WO2011036031A1 - An antimicrobial particle and a process for preparing the same - Google Patents
An antimicrobial particle and a process for preparing the same Download PDFInfo
- Publication number
- WO2011036031A1 WO2011036031A1 PCT/EP2010/062618 EP2010062618W WO2011036031A1 WO 2011036031 A1 WO2011036031 A1 WO 2011036031A1 EP 2010062618 W EP2010062618 W EP 2010062618W WO 2011036031 A1 WO2011036031 A1 WO 2011036031A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- antimicrobial
- composition
- particle
- clay
- octahedral
- Prior art date
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- 230000000845 anti-microbial effect Effects 0.000 title claims abstract description 131
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- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000004665 cationic fabric softener Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- SOROIESOUPGGFO-UHFFFAOYSA-N diazolidinylurea Chemical compound OCNC(=O)N(CO)C1N(CO)C(=O)N(CO)C1=O SOROIESOUPGGFO-UHFFFAOYSA-N 0.000 description 1
- 229960001083 diazolidinylurea Drugs 0.000 description 1
- 229960004698 dichlorobenzyl alcohol Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- WSDISUOETYTPRL-UHFFFAOYSA-N dmdm hydantoin Chemical compound CC1(C)N(CO)C(=O)N(CO)C1=O WSDISUOETYTPRL-UHFFFAOYSA-N 0.000 description 1
- KRHIGIYZRJWEGL-UHFFFAOYSA-N dodecapotassium;tetraborate Chemical class [K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-] KRHIGIYZRJWEGL-UHFFFAOYSA-N 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000013003 healing agent Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- ACGUYXCXAPNIKK-UHFFFAOYSA-N hexachlorophene Chemical compound OC1=C(Cl)C=C(Cl)C(Cl)=C1CC1=C(O)C(Cl)=CC(Cl)=C1Cl ACGUYXCXAPNIKK-UHFFFAOYSA-N 0.000 description 1
- 229960004068 hexachlorophene Drugs 0.000 description 1
- 229960003258 hexylresorcinol Drugs 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 239000003752 hydrotrope Substances 0.000 description 1
- 229940071206 hydroxymethylglycinate Drugs 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 229940051866 mouthwash Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- HLERILKGMXJNBU-UHFFFAOYSA-N norvaline betaine Chemical compound CCCC(C([O-])=O)[N+](C)(C)C HLERILKGMXJNBU-UHFFFAOYSA-N 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 239000006179 pH buffering agent Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- HWGNBUXHKFFFIH-UHFFFAOYSA-I pentasodium;[oxido(phosphonatooxy)phosphoryl] phosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O HWGNBUXHKFFFIH-UHFFFAOYSA-I 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 230000003711 photoprotective effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 235000010241 potassium sorbate Nutrition 0.000 description 1
- 239000004302 potassium sorbate Substances 0.000 description 1
- 229940069338 potassium sorbate Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 238000004626 scanning electron microscopy Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 244000005714 skin microbiome Species 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- DIORMHZUUKOISG-UHFFFAOYSA-N sulfoformic acid Chemical compound OC(=O)S(O)(=O)=O DIORMHZUUKOISG-UHFFFAOYSA-N 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229960003500 triclosan Drugs 0.000 description 1
- 239000007195 tryptone soya broth Substances 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/26—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests in coated particulate form
-
- 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
- A61K8/0241—Containing particulates characterized by their shape and/or structure
- A61K8/0254—Platelets; Flakes
- A61K8/0258—Layered structure
-
- 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
- A61K8/26—Aluminium; 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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/416—Quaternary ammonium compounds
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
-
- 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
- A61Q15/00—Anti-perspirants or body deodorants
-
- 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
- A61Q19/10—Washing or bathing preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/006—Antidandruff preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B33/00—Silicon; Compounds thereof
- C01B33/20—Silicates
- C01B33/36—Silicates having base-exchange properties but not having molecular sieve properties
- C01B33/38—Layered base-exchange silicates, e.g. clays, micas or alkali metal silicates of kenyaite or magadiite type
- C01B33/44—Products obtained from layered base-exchange silicates by ion-exchange with organic compounds such as ammonium, phosphonium or sulfonium compounds or by intercalation of organic compounds, e.g. organoclay material
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/40—Compounds of aluminium
- C09C1/42—Clays
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/02—Inorganic compounds ; Elemental compounds
- C11D3/12—Water-insoluble compounds
- C11D3/124—Silicon containing, e.g. silica, silex, quartz or glass beads
- C11D3/1246—Silicates, e.g. diatomaceous earth
- C11D3/1253—Layer silicates, e.g. talcum, kaolin, clay, bentonite, smectite, montmorillonite, hectorite or attapulgite
- C11D3/126—Layer silicates, e.g. talcum, kaolin, clay, bentonite, smectite, montmorillonite, hectorite or attapulgite in solid compositions
-
- 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
- A61K2800/41—Particular ingredients further characterized by their size
- A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
-
- 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
-
- 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
- A61K2800/60—Particulates further characterized by their structure or composition
- A61K2800/61—Surface treated
- A61K2800/612—By organic compounds
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2002/00—Crystal-structural characteristics
- C01P2002/80—Crystal-structural characteristics defined by measured data other than those specified in group C01P2002/70
- C01P2002/84—Crystal-structural characteristics defined by measured data other than those specified in group C01P2002/70 by UV- or VIS- data
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/80—Particles consisting of a mixture of two or more inorganic phases
- C01P2004/82—Particles consisting of a mixture of two or more inorganic phases two phases having the same anion, e.g. both oxidic phases
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2991—Coated
Definitions
- This invention relates to a bipolar antimicrobial particle for use in laundry detergent compositions, fabric conditioners, personal care and cosmetic compositions and a process for making the same.
- Antimicrobials are used widely in many technological fields like detergents and
- laundry including e.g. wash and fabric conditioning
- personal care including e.g.
- compositions for giving antimicrobial activity to the substrate for giving antimicrobial activity to the substrate.
- antimicrobial In today' s world most people are concerned about their health, hygiene and appearance. Therefore most of the consumer products use antimicrobial as one of the key ingredients. People use antimicrobial in oral hygiene products, in skin lotions and creams, in anti-perspirant and in many other formats. The objective of this product format is generally to deliver a suitable antimicrobial agent to a target substrate.
- Antimicrobial agents essentially reduce the microbial activity or inhibit growth of microorganisms on a surface or in a composition. In case of deodorants antimicrobial helps to reduce the malodour caused by the microbial activity in human sweat . Likewise in case of laundry compositions adding an
- antimicrobial molecule in the formulation and depositing it through main-wash or after-wash will reduce the microbial activity in the washing liquor and on the fabric thus avoiding malodour on the fabric.
- antimicrobial agent in personal wash, personal care and oral hygiene remains to be desired. Therefore washed fabrics end up with a relatively low amount of adsorbed antimicrobial and high dosing and/or repeated use are required in personal wash, personal care and oral hygiene. Accordingly the dosage of antimicrobial in the respective washing products is generally higher than required to compensate for the loss. Since
- antimicrobial agents are relatively expensive ingredients, it is desired to reduce the loss on rinsing.
- Clay with adsorbed antimicrobial is also known in literature. After the absorption people add this organoclay to a polymer matrix to form a nanocomposite is also known.
- WO2008/152417 discloses a method of preparing a polymer nanocomposite having antimicrobial properties
- WO2008/152417 uses a material in which
- antimicrobial agents are entrapped and adsorbed onto the clay surface dispersed in a polymeric matrix and doesn't provide a robust solution of making an antimicrobial particle as a singl entity with absolute increase in retention property. Hence a particle with immobilized antimicrobial agent remains to be desired.
- US 5,317,568 discloses the improvement of dispersibility of extender pigments in ink formulations by using as the extender pigment, a quaternary ammonium treated kaolin clay.
- the method disclosed in US 5,317,568 is not suitable for the purpose of the present invention
- Obj ects In view of the foregoing, it is an object of the present invention to provide a stabile antimicrobial agent immobilised on a carrier particle.
- antimicrobial molecules tagged by surface reaction onto naturally occurring asymmetric clay surfaces act as an antimicrobial particle with improved retention properties with improved stability.
- the present invention provides a bipolar
- a quaternary ammonium material comprising a single alkyl or alkenyl long chain having an average chain length greater than or equal to C20, or a quaternary ammonium material selected from
- CPC Cetylpyridinium chloride
- CAC Cetyltrimethylammonium Chloride
- CTAB Cetyltrimethylammonium Bromide
- BKC Benzalkonium Chloride
- Benzethonium chloride cetrimide
- Quaternium polyhexamethylene BH
- antimicrobial alcohols antimicrobial phenols, antimicrobial organic acids/salts, Zinc pyrithione, Ketoconazole, Octopirox R or combinations thereof .
- the invention provides a detergent
- composition comprising antimicrobial particle of the invention.
- the invention provides the use of the
- the invention provides the use of the
- antimicrobial activity on skin and scalp preferably non- therapeutical.
- the invention provides A process for
- bipolar antimicrobial particle which precursor is an asymmetric 1:1 or 2:1:1 clay particle having alternating tetrahedral and octahedral sheets terminating with a
- octahedral sheet at another external surface plane comprising the steps of (a) contacting the precursor with a mineral acid (b) adjusting the pH of the solution above 8 (c) adding a antimicrobial molecule to the mixture (d) heating the mixture to a temperature of 50 - 150 °C for about 30 minutes to 10 hours while stirring, and (e) separating the solid product comprising bipolar particulate antimicrobial.
- the invention provides a personal wash composition comprising antimicrobial particle of the invention and an acceptable base.
- the invention provides a deodorant
- composition comprising antimicrobial particle of the invention and an acceptable base.
- an asymmetric 1:1 or 2:1:1 clay particle having alternating tetrahedral and an octahedral sheets terminating with a tetrahedral and an octahedral sheet at exterior surface planes.
- Particle of 1:1 clay is particularly preferred as precursor.
- preferred 1 : 1 clays include kaolinite and serpentine subgroups of minerals.
- the species included within the kaolinite subgroup include but are not limited to kaolinite, dickite, halloysite and nacrite.
- the species within the serpentine subgroup include but are not limited to chrysolite, lizardite, and amesite.
- preferred 2:1:1 clays include chlorite group of minerals. Chlorite is sometimes wrongly referred to as 2:2 clay by some mineralogists.
- the chlorite comprises tetrahedral-octahedral-tetrahedral sheets like 2:1 clays, with an extra weakly bound brucite like layer between tetrahedral layers.
- the tetrahedral sheet preferably comprises coordinating
- the tetrahedral sheet may also comprise isomorphously substituted coordinating tetrahedral cations which are not silicon.
- Isomorphously substituted coordinating tetrahedral cations include, but are not limited to, cations of aluminum, iron or boron.
- the octahedral sheet preferably comprises coordinating
- the octahedral sheet may also comprise isomorphously substituted coordinating octahedral cations which are not aluminium.
- Isomorphously substituted coordinating octahedral cations include cations of magnesium or iron .
- the antimicrobial agent is attached to the coordinating cations on the exterior side of one of the
- coordinating cations on the exterior side of each of the tetrahedral and the octahedral surface sheets are attached to a antimicrobial molecule, with the proviso that the
- antimicrobial molecule attached to the coordinating cations on the exterior side of the tetrahedral surface sheet is not identical to the molecule attached to the coordinating cations on the exterior side of the octahedral surface sheet.
- the antimicrobial molecule is preferably attached to the coordinating cations on the external surface of the octahedral surface plane and is not preferably attached to coordination cations of non-exterior tetrahedral or octahedral plane or on the interior side of the surface sheets.
- antimicrobial ratio is between 1:0.001 and 1:0.1, more
- antimicrobial molecule is attached selectively to coordinating cations on the exterior plane of either the tetrahedral or the octahedral surface plane of asymmetric clay can be used to prepare the bipolar particulate antimicrobial according to the present invention.
- asymmetric clay can be used to prepare the bipolar particulate antimicrobial according to the present invention.
- the reaction is selective to only one of the exterior planes.
- selective is meant that more than 50% of the total antimicrobial molecule is present on one of the exterior planes, preferably more than 75%, more preferably than 80%, still more preferably than 90%, even more preferably than 95%, or even more than 99%.
- the chemical reaction or series of reactions wherein the same antimicrobial molecule attached to coordinating cations of both the surface sheets, viz octahedral and tetrahedral, are
- the particle has two spatially distinct exterior faces having distinct surface characteristics. It is envisaged that by selecting specific antimicrobial molecule having specific group, and selectively attaching them to coordinating cations of
- the invention provides a process for preparing a bipolar antimicrobial particle which precursor is an asymmetric 1:1 or 2:1:1 clay particle having alternating tetrahedral and octahedral sheets terminating with a
- octahedral sheet at another external surface plane comprising the steps of contacting the precursor with a mineral acid, adding a antimicrobial molecule to the mixture, adjusting the pH of the solution above 8, heating the mixture to a
- the raw clay is treated with a mineral acid preferably hydrochloric acid.
- the hydrochloric acid is used in a concentration range of 0.01 (N) to 1 (N) , preferably about 0.1 (N) .
- the clay particle with the acid is then stirred. The stirring is typically done for 10-60 minutes, preferably about 30 minutes.
- pH of the system is preferably adjusted to above 8 by adding 0.1 (M) NaOH to the solution.
- the desired antimicrobial molecules were added to the dispersion.
- the antimicrobial molecules are then added in a concentration of 0.001 to 30 percent of the total weight of the dispersion, preferably 0.01 to 5%.
- the solution is preferably heated for between 1 to 10 hours, preferably 4 to 8 hrs and more preferably about 6 hrs while stirring at 50°C to 150°C preferably 70°C to 90°C more preferably at 80°C while stirring. Separating the solid product comprising the bipolar particulate antimicrobial .
- the dispersion mixture is preferably centrifuged to obtain the bipolar antimicrobial particle as residue. Then it is preferably washed with copious amount of water and subsequently with a ketone solvent (e.g. acetone) . After that it is dried in an oven to get the final product.
- a ketone solvent e.g. acetone
- antimicrobial molecule is attached to the coordinating cations of the octahedral sheet preferable by covalent bonding.
- the antimicrobial particle made by this process has different wettability characteristics for two external surface planes. Antimicrobial group
- the anti micriobial group is preferably selected from the group of Quaternary ammonium salts such as Cetylpyridinium chloride (CPC) , Cetyltrimethylammonium Chloride (CTAC) ,
- CAB Cetyltrimethylammonium Bromide
- BKC Benzalkonium Chloride
- Benzethonium chloride cetrimide
- Quaternium Quaternium
- polyhexamethylene BH etc or from the group of antimicrobial alcohols such as Phenoxy ethanol, benzyl alcohol,
- hexachlorophene or from a group of antimicrobial phenols such as Triclosan, Thymol, dichlorophenol , 2-chloro-4-fluoro phenol, tetrafluorobenzoic acid, cresol, hexylresorcinol , microlides or from the group of antimicrobial organic acids/salts such as Benzoic acid/ sodium benzoate, Salicylic Acid/ Sodium
- hydroxymethyl glycinate cyclohexane diacetic acid monoamide, chloronicotinic acids, succinic acid, Peracetic acid or Zinc pyrithione, Ketoconazole, Octopirox R , or combinations thereof.
- antimicrobials are selected for the purpose of present invention to provide protection against skin bacteria such as Propionibacteria spp . , Corynebacteria spp . , Actinobacteriales , Staphylococci spp. (e.g. S. epidermidis) , Lactobacilales , Clostridiales , ⁇ -proteobacteria , ⁇ -proteobacteria , a- proteobacteria , Flavobacteriales , Bacteriodales , Malassezia yeasts (e.g. Malassezia furfur and Malassezia globosa) etc.
- Antimicrobial particles in detergent composition e.g. Malassezia furfur and Malassezia globosa
- the present invention provides a detergent composition for improved antimicrobial action on the fabrics and textiles.
- the particulate antimicrobial is preferably delivered to the fabric by a detergent composition.
- This detergent composition may be made by any conventional process.
- the particulate antimicrobial is preferably incorporated in 0.01% to 10% by weight of the detergent composition, more preferably from 0.1% to 5% by weight of the composition.
- surfactants may also be included in the detergent composition.
- zwitterionic surfactant or combinations thereof may be used in the detergent composition.
- the surfactants of the surfactant system may be chosen from the surfactants described well known textbooks like "Surface Active Agents" Vol. 1, by Schwartz & Perry, Interscience 1949, Vol. 2 by Schwartz, Perry & Berch, Interscience 1958, and/or the current edition of
- the surfactant is preferably incorporated to 50% by weight of the detergent composition, preferably at least 10% or even more than 15%, while generally less than 40% and even less than 30%. Although any concentration of surfactant may be used, suitable concentration is in the range of 0.5 to 3 grams per liter of the water after dissolution of the detergent
- builders may also be included in the detergent composition.
- Preferred builders include alkali metal
- the builder is preferably incorporated in 10% to 50% by weight of the detergent composition.
- Preferably 0% to 10% minors may also be incorporated in the detergent composition. These minors include perfumes, colours, pH modifier etc.
- the detergent composition is suitable for any kind of laundry and machine-wash (with horizontal axis or vertical axis) applications and for any kind of fabric like cotton, polyester, polycotton etc.
- the antimicrobial particle is preferably delivered to the fabrics and textiles through a fabric conditioner composition.
- This fabric conditioner is made by usual way of making any fabric conditioner composition.
- the particulate antimicrobial is preferably incorporated in 0.01% to 10% by weight of the detergent composition, more preferably from 0.1% to 5% by weight of the composition.
- the wash component will preferably include a fabric softening and/or conditioning compound (hereinafter referred to as "fabric softening compound”) , which may be a cationic or nonionic compound, as commonly used in the art.
- fabric softening compound a fabric softening and/or conditioning compound
- the fabric softening compounds may be water insoluble
- the compounds may be present in amounts of up to 8% by weight (based on the total amount of the composition) in which case the compositions are considered dilute, or at levels from 8% to about 50% by weight, in which case the compositions are considered concentrates.
- compositions suitable for delivery during the rinse cycle may also be delivered to the fabric in the tumble dryer if used in a suitable form.
- Suitable cationic fabric softening compounds are substantially water-insoluble quaternary ammonium materials comprising a single alkyl or alkenyl long chain having an average chain length greater than or equal to C2 0 or, more preferably, compounds comprising a polar head group and two alkyl or alkenyl chains having an average chain length greater than or equal to C14.
- the fabric softening compounds have two long chain alkyl or alkenyl chains each having an average chain length greater than or equal to Ci6. Most preferably at least 50% of the long chain alkyl or alkenyl groups have a chain length of Cis or above.
- Substantially water-insoluble fabric softening compounds are defined as fabric softening compounds having a solubility of less than 1 x 10-3 wt % in demineralised water at 20°C.
- the fabric softening compounds have a solubility of less than 1 x 10-4 wt%, more preferably less than 1 x 10-8 to 1 x 10-6 wt%.
- the compositions may alternatively or additionally contain water-soluble cationic fabric softeners.
- the compositions may comprise a cationic fabric softening compound and oil.
- the compositions may alternatively or additionally contain the polyol polyester (eg, sucrose polyester) compounds.
- compositions may alternatively or additionally contain nonionic fabric softening agents such as lanolin and derivatives thereof.
- the compositions may also suitably contain a nonionic stabilising agent.
- Suitable nonionic stabilising agents are linear Cs to C22 alcohols alkoxylated with 10 to 20 moles of alkylene oxide, C 1 0 to C20 alcohols, or mixtures thereof.
- the composition can also contain fatty acids, for example Cs to C24 alkyl or alkenyl monocarboxylic acids or polymers thereof.
- the fabric conditioning compositions may include soil release polymers such as block copolymers of polyethylene oxide and terephthalate ; amphoteric surfactants; zwitterionic quaternary ammonium compounds; and nonionic surfactants.
- the fabric conditioning compositions may be in the form of emulsions or emulsion precursors thereof.
- emulsifiers for example, sodium chloride or calcium chloride
- electrolytes for example, sodium chloride or calcium chloride
- pH buffering agents for example, sodium chloride or calcium chloride
- perfumes preferably from 0.1 to 5% by weight
- antimicrobial particles in shampoo composition can also be added to the formulation .
- Antimicrobial particles in shampoo composition can also be added to the formulation .
- This shampoo composition is made by usual way of making any shampoo composition.
- the particulate antimicrobial is preferably incorporated in 0.01% to 10% by weight of the shampoo composition, more
- composition preferably from 0.1% to 5% by weight of the composition.
- the shampoo composition may comprise of an anionic surfactant selected from alkyl ether sulphate, alkyl sulphate or
- anionic surfactants are Ci o to Ci 8 alkyl sulphate, and Ci o to Ci s alkyl ether sulphates containing 1 to 5 moles of ethylene oxide.
- anionic surfactants are Ci o to Ci 8 alkyl sulphate, and Ci o to Ci s alkyl ether sulphates containing 1 to 5 moles of ethylene oxide.
- surfactant a number of other types of anionic
- surfactant may also be included.
- the shampoo composition may also comprise of a sunscreen, or a mixture thereof, for photo protection.
- the shampoo composition may additionally comprise of co- surfactants such as Ci o _ Ci 8 alkyl or alkylamido propyl betaine, Ci o _ Ci8 fatty acid alkanolamide or mixtures thereof.
- co- surfactants such as Ci o _ Ci 8 alkyl or alkylamido propyl betaine, Ci o _ Ci8 fatty acid alkanolamide or mixtures thereof.
- the shampoo composition of the invention may also include minors which are commonly employed in shampoos like foam boosters, viscosity-adjusting agents, pearlescers, perfumes, dyes, colouring agents, thickeners, conditioning agents, proteins, polymers, buffering agents, preservatives etc.
- Antimicrobial for cosmetic application may selected from Salicylic acid, Zinc pyrithione, Ketoconazole, Octopirox R etc to protect against the dandruff causing yeasts.
- the present invention provides a cosmetic composition for improved antimicrobial actions on skin.
- antimicrobial is preferably delivered to the skin through a cosmetic composition.
- This cosmetic composition is made by usual way of making any skin formulation.
- the particulate antimicrobial is preferably incorporated in 0.05% to 10% by weight of the skin composition, more preferably from 0.1% to 10%, most preferably from 0.2 % to 5 % by weight of the composition.
- the skin cosmetic composition preferably comprises a
- composition cosmetically acceptable vehicle to act as a diluent, dispersant or carrier for other materials present in the composition, so as to facilitate their distribution when the composition is applied to the skin.
- concentrations of these in vanishing cream base is generally from 5%-25% by weight C 1 2-C20 fatty acids and 0.1%-10% by weight fatty acid soap.
- Vehicles other than water can include liquid or solid
- emollients emollients, solvents, humectants, thickeners and powders.
- Examples of each of these types of vehicles can be used singly or as mixtures of one or more vehicles.
- compositions of the present invention may comprise a wide range of other optional components like antioxidants, binders, biological additives, buffering agents, colorants, thickeners, polymers, astringents, fragrance, humectants, opacifying agents, conditioners, exfoliating agents, pH adjusters,
- cosmetic composition a personal care composition.
- compositions may be "leave ons", where the product is left to deliver actives/provide benefits on human substrate e.g. skin (including surfaces on face, hands, body, hair, lips, under arms) .
- Such personal care compositions also include “wash-off” products for cleaning surfaces of human body.
- the present invention provides a deodorant composition for improved antimicrobial actions on skin.
- antimicrobial is preferably delivered to the skin through a deodorant composition for protection against malodour.
- This deodorant composition is made by usual way of making any deodorant formulation.
- Deodorant compositions may be deliver through different product format e.g. deo-sprays, deo-sticks or roll-ons.
- the particulate antimicrobial is preferably incorporated in 0.05% to 10% by weight of the deo composition, more preferably from 0.1% to 10%, most preferably from 0.2 % to 5 % by weight of the composition.
- the deo formulations may further comprise conventional
- Deo cream compositions of the present invention for use as a deo-stick or roll-ons will include a deodorant active. Most preferable is an astringent salt which combines the properties of deodorancy and antiperspirancy . Amounts of the deodorant active may range from 0.1 to 70%.
- Deodorant actives according to the present invention also include materials other than those functioning as
- Deodorants should be capable of killing or hindering the growth of microorganisms that generate malodour or that promote the decomposition of body oils into odiferous fatty acids.
- Amounts of particulate antimicrobial of the invention may range from 0.1 to 1%, preferably 0.2 to 0.5% by weight .
- deodorant cosmetic creams of the present invention is that of a volatile emollient.
- the emollient is preferably selected from volatile polyorgansiloxanes, C7-C10 hydrocarbons and combinations thereof. These materials may be present in amounts from 1 to 70%, preferably from 10 to 50%, optimally from 25 to 35% by weight.
- volatile refers to those materials having a measurable pressure at ambient conditions .
- Deodorant cosmetic cream compositions of the present invention will also contains powdered filler/drying agent like starches, talc, fumed silica, finely divided silica, sodium bicarbonate, magnesium aluminium silicate and mixtures thereof. Clays could also be used as a powdered. Amounts of the powdered
- filler/drying agent will range from 1 to 40%, preferably from 10 to 35%, optimally from 15 to 30% by weight.
- a non-volatile liquid emollient optionally included within the deodorant cosmetic creams of the present invention.
- Non-volatile polyorganosiloxanes , C12-C40 hydrocarbons and combinations thereof may be suitable for this purpose. Amounts of this material may range from 1 to 40%, preferably from 5 to 25%, optimally from 10 to 20% by weight.
- Antimicrobial particles in hand-wash composition provides a hand-wash composition.
- the antimicrobial particle is preferably delivered to the hands by a hand-wash composition.
- This hand ⁇ wash composition is made by usual way of making any hand-wash composition .
- the particulate antimicrobial is preferably incorporated in 0.01% to 10% by weight of the hand-wash composition, more preferably from 0.1% to 5% by weight of the composition.
- the hand-wash composition may further comprise of one or more anionic surfactants, amphoteric and/or zwitterionic
- the anionic surfactant may be selected from aliphatic
- Zwitterionic surfactants are exemplified by those which can be broadly described as derivatives of aliphatic quaternary ammonium, phosphonium, and sulphonium compounds, in which the aliphatic radicals can be straight or branched chain, and wherein one of the aliphatic substituents contains from about 8 to about 18 carbon atoms and one contains an anionic group, e.g., carboxy, sulphonate, sulphate, phosphate, or phosphonate.
- the non-ionic which may be used includes in particular the reaction products of compounds having a hydrophobic group and a reactive hydrogen atom, for example aliphatic alcohols, acids, amides or alkyl phenols with alkylene oxides, especially ethylene oxide either alone or with propylene oxide.
- the composition may also comprises of humectants like low molecular weight alcohols such as ethanol, butanol or low molecular weight PEGs or glycerine.
- ingredients such as viscosity modifier, pearlizers, perfumes, vitamins, preservatives, dyes etc. may also be included in the composition.
- composition in minor quantity.
- Example 1 Preparation of antimicrobial particle of the
- Kaolinite Super shine 90, EICL
- 5g of Kaolinite was taken in a 500ml of 0. IN HC1 (Merck) solution and sonicated for 30 minutes. The pH is then increased to 9 by addition of NaOH (Merck) solution drop wise.
- NaOH Merck
- To this lOg CPC was added and the suspension was stirred over a magnetic stirrer (Spinpot) for 6 hours while maintaining the temperature of the solution at 75-80 °C.
- the suspension was then washed with water for about 10 times to remove the excess CPC and a final ethanol (Les Alcools De Commerce) wash was given.
- the clay was then dried in a hot air oven .
- Powder (diffuse reflectance) technique was utilized for this measurement.
- Clay as control and reacted clay of the invention were grounded with 50% w/w of KBr in a pestle and mortar and then IR was done on these powders.
- the IR spectrum of the reacted clay was compared against that of pure clay. New peaks were observed in the reacted clay at the wave numbers of 2926 cm “1 , 2855 cm “1 , 1487 cm “1 and 1466 cm “1 .
- the peaks at 2926 cm “1 and 2855 cm “1 are due to the C-C stretching of the alkyl chain of the CPC, while the peaks at 1487 cm “1 and 1466 cm “1 are due to the ring carbon and nitrogen of the CPC.
- Example 3 Retention comparison of antimicrobial molecule with the particle of the invention onto fabric.
- Example 4 Evaluation of antimicrobial activity of the particle of the invention Staphylococcus epidermidis was grown in Tryptone Soya Broth (TSB, HiMedia 30g/L) and shaker incubated for 18hrs at 37°C. The broth was centrifuged. The supernatant was decanted and the pellet was re-suspended 0.9% saline solution. The re-suspended solution was diluted to between 10 7 -10 8 cfu/mL with saline solution using a optical density calibration curve known to a skill person. 100 micro litres of this suspension of
- Solution protocol A sub culture of S .mutans was grown in BHI broth (ex Difco 37 g/L) and grown in a CO 2 incubator having 5% CO 2 at 37 °C for 15hrs. The grown culture broth was taken and the concentration was adjusted by dilution with BHI glucose broth (BHI ex Difco 37g/L and Glucose 2%) to 10 8 cfu/ml. Then 1 mL of the culture was mixed with 9 mL of a saline solution containing various concentrations of particle suspension of the invention resulting to the concentration as indicated in the Table 2 below. The samples were incubated as above for 2hrs .
- Antimicrobial particle of the invention (equivalent
- the model detergent contains: 0.6 g/L Na-LAS; 1.2 g/L
- antimicrobial versus antimicrobial particle of the invention antimicrobial versus antimicrobial particle of the invention.
- CPC was taken as the molecular antimicrobial for this purpose and CPC reacted clay particle was taken as the antimicrobial particle of the invention.
- the rinsing step was repeated twice with 20 mL of deionized water each.
- UV spectrophotometer Libda EZ210 Spectrophotometer
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Abstract
Description
Claims
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2010800422569A CN102575205A (en) | 2009-09-24 | 2010-08-30 | An antimicrobial particle and a process for preparing the same |
BR112012006098A BR112012006098B8 (en) | 2009-09-24 | 2010-08-30 | bipolar antimicrobial particle, washing composition, personal cleaning composition, deodorant composition, dental hygiene composition, process for preparing a bipolar antimicrobial particle and non-therapeutic use of clay particle |
CA2772849A CA2772849A1 (en) | 2009-09-24 | 2010-08-30 | An antimicrobial particle and a process for preparing the same |
ES10747052.8T ES2601859T3 (en) | 2009-09-24 | 2010-08-30 | Antimicrobial particle and process to prepare it |
MX2012003566A MX2012003566A (en) | 2009-09-24 | 2010-08-30 | An antimicrobial particle and a process for preparing the same. |
EA201200532A EA201200532A1 (en) | 2009-09-24 | 2010-08-30 | ANTIBACTERIAL PARTICLES AND METHOD FOR THEIR PRODUCTION |
AU2010297474A AU2010297474B2 (en) | 2009-09-24 | 2010-08-30 | An antimicrobial particle and a process for preparing the same |
EP10747052.8A EP2480651B1 (en) | 2009-09-24 | 2010-08-30 | An antimicrobial particle and a process for preparing the same |
US13/496,898 US20120177712A1 (en) | 2009-09-24 | 2010-08-30 | antimicrobial particle and a process for preparing the same |
ZA2012/01521A ZA201201521B (en) | 2009-09-24 | 2012-02-29 | An antimicrobial particle and a process for preparing the same |
Applications Claiming Priority (4)
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IN2222MU2009 | 2009-09-24 | ||
IN2222/MUM/2009 | 2009-09-24 | ||
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PCT/EP2010/062618 WO2011036031A1 (en) | 2009-09-24 | 2010-08-30 | An antimicrobial particle and a process for preparing the same |
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US (1) | US20120177712A1 (en) |
EP (1) | EP2480651B1 (en) |
CN (1) | CN102575205A (en) |
AU (1) | AU2010297474B2 (en) |
BR (1) | BR112012006098B8 (en) |
CA (1) | CA2772849A1 (en) |
CL (1) | CL2012000724A1 (en) |
EA (1) | EA201200532A1 (en) |
ES (1) | ES2601859T3 (en) |
MX (1) | MX2012003566A (en) |
PL (1) | PL2480651T3 (en) |
WO (1) | WO2011036031A1 (en) |
ZA (1) | ZA201201521B (en) |
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WO2014102032A1 (en) | 2012-12-27 | 2014-07-03 | Unilever N.V. | Oral care composition having an adduct of clay and antibacterial agent |
WO2017144260A1 (en) | 2016-02-23 | 2017-08-31 | Unilever N.V. | A disinfectant aqueous composition and method for treating substrates |
WO2019034387A1 (en) * | 2017-08-17 | 2019-02-21 | Unilever N.V. | Method of promoting remineralisation of teeth |
WO2019043713A1 (en) * | 2017-08-30 | 2019-03-07 | Nobio Ltd. | Compositions and medical devices comprising anti-microbial particles |
WO2020126317A1 (en) | 2018-12-21 | 2020-06-25 | Unilever N.V. | Antimicrobial compositions comprising modified clay and nonionic triblock copolymers |
WO2020126351A1 (en) | 2018-12-21 | 2020-06-25 | Unilever N.V. | Antimicrobial compositions comprising modified clay and biphenol |
WO2021104780A1 (en) | 2019-11-28 | 2021-06-03 | Unilever Ip Holdings B.V. | Antimicrobial compositions comprising modified clay and copolymers |
US11178867B2 (en) | 2016-02-25 | 2021-11-23 | Nobio Ltd. | Micro and nanoparticulate compositions comprising anti-microbially active groups |
WO2021259748A1 (en) | 2020-06-24 | 2021-12-30 | Unilever Ip Holdings B.V. | Compositions comprising zinc and antimicrobial agent |
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WO2023232570A1 (en) | 2022-05-31 | 2023-12-07 | Unilever Ip Holdings B.V. | Granules of clay-based antimicrobial particles |
WO2023232571A1 (en) | 2022-05-31 | 2023-12-07 | Unilever Ip Holdings B.V. | Spherical granules of clay-based antimicrobial particles |
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KR102200185B1 (en) * | 2014-10-30 | 2021-01-08 | (주)아모레퍼시픽 | Skin or Hair Washing Composition |
CN110113942A (en) | 2016-11-07 | 2019-08-09 | 朱比兰特生命科学有限公司 | Synergistic antimicrobial compositions |
EP3587505A1 (en) * | 2018-06-29 | 2020-01-01 | Aerogel ApS | Encapsulated biocides and biorepellents |
WO2021078685A1 (en) | 2019-10-23 | 2021-04-29 | Unilever Ip Holdings B.V. | Method of reducing dental hypersensitivity |
US11701317B2 (en) | 2021-03-24 | 2023-07-18 | L'oreal | Cosmetic compositions for removing makeup and methods thereof |
FR3124948B1 (en) * | 2021-07-09 | 2024-05-17 | Oreal | Cosmetic compositions for removing make-up and corresponding processes |
CN114479620A (en) * | 2022-03-07 | 2022-05-13 | 广东腐蚀科学与技术创新研究院 | Antifouling and anticorrosive paint capable of being coated underwater and preparation method thereof |
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Also Published As
Publication number | Publication date |
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AU2010297474B2 (en) | 2014-06-26 |
CN102575205A (en) | 2012-07-11 |
ZA201201521B (en) | 2013-05-29 |
EP2480651B1 (en) | 2016-08-03 |
BR112012006098B8 (en) | 2021-01-12 |
CL2012000724A1 (en) | 2012-10-19 |
PL2480651T3 (en) | 2017-08-31 |
BR112012006098B1 (en) | 2020-12-29 |
MX2012003566A (en) | 2012-04-30 |
BR112012006098A2 (en) | 2016-05-31 |
EA201200532A1 (en) | 2012-09-28 |
AU2010297474A1 (en) | 2012-03-29 |
US20120177712A1 (en) | 2012-07-12 |
ES2601859T3 (en) | 2017-02-16 |
EP2480651A1 (en) | 2012-08-01 |
CA2772849A1 (en) | 2011-03-31 |
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