Compositions for preventing, reducing or alleviating malodorous aldehydes and ketones and uses thereof

Abstract

The present disclosure relates to compositions capable of actively reducing malodor aldehydes and ketones, typically fragrance compositions. The present disclosure also relates to uses and methods of using such compositions to prevent, reduce or mitigate malodors caused by such malodorous aldehydes and ketones.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to European application No. 22180210.1 filed on June 21, 2022, the entire contents of which are expressly incorporated herein by reference. Technical Field

[0003] The present disclosure relates to compositions, typically fragrance compositions, that can actively reduce malodorous aldehydes and ketones. The present invention also relates to uses and methods of using such compositions to prevent or reduce malodors caused by such malodorous aldehydes and ketones. Background Art

[0004] Body odor is a general term for the odors that are naturally produced by the human body. The human body produces a range of substances that are usually degraded or transformed by natural processes such as auto-oxidation, bacterial action, enzymatic action, etc. The degradation or transformation of natural compounds secreted on the skin often produces compounds with an unpleasant odor. In small amounts, this odor may not be noticeable. However, excessive accumulation of such degradation or transformation products on the skin may result in a strong unpleasant odor.

[0005] For example, in some parts of India, many people use hair oil to care for their hair and wash their hair only once a week. Due to this habit, oxidation of fatty acids in scalp sebum and / or hair oil produces some foul-smelling aldehydes and ketones.

[0006] In addition, the so-called "old man smell" is a unique odor of middle-aged and elderly people. It is due to the degradation of lipid hydroperoxides in their skin, releasing foul-smelling aldehydes, mainly the compound 2-nonenal (see S. Haze et al., J. Invest. Dermatol. 116: 520-524 2001), and perhaps other lipid oxidation products.

[0007] Body odor comes not only from one's skin, hair or scalp, but also from one's clothing. When wearing clothing, sweat and oil from the wearer's skin are transferred to and absorbed by the clothing. Through auto-oxidation, bacterial action or enzymatic action, the skin lipids deposited on the clothing are oxidized to intermediate hydroperoxides, which further decompose to release malodorous aldehydes and other compounds. This can also cause body odor to be perceived by the wearer and / or people nearby the wearer.

[0008] Thus, there continues to be a need for compositions and methods for preventing, reducing or alleviating the olfactory perception of malodor resulting from the accumulation of malodorous aldehydes and ketones on the human body or other surfaces. Summary of the invention

[0009] The following aspects of the present disclosure are directed to addressing one or more of the above-mentioned problems.

[0010] In a first aspect, the present invention relates to a fragrance composition comprising:

[0011] a) an active component comprising at least one 1,3-dicarbonyl compound and optionally at least one basic compound, wherein the amount of 1,3-dicarbonyl compound is at least 10%, typically at least 20%, more typically at least 30% of the total weight of the composition; and

[0012] b) at least one ingredient selected from the group consisting of a fragrance carrier and a fragrance base, wherein the at least one ingredient is different from the at least one 1,3-dicarbonyl compound.

[0013] In a second aspect, the present disclosure relates to a perfumed consumer product comprising the fragrance composition described herein.

[0014] In a third aspect, the present disclosure relates to the use of a fragrance composition or a perfumed consumer product as described herein for preventing, reducing or alleviating malodorous aldehydes and ketones in the hair, scalp, skin, or any combination thereof of a subject.

[0015] In a fourth aspect, the present disclosure relates to the use of a fragrance composition or a perfumed consumer product as described herein for preventing, reducing or mitigating malodorous aldehydes and ketones on any inanimate surface, typically fabrics. DETAILED DESCRIPTION

[0016] As used herein, the terms "a", "an" or "the" mean "one or more" or "at least one", unless otherwise specified.

[0017] 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.

[0018] 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.

[0019] 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.

[0020] 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.

[0021] 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.

[0022] In a first aspect, the present invention relates to a fragrance composition comprising:

[0023] a) an active component comprising at least one 1,3-dicarbonyl compound and optionally at least one basic compound, wherein the amount of 1,3-dicarbonyl compound is at least 10%, typically at least 20%, more typically at least 30% of the total weight of the composition; and

[0024] b) at least one ingredient selected from the group consisting of a fragrance carrier and a fragrance base, wherein the at least one ingredient is different from the at least one 1,3-dicarbonyl compound.

[0025] Without being bound by a particular theory, the fragrance compositions described herein utilize a Knoevenagel condensation reaction, wherein at least one 1,3-dicarbonyl compound can form a carbon anion, which undergoes a nucleophilic addition reaction with the carbonyl carbon of a malodorous aldehyde or ketone, followed by elimination of H2O to form an unsaturated condensation product that is no longer malodorous or only slightly malodorous.

[0026] The 1,3-dicarbonyl compound is not particularly limited. However, in one embodiment, the at least one 1,3-dicarbonyl compound is a compound represented by formula (I),

[0027]

[0028] Wherein, R1 and R2 are each independently H, OH, C1-C 20 Alkyl, typically C1-C 10 Alkyl, more typically C1-C6 alkyl, or C1-C 20 Alkoxy, typically C1-C 10 Alkoxy, more typically C1-C6 alkoxy; or

[0029] R1 and R2 together form a 5- or 6-membered carbocyclic ring, optionally interrupted by one or more heteroatoms; wherein R1 and R2 may optionally contain one or more substituents selected from the group consisting of halogen, aryl, alkoxy, CN, NO2, OH, SH, SCH3, NH2, COOH and CONH2.

[0030] As used herein, the term "Cx-Cy" refers to an organic group wherein x and y are both integers, indicating that the group may contain from x to y carbon atoms per group.

[0031] As used herein, the term "alkyl" refers to a monovalent straight-chain or branched saturated hydrocarbon group, more typically a monovalent straight-chain or branched saturated (C1-C 40 ) hydrocarbon radicals, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, hexyl, 2-ethylhexyl, octyl, decyl, lauryl, hexadecyl, octadecyl, eicosyl, docosyl, triacontyl and tetracontyl.

[0032] As used herein, the term "alkoxy" refers to a monovalent group represented as -O-alkyl, wherein alkyl is as defined herein. Examples of alkoxy include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, and tert-butoxy.

[0033] As used herein, the term "aryl" refers to a monovalent unsaturated hydrocarbon group containing one or more six-membered carbocyclic rings, wherein the unsaturation can be represented by three conjugated double bonds. Aryl includes monocyclic aryl and polycyclic aryl. Polycyclic aryl refers to a monovalent unsaturated hydrocarbon group containing more than one six-membered carbocyclic ring, wherein the unsaturation can be represented by three conjugated double bonds, wherein adjacent rings can be interconnected or fused together by one or more bonds or divalent bridging groups. Examples of aryl include, but are not limited to, phenyl, anthracenyl, naphthyl, phenanthrenyl, fluorenyl and pyrenyl.

[0034] Any substituent or group described herein may be optionally substituted with one or more identical or different substituents described herein on one or more carbon atoms. For example, an alkyl group may be further substituted with an aryl group or another alkyl group. Any substituent or group described herein may also be optionally substituted with one or more substituents selected from the group consisting of halogen (e.g., F, Cl, Br, and I), nitro (NO2), cyano (CN), hydroxyl (OH), sulfenyl (SH), methylthio (SCH3), amino (NH2), carboxyl (COOH), amide (CONH), etc. on one or more carbon atoms.

[0035] Exemplary 1,3-dicarbonyl compounds include, but are not limited to, malonic acid, malonic esters, acetoacetic acid, acetoacetic esters, Meldrum's acid, and the like.

[0036] In one embodiment, R1 and R2 are each independently C1-C6 alkyl or C1-C6 alkoxy.

[0037] In another embodiment, R1 is C1-C6 alkyl, typically ethyl, and R2 is C1-C6 alkoxy, typically ethoxy.

[0038] In yet another embodiment, the at least one 1,3-dicarbonyl compound is ethyl acetoacetate.

[0039] Generally speaking, the amount of 1,3-dicarbonyl compound in the fragrance composition is at least 10% by weight, typically at least 20%, more typically at least 30% by weight of the total weight of the composition.

[0040] In one embodiment, the at least one 1,3-dicarbonyl compound is present in an amount of 10% to 99% by weight, typically 20% to 99%, more typically 30% to 99%, and even more typically 50% to 99% by weight of the total weight of the composition.

[0041] The fragrance composition may optionally include at least one basic compound. Without being bound by theory, the at least one basic compound activates the acidic hydrogen atoms on the at least one 1,3-dicarbonyl compound to promote the formation of a carbanion, which undergoes nucleophilic addition to the carbonyl carbon of the malodorous aldehyde or ketone. Although some malodor reduction still occurs in the absence of a basic compound, it is less efficient. Therefore, in one embodiment, the fragrance composition includes both the at least one 1,3-dicarbonyl compound and the at least one basic compound.

[0042] The basic compound can be any compound that can deprotonate the acidic proton between the two carbonyl groups of the 1,3-dicarbonyl compound, thereby forming a stable carbon anion that can react with the malodorous aldehyde and / or ketone. Suitable basic compounds include, but are not limited to, hydroxides, carbonates, bicarbonates, phosphates, dihydrogen phosphates, monohydrogen phosphates, sulfates, hydrogen sulfates of alkali metals and alkaline earth metals; and amines.

[0043] The amount of the at least one basic compound is not particularly limited. In one embodiment, the amount of the basic compound is 0% to 50% by weight, typically 0.1% to 40%, more typically 0.5% to 30%, more typically 1% to 10%, based on the total weight of the fragrance composition.

[0044] In one embodiment, the at least one basic compound is a compound represented by formula (II), or a salt thereof,

[0045]

[0046] Wherein R3 is H, aryl, C1-C 20 Alkyl, typically C1-C 10 Alkyl, more typically C1-C6 alkyl, or CHR a COOR b , where R a and R b Each independently is H, C1-C 20 Alkyl, typically C1-C 10 Alkyl, more typically C1-C6 alkyl;

[0047] R4 and R5 are each independently H, aryl, C1-C 20 Alkyl, typically C1-C 10 Alkyl, more typically C1-C6 alkyl, or CHR a COOR b , where R a and R b Each independently is H, C1-C 20 Alkyl, typically C1-C 10 Alkyl, more typically C1-C6 alkyl; or

[0048] R4 and R5 together form a 5- or 6-membered carbocyclic ring, optionally interrupted by one or more heteroatoms;

[0049] wherein R3, R4 and R5 may optionally contain one or more substituents selected from the group consisting of halogen, aryl, alkoxy, CN, NO2, OH, SH, SCH3, NH2, COOH and CONH2.

[0050] Exemplary compounds represented by formula (II) include, but are not limited to, primary, secondary and tertiary amines, carbocyclic amines, amino acids, and the like.

[0051] Although the pKa of the basic compound is not particularly limited, the pKa can be considered to optimize the catalytic efficiency. In one embodiment, the pKa of the at least one basic compound is>9.

[0052] In one embodiment, the at least one basic compound is selected from the group consisting of pyrrolidine, ethanolamine, diethylamine, triethylamine, tributylamine, piperidine, alanine, proline, dimethylalkylamine, diethanolalkylamine and mixtures thereof. One or more basic compounds can be used in any combination. As used herein, dimethylalkylamine refers to a compound of formula (II), wherein R4 and R5 are both methyl, and R3 is C8-C 16 Alkyl, such as C8, C 10 , C 12 , C 14 or C 16 Similarly, diethanolalkylamine refers to a compound represented by formula (II), wherein R4 and R5 are both ethyl substituted with OH, and R3 is C8-C 16 Alkyl, such as C8, C 10 , C 12 , C 14 or C 16 alkyl.

[0053] In some embodiments, the at least one basic compound is selected from the group consisting of ethanolamine, diethylamine, tributylamine, piperidine, alanine, proline, dimethylalkylamines, diethanolalkylamines, and mixtures thereof.

[0054] The weight ratio of the at least one 1,3-dicarbonyl compound to the at least one basic compound is not particularly limited. In one embodiment, the weight ratio of the at least one 1,3-dicarbonyl compound to the at least one basic compound is 50:50 to 99:1, typically 80:10 to 95:5, and more typically 85:15 to 95:5.

[0055] In some embodiments, the weight ratio of the at least one 1,3-dicarbonyl compound to the at least one basic compound is from 60:40 to 99:1, typically from 85:15 to 98:2.

[0056] The composition according to the present invention comprises at least one ingredient selected from the group consisting of a perfume carrier and a perfume base, wherein the at least one ingredient is different from the at least one 1,3-dicarbonyl compound.

[0057] As used herein, "fragrance carrier" refers to a material that is virtually neutral from a fragrance point of view, i.e., does not significantly change the sensory properties of the fragrance ingredients. The carrier can be liquid or solid. Exemplary liquid carriers include, but are not limited to, emulsifying systems, i.e., solvents and surfactant systems, or solvents commonly used in the fragrance industry. A detailed description of the properties and types of solvents commonly used in the fragrance industry is not exhaustive. However, suitable solvents include, but are not limited to, glycols, such as propylene glycol or butylene glycol; glycerol; dipropylene glycol and its monoethers, 1,2,3-propanetriol triacetate, dimethyl glutarate, dimethyl adipate, 1,3-diacetoxyprop-2-yl acetate, diethyl phthalate, isopropyl myristate, rosin resins (e.g., available from Eastman ), benzyl benzoate, benzyl alcohol, 2-(2-ethoxyethoxy)-1-ethanol, triethyl citrate, and mixtures thereof; and naturally derived solvents such as glycerol and vegetable oils, including palm oil, sunflower oil, linseed oil, and mixtures thereof.

[0058] Solid carrier refers to a material to which a fragrance composition or certain components of a fragrance composition can be chemically or physically bound. Generally speaking, such solid carriers are used to stabilize the composition, or to control the evaporation rate of the composition or certain components. Solid carriers are currently used in the art, and those skilled in the art know how to achieve the desired effect. However, as non-limiting examples of solid carriers, absorbent glues or polymers or inorganic materials can be cited, such as porous polymers, cyclodextrins, dextrins, maltodextrins, wood-based materials, organic or inorganic gels, clays, gypsum, talc or zeolites.

[0059] 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, methyl Cellulose, hydroxyethylcellulose, ethylcellulose, propylcellulose, 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 alcohol or fatty acid and mixtures thereof.

[0060] 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.

[0061] 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.

[0062] 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.

[0063] Other resins are obtained by mixing a polyol such as glycerol with a polyisocyanate such as 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 and trimethylolpropane (known under the trade name Known sources: those produced by polycondensation of Mitsui Chemicals), of which the trimer of xylylene diisocyanate with trimethylolpropane and the biuret of hexamethylene diisocyanate are preferred.

[0064] 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.

[0065] A perfume base is a composition comprising at least one perfuming co-ingredient. According to the present disclosure, the perfuming co-ingredient is different from the at least one 1,3-dicarbonyl compound and is a compound that imparts a hedonic effect, i.e., is primarily used to impart or modulate an odor. 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 odor of the composition in an active or pleasant manner, rather than merely having an odor. In addition to modifying or imparting an odor, a perfuming co-ingredient may impart additional benefits, such as persistence, burst, malodor counteracting, antimicrobial action, antiviral action, microbial stability or pest control.

[0066] The nature and types of perfuming co-ingredients present in the base do not warrant a more detailed description here, which in any case cannot be exhaustive, and a person skilled in the art will be able to choose them according to his general knowledge and according to the intended use or application and the desired organoleptic effect. In general, these perfuming co-ingredients belong to different chemical classes, such as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogen- or sulfur-containing heterocyclic compounds and essential oils, and may be of natural or synthetic origin. Suitable perfuming co-ingredients include compounds known to release various types of perfuming compounds in a controlled manner, generally called properfumes or profragrances.

[0067] The perfume base according to the present disclosure is not limited to the above-mentioned perfuming co-ingredients, and many other suitable auxiliary ingredients are listed in references known to those skilled in the art, for example, S. Arctander's book Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA or its updated versions, which are incorporated herein by reference.

[0068] For compositions comprising both a fragrance carrier and a fragrance base, other suitable fragrance carriers, in addition to those specified above, may also be ethanol, water / ethanol mixtures, limonene or other terpenes, isoparaffins, such as those sold under the trademark Those known in the art (available from Exxon Chemical), or glycol ethers and glycol ether esters, such as those sold under the trademark Those known as castor oils (available from Dow Chemical Company), or hydrogenated castor oils, such as those sold under the trademark RH 40 is known among those (available from BASF).

[0069] The fragrance composition may optionally comprise at least one fragrance adjuvant.

[0070] 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.

[0071] Exemplary perfume 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, fixatives, insect repellents, ointments, vitamins, and mixtures thereof.

[0072] A fixative, also called a "fixative", is an agent that has the ability to affect the way an observer or user perceives the odor of a composition into which it is incorporated, particularly the rate of evaporation and the intensity, over time, compared to the same perception without the fixative. In particular, the fixative allows the perception of its fragrance to be prolonged. Suitable fixatives include, but are not limited to: 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, hyaluronate disaccharide sodium salt, 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, hexadecyl nonanoate, fragrance precursors, cyclodextrins, encapsulating agents, and any combination thereof.

[0073] The fragrance composition of the present disclosure can be prepared according to any method known to those of ordinary skill in the art. Those of ordinary skill are fully capable of designing the best formula to achieve the desired effect by applying standard knowledge and concepts known to those of ordinary skill and utilizing conventional optimization methods to mix the above components to obtain the desired fragrance composition.

[0074] In a second aspect, the present disclosure relates to a perfumed consumer product comprising the fragrance composition described herein.

[0075] The perfumed consumer product may be:

[0076] - perfumes, such as fine perfume, splash perfume, eau de toilette, eau de perfum, cologne, shaving lotion or aftershave;

[0077] - fabric care products, such as liquid or solid detergents, detergent tablets, detergent bars, detergent pastes, detergent capsules, liquid fabric softeners, fabric softener tablets, fabric fragrance enhancers, laundry pretreaters, fabric refreshers, ironing water or laundry bleach,

[0078] - hair care products, such as shampoos, hair conditioners such as rinse-off conditioners or leave-in conditioners; hair creams, hair oils, hair styling products such as hair sprays, mousses or gels; hair dyes or hair perming products;

[0079] - skin care products, such as face creams, body-or-face creams, facial lotions, shaving products (which may be in the form of foam, cream, gel or oil), body and / or hand products (which may be in the form of lotions, creams, gels or oils), skin tightening products, depilatories, talcum powders, foot care creams or lotions, baby wipes, cleansing wipes, moisturizing wipes, tanning products or sunscreen products (which may be in the form of sprays, lotions, creams or oils), foot / hand care products, make-up, vanishing creams;

[0080] - skin cleansing products such as soap bars, shower gels, liquid hand soap, bath foams, mousses, oils or gels for the shower or bath; body scrubs, hygiene products or intimate cleansing products;

[0081] - body deodorant (deodorant) or antiperspirant products, such as body deodorant sprays, roll-ons, deodorant sticks, deodorant creams, antiperspirant sprays, antiperspirant sticks, roll-ons, antiperspirant sticks or antiperspirant creams;

[0082] -Nail products;

[0083] - Home care products such as disinfectants, mildew removers, furniture care products, hard surface wipes, dishwashing detergents, hard surface cleaners, leather care products or car care products.

[0084] In one embodiment, the fragrance consumer product is a hair care product selected from the group consisting of shampoo, rinse-off conditioner, and leave-in conditioner.

[0085] In another embodiment, the fragrance consumer product is a skin care and / or skin cleansing product selected from the group consisting of a body cream, a face cream, a dual purpose body or face cream, a shower gel, a soap bar, and a body scrub.

[0086] The amount of the fragrance composition in the perfumed consumer product is not particularly limited, but in one embodiment, the amount of the fragrance composition is 0.25% to 5%, typically 0.50% to 2%, more typically 0.75% to 1.5% by weight of the total amount of the perfumed consumer product.

[0087] The amount of the at least one 1,3-dicarbonyl compound in the perfumed consumer product is not particularly limited. In one embodiment, the amount of the at least one 1,3-dicarbonyl compound is from 0.01% to 4%, typically from 0.05% to 2%, more typically from 0.1% to 1.5% by weight of the total amount of the perfumed consumer product.

[0088] The amount of the at least one basic compound in the perfumed consumer product is not particularly limited, but in one embodiment, the amount of the at least one basic compound is from 0.0001% to 2% by weight of the total amount of the perfumed consumer product, typically from 0.0025% to 1%, more typically from 0.0025% to 0.5%, more typically from 0.02% to 0.3%.

[0089] In a third aspect, the present disclosure relates to the use of a fragrance composition or a perfumed consumer product as described herein for preventing, reducing or alleviating malodorous aldehydes and ketones in the hair, scalp, skin, or any combination thereof of a subject.

[0090] The use of the fragrance composition or perfumed consumer product described herein for preventing, reducing or alleviating malodorous aldehydes and ketones in the hair, scalp, skin or any combination thereof of a subject is achieved by using methods known to those skilled in the art. In one suitable method, the method comprises applying the fragrance composition or perfumed consumer product described herein to the hair, scalp, skin or any combination thereof of a subject (typically a human). In one embodiment, the method comprises massaging the fragrance composition or perfumed consumer product described herein onto the hair or scalp of a subject.

[0091] In a fourth aspect, the present disclosure relates to the use of a fragrance composition or a perfumed consumer product as described herein for preventing, reducing or mitigating malodorous aldehydes and ketones on any inanimate surface.

[0092] Malodors may originate from inanimate surfaces such as fabrics and textiles used for clothing, bedding, upholstery, etc., due to the transfer of sweat, lipids and / or oils from the user's skin. Sweat, lipids and / or oils deposited on surfaces may be oxidized to intermediate hydroperoxides by auto-oxidation, bacterial action or enzymatic action, which may further decompose to release malodorous aldehydes and other compounds. In a suitable method for reducing malodorous aldehydes and ketones on any inanimate surface, the method comprises contacting the fragrance composition or perfumed consumer product described herein with the inanimate surface.

[0093] In certain forms, the degradation of lipid hydroperoxides on the skin (particularly in the elderly) releases malodorous aldehydes, primarily the compound 2-nonenal. Thus, in one embodiment of the above use, the malodorous aldehydes comprise 2-nonenal.

[0094] The compositions, products, uses and methods according to the present disclosure are further illustrated by the following non-limiting examples.

[0095] Example 1. Analysis of the reduction of aldehydes and ketones in scalp malodor

[0096] In this example, a scalp malodor restoration product is used to represent scalp malodor. The components of the scalp malodor restoration product are shown in Table 1.

[0097] Table 1.

[0098] Element Amount (weight %) Benzaldehyde 1.30 Aldehyde C9 8.00 Geranyl acetone HLR 9.00 Methyl Heptenone 13.50 The balance together with other ingredients reaches 100 68.20

[0099] A mixture of a scalp malodor restoring substance, ethyl acetoacetate and various basic compounds was prepared according to the following Table 2. The amount of each component is expressed in parts by weight.

[0100] Table 2.

[0101] Components C1 A B C D E F G H l Scalp odor 100 100 100 100 100 100 100 100 100 100 Ethyl acetoacetate 90 90 90 90 90 Ethanolamine 10 10 Proline 10 10 Diethylamine 10 10 Tributylamine 10 10 DIPG 10 90 0 90 0 90 0 90 0

[0102] Each mixture was stirred until homogeneous and allowed to stand at room temperature for 2 hours. When the reaction was complete, the color changed from reddish orange to light yellow.

[0103] The scalp malodor restoration product alone (Comparative Example C1) and mixtures A to I were analyzed by GC-MS. 1 g of the product was placed in a 20 ml solid phase microextraction (SPME) vial and the degradation of aldehydes and ketones was measured from the headspace above the mixture.

[0104] The analysis was performed at room temperature using GC-MS (GC Agilent 5975B) and the SPME method (1 g sample / column DB-1ms, length 30 m×ID 25 mm×film thickness 0.25 μm / helium flow 1.2 ml / min, pressure 80.5 Kpa / split 20 / 60°C for 2 min, 7°C / min until 250°C).

[0105] The amounts of scalp malodor components remaining in mixtures A to I are shown in Table 3a and Table 3b below and are expressed in weight % relative to the starting scalp malodor restoration weight.

[0106] Table 3a.

[0107] Scalp malodor components C1 A B C D Benzaldehyde 1.3 1.16 0.009 0.006 0.87 Aldehyde C9 8.00 2.72 0.16 0.00 1.12 Methyl Heptenone 13.50 13.50 10.95 6.05 11.33 Geranyl acetone 9.00 8.07 4.12 3.69 7.26

[0108] Table 3b.

[0109] Scalp malodor components E F G H I Benzaldehyde 0.28 0.69 0.030 0.84 0.71 Aldehyde C9 0.055 1.37 0.0072 6.07 0.29 Methyl Heptenone 8.27 10.65 10.55 10.76 8.68 Geranyl acetone 4.84 7.26 6.04 7.66 4.27

[0110] Although the results of the analytical GC-MS confirmed that sample A containing only ethyl acetoacetate (without basic compounds) and samples containing only basic compounds (B, D, F, H) could already reduce the content of aldehydes and ketones present in scalp malodor, with the greatest impact on aldehyde C9, the combination of ethyl acetoacetate and basic compounds achieved significantly better reductions in both aldehydes and ketones, with the best results being obtained with ethanolamine as the basic compound. In this reaction, the basic compound enhances the reaction efficiency between the active substance and the malodorous aldehydes and ketones.

[0111] Example 2. Olfactory Assessment

[0112] Olfactory evaluation was performed on samples prepared according to Example 1. An evaluation scale of 1 to 7 was used (1 = no malodor / / 7 = very strong malodor). The olfactory evaluation results are reported in Table 4 below.

[0113] Table 4.

[0114] sample Odor intensity (1-7) C1 7 A 6 B 5 C 2 D 5 E 2.5 F 5 G 2.5 H 5 I 3

[0115] It was demonstrated that ethyl acetoacetate (A) alone or basic compounds (B, D, F, H) alone can reduce scalp malodor. However, the combination of ethyl acetoacetate and basic compounds was much more effective (C vs. A and B and C1, E vs. A and D and C1, G vs. A and F and C1, I vs. A and H and C1).

[0116] Therefore, the results of the analysis in Table 3 are consistent with the olfactory evaluation summarized in Table 4 .

[0117] Example 3. Efficiency of Scalp Malodor Reduction

[0118] Mixtures of ethyl acetoacetate and ethanolamine at different concentrations were tested to determine the best effect in reducing scalp malodor. A variety of mixtures of scalp malodor restorers (Table 1), ethyl acetoacetate and ethanolamine were prepared, wherein the amount of each component varied. The mixture was stirred until uniform and allowed to stand at room temperature for 2 hours. After the reaction was complete, the color changed from reddish orange to light yellow. The samples and the amounts of the components are summarized in Table 5 below, expressed in parts by weight.

[0119] Table 5.

[0120] Components C1 C J K L M N O P Q R S Scalp odor 100 100 100 100 100 100 100 100 100 100 100 100 Ethyl acetoacetate 0 90 90 90 90 80 50 50 30 30 30 10 Ethanolamine 0 10 5 1 0.5 10 10 2 10 5 2 10 DIPG 0 0 5 9 9.5 10 40 48 60 65 68 80

[0121] Samples J-S were analyzed by GC-MS according to the method described in Example 1. The results are summarized in Tables 6a and 6b below. The amount of scalp malodor components remaining in mixtures J-S is expressed in weight % relative to the weight of the starting scalp malodor restoration.

[0122] Table 6a.

[0123] Scalp malodor components C1 C J K L M Benzaldehyde 1.3 0.006 0.0065 0.53 0.56 0.0062 Aldehyde C9 8 0.00 0.015 0.47 0.54 0.013 Methyl Heptenone 13.50 6.05 6.75 8.41 8.82 6.74 Geranyl acetone 9 3.69 4.63 5.19 5.27 4.54

[0124] Table 6b.

[0125] Scalp malodor components N O P Q R S Benzaldehyde 0.0072 0.052 0.0074 0.060 0.20 0.067 Aldehyde C9 0.013 0.13 0.057 0.32 0.43 0.022 Methyl Heptenone 9.12 9.27 9.22 9.40 9.74 12.96 Geranyl acetone 6.41 7.01 7.30 8.43 8.50 8.50

[0126] It was observed that a reduction in the dose of the active compound ethyl acetoacetate or the basic compound ethanolamine resulted in a reduction in malodorous aldehydes and ketones on the scalp.

[0127] Comparing the results of 0.9% vs. 0.1% ethyl acetoacetate in the final application, it was found that 0.1% ethyl acetoacetate reduced the concentrations of malodorous aldehydes and ketones less. A reduction in aldehydes and ketones in scalp malodor was still noted, but to a lesser extent. The concentration of residual aldehydes was almost unchanged, but the concentration of residual ketones increased significantly (sample C vs. S).

[0128] Comparing the results of 0.1% vs. 0.005% ethanolamine in the final application, it was found that 0.005% ethanolamine had less effect on the reduction of aldehyde and ketone concentrations. The reduction of aldehydes and ketones in scalp malodor was still significant, but to a lesser extent, especially the reduction of benzaldehyde. The concentration of residual aldehyde C9 was almost unchanged, the concentration of residual ketones increased slightly, and the concentration of residual benzaldehyde increased significantly (sample C vs. L).

[0129] Example 4. Leave-on Conditioner

[0130] Leave-on conditioner compositions were prepared using the components and amounts summarized in Table 7 below.

[0131] Table 7.

[0132]

[0133] 1) EDTA B powder, source: BASF

[0134] 2) JAGUAR C14 S, source: Lubrizol

[0135] 3) Light liquid paraffin, source: Acros Organics

[0136] 4) GENAMIN CTAC, source: Clariant

[0137] 5) DEHYQUART C 4046, source: BASF

[0138] 6) Glycerin 85%, source: Brenntag

[0139] 7) XIAMETER MEM-949 Cationic Emulsion, Source: Xiameter

[0140] 8) KATHON CG, source: Sigma-Aldrich

[0141] Dissolve tetrasodium EDTA in water and then add guar gum while stirring until completely dispersed. Add paraffin and stir the mixture until slightly creamy. Add Genamin CTAC and stir the mixture until homogeneous. Then heat the mixture to 75°C. While stirring, add phase C and then cool the mixture to 40°C. Add phase D to the container and stir until a homogeneous mixture is obtained. The mixture begins to emulsify. While the mixture is emulsifying, add phases E and F. The emulsification process continues until a cream is obtained. Cool the mixture to 35°C and add the preservative. Keep emulsifying until the appropriate viscosity of the product is reached. A mixture of ethyl acetoacetate / ethanolamine (90 / 10) was prepared and used in a leave-on conditioner at a ratio of 0.50%.

[0142] 0.1 g of this leave-in conditioner was applied to a hair sample (0.5 g / 8 cm x 1 cm) and gently massaged with two fingers until the product was fully absorbed by the hair. The same hair sample was then contaminated with 0.050 g of a scalp malodor restorer (Table 1) diluted to 1% with isopropyl myristate. The hair sample was gently massaged with two fingers until the product was fully absorbed by the hair and then cut into 3 pieces and placed on a 20 ml SPME vial. The vial containing the hair sample was sealed and left at room temperature for 24 hours to allow the reaction to occur and then analyzed by GC-MS according to the procedure described in Example 1. This procedure was performed on 3 hair samples and the average results are reported in Table 8. The amount of scalp malodor components remaining on the hair sample is expressed as weight % relative to the weight of the starting scalp malodor restorer.

[0143] Table 8.

[0144] Components Scalp odor restorer only Leave-in conditioner Benzaldehyde 1.30 0.90 Aldehyde C9 8.00 3.69 Methyl Heptenone 13.50 7.54 Geranyl acetone 9.00 5.75

[0145] The measurement results summarized in Table 8 show that a leave-in conditioner containing 0.45% ethyl acetoacetate and 0.05% ethanolamine, when deposited on the hair, has a very good effect on the reduction of aldehydes and ketones present in the scalp malodor restoration. The measurement results show that the concentration of aldehydes and ketones is reduced by nearly half. In addition, among the aldehydes and ketones in the scalp malodor restoration, the aldehyde C9 and methyl heptenone have the most significant reduction effect.

[0146] Example 5. Rinse-off Conditioner

[0147] Rinse-off hair conditioner compositions were prepared using the components and amounts summarized in Table 9 below.

[0148] Table 9.

[0149]

[0150] 1) Genamin KDMP, Clariant

[0151] 2) Tylose H10 Y G4, Shin Etsu

[0152] 3) Lanette O, BASF

[0153] 4) Arlacel 165, Croda

[0154] 5)Incroquat Behenyl TMS-50-PA-(MH),Croda

[0155] 6) Brij S20, Croda

[0156] 7)Xiameter MEM-949,Dow Corning

[0157] 8) Alfa Aesar

[0158] Mix the ingredients of phase A until a homogeneous mixture is obtained. Dissolve the Tylose completely. Then heat the mixture to 70-75°C. Mix the ingredients of phase B and melt at 70-75°C. Then add the ingredients of phase B to phase A and stir well, continuing to mix until cooled to 60°C. Then add the ingredients of phase C while stirring and continue mixing until the mixture cools to 40°C. Adjust the pH with citric acid solution until the pH is 3.5-4.0. A mixture of ethyl acetoacetate / ethanolamine (90 / 10) was prepared and used in a rinse-off conditioner at a ratio of 0.50%.

[0159] 0.1 g of this rinse-off conditioner was applied to a hair sample (0.5 g / 8 cm x 1 cm) and gently massaged with two fingers until the product was fully absorbed by the hair. It was then immersed in a beaker containing 200 mL of warm water for 3 times (3 dips, 3 withdrawals). It was then immersed again in the same beaker, moving slowly back and forth 3 times in each direction. The same rinsing procedure was repeated with a second beaker containing 200 mL of warm water. Excess water was squeezed out of the hair sample using two fingers. The same hair sample was contaminated with 0.050 g of scalp malodor restorer diluted to 1% with isopropyl myristate (Table 1). The hair sample was gently massaged with two fingers until the product was fully absorbed by the hair and then cut into 3 pieces and placed on a 20 mL SPME vial. The vial containing the hair sample was closed and left at room temperature for 24 hours to allow the reaction to occur and then analyzed by GC-MS according to the procedure described in Example 1. This procedure was performed on 3 hair samples and the average results are reported in Table 10. The amount of scalp malodor components remaining on the hair sample is expressed as % by weight relative to the weight of the starting scalp malodor restoration material.

[0160] Table 10.

[0161] Components Scalp odor restorer only Rinse-off conditioner Benzaldehyde 1.3 0.93 Aldehyde C9 8 4.67 Methyl Heptenone 13.5 8.21 Geranyl acetone 9 7.08

[0162] The measurements summarized in Table 10 show that a rinse-off conditioner containing 0.45% ethyl acetoacetate and 0.05% ethanolamine, when deposited on the hair, has a positive effect on the reduction of aldehydes and ketones present in the scalp malodor restoration. The measurements show that the concentration of aldehydes and ketones was reduced by nearly one third. Furthermore, among the aldehydes and ketones in the scalp malodor restoration, the reduction effect was most significant for aldehyde C9 and methyl heptenone.

[0163] Example 6. Shampoo composition

[0164] Pearlescent shampoo compositions were prepared using the components and amounts summarized in Table 11 below.

[0165] Table 11.

[0166]

[0167] 1) EDETA B powder, BASF

[0168] 2) Jaguar C14 S, Rhodia

[0169] 3) Ucare Polymer JR-400, Noveon

[0170] 4)Sulfetal LA BE,Zschimmer&Schwarz

[0171] 5)Zetesol LA,Zschimmer&Schwarz

[0172] 6) Tego Betain F 50, Evonik

[0173] 7)Xiameter MEM-1691,Dow Corning

[0174] 8) Lanette 16, BASF

[0175] 9) Comperlan 100, Cognis

[0176] 10) Cutina AGS, Cognis

[0177] 11) Kathon CG, Rohm & Haas

[0178] 12) D-Panthenol, Roche

[0179] A premix of guar hydroxypropyltrimonium chloride and polyquaternium-10 was added to water and tetrasodium EDTA while mixing. When the mixture was homogeneous, NaOH was added. Then, the C phase ingredients were added. And the mixture was heated to 75°C. The D phase ingredients were added and mixed until homogeneous. The heating was stopped and the temperature of the mixture was lowered to room temperature. At 45°C, the E phase ingredients were added while mixing, and the final viscosity was adjusted with 25% NaCl solution and the pH was adjusted to 5.5-6 with 10% NaOH solution. A mixture of ethyl acetoacetate / ethanolamine (90 / 10) was prepared and applied in a pearlescent shampoo at a ratio of 0.50%.

[0180] 0.1 g of this shampoo was applied to a hair sample (0.5 g / 8 cm x 1 cm) and the hair sample was gently rinsed with two fingers until the product was well lathered. It was then immersed in a beaker containing 200 mL of warm water for 3 times (3 immersions, 3 withdrawals). It was then immersed again in the same beaker, moving slowly back and forth 3 times in each direction. The same rinsing procedure was repeated with a second beaker containing 200 mL of warm water. Excess water was squeezed out of the hair sample with two fingers. The same hair sample was contaminated with 0.050 g of scalp malodor restorer diluted to 1% with isopropyl myristate (Table 1). The hair sample was gently massaged with two fingers until the product was well absorbed by the hair, and then it was cut into 3 pieces and placed on a 20 mL SPME vial. The vial containing the hair sample was closed and left at room temperature for 24 hours to allow the reaction to occur, and then analyzed by GC-MS according to the procedure described in Example 1. This procedure was performed on 3 hair samples and the average results are reported in Table 12 below. The amount of scalp malodor components remaining on the hair sample is expressed as % by weight relative to the weight of the starting scalp malodor restoration material.

[0181] Table 12.

[0182] Components Scalp odor restorer only Shampoo Benzaldehyde 1.3 1.16 Aldehyde C9 8 7.15 Methyl Heptenone 13.5 11.01 Geranyl acetone 9 8.86

[0183] The measurements summarized in Table 12 show that when a shampoo containing 0.45% ethyl acetoacetate and 0.05% ethanolamine is deposited on the hair, it has a positive effect, albeit a small effect, on the reduction of aldehydes and ketones present in the scalp malodor reconstituted product. The measurements show that the concentrations of aldehydes and ketones were reduced by less than 20%. Furthermore, among the aldehydes and ketones present in the scalp malodor reconstituted product, the reduction effect was most significant for aldehyde C9 and methyl heptenone.

[0184] Example 7. Olfactory Assessment

[0185] Ethyl acetoacetate / ethanolamine (90 / 10) mixture was added to hair care applications at different concentrations (0.1 wt%, 0.3 wt%, and 0.5 wt%) to form T-AB samples.

[0186] Hair samples (10 g / 20 cm x 7 cm) were pre-treated with 1 g of each sample T to AB and then contaminated with 0.50 g of scalp malodor reconstitution diluted to 1% with isopropyl myristate (Table 1) using the same protocol as described in Examples 4, 5 and 6. The hair samples were then olfactorily evaluated by a panel of 5 people. An evaluation scale of 1 to 7 was used (1 = no malodor / / 7 = very strong malodor). The results of the olfactory evaluation are reported in Table 13 below.

[0187] Table 13.

[0188]

[0189] As shown in Table 13, different hair care applications containing a mixture of ethyl acetoacetate and ethanolamine can reduce scalp malodor. The best results for scalp malodor are achieved when the hair is pre-treated with a leave-in conditioner containing a mixture of ethyl acetoacetate and ethanolamine, followed by a rinse-off conditioner and finally a shampoo.

[0190] The use of ethyl acetoacetate at a concentration of 0.45% and ethanolamine at a concentration of 0.05% in a leave-on conditioner (Sample V) showed the best effect against malodorous aldehydes and ketones from the scalp. The malodor reduction was clearly perceived olfactorily, with a difference of 5 between the reference scalp malodor intensity and Sample V.

[0191] Example 8. Fragrance composition

[0192] Two fragrances were prepared, one fragrance (Fragrance A) did not contain any 1,3-dicarbonyl compounds or basic compounds, and the other fragrance (Fragrance B) contained 51% ethyl acetoacetate and 2% ethanolamine. In order to avoid side reactions between ethyl acetoacetate and / or ethanolamine and other ingredients in the fragrance, the fragrance was designed to contain no aldehydes (0.00%) and very low ketone content (1.6%). The fragrance composition is shown in Table 14 below.

[0193] Table 14.

[0194]

[0195] The scalp malodor restoration material (Table 1) was mixed with fragrance A at a ratio of 1:1 and with fragrance B at a ratio of 1:0.47 to obtain samples AC and AD.

[0196] Based on the composition of Fragrance A and Fragrance B, sample AC contains neither 1,3-dicarbonyl compounds nor basic compounds, while sample AD contains ethyl acetoacetate and ethanolamine. These samples were stirred until homogeneous and allowed to stand at room temperature for 2 hours. After the reaction was completed, a color change from reddish orange to light yellow was observed. 1 g of each sample was weighed in a 20 ml SPME vial, and the degradation of aldehydes and ketones present in scalp malodor was measured from the head space by GC-MS using the analytical method described previously. The analytical results are shown in Table 15. The amount of scalp malodor components remaining in samples AC and AD is expressed in weight % relative to the weight of the starting scalp malodor restoration.

[0197] Table 15.

[0198] Components Scalp odor restorer only Sample AC Sample AD Benzaldehyde 1.3 0.82 0.56 Aldehyde C9 8 5.88 0.07 Methyl Heptenone 13.50 10.01 8.17 Geranyl acetone 9 7.89 4.19

[0199] The measurements summarized in Table 15 show that a fragrance containing 51% ethyl acetoacetate and 2% ethanolamine significantly reduced aldehydes and ketones in scalp malodor.

[0200] Example 9. Olfactory Evaluation of Hair Samples

[0201] Fragrance A and Fragrance B were used in different hair care applications at the same dosage to form samples AC to AD (Table 16). Hair samples (10 g / 20 cm×7 cm) were pre-treated with 1 g of samples AC to AD and then contaminated with 0.50 g of scalp malodor restoration diluted to 1% with isopropyl myristate (Table 1) using the same protocol described in Example 7. The hair samples (10 g / 20 cm×7 cm) were subjected to olfactory evaluation by a panel of 5 experts. An evaluation scale of 1 to 7 was used (1=no malodor / / 7=very strong malodor). The results of the olfactory evaluation are reported in Table 16.

[0202] Table 16.

[0203]

[0204] It was verified that after using the hair care application containing Fragrance A (inactive ingredient), the perception of scalp malodor was reduced, but after using the hair care application containing Fragrance B (active ingredient), the effect on scalp malodor was much better.

[0205] Best results for scalp malodor are achieved when hair is pre-treated with a leave-in conditioner containing Fragrance B, followed by a rinse-off conditioner and shampoo.

[0206] Using 0.5% of Fragrance B in a leave-on conditioner showed the best results against malodorous aldehydes and ketones from the scalp (Samples AC).

[0207] The malodor was obviously reduced in the sense of smell, and the difference between the scalp malodor intensity reference value and samples AC was 6 (after 6 hours).

[0208] Example 10. Analysis of the reduction of trans-2-nonenal from "senior malodor"

[0209] A mixture of trans-2-nonenal, ethyl acetoacetate and ethanolamine ("Product A") was prepared (by weight, 100 parts of trans-2-nonenal, 90 parts of ethyl acetoacetate, and 10 parts of ethanolamine). The mixture was stirred until uniform and allowed to stand at room temperature for 2 hours. After the reaction was completed, the color changed from reddish orange to light yellow.

[0210] The "old man's malodor" reconstituted product (trans-2-nonenal) and its mixture with ethyl acetoacetate and ethanolamine were analyzed by GC-MS. 1 g of the product was placed in a 20 ml SPME vial and the degradation of trans-2-nonenal was measured from the headspace above the mixture.

[0211] The analysis was performed at room temperature using GC-MS (GC Agilent 5975B) and the SPME method (1 g sample / column DB-1ms, length 30 m×ID 25 mm×film thickness 0.25 μm / helium flow 1.2 ml / min, pressure 80.5 Kpa / split 20 / 60°C for 2 min, 7°C / min until 250°C).

[0212] The amount of residual malodor measured by GC-MS was 18.29 wt% of the starting "senior citizen malodor" reconstituted material weight. This result indicates that the mixture of ethyl acetoacetate and ethanolamine (90:10) significantly reduced trans-2-nonenal.

[0213] A panel of 5 experts conducted an olfactory evaluation of the samples emitted from the bottles. An evaluation scale of 1 to 7 was used (1 = no malodor / / 7 = very strong malodor). The results of the olfactory evaluation are reported in Table 17 below.

[0214] Table 17:

[0215] sample Odor intensity (1-7) Malodor in the elderly (reference) 7 A 1.5

[0216] The malodor was obviously reduced in the sense of smell (Table 17), and the difference between the malodor intensity reference value for the elderly and that of Product A was 5.5.

[0217] Example 11. Body Lotion Composition

[0218] Body lotion compositions were prepared using the components and amounts summarized in Table 18 below.

[0219] Table 18.

[0220]

[0221] 1) Arlacel 985

[0222] 2) Tefose 2561

[0223] 3) Biolip P 90

[0224] 4) Mineral oil 30-40CPS

[0225] 5) Petroleum jelly

[0226] 6) Nipaguard PO 5

[0227] 7) PNC 400

[0228] Heat phase A and phase B to 70-75°C separately. Add phase A to phase B and then apply vacuum. Stir the mixture and cool to 55°C after stirring for 15 minutes at room temperature (RT).

[0229] Cool the mixture to room temperature and add phenoxyethanol (and) piroctone olamine when the temperature reaches 45°C. Stir the mixture for 5 minutes and then add sodium carbomer. Stir the mixture for 3 minutes and then stop stirring for 15 minutes. When the temperature of the mixture reaches 30°C, continue stirring for another 15 minutes until the cream is uniform, shiny and free of lumps. If necessary, adjust the pH to 6.70-7.20 using Glydant, Phenonip or Nipaguard PO5, or to 6.30-7.00 using Nikkoguard.

[0230] Example 12. Evaluation of Body Lotion Compositions

[0231] Trans-2-nonenal ("senior malodor") was diluted to 0.1% in MIP and used as a malodor reference.

[0232] A mixture of ethyl acetoacetate and ethanolamine was weighed in a ratio of 90%:10% and applied to the body lotion composition of Example 11 at a dosage of 0.3%.

[0233] 0.40 g of water was evenly sprayed on two small wool swatches (11 cm x 6 cm, 1.00 g), one for the malodor reference ("Sample A") and the other for the body lotion ("Sample B"). Then 0.25 g of the malodor reference was evenly distributed on the center of each swatch using a dropper. The wool swatch was rubbed 10 times and placed on a hot plate at 32°C for 15 minutes. After 15 minutes, 0.6 g of the body lotion containing active ingredients (acetoacetate and ethanolamine) was evenly applied on the swatch of active sample B.

[0234] The samples were placed on a hot plate at 32°C for another 15 minutes to dry. The two wool samples (malodor reference sample A and active sample B) were then placed in separate 20 ml SPME vials and left at room temperature for 2 hours. After 2 hours, the degradation of trans-2-nonenal was measured by GC-MS from the headspace above the samples (determined by the presence of residual trans-2-nonenal).

[0235] The analysis was performed at room temperature using GC-MS (GC Agilent 5975B) and the SPME method (1 g sample / column DB-1ms, length 30 m×ID 25 mm×film thickness 0.25 μm / helium flow 1.2 ml / min, pressure 80.5 Kpa / split 20 / 60°C for 2 min, 7°C / min until 250°C).

[0236] GC-MS analysis was repeated 24 hours later. The results of these analyses are reported in Table 19 below.

[0237] Table 19.

[0238]

[0239] The measurement results summarized in Table 18 show that when a mixture of ethyl acetoacetate and ethanolamine (90:10) is applied at 0.3% in a body lotion, the presence of trans-2-nonenal can be significantly reduced.

[0240] The samples emitted from the bottles were subjected to an olfactory evaluation by a panel of 5 people. An evaluation scale of 1 to 7 was used (1 = no malodor / / 7 = very strong malodor). The results of the olfactory evaluation are reported in Table 20 below.

[0241] Table 20.

[0242]

[0243] The malodor was obviously reduced in the sense of smell (Table 20). After 24 hours, the difference between the malodor intensity reference value for the elderly and sample B was 4.5.

[0244] 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.

[0245] 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: a) an active ingredient comprising at least one 1,3-dicarbonyl compound and at least one basic compound, wherein the amount of 1,3-dicarbonyl compound is at least 20 wt %, more typically at least 30 wt %, based on the total weight of the composition; and b) at least one ingredient selected from the group consisting of a fragrance carrier and a fragrance base, wherein the at least one ingredient is different from the at least one 1,3-dicarbonyl compound.

2. The fragrance composition according to claim 1, wherein the at least one 1,3-dicarbonyl compound is a compound represented by formula (I), in R1 and R2 are each independently H, OH, C1-C 20 Alkyl, typically C1-C 10 Alkyl, more typically C1-C6 alkyl, or C1-C 20 Alkoxy, typically C1-C 10 Alkoxy, more typically C1-C6 alkoxy; or R1 and R2 together form a 5- or 6-membered carbocyclic ring, optionally interrupted by one or more heteroatoms; wherein R1 and R2 may optionally contain one or more substituents selected from the group consisting of halogen, aryl, alkoxy, CN, NO2, OH, SH, SCH3, NH2, COOH and CONH2.

3. The fragrance composition according to claim 1 or 2, wherein the at least one 1,3-dicarbonyl compound is ethyl acetoacetate.

4. The fragrance composition according to any one of claims 1 to 3, wherein the amount of the at least one 1,3-dicarbonyl compound is 10% to 99% by weight, typically 20% to 99%, more typically 30% to 99%, and even more typically 50% to 99% by weight of the total weight of the fragrance composition.

5. The fragrance composition according to any one of claims 1 to 4, wherein the amount of the basic compound is 0% to 50% by weight, typically 0.1% to 40%, more typically 0.5% to 30%, and even more typically 1% to 10% by weight of the total weight of the fragrance composition.

6. The fragrance composition according to any one of claims 1 to 5, wherein the at least one basic compound is a compound of formula (II) or a salt thereof, in R3 is H, aryl, C1-C 20 Alkyl, typically C1-C 10 Alkyl, more typically C1-C6 alkyl, or CHR a COOR b , where R a and R b Each independently is H, C1-C 20 Alkyl, typically C1-C 10 Alkyl, more typically C1-C6 alkyl; R4 and R5 are each independently H, aryl, C1-C 20 Alkyl, typically C1-C 10 Alkyl, more typically C1-C6 alkyl, or CHR a COOR b , where R a and R b Each independently is H, C1-C 20 Alkyl, typically C1-C 10 Alkyl, more typically C1-C6 alkyl; or R4 and R5 together form a 5- or 6-membered carbocyclic ring, optionally interrupted by one or more heteroatoms; wherein R3, R4 and R5 may optionally contain one or more substituents selected from the group consisting of halogen, aryl, alkoxy, CN, NO2, OH, SH, SCH3, NH2, COOH and CONH2.

7. The fragrance composition according to any one of claims 1 to 6, wherein the at least one basic compound has a pKa>9, typically selected from the group consisting of pyrrolidine, ethanolamine, diethylamine, triethylamine, tributylamine, piperidine, alanine, proline, dimethylalkylamine, diethanolalkylamine, and mixtures thereof.

8. The fragrance composition according to any one of claims 1 to 7, wherein the weight ratio of the at least one 1,3-dicarbonyl compound to the at least one basic compound is 50:50 to 99:1, typically 80:10 to 95:5, more typically 85:15 to 95:

5.

9. A perfumed consumer product comprising a fragrance composition according to any one of claims 1 to 8.

10. A perfumed consumer product according to claim 9, wherein the perfumed consumer product is a perfume, a fabric care product, a hair care product, a skin care product, a skin cleansing product, a body deodorant or antiperspirant product, a nail product or a home care product; typically a hair care product selected from the group consisting of a shampoo, a rinse-off conditioner and a leave-in conditioner.

11. A perfumed consumer product according to claim 9 or 10, wherein the perfumed consumer product is a skin care and / or skin cleansing product selected from the group consisting of a body cream, a face cream, a dual purpose body or face cream, a shower gel, a soap bar and a body scrub.

12. A perfumed consumer product according to any one of claims 9 to 11, wherein the amount of at least one 1,3-dicarbonyl compound is from 0.01% to 4%, typically from 0.05% to 2%, more typically from 0.1% to 1.5% by weight of the total amount of the perfumed consumer product.

13. A perfumed consumer product according to any one of claims 9 to 12, wherein the amount of the at least one basic compound is from 0.0001% to 2%, typically from 0.0025% to 1%, more typically from 0.0025% to 0.5%, more typically from 0.02% to 0.3% by weight of the total amount of the perfumed consumer product.

14. Use of a fragrance composition according to any one of claims 1 to 8 or a perfumed consumer product according to any one of claims 9 to 13 for preventing, reducing or alleviating malodorous aldehydes and ketones from the hair, scalp, skin or any combination thereof of a subject, typically a human being, or from any inanimate surface, typically a fabric.

15. The use according to claim 14, wherein the malodorous aldehyde comprises 2-nonenal.

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