WO2017046059A1 - Composition de parfum contenant des composés modulateurs de fragrance pour augmenter l'intensité de parfum - Google Patents

Composition de parfum contenant des composés modulateurs de fragrance pour augmenter l'intensité de parfum Download PDF

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Publication number
WO2017046059A1
WO2017046059A1 PCT/EP2016/071514 EP2016071514W WO2017046059A1 WO 2017046059 A1 WO2017046059 A1 WO 2017046059A1 EP 2016071514 W EP2016071514 W EP 2016071514W WO 2017046059 A1 WO2017046059 A1 WO 2017046059A1
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cas
perfume composition
modulator compound
odor modulator
odor
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PCT/EP2016/071514
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German (de)
English (en)
Inventor
Ursula Huchel
Andreas Gerigk
Hubert Smyrek
Manuela Materne
Ralf Bunn
Frank Rittler
Andreas Bauer
Isabelle LEVERT
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Henkel Ag & Co. Kgaa
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Publication of WO2017046059A1 publication Critical patent/WO2017046059A1/fr

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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
    • C11B9/0069—Heterocyclic compounds
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • 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
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
    • C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six 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
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0092—Heterocyclic compounds containing only N as heteroatom
    • 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
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0096—Heterocyclic compounds containing at least two different heteroatoms, at least one being nitrogen
    • 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
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • C11D3/0015—Softening compositions liquid
    • 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
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2096—Heterocyclic compounds
    • 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
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/28—Heterocyclic compounds containing nitrogen in the ring
    • 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
    • C11D3/16—Organic compounds
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/3427—Organic compounds containing sulfur containing thiol, mercapto or sulfide groups, e.g. thioethers or mercaptales
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair

Definitions

  • the invention relates to a perfume composition containing at least one odor modulator compound for increasing the fragrance intensity of the perfume composition and a consumer product containing such a perfume composition. Furthermore, the invention relates to a method for increasing the fragrance intensity of the perfume composition and to the use of at least one odor modulator compound for increasing the fragrance intensity of the perfume composition.
  • European Patent EP 1 976 855 B1 describes bicyclic oxazolidines which are used as perfume precursors and release a fragrance by slow hydrolysis, thereby generating a long-lasting fragrance.
  • European patent EP 2 087 089 B1 describes the use of perfume microcapsules as a depot system, wherein the capsules break open at a defined time and provide an intense fragrance in the short term.
  • this technology is associated with great technical effort and high costs and the capsule wall material has no direct function after breaking the capsules.
  • the object of the present invention was therefore to provide a perfume composition with an arbitrary but specific scent profile which has a higher scent intensity than conventional perfume compositions, without necessarily relying on complex technologies such as perfume precursors or depot systems.
  • X is nitrogen, sulfur or CR 3 ;
  • Y is oxygen, sulfur or NR 5 ;
  • R, R 2 and R 5 are each independently hydrogen or radicals of 1 to 6 carbon atoms
  • R 3 and R 4 are each independently hydrogen or 1 to 9 radicals
  • the ring of the formula (I) may each independently contain double bonds at the positions linked by broken lines, with the proviso that the at least one odor modulator compound, when X is nitrogen, is between X and
  • R and R 2 are each, independently or in each case, an integral part of the fused ring
  • Carbon atoms of R to R 5 may each be independently substituted by heteroatoms.
  • the fragrance intensity of a perfume composition containing at least one odor modulator compound according to the invention is increased.
  • an odor modulator compound of the present invention in a perfume composition the amount of perfume composition in a consumer product such as fabric treatment, cleaning, cosmetic or adhesive can be significantly reduced without reducing the intensity of the fragrance or substantially altering the fragrance profile of the perfume composition.
  • perfume compositions of the present invention because of the smaller amount necessary to achieve the same scent intensity, can be more stably incorporated into common consumer products than conventional perfume compositions.
  • Numeric ranges specified in the format "from x to y" include the above values.If multiple preferred numeric ranges are specified in this format, it is understood that all ranges resulting from the combination of the various endpoints, are also included. "At least one" as used herein refers to 1 or more, for example, 2, 3, 4, 5, 6, 7, 8, 9 or more In the context of ingredients of the perfume compositions described herein, this reference does not refer to Thus, for example, at least one odor modulator compound means one or more different odor modulator compounds, that is, one or more different types of odor modulator compounds. Together with quantities, the quantities given refer to the total amount of the corresponding designated type of ingredient, unless otherwise specified.
  • All features relating to "at least one odor modulator compound”, such as the odor threshold, ClogP value, amounts or ratios, are for each odor modulator compound, eg, if two odor modulator compounds are included in a specific tonnage range in the perfume composition in that both the first odor modulator compound is contained in the specific tonnage range and the second odor modulator compound is contained in the specific tonnage range.
  • a perfume composition comprises at least one perfume which contributes substantially to the achievement of a specific fragrance profile.
  • a fragrance may also be present in the form of a fragrance precursor compound or in the form of a fragrance depot system.
  • a perfume composition additionally comprises all adjuvants known in the art which themselves have no perceptible odor, but result in a better meterability, a prolonged fragrance or a similar effect, such as, for example, solvents or adhesion promoters.
  • fragrance and perfume are used synonymously in the context of the present invention.
  • a fragrance is a compound which has a characteristic odor and contributes to the achievement of a specific fragrance profile of a perfume composition. Fragrances also include those compounds which alter the fragrance profile of a perfume composition such that the fragrance acquires a certain depth, which the person skilled in the art usually knows as the complexity of a fragrance. However, a fragrance within the meaning of the present invention has no direct influence on the fragrance intensity of the perfume composition, as long as the perfume composition is used at a constant concentration.
  • the fragrance profile of a perfume composition is the specific fragrance a consumer perceives due to the fragrance it contains.
  • a fragrance for example, flowery, spicy, sweet, sour, tart, fresh, woody, fruity, leathery, oriental, animal, chypre, fougere, citrus, edible, green, musky, ozone, aldehydic, agry, aromatic or marine nose, whereby the special selection of the individual fragrances in the perfume composition complex fragrance profiles can be achieved and a flowery scent, for example, rose , Violets or lavender can smell.
  • a scent profile is therefore the characteristic scent of each perfume composition, which results from the fragrances used.
  • An odor modulator compound (GMV) in the context of the present invention is a compound which, although having an inherent odor, but in the concentration used, under the test conditions given below, not or not significantly to a change in the fragrance profile of the perfume composition containing at least one odor modulator compound , contributes.
  • An insignificant change in the fragrance profile of the perfume composition means that although the fragrance profile may differ slightly from the original fragrance profile of the perfume composition, it is still recognized by the skilled person as the original fragrance profile.
  • an odor modulator compound according to the present invention despite its low use concentration, has a significant influence on the consumer perceived fragrance intensity of the perfume composition, so that, for example, a lower amount of the perfume composition can be used to achieve the same fragrance intensity as in a conventional perfume composition without odor modulator compound.
  • An odor modulator compound therefore, unlike a fragrance contained in a perfume composition, does not define the fragrance profile, but rather enhances the fragrance intensity of the fragrance profile of the perfume composition as defined by the fragrances.
  • the at least one odor modulator compound does not substantially change the fragrance profile of the perfume composition, in principle any desired fragrance profile can be realized without the disturbing side notes being perceived.
  • X is nitrogen, sulfur or CR 3 ;
  • Y is oxygen, sulfur or NR 5 ;
  • R, R 2 and R 5 are each independently hydrogen or radicals of from 1 to 6
  • R 3 , R 4 are each independently of one another hydrogen or radicals having 1 to 9 Carbon atoms,
  • the ring of the formula (I) may each independently contain double bonds at the positions linked with broken lines, with the proviso that the at least one odor modulator compound, when X is nitrogen, is between X and the carbon atom of the ring of the formula (I), which is linked to R 4 , contains a double bond;
  • R 5 to R 5 may each independently be substituted by heteroatoms.
  • the positions linked by broken lines can each independently have double bonds.
  • double bonds are especially absent if, due to the choice of X or the radicals R to R 4, the natural valence of the atoms participating in the double bond are already saturated. This means that the atoms involved in the double bond must always be uncharged.
  • X represents sulfur
  • the bond between X and the carbon atom directly linked to R 4 can not be a double bond.
  • the radicals R to R 4 forms a double bond to one of the carbon atoms in the ring of the general formula (I)
  • the corresponding atom in the ring can no longer be involved in a double bond within the ring.
  • the carbon atoms of the ring of the formula (I) linked to R and R 2 may together form part of an annelated five- or six-membered ring, wherein the radicals R and R 2 are each, independently of one another, wholly or partly an integral part of the fused ring.
  • Annotated in this context means that two carbon rings share a carbon-carbon bond, namely the carbon atoms of the ring of the formula (I) linked to R and R 2 , where this bond may be a single or double bond.
  • the radicals R and R 2 are only partially integral with the fused ring, the non-integral constituents of the ring of the radicals R and R 2 may be in the form of a side chain of the fused ring, for example.
  • One or more methyl groups, methylene groups, methine groups or quaternary carbon atoms of R to R 5 of the at least one odor modulator compound may each be independently substituted by heteroatoms.
  • Heteroatoms in the context of the present invention are selected from the group consisting of nitrogen, oxygen, sulfur, silicon, selenium, fluorine, chlorine, bromine or iodine.
  • One or more methyl groups can be substituted by a heteroatom selected from the group nitrogen, oxygen, sulfur, silicon, selenium, fluorine, chlorine, bromine or iodine
  • one or more methylene groups can be selected by a heteroatom selected from the group nitrogen, oxygen, sulfur , Selenium or silicon
  • one or more methine groups may be substituted by a heteroatom selected from the group consisting of nitrogen or silicon
  • one or more quaternary carbon atoms may be substituted by silicon.
  • a terminal methyl group adjacent to a methylene group can be replaced by a hydroxy group or a sulfanyl group to give a methylene hydroxy group or a methylene thiol group.
  • an isopropyl group which is a radical having two methyl groups and a methine group or a derivative of the isopropyl group which is a group having a methyl group, a methylene group and a quaternary carbon atom may be, for example, the following substitutions
  • methyl groups, methylene groups, methine groups or quaternary carbon atoms of the radicals R to R 5 can be substituted as desired by heteroatoms, but with the exception of di- or polysulfides and diazo compounds, no two directly adjacent groups are simultaneously substituted by heteroatoms.
  • the at least one odor modulator compound in the context of the present invention preferably contains one to four heteroatoms selected from the group of nitrogen, oxygen or sulfur.
  • Preferred radicals R to R 5 are, for example, alkyl groups, alkenyl groups, aryl groups, hydroxy groups, alkanol groups, acyl groups, (alkyl) ester groups, (alkyl) thiol groups, thioether groups and (alkyl) aldehyde groups.
  • the at least one odor modulator compound in the context of the present invention preferably has a molecular weight of less than 250 g mol -1 , preferably less than 225 g mol -1 and even more preferably less than 200 g mol -1 .
  • the at least one odor modulator compound according to the invention enhances the fragrance intensity of the perfume composition, which is described by the efficiency factor (E).
  • the efficiency factor is a measure of the fragrance intensity of two identical fragrance combinations containing perfume compositions, wherein one of the two perfume compositions additionally contains at least one odor modulator compound in the context of the present invention.
  • a group of at least 34 well-trained individuals assesses the intensity of both perfume compositions and determines the perfume composition smelling more intense than the other, with the intensity of the perfume compositions being evaluated by exactly 34 odorily trained persons in the embodiments of this invention.
  • An odor modulator compound according to the invention increases the fragrance intensity of the perfume composition so that the efficiency factor has at least a value of 1.15. In a preferred embodiment, the efficiency factor has at least a value of 1.5, more preferably a value of at least 1.75 or even more preferably even a value of at least 2.
  • the perfume composition of the present invention contains one to six odor modulator compounds, preferably one to five odor modulator compounds, more preferably one to four odor modulator compounds, and most preferably one to three odor modulator compounds.
  • the at least one odor modulator compound based on the totality of all fragrances contained in the perfume composition in a weight ratio of not more than 1: 9, preferably not more than 1:49, more preferably not more than 1:99 and most preferably not more than 1: 299 used, the ratio always on the at least one fragrance as such and not related to a corresponding fragrance precursor compound or a fragrance depot system.
  • the at least one odor modulator compound is present in an amount of from 2% to 0.000001% by weight, preferably from 1.5% to 0.000001% by weight, more preferably from 1.0% by weight % to 0.000001 wt%, more preferably from 0.5 wt% to 0.000001 wt%, most preferably 0.25 wt% to 0.000001 wt%, wt% each based on the perfume composition ,
  • the low ratio of the at least one odor modulator compound compared to the fragrances contained in the perfume composition and the small amounts of the individual odor modulator ensures that the fragrance profile of the perfume composition changed at most insignificant, so that the expert further recognizes the fragrance profile of the original fragrance. Moreover, it is advantageous from an ecological and economic point of view to use only small amounts of the odor modulator compound.
  • the at least one odor modulator compound is selected from pyrroles, thiazoles, thiophenes, furans, oxazolines and / or oxazoles.
  • the octanol / water partition coefficient of an odor modulator compound is the ratio between its equilibrium concentration in octanol and in water. Since the distribution coefficients of the odor modulator compounds often have high values, for example 1000 or higher, they are more conveniently given in the form of their base 10 logarithm, one speaks of the so-called logP value.
  • the logP value of numerous odor modulator compounds is documented. However, the logP values are most conveniently calculated by the "CLOGP" program available from Daylight Chemical Information Systems, Inc., (Daylight CIS), Irvine, California.
  • the "calculated logP values" the ClogP values which are the most reliable and widely used estimates for this physicochemical property, are used in the context of this invention in the selection of odor modulator compounds.
  • the at least one odor modulator compound has a ClogP value of less than 2.5, preferably less than 2.0.
  • a small ClogP value is equivalent to a good water solubility of the at least one odor modulator compound under standard conditions according to IUPAC, ie 25 ° C and 1 bar air pressure.
  • the at least one odor modulator compound On account of the good solubility in water of the at least one odor modulator compound, on the one hand, it can readily react in an aqueous solution. on the other hand, when the water evaporates, eg when drying textiles treated with a perfume composition according to the invention, the at least one odor modulator compound is better entrained in the gas phase, whereby the odor intensity of the perfume composition can be additionally enhanced.
  • the at least one odor modulator compound is preferably characterized by a low odor threshold (ODT).
  • the odor threshold value is the lowest odor nor perceptible concentration of a substance.
  • a simple technique for determining the odor threshold value is dynamic olfactometry, where a direct sensory evaluation of the compounds takes place.
  • the odor threshold serves as a measure of the odor strength of a fragrance.
  • the odor threshold value (ODT) of the at least one odor modulator compound is determined according to DIN EN 13725: 2003 and is preferably less than 100 ppb, preferably less than 75 ppb, more preferably less than 50 ppb, even more preferably less than 35 ppb, even more preferably less than 10 ppb and on most preferably less than 1 ppb.
  • the odor threshold value is measured by the following method:
  • the olfactometer is placed in a specially designed room (measuring room) for the olfactometer, which is odor-neutral, can be well ventilated and, if necessary, can be force-ventilated via an activated carbon filter.
  • the volume fraction of carbon dioxide in the measuring room is less than 0.15 vol .-%, the air exchange rate is at least 4.4 m 3 / h per person.
  • the temperature in the measuring room is 22 ⁇ 3 ° C and is constant during the measurement. The measuring room is not exposed to direct sunlight and other disturbing sources of light and noise have been minimized as much as possible.
  • the olfactometer and any devices that come into direct or indirect contact with the odor modulator compound to be evaluated must be odorless and are inert with respect to their reactivity with the odor modulator compounds, such as glass, stainless steel or PTFE.
  • the airflow provided by the olfactometer must be at least 20 L / min, with the opening of the device at which the sensory evaluation is made so that the air velocity in the flowed-through orifice is at least 0.2 m / s.
  • the olfactometer is checked regularly, at least every twelfth compound by a reference measurement with n-butanol as the reference compound.
  • the assessment of the compounds will be carried out by at least four examiners, with the usual number of odor-trained men and women, all of whom are at least 16 years old. At the time of evaluation of the compounds, the examiners are not affected by disturbing factors such as contact with perfume, food, other stimulants or even by a cold or allergy.
  • the odor modulator compound is used to prepare standardized dilute solutions in an odorless solvent, for example dipropylene glycol (DPG), where the lowest concentration is well below the odor threshold. Subsequently, the solutions are measured by means of the olfactometer. The concentration of the compound to be evaluated is gradually increased, each concentration being doubled until the tester perceives an odor. Each odor modulator compound is measured three times each by each examiner and the arithmetic mean of all odor sensed concentrations forms the Odor Threshold (ODT).
  • DPG dipropylene glycol
  • the at least one odor modulator compound is selected from 2-ethyl-4-methylthiazole (CAS No. 15679-12-6), 2-isopropyl-4-methylthiazole (CAS No. 15679-13- 7), 2-isobutylthiazole (CAS # 18640-74-9), 2-acetylthiazole (CAS # 24295-03-2), 2,2 '- (dithiodimethylene) -difuran (CAS # 4437- 20-1), furfurylmercaptan (CAS No. 98-02-2), menthurane (CAS No. 494-90-6), homofuranol (CAS No. 27538-09-6), furaneol (CAS No. No. No.
  • furfurylideneacetone (CAS No. 10881 1-61- 6), 4-butyroxy-2,5-dimethyl-3 ( 2H) -furanone (CAS no. 1 14099-96-6), 2-acetylfuran (CAS no. 1 192-62-7), 2-acetyl-5-methylfuran (CAS No. 1 193-79-9), 2,4,5-trimethylthiazole (CAS No. 13623-1 1-5), 2- Methyl 5-thiomethyl furan (CAS No. 13678-59-6), furfuryl thioacetate (CAS No. 13678-68-7), furfuryl methylsulphide (CAS No.
  • furo- furyl thioformate (CAS No. 59020-90-5), 5-methylfurfural (CAS No. 620-02-0), furfuryl acetate (CAS No. 623-17-6), 3- (2 -Furyl) acrolein (CAS No. 623-30-3), 2-thienylmercaptan (CAS No. 6258-63-5), 2,5- Dimethylthiophene (CAS No. 638-02-8), 4-methyl-5-thiazoleethanol acetate (CAS No. 656-53-1), 4-methylthiazole (CAS No. 693-95-8), 2 -Furyl-2-propanone (CAS No.
  • the specified names of the odor modulator compounds are basically unambiguous and the skilled person has no problems identifying the corresponding substance, the CAS numbers of the odor modulator compounds have been indicated for the sake of simplicity. If, contrary to expectation, the specified name does not match the specified CAS number, the CAS number applies in case of doubt. Only in cases where it is obvious that the CAS number is incorrect, the given name is preferable to the CAS number.
  • the at least one odor modulator compound is selected from 2-ethyl-4-methylthiazole (CAS No. 15679-12-6), 2-isopropyl-4-methylthiazole (CAS No. 15679- 13-7), 2-isobutylthiazole (CAS No. 18640-74-9), 2-acetylthiazole (CAS No. 24295-03-2), 2,2 '- (dithiodimethylene) -difuran (CAS-No. No. 4437-20-1), furfuryl mercaptan (CAS No. 98-02-2), furfural propylene glycol acetal (CAS No. 4359-54-0), menthofuran (CAS No.
  • a perfume composition according to the invention may be contained in a consumer product, in particular a textile treatment agent, cleaning agent, cosmetics or an adhesive, which is the second object of the present invention.
  • the perfume composition of the present invention containing at least one odor modulator compound, the amount of perfume composition necessary to achieve a specific fragrance intensity can be advantageously at least 15% by weight, preferably at least 20% by weight, compared to the perfume composition without odor modulator compound even be reduced by at least 25 wt .-%.
  • the consumer product is a fabric treatment or cleaning composition containing at least one surfactant selected from anionic, cationic or nonionic surfactants.
  • the anionic surfactant used may preferably be sulfonates and / or sulfates.
  • the preferred total amount of anionic surfactant in the fabric treatment or cleaning agent is 7.5 to 65.0 wt .-%, and preferably 20.0 to 45 wt .-%, each based on the total agent.
  • Preferred surfactants of the sulfonate type are C9-i3-alkylbenzenesulfonates, olefin-sulfonates, ie mixtures of alkene and hydroxyalkanesulfonates and disulfonates, such as those from sulfonated C12-C18 monoolefins having an end or internal double bond with gaseous sulfur trioxide and subsequent alkaline or acidic hydrolysis of the sulfonation obtained.
  • Ci2-is-alkanesulfonates and the esters of ⁇ -sulfo fatty acids are also suitable.
  • Este rsulfo nate the esters of ⁇ -sulfo fatty acids
  • the ⁇ -sulfonated methyl esters of hydrogenated coconut, palm kernel or tallow fatty acids are also suitable.
  • Alk (en) ylsulfates are the alkali metal salts and in particular the sodium salts of the sulfuric monoesters of C 12-18 fatty alcohols, for example coconut fatty alcohol, tallow fatty alcohol, lauryl, myristyl, cetyl or stearyl alcohol or the C 10 -C 20 oxo alcohols and those Half-ester secondary alcohols of these chain lengths are preferred. From a washing-technical point of view, preference is given to the C 12 -C 16 -alkyl sulfates and C 12 -C 15 -alkyl sulfates and C 1 -C -alkyl sulfates. 2,3-alkyl sulfates are also suitable anionic surfactants.
  • fatty alcohol ether sulfates such as the sulfuric acid monoesters of straight-chain or branched C7-2i alcohols ethoxylated with from 1 to 6 mol of ethylene oxide, such as 2-methyl-branched C9-n alcohols having an average of 3.5 moles of ethylene oxide (EO) or C12- Fatty alcohols with 1 to 4 EO are suitable.
  • Suitable anionic surfactants are soaps.
  • Suitable are saturated and unsaturated fatty acid soaps, such as the salts of lauric acid, myristic acid, palmitic acid, stearic acid, (hydrogenated) erucic acid and behenic acid and, in particular, soap mixtures derived from natural fatty acids, for example coconut, palm kernel, olive oil or tallow fatty acids.
  • the anionic surfactants and the soaps may be in the form of their sodium, potassium or magnesium or ammonium salts.
  • the anionic surfactants are in the form of their ammonium salts.
  • Preferred counterions for the anionic surfactants are the protonated forms of choline, triethylamine, monoethanolamine or methylethylamine.
  • Cationic surfactants are preferably selected from esterquats and / or quaternary ammonium compounds (QAV) according to the general formula (R I ) (R ") (R 1 ") (R IV ) N + X " in which R 'to R IV for identical or different ⁇ -22-alkyl radicals, C7-28-arylalkyl radicals or heterocyclic Radicals, wherein two or, in the case of an aromatic incorporation as in pyridine, even three radicals together with the nitrogen atom form the heterocycle, for example a pyridinium or imidazoline compound, and X "represents halide ions, sulfate ions, hydroxide ions or similar anions QACs can be prepared by reacting tertiary amines with alkylating agents, such as, for example, methyl chloride, benzyl chloride, dimethyl sulfate, dodecyl bromide, but also ethylene oxide.
  • Cationic surfactants are present in the textile treatment or cleaning agents in amounts of preferably from 5% by weight to 50% by weight, in particular from 8% by weight to 30% by weight.
  • Suitable nonionic surfactants include alkoxylated fatty alcohols, alkoxylated fatty acid alkyl esters, fatty acid amides, alkoxylated fatty acid amides, polyhydroxy fatty acid amides, alkylphenol polyglycol ethers, amine oxides, alkyl polyglucosides, and mixtures thereof.
  • the nonionic surfactant used are preferably alkoxylated, advantageously ethoxylated, in particular primary, alcohols having preferably 8 to 18 carbon atoms and on average 4 to 12 moles of ethylene oxide (EO) per mole of alcohol, in which the alcohol radical can be linear or preferably methyl-branched in the 2-position or may contain linear and methyl-branched radicals in the mixture, as they are usually present in Oxoalkoholresten.
  • EO ethylene oxide
  • alcohol ethoxylates with linear radicals of alcohols of native origin having 12 to 18 carbon atoms, for example of coconut, palm, tallow or oleyl alcohol, and on average 5 to 8 EO per mole of alcohol are preferred.
  • the preferred ethoxylated alcohols include, for example, C 12-14-alcohols with 4 EO or 7 EO, C 7 -n-alcohol with 7 EO, cis-is alcohols with 5 EO, 7 EO or 8 EO, C 12 -is alcohols with 5 EO or 7 EO and mixtures of these.
  • the degrees of ethoxylation given represent statistical means which, for a particular product, may be an integer or a fractional number.
  • Preferred alcohol ethoxylates have a narrow homolog distribution (narrow rank ethoxylates, NRE).
  • NRE narrow rank ethoxylates
  • nonionic Surfactants can also be used fatty alcohols with more than 12 EO.
  • Nonionic surfactants containing EO and PO groups together in the molecule can also be used according to the invention. Also suitable are also a mixture of a (more) branched ethoxylated fatty alcohol and an unbranched ethoxylated fatty alcohol, such as a mixture of a Ci6-is fatty alcohol with 7 EO and 2-propylheptanol with 7 EO. With particular preference the agent according to the invention contains a C 12-18 fatty alcohol with 7 EO, a C-ms oxo alcohol with 7 EO and / or a C 13 -oxoalcohol with 8 EO as nonionic surfactant.
  • the total amount of nonionic surfactant of the textile treatment or cleaning agent is preferably 0.1 to 25 wt .-% and preferably 7 to 22 wt .-%, each based on the total agent.
  • the textile treatment or cleaning agents may contain further ingredients which further improve the performance and / or aesthetic properties of the composition depending on the intended use.
  • the textile treatment or cleaning agents Builder bleaches, bleach activators, bleach catalysts, esterquats, silicone oils, emulsifiers, thickeners, electrolytes, pH adjusters, fluorescent agents, dyes, Hydro tope, foam inhibitors, Anti Redepositionsstoff, solvents, enzymes, optical Whitening agents, anti-gelling agents, anti-shrinkage agents, anti-wrinkling agents, color transfer inhibitors, color protectants, wetting improvers, antimicrobial agents, germicides, fungicides, antioxidants, corrosion inhibitors, rinse aids, preservatives, antistatic agents, ironing auxiliaries, repellents and impregnating agents, pearlescing agents, polymers, swelling and anti-slip agents and UV Absorber included.
  • the amounts of the individual ingredients in the textile treatment or cleaning agents are each based on the intended use of the respective means and the skilled person is in principle familiar with the orders of magnitude of the amounts of ingredients to use or can refer to the corresponding technical literature.
  • the surfactant content will be higher or lower.
  • the surfactant content of, for example, detergents may be from 10 to 50% by weight, preferably from 12.5 to 30% by weight, and more preferably from 15 to 25% by weight while, for example, automatic dishwashing detergents include, for example 0.1 to 10 wt .-%, preferably from 0.5 to 7.5 wt .-% and in particular from 1 to 5 wt% may contain surfactants.
  • a textile treatment or cleaning agent preferably contains at least one water-soluble and / or water-insoluble, organic and / or inorganic builder.
  • the water-soluble organic builder substances include polycarboxylic acids, in particular citric acid and sugar acids, monomeric and polymeric aminopolycarboxylic acids, in particular methylglycine diacetic acid, nitrilotriacetic acid and ethylenediaminetetraacetic acid and polyaspartic acid, polyphosphonic acids, in particular aminotris (methylenephosphonic acid), ethylenediaminetetrakis (methylenephosphonic acid) and 1-hydroxyethane-1, 1-diphosphonic acid, polymeric hydroxy compounds such as dextrin and polymeric (poly) carboxylic acids, polymeric acrylic acids, methacrylic acids, maleic acids and copolymers thereof, which may also contain polymerized small amounts of polymerizable substances without carboxylic acid functionality.
  • polycarboxylic acids in particular citric acid and sugar acids
  • monomeric and polymeric aminopolycarboxylic acids in particular methylglycine diacetic acid, nitrilotriacetic acid and ethylenedi
  • Suitable, although less preferred, compounds of this class are copolymers of acrylic or methacrylic acid with vinyl ethers, such as vinylmethyl ethers, vinyl esters, ethylene, propylene and styrene, in which the acid content is at least 50% by weight.
  • the organic builder substances can, in particular for the preparation of liquid textile treatment or cleaning agents, in the form of aqueous solutions, preferably in the form of 30 to 50 wt .-% tiger aqueous solutions are used. All of the acids mentioned are generally used in the form of their water-soluble salts, in particular their alkali metal salts.
  • Organic builders may, if desired, be included in amounts of up to 40% by weight, more preferably up to 25% by weight, and preferably from 1% to 8% by weight. Quantities close to the stated upper limit are preferably used in paste-form or liquid, in particular water-containing, agents according to the invention. Laundry aftertreatment agents, such as fabric softeners, may optionally also be free of organic builder. Suitable water-soluble inorganic builder materials are, in particular, alkali metal silicates and polyphosphates, preferably sodium triphosphate.
  • Crystalline or amorphous alkali metal aluminosilicates if desired, in amounts of up to 50% by weight, preferably not more than 40% by weight and in liquid agents, in particular of 1% by weight, can be used as water-insoluble, water-dispersible inorganic builder materials. to 5 wt .-%, can be used.
  • suitable aluminosilicates have no particles with a particle size greater than 30 ⁇ m, and preferably consist of at least 80% by weight of particles having a size of less than 10 ⁇ m.
  • Suitable substitutes or partial substitutes for the said aluminosilicate are crystalline alkali silicates which may be present alone or in a mixture with amorphous silicates.
  • the alkali metal silicates useful as builders in the textile treatment or cleaning compositions preferably have a molar ratio of alkali metal oxide to SiO 2 below 0.95, in particular from 1: 1.1 to 1:12, and may be present in amorphous or crystalline form.
  • Preferred alkali metal silicates are the sodium silicates, in particular the amorphous sodium silicates, with a molar ratio of Na 2 O: SiO 2 of from 1: 2 to 1: 2.8.
  • Crystalline silicates which may be present alone or in a mixture with amorphous silicates are preferably crystalline phyllosilicates of the general formula Na.sub.2SixO.sub.2.sup.x + y.sub.2H.sub.2O, in which x, the so-called modulus, is a number from 1.9 to 4 and y is a number from 0 to 20 and preferred values for x are 2, 3 or 4.
  • Preferred crystalline phyllosilicates are those in which x in the abovementioned general formula assumes the values 2 or 3.
  • both beta- and delta-sodium disilicates Na2Si20s ⁇ y H2O are preferred.
  • amorphous alkali metal silicates can be used in textile treatment or cleaning agents.
  • a crystalline sodium layer silicate with a modulus of 2 to 3 is used, as can be prepared from sand and soda.
  • Crystalline sodium silicates with a modulus in the range from 1.9 to 3.5 are used in a further preferred embodiment of the textile treatment or cleaning agents.
  • the weight ratio of aluminosilicate to silicate is preferably 1:10 to 10: 1.
  • the weight ratio of amorphous alkali metal silicate to crystalline alkali metal silicate is preferably 1: 2 to 2: 1 and in particular 1: 1 to 2: 1.
  • Builders are, if desired, in the textile treatment or cleaning agents preferably in amounts up to 60 wt .-%, in particular from 5 wt .-% to 40 wt .-%, included.
  • Aftertreatment agents such as fabric softeners, are preferably free of inorganic builder.
  • Suitable enzymes which can be used in the textile treatment or cleaning agents are those from the class of the proteases, cutinases, amylases, pullulanases, hemicellulases, cellulases, lipases, oxidases and peroxidases and mixtures thereof. Particularly suitable are from fungi or bacteria, such as Bacillus subtilis, Bacillus licheniformis, Streptomyces griseus, Humicola lanuginosa, Humicola insolens, Pseudomonas pseudoalcaligenes or Pseudomonas cepacia derived enzymatic agents.
  • the optionally used enzymes can be adsorbed on carriers and / or embedded in coating substances in order to protect them against premature inactivation. They are, if desired, in the compositions preferably in amounts not exceeding 5 wt .-%, in particular from 0.2 wt .-% to 2 wt .-%, contained.
  • the textile treatment or cleaning agents may optionally contain as optical brighteners, for example, derivatives of diaminostilbene disulfonic acid or their alkali metal salts.
  • optical brighteners for example, derivatives of diaminostilbene disulfonic acid or their alkali metal salts.
  • Suitable examples are salts of 4,4'-bis (2-anilino-4-morpholino-1, 3,5-triazinyl-6-amino) stilbene-2,2'-disulfonic acid or compounds of similar construction, which instead of the Mor - Pholino group carry a diethanolamino group, a methylamino group, an anilino group or a 2-methoxyethylamino group.
  • Suitable foam inhibitors include, for example, organopolysiloxanes and mixtures thereof with microfine, optionally silanized silica and paraffin waxes and mixtures thereof with silanated silicic acid or bis-fatty acid alkylenediamides. It is also advantageous to use mixtures of various foam inhibitors, for example those of silicones, paraffins or waxes.
  • the foam inhibitors in particular silicone- and / or paraffin-containing foam inhibitors, are preferably bound to a granular, water-soluble or dispersible carrier substance. In particular, mixtures of paraffin waxes and bistearylethylenediamides are preferred.
  • the textile treatment or cleaning agents may also contain components which positively influence the oil and Fettauswaschles from textiles, so-called soil release agents. This effect becomes particularly clear when a textile is soiled, which has been previously washed several times with an agent containing this oil and fat dissolving component.
  • the preferred oil and fat dissolving components include, for example, nonionic cellulose ethers such as methylcellulose and methylhydroxypropylcellulose with a proportion of methoxyl groups of 15 to 30 wt .-% and hydroxypropoxyl groups of 1 to 15 wt .-%, each based on the nonionic Cellulose ethers, and the known from the prior art polymers of phthalic acid and / or terephthalic acid or derivatives thereof with monomeric and / or polymeric diols, especially polymers of ethylene terephthalates and / or polyethylene glycol terephthalates or anionic and / or nonionic modified derivatives thereof ,
  • the textile treatment or cleaning agents may also color transfer inhibitors, preferably in amounts of 0.1 wt .-% to 2 wt .-%, in particular 0.1 wt .-% to 1 wt .-%, containing, in a preferred embodiment of the invention polymers of vinylpyrrolidone , Vinylimidazole, vinylpyridine-N-oxide or copolymers thereof.
  • Graying inhibitors have the task of keeping suspended from the textile fiber dirt suspended in the fleet.
  • Water-soluble colloids of mostly organic nature are suitable for this purpose, for example starch, glue, gelatin, salts of ether carboxylic acids or ether sulfonic acids of starch or of cellulose or salts of acidic sulfuric acid esters of cellulose or starch.
  • water-soluble polyamides containing acidic groups are suitable for this purpose.
  • starch derivatives can be used, for example aldehyde starches.
  • cellulose ethers such as carboxymethylcellulose (Na salt), methylcellulose, hydroxyalkylcellulose and mixed ethers, such as methylhydroxyethylcellulose, methylhydroxypropylcellulose, methylcarboxymethylcellulose and mixtures thereof, for example in amounts of from 0.1 to 5% by weight, based on the compositions.
  • the fabric treatment or cleaning agent may be in liquid or solid form, with gels, foams, pastes, creams and aerosols also included.
  • water-free to anhydrous liquid textile treatment or cleaning agents may be in pre-portioned Form present, wherein the textile treatment or cleaning agent is filled in a water-soluble wrapper and thus may be part of a water-soluble packaging.
  • the textile treatment or cleaning agent is packaged in a water-soluble casing, it is preferred that the water content is less than 10% by weight based on the total agent and that anionic surfactants, if present, are in the form of their ammonium salts.
  • a solid textile treatment or cleaning agent may preferably be in the form of a powder, a granulate, a tablet, a tab or another shaped body having a defined geometry, such as a sphere, an oval or a cylinder.
  • a third aspect of the invention is a process for increasing the fragrance intensity of a perfume composition, characterized in that at least one odor modulator compound according to the general formula (I) is added to the perfume composition, mel (I),
  • X is nitrogen, sulfur or CR 3 ;
  • Y is oxygen, sulfur or NR 5 ;
  • R, R 2 and R 5 are each independently hydrogen or radicals of 1 to 6 carbon atoms
  • R 3 and R 4 are each independently hydrogen or 1 to 9 radicals
  • the ring of the formula (I) may each independently contain double bonds at the positions linked by broken lines, with the proviso that the at least one odor modulator compound, when X is nitrogen, is between X and
  • the carbon atoms of the ring of the formula (I) linked to R and R 2 may together form part of an annelated five- or six-membered ring, the
  • R and R 2 are each, independently or in each case, an integral part of the fused ring
  • R to R 5 may each be independently substituted by heteroatoms.
  • a fourth object of the invention is the use of at least one odor modulator compound according to the general formula (I) for increasing the fragrance intensity of a perfume composition
  • X is nitrogen, sulfur or CR 3 ;
  • Y is oxygen, sulfur or NR 5 ;
  • R, R 2 and R 5 are each independently hydrogen or radicals of 1 to 6 carbon atoms
  • R 3 and R 4 are each independently of one another hydrogen or radicals having 1 to 9 carbon atoms
  • the ring of the formula (I) may each independently contain double bonds at the positions linked by broken lines, with the proviso that the at least one odor modulator compound, when X is nitrogen, is between X and
  • the carbon atoms of the ring of the formula (I) linked to R and R 2 may together form part of an annelated five- or six-membered ring, the
  • R and R 2 are each, independently or in each case, an integral part of the fused ring
  • Carbon atoms of R to R 5 may each be independently substituted by heteroatoms.
  • perfume composition comprising at least one odor modulator compound according to the general formula (I),
  • X is nitrogen, sulfur or CR 3 ;
  • Y is oxygen, sulfur or NR 5 ;
  • R, R 2 and R 5 are each independently hydrogen or radicals of 1 to 6 carbon atoms
  • R 3 and R 4 are each independently hydrogen or 1 to 9 radicals
  • the ring of the formula (I) may each independently contain double bonds at the positions linked by broken lines, with the proviso that the at least one odor modulator compound, when X is nitrogen, is between X and
  • the carbon atoms of the ring of the formula (I) linked to R and R 2 may together form part of an annelated five- or six-membered ring, where the radicals
  • R and R 2 are each, independently or in each case, an integral part of the fused ring
  • Carbon atoms of R to R 5 may each be independently substituted by heteroatoms.
  • perfume composition according to item 1 characterized in that the perfume composition one to six odor modulator compounds, preferably one to five odor modulator compounds, more preferably one to four odor modulator compounds and on most preferably contains one to three odor modulator compounds.
  • Perfume composition according to item 1 or 2 characterized in that the at least one odor modulator compound based on the totality of all fragrances contained in the perfume composition in a weight ratio of not more than 1: 9, preferably not more than 1:49, more preferably not more than 1:99 and most preferably at most 1: 299 is used.
  • Perfume composition according to items 1 to 3, characterized in that the at least one odor modulator compound in an amount of 2 wt .-% to 0.000001 wt .-%, preferably from 1 .5 wt .-% to 0.000001 wt .-%, more preferably from 1.0 wt .-% to 0.000001 wt .-%, more preferably from 0.5 wt .-% to 0.000001 wt .-%, most preferably 0.25 wt .-% to 0.000001 wt .-% is contained, wt .-% in each case on the perfume composition.
  • Perfume composition according to one of the items 1 to 4 characterized in that the at least one odor modulator compound contains one to four heteroatoms selected from the group N, O or S.
  • Perfume composition according to one of the items 1 to 5 characterized in that the at least one odor modulator compound has a molecular weight of less than 250 g mol -1 , preferably less than 225 g mol -1 and even more preferably less than 200 g mol -1
  • Perfume composition according to one of the items 1 to 10 characterized in that the at least one odor modulator compound is selected from pyrroles, thiazoles, thiophenes, furans, oxazolines and oxazoles.
  • Perfume composition according to one of the items 1 to 1 characterized in that the at least one odor modulator compound is selected from 2-ethyl-4-methylthiazole (CAS No. 15679-12-6), 2-isopropyl-4-methylthiazole (CAS) No. 15679-13-7), 2-isobutylthiazole (CAS No.
  • Perfume composition according to one of the items 1 to 12, characterized in that the at least one odor modulator compound is selected from 2-ethyl-4-methylthiazole (CAS No. 15679-12-6), 2-isopropyl-4-methylthiazole (CAS no 15679-13-7), 2-isobutylthiazole (CAS No. 18640-74-9), 2-acetylthiazole (CAS No. 24295-03-2), 2,2 '- (dithiodimethylene) -difuran (CAS No. 4437-20-1), furfuryl mercaptan (CAS No. 98-02-2), furfural propylene glycol acetal (CAS No. 4359-54-0), menthofuran (CAS No.
  • Consumer product according to item 14 characterized in that the consumer product is a textile treatment or cleaning agent and contains at least one surfactant selected from anionic, cationic and / or nonionic surfactants.
  • a method for increasing the fragrance intensity of a perfume composition characterized in that at least one odor modulator compound according to the general formula (I) is added to a perfume composition, Formula (I),
  • X is nitrogen, sulfur or CR 3 ;
  • Y is oxygen, sulfur or NR 5 ;
  • R, R 2 and R 5 are each independently hydrogen or radicals of 1 to 6 carbon atoms
  • R 3 and R 4 are each independently hydrogen or 1 to 9 radicals
  • the ring of the formula (I) may each independently contain double bonds at the positions linked by broken lines, with the proviso that the at least one odor modulator compound, when X is nitrogen, is between X and
  • the carbon atoms of the ring of the formula (I) linked to R and R 2 may together form part of an annelated five- or six-membered ring, where the radicals
  • R and R 2 are each, independently or in each case, an integral part of the fused ring
  • Carbon atoms of R to R 5 may each be independently substituted by heteroatoms.
  • Method according to item 16 characterized in that one to six odor modulator compounds, preferably one to five odor modulator compounds, more preferably one to four odor modulator compounds and most preferably one to three odor modulator compounds are added to the perfume composition.
  • the at least one odor modulator compound contains one to four heteroatoms selected from the group N, O or S.
  • the at least one odor modulator compound is selected from 2-ethyl-4-methylthiazole (CAS No. 15679-12-6), 2-isopropyl-4-methylthiazole (CAS no 15679-13-7), 2-isobutylthiazole (CAS No. 18640-74-9), 2-acetylthiazole (CAS No. 24295-03-2), 2,2 '- (dithiodimethylene) -difuran (CAS No. 4437-20-1), furfuryl mercaptan (CAS No. 98-02-2), menthofuran (CAS No. 494-90-6), homofuranol (CAS No. 27538-09-6), furaneol (CAS No.
  • furfurylideneacetone (CAS No. 10881 1-61 -6), 4-butyroxy-2,5 dimethyl-3 (2H ) - furanone (CAS no. 1 14099-96-6), 2-acetylfuran (CAS No. 1 192-62-7), 2-acetyl-5-methylfuran (CAS No. 1 193-79-9), 2,4,5- Trimethylthiazole (CAS No. 13623-1 1-5), 2-methyl-5-thiomethylfuran (CAS No. 13678-59-6), furfurylthioacetate (CAS No. 13678-68-7), furfurylmethylsulphide (CAS No. No.
  • X is nitrogen, sulfur or CR 3 ;
  • Y is oxygen, sulfur or NR 5 ;
  • R, R 2 and R 5 are each independently hydrogen or radicals of 1 to 6 carbon atoms
  • R 3 and R 4 are each independently hydrogen or 1 to 9 radicals
  • the ring of the formula (I) may each independently contain double bonds at the positions linked by broken lines, with the proviso that the at least one odor modulator compound, when X is nitrogen, is between X and
  • R and R 2 are each, independently or in each case, an integral part of the fused ring
  • Carbon atoms of R to R 5 may each be independently substituted by heteroatoms.
  • the at least one odor modulator compound in an amount of 2 wt .-% to 0.000001 wt .-%, preferably from 1 .5 wt .-% to 0.000001 wt .-%, more preferably from 1.0% by weight to 0.000001% by weight, more preferably from 0.5% by weight to 0.000001% by weight, most preferably from 0.25% by weight to 0.000001% by weight, to the perfume composition, wt. % in each case based on the perfume composition.
  • the at least one odor modulator compound contains one to four heteroatoms selected from the group N, O or S.
  • the at least one odor modulator compound a molecular weight of less than 250 g mol -1 , preferably less than 225 g mol -1 and even more preferably less than 200 g mol -1
  • the at least one odor modulator compound is selected from pyrroles, thiazoles, thiophenes, furans, oxazolines and oxazoles.
  • the at least one odor modulator compound is selected from 2-ethyl-4-methylthiazole (CAS No. 15679-12-6), 2-isopropyl-4-methylthiazole (CAS no 15679-13-7), 2-isobutylthiazole (CAS No. 18640-74-9), 2-acetylthiazole (CAS No. 24295-03-2), 2,2 '- (dithiodimethylene) -difuran (CAS No.
  • furfuryl mercaptan (CAS No. 98-02-2), menthofuran (CAS No. 494-90-6), homofuranol (CAS No. 27538-09-6), furaneol (CAS No. 3658-77-3), 1- (2-benzofuranyl) -ethanone (CAS No. 1646-26-0), nerolone (CAS No. 2391 1-56-0), furfural-propylene glycol acetal (CAS No. 4359-54-0), furanol methyl ether (CAS No. 4077-47-8), sulfuryl (CAS No. 137-00-8), benzothiazole (CAS No.
  • Furfuryl isopropylsulphide (CAS # 1883-78-9), 2,4,5-trimethyloxazole (CAS # 20662-84-4), 2-methyl-2-thiazoline (CAS # 2346-00- 1), 2-methylthiazolidine (CAS No. 24050-16-6), 2-methyltetrahydrofuran-3-thioacetate (CAS No. 252736-41-7), 2-methyl-3-furanthiol (CAS No. 28588 -74-1), bis (2-methyl-3-tetrahydrofuran) di-sulphide (CAS No. 28588-75-2), 3 (5-methyl-2-furyl) butanal (CAS No.
  • the at least one odor modulator compound is selected from 2-ethyl-4-methylthiazole (CAS No. 15679-12-6), 2-isopropyl-4-methylthiazole (CAS no 15679-13-7), 2-isobutylthiazole (CAS No. 18640-74-9), 2-acetylthiazole (CAS No. 24295-03-2), 2,2 '- (dithiodimethylene) -difuran (CAS No. 4437-20-1), furfuryl mercaptan (CAS No. 98-02-2), furfural propylene glycol acetal (CAS No. 4359-54-0), menthofuran (CAS No.
  • Table 1 Perfume compositions contained in liquid detergents.
  • the efficiency factor E for the perfume composition with GMV from Table 1 versus the perfume composition without GMV is 1.92.
  • the odor intensity and fragrance profile of the liquid detergents were each judged at four different times, namely, product tanning, wet cotton terry toweling directly after washing, cotton terry toweling after one day drying, and four days drying. The evaluation was made according to the same method used to determine the efficiency factor. The fragrance intensity of both liquid detergents was rated identical at the time points tested. In addition, no significant differences were observed between the scent profiles of both liquid detergents.
  • DPG Dipropylene glycol
  • the efficiency factor E for the perfume composition with GMV from Table 2 versus the perfume composition without GMV is 1.33.
  • the odor intensity and scent profile of the powder detergents were each evaluated at four different times, namely, product rinse, wet cotton terry toweling immediately after washing, same cotton terry toweling after one day of drying, and four days of drying. The evaluation was made according to the same method used to determine the efficiency factor. The scent intensity of both powder detergents was rated identical at the time points tested. In addition, no significant differences were observed between the scent profiles of both powder detergents.
  • the efficiency factor E for the perfume composition with GMV from Table 23 versus the perfume composition without GMV is 1.69.
  • the odor intensity and fragrance profile of the fabric softeners were each evaluated at four different times, namely product tanning, wet cotton terry toweling directly after washing, drying on the same cotton terry toweling after one day, and drying after four days. The evaluation was made according to the same method used to determine the efficiency factor. The scent intensity of both fabric softeners was rated as identical at the time points tested. In addition, no significant differences were observed between the scent profiles of both fabric softeners.
  • the efficiency factor E for the perfume composition with GMV from Table 4 versus the perfume composition without GMV is 1.33.
  • Toilets were placed in fragrance cabins, so that no strange odors could interfere with the evaluation of the fragrance intensity and fragrance profile.
  • the toilets were then rinsed a total of 50 times with 6 L of water.
  • the WCs were rinsed four times at 15-minute intervals and then the fragrance intensity and the fragrance profile of the two liquid toilet rinse cleaners were evaluated after 1, 2, 4, 8 and 24 hours.
  • the evaluation was made after the same Method used to determine the efficiency factor.
  • the odor intensity of both liquid toilet rinse cleaners was rated identical at the time points tested. In addition, no significant differences were observed between the odor profiles of both liquid toilet rinse cleaners.
  • Shampoo identical to the first unperfumed shampoo was incorporated with 0.65% by weight of an odor modulator compound perfume composition.
  • the perfume compositions are given in Table 5.
  • Table 5 Perfume compositions contained in the shampoos.
  • the shampoos were dissolved in 35 ° C warm water (2.8 g shampoo / 180 mL water). Subsequently, 0.2 g of shampoo / 1 g of hair was massaged into the hair for 1 min before the shampoo was thoroughly rinsed out. The evaluation of the fragrance intensity and the fragrance profile was carried out in each case on freshly washed damp hair, after drying after 3, 6, 9, 24 and 48 h. The scent intensity of both shampoos was rated as identical at the time points tested. In addition, no significant differences were observed between the scent profiles of both shampoos.
  • the efficiency factor E for the perfume composition with GMV from Table 5 versus the perfume composition without GMV is 1.92.

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  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Fats And Perfumes (AREA)
  • Detergent Compositions (AREA)

Abstract

La présente invention concerne une composition de parfum contenant au moins un composé modulateur de fragrance pour augmenter l'intensité du parfum de la composition de parfum, et un produit de consommation contenant une telle composition de parfum. L'invention concerne également un procédé pour augmenter l'intensité du parfum de la composition de parfum, et l'utilisation d'au moins un composé modulateur de parfum pour augmenter l'intensité du parfum de la composition de parfum.
PCT/EP2016/071514 2015-09-17 2016-09-13 Composition de parfum contenant des composés modulateurs de fragrance pour augmenter l'intensité de parfum WO2017046059A1 (fr)

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DE102015217868.4 2015-09-17
DE102015217868.4A DE102015217868A1 (de) 2015-09-17 2015-09-17 Parfümzusammensetzung mit Geruchsmodulatorverbindungen zur Steigerung der Duftintensität

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WO2017046059A1 true WO2017046059A1 (fr) 2017-03-23

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Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3885051A (en) * 1972-10-30 1975-05-20 Int Flavors & Fragrances Inc Flavoring and aromatising with 3-acetyl-2,5-dialkyl furans or thiophenes
US4040987A (en) * 1976-10-07 1977-08-09 International Flavors & Fragrances Inc. 2-Alkyl-substituted-4,5-dimethyl thiazoline perfume and cologne compositions
DE2742391A1 (de) * 1976-10-07 1978-04-13 Int Flavors & Fragrances Inc 2-substituierte 4,5-dialkyl-delta hoch 3 -thiazoline, verfahren zu deren herstellung und ihre verwendung als organoleptische wuerzstoffe
EP1069116A1 (fr) * 1999-07-12 2001-01-17 Haarmann & Reimer Gmbh N-(2-Mercaptoéthyl)-1,3-thiazolidines et leur utilisation comme parfums et arômes
EP2404987A1 (fr) * 2009-03-06 2012-01-11 Shiseido Co., Ltd. Compositions de parfum
EP1976855B1 (fr) 2006-01-20 2012-08-15 Henkel AG & Co. KGaA Composes de 1-aza-3,7-dioxabicyclo[3.3.0]octane et leur utilisation en tant que precurseurs de parfum
EP2087089B1 (fr) 2006-11-22 2012-09-26 The Procter and Gamble Company Agent bénéfique contenant une particule de vectorisation
WO2012162331A2 (fr) 2011-05-26 2012-11-29 The Procter & Gamble Company Compositions comprenant un bouquet efficace de parfums
WO2014093828A2 (fr) * 2012-12-14 2014-06-19 The Procter & Gamble Company Compositions antitranspirantes et déodorantes

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3885051A (en) * 1972-10-30 1975-05-20 Int Flavors & Fragrances Inc Flavoring and aromatising with 3-acetyl-2,5-dialkyl furans or thiophenes
US4040987A (en) * 1976-10-07 1977-08-09 International Flavors & Fragrances Inc. 2-Alkyl-substituted-4,5-dimethyl thiazoline perfume and cologne compositions
DE2742391A1 (de) * 1976-10-07 1978-04-13 Int Flavors & Fragrances Inc 2-substituierte 4,5-dialkyl-delta hoch 3 -thiazoline, verfahren zu deren herstellung und ihre verwendung als organoleptische wuerzstoffe
EP1069116A1 (fr) * 1999-07-12 2001-01-17 Haarmann & Reimer Gmbh N-(2-Mercaptoéthyl)-1,3-thiazolidines et leur utilisation comme parfums et arômes
EP1976855B1 (fr) 2006-01-20 2012-08-15 Henkel AG & Co. KGaA Composes de 1-aza-3,7-dioxabicyclo[3.3.0]octane et leur utilisation en tant que precurseurs de parfum
EP2087089B1 (fr) 2006-11-22 2012-09-26 The Procter and Gamble Company Agent bénéfique contenant une particule de vectorisation
EP2404987A1 (fr) * 2009-03-06 2012-01-11 Shiseido Co., Ltd. Compositions de parfum
WO2012162331A2 (fr) 2011-05-26 2012-11-29 The Procter & Gamble Company Compositions comprenant un bouquet efficace de parfums
WO2014093828A2 (fr) * 2012-12-14 2014-06-19 The Procter & Gamble Company Compositions antitranspirantes et déodorantes

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