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WO2019170222A1 - Dépôt de substance active encapsulée sur les cheveux et un textile - Google Patents

Dépôt de substance active encapsulée sur les cheveux et un textile Download PDF

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Publication number
WO2019170222A1
WO2019170222A1 PCT/EP2018/055456 EP2018055456W WO2019170222A1 WO 2019170222 A1 WO2019170222 A1 WO 2019170222A1 EP 2018055456 W EP2018055456 W EP 2018055456W WO 2019170222 A1 WO2019170222 A1 WO 2019170222A1
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WO
WIPO (PCT)
Prior art keywords
composition
active substance
oil
capsule
polymer
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2018/055456
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English (en)
Inventor
Maryna MOROZ
Ranjita SHEGOKAR
Jörn WIEDEMANN
Falk Harzke
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Symrise AG
Original Assignee
Symrise AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Symrise AG filed Critical Symrise AG
Priority to PCT/EP2018/055456 priority Critical patent/WO2019170222A1/fr
Publication of WO2019170222A1 publication Critical patent/WO2019170222A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C11D3/50—Perfumes
    • C11D3/502—Protected perfumes
    • C11D3/505—Protected perfumes encapsulated or adsorbed on a carrier, e.g. zeolite or clay
    • 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
    • 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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
    • C11D17/0013—Liquid compositions with insoluble particles in suspension
    • 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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0039—Coated compositions or coated components in the compositions, (micro)capsules
    • 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
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/22—Carbohydrates or derivatives thereof
    • C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
    • 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
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/30—Amines; Substituted amines ; Quaternized amines
    • 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
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3723—Polyamines or polyalkyleneimines
    • 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
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3769—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines

Definitions

  • the present invention relates to the prolonged delivery of active substances, such as a fragrance or antimalodor active or cosmetic active or other active.
  • active substances such as a fragrance or antimalodor active or cosmetic active or other active.
  • the present invention discloses a composition for delivery of an active substance.
  • the present composition comprises or consists of at least one organic ammonium compound, at least one excipient including at least one first polymer, a capsule comprising an active substance; and optionally a solvent.
  • a product comprising the present composition for delivery of an active substance, a method for preparing the present composition for delivery of an active substance and the use of the present composition for delivery of an active substance are provided.
  • fragrances such as fragrances, fragrance mixtures or their actives.
  • Fragrance mixtures with a plurality of different fragrance notes are used in large numbers and countless variations in perfumes, scent mixtures (perfume compositions) and perfuming for a wide variety of different fields of use, including for example cleaning agents, fabric softeners, washing powders, liquid laundry detergents, shower gels, shampoos, deodorants, body lotions etc.
  • Compositions for delivery of active substances, such as detergent compositions have the tendency that the active substance dissipates over a period of time and is no longer perceptible, e.g. by the user, or even detectable.
  • compositions for delivery of an active substance are usually formulated with various ingredients, such as a solvents or excipients, which may be obtained from a natural source and/or chemically synthesized.
  • a solvents or excipients which may be obtained from a natural source and/or chemically synthesized.
  • the different constituents, including the active substance(s) evaporate over time from the composition.
  • a problem with conventional compositions for delivery of an active substance resides in that such products do not contain constituents allowing an increased persistence of the active substance(s) for an extended time period.
  • Conventional detergent compositions do not resist evaporation from the human body or garments.
  • conventional compositions for delivery of an active substance become diluted upon contact with water.
  • the active substance(s) may be washed out or even decompose upon contact with water or another solvent thereby reducing the effective life time of the active substance(s).
  • Conventional compositions for delivery of an active substance usually do not provide sustained release of the active substance from the product applied to the human or animal skin, or any other surface to be treated.
  • interactions of the active substances, in particular fragrances with other constituents of the formulation or premature evaporation of the lighter volatile components of the composition or a product comprising the composition occur very frequently. As a rule this leads to the olfactory impression of a fragrance changing or vanishing completely.
  • Encapsulation of active substances, in particular fragrances, is commonly used technique nowadays in order to keep active substances from undesired evaporation and provide long-lasting effect of the active principle underlying the active substances.
  • Encapsulation of active substances, in particular fragrances offers the possibility of reducing or completely preventing interactions in the product comprising an active substance or evaporation of the slightly volatile constituents.
  • the use of microcapsules provides release the constituent(s) under precisely defined conditions.
  • the microcapsules which contain fragrant substances it is necessary that the microcapsules enclose the fragrances, which are generally sensitive to oxidation, so that they are stable in storage and that only at the moment of the desired fragrance development the microcapsules are broken open by mechanical action.
  • Addition of encapsulated fragrance to laundry detergent and fabric treatment compositions as well as personal care products enables enhancing the fragrance experience several times higher.
  • US 2011/118161 A1 discloses a core-shell microcapsule enclosing an odorous substance, wherein the shell is made of one or more polysiloxanes bearing one or more amino groups and one or more polyisocyanates.
  • US 6,586,107 B2 discloses microcapsules having walls obtained by reacting polyisocyanates with guanidine compounds, wherein the polyisocyanates consists of a hexamethylene diisocyanate oligomer.
  • application of capsules in rinse-off cleaning products such as laundry detergents, shampoos, body washes etc. is a challenging task as special formulations are needed to facilitate an adhesion of capsules to different types of surfaces.
  • Such capsules should still exhibit sufficient stability for the respective applications, such as cleaning agents, fabric softeners, washing powders, liquid laundry detergents, shower gels, shampoos, deodorants, body lotions and other cosmetic products, and improved release properties. It would be therefore desirable to provide a composition for delivery of an active substance and method for its preparation that would be operative to increase the effective life of an active substance product once placed on different surfaces, such as human or animal hairs and textiles.
  • compositions for delivery of an active substance and method for its preparation which overcomes the disadvantages of the prior art by providing a composition that will extend the effective life of the active substance and/or the composition comprising the active substance.
  • Still another objective resides in the provision of a composition for delivery of an active substance offering improved deposition of capsules on surfaces, such as hair and/or textile surfaces, preferably along with good cleaning performance.
  • Still another objective of the present invention resides in the provision of a composition for delivery of an active substance which is equally suitable for application on hair and textile surfaces.
  • the present invention therefore concerns the provision of a composition for delivery of an active substance, the composition comprising or consisting of at least one organic ammonium compound, at least one excipient including at least one first polymer, a capsule comprising an active substance, and optionally a solvent and/or viscosity modifier.
  • the present invention also provides a product, preferably a perfumed product, comprising the present composition for delivery of an active substance, a method for preparing the composition for delivery of an active substance and the use of the present composition for delivery of an active substance, or preferably the present product, to perfume any surface, such as textiles, hair, skin surfaces and ambient air.
  • the present inventors explored different types of polymers and their concentrations that possibly interact with excipients, such as surfactants, and build complexes after dilution in high polar solvents, particularly water, thereby enabling deposition of capsules on hair or textile or other surfaces.
  • the present invention is based on the finding that complexes created during hair washing process using cationic polymers, in particular organic ammonium compounds and other supplementary surfactants and thickeners, have high substantivity to hair.
  • Usual shampoos do not show this phenomenon of complexation.
  • An isoelectric point of hair is rather low with a pH of about 3.67, thus the hair’s surface carries a net negative charge at any pH above the isoelectric point.
  • cationic polymers in particular one or more of organic ammonium complexes, thermosensitive polymers and thermoreversible polymers, build association complexes with an excipient, in particular with at least one first polymer, such as a surfactant, in solution when comes in contact with a high polar solvent, particularly water.
  • a high polar solvent particularly water.
  • Cationic polymer adsorbs the excipient, thus, the cationic charge of polymer becomes neutralized. In presence of a high polar solvent, particularly water, a polymer complex is formed.
  • Capsules are entangled in these complexes and preferably have a dso of 0,5 to 50 pm. These complexes have higher hair surface affinity compared to regular shampoo, thereby reducing capsules rinse off from hair shafts when in contact with water. These tiny complexes together with capsules thereby provide long lasting effect of the encapsulated active substances.
  • other ingredients such as one or more of silicones, gums, celluloses and polymers can be used.
  • the present capsules provide controlled release of the active ingredients, preferably the active substance, such as odor substances/fragrances, improved sensory properties in terms of odor development upon breaking the shell of the capsule is obtained.
  • the active substance such as odor substances/fragrances
  • active substance as used herein broadly pertains to compounds including active constituents, such as a fragrance (as understood by a person skilled in the art), a scent, an aroma, a freshener or freshening agent, a anti- malodor active, a neutral note, a cosmetic, nutraceutical, pharmaceutical active and optionally also an insect repellent, in particular a mosquito repellent, an insecticide, or a pheromone.
  • active constituents such as a fragrance (as understood by a person skilled in the art), a scent, an aroma, a freshener or freshening agent, a anti- malodor active, a neutral note, a cosmetic, nutraceutical, pharmaceutical active and optionally also an insect repellent, in particular a mosquito repellent, an insecticide, or a pheromone.
  • organic ammonium compound refers to positively charged quaternary ammonium cations (N + R I R2R3R 4 ), wherein Ri to R 4 are selected independently from each other from H or an organic residue with the proviso of presence of at least one organic residue, preferably two organic residues.
  • the organic residues may be one or more of linear aliphatic molecules, branched aliphatic molecules and/or cyclic aliphatic molecule.
  • the linear aliphatic molecule and/or the branched aliphatic molecule is preferably selected from C2-C20, preferably C3-C15, C 4 -Ci2, C5-C10, C6-C9, or C7-C8, linear alkyl.
  • the linear aliphatic molecule does not encompass an aromatic structure and/or a cyclic structure.
  • the cyclic aliphatic molecule has at least 1 , such as 2, 3 or 4, ring structures.
  • the least 1 , such as 2, 3 or 4, ring structures are preferably composed independently from each other from 3, 4, 5, 6, 7 or 8 membered rings.
  • the cyclic aliphatic molecule 2 to 20 C-atoms, such as 3 to 15, 4 to 12, 5 to 10, 6 to 9, or 7 to 8, C-atoms.
  • any of the linear aliphatic molecules, branched aliphatic molecules or cyclic aliphatic molecule preferably exhibits one or more hetero atoms, such as O and/or N.
  • the one or more hetero atoms may be also present in form of functional groups, such as a hydroxyl group, an amino group, a halogen, such as fluoride, chloride, bromide and iodine, or ether group.
  • the hetero atoms are present in form of several ether groups, such that a polyether is formed, and/or the hetero atoms are present in form of several hydroxyl groups, such that carbohydrates are formed.
  • the organic ammonium compound preferably exhibits a limited size/molecular weight, respectively.
  • suitable molecular weights includes approx. 150 g/mol to 1000 g/mol, preferably 200 g/mol to 900 g/mol, or 250 g/mol to 800 g/mol.
  • preferred organic ammonium compounds include polyquaterniums, and polymeric carbohydrate ammonium compounds.
  • Polyquaternium (PQ) is the International Nomenclature for Cosmetic Ingredients (I NCI) designation for several polycationic polymers that are used in the personal care industry.
  • the polyquaterniums may include one or more of PQ-5 to PQ-90, such as PQ-7 (e.g. Merquat 550) and PQ-10 (e.g.
  • Polymeric carbohydrate ammonium compounds are ammonium compounds in which polymeric, optionally substituted) carbohydrates form at least one organic residue.
  • Preferred polymeric carbohydrate ammonium compounds include a hydroxypropyl guar hydroxypropyltrimonium chloride, such as Jaguar C 162 and Jaguar LS, and a guar hydroxypropyltrimonium chloride, such as Jaguar C 500, Jaguar Excel and Jaguar Optima.
  • a thermosensitivepolymers may be employed.
  • thermosensitive polymer refers to polymers that at exhibit a drastic and discontinuous change of their physical properties with temperature.
  • a preferred definition is that a “thermosensitive polymer” exhibits a miscibility gap in its temperature-composition diagram.
  • thermosensitive polymers include one or more of cellulose, methoxy cellulose, carboxy cellulose, substituted celluloses can be used as alternatives.
  • Other thermosensitive polymers are known to the skilled person and may be easily selected in view of e.g. the ab above mentioned miscibility gap in their temperature-composition diagram. Alternatively, the thermosensitive polymers may be also easily tested and selected according to their capability of forming the above mentioned association complex.
  • thermoreversible polymers examples include thermoreversible polymers.
  • Thermoreversible polymers are well known in the art. Preferrerd thermoreversible polymers are for instance disclosed in Dawydoff W. et al.: Thermoreversible Gele auf Polysaccharidbasis (Obersichtselle); Molekular Nutrition & Food Research, Vol. 28 (3) (1984); pp. 241-260, the contents of which are incorporated by way of reference.
  • first polymer refers to a compound interacting with the at least one organic ammonium compound and the capsule in the presence of a solvent, particularly water, under formation of an association complex.
  • An “association complex” as used herein pertains to a complex which is only formed on the basis of week intermolecular interactions, such as hydrogen bonds, interaction of induced dipols and/or interaction of permanent dipols. Hence, an association complex usually does not encompass formation of a chemical bond. It is preferred that at least 2 first polymers, such as at least 3, 4 or 5 first polymers, are employed.
  • first polymers forming such association complexes with the at least one organic ammonium compound or thermosensitive polymer include one or more of surfactants, such as ether sulfates, preferably alkyl ether sulfates, more preferably sodium laureth sulfate (SLS) (e.g.
  • surfactants such as ether sulfates, preferably alkyl ether sulfates, more preferably sodium laureth sulfate (SLS) (e.g.
  • Hansanol NS 242 sodium lauryl sulfate, sodium myreth sulphate, ammonium lauryl sulphate, cocamidopropyl betaine, a sarcosinate, such as sodium laurosyl sarcosinate, an alkyl polyglycoside, a sulphosuccinate, such as diethylhexyl sodium sulfosuccinate, disodium laureth sulfosuccinate, disodium lauryl sulfosuccinate, a carboxylate, for example sodium lauryl glucose carboxylate; polyelectrolyte like cationic-anionic polymers (exhibiting strong and/or week dipole interactions); thermoactive polymers, thermostable polymers, gelling polymers, and silicones, such as dimethicone or polydimethylsiloxan.
  • a sarcosinate such as sodium laurosyl sarcosinate, an alkyl polyg
  • polyelectrolyte pertains to a water soluble polymer carrying ionic charge along the polymer chain. Depending upon the charge, these polymers are anionic or cationic.
  • the polyelectrolytes are available in a wide range of molecular weights and charge densities. Examples of thermosensitive polymers include one or more of cellulose, methoxy cellulose, carboxy cellulose, substituted celluloses can be used as alternatives.
  • excipient refers to any substance that serves as the vehicle or medium for a drug or other active substance. Hence, the excipient usually does not form a chemical bond with any of the other constituents of the present composition. It will be, however, appreciated that the excipient may form an association complex with any other constituent(s) even though this is not specifically envisaged.
  • the excipient preferably encompasses one or more of surfactants, cosolvents, preservatives, abrasives, antibacterial agents, anti-inflammatory agents, anti- irritants, irritation suppressants, antimicrobial agents, antioxidants, antiseptics, binders, buffers, chelating agents, deodorisers, emollients, fixatives, foaming agents, foam stabilisers, antifoams, foam boosters, fungicides, humectants, moisturisers, bleaching agents, stain removers, soil repellents, insect repellents, opacifiers, plasticisers, brighteners, abrasive agents, skin care agents, skin- protecting agents, skin-softening agents, skin-cooling agents, skin-warming agents, stabilisers, UV-absorbers, thickeners, vitamins, oils, waxes, fats, phospholipids, mono- or polyunsaturated fatty acids, a-hydroxy acids, polyhydroxy fatty acids,
  • “at least one organic ammonium compound” and“at least one excipient” and“at least one further fragrance” may refer to any number of different organic ammonium compounds and different excipients, respectively, such as 2 or more, preferably, 3 or more, 4 or more, 5 or more, 6 or more, 7 or more, 8 or more, 9 or more, or 10 or more.
  • indefinite article“a” or“an”, such as “a capsule”,“an active substance”,“a solvent” and“a viscosity modifier” indicates likewise that more than one of said constituent(s) may be present, such as 2 or more, preferably, 3 or more, 4 or more, 5 or more, 6 or more, 7 or more, 8 or more, 9 or more, or 10 or more.
  • suitable solvents are selected from the group consisting of water, ethanol, isopropanol, diethylene glycol monoethyl ether, glycerine, glycerol, polyethylene glycol (PG), such as polyethylene glycol BB, for instance BB 300, 1 ,2- butylene glycol, dipropylene glycol (DPG), dipropylene glycol monomethyl ether (DPM) diethyl phthalate, methyl methoxy butanol, triethyl citrate, isopropyl myristate, paraffins, tripropylene glycol methyl ether (TMP), dioctyl adipate (DOA), isopropyl myristate (IPM), synthetic isoparaffinic solvents, such as Isopar L, triethyl citrate (TEC) and mixtures thereof.
  • PG polyethylene glycol
  • BB polyethylene glycol
  • DPG dipropylene glycol
  • DPM dipropylene glycol monomethyl
  • Suitable and preferred solvents include ether acetates, such as propylene glycol methyl ether acetate and particularly dipropylene glycol methyl ether acetate (DPMA).
  • DPMA dipropylene glycol methyl ether acetate
  • a particularly preferred solvent is water.
  • A“high polar solvent” as used herein pertains to a solvent or a mixture of several solvents having a polarity which is equal to or higher than that of dimethyl sulfoxide (DMSO).
  • DMSO dimethyl sulfoxide
  • examples of such high polar solvent include, water, DMSO and any mixture of these compounds. It is assumed that the high polar solvent triggers formation of the association complex(es). It will be therefore readily understood that its presence in most detergent compositions, e.g. personal care product or laundry care product, is not necessarily required since the application of such a detergent composition is usually performed in the presence of water.
  • suitable viscosity modifiers encompass one or more cellulose derivatives, such as hydroxpropylmethyl cellulose or starch derivatives.
  • the term“capsule”,“core/shell capsule”, or“microcapsule” as used herein pertains generally to finely dispersed, liquid or solid phases, coated with film-forming polymers, wherein at the production of these the polymers deposit on the material to be covered after emulsification and coacervation or surface polymerization.
  • molten waxes which can, as micorparticles, further be covered with film-forming polymers are received by a matrix (“microsponge”).
  • particles are alternatingly coated with polyelectrolytes with different charge (“layer-by-layer”-method).
  • microscopically small capsules can be dried like powder.
  • polynuclear aggregates also called microspheres, are known, which contain two or more nuclei distributed in the continuous shell material.
  • Mono or polynuclear microcapsules can further be enclosed by an additional second, third, etc. shell.
  • the shell can consist of natural, semi-synthetic or synthetic materials. Natural shell materials are for example gum arabic, agar-agar, agarose, maltodextrines, alginic acid or the salts thereof, e.g.
  • cellulose esters and ethers are among other chemically modified celluloses, particularly cellulose esters and ethers, e.g. Cellulose acetate, Ethylcellulose, Hydroxypropylcellulose, Hydroxypropylmethylcellulose and Carboxymethylcellulose, as well as starch derivatives, especially starch ethers and esters.
  • Synthetic shell materials are for example polymers such as polyacrylates, polyamides, polyvinyl alcohols or polyvinylpyrrolidone.
  • the shell of the core-shell capsule is completely or at least partially impervious to the active agent(s), preferably any odorous substance/fragrance or combination of different odorous substances/fragrances, in the absence of mechanical load which occurs during the actual use of the present core-shell capsule, such as in an operated washing machine.
  • the term“at least partially” as used herein indicates that a portion, such as 10% or less, preferably 5%, 4%, 3%, 2%, or 1 % or less, (referred to the total amount of odorous substances/fragrances contained in the shell) of the odorous substances/fragrances may pass the shell within a time period of 3 days to 12 months, preferably 1 week to 6 months, more preferably 2 weeks to 2 months.
  • Exemplary microcapsules may exhibit the following shell material(s): gelatin and gum arabic; maritime collagen; alginic acid and agar-agar; lactose, microcrystalline cellulose and hydroxypropylmethylcellulose; modified starch, fatty acid esters, phospholipids; modified agar-agar; phospholipids; as well as chitosan and alginates.
  • microcapsules encompass:
  • Microcapsules consisting of a shell membrane and a matrix containing the active ingredients can for example be obtained by (a) preparing a matrix from gelling agents, cationic polymers and active ingredients, (b) where applicable, dispersing the matrix in an oil phase and (c) treatment of the dispersed matrix with aqueous solutions of anionic polymers and thereby, if necessary, removal of the oil phase.
  • Preferred capsule systems are listed in EP3061500, WO2016/134884, US 201 1/118161 A1 and US 6,586,107 B2, the contents of which are incorporated by way of reference in their entirety. Encapsulation of such mixtures of fragrances offers the possibility of reducing or completely preventing interactions in the perfumed product or evaporation of the slightly volatile constituents.
  • the use of microcapsules provides release the constituent(s) under precisely defined conditions. Thus for example in the case of microcapsules which contain fragrant substances it is necessary that the microcapsules enclose the fragrances, which are generally sensitive to oxidation, so that they are stable in storage and that only at the moment of the desired fragrance development the microcapsules are broken open by mechanical action.
  • the at least one organic ammonium compound is selected from the group consisting of a polyquaternium; preferably polyquaternium-7 and polyquaternium-10.
  • the polyquaternium may include one or more of PQ-5 to PQ-70, such as PQ-5, PQ-6, PQ-7, PQ-8, PQ-9, PQ-10, PQ-11 , PQ-12, PQ-13, PQ-14, PQ-15, PQ-16, PQ-17, PQ-18, PQ-19, PQ-20, PQ-22, PQ-24, PQ-27, PQ-28, PQ-29, PQ- 30, PQ-31 , PQ-32, PQ-33, PQ-34, PQ-35, PQ-36, PQ-37, PQ-39, PQ-42, PQ-43, PQ-44, PQ-45, PQ-46 and PQ-47 and so on.
  • Particularly preferred polyquaterniums include PQ-7 and/or PQ-10.
  • the first polymer includes an ether sulfate, preferably an alkyl ether sulfate.
  • An ether sulfate designates a compound wherein an ether or polyether group bridges a sulfate residue and an organic residue R 5 .
  • the ether group has the general structure -0-R 6 -0-, wherein R 6 is a linear aliphatic molecule or a branched aliphatic molecule of Ci-Cs, preferably C2-C6, C3-C5, or C 4 , linear or branched alkyl.
  • a polyether group consists of 2 or more, such as 3 or more, 4 or more, or 5 or more of the before mentioned ether groups, wherein R 5 may be the same or different.
  • the organic residue R 6 is a linear aliphatic molecule or a branched aliphatic molecule of C5-C20, preferably Cs-Ci6, C10-C14, or C12-C13 linear or branched alkyl.
  • An example of a particular preferred alkyl ether sulfate is sodium laureth sulfate (SLS).
  • the capsule has a d 5 o of 100 pm or less.
  • the capsule has an diameter dso of 0.5 pm to 90 pm, such as 0.6 pm to
  • capsules i.e. of a dso of 50 pm or less, in particular 0.5 pm to 50 pm, offer improved adhesion properties to hair in the present composition than particles of larger diameter.
  • capsules of a dso of 100 pm or less, in particular 0.5 pm to 100 pm offer improved adhesion properties to textile in the present composition than particles of larger diameter.
  • capsules of a large dso such as more than 100 pm, possibly offer a too low adherence to the treated surface, such as hairs and/or textile.
  • the diameter of the microcapsule is preferably determined by laser diffraction using a Malvern Mastersizer 3000 (according to the manufactures instructions). Obtained intensity values of the straylight are calculated into a dso value using a mathematical model, such as and preferably by Fraunhofer diffraction/approximation.
  • the dso value is the particle size at which 50 vol.-% of the microcapsules are finer than the dso value and 50 vol.-% are coarser.
  • the microcapsule is essentially spherical in shape.
  • Essentially spherical has the meaning that a deviation in each spatial direction is 10% or less, such as 5%, 4%, 3% or 1% or less. More preferably, the microcapsule is spherical in shape.
  • the capsule is a SymCap product of Symrise AG, particularly SymCap G or K.
  • any (synthetic or biodegradable) capsule may be employed provided that for instance criteria with respect to regulatory compliance are met.
  • the active substance is selected from the group consisting of a fragrance, an anti-malodor active, cooling agent, pharma/nutraceutical/cosmetic active, an insect repellent, and an insecticide.
  • the core of the core/shell capsule contains one or more odorous substances/fragrances as the active agent(s).
  • the odorous substances/fragrances are selected from the group consisting of extracts of natural raw materials such as essential oils, concretes, absolutes, resins, resinoids, balsams, tinctures such as for example ambergris tincture; amyris oil; angelica seed oil; angelica root oil; aniseed oil; valerian oil; basil oil; tree moss absolute; bay oil; armoise oil; benzoin resin; bergamot oil; beeswax absolute; birch tar oil; bitter almond oil; savory oil; buchu leaf oil; cabreuva oil; cade oil; calamus oil; camphor oil; cananga oil; cardamom oil; cascarilla oil; cassia oil; cassie absolute; castoreum absolute; cedar leaf oil; cedar wood oil; cistus oil; cit
  • cycloaliphatic ketones such as for example 1- (3,3-dimethylcyclohexyl)-4-penten-1 -one; 2,2-dimethyl-1 -(2,4-dimethyl-3- cyclohexen-1 -yl)-1 -propanone; 1 -(5,5-dimethyl-1 -cyclohexen-1 -yl)-4-penten-1 - one; 2,3,8,8-tetramethyM ,2,3,4,5,6,7,8-octahydro-2-naphthalenyl methyl ketone; methyl-2,6, 10-trimethyl-2, 5, 9-cyclododecatrienyl ketone; tert.-butyl-(2,4-dimethyl-
  • esters of cyclic alcohols such as for example 2-tert.- butylcyclohexyl acetate; 4-tert.-butylcyclohexyl acetate; 2-tert.-pentylcyclohexyl acetate; 4-tert.-pentylcyclohexyl acetate; 3,3,5-trimethylcyclohexyl acetate; decahydro-2-naphthyl acetate; 2-cyclopentylcyclopentyl crotonate; 3- pentyltetrahydro-2H-pyran-4-yl acetate; decahydro-2,5,5,8a-tetramethyl-2- naphthyl acetate; 4,7-methano-3a,4,5,6,7,7a-hexahydro-5- or 6-indenyl acetate; 4,7-methano-3a,4,5,6,7,7a-hexahydro-5- or 6-indenyl acetate; 4,
  • esters of araliphatic alcohols and aliphatic carboxylic acids such as for example benzyl acetate; benzyl propionate; benzyl isobutyrate; benzyl isovalerate; 2-phenylethyl acetate; 2-phenylethyl propionate; 2-phenylethyl isobutyrate; 2-phenylethyl isovalerate; 1-phenylethyl acetate; alpha- trichloromethylbenzyl acetate; alpha, alpha-dimethylphenylethyl acetate; alpha, alpha-dimethylphenylethyl butyrate; cinnamyl acetate; 2-phenoxyethyl isobutyrate; 4-methoxybenzyl acetate; araliphatic ethers such as for example 2- phenyl ethyl methyl ether; 2-phenyl ethy
  • -butyl-2, 6-dimethylacetophenone 4-phenyl-2- butanone; 4-(4-hydroxyphenyl)-2-butanone; 1-(2-naphthalenyl)ethanone; 2- benzofuranylethanone; (3-methyl-2-benzofuranyl)ethanone; benzophenone; 1 ,1 ,2,3,3, 6-hexamethyl-5-indanyl methyl ketone; 6-tert.
  • 3-methoxypyrazine phenyl ethers and phenyl esters such as for example estragole; anethole; eugenyl methyl ether; isoeugenyl methyl ether; diphenyl ether; beta-naphthyl methyl ether; beta-naphthyl ethyl ether; beta-naphthyl isobutyl ether; 1 ,4-dimethoxybenzene; eugenyl acetate; p-cresyl phenyl acetate; heterocyclic compounds such as for example 2,5-dimethyl-4-hydroxy-2H-furan-3-one; 2-ethyl-
  • the core comprises one or more odors substances selected from the group consisting of extracts of natural raw materials and also fractions thereof, or ingredients isolated therefrom; individual odorous substances from a group of hydrocarbons; aliphatic aldehydes and acetals thereof; aliphatic ketones and oximes thereof; aliphatic sulfur-containing compounds; aliphatic nitriles; esters of aliphatic carboxylic acids; formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates of acyclic terpene alcohols; acyclic terpene aldehydes and ketones and also dimethyl and diethyl acetals thereof; formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, he
  • Suitable flavours for producing the capsules of the present invention are preferably to be found e.g. in“Riechstoffe [Fragrances]”, in Steffen Arctander, in“Perfume and Flavor Chemicals”, Self-published, Montclair, N.J. 1969; H. Surburg, J. Panten, in“Common Fragrance and Flavor Materials”, 5th Edition, Wiley-VCH, Weinheim 2006.
  • the encapsulated flavour(s) and/or aroma(s) may be an aroma mixture of at least two flavours and/or aromas. Preferably, it is a mixture of at least three, four or more than five flavours and/or aromas. In most cases, the aroma mixtures are a mixture of many flavours and/or aromas. This has the advantage that the taste profile of the capsules can be influenced.
  • Suitable aroma molecules are well known in the art and may be derived from e.g. US 2017/190727 (A1 ) and US 2017/190727 (A1 ).
  • the aroma substance or these aroma substances preferably causes or cause a flavour impression, a flavour-modulating effect, a trigeminal effect and/or a salivatory stimulus.
  • Exemplary cooling agents comprise one or more of menthol and menthol derivatives (for example L-menthol, D-menthol, racemic menthol, isomenthol, neoisomenthol, neomenthol), menthyl ethers (for example (l-menthoxy)-1 ,2- propanediol, (1-menthoxy)-2-methyl-1 ,2-propanediol, l-menthyl methyl ether), menthyl esters (for example menthyl formate, menthyl acetate, menthyl isobutyrate, menthyl lactate, L-menthyl L-lactate, L-menthyl D-lactate, menthyl (2- methoxy)acetate, menthyl (2-methoxyethoxy)acetate, menthyl pyroglutamate), menthyl carbonates (for example menthyl propylene glycol carbonate, menthyl ethylene glycol carbonate, men
  • Menthol (L-menthol, D-menthol, racemic menthol, isomenthol, neoisomenthol, neomenthol), L-menthyl methyl ether, menthyl formate, menthyl acetate), menthone, isopulegol, l-(-)-isopulegol acetate) and cubebol have flavor effect.
  • Suitable cooling agents are well known in the art and may be derived from e.g. US 2017/216802 (A1 ), US 2010/273887 (A1 ), EP 2 033 688 (A2) and EP 1 958 627 (A2).
  • Insect repellents, pheromones and insecticides are well known in the art.
  • suitable insect repellents and insecticides in view of the application field.
  • Other possible active substances include dyes or colors. Said compounds may be included e.g. in a shampoo for obtaining a coloring effect of the hairs.
  • dyes or color formers include those which are commercially available in the art for producing carbonless copy papers and that are known not to react with isocyanates. Examples are compounds of the type of the triphenylmethane compounds, diphenylmethane compounds, bisindophthalide compounds, bisarylcarbazolylmethane compounds, xanthene compounds, benzoxazine compounds, thiazine compounds, and spiropyran compounds, especially those which are known for use as color formers for producing carbonless copy papers.
  • Colorformers Mixtures of a plurality of colorformers can also be used. Some useful colorformers are described, for example, in EP-A 591 ,106, EP-A 315,901 , EP-A 234,394, DE-A 3,622,262, and EP-A 187,329, the contents of which are incorporated by way of reference in their entirety. Dyes and colors may be advantageously used for providing color effects to human hair upon using in a shampoo. It will be furthermore appreciated that the active substance is not particularly limited. Conceivable further active substances generally include all compounds for which there exist applications from the field of microencapsulation. Such ingredients are well known in the art. Examples include, for instance, dyes such as color definers for the production of carbonless copy papers, and medicines for pharmaceutical applications.
  • Active substances for cosmetic applications are preferred. Also preferred are active substances which are odorous substances or odorous substance compositions, in particular for application in and/or perfuming of consumer goods. Either an individual odorous substance or a mixture of odorous substances (perfume composition, odorous substance composition) can be selected.
  • the odorous substances can be compounds both of synthetic and of natural origin.
  • the composition for delivery of an active substance comprises or consists of -0.1 to 5.0 wt.-% of the at least one organic ammonium compound and/or the at least one thermosensitive polymer;
  • the capsule comprising an active substance
  • the solvent preferably water.
  • the composition for delivery of an active substance comprises or consists of
  • the solvent preferably water.
  • the composition for delivery of an active substance comprises or consists of
  • the capsule comprising at least one fragrance
  • compositions for delivery of an active substance comprise:
  • polyquaternium-7 0.1 part by weight gum or related polysaccharide (e. g. guar gum) and 15 part by weight SLS (Formulation 1 B);
  • polyquaternium-10 0.1 part by weight gum or related polysaccharide (e. g. guar gum) and 32 part by weight SLS (Formulation 2B);
  • polyquaternium-10 0.1 part by weight gum or related polysaccharide (e. g. guar gum) and 15 part by weight SLS (Formulation 3B).
  • gum or related polysaccharide e. g. guar gum
  • compositions comprise further excipients, which may include at least one first polymer, and/or solvents according to their intended use.
  • the compositions in particular comprise one or more thickener (s) in suitable amounts.
  • the consistency, particularly visocosity, of the composition may be adapted to a specific type of applcator, such as a spraying device/atomizer.
  • a formulation comprising 0.3 to 2 parts by weight, preferably, 0.5 to 1.5 parts by weight, or 0.75 to 1 parts by weight, of an organic ammonium compound, and 8 to 20 parts by weight, preferably 10 to 15 parts by weight, or 12 to 14 parts by weight may be provided as constituent of a kit.
  • any of the above captioned formulations 1 A, 2A, 3A, 1 B, 2B and 3B may be provided as the constituent of a kit.
  • the kit may further encompass any of instructions, a personal care product, and a capsule comprising an active substance. According to the instructs, the user may mix the formulation with the personal care product encompassed in the kit or with any other personal care product (with the proviso that said personal care products encompasses a capsule with an active substance) of the user’s choice.
  • a shampoo is provided.
  • the shampoo has the composition indicated in table 2 to which 2 to 5 parts per weight of a capsule comprising a fragrance are added.
  • a method for preparing a composition for delivery of an active substance comprises or consists of the steps of:
  • step (d) adding a capsule comprising an active substance to the mixture of step (c).
  • a viscosity modifier is included.
  • a viscosity modifier may be added to any of steps (a), (b), (c) and/or (d).
  • first and second solvent may be any of the above mentioned solvent(s). It is particularly preferred that the first and second solvents are the same solvents, more preferably the first and second solvents are both water.
  • method steps (a), (b) and (c) are conducted under heating, preferably at a temperature of 60 to 95°C, more preferably 70 to 80°C.
  • method step (c) is followed by cooling to room temperature.
  • Room temperature as used herein pertains to a temperature of about 21 to 24°C, preferably, 22 to 23 °C.
  • the method for preparing the present composition further comprises step (e) adjusting a physiological pH and/or adding a third solvent and/or adding a further excipient to any of steps (a), (b), (c), (d), or (e).
  • the third solvent and further excipient may be any solvent(s) or exipient(s) outlined above.
  • a physiological pH as used herein depends from the intended use.
  • the physiological pH may be for instance in a range between 6.5 and 7.8, such as 7 to 7.5. Adjustment of the pH may require addition of an acid, such as citric acid, or any other acid or a base, such as sodium hydroxide, or any other base.
  • the third solvent may be any kind and number of the solvents listed above.
  • the further excipient may be any kind and number of the solvents listed above.
  • a shampoo according to the present invention is preferably prepared by the steps:
  • Phase A In a separate vessel disperse a polyquaternium in water under mixing. Heat up to 75°C and hydrate for 20 min;
  • Phase B In the tank disperse Carbopol Ultrez 10 in water under mixing and hydrate few minutes;
  • phase C add phase C to phase B in the listed order, heat to 75°C-80°C and mix until homogeneity;
  • composition of the different phases is indicated in table 1 with the proviso of adding 2 to 5 parts per weight of a capsule comprising a fragrance. It will be readily understood that merely the constituents of the phases needs to be present, whereas the amounts as mentioned in the table may be varied.
  • the capsule is preferably included in (6), more preferably in any of phases D, E, or F.
  • table 2 Another preferred shampoo according to the present invention is disclosed in table 2. It will be readily understood that merely the constituents to be present, whereas the amounts as mentioned in table 2 may be varied.
  • the composition for delivery of an active substance according the present invention is provided, which is produced or producible by the present method.
  • the use of the present composition as/in a detergent composition, preferably in one or more of personal care, laundry care, home care and air care is provided.
  • a product, preferably a perfumed product is provided.
  • the product comprises the present composition for delivery of an active substance, preferably wherein the product is a consumer goods product selected from the group consisting of personal care products, home care products and laundry care products.
  • Examples of personal-care products include shampoos, rinses, hair conditioners, soaps, creams, body washes such as shower or bath salts, body soap, body liquid, mousses, oils or gels, hygiene products, cosmetic preparations, body lotions, deodorants, antiperspirants, leave-on personal care applications including hair refresher and lotions; personal cleaners or sanitizers; and fabric care products such as fabric refreshers.
  • Rinse off products may be liquids, solids, pastes, or gels, of any physical form.
  • Examples of home-care products include solid or liquid detergents, all-purpose cleaners, fabric softeners and refreshers, ironing waters and detergents, softener and drier sheets, among which liquid, powder and tablet detergents and fabric softeners are preferred.
  • the perfumed product may be also present in the form of fine fragrance products including perfumes, after-shave lotions and colognes.
  • Preferred laundry care products include detergent-containing preparations, such as powder and liquid detergents and fabric softeners
  • detergents products are included such as detergent compositions or cleaning products for washing up or for cleaning various surfaces, for example intended for the treatment of textiles or hard surfaces, such as floors, tiles, stone-floors, etc.
  • the present composition is preferably used to perfume one or more of textiles, hair, skin, surfaces and/or ambient air. Furthermore, the use of the present composition as/in a deodorant, which deodorant preferably provides fine fragrance delivery, may be provided.
  • the present composition is particularly useful for laundry care of specific tissues, such as sport cloths and/or hospital cloths.
  • composition according to the present invention is preferably performed by employing the above mentioned product, preferably a perfumed product, comprising the present composition.
  • the product is preferably a consumer goods product selected from the group consisting of personal care products, home care products and laundry care products.
  • the use of the present composition as/in a composition for killing insects is provided, wherein the active substance includes an insecticide. Pheromones would be another active (pet or Zoo care market).
  • An animal such as a cattle, may be treated with the present composition or product according to the present invention comprising the present product.
  • the insecticide(s) encompassed by the capsules are released upon acting pressure or friction on treated surface regions. In consequence, release may take place upon rubbing (e.g. on any surface or ground). Treatment of various surface regions of the animal and/or the use of capsules of different composition may further assist in sustained release of the insecticide(s).
  • the use of the present composition for use as/in a food or beverage product is provided.
  • a preferred active substance include one or more dyes for e.g. providing the beverage or food a pleasant color, color effect or marking it as a unique feature.
  • the active substance may encompass an essential oil for providing a pleasant smell. In this manner for instance tiny precipitated drinks may be prepared.
  • the expression “have/contain” or “having/containing” designates an open enumeration and does not exclude other components apart from the expressly named components.
  • the expression“consists of” or“consisting of” designates a closed enumeration and excludes any other components apart from the expressly named components.
  • the expression“essentially consists of or “essentially consisting of” designates a partially closed enumeration and designates preparations which apart from the named components only have such further components as do not materially alter the character of the preparation according to the invention.
  • a preparation is described with the use of the expression“have” or“having”, this expressly includes preparations which consist of said components or essentially consist of said components.
  • FIG. 1 microscopic photographs of a conventional shampoo formulation (left) and corresponding shampoo formulations according to the present invention (right); Scale of 25 urn
  • Fig. 2 sensory data of a shampoo formulation which formed complexes according to the present invention on test hairs.
  • Example 1
  • compositions are further provided with 0.1 to 5.0 part by weight of the capsule, preferably SymCap, comprising at least one fragrance.
  • these compositions comprise further excipients and/or solvents according to their intended use.
  • Table 1 shows a finished formulation. Individual values are shown as parts by weight.
  • the composition is further provided with 0,1 to 5,0 part by weight of a capsule, preferably SymCap, comprising at least one fragrance.
  • the individual shampoo formulations according to table 1 are preferably prepared by the steps: (1 ) Phase A: In a separate vessel disperse a polyquaternium in water under mixing. Heat up to 75°C and hydrate for 20 min;
  • Phase B In the tank disperse Carbopol Ultrez 10 in water under mixing and hydrate few minutes;
  • phase C add phase C to phase B in the listed order, heat to 75°C-80°C and mix until homogeneity;
  • phase G is preferably included during (6), more preferably in any of phases D, E, or F.
  • Fig. 1 (formulation shampoo 1 B) show microscopic photographs. Precipitate formation in shampoo when added in water (1 : 3 ratio) without polymer combination (left) and with polymer combination (right) may be seen. The voluminous precipitates on both photographs on the right indicate formation of the present association complexes of organic ammonium compound/ first polymer/ capsule/thickener.
  • Said example shows the composition of a second shampoo formulation (table 2).
  • Said formulation furthermore comprises 2 to 5 parts by weight of capsules comprising a fragrance.
  • Table 2 shows a composition of a second shampoo, indicated in parts per weight.
  • the second shampoo furthermore comprises 2 to 5 parts by weight of capsules comprising a fragrance.
  • the individual values of the table are shown as parts by weight.
  • association complexes can be used to deliver fragrance, other actives, freshning agents, antimalodor actives etc.
  • the same mechanism can also be explored for food, drinks and flavour delivery.
  • the present composition may be applied:

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Abstract

La présente invention concerne une composition destinée à la distribution d'une substance active, la composition comprenant ou étant constituée d'au moins un composé d'ammonium organique et/ou d'au moins un polymère thermosensible ; d'au moins un excipient comprenant au moins un premier polymère ; d'une capsule comprenant une substance active ; et éventuellement d'un solvant et/ou d'un modificateur de viscosité. En outre, l'invention concerne un produit comprenant la présente composition destinée à la distribution d'une substance active, un procédé de préparation de la présente composition destinée à la distribution d'une substance active et l'utilisation de la présente composition destinée à la distribution d'une substance active.
PCT/EP2018/055456 2018-03-06 2018-03-06 Dépôt de substance active encapsulée sur les cheveux et un textile Ceased WO2019170222A1 (fr)

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