WO2025090783A1 - Compositions et procédés pour conférer un attribut de type sensation de propre - Google Patents
Compositions et procédés pour conférer un attribut de type sensation de propre Download PDFInfo
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- WO2025090783A1 WO2025090783A1 PCT/US2024/052836 US2024052836W WO2025090783A1 WO 2025090783 A1 WO2025090783 A1 WO 2025090783A1 US 2024052836 W US2024052836 W US 2024052836W WO 2025090783 A1 WO2025090783 A1 WO 2025090783A1
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- fragrance composition
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- dimethyloct
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- 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
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- 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
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
- C11B9/0019—Aliphatic compounds containing oxygen as the only heteroatom carbocylic acids; Salts or esters thereof
-
- 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
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
-
- 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
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
- C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
- C11B9/0049—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/50—Perfumes
Definitions
- compositions and methods including fragrance ingredients that impart a clean attribute.
- fragrance ingredients that evoke a desired perception or sensation is key to producing such fragrances.
- compositions and methods provided herein address these and other needs in the art.
- a fragrance composition having a clean attribute including one or moreof: 2,6-dimethyloct-7-en-2-ol and (e)-l-ethoxydec-l-ene, ethyl 5-norbornene-2-carboxylate, or both (e)-l -ethoxy dec- 1-ene and ethyl 5-norbornene-2-carboxylate; 2-tert-butylcyclohexyl acetate and methyl 3-methylcyclohexane-l-carboxylate; or 2,4-dimethylcyclohex-3- enecarbaldehyde and l-ethyl-2-methylpropyl crotonate.
- the 2,6- dimethyloct-7-en-2-ol and the (e)-l-ethoxydec-l-ene are present at a ratio in a range from 0.5:1 to 7500:1 2,6-dimethyloct-7-en-2-ol to (e)-l-ethoxydec-l-ene.
- the 2,6- dimethyloct-7-en-2-ol and the ethyl 5-norbornene-2-carboxylate are present at a ratio in a range from 1.8: 1 to 15000: 1 2,6-dimethyloct-7-en-2-ol to ethyl 5-norbomene-2-carboxylate.
- the 2-tert-butylcyclohexyl acetate and the methyl 3-methylcyclohexane-l- carboxylate are present at a ratio in a range from 0.18:1 to 666: 1 2-tert-butylcyclohexyl acetate to methyl 3 -methylcyclohexane- 1 -carboxylate.
- the 2,4-dimethylcyclohex-3- enecarbaldehyde and the l-ethyl-2-methylpropyl crotonate are present at a ratio in a range from 1 :0.15 to 1:401 2,4-dimethylcyclohex-3-enecarbaldehyde to l-ethyl-2-methylpropyl crotonate.
- the 2,6-dimethyloct-7-en-2-ol and the (e)-l -ethoxydec- 1-ene are present at a ratio of 6: 1 2,6-dimethyloct-7-en-2-ol to (e)-l-ethoxydec-l-ene.
- the 2,6- dimethyloct-7-en-2-ol and the ethyl 5-norbornene-2-carboxylate are present at a ratio of 59:1 2,6- dimethyloct-7-en-2-ol to ethyl 5-norbomene-2-carboxylate.
- the 2-tert- butylcyclohexyl acetate and the methyl 3-methylcyclohexane-l-carboxylate are present at a ratio of 3:1 2-tert-butylcyclohexyl acetate to methyl 3-methylcyclohexane-l -carboxylate.
- the 2,4-dimethylcyclohex-3-enecarbaldehyde and the l-ethyl-2-methylpropyl crotonate are present at a ratio of 1: 10 2,4-dimethylcyclohex-3-enecarbaldehyde to l-ethyl-2- methylpropyl crotonate.
- the 2,6-dimethyloct-7-en-2-ol is present at a concentration in a range of about 3.5 wt% to about 30 wt% of the total weight of the fragrance composition and the (e)-l-ethoxydec- 1-ene is present at a concentration in a range of about 0.004 wt% to about 6.7 wt% of the total weight of the fragrance composition.
- the 2,6-dimethyloct-7-en-2-ol is present at a concentration in a range of about 1.4 wt% to about 30 wt% of the total weight of the fragrance composition and the ethyl 5-norbornene-2-carboxylate is present at a concentration in a range of about 0.002 wt% to about 0.8 wt% of the total weight of the fragrance composition.
- the 2-tert-butylcyclohexyl acetate is present at a concentration in a range of about 3 wt% to about 33 wt% of the total weight of the fragrance composition and the methyl 3-methylcyclohexane-l-carboxylate is present at a concentration in a range of about 0.05 wt% to about 16 wt% of the total weight of the fragrance composition.
- the 2,4-dimethylcyclohex-3-enecarbaldehyde is present at a concentration in a range of about 0.049 wt% to about 1.25 wt% of the total weight of the fragrance composition and the l-ethyl-2-methylpropyl crotonate is present at a concentration in a range of about 0.19 wt% to about 19.7 wt% of the total weight of the fragrance composition.
- the fragrance composition includes at least two fragrances ingredients.
- the fragrance composition is a sketch, an accord, or a full fragrance.
- a consumer product containing a fragrance composition described herein containing a fragrance composition described herein.
- the consumer product is a cleaning product, home care product, fabric care product, personal care product, cosmetic product, or air care product.
- a method for producing a fragrance composition or a consumer product having a clean attribute including formulating one or more of: 2,6-dimethyloct-7-en-2-ol and (e)-l -ethoxydec- 1-ene, ethyl 5-norbomene-2-carboxylate, or both (e)-l -ethoxydec- 1-ene and ethyl 5-norbornene-2-carboxylate; 2-tert-butylcyclohexyl acetate and methyl 3- methylcyclohexane-1 -carboxylate; or 2,4-dimethylcyclohex-3-enecarbaldehyde and l-ethyl-2- methylpropyl crotonate; into a fragrance composition or consumer product.
- the fragrance composition is a new fragrance composition.
- the fragrance composition is an existing fragrance composition including one or more of 2,6- dimethyloct-7-en-2-ol, (e)-l -ethoxy dec- 1-ene, ethyl 5-norbornene-2-carboxylate, 2-tert- butylcyclohexyl acetate, methyl 3-methylcyclohexane-l -carboxylate, 2,4-dimethylcyclohex-3- enecarbaldehyde, or l-ethyl-2-methylpropyl crotonate.
- the fragrance composition is an existing fragrance composition that does not include one or more of 2,6- dimethyloct-7-en-2-ol, (e)-l -ethoxy dec- 1-ene, ethyl 5-norbornene-2-carboxylate, 2-tert- butylcyclohexyl acetate, methyl 3-methylcyclohexane-l -carboxylate, 2,4-dimethylcyclohex-3- enecarbaldehyde, or l-ethyl-2- methylpropyl crotonate.
- the 2,6- dimethyloct-7-en-2-ol and the (e)-l -ethoxydec- 1-ene are formulated into the fragrance composition or consumer product at a ratio in a range from 0.5: 1 to 7500: 1 2,6-dimethyloct-7-en-
- the 2,6-dimethyloct-7-en-2-ol and the ethyl 5-norbomene-2-carboxylate are formulated into the fragrance composition or consumer product at a ratio in a range from 1.8:1 to 15000:1 2,6-dimethyloct-7-en-2-ol to ethyl 5-norbornene-2- carboxylate.
- the 2-tert-butylcyclohexyl acetate and the methyl 3- methyl cyclohexane- 1 -carboxylate are formulated into the fragrance composition or consumer product at a ratio in a range from 0.18: 1 to 666:1 2-tert-butylcyclohexyl acetate to methyl 3- methylcyclohexane-1 -carboxylate.
- the 2,4-dimethylcyclohex-3- enecarbaldehyde and the l-ethyl-2-methylpropyl crotonate are formulated into the fragrance composition or consumer product at a ratio in a range from 1:0.15 to 1:401 2,4-dimethylcyclohex-
- the 2,6- dimethyloct-7-en-2-ol and the (e)-l-ethoxydec-l-ene are formulated into the fragrance composition or consumer product at a ratio of 6:1 2,6-dimethyloct-7-en-2-ol to (e)-l -ethoxy dec - 1-ene.
- the 2,6-dimethyloct-7-en-2-ol and the ethyl 5-norbomene-2- carboxylate are formulated into the fragrance composition or consumer product at a ratio of 59:1 2,6-dimethyloct-7-en-2-ol to ethyl 5-norbomene-2-carboxylate.
- the 2-tert- butylcyclohexyl acetate and the methyl 3-methylcyclohexane-l -carboxylate are formulated into the fragrance composition or consumer product at a ratio of 3 : 1 2-tert-butylcyclohexyl acetate to methyl 3-methylcyclohexane-l -carboxylate.
- the 2,4-dimethylcyclohex-3- enecarbaldehyde and the l-ethyl-2-methylpropyl crotonate are formulated into the fragrance composition or consumer product at a ratio of 1: 10 2,4-dimethylcyclohex-3-enecarbaldehyde to l-ethyl-2-methylpropyl crotonate.
- the 2,6-dimethyloct-7-en-2-ol is formulated into the fragrance composition or consumer product at a concentration in a range of about 3.5 wt% to about 30 wt% of the total weight of the fragrance composition or consumer product and the (e)-l -ethoxy dec- 1-ene is formulated into the fragrance composition or consumer product at a concentration in a range of about 0.004 wt% to about 6.7 wt% of the total weight of the fragrance composition or consumer product.
- the 2,6-dimethyloct-7-en- 2-ol is formulated into the fragrance composition or consumer product at a concentration in a range of about 1.4 wt% to about 30 wt% of the total weight of the fragrance composition or consumer product and the ethyl 5-norbornene-2-carboxylate is formulated into the fragrance composition or consumer product in a range of about 0.002 wt% to about 0.8 wt% of the total weight of the fragrance composition or consumer product.
- the 2-tert- butylcyclohexyl acetate is formulated into the fragrance composition or consumer product at a concentration in a range of about 3 wt% to about 33 wt% of the total weight of the fragrance composition or consumer product and the methyl 3-methylcyclohexane-l -carboxylate is formulated into the fragrance composition or consumer product at a concentration in a range of about 0.05 wt% to about 16 wt% of the total weight of the fragrance composition or consumer product.
- the 2,4-dimethylcyclohex-3-enecarbaldehyde is formulated into the fragrance composition or consumer product at a concentration in a range of about 0.049 wt% to about 1.25 wt% of the total weight of the fragrance composition or consumer product and the 1 -ethyl-2-methylpropyl crotonate is formulated into the fragrance composition or consumer product at a concentration in a range of about 0.19 wt% to about 19.7 wt% of the total weight of the fragrance composition or consumer product.
- a method of evoking a sense of clean in a subject including delivering a fragrance composition described herein or a consumer product described herein to a subject.
- the mammalian olfactory pathway is evolutionarily old neural circuitry that differs from canonical thalamocortical sensory pathways in that it forms direct and, in some cases, reciprocal connections with brain structures involved in emotion and memory.
- olfactory sensory neurons present in the nose convey sensory information to the olfactory bulb, located in the forebrain, where they form synapses with projection neurons that directly or indirectly target limbic system structures, including the hippocampus and amygdala, which are related to memory and emotion.
- the sense of smell is uniquely positioned neuroanatomically to quickly and directly impact a subject psychologically.
- Cleanliness is a desirable attribute as evidenced by the variety of consumer products, such as personal care products, home care products, fabric care products, cleaning products, air care products, and cosmetic products, among others, designed to promote a sensation of cleanliness and/or personal hygiene.
- a clean sensation may be desirable in a variety of circumstances and activities including, but not limited to, when interacting with others, for example in social, work, or school settings; while exercising, bathing, and generally cleaning the body; when caring for fabrics, for example when laundering clothing, linens, and other fabric items or cleaning upholstery, carpets, drapes, etc.; and when cleaning an environment, for example, during household or workplace cleaning activities.
- fragrances having a clean attribute i.e., that evoke a clean sensation in a subject upon exposure, have broad utility.
- Fragrances having a clean attribute may be used alone or in combination with other products or strategies useful for cleaning.
- a consumer product such as a personal care product, cleaning products, home care product, fabric care product, air care product, or cosmetic product, among others
- the fragrance having a clean attribute may enhance the subject’s sense of cleanliness when using the product. Further, others who encounter the fragrance having a clean attribute will also perceive a clean sensation.
- fragrance compositions that reliably evoke a clean sensation, however, is a difficult task.
- data collected from consumer tests can be both large and non-uniform (e.g., fragrances tested and/or the concentrations of fragrances tested differ across consumer tests), which can hinder the derivation of meaningful information from wide consumer testing.
- these difficulties were overcome to identify fragrance ingredient combinations and specific ratios and concentrations of such ingredients that reliably evoke a clean sensation in subjects upon exposure.
- the combinations of fragrance ingredients found to evoke a clean sensation in a subject were identified using an association rule mining method, for example as described in International patent application WO2023/107564, which is incorporated herein by reference in its entirety.
- the association rule mining method determined fragrance ingredient combinations and concentration and ratio ranges of the ingredients that when present in a fragrance increased the likelihood of evoking a sensation of clean in a subject.
- Use of the ingredient combinations, for example within the determined concentration ranges and ratios, in a fragrance composition or consumer product increased the number of subjects who found the composition or product to evoke a clean sensation. See, e.g., Section III.
- compositions e.g., fragrance compositions and consumer products, that contain combinations of ingredients that evoke a clean sensation.
- Fragrance compositions and/or consumer products including the combinations of fragrance ingredients that evoke a clean sensation are referred to as having a clean attribute.
- methods for producing and using such compositions are also provided.
- compositions and methods described herein are advantageous in that they provide an olfactory means of evoking a sensation of clean in a subject.
- the compositions provided herein are specifically designed to evoke the sensation of cleanliness in a subject and are thus referred to as having a clean attribute.
- Such compositions may be used alone or in combination with other cleanliness or cleaning strategies to promote a subject’s sense of clean.
- fragrance composition means the same and refer to a composition that is a mixture of fragrance ingredients including, for example, alcohols, aldehydes, ketones, esters, ethers, lactones, nitriles, natural extracts (e.g., essential oils, absolutes, CO2 extracts, enfleurages, isolates either pure or purified using physical processes), synthetic oils, mercaptans, etc., which are admixed so that the combined odors of the individual ingredients produce a fragrance.
- natural extracts e.g., essential oils, absolutes, CO2 extracts, enfleurages, isolates either pure or purified using physical processes
- synthetic oils mercaptans, etc.
- the term “subject” refers to the user of the fragrance (e.g., a fragrance composition or consumer product containing a fragrance composition) and/or the intended recipient of the fragrance, for example when it is used or administered by another.
- the term “subject” refers to a human or non-human subject.
- Non-limiting examples of non-human subjects include non-human primates, dogs, cats, mice, rats, guinea pigs, rabbits, pigs, fowl, horses, cows, goats, sheep, cetaceans, etc.
- the subject is a human.
- a subject may be referred to as a consumer.
- Impart, evoke, elicit, drive, induce, and grammatical variants thereof may be alternatively used to indicate a cause-and-effect relationship.
- a fragrance may evoke, induce, elicit, or drive a perception or sensation in a subject upon exposure to the fragrance.
- a fragrance having an attribute e.g., a clean attribute, causes a subject to perceive or sense the attribute upon exposure to the fragrance.
- the terms perceive, perception, sense, sensation, and grammatical variants thereof may be used alternatively to describe an effect evoked in a subject.
- compositions and consumer products including combinations of ingredients that evoke a clean sensation in a subject.
- the combinations of ingredients that evoke a clean sensation in a subject impart a clean attribute to the fragrance composition and/or consumer product. Therefore, fragrance compositions and consumer products having a clean attribute elicit a clean sensation in a subject.
- a fragrance composition having a clean attribute In another aspect is provided a consumer product including a fragrance composition having a clean attribute.
- a clean sensation includes a general sense of clean.
- a general sensation of clean or cleanliness may be detected and/or measured using, for example, declarative measures, such as questionnaires (see, e.g., Section III).
- the questionnaire may require a subject to rank the intensity of a clean sensation evoked by the fragrance.
- the questionnaire may require a subject to state whether the fragrance could be described as “clean.”
- the clean sensation includes related sensations of clean.
- the related sensation includes a sense of basic efficient cleaning, a sense of deep cleaning, a sense of soft or gentle cleaning, a sense of preventing or fighting malodors, and/or a sense of facilitating a cleaning process.
- these related sensations are also detectable and/or measurable using, for example, declarative measures, such as questionnaires.
- the questionnaire may require a subject to rank the intensity of the sensation evoked by the fragrance.
- the questionnaire may require a subject to select from a series of proposition descriptors one or more descriptors that best describe the sensation evoked by the fragrance. It should be appreciated that other methods known in the art may be used to evaluate a subject’s response to a fragrance, including, but not limited to, other declarative measures and psychological, physiological, and psychophysiological assessments.
- the sensation of clean includes one or more of a general sense of clean, a sense of basic efficient cleaning, a sense of deep cleaning, a sense of soft or gentle cleaning, a sense of preventing or fighting malodors, and a sense of facilitating a cleaning process.
- the clean sensation includes a general sense of clean, a sense of basic efficient cleaning, a sense of deep cleaning, a sense of soft or gentle cleaning, a sense of preventing or fighting malodors, and a sense of facilitating a cleaning process.
- fragrance ingredients could evoke a clean sensation in a broad (e.g., multi-country) group of subjects. See, e.g., Section III below. These combinations were identified using association rule mining methods, see e.g., WO2023/107564, which further determined the concentration and ratio ranges at which the identified ingredients could be combined to increase the likelihood of a subject experiencing a clean sensation from olfactory exposure. The presence of the ingredient combinations in full fragrances contained in consumer products resulted in an increased number of subjects identifying the fragrance as having a clean attribute. See, e.g., Section III.
- a fragrance composition that evokes a clean sensation including a fragrance ingredient combination determined to evoke a sense of clean.
- the fragrance ingredient combination that evokes a sense of clean is 2,6-dimethyloct-7-en-2-ol (dihydromyrcenol) and (e)-l-ethoxydec- 1-ene (Arctical).
- 2,6-dimethyloct-7-en-2-ol may also be referred to by the chemical names or synonyms dihydromyrcenol, 7-octen-2-ol,2,6-dimethyl; dimyrcetol; dihydroocimenol; dihydromuganol; dihydro myrcenol; dimyrcetol; tetrahydro convalol; lymolene; dihydromyrcenol; dihydromyrcenol; dimethyloctenol-2; octendimethyl-; dihydromyrcenol; 2,6- dimethyl-7-octenol-2; and 7-octen-2-ol, 2,6-dimethyl-.
- (e)-l -ethoxydec- 1-ene may also be referred to by the chemical names or synonyms Arctical, ether, ethyl 1 -decenyl, (e or z); 1 ethyl 1-decenyl; and artical.
- (e)-l -etho y dec- 1-ene is described in US patent 7,175,871.
- the fragrance ingredient combination that evokes a sense of clean includes 2,6-dimethyloct-7-en-2-ol (dihydromyrcenol) and ethyl 5-norbornene-2- carboxylate (TropicaliaTM).
- ethyl 5-norbornene-2-carboxylate is described in US patent 7,834,219.
- the fragrance ingredient combination that evokes a sense of clean includes 2-tert-butylcyclohexyl acetate (Verdox) and methyl 3- methylcyclohexane- 1 -carboxylate (Jamunate).
- Methyl 3 -methylcyclohexane- 1 -carboxylate may be referred to by the chemical names or synonyms Jamunate.
- 2-tert-butylcyclohexyl acetate may also be referred to by the chemical names or synonyms Verdox, cyclohexanol, 2-tert.
- Butyl acetate; cyclohexanol, 2-( 1,1 -dimethylethyl): acetate; ortho-vertenex; ortho tert. Butylcyclohexyl acetate; verdex; ortholate; ylanate ortho; pommelione; otbcha; ortholate; o- tert.butylcyclohexylacetate; nardoxyl; menthonate; cyclanyl acetate; agrumex he; butylcyclohexylacetate; butylcyclohexylacetate; dimethylethylcyclohexyl acetat; 2- tert.butylcyclohexyl acetate; o-tert.butylcyclohexyl acetate; and 2-(l,l-dimethylethyl)cyclohexyl acetate.
- the fragrance ingredient combination that evokes a sense of clean includes 2,4-dimethylcyclohex-3-enecarbaldehyde (Aid AA triplal BHT) and l-ethyl-2- methylpropyl crotonate (Cosmofruit).
- 2,4-dimethylcyclohex-3-enecarbaldehyde may also be referred to by the chemical names or synonyms Aid AA triplal BHT; 3-cyclohexene-l- carboxaldehyde, 3,5-dimethyl; agrumen aldehyde h&r; aldehyde aa triplal; agrumenal; vertocitral; triplal; ligustral; hivertal; cyclo vertal; cyclal c; alomural; dimethylcyclohexene- 1-carboxal; dimethyltetrahydrobenzaldehyde; dimethylcyclohexenyl- 1 -carbald; 2,4-dimethyl-3-cyclohexene- 1-carboxaldehyde; 2,4-dimethyltetrahydrobenzaldehyde; 2,4-dimethyl-3-cyclohexenyl-l- carbaldehyde; zestover.
- l-ethyl-2-methylpropyl crotonate may also be referred to by the chemical names or synonyms Cosmofruit.
- l-ethyl-2-methylpropyl crotonate is described in US patent 8,772,533.
- the presence of the fragrance ingredient combination determined to evoke a sensation of clean imparts a clean attribute to fragrance composition.
- a fragrance composition having a clean attribute including one or more of: (a) 2,6-dimethyloct-7-en-2-ol and (e)-l -ethoxydec- 1-ene, ethyl 5-norbornene-2- carboxylate, or both (e)-l -ethoxydec- 1-ene and ethyl 5-norbornene-2-carboxylate; (b) 2-tert- butylcyclohexyl acetate and methyl 3-methylcyclohexane-l-carboxylate; or (c) 2,4- dimethylcyclohex-3-enecarbaldehyde and l-ethyl-2-methylpropyl crotonate.
- the fragrance composition evokes a sense of clean in a subject.
- the evoked sense of clean is determined and/or measured using a declarative method.
- the evoked sense of clean is determined and/or measured using a questionnaire. Examples of suitable declarative measures and questionnaires are known in the art, and examples are described herein, including in Section III below.
- the fragrance composition having a clean attribute includes 2,6-dimethyloct-7-en-2-ol and (e)-l- ethoxydec-l-ene.
- the fragrance composition having a clean attribute includes 2,6-dimethyloct-7-en-2-ol and ethyl 5-norbornene-2-carboxylate. In some embodiments, the fragrance composition having a clean attribute includes 2,6-dimethyloct-7-en-2-ol, (e)-l- ethoxydec-l-ene, and ethyl 5-norbomene-2-carboxylate. In some embodiments, the fragrance composition having a clean attribute includes 2-tert-butylcyclohexyl acetate and methyl 3- methylcyclohexane-1 -carboxylate.
- the fragrance composition having a clean attribute includes 2,4-dimethylcyclohex-3-enecarbaldehyde and l-ethyl-2- methylpropyl crotonate. In some embodiments, the fragrance composition having a clean attribute includes any combination of the ingredient combinations in this or the above paragraph. In some embodiments, the fragrance composition having a clean attribute includes any combination of the ingredient combinations in this or the above paragraph, at concentrations or ratios of the ranges described below.
- the 2,6-dimethyloct-7-en-2-ol and (e)-l -ethoxydec- 1-ene are present in the fragrance composition at a ratio in the range of 0.5:1 to 7500:1 2,6-dimethyloct-7- en-2-ol to (e)-l -ethoxy dec- 1-ene.
- the 2,6-dimethyloct-7-en-2-ol and (e)-l- ethoxydec-l-ene are present in the fragrance composition at a ratio in the range of 875: 1 to 7500: 1
- 2,6-dimethyloct-7-en-2-ol to (e)-l -ethoxy dec- 1-ene 2,6-dimethyloct-7-en-2-ol to (e)-l -ethoxy dec- 1-ene.
- the 2,6-dimethyloct- 7-en-2-ol and (e)-l -ethoxydec- 1-ene are present in the fragrance composition at a ratio in the range of 4.5:1 to 7500: 1 2,6-dimethyloct-7-en-2-ol to (e)-l-ethoxydec-l-ene.
- the 2,6-dimethyloct-7-en-2-ol to (e)-l-ethoxydec-l-ene the 2,6-dimethyloct-7-en-2-ol to (e)-l-ethoxydec-l-ene.
- 2,6-dimethyloct-7-en-2-ol and (e)-l -ethoxy dec- 1-ene are present in the fragrance composition at a ratio in the range of 0.5: l to 875:1 2,6-dimethyloct-7-en-2-ol to (e)-l-ethoxydec- 1-ene.
- the 2,6-dimethyloct-7-en-2-ol and (e)-l-ethoxydec-l-ene are present in the fragrance composition at a ratio in the range of 4.5:1 to 875:1 2,6-dimethyloct-7-en-2-ol to (e)-l- ethoxydec-l-ene.
- the 2,6-dimethyloct-7-en-2-ol and (e)- 1 -ethoxy dec- 1- ene are present in the fragrance composition at a ratio in the range of 0.5 : 1 to 10: 1 2,6-dimethyloct- 7-en-2-ol to (e)-l -ethoxy dec- 1-ene. In some embodiments, the 2,6-dimethyloct-7-en-2-ol and (e)-
- 1 -ethoxy dec- 1-ene are present in the fragrance composition at a ratio in the range of 0.5:1 to 4.5:1
- 2,6-dimethyloct-7-en-2-ol to (e)-l -ethoxy dec- 1-ene 2,6-dimethyloct-7-en-2-ol to (e)-l -ethoxy dec- 1-ene.
- the 2,6-dimethyloct- 7-en-2-ol and (e)-l -ethoxy dec- 1-ene are present in the fragrance composition at a ratio of 6:1 2,6- dimethyloct-7-en-2-ol to (e)-l -ethoxy dec- 1-ene.
- 2-ol is present in the fragrance composition at a concentration in a range of about 3.5 wt% to about 30 wt% and the (e)-l -ethoxy dec- 1-ene is present in the fragrance composition at a concentration in a range of about 0.004 wt% to about 6.7 wt%.
- the wt% (weight percent) is with respect to the total fragrance composition.
- the 2,6-dimethyloct-7-en-2-ol and ethyl 5-norbomene-2- carboxylate are present in the fragrance composition at a ratio in the range of 1.8:1 to 15000:1 2,6-dimethyloct-7-en-2-ol to ethyl 5-norbomene-2-carboxylate.
- the 2,6- dimethyloct-7-en-2-ol and ethyl 5-norbomene-2-carboxylate are present in the fragrance composition at a ratio in the range of 714.5: 1 to 15000: 1 2,6-dimethyloct-7-en-2-ol to ethyl 5- norbornene-2-carboxylate.
- the 2,6-dimethyloct-7-en-2-ol and ethyl 5- norbornene-2-carboxylate are present in the fragrance composition at a ratio in the range of 37 : 1 to 15000:1 2,6-dimethyloct-7-en-2-ol to ethyl 5-norbomene-2-carboxylate.
- the 2,6-dimethyloct-7-en-2-ol and ethyl 5-norbornene-2-carboxylate are present in the fragrance composition at a ratio in the range of 1.8:1 to 714.5:1 2,6-dimethyloct-7-en-2-ol to ethyl 5- norbornene-2-carboxylate.
- the 2,6-dimethyloct-7-en-2-ol and ethyl 5- norbornene-2-carboxylate are present in the fragrance composition at a ratio in the range of 1.8: 1 to 714.5:1 2,6-dimethyloct-7-en-2-ol to ethyl 5-norbomene-2-carboxylate.
- the 2,6-dimethyloct-7-en-2-ol and ethyl 5-norbornene-2-carboxylate are present in the fragrance composition at a ratio in the range of 1.8:1 to 60:1 2,6-dimethyloct-7-en-2-ol to ethyl 5- norbornene-2-carboxylate.
- the 2,6-dimethyloct-7-en-2-ol and ethyl 5- norbornene-2-carboxylate are present in the fragrance composition at a ratio in the range of 1.8:1 to 37: 1 2,6-dimethyloct-7-en-2-ol to ethyl 5-norbornene-2-carboxylate.
- the 2,6-dimethyloct-7-en-2-ol and ethyl 5-norbornene-2-carboxylate are present in the fragrance composition at a ratio of 59:1 2,6-dimethyloct-7-en-2-ol to ethyl 5-norbomene-2-carboxylate.
- the 2,6-dimethyloct-7-en-2-ol is present in the fragrance composition at a concentration in a range of about 1.4 wt% to about 30 wt% and the ethyl 5-norbomene-2- carboxylate is present in the fragrance composition at a concentration in a range of about 0.002 wt% to about 0.8 wt%.
- the wt% (weight percent) is with respect to the total fragrance composition.
- the 2-tert-butylcyclohexyl acetate and methyl 3- methyl cyclohexane- 1 -carboxylate are present in the fragrance composition at a ratio in the range of 0.18:1 to 666:1 2-tert-butylcyclohexyl acetate to methyl 3-methylcyclohexane-l -carboxylate.
- the 2-tert-butylcyclohexyl acetate and methyl 3 -methylcyclohexane- 1- carboxylate are present in the fragrance composition at a ratio in the range of 2:1 to 666: 1 2-tert- butylcyclohexyl acetate to methyl 3-methylcyclohexane-l -carboxylate.
- the 2-tert-butylcyclohexyl acetate and methyl 3-methylcyclohexane-l-carboxylate are present in the fragrance composition at a ratio in the range of 60: 1 to 666:1 2-tert-butylcyclohexyl acetate to methyl 3-methylcyclohexane-l -carboxylate.
- the 2-tert-butylcyclohexyl acetate and methyl 3-methylcyclohexane-l -carboxylate are present in the fragrance composition at a ratio in the range of 0.18:1 to 60:1 2-tert-butylcyclohexyl acetate to methyl 3- methylcyclohexane- 1 -carboxylate.
- the 2-tert-butylcyclohexyl acetate and methyl 3-methylcyclohexane-l -carboxylate are present in the fragrance composition at a ratio in the range of 2: 1 to 60:1 2-tert-butylcyclohexyl acetate to methyl 3 -methylcyclohexane- 1- carboxylate.
- the 2-tert-butylcyclohexyl acetate and methyl 3- methylcyclohexane- 1 -carboxylate are present in the fragrance composition at a ratio in the range of 0.18: 1 to 5: 1 2-tert-butylcyclohexyl acetate to methyl 3-methylcyclohexane-l -carboxylate.
- the 2-tert-butylcyclohexyl acetate and methyl 3-methylcyclohexane-l- carboxylate are present in the fragrance composition at a ratio in the range of 0.18:1 to 2:1 2-tert- butylcyclohexyl acetate to methyl 3-methylcyclohexane-l -carboxylate. In some embodiments, the 2-tert-butylcyclohexyl acetate and methyl 3-methylcyclohexane-l-carboxylate are present in the fragrance composition at a ratio of 3:1 2-tert-butylcyclohexyl acetate to methyl 3- methyl cyclohexane- 1 -carboxylate.
- the 2,4-dimethylcyclohex-3-enecarbaldehyde and 1 -ethyl-2- methylpropyl crotonate are present in the fragrance composition at a ratio in the range of 1:16 to 1:401 2,4- dimethylcyclohex-3-enecarbaldehyde to l-ethyl-2-methylpropyl crotonate.
- the 2,4-dimethylcyclohex-3-enecarbaldehyde and 1 -ethyl-2- methylpropyl crotonate are present in the fragrance composition at a ratio in the range of 1:4 to 1:16 2,4- dimethylcyclohex-3-enecarbaldehyde to l-ethyl-2-methylpropyl crotonate.
- the 2,4-dimethylcyclohex-3-enecarbaldehyde and 1 -ethyl-2- methylpropyl crotonate are present in the fragrance composition at a ratio in the range of 1:0.15 to 1:15 2,4- dimethylcyclohex-3-enecarbaldehyde to l-ethyl-2-methylpropyl crotonate.
- the 2,4-dimethylcyclohex-3-enecarbaldehyde and 1 -ethyl-2- methylpropyl crotonate are present in the fragrance composition at a ratio in the range of 1:0.15 to 1:4 2,4- dimethylcyclohex-3-enecarbaldehyde to l-ethyl-2-methylpropyl crotonate.
- fragrance compositions having a clean attribute as described herein are widely applicable to any perfumery product, including perfumes and colognes, the perfuming of personal care products such as soaps, shower gels, and hair care products, fabric care products, air fresheners, and cosmetic preparations.
- fragrance compositions having a clean attribute provided herein are used to perfume cleaning agents, such as, but not limited to, detergents, dishwashing materials, scrubbing compositions, window cleaners and the like.
- fragrance compositions having a clean attribute can be used alone or in combination with other perfuming compositions, solvents, adjuvants, and the like.
- the nature and variety of the other ingredients that can also be employed are known to those with skill in the art. Many types of additional fragrances can be employed so long as the fragrance is complementary (i.e., compatible) with the other components being employed.
- the fragrance compositions having a clean attribute provided herein may be well-suited for use in a variety of consumer products and can be used as a neat fragrance formulation or may be encapsulated and/or delivered using a suitable carrier material.
- suitable carrier material include, for example, polymers, oligomers, other non-polymers such as surfactants, emulsifiers, lipids including fats, waxes and phospholipids, organic oils, mineral oils, petrolatum, natural oils, perfume fixatives, fibers, starches, sugars, and solid surface materials such as zeolite and silica.
- consumer products containing a fragrance composition having a clean attribute are consumer products containing a fragrance composition having a clean attribute.
- the consumer product is a cleaning product, home care product, fabric care product, personal care product, air care product, and/or cosmetic product.
- Consumer products may include, for example, perfumes, colognes, bar soaps, liquid soaps, shower gels, foam baths, cosmetics, skin care products such as creams, lotions and shaving products, hair care products for shampooing, rinsing, conditioning, bleaching, coloring, dyeing and styling, deodorants and antiperspirants, feminine care products such as tampons and feminine napkins, baby care products such as diapers, bibs and wipes, family care products such as bath tissues, facial tissues, paper handkerchiefs or paper towels, fabric products such as fabric softeners and fresheners, air care products such as air fresheners and fragrance delivery systems, cosmetic preparations, cleaning agents and disinfectants such as detergents, dishwashing materials, scrubbing compositions, glass and metal cleaners
- the consumer product is a shampoo and/or hair conditioner. In some embodiments, the consumer product is a bar soap or liquid soap. In some embodiments, the consumer product is a fabric cleaner. In some embodiments, the consumer product is a laundry detergent. In some embodiments, the consumer product is a cleaning product. [0044] In an aspect is provided a method of evoking sense of clean in a subject, including delivering a fragrance composition described herein or a consumer product described herein to a subject. In some embodiments, the delivering occurs by the subject using the fragrance composition or consumer product having a clean attribute.
- a subject who comes into contact with an object or area where a fragrance composition or consumer product having a clean attribute was used e.g., applied, washed, sprayed, or otherwise engaged as applicable, and the encounter evokes the sense of clean in the subject.
- the delivering occurs by a passive interaction with the fragrance composition or consumer product having a clean attribute.
- Also provided herein are methods for producing a fragrance composition or a consumer product having a clean attribute including formulating one or more of 2,6-dimethyloct-7-en-2-ol and (e)-l -ethoxydec- 1-ene and/or ethyl 5-norbornene-2-carboxylate, 2-tert-butylcyclohexyl acetate and methyl 3-methylcyclohexane-l-carboxylate, or 2,4-dimethylcyclohex-3- enecarbaldehyde and l-ethyl-2-methylpropyl crotonate into a fragrance composition or consumer product.
- formulating includes adding one or more ingredients, reducing one or more ingredients, or any combination thereof to a fragrance composition to impart the clean attribute.
- the fragrance ingredient combination may be directly formulated into a consumer product.
- a fragrance composition containing a fragrance ingredient combination that evokes the clean sensation may be directly formulated into a consumer product.
- the method includes formulating an ingredient combination described herein into a new fragrance composition.
- a new fragrance composition is meant a fragrance that does not currently exist. Therefore, a new fragrance composition may be specifically designed to have a clean attribute. In these cases, the method includes selecting the fragrance ingredient combination that evokes a clean sensation to be formulated into the new fragrance.
- the method includes formulating the ingredient combinations into an existing fragrance composition.
- the fragrance ingredient combination is added into the fragrance composition because the ingredients of the combination are not present in the existing fragrance.
- only one of the fragrance ingredients of the combination is added to the existing fragrance composition.
- the existing fragrance composition may originally include one of the fragrance ingredients of the combination, and thus, to deliver the clean sensation, the other fragrance ingredient of the combination is added to the existing fragrance.
- one fragrance ingredient of the combination of ingredients that evoke a clean sensation is newly added to the fragrance composition and the other fragrance ingredient of the combination is reduced in the fragrance composition because although it is present in the fragrance composition it must be reduced to achieve the concentrations or ratio needed to evoke the clean sensation.
- the method includes formulating the ingredient combinations into an existing fragrance composition where the ingredient combination is present but not at concentrations and/or at a ratio that evokes a clean sensation.
- the fragrance ingredients of a combination are, independently, added into or reduced in the existing fragrance composition to bring the ingredients into a concentration range or ratio range that evokes a clean sensation.
- both ingredients are added to increase the concentration of the ingredients in the fragrance composition.
- both ingredients are reduced in the composition to decrease the concentration of the ingredients in the fragrance composition.
- one ingredient is reduced in the composition to decrease the concentration of the ingredient in the fragrance composition and the other is added to increase the concentration of the ingredient in the fragrance composition.
- no change is made to one of ingredients of the combination and the other ingredient is added or reduced in the composition. In these cases, the formulation brings the fragrance ingredient combination into the ratio and/or concentration range that delivers the clean sensation.
- a fragrance composition having a clean attribute comprising one or more of: (a) 2,6- dimethyloct-7-en-2-ol and (e)-l -ethoxydec- 1-ene, ethyl 5-norbornene-2-carboxylate, or both (e)-
- 3-enecarbaldehyde and the 1 -ethyl-2-methylpropyl crotonate are present at a ratio in a range from 1 :0.15 to 1:401 2,4-dimethylcyclohex-3-enecarbaldehyde to l-ethyl-2-methylpropyl crotonate.
- 3-enecarbaldehyde and the l-ethyl-2- methylpropyl crotonate are present at a ratio of 1 : 10 2,4- dimethylcyclohex-3-enecarbaldehyde to 1 -ethyl-2- methylpropyl crotonate.
- fragrance composition of any one of embodiments 1-11 wherein the 2-tert- butylcyclohexyl acetate is present at a concentration in a range of about 3 wt% to about 33 wt% of the total weight of the fragrance composition and the methyl 3-methylcyclohexane-l- carboxylate is present at a concentration in a range of about 0.05 wt% to about 16 wt% of the total weight of the fragrance composition.
- fragrance composition of any one of embodiments 1-14, wherein the fragrance composition is a sketch, an accord, or a full fragrance.
- a consumer product comprising a fragrance composition of any one of embodiments 1-15.
- a method for producing a fragrance composition or a consumer product having a clean attribute comprising formulating one or more of: (a) 2,6-dimethyloct-7-en-2-ol and (e)-l- ethoxydec-l-ene, ethyl 5-norbornene-2-carboxylate, or both (e)-l -ethoxydec- 1-ene and ethyl 5- norbornene-2-carboxylate; (b) 2-tert-butylcyclohexyl acetate and methyl 3 -methylcyclohexane- 1- carboxylate; or (c) 2,4-dimethylcyclohex-3-enecarbaldehyde and l-ethyl-2- methylpropyl crotonate; into a fragrance composition or consumer product.
- fragrance composition is an existing fragrance composition comprising one or more of 2,6-dimethyloct-7-en-2-ol, (e)-l -ethoxydec- 1-ene, ethyl 5-norbomene-2-carboxylate, 2-tert-butylcyclohexyl acetate, methyl 3 -methylcyclohexane- 1- carboxylate, 2,4-dimethylcyclohex-3-enecarbaldehyde, or l-ethyl-2-methylpropyl crotonate.
- the fragrance composition is an existing fragrance composition comprising one or more of 2,6-dimethyloct-7-en-2-ol, (e)-l -ethoxydec- 1-ene, ethyl 5-norbomene-2-carboxylate, 2-tert-butylcyclohexyl acetate, methyl 3 -methylcyclohexane- 1- carboxylate, 2,4-dimethylcyclo
- fragrance composition is an existing fragrance composition that does not comprise one or more of 2,6-dimethyloct-7-en-2-ol, (e)-l -ethoxy dec- 1-ene, ethyl 5-norbornene-2-carboxylate, 2-tert-butylcyclohexyl acetate, methyl 3 -methylcyclohexane- 1 -carboxylate, 2,4-dimethylcyclohex-3-enecarbaldehyde, or l-ethyl-2- methylpropyl crotonate.
- a method of evoking a sense of clean in a subject comprising delivering a fragrance composition of any one of embodiments 1-15 or a consumer product of embodiment 16 or embodiment 17 to a subject.
- Example 1 Determination of fragrance ingredients that evoke a clean sensation in consumers.
- fragrances each containing 20 to 25 fragrance ingredients at known concentrations, were prepared. The fragrances were assessed using two test product applications: (1) a blind sniff test in beads wrapped into a dry towel for fabric care; and (2) a blind sniff test in dilution for body care.
- the panelists were each asked to group each of the 30 fragrances into 3-10 groups (with each fragrance being a member of only one group) based on how the fragrances smelled, i.e., grouping of fragrances perceived to be similar to each other. After the groups were created, the panelist was asked to describe the different groups using a questionnaire. Table El shows the portion of the questionnaire directed to quantifying a sense of clean evoked by the fragrances.
- Panelist responses were collected in a database and paired accordingly with each tested fragrance, including the concentrations of each ingredient in the fragrance.
- association rule mining as described in WO2023107564, was used to identify fragrance ingredient combinations with an increased likelihood of having a clean score of 8 or 9 and described by at least one phrase selected from “it provides basic efficient cleaning,” “it goes beyond deep cleaning,” “it provides a soft cleaning,” “it fights and prevents malodors,” and “it facilitates the cleaning process.”
- the term “Clean” is used to describe all responses of interest.
- Table E3 Ingredient combinations and concentration ranges, average ratio of ingredients, and lift for “Clean” rules.
- Table E4 Percentage of panelists who found any fragrance containing Rule 1 (see Table E3) to be “Clean.”
- Table E5 Percentage of panelists who found any fragrance containing Rule 2 (see Table E3) to be “Clean.”
- Table E6 Percentage of panelists who found any fragrance containing Rule 3 (see Table E3) to be “Clean.”
- Table E7 Percentage of panelists who found any fragrance containing Rule 4 (see Table E3) to be “Clean.”
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Abstract
L'invention concerne des compositions et des procédés comprenant des ingrédients de parfum qui confèrent un attribut de type sensation de propre.
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| US202363545722P | 2023-10-25 | 2023-10-25 | |
| US63/545,722 | 2023-10-25 |
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| WO2025090783A1 true WO2025090783A1 (fr) | 2025-05-01 |
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