WO2015123745A1 - Procédé de nanoencapsulation d'agents actifs en double émulsion inverse et produits résultants - Google Patents

Procédé de nanoencapsulation d'agents actifs en double émulsion inverse et produits résultants Download PDF

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Publication number
WO2015123745A1
WO2015123745A1 PCT/BR2015/000018 BR2015000018W WO2015123745A1 WO 2015123745 A1 WO2015123745 A1 WO 2015123745A1 BR 2015000018 W BR2015000018 W BR 2015000018W WO 2015123745 A1 WO2015123745 A1 WO 2015123745A1
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WIPO (PCT)
Prior art keywords
emulsion
phase
water
assets
inverse
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Ceased
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English (en)
Portuguese (pt)
Inventor
Adriano Marim de OLIVEIRA
Renato Rosafa GAVIOLI
Natalia Neto Pereira CERIZE
Maria Helena Ambrosio ZANIN
Kleber Lanigra GUIMARÃES
Lucilene Betega de PAIVA
Vitorio Giovanni Zanetti Ferraz
Moacir de MANCILHA
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IHARABRAS SA INDUSTRIAS QUIMICAS
Instituto de Pesquisa Tecnologicas do Estado Sao Paulo S/A (IPT)
Original Assignee
IHARABRAS SA INDUSTRIAS QUIMICAS
Instituto de Pesquisa Tecnologicas do Estado Sao Paulo S/A (IPT)
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Publication of WO2015123745A1 publication Critical patent/WO2015123745A1/fr
Anticipated expiration legal-status Critical
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Classifications

    • 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
    • A01N25/28—Microcapsules or nanocapsules
    • 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
    • A61K8/11—Encapsulated compositions
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • 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
    • A61K2800/10—General cosmetic use
    • 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
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/51—Nanocapsules; Nanoparticles
    • A61K9/5192—Processes

Definitions

  • the invention pertaining to the employment sector of pre-treated encapsulated organic ingredients for use in asset preparations applied to agrochemicals, pharmaceuticals, cosmetics, veterinary, food, paper, paints, adhesives, oil and gas, construction, textile , consists of a nanoencapsulated generation method based on the three-phase double emulsification, comprised of an active-rich inner phase to be encapsulated and a low water miscibility oil, an intermediate phase consisting of the encapsulant material dissolved in water and a phase. external compound composed of emulsifier dissolved in silicone.
  • the formation of the nano-encapsulated occurs after distillation of the aqueous intermediate phase and precipitation of the encapsulating material under the internal oily phase containing the active.
  • This method is capable of generating nanostructured shell-core special physical forms (nanoparticles) containing an oily core and a semipermeable polymeric shell dispersed in a silophilic hydrophobic phase, allowing the release of the active substance from within by diffusion or rapid release. by the breaking of the shell by the action of mechanical stress or solubilization.
  • the "NANOENCAPSULATION METHOD OF DUAL INVERSE EMULSION ASSETS AND RESULTANT PRODUCTS” presents a method for obtaining nanoencapsulated assets, generated as a dispersion in the silophilic phase, by means of a double phase nanoemulsion process followed by extraction of intermediate phase water by distillation and formation of nanocapsules.
  • This method presents as the use of a double inverse emulsion so that the active - hydrophobic or partially hydrophilic - is encapsulated in low water solubility oil by a hydrophilic polymer, and the resulting nano-encapsulated product is suspended in a medium. silophilic. 04.
  • the method comprises the execution of five consecutive processing phases, which allow the generation of nanoencapsulated, a) solubilization of the assets to be nanoencapsulated; b) pre-emulsifying a phase containing the assets solubilized in an immiscible or water-miscible solvent in a saturated aqueous solvent phase and containing encapsulant material; c) emulsifying this resulting preemulsion into a silophilic oil containing emulsifiers; d) nanoemulsification of this double emulsion; e) distillation for extraction of water from the intermediate phase and formation of nanocapsules.
  • the generated products are presented as a colloidal dispersion in silophilic medium.
  • the "Nanoencapsulation Method of Double Reverse Emulsion Assets and Resulting Products” enables different types of nanoencapsulated to be obtained and may be as high as 10% by mass in the final product, allowing a range of applications in various sectors of industry, such as pharmaceutical, cosmetic, veterinary, food, agrochemical, paper, inks, adhesives, oil and gas, construction, textile, among others, for the possibility of developing different compositions of nanoencapsulated containing assets that have incomplete solubility or partial in aqueous medium.
  • Leaching or degradation phenomena further reduce any possible residual effect of the product, making consecutive applications necessary in situations where use should be continued. Consecutive applications result in increased costs associated with product use, possible occupational risk due to operator exposure to the products, and increased amount of assets in the application environment.
  • Asset encapsulation techniques have been used to protect these assets from phenomena such as those described, offering advantages when using a particular asset, such as its controlled release to the medium by diffusion, or rapid release through disruption. of the shell due to the action of mechanical stress. This effect allows for fewer product applications containing the asset and greater security for users.
  • the particles showed improved resistance to thermal degradation and ultraviolet radiation, with ultraviolet degradation more than 10 times lower than free active.
  • Nanocapsulated production can be based on various methods such as solvent evaporation, emulsification and solvent diffusion, salting out, supercritical fluids, preformed polymer dispersion, polymerization of monomers, and nanocapsule production methods. from the gelling of ionic polymers.
  • the nanocapsulation process by the solvent evaporation method was the first method developed for the preparation of polymeric nanoparticles from preformed polymers.
  • polymeric solutions containing the active ingredient are prepared in volatile solvents and then simple emulsions are formed, which are converted to nanoparticle suspensions upon evaporation of the solvent.
  • This technique is the most used in the preparation of polymeric nanoparticles according to the current literature.
  • ES 2 194 590 A1 (ES2194590 A1, Biodegradable Microspheres with Extended Release and Preparation Procedure, FERRET, AND, ASIN, ME.GARC ⁇ A, J., TARIN, P., AROLA, R., RUTLL ⁇ N, M -, PÉREZ, A., 2001) a double w / o / w emulsion was used from a method in which the active was dissolved in the aqueous internal phase and it was emulsified into a hydrocarbon containing a dissolved polymer, and this emulsion was again emulsified into an aqueous phase containing emulsifiers. The organic solvent was then evaporated so that microparticles could be obtained.
  • the formed microcapsules encapsulate hydrophilic actives with the use of water insoluble polymer.
  • FR 2808703 A1 (FR2808703 A1 Proceeds from the preparation of a double monodisperse emulsion, FERNANDO, L. C, PHILIPPE, G., JAQUES, BJM, 2000) describes a method for obtaining a monodisperse double water emulsion. in oil in water (w / o / w) by mixing an aqueous phase into an oil phase followed by dilution in oil, and incorporating this pre-emulsion into a second aqueous phase by high pressure homogenization.
  • the "Nanoencapsulation Method of Double Reverse Emulsion Assets and Resulting Products” comprises a method for the nanoencapsulation of poorly water soluble assets. Encapsulation is achieved by dissolving the active in a water-immiscible or low-miscible solvent with a boiling point greater than water, which is pre-emulsified in an aqueous solution containing hydrophilic polymers. This preemulsion is again emulsified in a lipophilic oil, giving rise to a double inverse emulsion. The double inverse emulsion is further subjected to high pressure homogenization, and the resulting nanoemulsion is subjected to distillation to extract water from the intermediate phase.
  • the method makes it possible to obtain a suspension of core-shell nanoparticles containing poorly water-soluble active material dissolved in a core solvent and shell composed of solid hydrophilic polymer.
  • the external phase of the suspension is a hydrophobic silophilic type oil.
  • Figure 1 shows the size distribution curves for the 3.7% active sample, with the curves indicating triplicate measurements of the same sample.
  • Figure 3 - shows the size distribution curves for the 2.2% active sample, with the curves indicating triplicate measurements of the same sample.
  • Figure 4 Photomicrograph of nanocapsulated with 2.2% active nanometer order 027.
  • Figure 5 shows the size distribution curves for the 8.0% active sample, with the curves indicating triplicate measurements of the same sample.
  • Figure 7 - shows the size distribution curves for the 3.4% active sample, with the curves indicating triplicate measurements of the same sample.
  • Figure 9 - shows the size distribution curves for the 3.2% active sample, with the curves indicating triplicate measurements of the same sample.
  • the "Method of NANOENCAPSULATION OF INVERSE DUPLAEMULSION ASSETS AND RESULTING PRODUCTS" is a form of obtaining nanoencapsulated by double inverse emulsification followed by extraction of the intermediate phase by distillation.
  • This method is comprised of the execution of five consecutive processing steps that allows the generation of nanoencapsulates. These steps are: a) solubilization of the assets to be nanocapsulated; b) pre-emulsifying a phase containing the assets solubilized in a water immiscible or poorly miscible solvent in a saturated aqueous phase of the solvent and containing encapsulating material; c) emulsifying this resulting preemulsion into a silophilic oil containing emutants; d) nanoemulsification of this double emulsion; and e) distillation for water extraction from the intermediate phase and formation of nanocapsules.
  • step a) or organic phase is carried out by mechanical or magnetic stirring of the solvent and the actives to be nanocapsulated. Stirring is performed until complete solubilization of the assets at a temperature ranging from 5 to 90 ° C, preferably 23 ° C, with stirring from 5 to 3,000 rpm, preferably 400 rpm, at ambient pressure.
  • the solvent used should be immiscible or poorly water miscible and boiling higher than water, preferably 205 ° C.
  • the assets must be hydrophobic or partially hydrophilic or combinations of them.
  • the present invention may provide formulations containing chemical or biological active ingredient (s) acting in the desired area and may be at least one fungicide, insecticide, insecticide synergist, larvicide, arthropod repellent, mating disruptor, pheromone, acaricide, algaecide, virucide, nematicide, molluscicide, herbicide, herbicide protector, growth regulator, growth promoter, fruiting stimulant, flower and / or fruit preservative, early flower fall prevention ingredient and / or fruit, bird repellent, avicide, rodenticide, mammal repellent, herbivorism inhibitor, chemical sterilizer, but not limited to or mixture thereof, preferably active ingredients belonging to that group with a water solubility of less than 100 g / l.
  • the encapsulating material is natural or synthetic polymer such as polysaccharide polymers, animal or vegetable protein, chitosan, gums (gum arabic, xanthan gum, guar gum, carrageenan gum, cashew gum, tara gum, tragacanth gum). , Karaya gum, gati gum), cellulose derivatives (carboxymethyl cellulose, carboxyethyl cellulose, etc.), polyvinylpyrrolidone, polyacrylates, polyacrylamides, polyvinylcaprolactams, and mixtures thereof, preferably polysaccharides such as starch.
  • natural or synthetic polymer such as polysaccharide polymers, animal or vegetable protein, chitosan, gums (gum arabic, xanthan gum, guar gum, carrageenan gum, cashew gum, tara gum, tragacanth gum). , Karaya gum, gati gum), cellulose derivatives (carboxymethyl cellulose, carboxyethyl
  • the polymers are used dissolved in water in a concentration of 4% to 35% by weight, preferably 22%, the water used being saturated with the solvent that makes up the organic phase prior to solubilization of the polymers and the solvents being long chain esters, the aromatics , and hydrocarbons.
  • an organic or inorganic salt added at concentrations ranging from 0.1 to 10% by weight, preferably 1% w / w, which acts as an electrolyte for co-stabilization during the second emulsification step.
  • water soluble salts preferably mono or bivalent chlorides.
  • the second step (step b) that composes the method is the preemulsification of the two solutions (solvent active solution and polymer in water solution) described above. Preemulsification is carried out by mechanical or magnetic stirring of the organic phase in the aqueous phase at a minimum speed of 100 rpm, preferably 1,000 rpm, at a temperature ranging from 5 to 90 ° C, preferably 23 ° C and ambient pressure.
  • the ratio of organic phase to aqueous phase may vary from 1: 1 to 1: 50 by mass, since for high cost pharmaceutical actives the well-diluted system, preferably 1: 2 by mass may be used.
  • the third step (step c) is the emulsification of the preemulsion generated in step b) into a hydrophobic dilute emulsifier of the silophilic type, using emulsifiers compatible with the silophilic phase, for example, silicone emulsifiers or silicon-modified silicone. polyoxydeethylene.
  • This emulsification is performed by mechanical agitation of the pre-emulsion in the silophilic phase at speeds ranging from 100 to 30,000 rpm (which for high cost pharmaceutical actives can be used well diluted system), preferably 1,000 rpm; temperature ranging from 5 to 90 ° C, preferably 23 ° C and ambient pressure, and the pre-emulsion ratio in the silophilic phase may range from 2: 1 to 1: 20 by mass (for high cost pharmaceutical actives use the well-diluted system), preferably 1: 1 by mass.
  • the fourth step (step d) is the nanoemulsification of the double emulsion resulting from step c).
  • This nanoemulsification is carried out with the aid of high pressure homogenization, using a number of cycles from a minimum of 1 to that required to achieve the desired particle size, generally less than 20 cycles, preferably 5 cycles.
  • the pressure used in the process should be a minimum of 50 bar and a maximum of 2,000 bar, preferably 1000 bar.
  • the temperature employed in the process ranges from 10 to 100 ° C, preferably ambient.
  • step e is the extraction of water from the intermediate phase (external phase of the emulsion generated in step b) by distillation under reduced pressure, elevated temperature and moderate agitation. Distillation is conducted at a pressure of less than 760 mmHg, preferably 140 mmHg, and a temperature between 23 ° C and 90 ° C, preferably 50 ° C, for as long as necessary to remove water from the system, which may take from 10 minutes to 20 minutes. hours, usually 3 hours. ⁇
  • the obtained material was mixed with 100 g of a silica oil phase composed of silicone oil, Xiameter PMX-200 100 OffDow Corning), containing 10% emulsifier, SF-1540® (Momentivé), with the aid of stirrer at 000 ° C. rpm This emulsion was then subjected to 5 cycles of high pressure emulsification at 1000 bar pressure.
  • a silica oil phase composed of silicone oil, Xiameter PMX-200 100 OffDow Corning
  • 10% emulsifier SF-1540® (Momentivé)
  • the nanoemulsion resulting from this operation was subjected to distillation in a jacketed glass reactor, mechanically agitated, with water circulation at 50 ° C at 110 mmHg pressure for 7 hours.
  • the obtained material was mixed to 100 g of a siliaphilic phase composed of silicone oil, Xiameter PMX-200 100 CS® (Dow Corning J. containing 10% specific emulsifier SF-1540® (Momentive), with the aid of stirrer at 1000 rpm This emulsion was then subjected to 5 cycles of high pressure emulsification at 1000 bar pressure.
  • the nanoemulsion resulting from this operation was subjected to distillation in a jacketed glass reactor, mechanically agitated, with water circulation at 70 ° C, at a pressure of 170 mmHg, for 5 hours.
  • the resulting nanoencapsulated was subjected to particle size analysis by dynamic scattering technique, morphological scanning electron microscopy and total active content by high performance liquid chromatography.
  • Figure 3 shows the size distribution curve for the nanocapsules obtained, averaging around 350nm.
  • Figure 4 shows the morphology of the obtained particles.
  • the nanoemulsion resulting from this operation was subjected to distillation in a jacketed glass reactor, mechanically agitated, with water circulation at 35 ° C at a pressure of 95mmHg for 9 hours.
  • the resulting nanoencapsulated was subjected to particle size analysis by dynamic scattering technique, scanning electron microscopic morphology and total active content by high performance liquid chromatography.
  • Figure 5 shows the size distribution curve for the obtained nanocapsules, averaging around 300nm.
  • Figure 6 shows the morphology of the obtained particles.
  • the material obtained was mixed to 100 g of a silophilic phase composed of silicone oil, Xiameter PMX-200 100 CS® (Dow Corning). Containing 10% specific emulsifier SF-1540® (Momentive), with the aid of stirrer at 1000 rpm. This emulsion was then subjected to five cycles of high pressure emulsification at a pressure of 000 bar.
  • the nanoemulsion resulting from this operation was subjected to distillation in a jacketed glass reactor, mechanically agitated, with water circulation at 35 ° C, at a pressure of 235 mmHg, for 9 hours.
  • the resulting nanoencapsulated was subjected to particle size analysis by dynamic, morphological scanning electron microscopy and total active content by high performance liquid chromatography.
  • Figure 7 shows the size distribution curve for the obtained nanocapsules, averaging around 250 nm.
  • Figure 8 shows the morphology of the obtained particles.
  • the material obtained was mixed to 100 g of a silica oil phase composed of silicone oil, Xiameter PMX-200 100 CS® (Dow Corning), containing 10% specific emulsifier SF-1540® (Momentive), with the aid of stirrer at 1000 rpm. This emulsion was then subjected to five cycles of high pressure emulsification at 1000 bar pressure.
  • the nanoemulsion resulting from this operation was subjected to distillation in a 500 ml jacketed glass reactor with mechanical stirring, with water circulation at 70 ° C, at a pressure of 235 mmHg, for 5 hours.
  • the resulting nanoencapsulated was subjected to particle size analysis by dynamic scattering technique, scanning electron microscopy morphology and total active content by high performance liquid chromatography.
  • Figure 9 shows the size distribution curve for the obtained nanocapsules, averaging around 250 nm, and Figure 10 shows the morphology of the particles obtained.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Wood Science & Technology (AREA)
  • Birds (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • Organic Chemistry (AREA)
  • Toxicology (AREA)
  • Dentistry (AREA)
  • Epidemiology (AREA)
  • Agronomy & Crop Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dispersion Chemistry (AREA)
  • Dermatology (AREA)
  • Manufacturing Of Micro-Capsules (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention, intitulée "Procédé de nanoencapsulation d'agents actifs en double émulsion inverse et produits résultants", concerne un procédé d'obtention d'agents actifs nanoencapsulés, produits sous la forme d'une dispersion en phase silicophile, au moyen d'un procédé de nanoémulsion double en phase inverse, suivi d'une extraction d'eau de la phase intermédiaire par distillation et formation des nanocapsules. Ce procédé consiste en l'utilisation d'une double émulsion inverse, de sorte que l'agent actif - hydrophobe ou partiellement hydrophile - soit encapsulé dans une huile de faible solubilité dans l'eau par un polymère hydrophile, et que le produit nanoencapsulé résultant se trouve en suspension dans un milieu silicophile. Le procédé comprend l'exécution de cinq phases de traitement consécutives permettant de générer les produits nanoencapsulés, soit a) la solubilisation des agents actifs à nanoencapsuler, b) la pré-émulsification d'une phase contenant les agents actifs solubilisés dans un solvant non miscible ou faiblement miscible avec l'eau dans une phase aqueuse saturée du solvant et contenant une matière d'encapsulation, c) l'émulsification de la pré-émulsion résultante dans une huile silicophile contenant des émulsifiants, d) la nanoémulsification de cette double émultion, et e) la distillation pour extraction de l'eau de la phase intermédiaire et la formation des nanocapsules. Les produits générés se présentent sous la forme d'une dispersion colloïdale en milieu silicophile. L'invention, intitulée "Procédé de nanoencapsulation d'agents actifs en double émulsion inverse et produits résultants", permet l'obtention de différents types de produits nanoencapsulés, les teneurs en agents actifs pouvant atteindre 10% en masse du produit final, d'où un vaste champ d'applications dans divers secteurs de l'industrie, tels que l'industrie pharmaceutique, cosmétique, vétérinaire, alimentaire ou agrochimique, l'industrie du papier, des peintures, des adhésifs, du pétrole et du gaz, la construction civile et le textile, entre autres, compte tenue de la possibilité d'élaborer différentes compositions de produits nanoencapsulés contenant des agents actifs présentant une solubilité incomplète ou partielle en milieu aqueux.
PCT/BR2015/000018 2014-02-18 2015-02-19 Procédé de nanoencapsulation d'agents actifs en double émulsion inverse et produits résultants Ceased WO2015123745A1 (fr)

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BRBR1020140037209 2014-02-18
BR102014003720-9A BR102014003720B1 (pt) 2014-02-18 2014-02-18 Método de nanoencapsulação de ativos em dupla emulsão inversa e produtos resultantes

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Cited By (1)

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CN117982346A (zh) * 2024-03-08 2024-05-07 深圳市羽素生物科技有限公司 一种高稳定性胶态硫祛痘精华液及其制备方法

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BRPI1001959A2 (pt) * 2010-06-15 2012-03-06 Instituto De Pesquisas Tecnológicas Do Est. S. Paulo S/a - Ipt Nanocarreadores coloidais para ativos hidrofílicos e processo de produção
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US20100015236A1 (en) * 2006-09-14 2010-01-21 Shlomo Magdassi Pesticide nanoparticles obtained from microemulsions and nanoemulsions
BRPI1001959A2 (pt) * 2010-06-15 2012-03-06 Instituto De Pesquisas Tecnológicas Do Est. S. Paulo S/a - Ipt Nanocarreadores coloidais para ativos hidrofílicos e processo de produção
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117982346A (zh) * 2024-03-08 2024-05-07 深圳市羽素生物科技有限公司 一种高稳定性胶态硫祛痘精华液及其制备方法

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BR102014003720A2 (pt) 2016-02-02

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