EP4551186A1 - Compositions de parfum contenant du 1,3-butanediol - Google Patents

Compositions de parfum contenant du 1,3-butanediol

Info

Publication number
EP4551186A1
EP4551186A1 EP23757624.4A EP23757624A EP4551186A1 EP 4551186 A1 EP4551186 A1 EP 4551186A1 EP 23757624 A EP23757624 A EP 23757624A EP 4551186 A1 EP4551186 A1 EP 4551186A1
Authority
EP
European Patent Office
Prior art keywords
fragrance
typically
fragrance composition
weight
butanediol
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.)
Pending
Application number
EP23757624.4A
Other languages
German (de)
English (en)
Inventor
Madelyne PHAM
Anne-Victoire DE BAYNAST
Aude Daugeron Jouault
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.)
Firmenich SA
Original Assignee
Firmenich SA
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 Firmenich SA filed Critical Firmenich SA
Publication of EP4551186A1 publication Critical patent/EP4551186A1/fr
Pending legal-status Critical Current

Links

Classifications

    • 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
    • A61K8/345—Alcohols containing more than one hydroxy group
    • 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
    • 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
    • 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
    • C11D3/43—Solvents
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L9/00—Disinfection, sterilisation or deodorisation of air
    • A61L9/01—Deodorant compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • 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
    • C11D3/2003—Alcohols; Phenols
    • C11D3/2041—Dihydric alcohols
    • C11D3/2044—Dihydric alcohols linear

Definitions

  • the present disclosure relates to fragrance compositions, particularly fragrance compositions comprising 1 ,3-butanediol.
  • the present disclosure also relates to consumer products, such as leave-on products, for instance eau de toilette, eau de perfume, body sprays, deodorants, and the like, containing the said fragrance compositions.
  • VOCs volatile organic compounds
  • olfactive impact is the efficacy or intensity of a perfumery raw material during the first moments of product performance.
  • ethanol aids in providing olfactive impact.
  • Replacing ethanol with a solvent of lower volatility in fragrance products tends to reduce its olfactive impact, which is detrimental since impact is a very important characteristic of a fragrance as it provides the first impression about the fragrance.
  • solubility of the components of a fragrance Ethanol is useful in solubilizing fragrance components, many of which are lipophilic. Reduction of ethanol leads to reduction of solubility of fragrance components, often leading to undesirable outcomes.
  • fragrance compositions that are low in VOC content but can elicit desirable olfactive performance as well as solubility of fragrance components.
  • the present disclosure relates to a fragrance composition
  • a fragrance composition comprising at least: a) 1 ,3-butanediol, b) a fragrance component, wherein the fragrance component comprises greater than 25% by weight of perfumery ingredients having a vapor pressure above 0.0008 Torr at 25 °C, relative to the weight of the fragrance component, and c) a volatile solvent with a vapor pressure above 0.1 mmHg at 20°C in an amount not greater than 70%, typically 20% to 70%, by weight relative to the total weight of the fragrance composition.
  • the present disclosure relates to a consumer product comprising the fragrance composition described herein.
  • the present disclosure relates to a method for enhancing or modulating the perceived olfactive impact and/or long-lastingness of a fragrance composition, the method comprising combining 1 ,3-butanediol with a fragrance component, and a volatile solvent with a vapor pressure above 0.1 mmHg at 20°C to obtain the fragrance composition, wherein the volatile solvent with a vapor pressure above 0.1 mmHg at 20°C is in an amount not greater than 70%, typically 20% to 70%, by weight relative to the total weight of the fragrance composition.
  • FIG. 1 shows a comparison of the olfactive performance between a reference composition and inventive composition, both of which contain the same fragrance.
  • FIG. 2 shows a comparison of the olfactive performance between inventive compositions and their corresponding control formulation.
  • FIG. 3 shows a comparison of the olfactive performance between inventive compositions.
  • FIG. 4 shows another comparison of the olfactive performance between compositions of the present disclosure.
  • the terms “a”, “an”, or “the” means “one or more” or “at least one” unless otherwise stated.
  • compositions and methods are described in terms of “comprising,” “containing,” or “including” various components or steps, the compositions and methods can also “consist essentially of” or “consist of” the various components, substances and steps.
  • the term “consisting essentially of” shall be construed to mean including the listed components, substances or steps and such additional components, substances or steps which do not materially affect the basic and novel properties of the composition or method.
  • a composition in accordance with embodiments of the present disclosure that “consists essentially of” the recited components or substances does not include any additional components or substances that alter the basic and novel properties of the composition.
  • all technical and scientific terms used herein have the same meaning as is commonly understood by one of skill in the art to which this specification pertains.
  • any numerical range recited herein is intended to include all sub-ranges subsumed therein.
  • a range of “1 to 10” is intended to include all sub-ranges between and including the recited minimum value of 1 and the recited maximum value of 10; that is, having a minimum value equal to or greater than 1 and a maximum value of equal to or less than 10. Because the disclosed numerical ranges are continuous, they include every value between the minimum and maximum values. Unless expressly indicated otherwise, the various numerical ranges specified in this application are approximations.
  • the term “about” or “approximately” means an acceptable error for a particular value as determined by one of ordinary skill in the art, which depends in part on how the value is measured or determined.
  • the term “about” or “approximately” means within 1 , 2, 3, or 4 standard deviations. In certain embodiments, the term “about” or “approximately” means within 50%, 20%, 15%, 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, 1 %, 0.5%, or 0.05% of a given value or range.
  • stereoisomers such as enantiomers, diastereomers, anomers, epimers, and the like; and geometric isomers, such as cis/trans or E/Z isomers, of the recited chemical name or structure are contemplated.
  • stereoisomers may possess one stereocenter, giving rise to enantiomers, or more than one stereocenter, giving rise to diastereomers, each stereocenter having one of two different stereochemistries (i.e. , R or S).
  • Enantiomers may be characterized by their ability to rotate oncoming plane-polarized light to the right, designated as dextrorotatory, “(+)” or “D”, or to the left, designated as levorotatory, or “L”. Enantiomers may exist as racemic mixtures or scalemic mixtures. Geometric isomers refer to isomers in which the spatial relationship of atoms around a double bond are different, typically designated E or Z according to conventional understanding in the chemical art. Geometric isomers may also exist as mixtures of E and Z isomers. All of the aforementioned isomeric variations of the chemical names or structures recited herein are included.
  • the present disclosure relates to a fragrance composition
  • a fragrance composition comprising at least: a) 1 ,3-butanediol, b) a fragrance component, wherein the fragrance component comprises greater than 25% by weight of perfumery ingredients having a vapor pressure above 0.0008 Torr at 25 °C, relative to the weight of the fragrance component, and c) a volatile solvent with a vapor pressure above 0.1 mmHg at 20°C in an amount not greater than 70%, typically 20% to 70%, by weight relative to the total weight of the fragrance composition.
  • the amount of 1 ,3-butanediol also known as butylene glycol, may be present in any suitable amount. However, in some embodiments, 1 ,3-butanediol is present in an amount of at least 1 %, typically from 1 % to 50%, more typically 1 % to 30%, by weight relative to the total weight of the fragrance composition. 1 ,3-butanediol may be synthesized according to known methods or, typically, obtained from commercial sources.
  • the fragrance component comprises greater than 25% by weight of perfumery ingredients having a vapor pressure above 0.0008 Torr at 25 °C, relative to the weight of the fragrance component.
  • the fragrance component comprises greater than 45%, typically greater than 50%, more typically greater than 55%, by weight of perfumery ingredients having a vapor pressure above 0.0008 Torr at 25 °C, relative to the weight of the fragrance component.
  • the fragrance component comprises 45% to 99%, typically 55% to 99%, more typically 60% to 99%, by weight of perfumery ingredients having a vapor pressure above 0.0008 Torr at 25 °C, relative to the weight of the fragrance component.
  • Perfumery ingredients having a vapor pressure above 0.0008 Torr at 25 °C may be selected from perfumery ingredients known those of ordinary skill in the art.
  • the term “vapor pressure” means the partial pressure in air at a defined temperature for a given chemical species. It defines a chemical species’ desire to be in the gas phase rather than the liquid or solid state. The higher the vapor pressure, the greater the proportion of the material that will, at equilibrium, be found in a closed headspace. It is also related to the rate of evaporation of a perfuming ingredient which is defined in an open environment where material is leaving the system.
  • the vapor pressure of perfumery ingredients may be determined by any method known those of ordinary skill in the art, such as methods disclosed in International Patent Application Publication No. WO 2015/089246 A1.
  • Perfumery ingredients may be obtained from one or more of the following companies: Firmenich (Geneva, Switzerland), Symrise AG (Holzminden, Germany), Givaudan (Argenteuil, France), IFF (Hazlet, New Jersey), Bedoukian (Danbury, Connecticut), Sigma Aldrich (St. Louis, Missouri), Millennium Speciality Chemicals (Olympia Fields, Illinois), Polarone International (Jersey City, New Jersey), and Aroma & Flavor Specialities (Danbury, Connecticut).
  • the fragrance component comprises one or more perfumery ingredient selected from 6-Octen-1-ol, 3,7-dimethyl-; Benzoic acid, 2-(methylamino)-, methylester; 1 ,6-Octadien-3-ol, 3,7-dimethyl-; 1 ,6-Octadien-3-ol, 3,7-dimethyl-, 3- acetate; Acetic acid, phenylmethyl ester; Decanal; Cyclohexene, 1-methyl-4-(1- methylethenyl)-; Cyclohexene, 1 -methyl-4-(1-methylethenyl)-, (4R)-; Octanal; and mixture thereof.
  • the amount of the fragrance component in the fragrance composition is not particularly limited. However, in an embodiment, the fragrance component is present in an amount of less than 50%, typically from 1 % to 50%, more typically from 1 % to 15%, by weight relative to the total weight of the fragrance composition.
  • the volatile solvent with a vapor pressure above 0.1 mmHg at 20°C is present in an amount not greater than 70%. In an embodiment, the volatile solvent with a vapor pressure above 0.1 mmHg at 20°C is present in an amount of from 20% to 70%, by weight relative to the total weight of the fragrance composition. In another embodiment, the volatile solvent with a vapor pressure above 0.1 mmHg at 20°C is present in an amount of from 50% to 70%, by weight relative to the total weight of the fragrance composition. In another embodiment, the volatile solvent with a vapor pressure above 0.1 mmHg at 20°C is in an amount not greater than 50%.
  • the volatile solvent with a vapor pressure above 0.1 mmHg at 20°C is present in an amount of from 20% to 50%, by weight relative to the total weight of the fragrance composition. In an embodiment, the volatile solvent with a vapor pressure above 0.1 mmHg at 20°C is present in an amount of from 40%, 41 %, 42%, 43%, 44%, 45%, 46%, 47%, 48%, or 49%, to 50%, by weight relative to the total weight of the fragrance composition.
  • Exemplary volatile solvents with a vapor pressure above 0.1 mmHg at 20°C include, but are not limited to, ethanol, methanol, propanol, isopropanol, butanol, and mixtures thereof.
  • the volatile solvent with a vapor pressure above 0.1 mmHg at 20°C comprises ethanol.
  • ethanol is present in an amount of from 40%, 41 %, 42%, 43%, 44%, 45%, 46%, 47%, 48%, or 49%, to 50%, by weight relative to the total weight of the fragrance composition.
  • the fragrance composition according to the present disclosure may further comprise at least one amphiphilic organic solvent different from 1 ,3-butanediol and that is characterized by a log P greater than or equal to -2 and less than or equal to 2.
  • log P refers to the logarithm (base 10) of the partition coefficient (P), which is defined as the ratio of a compound’s organic (typically, oil)-to-aqueous phase concentrations.
  • P partition coefficient
  • Log P values may be determined empirically or calculated. In some embodiments, the log P values are calculated. Calculated log P, or C log P, may be obtained for each single perfuming ingredient according to methods known to those of ordinary skill in the art.
  • C log P can be obtained according to the program EPI suite (4.0); EPA (US Environmental Protection Agency) and Syracuse Research Corporation (SRC), 2000.
  • C log P may be calculated according to a method described by Suzuki T. 1992, CHEMICALC 2, QCPE Program No 608, Department of chemistry, Indiana University; Suzuki T., Kudo Y. J. Comput.-Aided Mol. Design 1990, 4, 155; Suzuki T., J. Com put. -Aided Mol. Design 1991 , 5, 149.
  • C log P may be determined using an application available at the following website: http://www.daylight.com/daycgi/clogp.
  • the at least one amphiphilic organic solvent is selected from the group consisting of glycols, typically 1 ,2-alkanediols, such as 1 ,2-propanediol, 1 ,2- butanediol, 1 ,2-pentanediol, 1 ,2-hexanediol, 1 ,2-heptanediol, and 1 ,2-octanediol, and 1 ,3-alkanediols, such as 1 ,3-propanediol, 2-methyl-1 ,3-propanediol, and 3- methyl-1 ,3-butanediol; 1 ,4-alkanediols, such as 1 ,4-butanediol; dipropylene glycol, polyalkylene glycols, typically polyethylene glycols, polypropylene glycols, and poly(ethylene/propylene) glycols; C
  • the fragrance composition further comprises a 1 ,2-alkanediol, typically 1 ,2-propanediol.
  • the fragrance composition further comprises 1 ,2-propanediol and one or more amphiphilic organic solvents selected from the group consisting of glycols, typically 1 ,2-alkanediols, such as 1 ,2- butanediol, 1 ,2-pentanediol, 1 ,2-hexanediol, 1 ,2-heptanediol, and 1 ,2-octanediol, and 1 ,3-alkanediols, such as 1 ,3-propanediol, 2-methyl-1 ,3-propanediol, and 3- methyl-1 ,3-butanediol; 1 ,4-alkanediols, such as 1 ,4-butanediol; dipropy
  • the amount of the at least one amphiphilic organic solvent is not particularly limited. However, in an embodiment, the at least one amphiphilic organic solvent is present in an amount of from 0.1% to 50%, typically 0.1 % to 30%, more typically 5% to 15%, by weight relative to the total weight of the fragrance composition.
  • the fragrance composition may further comprise a perfuming co-ingredient.
  • a perfuming co-ingredient refers to ingredients that impart a hedonic effect, i.e. , used for the primary purpose of conferring or modulating an odor.
  • such a co-ingredient to be considered as being a perfuming one, must be recognized by a person skilled in the art as being able to impart or modify in a positive or pleasant way the odor of a composition, and not just as having an odor.
  • Perfuming co-ingredients may impart an additional benefit beyond that of modifying or imparting an odor, such as long-lasting, blooming, malodour counteraction, antimicrobial effect, antiviral effect, microbial stability, or pest control.
  • perfuming co-ingredients do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of his general knowledge and according to the intended use or application and the desired organoleptic effect.
  • these perfuming co-ingredients belong to chemical classes as varied as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulphurous heterocyclic compounds, and essential oils.
  • Perfuming co-ingredients can be of natural or synthetic origin. Suitable perfumery co- ingredients are in any case listed in reference texts such as the book by S.
  • the fragrance composition further comprises at least one fragrance modulator.
  • Fragrance modulators also known as fixatives, are agents having the capacity to affect the manner in which the odor, and in particular the evaporation rate and intensity, of the compositions incorporating said modulator can be perceived by an observer or user thereof, over time, as compared to the same perception in the absence of the modulator.
  • the modulator allows prolonging the time during which their fragrance is perceived.
  • fragrance modulators suitable for use according to the present disclosure include, but are not limited to, caprylyl alcohol, octanol, butyloctanol, isotridecyl alcohol, hexyldecanol, isostearyl alcohol, octyldecanol, octyldodecanol, decyltetradecanol, tetradecyloctadecanol, PPG-20 methyl glucose ether, methyl glucoside polyol; ethyl glucoside polyol; propyl glucoside polyol; isocetyl alcohol; PPG-3 myristyl ether; neopentyl glycol diethylhexanoate; sucrose laurate; sucrose dilaurate, sucrose myristate, sucrose palmitate, sucrose stearate, sucrose distearate, sucrose tristearate, hyaluronic acid disaccharide
  • the at least one fragrance modulator is hexyldecanol.
  • the fragrance composition may further comprise water.
  • water is present in an amount of from 0.1 % to 99%, typically 0.1 % to 30%, more typically 10% to 30%, by weight relative to the total weight of the fragrance composition.
  • the fragrance composition described herein may comprise a solid carrier.
  • the fragrance composition or some element of the fragrance composition, such as the fragrance component, can be chemically or physically bound.
  • such solid carriers are employed either to stabilize the composition, or to control the rate of evaporation of the compositions or of some ingredients.
  • Solid carriers are of current use in the art and a person skilled in the art knows how to reach the desired effect. Suitable solid carriers include, but are not limited to, absorbing gums or polymers or inorganic materials, such as porous polymers, cyclodextrines, dextrines, maltodextrines wood-based materials, organic or inorganic gels, clays, gypsum talc or zeolites.
  • suitable solid carriers include encapsulating materials.
  • suitable materials may comprise wall-forming and plasticizing materials, such as glucose syrups, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetates, polyvinylalcohols, proteins or pectins, plant gums such as acacia gum (Gum Arabic), urea, sodium chloride, sodium sulphate, zeolite, sodium carbonate, sodium bicarbonate, clay, talc, calcium carbonate, magnesium sulfate, gypsum, calcium sulfate, magnesium oxide, zinc oxide, titanium dioxide, calcium chloride, potassium chloride, magnesium chloride, zinc chloride, carbohydrates, saccharides such as sucrose, mono-, di-, and polysaccharides and derivatives such as chitosan, starch, cellulose, carboxymethyl methylcellulose, methylcellulose, hydroxyethyl cellulose, ethyl cellulose, propyl cellulose, polyols/sugar alcohols such
  • encapsulating materials are described in reference texts known to those of skill in the art, such as H. Scherz, Hydrokolloide: Stabilisatoren, Dickungs- und Geliersch in Strukturn, Band 2 der committee füren Herbert Strukturchemie, claritat, Behr's Verlag GmbH & Co., Hamburg, 1996.
  • the encapsulation is a well-known process to a person skilled in the art, and may be performed, for instance, by using techniques such as spray-drying, agglomeration or yet extrusion; or consists of a coating encapsulation, including coacervation and complex coacervation techniques.
  • exemplary solid carriers include core-shell capsules with resins of aminoplast, polyamide, polyester, polyurea or polyurethane type, and mixtures threof, made using techniques well-known to those of ordinary skill in the art, such as phase separation induced by polymerization, interfacial polymerization, coacervation, or a combination thereof, optionally in the presence of a polymeric stabilizer or of a cationic copolymer.
  • Resins may be produced by the polycondensation of an aldehyde (e.g., formaldehyde, 2,2-dimethoxyethanal, glyoxal, glyoxylic acid or glycolaldehyde, and mixtures thereof) with an amine such as urea, benzoguanamine, glycoluryl, melamine, methylol melamine, methylated methylol melamine, guanazole and the like, as well as mixtures thereof.
  • an aldehyde e.g., formaldehyde, 2,2-dimethoxyethanal, glyoxal, glyoxylic acid or glycolaldehyde, and mixtures thereof
  • an amine such as urea, benzoguanamine, glycoluryl, melamine, methylol melamine, methylated methylol melamine, guanazole and the like, as well as mixtures thereof.
  • Urac® oil: Cytec Technology Corp.
  • Cymel® oil: Cytec Technology Corp.
  • Urecoll® Urecoll®
  • Luracoll® origin: BASF
  • Suitable resins are the those produced by the polycondensation of a polyol, like glycerol, and a polyisocyanate, for example, a trimer of hexamethylene diisocyanate, a trimer of isophorone diisocyanate or xylylene diisocyanate or a Biuret of hexamethylene diisocyanate or a trimer of xylylene diisocyanate with trimethylolpropane (marketed as Takenate® by Mitsui Chemicals), among which a trimer of xylylene diisocyanate with trimethylolpropane and a Biuret of hexamethylene diisocyanate are of mention.
  • a polyol like glycerol
  • a polyisocyanate for example, a trimer of hexamethylene diisocyanate, a trimer of isophorone diisocyanate or xylylene diisocyanate or a Bi
  • the fragrance composition may optionally comprise at least one perfumery adjuvant.
  • the at least one perfumery adjuvant is an ingredient capable of imparting an additional added benefit such as a color, a particular light resistance, chemical stability, etc.
  • an additional added benefit such as a color, a particular light resistance, chemical stability, etc.
  • Exemplary perfumery adjuvants include, but are not limited to, viscosity agents (e.g., surfactants, thickeners, gelling and/or rheology modifiers), stabilizing agents (e.g., preservatives, antioxidant, heat/light and or buffers or chelating agents, such as BHT), coloring agents (e.g., dyes and/or pigments), preservatives (e.g. antibacterial or antimicrobial or antifungal or anti irritant agents), abrasives, skin cooling agents, insect repellants, ointments, vitamins and mixtures thereof.
  • viscosity agents e.g., surfactants, thickeners, gelling and/or rheology modifiers
  • stabilizing agents e.g., preservatives, antioxidant, heat/light and or buffers or chelating agents, such as BHT
  • coloring agents e.g., dyes and/or pigments
  • preservatives e.g. antibacterial or antimicrobial or antifung
  • fragrance compositions according to the present disclosure may be prepared according to any method known to those of ordinary skill in the art.
  • the ordinarily- skilled artisan is perfectly able to design optimal formulations for the desired effect by admixing the above mentioned components to arrive at the desired composition by applying standard knowledge and concepts known to those of ordinary skill and by utilizing routine optimization methodologies.
  • the present disclosure relates to a consumer product comprising the fragrance composition described herein.
  • the form of the consumer product is not particularly limited.
  • the consumer product is a perfume, a body-care product, a cosmetic preparation, a skincare product, a fabric care product, an air care product, or a home care product.
  • the consumer product is a fine perfume, a splash, an eau de toilette, an eau de perfume, a cologne, a body mist, a body spray, a hair mist, a shave or after-shave lotion, a shampoo, a coloring preparation, a color care product, a hair shaping product, a dental care product, a disinfectant, an intimate care product, a hair spray, a vanishing cream, a deodorant or antiperspirant, hair remover, tanning or sun product, a nail product, a skin cleansing, a makeup, a perfumed soap, a shower or bath mousse, oil or gel, a foot/hand care products, a hygiene product, a liquid or solid or unit-dose detergent, a fabric softener, a solid or liquid fabric scentbooster, a fabric refresher, an ironing water, an air freshener, a “ready to use” powdered air freshener, a mold remover, a furniture care product, a wipe,
  • the amount of the fragrance composition in the consumer product is not particularly limited.
  • the consumer product comprises the fragrance composition in an amount from 1 % to 100%, typically 1% to 95%, more typically from 2% to 80%, still more typically from 3% to 70%, by weight relative to the total weight of the consumer product.
  • the consumer product comprises the fragrance composition in an amount from 1 % to 30%, typically from 2% to 20%, more typically from 3% to 10%, by weight relative to the total weight of the consumer product.
  • the present disclosure relates to a method for enhancing or modulating the perceived olfactive impact and/or long-lastingness of a fragrance composition, the method comprising combining 1 ,3-butanediol with a fragrance component, and a volatile solvent with a vapor pressure above 0.1 mmHg at 20°C to obtain the fragrance composition, wherein the volatile solvent with a vapor pressure above 0.1 mmHg at 20°C is in an amount not greater than 70%, typically 20% to 70%, by weight relative to the total weight of the fragrance composition.
  • combining 1 ,3-butanediol with the fragrance component and the volatile solvent with a vapor pressure above 0.1 mmHg at 20°C may be achieve using any suitable method known to those of ordinary skill in the art.
  • the components may be weighed and then mixed, typically by stirring, until homogeneous.
  • the fragrance compositions according to the present disclosure are generally homogeneous and transparent.
  • ther term “homogeneous” means that all components of the composition are completely solubilized and the composition is uniform throughout.
  • the term “transparent” means that the composition has the property of transmitting light without appreciable light scattering. Transparency of a composition can be assessed by determining its turbidity expressed in NTU (Nephelometric Turbidity Units) using a turbidimeter, measured in a 2.5 cm cell at 25°C, at wavelengths between 400 and 600 nm. In some embodiments, the composition has a turbidity comprised between 0 and 20 NTU.
  • Mention is made of the use of 1 ,3-butanediol to enhance or modulate the perceived olfactive impact and/or long-lastingness of a fragrance composition comprising a fragrance component and a volatile solvent with a vapor pressure above 0.1 mmHg at 20°C in an amount not greater than 70%, typically 20% to 70%, by weight relative to the total weight of the fragrance composition.
  • compositions, products, methods, and uses, according to the present disclosure are further illustrated by the following non-limiting examples.
  • Eau de Toilettes according to the present disclosure were made by combining a fragrance (“Fragrance A”) with the components and amounts summarized in Table 1 below.
  • Fragrance A typically fragrance oil
  • “Fragrance A” had an inverted pyramid structure and contained the perfumery ingredients listed in Table 2 below. Table 2.
  • Example 2 Sensory panel A sensory panel was performed in order to compare the reference EDT (“Contrail”) and inventive EDT (“EDT1”), both of which contain Fragrance A, to measure olfactive performance.
  • H1 The sample with technology is more intense than the sample without technology, in terms of overall intensity.
  • FIG. 1 shows a comparison of the olfactive performance between a reference EDT (“ControH”) and inventive EDT (“EDT1”), both of which contain the same fragrance.
  • the results of the sensory panel presented in FIG. 1 show a significant higher performance of Fragrance A in EDT1 compared to the reference EDT at all time points. Therefore, it has been shown that the EDT1 provides more impact and long-lastingness to the fragrance compared to Reference EDT.
  • fragrances characterized by percentage of ingredients having vapor pressure above and below 0.0008 Torr (at 25 °C) (Table 3), control formulations (Table 4), and inventive formulations (Table 5) are shown below.
  • FIG. 2 shows a comparison of the olfactive performance between the inventive EDTs in Table 5 as compared to their corresponding control formulation in Table 4.
  • Table 6 summarizes the p-values of the results shown in FIG. 2.
  • olfactive impact and long-lastingness was achieved by the inventive low VOC EDTs. It was found that olfactive impact and long-lastingness increased with the percentage of fragrance materials having a vapor pressure above 0.0008 Torr at 25°C.
  • EDT9 and EDT10 were compared using the methodology described in Example 2, EDT9 being considered the reference.
  • FIG. 3 shows a comparison of the olfactive performance between EDT9 and EDT10.
  • the results show a significantly higher performance of Fragrance SR in EDT10 compared to EDT9. Therefore, it has been shown that 10% 1 ,3-butanediol provides more impact to the Fragrance SR than 5% 1 ,3-butanediol.
  • Example 5 Use of a fragrance modulator
  • a sensory panel was performed to compare EDT9 according to Example 4 and Fragrance SR in a low VOC EDT (“EDT11”) containing 1 % of a fragrance modulator, hexyldecanol, as shown in Table 8.
  • EDT9 and EDT11 were compared using the methodology described in Example 2 in which EDT9 was considered the reference.
  • FIG. 4 shows a comparison of the olfactive performance between EDT9 and EDT 11 .
  • the results of the sensory panel show a significantly higher performance of Fragrance SR in EDT1 1 compared to EDT9, indicating that the addition of hexyldecanol provides greater impact to the Fragrance SR.
  • EDT 12 and EDT 13 were prepared in order to study the influence of the addition of hexyldecanol on solubility.
  • the EDT formulations were placed under extreme conditions of temperature variations for 6 days: 3 cycles of 24h @ -20°C /24 h @ +25°C. At the end of the test, the aspect of each sample was evaluated.

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Abstract

La présente invention concerne des compositions de parfum, en particulier des compositions de parfum comprenant du 1,3-butanediol. La présente invention concerne également des produits de consommation, tels que des produits sans rinçage, par exemple de l'eau de toilette, de l'eau de parfum, des sprays corporels, des déodorants et analogues, contenant lesdites compositions de parfum.
EP23757624.4A 2022-08-31 2023-08-17 Compositions de parfum contenant du 1,3-butanediol Pending EP4551186A1 (fr)

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EP22193249 2022-08-31
PCT/EP2023/072636 WO2024046769A1 (fr) 2022-08-31 2023-08-17 Compositions de parfum contenant du 1,3-butanediol

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FR3166543A1 (fr) * 2024-09-25 2026-03-27 Marc Grosman Composition parfumée contenant une quantité d'eau ou d’eau hydrogénée et plus ou moins exempte d'éthanol et comprenant au moins un composé de formule ( C4H10O2 ), et au moins une matière colorante hydrosoluble et une substance parfumante.

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US4396670A (en) 1980-04-08 1983-08-02 The Wiggins Teape Group Limited Process for the production of microcapsules
US8389466B2 (en) * 2008-04-07 2013-03-05 Symrise Ag Use of carboxylic acid esters as a fragrance substance
US9814661B2 (en) 2013-12-13 2017-11-14 The Procter & Gamble Company Fragrance compositions
EP3920881A1 (fr) * 2019-02-04 2021-12-15 Symrise AG Activité antimicrobienne d'esters d'acides gras et combinaisons de ceux-ci
JP2020132547A (ja) * 2019-02-15 2020-08-31 国立大学法人 東京医科歯科大学 白髪抑制・改善剤、及び、その製造方法
EP4076362A1 (fr) * 2020-02-04 2022-10-26 Firmenich SA Formulations offrant une performance parfumée de longue durée
CN115397385A (zh) * 2020-03-31 2022-11-25 弗门尼舍有限公司 包含固体脂质材料的水包油乳液
JP7458639B2 (ja) * 2020-11-02 2024-04-01 シヤチハタ株式会社 スタンプ台用、朱肉用又は浸透印用香料組成物

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