Fragrance composition containing 1, 3-butanediol

Abstract

The invention relates to a fragrance composition, in particular to a fragrance composition containing 1, 3-butanediol. The disclosure also relates to consumer products containing the fragrance composition, such as resident products, such as light perfumes, light essences, body spices, body perfumes, and the like.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to European application No. 22193249.4 filed on August 31, 2022, which is hereby incorporated by reference as if set forth in its entirety herein. Technical Field

[0003] The present disclosure relates to fragrance compositions, in particular to fragrance compositions comprising 1,3-butylene glycol. The present disclosure also relates to consumer products containing the fragrance compositions, such as leave-on products, such as eau de toilette, eau de parfum, body spray, deodorant, etc. Background Art

[0004] The use of ethanol in consumer products, especially personal care products, is controversial. This controversy is due to religious beliefs, environmental impacts, and the tendency to irritate the skin. As a result, there has been a growing trend over the past decade to reduce the use of ethanol in personal care products. Many industries, especially the fragrance industry, are facing a potential new CARB regulation that seeks to limit the percentage of volatile organic compounds (VOCs) in personal fragrance products with a fragrance content of ≤10% to 50% by January 2031.

[0005] However, there are challenges in reducing the ethanol content in fragrance products. One challenge is the reduction in olfactory impact, which is the potency or intensity of the fragrance raw materials in the initial moments of product performance. Since ethanol is very volatile, it helps provide olfactory impact. Replacing ethanol with less volatile solvents in fragrance products tends to reduce its olfactory effect, which is unfavorable because impact is a very important characteristic of fragrance because it provides the first impression of the fragrance. Another challenge is the reduction in solubility of the components in the fragrance. Ethanol can be used to dissolve fragrance components, many of which are lipophilic. Reducing ethanol will result in a reduction in the solubility of fragrance components, often leading to undesirable results.

[0006] Therefore, there is a continuing need for fragrance compositions that are low in VOCs but still provide the desired olfactory performance and solubility of fragrance components. Summary of the invention

[0007] The following aspects of the present disclosure are directed to addressing one or more of the above-mentioned issues.

[0008] In a first aspect, the present disclosure relates to a fragrance composition comprising at least:

[0009] a) 1,3-butanediol,

[0010] b) a fragrance component, wherein the fragrance component comprises more than 25% by weight, relative to the weight of the fragrance component, of a perfume ingredient having a vapor pressure greater than 0.0008 Torr at 25°C, and

[0011] c) a volatile solvent having a vapor pressure higher than 0.1 mmHg at 20° C., the content of which does not exceed 70% by weight, and is typically 20% to 70% by weight, relative to the total weight of the fragrance composition.

[0012] In a second aspect, the present disclosure is directed to a consumer product comprising the fragrance composition described herein.

[0013] In a third aspect, the present disclosure relates to a method for enhancing or adjusting the perceived olfactory impact and / or persistence of a fragrance composition, the method comprising mixing 1,3-butanediol with a fragrance component and a volatile solvent having a vapor pressure higher than 0.1 mmHg at 20°C to obtain the fragrance composition, wherein the content of the volatile solvent having a vapor pressure higher than 0.1 mmHg at 20°C is no more than 70% by weight, typically 20% to 70%, relative to the total weight of the fragrance composition. BRIEF DESCRIPTION OF THE DRAWINGS

[0014] Figure 1 Shown is a comparison of the olfactory performance between a reference composition and a composition according to the invention, both containing the same fragrance.

[0015] Figure 2 A comparison of the olfactory performance between the compositions of the invention and their corresponding control formulations is shown.

[0016] Figure 3 A comparison of olfactory performance between various compositions of the present disclosure is shown.

[0017] Figure 4 Another comparison of olfactory performance between various compositions of the present disclosure is shown. DETAILED DESCRIPTION

[0018] As used herein, the terms "a", "an" or "the" mean "one or more" or "at least one" unless otherwise specified.

[0019] Although compositions and methods are described in terms of "comprising," "containing," or "including" various components or steps, compositions and methods may also "consist essentially of" or "consist of" the various components, materials, and steps. As used herein, the term "consist essentially of" should be interpreted as including the listed components, materials, or steps and such additional components, materials, or steps that do not materially affect the basic and novel properties of the composition or method. In some embodiments, a composition "consisting essentially of" according to an embodiment of the present disclosure does not include any additional components or materials that change the basic and novel properties of the composition.

[0020] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this specification belongs.

[0021] It should be understood that any numerical range described herein is intended to include all subranges contained therein. For example, a range of "1 to 10" is intended to include all subranges between the stated minimum value of 1 and the stated maximum value of 10; that is, having a minimum value equal to or greater than 1 and a maximum value equal to or less than 10. Since the disclosed numerical ranges are continuous, they include every value between the minimum and maximum values. Unless otherwise expressly stated, the various numerical ranges specified in this application are approximate.

[0022] As used herein, unless otherwise indicated, the term "about" or "approximately" refers to the acceptable error of a particular value determined by one skilled in the art, which depends in part on how the value is measured or determined. In certain embodiments, the term "about" or "approximately" refers to within 1, 2, 3, or 4 standard deviations. In certain embodiments, the term "about" or "approximately" refers to 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.

[0023] Throughout this disclosure, various publications may be incorporated by reference. If the meaning of any term in these publications incorporated by reference conflicts with the meaning of the term in this disclosure, the meaning of the term in this disclosure takes precedence unless otherwise stated.

[0024] In the entire disclosure, various chemical names and structures can be listed. Unless otherwise stated, any stereoisomers of the listed chemical names or structures are considered, such as enantiomers, diastereomers, anomers, epimers, etc.; and geometric isomers, such as cis / trans or E / Z isomers. It will be understood by those of ordinary skill in the art that stereoisomers can have a stereocenter, thereby producing enantiomers, or have multiple stereocenters, thereby producing diastereomers, each stereocenter having one of two different stereochemicals (i.e., R or S). Enantiomers are characterized in that they can rotate the oncoming plane polarized light to the right, referred to as right-handed, "(+)" or "D", or rotate to the left, referred to as left-handed, "(-)" or "L". Enantiomers can exist as racemic mixtures or non-racemic (scalemic, ratio optical rotation) mixtures. Geometric isomers refer to isomers that differ in the spatial relationship of atoms around a double bond and are usually designated as E or Z as commonly understood in the chemical art. Geometric isomers may also exist as a mixture of E and Z isomers. All such isomeric variations of the chemical names or structures described herein are included.

[0025] In a first aspect, the present disclosure relates to a fragrance composition comprising at least:

[0026] a) 1,3-butanediol,

[0027] b) a fragrance component, wherein the fragrance component comprises more than 25% by weight, relative to the weight of the fragrance component, of a perfume ingredient having a vapor pressure greater than 0.0008 Torr at 25°C, and

[0028] c) a volatile solvent having a vapor pressure higher than 0.1 mmHg at 20° C., the content of which does not exceed 70% by weight, and is typically 20% to 70% by weight, relative to the total weight of the fragrance composition.

[0029] The content of 1,3-butanediol (also known as butanediol / butylene glycol) can be present in any suitable amount. However, in some embodiments, the content of 1,3-butanediol is at least 1% by weight relative to the total weight of the fragrance composition, typically 1% to 50%, more typically 1% to 30%. 1,3-butanediol can be synthesized according to known methods, or is generally obtained from commercial sources.

[0030] The fragrance component comprises greater than 25% by weight, relative to the weight of the fragrance component, of a perfume ingredient having a vapor pressure greater than 0.0008 Torr at 25°C.

[0031] In some embodiments, the fragrance component comprises greater than 45%, typically greater than 50%, more typically greater than 55% by weight, relative to the weight of the fragrance component, of perfume ingredients having a vapor pressure greater than 0.0008 Torr at 25°C.

[0032] In other embodiments, the fragrance component comprises 45% to 99%, typically 55% to 99%, more typically 60% to 99% by weight relative to the weight of the fragrance component of perfume ingredients having a vapor pressure above 0.0008 Torr at 25°C.

[0033] Fragrance ingredients having a vapor pressure above 0.0008 torr at 25°C may be selected from fragrance ingredients known to those of ordinary skill in the art. As used herein, the term "vapor pressure" refers to the partial pressure of air for a given chemical at a specified temperature. It defines that the chemical is expected to be in the gas phase rather than in the liquid or solid state. The higher the vapor pressure, the greater the proportion of the material found in the closed head space at equilibrium. It is also related to the evaporation rate of the fragrance ingredient, which is defined in the open environment of the material leaving the system. The vapor pressure of the fragrance ingredient can be determined by any method known to those of ordinary skill in the art, such as the method disclosed in International Patent Application Publication No. WO 2015 / 089246A1.

[0034] In one suitable method, to determine the vapor pressure of a flavor material, one may visit the website "https: / / scifinder.cas.org / scifinder / view / scifinder / scifinderExplore.jsf" and follow the steps listed to obtain the vapor pressure:

[0035] 1. Enter the CAS registration number of the specific fragrance material.

[0036] 2. Select Vapor Pressure from the search results.

[0037] 3. Record the vapor pressure (in Torr at 25°C).

[0038] SciFinder uses Advanced Chemistry Development (ACD / Labs) software version 11.02 ( 1994-2013). If the CAS number for a particular fragrance material is unknown or does not exist, the vapor pressure can be determined directly using the ACD / Labs reference procedure.

[0039] Exemplary fragrance ingredients having a vapor pressure greater than 0.0008 Torr at 25°C include, but are not limited to, the following:

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055] **Sources: Fragrance ingredients were available from one or more of the following companies: Firmenich (Geneva, Switzerland), Symrise AG (Holzminden, Germany), Givaudan (Argenteuil, France), IFF (Hazlett, NJ), Bedoukian (Danbury, CT), Sigma Aldrich (St. Louis, MO), Millennium Speciality Chemicals (Olympia Fields, IL), Polaone International (Jersey City, NJ), and Aroma & Flavor Specialities (Danbury, CT).

[0056] In one embodiment, the fragrance component comprises one or more fragrance ingredients selected from the group consisting of: 6-octen-1-ol, 3,7-dimethyl-; benzoic acid, 2-(methylamino)-, methyl ester; 1,6-octadien-3-ol, 3,7-dimethyl-; 1,6-octadien-3-ol, 3,7-dimethyl-, 3-acetate; acetate, phenyl methyl ester; decanal; cyclohexene, 1-methyl-4-(1-methylvinyl)-; cyclohexene, 1-methyl-4-(1-methylvinyl)-, (4R)-; octanal; and mixtures thereof.

[0057] The amount of the fragrance component in the fragrance composition is not particularly limited, but in one embodiment, the fragrance component is present in an amount less than 50% by weight relative to the total weight of the fragrance composition, typically 1% to 50%, more typically 1% to 15%.

[0058] The amount of volatile solvents having a vapor pressure higher than 0.1 mmHg at 20°C is not more than 70%. In one embodiment, the amount of volatile solvents having a vapor pressure higher than 0.1 mmHg at 20°C is 20% to 70% by weight relative to the total weight of the fragrance composition. In another embodiment, the amount of volatile solvents having a vapor pressure higher than 0.1 mmHg at 20°C is 50% to 70% by weight relative to the total weight of the fragrance composition. In another embodiment, the amount of volatile solvents having a vapor pressure higher than 0.1 mmHg at 20°C is not more than 50%. In one embodiment, the amount of volatile solvents having a vapor pressure higher than 0.1 mmHg at 20°C is 20% to 50% by weight relative to the total weight of the fragrance composition. In one embodiment, the volatile solvent having a vapor pressure above 0.1 mmHg at 20°C is present in an amount of 40%, 41%, 42%, 43%, 44%, 45%, 46%, 47%, 48% or 49% to 50% by weight relative to the total weight of the fragrance composition.

[0059] Exemplary volatile solvents having a vapor pressure above 0.1 mmHg at 20° C. include, but are not limited to, ethanol, methanol, propanol, isopropanol, butanol, and mixtures thereof. In one embodiment, the volatile solvent having a vapor pressure above 0.1 mmHg at 20° C. comprises ethanol.

[0060] In one embodiment, ethanol is present in an amount of 40%, 41%, 42%, 43%, 44%, 45%, 46%, 47%, 48% or 49% to 50% by weight relative to the total weight of the fragrance composition.

[0061] The fragrance composition according to the invention may also comprise at least one amphiphilic organic solvent different from 1,3-butanediol and characterized by a log P greater than or equal to −2 and less than or equal to 2.

[0062] As used herein, "log P" refers to the logarithm (base 10) of the partition coefficient (P), which is defined as the ratio of the organic phase (usually oil) to the aqueous phase concentration of a compound. Log P describes the partition coefficient of a compound in a two-phase system consisting of octanol and water (Log P = Log (C 辛醇 / C 水 )). This parameter provides a measure of the hydrophilic / lipophilic properties of a compound: the higher the Log P, the more lipophilic the compound. The Log P value can be determined empirically or calculated. In some embodiments, the log P values ​​of the components of the fragrance composition are calculated. The calculated log P or C log P can be obtained for each single perfuming ingredient according to methods known to those of ordinary skill in the art. For example, 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. In another example, C log P can be calculated according to the method described in 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. Comput.-Aided Mol. Design 1991, 5, 149. In yet another example, C log P may be determined using an application provided by the following website: http: / / www.daylight.com / daycgi / clogp.

[0063] In one embodiment, the at least one amphiphilic organic solvent is selected from the group consisting of: diols, typically 1,2-alkanediols, such as 1,2-propylene glycol, 1,2-butylene glycol, 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol and 1,2-octanediol; and 1,3-alkanediols, such as 1,3-propylene glycol, 2-methyl-1,3-propylene glycol and 3-methyl-1,3-butylene glycol; 1,4-alkanediols, such as 1,4-butylene glycol; dipropylene glycol; polyalkylene glycols, typically polyethylene glycol, polypropylene glycol and poly(ethylene / propylene) glycol; C1-C2 citric acid; 10 Alkyl esters, typically triethyl citrate; and combinations thereof.

[0064] In one embodiment, the fragrance composition further comprises 1,2-alkanediol, typically 1,2-propylene glycol. In some embodiments, the fragrance composition further comprises 1,2-propylene glycol and one or more amphiphilic organic solvents selected from the group consisting of: diols, 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-propylene glycol, 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 glycol, polypropylene glycol and poly(ethylene / propylene) glycol; C1-C1 of citric acid; 10 Alkyl esters, typically triethyl citrate; and combinations thereof.

[0065] The amount of the at least one amphiphilic organic solvent is not particularly limited. However, in one embodiment, the at least one amphiphilic organic solvent is present in an amount of 0.1% to 50% by weight, typically 0.1% to 30%, more typically 5% to 15% by weight relative to the total weight of the fragrance composition.

[0066] The fragrance composition may also contain a perfuming co-ingredient. As used herein, a perfuming co-ingredient refers to an ingredient that imparts a hedonic effect, i.e., an ingredient that is primarily used to impart or modulate a scent. In other words, to be considered a perfuming co-ingredient, such a co-ingredient must be recognized by a person skilled in the art as being able to impart or modify the scent of the composition in an active or pleasant manner, rather than merely possessing a scent. In addition to modifying or imparting a scent, a perfuming co-ingredient may impart additional benefits, such as persistence, burst, malodor counteracting, antimicrobial action, antiviral action, microbial stability, or pest control.

[0067] The property and type of the flavoring auxiliary component do not guarantee a more detailed description here, and it is impossible to be exhaustive in any case, and those skilled in the art can select them according to their common sense and according to the intended use or application and the required organoleptic effect. Generally speaking, these flavoring auxiliary components belong to different chemical classifications, such as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogen-containing or sulfur-containing heterocyclic compounds and essential oils, and the flavoring auxiliary component can be natural or synthetic. In any case, suitable flavoring auxiliary components are listed in references such as S.Arctander's work Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA or its updated version or other works of similar nature, and in the patent literature abundant in the field of flavors. It should also be understood that the auxiliary component can also be a compound known to release various types of flavoring compounds (properfume or profragrance) in a controlled manner.

[0068] In one embodiment, the fragrance composition further comprises at least one fragrance modulator.

[0069] A fragrance modulator, also called a fixative, is an agent that has the ability to influence the way an observer or user perceives the odor of a composition into which it is incorporated, in particular the rate of evaporation and the intensity, over time, compared to the same perception without the modulator. In particular, the modulator allows the fragrance to be perceived for a longer period of time.

[0070] Examples of suitable fragrance modulators for use in accordance with the present disclosure include, but are not limited to, caprylyl alcohol, octanol, butyloctanol, isotridecyl alcohol, hexyldecyl alcohol, isostearyl alcohol, octyldecyl alcohol, octyldodecanol, decyltetradecyl alcohol, myristyl octadecyl alcohol, 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 fatty acid ester, sodium hyaluronate disaccharide, sodium hyaluronate, propylene glycol propyl ether; dicetyl ether; polyglyceryl-4 ether; isoceteth-5; isoceteth-7, isoceteth-10; isoceteth-12; isoceteth-15; isoceteth-20; isoceteth-25; isoceteth-30; disodium laurylamphodipropionate; hexaethylene glycol monododecyl ether; and mixtures thereof; neopentyl glycol diisononanoate; cetearyl ethylhexanoate; panthenol ethyl ether, DL-panthenol, hexadecyl nonanoate, octadecyl nonanoate, fragrance precursors, cyclodextrins, encapsulating agents, and any combination thereof.

[0071] In one embodiment, the at least one fragrance modulator is hexyldecanol.

[0072] The fragrance composition may further comprise water. In one embodiment, the water is present in an amount of 0.1% to 99% by weight, typically 0.1% to 30%, more typically 10% to 30% by weight relative to the total weight of the fragrance composition.

[0073] The fragrance composition described herein may include a solid carrier. The fragrance composition or certain ingredients of the fragrance composition, such as fragrance components, can be chemically or physically bound thereto. In general, such solid carriers are used to stabilize the composition, or to control the evaporation rate of the composition or certain ingredients. Solid carriers are currently used in the art, and those skilled in the art know how to achieve the desired effect. Suitable solid carriers include, but are not limited to, absorbent glues or polymers or inorganic materials, such as porous polymers, cyclodextrins, dextrins, maltodextrins, wood-based materials, organic or inorganic gels, clays, gypsum, talc or zeolites.

[0074] Other suitable solid carriers include encapsulating materials. Examples of such materials may include wall-forming materials and plasticizers, such as glucose syrup, natural or modified starch, hydrocolloids, cellulose derivatives, polyvinyl acetate, polyvinyl alcohol, proteins or pectins, plant gums such as acacia gum (gum arabic), urea, sodium chloride, sodium sulfate, 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, sugars such as sucrose, monosaccharides, disaccharides, trisaccharides and polysaccharides and derivatives such as chitosan, starch, cellulose, carboxymethyl methylcellulose, methylcellulose Cellulose, hydroxyethyl cellulose, ethyl cellulose, propyl cellulose, polyols / sugar alcohols such as sorbitol, maltitol, xylitol, erythritol and isomalt, polyethylene glycol (PEG), polyvinyl pyrrolidone (PVP), polyvinyl alcohol, acrylamide, acrylates, polyacrylic acid and related substances, maleic anhydride copolymers, amine functional polymers, vinyl ethers, styrene, polystyrene sulfonates, vinyl acid, ethylene glycol-propylene glycol block copolymers, vegetable gums, acacia gum, pectin, xanthan gum, alginates, carrageenan, citric acid or any water-soluble solid acid, fatty alcohols or fatty acids and mixtures thereof.

[0075] Other suitable encapsulating materials are described in references known to the person skilled in the art, for example H. Scherz, Hydrokolloide: Stabilisatoren, Dickungs- und Geliermittel in Lebensmitteln, Band2 der Schriftenreihe Lebensmittelchemie, Behr's Verlag GmbH & Co., Hamburg, 1996. Encapsulation is a process well known to the person skilled in the art and may be performed, for example, using techniques such as spray drying, agglomeration or extrusion; or consist of coating encapsulation including coacervation and complex coacervation techniques.

[0076] Other exemplary solid supports include core-shell capsules having aminoplast, polyamide, polyester, polyurea or polyurethane type resins and mixtures thereof, which are prepared using techniques well known to those skilled in the art, such as by polymerization-induced phase separation, interfacial polymerization, coacervation or a combination thereof, optionally in the presence of a polymer stabilizer or a cationic copolymer.

[0077] The resins may be produced by polycondensation of aldehydes such as formaldehyde, 2,2-dimethoxyacetaldehyde, glyoxal, glyoxylic acid or glycolaldehyde and mixtures thereof with amines such as urea, benzoguanamine, glycoluril, melamine, methylolmelamine, methylated methylolmelamine, guanazole, and the like and mixtures thereof. Alternatively, preformed resins may be used, such as those sold under the trademark (Source: Cytec Technology Corp.), (Source: Cytec TechnologyCorp.), or (Source: BASF) Those that are commercially available.

[0078] Other suitable resins are prepared by reacting a polyol such as glycerol with a polyisocyanate such as a trimer of hexamethylene diisocyanate, a trimer of isophorone diisocyanate or xylylene diisocyanate or the biuret of hexamethylene diisocyanate, or a trimer of xylylene diisocyanate and trimethylolpropane (known under the trade name Those produced by polycondensation of xylylene diisocyanate (source: Mitsui Chemicals), of which the trimer of xylylene diisocyanate with trimethylolpropane and the biuret of hexamethylene diisocyanate are preferred.

[0079] Encapsulation of fragrances by condensation of amino resins, i.e., melamine-based resins, with aldehydes is well known in the art. Relevant publications include, but are not limited to, Acta Polymerica, 1989, vol. 40, pages 243, 325, and 683 by K. Dietrich et al., and 1990, vol. 41, page 91, and U.S. Pat. No. 4,396,670 issued on August 2, 1983. General knowledge of encapsulation technology is very important and cannot be exhaustive. More recent targeted publications also relate to suitable uses of such microcapsules, representative articles such as K. Bruyninckx and M. Dusselier, ACS Sustainable Chemistry & Engineering, 2019, vol. 7, pages 8041-8054. These publications are incorporated herein by reference.

[0080] The fragrance composition may optionally comprise at least one fragrance adjuvant.

[0081] The at least one perfume adjuvant is an ingredient capable of imparting additional additional benefits such as colour, specific lightfastness, chemical stability, etc. A detailed description of the nature and types of adjuvants commonly used in perfuming compositions cannot be exhaustive, but it must be mentioned that said ingredients are well known to the person skilled in the art.

[0082] Exemplary flavor adjuvants include, but are not limited to, viscosity agents (e.g., surfactants, thickeners, gelling agents and / or rheology modifiers), stabilizers (e.g., preservatives, antioxidants, heat / light and / or buffers or chelating agents, such as BHT), colorants (e.g., dyes and / or pigments), preservatives (e.g., antibacterial or antimicrobial or antifungal or anti-irritants), abrasives, skin cooling agents, insect repellents, ointments, vitamins, and mixtures thereof.

[0083] The fragrance composition of the present disclosure can be prepared according to any method known to those of ordinary skill in the art. Ordinary technicians are fully capable of designing the best formula to achieve the desired effect by applying standard knowledge and concepts known to ordinary technicians and using conventional optimization methods to mix the above components to obtain the desired composition.

[0084] In a second aspect, the present disclosure is directed to a consumer product comprising the fragrance composition described herein.

[0085] The form of the consumer product is not particularly limited. In one embodiment, the consumer product is a perfume, a body care product, a cosmetic preparation, a skin care product, a fabric care product, an air care product or a home care product.

[0086] In another embodiment, the consumer product is a fine perfume, a splash, an eau de toilette, an eau de perfum, a cologne, a body mist, a body spray, a hair mist, a shaving lotion or aftershave, a shampoo, a dye preparation, a color care product, a hair styling product, a dental care product, a disinfectant, an intimate care product, a hair spray, a vanishing cream, a deodorant or antiperspirant, a depilatory, a tanning product or a sunscreen product, a nail product, a skin cleanser, a make-up product, a soap, a shower or bath mousse, a bath oil or shower gel, a foot / hand care product, a hygiene product, a liquid or solid or single-dose detergent, a fabric softener, a solid or liquid fabric fragrance enhancer, a fabric refresher, an ironing water, an air freshener, a "ready-to-use" powdered air freshener, a mildew remover, a furniture care product, a wipe, a dishwashing detergent or a hard surface cleaner, a leather care product, or a car care product.

[0087] The amount of the fragrance composition in the consumer product is not particularly limited. In one embodiment, the amount of the fragrance composition contained in the consumer product is 1% to 95% by weight, typically 2% to 80%, more typically 3% to 70% relative to the total weight of the consumer product.

[0088] In one embodiment, the consumer product comprises the fragrance composition in an amount of 1% to 30% by weight relative to the total weight of the consumer product, typically 2% to 20%, more typically 3% to 10%.

[0089] In a third aspect, the present disclosure relates to a method for enhancing or adjusting the perceived olfactory impact and / or persistence of a fragrance composition, the method comprising mixing 1,3-butanediol with a fragrance component and a volatile solvent having a vapor pressure higher than 0.1 mmHg at 20°C to obtain the fragrance composition, wherein the content of the volatile solvent having a vapor pressure higher than 0.1 mmHg at 20°C is no more than 70% by weight, typically 20% to 70%, relative to the total weight of the fragrance composition.

[0090] Generally, 1,3-butanediol can be mixed with the fragrance components and a volatile solvent having a vapor pressure above 0.1 mmHg at 20° C. using any suitable method known to those skilled in the art. For example, the components can be weighed and then mixed (typically by stirring) until homogeneous.

[0091] The fragrance compositions according to the present disclosure are typically homogeneous and transparent. As used herein, the term "homogeneous" means that all components of the composition are completely dissolved and the composition is uniform throughout. As used herein, the term "transparent" means that the composition has the property of transmitting light without significant light scattering. The transparency of the composition can be assessed by determining its turbidity using a turbidimeter, the turbidity is expressed in NTU (nephelometric turbidity units), and the measurement is performed in a 2.5 cm cell at 25° C. at a wavelength of 400 to 600 nm. In some embodiments, the turbidity of the composition is 0 to 20 NTU.

[0092] The use of 1,3-butanediol for enhancing or adjusting the perceived olfactory impact and / or persistence of a fragrance composition is mentioned, the fragrance composition comprising a fragrance component and a volatile solvent having a vapor pressure higher than 0.1 mmHg at 20° C., the content of the volatile solvent not exceeding 70% by weight, typically 20% to 70% relative to the total weight of the fragrance composition.

[0093] The compositions, products, methods and uses according to the present disclosure are further illustrated by the following non-limiting examples.

[0094] Example 1. Eau de Toilette (EDT) according to the present disclosure

[0095] Eau de toilette (EDT) is made by combining a fragrance ("Fragrance A") with the components and amounts summarized in Table 1 below. To obtain the composition of the present disclosure, all organic solvents are weighed and mixed in a beaker under magnetic stirring. Fragrance (typically in the form of fragrance oil) is added to the mixture. Water is added and the solution is stirred until homogeneous.

[0096] Table 1.

[0097] Components Comparison 1 EDT1 EDT2 EDT3 EDT4 (weight%) (weight%) (weight%) (weight%) (weight%) 1,3-Butanediol - 13 5 10 5 <![CDATA[1,2 - propylene glycol 1) > - 13 13 8 12 <![CDATA[Hexyldecanol 2) > - - - - 1 Fragrance A 10 10 4 4 4 Ethanol 75 50 50 50 50 Water (deionized water) 15 14 28 28 28

[0098] 1)Radianol 4710; Source: Oleon

[0099] 2)Eutanol G16; Source: BASF

[0100] "Fragrance A" has an inverted pyramid structure and contains the fragrance ingredients listed in Table 2 below.

[0101] Table 2.

[0102] Fragrance A ingredient Decanal Octanal 1-[(2RS,3RS,8aRS)-2,3,8,8-tetramethyl-1,2,3,5,6,7,8,8a-octahydro-2-naphthyl]ethanone Benzyl acetate (-)-(5R)-5-Isopropenyl-2-methyl-2-cyclohexen-1-one (2Z)-3,7-Dimethyl-2,6-octadienal (+-)-3,7-Dimethyl-6-octen-1-ol (+-)-3-Methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-pentanol (2E,4Z)-2,4-Decadienoic acid ethyl ester (3E,5Z)-1,3,5-Undecatriene Lavender oil 1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene (+-)-4-Isopropenyl-1-methylcyclohexene (-)-(3R)-3,7-Dimethyl-1,6-octadien-3-ol (+-)-3,7-Dimethyl-1,6-octadien-3-yl acetate Methyl 2-(Methylamino)benzoate Petitgrain essential oil 2-[1-(3,3-dimethylcyclohexyl)ethoxy]-2-oxoethyl]propionate (1RS,2SR,4RS)-2-Methoxy-4-propylcyclohexanol Dipropylene glycol

[0103] Example 2. Sensory Panel

[0104] A sensory panel evaluation was conducted to compare a reference EDT ("Control 1") and an inventive EDT ("EDT1"), both containing Fragrance A, to measure olfactory performance.

[0105] Preheat a Prazitherm PZ72 slide heater to 32°C for 30 minutes. Place a blotter on a precision heating plate. Use an adjustable volume pipette to drop 20 μL of solution directly onto the center of the blotter and evaporate at 32°C. Randomly arranged blotters were evaluated by 7 panelists at different times (t = 0 minutes (initial), 2 hours, 4 hours, and 6 hours).

[0106] The method used was a 3-Alternative Forced Choice test. For each time point, the panelists were presented with 3 samples, two of which were reference EDTs ("Control 1") and one of which was an inventive EDT1.

[0107] Panelists pointed to the samples that they considered to have higher overall strength.

[0108] Assumptions:

[0109] H0: There is no difference between the two samples.

[0110] H1: In terms of overall strength, samples that include technology are stronger than samples that do not include technology.

[0111] Related risks:

[0112] H0 is rejected = α risk:

[0113] Risks associated with false positives, concluding that products are different when they are not.

[0114] Data were analyzed using binomial statistics.

[0115] Data interpretation:

[0116] If a p-value is obtained for α ≤ 0.05, then the sample containing the technology is stronger than the sample without the technology in terms of overall strength,

[0117] If a p-value is obtained for α of 0.05 < α ≤ 0.10, it is determined that there is a trend difference,

[0118] If a p-value is obtained for α>0.10, then the samples are not significantly different.

[0119] The sensory evaluation results are as follows Figure 1 shown. Figure 1 Shown is a comparison of the olfactory performance of a reference EDT ("Control 1") and an EDT according to the invention ("EDT1"), both containing the same fragrance. Figure 1 The sensory panel results presented in show that at all time points, fragrance A in EDT1 performed significantly higher than the reference EDT. Therefore, EDT1 provided greater impact and persistence to the fragrance compared to the reference EDT.

[0120] Example 3. Influence of Fragrance Composition

[0121] To investigate the effect of fragrance composition (characterized by the vapor pressure of fragrance ingredients) on the impact and longevity of the EDT of the present invention, several fragrances were subjected to sensory panel evaluation. The fragrances characterized by the percentage of ingredients with vapor pressures above and below 0.0008 Torr (at 25°C) (Table 3), the control formulation (Table 4), and the present invention formulation (Table 5) are shown below.

[0122] Table 3.

[0123]

[0124] Table 4.

[0125] Components Comparison 2 Comparison 3 Comparison 4 Comparison 5 (weight%) (weight%) (weight%) (weight%) Fragrance ICE 10 - - - Fragrance SR - 10 - - Fragrance GG - - 10 - Fragrance LFB - - - 10 Ethanol 75 75 75 75 Water (deionized water) 15 15 15 15

[0126] Table 5.

[0127] Components EDT5 EDT6 EDT7 EDT8 (weight%) (weight%) (weight%) (weight%) 1,3-Butanediol 13 13 13 13 1,2-Propanediol 13 13 13 13 Fragrance ICE 10 - - - Fragrance SR - 10 - - Fragrance GG - - 10 - Fragrance LFB - - - 10 Ethanol 50 50 50 50 Water (deionized water) 14 14 14 14

[0128] Using the method described in Example 2, the inventive EDTs in Table 5 were compared to their corresponding control formulations in Table 4.

[0129] The results of the sensory panel are summarized in Figure 2 middle. Figure 2 The olfactory performance comparison between the EDT of the present invention in Table 5 and its corresponding control formulation in Table 4 is shown. The following Table 6 summarizes Figure 2 The p-values ​​for the results are shown in .

[0130] Table 6.

[0131]

[0132] According to these results, the low VOC EDT of the present invention achieves olfactory impact and persistence. It was found that olfactory impact and persistence increase with increasing percentage of fragrance material having a vapor pressure above 0.0008 Torr at 25°C.

[0133] Example 4. Effect of 1,3-butanediol dosage.

[0134] To investigate the effect of 1,3-BDO dosage on fragrance impact, a sensory panel was conducted to compare a fragrance SR in a low VOC formulation containing 5% 1,3-BDO and a fragrance SR in a low VOC formulation containing 10% 1,3-BDO. The two low VOC formulations are shown in Table 7 below.

[0135] Table 7.

[0136] Components EDT9 EDT10 (weight%) (weight%) 1,3-Butanediol 5 10 1,2-Propanediol 13 8 Fragrance SR 4 4 Ethanol 50 50 Water (deionized water) 28 28

[0137] EDT9 and EDT10 were compared using the method described in Example 2, with EDT9 being considered as the reference.

[0138] The results of the sensory panel are summarized in Figure 3 middle. Figure 3 A comparison of the olfactory performance between EDT9 and EDT10 is shown. The results show that the performance of the fragrance SR is significantly higher in EDT10 compared to EDT9. Thus, it has been shown that 10% 1,3-butanediol provides a greater impact to the fragrance SR compared to 5% 1,3-butanediol.

[0139] Example 5. Use of fragrance regulator

[0140] To investigate the effect of adding a fragrance modifier (or fixative), a sensory panel test was conducted to compare the fragrance SR in EDT9 according to Example 4 with that in a low VOC EDT ("EDT11") containing 1% fragrance modifier hexyldecanol, as shown in Table 8.

[0141] Table 8.

[0142] Components EDT11 (weight%) 1,3-Butanediol 5 1,2-Propanediol 12 Hexyldecanol 1 Fragrance SR 4 Ethanol 50 Water (deionized water) 28

[0143] EDT9 and EDT11 were compared using the method described in Example 2, with EDT9 considered as the reference.

[0144] The results of the sensory panel are summarized in Figure 4 middle. Figure 4Shown is a comparison of the olfactory performance between EDT9 and EDT11. The sensory panel results showed that the performance of Fragrance SR was significantly higher in EDT11 compared to EDT9, indicating that the addition of Hexyldecanol provided greater impact to Fragrance SR.

[0145] Example 6. Solubility test

[0146] This testing was conducted on a fragrance ("Fragrance QS") that contained a significant amount of fragrance ingredients characterized by a log P greater than 5 and which would cause solubility issues in hydroalcoholic solutions due to the high lipophilic content. Two low VOC formulations were prepared, as shown in Table 9 below.

[0147] Table 9.

[0148] Components EDT12 EDT13 (weight%) 1,3-Butanediol 5 5 1,2-Propanediol 13 12 Hexyldecanol - 1 Fragrance QS 4 4 Ethanol 50 50 Water (deionized water) 28 28

[0149] To study the effect of adding hexyldecanol on solubility, EDT12 and EDT13 were prepared. The EDT formulations were subjected to extreme temperature changes for 6 days: 3 cycles of 24 hours @ -20°C / 24 hours @ +25°C. At the end of the test, the appearance of each sample was evaluated.

[0150] Slight phase separation was observed in EDT12, while EDT13 was clear and homogeneous. Therefore, it was shown that the addition of hexyldecanol can improve the solubility of lipophilic fragrance ingredients.

[0151] The disclosed subject matter has been described with reference to specific details of particular embodiments. Unless such details are included in the appended claims, such details should not be construed as limitations on the scope of the disclosed subject matter.

[0152] Therefore, the exemplary embodiments described herein are well suited for achieving the objects and advantages described and those inherent therein. The specific embodiments disclosed above are illustrative only, as the exemplary embodiments described herein may be modified and practiced in different but equivalent manners, which will be apparent to those of ordinary skill in the art having the benefit of the teachings herein. In addition, the details of construction or design shown herein are not subject to any limitations except as described in the following claims. Therefore, it is apparent that the specific illustrative embodiments disclosed above may be changed, combined or modified, and all such variations are considered to be within the scope and spirit of the exemplary embodiments described herein. The exemplary embodiments described herein, which are illustratively disclosed herein, may be appropriately practiced in the absence of any elements not specifically disclosed herein and / or any optional elements disclosed herein.

Claims

1. A fragrance composition, comprising at least: a) 1,3-butanediol, b) a fragrance component, wherein the fragrance component comprises more than 25% by weight, relative to the weight of the fragrance component, of a perfume ingredient having a vapor pressure greater than 0.0008 Torr at 25°C, and c) a volatile solvent having a vapor pressure higher than 0.1 mmHg at 20° C., the content of which does not exceed 70% by weight, and is typically 20% to 70% by weight, relative to the total weight of the fragrance composition.

2. The fragrance composition according to claim 1, wherein the amount of 1,3-butanediol present is at least 1% by weight relative to the total weight of the fragrance composition, typically 1% to 50%, more typically 1% to 30%.

3. A fragrance composition according to claim 1 or 2, wherein the fragrance component is present in an amount of less than 50% by weight relative to the total weight of the fragrance composition, typically 1% to 50%, more typically 1% to 15%.

4. A fragrance composition according to any one of claims 1 to 3, wherein the fragrance component comprises more than 45%, typically more than 50%, more typically more than 55% by weight of a perfume ingredient having a vapor pressure of more than 0.0008 Torr at 25°C, relative to the weight of the fragrance component.

5. A fragrance composition according to claim 4, wherein the fragrance component comprises 45% to 99%, typically 55% to 99%, more typically 60% to 99% by weight of a perfume ingredient having a vapor pressure above 0.0008 Torr at 25°C, relative to the weight of the fragrance component.

6. The fragrance composition according to any one of claims 1 to 5, further comprising at least one amphiphilic organic solvent different from 1,3-butanediol and characterized by a log P greater than or equal to -2 and less than or equal to 2.

7. The fragrance composition according to claim 6, wherein the at least one amphiphilic organic solvent is selected from the group consisting of: diols, typically 1,2-alkanediols, such as 1,2-propylene glycol, 1,2-butylene glycol, 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol and 1,2-octanediol; and 1,3-alkanediols, such as 1,3-propylene glycol, 2-methyl-1,3-propylene glycol and 3-methyl-1,3-butanediol; 1,4-alkanediols, such as 1,4-butylene glycol; dipropylene glycol; polyalkylene glycols, typically polyethylene glycol, polypropylene glycol and poly(ethylene / propylene) glycol; C1-C2 citric acid; 10 Alkyl esters, typically triethyl citrate; and combinations thereof.

8. A fragrance composition according to claim 6 or 7, wherein the at least one amphiphilic organic solvent is present in an amount of 0.1% to 50% by weight, typically 0.1% to 30%, more typically 5% to 15% by weight relative to the total weight of the fragrance composition.

9. The fragrance composition according to any one of claims 1 to 8, wherein the content of the volatile solvent having a vapor pressure higher than 0.1 mmHg at 20°C is not more than 50% by weight relative to the total weight of the fragrance composition, typically 20% to 50%.

10. The fragrance composition according to any one of claims 1 to 9, further comprising at least one fragrance modulator.

11. The fragrance composition according to claim 10, wherein the at least one fragrance modulator is hexyldecanol.

12. The fragrance composition according to any one of claims 1 to 11, further comprising water.

13. A fragrance composition according to claim 12, wherein water is present in an amount of 0.1% to 99% by weight, typically 0.1% to 30%, more typically 10% to 30% by weight relative to the total weight of the fragrance composition.

14. A consumer product comprising the fragrance composition according to any one of claims 1 to 13.

15. The consumer product according to claim 14, wherein the consumer product is a perfume, a body care product, a cosmetic preparation, a skin care product, a fabric care product, an air care product or a home care product.

16. The consumer product according to claim 14 or 15, wherein the consumer product is a high-quality perfume, a perfume to be spread, an eau de toilette, an eau de parfum, a cologne, a moisturizing body spray, a body fragrance, a moisturizing hair spray, a shaving lotion or aftershave, a shampoo, a dyeing preparation, a color care product, a hair styling product, a dental care product, a disinfectant, an intimate care product, a hair spray, a vanishing cream, a deodorant or antiperspirant, a depilatory, a tanning product or a sunscreen product, a nail care product, a skin cleanser, a make-up product, a soap, a shower or bath mousse, a bath oil or a shower gel, a foot / hand care product, a hygiene product, a liquid or solid or single-dose detergent, a fabric softener, a solid or liquid fabric fragrance enhancer, a fabric refresher, an ironing water, an air freshener, a "ready-to-use" powdered air freshener, a mildew remover, a furniture care product, a wipe, a dishwashing detergent or a hard surface cleaner, a leather care product, or a car care product.

17. A method for enhancing or adjusting the perceived olfactory impact and / or persistence of a fragrance composition, the method comprising mixing 1,3-butanediol with a fragrance component and a volatile solvent having a vapor pressure higher than 0.1 mmHg at 20°C to obtain the fragrance composition, wherein the content of the volatile solvent having a vapor pressure higher than 0.1 mmHg at 20°C does not exceed 70% by weight, typically 20% to 70% relative to the total weight of the fragrance composition.

18. Use of 1,3-butanediol for enhancing or adjusting the perceived olfactory impact and / or persistence of a fragrance composition comprising a fragrance component and a volatile solvent having a vapor pressure higher than 0.1 mmHg at 20°C, the content of the volatile solvent not exceeding 70% by weight, typically 20% to 70% relative to the total weight of the fragrance composition.

Images