WO2024096037A1 - Composition de parfum et produit de consommation - Google Patents

Composition de parfum et produit de consommation Download PDF

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Publication number
WO2024096037A1
WO2024096037A1 PCT/JP2023/039359 JP2023039359W WO2024096037A1 WO 2024096037 A1 WO2024096037 A1 WO 2024096037A1 JP 2023039359 W JP2023039359 W JP 2023039359W WO 2024096037 A1 WO2024096037 A1 WO 2024096037A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
mass
mixture
fragrance composition
fragrance
Prior art date
Application number
PCT/JP2023/039359
Other languages
English (en)
Japanese (ja)
Inventor
健司 田沼
ケント エイチ． ロンバード
結菜 寄立
Original Assignee
高砂香料工業株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 高砂香料工業株式会社 filed Critical 高砂香料工業株式会社
Publication of WO2024096037A1 publication Critical patent/WO2024096037A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes

Definitions

  • the present invention relates to fragrance compositions and consumer products.
  • the compounds developed each have different characteristics in terms of fragrance, etc., so compounds with different fragrance tones are required depending on the purpose of use.
  • the present inventors have discovered that a compound having a pulegone oxime structure or a compound having a piperitone oxime structure, or a mixture containing said compounds in a specific ratio, has a unique odor, and have completed the present invention.
  • the present invention relates to the following fragrance composition, etc.
  • a fragrance composition having a unique fragrance By adding the compound or mixture of the present invention, a fragrance composition having a unique fragrance can be obtained.
  • This composition can be used in a wide range of consumer products as a fragrance or fragrance composition for cosmetics, health and hygiene products, etc.
  • the fragrance composition according to an embodiment of the present invention is also described as "the fragrance composition according to the present embodiment.”
  • the compound represented by formula (1a) will be referred to as “compound (1a)”. The same applies to other compounds.
  • the fragrance composition according to this embodiment is characterized by containing the following compounds (1a), (1b), (2a), and (2b), or a mixture containing said compounds in a specific ratio.
  • Compounds (1a) and (1b) are compounds having a pulegone oxime structure
  • compounds (2a) and (2b) are compounds having a piperitone oxime structure.
  • the fragrance composition according to the present embodiment is a fragrance composition containing at least one of the following mixture (A) and mixture (B).
  • the mixture (A) preferably contains 30% by mass or more of the compound (1a) and 70% by mass or less of the compound (1b).
  • Mixture (B) preferably contains 90% by mass or more of compound (2a) and 10% by mass or less of compound (2b).
  • the fragrance composition according to this embodiment contains at least one of compound (1a) and compound (2a).
  • the ratio of compound (1a) to compound (2a) is preferably such that, when the total of compound (1a) and compound (2a) is 100% by mass, compound (1a) is 100% by mass and compound (2a) is 0 to 100% by mass.
  • a fragrance composition containing substantially at least one of compound (1a) and compound (2a) is particularly preferred.
  • the content of compounds (1a), (1b), (2a), and (2b) in the fragrance composition according to this embodiment is determined depending on the composition, but is preferably 0.00001 to 30% by mass, more preferably 0.01 to 20% by mass, and even more preferably 0.01 to 10% by mass, respectively, of the total fragrance composition.
  • Compounds (1a), (1b), (2a), and (2b) in the fragrance composition of the present invention can be synthesized by the method described in the Examples below.
  • the fragrance composition according to this embodiment may also contain one or more of other commonly used fragrance retainers.
  • other fragrance retainers include ethylene glycol, propylene glycol, dipropylene glycol, glycerin, hexylene glycol, benzyl benzoate, triethyl citrate, diethyl phthalate, hercolin, and medium-chain fatty acid triglycerides.
  • the fragrance composition according to the present embodiment may contain a commonly used blended fragrance.
  • the fragrance composition thus obtained can impart a fresh and highly palatable fragrance.
  • the fragrance composition according to the present embodiment can be used as a fragrance component in an amount commonly used in the industry to impart a unique fragrance to consumer products, thereby increasing their commercial value.
  • consumer products include fragrance products, cosmetics, toiletry products, air care products, daily necessities, miscellaneous goods, oral care products, detergents, fabric softeners, and quasi-drugs.
  • Fragrance products can include, for example, perfumes, eau de perfumes, eau de toilettes, eau de colognes, and the like.
  • cosmetics include basic cosmetics such as face wash cream, vanishing cream, cleansing cream, cold cream, massage cream, milky lotion, lotion, serum, pack, makeup remover, etc.; makeup cosmetics such as foundation, lipstick, etc.; hair cosmetics such as hair tonic, hair liquid, hair spray, etc.; sunscreen cosmetics such as tanning products and sunscreen products; and medicated cosmetics such as antiperspirants, body deodorants, aftershave lotions and gels, permanent wave agents, medicated soaps, medicated shampoos, and medicated skin cosmetics.
  • Toiletry products include hair care products such as shampoo, rinse, rinse-in-shampoo, conditioner, treatment, hair pack, etc.; skin care products such as lip balm, hand cream, etc., soaps such as cosmetic soap, bath soap, etc.; body care products such as body soap, body shampoo, hand soap, etc.; bath additives such as bath salts (bath salts, bath tablets, bath liquid, etc.), foam baths (bubble baths, etc.), bath oils (bath perfumes, bath capsules, etc.), milk baths, bath jellies, bath cubes, etc.
  • hair care products such as shampoo, rinse, rinse-in-shampoo, conditioner, treatment, hair pack, etc.
  • skin care products such as lip balm, hand cream, etc.
  • soaps such as cosmetic soap, bath soap, etc.
  • body care products such as body soap, body shampoo, hand soap, etc.
  • bath additives such as bath salts (bath salts, bath tablets, bath liquid, etc.), foam baths (bubble baths, etc.
  • Air care products include, for example, aerosols, sprays, powder sprays, etc.
  • Examples of everyday items include deodorants and air fresheners.
  • miscellaneous goods examples include tissue paper, toilet paper, etc.
  • oral care products examples include toothpaste, mouthwash, mouth spray, and gargle.
  • detergents heavy-duty laundry detergents, light-duty laundry detergents, liquid detergents, laundry soaps, compact detergents, powdered soaps, etc.; as fabric softeners, liquid softeners, dryer sheets, etc.; as cleaning agents, cleansers, furniture care, house cleaners, toilet cleaners, bathroom cleaners, glass cleaners, mold removers, drain cleaners, etc.; as kitchen detergents, kitchen soaps, synthetic kitchen soaps, dishwashing detergents, dishwasher detergents, etc.; as bleaches, oxidation bleaches (chlorine bleaches, oxygen bleaches, etc.), reduction bleaches (sulfur bleaches, etc.), optical bleaches, etc.; air care products include aerosols (spray type, powder spray), candles, wax melts, car fresheners, free-standing, spray type or plug-in type deodorants and fragrances (solid type, gel type, liquid type, etc.); pet care products include pet deodorants, pet toilet deodorants, pet shampoos, pet conditioners; miscellane
  • Quasi-drugs include, for example, patches and ointments.
  • the fragrance composition according to this embodiment when used in the above-mentioned products, it may be used in any form selected according to the purpose, such as in its original state, or in a liquid state dissolved in, for example, alcohols, polyhydric alcohols such as propylene glycol, or glycerin; in a solubilized or dispersed state solubilized or dispersed using a surfactant such as a nonionic surfactant, anionic surfactant, cationic surfactant, or amphoteric surfactant; or in a microcapsule state obtained by treating with an encapsulating agent.
  • a surfactant such as a nonionic surfactant, anionic surfactant, cationic surfactant, or amphoteric surfactant
  • the fragrance composition according to this embodiment may be encapsulated in an encapsulating agent such as cyclodextrin to stabilize and sustain the release of the fragrance composition.
  • an encapsulating agent such as cyclodextrin to stabilize and sustain the release of the fragrance composition.
  • a consumer product comprising the fragrance composition according to any one of [1] to [3].
  • the consumer product is selected from fragrance products, cosmetics, toiletry products, air care products, daily necessities, miscellaneous goods, oral care products, detergents, and quasi-drugs.
  • Example 3 Reference Example 1
  • Example 3 Compared to the mixture of Example 1, the mixture of Example 2, in which the ratio of Z isomer (compound (1a)) was increased, had a clearly stronger odor, and it was found that the pure Z isomer (Example 3, compound (1a)) had an even stronger odor. On the other hand, the E isomer (Reference Example 1, compound (1b)) had a significantly weaker odor, and the quality of the odor was also different from that of the Z isomer, possessing a herbal aroma.
  • Example 5 Increase in the ratio of compound (2a) 100 mL of hexane and 100 mL of ethyl acetate were added to 110 g of the mixture obtained in Example 4, and the mixture was heated to 50° C. and dissolved. The mixture was cooled to room temperature, and the flesh-colored solid that precipitated was collected, thereby obtaining 50 g of a mixture in which the ratio of compound (2a):compound (2b) was 90:10 and the amount of compound (2a) was increased.
  • Example 6 Reference Example 2
  • Example 6 Isolation of Compound (2a) and Compound (2b)
  • Example 5 The mixture of Example 5, in which the ratio of Z isomer (compound (2a)) was increased, was found to have a clearly stronger odor than the mixture of Example 4, and the pure Z isomer (Example 6, compound (2a)) had an even stronger odor.
  • the E isomer Reference Example 2, compound (2b)
  • the quality of the odor was also found to be different from that of the Z isomer, having a green, cassis odor.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne une composition de parfum contenant au moins l'un parmi un mélange (A) et un mélange (B). Le mélange (A) comprend au moins 15 % en masse d'un composé (1a) et 85 % en masse d'un composé (1b), et le mélange (B) comprend 55 % en masse d'un composé (2a) et 45 % en masse d'un composé (2b). (La somme du composé (1a) et du composé (1b) est de 100 % en masse, et la somme du composé (2a) et du composé (2b) est de 100 % en masse).
PCT/JP2023/039359 2022-11-02 2023-10-31 Composition de parfum et produit de consommation WO2024096037A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202263421772P 2022-11-02 2022-11-02
US63/421,772 2022-11-02

Publications (1)

Publication Number Publication Date
WO2024096037A1 true WO2024096037A1 (fr) 2024-05-10

Family

ID=90930601

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2023/039359 WO2024096037A1 (fr) 2022-11-02 2023-10-31 Composition de parfum et produit de consommation

Country Status (1)

Country Link
WO (1) WO2024096037A1 (fr)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07258684A (ja) * 1994-03-18 1995-10-09 Givaudan Roure Internatl Sa 着臭剤及び／又はフレーバー組成物

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07258684A (ja) * 1994-03-18 1995-10-09 Givaudan Roure Internatl Sa 着臭剤及び／又はフレーバー組成物

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
BERRADA, M. et al. Essais de valorisation de l'essence de menthe Pouliot (mentha plegium), Synthese de diverses aziridines a partir des oximes de la (+)pulegone et de l'un de ses derives, la (-)methyl-2 isopulegone. Bulletin de la Societe Chimique de France. 1985, no. 5, pp. 937-946, ISSN: 0037-8968 *
FERRERO, LOUIS: "Aziridines saturCes et insaturCes. Synth'eses par rCduction de cyclohexCnones oximes et Ctudes spectroscopiques", CANADIAN JOURNAL OF CHEMISTRY., vol. 53, no. 21, 1 January 1975 (1975-01-01), pages 3227 - 3239, XP093169106 *

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