Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
  • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
  • C07C49/24—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
  • C07C49/245—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups containing six-membered aromatic rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
  • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
  • C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
  • A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
  • A01N31/16—Oxygen or sulfur directly attached to an aromatic ring system with two or more oxygen or sulfur atoms directly attached to the same aromatic ring system
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
  • A01N35/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aliphatically bound aldehyde or keto groups, or thio analogues thereof; Derivatives thereof, e.g. acetals
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
  • A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
  • A01P3/00—Fungicides
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
  • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
  • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
  • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
  • A23L3/3463—Organic compounds; Microorganisms; Enzymes
  • A23L3/3481—Organic compounds containing oxygen
  • A23L3/3499—Organic compounds containing oxygen with doubly-bound oxygen
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
  • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
  • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
  • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
• • 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
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P17/00—Drugs for dermatological disorders
• • 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
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
  • C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
• • 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
  • A61K2800/524—Preservatives
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
  • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
  • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
  • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Definitions

• the present invention relates to the use of vanillin derivatives especially as preserving agents in cosmetic, dermatological or pharmaceutical, or even nutraceutical or oral cosmetic compositions; the invention also relates to novel compounds that may be used in cosmetics, dermatology or pharmacy, or even nutraceutics or oral cosmetics, in particular as preserving agents, and also to compositions comprising these compounds.
• preserving agents are increasingly searching for environmentally friendly, in particular non-ecotoxic, preserving agents.
• effectiveness of the preserving agents conventionally used is variable and their formulation can pose problems, in particular of incompatibility, or even of destabilization, of formulas, in particular of emulsions.
• One object of the present invention is to propose novel preserving agents which in particular have a broad antimicrobial spectrum, at least as broad, or even broader, than that of the already existing compounds, and which do not have the drawbacks of the prior art, in particular which have specific physicochemical properties making it possible to protect cosmetic formulas against microbial contamination while at the same time being well tolerated.
• a subject of the invention is therefore the use as a preserving agent, in particular in a cosmetic, dermatological, pharmaceutical, nutraceutical or oral cosmetic composition, of at least one compound of formula (I):
• preserving agent is intended to mean a substance which is commonly added to a composition in order to preserve said composition with respect to a contaminating agent.
• the compounds of formula (I) according to the invention are used as an antimicrobial and/or antibacterial and/or antifungal agent.
• Another subject of the invention is a process for preserving a cosmetic, dermatological, pharmaceutical, nutraceutical or oral cosmetic composition, characterized in that it consists in incorporating into the said composition at least one compound of formula (I).
• the compounds correspond to formula (I), in which:
• composition does not comprise any preserving agents other than those of formula (I).
• composition does not contain parabens.
• compositions comprising at least one compound of formula (I) or of formula (I′) also form a subject of the present invention.
• the compounds of formula (I) can be readily prepared by those skilled in the art on the basis of their general knowledge. Mention may be made especially of the following bibliographic references: J. Asian Natural Products Research, 2006, 8(8), 683-688; Helv. Chimica Acta, 2006, 89(3), 483-495; Chem. Pharm. Bull., 2006, 54(3), 377-379; and Bioorg. J. Med. Chem. Lett., 2004, 14(5), 1287-1289.
• the compounds of formula (I), alone or as a mixture, may be used in a proportion of from 0.01% to 5% by weight and in particular 0.1% to 2.5% by weight, relative to the weight of the composition, in cosmetic, dermatological or pharmaceutical compositions.
• the cosmetic, dermatological or pharmaceutical compositions moreover comprise a cosmetically, dermatologically or physiologically acceptable medium, i.e. a medium that is compatible with keratin materials such as facial or bodily skin, the lips, the hair, the eyelashes, the eyebrows and the nails.
• a cosmetically, dermatologically or physiologically acceptable medium i.e. a medium that is compatible with keratin materials such as facial or bodily skin, the lips, the hair, the eyelashes, the eyebrows and the nails.
• compositions according to the invention may be in any galenical form conventionally used, in particular for topical application, and in particular in the form of aqueous or aqueous/alcoholic solutions, of oil-in-water (O/W), water-in-oil (W/O) or multiple (triple: W/O/W or O/W/O) emulsions, of aqueous gels or of dispersions of a fatty phase in an aqueous phase using spherules, it being possible for these spherules to be polymeric nanoparticles, such as nanospheres and nanocapsules, or lipid vesicles of ionic and/or nonionic type (liposomes, niosomes or oleosomes), of nanoemulsions, or of thin films.
• These compositions are prepared according to the usual methods.
• compositions according to the invention may be more or less fluid and may have the appearance of a white or coloured cream, an ointment, a milk, a lotion, a serum, a paste or a foam. They can optionally be applied to the skin in the form of an aerosol. They can also be in solid form, for example in the form of a stick.
• composition according to the invention may in particular be in the form of:
• physiologically acceptable medium in which the compounds can be used, and also its constituents, their amount, the galenical form of the composition and the method for preparing said composition may be chosen by those skilled in the art on the basis of their general knowledge as a function of the type of composition desired.
• the composition may comprise any fatty substance normally used in the field of application envisaged. Mention may in particular be made of silicone fatty substances such as silicone oils, gums and waxes and also nonsilicone fatty substances such as oils, pastes and waxes of plant, mineral, animal and/or synthetic origin.
• the oils may be volatile or non-volatile.
• silicone oils mention may be made of volatile or non-volatile polydimethylsiloxanes (PDMSs) with a linear or cyclic silicone chain, which are liquid or pasty at room temperature, in particular cyclopolydimethylsiloxanes such as cyclohexasiloxane; polydimethylsiloxanes comprising alkyl, alkoxy or phenyl groups, which are pendent or at the end of a silicone chain, these groups containing from 2 to 24 carbon atoms; phenylsilicones, for instance phenyl trimethicones, phenyl dimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyl dimethicones, diphenylmethyldiphenyltrisiloxanes or 2-phenylethyl trimethylsiloxy silicates, and polymethylphenylsiloxanes.
• PDMSs volatile or non-volatile polydimethylsi
• liquid triglycerides of fatty acids containing from 4 to 10 carbon atoms for instance heptanoic or octanoic acid triglycerides, or alternatively, for example, sunflower oil, maize oil, soybean oil, marrow oil, grapeseed oil, sesame seed oil, hazelnut oil, apricot oil, macadamia oil, arara oil, castor oil, avocado oil, caprylic/capric acid triglycerides, jojoba oil and shea butter oil.
• fatty substance that can be used, of:
• the composition may also comprise an aqueous medium that comprises water, an aqueous-alcoholic medium containing a C2-C6 alcohol such as ethanol or isopropanol, or an organic medium comprising standard organic solvents such as C2-C6 alcohols, in particular ethanol and isopropanol, glycols such as propylene glycol, and ketones.
• a C2-C6 alcohol such as ethanol or isopropanol
• an organic medium comprising standard organic solvents such as C2-C6 alcohols, in particular ethanol and isopropanol, glycols such as propylene glycol, and ketones.
• composition according to the invention may also comprise the adjuvants that are customary in the cosmetic and dermatological fields, such as thickeners, emulsifiers, surfactants, gelling agents, active cosmetic agents, fragrances, fillers, dyestuffs, moisturizers, vitamins and polymers.
• adjuvants that are customary in the cosmetic and dermatological fields, such as thickeners, emulsifiers, surfactants, gelling agents, active cosmetic agents, fragrances, fillers, dyestuffs, moisturizers, vitamins and polymers.
• the amounts of these various adjuvants are those conventionally used in the fields under consideration, for example from 0.001% to 20% of the total weight of the composition.
• These adjuvants and the concentrations thereof must be such that they are not detrimental to the advantageous properties of the compounds according to the invention.
• the pH of the compositions according to the invention when they comprise at least one aqueous phase (for example aqueous solutions, emulsions), is preferably between 4 and 9, preferably between 4 and 7, advantageously between and 6.
• the antimicrobial efficacy of a compound of formula (I) was evaluated via the Challenge Test or artificial contamination method.
• the method of the challenge test consists of an artificial contamination of the sample with collection microbial strains (bacteria, yeasts and moulds) and evaluation of the number of revivable microorganisms seven days after the inoculation.
• the gram-negative bacteria Escherichia coli and Pseudomonas aeruginosa
• gram-positive bacteria Enterococcus faecalis
• yeast Candida albicans
• mould Aspergillus niger
• the content of microorganisms present in the product corresponds after homogenization to a concentration of 10 6 microorganisms per gram of product, i.e. inoculation to 1% of an inoculum containing 10 8 microorganisms per ml. After 7 days of contact time between the microorganisms and the product at 22° C. ⁇ 2° C. and in darkness, decimal dilutions are performed and the number of revivable microorganisms remaining in the product is counted.
• An emulsion is prepared, comprising (weight %): sorbitan tristearate (Span 65 V ® from Croda) 0.9% polyethylene glycol stearate (40 OE) 2% (Myrj 52 P ® from Croda) glyceryl mono-distearate (36/64)/potassium 3% stearate mixture fatty acids of plant origin (53/44/3 1% stearic acid/palmitic acid/myristic acid) glycerol 3% cyclopentasiloxane 5% hydrogenated isoparaffin 7.2% white petroleum jelly 4% cetyl alcohol 4% myristyl myristate 2% fillers 0.8% compound tested in Example 1 2% water qs 100%
• An O/W emulsion is prepared, comprising (weight %): sodium hydroxide 0.03% liquid petroleum jelly 10% 2-ethylhexyl palmitate 10% acrylic acid/stearyl methacrylate copolymer 0.1% polymerized in an ethyl acetate/cyclohexane mixture glycerol 5% mixture of cetylstearyl glucoside and of 2.45% cetyl and stearyl alcohols (12/46/42) compound tested in Example 1 2% microbiologically clean deionized water qs 100%
• a lotion is prepared, comprising (weight %): allantoin 0.05% sodium chloride 0.09% citric acid qs pH 7 ⁇ 0.2 cornflower water 1% hexylene glycol (2-methyl-2,4-pentanediol) 1% glycerol 5% sodium N-cocoylamidoethyl-N-ethoxycarboxymethyl 1.1% glycinate sodium/magnesium lauryl ether sulfate 0.45% (80/20) 40 OE (52% SM) compound tested in Example 1 1.5% microbiologically clean deionized water qs 100%

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• Life Sciences & Earth Sciences (AREA)
• Health & Medical Sciences (AREA)
• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• General Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• Veterinary Medicine (AREA)
• Public Health (AREA)
• Animal Behavior & Ethology (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Epidemiology (AREA)
• Plant Pathology (AREA)
• Wood Science & Technology (AREA)
• Environmental Sciences (AREA)
• Zoology (AREA)
• Dermatology (AREA)
• Birds (AREA)
• Pharmacology & Pharmacy (AREA)
• Emergency Medicine (AREA)
• Medicinal Chemistry (AREA)
• Pest Control & Pesticides (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Agronomy & Crop Science (AREA)
• Dentistry (AREA)
• Microbiology (AREA)
• Bioinformatics & Cheminformatics (AREA)
• Nutrition Science (AREA)
• Food Science & Technology (AREA)
• Polymers & Plastics (AREA)
• Materials Engineering (AREA)
• Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
• Mycology (AREA)
• Cosmetics (AREA)
• Medicinal Preparation (AREA)
• Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
• Coloring Foods And Improving Nutritive Qualities (AREA)

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Citations (3)

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• 2009
  • 2009-10-01 FR FR0956843A patent/FR2950884B1/fr active Active
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• 2010
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  • 2010-09-16 KR KR1020127010047A patent/KR101502809B1/ko active IP Right Grant
  • 2010-09-16 WO PCT/FR2010/051926 patent/WO2011039445A1/fr active Application Filing
  • 2010-09-16 KR KR1020147032018A patent/KR101676551B1/ko active IP Right Grant
  • 2010-09-16 EP EP10770573.3A patent/EP2483228B1/fr active Active
  • 2010-09-16 US US13/499,503 patent/US20120251460A1/en not_active Abandoned
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• 2016
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