivatives, and in particular polyols and polyol derivatives (eg glycerol, diglycerol, triglycerol, ethylene glycol, Propylene glycol, butylene glycol, erythritol, 1,2,6-hexanetriol, polyethylene glycols such as PEG-4, PEG-6, PEG-7, PEG-8, PEG-9, PEG-10, PEG-12, PEG-14, PEG-16, PEG-18, PEG-20), sugars and sugar derivatives (including fructose, glucose, maltose, maltitol, mannitol, inositol, sorbito
  • biogenic active substances include tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, (deoxy) ribonucleic acid and their fragmentation products, ⁇ -glucans, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudoceramides, essential oils , Plant extracts, such as Prunus extract, Bambaranussexschreib and vitamin complexes to understand.
  • Antioxidants interrupt the photochemical reaction chain, which is triggered when UV radiation penetrates into the skin.
  • Typical examples are amino acids (eg glycine, histidine, tyrosine, tryptophan) and their derivatives, midazoles (eg urocaninic acid) and their derivatives, peptides such as D, L-carnosine, D-carnosine, L-carnosine and their derivatives ( eg anserine), carotenoids, carotenes (eg carotene, ⁇ -carotene, lycopene) and their derivatives, chlorogenic acid and its derivatives, lipoic acid and its derivatives (eg dihydrolipropylic acid), aurothioglucose, propylthiouracil and other thiols (eg thioredoxin, gluta- thion, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl,
  • deodorants counteract, cover or eliminate body odors. Body odors are caused by the action of skin bacteria on apocrine sweat, forming unpleasant-smelling degradation products. Accordingly, deodorants contain active substances which act as antimicrobials, enzyme inhibitors, odor absorbers or odor maskers.
  • Anti-sprouting agents As germ-inhibiting agents are basically all effective against Gram-positive bacteria substances such.
  • Enzyme inhibitors are suitable as enzyme inhibitors. These are preferably trialkyl citrates such as trimethyl citrate, tripropy citrate, triisopropyl citrate, tributyl citrate and in particular triethyl citrate (Hydagen® CAT). The substances inhibit the enzyme activity and thereby reduce odors.
  • trialkyl citrates such as trimethyl citrate, tripropy citrate, triisopropyl citrate, tributyl citrate and in particular triethyl citrate (Hydagen® CAT).
  • esterase inhibitors include sterol sulfates or phosphates, such as, for example, lanosterol, cholesterol, campesterol, stigmasterol and sitosterol sulfate or phosphate, dicarboxylic acids and their esters, for example glutaric acid, glutaric acid monoethyl ester, glutaric acid diethyl ester, Adipic acid, adipic acid monoethyl ester, diethyl adipate, malonic acid and diethyl malonate, hydroxycarboxylic acids and their esters, for example citric acid, malic acid, tartaric acid or diethyl tartrate, and zinc glycinate. Odor absorber.
  • dicarboxylic acids and their esters for example glutaric acid, glutaric acid monoethyl ester, glutaric acid diethyl ester, Adipic acid, adipic acid monoethyl ester, diethyl adipate, malonic acid
  • Suitable odor absorbers are substances that absorb and largely retain odor-forming compounds. They reduce the partial pressure of the individual components and thus also reduce their propagation speed. It is important that perfumes must remain unimpaired. Odor absorbers have no activity against bacteria. They contain, for example, as a main component of a complex zinc salt of ricinoleic acid or special, largely odorless fragrances, which are known in the art as "fixatives", such. B. Extracts of Labdanum or Styrax or certain Abietinklarivate. Odor maskers are fragrances or perfume oils which, in addition to their function as odor maskers, give the deodorants their respective scent. Examples of perfume oils are mixtures of natural and synthetic fragrances.
  • Natural fragrances are extracts of flowers, stems and leaves, fruits, fruit peel, roots, woods, herbs and grasses, needles and twigs, as well as resins and balsams. Furthermore, animal raw materials come into question, such as civet and Castoreum.
  • Typical synthetic fragrance compounds are products of the ester type, ethers, aldehydes, ketones, alcohols and hydrocarbons.
  • Fragrance compounds of the ester type are, for example, benzyl acetate, p-tert-butylcyclohexyl acetate, linalyl acetate, phenylethyl acetate, linalyl benzoate, benzyl formate, allylcyclohexyl propionate, styrallyl propionate and benzyl salicylate.
  • the ethers include, for example, benzyl ethyl ether, to the aldehydes, for example, the linear alkanals having 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamen aldehyde, hydroxycitronellal, lilial and bourgeonal, to the ketones such as the Jonone and Methylcedrylketon to the alcohols anethole, Citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol, the hydrocarbons mainly include the terpenes and balsams.
  • fragrance oils which are mostly used as aroma components, are suitable as perfume oils, eg sage oil, chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon oil, lime blossom oil, juniper berry oil, vetiver oil, oliban oil, galbanum oil, labdanum oil and lavandin oil.
  • Antiperspirants reduce the formation of sweat by influencing the activity of eccrine sweat glands and thus counteract underarm wetness and body odor.
  • Aqueous or anhydrous formulations of antiperspirants typically contain the following ingredients:
  • bodybuilder • auxiliaries such as B. thickener or complexing agent and / or
  • non-aqueous solvents such as ethanol, propylene glycol and / or glycerol.
  • Salts of aluminum, zirconium or zinc are especially suitable as astringent antiperspirant active ingredients.
  • suitable antiperspirant active ingredients are e.g. Aluminum chloride, aluminum chlorohydrate, aluminum dichlorohydrate, aluminum sesquichlorohydrate and their complex compounds, eg. With propylene glycol-1,2.
  • antiperspirants may contain customary oil-soluble and water-soluble adjuvants in smaller amounts. Such oil-soluble adjuvants may be e.g. be:
  • Usual water-soluble additives are e.g. Preservatives, water-soluble fragrances, pH adjusters, e.g. Buffer mixtures, water-soluble thickeners, e.g. water-soluble natural or synthetic polymers such as e.g. Xanthan gum, hydroxyethylcellulose, polyvinylpyrrolidone or high molecular weight polyethylene oxides.
  • hydrotropes such as, for example, ethanol, isopropyl alcohol, or polyols; These substances largely correspond to the initially described carriers.
  • Polyols contemplated herein preferably have from 2 to 15 carbon atoms and at least two hydroxyl groups.
  • the polyols may contain other functional groups, in particular amino groups, or be modified with nitrogen. Typical examples are
  • Alkylene glycols such as ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol, and polyethylene glycols having an average molecular weight of 100 to 1,000 daltons;
  • Methylol compounds in particular trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol;
  • Lower alkyl glucosides especially those having 1 to 8 carbons in the alkyl radical, such as, for example, methyl and butyl glucoside;
  • Sugar alcohols having 5 to 12 carbon atoms such as sorbitol or mannitol,
  • sugars having 5 to 12 carbon atoms such as glucose or sucrose; • amino sugars, such as glucamine;
  • Dialcoholamines such as diethanolamine or 2-amino-l, 3-propanediol.
  • preservatives examples include phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid and the silver complexes known under the name Surfacine® and the further classes of compounds listed in Appendix 6, Parts A and B of the Cosmetics Regulation.
  • Surfacine® the further classes of compounds listed in Appendix 6, Parts A and B of the Cosmetics Regulation.
  • Natural fragrances are extracts of flowers (lily, lavender, roses, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (aniseed, coriander, caraway, juniper), fruit peel (bergamot, lemon, Oranges), roots (mace, angelica, celery, cardamom, costus, iris, caulm), wood (pine, sandal, guaiac, cedar, rosewood), herbs and grasses (tarragon, lemongrass, sage, Thyme), needles and twigs (spruce, fir, pine, pines), resins and balsams (galbanum, elemi, benzoin, myrrh, olibanum, opoponax).
  • Typical synthetic fragrance compounds are ester type products, ethers, aldehydes, ketones, alcohols and hydrocarbons. Fragrance compounds of the ester type are, for example, benzyl acetate, phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linalyl acetate, dimethylbenzylcarbinyl acetate, phenylethyl acetate, linalyl benzoate, benzylformate, ethylmethylphenylglycinate, allylcyclohexylpropionate, styrallylpropionate and benzylsalicylate.
  • the ethers include, for example, benzyl ethyl ether, to the aldehydes, for example, the linear alkanals having 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamen aldehyde, hydroxycitronellal, lilial and Bourgeonal, to the ketones, for example, the Jonone, -lsomethylionon and Methylcedrylketon,
  • the alcohols include anethole, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol; the hydrocarbons mainly include the terpenes and balms.
  • fragrance oils are suitable as perfume oils, for example sage oil, chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon oil, lime blossom oil, juniper berry oil, vetiver oil, oliban oil, galbanum oil, labolanum oil and lavandin oil.
  • Suitable flavors are, for example, peppermint oil, spearmint oil, aniseed oil, star aniseed oil, caraway oil, eucalyptus oil, fennel oil, lemon oil, wintergreen oil, clove oil, menthol and the like. Dyes
  • dyes the substances suitable and suitable for cosmetic purposes can be used, as they are compiled, for example, in the publication "Cosmetic Colorants” of the Dye Commission of the Irish Klastician, Verlag Chemie, Weinheim, 1984, pp. 81-106. Examples are Kochillerot A (Cl 16255), Patent Blue V (C.1.42051), Indigotin (C.1.73015), chlorophyllin (C.1.75810), quinoline yellow (C.1.47005), titanium dioxide (C.1.77891), indanthrene blue RS ( Cl 69800) and Krapplack (Cl58000). As a luminescent dye and luminol may be included. These dyes are usually used in concentrations of 0.001 to 0.1 wt .-%, based on the total mixture.
  • the total amount of auxiliaries and additives may be 1 to 50, preferably 5 to 40 wt .-% - based on the means - amount.
  • the preparation of the agent can be carried out by conventional cold or hot processes; It is preferable to work according to the phase inversion temperature method. INDUSTRIAL APPLICABILITY
  • Another object of the invention relates to a non-therapeutic method for the prevention and / or treatment of human skin against signs of degeneration and aging, which are not caused or not exclusively by the influence of light, wherein a preparation according to the first or the second Subject of the invention or a cosmetic agent of the type described above topically applied. It has been found that the topical administration of about 1 to about 5 g of these preparations or agents at least once, better twice a day over a period of at least 7 to 14 days to measurable results, especially as regards the depth of wrinkles leads.
  • the preparations and compositions are particularly effective in female consumers in the range of 35 to 55 years.
  • R 1 is H or CH 3 and R 2 is H or COOH, or salts thereof for the prevention and / or treatment of degeneration and aging phenomena of Human skin that is not or not exclusively caused by the influence of light.
  • the use may optionally be in combination with UV sun protection factors.
  • this use also includes
  • the present invention has an impact on the formation of dermal macromolecules, the degradation of which, in turn, is an important cause of skin aging or skin degeneration.
  • dermal macromolecules the degradation of which, in turn, is an important cause of skin aging or skin degeneration.
  • dermal macromolecules are, in principle, to be understood as meaning all macromolecules which can be found directly as constituents of the skin either in the basal membrane between the dermis and the epidermis or in the dermis and epidermis.
  • the dermal macromolecules are those selected from the group consisting of glycosaminoglycans, in particular chondroitin sulfate, keratan sulfate, dermatan sulfate and hyaluronic acid and its salts, collagen, in particular type II I collagen, elastin, fibronectin, proteoglycans and their salts.
  • glycosaminoglycans are also referred to as mucopolysaccharides. These are negatively charged, long unbranched polysaccharides (glycans), which consist of 1,4-linked units of dissacharides in which one mole of a uronic acid (D-glucuronic acid or, for example, L-iduronic acid) with the 3-position of a N-acetylated amino sugars (glycosamines) are glycosidically linked.
  • the glycosaminoglycans are bound in the tissue to several chains of a core protein (core protein) and thus form the proteoglycans.
  • the chondrotin sulfate is one of the glycosaminoglycans. It occurs in tissue as chondroitin-4-sulphate or as chondroitin-6-sulphate and consists inter alia of D-glucuronic acid and N-acetyl-D-galactosamine. The molar mass is between 5,000 and 50,000.
  • the non-anticoagulating glycosaminoglycan dermatan sulfate also known as beta-heparin, consists of L-iduronic acid or D-glucuronic acid, N-acetyl-D-galactosamine and sulfate groups. The molar mass of deramtansulfate is between 15,000 and 40,000.
  • Hyaluronic acid is an acid glycosaminoglycan.
  • the basic building block of hyaluronic acid is an aminodisaccharide composed of D-glucuronic acid and N-acetyl-D-glucosamine in (beta 1-3) glycosidic linkage with the next unit (beta l-4) glycosidically linked.
  • hyaluronic acid has no sulfate groups and is not protein bound in the tissue.
  • Collagen consists of protein fibers and occurs in human skin in three different types (type I, II I and IV).
  • the individual polypeptide chains each containing much of the amino acid proline and every three residues of glycine, are wrapped around each other in a triple helix.
  • the collagen fibers are synthesized as tropocollagen in the fibroblasts and secreted into the extracellular matrix.
  • the stimulation of the collagen synthesis according to the invention leads to an increase in the production of collagen and thus to an increased intermolecular solidification of the dermis and thereby to a firmer appearing skin.
  • the elastin is also a fibrous protein. These are unstructured covalently cross-linked polypeptide chains that form a rubber-like elastic material. The elastin is released into the extracellular matrix in the skin cells after synthesis.
  • the stimulation according to the invention of the synthesis of the elastin polypeptide chains leads to an increase in the production of elastin and thus to an increase in the elasticity of the skin.
  • Fibronectin represents a group of high molecular weight glycoproteins (M R of the dimer ca. 440 000-550 000) found in the extracellular matrix and extracellular fluids.
  • the fibronectin dimer connected by two disulfide bridges, an elongated molecule measuring 600x25 ⁇ , binds by linear combination of three distinct repeating domains and the like.
  • a. Collagens, glycosaminoglycans, proteoglycans, fibrin (ogen), deoxyribonucleic acids, immunoglobulins, plasminogen, plasminogen activator, thrombospondin, cells and microorganisms. Due to these properties it conveys z. The adhesion of connective tissue cells to collagen fibrils or of thrombocytes and fibroblasts to fibrin (contribution to wound healing).
  • proteoglycans like the glycoproteins, consist of carbohydrates and of proteins, but in proteoglycans, the proportion of polysaccharides predominates.
  • the proteoglycans of the skin contain dermatan sulfate. Approximately 140 such proteoglycans are non-covalently attached to a hyaluronic acid chain to molecular aggregates with an average molar mass of approximately 2 million with the aid of smaller proteins (link proteins).
  • the polyanionic aggregates which are distinguished by their ability to bind water, can form solid gels which impart elasticity and tensile strength to the supporting tissue (extracellular matrix). In mucus, they protect the epithelia.
  • the inventive stimulation of the synthesis of proteoglycans and hyaluronic acid leads to a greater amount of extracellular matrix and thus to increased elasticity and tensile strength.
  • Glycation is a non-enzymatic reaction of glucose or other sugars with proteins to glycoproteins. This reaction leads to unintentional changes in the collagen and elastin and thus to changes in the extracellular matrix. The function of collagen and the extracellular matrix are disturbed.
  • the prevention of glycation according to the invention leads to a reduction in the non-enzymatic change in collagen and elastin and thus in the prevention of a reduced function of the extracellular matrix.
  • G6PDH glucose-6-phosphate dehydrogenase
  • the G6PDH activity was determined in vitro on human fibroblasts by the enzymatic method of Okada, the DNA content by the method of Desaulniers. The results are summarized in Table 1. The results are given in each case of 3 series of measurements with triple determination in% -rel compared to a blank.
  • apoptosis is a natural targeted cell death of certain unwanted or damaged cells. It is an active process of cells (suicide on command). Skin aging in particular leads to induced apoptosis of the skin cells due to a lack of growth factors in the skin. In the cells affected by apoptosis, the specific enzyme endonuclease degrades the nuclear DNA and transports the DNA fragments into the cytoplasm.
  • the cells were recovered by trypsinization by the method of Dunnebacke and Zitcer described in: Cell and tissue culture, eds .: J. Paul, Churchill Livingstone, 1975 , P. 226. After trypsinization, the cells were centrifuged and counted. Subsequently, the content of BrdU in DNA fragments from the cytoplasm was determined by means of the ELISA test (ELISA kit from Roche). The content of BrdU is a measure of the DNA fragments that have been released from the nucleus, the nucleus, into the cytoplasm. The results were expressed in terms of one million cells and expressed as a percentage of the control. The results are summarized in the following Table 2.
  • the aim of these studies is to demonstrate a stimulating activity of carnosines on the synthesis of dermal macromolecules on human fibroblast cultures in vitro.
  • the dermis is composed of cells (fibroblasts and mast cells), tissue components (collagen and elastin) and so-called basic substances.
  • These basic substances include, for example, glycosaminoglycan (GAG), hyaluronic acid, chondroitin sulfate, dermatan sulfate and glycoproteins.
  • GAG glycosaminoglycan
  • hyaluronic acid chondroitin sulfate
  • dermatan sulfate glycoproteins.
  • Skin aging reduces the intermolecular solidification and elasticity of the dermis and thereby the firmness of the skin.
  • the number of skin cells present, in particular the fibroblasts is reduced in the course of skin aging.
  • the collagen fibers become fragmented over time and the proportion of insoluble to soluble collagen increases. Fine dermal elastic fibers are coarsened and destroyed. The synthesis of GAG (glycosaminoglycan) is reduced. All of these processes contribute to skin aging and its manifestations, such as wrinkles and the lack of firmness of the skin.
  • GAG glycosaminoglycan
  • the measurement method is based on a staining of macromolecules in a culture of human fibroblasts, which builds up a collagen gel or collagen lattice fibers with type I collagen. Certain regions of these fibers are quantified by staining reagents on the proportion of said macromolecules.
  • a suspension of human fibroblasts mixed with a solution of collagen type I (1-2 mg / ml).
  • DM EM Dulbecco Minimum Essential Medium, Life Technology Sari Company
  • FCS Fetal Calf Serum
  • Elastase is a protease secreted by the fibroblasts in inflammatory conditions and is useful for the degradation of dermal macromolecules, e.g. Collagen and elastin and thus responsible for skin aging.
  • pancreatic elastase (a serine protease) was assayed and labeled as substrate elastin with a chromogenic synthetic substrate.
  • the system was incubated with the drugs for 30 min at room temperature and then determined after centrifugation, the optical density of the dye at 410 nm.
  • the amount used of the extracts was 0.3 percent by weight.
  • Type I collagen was treated with glucose and the extracts at 45 ° C for a period of 21 days. Subsequently, the suspensions were centrifuged and the content of Schiff bases in the supernatant liquid was determined by fluorescence measurement at 430 nm. The results are summarized in Table 5. The data relate again to the control as standards (without extract and without glucose).

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Abstract

L'invention concerne une préparation contenant au moins un composé représenté par formule (I) à la condition que R1 représente H ou CH3 et R2 représente H ou COOH, ou les sels correspondants, destinée à être utilisée comme médicament pour la prévention et/ou le traitement des phénomènes de dégénération et de vieillissement de la peau qui ne sont pas dus, ou pas exclusivement dus, à l'effet du rayonnement lumineux.
EP15813021.1A 2015-12-15 2015-12-15 Préparations contenant des carnosines Pending EP3389619A1 (fr)

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PCT/EP2015/079711 WO2017101976A1 (fr) 2015-12-15 2015-12-15 Préparations contenant des carnosines

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EP3389619A1 true EP3389619A1 (fr) 2018-10-24

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EP15813021.1A Pending EP3389619A1 (fr) 2015-12-15 2015-12-15 Préparations contenant des carnosines
EP16816649.4A Active EP3389621B1 (fr) 2015-12-15 2016-12-15 Émulsions contenant des filtres uv et des carnosines

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US (2) US10857085B2 (fr)
EP (2) EP3389619A1 (fr)
JP (1) JP7053466B2 (fr)
KR (1) KR102085469B1 (fr)
CN (1) CN108430448B (fr)
AU (1) AU2016374457B2 (fr)
BR (1) BR112018011765B1 (fr)
ES (1) ES2935773T3 (fr)
PL (1) PL3389621T3 (fr)
WO (2) WO2017101976A1 (fr)

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Publication number Priority date Publication date Assignee Title
WO2024061476A1 (fr) * 2022-09-19 2024-03-28 Symrise Ag Méthode pour prévenir, atténuer et/ou traiter des affections cutanées induites par ptgs2 et des dysfonctions associées

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Also Published As

Publication number Publication date
EP3389621B1 (fr) 2022-10-19
AU2016374457B2 (en) 2022-07-07
ES2935773T3 (es) 2023-03-09
AU2016374457A1 (en) 2018-07-05
KR102085469B1 (ko) 2020-03-05
US10857085B2 (en) 2020-12-08
BR112018011765B1 (pt) 2021-12-14
KR20180094078A (ko) 2018-08-22
CN108430448A (zh) 2018-08-21
EP3389621A1 (fr) 2018-10-24
CN108430448B (zh) 2021-10-01
WO2017101976A1 (fr) 2017-06-22
JP7053466B2 (ja) 2022-04-12
PL3389621T3 (pl) 2023-06-12
US10688032B2 (en) 2020-06-23
US20180369116A1 (en) 2018-12-27
JP2018537492A (ja) 2018-12-20
WO2017102971A1 (fr) 2017-06-22
BR112018011765A2 (pt) 2018-12-04
US20180360723A1 (en) 2018-12-20

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