ENCAPSULATED FRAGRANCE MIXTURES

Abstract

The invention relates to fragrance mixtures comprising at least one 60 wt.-% fragrance molecules which are characterized such that they are oriented along a virtual axis X, Y and Z, having a dimension of X>5 angstrom, Y>3 angstrom and angstrom.

Claims

1. A fragrance mixture comprising at least 60% by weight of fragrance molecules, wherein, when they are aligned along a virtual set of axes X, Y and Z, they have dimensions of X>5 angströms, Y>3 angströms and Z>2 angströms, with the proviso that the number of different fragrances in the mixture is at least 2.

2. The fragrance mixture as claimed in claim 1, wherein the odor threshold value (OTV) of the individual fragrance molecules in the mixture is less than 10 ppm.

3. The fragrance mixture as claimed in claim 1, wherein the number of different fragrances in the mixture is not more than 10.

4. The fragrance mixture as claimed in claim 1, wherein at least one of the fragrances is present in the mixture in a concentration of at least 10% by weight, preferably at most 60% by weight.

5. The fragrance mixture as claimed in claim 1, wherein at least one of the fragrances in the mixture has a sulfur or nitrogen atom, and is preferably a nitrile group.

6. The fragrance mixture as claimed in claim 1, wherein at least one of the fragrances in the mixture has a molar mass of greater than 120 g/mol.

7. The fragrance mixture as claimed in claim 1, wherein the fragrances in the mixture have a log K.sub.ow value of 1 to 10.

8. The fragrance mixture as claimed in claim 1, wherein at least 80% by weight of the fragrance molecules have dimensions of X>7 angströms, Y >4 angströms and Z>2 angströms.

9. The fragrance mixture as claimed in claim 1, wherein the fragrance mixture contains only very little solvent, if any.

10. A capsule comprising a fragrance mixture as claimed in claim 1.

11. The capsule as claimed in claim 10, wherein the capsule has an average diameter between 1 μm and 8 mm.

12. A consumer product comprising a fragrance mixture as claimed in claim 1.

13. The consumer product as claimed in claim 12, selected from the group consisting of washing and cleaning compositions, cosmetic products, perfume articles and cosmetic cleansers.

14. A consumer product comprising a capsule as claimed in claim 10.

15. The consumer product as claimed in claim 14, selected from the group consisting of washing and cleaning compositions, cosmetic products, perfume articles and cosmetic cleansers.

Description

EXAMPLES

Examples 1 TO 10, Comparative Examples C1 TO C3

Calculations of the Fragrance Molecules

[0060] The structures of individual fragrance molecules were subjected to force field energy minimization, taking account of the stereochemistry, provided that this is known with certainty, and aligned along a virtual set of axes for further calculation. Subsequently, a virtual box was created around the particular structures and the size of the box was recorded for further calculation (unit of measurement: angströms). Examples 1 to 10 are in accordance with the invention; examples C1 to C3 serve for comparison.

[0061] Software: from Schrödinger LLC [0062] Maestro Version 9.5.014 [0063] Module: MacroModel [0064] Force field: OPLS2005 [0065] Parameters: gas phase, constant dielectric

TABLE-US-00001 TABLE 1 Data for the fragrances calculated that are usable in accordance with the invention Dimensions [angstroms] OTV log Weight Ex. Compound Structure x y z ppm Kow mol/g 1 Rose oxide (FEMA 3236) [00002] 9.11 4.76 4.55 0.5 3.58 154.3 2 Aldehyde C16 (FEMA 2444) [00003] 8.07 7.16 4.82 0.2 3 206.2 3 Agrunitrile (citronellylnitrile, CAS 51566-62-2) [00004] 10.56 4.01 3.43 1 3.55 151.3 4 Methyl octyne carbonate (CAS 111-80-8) [00005] 12.04 6.29 2.24 0.2 3.1 168.2 5 Bucco leaf oil [00006] 7.67 5.64 4.64 0.2 6 Pre-cyclemone B (CAS 52474-60-9) [00007] 11.58 4.87 4.40 0.5 5.19 206.3 7 Allyl amyl glycolate (CAS 67634-00-8) [00008] 11.72 5.24 4.56 0.1 2.34 186.3 8 Thiocineol (FEMA 4108) [00009] 7.02 5.29 4.93 <0.01 3.95 170.3 9 2-Isobutyl-3- methoxypyrazine (FEMA 3132) [00010] 7.50 6.99 4.47 0.1 2.86 166.2 10  cis-4-Decenal (FEMA 3264) [00011] 11.50 5.83 3.50 0.2 3.55 154.3 C1 Aldehyde C-7 (FEMA 2540) [00012] 9.64 2.59 1.73 114.2 C2 Ethyl butyrate (FEMA 2427) [00013] 9.20 2.93 1.76 116.2 C3 Diphenyl oxide (CAS 32576-61-7) [00014] 10.08 4.81 0.0 170.2

Use Examples 1: Fragrance Mixtures I TO V

[0066] The suitable fragrances from table 1 were mixed in different formulations to give fragrance mixtures I to V and then encapsulated.

[0067] Production of the Capsules

[0068] A cylindrical 1 L stirred vessel with an installed stirrer unit (dissolver) was initially charged, while stirring gently, with 200 g of water, 35 g of a 20% by weight aqueous solution of a protective colloid, 40.5 g of a 70% by weight aqueous solution of the melamine-formaldehyde resin mixture (e.g. Luracoll SD from BASF).

Then the stirrer speed of the dissolver was increased to such an extent that good mixing was achieved. Still while mixing, 200 g of fragrance oil mixture to be encapsulated were then added gradually. The mixture was adjusted to 30-40° C. and the dissolver speed was set to 1200 rpm. Subsequently, X g of 10% by weight formic acid were added and the dissolver speed was reduced to 1000 rpm. After about 20 min, capsules formed. As soon as the desired capsule size had been attained, the speed of rotation of the dissolver was lowered to 1000 rpm and the capsule dispersion was stirred at 30-40° C. and 1000 rpm for half an hour.
The results are compiled in table 2.

TABLE-US-00002 TABLE 2 Inventive fragrance mixtures I to V Fragrance mixtures Compound I II III IV V Rose oxide 50 50 50 50 100 Aldehyde C16 — — — 450 — Agrunitrile 200 195 195 20 200 Diphenyl oxide — — — — 2 Bucco leaf oil — — — 2 — Precyclemone B 300 280 290.5 — 260 Allyl amyl glycolate 400 380 392 450 400 Thiocineol — 40 20 60 2-Isobutyl-3- — 5 2.5 — 8 methoxypyrazine cis-4-Decenal 50 50 50 18 30 Total amount 1000 1000 1000 1000 1000

Use Example 2

[0069] Stability Test of the Encapsulated Fragrance Mixtures I to V

[0070] The resultant capsule dispersions were extracted with acetone to determine the free (unencapsulated) oil content, and the concentration of the fragrance mixtures in the extract obtained was determined.

[0071] To determine the total oil content, the resultant capsule dispersions were exhaustively extracted with a suitable solvent (e.g. ethanol, acetone). This extract was made up to a known volume and the content of the fragrance mixture was determined.

The results are compiled in table 3.

TABLE-US-00003 TABLE 3 Determination of the capsule quality (all figures in % by weight) Total content of average amount of Capsules with Free oil, Oil, fragrance in a fragrance mixture unencapsulated* total amount capsule I 0.00 0.0 33.0 II 0.02 0.86 27.9 III 0.00 0.14 31.7 IV 0.00 0.16 34.5 V 0.00 0.00 33.7

Use Example 3

Stability Test in Fabric Softeners

[0072] A commercial perfume-free fabric softener formulation having an ester quat content of about 15% was admixed with 0.5 g of the encapsulated fragrance mixtures I to V and stored at 40° C. After a storage time of 1, 4, 8 and 12 weeks, the content of the odorants that had diffused into the bulk was determined with the aid of headspace measurements in the air phase above. The results are compiled in table 4. What is reported is the percentage of the oil still remaining in the capsule.

TABLE-US-00004 TABLE 4 Stability test (figures in % in relation to the starting formulation) Capsules with Stability of the capsules fragrance in the fabric softener at 40° C. mixture 1 week 4 weeks 8 weeks 12 weeks I 100 97 74 35 II 89 82 58 24 III 99 91 55 25 IV 100 97 69 47 V 100 94 57 11

Use Example 4

Impact of the Capsules Comprising Fragrance Mixtures I to V

[0073] A commercial perfume-free fabric softener formulation of the Vernell® type was admixed with 0.01% by weight of the encapsulated fragrance mixtures Ito V. Subsequently, about 20 g of this mixture were washed onto 2 kg of terrycloth towels in a standard European domestic washing machine. After the spin cycle, the towels were removed and dried. Subsequently, the towels were rubbed repeatedly by a panel consisting of 4 experienced testers and the intensity of the olfactory evolution (“impact”) was assessed on a scale from 1 (weak) to 10 (very strong). The results are compiled in table 5. What are reported are the mean values from 3 successive test series.

TABLE-US-00005 TABLE 5 Impact Capsules with fragrance Odor intensity mixture Tester 1 Tester 2 Tester 3 Tester 4 I 8 7 7 8 II 7 6 7 7 III 8 8 7 5 IV 8 9 8 8 V 8 9 7 7

Formulation Examples

[0074]

TABLE-US-00006 TABLE 6 Bar soaps Composition A1 A2 A3 Sodium C12/14 Olefin Sulfonate 40.0 — — Disodium Lauryl Sulfosuccinate — 40.0 — Lauryl Glucoside 15.0 15.0 55.0 Cetylstearyl Alcohol 12.0 12.0 12.0 Paraffin Oil (m.p. 54 to 56° C.) 8.0 8.0 8.0 Maize Starch, degraded 8.0 8.0 8.0 Palmitic Acid (and) Stearic Acid 5.5 5.5 5.5 Glyceryl Stearate 2.0 2.0 2.0 Coco Glyceride 2.0 2.0 2.0 Polyquaternium-7 1.0 1.0 1.0 Perfume oil 1.0 1.0 1.0 Titanium dioxide 0.5 0.5 0.5 Capsules with fragrance mixture I 0.5 0.5 0.5 Water ad 100

TABLE-US-00007 TABLE 7 Syndet soaps Composition B1 B2 B3 Lauryl Glucoside 15.0 15.0 15.0 Sodium C12/14 Olefin Sulfonate 40.0 40.0 — Sodium Lauryl Sulfate — — 40.0 Paraffin Oil (m.p. 54° C.) 8.0 8.0 8.0 Tallow Fatty Alcohol 7.0 7.0 7.0 Maize starch 17.0 — 17.0 Dextrose — 17.0 — Coco Fatty Acids 10.0 10.0 10.0 Titanium dioxide 1.0 1.0 1.0 Capsules with fragrance mixture II 0.5 — 0.5 Capsules with fragrance mixture III — 0.5 — Water ad 100

TABLE-US-00008 TABLE 8 Universal cleaner in gel form Composition C1 C2 C3 C4 C5 C6 Lauryl Glucoside 5.0 1.5 1.5 1.5 5.0 1.5 Decyl Glucoside — 3.5 3.5 3.5 — 3.5 Sodium Lauryl Sulfate 9.0 6.0 3.0 — 9.0 6.0 Sodium Laureth Sulfate — 3.0 — — — 3.0 Cocamidopropyl Betaine — — 6.0 9.0 — — Ethanol 3.5 3.5 3.5 3.5 3.5 3.5 Citric Acid Monohydrate 3.6 3.6 3.6 3.6 3.6 3.6 Sodium Hydroxide 0.5 0.5 0.5 0.5 0.5 0.5 Laurylamine + 1EO 4.5 3.0 5.0 2.5 — — Hexanediol-1,6 — 0.5 — 0.5 — Capsules with fragrance mixture IV 0.5 — 0.5 — 0.5 — Capsules with fragrance mixture V — 0.5 — 0.5 — 0.5 Water ad 100

TABLE-US-00009 TABLE 9 Powder washing composition Composition E1 E2 E3 E4 E5 E6 Sodium Laureth-1 Sulfate 12.0 8.0 8.0 4.0 4.0 — Dodecylbenzene Sulfonate — — 4.0 8.0 4.0 8.0 Sodium Lauryl Sulfate — 4.0 — — 4.0 4.0 Coco Fatty Acid, Sodium Salt 1.0 1.0 1.0 1.0 1.0 1.0 Coco Glucosides — — — 7.0 — — Laureth-5 7.0 7.0 7.0 — 7.0 7.0 Zeolite A 24.0 24.0 24.0 24.0 24.0 24.0 Sodium silicate, amorphous 3.0 3.0 3.0 3.0 3.0 3.0 (modulus 1:2) Sodium carbonate 12.0 12.0 12.0 12.0 12.0 12.0 Polymeric polycarboxylate 5.5 5.5 5.5 5.5 5.5 5.5 Perborate monohydrate 16.0 16.0 16.0 16.0 16.0 16.0 Tetracetylethylenediamine 5.5 5.5 5.5 5.5 5.5 5.5 Carboxymethylcellulose 0.3 0.3 0.3 0.3 0.3 0.3 Optical brightener 0.2 0.2 0.2 0.2 0.2 0.2 Enzyme granulate (protease) 1.0 1.0 1.0 1.0 1.0 1.0 Capsules with fragrance 0.5 — 0.5 — 0.5 — mixture I Capsules with fragrance — 0.5 — 0.5 — 0.5 mixture V Water ad 100

TABLE-US-00010 TABLE 10 Manual dishwashing composition Composition F1 F2 F3 F4 Sodium Laureth-1 Sulfate 15 15 15 15 Sodium Laureth-2 Sulfate 15 — — — Sodium Lauryl Sulfate — 15 — — Coco Glucosides — — 15 — Sodium Octyl Sulfosuccinate — — 15 Cocamidopropyl Betaine 1 3 3 3 Capsules with fragrance mixture III 0.5 — 0.5 — Capsules with fragrance mixture IV — 0.5 — 0.5 Water ad 100

TABLE-US-00011 TABLE 11 Cleaning composition Compositon G1 G2 G3 G4 G5 G6 C.sub.12/16-Alkyl sulfate sodium salt 5.0 5.0 4.0 0 5.0 0 C.sub.16/18-Tallow fatty alcohol + 25EO 3.0 3.0 4.0 0 0 5.0 C.sub.12/14-Coconut alkyl oligoglucoside 1.0 2.0 2.0 5.0 0 0 Sodium metasilicate 15.0 15.0 15.0 15.0 15.0 15.0 Sodium carbonate 26.0 24.0 24.0 30.0 30.0 30.0 Sulfonated styrene/MA copolymer, — 2.0 2.0 — — — sodium salt Capsules with fragrance mixture II 0.5 — 0.5 — 0.5 — Capsules with fragrance mixture IV — 0.5 — 0.5 — 0.5 Sodium tripolyphosphate ad 100

TABLE-US-00012 TABLE 12 Cosmetic creams Composition H1 H2 H3 H4 H5 Glyceryl Sterate (and) Ceteareth 12/20 5.0 5.0 4.0 — — (and) Cetearyl Alcohol (and) Cetyl Palmitate Ceteareth-12 — — 1.0 — — Polyglyceryl-3 Isostearate — — — 4.0 — Polyglyceryl-2 Dipolyhydroxystearate — — — — 4.0 Glyceryl Oleate — — — 2.0 — PEG-7 Glyceryl Cocoate — — — — 2.0 Dicaprylyl Ether — — — 5.0 6.0 Hexyldecanol (and) Hexyldecyl Laurate — — 3.0 10.0  9.0 Cetearyl Isononanoate 3.0 3.0 — — — Decyl Oleate 3.0 3.0 — — — Coco Caprylate Caprate — — 3.0 5.0 5.0 Beeswax — — — 7.0 5.0 Hydrolyzed Elastin 2.0 — — — — Hydrolyzed Collagen — 2.0 — — — Hydrolyzed Wheat Gluten — — 0.5 — — Sodium Cocoyl Hydrolyzed Wheat Protein — — — 0.5 0.5 Glycol Distearate (and) Laureth-4 (and) 5.0 5.0 4.0 — — Cocamidopropyl Betaine Glycerol (86% strength by weight) — — 1.0 — — Capsules with fragrance mixture III 0.5 — 0.5 — 0.5 Capsules with fragrance mixture V — 0.5 — 0.5 — Water ad 100