WO2025153182A1 - Fragrance mixtures comprising aromatic nitriles - Google Patents
Fragrance mixtures comprising aromatic nitrilesInfo
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- WO2025153182A1 WO2025153182A1 PCT/EP2024/051132 EP2024051132W WO2025153182A1 WO 2025153182 A1 WO2025153182 A1 WO 2025153182A1 EP 2024051132 W EP2024051132 W EP 2024051132W WO 2025153182 A1 WO2025153182 A1 WO 2025153182A1
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- Prior art keywords
- methyl
- oil
- acetate
- ethyl
- dimethyl
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
- C11B9/0065—Nitriles
Definitions
- Fragrance mixtures comprising aromatic nitriles
- the present refers to the area of fragrances and concerns fragrance mixtures comprising aromatic nitriles with improved scent notes.
- At least one solvent wherein said at least one secondary fragrance belongs to the group of fragrances exhibiting at least one of the following scent notes: fruity; woody; floral; aromatic/herbal; citrus; spicy; and green.
- aromatic nitriles in general, more particular certain benzonitriles, in particular 3,4-dimethyl benzonitrile are capable to improve the olfactory profile of a number of defined secondary fragrances.
- the nitriles are able to provide to said secondary fragrances more volume, body, richness and complexity. They add notes like, orange, mango, hyacinth and/or pepper an enhance spiciness and balsamic and sandal notes. This is even more surprising, since the nitriles themselves show a strong cinnamon note.
- the nitriles improve the long-lasting effect of the secondary fragrances, in particular in the presence of specific solvents.
- compositions according to the invention comprise as component (a) aromatic nitriles according to formula (II) wherein R 2 , R 3 independently of one another represent hydrogen or linear or branched Ci- Cw-alkyl, which is optionally substituted with hydroxy or Ci -C4-a Ikyl or linear or branched Ci- C -alkoxy, which is optionally substituted with hydroxy or Ci -C4-alkyl.
- the most preferred compound is 3,4-dimethyl benzonitrile, available from Symrise AG.
- the secondary fragrances may belong to one, two or more of the following scent categories, as they are common and standard in perfume industry: fruity; woody; floral; aromatic/herbal; citrus; spicy; and green.
- mixtures according to the present invention may include 1, 2, 3, 4, 5 or even more secondary fragrances from the list provided above, binary and ternary combinations are preferred.
- a first preferred embodiment refers to binary mixtures of components (a) and (b.)
- the secondary fragrances (b) are preferably selected from the following groups: fruity scent note: 2-methyl butyl isovalerate, acetyl butyryl, aldehyde C14 so-called, aldehyde C16 so-called, aldehyde C18 so-called, allyl heptylate, amyl acetate, amyl butyrate, amyl capronate, amyl formate, anisyl acetone, cis-2-tert-butylcyclohexyl acetate, (2-tert-butylcyclohexyl) acetate, benzyl butyrate, benzyl isobutyrate, benzyl isovalerate, butyl acetate, butyl butyrate, benzyl isobutyrate, benzyl isovalerate, butyl acetate, butyl butyrate
- citrus scent note are selected from the group consisting of 3,7-dimethyl-6-octene-1 - nitrile, decanal, 6,6-dimethoxy-2,5,5-trimethylhex-2-ene, bergamot oil, ethyl 6- acetoxyhexanoate, cedrat oil, citral diethyl acetal, citral, 2,4-Dimethyl-3-cyclohexene-1 - methanyl acetate, Citronella oil, Citronellal, (E)-3-Methyl-5-phenylpent-2-enenitrile and (Z)-3-Methyl-5-phenylpent-2-enitrile, alpha Ethenyl-alpha-methyl-benzenepropane nitrile, 2,4,4,7-tetramethyl-6-octen-3-one, (+/-)-2,8-Epithio-cis-p-menthane, 3- Mercapto-
- the most preferred primary fragrances (a) is 3,4-dimethyl benzonitrile.
- the fragrance mixtures according to the present invention incorporate solvents (component c) in perfumery grade as for example water, ben- zyl alcohol, benzyl benzoate, diethyl phthalate, dipropylene glycol, ethyl alcohol (ethanol), zso-propyl myristate, triethyl citrate, dipropyleneglycol methyl ether (Downol 0 DPM), petroleum distillates such as for example IsoPar L (Exxon), triacetin and their mixtures.
- solvents component c
- perfumery grade as for example water, ben- zyl alcohol, benzyl benzoate, diethyl phthalate, dipropylene glycol, ethyl alcohol (ethanol), zso-propyl myristate, triethyl citrate, dipropyleneglycol methyl ether (Downol 0 DPM), petroleum distillates such as for example IsoPar L (Exxon), triacet
- Particular preferred are ethanol, dipropylene glycol and triethyl citrate and mixtures thereof.
- Another object of the present invention refers to a perfume preparation comprising the mixtures as defined above and at least 1, 2, 3, 4, 5 or more tertiary fragrances or perfume oils, preferably different from components (a), but might overlap with components (b).
- Suitable fragrances and perfume oils can be selected from the group consisting of
- Suitable alcohols known to the expert by their tradenames encompass for example 1 -(2-tert- butylcyclohexyl)oxybutan-2-ol (139504-68-0; Amber core); 2,6-di-tert-butyl-p-cresol (128-37- 0; BHT Ionol); (Z)-3-methyl-5-(2,2,3-trimethyl-1 -cyclopent-3-enyl)pent-4-en-2-ol (67801 -20- 1; Ebanol); 4-methyl-2-(2-methylpropyl)oxan-4-ol (63500-71 -0; Florosa/ Pyranol); [(1 R.,2S)-1- methyl-2-[[(1 R.,3S,5S)-1 , 2, 2-trimethyl-3-bicyclo[3.1.0]hexanyl]methyl]cyclopropyl] methanol (198404-98-7; Javanol); (3R)-1-[(1 R,6S
- Suitable amines, amides and nitriles known to the expert by their tradenames encompass for example 3,7-dimethyloct-6-enenitrile (51566-62-2; Argunitril); (E/Z)-3-methyl-5-phenylpent- 2-enenitrile (53243-59-7; 53243-60-0; 93893-89-1; Citronitrile); 3,7-dimethylnona-2,6-enitrile (61792-11 -8; Lemonile); 4-[(3E)-4,8-dimethylnona-3,7-dienyl]pyridine (38462-23- 6; Maritima); tridec-2-enenitrile (22629-49-8; Ozonil); 2-cyclohexylidene-2-phenylacetonitrile (10461-98-0; Peonile); and mixtures thereof.
- Suitable ethers known to the expert by their tradenames encompass for example (3aR,5aS,9aS,9bR)-3a, 6,6, 9a-tetramethyl-2, 4, 5, 5a, 7,8,9, 9b-octahydro-1 H-benzo[e][1] benzofuran (6790-58-5; Ambroxide); 5-hexyl-4-methyloxolan-2-one (67663-01 -8; Aprifloren); cy- clohexadec-2-en-1 -one (2550-59-6; 3100-36-5; 88642-03-9; Aurelione); 3,4-diethyl-2,5- dimethylcyclohex-2-en-1 -one (68845-36-3; Azarrow); 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8- hexamethylcyclopenta(g)-2-benzopyran (1222-05-5; Galaxolide); (2R,4S)-2-methyl-4
- Suitable ketones known to the expert by their tradenames encompass for example 7-methyl-
- the solvents are selected from the group consisting of water, benzyl alcohol, benzyl benzoate, diethyl phthalate, dipropylene glycol, ethyl alcohol, zso-propyl myristate, triethyl citrate, dipropyleneglycol methyl ether, petroleum distillates, triacetin and mixtures thereof.
- the preferred solvents are selected from the group consisting of ethanol, dipropylene glycol, triethyl citrate and mixtures thereof.
- the primary fragrance is 3,4-dimethyl benzonitrile
- the secondary fragrances are selected from homomenthyl acetate, myrcene, phellandrene, phenoxyethyl isobutyrate, 2-ethyl-4-(2,2,3-trimethylcyclopent-3-en-yl)-but-2-en- l-ol, isobutyric acid-1 -hydroxy-2, 2, 4-trimethyl-3-pentyl ester and isobutyric cid-3- hydroxy-2, 2, 4-trimethyl-1 -pentyl ester and mixtures thereof; and the solvents are selected from the group consisting of ethanol, dipropylene glycol, triethyl citrate and mixtures thereof.
- the primary fragrance is 3,4-dimethyl benzonitrile
- the secondary fragrances are selected from homomenthyl acetate, myrcene, phellandrene, phenoxyethyl isobutyrate, 2-ethyl-4-(2,2,3-trimethylcyclopent-3-en-yl)-but-2-en- l -ol, isobutyric acid-1 -hydroxy-2, 2, 4-trimethyl-3-pentyl ester and isobutyric cid-3- hydroxy-2, 2, 4-trimethyl-1 -pentyl ester and mixtures thereof; and the solvent is ethanol.
- Formulation 1 stands for any of the fragrance mixtures according to Examples 1 to 75.
- Liquid soap (Amounts in % b.w.)
- Zirconium suspensoid antiperspirant stick (Amounts in % b.w.)
- Antiperspirant formulations (Amounts in % b.w.)
- Cream (Amounts in % b.w.)
- Cream (Amounts in % b.w.)
- Moisturizing body care cream (Amounts in % b.w.)
- Anti-wrinkle cream (Amounts in % b.w.)
- Moisturizing and disinfecting face mask (Amounts in % b.w.)
- Sprayable disinfecting gel (Amounts in % b.w.)
- Cosmetic sun protection composition (Amounts in % b.w.)
- Liquid detergent concentrate (Amounts in % b.w.) Table F53
- Dish washing concentrate (Amounts in % b.w.)
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
Abstract
Suggested are new fragrance compositions comprising or consisting of aromatic nitriles, specific secondary fragrances and optionally solvents. Said nitriles are capable already in amounts below 5 wt.-percent to modulate, intensify and/or increase the long-lasting effect of said secondary fragrances.
Description
Fragrance mixtures comprising aromatic nitriles
AREA OF INVENTION
[0001] The present refers to the area of fragrances and concerns fragrance mixtures comprising aromatic nitriles with improved scent notes.
BACKGROUND OF THE INVENTION
[0002] On the part of perfumery, there is a great demand for fragrances, especially notes, which allow an expansion of the perfumery palette. The demand is particularly high for fragrances which, in small doses, have a great effect on other fragrances and change them for the better, for example in terms scent recognition ("modulation"), intensity and long-lasting effect.
RELEVANT PRIOR ART
[0003] Aromatic nitriles are well known synthetic intermediates for both the chemical industry [see March's Advanced Organic Chemistry, Reactions, Mechanisms and Structure, John Wiley and Sons, Inc., New York, 2007], and the perfume industry.
[0004] A suitable process for obtaining aromatic nitriles encompasses the use of cyanide sources such as for example CuCN, KCN, NaCN, Zn(CN)2, TMSCN or in the transformation of arylhalogenides into nitriles [see Kim et al., Angewandte Chemie, Vol. 124, p 12114 ff (2012)].
[0005] EP 0550762 Al (KAO) refers to a process for producing a nitrile by heating an aldoxime in the presence of one or more catalysts selected from hydroxides of alkali metals, alcoholates of alkali metals, hydroxides of alkaline earth metals and alcoholates of alkaline earth metals, and distilling off water formed in the course of the reaction from the reaction system.
[0006] EP 2979682 A1 (SYMRISE) claims fragrance compositions comprising aromatic nitriles such as for example 3,4-dimethyl benzonitrile in combination with specific solvents.
OBJECT OF THE INVENTION
[0007] Therefore, it has been the object of the present invention providing new fragrance mixtures, showing improvements in performance. Desired are in particular primary fragrances i
which are capable of modulating, intensifying and increasing the long-lasting effect of other secondary fragrances in small amount, preferably in amount below 5 wt.-percent, more preferably less than 3 wt.-percent and most preferably less than 0.5 wt.-percent.
BRIEF DESCRIPTION OF THE INVENTION
[0008] A first object of the present invention refers to a fragrance mixture comprising or consisting of
(a) at least one a primary fragrance according to general formula (I)
wherein R1, R2, R3, R4, and R5 independently of one another represent hydrogen or linear or branched Ci-Cio-alkyl, which is optionally substituted with hydroxy or Ci -C4-alkyl or linear or branched Ci-Cio-alkoxy, which is optionally substituted with hydroxy or Ci- C4-alkyl,
(b) at least one secondary fragrance different from component (a) and optionally
(c) at least one solvent, wherein said at least one secondary fragrance belongs to the group of fragrances exhibiting at least one of the following scent notes: fruity; woody; floral; aromatic/herbal; citrus; spicy; and green.
[0009] Surprisingly, it has been observed, that aromatic nitriles in general, more particular certain benzonitriles, in particular 3,4-dimethyl benzonitrile are capable to improve the olfactory profile of a number of defined secondary fragrances. In particular, the nitriles are able to provide to said secondary fragrances more volume, body, richness and complexity. They add notes like, orange, mango, hyacinth and/or pepper an enhance spiciness and balsamic and sandal notes. This is even more surprising, since the nitriles themselves show a strong cinnamon note. Moreover, the nitriles improve the long-lasting effect of the secondary fragrances, in particular in the presence of specific solvents.
[0010] With regard to the specific scent categories the following perfuming effects are achieved:
Aromatic nitriles
[0011] The aromatic nitriles forming component (a) and hereinafter forming the of "primary fragrances" represent known compounds, which are obtainable according to standard procedures of organic chemistry. Reference is made for example to applicant's earlier application EP 2979682 A1. In a preferred embodiment the compositions according to the invention comprise as component (a) aromatic nitriles according to formula (II)
wherein R2, R3 independently of one another represent hydrogen or linear or branched Ci- Cw-alkyl, which is optionally substituted with hydroxy or Ci -C4-a Ikyl or linear or branched Ci- C -alkoxy, which is optionally substituted with hydroxy or Ci -C4-alkyl.
[0012] More preferably the compositions according to the invention include aromatic nitriles according to formula, wherein the R2 and R3 substituents of the aromatic nitrile represent methyl.
[0013] Examples of suitable aromatic nitriles forming component (a) encompass the following species:
• 3,4-dimethyl benzonitrile;
• 4-(2-methylpropyl) benzonitrile;
• 3-methyl benzonitrile;
• 2-methoxy benzonitrile;
• 3,4-dimethoxy benzonitrile;
• 4-methoxybenzonitrile and mixtures thereof.
[0014] The most preferred compound is 3,4-dimethyl benzonitrile, available from Symrise AG.
Secondary fragrances
[0015] As explained above, the secondary fragrances may belong to one, two or more of the following scent categories, as they are common and standard in perfume industry: fruity; woody; floral; aromatic/herbal; citrus; spicy; and green.
[0016] In other words, the fragrances belonging to one of the groups share the same olfactory sensation. The following Tables A to G provide examples for each of these categories, without claiming to be complete.
Table A
Examples for fragrances with fruity scent note
Table B
Examples for fragrances with woody scent note
Table C
Examples for fragrances with floral scent note
Table D
Examples for fragrances with aromatic/herbal scent note
Table E
Examples for fragrances with citrus scent note
Table F
Examples for fragrances with green scent note
Table G
Examples for fragrances with spicy scent note
Binary, ternary and multiple fragrance mixtures
[0017] While the mixtures according to the present invention may include 1, 2, 3, 4, 5 or even more secondary fragrances from the list provided above, binary and ternary combinations are preferred.
[0018] Therefore, a first preferred embodiment refers to binary mixtures of components (a) and (b.) In such case the secondary fragrances (b) are preferably selected from the following groups: fruity scent note: 2-methyl butyl isovalerate, acetyl butyryl, aldehyde C14 so-called, aldehyde C16 so-called, aldehyde C18 so-called, allyl heptylate, amyl acetate, amyl butyrate, amyl capronate, amyl formate, anisyl acetone, cis-2-tert-butylcyclohexyl acetate, (2-tert-butylcyclohexyl) acetate, benzyl butyrate, benzyl isobutyrate, benzyl isovalerate, butyl acetate, butyl butyrate, benzyl isobutyrate, benzyl isovalerate, butyl acetate, butyl butyrate, butyl caprylate, butyl formate, butyl isobutyrate, butyl isovalerate, butyl propionate, butyl salicylate, butyric acid, norborn-5-en-yl acetate, caproic acid, cyclohexyl acetate, cyclohexyl butyrate, 1 -cyclohexyl-(2E)-but-2-enoate, davana oil, delta decalactone, gamma decalactone, diethyl malonate, delta dodecalactone, gamma dodecalactone, ethyl acetate, ethyl butyrate, ethyl caprinate, ethyl capronate, ethyl caprylate, ethyl formate, ethyl heptoate, ethyl-3- hydroxyhexa noate, ethyl isobutyrate, ethyl isovalerate, ethyl laurate, ethyl levulinate, ethyl-2-methyl butyrate, ethyl pelargonate, ethyl- 3-phenylglycidate, ethyl propionate, ethyl valerate, ethyl-2-tertbutylcyclohexyl carbonate, ethyl-2,4-dimethyl-1,3-dioxolane-2-acetate, 4-(4-hydroxyphenyl) butane-2- one, 4-4(4-hydroxyphenyl) butane-2-one methyl ether, ethyl tricyclo [5.2.1.0 2.6] dec- ane-2-carboxylate, 4-methylpentane-2-yl-( E)-but-2-enoate, furfuryl acetate, gammaheptalactone, heptanoic acid, heptyl acetate, gamma-hexalactone, hexyl acetate, hexyl butyrate, hexyl caproate, hexyl caprylate, hexyl formate, hexyl isobutyrate, hexyl isovalerate, Hexyl-2-methylbutanoate, hexyl propionate, isoamly acetate, isoamyl butyrate, isoamyl capronate, isobutyl butyrate, isobutyl isovalerate, isobutyric acid, 1,3-dimethyl- 3-butenyl 2-methylpropionate, isoprenyl acetate, isopropyl acetate, isovaleric acid, isovaleric aldehyde, ethyl (2-methyl-1,3-dioxolan-2-yl)-acetate, 4,4a,5,9b-tetrahydro-2,4- dimethyl-indeno[1,2-d]-1,3-dioxin, maltol isobutyrate, ethyl-2-methyl pentanoate,
ethyl-3,5,5-trimethyl hexanoate, methyl acetate, 2-methyl butyl acetate, 2-methyl butyraldehyde, methyl butyrate, methyl caproate, methyl caprylate, 2-methyl methylbutyrate, methyl thiobutyrate, 2-methyl butyric acid, 2, 2-methyl pentenoic acid, delta nonalactone, norborn-5-en-yl acetate, delta octalactone, gamma octalactone, 2- (ethoxymethyl)-1 -methyl-3-(1 -methylethen€-cyclopentene, diethyl (E)-2-methylbut-2- enedioate, 2-methylpentyl-2-methylvalerate, propyl aceta'e, propyl propionate, 1,1 '- Bi(cyclopentyl)-2-yl (2E)-but-2-enoate, (E)-4-methyldec-3-en-5-ol, delta undecalactone, valeric acid, gamma valerolactone: woody scent note: 2-methyl-5-(5,5,6-trimethyl-bicyclo[2.2.1]-hept-2-yl) cyclohexanone, 1 -(2-tert-butylcyclohexyl)oxybutan-2-ol, 2H-lndeno[4,5-b] furan, decahydro- 2,2, 6, 6,7,8, 8-heptamethyl, dodecahydro-3,3-8,11 a-tetramethyl-5H-3, 5a- epoxynapht(2,1 -c)oxepin, 3a,6,6,9a-Tetramethyldodecahydronaphtho[2,1 -b]furan, (eth- oxymethoxy)-cyclododecane, (E)-Ambra-13,18(28)-dien-8-ol, ambrinol, (4aR,5R,7aS,9R)- Octahydro-2,2,5,8,8,9ahexamethyl-4H-4a,9-methanoazuleno[5,6-d]-1,3-dioxole, (3aS,4aR,5R,7aS,9R,9aR)-Octahydro-2,5,8,8,9a-pentamethyl-2-propyl-4H-4a,9- methanoazuleno[5,6-d]-1,3-dioxole, dodecahydro-3a,6,6,9a-tetramethyl- naphtho[2,1 - b]furan, (3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1 -b]furan, amyris oil, 8oc,9oc-epoxycedrane, (+) 2,6,9-trimethyl-2,5,9-cyclododecatrien-1 -ol, 2- methyl-3-({1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}oxy)propan-1 -ol, boya oil, beta- 2,2, 3-Tetramethylcyclopent-3-ene1 -butanol, alpha-decahydro-2, 2,4, 8-tetramethyl-4, 8- methanoazulen-9-yl acetate, (1 R,3E,5S,9S)- 4,11,11 -trimethyl-8-methylene- Bicy- clo[7.2.0]undec-3-en-5-ol, 1,2, 3,5,6, 7-hexahydro- 1,1, 2,3, 3-pentamethyl-4H-inden-4- one, cedarwood oil, [3R-(3oc,3a|3,6a,7|3,8aa)]-octahydro-6-methoxy-3,6,8,8-tetramethyl- 1 H-3a,7-methanoazulene + (3R, 3aS,6R,7R, 8aS)-octahydro-6-methoxy-3, 6,8,8- tetramethyl-1 H-3a,7-methanoazulene, cedrene, cedrenol, cedrol, cedroxid, cedryl acetate, 3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1 H-benzo[e][1]benzofuran, clearwood, cyclododecyl formate, cypriol oil, dynamone, (Z)-3-methyl-5-(2,2,3- trimethyl-1 -cyclopent-3-enyl)pent-4-en-2-ol, (E)-2-methyl-1-(6-methyl-6- bicyclo[2.2.1]hept-2-enyl)pent-1-en-3-ol mixture, 1 -(2,6,6-Trimethyl-2-cyclohexen-1 - yl)-3-pentanone, guaiac wood oil, guaiacol, guaiyl acetate, hydrocarboresin B, 2- cyclododecylpropan-1 -ol, 1 -(2,3,8, 8-Tetramethyl-1, 3, 4,5,6, 7-hexahydronaphthalen-2- yl)ethanone, isobornyl cyclohexanol, bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, pro- panoate, 2H-2,4a-methanonaphthalene, [1-Methyl-2-[(1,2,2-trimethylbicyclo[3.1.0]hex- 3-yl)methyl]cyclopropyl]methanol (mixture of diastereoisomers), 5-Butyl-2-yl-2-(2,4- dimethyl-1-cyclohex-3-enyl)-5-methyl-1,3-dioxane, 4-(1 -Ethoxyvinyl)-3, 3,5,5- tetramethyl-cyclohexan-1 -one, Methyl diisoamyl carbinol, 1 R,2S,7S,9S)-3,3,7-trimethyl- 8-methylentricyclo-[5.4.0.02,9]undecan, alpha-Ethyl-2,2,6- trimethylcyclohexanepropanol, 1 -Methyl-1 -methoxycyclododecane, 3,3-Dimethyl-5- (2,2,3- trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, alpha-Propyl-2,2,6-trimethyl- cyclohexanepropanol, 2,4-Dimethyl-2-(1,1,4,4-tetramethyltetralin-6-yl)-1,3-dioxolane,
labdanum ethanone, 3,7- dimethyl-7-methoxy-2-octanol, 1,3, 6, 7- tetramethylbicyclo[4.4.0]dec-7-en-2-yl formate, 1,1-dimethoxy-cyclododecane, methoxycyclododecane, patchouli oil, 1-[4-(1,1-dimethylethyl)phenyl]-ethanone, 1, 1,5,5- Tetramethylhexahydro-2H-2,4a-methanonaphthalen-8(5H)-one, 3,3-Dimethyl-5-(2,2,3- trimethyl-3-cyclopente'-1-yl)-4-penten-2-ol, 3,7’-Dimethyl-3,4,4a,5,8,8a- hexahydrospiro-(1,4-m'thanonaphthalene- 2(1 H),2'-oxirane), 2-(1,1-Dimethylethyl)-4- methylcyclohexanol, 2-(1,1-Dimethylethyl)-4-methylcyclohexanol, 2-Methyl-4-(2,2,3- trimethyl- 3-cyclopneten-1 -yl)-2-buten-1 -ol, 3-methyl-5-(2,2,3-trimethylcyclopent-3- en-1-yl)pentan-2-ol, sandalwood oil, (2E)-2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1- yl)-buten-1 -ol, 2-Ethyl-4-(2,2,3-trimethylcyclopent-3-en-1 -yl)but-2-en-1 -ol, sclareolide, 1,3,4,5,6,7-hexahydro-7-methoxy-1,1,5,5-tetramethyl-2H-2,4a-methanonaphthalene, 1,1,5,5-Tetramethyl-octahydro-2,4a-methanonaphthalene-8a-ol, 1 -(2,2,6-
Trimethylcyclohexyl)hexan-3-ol, trimofix, methyl cedryl ketone, 1,3-Dimethyl-3- phenylbutylacetate, 4-Methyl-4-phenylpentan-2-one, 4-Cyclohexyl-4-methylpentan-2- one, vetiver oil, 4,8-Dimethyl-2-propan-2-ylidene-3,3a,4,5,6,8a-hexahydro-1 H-azulen-6- ol, (4,8-dimethyl-2-propan-2-ylidene-3,3a,4,5,6,8a-hexahydro-1 H-azulen-6-yl) acetate, 1 ',1 ,,5,,5'-Tetramethylhexahydro-spiro[1,3-dioxolane-2,8,(5,H)-2H-2,4a- methanonaphthalene] floral scent note: 4-(3-methylbutyl)cyclohexan-1-ol, allyl-alpha-ionone, alpha-amyl cinnamic aldehyde, isopentyl phenethyl ether, benzophenone, benzyl acetate, benzyl acetone, benzyl propionate, benzyl salicylate, 2-ethoxy-2,6,6-trimethyl-9- methylenebicyclo[3.3.1]nonane, 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2- butenal, 3-[4-(1,1-dimethylethyl)-phenyl]-propanal), cabreuva oil, methylbenzodioxepi- non, cananga oil, 3-(4-methoxyphenyl)-2-methylpropanal, (3-methoxy-2- methylpropyl)-benzene, 2-methyl-4-(2,6,6-trimethyl-2(1)-cyclohexen-1-yl)butanal, Isomethyl-alpha-ionone, Citronellol, Citronellyl acetate, Citronellyl butyrate, citronellyl formate, citronellyl isobutyrate, citronellyl isovaleriate, citronellyl propionate, citronellyl tiglate, ortho-methoxybenzyl ethyl ether, 3-(p-cumenyl)-2-methylpropionaldehyd, 3-(4- isopropylphenyl)propanal, 1-(3,3-Dimethylcyclohexyl)ethyl acetate, Cyclohexyl salicylate, 2-Methyl-3-(4-tert-butylphenyl)propanol, 1,2,3,4,5,6,7,8-octahydro-5,5-dimethyl-2- Naphthalenecarboxaldehyde; 1,2,3,4,5,6,7,8-octahydro-8,8-dimethyl-2-
Naphthalenecarboxaldehyde, (E)-1-(2,6,6-trimethyl-1-cyclohexa-1,3-dienyl)but-2-en-1- one; (2E)- 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)- 2-buten-1-one, (E)-1 -(2,6,6- tri methyl - 1 -cyclohex-2-enyl)but-2-en-1 -one, (E)-1 -(2,6,6-trimethyl-1 -cyclohex-2- enyl)but-2-en-1 -one, (E)-1 -(2,6,6-trimethyl-1 -cyclohexenyl)but-2-en-1 -one, 1 -(2,6,6- trimethyl-1-cyclohex-3-enyl)but-2-en-1-one, trans, trans-2,4-decadienal, 2-pentyl- cyclopropan-1 -ol, 2-pentyl-cyclopentanone, 4-(2,6,6-trimethyl-1 -cyclohexenyl)-2- butanone, 3-methyl-2-pentyl-2-cyclopenten-1 -on, tetrahydro-4-methyl-2-(2- methylpropyl)- 2H-pyran, dimethal anthranilate, dimethyl sulfoxide, dipheynl oxide, (E)- 4-ethyloct-3-enenitrile, dimethyl sulfide, tetrahydro-4-methyl-2-phenyl-2H-pyran, 4-
(octahydro-4, 7-methano-5H-inden-5-ylidene)butanal, ethyl linalyl acetal, ethyl anthranilate, ethyl benzoate, ethyl linalool, cyclohexa-1,3-diene-1 -carboxylic acid, 2,6,6- trimethyl-ethyl ester, ethyl salicylate, farnesol, farnesyl acetate, 3-(3- isopropylphenyl)butanal, 4-methyl-2-(2-methylpropyl)oxan-4-ol, 2,6-dimethyl-2- heptanol, 2-methyldecanenitrile, ethyl 2-acetylocta noate, (2E)-3,7-dimethylocta-2,6- dien-1 -ol, geranium oil, geranyl acetate, geranyl acetone, geranyl benzoate, geranyl butyrate, geranyl ethyl ether, genaryl formate, genaryl isobutyrate, genaryl isovalerate, geranyl methyl ether, geranyl propionate, geranyl tiglate, 2-[5(6)-Methyl-7(8)-(1 - methylethyl)bicyclo[2.2.2]oct-5-en-2-yl]-1,3-dioxolane, geranium dihydropyran, methyl 3-oxo-2-pentylcyclopentaneacetate, methylenedioxyphenyl-methylpropanal, hexen-3- yl salicylate (cis), hexyl benzoate, alpha-hexyl cinnamic aldehyde, hexyl salicylate, 2,3- dihydro-1,1 -dimethyl-1 H-indene-ar-propanal, hydroxy citronellol, indene, Tetrahy- droindeno dioxin, Indole, (3E)-4-(2,6,6-trimethylcyclohex-2-en-1 -yl)but-3-en-2-one, 4- (2,6,6-T rimethylcyclohex-1 -en-1 -yl)but-3-en-2-one, 4-(2,2,6-T rimethyl-2- cyclohexenyl)3-methyl-3-buten-2-one, N-methyl ionone, Non-2-enenitrile, 4-(2, 5,6,6- tetramethyl-2-cyclohexen-1 -yl)- 3-buten-2-one, 4-(2,5,6,6-Tetramethyl-2-cyclohexen-1 - yl)-3-buten-2-one (main component), Isoamyl acetate, Isobutyl salicylate, Isocyclo geraniol, 2-Hexyl-2-cyclopenten-1-one, 1,5-anhydro-2,4-dideoxy-2-pentyl-3-acetate- pentitol, jasmine absolute, tetrahydro-6-(2-pentenyl)-2H-pyran-2-one, 6-(pent-3-en-1 - yl)-tetrahydro-2H-pyran-2-one, 3-methyl-2-[(2Z)-pent-2-en-1 -yl]cyclopent-2-en-1 -one, 2-hexyl-2-cyclopenten-1-ol, 3-pentyl-4-tetrahydropyranyl acetate, tetrahydro-3-pentyl- 2H-pyran-4-yl acetate, 1,3, 4,6,7, 8a-hexahydro- 1,1,5, 5-tetramethyl-2H-2, 4a-
Methanonaphthalen-8(5H)-one, 5-hexyl-5-methyloxolan-2-one, decahydro-2, 8,8- trimethylnaphthalene-2,4a-carbolactone, 3-(4-tert-butylphenyl)butanal, (4R.)-4-(1 - methylethyl)-1 -cyclohexene-1 -propanal, 2,5-dimethyl-2-indan methanol, linalool, linalool oxide, 4-(4-hydroxy-4-methyl-pentyl)-3-cyclohexen-1 -carboxyaldehyde, oc-methyl- cyclohexanepropanol, beta,beta-3-trimethyl-benzenepropanol, (Z+E)-para- menthan-7- ol, 3-methyl-5-phenylpentanal, methyl anthranilat, methyl benzoat, methyl diphenyl ether, methyl geraniate, methyl heptin carbonate, (E)-3-methyl-4-(2,6,6-trimethyl-1 - cyclohex-2-enyl)but-3-en-2-one, methyl-[(1 R,2R)-3-oxo-2-((Z)-pent-2- enyl)cyclopentyl]acetat, methyl naphthyl ketone, methyl octin carbonate, Methyl pentaoic acid-2, Methyl salicylate, mimosa absolute, 1 -(4-isopropyl-cyclohexyl) ethanol, 3- methyl-4-phenylbutan-2-ol, 2,2-dimethyl-3-phenylpropan-1 -ol, Acetic acid octahydro- 4,7-methano-inden-5-ylmethyl ester, narcisse absolute, Methyl 2-nonenoate, Nerol, Neroli oil, 3,7,11 -Trimethyl-1,6,10-dodecatrien-3-ol, Ethyl-2-naphthylether, 2- Methoxynaphthalin, 1 -(3-methyl-1 -benzofuran-2-yl)ethan-1 -one, Neryl acetate, trans, cis-2,6-Nonadienal, trans, trans-2,4-Nonadiena, 2,6-Nonadienol, 10- hydroxymethylene-2-pinene, orange flower absolute, 4-(2-methylbutan-2- yl)cyclohexan-1 -one, orris absolute, orris resin, palmarosa oil, 3-[(2Z)-3-hexenyloxy]- propanenitrile, 1,1 -dimethoxynon-2-yne, Nonanoic acid, Pentyl salicylate, Pentyl salicylate, 2-cyclohexylidene-2-phenylacetonitrile, Petitgrain oil, 2-Phenoxyethyl-2-
methylpropanoate, 3-Methyl-5-phenylpentan-1 -ol, Phenyl salicylate, Phenylethyl acetate, Phenylethyl alcohol, Phenylethyl benzoate, phenylethyl butyrate, Phenylethyl isovalerate, Phenylethyl methyl ether, Phenylethyl phenylacetate, Phenylethyl pivalate, Phenylethyl propionate, Phenylethyl salicylate, Phenylethyl tiglate, Phenylpropyl acetate, Prenyl salicylate, 2,6,10-Trimethyl-5,9-undecadien-1 -ol, 2-Hexylcyclopentanone, 2- Hexylcyclopentanone, 2-Heptylcyclopentanone, Ethyl-2,3,6-trimethylcyclohexyl carbonate, Methyl-2,2-dimethyl-6-methylenecyclohexanecarboxylate, oc-
(Trichloromethyl)benzyl acetate, beta-Methyl-benzenepentanol, Rose absolute, tetra- hydro-4-methyl-2-(2-methyl-1 -propen-1 -yl)- 2H pyran, 4-Methyl-2-phenyl-3,6- dihydro-2H-pyran, 4-Methyl-6-phenyl-3,6-dihydro-2H-pyran, 4-Methylene-2- phenyltetrahydro-2H-pyran, 2-Methyl-3-[4-(2-methylpropyl)phenyl]propanal, alpha- Terpineol, Tetrahydro linalool, Tetrahydro geraniol, Thiogeraniol, Tuberrose absolute, (E)-4-methyldec-3-en-5-ol, 2,2,5-Trimethyl-5-pentylcyclopentan-1 -one, Methyl 2-[[3- [4-(1,1 -dimethylethyl)phenyl]-2-methylpropylidene]amino] benzoate, 1 -Methyl-4-(4- methylpentyl)-3-cyclohexenecarbaldehyde, 4-(4-Methyl pent-3-enyl) cyclohex-3-ene-1 - carbaldehyde, Violet leaves absolute, cyclooct-4-en-1-yl methyl carbonate, 2,6- nonadienenitrile, Ylang Ylang oil: aromatic/herbal scent note: Cyclohexane-1 -methanol, alpha, 3, 3-trimethyl formate, Artemisia oil, Bornyl acetate, Camphene, Camphor, D,L, Caraway oil, Carvacrol, Carveol, L, Carvomenthone, Carvone D, Carvone L, Cedar leave oil, 1,3,3-Trimethyl-2- oxabicyclo[2.2.2]octane, Clary sage oil, 3a,4,5,6,7,7a-Hexahydro-1 H-4,7-methanoinden- 5-yl 2-methylpropanoate, p-Cymene, Cypress oil, Di hydrocarvone, Dill oil, 1 - Methoxyhexane, 1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane, Eucalyptus oil, Fenchol, 1,3,3-Trimethyl-2-norbornanyl acetate, fir absolute, fir balsam, 1 -(3,3- Dimethylcyclohexyl)ethanone, 3a,4,5,6,7,7a-Hexahydro-4,7-methanoinden-6-yl acetate, Tricyclodecenyl propionate, isoborneol, isobornyl acetate, isobornyl propionate, isobutyl menthone, isomenthone, isopropyl cyclohexanol, juniper berry oil, laurel noble leaf oil, lavandin oil, lavender oil, marjoram oil, mentha arvensis oil, menthol, menthol L/isomenthol, menthyl acetate, (3,3,5-trimethylcyclohexyl) acetate, 6,6-dimethyl-2- norpinene-2-ethanolacetate, origanum oil, 4-tert-Butylcyclohexyl acetate, pennyroyal oil, peppermint oil, pine needle absolute, pine oil, 6,6-dimethyl-bicyclo[3.1.1]hept-2- ene-2-propanal, Octahydro-7-methyl-1,4-methanonaphthalen-6(2H)-one, 4-Acetoxy-4- methyl-2-propyltetrahydro-2H-pyran, spearmint oil, spike oil, tea tree oil, Terpinen-4- ol, 2,6,6,10-Tetramethyl-1 -oxaspiro[4.5]dec-9-ene, thuja oil, [1S-(1a,4a,5a)]4-methyl-1 - (1 -methylethyl)-bicyclo[3.1.0]hexan-3-one, thyme oil, thymol, turpentine oil, 2-tert- Butylcyclohexanol, wormwood oil; and mixtures thereof. citrus scent note are selected from the group consisting of 3,7-dimethyl-6-octene-1 - nitrile, decanal, 6,6-dimethoxy-2,5,5-trimethylhex-2-ene, bergamot oil, ethyl 6- acetoxyhexanoate, cedrat oil, citral diethyl acetal, citral, 2,4-Dimethyl-3-cyclohexene-1 - methanyl acetate, Citronella oil, Citronellal, (E)-3-Methyl-5-phenylpent-2-enenitrile and
(Z)-3-Methyl-5-phenylpent-2-enenitrile, alpha Ethenyl-alpha-methyl-benzenepropane nitrile, 2,4,4,7-tetramethyl-6-octen-3-one, (+/-)-2,8-Epithio-cis-p-menthane, 3- Mercapto-|3,4-dimethylcyclohexaneethanethiol, Cyclohexyl ethylacetate, Dihydromyr- cenol, Dihydromyrcenil acetate, Dimethyl octenone, Ethyl linalyl acetate, Eucalyptus oil, Grapefruit oil, 3-Methyl-5-phenylpentanenitrile, Lemon oil, Lemongrass oil, 3,7- Dimethyl-2(3),6-nonadienonitrile, 1 -Methyl-4-(1 -methylethenyl)cyclohexene, Lime oil, Linalyl acetate, Linalyl benzoate, Linalyl butyrate, Linalyl formate, Linalyl isobutyrate, Linalyl propionate, Litsea Cubeba oil, (E)-2, 12-Tridecadiennitrile and (E)-3,12- Tridecadiennitrile + (Z)-3,12-Tridecadiennitrile, (E)-2-dodecenal, mandarin oil, 2- methyl-4-propyl-1,3-oxathiane, myrcenyl acetate, trimethyl-3,5,5-hexyl acetate, (4R,4aS,6R)-6-lsopropenyl-4,4a-dimethyl-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalinon, (3Z,6E)-8-ocimenyl acetate, orange oil, 2-Ethyl-N-methyl-N-(3- methylphenyl)butanamide, 2,6-dimethyl-10-methylene-2,6,11 -dodecatrienal, (2S)-2- (1,1 -dimethylpropoxy)-propyl propanoate, tangerine oil, (E/Z)-6,10-Dimethylundeca- 5,9-dien-2-yl acetate, Terpinyl acetate, Tetrahydro linalyl acetate, Tetrahydromyrcenol green scent note: allyl amyl glycolate, sec-butyl-3-methylbutanthioate, 2,4-dimethyl- 3-cyclohexen-1 -carbaldehyde (main component), allyl (cyclohexyloxy)-acetate, dibutyl sulfide, 2-ethyl-3,5(6)-dimethylpyrazine, 2,3-dimethylpyrazine, 2,5-dimethylpyrazine, 2,6-dimethylpyrazine, 1 -(5,5-dimethyl-1 -cyclohexen-1 -yl)-4-penten-1 -one, 2- ethylpyrazine, 2,4,6-trimethyl-4-phenyl-1,3-dioxane, galbanol, 1 -(5,5-Dimethylcyclohex- 1 -en-1 -yl)pent-4-en-1 -one, N,2-Dimethyl-N-phenylbutyramide, 2-[6(5)-Methyl-8(7)-(1 - methylethyl)bicyclo[2.2.2]oct-5-en-2-yl]-1,3-dioxolane, 3,3,5-Trimethylcyclohexyl ethyl ether, 2-trans-hexenal, 3-trans-hexenol, 3-cis-hexenol, 2-trans-hexenol, 3- hexenylacetate (cis/trans), 3-cis-hexenylacetate, 2-trans-hexenylacetate, 3-cis- hexenylbenzoate, 3-cis-hexenylbutyrate, 3-cis-hexenylcaproate, 3-cis-hexenylacetal, 3- cis-hexenylformate, 3-cis-hexenylisobutyrate, 3-cis-hexenylisovalerate, 3-cis- hexenyllactate, 3,2-cis-hexenylmethylbutyrate, 3-cis-hexenylpropionate, 3-cis- hexenyltiglate, hexenyl tiglate, (2,2-Dimethoxy-1 -methylethyl)benzene, 2-lsobutyl-3- methoxypyrazine, 2,4,6-Trimethyl-3-cyclohexene-1 -carboxaldehyde, 2-lsopropyl-3- methoxypyrazine, 2-lsopropyl-4-methylthiazole, (Z)-Hex-3-en-1 -yl methyl carbonate, (3E)-1 -(1 -Methoxypropoxy)-3-hexene, 2,4-Dimethyl-3-cyclohexencarboxaldehyde, 2,4- Dimethyl-tetrahydroindenodioxine, 2,6-Dimethyl-5-heptenal, Octa hyd ro- 1 H -4,7- methanoindene-1 -carbaldehyde, Methyl-dihydrocyclopentapyrazine, methyl 2- nonynate, 2- methyl pyrazine, 3,3,5-Trimethylcyclohexyl acetate, 1 -(5,5- dimethyl-1 - cyclohexen-1-yl)-4-Penten-1 -one, 3,5,6-trimethyl-3-cyclohexene-1 -carboxaldehyde, 6- cis-nonenol, 1 -Octen-3-ol, Phenylacetaldehyde, Phenylacetataldehyde dimethylacetal, 8-ocimen-1 -yl acetate, 5H,5M Cyclopenta parzine, Tetrahydro-2, 4-dimethyl-4-phenyl- furan, 6-Ethylideneoctahydro-5,8-Methano-2H-1 -benzopyran, 1 -Spiro[4.5]dec-7-en-7- yl-4-penten-1 -one, 5-Methyl-3-heptanone oxime, 1 -Phenylethyl acetate, 1 -Phenylethyl alcohol, 1 -Phenylethyl propionate, beta-Methyl-benzenepropanal, 2-propenyl-p-
cymene, 4-ethenyl-2-(2-methylpropyl)-1,3-dioxolane, 2,4,6-Trimethyl-4-phenyl-1,3- dioxane, 3-(Methylthio)propyl butyrate, 2,4-Dimethylcyclohex-3-ene-1 -carbaldehyde, Dimethyl-3-cyclohexene-1 -carboxaldehyde, Methyl 2-{[(1 E)-(2,4-dimethylcyclohex-3- en-1 -yl)methylene]amino}benzoate, sec-Butyl-3-methylbutanthioate, 2,4-Dimethyl-3- cyclohexen-1-carbaldehyde, Allyl (cyclohexyloxy)acetate, Dibutyl sulfide, 2-Ethyl-3,5(6)- dimethylpyrazine, and mixtures thereof. spicy scent note: allspice oil, benzyl cinnamate, isoeugenyl benzyl ether, caryophyllene, cassia oil, methylcinnamic alcohol, cinnamic acid, Cinnamic alcohol, Cinnamic aldehyde, Cinnamic leaf oil, Cinnamon oil, Cinnamyl acetate, Cinnamyl cinnamate, Cinnamyl formate, Cinnamyl isobutyrate, Cinnamyl isovalerate, Cinnamyl nitrile, Clove bud oil, Clove leaf oil, Cumin oil, Cuminic alcohol, Cuminic aldehyde, Cuminic nitrile, Cuminyl acetate, Dihydroeugenol, Ethyl cinnamate, Eugenol, Eugenol methyl ether, Eugenyl acetate, Gingergrass oil, 2-Methoxycinnamaldehyde, Isoamyl cinnamate, Isobutyl cinnamate, Isoeugenol, isoeugenol acetate, Isoeugenol methyl ether, Linalyl cinnmate, Mace oil, 5(or 6)- Methyl-7(or 8)-(1 -methylethyl)bicyclo[2.2.2]oct-5-ene-carbaldehyde, Methoxy cinnamic aldehyde, Methyl cinnamate, Methyl cinnamic aldehyde, 2-Ethoxy-4- (methoxymethyl)phenol, 7-methyl-3-methylene-1,6-octadiene, Nutmeg oil, p-Mentha- 1,8-dien-7-al, Phenylethyl cinnamate, Phenylpropyl alcohol, Phenylpropyl aldehyde, 3- Phenylpropyl isobutyrate, Pimento oil, 2,3,3-Trimethylindan-1 -one, 2,6,6- trimethylcyclohexa-1,3-dienylmethanal, 1,2-dimethoxybenzol; and mixtures thereof.
[0019] In such case, said primary (a) and said two secondary fragrances (bl, b2) can be present in the mixture in ratios by weight (a):(b1 +b2) of from about 0.1 :99.9 to about 10:90, preferably from about 2:98 to about 3:97, and more preferably about 2.5:97.5
[0020] Regardless, whether binary or ternary mixtures are obtained, in all cases the preferred primary fragrances (a) are selected from the group consisting of
• 3,4-dimethyl benzonitrile;
• 4-(2-methylpropyl) benzonitrile;
• 3-methyl benzonitrile;
• 2-methoxy benzonitrile;
• 3,4-dimethoxy benzonitrile;
• 4-methoxy benzonitrile and mixtures thereof.
[0021] The most preferred primary fragrances (a) is 3,4-dimethyl benzonitrile.
Solvents
[0022] In another preferred embodiment the fragrance mixtures according to the present invention incorporate solvents (component c) in perfumery grade as for example water, ben-
zyl alcohol, benzyl benzoate, diethyl phthalate, dipropylene glycol, ethyl alcohol (ethanol), zso-propyl myristate, triethyl citrate, dipropyleneglycol methyl ether (Downol0 DPM), petroleum distillates such as for example IsoPar L (Exxon), triacetin and their mixtures.
[0023] Particular preferred are ethanol, dipropylene glycol and triethyl citrate and mixtures thereof.
[0024] Said solvents can be present in the mixture in an amount of up to 25 wt.-percent, preferably in amounts of from about 1 to about 20 wt.-percent, more preferably from about 2 to about 15 wt.-percent and most preferably from about 5 to about 10 wt.-percent.
[0025] With regard to long-lasting effects a combination of 3,4-dimethyl benzonitrile, one or two of the preferred secondary fragrances and one of the preferred solvents, in particular ethanol, has been found working best.
PERFUME PREPARATIONS
[0026] Another object of the present invention refers to a perfume preparation comprising the mixtures as defined above and at least 1, 2, 3, 4, 5 or more tertiary fragrances or perfume oils, preferably different from components (a), but might overlap with components (b).
[0027] Suitable fragrances and perfume oils can be selected from the group consisting of
• alcohols,
• aldehydes,
• amines, amides, nitriles,
• esters,
• ethers,
• ketones,
• lactones
• and mixtures thereof.
[0028] In the following these groups are illustrated by various examples, distinguishing between fragrances or perfume oil which are known to the expert by their tradenames or their trivial names.
Alcohols
Suitable alcohols known to the expert by their tradenames encompass for example 1 -(2-tert- butylcyclohexyl)oxybutan-2-ol (139504-68-0; Amber core); 2,6-di-tert-butyl-p-cresol (128-37- 0; BHT Ionol); (Z)-3-methyl-5-(2,2,3-trimethyl-1 -cyclopent-3-enyl)pent-4-en-2-ol (67801 -20- 1; Ebanol); 4-methyl-2-(2-methylpropyl)oxan-4-ol (63500-71 -0; Florosa/ Pyranol); [(1 R.,2S)-1- methyl-2-[[(1 R.,3S,5S)-1 , 2, 2-trimethyl-3-bicyclo[3.1.0]hexanyl]methyl]cyclopropyl] methanol (198404-98-7; Javanol); (3R)-1-[(1 R,6S)-2,2,6-trimethylcyclohexyl]hexan-3-ol; (3S)-1 -[(1 R,6S)- 2,2,6-trimethylcyclohexyl]hexan-3-ol (70788-30-6; Norlimbanol); 3-methyl-5-phenylpentan-1-
ol (55066-48-3; Phenoxanol); (E)-3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1 -yl)-4- penten-2-ol (107898-54-4; Polysantol); 5-(3-methylphenyl)pentan-1-ol (25634-93-9; Rosa- phen); 3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1 -yl)pentan-2-ol (1471313-03-7; 65113-99- 7; Sandalore); (2E)-2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1 -yl)-buten-1 -ol + 2-ethyl-4- (2,2,3-trimethyl-3-cyclopenten-1 -yl)-2-buten-1 -ol (106185-75-5; 28219-61-6; Sandranol); (E)- 4-methyldec-3-en-5-ol (81782-77-6; Undecavertol); 3-[5,5,6-Trimethylbicyclo[2.2.1]hept-2- yl]cyclohexan-1 -ol (70955-71 -4; Sandela) and mixtures thereof.
Suitable alcohols known to the expert by their trivial names encompass for example hexan-1 - ol; octan-1 -ol; decan-1 -ol; dodecan-1 -ol; Borneol; Isoborneol; Citronellol; L-Citronellol; Dihydro Eugenol; Dihydro Myrcenol; Dimethyl Benzyl Carbinol; Ethyl Linalool; Eugenol; Geraniol; Cis-3-Hexenol; Isobornyl Cyclohexanol; Linalool; Nerolidol; Phenylethyl alcohol; Phenylethyl Dimethyl Carbinol; Phenylpropyl Alcohol; Propenyl Guaethol; Sulfurol; alpha-Terpineol; Tetrahydro Linalool; Thymol and mixtures thereof.
Aldehydes
Suitable aldehydes known to the expert by their tradenames encompass for example 2,6,10- trimethylundec-9-enal (141 -13-9; Adoxal; Farenal); alpha-,3,3-trimethyl- cyclohexanemethanolformate (25225-08-5; Aphermate); 4-(1, 1 -dimethylethyl)- benzenepropanal (18127-01 -0; Bourgeonal); 6-methoxy-2,6-dimethyloctanal (929253-05-4; Calypsone); 4-methoxy-.alpha.-methyl-benzenepropanal (5462-06-6; Canthoxal); a, 2,2,6- tetramethylcyclohexenebutanal (65405-84-7; Cetonal); 8,8-dimethyl-1,2,3,4,5,6,7,8-octahydro-
2-naphthaldehyde + 1,2,3,4,5,6,7,8-octahydro-5,5-dimethyl-2-naphthalenecarboxaldehyde (68991 -96-8; 68991 -97-9; Cyclomyral); 4-(octahydro-4,7-methano-5H-inden-5-ylidene butanal (30168-23-1; Dupical); 4,8-dimethyl-4,9-decadienal (71077-31 -1; Floral Super); 3-(4- ethylphenyl)-2,2-dimethylpropanal + 3-(2-ethylphenyl)-2,2-dimethylpropanal (67634-15-5; 67634-14-4; Florazon); beta-methyl-3-(1-methylethyl)-benzenepropanal (12509-85-5; Florhy- dral); methylenedioxyphenyl-methylpropanal (1205-17-0; Helional); oc,4- dimethylbenzenepropanal (41496-43-9; Jasmorange, Satinaldehyde); (Z,E)-2,4-dimethyl cy- clohex-3-ene-1-carbaldehyde (68039-49-6; 68737-61-1; Ligustral, Tripalal, Cyclal C, Vertocitral) ; 3-(4-tert-butylphenyl)butanal (80-54-6; Lilial); (1 R)-|3,4-dimethyl-3-cyclohexene- 1 -propanal (199445-85-7; Liminal); (4R)-4-(1 -Methylethyl)-1 -cyclohexene-1-propanal (1378867-81 -2; Lilybelle); (4S)-4-(1 -Methylethyl)-1 -cyclohexene-1 -propanal (1378867-82-3; Lilybelle Isomer); 4-(4-Hydroxy-4-methyl-pentyl)-3-cyclohexen-1 -carboxyaldehyde (130066- 44-3; Lyral); 6-methyl-1 -8-yl-methyleth l-bicyclo[2.2.2]oct-5-ene-2-carboxaldehyde (67845- 30-1; Maceal); (±)-2,6-Dimethyl-5-heptenal (106-72-9; Melonal); (E)-2,6,10-trimethylundeca- 5,9-dienal (54082-68-7; Oncidal); 6,6-Dimethyl-2-norpinene-2-propionaldehyde (33885-51 -7; Pinoacet aldehyde); 1 -methyl-4-(4-methyl-3-pentenyl)cyclohex-3-ene-1 -carboxaldehyde + 6,6-dimethyl-2-norpinene-2-propionaldehyde (119652-81 -2; 52475-86-2; Precyclemone B);
3-phenylbutanal (16251 -77-7; Trifernal); octahydro-5-methoxy-4,7-methano-1 H-indene-2-
carboxaldehyde (86803-90-9; Scentenal); rel-(3aR,4R,5R,7R,7aR)-octahydro-4,7-methano-1 H- indene-5-carboxaldehyde (145374-28-3; Vertral); 4-(4-methyl pent-3-enyl) cyclohex-3-ene-1 - carbaldehyde (37677-14-8; Vertomugal); and mixtures thereof.
Further on, aldehydes known to expert by their trivial name encompass for example Hexanal; Heptanal; Octanal; 2-Nonen-1 -al; Nonanal; Decanal; Undecenal; 2-Methyldecanal; 10- Undecenal; Undecanal; Dodecanal; 2-Methylundecanal; Anisic Aldehyde; Benzaldehyde; Citral; Citronellal; Cinnamaldehyde; Cuminic Aldehyde; Cyclamen aldehyde; Dihydrocitronellal; trans-2-dodecanal; Ethyl Vanillin; Geranial; Heliotropin/Piperonal; trans-2-hexenal; Alpha- hexyl-cinnamic aldehyde; Hydratropic Aldehyde; Hxdroxy Citronellal; Isocyclocitral;; Methox- ycitronellal; Neral; Phenylacetaldehyde; Tangerinal; Cyclamen Homoaldehyde; Vanillin; and mixtures thereof.
Amines, amides, and nitriles
Suitable amines, amides and nitriles known to the expert by their tradenames encompass for example 3,7-dimethyloct-6-enenitrile (51566-62-2; Argunitril); (E/Z)-3-methyl-5-phenylpent- 2-enenitrile (53243-59-7; 53243-60-0; 93893-89-1; Citronitrile); 3,7-dimethylnona-2,6- dienenitrile (61792-11 -8; Lemonile); 4-[(3E)-4,8-dimethylnona-3,7-dienyl]pyridine (38462-23- 6; Maritima); tridec-2-enenitrile (22629-49-8; Ozonil); 2-cyclohexylidene-2-phenylacetonitrile (10461-98-0; Peonile); and mixtures thereof.
Suitable amines, amides or nitriles known to the expert by their trivial names encompass for example indol
Esters
Suitable esters known to the expert by their tradenames encompass for example cis-2-tert- butylcyclohexyl acetate + (2-tert-butylcyclohexyl) acetate (20298-69-5; 88-41 -5; Argumex HC I LC); ethyl 3-methyl-3-phenyloxirane-2-carboxylate (77-83-8; Aldehyde C16 so-called); prop- 2-enyl 2-cyclohexyloxyacetate (68901 -15-5; Cyclogalbanat); methyl 2,4-dihydroxy-3,6- dimethylbenzoate (4707-47-5; Evernyl); 4-methylpentan-2-y€E)-but-2-enoate (35206-51 -0; Frutinat); ethyl 2-ethyl-6,6-dimethylcyclohex-2-ene-1 -carboxylate (57934-97-1; 77851 -07-1; Givescone); methyl 3-oxo-2-pentylcyclopentaneacetate (24851 -98-7; Hedione); 2-'1-'3',3'- dimet'yl-1 '-cyclohexyl)ethoxy)-2-methyl propyl propanoate (141773-73-1; Helvetolide); 3a,4,5,6,7,7a-hexahydro-4,7-methanoinden-6-yl acetate (5413-60-5; Herbalflorat); 3a,4,5,6,7,7a-hexahydro-4,7-methanoinden-6-yl acetate (5413-60-5; Herbalflorat); [(Z)-hex-3- enyl] methyl carbonate (67633-96-9; Leafovert); ethyl 2-methylpentanoate (39255-32-8; Man- zanate); 2-[1 -(3,3-Dimethylcyclohexyl)ethoxy]-2-oxoethyl propionate (236391 -76-7; Roman- dolide); ethyl 2-cyclopent-2-en-1-ylacetate (15848-49-4; Sultanene); (1 S,2R,5S)-5-methyl-2- (1 -methylethyl)-cyclohexanolacetate + [(1 R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]- acetate (29066-34-0; 89-48-5; Symfresh RF / Menthylacetate); 3-hydroxy-2,2,4-
trimethylpentyl 2-methylpropanoate (25265-77-4; Symfresh NX); (4-methyl-4-phenylpentan- 2-yl)-acetate (68083-58-9; Vertikolacetat); and mixtures thereof. €"'
Suitable esters known to the expert by their trivial names encompass for example Allyl Amyl Glycolate; Allyl Caproate; Allyl Cyclohexyl Propionate; Allyl Heptoate; Benzyl Acetate; Benzyl Salicylate; Citronellyl Acetate; Dimethyl Benzyl Carbinyl Acetate ; Dimethyl Benzyl Carbinyl Butyrate; Ethyl Butyrate; Ethyl Caproate; Trans/Cis-2,4-Ethyl Decadienoate; Ethyl-2-Methyl Butyrate; Ethylene Brassylate ; Geranyl Acetate; Herbyl Propionate; Cis/Trans-3-Hexenyl Acetate; Cis-3 Hexenyl Acetate; Cis-3 Hexenyl Butyrate; Cis-3-Hexenyl Isobutyrate; Cis-3-Hexenyl Salicylate; Hexyl Acetate; Hexyl Butyrate; Hexyl Isobutyrate; Hexyl Salicylate; Isoamyl Acetate; Isobornyl Acetate; Isobutyl Acetate; Isoeugenyl Acetate; Linalyl Acetate; Methyl Octin Carbonate; Neryl Acetate; Phenylethyl Butyrate; Phenylethyl Cinnamate; Prenyl Acetate; Styralyl Acetate; Methylanthranilat; and mixtures thereof. €
Ethers
Suitable ethers known to the expert by their tradenames encompass for example (3aR,5aS,9aS,9bR)-3a, 6,6, 9a-tetramethyl-2, 4, 5, 5a, 7,8,9, 9b-octahydro-1 H-benzo[e][1] benzofuran (6790-58-5; Ambroxide); 5-hexyl-4-methyloxolan-2-one (67663-01 -8; Aprifloren); cy- clohexadec-2-en-1 -one (2550-59-6; 3100-36-5; 88642-03-9; Aurelione); 3,4-diethyl-2,5- dimethylcyclohex-2-en-1 -one (68845-36-3; Azarbre); 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8- hexamethylcyclopenta(g)-2-benzopyran (1222-05-5; Galaxolide); (2R,4S)-2-methyl-4-propyl-
1.3-oxathiane + 2-methyl-4-propyl-1,3-oxathiane (59323-76-1, 261 -699-8; Oxane/Ox'nthia; 3,7'-Dimethyl-3,4,4a,5,8,8a-hexahydrospiro-(1,4-methanonaphthale'e- 2(1 H),2’-oxirane) (41816-03-9; Rhubofix); and mixtures thereof"
Suitable ethers known to the expert by their trivial names encompass for example Anethol; Lime Oxide; Nerolin Yara Yara; Orange Flower Ether; and mixtures thereof.
Ketones
Suitable ketones known to the expert by their tradenames encompass for example 7-methyl-
3.4-dihydro-2H-1,5-benzodioxepin-3-one (249-320-4; Calone); 1,2,3,5,6,7-hexahydro- 1,1,2,3,3-pentamethyl-4H-inden-4-one (251 -649-3; Cashmeran); [3R-(3oc,3a|3,6a,7|3,8aa)]- octahydro-6-methoxy-3,6,8,8-tetramethyl-1 H-3a,7-methanoazulene + (3R,3aS,6R,7R,8aS)- octahydro-6-methoxy-3,6,8,8-tetramethyl-1 H-3a,7-methanoazulene (19870-74-7; 67874-81 - 1; Cedramber); 3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1 H-benzo[e][1]benzofuran (3738-00-9; Cetalox); 1 -(5,5-dimethyl-1-cyclohexenyl)pent-4-en-1 -one (56973-85-4; Dynascone, Galbascone); 1 -[bis(2-hydroxypropyl)amino]propan-2-ol; 5-methylhept-2-en-4- one (102322-83-8; 81925-81 -7; Filbertone); 4-(4-hydroxyphenyl)butan-2-one (5471 -51 -2; Frambinon); (8E)-cyclohexadec-8-en-1 -one (3100-36-5; Globanone); 4-(2, 5,6,6- tetramethylcyclohex-2-enyl)but-3-en-2-one (201 -219-6; Alpha Irone); 1-(2,3,8,8-tetramethyl- 1,3,4,5,6,7-hexahydronapht ft he lyl)ethanone (54464-57-2; Iso E Super); cyclohexadecanone
(2550-52-9; Isomuscone); 5,5,9, 13-tetramethyl-14, 16- dioxatetracyclo[11.2.1.01, 10.04, 9]hexadecane (57345-19-4; Ketamber); 5-hexyl-5- methyloxolan-2-one (7011 -83-8; Lact€smone); (E)-3-methyl-4-(2,6,6-trimethyl-1-cyclohex-2- enyl)but-3-en-2-one (127-51 -5; Methyl Ionone Gamma Coeur); N-1 -(2,6,6-trimethyl-1 - cyclohex-2-enyl)pent-1-en-3-one (1335-46-2; Methyl Ionone Gamma Pure); (5E)-3- methylcyclopentadec-5-en-1 -one; (5E)-3-methylcyclopentadec-5-en-1 -one (63314-79-4; 82356-51-2; Muscenone); 3-methylcyclopentadecan-1 -one (541 -91 -3; Muscone); 2-[2-(4- methyl-1 -cyclohex- ft he li neyl]cyclopentan-1 -one (95962-14-4; Nectaryl); 1 -(3-methyl-1 - benzofuran-2-yl)ethan-1 -one (23911 -56-0; Nerolione); octahydro-7-methyl-1,4- methanonaphthalen-6(2H)-one (41724-19-0; Plicatone); 1 -(3,5,5,6,8,8-hexamethyl-6,7- dihydrona ft he l-2-yl)ethanone + 1 -(3,5,5,6,8,8-hexamethyl-6,7-dihydrona ft he I-2- yl)ethanone (1506-02-1; 21145-77-7; Tonalide); 2,2,5-trimethyl-5-pentylcyclopentan-1 -one (65443-14-3; Veloutone); and mixtures thereof, ft he li ne ft he I
Suitable ketones known to the expert by their trivial names encompass for example Dama- scenone; Alpha Damascene; Beta Damascene; Delta Damascene; Beta Dihydro Ionone; Dihydro Jasmone; Ethyl Maltol; Gamma Hexalactone; Alpha Ionone; Beta Ionone; Jasmin Lactone; Jasmolactone CNC; Jasmone Cis; Maltol; Methyl Ionone; and mixtures thereof. €€
Lactones
Suitable lactones known to the expert by their trade names encompass for example 5- heptyloxolan-2-one (104-67-6; Aldehyde C14 So-Called); 5-pentyloxolan-2-one (203-219-1; Aldehyde C18 So-Called); (9Z)-17-oxacycloheptadec-9-en-1 -one (28645-51 -4; Ambrettolide); (12E)-1-oxacyclohexadec-12-en-2-one + (3E)-oxacyclohexadec-3-en-2-one (111879-80-2; 34902-57-3; Globalide); 16-oxacyclohexadecan-1-one (106-02-5; Supra Macrolide), and mixtures thereof.
Further on, lactones known to expert by their trivial name encompass for example Delta Decalactone; Gamma Decalactone; Gamma Octalactone; Rose Oxide High Cis; and mixtures thereof.
Etherical oils and extracts
Suitable fragrances and perfume oils can also be chosen from etherical or essential oils and extracts, such as for example Ambrette Seed Absolue; Amyris Oil; Angelica Root Oil; Apricot Seed Oil; Artemisia Oil; Basil Oil; Bay Oil; Beeswax Abs; Benzoin Resinoid; Bergamot Oil; Boya; Cabreuva Oil; Cade Oil; Cananga Oil Java; Caraway Oil; Cardamom Abs./Oil; Carrot Seed Oil; Cassia Oil; Cassie Abs. A Egypt; Cassis Abs. Burgundy; Castroreum Abs.; Cedar Leaf Oil; Cedarwood Oil; Cedarwood Oil; Cedarwood Oil Atlas; Celery Seed Oil; Chamomile Oil Blue; Chamomile Oil Roman; Cinnamon Bark Oil; Cinnamon Leaf Oil; Cistus Labdanum Abs.SIS; Cis- tus Oil; Citronella Oil Formosa/Java; Clary Sage Oil; Clove Bud Oil; Clove Leaf Oil; Coconut Oil;
Copaiba Balsam Oil; Coriander Oil; Cumin Oil; Cypress Oil; Cypriol Oil; Davana Oil; Dill Weed Oil; Dynamone; Elemi Oil I Gum; Estragon Oil; Eucalyptus Oil Citriodora; Fennel Oil Sweet; Fir Balsam Abs.; Fucus Abs.; Galbanum Oil; Geranium Oil; Ginger Extract I Oil; Grapefriut Oil White; Guaiac Wood Oil; Gurjun Balsam Oil; Hay Abs; Hydrocarboresin B; Immortelle Abs.; Jasmin Abs.; Jasmin Abs. Sambac; Juniper Berry Oil R.S; Labdanum Abs. I Resinoide; Laurel Noble Leaf Oil FLS; Lavandin Oil; Lavender Oil White; Lemon Oil; Lemon Oil Terpenes; Lemon Oil Winter; Lemongrass Oil; Lentisque Abs.; Lime Oil; Lime Oil Terpenes; Litsea Cubeba Oil; Longoza Oil; Lovage Root Oil; Mace Oil Dist. Low Safrol; Mace Oil; Magnolia Flower Oil; Magnolia Leaf Oil; Mandarin Oil; Marjoram Oil; Mentha Arv. Oil; Mimosa Abs.; Mousse C Abs.; Myrrh Oil; Myrtle Oil; Narcisse Abs.; Neroli Oil; Nutmeg Oil; Olibanum Oil; Opoponax Oil / Resinoid; Orange Flower Abs.; Orange Oil; Origanum Oil; Osmanthus Abs.; Palmarosa Oil; Parsley Leaf Oil; Parsley Seed Oil; Patchouli Oil; Pepper Black Oil; Pepper Oil I Abs. Sichuan Type; Peppermint Oil; Peru Balsam Oil; Petitgrain Bigaeade Abs.; Petitgrain Oil Citronnier; Pimento Leaf Oil; Pine Needle Abs.; Pine Needle Oil; Pink Pepper Leaf Oil; Red Berry Extract; Red Berry Oil; Rose Abs.; Rosemary Oil; Rum CO2 Extract; Sage Officinale Oil Dalm; Sandalwood Oil; Spearmint Oil; Spike Oil ; Star Anise Oil; Styrax Oil; Sweet Almond Oil; Tagetes Oil; Tangerine Cravo Oil Brazil; Tea Tree Oil; Thuja Oil; Thyme Oil; Timut Pepper Oil; Tonka Bean Abs.; Tuberose Abs.; Tumeric Oil ; Turpentine Oil; Vanilla Abs; Vetiver Oil/Abs; Violet Leaves Abs.; Wheat Bran Abs.; Wormwood Oil; Ylang Ylang Oil; and mixtures thereof.
[0029] Another object of the present invention refers to a method for preparing said perfume preparation, comprising or consisting of tllowing steps:
(6) (i) providing the fragrance mixture as defined above;
(ii) providing at least 1, 2, 3, 4, 5 or more tertiary fragrances, particularly those chosen from the list provided above; and
(iii) adding about 1 to about 100 parts of component (i) to 900 to 999 parts of component (ii) to get 1,000 parts of the preparation. +
CUSTOMER PRODUCTS
[0030] Another object of the present application refers to customer products, more precisely cosmetic, detergent or household products, obtained according to tllowing steps:
(6) (i) providing the fragrance mixture or the perfume preparation as defined above;
(ii) providing a cosmetic, detergent or household base composition;
(iii) adding about 10 to about 100 parts of component (i) to 990 to 999 parts of component (ii) to get 1,000 parts of the product.
[0031] Also claimed is a method for preparing a cosmetic, detergent or household products, comprising or consisting of tllowing steps:
(6) (i) providing the fragrance mixture or the perfume preparation as defined above;
(ii) providing a cosmetic, detergent or household base composition;
(iii) adding about 10 to about 100 parts of component (i) to 990 to 999 parts of component (ii) to get 1,000 parts of the product.
[0032] The term "base formulation" means the complete consumer product, for example a shampoo, a body lotion, a liquid detergent or softener, which only lacks the addition of the fragrance mixture or perfume preparation according to the invention. To avoid any doubts, step (iii) means that a specific amount of the fragrance mixture or the perfume preparation is blended with a corresponding amount of the base to provide 1000 parts or 100 wt.-percent.
INDUSTRIAL APPLICATION
[0033] Another object of the present invention concerns a method of modulating, intensifying and/or increasing the long-lasting of a fragrance comprising or consisting of flowing steps:
(6) (i) providing at least one a primary fragrance according to general formula (I)
wherein R1, R2, R3, R4, and R5 independently of one another represent hydrogen or linear or branched Ci-Cio-alkyl, which is optionally substituted with hydroxy or Ci -C4-alkyl or linear or branched Ci-Cio-alkoxy, which is optionally substituted with hydroxy or Ci- C4-alkyl,
(ii) providing at least one secondary fragrance different from component (a), said at least one secondary fragrance exhibiting at least one of the following scent notes: fruity; woody; floral; aromatic/herbal; citrus; spicy; and
green.
(iii) optionally providing at least one solvent;
(iv) blending components (i), (ii) and optionally (iii).
[0034] In a preferred embodiment of said primary fragrances are selected from the group consisting of
• 3,4-dimethyl benzonitrile;
• 4-(2-methylpropyl) benzonitrile;
• 3-methyl benzonitrile;
• 2-methoxy benzonitrile;
• 3,4-dimethoxy benzonitrile;
• 4-methoxy benzonitrile and mixtures thereof.
[0035] The over-all preferred primary fragrance to be used in this method is 3,4-dimethyl benzonitrile.
[0036] The preferred secondary fragrances are selected from the group consisting of homomenthyl acetate, myrcene, phellandrene, phenoxyethyl isobutyrate, 2-ethyl-4-(2,2,3- trimethylcyclopent-3-en-yl)-but-2-en-1-ol, isobutyric acid- 1 -hydroxy-2, 2, 4-trimethyl-3-pentyl ester and isobutyric cid-3-hydroxy-2, 2, 4-trimethyl-1 -pentyl ester and mixtures thereof.
[0037] The solvents are selected from the group consisting of water, benzyl alcohol, benzyl benzoate, diethyl phthalate, dipropylene glycol, ethyl alcohol, zso-propyl myristate, triethyl citrate, dipropyleneglycol methyl ether, petroleum distillates, triacetin and mixtures thereof.
[0038] The preferred solvents are selected from the group consisting of ethanol, dipropylene glycol, triethyl citrate and mixtures thereof.
[0039] In a preferred embodiment the primary fragrance is 3,4-dimethyl benzonitrile; the secondary fragrances are selected from homomenthyl acetate, myrcene, phellandrene, phenoxyethyl isobutyrate, 2-ethyl-4-(2,2,3-trimethylcyclopent-3-en-yl)-but-2-en- l-ol, isobutyric acid-1 -hydroxy-2, 2, 4-trimethyl-3-pentyl ester and isobutyric cid-3- hydroxy-2, 2, 4-trimethyl-1 -pentyl ester and mixtures thereof; and the solvents are selected from the group consisting of ethanol, dipropylene glycol, triethyl citrate and mixtures thereof.
[0040] I n an even more preferred embodiment the primary fragrance is 3,4-dimethyl benzonitrile; the secondary fragrances are selected from homomenthyl acetate, myrcene, phellandrene, phenoxyethyl isobutyrate, 2-ethyl-4-(2,2,3-trimethylcyclopent-3-en-yl)-but-2-en-
l -ol, isobutyric acid-1 -hydroxy-2, 2, 4-trimethyl-3-pentyl ester and isobutyric cid-3- hydroxy-2, 2, 4-trimethyl-1 -pentyl ester and mixtures thereof; and the solvent is ethanol.
[0041] Also claimed is the use of at least one a primary fragrance according to general formula (I)
wherein R1, R2, R3, R4, and R5 independently of one another represent hydrogen or linear or branched Ci-C -alkyl, which is optionally substituted with hydroxy or Ci-C4-alkyl or linear or branched Ci-Cio-alkoxy, which is optionally substituted with hydroxy or Ci -C4-alkyl, for modulating, intensifying and/or increasing the long-lasting of at least one fragrance, said at least one secondary fragrance exhibiting at least one of the following scent notes: fruity; woody; floral; aromatic/herbal; citrus; spicy; and green.
Preferably, said primary fragrances are added to said secondary fragrances in an amount of from about 0.1 to about 30 wt. -percent, more preferably from about 2 to about 5 wt. -percent - calculated on the final
EXAMPLES
Examples 1 -10 Olfactory evaluation of binary fragrance mixtures comprising 3,4-dimethyl benzonitrile and fragrances with fruity scent note
Examples 11-20
Olfactory evaluation of binary fragrance mixtures comprising 3,4-dimethyl benzonitrile and fragrances with woody scent note
Examples 21-32
Olfactory evaluation of binary fragrance mixtures comprising 3,4-dimethyl benzonitrile and fragrances with floral scent note
Examples 32 - 41
Olfactory evaluation of binary fragrance mixtures comprising 3,4-dimethyl benzonitrile and fragrances with aromatic and/or herbal scent note
Examples 42 - 51
Olfactory evaluation of binary fragrance mixtures comprising 3,4-dimethyl benzonitrile and fragrances with citrus scent note
Examples 52 - 61
Olfactory evaluation of binary fragrance mixtures comprising 3,4-dimethyl benzonitrile and fragrances with spicy scent note
Examples 62 - 71
Olfactory evaluation of binary fragrance mixtures comprising 3,4-dimethyl benzonitrile and fragrances with green scent note
Example 72-75
Olfactory evaluation of ternary fragrance mixtures
Example 76
Spicy perfume
Example 77
Woody perfume
Example 78
Floral perfume
Example 79
Aromatic perfume
Example 80
Citrus perfume
Example 81
Spicy perfume
Example 82
Green perfume
FORMULATION EXAMPLES
The following examples F1 to F55 show various formulations for cosmetic and detergent compositions. Formulation 1 stands for any of the fragrance mixtures according to Examples 1 to 75.
Table F1
Liquid soap; transparent (Amounts in % b.w.)
Table F2
Syndet soap; liquid (Amounts in % b.w.)
Table F3
Cosmetic lotion for body wash (Amounts in % b.w.)
Table F4
Cosmetic lotion for body wash with Triclosan (Amounts in % b.w.)
Table F5
Intimate wash (Amounts in % b.w.)
Table F6
Liquid soap (Amounts in % b.w.)
Table F7
Shampoo (Amounts in % b.w.)
Table F8
2-in- 1 Shampoo (Amounts in % b.w.)
Table F9
Anti-dandruff Shampoo (Amounts in % b.w.)
Table F10
Hair conditioner with Crinipan. rinse-off (Amounts in % b.w.)
Table F11
Sprayable hair conditioner With zinc pyrithrione. leave-on (Amounts in % b.w.)
Table F12
Hair conditioner with UV protection (Amounts in % b.w.)
Table 13
Shower gel (Amounts in % b.w.)
Table F14
Shaving foam (Amounts in % b.w.)
Table F15
Depilatory cream (Amounts in % b.w.)
Table F16
After Shave Tonic (Amounts in % b.w.)
Table F17
Deodorant formulation in the form of a roll-on gel (Amounts in % b.w.)
Table F18
Clear deo anti-perspirant roll-on (Amounts in % b.w.)
Table F19
Deodorant stick (Amounts in % b.w.)
Table F20
Zirconium suspensoid antiperspirant stick (Amounts in % b.w.)
Table F21
Deodorant pump spray with SymClariol (Amounts in % b.w.)
Table F22
Antiperspirant formulations (Amounts in % b.w.)
Table F23
Deodorant spray with Triclosan (Amounts in % b.w.)
Table F24
O/W lotion (Amounts in % b.w.)
Table F25
Body lotion (Amounts in % b.w.)
Table F26
Cream (Amounts in % b.w.)
Table F27
Cream (Amounts in % b.w.)
Table F28
Hand and body cream (Amounts in % b.w.)
Table F29
Face cream (Amounts in % b.w.)
Table F30
Moisturizing body care cream (Amounts in % b.w.)
Table F31
Anti-wrinkle cream (Amounts in % b.w.)
Table F32
Functional skin oil for disinfection (Amounts in % b.w.)
Table F33
Septic wound cream (Amounts in % b.w.)
Table F34
Moisturizing and disinfecting face mask (Amounts in % b.w.)
Table F35
Sprayable disinfecting gel (Amounts in % b.w.)
Table F36
Mineral wash and cleaning gel (Amounts in % b.w.)
Table F37
Anti-acne wash (Amounts in % b.w.)
Table F38
Cosmetic sun protection composition (Amounts in % b.w.)
Table F39
Sun protection spray (Amounts in % b.w.)
Table F40
Sunscreen spray 0/W. SPE 15-20 (Amounts in % b.w.)
Table F41
Sun protection soft cream (W/0). SPF 40 (Amounts in % b.w.)
Table F42
Sun protection milk (W/0) (Amounts in % b.w.)
Table F43
After sun gel (Amounts in % b.w.)
Table F44
After sun lotion (Amounts in % b.w.)
Table F45
Hair styling gel (Amounts in % b.w.)
Table F46
Silicone emulsion (Amounts in % b.w.)
Table F47
Microemulsion gel (Amounts in % b.w.)
Table F48
Air freshener in gel form (Amounts in % b.w.)
Table F49
Cleaner. APC liquid, alkaline pH 8-10 (Amounts in % b.w.)
Table F50 Fabric softener (Amounts in % b.w.)
Table F51
Liquid detergent (Amounts in % b.w.)
Table F52
Liquid detergent concentrate (Amounts in % b.w.)
Table F53
Toilet cleaner (Amounts in % b.w.)
Table F54
Dish washing concentrate (Amounts in % b.w.)
Table F55
Dish washing concentrate (Amounts in % b.w.)
Table F56
Solution for wet wipes (Amounts in % b.w.)
Claims
1. A fragrance mixture comprising or consisting of
(a) at least one a primary fragrance according to general formula (I)
wherein R1, R2, R3, R4, and R5 independently of one another represent hydrogen or linear or branched Ci -C -alkyl, which is optionally substituted with hydroxy or Ci- C4-alkyl or linear or branched Ci-Cio-alkoxy, which is optionally substituted with hydroxy or Ci -C4-alkyl,
(b) at least one secondary fragrance different from component (a) and optionally
(c) at least one solvent, wherein said at least one secondary fragrance belongs to the group of fragrances exhibiting at least one of the following scent notes: fruity; woody; floral; aromatic/herbal; citrus; spicy; and green.
2. The fragrance mixture according to Claim 1, wherein component (a) follows formula (II)
wherein R2, R3 independently of one another represent hydrogen or linear or branched Ci -Cio-alkyl, which is optionally substituted with hydroxy or Ci-C4-alkyl or linear or branched Ci-Cio-alkoxy, which is optionally substituted with hydroxy or Ci -C4-alkyl.
3. The fragrance mixture according to any of Claims 1 or 2, wherein said primary fragrance (a) is selected from the group consisting of
• 3,4-dimethyl benzonitrile;
• 4-(2-methylpropyl) benzonitrile;
• 3-methyl benzonitrile;
• 2-methoxy benzonitrile;
• 3,4-dimethoxy benzonitrile;
• 4-methoxy benzonitrile and mixtures thereof.
4. The fragrance mixture according to any of the preceding Claims 1 to 3, wherein said primary fragrance (a) is 3,4-dimethyl benzonitrile.
5. The fragrance mixture according to any of the preceding Claims 1 to 4, wherein said secondary fragrances (b) exhibiting a fruity scent note are selected from the group consisting of 2-methyl butyl isovalerate, acetyl butyryl, aldehyde C14 so-called, aldehyde C16 so-called, aldehyde C18 so-called, allyl heptylate, amyl acetate, amyl butyrate, amyl capronate, amyl formate, anisyl acetone, cis-2-tert-butylcyclohexyl acetate, (2-tert- butylcyclohexyl) acetate, benzyl butyrate, benzyl isobutyrate, benzyl isovalerate, butyl acetate, butyl butyrate, benzyl isobutyrate, benzyl isovalerate, butyl acetate, butyl butyrate, butyl caprylate, butyl formate, butyl isobutyrate, butyl isovalerate, butyl propionate, butyl salicylate, butyric acid, norborn-5-en-yl acetate, caproic acid, cyclohexyl acetate, cyclohexyl butyrate, 1 -cyclohexyl-(2E)-but-2-enoate, davana oil, delta decalactone, gamma decalactone, diethyl malonate, delta dodecalactone, gamma dodecalactone, ethyl acetate, ethyl butyrate, ethyl caprinate, ethyl capronate, ethyl caprylate, ethyl formate, ethyl heptoate, ethyl-3- hydroxy hexa noate, ethyl isobutyrate, ethyl isovalerate, ethyl laurate, ethyl levulinate, ethyl-2-methyl butyrate, ethyl pelargonate, ethyl-3- phenylglycidate, ethyl propionate, ethyl valerate, ethyl-2-tertbutylcyclohexyl carbonate,
ethyl-2,4-dimethyl-1,3-dioxolane-2-acetate, 4-(4-hydroxyphenyl) butane-2-one, 4-4(4- hydroxyphenyl) butane-2-one methyl ether, ethyl tricyclo [5.2.1.0 2.6] decane-2- carboxylate, 4-methylpentane-2-yl-( E)-but-2-enoate, furfuryl acetate, gammaheptalactone, heptanoic acid, heptyl acetate, gamma-hexalactone, hexyl acetate, hexyl butyrate, hexyl caproate, hexyl caprylate, hexyl formate, hexyl isobutyrate, hexyl isovalerate, Hexyl-2-methylbutanoate, hexyl propionate, isoamly acetate, isoamyl butyrate, isoamyl capronate, isobutyl butyrate, isobutyl isovalerate, isobutyric acid, 1,3-dimethyl- 3-butenyl 2-methylpropionate, isoprenyl acetate, isopropyl acetate, isovaleric acid, isovaleric aldehyde, ethyl (2-methyl-1,3-dioxolan-2-yl)-acetate, 4,4a,5,9b-tetrahydro-2,4- dimethyl-indeno[1,2-d]-1,3-dioxin, maltol isobutyrate, ethyl-2-methyl pentanoate, ethyl-3,5,5-trimethyl hexanoate, methyl acetate, 2-methyl butyl acetate, 2-methyl butyraldehyde, methyl butyrate, methyl caproate, methyl caprylate, 2-methyl methylbutyrate, methyl thiobutyrate, 2-methyl butyric acid, 2, 2-methyl pentenoic acid, delta nonalactone, norborn-5-en-yl acetate, delta octalactone, gamma octalactone, 2- (ethoxymethyl)-1 -methyl-3-(1 -methylethen€-cyclopentene, diethyl (E)-2-methylbut-2- enedioate, 2-methylpentyl-2-methylvalerate, propyl aceta'e, propyl propionate, 1,1 '- Bi(cyclopentyl)-2-yl (2E)-but-2-enoate, (E)-4-methyldec-3-en-5-ol, delta undecalactone, valeric acid, gamma valerolactone:
6. The fragrance mixture according to any of the preceding Claims 1 to 6, wherein said secondary fragrances (b) exhibiting a woody scent note are selected from the group consisting of 2-methyl-5-(5,5,6-trimethyl-bicyclo[2.2.1]-hept-2-yl) cyclohexanone, 1-(2- tert-butylcyclohexyl)oxybutan-2-ol, 2H-lndeno[4,5-b] furan, decahydro-2, 2, 6, 6, 7,8,8- heptamethyl, dodecahydro-3,3-8,11a-tetramethyl-5H-3,5a-epoxynapht(2,1 -c)oxepin, 3a,6,6,9a-Tetramethyldodecahydronaphtho[2,1 -b]furan, (ethoxymethoxy)- cyclododecane, (E)-Ambra-13,18(28)-dien-8-ol, ambrinol, (4aR,5R,7aS,9R)-Octahydro- 2,2,5,8,8,9ahexamethyl-4H-4a,9-methanoazuleno[5,6-d]-1,3-dioxole, (3aS,4aR,5R,7aS,9R,9aR)-Octahydro-2,5,8,8,9a-pentamethyl-2-propyl-4H-4a,9- methanoazuleno[5,6-d]-1,3-dioxole, dodecahydro-3a,6,6,9a-tetramethyl- naphtho[2,1 - b]furan, (3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1 -b]furan, amyris oil, 8oc,9oc-epoxycedrane, (+) 2,6,9-trimethyl-2,5,9-cyclododecatrien-1 -ol, 2- methyl-3-({1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}oxy)propan-1 -ol, boya oil, beta- 2,2, 3-Tetramethylcyclopent-3-ene1 -butanol, alpha-decahydro-2, 2,4, 8-tetramethyl-4, 8- methanoazulen-9-yl acetate, (1 R,3E,5S,9S)- 4,11,11 -trimethyl-8-methylene- Bicy- clo[7.2.0]undec-3-en-5-ol, 1,2, 3,5,6, 7-hexahydro- 1,1, 2,3, 3-pentamethyl-4H-inden-4- one, cedarwood oil, [3R-(3oc,3a|3,6a,7|3,8aa)]-octahydro-6-methoxy-3,6,8,8-tetramethyl- 1 H-3a,7-methanoazulene + (3R, 3aS,6R,7R, 8aS)-octahydro-6-methoxy-3, 6,8,8- tetramethyl-1 H-3a,7-methanoazulene, cedrene, cedrenol, cedrol, cedroxid, cedryl acetate, 3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1 H-benzo[e][1]benzofuran, clearwood, cyclododecyl formate, cypriol oil, dynamone, (Z)-3-methyl-5-(2,2,3- trimethyl-1 -cyclopent-3-enyl)pent-4-en-2-ol, (E)-2-methyl-1-(6-methyl-6-
bicyclo[2.2.1 ] hept-2-enyl)pent- 1 -en-3-ol mixture, 1-(2,6,6-Trimethyl-2-cyclohexen-1- yl)-3-pentanone, guaiac wood oil, guaiacol, guaiyl acetate, hydrocarboresin B, 2- cyclododecylpropan-1-ol, 1 -(2,3,8, 8-Tetramethyl-1, 3, 4,5,6, 7-hexahydronaphthalen-2- yl)ethanone, isobornyl cyclohexanol, bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, pro- panoate, 2H-2,4a-methanonaphthalene, [1-Methyl-2-[(1,2,2-trimethylbicyclo[3.1.0]hex- 3-yl)methyl]cyclopropyl]methanol (mixture of diastereoisomers), 5-Butyl-2-yl-2-(2,4- dimethyl-1-cyclohex-3-enyl)-5-methyl-1,3-dioxane, 4-(1 -Ethoxyvinyl)-3, 3,5,5- tetramethyl-cyclohexan-1-one, Methyl diisoamyl carbinol, 1 R,2S,7S,9S)-3,3,7-trimethyl- 8-methylentricyclo-[5.4.0.02,9]undecan, alpha-Ethyl-2,2,6- trimethylcyclohexanepropanol, 1 -Methyl-1 -methoxycyclododecane, 3,3-Dimethyl-5- (2,2,3- trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, alpha-Propyl-2,2,6-trimethyl- cyclohexanepropanol, 2,4-Dimethyl-2-(1,1,4,4-tetramethyltetralin-6-yl)-1,3-dioxolane, labdanum ethanone, 3,7- dimethyl-7-methoxy-2-octanol, 1,3, 6, 7- tetramethylbicyclo[4.4.0]dec-7-en-2-yl formate, 1,1-dimethoxy-cyclododecane, methoxycyclododecane, patchouli oil, 1-[4-(1,1-dimethylethyl)phenyl]-ethanone, 1, 1,5,5- Tetramethylhexahydro-2H-2,4a-methanonaphthalen-8(5H)-one, 3,3-Dimethyl-5-(2,2,3- trimethyl-3-cyclopente'-1-yl)-4-penten-2-ol, 3,7’-Dimethyl-3,4,4a,5,8,8a- hexahydrospiro-(1,4-m'thanonaphthalene- 2(1 H),2’-oxirane), 2-(1,1-Dimethylethyl)-4- methylcyclohexanol, 2-(1,1-Dimethylethyl)-4-methylcyclohexanol, 2-Methyl-4-(2,2,3- trimethyl- 3-cyclopneten-1 -yl)-2-buten-1 -ol, 3-methyl-5-(2,2,3-trimethylcyclopent-3- en-1-yl)pentan-2-ol, sandalwood oil, (2E)-2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1- yl)-buten-1 -ol, 2-Ethyl-4-(2,2,3-trimethylcyclopent-3-en-1 -yl)but-2-en-1 -ol, sclareolide, 1,3,4,5,6,7-hexahydro-7-methoxy-1,1,5,5-tetramethyl-2H-2,4a-methanonaphthalene, 1,1,5,5-Tetramethyl-octahydro-2,4a-methanonaphthalene-8a-ol, 1 -(2,2,6-
Trimethylcyclohexyl)hexan-3-ol, trimofix, methyl cedryl ketone, 1,3-Dimethyl-3- phenylbutylacetate, 4-Methyl-4-phenylpentan-2-one, 4-Cyclohexyl-4-methylpentan-2- one, vetiver oil, 4,8-Dimethyl-2-propan-2-ylidene-3,3a,4,5,6,8a-hexahydro-1 H-azulen-6- ol, (4,8-dimethyl-2-propan-2-ylidene-3,3a,4,5,6,8a-hexahydro-1 H-azulen-6-yl) acetate, 1 ,,1 ,,5,,5,-Tetramethylhexahydro-spiro[1,3-dioxolane-2,8,(5,H)-2H-2,4a- methanonaphthalene]
7. The fragrance mixture according to any of the preceding Claims 1 to 4, wherein said secondary fragrances (b) exhibiting a floral scent note are selected from the group consisting of 4-(3-methylbutyl)cyclohexan-1-ol, allyl-alpha-ionone, alpha-amyl cinnamic aldehyde, isopentyl phenethyl ether, benzophenone, benzyl acetate, benzyl acetone, benzyl propionate, benzyl salicylate, 2-ethoxy-2,6,6-trimethyl-9- methylenebicyclo[3.3.1]nonane, 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2- butenal, 3-[4-(1,1-dimethylethyl)-phenyl]-propanal), cabreuva oil, methylbenzodioxepi- non, cananga oil, 3-(4-methoxyphenyl)-2-methylpropanal, (3-methoxy-2- methylpropyl)-benzene, 2-methyl-4-(2,6,6-trimethyl-2(1)-cyclohexen-1-yl)butanal, Isomethyl-alpha-ionone, Citronellol, Citronellyl acetate, Citronellyl butyrate, citronellyl
formate, citronellyl isobutyrate, citronellyl isovaleriate, citronellyl propionate, citronellyl tiglate, ortho-methoxybenzyl ethyl ether, 3-(p-cumenyl)-2-methylpropionaldehyd, 3-(4- isopropylphenyl)propanal, 1 -(3,3-Dimethylcyclohexyl)ethyl acetate, Cyclohexyl salicylate, 2-Methyl-3-(4-tert-butylphenyl)propanol, 1,2,3,4,5,6,7,8-octahydro-5,5-dimethyl-2- Naphthalenecarboxaldehyde; 1,2,3,4,5,6,7,8-octahydro-8,8-dimethyl-2-
Naphthalenecarboxaldehyde, (E)-1-(2,6,6-trimethyl-1 -cyclohexa-1,3-dienyl)but-2-en-1 - one; (2E)- 1 -(2,6,6-trimethyl-1,3-cyclohexadien-1 -yl)- 2-buten-1 -one, (E)-1 -(2,6,6- tri methyl - 1 -cyclohex-2-enyl)but-2-en-1 -one, (E)-1 -(2,6,6-trimethyl-1 -cyclohex-2- enyl)but-2-en-1 -one, (E)-1 -(2,6,6-trimethyl-1 -cyclohexenyl)but-2-en-1 -one, 1 -(2,6,6- trimethyl-1 -cyclohex-3-enyl)but-2-en-1 -one, trans, trans-2,4-decadienal, 2-pentyl- cyclopropan-1 -ol, 2-pentyl-cyclopentanone, 4-(2,6,6-trimethyl-1 -cyclohexenyl)-2- butanone, 3-methyl-2-pentyl-2-cyclopenten-1 -on, tetrahydro-4-methyl-2-(2- methylpropyl)- 2H-pyran, dimethal anthranilate, dimethyl sulfoxide, dipheynl oxide, (E)- 4-ethyloct-3-enenitrile, dimethyl sulfide, tetrahydro-4-methyl-2-phenyl-2H-pyran, 4- (octahydro-4,7-methano-5H-inden-5-ylidene)butanal, ethyl linalyl acetal, ethyl anthranilate, ethyl benzoate, ethyl linalool, cyclohexa-1,3-diene-1 -carboxylic acid, 2,6,6- trimethyl-ethyl ester, ethyl salicylate, farnesol, farnesyl acetate, 3-(3- isopropylphenyl)butanal, 4-methyl-2-(2-methylpropyl)oxan-4-ol, 2,6-dimethyl-2- heptanol, 2-methyldecanenitrile, ethyl 2-acetylocta noate, (2E)-3,7-dimethylocta-2,6- dien-1 -ol, geranium oil, geranyl acetate, geranyl acetone, geranyl benzoate, geranyl butyrate, geranyl ethyl ether, genaryl formate, genaryl isobutyrate, genaryl isovalerate, geranyl methyl ether, geranyl propionate, geranyl tiglate, 2-[5(6)-Methyl-7(8)-(1 - methylethyl)bicyclo[2.2.2]oct-5-en-2-yl]-1,3-dioxolane, geranium dihydropyran, methyl 3-oxo-2-pentylcyclopentaneacetate, methylenedioxyphenyl-methylpropanal, hexen-3- yl salicylate (cis), hexyl benzoate, alpha-hexyl cinnamic aldehyde, hexyl salicylate, 2,3- dihydro-1,1 -dimethyl-1 H-indene-ar-propanal, hydroxy citronellol, indene, Tetrahy- droindeno dioxin, Indole, (3E)-4-(2,6,6-trimethylcyclohex-2-en-1 -yl)but-3-en-2-one, 4- (2,6,6-T rimethylcyclohex-1 -en-1 -yl)but-3-en-2-one, 4-(2,2,6-T rimethyl-2- cyclohexenyl)3-methyl-3-buten-2-one, N-methyl ionone, Non-2-enenitrile, 4-(2, 5,6,6- tetramethyl-2-cyclohexen-1 -yl)- 3-buten-2-one, 4-(2,5,6,6-Tetramethyl-2-cyclohexen-1 - yl)-3-buten-2-one (main component), Isoamyl acetate, Isobutyl salicylate, Isocyclo geraniol, 2-Hexyl-2-cyclopenten-1-one, 1,5-anhydro-2,4-dideoxy-2-pentyl-3-acetate- pentitol, jasmine absolute, tetrahydro-6-(2-pentenyl)-2H-pyran-2-one, 6-(pent-3-en-1 - yl)-tetrahydro-2H-pyran-2-one, 3-methyl-2-[(2Z)-pent-2-en-1 -yl]cyclopent-2-en-1 -one, 2-hexyl-2-cyclopenten-1-ol, 3-pentyl-4-tetrahydropyranyl acetate, tetrahydro-3-pentyl- 2H-pyran-4-yl acetate, 1,3, 4,6,7, 8a-hexahydro- 1,1,5, 5-tetramethyl-2H-2, 4a-
Methanonaphthalen-8(5H)-one, 5-hexyl-5-methyloxolan-2-one, decahydro-2, 8,8- trimethylnaphthalene-2,4a-carbolactone, 3-(4-tert-butylphenyl)butanal, (4R.)-4-(1 - methylethyl)-1 -cyclohexene-1 -propanal, 2,5-dimethyl-2-indan methanol, linalool, linalool oxide, 4-(4-hydroxy-4-methyl-pentyl)-3-cyclohexen-1 -carboxyaldehyde, oc-methyl- cyclohexanepropanol, beta,beta-3-trimethyl-benzenepropanol, (Z+E)-para- menthan-7-
ol, 3-methyl-5-phenylpentanal, methyl anthranilat, methyl benzoat, methyl diphenyl ether, methyl geraniate, methyl heptin carbonate, (E)-3-methyl-4-(2,6,6-trimethyl-1 - cyclohex-2-enyl)but-3-en-2-one, methyl-[(1 R,2R)-3-oxo-2-((Z)-pent-2- enyl)cyclopentyl]acetat, methyl naphthyl ketone, methyl octin carbonate, Methyl pentaoic acid-2, Methyl salicylate, mimosa absolute, 1 -(4-isopropyl-cyclohexyl) ethanol, 3- methyl-4-phenylbutan-2-ol, 2,2-dimethyl-3-phenylpropan-1 -ol, Acetic acid octahydro- 4,7-methano-inden-5-ylmethyl ester, narcisse absolute, Methyl 2-nonenoate, Nerol, Neroli oil, 3,7,11 -Trimethyl-1,6,10-dodecatrien-3-ol, Ethyl-2-naphthylether, 2- Methoxynaphthalin, 1 -(3-methyl-1 -benzofuran-2-yl)ethan-1 -one, Neryl acetate, trans, cis-2,6-Nonadienal, trans, trans-2,4-Nonadiena, 2,6-Nonadienol, 10- hydroxymethylene-2-pinene, orange flower absolute, 4-(2-methylbutan-2- yl)cyclohexan-1 -one, orris absolute, orris resin, palmarosa oil, 3-[(2Z)-3-hexenyloxy]- propanenitrile, 1,1 -dimethoxynon-2-yne, Nonanoic acid, Pentyl salicylate, Pentyl salicylate, 2-cyclohexylidene-2-phenylacetonitrile, Petitgrain oil, 2-Phenoxyethyl-2- methylpropanoate, 3-Methyl-5-phenylpentan-1 -ol, Phenyl salicylate, Phenylethyl acetate, Phenylethyl alcohol, Phenylethyl benzoate, phenylethyl butyrate, Phenylethyl isovalerate, Phenylethyl methyl ether, Phenylethyl phenylacetate, Phenylethyl pivalate, Phenylethyl propionate, Phenylethyl salicylate, Phenylethyl tiglate, Phenylpropyl acetate, Prenyl salicylate, 2,6,10-Trimethyl-5,9-undecadien-1 -ol, 2-Hexylcyclopentanone, 2- Hexylcyclopentanone, 2-Heptylcyclopentanone, Ethyl-2,3,6-trimethylcyclohexyl carbonate, Methyl-2,2-dimethyl-6-methylenecyclohexanecarboxylate, oc-
(Trichloromethyl)benzyl acetate, beta-Methyl-benzenepentanol, Rose absolute, tetra- hydro-4-methyl-2-(2-methyl-1 -propen-1 -yl)- 2H pyran, 4-Methyl-2-phenyl-3,6- dihydro-2H-pyran,
4-Methyl-6-phenyl-3,6-dihydro-2H-pyran, 4-Methylene-2-phenyltetrahydro-2H- pyran, 2-Methyl-3-[4-(2-methylpropyl)phenyl]propanal, alpha-Terpineol, Tetrahydro linalool, Tetrahydro geraniol, Thiogeraniol, Tuberrose absolute, (E)-4-methyldec-3-en-
5-ol, 2,2,5-Trimethyl-5-pentylcyclopentan-1-one, Methyl 2-[[3-[4-(1 , 1 - dimethylethyl)phenyl]-2-methylpropylidene]amino] benzoate, 1-Methyl-4-(4- methylpentyl)-3-cyclohexenecarbaldehyde, 4-(4-Methyl pent-3-enyl) cyclohex-3-ene-1 - carbaldehyde, Violet leaves absolute, cyclooct-4-en-1-yl methyl carbonate, 2,6- nonadienenitrile, Ylang Ylang oil:
8. The fragrance mixture according to any of the preceding Claims 1 to 7, wherein said fragrances exhibiting an aromatic/herbal scent note are selected from the group consisting of Cyclohexane-1 -methanol, alpha, 3, 3-trimethyl formate, Artemisia oil, Bornyl acetate, Camphene, Camphor, D,L, Caraway oil, Carvacrol, Carveol, L, Carvomenthone, Carvone D, Carvone L, Cedar leave oil, 1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane, Clary sage oil, 3a,4,5,6,7,7a-Hexahydro-1 H-4,7-methanoinden-5-yl 2-methylpropanoate, p- Cymene, Cypress oil, Di hydrocarvone, Dill oil, 1 -Methoxyhexane, 1,3,3-Trimethyl-2- oxabicyclo[2.2.2]octane, Eucalyptus oil, Fenchol, 1,3,3-Trimethyl-2-norbornanyl acetate,
fir absolute, fir balsam, 1 -(3,3-Dimethylcyclohexyl)ethanone, 3a,4,5,6,7,7a-Hexahydro- 4,7-methanoinden-6-yl acetate, Tricyclodecenyl propionate, isoborneol, isobornyl acetate, isobornyl propionate, isobutyl menthone, isomenthone, isopropyl cyclohexanol, juniper berry oil, laurel noble leaf oil, lavandin oil, lavender oil, marjoram oil, mentha arvensis oil, menthol, menthol L/isomenthol, menthyl acetate, (3,3,5- trimethylcyclohexyl) acetate, 6,6-dimethyl-2-norpinene-2-ethanolacetate, origanum oil, 4-tert-Butylcyclohexyl acetate, pennyroyal oil, peppermint oil, pine needle absolute, pine oil, 6,6-dimethyl-bicyclo[3.1.1]hept-2-ene-2-propanal, Octahydro-7-methyl-1,4- methanonaphthalen-6(2H)-one, 4-Acetoxy-4-methyl-2-propyltetrahydro-2H-pyran, spearmint oil, spike oil, tea tree oil, Terpinen-4-ol, 2,6,6,10-Tetramethyl-1 - oxaspiro[4.5]dec-9-ene, thuja oil, [1 S-(1a,4a,5a)]4-methyl-1 -(1 -methylethyl)- bicyclo[3.1.0]hexan-3-one, thyme oil, thymol, turpentine oil, 2-tert-Butylcyclohexanol, wormwood oil; and mixtures thereof.
9.. The fragrance mixture according to any of the preceding Claims 1 to 8, wherein said secondary fragrances (b) exhibiting a citrus scent note are selected from the group consisting of 3, 7-dimethyl-6-octene-1 -nitrile, decanal, 6,6-dimethoxy-2,5,5- trimethylhex-2-ene, bergamot oil, ethyl 6-acetoxyhexa noate, cedrat oil, citral diethyl acetal, citral, 2,4-Dimethyl-3-cyclohexene-1 -methanyl acetate, Citronella oil, Citronellal, (E)-3-Methyl-5-phenylpent-2-enenitrile and (Z)-3-Methyl-5-phenylpent-2-enenitrile, alpha Ethenyl-alpha-methyl-benzenepropane nitrile, 2,4,4,7-tetramethyl-6-octen-3-one, (+/-)-2,8-Epithio-cis-p-menthane, 3-Mercapto-|3,4-dimethylcyclohexaneethanethiol, Cyclohexyl ethylacetate, Dihydromyrcenol, Dihydromyrcenil acetate, Dimethyl oc- tenone, Ethyl linalyl acetate, Eucalyptus oil, Grapefruit oil, 3-Methyl-5- phenylpentanenitrile, Lemon oil, Lemongrass oil, 3,7-Dimethyl-2(3),6-nonadienonitrile, 1 -Methyl-4-(1 -methylethenyl)cyclohexene, Lime oil, Linalyl acetate, Linalyl benzoate, Linalyl butyrate, Linalyl formate, Linalyl isobutyrate, Linalyl propionate, Litsea Cubeba oil, (E)-2, 12-Tridecadiennitrile and (E)-3, 12-Tridecadiennitrile + (Z)-3,12-Tridecadiennitrile, (E)-2-dodecenal, mandarin oil, 2-methyl-4-propyl-1,3-oxathiane, myrcenyl acetate, tri- methyl-3,5,5-hexyl acetate, (4R,4aS,6R)-6-lsopropenyl-4,4a-dimethyl-4,4a,5,6,7,8- hexahydro-2(3H)-naphthalinon, (3Z,6E)-8-ocimenyl acetate, orange oil, 2-Ethyl-N- methyl-N-(3-methylphenyl)butanamide, 2,6-dimethyl-10-methylene-2,6,11 - dodecatrienal, (2S)-2-(1,1 -dimethylpropoxy)-propyl propanoate, tangerine oil, (E/Z)- 6,10-Dimethylundeca-5,9-dien-2-yl acetate, Terpinyl acetate, Tetrahydro linalyl acetate, Tetrahydromyrcenol
10. The fragrance mixture according to any of the preceding Claims 1 to 9, wherein said secondary fragrances exhibiting a green scent note are selected from the group consisting of allyl amyl glycolate, sec-butyl-3-methylbutanthioate, 2,4-dimethyl-3- cyclohexen-1-carbaldehyde (main component), allyl (cyclohexyloxy)-acetate, dibutyl sulfide, 2-ethyl-3,5(6)-dimethylpyrazine, 2,3-dimethylpyrazine, 2,5-dimethylpyrazine, 2,6-dimethylpyrazine, 1 -(5,5-dimethyl-1 -cyclohexen-1 -yl)-4-penten-1 -one, 2-
ethylpyrazine, 2,4,6-trimethyl-4-phenyl-1,3-dioxane, galbanol, 1 -(5,5-Dimethylcyclohex- 1 -en-1 -yl)pent-4-en-1 -one, N,2-Dimethyl-N-phenylbutyramide, 2-[6(5)-Methyl-8(7)-(1 - methylethyl)bicyclo[2.2.2]oct-5-en-2-yl]-1,3-dioxolane, 3,3,5-Trimethylcyclohexyl ethyl ether, 2-trans-hexenal, 3-trans-hexenol, 3-cis-hexenol, 2-trans-hexenol, 3- hexenylacetate (cis/trans), 3-cis-hexenylacetate, 2-trans-hexenylacetate, 3-cis- hexenylbenzoate, 3-cis-hexenylbutyrate, 3-cis-hexenylcaproate, 3-cis-hexenylacetal, 3- cis-hexenylformate, 3-cis-hexenylisobutyrate, 3-cis-hexenylisovalerate, 3-cis- hexenyllactate, 3,2-cis-hexenylmethylbutyrate, 3-cis-hexenylpropionate, 3-cis- hexenyltiglate, hexenyl tiglate, (2,2-Dimethoxy-1 -methylethyl)benzene, 2-lsobutyl-3- methoxypyrazine, 2,4,6-Trimethyl-3-cyclohexene-1 -carboxaldehyde, 2-lsopropyl-3- methoxypyrazine, 2-lsopropyl-4-methylthiazole, (Z)-Hex-3-en-1 -yl methyl carbonate, (3E)-1 -(1 -Methoxypropoxy)-3-hexene, 2,4-Dimethyl-3-cyclohexencarboxaldehyde, 2,4- Dimethyl-tetrahydroindenodioxine, 2,6-Dimethyl-5-heptenal, Octa hyd ro- 1 H -4,7- methanoindene-1 -carbaldehyde, Methyl-dihydrocyclopentapyrazine, methyl 2- nonynate, 2- methyl pyrazine, 3,3,5-Trimethylcyclohexyl acetate, 1 -(5,5- dimethyl-1 - cyclohexen-1-yl)-4-Penten-1 -one, 3,5,6-trimethyl-3-cyclohexene-1 -carboxaldehyde, 6- cis-nonenol, 1 -Octen-3-ol, Phenylacetaldehyde, Phenylacetataldehyde dimethylacetal, 8-ocimen-1 -yl acetate, 5H,5M Cyclopenta parzine, Tetrahydro-2, 4-dimethyl-4-phenyl- furan, 6-Ethylideneoctahydro-5,8-Methano-2H-1 -benzopyran, 1 -Spiro[4.5]dec-7-en-7- yl-4-penten-1 -one, 5-Methyl-3-heptanone oxime, 1 -Phenylethyl acetate, 1 -Phenylethyl alcohol, 1 -Phenylethyl propionate, beta-Methyl-benzenepropanal, 2-propenyl-p- cymene, 4-ethenyl-2-(2-methylpropyl)-1,3-dioxolane, 2,4,6-Trimethyl-4-phenyl-1,3- dioxane, 3-(Methylthio)propyl butyrate, 2,4-Dimethylcyclohex-3-ene-1 -carbaldehyde, Dimethyl-3-cyclohexene-1 -carboxaldehyde, Methyl 2-{[(1 E)-(2,4-dimethylcyclohex-3- en-1 -yl)methylene]amino}benzoate, sec-Butyl-3-methylbutanthioate, 2,4-Dimethyl-3- cyclohexen-1-carbaldehyde, Allyl (cyclohexyloxy)acetate, Dibutyl sulfide, 2-Ethyl-3,5(6)- dimethylpyrazine, and mixtures thereof.
:11. The fragrance mixture according to any of the preceding Claims 1 to 10, wherein said secondary fragrances (b) exhibiting a spicy scent note are selected from the group consisting of allspice oil, benzyl cinnamate, isoeugenyl benzyl ether, caryophyllene, cassia oil, methylcinnamic alcohol, cinnamic acid, Cinnamic alcohol, Cinnamic aldehyde, Cinnamic leaf oil, Cinnamon oil, Cinnamyl acetate, Cinnamyl cinnamate, Cinnamyl formate, Cinnamyl isobutyrate, Cinnamyl isovalerate, Cinnamyl nitrile, Clove bud oil, Clove leaf oil, Cumin oil, Cuminic alcohol, Cuminic aldehyde, Cuminic nitrile, Cuminyl acetate, Dihydroeugenol, Ethyl cinnamate, Eugenol, Eugenol methyl ether, Eugenyl acetate, Gingergrass oil, 2-Methoxycinnamaldehyde, Isoamyl cinnamate, Isobutyl cinnamate, Isoeugenol, isoeugenol acetate, Isoeugenol methyl ether, Linalyl cinnmate, Mace oil, 5(or 6)- Methyl-7(or 8)-(1 -methylethyl)bicyclo[2.2.2]oct-5-ene-carbaldehyde, Methoxy cinnamic aldehyde, Methyl cinnamate, Methyl cinnamic aldehyde, 2-Ethoxy-4- (methoxymethyl)phenol, 7-methyl-3-methylene-1,6-octadiene, Nutmeg oil, p-Mentha-
1,8-dien-7-al, Phenylethyl cinnamate, Phenylpropyl alcohol, Phenylpropyl aldehyde, 3- Phenylpropyl isobutyrate, Pimento oil, 2,3,3-Trimethylindan-1-one, 2,6,6- trimethylcyclohexa-1,3-dienylmethanal, 1,2-dimethoxybenzol; and mixtures thereof.
12. The fragrance mixture according to any of the preceding Claims 1 to 11, comprising one, two, three or more fragrances selected from component (b).
13. The fragrance mixture according to any of the preceding Claims 1 to 12, wherein said primary and said secondary fragrances are present in the mixture in ratios by weight of from about 0.1:99.9 to about 30:70 wt.-percent.
14. The fragrance mixture according to any of the preceding Claims 1 to 13, wherein said primary and said secondary fragrances are present in the mixture in ratios by weight of from about 1:99 to about 5:95 wt.-percent.
15. The fragrance mixture according to any of the preceding Claims 1 to 14, wherein said solvents (c) are selected from the group consisting of water, benzyl alcohol, benzyl benzoate, diethyl phthalate, dipropylene glycol, ethyl alcohol, zso-propyl myristate, triethyl citrate, dipropyleneglycol methyl ether, petroleum distillates, triacetin and their mixtures.
16. The fragrance mixture according to any of the preceding Claims 1 to 15, wherein said solvents (c) are selected from the group consisting of ethanol, dipropylene glycol, triethyl citrate and mixtures thereof.
17. The fragrance mixture according to any of the preceding Claims 1 to 16, wherein said solvents (c) are present in the mixture to an amount of up to 25 wt.-percent.
18. A perfume preparation comprising the mixture of any of the preceding Claims 1 to 17 and at least 1, 2, 3, 4, 5 or more tertiary fragrances, different from components (a) and (b).
19. A method for preparing a perfume preparation, comprising or consisting of the following steps:
(i) providing the fragrance mixture according to any of the Claims 1 to 17;
(ii) providing at least 1, 2, 3, 4, 5 or more tertiary fragrances; and
(iii) adding about 1 to about 100 parts of component (i) to 900 to 999 parts of component (ii) to get 1,000 parts of the preparation.
20. A cosmetic, detergent or household product, obtained according to the following steps:
(i) providing the mixture of any of the preceding Claims 1 to 17 or the perfume preparation of Claim 18;
(ii) providing a cosmetic, detergent or household base composition;
(iii) adding about 10 to about 100 parts of component (i) to 990 to 999 parts of component (ii) to get 1,000 parts of the product.
21. A method for preparing a cosmetic, detergent or household product, comprising or consisting of the following steps:
(i) providing the mixture of any of the preceding Claims 1 to 17 or the perfume preparation of Claim 18;
(ii) providing a cosmetic, detergent or household base composition;
(iii) adding about 10 to about 100 parts of component (i) to 990 to 999 parts of component (ii) to get 1,000 parts of the product.
22. A method of modulating, intensifying and/or increasing the long-lasting of a fragrance comprising or consisting of the following steps:
(i) providing at least one a primary fragrance according to general formula (I)
wherein R1, R2, R3, R4, and R5 independently of one another represent hydrogen or linear or branched Ci -Cio-alkyl, which is optionally substituted with hydroxy or Ci- C4-alkyl or linear or branched Ci-Cio-alkoxy, which is optionally substituted with hydroxy or Ci -C4-alkyl,
(ii) providing at least one secondary fragrance different from component (a), said at least one secondary fragrance exhibiting at least one of the following scent notes: fruity; woody; floral; aromatic/herbal; citrus; spicy; and green.
(iii) optionally providing at least one solvent;
(iv) blending components (i), (ii) and optionally (iii).
23. The method according to Claim 22, wherein said primary fragrances are selected from the group consisting of
• 3,4-dimethyl benzonitrile;
• 4-(2-methylpropyl) benzonitrile;
• 3-methyl benzonitrile;
• 2-methoxy benzonitrile;
• 3,4-dimethoxy benzonitrile;
• 4-methoxy benzonitrile and mixtures thereof.
24. The method according to Claim 22 and/or 23, wherein said primary fragrance is 3,4- dimethyl benzonitrile.
25. The method according to any of the preceding Claims 22 to 24, wherein said solvents are selected from the group consisting of water, benzyl alcohol, benzyl benzoate, diethyl phthalate, dipropylene glycol, ethyl alcohol, zso-propyl myristate, triethyl citrate, dipropylene glycol methyl ether, petroleum distillates, triacetin and mixtures thereof.
26. The method according to any of the preceding claims 22 to 25, wherein said solvents are selected from the group consisting of ethanol, dipropylene glycol, triethyl citrate and mixtures thereof.
27. The use of at least one a primary fragrance according to general formula (I)
wherein R1, R2, R3, R4, and R5 independently of one another represent hydrogen or linear or branched Ci-Cio-alkyl, which is optionally substituted with hydroxy or Ci -C4-alkyl or linear or branched Ci-Cio-alkoxy, which is optionally substituted with hydroxy or Ci- C4-alkyl, for modulating, intensifying and/or increasing the long-lasting of one secondary fragrance different from component (a), said at least one secondary fragrance exhibiting at least one of the following scent notes: fruity; woody; floral; aromatic/herbal; citrus; spicy; and green
28. The use according to Claim 27, wherein said primary fragrances are added to said secondary fragrances in an amount of from about 0.1 to about 30 wt.-percent - calculated on the final mixture.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP2024/051132 WO2025153182A1 (en) | 2024-01-18 | 2024-01-18 | Fragrance mixtures comprising aromatic nitriles |
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| Application Number | Priority Date | Filing Date | Title |
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| PCT/EP2024/051132 WO2025153182A1 (en) | 2024-01-18 | 2024-01-18 | Fragrance mixtures comprising aromatic nitriles |
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| Application Number | Title | Priority Date | Filing Date |
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| PCT/EP2024/051132 Pending WO2025153182A1 (en) | 2024-01-18 | 2024-01-18 | Fragrance mixtures comprising aromatic nitriles |
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Citations (7)
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| US4040986A (en) * | 1975-02-11 | 1977-08-09 | Naarden International N.V. | Preparation of 4-methoxybenzonitrile perfume compositions |
| EP0550762A1 (en) | 1991-07-25 | 1993-07-14 | Kao Corporation | Process for producing nitrile |
| EP1174117A1 (en) * | 2000-07-21 | 2002-01-23 | Givaudan SA | Fragrance composition comprising a mixture of nitriles |
| JP2009096928A (en) * | 2007-10-18 | 2009-05-07 | Kao Corp | Fragrance composition |
| EP2940005A1 (en) * | 2012-12-26 | 2015-11-04 | Kao Corporation | Nitrile compound |
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| US20230159854A1 (en) * | 2020-05-11 | 2023-05-25 | Symrise Ag | A fragrance composition |
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|---|---|---|---|---|
| US4040986A (en) * | 1975-02-11 | 1977-08-09 | Naarden International N.V. | Preparation of 4-methoxybenzonitrile perfume compositions |
| EP0550762A1 (en) | 1991-07-25 | 1993-07-14 | Kao Corporation | Process for producing nitrile |
| EP1174117A1 (en) * | 2000-07-21 | 2002-01-23 | Givaudan SA | Fragrance composition comprising a mixture of nitriles |
| JP2009096928A (en) * | 2007-10-18 | 2009-05-07 | Kao Corp | Fragrance composition |
| EP2940005A1 (en) * | 2012-12-26 | 2015-11-04 | Kao Corporation | Nitrile compound |
| EP2979682A1 (en) | 2014-07-30 | 2016-02-03 | Symrise AG | A fragrance composition |
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