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COMPOSITION COMPRISING FRAGRANCE ISO-PROPLYIDENE GLYCOL

20220378970 · 2022-12-01

    Inventors

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    International classification

    Abstract

    The present invention relates to a composition comprising at least one fragrance ingredient, one or more solvents and water, a method for obtaining such a composition in the form of a homogeneous composition, and to the use of such a composition to release a fragrance in an atmosphere in a controlled way.

    Claims

    1. A composition comprising at least one fragrance ingredient, (2,2-dimethyl-1,3-dioxolan-4-yl)methanol and water, wherein the maximum level of water in the composition is given by Equation 1:
    W(%)=(63±30)exp.sup.((−0.38±0.025)(ClogP))  (Equation 1) wherein (ClogP) is the weighted average ClogP of the at least one fragrance ingredient.

    2. The composition according to claim 1, comprising: a) from 5 to 40 wt.-% of at least one fragrance ingredient; b) from 20 to 90 wt.-% of (2,2-dimethyl-1,3-dioxolan-4-yl)methanol; and c) from 5 to 40 wt.-% of water.

    3. The composition according to claim 1, additionally comprising one or more compounds selected from the group consisting of: 2,2′-oxydi-1-propanol, 1,1′-oxydi-2-propanol, 2-(2-hydroxypropoxy)-1-propanol, triethyl 2-hydroxypropane-1,2,3-tricarboxylate and 1,2,3-triacetoxy propane.

    4. The composition according to claim 3, comprising: a) from 10 to 30 wt.-% of at least one fragrance ingredient; b) from 40 to 80 wt.-% of compounds selected from the group consisting of: (2,2-dimethyl-1,3-dioxolan-4-yl)methanol, 2,2′-oxydi-1-propanol, 1,1′-oxydi-2-propanol, 2-(2-hydroxypropoxy)-1-propanol isomers, triethyl 2-hydroxypropane-1,2,3-tricarboxylate and 1,2,3-triacetoxy propane; and c) from 10 to 35 wt.-% of water.

    5. The composition according to claim 1, comprising at least two fragrance ingredients.

    6. The composition according to claim 1, wherein the weighted average ClogP of the at least one fragrance ingredient or at least two fragrance ingredients, respectively, is 4 or less based on the total weight of the at least one fragrance ingredient present in the composition.

    7. The composition according to claim 1, wherein at least 70 wt.-% of the at least two fragrance ingredients or at least two fragrance ingredients, respectively, have a ClogP of 4 or less.

    8. The composition according to claim 1, wherein less than 30 wt.-% of the at least one fragrance ingredient or at least two fragrance ingredients, respectively, have a ClogP of 4 or more.

    9. The composition according to claim 1, further comprising at least one fragrance filler selected from the group consisting of: diethyl propanedioate, ethyl 3-oxobutanoate, benzyl alcohol, 2-phenylethanol, tetrahydro-4-methyl-2-(2-methylpropyl)-2H-pyran-4-ol, benzaldehyde, benzyl acetate, 3-methylbutyl acetate, 1-phenylethyl acetate, 2-(4-methylcyclohex-3-en-1-yl)propan-2-ol, 3aR,6S,7aS)-3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden-6-yl acetate, (2,6-dimethyloct-7-en-2-ol, -ethyl hexanoate, 3,7-dimethylocta-1,6-dien-3-ol); hexyl acetate, (E)-3,7-dimethylnona-1,6-dien-3-ol, 3,7-dimethyloct-6-en-3-ol, ethyl heptanoate, 2-(sec-butyl)cyclohexanone, 2,6-dimethyloct-7-en-2-ol, 3,7-dimethyloctan-3-ol, 2,6-dimethyloctan-2-ol, 7-isopropyl-8,8-dimethyl-6,10-dioxaspiro[4.5]decane, 3-(2-methylpropyl)-1-methylcyclohexanol, (2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl acetate.

    10. The composition according to claim 1, comprising at least one hydrosol selected from the group consisting of: blackcurrant, camphor, celery seed, chamomile, cinnamon, clove, copal, cypress, eucalyptus, fennel, ginger, helichyrsum, jambora, jasmine, juniper berries, lemongrass, lavender, lemon, lime, litsea cubeba, mint, myrrh, neroli, nutmeg, passion fruit, peppermint, pine needle, plum, rose geranium, Bulgarian rose, rosemary, sage, sandalwood, tea tree, vanilla, yuzu, and ylang ylang hydrosols.

    11. The composition according to claim 1, comprising less than 5 wt.-% of surfactants.

    12. A method of obtaining a homogeneous composition according to claim 1, the method comprising the steps of: a) providing a fragrance comprising at least one fragrance ingredient; b) admixing the fragrance provided in step (a) with (2,2-dimethyl-1,3-dioxolan-4-yl)methanol, and optionally one or more compounds selected from the group consisting of: 2,2′-oxydi-1-propanol, 1,1′-oxydi-2-propanol, 2-(2-hydroxypropoxy)-1-propanol, triethyl 2-hydroxypropane-1,2,3-tricarboxylate and 1,2,3-triacetoxy propane, and water, in such a way that the sum of the concentrations of the fragrance, the one or more solvents and the water is equal to 100 wt.-%, forming thereby a composition; c) determining whether the composition formed in step (b) is homogeneous or phase separated; d) locating the composition on a ternary diagram and labelling as homogeneous or phase separated; e) repeating steps (a) to (d) by varying the concentrations of the fragrance, with (2,2-dimethyl-1,3-dioxolan-4-yl)methanol, and optionally one or more compounds selected from the group consisting of 2,2′-oxydi-1-propanol, 1,1′-oxydi-2-propanol, 2-(2-hydroxypropoxy)-1-propanol, triethyl 2-hydroxypropane-1,2,3-tricarboxylate and 1,2,3-triacetoxy propane, and the water, until the realm of corresponding homogeneous compositions can be delimited in a ternary phase diagram; f) selecting a homogeneous composition within the realm determined in step e).

    13. A consumer product comprising the composition according to claim 1.

    14. The consumer product according to claim 13 wherein the consumer product is an air freshening product, an activated air freshening device, or a passive air freshening device, or a cartridge or refill for use in an active air freshener device or a passive air freshener device.

    15. The consumer product according to claim 14, wherein the activated air freshening device is an electrical plug-in air freshening device capable of providing the fragrance composition to the air.

    16. A method of releasing the composition of claim 1 in an atmosphere in a controlled way, from an activated air freshening device, or a passive air freshening device, an electrical plug-in air freshening device capable of providing the fragrance to the air.

    Description

    [0134] Further features and particular advantages of the present invention become apparent from the Figures and the following examples.

    [0135] It is shown in:

    [0136] FIG. 1: Distribution of ClogP values in fragrances A to H, used in the examples;

    [0137] FIG. 2: Ternary diagram corresponding to fragrance D (weighted average ClogP=2.04);

    [0138] FIG. 3: Ternary diagram corresponding to fragrance F (weighted average ClogP=3.04);

    [0139] FIG. 4: Ternary diagram corresponding to fragrance H (weighted average ClogP=3.56);

    [0140] FIG. 5: Evaporation curves of composition XIV at 65° C. and 80° C.;

    [0141] FIG. 6: Evaporation curves of compositions IX through XIII at 80° C.

    EXAMPLE 1: DETERMINATION OF OPTIMAL COMPOSITIONS

    [0142] In a first step, a series of fragrances were prepared by admixing fragrance ingredients. The weighted average ClogP of each fragrance was calculated using Equation 2. Forming 8 different fragrances, the weighted average ClogP was between 1.29 and 3.56 (Table 1).

    TABLE-US-00001 TABLE 1 Fragrances utilized in this example with their weighted average ClogP A B C D E F G H ClogP DIPROPYLENE GLYCOL 0.5 1.0 −0.7 ACETOACET ETHYLE 7.0 28.0 23.5 73.0 0.3 TRIETHYL CITRATE 0.9 0.8 7.0 2.0 1.2 ALC PHENYL ETHYLIQUE 2.4 3.4 5.9 5.0 6.0 1.3 FLOROSA HC 15.0 16.0 2.0 1.4 COUMARINE PURE CRIST 2.0 0.8 0.6 1.4 HYDROXYCITRONELLAL SYNT 1.5 1.5 ALC CINNAMIQUE SYNT 0.3 0.8 2.0 1.6 ALC PHENYL PROPYLIQUE 3.0 1.0 1.7 AUBEPINE PARA CRESOL 2.0 1.0 2.5 2.0 1.8 ETHYL VANILLINE 0.5 0.4 2.5 1.5 1.7 0.2 1.8 ACET BENZYLE 31.0 3.0 22.0 13.0 2.0 ALD CINNAMIQUE 0.7 2.0 2.3 2.0 METHYL-2-BUTYRATE ETHYLE 2.0 2.3 2.1 CARVONE LAEVO 1.5 3.0 2.2 CAMPHOR 1.0 1.0 8.0 2.2 GARDENOL 1.0 5.0 2.3 PHENYL ETHYL ACETATE 5.0 1.0 1.0 2.3 CYCLAL C 2.5 2.4 DECALACTONE GAMMA 1.5 2.4 MAGNOLAN 1.3 2.0 2.4 EUGENOL 2.1 0.9 0.3 0.3 2.4 MANZANATE 0.5 1.5 1.0 2.6 TERPINEOL ALPHA 1.0 0.5 2.0 1.0 2.6 LINALOOL 7.0 11.0 3.0 3.0 3.0 3.0 2.7 ACET HEXYLE 0.2 1.0 1.0 3.0 2.8 HEDIONE 0.8 2.5 4.6 2.3 0.8 11.0 12.6 10.3 2.9 JASMACYCLENE 1.0 1.5 7.0 2.0 4.0 2.9 PECHE PURE 0.1 2.0 1.0 2.0 4.0 2.0 2.9 CITRAL LEMAROME N 1.0 1.0 8.0 2.9 GERANIOL 5.0 4.0 1.0 4.0 2.0 1.0 3.0 CINNAMATE ETHYLE 1.0 1.0 3.0 BRASSYLATE ETHYLENE 6.0 2.0 7.7 7.0 3.0 DIHYDRO MYRCENOL 4.0 4.3 3.0 3.0 ETHYL LINALOL 11.1 6.0 2.5 5.2 3.3 CITRONELLOL 13.5 1.0 4.4 3.3 FLOROCYCLENE 5.0 3.4 OENANTHATE ETHYLE 1.0 1.5 4.0 3.4 TETRAHYDRO LINALOL 7.5 2.5 7.0 7.0 3.5 ACET LINALYLE SYNT 4.0 3.6 2.4 4.0 7.0 5.0 3.7 FLORHYDRAL 1.5 2.0 3.7 IONONE BETA 0.7 0.5 0.7 0.6 3.0 1.0 3.8 ISORALDEINE 70 2.0 2.4 2.0 3.5 1.8 3.3 4.0 AGRUMEX 0.5 3.0 11.0 5.0 3.2 4.1 SALICYLATE BENZYLE 1.2 2.6 2.0 0.6 5.7 3.0 4.2 CASHMERAN 2.0 4.6 4.2 ACET CITRONELLYLE 2.7 4.2 NYMPHEAL 3.7 4.3 SYLKOLIDE 1.3 2.0 0.3 3.9 4.4 TERPINENE GAMMA 1.4 3.8 4.4 ALD A AMYL CINNAMIQUE 1.0 0.8 10.0 10.0 4.5 SALICYLATE HEXENYLE-3-CIS 2.8 1.1 2.0 4.5 ISO E SUPER 4.8 0.6 2.7 5.0 4.9 SERENOLIDE 2.9 1.0 9.2 0.6 3.0 6.9 5.4 ACET P T BUTYL CYCLOHEXYLE 10.0 10.0 4.1 FRESKOMENTHE 2.3 2.8 Average ClogP 2.64 2.04 2.60 2.09 1.29 3.04 3.31 3.56

    [0143] The distribution of ClogP values within each fragrance is represented in Table 2, emphasizing the proportion of ingredients having ClogP values within pre-defined ranges.

    TABLE-US-00002 TABLE 2 Distribution of ClogP values within the fragrances of Table 1 ClogP A B C D E F G H <=0 0.50 0.00 1.00 0.00 0.00 0.00 0.00 0.00 0-1 7.00 28.00 0.00 23.50 73.00 0.00 0.00 0.00 1-2 35.40 23.70 47.30 25.50 6.50 0.80 13.70 8.80 2-3 14.80 13.30 24.10 31.90 0.80 59.80 25.90 22.60 3-4 30.80 27.60 5.30 4.60 2.00 26.50 27.20 25.20 4-5 11.50 4.50 21.30 14.50 8.50 12.30 30.20 36.50   >5 0.00 2.90 1.00 0.00 9.20 0.60 3.00 6.90 Total 100.00 100.00 100.00 100.00 100.00 100.00 100.00 100.00 Average ClogP 2.64 2.04 2.60 2.09 1.29 3.04 3.31 3.56

    [0144] The distributions of Table 2 are visualized graphically in FIG. 1. Both Table 2 and FIG. 1 show the diversity of the fragrances in terms of the ClogP ranges represented.

    [0145] In a second step, each fragrance was combined with isopropylidene glycerol and deionized water in variable proportions in such a way that the sum of the weight percentages was always 100%. A number of 9 to 12 different compositions were obtained in this way.

    [0146] In a third step, the locations of all compositions for each fragrance compositions were reported on a ternary phase diagram.

    [0147] As apparent from the diagrams of FIG. 2 to 4, increasing the weighted average ClogP of the fragrance, the realm of the diagram where the composition is homogeneous is shifted in the direction of low water and high isopropylidene glycerol concentrations. Concomitantly, the extension of this homogeneous realm decreases, confirming the decrease of affinity of the fragrance with the isopropylidene glycerol/water solvent system.

    [0148] FIG. 2 also shows the concentration coordinate of each of the three components (isopropylidene glycerol {IPG}, fragrance {FI} and water {W}) are read on such ternary diagram.

    EXAMPLE 2: EXAMPLES OF COMPOSITIONS ACCORDING TO THE INVENTION WITH ISOPROPYLIDENE GLYCEROL

    [0149] A series of homogeneous and water-clear compositions were prepared having the concentrations shown in Table 3.

    TABLE-US-00003 TABLE 3 Homogeneous and water-clear compositions according to the present invention with isopropylidene glycerol Fragrance Fragrance Isopropylidene (average ClogP) [%] glycerol [%] Water [%] 1 E (1.29) 30 45 25 II B (2.04) 30 50 20 III C (2.60) 10 50 40 (limit, see text) IV C (2.60) 10 55 35 V C (2.60) 20 60 20 VI F (3.07) 20 60 20 VII H (3.56) 20 60 20 VIII H (3.56) 10 25 65

    [0150] As apparent from Table 3, homogeneous and water-clear compositions may be obtained with up to 30 wt.-% fragrance ingredients or up to 35 wt.-% deionized water, depending on the weighted average ClogP of the fragrance. Sample III was slightly turbid and may be therefore considered as the limit of solubility of 10 wt.-% fragrance C in the isopropylidene/water solvent system at 40 wt.-% water.

    EXAMPLE 3: COMPOSITIONS ACCORDING TO THE INVENTION WITH ADDITIONAL SOLVENTS

    [0151] Table 4 show a series of homogeneous and water-clear compositions comprising isopropylidene glycerol and other solvents.

    TABLE-US-00004 TABLE 4 Homogeneous and water-clear compositions according to the present invention with solvent mixtures Fragrance Fragrance Water IPG DPG TEC TRI Fragrance (av. ClogP) [%] [%] [%] [%] [%] [%] IX C (2.60) 20 20 60 X C (2.04) 20 20 45 15 XI C (2.60) 20 20 40 10 10 XII C (2.60) 20 20 30 20 10 XIII C (2.60) 20 20 30 15 15 XIV F (3.04) 20 20 60 XV F (3.04) 20 20 45 15 XVI F (3.04) 20 20 40 10 10 XVII F (3.04) 20 20 30 20 10 IPG = isopropylidene glycerol ((2,2-dimethyl-1,3-dioxolan-4-yl)methanol); DPG = dipropylene glycol (2,2′-oxydi-1-propanol, 1,1′-oxydi-2-propanol, and 2-(2-hydroxypropoxy)-1-propanol isomer mixture); TEC = triethyl citrate (triethyl 2-hydroxypropane-1,2,3-tricarboxylate); TRI = triacetine (1,2,3-triacetoxypropane).

    EXAMPLE 4: EXAMPLES OF EVAPORATION CURVES

    [0152] 25 ml of composition XIV was transferred in the vessel of an electrical plug-in air freshener device having an operating temperature of 65° C. Another 25 ml portion of composition XIV was transferred in the vessel of another electrical plug-in air freshener device having an operating temperature of 80° C. Both devices were switched on and the evaporation process was quantified by monitoring the device weight loss as a function of time. The percentage of weight loss was calculated by applying Equation 6:


    F(t)=[w(t.sub.0)−w(t)]/w(t.sub.0)  (Equation 6),

    [0153] wherein w(t) is the weight at a given time t and w(t.sub.0) is the weight at the starting time t.sub.0.

    [0154] As Apparent from FIG. 5, the evaporation of composition XIV is too fast at 80° C. with respect to the desired device operational duration (at least 30 days), whereas it is optimal at 65° C. This composition is therefore well adapted to low temperature electrical plug-in devices.

    [0155] In FIGS. 5 and 6 {A} means “elapsed days” and {B} means weight loss in %

    [0156] The evaporation of composition IX, having same solvent composition as composition XIV is compared to the evaporation of compositions X though XIII in FIG. 6.

    [0157] As apparent from FIG. 6 replacing 15 or 20 wt.-% of isopropylidene glycerol with dipropylene glycol or dipropylene glycol and triacetin only slightly decreases the rate of evaporation of the composition. The introduction of triethyl citrate has a more pronounced impact in lowering the rate of evaporation. The optimal composition is found for composition XII. These results show that it is possible to optimize the evaporation of compositions comprising a fragrance and water by selecting solvents having a sustainable environmental profile.