WO2024137340A1 - Fragrance compositions and uses thereof - Google Patents
Fragrance compositions and uses thereof Download PDFInfo
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- WO2024137340A1 WO2024137340A1 PCT/US2023/084072 US2023084072W WO2024137340A1 WO 2024137340 A1 WO2024137340 A1 WO 2024137340A1 US 2023084072 W US2023084072 W US 2023084072W WO 2024137340 A1 WO2024137340 A1 WO 2024137340A1
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- 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
- A61K8/60—Sugars; Derivatives thereof
- A61K8/602—Glycosides, e.g. rutin
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- 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
- A61K8/60—Sugars; Derivatives thereof
- A61K8/608—Derivatives containing from 2 to 10 oxyalkylene groups
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
Definitions
- Inventive subject matter herein relates to the field of perfumery.
- it provides compositions comprising fragrance materials and at least one substantially non- odorous fragrance modulator for creating a bottom-heavy driven fragrance profile that are over-dosed with respect to the base note character without a harsh perception by a panel of experts or professional evaluators or individual experts or professional evaluators.
- the invention also relates to methods of making and using said compositions.
- BACKGROUND OF THE DISCLOSURE Fragrances can include fragrance components that can be classified, in part, by their volatility. Accordingly, these fragrance components may be referred to as a high-, moderate-, or low-volatility fragrance components. Different fragrances may be dominated by any one or more of these component such that the fragrance may be associated with different perceptions by a user. Furthermore, although the low-volatility fragrance may be present for a comparatively longer period of time, compositions including a relatively high amount of specific low and moderate-volatility fragrance materials (e.g., an over-dose) may be perceived as having a harsh and unpleasant perception by a panel of experts or professional evaluators or individual experts or professional evaluators.
- specific low and moderate-volatility fragrance materials e.g., an over-dose
- a fragrance composition includes less than or equal to 2 wt% glucam.
- the fragrance composition further includes a fragrance component comprising d-limonene (CAS No.5989-27-5), Indole (CAS No.
- Thujopsene (CAS No.470-40-6), alpha – cedrene (CAS No.469-61-4), beta – cedrene (CAS No.546-28-1), beta ionone (CAS No.14901-07-6), Methyl Anthranilate (CAS No.134-20-3), Cedramber (CAS No.67874-81-1), cyclamen aldehyde (CAS No.103-95-7), Ambroxan (CAS No.6790-58-5), Mysore acetate (CAS No.30772-69-1), Polywood (CAS No.98676-96-1), Boisambrene forte (CAS No.58567-11-6), alpha-iso-methylionone (CAS No.127-51-5), Helional (CAS No.
- At least one of the low volatile fragrance material, the moderate volatile fragrance material, and the high volatile fragrance material is present in the fragrance component for a period of time that is longer than a corresponding fragrance component that is free of the substantially non-odorous fragrance modulator.
- the characteristics of the composition can provide rules for objectively classifying fragrance materials according to their volatility using their vapor pressures defined at suitable temperature, instead of their characters.
- the objective rules operate irrespective of perfumers performing the classification.
- the rules classify the fragrance materials into low, moderate or high volatile fragrance materials for formulating into fragrance mixtures.
- the presence of the modulator can allow for compositions where the perception of the panel of experts or professional evaluators or individual experts or professional evaluators is driven by the moderate and low-volatility fragrance materials.
- the modulator allows for overdosing of at least one of the low and moderate volatility fragrance materials.
- the fragrance component can include multiple high or moderate volatile materials.
- an individual high or low volatile material may be present in an amount greater than a corresponding material in a traditional fragrance—thus constituting an overdose.
- the typical harshness, as perceived by a panel of experts or professional evaluators or individual experts or professional evaluators panel of experts or professional evaluators or individual experts or professional evaluators can be minimized at least in part by the presence of the modulator.
- the low-volatility fragrance material is a natural material and is over-dosed, which absent the modulator, produces a harshness that is not acceptable to a panel of experts or professional evaluators or individual experts or professional evaluators.
- articles such as “a” and “an” when used in a claim are understood to mean one or more of what is claimed or described.
- the terms “include”, “includes” and “including” are meant to be non- limiting.
- the term “body splash” means a body care formulation that is applied to the body.
- the body splash is applied to the body after bathing and provides a subtle hint of scent to the body.
- Body splashes are commonly used by consumers who prefer less strong fragrance compositions.
- a body splash may comprise an ethanol-free composition according to the present invention which comprises from 0.2-8 wt%, relative to the total weight of the composition, of a fragrance component.
- the body splash may further comprise alkyl polyglucosides as non-ionic surfactants.
- body spray means a formulation comprising fragrance materials intended to be applied to the body to prevent or mask body odor caused by the bacterial breakdown of perspiration on the body (e.g., armpits, feet, and other areas of the body).
- the body spray may also provide a fragrance expression to the consumers.
- compositions are applied as an aerosol spray in an effective amount on the skin of a consumer.
- composition includes a fine fragrance composition intended for application to a body surface, such as for example, skin or hair, e.g., to impart a pleasant odor thereto, or cover a malodour thereof. They are generally in the form of perfume concentrates, perfumes, eau de perfumes, eau de toilettes, aftershaves, or colognes.
- the fine fragrance compositions may be an ethanol-based composition.
- composition may also include a cosmetic composition, which comprises a fragrance material for the purposes of delivering a pleasant smell to drive consumer acceptance of the cosmetic composition.
- composition may also include body splashes or body sprays.
- composition may also include cleaning compositions, such as fabric care composition or home care compositions, including air care compositions (e.g., air fresheners), for use on clothing or other substrates such as hard surfaces (e.g., dishes, floors, countertops).
- additional non- limiting examples of “composition” may also include facial or body powder, deodorant, foundation, body/facial oil, mousse, creams (e.g., cold creams), waxes, sunscreens and blocks, bath and shower gels, lip balms, self-tanning compositions, masks and patches.
- the term “consumer” means both the user of the composition and the observer nearby or around the user.
- fragment material and “fragrance materials” relates to a perfume raw material (“PRM”), or a mixture of perfume raw materials (“PRMs”), that are used to impart an overall pleasant odor or fragrance profile to a composition.
- “Fragrance materials” can encompass any suitable perfume raw materials for fragrance uses, including materials such as, for example, alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpene hydrocarbons, nitrogenous or sulfurous heterocyclic compounds and essential oils.
- materials such as, for example, alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpene hydrocarbons, nitrogenous or sulfurous heterocyclic compounds and essential oils.
- naturally occurring plant and animal oils and exudates comprising complex mixtures of various chemical components are also known for use as “fragrance materials”.
- perfume raw materials which comprise a known natural oil can be found by reference to Journals commonly used by those skilled in the art such as “Perfume and Flavourist” or “Journal of Essential Oil Research”, or listed in reference texts such as the book by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA and more recently re-published by Allured Publishing Corporation Illinois (1994). Additionally, some perfume raw materials are supplied by the fragrance houses (Firmenich, International Flavors & Fragrances, Givaudan, Symrise) as mixtures in the form of proprietary specialty accords.
- Non-limiting examples of the fragrance materials useful herein include pro-fragrances such as acetal pro-fragrances, ketal pro-fragrances, ester pro- fragrances, hydrolyzable inorganic-organic pro-fragrances, and mixtures thereof.
- the fragrance materials may be released from the pro-fragrances in a number of ways. For example, 0 the fragrance may be released as a result of simple hydrolysis, or by a shift in an equilibrium reaction, or by a pH-change, or by enzymatic release.
- the term “fragrance profile” means the description of how the fragrance is perceived by the human nose at any moment in time. The fragrance profile may change over time.
- a fragrance profile is composed of 2 characteristics: ‘intensity’ and ‘character’.
- the ‘intensity’ relates to the perceived strength whilst ‘character’ refers to the odor impression or quality of the perfume, e.g., fruity, floral, woody, etc.
- the terms “modulator”, and “fragrance modulator” are used interchangeably to designate an agent having the capacity to affect the fragrance profile, such as for example, by impacting the fragrance materials’ evaporation rate.
- the modulator may mediate its effect by lowering the vapor pressure of the fragrance materials and increasing their adherence to the substrate (skin and/or hair) thus ensuring a less harsh impression of the overdosed fragrance.
- the fragrance profile preferably the fragrance components composition attributable to the moderate and low volatile fragrance materials, alone or individually, of the composition can be perceived by a panel of experts or professional evaluators or individual experts or professional evaluators, without the perceived harshness of overdosing (e.g., greater than about 30 wt% of the composition) of the low and moderate fragrance materials is mitigated or absent, as compared to the same perception in the absence of the modulator.
- Suitable examples of the modulator are provided herein below.
- the term “substantially non-odorous” means an agent that does not impart an odor of its own when added into a composition of the present invention.
- a “substantially non-odorous fragrance modulator” does not impart a new odor that alters the character of the fragrance profile of the composition to which it is added.
- substantially non-odorous also encompasses an agent that may impart a minimal or slight odor of its own when added into a composition of the present invention.
- the odor imparted by the “substantially non-odorous fragrance modulator” is generally undetectable or tends to not substantively alter the character of the fragrance profile of the composition to which it is added initially or preferably over time.
- substantially non- odorous also includes materials that are perceivable only by a minority of people or those materials deemed “anosmic” to the majority of people.
- substantially non-odorous also includes materials that may, from particular suppliers, contain an odor due to impurities, such as when the materials contain the impurities at not more than about 5 wt%, preferably not more than 1 wt%, often even not more than 1 part per million (ppm). These impurities maybe removed by purification techniques known in the art as required to make them suitable for use in fragrance compositions of the present invention.
- vapor pressure means the partial pressure in air at a defined temperature (e.g., 25 °C) and standard atmospheric pressure (760 mmHg) for a given chemical species. It defines a chemical species’ desire to be in the gas phase rather than the liquid or solid state.
- the vapor pressure is determined according to the reference program Advanced Chemistry Development (ACD/Labs) Software Version 14.02, or preferably the latest version update). It is understood that the test methods that are disclosed in the Test Methods Section of the present application must be used to determine the respective values of the parameters of Applicants’ inventions as described and claimed herein. In all embodiments of the present invention, all percentages are by weight of the total composition, as evident by the context, unless specifically stated otherwise.
- fragrance compositions can include at least a fragrance component and modulator.
- the fragrance component can include a wide variety of fragrance materials.
- the fragrance materials can be grouped in terms of their volatility. Generally, the materials can be grouped as low volatile fragrance materials, moderate volatile fragrance materials, and high volatile fragrance materials.
- Each group of materials can be associated with various perceptions by a panel of experts or professional evaluators or individual experts or professional evaluators. While not so limited, a high volatile fragrance may be associated with a citrus character; a moderate voile fragrance may be associated with a spicy character; and a low volatile fragrance may be associated with a woody character.
- Each group of fragrance materials can include synthetic materials or natural materials. The volatility of the fragrance materials can be in reference to an individual fragrance material. Alternatively, in cases where a combination of materials produce a fragrance the volatility may be in reference to that aggregation.
- the fragrance component can be present in an amount of from about 0.04 wt% to 30 wt%, 1 wt% to about 30 wt%, about 5 wt% to about 30 wt%, or less than, equal to, or greater than about 0.04 wt%, 0.5, 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, 5, 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 9.5, 10, 10.5, 11, 11.5, 12, 12.5, 13, 13.5, 14, 14.5, 15, 15.5, 16, 16.5, 17, 17.5, 18, 18.5, 19, 19.5, 20, 20.5, 21, 21.5, 22, 22.5, 23, 23.5, 24, 24.5, 25, 25.5, 26, 26.5, 27, 27.5, 28, 28.5, 29, 29.5, or about 30 wt% relative to the composition.
- the modulator can be present in an amount of from about 0.1 wt% to about 20 wt%, about 0.5 wt% to about 20 wt%, or less than, equal to, or greater than about 0.1 wt%, 0.5, 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, 5, 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 9.5, 10, 10.5, 11, 11.5, 12, 12.5, 13, 13.5, 14, 14.5, 15, 15.5, 16, 16.5, 17, 17.5, 18, 18.5, 19, 19.5, or about 20 wt% relative to the composition.
- the “fragrance materials” have been classified as low, moderate or high volatile fragrance materials according to their volatility by their vapor pressure.
- fragrance materials are a natural oil, extract or absolute, which comprises a mixture of several compounds
- the vapor pressure of the complete oil should be treated a mixture of the individual perfume raw material components using the reference program cited above.
- the individual components and their level, in any given natural oil or extract can be determined by direct injection of the oil into a GC-MS column for analysis as known by one skilled in the art.
- the vapor pressure, using the reference program cited above should preferably be obtained from the supplier.
- the fragrance component comprises at least one low volatile fragrance material.
- the composition can include at least 3 low volatile fragrance materials, or at least 4 low volatile fragrance materials, or at least 5 low volatile fragrance materials, or at least 7 low volatile fragrance materials.
- the amount of the low fragrance material present in the fragrance component can vary depending on the specific application.
- the low volatile fragrance material can be greater than about 30 wt% of the fragrance component, greater than about 40 wt%, greater than about 50 wt%, greater than about 60 wt%, about 31 wt% to about 60 wt%, about 40 wt% to about 50 wt%, or less than, equal to, or greater than about 30 wt%, 31, 35, 40, 45, 50, 55, 60, 65, 70 ,or 75 wt%. If there are more than one low volatile fragrance materials, then the ranges provided hereinabove cover the total of all the low volatile fragrance materials. Examples of suitable low volatile fragrances materials are provided in Table 1A and 1B below.
- the low volatile fragrance material is selected from at least 1 material, or at least 2 materials, or at least 3 materials, or at least 5 materials, at least 7, at least 8, at least 10, or at least 12 low volatile fragrance materials as disclosed in Table 1A.
- Natural fragrance materials or oils having an aggregrate vapour pressure less than 0.001 Torr (0.000133 kPa) at 25 °C are provided in Table 1B.
- the low volatile fragrance materials may be obtained from one or more of the following companies: Firmenich (Geneva, Switzerland), Symrise AG (Holzminden, Germany), Givaudan (Argenteuil, France), IFF (Hazlet, New Jersey), Bedoukian (Danbury, Connecticut), Sigma Aldrich (St. Louis, Missouri), Millennium Specialty Chemicals (Olympia Fields, Illinois), Polarone International (Jersey City, New Jersey), and Aroma & Flavor Specialties (Danbury, Connecticut).
- the fragrance component includes at least one moderate volatile fragrance material or aggregate of volatile fragrance materials having a vapor pressure in the range of 0.1 Torr to 0.001 Torr (0.0133 kPa to 0.000133 kPa) at 25 °C.
- the composition according to the present disclosure can include at least 3 moderate volatile fragrance materials, or at least 5 moderate volatile fragrance materials, or at least 7 moderate volatile fragrance materials.
- Compositions of the present invention can include high levels of the moderate volatile fragrance materials present in an amount of from about 30 wt% to about 70 wt%, about 35 wt% to about 60 wt%, or less than equal to, or greater than about 30 wt%, 35, 40, 45, 50, 55, 60, 65, or 70 wt% of the fragrance component. If there are more than one moderate volatile fragrance materials, then the ranges provided hereinabove cover the total of all of the moderate volatile fragrance materials. Suitable examples of moderate volatile fragrances materials are provided in Table 2A and 2B below.
- moderate volatile fragrance materials having a vapor pressure in the range of 0.1 Torr to 0.001 Torr (0.0133 kPa to 0.000133 kPa) at 25 °C are provided in Table 2 Moderate Volatile Fragrance Materials.
- the moderate volatile fragrance material is selected from at least 1 material, or at least 2 materials, or at least 3 materials, or at least 5 materials, or at least 7 moderate volatile fragrance materials as disclosed in Table 2A.
- Natural fragrance materials or oils having an aggregrate vapour pressure between 0.1 Torr to 0.001 Torr (0.0133 kPa to 0.000133 kPa) at 25 °C are provided in Table 2B.
- Moderate Volatile Natural Oils Moderate Volatile Natural Oils.
- the fragrance component includes at least one high volatile fragrance material having a vapor pressure greater than 0.1 Torr (0.0133 kPa) at 25 °C.
- the high volatile fragrance material can include at least 2 high volatile fragrance materials, 3 high volatile fragrance materials, or at least 5 high volatile fragrance materials, or at least 7 high volatile fragrance materials.
- the high volatile fragrance material can be present in an amount ranging from about 0.1 wt% to about 30 wt% of the fragrance component, about 1 wt% to about 30 wt%, about 5 wt% to about 30 wt%, or less than, equal to, or greater than about 0.1 wt%, 0.5, 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, 5, 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 9.5, 10, 10.5, 11, 11.5, 12, 12.5, 13, 13.5, 14, 14.5, 15, 15.5, 16, 16.5, 17, 17.5, 18, 18.5, 19, 19.5, 20, 20.5, 21, 21.5, 22, 22.5, 23, 23.5, 24, 24.5, 25, 25.5, 26, 26.25, 27, 27.5, 28, 28.5, 29, 29.5, or about 30 wt%.
- the ranges provided hereinabove cover the total of all of the high volatile fragrance materials.
- Suitable examples of high volatile fragrances materials are provided in Tables 3A and 3B below.
- the high volatile fragrance material is selected from at least 1 material, or at least 2 materials, or at least 3 materials, or at least 5 materials, at least 7 materials, or at least 9 high volatile fragrance materials as disclosed in Table 3A.
- Natural fragrance materials or oils having an aggregrate vapour pressure greater than 0.1 Torr (0.0133 kPa) at 25 °C are provided in Table 3B.
- [Table 3A] High Volatile Fragrance Materials * Vapor Pressures are acquired as described in the Test Methods Section.
- composition further comprises at least one substantially non-odorous fragrance modulator as described herein below. Suitable examples of the substantially non-odorous fragrance modulators are provided in Table 4 below.
- the substantially non-odorous fragrance modulator can be present in an amount of from about 0.1 wt% to about 20 wt% relative to the total weight of the composition of the composition, about 0.5 wt% to about 18 wt%, about 2.5 wt% to about 15 wt%, or less than, equal to, or greater than about 0.1 wt%, 0.5, 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, 5, 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 9.5, 10, 10.5, 11, 11.5, 12, 12.5, 13, 13.5, 14, 14.5, 15, 15.5, 16, 16.5, 17, 17.5, 18, 18.5, 19, 19.5, 20 wt%.
- the substantially non-odorous fragrance modulator can be a liquid at temperatures lower than 100 °C, such as at ambient temperature.
- the substantially non-odorous fragrance modulators may be fully miscible with the fragrance materials to form a single phase liquid.
- co- solvents e.g., dipropylene glycol (DPG), triethyl citrate, or others well known to those skilled in the art
- the effect of the substantially non-odorous fragrance modulator on the fragrance profile can be improved.
- improved it is meant that the fragrance profile of the composition, particular the components contributed by at least one of the low and high volatile fragrance materials, can be perceived by the panel of experts or professional evaluators or individual experts or professional evaluators at later time points such as, for example, 1 hour, 2 hours, 3 hours, 4 hours, 5 hours, 6 hours, 7 hours, 8 hours, 10 hours, and possibly all the way up to 24 hrs after application as compared to controls, e.g., lacking any of the disclosed non-odorous fragrance modulators such as Glucam.
- the substantially non-odorus modulator is Glucam
- the Glucam is less than or equal to 2 wt% of the composition.
- improved it can mean that the perception by the panel of experts or professional evaluators or individual experts or professional evaluators, of a harshness of the composition being loaded with greater than 30 wt% of the low-fragrance material is reduced or eliminated.
- Suitable examples of non-odorous modulators can include methyl glucoside polyol, ethyl glucoside polyol, propyl glucoside polyol, or mixtures thereof.
- Further examples can include from polypropylene glycol-10 methyl glucose ether, ethoxylated methyl glucose ether, polypropylene glycol-20 methyl glucose ether, caprylyl/capryl glucoside, undecyl glucoside, and mixtures thereof.
- the composition can be substantially free of isocetyl alcohol, diisobutyl adipate, diisoamyl adipate, polypropylene glycol-3 myristyl ether, and neopentyl glycol diethyl hexanoate, neopentyl glycol diisononanoate, cetearyl ethyl hexanoate, and their mixtures, or a mixture thereof, althought the composition can optionally include these.
- non-odorous modulators include: a compound of formula (I): wherein: R 1 is hydrogen, alkyl, alkenyl or alkynyl; R 2 is selected from hydrogen, (C 2 -C 20 )alkyl, (C 2 -C 20 )alkenyl, (C 2 -C 20 )alkynyl, -[R 6 R 7 (R 8 )0]wR 9 ,wherein w is from 1 to 10, preferably 2 to 9; R 3 is selected from hydrogen, alkyl, alkenyl, alkynyl, -[R 6 R ⁇ R 8 )0]yR 9 ,wherein y is from 1 to 10 or 2 to 9; R 4 is selected from hydrogen, alkyl, alkenyl, alkynyl, -[R 6 R ⁇ R 8 )0 ]xR 9 ,wherein x is from 1 to 10, preferably 2 to 9; R 5 is selected from hydrogen, alkyl, alkenyl, alkynyl
- C 6 H x O y is a hexose residue, wherein x is an integer from 7 to 11, and y is an integer from 1 to 5; z is an integer from 1 to 5; and R 1d is C 4 -C 20 hydrocarbon group; and Diethylene Glycol Ether derivatives having the formula (VIII) or formula (IX): wherein: C 5 H c O d is a pentose residue, wherein c is an integer from 6 to 8, and d is an integer from 1 to 3; e is an integer from 2 to 4; a nd R 1e is C1-C6 alkyl group; and (IX).
- C 6 H f O g is a hexose residue, wherein f is an integer from 7 to 10, and g is an integer from 1 to 4; h is an integer from 2 to 5; a nd R 1f is C1-C6 alkyl group; Hydroquinone Glycoside derivatives having the formula (X): (X).
- R 1i is C4-C5 alkyl; alkylene; and R 3i is C4-C5 alkyl; and Aliphatic Ether derivatives having the formula (XIII): (XIII).
- a and b are integers such that the sum of a and b is from 1 to 4; and R 4i is an aliphatic chain comprising from 8 to 18 carbons; N-hexadecyl n-nonanoate, Noctadecyl n-nonanoate and their mixtures; Tricyclodecane Amide derivatives selected from the group consisting of: the compounds of formula (XIV): wherein: X is selected from: Y is hydrogen, or a halogen; and each R 1j is independently selected from a hydrogen, or C 1 -C 4 alkyl; the compounds of formula (XV): (XV).
- each R 2j is independently selected from a hydrogen, methyl, ethyl or C 3 - C 18 alkyl, cycloalkyl or cycloheteroalkyl, with the proviso that both R 2e groups are not hydrogen; and mixtures of the compounds of formulae (XII) and (XIII); and mixtures thereof.
- Tables 4(a) and 4(b) provide lists of suitable non-odorous fragrance modulators. [Table 4(a)] Substantially Non-Odorous Fragrance Modulators 1 available as GLUCAMTM P-20. 2 available as GlucamTM E-20. 3 available as Plantacare ® 810 UP. 3a available as Simulsol ® SL 11W.
- non-odorous fragrance modulator is selected from the group of materials disclosed in Table 4(b).
- Table 4(b) Substantially Non-Odorous Fragrance Modulators
- the substantially non-odorous fragrance modulators associate to the low-volatility fragrance materials to allow for high wt% (e.g., greater than 30 wt%) of the composition to allow the low-volatility fragrance materials to drive the perceived character of the fragrance, while mitigating or eliminating a perceived harshness of the composition by the user.
- the composition according to the present invention can include a volatile solvent present in the amount of from about 20 wt% to about 99 wt% relative to the total weight of the composition, about 30 wt% to about 80 wt%, about 55 wt% to about 75 wt%, or less than, equal to, or greater than about 20 wt%, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, or about 99 wt%, and wherein the solvent is a branch or unbranched C1 to C10 alkyl, akenyl or alkynyl group having at least one alcohol moiety, preferably ethanol, or isopropanol, or other alcohols (e.g., methanol, propanol, isopropanol, butanol, and mixtures thereof) commonly found in commercial fine fragrance products.
- a volatile solvent present in the amount of from about 20 wt% to about 99 wt% relative to the total weight of the composition
- ethanol may be present in any of the compositions of the present invention, and more specifically, it will form from about 5 wt% to about 95 wt%, or even from about 10 wt% to about 80 wt%, 25 wt% to about 75 wt% of the composition, or combinations thereof, relative to the total weight of the composition.
- ethanol may be present in an amount of from about 10 wt% or 25 wt% to about 75 wt% or 80 wt%, relative to the total weight of the composition.
- the ethanol useful in the present invention may be any acceptable quality of ethanol, compatible and safe for the specific intended use of the composition such as, for example, topical applications of fine fragrance or cosmetic compositions.
- water may be present in any of the compositions of the present invention, and more specifically, it may not exceed about 95 wt% relative to the total weight of the composition, about 90 wt% or less, about 85 wt% or less, about 80 wt% or less, about 75 wt% or less, about 70 wt% or less, about 65 wt% or less, about 60 wt% or less, about 55 wt% or less, about 50 wt% or less, about 45 wt% or less, about 40 wt% or less, about 35 wt% or less, about 30 wt% or less, about 20 wt% or less, about 10 wt%, or less than, equal to, or greater than about 95 wt%, 90, 85, 80, 75, 70, 65, 60, 55, 50 ,45, 40, 30, 35, 30, 25, 20, 15, 10, or 5 wt%.
- water may be present in an amount of from about 5 wt% or about 95 wt%
- the level of water should not be so high that the product becomes cloudy thus negatively impacting the product aesthetics.
- the amount of water present in the composition may be from the water present in the volatile solvent (e.g., ethanol) used in the composition, as the case may be.
- the composition may comprise a non-volatile solvent or a mixture of non-volatile solvents.
- Non-limiting examples of non-volatile solvents include benzyl benzoate, diethyl phthalate, isopropyl myristate, propylene glycol, dipropylene glycol, triethyl citrate, and mixtures thereof. These solvents often are introduced to the product via the perfume oil as many perfume raw materials may be purchased as a dilution in one of these solvents. Where non-volatile solvents are present, introduced either with the perfume materials or separately, then for the purposes of calculating the proportion of fragrance component having a vapor pressure of less than 0.001 Torr (0.000133 kPa) at 25 °C the total fragrance components does not include non-volatile solvents.
- non-volatile solvents are present, introduced either with the perfume materials or separately, then for the purposes of calculating the total level of fragrance component this does not include non-volatile solvents.
- the non-volatile solvent may be included at a weight ratio of the non- volatile solvent to the cyclic oligosaccharide of less than 1:1, less than 1:2, less than 1:10, or less than 1:100.
- compositions of the present invention can include an entrapment material at a level such that the weight ratio of the entrapment material to the fragrance materials is in the range of from about 1:20 to about 20:1.
- the composition may comprise an entrapment material present in the amount of from about 0.001 wt% to about 40 wt%, from about 0.1 wt% to about 25 wt%, from about 0.3 wt% to about 20 wt%, from about 0.5 wt% to about 10 wt%, or from about 0.75 wt% to about 5 wt%, relative to the total weight of the composition.
- compositions disclosed herein may include from 0.001 wt% to 40%, from 0.1 wt% to 25 wt%, from 0.3 wt% to 20 wt%, from 0.5 wt% to 10 wt% or from 0.75 wt% to 5 wt%, relative to the total weight of the composition, of a cyclic oligosaccharide.
- Suitable entrapment materials for use herein are selected from polymers; capsules, microcapsules and nanocapsules; liposomes, absorbents; cyclic oligosaccharides and mixtures thereof. Preferred are absorbents and cyclic oligosaccharides and mixtures thereof.
- cyclic oligosaccharides see PCT Publication Nos. WO2000/67721 (Procter & Gamble); and WO2000/67720 (Procter & Gamble); and U.S. Patent No. 6,893,647 (Procter & Gamble)).
- cyclic oligosaccharide means a cyclic structure comprising six or more saccharide units.
- Preferred for use herein are cyclic oligosaccharides having six, seven or eight saccharide units and mixtures thereof, more preferably six or seven saccharide units and even more preferably seven saccharide units.
- the cyclic oligosaccharide of the compositions used for the present invention may comprise any suitable saccharide or mixtures of saccharides.
- suitable saccharides include, but are not limited to, glucose, fructose, mannose, galactose, maltose and mixtures thereof.
- preferred for use herein are cyclic oligosaccharides of glucose.
- the preferred cyclic oligosaccharides for use herein are ⁇ -cyclodextrins or ⁇ -cyclodextrins, or mixtures thereof, and the most preferred cyclic oligosaccharides for use herein are ⁇ - cyclodextrins.
- the cyclic oligosaccharide, or mixture of cyclic oligosaccharides, for use herein may be substituted by any suitable substituent or mixture of substituents.
- the use of the term “mixture of substituents” means that two or more different suitable substituents can be substituted onto one cyclic oligosaccharide.
- the derivatives of cyclodextrins consist mainly of molecules wherein some of the OH groups have been substituted.
- Suitable substituents include, but are not limited to, alkyl groups; hydroxyalkyl groups; dihydroxyalkyl groups; (hydroxyalkyl)alkylenyl bridging groups such as cyclodextrin glycerol ethers; aryl groups; maltosyl groups; allyl groups; benzyl groups; alkanoyl groups; cationic cyclodextrins such as those containing 2-hydroxy-3-(dimethylamino) propyl ether; quaternary ammonium groups; anionic cyclodextrins such as carboxyalkyl groups, sulphobutylether groups, sulphate groups, and succinylates; amphoteric cyclodextrins; and mixtures thereof.
- the substituents may be saturated or unsaturated, straight or branched chain.
- Preferred substituents include saturated and straight chain alkyl groups, hydroxyalkyl groups and mixtures thereof.
- Preferred alkyl and hydroxyalkyl substituents are selected from C1-C8 alkyl or hydroxyalkyl groups or mixtures thereof, more preferred alkyl and hydroxyalkyl substituents are selected from C1-C6 alkyl or hydroxyalkyl groups or mixtures thereof, even more preferred alkyl and hydroxyalkyl substituents are selected from C1-C4 alkyl or hydroxyalkyl groups and mixtures thereof.
- Especially preferred alkyl and hydroxyalkyl substituents are propyl, ethyl and methyl, more especially hydroxypropyl and methyl and even more preferably methyl.
- Suitable cyclic oligosaccharides for use in the present invention are unsubstituted, or are substituted by only saturated straight chain alkyl, or hydroxyalkyl substituents. Therefore, preferred examples of cyclic oligosaccharides for use herein are ⁇ -cyclodextrin, ⁇ - cyclodextrin, methyl- ⁇ -cyclodextrin, methyl- ⁇ -cyclodextrin, hydroxypropyl- ⁇ -cyclodextrin and hydroxypropyl- ⁇ -cyclodextrin.
- cyclic oligosaccharides for use herein are methyl- ⁇ -cyclodextrin and methyl- ⁇ -cyclodextrin. These are available from Wacker-Chemie GmbH Hanns-Seidel-Platz 4, Munchen, DE under the tradename Alpha W6 M and Beta W7 M respectively.
- the cyclic oligosaccharides of the compositions used for the present invention can be soluble in water, ethanol, or both water and ethanol.
- “soluble” means at least about 0.1 g of solute dissolves in 100 mL of solvent, at 25 °C and 1 standard atmospheric pressure (760 mmHg).
- the cyclic oligosaccharides for use herein have a solubility of at least about 1 g/100 mL, at 25 °C and 1 atm of pressure. In some examples, cyclic oligosaccharides are only present at levels up to their solubility limits in a given composition at room temperature. A person skilled in the art will recognize that the levels of cyclic oligosaccharides used in the present invention will also be dependent on the components of the composition and their levels, for example the solvents used or the exact fragrance oils, or combination of fragrance oils, present in the composition. Therefore, although the limits stated for the entrapment material are preferred, they are not exhaustive. Propellants The compositions described herein may include a propellant.
- propellants include compressed air, nitrogen, inert gases, carbon dioxide, and mixtures thereof.
- Propellants may also include gaseous hydrocarbons like propane, n-butane, isobutene, cyclopropane, and mixtures thereof.
- Halogenated hydrocarbons like 1,1- difluoroethane may also be used as propellants.
- propellants include 1,1,1,2,2-pentafluoroethane, 1,1,1,2-tetrafluoroethane, 1,1,1,2,3,3,3- heptafluoropropane, trans-1,3,3,3-tetrafluoroprop-1-ene, dimethyl ether, dichlorodifluoromethane (propellant 12), 1,1-dichloro-1,1,2,2-tetrafluoroethane (propellant 114), 1-chloro-1,1-difluoro-2,2-trifluoroethane (propellant 115), 1-chloro-1,1- difluoroethylene (propellant 142B), 1,1-difluoroethane (propellant 152A), monochlorodifluoromethane, and mixtures thereof.
- propellants suitable for use include, but are not limited to, A-46 (a mixture of isobutane, butane and propane), A-31 (isobutane), A-17 (n-butane), A-108 (propane), AP70 (a mixture of propane, isobutane and n- butane), AP40 (a mixture of propane, isobutene and n-butane), AP30 (a mixture of propane, isobutane and n-butane), and 152A (1,1 diflouroethane).
- A-46 a mixture of isobutane, butane and propane
- A-31 isobutane
- A-17 n-butane
- A-108 propane
- AP70 a mixture of propane, isobutane and n- butane
- AP40 a mixture of propane, isobutene and n-butane
- AP30 a mixture of propane, isobutane and
- the propellant may have a concentration from about 15%, 25%, 30%, 32%, 34%, 35%, 36%, 38%, 40%, or 42% to about 70%, 65%, 60%, 54%, 52%, 50%, 48%, 46%, 44%, or 42% by weight of the total fill of materials stored within the container.
- Antiperspirant Active The compositions described herein may be free of, substantially free of, or may include an antiperspirant active (e.g., any substance, mixture, or other material having antiperspirant activity). Examples of antiperspirant actives include astringent metallic salts, like the inorganic and organic salts of aluminum, zirconium and zinc, as well as mixtures thereof.
- Such antiperspirant actives include, for example, the aluminum and zirconium salts, such as aluminum halides, aluminum hydroxyhalides, zirconyl oxyhalides, zirconyl hydroxyhalides, and mixtures thereof.
- the composition consists essentially of the recited ingredients but may contain small amounts (not more than about 10 wt%, preferably no more than 5 wt%, or preferably no more than 2 wt% thereof, relative to the total weight of the composition) of other ingredients that do not impact on the fragrance profile, particularly the evaporation rate and release of the fragrance materials.
- a fine fragrance composition may comprise stabilizing or anti-oxidant agents, UV filters or quenchers, or colouring agents, commonly used in perfumery.
- compositions for cosmetic use include, but are not limited to, alcohol denaturants such as denatonium benzoate; UV stabilizers such as benzophenone-2; antioxidants such as tocopheryl acetate; preservatives such as phenoxyethanol, benzyl alcohol, methyl paraben, and propyl paraben; dyes; pH adjusting agents such as lactic acid, citric acid, sodium citrate, succinic acid, phosphoric acid, sodium hydroxide, and sodium carbonate; deodorants and anti-microbials such as farnesol and zinc phenolsulphonate; humectants such as glycerine; oils; skin conditioning agents such as allantoin; cooling agents such as trimethyl isopropyl butanamide and menthol; silicones; solvents such as hexylene glycol; hair-hold polymers such as those described in PCT Publication No.
- alcohol denaturants such as denatonium benzoate
- UV stabilizers such as benzophenone-2
- the composition of the present invention is a mixture of fragrance materials possibly together with other ingredients such as, for example, perfume carriers.
- perfume carrier it is meant to include materials which are practically neutral from a perfumery point of view, e.g., which does not significantly alter the organoleptic properties of perfuming components.
- the perfume carrier may be a compatible liquid or solid fillers, diluents, and the like.
- compatible means that the components of the compositions of this invention are capable of being combined with the primary actives of the present invention, and with each other, in a manner such that there is no interaction which would substantially reduce the efficacy of the composition under ordinary use situations.
- the type of carrier utilized in the present invention depends on the type of product desired and may comprise, but are not limited to, solutions, aerosols, emulsions (including oil-in-water or water-in-oil), gels, and liposomes.
- the carrier is a liquid and will be a solvent such as, for example, dipropyleneglycol, diethyl phthalate, isopropyl myristate, benzyl benzoate, 2-(2- ethoxyethoxy)-l-ethanol, or ethyl citrate (triethyl citrate).
- a solvent such as, for example, dipropyleneglycol, diethyl phthalate, isopropyl myristate, benzyl benzoate, 2-(2- ethoxyethoxy)-l-ethanol, or ethyl citrate (triethyl citrate).
- the compositions for use in the present invention may take any form suitable for use, such as for perfumery or cosmetic use.
- compositions for use in the present invention take the form of a vapor spray.
- compositions of the present invention can be further added as an ingredient to other compositions, preferably fine fragrance or cosmetic compositions, in which they are compatible. As such they can be used within solid composition or applied substrates etc.
- the spray dispenser may comprise an aerosolized composition (e.g., a composition comprising a propellant) within the vessel as well.
- aerosolized composition e.g., a composition comprising a propellant
- Other non-limiting examples of spray dispensers include non-aerosol dispensers (e.g., vapor sprays), manually activated dispensers, pump-spray dispensers, or any other suitable spray dispenser available in the art.
- Methods of Using the Compositions The composition of the present invention according to any embodiments described herein is a useful perfuming composition, which can be advantageously used as consumer products intended to perfume any suitable substrate.
- substrate means any surface to which the composition of the present invention may be applied to without causing any undue adverse effect.
- this can include a wide range of surfaces including human or animal skin or hair, paper (fragranced paper), air in a room (air freshener or aromatherapy composition), fabric, furnishings, dishes, hard surfaces and related materials.
- Preferred substrates include body surfaces such as, for example, hair and skin, most preferably skin.
- the composition of the present invention may be used in a conventional manner for fragrancing a substrate.
- An effective amount of the composition such as from about 1 ⁇ L to about 100 mL, preferably from about 10 ⁇ L to about 1,000 ⁇ L, more preferably from about 25 ⁇ L to about 500 ⁇ L, from about 50 ⁇ L to about 100 ⁇ L, from about 100 ⁇ L to about 20 mL, or combinations thereof, is applied to the suitable substrate.
- an effective amount of the composition of the present invention is less than, equal to, or greater than about 1 ⁇ L, 10 ⁇ L, 25 ⁇ L or 50 ⁇ L to about 100 ⁇ L, 500 ⁇ L, 1,000 ⁇ L, 10,000 ⁇ L, 10 mL, 20 mL, 25 mL, 30 mL, 40 mL, 50 mL, 60 mL, 70 mL, 80 mL, 90 mL, or 100 mL.
- the composition may be applied by hand or applied utilizing a delivery apparatus such as, for example, vaporizer or atomizer.
- the composition is allowed to dry after its application to the substrate.
- the scope of the present invention should be considered to cover one or more distinct applications of the composition or the continuous release of a composition via a vaporizer or other type of atomizer.
- the present disclosure provides a method for imparting, intensifying, or modifying an odor on human skin or human hair, comprising applying to human skin and/or human hair the composition of the present invention.
- notes or characters that can be enhanced include those chosen from a citrus-type note, green-type note, spicy-type note, cinnamon-type notes, pepper-type notes, cumin-type notes, ginger-type notes, floral-type notes, woody-type notes, cedarwood-type notes, sandalwood type notes, vetyver-type notes, leather-type note, smoky-type note, musk-type notes, and mixtures thereof.
- the fragrance profile or character of the composition of the present invention is detectable by a panel of experts or professional evaluators or individual experts or professional evaluators at later time points such as, for example, 30 mins, 1 hour, 2 hours, 3 hours, 4 hours, 5 hours, 6 hours, 7 hours, 8 hours, 10 hours, and possibly all the way up to 24 hours after application of the composition to a substrate as compared to controls (e.g., those without modulators).
- the present invention is also directed to a method of producing a consumer product comprising bringing into contact or mixing into the product an organoleptically active quantity of a composition of the present invention.
- EXAMPLES The effect on fragrance ingredients of adding 2% of Glucam P20 (molecular booster) is studied.
- Gerstel MPS Parameters GC Parameters: MS Detector: Experiment description ⁇ 20 ⁇ L of EDT were added to the wide end of the blotter, using a calibrated pipette. ⁇ The blotter + EDT system was left at room temperature to evaporate 5 minutes and up to 30hrs. ⁇ The wide tip of the blotter, where the fragrance was pipetted, was then cut into a 20mL HS vial. ⁇ The vial was immediately sealed, and subsequently analyzed on the GCMS. ⁇ The length of the blotter cut was consistently the same across the different samples (3- 3.5cm) such that it does not contact with the SPME during the extraction step.
- Aspect 1 provides a fragrance composition, comprising: less than or equal to 2 wt% glucam; and a fragrance component comprising d-limonene (CAS No.5989-27-5), Indole (CAS No.120-72-9), Thujopsene (CAS No.470-40-6), alpha – cedrene (CAS No.469-61-4), beta – cedrene (CAS No.546-28-1), beta ionone (CAS No.14901-07-6), Methyl Anthranilate (CAS No.134-20-3), Cedramber (CAS No.67874-81-1), cyclamen aldehyde (CAS No.
- Aspect 2 provides the composition of Aspect 1, wherein the fragrance component is present in an amount of from about 0.04 wt% to about 30 wt%, relative to the total weight of the composition.
- Aspect 3 provides the composition of any one of Aspects 1 or 2, wherein the fragrance component is present in an amount of from about 0.5 wt% to about 25 wt%, relative to the total weight of the composition.
- Aspect 4 provides the composition of any one of Aspects 1-3, wherein the fragrance component is present in an amount of from about 5 wt% to about 20 wt%, relative to the total weight of the composition .
- Aspect 5 provides the composition of any one of Aspects 1-4, wherein the composition is in the form of a perfume, an eau de toilette, an eau de perfume, a cologne, a body splash, a lotion, a cream, a shampoo, a conditioner, a hair mist, a body oil, a deodorant, a solid fragrance, or a body spray
- Aspect 6 provides the composition according to any one of Aspects 1-5, wherein the composition is in the form of a perfume
- Aspect 7 provides the composition of any one of Aspects 1-6, wherein the fragrance component is selected from a citrus-type note, green-type note, spicy-type note, cinnamon- type notes, pepper-type notes, cumin-type notes, ginger-type notes, juniper-type notes, fruity
- Aspect 8 provides the composition according to any one of Aspects 1-7, wherein a remanence of the fragrance component after 30 hours is in a range of 1.1 times to 10 times higher than a remancene of the fragrance component in a corresponding composition that is free of glucam.
- Aspect 9 provides the composition of any one of Aspects 1-8, wherein a remanence of the fragrance component after 30 hours is in a range of 1.1 times to 5.1 times higher than a remancene of the fragrance component in a corresponding composition that is free of glucam.
- Aspect 10 provides the composition of any one of Aspects 1-9, wherein the composition comprises ethanol in a range of from about 70 wt% to about 85 wt%, relative to the total weight of the composition.
- Aspect 11 provides the composition of any one of Aspects 1-9, wherein the composition comprises ethanol in a range of from about 77 wt% to about 82 wt%, relative to the total weight of the composition.
- Aspect 12 provides the composition of any one of Aspects 1-11, wherein the glucam is present in a range of from 0.2 wt% to 2 wt% relative to the total weight of the composition.
- Aspect 13 provides the composition of any one of Aspects 1-12, wherein the glucam is present in a range of from 0.3 wt% to 1.5 wt% relative to the total weight of the composition.
- Aspect 14 provides the composition of any one of Aspects 1-12, wherein the glucam is present in a range of from 0.5 wt% to 1 wt% relative to the total weight of the composition.
- Aspect 15 provide the composition of any one of Aspects 1-14, wherein wherein the fragrance component comprises: at least one low volatile fragrance material having a vapor pressure less than 0.001 Torr (0.000133 kPa) at 25 °C present in an amount greater than 30 wt%, relative to the total weight of the fragrance component; at least one moderate volatile fragrance material having a vapor pressure in the range of 0.1 Torr to 0.001 Torr (0.0133 kPa to 0.000133 kPa) at 25 °C present in an amount of from about 30 wt% to about 70 wt%, relative to the total weight of the fragrance component; and at least one high volatile fragrance material having a vapor pressure greater than 0.1 Torr (0.0133 kPa) at 25 °C present in an amount of from about 0.1 wt% to about 30 wt% relative to the total weight of the fragrance component.
- Aspect 16 provides a method of making the composition of any one of Aspects 1-15, the method comprising combining the fragrance component and
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Abstract
Description
Claims
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP23838323.6A EP4637702A1 (en) | 2022-12-21 | 2023-12-14 | Fragrance compositions and uses thereof |
| CN202380092492.9A CN120603572A (en) | 2022-12-21 | 2023-12-14 | Fragrance composition and use thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FRFR2214041 | 2022-12-21 | ||
| FR2214041A FR3143998A1 (en) | 2022-12-21 | 2022-12-21 | PERFUME COMPOSITIONS AND THEIR USES |
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| WO2024137340A1 true WO2024137340A1 (en) | 2024-06-27 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2023/084072 Ceased WO2024137340A1 (en) | 2022-12-21 | 2023-12-14 | Fragrance compositions and uses thereof |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP4637702A1 (en) |
| CN (1) | CN120603572A (en) |
| FR (1) | FR3143998A1 (en) |
| NL (1) | NL2036451B1 (en) |
| WO (1) | WO2024137340A1 (en) |
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- 2023-12-14 EP EP23838323.6A patent/EP4637702A1/en active Pending
- 2023-12-14 CN CN202380092492.9A patent/CN120603572A/en active Pending
- 2023-12-14 WO PCT/US2023/084072 patent/WO2024137340A1/en not_active Ceased
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Also Published As
| Publication number | Publication date |
|---|---|
| NL2036451B1 (en) | 2024-09-09 |
| EP4637702A1 (en) | 2025-10-29 |
| CN120603572A (en) | 2025-09-05 |
| FR3143998A1 (en) | 2024-06-28 |
| NL2036451A (en) | 2024-06-26 |
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