WO2022269481A1 - Formulation topique antimicrobienne - Google Patents
Formulation topique antimicrobienne Download PDFInfo
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- WO2022269481A1 WO2022269481A1 PCT/IB2022/055735 IB2022055735W WO2022269481A1 WO 2022269481 A1 WO2022269481 A1 WO 2022269481A1 IB 2022055735 W IB2022055735 W IB 2022055735W WO 2022269481 A1 WO2022269481 A1 WO 2022269481A1
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- WIPO (PCT)
- Prior art keywords
- acid
- substance
- compounds
- formulation
- antimicrobial
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- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
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- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
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- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
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- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
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- A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
- A61L2/0005—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor for pharmaceuticals, biologicals or living parts
- A61L2/0082—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor for pharmaceuticals, biologicals or living parts using chemical substances
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- A61L2101/00—Chemical composition of materials used in disinfecting, sterilising or deodorising
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Definitions
- the invention relates to a topical antimicrobial formulation.
- formulations intended to be applied to the skin and in particular to the hands, for hygiene purposes and/or to prevent the spread of diseases.
- Such formulations are generally used without rinsing, in addition to and/or replacing washing with soap and water, and can more particularly be used by caregivers in the context of health care or when travelling. , both personal and professional as well as by children, particularly in schools, and more generally in the event of a risk of skin exposure with a possibly contaminated surface.
- formulations are intended to kill, deactivate or slow the growth of microbes harmful to human health, such as bacteria, yeasts, fungi and/or viruses.
- Antimicrobial formulations are known, called hydroalcoholic solutions, which contain an alcohol, in particular ethanol and/or isopropanol, mixed with an antimicrobial agent, for example a positively charged surfactant, of the quaternary ammonium type.
- hydroalcoholic solutions which contain an alcohol, in particular ethanol and/or isopropanol, mixed with an antimicrobial agent, for example a positively charged surfactant, of the quaternary ammonium type.
- Antimicrobial formulations which comprise an acid substance comprising at least one organic acid diluted in an aqueous solvent by exhibiting a deleterious action against microbes, said acid substance having a pKa acidity constant which is less than 6.
- These formulations are particularly effective because, in addition to being easily bio-sourced and biodegradable, they have low volatility in the air and low dermal absorption, which increases the effectiveness of their antimicrobial action when applied to a user's skin.
- the known formulations do not give complete satisfaction, because of their low dermo-compatibility induced by their acid pH, in particular lower than the pKa of the acid, which is necessary for their effectiveness. In particular, in the case of repeated applications, they may lead to the appearance of undesirable effects for the skin, in particular drying, redness and/or irritation of the epidermis.
- the invention aims to improve the prior art by proposing in particular a formulation which comprises an antimicrobial organic acid substance, in order to benefit from the advantages relating to biosourceability, biodegradability and persistence on the epidermis, while presenting dermo-compatibility improved.
- the invention proposes a topical antimicrobial formulation comprising an acidic substance comprising at least one organic acid diluted in an aqueous solvent while exhibiting a deleterious action against microbes, said acidic substance having an acidity constant pKa which is less than 6, said formulation further comprising:
- a basic substance comprising at least one base, the amount of basic substance in the formulation being such that the pH of said formulation is between the pKa of the acidic substance and 8;
- booster substance which is capable of biochemically interacting with the membrane of microbes to facilitate the deleterious action of the acidic substance on said microbes
- said booster substance comprising at least one compound referenced in the INCI database chosen from amphiphilic compounds, chelating compounds having a capacity for association with divalent ions or sterols, polyphenolic compounds.
- the invention relates to a topical antimicrobial formulation, in particular intended to be applied to the skin, in particular to the hands of a user, for hygiene purposes and/or to combat the spread of diseases.
- the formulation comprises an acid substance comprising at least one organic acid diluted in an aqueous solvent by exhibiting a deleterious action against microbes.
- the acid substance has a pKa acidity constant that is less than 6.
- the pKa considered is that of the weakest acid.
- the acidic substance may in particular exhibit virucidal activity, for example against viruses such as:
- herpes in particular HVEl (for "Equine Herpes Virus type 1");
- AdV5 for “Adenovirus 5”
- coronaviruses in particular SARS-COV-2 (for English “Severe Acute Respiratory Syndrome Coronavirus 2”).
- the acidic substance may also have other antimicrobial functions, in particular against bacteria (antibacterials), yeasts (yeast killers), and/or fungi (antifungals).
- the organic acid is chosen in particular from carboxylic acids, that is to say acids having a carboxyl group.
- carboxylic acids that is to say acids having a carboxyl group.
- these acids there are in particular the following components: lactic acid, citric acid, tartaric acid, acetic acid, adipic acid, anisic acid, malic acid, succinic acid , benzoic acid, cholic acid, ascorbic acid, dehydroacetic acid, deoxycholic acid, glucuronic acid, glycolic acid, fumaric acid, formic acid, gluconic acid , glutamic acid, guanylic acid, folic acid, fulvic acid, sorbic acid, glycyrrhizic acid, kojic acid, itaconic acid, mellisic acid, hyaluronic acid, amino acids, glutaric acid, glyoxylic acid, humic acids, hippuric acid, inosic acid, levulinic acid, perillic
- the organic acid can also be chosen from acids derived from vegetable oils, such as: safflower acids, rapeseed acids, coconut and copra acids, jojoba acids, palm acids, corn, soy acids, uric acid, as well as fatty acids, in particular fatty acids comprising between 3 and 24 carbon atoms (C3 to C24), including unsaturated and functionalized fatty acids.
- acids derived from vegetable oils such as: safflower acids, rapeseed acids, coconut and copra acids, jojoba acids, palm acids, corn, soy acids, uric acid, as well as fatty acids, in particular fatty acids comprising between 3 and 24 carbon atoms (C3 to C24), including unsaturated and functionalized fatty acids.
- the formulation comprises between 1% and 10% by weight, and preferably between 1% and 5% by weight, of acid substance in which the at least one organic acid used is referenced in the INCI base (for English “International Nomenclature of Cosmetic Ingredients”).
- the acidic substance comprises an organic acid or a mixture of organic acids, the individual concentrations of which are arranged to give the formulation a safety margin greater than 100 (MOS, for “Margin of Safety”).
- MOS margin is calculated according to standard methods in the field of toxicology, from the dermal absorption and the NOAEL value (for "Dosage without observable harmful effect") of each component of the formulation, as well as the scenario of 'exposure.
- the acidic substance comprises at least one organic acid chosen from lactic acid, lauric acid, citric acid, oleic acid, or a mixture of at least two of these compounds.
- the formulation further comprises a basic substance comprising at least one base, the amount of basic substance in said formulation being such that the pH of said formulation is between the pKa of the acidic substance and 8..
- the addition of a basic substance makes it possible to limit the total acidity of the formulation, in order to improve its dermo-compatibility, and thus to limit the risk of irritation and/or redness, in particular after several applications on the a user's skin.
- the formulation may comprise an amount of basic substance suitable for giving it a pH of the order of 5, which corresponds approximately to the minimum pH value of healthy human skin.
- the basic substance comprises at least one base chosen from organic acid salts, in particular sodium lactate and/or potassium lactate, clays, in particular bentonite and/or montmorillonite, sodium hydroxide, potassium hydroxide, triethanolamine, butylethanolamine, disodium carbonates, dipotassium carbonates, disodium phosphates, dipotassium phosphates, or a mixture of at least two of these compounds.
- organic acid salts in particular sodium lactate and/or potassium lactate
- clays in particular bentonite and/or montmorillonite
- sodium hydroxide potassium hydroxide
- triethanolamine butylethanolamine
- disodium carbonates dipotassium carbonates
- disodium phosphates dipotassium phosphates
- dipotassium phosphates or a mixture of at least two of these compounds.
- the basic substance comprises sodium hydroxide, optionally mixed with a clay, in particular based on bentonite and/or montmorillonite.
- organic acids When mixed in a formulation at a pH above their respective pKa constants, organic acids chemically react to produce salts, for example sodium salt or potassium salt, depending on the acid(s) used, which greatly attenuates or even deactivates their antimicrobial properties, and thus reduce the effectiveness of the formulation.
- the concentration of its organic form decreases all the more as the pH value of said formulation increases.
- the concentration of its acid form is greater than 5% of the total concentration of said organic acid, while this percentage drops to 0. .5% for a pH between pKa+1 and pKa+2.
- the formulation further comprises between 0.1% and 15% by weight, and preferably between 1% and 10% by weight, of a booster substance which is capable of biochemically interacting with the membrane of the microbes to facilitate the deleterious action of the acidic substance on said microbes.
- the booster substance makes it possible to stimulate the deleterious action of the acidic substance.
- the booster substance comprises at least one compound referenced in the INCI database chosen from:
- the booster substance may comprise at least one amphiphilic compound having a critical micellar concentration (CMC) value of between 1 mM and 400 mM, in particular between 10 mM and 100 mM.
- CMC critical micellar concentration
- the booster substance comprises at least one amphiphilic compound chosen from glyceryl laurate, glyceryl caprate, glyceryl caprylate, glyceryl palmitate, glyceryl stearate, quaternary ammoniums, saponins or a mixture of at least two of these compounds.
- the amphiphilic compound can also be chosen in the INCI base from fatty alcohols, ethoxylated alcohols, an amphiphilic compound with a betaine, phosphate or sulphate group, alkylated sugars, polylyglyceryl, polysorbate or a mixture of at least two of these compounds.
- the formulation may in particular comprise:
- Amphiphilic compounds have a molecular structure with a hydrophobic part having an affinity for membrane lipids and a hydrophilic part having an affinity for aqueous media. They can interact with the membrane lipid bilayer of microbes, in order to destabilize the membrane. Indeed, insofar as this lipid bilayer is mainly composed of phospholipids, certain amphiphilic compounds can reduce its coherence, and thus facilitate the penetration with the membrane of the acidic antimicrobial substance.
- the booster substance may also comprise at least one chelating compound which has a LogK constant for interaction with divalent ions or sterols greater than 4, and in particular greater than 8.
- This chelating compound may be chosen from EDTA (ethylenediaminetetraacetic acid) or one of its salts, cyclodextrin or one of its derivatives, phytic acid or one of its salts, oxalic acid or one of its salts, or a mixture of at least two of these compounds.
- microbe membranes include divalent ions, such as magnesium and calcium, or sterols, which increase their stability.
- divalent ions such as magnesium and calcium, or sterols
- the use of chelating compounds with appropriate LogK constants makes it possible to annihilate the effect of divalent ions and/or sterols and to reduce the stability of the membrane, which facilitates the penetration of said membrane by the acidic antimicrobial substance.
- the booster substance may also comprise at least one polyphenolic compound, chosen in particular from quercetin, oleuropein, caffeic acid, gallic acid, epigallocatechin, epigallocatechin-gallate, tannins, tannic acids, fulvic acids, humic acids, plant extracts, in particular based on olive, tea, cocoa, coffee, cassia, or a mixture of at least two of these compounds.
- at least one polyphenolic compound chosen in particular from quercetin, oleuropein, caffeic acid, gallic acid, epigallocatechin, epigallocatechin-gallate, tannins, tannic acids, fulvic acids, humic acids, plant extracts, in particular based on olive, tea, cocoa, coffee, cassia, or a mixture of at least two of these compounds.
- the presence of phenolic and/or polyphenolic compounds can contribute to the destabilization of the membranes of microbes, by interaction between the hydroxyl/benzoic groups of said compounds and the proteins of said membranes.
- the booster substance comprises compounds whose individual concentrations are arranged to give the formulation a MOS margin greater than 100 MOS, in order to guarantee said formulation good compatibility with the epidermis even in the event of applications repeated.
- the booster substance comprises a mixture based on glyceryl stearate, glyceyl laurate and xanthan, optionally mixed with benzalkonium chloride, cetrimonium chloride and/or methylcyclodextrin.
- the formulation may also comprise at least one additional compound having a dermo-compatible function, and in particular a dermo-cosmetic function, in order to provide an additional beneficial effect for maintaining the epidermis.
- the formulation may comprise at least one additional compound which has at least one dermo-cosmetic function chosen from: - the moisturizing and/or humectant functions, in order to increase the water content of the skin, in particular of the upper layers (for the humectant functions); and or
- the lipid-replenishing functions in order to reconstitute the lipids of the upper layers of the skin.
- the formulation may comprise at least one dermo-cosmetic compound chosen from an oil, shea butter, glycerol, triheptanoin, p-mentanediol, dibutyl adipate, a fatty alcohol or a mixture of at least two of these compounds.
- the formulation may in particular comprise:
- the formulation may also comprise an additional compound having a homogenizing function, in particular based on microcrystalline cellulose, in order to improve the distribution in the aqueous solvent of the various compounds of the formulation, in particular the compounds which have lipophilic groups.
- the solvent of the formulation consists mainly of water, the percentage of which by weight is adjusted according to the percentage by weight desired for the other compounds of the said formulation.
- Such a solvent has advantages in terms of dermo-compatibility, in that it makes it possible to reduce the risks of allergies and/or irritation for the skin, in particular in the context of repeated applications.
- the formulation can also comprise an additional organic solvent, in particular based on hexanediol.
- additional compounds are referenced in the I NCI database, and are also chosen to satisfy the toxicological criterion relating to the MOS margin described above.
- weight percentages refer to the total weight of said formulation.
- CMV42 a first “test” formulation, which contains the following ingredients:
- - as booster compounds o 6.5% by weight of glyceryl stearate (amphiphile); o 3% by weight of glyceryl laurate (amphiphile); o 0.4% by weight of xanthan (amphiphile).
- CMV40 A second "control" formulation, called CMV40, was also prepared, which differs from the CMV42 formulation in that it does not contain lactic acid or glyceryl laurate, and also included the other compounds listed above. in the same percentages.
- dermo-cosmetic compounds o 2% by weight of almond oil (moisturizer); o 0.1% by weight of shea butter (moisturizer); o 2% by weight of glycerol (humectant);
- microcrystalline cellulose - 0.05% by weight of microcrystalline cellulose
- a CMV42 formulation was also prepared as described in example 1, as well as three other "test" formulations CMV41, CMV43 and CMV44 according to the invention, which differ from the CMV42 formulation by the addition of additional ingredients, to to know :
- each of these formulations was tested according to a protocol similar to that of Examples 1 and 2, with a single dilution rate (10 3 ) and a contact time of 30 seconds between each formulation and the virus.
- lactic acid in particular: o alone (formulations CMV42, CMV44); or o in combination with (formulation CMV43):
- antimicrobial organic acids o 1% by weight of lactic acid; o 1% by weight of citric acid;
- - as booster compounds o 6% by weight of glyceryl stearate (amphiphile); o 1% by weight of glyceryl laurate (amphiphile); o 0.5% by weight of xanthan (amphiphile); o 0.13% by weight of benzalkonium chloride (amphiphile);
- - as dermo-cosmetic compounds o 7% by weight of almond oil (moisturizer); o 2.5% by weight of glycerol (humectant); o 1% by weight of triheptanoine (humectant); o 2% by weight of dibutyl adipate (emollient); o 1.5% by weight of shea butter (emollient); o 5% by weight of a fatty alcohol (emollient);
- This formulation was then tested in contact with a solution of cells infected with the HVE1 virus identical to those prepared for the previous examples, and following a similar experimentation protocol, with the exception of a contact time with the virus. of 60 seconds and a single dilution rate of 10-3 .
- a CMV910 formulation was prepared as described in Example 3.2, and mixed at a percentage of 97% in a solution comprising cells from an African green monkey renal epithelial cell line. (Vero-E6) infected with the SARS-CoV-2 virus, with a viral load of 6.10 7 TCID50/ml. The exposure time of the formulation to the virus was 60 seconds. At the end of this contact, a reduction in the viral load of greater than 99.99% was observed, which demonstrates an increased and rapid virucidal efficacy of the CMV910 formulation against the SARS-COV-2 virus.
- CMV40, CMV42, CMV43, CMV44 formulations identical to those used in Example 3 were prepared, as well as a fifth CMV45 formulation according to the invention, the composition of which differs from that of the CMV42 formulation by the addition of 2% by weight of p-menthanediol as a humectant compound.
- - as booster compounds o 6.5% by weight of glyceryl stearate (amphiphile); o 3% by weight of glyceryl laurate (amphiphile); o 0.4% by weight of xanthan (amphiphile).
- dermo-cosmetic compounds o 2% by weight of almond oil (moisturizer); o 0.1% by weight of shea butter (moisturizer); o 2% by weight of glycerol (humectant);
- microcrystalline cellulose - 0.05% by weight of microcrystalline cellulose
- CMVT "control" formulation contained only the aforementioned compounds, and no organic acids, the following compounds were added to each test formulation:
- CMV4 methyl cyclodextrin
- these pre-impregnated tissues were coated with a solution containing Vero-E6 cells infected with the SARS-COV-2 virus, with a viral load of 10 ⁇ l at 10 5 TCID50/2.25 cm 2 , counting a formulation/virus contact time of 5 minutes.
- anti-microbial organic acids o 2% by weight of lauric acid; o 1% by weight of oleic acid;
- booster compounds o 5% by weight of glyceryl stearate; o 2% by weight of glyceryl laurate; o 0.5% by weight of xanthan;
- a CMV910 “test” formulation was prepared as described in examples 3.2 and 4, which was applied to a Textile StreriWip fabric with an exposure time of 3 hours and in a quantity of 60 mg/2.25 cm 2 .
- Example 6.1 A solution of infected cells identical to that used in Example 6.1 was then applied to this textile, counting an exposure time of 5 minutes, at the end of which we observed the results, which revealed a reduction in the viral load greater than 98% after 3 hours of impregnation of the formulation tested, ie a result slightly higher than that observed with the “test” formulations of Example 6.1.
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EP22827791.9A EP4358927A1 (fr) | 2021-06-21 | 2022-06-21 | Formulation topique antimicrobienne |
CN202280050170.3A CN117642145A (zh) | 2021-06-21 | 2022-06-21 | 局部抗微生物配制剂 |
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WO2007142967A2 (fr) * | 2006-05-31 | 2007-12-13 | The Dial Corporation | Préparations antimicrobiennes contenant de l'alcool d'efficacité améliorée |
US20090087502A1 (en) * | 2007-09-27 | 2009-04-02 | Simon Jameson | Non-toxic Antimicrobial Composition |
WO2017216722A2 (fr) * | 2016-06-13 | 2017-12-21 | Vyome Biosciences Pvt. Ltd. | Compositions antifongiques synergiques et leurs procédés |
CN108210393A (zh) * | 2018-03-29 | 2018-06-29 | 李皆延 | 一种抗菌保湿去角质沐浴露及其制备方法 |
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DE4329517C2 (de) * | 1993-08-30 | 1996-04-04 | Schuelke & Mayr Gmbh | Waschende Händedesinfektions- und Händedekontaminationsmittel auf Basis naturidentischer, aromatischer Alkohole |
FR2813189B1 (fr) * | 2000-08-31 | 2003-02-28 | Oreal | Creme cosmetique moussante pour le traitement des peaux grasses |
US7569530B1 (en) * | 2003-06-20 | 2009-08-04 | The Procter & Gamble Company | Antimicrobial compositions, products and methods employing same |
US20080267904A1 (en) * | 2004-12-09 | 2008-10-30 | The Dial Corporation | Compositions Having A High Antiviral And Antibacterial Efficacy |
EP1827098A2 (fr) * | 2004-12-09 | 2007-09-05 | The DIal Corporation | Compositions presentant une efficacite antivirale et antibacteriennne elevee |
BRPI0518406A2 (pt) * | 2004-12-09 | 2008-11-18 | Dial Corp | composiÇÕes tendo uma alta eficÁcia antiviral e antibacteriana |
CN105832573A (zh) * | 2016-04-19 | 2016-08-10 | 南京巨鲨显示科技有限公司 | 一种胺类抗菌洗手液 |
CN106491441A (zh) * | 2016-11-30 | 2017-03-15 | 桂林理工大学 | 一种杀菌抑菌湿巾及制作方法 |
CN107468569A (zh) * | 2017-08-24 | 2017-12-15 | 林福运 | 一种儿童洗手液 |
BR112020020812A2 (pt) * | 2018-04-09 | 2021-01-19 | Rhodia Operations | Composições e métodos para desinfecção de longa duração |
CN110755340A (zh) * | 2019-05-21 | 2020-02-07 | 义乌喵小乐宠物用品有限公司 | 一种含有天然植物提取物成分的护肤沐浴液及其制备方法 |
CN110693734A (zh) * | 2019-11-08 | 2020-01-17 | 高煜浩 | 一种儿童用洗手液及其制备方法 |
CN112741795A (zh) * | 2021-02-22 | 2021-05-04 | 龚俊豪 | 一种含有天然植物提取物成分的护肤沐浴露及制备方法 |
CN112773739A (zh) * | 2021-03-13 | 2021-05-11 | 青岛广恩技术研发有限公司 | 一种抗菌洗手液及其制备方法 |
-
2021
- 2021-06-21 FR FR2106594A patent/FR3124080B1/fr active Active
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2022
- 2022-06-21 WO PCT/IB2022/055735 patent/WO2022269481A1/fr active Application Filing
- 2022-06-21 CN CN202280050170.3A patent/CN117642145A/zh active Pending
- 2022-06-21 EP EP22827791.9A patent/EP4358927A1/fr active Pending
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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GB1106945A (en) * | 1966-01-31 | 1968-03-20 | Medisan Ab | Shampoo preparation |
WO2007142967A2 (fr) * | 2006-05-31 | 2007-12-13 | The Dial Corporation | Préparations antimicrobiennes contenant de l'alcool d'efficacité améliorée |
US20090087502A1 (en) * | 2007-09-27 | 2009-04-02 | Simon Jameson | Non-toxic Antimicrobial Composition |
WO2017216722A2 (fr) * | 2016-06-13 | 2017-12-21 | Vyome Biosciences Pvt. Ltd. | Compositions antifongiques synergiques et leurs procédés |
CN108210393A (zh) * | 2018-03-29 | 2018-06-29 | 李皆延 | 一种抗菌保湿去角质沐浴露及其制备方法 |
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FR3124080A1 (fr) | 2022-12-23 |
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CN117642145A (zh) | 2024-03-01 |
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