• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:

    公开号:BR112012007257B1
    申请号:R112012007257-9
    申请日:2010-09-16
    公开日:2018-07-31
    发明作者:Dalko Maria
    申请人:L'oreal；
    IPC主号:
    专利说明:

    (54) Title: USE OF AT LEAST ONE COMPOUND, PROCESS FOR THE CONSERVATION OF A COMPOSITION, COMPOSITION AND COSMETIC AND DERMATOLOGICAL COMPOSITIONS (51) Int.CI .: C07C 49/245; A61K 8/35; A61K 47/10 (30) Unionist Priority: 10/01/2009 FR 0956843, 10/06/2009 US 61 / 248,999, 11/17/2009 FR 0958082 (73) Holder (s): LOREAL (72) Inventor (s) ): MARIA DALKO (85) National Phase Start Date: 03/30/2012
    1/14 “USE OF AT LEAST ONE COMPOUND, PROCESS FOR THE CONSERVATION OF A COMPOSITION, COMPOSITION AND COSMETIC AND DERMATOLOGICAL COMPOSITIONS”
    Field of the Invention [001] The present invention relates to the use of vanillin derivatives, in particular as a preservative in cosmetic, dermatological or pharmaceutical compositions, preferably nutraceutical or oral cosmetics; the present invention also relates to new compounds capable of being used in cosmetics, dermatology or pharmacy, preferably nutraceutical or oral cosmetics, in particular as a preservative, as well as the compositions comprising these compounds.
    Background of the Invention [002] It is customary to introduce chemical preservatives in cosmetic or dermatological compositions to combat the development of microorganisms in these compositions, which would quickly make them unsuitable for use. In particular, it is necessary to protect the compositions against microorganisms that may develop inside the composition, for example, during its manufacture and also against those that the user may introduce into the composition by manipulating it. especially when gripping conditioned products in pot with your fingers. Commonly used chemical preservatives are, in particular, parabens, organic acids or formaldehyde-releasing compounds. These preservatives, however, have the disadvantage of causing irritation, particularly on sensitive skin, when they are present at relatively high rates. In addition, driven by a concern for the environment, consumers are increasingly looking for conservation agents that respect the environment, in particular non-ecotoxic. Furthermore, the effectiveness of the preservatives used classically varies and their formulation can
    Petition 870180042525, of 05/21/2018, p. 11/29
    2/14 give rise to problems, in particular incompatibility and even destabilization, of formulas, in particular emulsions.
    [003] The purpose of the present invention is to propose new preservative agents that have in particular a broad antimicrobial spectrum, at least as wide and, preferably, greater than that of existing compounds and that do not present the drawbacks of the state of the art, particular that they possess specific physicochemical properties that allow to protect the cosmetic formulas of the microbial contamination and that are at the same time well tolerated.
    Brief Description of the Invention [004] An object of the present invention is, therefore, the use as a preservative agent, in particular in a cosmetic, dermatological, pharmaceutical, nutraceutical or oral cosmetic composition, of at least one compound of formula (I):
    - R2 represents a hydrogen atom and R3 represents a linear (saturated) alkyl radical with C1-C6, eventually replaced by a hydroxyl group; or an alkenyl radical (unsaturated C = C) linear with C2C6, or a linear alkenyl radical with C2-C12 substituted by a hydroxyl group;
    - or R2 represents a methyl or ethyl radical and R3 represents a linear (saturated) alkyl radical with C1-C12, optionally substituted by a hydroxyl group; or an alkenyl radical (unsaturated C = C) linear with C2C12, eventually substituted by a hydroxyl group.
    Petition 870180042525, of 05/21/2018, p. 12/29
    3/14 [005] By preservative agent, is meant a substance that is commonly added to a composition in order to ensure its preservation against a contaminating agent. Advantageously, the compounds of formula (I) according to the present invention are used as an antimicrobial and / or antibacterial and / or antifungal agent.
    [006] Another object of the present invention is a process of preserving a cosmetic, dermatological, pharmaceutical, nutraceutical or oral cosmetic composition, characterized by the fact that it consists of incorporating to said composition at least one compound of formula (I).
    [007] Preferably, the compounds correspond to formula (I), in which:
    - (i) R2 is H and R3 represents a methyl, ethyl, propyl, butyl or pentyl radical, possibly substituted by an OH and in particular of structure
    -CH2-CH (OH) -R5 with R5 representing a linear alkyl radical with C1C4; or a C2-C6 alkenyl radical, in particular a -CH = CHR4 radical with R4 representing a linear alkyl radical with C1-C4; or else
    - (ii) R2 represents CH3 and R3 represents (i) a C1-C10 alkyl radical, in particular methyl, ethyl, propyl, butyl, pentyl or hexyl; (ii) a C2-C10 alkenyl radical, in particular a -CH = CH-R4 with R4 radical representing a linear C1-C6 alkyl radical; or (iii) a hydroxyalkyl radical of structure -CH2-CH (OH) -R5 with R5 representing a linear alkyl radical with C1-C10, preferably with C4-C10.
    [008] Of course, a mixture of compounds of formula (I) can be used.
    [009] Preferably, the composition does not comprise preservatives other than those of formula (I). In particular, the composition does not contain parabens.
    Petition 870180042525, of 05/21/2018, p. 13/29
    4/14 [010] Certain compounds of formula (I) are new and are also an object of the present invention; these are the following compounds of formula (I '):
    - R2 represents a hydrogen atom and R3 represents a linear (saturated) alkyl radical with C2-C6, eventually replaced by a hydroxyl group; or an alkenyl radical (unsaturated C = C) linear with C2C6, or a linear alkenyl radical with C2-C12 substituted by a hydroxyl group;
    - or R2 represents a methyl or ethyl radical and R3 represents a linear (saturated) alkyl radical with C1-C12, optionally substituted by a hydroxyl group; or an alkenyl radical (unsaturated C = C) linear with C2-C12, eventually substituted by a hydroxyl group.
    [011] Preferably, in formula (I '),
    - (i) R2 is H and R3 represents an ethyl, propyl, butyl or pentyl radical, optionally substituted by an OH and in particular of structure -CH2-CH (OH) -R5 with R5 representing a linear alkyl radical with C1C4; or a C2-C6 alkenyl radical, in particular a -CH = CHR4 radical with R4 representing a linear alkyl radical with C1-C4; or
    - (ii) R2 represents CH3 and R3 represents (i) a C1-C10 alkyl radical, in particular methyl, ethyl, propyl, butyl, pentyl or hexyl; (ii) a C2-C10 alkenyl radical, in particular a -CH = CH-R4 with R4 radical representing a linear C1-C6 alkyl radical; or (iii) a hydroxyalkyl radical of structure -CH2-CH (OH) -R5 with R5 representing a radical
    Petition 870180042525, of 05/21/2018, p. 14/29
    5/14 linear alkyl with C1-C10, preferably with C4-C10.
    [012] Particular mention may be made of the following compounds of formula (I) or (I '):
    [013] Cosmetic, dermatological or pharmaceutical compositions and nutraceutical or oral cosmetic compositions comprising at least one compound of formula (I), or of formula (I '), also form an object of the present invention.
    Detailed Description of the Invention [014] The compounds of formula (I) can be easily prepared by the person skilled in the art based on his general knowledge. In particular, the following bibliographical references can be cited: 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. Med. Chem. Lett., 2004, 14 (5), 1287-1289.
    [015] They can thus be prepared from ethylvaniline as follows:
    Petition 870180042525, of 05/21/2018, p. 15/29
    6/14
    r R3
    R2
    1) Na0H / H20
    2) HCI
    [016] The compounds of formula (I), alone or in mixture, can be used at the rate of 0.01% to 5% by weight, in particular 0.1% to 2.5% by weight, with weight of the composition, in cosmetic, dermatological or pharmaceutical compositions.
    [017] Cosmetic, dermatological or pharmaceutical compositions also comprise a cosmetic, dermatological or pharmaceutically acceptable medium, that is, compatible with keratin substances such as the skin of the face or body, lips, hair, eyelashes, eyebrows. and nails.
    [018] The compositions according to the present invention can be presented in any classically used galenic forms, in particular for topical application and, in particular in the form of aqueous, hydroalcoholic solutions, of oil-in-water emulsions (O / A ) or water-in-oil (E / H) or multiple (triple: W / O / W or O / W / O), aqueous gels, or dispersions of a grease phase in an aqueous phase by means of spherules, which spherules can be polymeric nanoparticles such as nanospheres and nanocapsules, or lipid vesicles of ionic and / or nonionic type (liposomes, niosomes, oleosomes), nanoemulsions, or thin films. These compositions are prepared according to the usual methods.
    [019] The compositions according to the present invention
    Petition 870180042525, of 05/21/2018, p. 16/29
    7/14 can be more or less fluid and have the appearance of a white or colored cream, an ointment, a milk, a lotion, a serum, a paste, a mousse. They can eventually be applied to the skin as an aerosol. They can also be presented in solid form and, for example, in stick form.
    [020] The composition according to the present invention can in particular take the form of:
    - a make-up product for the face, body or lips;
    - an aftershave gel or lotion;
    - a depilatory cream;
    - a body hygiene composition, such as a shower gel or shampoo;
    - a pharmaceutical composition;
    - a solid composition, such as a soap or a cleaning bar;
    - an aerosol composition which also comprises a pressure-propelling agent;
    - a styling lotion, a cream or a styling gel, a dye composition, a hair restructuring lotion, a perm composition, a lotion or a fall protection gel;
    - a composition for oral use.
    [021] The physiologically acceptable medium in which the compounds can be used, as well as their components, their quantity, the galenical form of the composition and their way of preparation, can be chosen by the technician on the subject based on his general knowledge according to the type of composition desired.
    Petition 870180042525, of 05/21/2018, p. 17/29
    8/14 [022] In particular, the composition can comprise any fatty body commonly used in the considered field of application. Particular mention can be made of silicone fatty bodies such as oils, gums and silicone waxes, as well as non-silicone fatty bodies, such as oils, pastes and waxes of vegetable, mineral, animal and / or synthetic. The oils may possibly be volatile or non-volatile.
    [023] Among silicone oils, volatile or non-volatile polydimethylsiloxanes (PDMS) with linear or cyclic silicone chain, liquid or pasty at room temperature, in particular cyclopolidimethylsiloxanes such as cyclohexassiloxane; polydimethylsiloxanes containing alkyl, alkoxy or phenyl groups, pendant or at the end of a silicon chain, groups containing 2 to 24 carbon atoms; phenylated silicones such as phenyltrimethicones, phenyldimethicones, phenyltrimethylsiloxidiphenyl siloxanes, diphenyl-dimethicones, diphenylmethyldiphenyltrysiloxanes, 2-phenylethyltrimethylsiloxysilicates and polymethylphenylsiloxates; Hydrocarbon oils of vegetable origin include liquid fatty acid triglycerides containing 4 to 10 carbon atoms such as heptanoic or octanoic acid triglycerides or, for example, sunflower, corn and soybean oils , pumpkin, grape, sesame, hazelnut, apricot, macadamia, macaw, sunflower, castor, avocado, triglycerides of caprylic / capric acids; jojoba oil, shea butter oil.
    [024] The following may also be mentioned as a fatty body that can be used:
    - fatty acids containing 8 to 32 carbon atoms;
    - synthetic esters and ethers, in particular of the formula R 1 COOR 2 and R 1 OR 2 where R 1 represents the residue of a fatty acid which
    Petition 870180042525, of 05/21/2018, p. 18/29
    9/14 contains 8 to 29 carbon atoms and R 2 represents a hydrocarbon chain, branched or unbranched, which contains 3 to 30 carbon atoms, such as Purcelin oil, isononyl isononanoate, isopropyl myristate, ethyl-2-hexyl palmitate, octyl-2-dodecyl stearate, octyl-2-dodecyl erucate, isostearyl isostearate; hydroxylated esters such as isostearyl-lactate, octyhydroxy-stearate, octyldodecyl hydroxystistate, diiso-stearylmalate, triisocetyl citrate, heptanoates, octanoates, fatty alcohol decanoates; polyol esters, such as propylene glycol dioctanoate, neopentylglycol diheptanoate and diethylene glycol diisononanoate; and pentaerythritol esters such as pentaerythrityl tetraisoestearate;
    - linear or branched hydrocarbons, of mineral or synthetic origin, such as paraffin oils, volatile or not and their derivatives, petroleum jelly, polydecenes, hydrogenated polyisobutene, such as parléam oil;
    - fatty alcohols containing 8 to 26 carbon atoms, such as cetyl alcohol, stearyl alcohol and its mixture (cetylstearyl alcohol), octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, alcohol oleic or linoleic alcohol.
    [025] The composition may also comprise an aqueous medium comprising water, a hydroalcoholic medium containing an alcohol with C2-C6, such as ethanol or isopropanol, or an organic medium comprising usual organic solvents such as alcohols with C2- C6, in particular ethanol and isopropanol, glycols such as propylene glycol, ketones.
    [026] The composition according to the present invention can also comprise the usual adjuvants in the cosmetic and dermatological fields, such as thickeners, emulsifiers, surfactants, gelling agents, cosmetic assets, perfumes, fillers, materials
    Petition 870180042525, of 05/21/2018, p. 19/29
    10/14 colorants, moisturizers, vitamins, polymers. The amounts of these different adjuvants are those used classically in the fields considered, for example, from 0.001 to 20% of the total weight of the composition. Such adjuvants, as well as their concentrations, must be chosen so as not to impair the advantageous properties of the compounds according to the present invention.
    [027] The pH of the compositions according to the present invention, when they comprise at least one aqueous phase (aqueous solutions, emulsions, for example), is preferably between 4 and 9, preferably between 4 and 7 , advantageously between 5 and 6.
    [028] The present invention is illustrated in more detail in the following exemplary embodiments.
    Example 1
    Determination of the Antimicrobial Activity of a Compound According to the Invention [029] The antimicrobial effectiveness of a compound of formula (I) was assessed by the Challenge Test method or artificial contamination.
    Tested compound
    Protocol [030] The challenge-test method consists of artificial contamination of the sample by microbial collection strains (bacteria, yeasts and molds) and an assessment of the number of revivifiable microorganisms seven days after inoculation.
    Petition 870180042525, of 05/21/2018, p. 20/29
    11/14 [031] In order to verify the effect of compounds of formula (I), the antimicrobial activity of a cosmetic formula containing, respectively, 2% of the compound according to the present invention was compared with the same formula alone ( control), after inoculation of approximately 10 6 CFU (Units that form colonies) / gram of cosmetic formula.
    Cosmetic Formula (% by Weight)
    - Sorbitan tristearate (Span 65 V® from Croda) 0.9% - Polyethylene glycol stearate (40 OE) (Myrj 52 P® from Croda) 2.0% - Mixture of glyceryl mono-distearate (36/64) / potassium stearate 3.0% - Fatty acids of vegetable origin (stearic acid / palmitic acid / myristic acid 53/44/3) 1.0% - Cetyl alcohol 3.8% - myristyl myristate 2.0% - Cyclopentasiloxane 5.0% - Loads 0.8% - Glycerin 3.0% - Hydrogenated isoparaffin 7.2% - White Vaseline 4.0% - Water qsp 100%
    Microorganism cultures [032] 5 pure microorganism cultures are used.
    germs Transplantation Medium T ° atcc Escherichia coli (Ec) Soy triptocaseína 35 ° C 8739 Enterococcus faecalis (Ef) Soy triptocaseína 35 ° C 33186 Pseudomonas aeruginosa (Pa) Soy triptocaseína 35 ° C 19429 Candida albicans (Ca) Sabouraud 35 ° C 10231 Aspergillus niger (An) Malt 35 ° C 6275
    ATCC = American Type Culture Collection.
    [033] Strains of gram bacteria - (Escherichia coli and
    Pseudomonas aeruginosa), gram + bacteria (Enterococcus faecalis), yeast (Candida albicans) and mold (Aspergillus niger) are inseminated in a transplant medium, the day before for the bacteria and the
    Petition 870180042525, of 05/21/2018, p. 21/29
    12/14 yeast and 5 days before inoculation for mold.
    [034] The day of inoculation:
    - a suspension in tryptone salt diluent is prepared respectively for bacteria and yeast, in order to obtain in the spectrophotometer a suspension with an optical density between 35% and 45% of light transmitted at 544 nm;
    - for mold, the spores are removed by washing the agar with 6 to 7 ml of collection solution and the suspension is placed in a sterile flask or tube.
    [035] After homogenizing the microbial suspension, 0.2 ml of inoculum is introduced into each pill (the suspensions are pure: between 1x10 8 and 3 χ 10 8 CFU per ml) and the microbial suspension is perfectly homogenized with a spatula in the 20 g of product (= Cosmetic formula).
    [036] The rate of microorganisms present in the product corresponds after homogenization to a concentration of 10 6 germs per gram of product, that is, the inoculation at 1% of an inoculum at 10 8 germs per ml.
    [037] After 7 days of contact time between the germs and the product at 22 ° C ± 2 ° C and in the dark, decimal dilutions are made and the number of revivable microorganisms that remain in the product is counted.
    Results:
    Number of UFC / gram of product at T7 days Compound Rate E. coli P. aeruginosa E. faecalis C. albicans A. niger 2% <200 <200 <200 <200 3.4 10 5
    Petition 870180042525, of 05/21/2018, p. 22/29
    13/14 <200 CFU: method sensitivity threshold.
    Example 2 [038] An emulsion is prepared which comprises (% by weight):
    - Sorbitan tristearate (Span 65 V® from Croda) 0.9% - Polyethylene glycol stearate (40 OE) (Myrj 52 P® from Croda) 2% - Mixture of glyceryl mono-distearate (36/64) / potassium stearate 3% - Fatty acids of vegetable origin (stearic acid / palmitic acid / myristic acid 53/44/3) 1% - Glycerin 3% - Cyclopentasiloxane 5% - Hydrogenated isoparaffin 7.2% - White Vaseline 4% - Cetyl alcohol 4% - myristyl myristate 2% - Loads 0.8% - compound tested in example 1 2% - Water qsp 100%
    Example 3 [039] An O / W emulsion is prepared which comprises (% by weight):
    - sodium hydroxide 0.03% - petroleum jelly 10% - 2-ethyl hexyl palmitate 10% - acrylic acid / stearyl methacrylate copolymer polymerized in an ethyl acetate / cyclohexane mixture 0.1% - glycerol 5% - mixture of cetylstearyl glycoside and cetyl alcohols,stearyl (12/46/42) 2.45% - compound tested in example 1 2% - microbiologically clean deionized water qsp 100%
    Example 4 [040] A lotion is prepared which comprises (% by weight):
    - allantoin 0.05% - sodium chloride 0.09% - Citric acid qsp pH 7 ± 0.2 - corn water 1% - hexylene glycol (2 methyl-2,4 pentanediol) 1% - glycerol 5% - N-cocoylamidoethyl, sodium N-ethoxycarboxymethyl glycionate 1.1% - sodium lauryl ether / magnesium sulfate (80/20) 4OE 0.45%
    Petition 870180042525, of 05/21/2018, p. 23/29
    14/14
    (52% MS) - compound tested in example 1 1.5% - microbiologically clean deionized water qsp 100%
    Petition 870180042525, of 05/21/2018, p. 24/29
    1/4
    权利要求:
    Claims (11)
    [1]
    Claims
    1. USE OF AT LEAST ONE COMPOUND, characterized by being a preservative agent in a cosmetic or dermatological composition, being the compound of formula:
    [2]
    2. USE, according to claim 1, characterized in that the compound, alone or in mixture, is present at the rate of 0.01% to 5% by weight, in particular from 0.1% to 2.5% by weight, in relation to the weight of the composition.
    [3]
    USE, according to either of claims 1 or 2, characterized in that the composition comprises a physiologically acceptable medium that comprises at least one ingredient chosen from: the silicone fatty bodies, such as oils, gums and silicone waxes; non-silicone fatty bodies, such as oils, pastes and waxes of vegetable, mineral, animal and / or synthetic origin; fatty acids containing 8 to 32 carbon atoms; esters and synthetic ethers, in particular of the formula R 1 COOR 2 and R 1 OR 2 where R 1 represents the residue of a fatty acid containing 8 to 29 carbon atoms and R 2 represents a branched hydrocarbon chain or unbranched, containing 3 to 30 carbon atoms; linear or branched hydrocarbons, of mineral or synthetic origin; fatty alcohols containing 8 to 26 carbon atoms; Water; alcohols with C2-C6; glycols, such as propylene glycol, ketones; thickeners, emulsifiers, surfactants, gelling agents, cosmetic actives, perfumes, fillers, coloring materials,
    Petition 870180042525, of 05/21/2018, p. 25/29
    2/4 moisturizers, vitamins and polymers.
    [4]
    4. USE, according to any one of claims 1 to 3, characterized in that the composition is in the form of a make-up product for the face, body or lips; an aftershave gel or lotion; a depilatory cream; a body care composition, such as a shower gel or shampoo; a pharmaceutical composition; a solid composition, such as a soap or a cleaning bar; an aerosol composition which also comprises a pressure-propelling agent; a styling lotion, a cream or a styling gel, a dye composition, a hair restructuring lotion, a perm composition, a lotion or an anti-hair loss gel; or a composition for oral use.
    [5]
    5. PROCESS FOR THE CONSERVATION OF A COMPOSITION, cosmetic or dermatological, characterized in that it consists of incorporating to said composition at least one compound as defined in claim 1.
    [6]
    6. COMPOUND, characterized by being of formula:
    [7]
    7. COSMETIC COMPOSITION, characterized by comprising the compound as defined in claim 6 as a preservative agent, and a physiologically acceptable medium comprising at least one ingredient chosen from: silicone fatty substances, non-silicone fatty substances, glycols, ketones, thickeners, emulsifiers, surfactants, gelling agents, fragrances, fillers, coloring materials, moisturizers, vitamins and polymers.
    Petition 870180042525, of 05/21/2018, p. 26/29
    3/4
    [8]
    8. DERMATOLOGICAL COMPOSITION, characterized by comprising the compound as defined in claim 6 as a preservative agent, and a physiologically acceptable medium comprising at least one ingredient chosen from: silicone fatty substances, non-silicone fatty substances, glycols, ketones, thickeners, emulsifiers, surfactants, gelling agents, fragrances, fillers, coloring materials, moisturizers, vitamins and polymers.
    [9]
    COMPOSITION according to either of claims 7 or 8, characterized in that the compound of formula (I), alone or in mixture, is present at the rate of 0.01% to 5% by weight, in particular 0.1 % to 2.5% by weight, based on the weight of the composition.
    [10]
    10. COMPOSITION according to claim 9, characterized in that it comprises a physiologically acceptable medium that comprises at least one ingredient chosen from: the silicone fatty bodies, such as oils, gums and silicone waxes; non-silicone fatty bodies such as oils, pastes and waxes of vegetable, mineral, animal and / or synthetic origin; fatty acids containing 8 to 32 carbon atoms; esters and synthetic ethers, in particular of the formula R 1 COOR 2 and R 1 OR 2 where R 1 represents the residue of a fatty acid containing 8 to 29 carbon atoms and R 2 represents a branched hydrocarbon chain or unbranched, containing 3 to 30 carbon atoms; linear or branched hydrocarbons, of mineral or synthetic origin; fatty alcohols containing 8 to 26 carbon atoms; Water; alcohols with C2-C6; glycols, such as propylene glycol, ketones; thickeners, emulsifiers, surfactants, gelling agents, cosmetic actives, perfumes, fillers, coloring materials, moisturizers, vitamins, polymers.
    [11]
    11. COMPOSITION, according to any of the
    Petition 870180042525, of 05/21/2018, p. 27/29
    Claims 7, 9 or 10, characterized in that it is in the form of a make-up product for the face, body or lips; an aftershave gel or lotion; a depilatory cream; a body care composition, such as a shower gel or shampoo; a solid composition, such as a soap or a cleaning bar; an aerosol composition which also comprises a pressure-propelling agent; a styling lotion, a cream or a styling gel, a dye composition, a hair restructuring lotion, a perm composition, a lotion or an anti-hair loss gel; of a composition for oral use.
    Petition 870180042525, of 05/21/2018, p. 28/29
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    法律状态:
    2017-10-10| B07A| Technical examination (opinion): publication of technical examination (opinion)|
    2018-02-20| B07A| Technical examination (opinion): publication of technical examination (opinion)|
    2018-07-03| B09A| Decision: intention to grant|
    2018-07-31| B16A| Patent or certificate of addition of invention granted|
    优先权:
    申请号 | 申请日 | 专利标题
    FR0956843A|FR2950884B1|2009-10-01|2009-10-01|USE OF VANILLIN DERIVATIVES AS A PRESERVATIVE, METHOD OF PRESERVATION, COMPOUNDS AND COMPOSITION|
    FR0956843|2009-10-01|
    US24899909P| true| 2009-10-06|2009-10-06|
    US61/248,999|2009-10-06|
    FR0958082A|FR2950805B1|2009-10-01|2009-11-17|USE OF VANILLIN DERIVATIVES AS A PRESERVATIVE, METHOD OF PRESERVATION, COMPOUNDS AND COMPOSITION|
    FR0958082|2009-11-17|
    PCT/FR2010/051926|WO2011039445A1|2009-10-01|2010-09-16|Use of vanillin derivatives as a preservative, preservation method, compounds, and composition|
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