WO2014162311A1 - Capsules réglables à base de sol-gel comprenant des fragrances, et des arômes et leurs utilisations - Google Patents

Capsules réglables à base de sol-gel comprenant des fragrances, et des arômes et leurs utilisations Download PDF

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Publication number
WO2014162311A1
WO2014162311A1 PCT/IL2014/050323 IL2014050323W WO2014162311A1 WO 2014162311 A1 WO2014162311 A1 WO 2014162311A1 IL 2014050323 W IL2014050323 W IL 2014050323W WO 2014162311 A1 WO2014162311 A1 WO 2014162311A1
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Prior art keywords
micro
composition
particles
fragrant
sol
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PCT/IL2014/050323
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English (en)
Inventor
David Avnir
Marzia Sciortino
Mario Pagliaro
Rosaria Ciriminna
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Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd.
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Publication of WO2014162311A1 publication Critical patent/WO2014162311A1/fr

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    • 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
    • A61K8/0279—Porous; Hollow
    • 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
    • A61K8/25—Silicon; 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/347—Phenols
    • 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
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • 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
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • 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
    • B01J13/06—Making microcapsules or microballoons by phase separation
    • B01J13/14—Polymerisation; cross-linking
    • B01J13/18—In situ polymerisation with all reactants being present in the same phase
    • 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
    • C11D3/50—Perfumes
    • C11D3/502—Protected perfumes
    • C11D3/505—Protected perfumes encapsulated or adsorbed on a carrier, e.g. zeolite or clay
    • 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
    • A61K2800/56—Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations

Definitions

  • Microencapsulation of aromas and fragrances is an important technology applied to control their release profiles and improve the efficiency of their use in a wide range of consumer products.
  • Most encapsulation techniques for developing microencapsulated fragrances and aromas are adapted from existing methods developed in pharmacy, in the food industry, in agriculture and in cosmetics; and are still being optimised in terms of performance, scaling up and costs (J. J. G. van Soest, Encapsulation of Fragrances and Flavours: a Way to Control Odour and Aroma in Consumer Products, In "Flavours and Fragrances", R. G. Berger (Ed.), Springer: Berlin, 2007).
  • Techniques employed in these industries include coacervation, liposome-entrapment, spray-drying and supercritical CO 2 encapsulation, among others.
  • Boettcher and co-workers were the first to investigate organic liquids embedded in silica sol-gel glasses, as reported in Advanced Materials 11 (1999) 138-141.
  • the authors investigated many different liquids in subsequent years, including trials to encapsulate different perfumes to prepare prolonged fragrant paper, textiles and other materials.
  • the problem is that since a perfume consists normally of three different liquids with very different optimized volatility, by adsorption and sol-gel immobilization the relation of volatility is changed and therefore the original scent is changed.
  • US Patent 4,788,164 describes a micro-porous inorganic oxide glass monolith doped with a volatile organic component and a nonvolatile organic component for sustained release. No mention is made, however, of the sol-gel small particles or small capsules, or of controlling the release profile of the components.
  • US Patent 7,258,874 discloses sol-gel microcapsules and methods for their preparation and use in controlled release applications. However, these methods are well suited for the entrapment of only water-soluble components in silica-based micro-particles, as it describes the preparation of ceramic particles from reverse micelle solution (water-in-oil, W/O).
  • sol-gel micro-encapsulation technology from an oil-in-water (O/W) emulsion described in US Patent 6,303,149 offers large potential in the context of the perfume industry.
  • the method affords 0.01-100 microns sol-gel core-shell hydrophilic microcapsules loaded with up to 80% w/w functional molecules, as stable aqueous suspensions for further formulation.
  • the technology described in US Patent 6,303,149 does not mention the possibility to organically modify the surface of the inorganic silica shell around entrapped actives in order to alter the odor profile of fragrances and aromas.
  • US Patent 6,303, 149 does not mention the possibility to entrap different components in different matrices in order to achieve the desired release profile.
  • compositions and methods to control the release kinetic profiles of multiple fragrances and aromas through the encapsulation of one or more fragrant mixtures in metal oxides and semi-metal oxide-based small particles are disclosed.
  • the resulting solid particles are advantageously used in applications where specific component-selective controlled release of the fragrance or aroma actives is required, either to preserve the original sensory feeling, or to create new ones by changing the classical order of release of top notes, medium notes and bottom notes.
  • the technology is ideally suited to stabilize and protect environmentally benign but unstable fragrances such as essential oils, thereby opening the route to the efficient utilization of essential oils in a number of applications, ranging from personal care to nutritional products.
  • the invention also discloses a method for formulating fragrances in water instead than in ethanol while diminishing the harmful interaction between the entrapped fragrance molecules and the skin.
  • the present invention relates to selectively control the release of the entrapped fragrances through tailored control of the properties of the organosilica shell, and in particular its hydrophobicity/hydrophilicity balance and textural properties (specifically pore volume and/or surface area).
  • the diameter size of the microcapsules is in the range of 0.01-
  • the shell thickness of the capsules can be controlled by varying the relative amount of monomer, such as MTMS (methyl trimethoxysilane), added to the oil phase which may vary from about 5 to about 80 weight percent.
  • monomer such as MTMS (methyl trimethoxysilane)
  • the present invention relates to the use of the sol-gel microencapsulation technology for producing solid particles doped with different fragrance chemicals which, upon release, preserves the original sensorial feeling, because the release of different encapsulants in different micro -particles takes place at similar rate.
  • this invention creates for perfumers the ability to create new smell-mixtures as it offers the opportunity to bring to a similar rate the release of different encapsulants, either from a mixture of particles, or from particles containing a mixture. This solves the traditional difficulty for perfumers to mix smells, because the volatility is different, and therefore the total overall smell changes with time.
  • a method for the preparation of stable suspensions of sol-gel-encapsulated perfumes suspended in water which can be used in sprays or applied directly, and which do not impart undue skin-feel.
  • a method for using biodegradable fragrances with no environmental effects such as for example musk odorants, which could not be used before because of low chemical stability during storage in the perfume.
  • the fragrance material comprises a plurality of fragrant components.
  • At least two components of the plurality of fragrant components are released in different predetermined profiles.
  • At least two fragrant components are comprised in different sol-gel micro-particles. [0033] In some embodiments, at least two fragrant components are comprised in the same sol-gel micro-particles.
  • the sol-gel micro-particles are selected from the group consisting of full-matrix micro-particles, core/shell micro-particles, multi-shell micro-particles and any combination thereof. Each possibility represents a separate embodiment of the present invention.
  • the sol-gel micro-particles are at least partly coated by a metal-oxide layer.
  • the sol-gel micro-particles are porous full-matrix micro- particles, and wherein the at least one fragrant component is comprised in the internal cavities of the full-matrix micro-particles.
  • the porous full-matrix micro-particles have a predetermined matrix hydrophilic-lipophilic balance (HLB) level, a predetermined matrix surface area and a predetermined matrix porosity level.
  • HLB matrix hydrophilic-lipophilic balance
  • the sol-gel micro-particles are core/shell micro-particles, and wherein the at least one fragrant component is comprised in the core of the core/shell micro-particles.
  • the core/shell micro-particles have a predetermined shell hydropWlic-lipophilic balance (HLB) level, a predetermined shell surface area and a predetermined shell porosity level.
  • the sol-gel micro-particles are multi-shell micro- particles, and wherein the at least one fragrant component is comprised in at least one shell of the multi-shell micro-particle.
  • At least two fragrant components of the plurality of fragrant components have similar intrinsic volatilities.
  • the natural fragrant component is extracted from a plant or an animal.
  • a plant or an animal Each possibility represents a separate embodiment of the present invention.
  • the fragrant component is a synthetic fragrant component or a mixture thereof.
  • the synthetic fragrant component is selected from the group consisting of 7-Methylbenzo[b][l,4]dioxepin-3-one (Calone), salicylates aldehydes and aromatic aldehydes. Each possibility represents a separate embodiment of the present invention.
  • the fragrant component is a biodegradable chemical of low chemical stability.
  • M is selected from the group consisting of Si, Al, Ti, Zn and Zr. Each possibility represents a separate embodiment of the present invention.
  • P is selected from the group consisting of alkyl and aryl group. Each possibility represents a separate embodiment of the present invention.
  • the additive is selected from the group consisting of a preservative, an emulsifier, a biocide, a sunscreen compound, a color, a pigment, an antibacterial compound, a skin-used vitamin and any combination thereof.
  • a preservative an emulsifier
  • a biocide a biocide
  • a sunscreen compound a color, a pigment, an antibacterial compound, a skin-used vitamin and any combination thereof.
  • the composition described above is essentially devoid of alcohols. [0065] In some embodiments, the composition described above is essentially devoid of ethanol.
  • the composition described above is in a powder form.
  • the composition described above is semi-transparent or fully transparent when suspended in cosmetic or skin care formulations and applied to skin.
  • the micro-capsules are combined in a predetermined proportion to obtain a predetermined perception profile; release profile; order of release of at least one fragrant component; duration of release of at least one fragrant component; or strength of the initial perception of at least one fragrant component.
  • the perception profile is a time-dependent perception profile, determined by the duration of perception or the rate of release of the fragrance material from the microcapsules.
  • the micro-capsules are combined in a predetermined proportion to retain the original scent of the fragrance material before encapsulation.
  • the composition described above is for use as an odor- producing material or as a malodor-masking agent in personal care products. Each possibility represents a separate embodiment of the present invention.
  • the present invention further provides, in an aspect, a personal care product comprising the composition described above.
  • the personal care product described above is selected from the group consisting of soap, a detergent, a fabric softener, a lotion, a cream, a body wash, a shampoo and a deodorant. Each possibility represents a separate embodiment of the present invention.
  • the present invention also provides, in an aspect, a method for manipulating the time-dependent release profile of a mixture of fragrant components, comprising encapsulating at least one fragrant component in sol-gel micro-capsules, wherein each one of the at least one fragrant components is encapsulated in micro-capsules having a predetermined hydropWlic-lipophilic balance (HLB) level, a predetermined surface area and a predetermined porosity.
  • HLB hydropWlic-lipophilic balance
  • the present invention also provides, in an aspect, a method for retaining the odor of a mixture of fragrant components, comprising encapsulating each fragrant component separately in sol-gel micro-capsule of similar structure, and mixing the micro-capsules.
  • the present invention also provides, in an aspect, a method for protecting and stabilizing a biodegradable fragrant component, comprising entrapping the biodegradable fragrant component within the sol-gel micro-particles composition described above.
  • Figure 2 is a SEM image of a sample of 10% methyl- modified silica micro- particles co-doped with 2 fragrances.
  • Figure 3 is a SEM image of a sample of 100% methyl-modified silica micro- particles co-doped with 2 fragrances.
  • Figures 4A and 4B are bar graphs depicating the amount of encapsulant
  • Figures 5A and 5B are SEM images of a sample of 100% TEOS micro- particles doped with bergamot oil.
  • Figures 6 A and 6B are pie graphs depicating the desorption profile of free bergamot oil (A) and bergamot oil encapsulated in 100% TEOS micro-particles (B).
  • the carrier microcapsules of the present invention solve this problem, as the relative volatility and order of release of smells is controlled by the components of their matrices, and by the release of different encapsulants, either from a mixture of particles, or from particles containing a mixture, as further explained below.
  • the ability to release top notes and bottom notes at a similar rate or at reversed rates creates for performers the ability, for the first time, to create new smell-mixtures.
  • the encapsulation method described here is a non-trivial and a major step forwards in providing an efficient tool for that goal.
  • fragrances formulated either in ethanol or in water are actually perfume oils with ethanol used as filler and sometime water.
  • the primary purpose of ethanol is to cause the perfume oils to evaporate faster than they would by themselves, sometimes as much as 15 times more quickly.
  • the overall consequences are that the perfume is perceived considerably stronger than it actually is, while the scent fades dramatically within 1 or 2 hours as the perfume oils evaporate along with the alcohol.
  • Fragrance molecules can easily penetrate the skin into sub-cutaneous layers, and in fact this is a cause of skin rashes more than ethanol is. As toxicity of these molecules has never been evaluated (especially the synthetic ones), the encapsulation has the advantage of greatly dimmshing the skin penetration of these molecules.
  • the capsules which must be larger than 100 nm, release their volatiles to the environment long after the solvent has evaporated.
  • Ethanol furthermore, has the further major disadvantage of easily carrying the fragrance molecules across the skin barrier into sub-cutaneous layers.
  • Another advantage offered by the present invention lies in the possibility to disperse hydrophobic fragrances in water. Most of the fragrances indeed are oils and the perfume industry continues to use ethanol heavily. Avoiding the usage of ethanol is an unmet, urgent need in the quest of healthy and green cosmetics, reducing the frequency of perfume dermatitis in humans, as described by E. M. Jackson in American Journal of Contact Dermatitis 9 (1998)193-195.
  • the technology is also ideally suited to stabilize and protect chemically and photo-chemically labile or sensitive essential oils thereby enabling efficient utilization of essential oils in a number of applications, ranging from personal care to household, laundry and nutritional products.
  • a crucial advantage provided by the present invention lies in a positive consequence for human health and the environment, associated with the environmentally benign nature of the capsules made according to the present invention.
  • Ubiquitous toxic synthetic fragrances indeed, can be replaced by sol-gel derived micro-particles encapsulating unstable essential oils and other natural fragrances whose poor chemical and photochemical stability has thus far prevented widespread utilization.
  • the essential oils become more resistant towards air, humidity, high temperature and solar light, namely all factors which can lead to the rapid evaporation and to the degradation of some active components.
  • essential oils (EOs) become a viable alternative in agriculture, food, cosmetic and pharmaceutical industries and medicine making possible a safer and better life in a protected environment.
  • the present invention relates to controlled release microparticles containing entrapped fragrance molecules, produced using the sol-gel technology.
  • the microparticles can be core shell silica based particles, full matrix silica based particles, or multi-shell type particles.
  • the present invention provides controlled release microcapsules containing microencapsulated fragrance molecules, produced using the sol-gel technology.
  • the present invention relates to selectively controlling the release of the entrapped fragrances through tailored control of the properties of the organosilica shell, and in particular its HLB and textural properties (specific pore volume and surface area).
  • the present invention relates to encapsulation of a mixture of fragrance chemicals which, upon release, preserves the original sensorial feeling, while controlling the release order, the release rate and thereby the duration of release of the fragrances.
  • Each component of a mixture of fragrances can be released in a controlled manner from a single type of particle or each component can be individually controlled in different particles..
  • the microcapsule is an organosilica capsule and has a core-shell structure.
  • a process for preparing sol-gel microcapsules loaded with fragrance and aroma molecules from oil-in-water emulsions comprising the steps of a) emulsifying the water insoluble solution, containing the sol-gel precursors and the functional molecules to be loaded, in an aqueous solution and b) stirring the emulsion obtained in step (a) with an acidic, neutral or basic aqueous solution to obtain loaded sol-gel microcapsules in a suspension, and c) optionally drying the mixture resulting from step b) with a mild evaporation treatment.
  • these sol-gel precursors are metal or semi-metal alkoxide monomers, or metal ester monomers, or semi-metal ester monomers or monomers of the formula M(R)n(P)m, wherein M is a metallic or semi metallic element, R is a hydrolyzable substituent, n is an integer from 2 to 6, P is a non polymerizable substituent and m is an integer from 0 to 6, or partially hydrolyzed and partially condensed polymer thereof, or any mixture thereof.
  • said sol-gel precursors are silicon alkoxide monomers, or silicon ester monomers, or monomers of the formula Si(R)n(P)m, where R is a hydrolyzable substituent, n is an integer from 2 to 4, P is a non polymerizable substituent and m is an integer from 0 to 4, or partially hydrolyzed and partially condensed polymer thereof, or any mixture thereof.
  • said sol-gel precursors are titanium alkoxide monomers, or titanium ester monomers, or monomers of the formula Ti(R)n(P)m, where R is a hydrolyzable substituent, n is an integer from 2 to 6, P is a non polymerizable substituent and m is an integer from 0 to 6, or partially hydrolyzed and partially condensed polymer thereof, or any mixture thereof.
  • the sol-gel precursors are zinc or zirconium alkoxide monomers, or zinc or zirconium ester monomers, or monomers of the formula Zn(R)n(P)m or Zr(R)n(P)m, where R is a hydrolyzable substituent, n is an integer from 2 to 6, P is a non polymerizable substituent and m is an integer from 0 to 6, or partially hydrolyzed and partially condensed polymer thereof, or any mixture thereof.
  • the microcapsules are fully alkylated organosilica particles obtained following the approach described in B. Fei et al. Chemistry Letters 35 (2006) 622, through self-catalytic sol-gel reaction of an alkyl-modified silane such as MTMS and an aminopropyl-modified silane such as 3-aminopropyl trimethoxysilane (ATMS) at oil/water interface without surfactant or other mediating reagents.
  • an alkyl-modified silane such as MTMS
  • an aminopropyl-modified silane such as 3-aminopropyl trimethoxysilane (ATMS)
  • fragrance compound examples include essential oils, citrus (orange, lemon and lime - oil top note fractions), magnolia and/or terpenes.
  • the fragrance compound is added as a liquid.
  • about 0.001 to about 1 mole equivalents of the flavor compound can be used, based on the molar amount of the silicon alkoxide.
  • about 0.004 to about 0.02 mole equivalents are used.
  • the present invention relates to the use of the sol-gel microencapsulation technology to create either a mixture of doped particles in which the release of different encapsulants takes place at similar rate, or particles containing a mixture in fragrances in which the release of different encapsulants takes place at the desired, tailored rate.
  • the present invention relates to the synthesis of colloidal hydrophilic sol-gel particles entrapping the hydrophobic low molecular weight essential oils comprising the vast majority of compounds used in the fragrance industry, thus allowing the possibility to formulate in aqueous phase that can normally be performed in ethanol/water phase only.
  • the present invention relates to capsules that release the encapsulated fragrance either by diffusion through the porous capsule shell or by rupture of the shell induced by mechanical forces.
  • the present invention relates to encapsulated perfume capsules wherein speed and duration of release is dictated by the volatility of the encapsulated perfume materials and by the shell chemical composition and textural properties.
  • the present invention relates to entrapped fragrance chemicals of high volatility when rapid release, and thus consumer perception of fragrance, is desired.
  • typical rates of release from the embedded silica capsules at room temperature are about 0.001 mmol/h, so that less than 5% fragrance leaches out of the capsule after 4 weeks.
  • fragrance or use can be combined or interverted freely.
  • mixture of two fragrances such as geraniol and citronellal can be used in a preferred amount (such as ca. 0.004 to ca. 0.02 mole equivalents) with a typical amount of the condensation catalyst (such as about 0.002 to about 0.12 mole equivalents) with a TEOS:MTMS (90:10 in molar terms) precursor mixture.
  • a preferred amount such as ca. 0.004 to ca. 0.02 mole equivalents
  • condensation catalyst such as about 0.002 to about 0.12 mole equivalents
  • TEOS:MTMS 90:10 in molar terms
  • fragrance-containing silica or organosilica micro-particle defined herein can be used on its own or be part of a fragrance bearing device or other supporting material.
  • the present invention provides, inter alia, fragrance-containing sol-gel microcapsules of tuneable or predetermined scent containing an active fragrance material in their core, prepared in a process comprising steps of emulsifying a water insoluble solution, comprising an appropriate amount of sol-gel precursors and the functional fragrance molecules to be loaded, in an aqueous solution with surfactants, followed by mixing and stirring the sol- gel precursor and fragrance oil emulsified mixture obtained with a neutral, acidic or basic aqueous solution to obtain loaded sol-gel microcapsule particles in suspension.
  • the active material is a single molecular fragrance or a combination of fragrances, including commercial fragrance mixtures such as perfumes.
  • two or more sets of different capsules containing different fragrance chemicals having varying volatilities are prepared and combined in the desired proportion to obtain the require duration and rate of release, and thus of time- dependent perception.
  • the fragrance or fragrances are combined with a co- solvent to tailor the overall hydrophilic-hydrophobic balance of the blend, or to modify the vapor pressure of the resulting microcapsule materials.
  • the fragrance is of natural origin, namely extracted from plant or animal source materials, and is derived from an essential oil or mixture thereof including, but not limited to, hyacinth, jasmine, magnolia, orchids, vanilla, and the like.
  • the fragrance is of synthetic origin, including synthetic substances such as those found in many modern perfumes such as for instance Calone, salicylates and aromatic aldehydes artificially created either to match the fragrant compounds found in various natural fragrances or to create entirely new fragrances.
  • the embedded fragrances are biodegradable chemicals which could not be used before because of the low chemical stability during processing, storage or usage.
  • the process described above comprises the further step of isolating and washing the microcapsules by filtration and re-suspension in water, through centrifugation or by evaporation and re-suspension in water or by dialysis.
  • the oil solution or the aqueous solution contain additives to improve the product, including preservatives, emulsifiers and biocides.
  • other actives such as sunscreens, colors, antibacterials, and skin-used vitamins are co-entrapped in the capsule core.
  • the sol-gel precursor is a metal or semi- metal alkoxide monomer, or a metal ester monomer, or a semi-metal ester monomer of the general formula M(R)n (P)m, wherein M is a metallic or semi metallic element such as Si, Al, Ti, Zn and Zr, R is a hydrolyzable substituent, n is an integer from 2 to 6, P is a non polymerizable substituent such as alkyl or aryl group and m is an integer from 0 to 6, or partially hydrolyzed and partially condensed polymer thereof, or any mixture thereof.
  • M is a metallic or semi metallic element such as Si, Al, Ti, Zn and Zr
  • R is a hydrolyzable substituent
  • n is an integer from 2 to 6
  • P is a non polymerizable substituent such as alkyl or aryl group
  • m is an integer from 0 to 6, or partially hydrolyzed and partially condensed polymer thereof, or any mixture thereof.
  • the sol-gel precursor is selected from the group consisting of but not limited to TMOS, MTMS, TEOS and mixtures thereof.
  • the present invention also provides fragrance-containing sol-gel microcapsules retaining the original scent of non-entrapped fragrance molecules, as substantially described and illustrated herein.
  • the present invention also provides a process for altering the odor of a mixture of fragrances through co-entrapment of odorant molecules in sol-gel capsules or combining a mixture of doped particles by tailoring the initial sol-gel chemistry so as to provide the required HLB level and textural properties to the encapsulant material.
  • the present invention also provides a process where the time dependence profile of the release of various fragrant components in a mixture is controlled by tailoring the porosity and HLB of the shell with suitably selected sol-gel monomers.
  • the present invention also provides a process for retaining the odor of a mixture of fragrances through entrapment of odorant molecules in different sol-gel capsules of similar structure and mixing these different capsules.
  • the present invention also provides a process to use hydrophilic odorant capsules to form water-based formulations avoiding the need of ethanol and thus preventing unwanted skin effects.
  • the present invention also provides a process to use the sol-gel encapsulation process described in claim 1 to protect and stabilize delicate biodegradable fragrance molecules or combination thereof.
  • the present invention mainly provides the products obtained by the process described above.
  • the products are in a suspension form.
  • fragment component refers to any man-made or natural compound or molecule the presence of which is capable of being detected by a mammal, preferably a human.
  • predetermined release profile refers to the desired odor, smell or fragrance being manipulated in at least one aspect relative to the odor, smell or fragrance of a corresponding active fragrance material or fragrant component in free form.
  • M is selected from the group consisting of Si, Al, Ti, Zn and Zr. Each possibility represents a separate embodiment of the present invention.
  • At least one of the micro-particles further comprises an additive.
  • the additive is selected from the group consisting of a preservative, an emulsifier, a biocide, a sunscreen compound, a color, a pigment, an antibacterial compound, a skin-used vitamin and any combination thereof. Each possibility represents a separate embodiment of the present invention.
  • Nerol ((Z)-3,7-dimethyl-2,6-octadien-l-ol) has a sweet, fresh rose odor, and its low boiling point (22.5 °C) causes it to evaporate rapidly upon contact with the heat of human body. Once entrapped in the organosilica capsules desribed herein, however, it becomes a bottom note as its odour now lasts for several weeks.
  • Example 5 The data and discussion provided in Example 5 may theoretically lead to the concept that if some molecules are retained by the matrix of the microcapsule, their smell should be released relatively slowly and therefore be detectable (e.g by the nose) for longer time periods in the microcapsules.

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Abstract

La présente invention concerne des compositions comprenant des micro-capsules à base de sol-gel contenant des fragrances, particulièrement utiles dans de nombreux secteurs de l'industrie. La présente invention concerne de manière générale le contrôle de la libération des profils cinétiques de fragrances et d'arômes multiples à travers l'encapsulation d'au moins un mélange de parfum dans des micro-particules à base d'oxydes métalliques et d'oxydes semi-métalliques et l'utilisation des particules solides ainsi obtenues dans des applications qui requièrent une libération contrôlée réglable sélective dans ses constituants des agents actifs de la fragrance ou de l'arôme, soit pour conserver la sensation sensorielle d'origine, soit pour en créer de nouvelles en changeant l'ordre classique de libération des notes supérieures, des notes moyennes et des notes inférieures. L'invention concerne également un procédé permettant d'élaborer des fragrances dans de l'eau plutôt que dans de l'éthanol tout en diminuant l'interaction nocive entre les molécules de fragrance piégées et la peau.
PCT/IL2014/050323 2013-04-01 2014-04-01 Capsules réglables à base de sol-gel comprenant des fragrances, et des arômes et leurs utilisations WO2014162311A1 (fr)

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Cited By (7)

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Publication number Priority date Publication date Assignee Title
WO2018082914A1 (fr) * 2016-11-03 2018-05-11 Unilever Plc Compositions éthanoliques comprenant du parfum
CN108676615A (zh) * 2018-04-25 2018-10-19 上海应用技术大学 一种纳米缓释香精的制备方法
CN109287628A (zh) * 2018-09-18 2019-02-01 广西大学 一种纳米二氧化硅抗菌微胶囊的制备工艺
CN111851078A (zh) * 2019-04-28 2020-10-30 杭州诺邦无纺股份有限公司 一种芳香非织造布及其制备方法
US10934504B2 (en) 2016-11-03 2021-03-02 Conopco, Inc. Laundry treatment compositions comprising perfume and silica microparticles
WO2022023110A1 (fr) * 2020-07-29 2022-02-03 Givaudan Sa Améliorations apportées ou se rapportant à des composés organiques
WO2022181387A1 (fr) * 2021-02-24 2022-09-01 株式会社カネカ Particules creuses ainsi que procédé de fabrication de celles-ci, et application de ces particules creuses

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018082914A1 (fr) * 2016-11-03 2018-05-11 Unilever Plc Compositions éthanoliques comprenant du parfum
US10934504B2 (en) 2016-11-03 2021-03-02 Conopco, Inc. Laundry treatment compositions comprising perfume and silica microparticles
CN108676615A (zh) * 2018-04-25 2018-10-19 上海应用技术大学 一种纳米缓释香精的制备方法
CN109287628A (zh) * 2018-09-18 2019-02-01 广西大学 一种纳米二氧化硅抗菌微胶囊的制备工艺
CN111851078A (zh) * 2019-04-28 2020-10-30 杭州诺邦无纺股份有限公司 一种芳香非织造布及其制备方法
CN111851078B (zh) * 2019-04-28 2022-11-15 杭州诺邦无纺股份有限公司 一种芳香非织造布及其制备方法
WO2022023110A1 (fr) * 2020-07-29 2022-02-03 Givaudan Sa Améliorations apportées ou se rapportant à des composés organiques
WO2022181387A1 (fr) * 2021-02-24 2022-09-01 株式会社カネカ Particules creuses ainsi que procédé de fabrication de celles-ci, et application de ces particules creuses

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