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Example 8Synthesis of 3-\[(4R)-4-isopropylcyclohexen-1-yl)propanal (Ia)- \[0281\]\ \ \ \ \ \ - \[0282\]\ \ A mixture of 24 g of (4R)-2-(1-butoxyethoxy)-4-isopropyl-1-methylene cyclohexane (77%, 72 mmol, 1.00 equiv., formula (IIa) as defined above) and 2.5 g hexanoic acid (21 mmol, 0.30 equiv.) in 25 g Malotherm S is heated at 200° C. for 2 hours. During this, the low-boiling products are distilled off. Then the reaction mixture is cooled at room temperature and distilled over soda. 14.7 g of 3-\[(4R)-4-isopropylcyclohexen-1-yl\]-propanal (formula (Ia) as defined above) is isolated at a purity of 52% and with 96.6% ee. This corresponds to a yield of 58% of theory. Some of the product is purified on a column (cyclohexane: ethyl acetate 100:3, 3.34 g, purity 96.5%).\ \ - \[0283\]\ \ \[α\]D22=+108° (c=0.07 in ethanol).—GC with chiral stationary phase (Hydrodex-b-TBADc, 25 m×0.25 mm, 40° C.−1° C./min.−180° C.): Rt=79.08 (98.3%), 79.30 (1.7%).—MS: m/z (%)=180 (M+″ 10), 162 (7), 147 (7), 136 (34), 119 (24), 109 (18), 93 (100), 79 (41), 67 (56), 55 (34), 41 (69), 27 (33).—1H NMR (400 MHz, CDCl3): δ (ppm)=0.87 (d, J=6.8 Hz, 3H), 0.88 (d, J=0.88 Hz, 3H), 1.16-1.28 (m, 2H), 1.42-1.50 (m, 1H), 1.66-1.80 (m, 2H), 1.94-2.06 (m, 3H), 2.28 (t, J=7.5 Hz, 2H), 2.49-2.54 (m, 2H), 5.39-5.43 (m, 1H), 9.75 (t, J=1.9 Hz, 1H).—13C NMR (100 MHz, CDCl3): δ (ppm)=19.6 (CH3), 19.9 (CH3), 26.3 (CH2), 28.8 (CH2), 29.2 (CH2), 29.7 (CH2), 32.2 (CH), 40.0 (CH), 41.9 (CH2), 121.8 (CH), 135.5 (cquart), 202.8 (CHO).\ \ Example 9 Fine Fragrance (Perfume Oil)- \[0284\]\ \ - | | |\ | --- | --- |\ | | |\ | | Parts by weight |\ \ \ \ | | | |\ | --- | --- | --- |\ | | | Perfume |\ | | | oil A2 |\ | | | (according |\ | | Perfume oil A1 | to the |\ | Fragrances | (comparison) | invention) |\ | |\ \ \ \ | | | |\ | --- | --- | --- |\ | ETHYL ACETOACETATE | 4.0 | 4.0 |\ | HEXENOL CIS-3 10% DPG | 3.0 | 3.0 |\ | HEXENYL ACETATE CIS-3 10% DPG | 3.0 | 3.0 |\ | HEXENYL BENZOATE CIS-3 10% DPG | 3.0 | 3.0 |\ | VERTOCITRAL 10% DPG | 5.0 | 5.0 |\ | CYCLOGALBANAT ® 10% DPG | 3.0 | 3.0 |\ | STYRALYL ACETATE 10% DPG | 6.0 | 6.0 |\ | BERGAMOT OIL BERGAPTEN FREE FF | 6.0 | 6.0 |\ | MANDARY OIL DIST. DECOL. | 15.0 | 15.0 |\ | METHYL ANTHRANILATE 10% DPG | 5.0 | 5.0 |\ | RED BERRY EXTR. | 2.0 | 2.0 |\ | DECALACTONE GAMMA | 2.0 | 2.0 |\ | ALLYL CAPROATE 10% DPG | 5.0 | 5.0 |\ | PRUNELLA TYPE BASE | 6.0 | 6.0 |\ | HELIONAL | 20.0 | 20.0 |\ | MUGETANOL | 10.0 | 10.0 |\ | ETHYL LINALOOL | 35.0 | 35.0 |\ | CITRONELLOL 950 | 10.0 | 10.0 |\ | GERANIOL SUPER | 3.0 | 3.0 |\ | ROSAPHEN ® | 8.0 | 8.0 |\ | CITRONELLYL ACETATE EXTRA | 2.0 | 2.0 |\ | DAMASCONE BETA 10% DPG | 6.0 | 6.0 |\ | BENZYL ACETATE | 10.0 | 10.0 |\ | HEDION HC/30 | 30.0 | 30.0 |\ | HEDIONE | 140.0 | 140.0 |\ | HEXYL CINNAMIC ALDEHYDE ALPHA | 30.0 | 30.0 |\ | LACTOJASMONE | 3.0 | 3.0 |\ | BENZYL SALICYLATE | 80.0 | 80.0 |\ | HEXENYL SALICYLATE CIS-3 | 30.0 | 30.0 |\ | METHYL IONONE GAMMA COEUR | 3.0 | 3.0 |\ | CLOVE BUD OIL | 1.0 | 1.0 |\ | VANILLIN | 1.5 | 1.5 |\ | COUMARIN | 1.0 | 1.0 |\ | AMBERWOOD ® F | 5.0 | 5.0 |\ | CASHMERAN | 8.0 | 8.0 |\ | CEDRENE | 15.0 | 15.0 |\ | ISO E SUPER NON DISCOLORING | 50.0 | 50.0 |\ | BRAHMANOL ® | 25.0 | 25.0 |\ | SANDALORE | 5.0 | 5.0 |\ | AMBROXIDE | 2.0 | 2.0 |\ | AMBRETTOLIDE | 5.0 | 5.0 |\ | AURELIONE ® | 16.0 | 16.0 |\ | GLOBALIDE ® | 24.0 | 24.0 |\ | MACROLIDE ® SUPRA | 16.0 | 16.0 |\ | INDOLE FF 10% DPG | 5.0 | 5.0 |\ | 3-\[(4R)-4-Isopropylcyclohexen-1-yl\]propanal | | 50.0 |\ | DIPROPYLENE GLYCOL | 332.5 | 282.5 |\ | | 1000.0 | 1000.0 |\ | |\ \ - \[0285\]\ \ At a dosage of 6 wt % of perfume oil A1 or A2 in ethanol, the findings are as follows: By adding 3-\[(4R)-4-isopropylcyclohexen-1-yl\]propanal in perfume oil A2 the floral note is intensified relative to perfume oil A1 (without 3-\[(4R)-4-isopropylcyclohexen-1-yl\]propanal). Furthermore, 3-\[(4R)-4-isopropylcyclohexen-1-yl\]propanal endows the composition with perfume oil A2 more power and fullness than the composition with perfume oil A1; on the whole, addition of 3-\[(4R)-4-isopropylcyclohexen-1-yl\]propanal results in an odor impression reminiscent of lily of the valley.\ \ Example 10Body Lotion- \[0286\]\ \ - | |\ | :-: |\ | Component | wt % | wt % |\ | --- | --- | --- |\ | |\ | :-: |\ | Paraffin oil | 5.00 | 5.00 |\ | Isopropyl palmitate | 5.00 | 5.00 |\ | Cetyl alcohol | 2.00 | 2.00 |\ | Beeswax | 2.00 | 2.00 |\ | Ceteareth-20 | 2.00 | 2.00 |\ | PEG-20-glyceryl stearate | 1.50 | 1.50 |\ | Glycerol | 3.00 | 3.00 |\ | Phenoxyethanol | 0.50 | — |\ | Parabens (mixture of methyl, ethyl, propyl, butyl, | — | 0.50 |\ | isobutyl paraben) |\ | Perfume oil B1 or B2 | 0.50 | 0.50 |\ | Water | to 100 | to 100 |\ | |\ \ - \[0287\]\ \ Composition of the perfume oil B1 or B2:\ \ - | | |\ | --- | --- |\ | | |\ | | Parts by weight |\ \ \ \ | | | |\ | --- | --- | --- |\ | | | Perfume oil |\ | | | B2 |\ | | Perfume oil | (according |\ | | B1 | to the |\ | Fragrances | (comparison) | invention) |\ | |\ \ \ \ | | | |\ | --- | --- | --- |\ | NONADIENAL TRANS, CIS-2.6 5% TEC | 2.0 | 2.0 |\ | 20% DPG |\ | ETHYL ACETOACETATE | 3.0 | 3.0 |\ | FARENAL ® 10% DPG | 5.0 | 5.0 |\ | VERTOCITRAL | 3.0 | 3.0 |\ | CYCLOGALBANAT ® 10% DPG | 2.0 | 2.0 |\ | STYRALYL ACETATE | 3.0 | 3.0 |\ | MELONAL ® | 0.5 | 0.5 |\ | DIHYDROMYRCENOL | 15.0 | 15.0 |\ | LINALYL ACETATE | 20.0 | 20.0 |\ | LEMON OIL TERPENE FLAVOR WONF | 8.0 | 8.0 |\ | EUCALYPTOL NATURAL. 10% DPG | 0.5 | 0.5 |\ | HEXYL ACETATE | 1.5 | 1.5 |\ | ISOAMYL ACETATE 10% DPG | 4.0 | 4.0 |\ | PRENYL ACETATE 10% DPG | 4.0 | 4.0 |\ | ALDEHYDE C14 SO-CALLED | 2.0 | 2.0 |\ | ETHYL METHYL BUTYRATE-2 | 1.0 | 1.0 |\ | ALLYL CYCLOHEXYL PROPIONATE | 2.0 | 2.0 |\ | ALDEHYDE C16 SO-CALLED | 1.0 | 1.0 |\ | FRAGOLANE ® | 0.5 | 0.5 |\ | MAJANTOL ® | 25.0 | 25.0 |\ | LINALOOL | 40.0 | 40.0 |\ | DIMETHYL BENZYL CARBINOL | 10.0 | 10.0 |\ | TERPINEOL PURE | 10.0 | 10.0 |\ | PHENIRAT ® | 30.0 | 30.0 |\ | CITRONELLOL 950 | 15.0 | 15.0 |\ | GERANIOL 60 | 10.0 | 10.0 |\ | CITRONELLYL ACETATE EXTRA | 2.0 | 2.0 |\ | HEDIONE | 90.0 | 90.0 |\ | HEXYL CINNAMIC ALDEHYDE ALPHA | 35.0 | 35.0 |\ | HEXYL SALICYLATE | 160.0 | 160.0 |\ | METHYL OCTIN CARBONATE 10% DPG | 2.0 | 2.0 |\ | CALONE 1951 10% DPG | 1.0 | 1.0 |\ | GALAXOLIDE 50% IN IPM | 20.0 | 20.0 |\ | ANETHOLE SUPRA 21.5 CELSIUS | 2.0 | 2.0 |\ | AGRUMEX HC | 15.0 | 15.0 |\ | ORYCLON SPECIAL | 40.0 | 40.0 |\ | 3-\[(4R)-4-Isopropylcyclohexen-1-yl\]propanal | | 15.0 |\ | DIPROPYLENE GLYCOL | 415.0 | 400.0 |\ | | 1000.0 | 1000.0 |\ | |\ \ - \[0288\]\ \ At a dosage of 0.5 wt % of perfume oil B1 or B2 in the body lotion, the findings are as follows: due to the proportion of 3-\[(4R)-4-isopropylcyclohexen-1-yl\]propanal, the body lotion containing perfume oil B2 has a stronger and more natural floral note than the body lotion that contains perfume oil B1 (without 3-\[(4R)-4-isopropylcyclohexen-1-yl\] propanal). Furthermore, the body lotion with perfume oil B2 displays a more cosmetic top note and a creamier bottom note than the body lotion with perfume oil B1; on the whole, addition of 3-\[(4R)-4-isopropylcyclohexen-1-yl\]propanal results in an odor impression reminiscent of lily of the valley.\ \ Example 11 Fabric Softener- \[0289\]\ \ - | |\ | :-: |\ | Material | Manufacturer | Chemical name | Function | wt % |\ | --- | --- | --- | --- | --- |\ | |\ | :-: |\ | |\ \ \ \ | | | | | |\ | --- | --- | --- | --- | --- |\ | Deionized water | | Water | Solvent | 72.4 |\ | Rewoquat WE 18 | Evonik | Dialkylesterammonium | Cationic | 16.6 |\ | | Goldschmidt | ethosulfate | surfactant |\ | | GmbH |\ | Mergal K9N | Honeywell | 5-Chloro-2-methyl-3- | Preservative | 0.10 |\ | | Austria GmbH | (2H)-isothiazolone and |\ | | | 2-methyl-3-(2H)- |\ | | | isothiazolone |\ | Dow Corning 1520 | Dow Corning | Polydimethylsiloxane | Antifoaming | 0.30 |\ | Antifoam | GmbH, | | agent |\ | Magnesium chloride | | Magnesium chloride | Consistency | 10.00 |\ | 1% solution | | solution | agent |\ | Perfume Oil C1 or C2 | Symrise | | Perfume | 0.60 |\ | | | | (fragrance) |\ | |\ \ - \[0290\]\ \ Composition of perfume oil C1 or C2:\ \ - | | |\ | --- | --- |\ | | |\ | | Parts by weight |\ \ \ \ | | | |\ | --- | --- | --- |\ | | | Perfume oil |\ | | | C2 |\ | | Perfume oil | (according |\ | | C1 | to the |\ | Fragrances | (comparison) | invention) |\ | |\ \ \ \ | | | |\ | --- | --- | --- |\ | ALDEHYDE C10 | 0.5 | 0.5 |\ | ALDEHYDE C11 ISO | 2.0 | 2.0 |\ | ALDEHYDE C11 UNDECYLENIC | 12.0 | 12.0 |\ | ALDEHYDE C12 MNA | 6.0 | 6.0 |\ | FARENAL ® | 1.0 | 1.0 |\ | VERTOCITRAL | 8.0 | 8.0 |\ | ALLYL AMYL GLYCOLATE | 1.0 | 1.0 |\ | STYRALYL ACETATE | 1.5 | 1.5 |\ | DIHYDROMYRCENOL | 65.0 | 65.0 |\ | AGRUNITRIL | 1.0 | 1.0 |\ | PEONILE | 15.0 | 15.0 |\ | METHYL ANTHRANILATE | 10.0 | 10.0 |\ | NEROLIONE 10% DPG | 1.5 | 1.5 |\ | ROSEMARY OIL BM | 7.0 | 7.0 |\ | SAGE OFFICINALE OIL DALM. | 3.0 | 3.0 |\ | ISOBORNYL ACETATE | 40.0 | 40.0 |\ | PRENYL ACETATE | 0.5 | 0.5 |\ | ISOAMYL BUTYRATE E | 0.5 | 0.5 |\ | ALDEHYDE C14 SO-CALLED | 5.0 | 5.0 |\ | MANZANATE | 0.5 | 0.5 |\ | MUGETANOL | 5.0 | 5.0 |\ | DIMETHYL BENZYL CARBINYL | 2.5 | 2.5 |\ | ACETATE |\ | ROSE OXIDE D | 3.0 | 3.0 |\ | ANTHER | 0.5 | 0.5 |\ | PHENYLETHYL ALCOHOL | 35.0 | 35.0 |\ | CITRONELLOL 950 | 15.0 | 15.0 |\ | GERANIOL 60 | 10.0 | 10.0 |\ | ISODAMASCON ® | 2.0 | 2.0 |\ | ROSACETATE | 35.0 | 35.0 |\ | CRESYL METHYL ETHER PARA | 0.5 | 0.5 |\ | BENZYL ACETATE | 20.0 | 20.0 |\ | HEXYL CINNAMIC ALDEHYDE ALPHA | 40.0 | 40.0 |\ | METHYL BENZOATE | 1.0 | 1.0 |\ | AMYL SALICYLATE N/ISO | 10.0 | 10.0 |\ | BENZYL SALICYLATE | 70.0 | 70.0 |\ | MYSORE ACETATE | 15.0 | 15.0 |\ | PARMANYL ® | 0.5 | 0.5 |\ | EUGENOL | 10.0 | 10.0 |\ | ETHYL VANILLIN | 0.5 | 0.5 |\ | COUMARIN | 3.0 | 3.0 |\ | AGRUMEX HC | 45.0 | 45.0 |\ | HERBAFLORAT | 25.0 | 25.0 |\ | AMBERWOOD ® F | 5.0 | 5.0 |\ | ISO E SUPER | 170.0 | 170.0 |\ | PATCHOULI OIL DECOL. | 2.5 | 2.5 |\ | SANDRANOL ® | 10.0 | 10.0 |\ | ISOBUTYL QUINOLINE | 1.0 | 1.0 |\ | EVERNYL | 0.5 | 0.5 |\ | AMBROXIDE | 1.0 | 1.0 |\ | GALAXOLIDE 50% IN IPM | 120.0 | 120.0 |\ | INDOFLOR ® CRYST. | 0.5 | 0.5 |\ | 3-\[(4R)-4-Isopropylcyclohexen-1-yl\]propanal | | 60.0 |\ | DIPROPYLENE GLYCOL | 220.0 | 160.0 |\ | | 1000.0 | 1000.0 |\ | |\ \ - \[0291\]\ \ At a dosage of 0.6 wt % of perfume oil C1 or C2 in the fabric softener, the findings are as follows: due to the proportion of 3-\[(4R)-4-isopropylcyclohexen-1-yl\]propanal, the fabric softener containing perfume oil C2 has a more natural, fresher floral note than the fabric softener that contains perfume oil C1 (without 3-\[(4R)-4-isopropylcyclohexen-1-yl\] propanal); on the whole, addition of 3-\[(4R)-4-isopropylcyclohexen-1-yl\]propanal results in an odor impression reminiscent of lily of the valley.\ \ Example 12 Soap- \[0292\]\ \ - | |\ | :-: |\ | Material | Manufacturer | Chemical name | Function | wt % |\ | --- | --- | --- | --- | --- |\ | |\ | :-: |\ | |\ \ \ \ | | | | | |\ | --- | --- | --- | --- | --- |\ | Deionized water | | Water | Solvent | 2.0 |\ | Soap Base Mix | Various | Sodium | Surfactants | 95.8 |\ | | | tallowates/ |\ | | | palmitates |\ | Titanium dioxide | Kronos Titan | Titanium | Pigment/ | 1.0 |\ | | GmbH, | dioxide | Lightening |\ | | Germany | | agent |\ | Perfume oil D1 | Symrise | | Perfume | 1.2 |\ | or D2 | | | (fragrance) |\ | |\ \ - \[0293\]\ \ Composition of perfume oil D1 or D2:\ \ - | | |\ | --- | --- |\ | | |\ | | Parts by weight |\ \ \ \ | | | |\ | --- | --- | --- |\ | | | Perfume oil |\ | | | D2 |\ | | Perfume oil | (according |\ | | D1 | to the |\ | Fragrances | (comparison) | invention) |\ | |\ \ \ \ | | | |\ | --- | --- | --- |\ | ALDEHYDE C 8 | 10.0 | 10.0 |\ | ALDEHYDE C10 | 14.0 | 14.0 |\ | ALDEHYDE C11 UNDECYLIC | 5.0 | 5.0 |\ | ALDEHYDE C12 MNA | 4.0 | 4.0 |\ | ISOAMYL ALCOHOL | 6.0 | 6.0 |\ | VERTOCITRAL | 4.0 | 4.0 |\ | ALLYL AMYL GLYCOLATE | 4.0 | 4.0 |\ | DIHYDROMYRCENOL | 120.0 | 120.0 |\ | CITRAL 95 | 30.0 | 30.0 |\ | AGRUNITRIL | 80.0 | 80.0 |\ | CITRONITRILE | 40.0 | 40.0 |\ | CITRYLAL | 4.0 | 4.0 |\ | ORANGE OIL TERPENES | 250.0 | 250.0 |\ | METHYL ANTHRANILATE | 1.5 | 1.5 |\ | TERPINEOL HEAD FRACTION | 10.0 | 10.0 |\ | EUCALYPTOL NAT. | 10.0 | 10.0 |\ | THYMOL CRYST | 6.0 | 6.0 |\ | BORNYL ACETATE L CRYST. | 82.5 | 82.5 |\ | CAMPHOR DL | 20.0 | 20.0 |\ | JASMAPRUNAT | 5.0 | 5.0 |\ | ALDEHYDE C14 SO-CALLED | 2.0 | 2.0 |\ | MANZANATE | 0.5 | 0.5 |\ | ALLYL HEPTOATE | 2.5 | 2.5 |\ | ROSE OXIDE L | 0.5 | 0.5 |\ | DAMASCONE ALPHA | 0.5 | 0.5 |\ | HEDIONE | 10.0 | 10.0 |\ | AMYL SALICYLATE N/ISO | 60.0 | 60.0 |\ | HEXYL SALICYLATE | 35.0 | 35.0 |\ | COUMARIN | 2.5 | 2.5 |\ | AGRUMEX HC | 30.0 | 30.0 |\ | ORYCLON SPECIAL | 55.0 | 55.0 |\ | PATCHOULI OIL DECOL. | 2.0 | 2.0 |\ | SANDRANOL ® | 1.5 | 1.5 |\ | TONALIDE | 2.0 | 2.0 |\ | 3-\[(4R)-4-Isopropylcyclohexen-1-yl\]propanal | | 40.0 |\ | DIPROPYLENE GLYCOL | 130.0 | 90.0 |\ | | 1000.0 | 1000.0 |\ | |\ \ - \[0294\]\ \ At a dosage of 1.2 wt % of perfume oil D1 or D2 in the soap, the findings are as follows: due to the proportion of 3-\[(4R)-4-isopropylcyclohexen-1-yl\]propanal, the soap containing perfume oil D2 has a round, aldehyde note, in contrast to the soap that contains perfume oil D1 (without 3-\[(4R)-4-isopropylcyclohexen-1-yl\] propanal). Furthermore, the soap with perfume oil D2 radiates more naturalness and fullness than the soap with perfume oil D1; on the whole, addition of 3-\[(4R)-4-isopropylcyclohexen-1-yl\]propanal results in an odor impression reminiscent of lily of the valley.\ \ Example 13 Washing Powder- \[0295\]\ \ - | |\ | :-: |\ | Material | Manufacturer | Chemical name | Function | wt % |\ | --- | --- | --- | --- | --- |\ | |\ | :-: |\ | |\ \ \ \ | | | | | |\ | --- | --- | --- | --- | --- |\ | Sodium metasilicate | Akzo Nobel | Sodium metasilicate | | 48.0 |\ | pentahydrate | Chemicals, | pentahydrate |\ | | Germany |\ | Sodium hydrogen | Various | Sodium hydrogen | Alkali | 15.0 |\ | carbonate | | carbonate |\ | Sodium percarbonate | Various | Sodium carbonate | Bleach | 15.0 |\ | | | peroxyhydrate |\ | Peractive AC blue | Clariant | TAED/Na-carboxy- | Activator | 5.00 |\ | | GmbH, | methylcellulose |\ | | Germany |\ | Genapol OA-080 | Clariant | Oxoalcohol C14-15, | Non-ionic | 3.00 |\ | | GmbH, | 8EO | surfactant |\ | | Germany |\ | Texapon K12 powder | Cognis | Sodium lauryl sulfate | Anionic | 7.00 |\ | | Germany | C12 | surfactant |\ | | GmbH |\ | Tinopal CBS-X | Ciba, | | Brightener | 0.50 |\ | | Germany |\ | Savinase 6.0 T, Type W | Novozymes | Protease | Enzyme | 0.40 |\ | Termamyl 120 T | Novozymes | Alpha-amylase | Enzyme | 0.30 |\ | Sodium sulfate | Various | Sodium sulfate | Filler | 5.50 |\ | Perfume oil E1 or E2 | Symrise | | Perfume | 0.30 |\ | | | | (fragrance) |\ | |\ \ - \[0296\]\ \ Composition of perfume oil E1 or E2:\ \ - | | |\ | --- | --- |\ | | |\ | | Parts by weight |\ \ \ \ | | | |\ | --- | --- | --- |\ | | | Perfume oil |\ | | | E2 |\ | | Perfume oil | (according |\ | | E1 | to the |\ | Fragrances | (comparison) | invention) |\ | |\ \ \ \ | | | |\ | --- | --- | --- |\ | ALDEHYDE C 8 | 0.5 | 0.5 |\ | HEXENOL CIS-3 | 3.5 | 3.5 |\ | VERTOCITRAL | 15.0 | 15.0 |\ | STYRALYL ACETATE | 3.0 | 3.0 |\ | MELONAL ® | 2.0 | 2.0 |\ | DIHYDROMYRCENOL | 60.0 | 60.0 |\ | CITRAL 95 | 6.0 | 6.0 |\ | ORANGE OIL TERPENES | 20.0 | 20.0 |\ | EUCALYPTUS OIL GLOBULUS 80/85% | 10.0 | 10.0 |\ | MENTHONE L/ISOMENTHONE D 82/18 | 1.5 | 1.5 |\ | HEXYL ACETATE 10% DPG | 5.0 | 5.0 |\ | ISOPENTYRATE | 4.0 | 4.0 |\ | ETHYL CAPROATE | 1.0 | 1.0 |\ | ETHYL METHYL BUTYRATE-2 | 6.0 | 6.0 |\ | LINALOOL | 10.0 | 10.0 |\ | DIMETHYL BENZYL CARBINYL | 15.0 | 15.0 |\ | BUTYRATE |\ | PHENYLETHYL ALCOHOL | 15.0 | 15.0 |\ | CITRONELLOL 950 | 20.0 | 20.0 |\ | GERANIOL 60 | 20.0 | 20.0 |\ | ISODAMASCON ® | 10.0 | 10.0 |\ | CRESYL METHYL ETHER PARA | 1.0 | 1.0 |\ | BENZYL ACETONE | 50.0 | 50.0 |\ | HEXYL CINNAMIC ALDEHYDE ALPHA | 60.0 | 60.0 |\ | DIHYDROJASMONE | 1.0 | 1.0 |\ | METHYL BENZOATE | 0.5 | 0.5 |\ | HEXYL SALICYLATE | 10.0 | 10.0 |\ | LEGUMINAL | 6.0 | 6.0 |\ | IONONE BETA | 20.0 | 20.0 |\ | ISORALDEINE 70 | 45.0 | 45.0 |\ | EUGENOL | 2.0 | 2.0 |\ | ACETOPHENONE 1% DPG | 5.0 | 5.0 |\ | AGRUMEX HC | 60.0 | 60.0 |\ | ORYCLON SPECIAL | 40.0 | 40.0 |\ | HERBAFLORAT | 10.0 | 10.0 |\ | HERBYL PROPIONATE | 20.0 | 20.0 |\ | KOAVONE | 20.0 | 20.0 |\ | VERTOFIX | 40.0 | 40.0 |\ | ISO E SUPER | 150.0 | 150.0 |\ | SANDRANOL ® | 20.0 | 20.0 |\ | AMBROXIDE | 2.0 | 2.0 |\ | 3-\[(4R)-4-Isopropylcyclohexen-1-yl\]propanal | | 60.0 |\ | DIPROPYLENE GLYCOL | 270.0 | 210.0 |\ | | 1000.0 | 1000.0 |\ | |\ \ - \[0297\]\ \ At a dosage of 0.3 wt % of perfume oil E1 or E2 in the washing powder (powder detergent), the findings are as follows: the proportion of 3-\[(4R)-4-isopropylcyclohexen-1-yl\]propanal produces, in the washing powder containing perfume oil E2, an intensification of the green notes relative to the washing powder that contains perfume oil E1 (without 3-\[(4R)-4-isopropylcyclohexen-1-yl\]propanal). Furthermore, the composition of the washing powder with perfume oil E2 radiates altogether more freshness than the washing powder with perfume oil E1; on the whole, addition of 3-\[(4R)-4-isopropylcyclohexen-1-yl\]propanal results in an odor impression reminiscent of lily of the valley.\ \ Example 14 General-Purpose Cleaner- \[0298\]\ \ - | |\ | :-: |\ | Material | Manufacturer | Chemical name | Function | wt % |\ | --- | --- | --- | --- | --- |\ | |\ | :-: |\ | |\ \ \ \ | | | | | |\ | --- | --- | --- | --- | --- |\ | Deionized water | | Water | Solvent | 59.6 |\ | Mergal K9N | Troy Chemie, | 5-Chloro-2-methyl-3-(2H)- | Preservative | 0.1 |\ | | Seelze | isothiazolone and 2-methyl- |\ | | | 3-(2H)-isothiazolone |\ | Trisodium citrate | Various | Trisodium citrate dihydrate | Complexing | 3.0 |\ | dihydrate | | | agent |\ | Zetesol NL-2 | Zschimmer & | Fatty alcohol C12-14- | Anionic | 30.0 |\ | | Schwarz, | sulfate, sodium | surfactant |\ | | Germany |\ | Imbentin C/125/055 | Dr. W. Kolb | Fatty alcohol C12-C15, 8EO | Non-ionic | 5.0 |\ | | AG chem. | | surfactant |\ | Ethanol 96% | Various | Ethanol | Solvent | 2.0 |\ | Perfume oil F1 or | Symrise | | Perfume | 0.3 |\ | F2 | | | (fragrance) |\ | |\ \ - \[0299\]\ \ Composition of perfume oil F1 or F2:\ \ - | | |\ | --- | --- |\ | | |\ | | Parts by weight |\ \ \ \ | | | |\ | --- | --- | --- |\ | | | Perfume oil |\ | | | F2 |\ | | Perfume oil | (according |\ | | F1 | to the |\ | Fragrances | (comparison) | invention) |\ | |\ \ \ \ | | | |\ | --- | --- | --- |\ | ALDEHYDE C10 | 0.5 | 0.5 |\ | ALCOHOL C10 | 6.0 | 6.0 |\ | HEXENOL CIS-3 | 1.0 | 1.0 |\ | LIMONENAL | 4.0 | 4.0 |\ | VERTOCITRAL | 8.0 | 8.0 |\ | PHENYLACETALDEHYDE 50% DPG | 1.0 | 1.0 |\ | MINTONAT | 15.5 | 15.5 |\ | METHYL ANTHRANILATE | 1.0 | 1.0 |\ | HEXYL ACETATE | 20.0 | 20.0 |\ | ALLYL HEPTOATE | 1.0 | 1.0 |\ | LINALOOL | 30.0 | 30.0 |\ | DIMETHYL BENZYL CARBINYL | 2.0 | 2.0 |\ | ACETATE |\ | PHENYLETHYL ALCOHOL | 150.0 | 150.0 |\ | CITRONELLOL 950 | 130.0 | 130.0 |\ | GERANIOL SUPER | 35.0 | 35.0 |\ | GERANYL ACETATE PURE | 10.0 | 10.0 |\ | BENZYL ACETATE | 55.0 | 55.0 |\ | HEDIONE | 15.0 | 15.0 |\ | HEXYL CINNAMIC ALDEHYDE ALPHA | 130.0 | 130.0 |\ | CINNAMIC ALCOHOL | 6.0 | 6.0 |\ | ACETOPHENONE 10% DPG | 1.0 | 1.0 |\ | JACINTHAFLOR ® | 4.0 | 4.0 |\ | ISO E SUPER | 20.0 | 20.0 |\ | GALAXOLIDE 50% IN IPM | 35.0 | 35.0 |\ | INDOFLOR ® CRYST. | 1.0 | 1.0 |\ | BHT IONOL | 8.0 | 8.0 |\ | 3-\[(4R)-4-Isopropylcyclohexen-1-yl\]propanal | | 60.0 |\ | DIPROPYLENE GLYCOL | 370.0 | 310.0 |\ | | 1000.0 | 1000.0 |\ | |\ \ - \[0300\]\ \ At a dosage of 0.3 wt % of perfume oil F1 or F2 in the general-purpose cleaner, the findings are as follows: the proportion of 3-\[(4R)-4-isopropylcyclohexen-1-yl\]propanal produces, in the general-purpose cleaner containing perfume oil F2, an intensification of the floral note relative to the general-purpose cleaner that contains perfume oil F1 (without 3-\[(4R)-4-isopropylcyclohexen-1-yl\]propanal). Moreover, the composition of the general-purpose cleaner with perfume oil F2 seems much creamier and fresher than that of the general-purpose cleaner with perfume oil F1; on the whole, addition of 3-\[(4R)-4-isopropylcyclohexen-1-yl\]propanal results in an odor impression reminiscent of lily of the valley.\ \ Example 15 Shampoo- \[0301\]\ \ - | |\ | :-: |\ | Material | Manufacturer | INCI Name | wt % |\ | --- | --- | --- | --- |\ | |\ | :-: |\ | |\ \ \ \ | | | | |\ | --- | --- | --- | --- |\ | Deionized water | | Water | 71.5 |\ | Plantacare PS 10 | Cognis Germany | Sodium Laureth Sulfate, | 20.0 |\ | | GmbH | Lauryl Glucoside |\ | Euperlan PK 771 | Cognis Germany | Glycol Distearate, Sodium | 6.0 |\ | | GmbH | Lauryl Sulfate, Cocamide |\ | | | MEA, Laureth-10 |\ | Dragocid Liquid | Symrise | Phenoxyethanol, | 0.5 |\ | | | Methylparaben, |\ | | | Ethylparaben, |\ | | | Butylparaben, |\ | | | Propylparaben, |\ | | | Isobutylparaben |\ | Sodium chloride | | Sodium Chloride | 1.4 |\ | Citric acid | | Citric Acid | 0.1 |\ | monohydrate |\ | crystalline |\ | Perfume oil G1 | Symrise | Perfume (Fragrance) | 0.5 |\ | or G2 |\ | |\ \ - \[0302\]\ \ Composition of perfume oil G1 or G2:\ \ - | | |\ | --- | --- |\ | | |\ | | Parts by weight |\ \ \ \ | | | |\ | --- | --- | --- |\ | | | Perfume oil |\ | | | G2 |\ | | Perfume oil | (according |\ | | G1 | to the |\ | Fragrances | (comparison) | invention) |\ | |\ \ \ \ | | | |\ | --- | --- | --- |\ | FARENAL ® | 3.0 | 3.0 |\ | FLORAZON | 0.5 | 0.5 |\ | HEXENYL ACETATE CIS-3 | 3.0 | 3.0 |\ | VERTOCITRAL | 1.0 | 1.0 |\ | DYNASCONE 10% DPG | 2.0 | 2.0 |\ | CYCLOGALBANAT ® | 2.0 | 2.0 |\ | STYRALYL ACETATE | 1.5 | 1.5 |\ | DIHYDROMYRCENOL | 6.0 | 6.0 |\ | OXANTHIA 50% IN TEC 10% DPG | 10.0 | 10.0 |\ | LEMON OIL ITAL. | 10.0 | 10.0 |\ | ORANGE OIL BRASIL | 50.0 | 50.0 |\ | HEXYL ACETATE | 2.0 | 2.0 |\ | ISOAMYL ACETATE | 0.5 | 0.5 |\ | PRENYL ACETATE | 0.5 | 0.5 |\ | ETHYL BUTYRATE 10% DPG | 2.0 | 2.0 |\ | ALDEHYDE C14 SO-CALLED | 25.0 | 25.0 |\ | DECALACTONE GAMMA | 5.0 | 5.0 |\ | ETHYL METHYL BUTYRATE-2 | 1.0 | 1.0 |\ | ALLYL CAPROATE | 1.5 | 1.5 |\ | ALLYL CYCLOHEXYL PROPIONATE | 3.0 | 3.0 |\ | ALLYL HEPTOATE | 2.5 | 2.5 |\ | MELOZONE | 2.0 | 2.0 |\ | CALONE 1951 | 0.5 | 0.5 |\ | MUGETANOL | 10.0 | 10.0 |\ | LINALOOL | 25.0 | 25.0 |\ | DIMETHYL BENZYL CARBINYL | 6.0 | 6.0 |\ | ACETATE |\ | DIMETHYL BENZYL CARBINYL | 4.0 | 4.0 |\ | BUTYRATE |\ | PHENYLETHYL ACETATE | 1.5 | 1.5 |\ | PHENYLETHYL ALCOHOL | 15.0 | 15.0 |\ | CITRONELLOL 950 | 10.0 | 10.0 |\ | GERANIOL SUPER | 5.0 | 5.0 |\ | GERANYL ACETATE PURE | 15.0 | 15.0 |\ | ISODAMASCON ® | 2.0 | 2.0 |\ | BENZYL ACETATE | 15.0 | 15.0 |\ | HEDIONE | 90.0 | 90.0 |\ | HEXYL CINNAMIC ALDEHYDE ALPHA | 35.0 | 35.0 |\ | JASMONE CIS | 0.5 | 0.5 |\ | BENZYL SALICYLATE | 80.0 | 80.0 |\ | HEXENYL SALICYLATE CIS-3 | 30.0 | 30.0 |\ | ISORALDEINE 70 | 35.0 | 35.0 |\ | HERBAFLORAT | 15.0 | 15.0 |\ | ISO E SUPER | 15.0 | 15.0 |\ | ISOBORNYL CYCLOHEXANOL | 30.0 | 30.0 |\ | BRAHMANOL ® | 10.0 | 10.0 |\ | AMBROXIDE | 1.5 | 1.5 |\ | GLOBALIDE ® | 5.0 | 5.0 |\ | GALAXOLIDE 50% IN DPG | 120.0 | 120.0 |\ | 3-\[(4R)-4-Isopropylcyclohexen-1-yl\]propanal | | 65.0 |\ | DIPROPYLENE GLYCOL | 290.0 | 225.0 |\ | | 1000.0 | 1000.0 |\ | |\ \ - \[0303\]\ \ At a dosage of 0.5 wt % of perfume oil G1 or G2 in the shampoo, the findings are as follows: addition of 3-\[(4R)-4-isopropylcyclohexen-1-yl\]propanal intensifies, in the shampoo containing perfume oil G2, the watery-fruity character relative to the shampoo that contains perfume oil G1 (without 3-\[(4R)-4-isopropylcyclohexen-1-yl\]propanal). Moreover, in the shampoo with perfume oil G2, the diffusivity is increased relative to the shampoo with perfume oil G1; on the whole, addition of 3-\[(4R)-4-isopropylcyclohexen-1-yl\]propanal results in an odor impression reminiscent of lily of the valley.\ \ - \[0304\]\ \ Example 16\ \ Shower Gel- \[0305\]\ \ - | |\ | :-: |\ | Material | Manufacturer | INCI Name | wt % |\ | --- | --- | --- | --- |\ | |\ | :-: |\ | |\ \ \ \ | | | | |\ | --- | --- | --- | --- |\ | Deionized water | | Water | 76.3 |\ | Plantacare PS 10 | Cognis | Sodium Laureth Sulfate, | 20.0 |\ | | Germany | Lauryl Glucoside |\ | | GmbH |\ | Dragocid liquid | Symrise | Phenoxyethanol, | 0.5 |\ | | | Methylparaben, |\ | | | Ethylparaben, |\ | | | Butylparaben, |\ | | | Propylparaben, |\ | | | Isobutylparaben |\ | Sodium chloride | | Sodium Chloride | 1.4 |\ | Citric acid | | Citric Acid | 1.3 |\ | monohydrate |\ | crystalline |\ | Perfume oil G1 or G2 | Symrise | Perfume (Fragrance) | 0.5 |\ | from example 15 |\ | |\ \ - \[0306\]\ \ At a dosage of 0.5 wt % of perfume oil G1 or G2 in the shower gel, the findings are as follows: the addition of 3-\[(4R)-4-isopropylcyclohexen-1-yl\]propanal endows the shower gel containing perfume oil G2 with a more natural and caring note relative to the shower gel that contains perfume oil G1 (without 3-\[(4R)-4-isopropylcyclohexen-1-yl\]propanal); on the whole, addition of 3-\[(4R)-4-isopropylcyclohexen-1-yl\]propanal results in an odor impression reminiscent of lily of the valley.\ \ Example 17 Transparent Deodorant Sticks (Formulations A and B) or Deodorant Cream Sticks (Formulations C and D)- \[0307\]\ \ - | |\ | :-: |\ | | A | B | C | D |\ | --- | --- | --- | --- | --- |\ | Component | wt % | wt % | wt % | wt % |\ | --- | --- | --- | --- | --- |\ | |\ | :-: |\ | Aluminum zirconium | 25.00 | 20.00 | 25.00 | 20.00 |\ | tetrachlorohydrate - glycine |\ | complex |\ | Dimethicone (10 cst) | — | — | 5.00 | 5.00 |\ | Cyclopentasiloxane | — | 0.50 | 1.00 | 0.50 |\ | Petroleum jelly | 5.00 | 4.70 | 5.00 | 5.00 |\ | Ozokerite | 1.00 | 1.50 | — | — |\ | Stearyl alcohol | 12.00 | 12.00 | — | — |\ | 2-Butyloctanoic acid | 0.50 | — | 0.50 | — |\ | Wax | — | — | 1.25 | 1.25 |\ | PPG-14 butyl ether | 9.00 | 9.00 | — | — |\ | Hardened rapeseed oil | — | — | 5.00 | 5.00 |\ | Silicon dioxide | — | — | 1.00 | — |\ | Farnesol | 0.25 | — | 0.25 | — |\ | Paraffin oil | 0.50 | 0.50 | — | — |\ | Hydrogenated castor oil (castor | 3.50 | 3.50 | — | — |\ | wax) |\ | Talc | 4.00 | 4.00 | — | — |\ | Behenyl alcohol | 0.20 | 0.20 | — | — |\ | d-Panthenyltriacetate | 1.00 | 1.00 | — | — |\ | Preservative | q.s. | q.s. | q.s. | q.s. |\ | Perfume oil H1 or H2 | 1.50 | — | 1.15 | — |\ | Perfume oil G2 from example 15 | | 0.90 | — | 0.75 |\ | Water | to 100 | to 100 | to 100 | to 100 |\ | |\ \ - \[0308\]\ \ Composition of perfume oil H1 or H2\ \ - | | |\ | --- | --- |\ | | |\ | | Parts by weight |\ \ \ \ | | | |\ | --- | --- | --- |\ | | | Perfume oil |\ | | | H2 |\ | | Perfume oil | (according |\ | | H1 | to the |\ | Fragrances | (comparison) | invention) |\ | |\ \ \ \ | | | |\ | --- | --- | --- |\ | ALDEHYDE C10 | 0.5 | 0.5 |\ | ALDEHYDE C12 MNA 10% DPG | 2.0 | 2.0 |\ | MINTONAT | 40.0 | 40.0 |\ | MELOZONE | 0.5 | 0.5 |\ | VERTOCITRAL | 6.0 | 6.0 |\ | DIHYDRO MYRCENOL | 120.0 | 120.0 |\ | TETRAHYDRO MYRCENOL | 10.0 | 10.0 |\ | AGRUNITRIL | 1.0 | 1.0 |\ | ORANGE OIL BRASIL | 10.0 | 10.0 |\ | TAMARINE TYPE BASE | 10.0 | 10.0 |\ | HEXYL ACETATE | 6.0 | 6.0 |\ | ALDEHYDE C14 SO-CALLED | 1.0 | 1.0 |\ | TETRAHYDRO LINALOOL | 40.0 | 40.0 |\ | DIMETHYL BENZYL CARBINYL | 5.0 | 5.0 |\ | BUTYRATE |\ | ORANGE FLOWER ETHER | 5.0 | 5.0 |\ | PHENYLETHYL ACETATE | 6.5 | 6.5 |\ | PHENYLETHYL ALCOHOL | 15.0 | 15.0 |\ | GERANIOL SUPER | 30.0 | 30.0 |\ | ROSAPHEN ® | 25.0 | 25.0 |\ | ISODAMASCON ® | 0.5 | 0.5 |\ | HEDIONE | 300.0 | 300.0 |\ | UNDECAVERTOL | 0.5 | 0.5 |\ | ALLYL IONONE | 2.5 | 2.5 |\ | IONONE BETA | 10.0 | 10.0 |\ | EUGENOL | 4.0 | 4.0 |\ | ISO E SUPER | 30.0 | 30.0 |\ | BRAHMANOL ® | 2.0 | 2.0 |\ | AMBROXIDE | 2.0 | 2.0 |\ | GLOBALIDE ® | 12.0 | 12.0 |\ | GLOBANONE ® | 8.0 | 8.0 |\ | MACROLIDE ®SUPRA | 45.0 | 45.0 |\ | 3-\[(4R)-4-Isopropylcyclohexen-1-yl\]propanal | | 50.0 |\ | DIPROPYLENE GLYCOL | 300.0 | 250.0 |\ | | 1000.0 | 1000.0 |\ | |\ \ Example 18 Antiperspirant Roll-On- \[0309\]\ \ - | |\ | :-: |\ | Component | wt % | wt % |\ | --- | --- | --- |\ | |\ | :-: |\ | Caprylyl trimethicone (SilCare TM Silicone 31 M 50) | 0.30 | 0.30 |\ | Steareth-20 (GENAPOL TM HS 200) | 3.00 | 3.00 |\ | Steareth-2 (GENAPOL TM HS 020) | 1.50 | 1.50 |\ | Dicaprylyl ether (Cetiol TM OE) | 2.00 | 2.00 |\ | Coco caprylate/caprate (Cetiol TM LC) | 2.00 | 2.00 |\ | Glycerin | 2.00 | 2.00 |\ | Glyceryl stearate (Cutina TM GMS) | 2.00 | 2.00 |\ | Octyldodecanol (Eutanol TM G) | 1.00 | 1.00 |\ | Stearyl alcohol | 2.50 | 2.50 |\ | Aluminum chlorohydrate according to example 1 | 10.00 | 10.00 |\ | of EP 1321431 |\ | Avocado Extract _Persea Gratissima_ | 0.30 | 0.20 |\ | Perfume oil G2 from example 15 | 0.50 | — |\ | Perfume oil H2 from example 17 | — | 0.60 |\ | Water | to 100 | to 100 |\ | |\ \ Example 19 Antiperspirant Stick- \[0310\]\ \ - | |\ | :-: |\ | Component | wt % | wt % |\ | --- | --- | --- |\ | |\ | :-: |\ | |\ \ \ \ | | | |\ | --- | --- | --- |\ | Phenyl trimethicone (SilCare TM Silicone 15 M 50) | 13.50 | 13.50 |\ | Cetearyl alcohol | to 100 | to 100 |\ | Cetiol CC (dicaprylyl carbonate) | 13.50 | 13.50 |\ | Stearic acid | 3.50 | 3.50 |\ | PEG-40-hydrogenated castor oil (Emulsogen TM HCO | 4.10 | 4.10 |\ | 040) |\ | PEG-8 distearate (Cithrol 4 DS) | 4.10 | 4.10 |\ | Petroleum jelly | 6.90 | 6.90 |\ | Aluminum chlorohydrate | 13.80 | 13.80 |\ | Aluminum Zirconium Trichlorohydrex Gly | 19.50 | 20.00 |\ | Ethylhexylglycerin (octoxyglycerin) | 0.30 | 0.20 |\ | 4-Methyl-4-phenyl-2-pentanol (Vetikol) | 0.25 | 0.10 |\ | Perfume oil A2 from example 9 | 1.00 | — |\ | Perfume oil G2 from example 15 | — | 0.80 |\ | |\ \ Example 20 Aerosol Spray- \[0311\]\ \ - | |\ | :-: |\ | Component | wt % | wt % | wt % |\ | --- | --- | --- | --- |\ | |\ | :-: |\ | Octyldodecanol | 0.50 | — | 0.50 |\ | Phenoxyethanol | — | — | 0.30 |\ | 1,2-Pentanediol | 1.00 | 1.00 | 0.50 |\ | 1,2-Hexanediol | 0.25 | 0.15 | 0.25 |\ | 1,2-Octanediol | 0.25 | 0.25 | 0.25 |\ | Farnesol | — | 0.25 | 0.15 |\ | Ethylhexylglycerin (octoxyglycerin) | 0.50 | 0.30 | 0.50 |\ | Perfume oil A2 from example 9 | 0.80 | — | 0.50 |\ | Perfume oil H2 from example 17 | — | 1.15 | 0.50 |\ | Ethanol | to 100 | to 100 | to 100 |\ | |\ \ - \[0312\]\ \ The mixture obtained after mixing the components given in each case is filled with a propane-butane mixture (2:7) in the weight ratio 2:3 in an aerosol container.\ \ Example 21 Hair Conditioner with UV Protection- \[0313\]\ \ - | |\ | :-: |\ | Component | INCI Name | wt % | wt % |\ | --- | --- | --- | --- |\ | |\ | :-: |\ | Lanette O | Cetearyl Alcohol | 4.00 | 4.00 |\ | Dragoxat 89 | Ethylhexyl Isononanoate | 4.00 | 4.00 |\ | Emulsiphos | Potassium Cetyl Phosphate, | 0.50 | 0.50 |\ | | Hydrogenated Palm Glycerides |\ | Natrosol 250 HR | Hydroxyethylcellulose | 0.25 | 0.25 |\ | Neo Heliopan Hydro | Phenylbenzimidazole Sulfonic Acid | 2.00 | 2.00 |\ | L-arginine | Arginine | 1.20 | 1.20 |\ | Benzophenone-4 | Benzophenone-4 | 0.50 | 0.50 |\ | Neo Heliopan AP | Disodium Phenyl Dibenzimidazole | 0.50 | 1.00 |\ | | Tetrasulfonate |\ | Edeta BD | Disodium EDTA | 0.05 | 0.05 |\ | Dragocide liquid | Phenoxyethanol (=and) Methylparaben | 0.80 | 0.80 |\ | | (=and) Butylparaben (=and) |\ | | Ethylparaben (=and) Propylparaben |\ | Dow Corning 949 cationic | Amodimethicone, Cetrimonium | 2.00 | 2.00 |\ | emulsion | Chloride, Trideceth-12 |\ | Dow Corning 5200 | Laurylmethicone Copolyol | 0.50 | 0.50 |\ | Perfume oil B2 from example | Perfume | 0.95 | — |\ | 10 |\ | Perfume oil H2 from example | Perfume | | 1.25 |\ | 17 |\ | Water | Water (Aqua) | to 100 | to 100 |\ | |\ \ Example 22 Sunscreen Spray- \[0314\]\ \ - | |\ | :-: |\ | Part | Raw materials | INCI Designation | wt % |\ | --- | --- | --- | --- |\ | |\ | :-: |\ | |\ \ \ \ | | | | |\ | --- | --- | --- | --- |\ | A | Water, demineralized | Water (aqua) | 69.50 |\ | | Glycerol | Glycerol | 4.00 |\ | | 1,3-Butylene glycol | Butylene Glycol | 5.00 |\ | | D-panthenol | Panthenol | 0.50 |\ | | Lara care A-200 | Galactoarabinan | 0.25 |\ | B | Baysilone oil M 10 | Dimethicone | 1.00 |\ | | Edeta BD | Disodium EDTA | 0.10 |\ | | Copherol 1250 | Tocopheryl Acetate | 0.50 |\ | | Cetiol OE | Dicaprylyl Ether | 3.00 |\ | | Neo Heliopan ® HMS | Homosalate | 5.00 |\ | | Neo Heliopan ® AV | Ethylhexyl Methoxycinnamate | 6.00 |\ | | Neo Heliopan ® 357 | Butyl Methoxydibenzoylmethane | 1.00 |\ | | Corapan TQ | Diethylhexylnaphthalate | 2.00 |\ | | Alpha Bisabolol | Bisabolol | 0.10 |\ | | Pemulen TR-2 | Acrylates/C10-30 Alkyl Acrylate | 0.25 |\ | | | Crosspolymer |\ | C | Phenoxyethanol | Phenoxyethanol | 0.70 |\ | | Solbrol M | Methylparaben | 0.20 |\ | | Solbrol P | Propylparaben | 0.10 |\ | D | NAOH, 10% | Sodium Hydroxide | 0.60 |\ | E | Perfume oil B2 from | Fragrance (Perfume) | 0.20 |\ | | example 10 |\ | |\ \ - \[0315\]\ \ Method of production: Dissolve Lara Care A-200 in the other constituents of part A, with stirring. Weigh out all the raw materials of part B (without Pemulen) and dissolve the crystalline substances, with heating. Add and disperse the Pemulen. Add part B to part A and homogenize for 1 minute. Add parts C-E and homogenize for a further 1-2 minutes with the Ultra Turrax.\ \ Example 23 Sunscreen Soft Cream (W/O), Sun Protection Factor (SPF) 40- \[0316\]\ \ - | |\ | :-: |\ | Part | Raw materials | INCI designation | wt % |\ | --- | --- | --- | --- |\ | |\ | :-: |\ | |\ \ \ \ | | | | |\ | --- | --- | --- | --- |\ | A | Dehymuls PGPH | Polyglyceryl-2 Dipolyhydroxy | 5.00 |\ | | | Stearate E |\ | | Copherol 1250 | Tocopheryl Acetate E | 0.50 |\ | | Permulgin 3220 | Ozokerite | 0.50 |\ | | Zinc stearate | Zinc Stearate E | 0.50 |\ | | Tegosoft TN | C12-15 Alkyl Benzoate E | 10.00 |\ | | Neo Heliopan ® | Isoamyl-P-Methoxycinnamate E | 2.00 |\ | | E1000 |\ | | Neo Heliopan ® 303 | Octocrylene E | 5.00 |\ | | Neo Heliopan ® MBC | 4-Methylbenzylidene Camphor | 3.00 |\ | | Zinc oxide neutral | Zinc Oxide E | 5.00 |\ | B | Water, distilled | Water (Aqua) | to 100 |\ | | EDETA BD | Disodium EDTA | 0.10 |\ | | Glycerin | Glycerin | 4.00 |\ | | Phenoxyethanol | Phenoxyethanol | 0.70 |\ | | Solbrol M | Methylparaben | 0.20 |\ | | Solbrol P | Propylparaben | 0.10 |\ | | Magnesium sulfate | Magnesium Sulfate | 0.50 |\ | C | Perfume oil B2 from | Perfume (Fragrance) | 0.30 |\ | | example 10 |\ | |\ \ - \[0317\]\ \ Method of production: Heat part A to approx. 85° C. Heat part B (without zinc oxide) to approx. 85° C.; add zinc oxide and disperse with the Ultra Turrax. Add B to A. Leave to cool, with stirring. Add part C and then homogenize.\ \ Example 24 Sunscreen Milk (W/O)- \[0318\]\ \ - | |\ | :-: |\ | Part | Raw materials | INCI Designation | wt % |\ | --- | --- | --- | --- |\ | |\ | :-: |\ | |\ \ \ \ | | | | |\ | --- | --- | --- | --- |\ | A | Dehymuls PGPH | Polyglyceryl-2 | 3.00 |\ | | | Dipolyhydroxystearate |\ | | Beeswax 8100 | Beeswax | 1.00 |\ | | Monomuls 90-O-18 | Glyceryl Oleate | 1.00 |\ | | Zinc stearate | Zinc Stearate | 1.00 |\ | | Cetiol SN | Cetearyl Isononanoate | 5.00 |\ | | Cetiol OE | Dicaprylyl Ether | 5.00 |\ | | Tegosoft TN | C12-15 Alkyl Benzoate | 4.00 |\ | | Vitamin E | Tocopherol | 0.50 |\ | | Solbrol P | Propylparaben | 0.10 |\ | | Neo Heliopan ® OS | Ethylhexyl Salicylate | 5.00 |\ | | Neo Heliopan ® AV | Ethylhexyl Methoxycinnamate | 7.50 |\ | | Uvinul ® T150 | Ethylhexyl Triazone | 1.50 |\ | B | Water, distilled | Water (Aqua) | to 100 |\ | | Trilon BD | Disodium EDTA | 0.10 |\ | | Glycerin | Glycerin | 5.00 |\ | | Solbrol M | Methylparaben | 0.20 |\ | | Phenoxyethanol | Phenoxyethanol | 0.70 |\ | | Neo Heliopan ® AP | Disodium Phenyl | 15.00 |\ | | 10% solution, neutralized | Dibenzimidazole |\ | | with NAOH | Tetrasulfonate |\ | C | Perfume oil G2 from | Perfume (Fragrance) | 0.25 |\ | | example 15 |\ | | Alpha bisabolol | Bisabolol | 0.10 |\ | |\ \ - \[0319\]\ \ Method of production: Heat part A to approx. 85° C. Heat part B to approx. 85° C. Add B to A. Leave to cool, with stirring. Add part C and then homogenize.\ \ Example 25 Permanent Hair Colorant- \[0320\]\ \ Part A—Hair coloring base:\ \ - | | |\ | --- | :-: |\ | | Raw materials | wt % |\ | --- | --- | --- |\ | | |\ | --- | :-: |\ | |\ \ \ \ | | | |\ | --- | --- | --- |\ | | Sodium myreth sulfate (e.g. texapon K14 S/K, Cognis) | 2.80 |\ | | Linoleamidopropyl PG-dimonium chloride phosphate | 1.00 |\ | | (Arlasilk Phospholipid EFA, Uniqema) |\ | | Caprylyl/capryl glucoside (Plantacare 810 UP, Cognis) | 2.00 |\ | | Sodium laureth-6 carboxylate (Akypo Soft 45 NV, Kao) | 10.00 |\ | | Cetearyl alcohol | 8.00 |\ | | Octyldodecanol | 1.00 |\ | | Ceteareth-12 | 0.50 |\ | | Ceteareth-20 | 0.50 |\ | | KOH, 50% in water | 0.70 |\ | | Toluene-2,5-diamine sulfate (oxidizing dye) | 0.90 |\ | | Resorcinol | 0.20 |\ | | m-Aminophenol | 0.06 |\ | | 4-Chlororesorcinol | 0.15 |\ | | Ascorbic acid | 0.10 |\ | | Sodium sulfite | 0.15 |\ | | Ammonia, 25% in water | 6.00 |\ | | Etidronic acid | 0.20 |\ | | Polyquaternium-2 (Mirapol A15, Rhodia) | 0.20 |\ | | Perfume oil G2 from example 15 | 0.30 |\ | | Water | 65.24 |\ | | |\ \ - \[0321\]\ \ Part B—Developer:\ \ - | | |\ | --- | :-: |\ | | Raw materials | wt % |\ | --- | --- | --- |\ | | |\ | --- | :-: |\ | |\ \ \ \ | | | |\ | --- | --- | --- |\ | | Cetostearyl alcohol | 8.00 |\ | | Ceteareth-20 | 2.50 |\ | | Steartrimonium chloride (Dehyquart B, Cognis) | 1.00 |\ | | 2,6-Dicarboxypyridine | 0.10 |\ | | Paraffin oil | 0.30 |\ | | Etidronic acid | 0.40 |\ | | Propylene glycol | 0.40 |\ | | Sodium benzoate | 0.04 |\ | | Hydrogen peroxide, 50% in water | 12.00 |\ | | KOH, 50% in water, added to pH = 3.5 | q.s. |\ | | Water | To 100 |\ | | |\ \ - \[0322\]\ \ Application: The hair coloring basis according to the invention (part A) and the developer according to the invention (part B) are stirred together in a 1:1 weight ratio and applied to the hair.\ \ Example 26 Hair Coloring Cream for a Blonde Shade- \[0323\]\ \ - | |\ | :-: |\ | Part | Material | Manufacturer | INCI Name | wt % |\ | --- | --- | --- | --- | --- |\ | |\ | :-: |\ | |\ \ \ \ | | | | | |\ | --- | --- | --- | --- | --- |\ | A | Oxowax | LCW, France | Cetyl alcohol, | 21.00 |\ | | | | Oleyl alcohol, |\ | | | | Cetearyl alcohol, |\ | | | | Stearic acid |\ | | Volpo CS 25 | Croda GmbH, | Ceteareth25 | 4.00 |\ | | | Germany |\ | | Berol 175 | Brenntag eurochem | Laureth-8 | 10.00 |\ | | | GmbH, Germany |\ | | Lanette ® E | Cognis Germany | Sodium Cetearyl | 1.00 |\ | | | GmbH | Sulfate |\ | | Covaquat 16 | LCW, France | Polyquaternium-6 | 4.00 |\ | | Water | | Water (Aqua) | 49.30 |\ | B | Ammonia (20% | Merk Eurolab | Ammonia | 10.20 |\ | | in water) |\ | C | Perfume oil G2 | Symrise | Perfume | 0.50 |\ | | from example 15 |\ | |\ \ - \[0324\]\ \ Method of Production:\ \ - \[0325\]\ \ Mix together Part A, B and C except Covaquat 16 and heat for 20 minutes at 80° C. Once the product is homogeneous, leave to cool. Add Covaquat 16 at 50° C. When the product begins to thicken, stop stirring. Add NH4OH at room temperature and stir the mixture until homogeneous.\ \ Example 27 Air Freshener Aerosol Spray, Water-Based (W/O Alcohol)- \[0326\]\ \ - | |\ | :-: |\ | Material | Manufacturer | INCI Name | wt % |\ | --- | --- | --- | --- |\ | |\ | :-: |\ | |\ \ \ \ | | | | |\ | --- | --- | --- | --- |\ | Imbentin C/125/030 | Symrise | C12-15 pareth-3 | 0.25 |\ | Imbentin AG/100/080 | Symrise | deceth-8, Ziegler alcohol | 1.00 |\ | Perfume oil H2 from | Symrise | Perfume | 1.25 |\ | example 17 |\ | Water, demineralized | | Aqua | 22.50 |\ | Propellant gas 4.2 bar | | | 75.00 |\ | |\ \ - \[0327\]\ \ Method of production: Mix together all the raw materials in the order given.\ \ Example 28 Liquid Air Freshener Pump-Spray- \[0328\]\ \ - | |\ | :-: |\ | Material | Manufacturer | INCI Name | wt % |\ | --- | --- | --- | --- |\ | |\ | :-: |\ | |\ \ \ \ | | | | |\ | --- | --- | --- | --- |\ | Water, demineralized | | Aqua | 90.70 |\ | Ethanol 96% | Symrise | Ethanol | 4.00 |\ | Empilan KCL 11/90 | Stockmeier | Alcohol C12-15 11EO | 3.00 |\ | | Chemie GmbH |\ | | &Co. KG |\ | Isopropanol | Symrise | Propan-2-ol | 1.00 |\ | Sodium hydrogen | Symrise | Sodium bicarbonate | 0.20 |\ | carbonate p.a. |\ | Parmetol A 26 | Hoesch Julius | Mixture of 5-chloro-2- | 0.10 |\ | | | methyl-2H-isothiazol-3- |\ | | | one and 2-methyl-2H- |\ | | | isothiazol-3-one |\ | Perfume oil F2 from | Symrise | Perfume | 1.00 |\ | example 14 |\ | |\ \ - \[0329\]\ \ Method of production: Mix together all the raw materials in the order given. Adjust the pH.\ \ Example 29 Deodorizing Air Freshener Pump/Wick 5% Fragrance- \[0330\]\ \ - | |\ | :-: |\ | Part | Material | Manufacturer | INCI Name | wt % |\ | --- | --- | --- | --- | --- |\ | |\ | :-: |\ | |\ \ \ \ | | | | | |\ | --- | --- | --- | --- | --- |\ | A | Water, demineralized | | Aqua | 67.32 |\ | | Sequion 40 NA 32 | Polygon | | 1.25 |\ | | | Chemie |\ | | Triethanolamine pur C | Symrise | Triethanolamine | 0.30 |\ | | Rewoderm S 1333 | Goldschmidt | DiNa-ricinoleamide of | 2.33 |\ | | | AG | MEA-sulfosuccinate |\ | | Tego Sorb Conc. 50 | Evonik | Alcohol C12-14, ethoxylated | 0.50 |\ | | | | (2-5 EO) + Zn-ricinoleate |\ | | Ethanol 96% | Symrise | Ethanol | 20.00 |\ | B | Perfume oil E2 from example | Symrise | Perfume | 5.00 |\ | | 13 |\ | | Solubilizer | Symrise | | 3.00 |\ | C | Lactic acid | Symrise | Propanoic acid, 2-hydroxy- | 0.30 |\ | | | | propionic acid, Lactol |\ | |\ \ - \[0331\]\ \ Method of production: Mix together materials of Part A in the order given. Mix together materials of Part B. When Part A is clear, add Part B. Then add Part C and stir until the mixture is homogeneous.\ \ Example 30 Candle- \[0332\]\ \ - | | |\ | --- | :-: |\ | | Material | wt % |\ | --- | --- | --- |\ | | |\ | --- | :-: |\ | |\ \ \ \ | | | |\ | --- | --- | --- |\ | | Candle wax | 95.00 |\ | | Perfume oil D2 from example 12 | 5.00 |\ | | |\ \ - \[0333\]\ \ Method of production: Melt the candle wax and stir. Add the perfume oil, stir well. Cast into the desired shape.\ \ Example 31 WC Block- \[0334\]\ \ - | |\ | :-: |\ | Part | Material | Manufacturer | INCI Name | wt % |\ | --- | --- | --- | --- | --- |\ | |\ | :-: |\ | |\ \ \ \ | | | | | |\ | --- | --- | --- | --- | --- |\ | A | Imbentin C/125/200 | Dr. W. Kolb AG | C12/15 pareth-20 | 4.00 |\ | | Rewomid C 212 | Goldschmidt AG | Cocamide MEA | 6.00 |\ | | Marlon ARL | Sasol GmbH | C10-13, ABS-Na, | 42.00 |\ | | | | powder |\ | B | Sodium sulfate | Symrise | Sodium sulfate | 42.00 |\ | | pharm. (E514) |\ | | Perfume oil F2 from | Symrise | Perfume | 6.00 |\ | | example 14 |\ | |\ \ - \[0335\]\ \ Method of production: Melt Part A. Mix in Part B in a mixer-kneader. Form in the extruder at 35-40° C. to a WC block.\ \ Example 32 Synthesis of 3-\[(4S)-4-isopropylcyclohexen-1-yl\]propanal (Ib)- \[0336\]\ \ \ \ \ \ - \[0337\]\ \ The aldehyde 3-\[(4S)-4-isopropylcyclohexen-1-yl\]propanal (formula (Ib) as defined above) is produced starting from I-(−)-limonene (79.5% ee, formula (VIb) as defined above) similarly to the synthesis of 3-\[(4R)-4-isopropylcyclohexen-1-yl\] propanal (Ia) (examples 4 to 8). The product is obtained with a purity of 97% and with 78% ee.\ \ Example 33 Substantivity- \[0338\]\ \ The substantivity test is a test for determining the sensory adherence of a substance on smelling strips. The fragrances to be investigated (compound of formula (Ia), compound of formula (Ib) and Lilial® as benchmark) are each applied in the form of a 10% solution in triethyl citrate (TEC) on a coded smelling strip by dipping and are assessed for intensity at specified time intervals by 15 testers. The 15 testers assess the odor intensity on a scale from 1=odorless to 9=very strong. The results (odor intensity I as a function of the time elapsed t in days d since dipping of the smelling strips) are in shown FIG. 1.\ \ - \[0339\]\ \ The odor intensity is assessed at the following time intervals after dipping of the smelling strips: 1 hour or less (shown in FIG. 1 as time point “0 days”); 1 day; 2 days; 3 days; 4 days; 7 days; 8 days; 9 days. To ensure that the testers are not influenced, the coded smelling strips are not arranged in a chronological order on the smelling strip stand.\ \ - \[0340\]\ \ The odor intensity of the compound of formula (Ia) (black filled bar) is assessed in the fresh state and for a period of up to 3 days by the testers in comparison with Lilial® (black cross-hatched bar) as stronger, and after 4 to 7 days at least comparable to Lilial®. After 9 days, a higher odor intensity of the compound of formula (Ia) compared to Lilial® is observed again.\ \ - \[0341\]\ \ The odor intensity of compound (Ib) (black dotted bar) is, in the fresh state, stronger than that of Lilial® (black cross-hatched bar) and after one day is comparable to Lilial®. After that, the odor intensity of the compound of formula (Ib) at first decreases more than for Lilial® and the compound of formula (Ia), but after 7 to 9 days the values are comparable or slightly higher than with Lilial®.\ \ \ ### Claims (22) Hide Dependent translated from\ \ **1**. A compound selected from the group consisting of a compound of formula (Ia)\ \ \ \ and a compound of formula (Ib)\ \ \ \ **2**. A mixture, comprising a compound of formula (Ia) and a compound of formula (Ib), as defined in claim 1.\ \ **3**. A mixture according to claim 2, wherein\ \ the mass ratio of the compound of formula (Ia) to the compound of formula (Ib) is in the range from 0.01 to 99.99 and/or\ \ the total proportion of compounds of formulas (Ia) and (Ib) is greater than 0.01 wt.\ \ **4**. (canceled)\ \ **5**. (canceled)\ \ **6**. A fragrance preparation, comprising:\ \ a compound of formula (I)\ \ \ \ and\ \ an additional fragrance that is not a compound of formula (I).\ \ **7**. A fragrance preparation according to claim 6, wherein the amount of a compound of formula (Ia)\ \ \ \ and/or a compound of formula (Ib)\ \ \ \ is in the range from 0.0001 to 40 wt relative to the total weight of the fragrance preparation.\ \ **8**. A fragrance preparation according to claim 6 comprising an additional fragrance with an odor note of lily of the valley.\ \ **9**. A fragrance preparation according to claim 6, wherein\ \ (i) the amount of the compound of formula (Ia) is sufficient to endow the fragrance preparation with an odor note of lily of the valley,\ \ and/or\ \ (ii) an additional fragrance of the fragrance preparation imparts an odor note of lily of the valley, wherein the amount of the compound of formula (Ia) is sufficient, in comparison with a comparative fragrance preparation of otherwise identical composition without the compound of formula (Ia), to modify and/or to intensify the odor note of lily of the valley,\ \ and/or\ \ (iii) the amount of the compound of formula (Ia) is sufficient to endow the fragrance preparation with an impression selected from the group consisting of natural, caring, complex and radiant\ \ and/or\ \ (iv) the amount of the compound of formula (Ia) is sufficient to modify and/or to intensify an impression selected from the group consisting of natural, caring, complex and radiant in comparison with a comparative fragrance preparation of otherwise identical composition without the compound of formula (Ia)\ \ and/or\ \ (v) the amount of the compound of formula (Ib) is sufficient to endow the fragrance preparation with an odor note of lily of the valley,\ \ and/or\ \ (vi) an additional fragrance of the fragrance preparation imparts an odor note of lily of the valley, wherein the amount of the compound of formula (Ib) is sufficient, in comparison with a comparative fragrance preparation of otherwise identical composition without the compound of formula (Ib), to modify and/or to intensify the odor note of lily of the valley.\ \ **10**. A perfumed product comprising\ \ a compound of formula (I) as defined in claim 1 in a sensorially effective amount.\ \ **11**. A perfumed product according to claim 10, wherein the amount of a compound of formula (Ia) and/or a compound of formula (Ib) is in the range from 0.0001 to 5 wt %, relative to the total weight of the product.\ \ **12**. A perfumed product according to claim 10, selected from the group consisting of washing and cleaning products, hygiene products, and care products.\ \ **13**. A method for of providing skin, hair, surfaces, or textile fibers with an odor note of lily of the valley comprising applying a fragrance preparation according to claim 6 to the skin, hair, surfaces, or textile fibers.\ \ **14**. A method for producing the compound of formula (I)\ \ \ \ comprising an acid-catalyzed reaction of an acetal of formula (II),\ \ \ \ wherein R is a linear or branched, saturated or unsaturated alkyl group with 1 to 10 carbon atoms.\ \ **15**. An acetal of formula (II)\ \ \ \ wherein R is a linear or branched, saturated or unsaturated alkyl group with 1 to 10 carbon atoms.\ \ **16**. A method for producing a compound of formula (Ia) or a compound of formula (Ib) as defined in claim 1, or a mixture of compounds of formula (Ia) and (Ib), comprising the use\ \ of d-(+) limonene as educt for producing the compound of formula (Ia),\ \ of 1-(−) limonene as educt for producing the compound of formula (Ib) as, or\ \ of a mixture containing d-(+) limonene and 1-(−) limonene as educt for producing a mixture containing the compound of formula (Ia) and the compound of formula (Ib).\ \ **17**. A method for producing a compound of formula (I) as defined in claim 6 comprising pyrolysis of the spirolactone of formula (VIII) to form the compound of formula (I)\ \ \ \ **18**. A method for mediating, intensifying and/or modifying an odor note of lily of the valley to a substance comprising bringing the substance into contact with a compound according to claim 1.\ \ a compound of formula (I),\ \ **19**. A method for mediating, intensifying and/or modifying an odor note of lily of the valley to a substance comprising bringing the substance into contact with a mixture according to claim 2.\ \ **20**. A method for mediating, intensifying and/or modifying an odor note of lily of the valley to a substance comprising bringing the substance into contact with a fragrance preparation according to claim 6.\ \ **21**. A method for mediating, intensifying and/or modifying an odor note of lily of the valley to a substance comprising bringing the substance into contact with a fragrance preparation according to claim 7.\ \ **22**. A method for increasing the sub stantivity and/or the retention of a fragrance comprising combining the fragrance with a compound of formula (I) as defined in claim 6.


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Fetched public patent page; stored extracted spans only, not bulk full text.

“Standard” systems refer to those that are “pre-loaded” with the intent of keeping the pre-loaded perfume associated with the polymer until the moment or moments of perfume release. Such polymers may also suppress the neat product odor and provide a bloom and/or longevity benefit depending on the rate of perfume release. One challenge with such systems is to achieve the ideal balance between 1) in-product stability (keeping perfume inside carrier until you need it) and 2) timely release (during use or from dry situs). Achieving such stability is particularly important during in-product storage and product aging. This challenge is particularly apparent for aqueous-based, surfactant-containing products, such as heavy duty liquid laundry detergents. Many “Standard” matrix systems available effectively become “Equilibrium” systems when formulated into aqueous-based products. One may select an “Equilibrium” system or a Reservoir system, which has acceptable in-product diffusion stability and available triggers for release (e.g., friction). “Equilibrium” systems are those in which the perfume and polymer may be added separately to the product, and the equilibrium interaction between perfume and polymer leads to a benefit at one or more consumer touch points (versus a free perfume control that has no polymer-assisted delivery technology). The polymer may also be pre-loaded with perfume; however, part or all of the perfume may diffuse during in-product storage reaching an equilibrium that includes having desired perfume raw materials (PRMs) associated with the polymer. The polymer then carries the perfume to the surface, and release is typically via perfume diffusion. The use of such equilibrium system polymers has the potential to decrease the neat product odor intensity of the neat product (usually more so in the case of pre-loaded standard system). Deposition of such polymers may serve to “flatten” the release profile and provide increased longevity. As indicated above, such longevity would be achieved by suppressing the initial intensity and may enable the formulator to use more high impact or low odor detection threshold (ODT) or low Kovats Index (KI) PRMs to achieve FMOT benefits without initial intensity that is too strong or distorted. It is important that perfume release occurs within the time frame of the application to impact the desired consumer touch point or touch points. Suitable micro-particles and micro-latexes as well as methods of making same may be found in USPA 2005/0003980 A1. Matrix systems also include hot melt adhesives and perfume plastics. In addition, hydrophobically modified polysaccharides may be formulated into the perfumed product to increase perfume deposition and/or modify perfume release. All such matrix systems, including for example polysaccarides and nanolatexes may be combined with other PDTs, including other PAD systems such as PAD reservoir systems in the form of a perfume microcapsule (PMC). Polymer Assisted Delivery (PAD) matrix systems may include those described in the following references: US Patent Applications 2004/0110648 A1; 2004/0092414 A1; 2004/0091445 A1 and 2004/0087476 A1; and U.S. Pat. Nos. 6,531,444; 6,024,943; 6,042,792; 6,051,540; 4,540,721 and 4,973,422.


IV. Amine Assisted Delivery (AAD): The amine-assisted delivery technology approach utilizes materials that contain an amine group to increase perfume deposition or modify perfume release during product use. There is no requirement in this approach to pre-complex or pre-react the perfume raw material(s) and amine prior to addition to the product. In one aspect, amine-containing AAD materials suitable for use herein may be non-aromatic; for example, polyalkylimine, such as polyethyleneimine (PEI), or polyvinylamine (PVAm), or aromatic, for example, anthranilates. Such materials may also be polymeric or non-polymeric. In one aspect, such materials contain at least one primary amine. This technology will allow increased longevity and controlled release also of low ODT perfume notes (e.g., aldehydes, ketones, enones) via amine functionality, and delivery of other PRMs, without being bound by theory, via polymer-assisted delivery for polymeric amines. Without technology, volatile top notes can be lost too quickly, leaving a higher ratio of middle and base notes to top notes. The use of a polymeric amine allows higher levels of top notes and other PRMS to be used to obtain freshness longevity without causing neat product odor to be more intense than desired, or allows top notes and other PRMs to be used more efficiently. In one aspect, AAD systems are effective at delivering PRMs at pH greater than about neutral. Without wishing to be bound by theory, conditions in which more of the amines of the AAD system are deprotonated may result in an increased affinity of the deprotonated amines for PRMs such as aldehydes and ketones, including unsaturated ketones and enones such as damascone. In another aspect, polymeric amines are effective at delivering PRMs at pH less than about neutral. Without wishing to be bound by theory, conditions in which more of the amines of the AAD system are protonated may result in a decreased affinity of the protonated amines for PRMs such as aldehydes and ketones, and a strong affinity of the polymer framework for a broad range of PRMs. In such an aspect, polymer-assisted delivery may be delivering more of the perfume benefit; such systems are a subspecies of AAD and may be referred to as Amine-Polymer-Assisted Delivery or APAD. In some cases when the APAD is employed in a composition that has a pH of less than seven, such APAD systems may also be considered Polymer-Assisted Delivery (PAD). In yet another aspect, AAD and PAD systems may interact with other materials, such as anionic surfactants or polymers to form coacervate and/or coacervates-like systems. In another aspect, a material that contains a heteroatom other than nitrogen, for example sulfur, phosphorus or selenium, may be used as an alternative to amine compounds. In yet another aspect, the aforementioned alternative compounds can be used in combination with amine compounds. In yet another aspect, a single molecule may comprise an amine moiety and one or more of the alternative heteroatom moieties, for example, thiols, phosphines and selenols. Suitable AAD systems as well as methods of making same may be found in US Patent Applications 2005/0003980 A1; 2003/0199422 A1; 2003/0036489 A1; 2004/0220074 A1 and U.S. Pat. No. 6,103,678.


VI. Starch Encapsulated Accord (SEA): The use of a starch encapsulated accord (SEA) technology allows one to modify the properties of the perfume, for example, by converting a liquid perfume into a solid by adding ingredients such as starch. The benefit includes increased perfume retention during product storage, especially under non-aqueous conditions. Upon exposure to moisture, a perfume bloom may be triggered. Benefits at other moments of truth may also be achieved because the starch allows the product formulator to select PRMs or PRM concentrations that normally cannot be used without the presence of SEA. Another technology example includes the use of other organic and inorganic materials, such as silica to convert perfume from liquid to solid. Suitable SEAs as well as methods of making same may be found in USPA 2005/0003980 A1 and U.S. Pat. No. 6,458,754 B1.


VIII. Pro-Perfume (PP): This technology refers to perfume technologies that result from the reaction of perfume materials with other substrates or chemicals to form materials that have a covalent bond between one or more PRMs and one or more carriers. The PRM is converted into a new material called a pro-PRM (i.e., pro-perfume), which then may release the original PRM upon exposure to a trigger such as water or light. Pro-perfumes may provide enhanced perfume delivery properties such as increased perfume deposition, longevity, stability, retention, and the like. Pro-perfumes include those that are monomeric (non-polymeric) or polymeric, and may be pre-formed or may be formed in-situ under equilibrium conditions, such as those that may be present during in-product storage or on the wet or dry situs. Nonlimiting examples of pro-perfumes include Michael adducts (e.g., beta-amino ketones), aromatic or non-aromatic imines (Schiff bases), oxazolidines, beta-keto esters, and orthoesters. Another aspect includes compounds comprising one or more beta-oxy or beta-thio carbonyl moieties capable of releasing a PRM, for example, an alpha, beta-unsaturated ketone, aldehyde or carboxylic ester. The typical trigger for perfume release is exposure to water; although other triggers may include enzymes, heat, light, pH change, autoxidation, a shift of equilibrium, change in concentration or ionic strength and others. For aqueous-based products, light-triggered pro-perfumes are particularly suited. Such photo-pro-perfumes (PPPs) include but are not limited to those that release coumarin derivatives and perfumes and/or pro-perfumes upon being triggered. The released pro-perfume may release one or more PRMs by means of any of the above mentioned triggers. In one aspect, the photo-pro-perfume releases a nitrogen-based pro-perfume when exposed to a light and/or moisture trigger. In another aspect, the nitrogen-based pro-perfume, released from the photo-pro-perfume, releases one or more PRMs selected, for example, from aldehydes, ketones (including enones) and alcohols. In still another aspect, the PPP releases a dihydroxy coumarin derivative. The light-triggered pro-perfume may also be an ester that releases a coumarin derivative and a perfume alcohol. In one aspect the pro-perfume is a dimethoxybenzoin derivative as described in USPA 2006/0020459 A1. In another aspect the pro-perfume is a 3′, 5′-dimethoxybenzoin (DMB) derivative that releases an alcohol upon exposure to electromagnetic radiation. In yet another aspect, the pro-perfume releases one or more low ODT PRMs, including tertiary alcohols such as linalool, tetrahydrolinalool, or dihydromyrcenol. Suitable pro-perfumes and methods of making same can be found in U.S. Pat. Nos. 7,018,978 B2; 6,987,084 B2; 6,956,013 B2; 6,861,402 B1; 6,544,945 B1; 6,093,691; 6,277,796 B1; 6,165,953; 6,316,397 B1; 6,437,150 B1; 6,479,682 B1; 6,096,918; 6,218,355 B1; 6,133,228; 6,147,037; 7,109,153 B2; 7,071,151 B2; 6,987,084 B2; 6,610,646 B2 and 5,958,870, as well as can be found in USPA 2005/0003980 A1 and USPA 2006/0223726 A1.


Solid-Phase Micro-Extraction (SPME)-Gas Chromatography/Mass Spectrometry is used to measure the level of perfume raw materials in the headspace of products. 1.0 grams of the 1 week at 40 degrees Centigrade aged sample (shampoo or conditioner) are placed into a clean 20 ml headspace vial and allowed to equilibrate for at least 2 hours at room temperature.


50/30; 5 minutes; 3 minutes; 4.67 minute

Analysis Procedure: - 1\. Transfer sample to proper sample tray and proceed with SPME-GC-MS analysis. - 2\. Start sequence of sample loading and analysis. In this step, the sample is allowed to equilibrate for at least two hours on the auto sampler tray, then sampled directly from the tray. The SPME fiber assembly is DVB/CAR/PDMS (50/30 um, 24 ga, 1 cm length). Sampling time is 5 minutes. - 3\. Injector temperature is at 260 C. - 4\. Then GC-MS analysis run is started. Desportion time is 5 minutes. - 5\. The following temperature program is used: - i) an initial temperature of about 50° C. which is held for 3 minutes, - ii) increase the initial temperature at a rate of about 6° C./min until a temperature of about 250° C. is reached, then 25° C./min to 275° C., hold at about 275° C. for 4.67 minute. - 6\. Perfume compounds are identified using the MS spectral libraries of John Wiley & Sons and the National Institute of Standards and Technology (NIST), purchased and licensed through Hewlett Packard. - 7\. Chromatographic peaks for specific ions are integrated using the Chemstation software obtained from Agilent Technologies, Inc., Wilmington, Del., USA. - 8\. The ratio for each PRM is calculated by dividing the peak area for the perfume raw material in Sample A by the peak area in Sample B. - 9\. Each ratio is then weighted by that perfume raw material's weight composition in the perfume. - 10\. The Headspace Ratio is calculated as the sum of the individual perfume raw material ratios obtained in step 9.