Previous attempts to overcome these problems have been through the use of various "fixatives" or "modulators" to retard the evaporation of the more volatile fragrance ingredients present in fragrance compositions. For instance, [U.S. Patent No. 4,313,855](https://patents.google.com/patent/US4313855) (Dragoco) describes the use in cosmetic compositions of 1-(2,6,6-trimethylcyclohexyl)-hexane-3-ol as an odourless fixative for increasing the perfume's intensity. [U.S. Patent No. 6,147,049](https://patents.google.com/patent/US6147049) (Givaudan) discloses a perfume fixative derived from tera-hydronaphthalenese for use in a wide range of fragrance compositions. [U.S. Patent No. 6,440,400B1](https://patents.google.com/patent/US6440400) (Takasago Perfumery) describes a composition using trimethylcyclohexane derivatives as perfuming-holding agents and melanin-formation inhibitors. [U.S. Patent No. 6,737,396B2](https://patents.google.com/patent/US6737396) (Firmenich) describes a perfume composition formed by mixing 2-30%, relative to the weight of the composition, of a fixative, (1-ethoxyethoxy)cyclododecane, to fix or exalt the musky or aromatic-type notes. [U.S. Patent No. 7,538,081](https://patents.google.com/patent/US7538081) (Takasago Perfumery) approaches the same problem of fixing a perfume and/or extending the perfume release from a fragrance composition. More particularly, said document describes the use of L-menthoxy ether derivatives as fixatives in fragrance compositions comprising at least one note selected from: floral, citrus, fruity, green, mint, herb and marine. JP Patent No. 61-083114 (Kanebo) describes ether derivatives as aroma-preserving agent for fine perfume composition. JP Patent No. 61-063612 (Kanebo) discloses diethylene glycol ether derivatives as fragrance adjusting agent showing effects as a fixative and a solubilizer. JP Patent No. 62-084010 (Shiseido) describes hydroquinone glycoside as perfume fixatives applicable for all kinds of perfume and blended perfume. On the other hand, PCT Publication No. WO85/04803 (Diagnostica) describes the use of hyaluronic acid/ hyaluronate as fixatives ( _via_ molecular encapsulation) in fragrance products to improve persistence of the fragrance. EP 1 186 289 describes fragrance compositions having excellent diffusivity and a long-lasting effect by incorporating a novel fixative in the composition, wherein the fixative is a 2-(L-menthoxy)alkanol derivative. EP 1 103 250 describes oil-in-polyhydric-alcohol type warming base agents containing a polyhydric alcohol, a sucrose fatty acid ester and an oil, having superior makeup removal effect, safety, stability and warming sensation. [WO 2014/090959](https://patents.google.com/patent/WO2014090959) discloses perfuming compositions that are free of ethanol in the form of transparent, clear microemulsions containing a fragrance, a solvent, non-ionic and ionic surfactants, a cooling hydrotrope and water. [US 2003/228334](https://patents.google.com/patent/US20030228334) relates to oil-in-water emulsions having a mattifying effect on the skin. The emulsions comprise a hydrophilic, non-organically modified magnesium aluminum silicate or a bentonite clay and a polyol in the water phase; and a volatile lipophilic solvent and a high melting point lipophilic plasticizer in the oil phase; and a surfactant system incuding non-toxic metal alkyl sulfates and/or sucrose esters. [DE 197 18 777](https://patents.google.com/patent/DE19718777) discloses the use of one or more di- or oligo-saccharide fatty acid esters as anti-adhesive agents against microorganisms, viruses, parasites and protozoa.


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The inventors have surprisingly discovered a revolutionary new way of objectively classifying fragrance materials and then formulating those fragrance materials into complex fragrance mixtures having improved fragrance profile fidelity and longevity. Essentially, the solution is to formulate the fragrance materials having low levels (10 to 30 wt% relative to the total weight of the fragrance materials) of the low volatile fragrance materials in the presence of a substantially non-odorous fragrance modulator to provide for improved or enhanced longevity and/or fidelity of the fragrance profile, particularly amongst characters attributable to volatile fragrance materials. In fact, the inventors have discovered that in the complete absence of the low volatile fragrance materials or at very low levels of the low volatile fragrance materials (less than 10 wt% relative to the total weight of the fragrance materials), there is insufficient character complexity and roundness of the fragrance profile for consumer acceptance of the composition. Therefore the level of low volatile fragrance materials needs to be carefully chosen between 10 and 30 wt% to balance consumer acceptance and the desired improved or enhanced longevity and/or fidelity of the fragrance profile, particularly amongst characters attributable to volatile fragrance materials.


At the testing facility, 50 µL samples of the compositions and the controls are applied to glass slides and placed on a hot plate at 32 °C to represent skin temperature for varying durations. It is important that glass slides of samples that are to be later compared are prepared at the same time. The panelists are asked to evaluate the perceived fragrance profile (intensity and/or character) of each glass slide sample at a given time point. Slides are presented coded so that their identity is not known by the panelists. Within a given time point panelists evaluate the slides in a random order and are able to revisit their assessment as they work through the slides at that time point. Their assessments are recorded. In the subsequent analysis, the data for strength and character comparisons are drawn from the independent assessments carried out at a given time point. Only when using the character difference scale below are any 2 products physically directly compared to each other. Panelists are selected from individuals who are either trained to evaluate fragrances according to the scales below or who have experience with fragrance evaluation in the industry. Typically, around 6 to 10 panellists are used to evaluate a given product and its control.


The panelists are asked to give a score on a scale of 0 to 5 for perceived fragrance intensity according to the odour intensity scale set out in Table 4 herein below. Table 4 - Odour Intensity Scale


5\. Multiple glass capillaries are prepared in the same way and left to evaporate at ambient temperature for pre-determined periods of time, such as for example 10, 15, 30 mins, 1 hr, 2 hrs, 3 hrs, 4 hrs, 5 hrs, and up to 6 hrs, before being introduced to the headspace vial and sealed.


Compositions disclosed in Tables 18(a) and 19(a)-19(b) are applied to glass slides in accordance with the protocol described in the Method Section and a panel of around 6-10 experienced panelists evaluate the perceived fragrance profile at initial time 0, then at various time points, typically 1 hour, 2 hours, 3 hours, 4 hours and 6 hours post application. Panelists are asked to score the compositions for the longevity of the fragrance profile on a scale of 0 to 5, wherein 0 represents a no fragrance is detected and 5 represents a very strong fragrance intensity is detected; and for fragrance profile fidelity on a scale of 0 to 3 wherein 0 represents not detectable and 3 represents it being the dominant character. The results of the panelists are then averaged and discussed below.

6-10; 1 hour; 2 hours; 3 hours; 4 hours; 6 hours; 0 to 5; 0 to 3


Figure 1 shows the fragrance intensity profile of Composition R as evaluated by 10 panelists, which comprises the substantially non-odorous fragrance modulator sucrose myristate and the single fragrance material, ethyl safranate. Addition of the substantially non-odorous fragrance modulator maintains the intensity of the fragrance material for up to 6 hours whilst the control, Composition S, in the absence of the substantially non-odorous fragrance modulator, drops in fragrance intensity profile over the 6 hours. The substantially non-odorous fragrance modulator acts to maintain the continued evaporation over time of the fragrance material. Statistical analysis using the Tukey correction for multiple comparisons confirms the statistically significant difference at 0 hours (p = 0.0015), 1hour (p = 0.0033), 3hours (p = 0.0015) and 6 hours ((p = 0.0152) all at 95% significance level ( _i.e.,_ p < 0.05).


Figure 2 shows the fragrance intensity profile of Composition P as evaluated by 10 panellists, which comprises the substantially non-odorous fragrance modulator sucrose myristate and the single fragrance material, Dimethylbenzyl carbinol. Addition of the substantially non-odorous fragrance modulator maintains the intensity of the fragrance material for up to 6 hours whilst the control, Composition Q, in the absence of the substantially non-odorous fragrance modulator, drops in fragrance intensity profile over the 6 hours. The substantially non-odorous fragrance modulator acts to maintain the continued evaporation over time of the fragrance material. Statistical analysis using the Tukey correction for multiple comparisons confirms the statistically significant difference at 1hour (p = 0.0581) at 90% significance level ( _i.e.,_ p < 0.1), 3hours (p = 0.0311) at 95% significance level ( _i.e.,_ p < 0.05).


Figure 3 shows the fragrance intensity profile of Composition T as evaluated by 10 panelists, which comprises the substantially non-odorous fragrance modulator sucrose myristate and the single fragrance material phenethyl alcohol (PEA). Addition of the substantially non-odorous fragrance modulator maintains the intensity of the fragrance material for up to 6 hours whilst the control, Composition U, in the absence of the substantially non-odorous fragrance modulator, drops in fragrance intensity profile over the 6 hours. The substantially non-odorous fragrance modulator acts to maintain the continued evaporation over time of the fragrance material. Statistical analysis using the Tukey correction for multiple comparisons confirms the statistically significant difference at 1 hour (p < 0.0001), 3 hours (p = 0.0016) and 6 hours (p= 0.0003) all at 95% significance level ( _i.e.,_ p < 0.05).


Figure 4 shows the fragrance intensity profile of Composition ZZ as evaluated by 11 panelists, which comprises the substantially non-odorous fragrance modulator hydroquinone beta-D-glycoside and the single fragrance material, eugenol. Addition of the substantially non-odorous modulator maintains the intensity of the fragrance material for up to 6 hours whilst the control, Composition ZZZ, in the absence of the substantially non-odorous fragrance modulator, drops in fragrance intensity profile over the 6 hours. The substantially non-odorous fragrance modulator acts to maintain the continued evaporation over time of the fragrance material. Statistical analysis using the Tukey correction for multiple comparisons confirms the statistically significant difference at 1 hour (p = 0.0008) and 3 hours (p = 0.0123) all at 95% significance level ( _i.e.,_ p < 0.05).


(b) Effects of the Substantially Non-Odorous Fragrance Modulators on the Fragrance Profile Longevity of Compositions having Reduced Levels of Low Volatile Fragrance Materials (between 10 to 30 wt% relative to the total weight of the Fragrance Materials) vs. Compositions having Traditional Levels of Low Volatile Fragrance Materials (Greater than 30 wt% relative to the total weight of the Fragrance Materials) and No Substantially Non-Odorous Fragrance Modulator- \[0119\]


Panelists are asked to score the compositions for the intensity of the fragrance on a scale of 0 to 5, wherein 0 represents no fragrance intensity is detected and 5 represents a very strong fragrance intensity is detected. The results of the panel test are then averaged. The results show the effect of the substantially non-odorous fragrance modulator and reduced levels of low volatile fragrance materials for any one of the inventive Compositions A, D, G, J and M on fragrance profile longevity versus control Compositions C, F, I, L and O in the absence of a substantially non-odorous modulator. Alternatively, the results show the effect of the substantially non-odorous fragrance modulator and reduced levels of low volatile fragrance materials for any one of the inventive Compositions A, D, G, J and M on fragrance profile longevity versus traditional Compositions B, E, H, K and N in the presence of the substantially non-odorous fragrance modulator.


Fragrance profile longevity, is maintained for up to at least 6 hours in the presence of the substantially non-odorous fragrance modulator whilst it drops in the absence of the substantially non-odorous fragrance modulator (data not shown). Without wishing to be bound by theory, it is believed that the substantially non-odorous fragrance modulator acts to maintain the continued evaporation over time of the fragrance materials, particular the volatile fragrance materials. The effect of the improved fragrance profile longevity of the present invention are noticeable at 1, 3 and 6 hours.


The test demonstrates the character retention over time of a fragrance composition. The results show the effect of the substantially non-odorous fragrance modulator and reduced levels of low volatile fragrance materials for any one of the inventive Compositions A, D, G, J, and M on fragrance profile longevity versus control Compositions C, F, I, L, and O, in the absence of the substantially non-odorous modulator. Alternatively, results show the effect of the substantially non-odorous fragrance modulator and reduced levels of low volatile fragrance materials for any one of the inventive Compositions A, D, G, J, and M on fragrance profile longevity versus traditional Compositions B, E, H, K, and N, in the presence of the substantially non-odorous fragrance modulator. Fragrance profile fidelity, particularly characters attributable to the volatile fragrance materials are maintained for up to at least 1 hour in the presence of the substantially non-odorous fragrance modulator whilst they drop in the absence of the substantially non-odorous fragrance modulator.


17. A method to enhance the fragrance profile of a composition, preferably improve the longevity of a character, preferably a floral character, of a composition, comprising bringing into contact or mixing at least one substantially non-odorous fragrance modulator with at least one low volatile fragrance material according to a composition as defined according to any one of claims 1-16.


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Bei einer Dosierung von 0.3 Gew.- % des Parfümöls F1 bzw. F2 im Allzweckreiniger ergibt sich folgender Befund: der Anteil von 3-\[(4R)-4-Isopropylcyclohexen-1-yl)propanal bewirkt in dem das Parfümöl F2 enthaltenden Allzweckreiniger eine Verstärkung der blumigen Note gegenüber dem Allzweckreiniger, der das Parfümöl F1 (ohne 3-\[(4R)-4-Isopropylcyclohexen-1-yl\]propanal) enthält. Ferner erscheint die Komposition des Allzweckreinigers mit dem Parfümöl F2 viel cremiger und frischer als die des Allzweckreinigers mit dem Parfümöl F1.At a dosage of 0.3% by weight of the perfume oil F1 or F2 in the all-purpose cleaner, the following result is obtained: the proportion of 3 - \[(4R) -4-isopropylcyclohexen-1-yl) propanal causes in the perfume oil F2-containing all-purpose cleaner a Reinforcing the floral note over the all-purpose cleaner containing perfume oil F1 (without 3 - \[(4R) -4-isopropylcyclohexen-1-yl\] propanal). Furthermore, the composition of the all-purpose cleaner appears with the perfume oil F2 much creamier and fresher than the all-purpose cleaner with the perfume oil F1.\ \ **BEISPIEL 15AEXAMPLE 15A**Shampoo (Mengenangaben als Gew.-%)Shampoo (amounts in% by weight)\ \ **Materialmaterial****HerstellerManufacturer****INCI-NameINCI name****Anteilproportion of**Entionisiertes WasserDeionized waterWaterWater71,571.5Plantacare PS 10Plantacare PS 10Cognis Deutschland GmbHCognis Germany GmbHSodium Laureth Sulfate, Lauryl GlucosideSodium Laureth Sulfate, Lauryl Glucoside20,020.0Euperlan PK 771Euperlan PK 771Cognis Deutschland GmbHCognis Germany GmbHGlycol Distearate, Sodium Lauryl Sulfate, Cocamide MEA, Laureth-1 0Glycol Distearate, Sodium Lauryl Sulfate, Cocamide MEA, Laureth-1 06,06.0Dragocid LiquidDragocid LiquidSymriseSymrisePhenoxyethanol, Methylparaben, Ethylparaben, Butylparaben, Propylparaben, IsobutylparabenPhenoxyethanol, methylparaben, ethylparaben, butylparaben, propylparaben, isobutylparaben0,50.5Natrium ChloridSodium chlorideSodium ChlorideSodium Chloride1,41.4Citronensäure Monohydrat kristallinCitric acid monohydrate crystallineCitric AcidCitric Acid0,10.1Parfumöl G1 bzw. G2Perfume oil G1 or G2SymriseSymriseParfum (Fragrance)Perfume (fragrance)0,50.5\ \ **BEISPIEL 15BEXAMPLE 15B**Zusammensetzung des Parfümöls G1 bzw. G2 (Mengenangaben als Gew.-%)Composition of the perfume oil G1 or G2 (amounts in% by weight)\ \ **RIECHSTOFFEfragrances****Parfümöl G1 (Vergleich)Perfume oil G1 (comparison)****Parfümöl G2 (Erfindungsgemäß)Perfume oil G2 (according to the invention)**FARENAL(R)FARENAL (R)3,03.03,03.0FLORAZONFLORAZON0,50.50,50.5HEXENYL ACETATE CIS-3HEXENYL ACETATE CIS-33,03.03,03.0VERTOCITRALVERTOCITRAL1,01.01,01.0DYNASCONE 10 % DPGDYNASCONE 10% DPG2,02.02,02.0CYCLOGALBANAT(R)Cyclogalbanate (R)2,02.02,02.0STYRALYL ACETATESTYRALYL ACETATE1,51.51,51.5DIHYDRO MYRCENOLDIHYDRO MYRCENOL6,06.06,06.0OXANTHIA 50 % IN TEC 10 % DPGOXANTHIA 50% IN TEC 10% DPG10,010.010,010.0LEMON OIL ITAL.LEMON OIL ITAL.10,010.010,010.0ORANGE OIL BRASILORANGE OIL BRASIL50,050.050,050.0HEXYL ACETATEHEXYL ACETATE2,02.02,02.0ISOAMYL ACETATEISOAMYL ACETATE0,50.50,50.5PRENYLACETATEPRENYLACETATE0,50.50,50.5ETHYL BUTYRATE 10 % DPGETHYL BUTYRATE 10% DPG2,02.02,02.0ALDEHYDE C14 SO-CALLEDALDEHYDE C14 SO-CALLED25,025.025,025.0DECALACTONE GAMMADECALACTONE GAMMA5,05.05,05.0ETHYL METHYL BUTYRATE-2ETHYL METHYL BUTYRATE-21,01.01,01.0ALLYL CAPROATEALLYL CAPROATE1,51.51,51.5ALLYL CYCLOHEXYL PROPIONATEALLYL CYCLOHEXYL PROPIONATE3,03.03,03.0ALLYL HEPTOATEALLYL HEPTOATE2,52.52,52.5MELOZONEMELOZONE2,02.02,02.0CALONE 1951CALONE 19510,50.50,50.5MUGETANOLMUGETANOL10,010.010,010.0LINALOOLLINALOOL25,025.025,025.0DIMETHYL BENZYL CARBINYL ACETATEDIMETHYL BENZYL CARBINYL ACETATE6,06.06,06.0DIMETHYL BENZYL CARBINYL BUTYRATDIMETHYL BENZYL CARBINYL BUTYRATE4,04.04,04.0PHENYLETHYL ACETATEPHENYLETHYL ACETATE1,51.51,51.5PHENYLETHYL ALCOHOLPHENYLETHYL ALCOHOL15,015.015,015.0CITRONELLOL 950CITRONELLOL 95010,010.010,010.0GERANIOL SUPERGERANIOL SUPER5,05.05,05.0GERANYL ACETATE PUREGERANYL ACETATE PURE15,015.015,015.0ISODAMASCON(R)Isodamascone (R)2,02.02,02.0BENZYL ACETATEBENZYL ACETATE15,015.015,015.0HEDIONEHEDIONE90,090.090,090.0HEXYL CINNAMIC ALDEHYDE ALPHAHEXYL CINNAMIC ALDEHYDE ALPHA35,035.035,035.0JASMONE CISJASMONE CIS0,50.50,50.5BENZYL SALICYLATEBENZYL SALICYLATE80,080.080,080.0HEXENYL SALICYLATE CIS-3HEXENYL SALICYLATE CIS-330,030.030,030.0ISORALDEINE 70ISORALDEINE 7035,035.035,035.0HERBAFLORATHERBAFLORAT15,015.015,015.0ISO E SUPERISO E SUPER15,015.015,015.0ISOBORNYL CYCLOHEXANOLISOBORNYL CYCLOHEXANOL30,030.030,030.0BRAHMANOL(R)Brahmanol (R)10,010.010,010.0AMBROXIDEAMBROXIDE1,51.51,51.5GLOBALIDE(R)GLOBALIDE (R)5,05.05,05.0GALAXOLIDE 50 % IN DPGGALAXOLIDE 50% IN DPG120,0120.0120,0120.0**3-\[(4 _R_)-4-Isopropylcyclohexen-1-yl\]propanal3 - propanal \[(4 _R)_ -4-Isopropylcyclohexen-1-yl\]****65,065.0**DIPROPYLENE GLYCOLDIPROPYLENE GLYCOL290,0290.0225,0225.01.000,01,000.01.000,01,000.0\ \ Bei einer Dosierung von 0.5 Gew.- % des Parfümöls G1 bzw. G2 im Shampoo ergibt sich folgender Befund: der Zusatz 3-\[(4 _R_)-4-Isopropylcyclohexen-1-yl\]propanal verstärkt in dem das Parfümöl G2 enthaltenden Shampoo den wässrigen-fruchtigen Charakter gegenüber dem Shampoo, welches das Parfümöl G1 (ohne 3-\[(4 _R_)-4-Isopropylcyclohexen-1-yl\]propanal) enthält. Zudem ist in dem Shampoo mit dem Parfümöl G2 die Diffusivität erhöht gegenüber dem Shampoo mit der Parfümöl G1.At a dosage of 0.5% by weight of the perfume oil G1 and G2 in the shampoo to the following findings obtained: the addition of 3 - \[-4-Isopropylcyclohexen-1-yl (4 _R)\]_ propanal shampoo amplified in the perfume oil G2 containing the aqueous fruity character compared to the shampoo, which (without 3 - \[(4 _R)_ -4-Isopropylcyclohexen-1-yl\] propanal) the perfume oil contains G1. In addition, in the shampoo with the perfume oil G2, the diffusivity increases over the shampoo with the perfume oil G1.\ \ **BEISPIEL 16AEXAMPLE 16A**Duschgel (Mengenangaben als Gew.-%)Shower gel (amount as wt .-%)\ \ **Materialmaterial****HerstellerManufacturer****INCI-NameINCI name****Anteilproportion of**Entionisiertes WasserDeionized waterWasserwater76,376.3Plantacare PS 10Plantacare PS 10Cognis Deutschland GmbHCognis Germany GmbHSodium Laureth Sulfate, Lauryl GlucosideSodium Laureth Sulfate, Lauryl Glucoside20,020.0Dragocid LiquidDragocid LiquidSymriseSymrisePhenoxyethanol, Methylparaben, Ethylparaben, Butylparaben, Propylparaben, IsobutylparabenPhenoxyethanol, methylparaben, ethylparaben, butylparaben, propylparaben, isobutylparaben0,50.5Natriumchloridsodium chlorideSodium ChlorideSodium Chloride1,41.4Citronensäure Monohydrat kristallinCitric acid monohydrate crystallineCitric AcidCitric Acid1,31.3Parfumöl G1 bzw. G2 aus Beispiel 15Perfume oil G1 or G2 from Example 15SymriseSymriseParfum (Fragrance)Perfume (fragrance)0,50.5\ \ Bei einer Dosierung von 0.5 Gew.- % des Parfümöls G1 bzw. G2 im Duschgel ergibt sich folgender Befund: der Zusatz von 3-\[(4 _R_)-4-Isopropylcyclohexen-1-yl\]propanal verleiht dem das Parfümöl G2 enthaltenden Duschgel eine natürlichere und pflegendere Note gegenüber dem Duschgel, welches das Parfümöl G1 (ohne 3-\[(4 **R**)-4-Isopropylcyclohexen-1-yl\]propanal) enthält.At a dosage of 0.5% by weight of the perfume oil G1 and G2 in the gel is the following results obtained: the addition of 3 - \[(4 _R)_ -4-Isopropylcyclohexen-1-yl\] propanal gives the gel the perfume oil G2 containing a natural and pflegendere Note opposite the shower gel, which (without 3 - \[(4 **R)** -4-Isopropylcyclohexen-1-yl\] propanal) the perfume oil contains G1.\ \ **BEISPIEL 17AEXAMPLE 17A**Transparente Deo-Stifte (Formulierungen A und B) bzw. Deo-Creme-Stifte (Formulierungen C und D) (Mengenangaben als Gew.-%)Transparent deodorant sticks (formulations A and B) or deodorant cream sticks (formulations C and D) (amounts in% by weight)\ \ **KOMPONENTECOMPONENT****AA****BB****CC****DD**Aluminium Zirconium Tetrachlorohydrat - Glycin KomplexAluminum zirconium tetrachlorohydrate - glycine complex25,0025,0020,0020.0025,0025,0020,0020.00Dimethicon (10 Cst)Dimethicone (10 Cst)----5,005.005,005.00Cyclopentasiloxancyclopentasiloxane--0,500.501,001.000,500.50Petrolatumpetrolatum5,005.004,704.705,005.005,005.00Ozokeritozokerite1,001.001,501.50----Stearylalkoholstearyl12,0012,0012,0012,00----2-Butyloctansäure2-butyl octanoic0,500.50--0,500.50--Wachswax----1,251.251,251.25PPG-14 ButyletherPPG-14 butyl ether9,009.009,009.00----Gehärtetes RapsölHardened rapeseed oil----5,005.005,005.00Siliciumdioxidsilica----1,001.00--Farnesolfarnesol0,250.25--0,250.25--Paraffinölparaffin oil0,500.500,500.50----Hydriertes Rizinusöl (castor wax)Hydrogenated castor oil (castor wax)3,503.503,503.50----Talktalc4,004.004,004.00----Behenylalkoholbehenyl0,200.200,200.20----d-Panthenyltriacetatd-panthenyl1,001.001,001.00----Konservierungsmittelpreservativeq.s.q.s.q.s.q.s.q.s.q.s.q.s.q.s.Parfümöl H1 bzw. H2Perfume oil H1 or H21,501.50--1,151.15--Parfümöl G2 aus Beispiel 15Perfume oil G2 from Example 150,900.90--0,750.75WasserwaterAd 100Ad 100Ad 100Ad 100Ad 100Ad 100Ad 100Ad 100\ \ **BEISPIEL 17BEXAMPLE 17B**Zusammensetzung des Parfümöls H1 bzw. H2 (Mengenangaben als Gew.-%)Composition of the perfume oil H1 or H2 (amounts in% by weight)\ \ **RIECHSTOFFEfragrances****Parfümöl H1 (Vergleich)Perfume oil H1 (comparative)****Parfümöl H2 (Erfindugsgemäß)Perfume oil H2 (according to the invention)**ALDEHYDE C10ALDEHYDE C100,50.50,50.5ALDEHYDE C12 MNA 10 % DPGALDEHYDE C12 MNA 10% DPG2,02.02,02.0MINTONATMINTONAT40,040.040,040.0MELOZONEMELOZONE0,50.50,50.5VERTOCITRALVERTOCITRAL6,06.06,06.0DIHYDRO MYRCENOLDIHYDRO MYRCENOL120,0120.0120,0120.0TETRAHYDRO MYRCENOLTETRAHYDRO MYRCENOL10,010.010,010.0AGRUNITRILAGRUNITRIL1,01.01,01.0ORANGE OIL BRASILORANGE OIL BRASIL10,010.010,010.0TAMARINE TYPE BASETAMARINE TYPE BASE10,010.010,010.0HEXYLACETATEHEXYLACETATE6,06.06,06.0ALDEHYDE C14 SO-CALLEDALDEHYDE C14 SO-CALLED1,01.01,01.0TETRAHYDRO LINALOOLTETRAHYDRO LINALOOL40,040.040,040.0DIMETHYL BENZYL CARBINYL BUTYRATDIMETHYL BENZYL CARBINYL BUTYRATE5,05.05,05.0ORANGE FLOWER ETHERORANGE FLOWER ETHER5,05.05,05.0PHENYLETHYL ACETATEPHENYLETHYL ACETATE6,56.56,56.5PHENYLETHYL ALCOHOLPHENYLETHYL ALCOHOL15,015.015,015.0GERANIOL SUPERGERANIOL SUPER30,030.030,030.0ROSAPHEN(R)Rosaphen (R)25,025.025,025.0ISODAMASCON(R)Isodamascone (R)0,50.50,50.5HEDIONEHEDIONE300,0300.0300,0300.0UNDECAVERTOLundecavertol0,50.50,50.5ALLYL IONONEALLYL IONONE2,52.52,52.5IONONE BETAIONONE BETA10,010.010,010.0EUGENOLEUGENOL4,04.04,04.0ISO E SUPERISO E SUPER30,030.030,030.0BRAHMANOL(R)Brahmanol (R)2,02.02,02.0AMBROXIDEAMBROXIDE2,02.02,02.0GLOBALIDE(R)GLOBALIDE (R)12,012.012,012.0GLOBANONE(R)GLOBANONE (R)8,08.08,08.0MACROLIDE(R) SUPRAMACROLIDE (R) SUPRA45,045.045,045.03-\[(4 _R_)-4-Isopropylcyclohexen-1-yl\]propanal3 - propanal \[(4 _R)_ -4-Isopropylcyclohexen-1-yl\]50,050.0DIPROPYLENE GLYCOLDIPROPYLENE GLYCOL300,0300.0250,0250.01.000,01,000.01.000,01,000.0\ \ **BEISPIEL 18EXAMPLE 18**Antiperspirant-Roll-On (Mengenangaben als Gew.-%)Antiperspirant roll-on (amounts in% by weight)\ \ **Komponentecomponent****AA****BB**Caprylyl Trimethicon (SilCare TM Silicone 31 M 50)Caprylyl trimethicone (SilCare ™ Silicone 31 M 50)0,300.300,300.30Steareth-20 (GENAPOL TM HS 200)Steareth-20 (GENAPOL ™ HS 200)3,003.003,003.00Steareth-2 (GENAPOLTM HS 020)Steareth-2 (GENAPOLTM HS 020)1,501.501,501.50Dicaprylyl Ether (Cetiol TM Ö)Dicaprylyl ether (Cetiol ™ Ö)2,002.002,002.00Coco Caprylat/Caprat (Cetiol TM LC)Coco Caprylate / Caprate (Cetiol TM LC)2,002.002,002.00Glyceringlycerin2,002.002,002.00Glyceryl Stearat (Cutina TM GMS)Glyceryl Stearate (Cutina TM GMS)2,002.002,002.00Octyldodecanol (Eutanol TM G)Octyldodecanol (Eutanol ™ G)1,001.001,001.00Stearyl alkoholStearyl alcohol2,502.502,502.50Aluminiumchlorohydrat gemäss Beispiel 1 der EP 1321431Aluminum chlorohydrate according to Example 1 of EP 1321431 10,0010.0010,0010.00Avocado Extract Persea GratissimaAvocado Extract Persea Gratissima0,300.300,200.20Parfümöl G2 aus Beispiel 15Perfume oil G2 from Example 150,500.50--Parfümöl H2 aus Beispiel 17Perfume oil H2 from Example 17--0,600.60WasserwaterAd 100Ad 100Ad 100Ad 100\ \ **BEISPIEL 19EXAMPLE 19**Antiperspirant-Stick (Mengenangaben als Gew.-%)Antiperspirant stick (amount as wt .-%)\ \ **Komponentecomponent****AA****BB**Phenyl Trimethicon (SilCare TM Silicone 15 M 50)Phenyl Trimethicone (SilCare ™ Silicone 15 M 50)13,5013.5013,5013.50Cetearyl AlkoholCetearyl alcoholAd 100Ad 100Ad 100Ad 100Cetiol CC (Dicaprylyl Carbonat)Cetiol CC (dicaprylyl carbonate)13,5013.5013,5013.50Stearinsäurestearic acid3,503.503,503.50PEG-40-Hydriertes Rizinusöl (Emulsogen TM HCO 040)PEG-40 hydrogenated castor oil (Emulsogen ™ HCO 040)4,104.104,104.10PEG-8 Distearate (Cithrol 4 DS)PEG-8 distearate (Cithrol 4 DS)4,104.104,104.10Petrolatumpetrolatum6,906.906,906.90Aluminiumchlorohydrataluminum chlorohydrate13,8013.8013,8013.80Aluminium Zirconium Trichlorohydrex GlyAluminum Zirconium Trichlorohydrex Gly19,5019.5020,0020.00Ethylhexylglycerin (Octoxyglycerin)Ethylhexylglycerol (octoxyglycerol)0,300.300,200.204-Methyl-4-phenyl-2-pentanol (Vetikol)4-methyl-4-phenyl-2-pentanol (Vetikol)0,250.250,100.10Parfümöl A2 aus Beispiel 9Perfume oil A2 from Example 91,001.00--Parfümöl G2 aus Beispiel 15Perfume oil G2 from Example 15--0,800.80\ \ **BEISPIEL 20EXAMPLE 20**Aerosolspray (Mengenangaben als Gew.-%)Aerosol spray (amount as wt .-%)\ \ **Komponentecomponent****AA****BB****CC**Octyldodecanoloctyldodecanol0,500.50--0,500.50Phenoxyethanolphenoxyethanol----0,300.301,2-Pentandiol1,2-pentanediol1,001.001,001.000,500.501,2-Hexandiol1,2-hexanediol0,250.250,150.150,250.251,2-Octandiol1,2-octanediol0,250.250,250.250,250.25Farnesolfarnesol--0,250.250,150.15Ethylhexylglycerin (Octoxyglycerin)Ethylhexylglycerol (octoxyglycerol)0,500.500,300.300,500.50Parfümöl A2 aus Beispiel 9Perfume oil A2 from Example 90,800.80--0,500.50Parfümöl H2 aus Beispiel 17Perfume oil H2 from Example 17--1,151.150,500.50EthanolethanolAd 100Ad 100Ad 100Ad 100Ad 100Ad 100\ \ Die nach Zusammenmischen der jeweils angegebenen Komponenten erhaltene Mischung wird mit einem Propan-Butan-Gemisch (2:7) im Gewichtsverhältnis 2 : 3 in einen Aerosolbehälter abgefüllt.The mixture obtained after mixing together the specified components is filled with a propane-butane mixture (2: 7) in a weight ratio of 2: 3 in an aerosol container.\ \ **BEISPIEL 21EXAMPLE 21**Haarconditioner mit UV-Schutz (Mengenangaben als Gew.-%)Hair conditioner with UV protection (amount as wt .-%)\ \ **Komponentecomponent****INCI NameINCI name****AA****BB**Lanette OLanette OCetearyl AlcoholCetearyl Alcohol4,004.004,004.00Dragoxat 89Dragoxat 89Ethylhexyl IsononanoateEthylhexyl isononanoate4,004.004,004.00EmulsiphosEmulsiphosPotassium Cetyl Phosphate, Hydrogenated Palm GlyceridesPotassium Cetyl Phosphate, Hydrogenated Palm Glycerides0,500.500,500.50Natrosol 250 HRNatrosol 250 HRHydroxyethylcellulosehydroxyethyl0,250.250,250.25Neo Heliopan HydroNeo Heliopan HydroPhenylbenzimidazole Sulfonic AcidPhenylbenzimidazole sulfonic acid2,002.002,002.00L- ArgininL-arginineArginineArginine1,201.201,201.20Benzophenon-4Benzophenone-4Benzophenone-4Benzophenone-40,500.500,500.50Neo Heliopan APNeo Heliopan APDisodium Phenyl Dibenzimidazole TetrasulfonateDisodium phenyl dibenzimidazole tetrasulfonates0,500.501,001.00Edeta BDEdeta BDDisodium EDTADisodium EDTA0,050.050,050.05Dragocide LiquidDragocide LiquidPhenoxyethanol (and) Methylparaben (and) Butyparaben (and) Ethyparaben (and) PropylparabenPhenoxyethanol (and) Methylparaben (and) Butyparaben (and) Ethyparaben (and) Propylparaben0,800.800,800.80Dow Corning 949 Cationic EmulsionDow Corning 949 Cationic EmulsionAmodimethicone, Cetrimonium Chloride, Trideceth-12Amodimethicone, Cetrimonium Chloride, Trideceth-122,002.002,002.00Dow Corning 5200Dow Corning 5200Laurylmethicone CopolyolLaurylmethicone copolyol0,500.500,500.50Parfümöl B2Perfume oil B2ParfumPerfume0,950.95--Parfümöl H2Perfume oil H2ParfumPerfume1,251.25WasserwaterWater (Aqua)Water (aqua)Ad 100Ad 100Ad 100Ad 100\ \ **BEISPIEL 22EXAMPLE 22**Sonnenschutzspray (Mengenangaben als Gew.-%)Sunscreen spray (amounts in% by weight)\ \ **Phasephase****Rohstofferaw materials****INCI BezeichnungINCI name****Anteilproportion of****AA**Wasser, demineralisiertWater, demineralizedWater (Aqua)Water (aqua)69,5069,50GlyceringlycerinGlyceringlycerin4,004.001,3 Butylenglykol1,3 butylene glycolButylene GlycolButylene glycol5,005.00D-PanthenolD-panthenolPanthenolpanthenol0,500.50Lara Care A-200Lara Care A-200GalactoarabinanGalactoarabinan0,250.25**BB**Baysiloneöl M 10Baysilone oil M 10DimethiconeDimethicone1,001.00Edeta BDEdeta BDDisodium EDTADisodium EDTA0,100.10Copherol 1250Copherol 1250Tocopheryl AcetateTocopheryl acetate0,500.50Cetiol ÖCetiol ÖDicaprylyl EtherDicaprylyl ether3,003.00Neo Heliopan (R) HMSNeo Heliopan (R) HMSHomosalateHomosalate5,005.00Neo Heliopan (R) AVNeo Heliopan (R) AVEthylhexyl MethoxycinnamateEthylhexyl methoxycinnamate6,006.00Neo Heliopan(R) 357Neo Heliopan (R) 357Butyl MethoxydibenzoylmethaneButyl methoxydibenzoylmethane1,001.00Corapan TQCorapan TQDiethylhexylnaphthalateDiethylhexylnaphthalate2,002.00Alpha BisabololAlpha bisabololBisabololbisabolol0,100.10Pemulen TR-2Pemulen TR-2Acrylates/C10-30 Alkyl Acrylate CrosspolymerAcrylates / C10-30 Alkyl Acrylate Crosspolymer0,250.25**CC**PhenoxyethanolphenoxyethanolPhenoxyethanolphenoxyethanol0,700.70Solbrol MSolbrol MMethylparabenmethylparaben0,200.20Solbrol PSolbrol PPropylparabenPropylparaben0,100.10**DD**NaOH, 10 % igNaOH, 10%Sodium HydroxideSodium hydroxides0,600.60**Ee**Parfümöl B2Perfume oil B2Fragrance (Parfum)Fragrance (perfume)0,200.20\ \ Herstellungsverfahren: Lara Care A-200 unter Rühren in den anderen Bestandteilen von Teil A lösen. Alle Rohstoffe des Teils B (ohne Pemulen) einwiegen und die kristallinen Substanzen unter Erwärmen lösen. Pemulen eindispergieren. Teil B zu Teil A geben und 1 Minute homogenisieren. Teile C-E zugeben und nochmals 1-2 Minuten mit dem Ultra Turrax homogenisieren.Method of preparation: Dissolve Lara Care A-200 with stirring in the other components of Part A. Weigh all raw materials of part B (without pemulen) and dissolve the crystalline substances by heating. Disperse pemulen. Add part B to part A and homogenize for 1 minute. Add parts C-E and homogenize with the Ultra Turrax for another 1-2 minutes.\ \ **BEISPIEL 23EXAMPLE 23**Sonnenschutz Softcreme (W/O). Lichtschutzfaktor (SPF) 40 (Mengenangaben als Gew.-%)Sunscreen soft cream (W / O). Sun protection factor (SPF) 40 (amounts in% by weight)\ \ **Phasephase****Rohstofferaw materials****INCI BezeichnungINCI name****Anteilproportion of****AA**Dehymuls PGPHDehymuls PGPHPolyglyceryl-2 DipolyhydroxystearatePolyglyceryl-2 dipolyhydroxystearates5,005.00Copherol 1250Copherol 1250Tocopheryl acetateTocopheryl acetate0,500.50Permulgin 3220Permulgin 3220Ozokeriteozocerites0,500.50Zinkstearatzinc stearateZinc StearateZinc stearate0,500.50Tegosoft TNTegosoft TNC12-15 Alkyl BenzoateC12-15 alkyl benzoates10,0010.00Neo Heliopan(R) E1000Neo Heliopan (R) E1000Isoamyl-p-MethoxycinnamateIsoamyl p-methoxycinnamate2,002.00Neo Heliopan(R) 303Neo Heliopan (R) 303OctocryleneOctocrylene5,005.00Neo Heliopan(R) MBCNeo Heliopan (R) MBC4-Methylbenzylidene Camphor4-methylbenzylidene camphor3,003.00Zinkoxid neutralZinc oxide neutralZinc OxideZinc oxides5,005.00BBWasser, destilliertWater, distilledWater (Aqua)Water (aqua)Ad 100Ad 100EDETA BDEDETA BDDisodium EDTADisodium EDTA0,100.10GlyceringlycerinGlyceringlycerin4,004.00PhenoxyethanolphenoxyethanolPhenoxyethanolphenoxyethanol0,700.70Solbrol MSolbrol MMethylparabenmethylparaben0,200.20Solbrol PSolbrol PPropylparabenPropylparaben0,100.10Magnesiumsulfatmagnesium sulfateMagnesium SulfateMagnesium sulphates0,500.50**CC**Parfümöl B2 aus Beispiel 10Perfume oil B2 from Example 10Parfum (Fragrance)Perfume (fragrance)0,300.30\ \ Herstellungsverfahren: Teil A auf ca. 85 °C erhitzen. Teil B (ohne Zinkoxid) auf ca. 85 °C erhitzen; Zinkoxid mit dem Ultra Turrax eindispergieren. B zu A geben. Unter Rühren abkühlen lassen. Teil C zugeben und anschließend homogenisieren.Method of preparation: Heat part A to approx. 85 ° C. Heat part B (without zinc oxide) to about 85 ° C; Zinc oxide with the Ultra Turrax einispergieren. Give B to A. Allow to cool while stirring. Add Part C and then homogenize.\ \ **BEISPIEL 24EXAMPLE 24**Sonnenschutzmilch (W/O) (Mengenangaben als Gew.-%)Sunscreen milk (W / O) (amounts in% by weight)\ \ **Phasephase****Rohstofferaw materials****INCI BezeichnungINCI name****Anteilproportion of****AA**Dehymuls PGPHDehymuls PGPHPolyglyceryl-2 DipolyhydroxystearatePolyglyceryl-2 dipolyhydroxystearates3,003.00Bienenwachs 8100Beeswax 8100BeeswaxBeeswax1,001.00Monomuls 90-0-18Monomuls 90-0-18Glyceryl OleateGlyceryl Oleate1,001.00Zinkstearatezinc stearateZinc stearateZinc stearate1,001.00Cetiol SNCetiol SNCetearyl IsononanoateCetearyl Isononanoate5,005.00Cetiol ÖCetiol ÖDicaprylyl EtherDicaprylyl ether5,005.00Tegosoft TNTegosoft TNC12-15 Alkyl BenzoateC12-15 alkyl benzoates4,004.00Vitamin EVitamin ETocopheroltocopherol0,500.50Solbrol PSolbrol PPropylparabenPropylparaben0,100.10Neo Heliopan(R) OSNeo Heliopan (R) OSEthylhexyl SalicylateEthyl hexyl salicylates5,005.00Neo Heliopan(R) AVNeo Heliopan (R) AVEthylhexyl MethoxycinnamateEthylhexyl methoxycinnamate7,507.50Uvinul(R) T150Uvinul (R) T150Ethylhexyl TriazoneEthylhexyl triazone1,501.50**BB**Wasser, destilliertWater, distilledWater (Aqua)Water (aqua)Ad 100Ad 100Trilon BDTrilon BDDisodium EDTADisodium EDTA0,100.10GlyceringlycerinGlyceringlycerin5,005.00Solbrol MSolbrol MMethylparabenmethylparaben0,200.20PhenoxyethanolphenoxyethanolPhenoxyethanolphenoxyethanol0,700.70Neo Heliopan(R) AP 10 % ige Lösung, neutralisiert mit NaOHNeo Heliopan (R) AP 10% solution neutralized with NaOHDisodium Phenyl Dibenzimidazole TetrasulfonateDisodium phenyl dibenzimidazole tetrasulfonates15,0015.00**CC**Parfümöl G2 aus Beispiel 15Perfume oil G2 from Example 15Parfum (Fragrance)Perfume (fragrance)0,250.25Alpha BisabololAlpha bisabololBisabololbisabolol0,100.10\ \ Herstellungsverfahren: Teil A auf ca. 85 °C erhitzen. Teil B auf ca. 85 °C erhitzen. B zu A geben. Unter Rühren abkühlen lassen. Teil C zugeben und anschließend homogenisieren.Method of preparation: Heat part A to approx. 85 ° C. Heat part B to approx. 85 ° C. Give B to A. Allow to cool while stirring. Add Part C and then homogenize.\ \ **BEISPIEL 25AEXAMPLE 25A**Permanent-Haarfärbemittel Teil AHaarfärbungsbase (Mengenangaben als Gew.-%)Permanent Hair Dye Part AHair Dyeing Base (amount by weight%)\ \ **Rohstofferaw materials****Anteilproportion of**Natrium Myreth Sulfat (z. B. Texapon K14 S/K, Cognis)Sodium myreth sulfate (eg Texapon K14 S / K, Cognis)2,802.80Linoleamidopropyl PG-dimonium chlorid phosphat (Arlasilk Phospholipid EFA, Uniqema)Linoleamidopropyl PG-dimonium chloride phosphate (Arlasilk Phospholipid EFA, Uniqema)1,001.00Caprylyl- / Capryl glucosid (Plantacare 810 UP, Cognis)Caprylyl / capryl glucoside (Plantacare 810 UP, Cognis)2,002.00Natrium Laureth-6 Carboxylat (Akypo Soft 45 NV, Kao)Sodium Laureth-6 Carboxylate (Akypo Soft 45 NV, Kao)10,0010.00Cetearylalkoholcetearyl8,008.00Octyldodecanoloctyldodecanol1,001.00Ceteareth-12Ceteareth-120,500.50Ceteareth-20Ceteareth-200,500.50KOH, 50 % ig in WasserKOH, 50% in water0,700.70Toluol-2,5-diamine sulfat (oxidierende Farbstoff)Toluene-2,5-diamine sulfate (oxidizing dye)0,900.90Resorcinresorcinol0,200.20m-aminophenolm-aminophenol0,060.064-chlororesorcin4-chlororesorcin0,150.15Ascorbinsäureascorbic acid0,100.10Natriumsulfitsodium0,150.15Ammoniak, 25 % in WasserAmmonia, 25% in water6,006.00Etidronsäureetidronic0,200.20Polyquaternium-2 (Mirapol A15, Rhodia)Polyquaternium-2 (Mirapol A15, Rhodia)0,200.20Parfümöl G2 aus Beispiel 15Perfume oil G2 from Example 150,300.30Wasserwater65,2465.24\ \ **BEISPIEL 25AEXAMPLE 25A**Permanent-Haarfärbemittel Teil B - Entwickler (Mengenangaben als Gew.-%)Permanent Hair Dye Part B - Developer (by weight%)\ \ **Rohstoffe****Anteil**Ketostearylalkohol8.00Ceteareth-202.50Steartrimonium Chlorid (Dehyquart B, Cognis)1.002,6-dicarboxypyridin0.10Paraffinöl0.30Etidronsäure0.40Propylenglykol0.40Natriumbenzoat0.04Wasserstoffperoxid, 50 % in Wasser12.00KOH, 50 % in Water, zugegeben bis pH = 3.5q.s.WasserAd 100\ Anwendung: Die erfindungsgemäße Haarfärbungsbasis (Teil A) und der erfindungsgemäße Entwickler (Teil B) werden in einem Gewichtsverhältnis von 1:1 Verhältnis zusammen gerührt und auf die Haare aufgetragen.**raw materials****proportion of** cetostearyl 8:00 Ceteareth-20 2:50 Steartrimonium chloride (Dehyquart B, Cognis) 1:00 2,6-dicarboxypyridine 12:10 paraffin oil 12:30 etidronic 12:40 propylene glycol 12:40 sodium benzoate 12:04 Hydrogen peroxide, 50% in water 12:00 KOH, 50% in water, added until pH = 3.5 qs water Ad 100 Application: The hair coloring base (part A) according to the invention and the developer according to the invention (part B) are stirred together in a weight ratio of 1: 1 ratio and applied to the hair.\ \ **BEISPIEL 26EXAMPLE 26**Haarfärbungscreme für eine blonde Farbtönung (Mengenangaben als Gew.-%)Hair dyeing cream for a blonde tint (amounts in% by weight)\ \ **Phasephase****Materialmaterial****HerstellerManufacturer****INCI-NameINCI name****Anteilproportion of****AA**OxowaxOxowaxLCWLCWCethyl alcohol, Oleyl alcohol, Cetearyl alcohol, Stearic acidCethyl alcohol, oleyl alcohol, cetearyl alcohol, stearic acid21,0021,00Volpo CS 25Volpo CS 25CrodaCrodaCeteareth25Ceteareth254,004.00Berol 175175Brenntag EurochemBrenntag EurochemLaureth-8Laureth-810,0010.00Lanette(R) ELanette (R) ECognisCognisSodium Cetearyl SulfateSodium Cetearyl Sulfate1,001.00Covaquat 16Covaquat 16LCWLCWPolyquaternium-6Polyquaternium-64,004.00WasserwaterWater (Aqua)Water (aqua)49,3049,30**BB**Ammoniak (20 % in Wasser)Ammonia (20% in water)Merk EurolabMerk EurolabAmmoniaAmmonia10,2010.20**CC**Parfümöl G2Perfume oil G2SymriseSymriseParfumPerfume0,500.50\ \ Herstellungsverfahren: Teil A, B und C außer Covaquat 16 zusammen mischen und 20 Minuten bei 80 °C erhitzen. Nachdem das Produkt homogen ist, abkühlen lassen. Covaquat 16 bei 50 °C dazugeben. Wenn das Produkt anfängt zu verdicken die Rührung stoppen. Bei Raumtemperatur NH4OH dazugegeben und die Mischung bis zur Homogenisierung rühren.Method of preparation: Mix together parts A, B and C except Covaquat 16 and heat at 80 ° C for 20 minutes. After the product is homogeneous, allow to cool. Add Covaquat 16 at 50 ° C. When the product starts thickening stop the stirring. NH 4 OH is added at room temperature and the mixture is stirred until homogenization.\ \ **BEISPIEL 27EXAMPLE 27**Lufterfrischer Aerosolspray, aus Wasserbasis (w/o Alkohol) (Mengenangaben als Gew.-%)Air freshener aerosol spray, water-based (w / o alcohol) (amounts in% by weight)\ \ **Materialmaterial****HerstellerManufacturer****INCI-NameINCI name****Anteilproportion of**Imbentin C/125/030Imbentin C / 125/030SymriseSymriseC12-15 pareth-3C12-15 pareth-30,250.25Imbentin AG/100/080Imbentin AG / 100/080SymriseSymrisedeceth-8, Ziegler alcoholdeceth-8, Ziegler alcohol1,001.00Parfümöl H2 aus Beispiel 17Perfume oil H2 from Example 17SymriseSymriseParfumPerfume1,251.25Wasser, demineralisiertWater, demineralizedAquaAqua22,5022,50Treibgas 4,2 barPropellant gas 4.2 bar75,0075.00\ \ Herstellungsverfahren: Alle Rohstoffe in der angegebenen Reihenfolge zusammenmischen.Method of preparation: Mix all raw materials together in the order listed.\ \ **BEISPIEL 28EXAMPLE 28**Flüssiges Lufterfrischer Pumpspray (Mengenangaben als Gew.-%)Liquid air freshener pump spray (amounts in% by weight)\ \ **Meterialmeterial****HerstellerManufacturer****INCI-NameINCI name****Anteilproportion of**Wasser, demineralisiertWater, demineralizedAquaAqua90,7090,70Ethanol 96 %Ethanol 96%SymriseSymriseEthanolethanol4,004.00Empilan KCL 11/90Empilan KCL 11/90Stockmeierstock MeierAlcohol C12-15 11EOAlcohol C12-15 11EO3,003.00IsopropanolisopropanolSymriseSymrisePropan-2-olPropane-2-ol1,001.00Natriumhydrogencarbonat p.A..Sodium hydrogencarbonate p.A ..SymriseSymriseSodiumbicarbonatsodium bicarbonate0,200.20Parmetol A 26Parmetol A 26Hösch JuliusPanty JuliusMixture of 5-Chloro-2-methyl-2H-isothiazol-3-one and 2-Methyl-2 _H_-isothiazol-3-oneMixture of 5-Chloro-2-methyl-2H-isothiazol-3-one and 2-methyl-2 _H_ isothiazole-3-one0,100.10Parfümöl F2Perfume oil F2SymriseSymriseParfumPerfume1,001.00\ \ Herstellungsverfahren: Alle Rohstoffe in der angegebenen Reihenfolge zusammen mischen. pH-Wert anpassen.Method of preparation: Mix all raw materials together in the order listed. Adjust pH.\ \ **BEISPIEL 29EXAMPLE 29**Deodorierender Lufterfrischer Pumpe/Docht 5 % Duftstoff (Mengenangaben als Gew.-%)Deodorizing air freshener pump / wick 5% perfume (amount as wt%)\ \ **Phasephase****Materialmaterial****HerstellerManufacturer****INCI-NameINCI name****Anteilproportion of****AA**Wasser, demineralisiertWater, demineralizedAquaAqua67,3267.32Sequion 40 NA 32Sequion 40 NA 32Polygon ChemiePolygon chemistry1,251.25Triethanolamin pur CPure triethanolamine CSymriseSymriseTriethanolamineTriethanolamine0,300.30Rewoderm S 1333Rewoderm S 1333GoldschmidtGoldschmidtDiNa-Ricinoleamido MEA-SulfosuccinatDiNa-ricinoleamido MEA sulfosuccinate2,332.33Tego Sorb Conc. 50Tego Sorb Conc. 50EvonikEvonikAlcohol C12-14, ethoxylated (2-5 EO) + Zn-RicinoleatAlcohol C12-14, ethoxylated (2-5 EO) + Zn-ricinoleate0,500.50Ethanol 96 %Ethanol 96%SymriseSymriseEthanolethanol20,0020.00**BB**Parfümöl E2Perfume oil E2SymriseSymriseParfumPerfume5,005.00LösungsvermittlersolubilizersSymriseSymrise3,003.00**CC**Milchsäurelactic acidSymriseSymrisePropanoic acid, 2-hydroxypropionic acid, LactolPropanoic acid, 2-hydroxypropionic acid, lactol0,300.30\ \ Herstellungsverfahren: Materialien des Teils A in der angegebenen Reihenfolge zusammen mischen. Materialien des Teil B zusammen mischen. Wenn Teil A klar ist, Teil B dazugeben. Anschließend Teil C zugeben und rühren bis die Mischung homogen ist.Method of preparation: Mix together the materials of Part A in the order listed. Mix materials of part B together. If part A is clear, add part B. Then add part C and stir until the mixture is homogeneous.\ \ **BEISPIEL 30EXAMPLE 30**WC-Stein (Mengenangaben als Gew.-%)WC-Stein (quantities as wt .-%)\ \ **Phasephase****Materialmaterial****HerstellerManufacturer****INCI-NameINCI name****Anteilproportion of****AA**Imbentin C/125/200Imbentin C / 125/200Dr. W. KolbDr. W. KolbC12/15 pareth-20C12 / 15 pareth-204,004.00Rewomid C 212Rewomid C 212GoldschmidtGoldschmidtCocamide MEACocamide MEA6,006.00Marion ARLMarion ARLSasolSasolC10-13, ABS-Na, PulverC10-13, ABS-Na, powder42,0042,00**BB**Natriumsulfat pharm. (E514)Sodium sulfate pharm. (E514)SymriseSymriseSodium sulfateSodium sulfate42,0042,00Parfümöl F2Perfume oil F2SymriseSymriseParfumPerfume6,006.00\ \ Herstellungsverfahren: Teil A schmelzen lassen. Teil B dazu mischen mit Hilfe eines Mischkneters. Im Extruder bei 35-40 °C zu einem WC-Stein formen.Method of preparation: let part A melt. Mix part B with a mixing mixer. Form in the extruder at 35-40 ° C to a toilet block.\ \ **BEISPIEL 31EXAMPLE 31**Kerze (Mengenangaben als Gew.-%)Candle (quantities as wt .-%)\ \ **Materialmaterial****Anteilproportion of**Kerzenwachscandle wax95,0095,00Parfümöl D2Perfume oil D25,005.00\ \ Herstellungsverfahren: Das Kerzenwachs schmelzen lassen und rühren. Das Parfümöl dazugeben, gut rühren. In die gewünschte Form gießen.Method of production: Melt the candle wax and stir. Add the perfume oil, stir well. Pour into the desired shape.\ \ **BEISPIEL 32EXAMPLE 32**Synthese von 3-\[(4 _S_)-4-Isopropylcyclohexen-1-yl\]propanal (Ib)Synthesis of 3 - \[(4 _S)_ -4- Isopropylcyclohexen-1-yl\] propanal (Ib)\ \ \ \ \ \ Der Aldehyd 3-\[(4 _S_)-4-Isopropylcyclohexen-1-yl\]propanal (Formel (Ib) wie oben definiert) wird ausgehend von I-(-)-Limonen (79.5 % ee, Formel (Vlb) wie oben definiert) analog zu der Synthese von 3-\[(4 _R_)-4-Isopropylcyclohexen-1-yl\] propanal (la) (Beispiele 4 bis 8) hergestellt. Das Produkt wird mit einer Reinheit von 97 % und mit 78 % ee erhalten.The aldehyde 3 - \[(4 _S)_ -4-Isopropylcyclohexen-1-yl\] propanal (formula (Ib) as defined above) on the basis of I is - (-) - limonene ((79.5% ee, formula VIb) as defined above ) analogous to the synthesis of 3 - (\[(4 _R)_ -4-Isopropylcyclohexen-1-yl\] propanal (la) produced Examples 4 to 8). The product is obtained with a purity of 97% and with 78% ee.\ \ **BEISPIEL 33EXAMPLE 33**Substantivitätsubstantivity\ \ Der Substantivitätstest ist ein Test zur Bestimmung der sensorischen Haftung eines Stoffes auf Riechstreifen. Die zu untersuchenden Riechstoffe (Verbindung der Formel (la), Verbindung der Formel (Ib) und Lilial® als Benchmark) werden in Form einer 10 %igen Lösung in Triethylcitrat (TEC) jeweils auf einen codierten Riechstreifen getaucht und in definierten zeitlichen Abständen von 15 Prüfern bezüglich der Intensität beurteilt. Die 15 Probanden bewerten die Geruchsintensität auf einer Skala von 1 = geruchlos bis 9 = sehr stark. Die Ergebnisse (Geruchsintensität I in Abhängigkeit von der seit dem Eintauchen des Riechstreifen vergangenen Zeit t in Tagen d) sind in Figur 1 dargestellt.The substantivity test is a test for determining the sensory adhesion of a substance to smelling strips. The fragrances to be investigated (compound of the formula (Ia), compound of the formula (Ib) and Lilial® as benchmark) are in the form of a 10% solution in triethyl citrate (TEC) immersed in each case on a coded smelling strip and at defined time intervals of 15 Examiners assessed the intensity. The 15 subjects rated the odor intensity on a scale from 1 = odorless to 9 = very strong. The results (odor intensity I as a function of the time t since the immersion of the scent strip in days d) are in FIG. 1 shown.\ \ Die Geruchsintensität wird in folgenden zeitlichen Abständen nach dem Eintauchen der Riechstreifen bewertet: 1 Stunde oder weniger (in Figur 1 als Zeitpunkt "0 Tage" bezeichnet); 1 Tag; 2 Tage; 3 Tage; 4 Tage; 7 Tage; 8 Tage; 9 Tage. Um sicherzustellen, dass die Probanden nicht beeinflusst werden, sind die codierten Riechstreifen nicht in einer chronologischen Reihenfolge auf dem Riechstreifenständer angeordnet.The odor intensity is evaluated at the following intervals after immersion of the smelling strips: 1 hour or less (in FIG. 1 as time "0 days"); 1 day; 2 days; 3 days; 4 days; 7 days; 8 days; 9 days. To ensure that the subjects are not affected, the coded smelling strips are not arranged in a chronological order on the smelling strip stand.\ \ Die Geruchsintensität der Verbindung der Formel (la) (schwarz ausgefüllter Balken) wird im frischen Zustand und über einen Zeitraum bis zu 3 Tagen von den Probanden im Vergleich zu Lilial® (schwarz schraffierter Balken) als stärker, und nach 4 bis 7 Tagen zumindest vergleichbar mit Lilial® eingeschätzt. Nach 9 Tagen wird sogar erneut eine im Vergleich zu Lilial(R) höhere Geruchsintensität der Verbindung der Formel (la) beobachtet.The odor intensity of the compound of formula (Ia) (solid black bar) when fresh and over a period of up to 3 days from subjects compared to Lilial® (black hatched bar) is at least comparable, and after 4 to 7 days at least rated with Lilial®. After 9 days even a higher odor intensity of the compound of the formula (Ia) is observed again compared with Lilial (R).\ \ Auch die Geruchsintensität der Verbindung (Ib) (schwarz gepunkteter Balken) ist im frischen Zustand stärker als die von Lilial® (schwarz schraffierter Balken) und nach einem Tag vergleichbar mit Lilial®. Danach nimmt die Geruchsintensität der Verbindung der Formel (Ib) zunächst stärker ab als bei Lilial® und der Verbindung der Formel (la), nach 7 bis 9 Tagen sind die Werte jedoch vergleichbar oder leicht höher als bei Lilial®.The odor intensity of the compound (Ib) (black dotted bars) in the fresh state is stronger than that of Lilial® (black hatched bar) and after one day comparable to Lilial®. Thereafter, the odor intensity of the compound of formula (Ib) initially decreases more than in Lilial® and the compound of formula (Ia), but after 7 to 9 days, the values are comparable or slightly higher than in Lilial®.\ \ ### Claims (17) Hide Dependent translated from\ \ 01. Compound selected from formula (Ia)\ \ \ \ \ 02. Mixture, comprising or consisting of\ \ \ (i) a compound of formula (Ia)\ \ \ \ \ \ \ \ \ (ii) a compound of formula (Ib)\ \ \ \ \ 03. Mixture of claim 2, **characterized in that**,\ \ \ (a) 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, preferably in the range from 0.1 to 99.9, preferably in the range from 0.5 to 99.5, preferably in the range from 1.0 to 99.0, preferably in the range from 1.5 to 98.5, preferably in the range from 2.0 to 98.0 and/or\ \ \ \ (b) the total amount of the compounds of formula (Ia) and (Ib) is greater than 0.01 w.t.%, preferably greater than 1 w.t.%, preferably greater than 10 w.t.%, more preferably greater than 50 w.t.%, most preferred greater than 90 w.t.%, relative to the total weight of the mixture comprising compounds (Ia) and/or (Ib).\ \ 04. Use of a compound of formula (Ia) as defined in claim 1 or a mixture consisting of the compound of formula (Ia) as defined in claim 1 and the compound of formula (Ib) as defined in claim 2\ \ \ (i) as fragrance, in particular as lily of the valley fragrance and/or\ \ \ \ (ii) as an agent for increasing the substantivity and/or the retention of a fragrance preparation; and/or\ \ \ \ (iii) as fixative.\ \ 05. The use of claim 4, wherein\ \ \ (a) the compound of formula (Ia) as defined in claim 1 is used for mediating, modifying or intensifying an odor note of lily of the valley and optionally one, several or all odor notes selected from the group consisting of floral, sweet, watery, powdery and ozone-like; and/or\ \ \ \ (b) the compound of formula (Ia) as defined in claim 1 is used for mediating, modifying or intensifying an odor note of lily of the valley and optionally one, several or all odor notes selected from the group consisting of fruity, green, watery and aldehyde-like.\ \ 06. A fragrance preparation, in particular perfume oil, preferably with an odor note of lily of the valley, consisting of or comprising\ \ \ (i) compound of formula (Ia) as defined in claim 1 or a mixture consisting of the compound of formula (Ia) as defined in claim 1 and the compound of formula (Ib) as defined in claim 2, and\ \ \ \ (ii) one, 2, 3, 4, 5, 6, 7, 8, 9, 10 or more further fragrances, which are not the compound of formula (I)\ \ \ \ \ 07. A fragrance preparation, in particular a perfume oil of claim 6, **characterized in that**, the amount of the formula (Ia) as defined in claim 1 and/or the compound of formula (Ib) as defined in claim 2, is in the range from 0,0001 to 40 w.t.%. preferably in the range from 0,001 to 25 w.t.%, each based on the total weight of the fragrance preparation.\ \ 08. A fragrance preparation, in particular a perfume oil according to any of claims 6 or 7, comprising one, 2, 3 or more further fragrances with an odor note of lily of the valley and optionally one, several or all odor notes selected from the group consisting of floral, sweet, watery, ozone-like, woody, ambered, musky, fruity, animal.\ \ 09. A fragrance preparation, in particular a perfume oil according to any of claim 6 to 8,\ \ \ (i) the amount of compound of formula (Ia) is sufficient to mediate an odor note of lily of the valley and optionally one, several or all odor notes mediate notes selected from the group consisting of floral, sweet, watery, powdery and ozone-like to the fragrance preparation, and/or\ \ \ \ (ii) one, several or all further fragrances of the fragrance preparation mediate an odor note of lily of the valley and optionally one, several or all odor notes mediate notes selected from the group consisting of floral, sweet, watery, powdery and ozone-like and the amount of the compound of formula (Ia) is sufficient in comparison to an identical composed comparison fragrance preparation without the compound of formula (Ia) to modify and/or intensify the odor note of lily of the valley and optionally one, several or all odor notes selected from the group consisting of floral, sweet, watery, powdery and ozone-like, and/or\ \ \ \ (iii) the amount of compound of formula (Ia) is sufficient to mediate an odor note of lily of the valley and optionally one, several or all odor notes mediate notes selected from the group consisting of fruity, green, watery and aldehyde-like to the fragrance preparation, and/or\ \ \ \ (iv) one, several or all further fragrances of the fragrance preparation mediate an odor note of lily of the valley and optionally one, several or all odor notes mediate notes selected from the group consisting of fruity, green, watery and aldehyde-like and the amount of the compound of formula (Ib) is sufficient in comparison to an identical composed comparison fragrance preparation without the compound of formula (Ib) to modify and/or intensify the odor note of lily of the valley and optionally one, several or all odor notes selected from the group consisting of fruity, green, watery and aldehyde-like.\ \ 10. Perfumed product comprising compound of formula (Ia) as defined in claim 1 or a mixture consisting of the compound of formula (Ia) as defined in claim 1 and the compound of formula (Ib) as defined in claim 2, preferably in a sensory effective amount.\ \ 11. Perfumed product of claim 10, **characterized in that**, the amount of the formula (Ia) as defined in claim 1 is in the range from 0,0001 to 5 w.t.%. preferably in the range from 0,001 to 2,5 w.t.%, each based on the total weight of the product.\ \ 12. Perfumed product of claims 10 or 11, selected from the group consisting of washing and cleaning products, hygiene or care products, in particular from the area of body and hair care, cosmetics and household products, fine fragrance (perfume), air care (especially candles), air fresheners.\ \ 13. Method of providing skin, hair, surfaces, or textile fibers with an odor note of lily of the valley comprising the following steps:\ \ \ (a) Providing a fragrance preparation, preferably according to any claims 6 to 9, comprising\ \ \ \ (b) compounds of the formula (Ia) as defined in claim 1 or a mixture consisting of the compound of formula (Ia) as defined in claim 1 and the compound of formula (Ib) as defined in claim 2, and\ \ \ \ (c) one or several further fragrances which are not compound of formula (Ia) or (Ib), wherein the amount of compound of formula (I) in the fragrance preparation is sufficient for mediating, modifying and/or intensifying an odor note of lily of the valley;\ \ \ \ (d) applying the fragrance preparation to the skin, hair, surfaces, or textile fibers.\ \ 14. Method for producing the compound of formula (I) as defined in claim 4, comprising the step of acid catalyzed reaction of an acetal of formula (II), so that the compound of formula (I) is formed\ \ \ \ \ \ wherein the group R in the acetal of formula (IIa) is a branched or unbranched, saturated or unsaturated alkyl group with 1 to 10 carbon atoms, preferably a butyl group.\ \ 15. Acetal of formula (II)\ \ \ \ \ \ wherein the group R in the acetal of formula (IIa) is a branched or unbranched, saturated or unsaturated alkyl group with 1 to 10 carbon atoms, preferably a butyl group.\ \ 16. Use of\ \ \ (i) d-(+) limonene as educt for producing the compound of formula (I) as defined in claim 1, or\ \ \ \ (ii) a mixture containing d-(+) limonene and 1-(-) limonene as educt for producing a mixture containing the compound of formula (Ia) as defined in claim 1 and the compound of formula (Ib) as defined in claim 2.\ \ 17. Method for mediating, intensifying and/or modifying an odor note of lily of the valley and optionally one, several or all odor notes selected from the group consisting of floral, sweet, watery, powdery and ozone-like, comprising the following steps: mixing or bringing in contact of the compound of formula (Ia) as defined in claim 1 or a mixture according toany claims 2 or 3, or a fragrance preparation of any claims 6 to 9, preferably in a sensory effective amount with a product.


Previous attempts to overcome these problems have been through the use of various “fixatives” or “modulators” to retard the evaporation of the more volatile fragrance ingredients present in fragrance compositions. For instance, U.S. Pat. No. 4,313,855 (Dragoco) describes the use in cosmetic compositions of 1-(2,6,6-trimethylcyclohexyl)-hexane-3-ol as an odourless fixative for increasing the perfume's intensity. U.S. Pat. No. 6,147,049 (Givaudan) discloses a perfume fixative derived from tera-hydronaphthalenese for use in a wide range of fragrance compositions. U.S. Pat. No. 6,440,400B1 (Takasago Perfumery) describes a composition using trimethylcyclohexane derivatives as perfuming-holding agents and melanin-formation inhibitors. U.S. Pat. No. 6,737,396B2 (Firmenich) describes a perfume composition formed by mixing 2-30%, relative to the weight of the composition, of a fixative, (1-ethoxyethoxy)cyclododecane, to fix or exalt the musky or aromatic-type notes. U.S. Pat. No. 7,538,081 (Takasago Perfumery) approaches the same problem of fixing a perfume and/or extending the perfume release from a fragrance composition. More particularly, said document describes the use of L-menthoxy ether derivatives as fixatives in fragrance compositions comprising at least one note selected from: floral, citrus, fruity, green, mint, herb and marine. JP Patent No. 61-083114 (Kanebo) describes ether derivatives as aroma-preserving agent for fine perfume composition. JP Patent No. 61-063612 (Kanebo) discloses diethylene glycol ether derivatives as fragrance adjusting agent showing effects as a fixative and a solubilizer. JP Patent No. 62-084010 (Shiseido) describes hydroquinone glycoside as perfume fixatives applicable for all kinds of perfume and blended perfume. On the other hand, PCT Publication No. WO85/04803 (Diagnostica) describes the use of hyaluronic acid/hyaluronate as fixatives (via molecular encapsulation) in fragrance products to improve persistence of the fragrance.


The inventors have surprisingly discovered a revolutionary new way of objectively classifying fragrance materials and then formulating those fragrance materials into complex fragrance mixtures having improved fragrance profile fidelity and longevity. Essentially, the solution is to formulate the fragrance materials having low levels (10 to 30 wt % relative to the total weight of the fragrance component) of the low volatile fragrance materials in the presence of a substantially non-odorous fragrance modulator to provide for improved or enhanced longevity and/or fidelity of the fragrance profile, particularly amongst characters attributable to volatile fragrance materials. In fact, the inventors have discovered that in the complete absence of the low volatile fragrance materials or at very low levels of the low volatile fragrance materials (less than 10 wt % relative to the total weight of the fragrance component), there is insufficient character complexity and roundness of the fragrance profile for consumer acceptance of the composition. Therefore the level of low volatile fragrance materials needs to be carefully chosen between 10 and 30 wt % to balance consumer acceptance and the desired improved or enhanced longevity and/or fidelity of the fragrance profile, particularly amongst characters attributable to volatile fragrance materials.


At the testing facility, 50 μL samples of the compositions and the controls are applied to glass slides and placed on a hot plate at 32° C. to represent skin temperature for varying durations. It is important that glass slides of samples that are to be later compared are prepared at the same time. The panelists are asked to evaluate the perceived fragrance profile (intensity and/or character) of each glass slide sample at a given time point. Slides are presented coded so that their identity is not known by the panelists. Within a given time point panelists evaluate the slides in a random order and are able to revisit their assessment as they work through the slides at that time point. Their assessments are recorded. In the subsequent analysis, the data for strength and character comparisons are drawn from the independent assessments carried out at a given time point. Only when using the character difference scale below are any 2 products physically directly compared to each other. Panelists are selected from individuals who are either trained to evaluate fragrances according to the scales below or who have experience with fragrance evaluation in the industry. Typically, around 6 to 10 panellists are used to evaluate a given product and its control.


The panelists are asked to give a score on a scale of 0 to 5 for perceived fragrance intensity according to the odour intensity scale set out in Table 4 herein below.


1 hr; 2 hrs; 3 hrs; 4 hrs; 5 hrs; 6 hrs; 50/30

- 1\. The test and control compositions as described in the Example section are used for the evaluation. - 2\. Capillaries of about 2 cm to 3.5 cm, with one sealed end are cut from a Sigma Aldrich “Stuart™ melting point tube” product code Z673269, or equivalent. A suitable fixed volume chosen between 50 and 200 μL of the composition is pipetted into the well of a VWR Tissue Culture 96 F well plate, or equivalent. The sealed end of the glass capillary is dipped into the filled well and left for at least 15 secs to wet the surface of the glass. Care must be taken not to contact the glass capillary with the sides of the well by maintaining it straight and approximately in the center of the well. - 3\. The glass capillary is then removed from the well and inverted or transferred onto a stable surface or into a holder and allowed to evaporate at ambient conditions for a set period of time. A windshield may be used to reduce high air turbulence. - 4\. The glass capillary is then introduced into an empty 20 mL HS vial, which is immediately closed with a PTFE cap. The time at which this takes place is determined to be time T=initial (i.e., T=10 mins). - 5\. Multiple glass capillaries are prepared in the same way and left to evaporate at ambient temperature for pre-determined periods of time, such as for example 10, 15, 30 mins, 1 hr, 2 hrs, 3 hrs, 4 hrs, 5 hrs, and up to 6 hrs, before being introduced to the headspace vial and sealed. - 6\. The HS vial is then analysed on an Agilent GC system 6890 equipped with a Gerstel MPS 2 autosampler, or equivalent, capable of performing SPME injections. A SPME fiber assembly DVB/CAR/PDMS (50/30 μm, 1 cm length) is required. A GC column such as a DB-5MS, ZB-5MSi models, or equivalent phase, with a length of 30 m, an inner diameter of 0.25 mm and a film thickness of 1 μm is used. - 7\. The SPME HS parameters are set to the values indicated as follows:


FIG. 1 shows the fragrance intensity profile of Composition R as evaluated by 10 panelists, which comprises the substantially non-odorous fragrance modulator sucrose myristate and the single fragrance material, ethyl safranate. Addition of the substantially non-odorous fragrance modulator maintains the intensity of the fragrance material for up to 6 hours whilst the control, Composition S, in the absence of the substantially non-odorous fragrance modulator, drops in fragrance intensity profile over the 6 hours. The substantially non-odorous fragrance modulator acts to maintain the continued evaporation over time of the fragrance material. Statistical analysis using the Tukey correction for multiple comparisons confirms the statistically significant difference at 0 hours (p=0.0015), 1 hour (p=0.0033), 3 hours (p=0.0015) and 6 hours ((p=0.0152) all at 95% significance level (i.e., p<0.05).


FIG. 2 shows the fragrance intensity profile of Composition P as evaluated by 10 panellists, which comprises the substantially non-odorous fragrance modulator sucrose myristate and the single fragrance material, Dimethylbenzyl carbinol. Addition of the substantially non-odorous fragrance modulator maintains the intensity of the fragrance material for up to 6 hours whilst the control, Composition Q, in the absence of the substantially non-odorous fragrance modulator, drops in fragrance intensity profile over the 6 hours. The substantially non-odorous fragrance modulator acts to maintain the continued evaporation over time of the fragrance material. Statistical analysis using the Tukey correction for multiple comparisons confirms the statistically significant difference at 1 hour (p=0.0581) at 90% significance level (i.e., p<0.1), 3 hours (p=0.0311) at 95% significance level (i.e., p<0.05).


FIG. 3 shows the fragrance intensity profile of Composition T as evaluated by 10 panelists, which comprises the substantially non-odorous fragrance modulator sucrose myristate and the single fragrance material phenethyl alcohol (PEA). Addition of the substantially non-odorous fragrance modulator maintains the intensity of the fragrance material for up to 6 hours whilst the control, Composition U, in the absence of the substantially non-odorous fragrance modulator, drops in fragrance intensity profile over the 6 hours. The substantially non-odorous fragrance modulator acts to maintain the continued evaporation over time of the fragrance material. Statistical analysis using the Tukey correction for multiple comparisons confirms the statistically significant difference at 1 hour (p<0.0001), 3 hours (p=0.0016) and 6 hours (p=0.0003) all at 95% significance level (i.e., p<0.05).


FIG. 4 shows the fragrance intensity profile of Composition ZZ as evaluated by 11 panelists, which comprises the substantially non-odorous fragrance modulator hydroquinone beta-D-glycoside and the single fragrance material, eugenol. Addition of the substantially non-odorous modulator maintains the intensity of the fragrance material for up to 6 hours whilst the control, Composition ZZZ, in the absence of the substantially non-odorous fragrance modulator, drops in fragrance intensity profile over the 6 hours. The substantially non-odorous fragrance modulator acts to maintain the continued evaporation over time of the fragrance material. Statistical analysis using the Tukey correction for multiple comparisons confirms the statistically significant difference at 1 hour (p=0.0008) and 3 hours (p=0.0123) all at 95% significance level (i.e., p<0.05).


(b) Effects of the Substantially Non-Odorous Fragrance Modulators on the Fragrance Profile Longevity of Compositions Having Reduced Levels of Low Volatile Fragrance Materials (Between 10 to 30 wt % Relative to the Total Weight of the Fragrance Component) Vs. Compositions Having Traditional Levels of Low Volatile Fragrance Materials (Greater than 30 wt Relative to the Total Weight of the Fragrance Component) and No Substantially Non-Odorous Fragrance Modulator


- a.) Matrix Systems: The fragrance is dissolved or dispersed in a polymer matrix or particle. Perfumes, for example, may be 1) dispersed into the polymer prior to formulating into the product or 2) added separately from the polymer during or after formulation of the product. Diffusion of perfume from the polymer is a common trigger that allows or increases the rate of perfume release from a polymeric matrix system that is deposited or applied to the desired surface (situs), although many other triggers are know that may control perfume release. Absorption and/or adsorption into or onto polymeric particles, films, solutions, and the like are aspects of this technology. Nano- or micro-particles composed of organic materials (e.g., latexes) are examples. Suitable particles include a wide range of materials including, but not limited to polyacetal, polyacrylate, polyacrylic, polyacrylonitrile, polyamide, polyaryletherketone, polybutadiene, polybutylene, polybutylene terephthalate, polychloroprene, poly ethylene, polyethylene terephthalate, polycyclohexylene dimethylene terephthalate, polycarbonate, polychloroprene, polyhydroxyalkanoate, polyketone, polyester, polyethylene, polyetherimide, polyethersulfone, polyethylenechlorinates, polyimide, polyisoprene, polylactic acid, polymethylpentene, polyphenylene oxide, polyphenylene sulfide, polyphthalamide, polypropylene, polystyrene, polysulfone, polyvinyl acetate, polyvinyl chloride, as well as polymers or copolymers based on acrylonitrile-butadiene, cellulose acetate, ethylene-vinyl acetate, ethylene vinyl alcohol, styrene-butadiene, vinyl acetate-ethylene, and mixtures thereof. - “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 polysaccharides 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 Application 2004/0110648 A1 and U.S. Pat. No. 6,531,444. - Silicones are also examples of polymers that may be used as PDT, and can provide perfume benefits in a manner similar to the polymer-assisted delivery “matrix system”. Such a PDT is referred to as silicone-assisted delivery (SAD). One may pre-load silicones with perfume, or use them as an equilibrium system as described for PAD. Suitable silicones as well as making same may be found in USPA 20050143282A1. Functionalized silicones may also be used as described in USPA 2006/003913 A1. Examples of silicones include polydimethylsiloxane and polyalkyldimethylsiloxanes. Other examples include those with amine functionality, which may be used to provide benefits associated with amine-assisted delivery (AAD) and/or polymer-assisted delivery (PAD) and/or amine-reaction products (ARP). Other such examples may be found in USPA 2005/0003980 A1. - b.) Reservoir Systems: Reservoir systems are also known as a core-shell type technology, or one in which the fragrance is surrounded by a perfume release controlling membrane, which may serve as a protective shell. The material inside the microcapsule is referred to as the core, internal phase, or fill, whereas the wall is sometimes called a shell, coating, or membrane. Microparticles or pressure sensitive capsules or microcapsules are examples of this technology. Microcapsules of the current invention are formed by a variety of procedures that include, but are not limited to, coating, extrusion, spray-drying, interfacial, in-situ and matrix polymerization. The possible shell materials vary widely in their stability toward water. Among the most stable are polyoxymethyleneurea (PMU)-based materials, which may hold certain PRMs for even long periods of time in aqueous solution (or product). Such systems include but are not limited to urea-formaldehyde and/or melamine-formaldehyde. Gelatin-based microcapsules may be prepared so that they dissolve quickly or slowly in water, depending for example on the degree of cross-linking. Many other capsule wall materials are available and vary in the degree of perfume diffusion stability observed. Without wishing to be bound by theory, the rate of release of perfume from a capsule, for example, once deposited on a surface is typically in reverse order of in-product perfume diffusion stability. As such, urea-formaldehyde and melamine-formaldehyde microcapsules for example, typically require a release mechanism other than, or in addition to, diffusion for release, such as mechanical force (e.g., friction, pressure, shear stress) that serves to break the capsule and increase the rate of perfume (fragrance) release. Other triggers include melting, dissolution, hydrolysis or other chemical reaction, electromagnetic radiation, and the like. Suitable capsule wall materials include, in addition to aminoplasts, polyvinyl alcohol, polyvinyl pyrrolidone, polyethylene glycol, polysaccharides and modified polysaccharides, gel forming proteins, modified celluloses such as carboxymethylcelluloses and hydroxyethylcelluloses, polyacrylates, polyureas, polyurethanes and mixtures thereof. The capsules may be further coated with an additional coating that can improve the deposition and/or retention of the capsule on the desired surface. Suitable coating materials include a cationic polymer selected from the group consisting of selected from the group consisting of polysaccharides, cationically modified starch, cationically modified guar, polysiloxanes, poly diallyl dimethyl ammonium halides, copolymers of poly diallyl dimethyl ammonium chloride and vinyl pyrrolidone, acrylamides, imidazoles, imidazolinium halides, imidazolium halides, poly vinyl amine, copolymers of poly vinyl amine and N-vinyl formamide to the surface of the capsule to form a cationically coated polymer encapsulated material. Typical capsules have a diameter of 1 micron to 500 microns. The use of pre-loaded microcapsules requires the proper ratio of in-product stability and in-use and/or on-surface (on-situs) release, as well as proper selection of PRMs. Microcapsules that are based on urea-formaldehyde and/or melamine-formaldehyde are relatively stable, especially in near neutral aqueous-based solutions. These materials may require a friction trigger which may not be applicable to all product applications. Other microcapsule materials (e.g., gelatin) may be unstable in aqueous-based products and may even provide reduced benefit (versus free perfume control) when in-product aged.


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 (Schiffs 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. No. 7,018,978 B2.


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 (Schiffs 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. No. 7,018,978 B2.