FRAGRANCE MIXTURES CONTAINING TRICYCLO[5.2.1.0]-DECANE-8-ETHYL ETHER

Abstract

Described is in particular a fragrance mixture, preferably perfume oil, comprising the components (a) (tricyclo[5.2.1.0]-decane-8-ethyl ether)

##STR00001##

and additionally (b) one or more fragrance(s), preferably with a floral odor note, from the group consisting of alcohols and aldehydes having a molecular weight of 210 g/mol or less and/or (c) one or more fragrance(s) from the group consisting of ketones, ethers and esters having a molecular weight in the range from 190 g/mol to 250 g/mol. Furthermore, the present invention relates to methods for producing fragrance mixtures according to the invention, in particular perfume oils, perfumed products containing a fragrance mixture according to the invention, methods for producing perfumed products according to the invention as well as the use of the compound of formula (I) for enhancing the natural freshness and/or radiance and/or for masking or reducing greasy, technical and/or metallic notes of one or more fragrances different from the compound of formula (I).

Claims

1. A fragrance mixture comprising: (a) a compound of formula (I) ##STR00009## and additionally: (b) one or more fragrance(s) selected from the group consisting of alcohols and aldehydes having a molecular weight of 210 g/mol or less, and/or (c) one or more fragrance(s) selected from the group consisting of ketones, ethers and esters having a molecular weight in the range of 190 g/mol to 250 g/mol.

2. The fragrance mixture according to claim 1, wherein the component (b) comprises two or more different fragrances; and/or the component (c) comprises two or more different fragrances.

3. The fragrance mixture according to claim 1, wherein the mass ratio of the total amount of the fragrance(s) of the component (b) to the total amount of the compound of formula (I) is greater than or equal to 99:1, and/or the mass ratio of the total amount of the fragrance(s) of the component (c) to the total amount of the compound of formula (I) is greater than or equal to 99:1.

4. The fragrance mixture according to claim 1, wherein the one or more fragrances of the component (b) each have a molecular weight in the range of 140 to 170 g/mol.

5. The fragrance mixture according to claim 1, wherein the one or more fragrances of the component (c) are selected from the group consisting of methyl dihydrojasmonate, benzylsalicylate, cis-3-hexenyl salicylate, isoamyl salicylate, hexyl salicylate, 2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-naphthalenylmethylketone, linalyl acetate, ethyllinalyl acetate, cedryl methyl ether, cedryl methyl ketone, cedryl acetate, (4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methano azuleno(5,6-d)-1,3-dioxole), 1,1,5,5-tetra methyl-hexahydro-spiro[1.3-dioxolane-2.8(5H)-2H-2.4a]methanonaphthalene, cyclododecyl methyl ether, (ethoxymethoxy)cyclododecane, decahydro-beta-naphthyl acetate, 4,7-methano-3a,4,5,6,7,7a-hexahydro-5(-6)-indenyl acetate, allyl-3-cyclohexyl propionate, allyl cyclohexyloxy acetate, benzylbenzoate, benzylcinnamate, oxacyclohexa-decan-2-one, 15-hydroxy-pentadecanonic acid lactone, 5-cyclohexadecen-1-one, 3-methyl-cyclopentadecenone, 1,3,4,6,7,8-hexahydro-4,6,6,6,7,8,8-hexamethyl, cyclopenta[g]-2-benzopyran, 2-[1-(3,3-dimethylcyclohexyl)ethoxy]-2-methyl-,1-propanoate, 1,4-dioxacycloheptadecane-5,17-dione, 3-methy-cyclopentadecanone, 8-cyclohexadecen-1-one, 3a,6,6,9a-tetramethyl dodecahydronaphtho[2,1-b]furan, alpha-iron, beta-iron, alpha-n-methylionone, beta-n-methylionone, alpha-isomethylionone, beta-isomethylionone and allylionone, and/or wherein the one or more fragrances of the component (b) are selected from the group consisting of 2-methyl-3-(4-tert-butylphenyl)propanal, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarboxaldehyde, 2-methyl-4-(2,2,6-trimethyl-1-cyclohexen-1-yl)-2-butenal, 1-Methyl-4-(4-methyl-3-penten-1-yl)-3-cyclohexene carboxaldehyde, 3-(3-isopropyl-phenyl)-butyraldehyde, (E)-2,6,10-trimethyl-undeca-5,9-dienal, benzo[1,3]dioxole-5-carbaldehyde, 2,2-dimethyl-3-phenyl-propan-1-ol, 2,2-Dimethyl-3-m-tolyl-propan-1-ol, 1-(4-isopropyl-cyclohexyl)-ethanol, (4-isopropyl-cyclohexyl)-methanol, 2-phenyl-ethanol, 2-isobutyl-4-methyl-tetrahydro-pyran-4-ol, 3,7-dimethyl-octa-1,6-dien-3-ol, (Z)-3,7-dimethyl-octa-2,6-dien-1-ol, (E)-3,7-dimethyl-octa-2,6-dien-1-ol, 3,7-dimethyl-oct-6-en-1-ol, 2,6-dimethyl-oct-7-en-2-ol, 3,7-dimethyl-octan-1-ol, 2-methyl-6-methylenoct-7-en-2-ol and (E/Z)-3,7-dimethyl-nona-1,6-dien-3-ol.

6. A method for producing a fragrance mixture according to claim 1 comprising mixing the component (a) with the component (b) and/or with the component (c).

7. The method according to claim 6 wherein the mass ratio of the total amount of the fragrance(s) of the component (b) to the total amount of the compound of formula (I) is greater than or equal to 99:1, and/or the mass ratio of the total amount of the fragrance(s) of the component (c) to the total amount of the compound of formula (I) is greater than or equal to 99:1.

8. A method of enhancing a natural freshness and/or radiance and/or masking or reducing greasy, technical and/or metallic notes of one or more fragrances other than a compound of formula (I) comprising: ##STR00010## mixing the one or more fragrances other than the compound of formula (I) with an amount of the compound of formula (I) sufficient to enhance the natural freshness and/or radiance of the one or more fragrances other than the compound of formula (I) and/or to mask or reduce greasy, technical and/or metallic notes.

9. The method according to claim 8, wherein the one or more fragrances other than the compound of formula (I) are selected from: (b) one or more fragrance(s) selected from the group consisting of alcohols and aldehydes having a molecular weight of 210 g/mol or less, and/or (c) one or more fragrance(s) selected from the group consisting of ketones, ethers and esters having a molecular weight in the range of 190 g/mol to 250 g/mol.

10. The method according to claim 9, wherein the mass ratio of the total amount of the fragrance(s) of the component (b) to the total amount of the compound of formula (I) is greater than or equal to 99:1 and/or the mass ratio of the total amount of the fragrance(s) of the component (c) to the total amount of the compound of formula (I) is greater than or equal to 99:1.

11. A perfumed product comprising a fragrance mixture according to claim 1 in a sensory effective amount.

12. The perfumed product according to claim 11, wherein the product is selected from the group consisting of: perfume extracts, eau de parfums, eau de toilettes, shaving lotions, eau de colognes, pre-shave products, splash colognes, perfumed refreshing wipes, acidic, alkaline and neutral detergents, textile fresheners, ironing aids, liquid laundry detergents, powdered laundry detergents, laundry pre-treatment agents, fabric softeners, laundry soaps, laundry tablets, disinfectants, surface disinfectants, air fresheners, aerosol sprays, waxes and polishes, body care products, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, after-shave creams and lotions, tanning creams and lotions, hair care products, deodorants and antiperspirants, decorative cosmetic products, candles, lamp oils, incense sticks, insecticides, repellents and fuels.

13. A method of producing a perfumed product comprising: i) providing a fragrance mixture according to claim 1 in a sensory effective amount, (ii) providing one or more other components of the perfumed product to be produced; and (iii) contacting or mixing the one or more other components provided in (ii) with a sensory effective amount of the fragrance mixture provided in (i).

14. (canceled)

15. A method of producing a perfumed product comprising: I) providing one or more components of the perfumed product to be prepared which are not the components (a), (b) or (c) of the fragrance mixture according to claim 1, II) mixing the one or more component provided in I) with the component (b) and/or the component (c), and III) contacting or mixing the mixture produced in II) with an amount of the compound of formula (I) sufficient to enhance a natural freshness and/or radiance of one or more fragrances of the component (b) and/or the component (c) and/or to mask or reduce greasy, technical and/or metallic notes.

16. The fragrance mixture according to claim 1 that is a perfume oil.

17. The fragrance mixture according to claim 1 comprising the component (b).

18. The fragrance mixture according to claim 17, wherein the mass ratio of the total amount of the fragrance(s) of the component (b) to the total amount of the compound of formula (I) is greater than or equal to 99.9:0.1.

19. The fragrance mixture according to claim 1 comprising the component (c).

20. The fragrance mixture according to claim 19, wherein the mass ratio of the total amount of the fragrance(s) of the component (c) to the total amount of the compound of formula (I) is greater than or equal to 99.9:0.1.

Description

EXAMPLES

[0094] Abbreviations used: Dipropylene glycol (DPG), diethyl phthalate (DEP), triethyl citrate (TEC), isopropyl myristate (IPM); nat.=natural.

[0095] HEDIONE (HC/30) contains at least 30% by weight of the cis isomer and nearly 70% by weight of the trans-isomer of methyldihydrojasmonat.

[0096] For explanations of product names of fragrances refer to e.g. S. Arctander, Perfume and Flavor Materials, Vol. I and II, Montclair, N. J., 1969, self-published or H. Surburg, J. Panten, Common Fragrance and Flavor Materials, 5 th. Ed., Wiley-VCH, Weinheim 2006.

1 Example: Perfume Oil P1

[0097]

TABLE-US-00001 Preferred application: All-purpose cleaner 0.4% Aldehyde C 8 20.00 Aldehyde C11 MOA 10.00 Limonenal 2.00 Mintonat 120.00 Dihydro myrcenol 50.00 Lemon oil 10.00 Litesea cubeba oil 40.00 Citronitrile 10.00 Eucalyptus oil citriodora 50.00 Citronella oil 40.00 Orange oil 130.00 Terpineol 20.00 Lavandin oil 50.00 Rosemary oil 5.00 Eucalyptus oil 5.00 Aromabase apple green 20.00 Rosaphen 20.00 Benzyl acetate 150.00 Coumarin 20.00 Timberide 2.00 Dipropylene glycol 226.00 1,000.00

[0098] With addition of 0.5% of a 1% solution (in DPG) of tricyclo[5.2.1.0]-decane-8-ethyl ether the mixture becomes rounder, more harmonious, more natural, stronger and less technical.

[0099] With addition of 1% of a 1% solution (in DPG) of tricyclo[5.2.1.0]-decane-8-ethyl ether, the mixture becomes stronger in the top note and gives an additional mandarin note.

2. Example: Perfume Oil P2

[0100]

TABLE-US-00002 Preferred application: Shower gel 0.5% Limonenal 10% 4.00 Florazon 1.00 Leafovert 6.00 Vertocitral 14.00 Phenylacetald. dimethyl acetal 10.00 Cyclogalbant 10.00 Floropal 7.00 Mintonat 50.00 Lemongrass oil rect. 8.00 Orange oil 40.00 Claritone 15.00 Rosemary oil 5.00 Artemisia oil 5.00 Thyme oil white 1.00 Pine needle oil 4.00 Hexyl acetate 20.00 Ethyl methyl butyrate-2 2.00 Allyl cyclohexyl propionate 3.00 Peach total 1.00 Melon concentrate 12.00 Lilax soft 100.00 Linalool 55.00 Geranium RCO 7.00 Phenylethyl alcohol 60.00 Geraniol supra 70.00 Geranyl acetate pure 20.00 Benzyl acetate 24.00 Hedione 90.00 Hexyl cinnamic aldehyde alpha 60.00 Hexenyl salicylate Cis-3 60.00 Parmanyl 3.00 lsoeugenol 2.00 Coumarin 3.00 Vetikolacetat 2.00 Corps racine 0.1% 7.00 Evernyl 10% 14.00 Ambrettolide 5.00 Globanone 90.00 Dipropylene glycol 110.00 Triethyl citrate 1,000.00

[0101] With addition of 0.5% of a 1% solution (in DPG) of tricyclo[5.2.1.0]-decane-8-ethyl ether, the mixture becomes rounder and fresher.

[0102] By adding 1% of a 1% solution (in DPG) of tricyclo[5.2.1.0]-decane-8-ethylether, the mixture becomes more floral and more towards white flower.

3. Example: Perfume Oil P3

[0103]

TABLE-US-00003 Preferred application: Fabric softener 0.8% Aldehyde C11 undecylenic 10% 15.00 Florazon 10.00 Mintonat 10.00 Dihydro myrcenol 40.00 Mandaril 10% 10.00 Orange Oil 70.00 Nerolione 10% 15.00 Majantol 60.00 Tetrahydro linalool 50.00 Phenylethyl alcohol 70.00 Citronellol 950 50.00 Citronellyl acetate extra 20.00 Isodamascon 10% 10.00 Benzyl acetate 30.00 Hedione 30.00 Hexyl cinnamic aldehyde alpha 20.00 Hexyl salicylate 100.00 Eugenol 10.00 Heliotropin 20.00 Ethyl vanillin 10% 30.00 Herbyl propionate 100.00 Iso E super 100.00 Patchouli oil 10.00 Timberide 5.00 Corps racine 0.1% 7.00 Evernyl 10% 5.00 Galaxolide type base 100.00 Triethyl citrate 3.00 1,000.00

[0104] By adding 0.5% of a 1% solution (in DPG) of tricyclo[5.2.1.0]-decane-8-ethyl ether the mixture becomes rounder, less technical and more natural.

[0105] By adding 1% of a 1% solution (in DPG) of tricyclo[5.2.1.0]-decane-8-ethylether, the mixture becomes more flowery and more towards white flower.

4. Example: Perfume Oil P4

[0106]

TABLE-US-00004 Preferred application: Fabric softener 0.8% Aldehyde C12 5.00 Alcohol C 6 10.00 Dihydro myrcenol 30.00 Claritone 10.00 Petitgrain oil parag. 5.00 Methyl naphtyl ketone beta cryst 10.00 Lavandin grosso 20.00 Rosemary oil tun. 10.00 Hexyl acetate 5.00 Cyclamen aldehyde 10.00 Mugetanol 40.00 Majantol 30.00 Tetrahydro muguol 20.00 Base muguet B 20.00 Tetrahydro linalool 40.00 Dimethyl benzyl carbinyl acetate 30.00 Terpineol pure 20.00 Rose oxide HC 10% 20.00 Phenyl ethyl alcohol 60.00 Base rose pamela-Y 30.00 Tetrahydrogeraniol 10.00 Isodamascon 10% 20.00 Benzyl acetone 40.00 Hexyl salicylate 140.00 Parmanyl 10% 10.00 Ionone beta 10.00 Isoraldeine 50.00 Base ylang B 15.00 Anisic aldehyde pure 10.00 Herbaflorat 30.00 Herbyl proprionate 60.00 Iso E Super 120.00 Sandel 80 20.00 Ysamber K 10.00 Globanone 30.00 Dipropylene glycol 1000.00

[0107] By adding 0.5% of a 1% solution (in DPG) of tricyclo[5.2.1.0]-decane-8-ethyl ether to the mixture, the mixture becomes rounder, more flowery and goes in the direction of lavender.

[0108] By adding 1% of a 1% solution (in DPG) of tricyclo[5.2.1.0]-decane-8-ethylether, the mixture becomes more voluminous and acts more strongly towards white flowering.

5. Example: Perfume Oil P5

[0109]

TABLE-US-00005 Preferred application: Body Lotion 0.3% Aldehyde C14 SOG 5.00 Allylamylglycolat 2.00 Allylcyclohexylpropionate 2.00 Allylheptylate 5.00 Allylionone 1.00 Ambroxide 10% IPM 4.00 Benzyl acetate 2.00 Benzyl salicylate 21.50 Bourgeonal 4.00 Damascon alpha 10% DPG 1.00 Dihydromyrcenol 20.00 Dimethyl benzylcarbinyl acetate 10.00 Farenal 1.00 Frambinon 10% DPG 3.00 Geranylacetate pure 4.00 Hedion 200.00 Indoflor crist 10% DPG 5.50 lonone alpha 10.00 Iso e super 40.00 Jasmon cis 1.00 Leafovert 2.00 Macrolide supra 30.00 Majantol 50.00 Manzanate 10% IPM 4.00 Mayol 55.00 Methylphenylacetate 10% DPG 2.00 Mintonat 5.00 Nonadienal trans. 2.00 cis-2.6 5% TEC 1% DPG Patchouli oil 2.00 Phenylethyl alcohol 15.00 Phenylethyldimethylcarbinol 7.00 Roseaphene 20.00 Rose oxidi L 1% DPG 5.00 Sandranol 5.00 Tetrahydromuguol 40.00 Undecavertol 2.00 Veloutone 10% DPG 3.00 Vertocitral 2.00 Vertomugual 1.00 Dipropylene glycol 406.00 1,000.00

[0110] By adding 0.5% of a 1% solution (in DPG) of tricyclo[5.2.1.0]-decane-8-ethyl ether the mixture becomes rounder, fresher and more natural.

[0111] By adding 1% of a 1% solution (in DPG) of tricyclo[5.2.1.0]-decane-8-ethylether, the mixture becomes more voluminous and acts more strongly in the direction of white flower (jasmine).

6. Example: Description of Odor of Preferred Fragrances after Addition of Tricyclo[5.2.1.0]-Decane-8-Ethyl Ether

[0112]

TABLE-US-00006 Mass ratio of the fragrance to the Odor description compound of in comparison formula (I) to the odor of Fragrance Type (1% in DPG) the pure fragrance Mugetanol Alcohol 99:1.0 softer, more natural, more (M = 170) flowery, more radiant not so greasy, not so earthy Dihydro- Alcohol 99:1.0 less unpleasant top note, myrcenol more natural lavender-like, (M = 156) more flowery Linalool Alcohol 99:1.0 less metallic top note, (M = 154) fresher, more natural Geraniol Alcohol 99:1.0 less greasy, less metallic, (M = 154) rounder, stronger, more natural, more volume Citronellol Alcohol 99:1.0 less greasy, rounder, natural, (M = 156) more floral Phenoxanol Alcohol 99:1.0 less greasy, more floral, (M = 178) more natural Lilial Aldehyde 99:1.0 less metallic, fresher, more (M = 204) natural, stronger like lily of the valley Aldehyd Aldehyde 99:1.0 less greasy, less metallic, MNA clear, brighter, rounder (M = 184) Melonal Aldehyde 99:1.0 less metallic, rounder, more (M = 140) natural, more aldehydeic, cleaner Hedion Ketone/ 99:1.0 less greasy, more flowery, (M = 226) Ester rounder, more natural, more jasmine like para tert.-butyl- Ketone 99:1.0 less metallic, rounder, more cyclohexanone harmonious, more woody (M = 154) Oryclon Ester 100:1.0 less metallic, rounder, more (M = 198) harmonious, fresher, stronger

7. Formulation Examples

[0113] The perfume oils P1, P2, P3, P4 or P5 according to the invention from the above perfume oil examples 1 to 5 (i.e. with compound of formula (I) to be used according to the invention) were incorporated separately into the following formulations (products).

[0114] The olfactory effects described above for the respective perfume oil were also observed in the following formulations.

Example F1Laundry Detergent Powder

[0115]

TABLE-US-00007 Weight Weight Material Chemical Name Function % % Sodium Sodium metasilicate Ad 100 Ad 100 metasilicate pentahydrate pentahydrate Sodium hydrogen Sodium hydrogen Alkali 15.0 15.0 carbonate carbonate Sodium Sodium carbonate Bleaching 15.0 15.0 percarbonate peroxyhydrate agent Peractive AC TAED/Sodium Activator 5.00 5.00 Blue carboxymethyl cellulose Genapol OA-080 OxoAlcohol C14-15. Nonionic 3.00 3.00 8EO surfactant Texapon K12 Sodium lauryl sulphate Anionic 7.00 7.00 Powder C12 surfactant Tinopal CBS-X Brightener 0.50 0.50 Savinase 6.0 T, Protease Enzyme 0.40 0.40 Type W Termamyl 120 T Alpha-Amylase Enzyme 0.30 0.30 Sodium sulphate Sodium sulphate Filler 5.50 5.50 Perfume oil P1, Perfume 0.30 0.50 P2, P3, P4 (Fragrance) respectively. P5

Example F2all-Purpose Cleaner

[0116]

TABLE-US-00008 Weight Weight Material Chemical Name Function % % Deionized Water Solvents Ad 100 Ad 100 water Mergal K9N 5-Chloro-2- Preservative 0.1 0.1 methyl-3-(2H)- isothiazolone and 2-methyl-3-(2H)- isothiazolone Tri sodium Tri sodium citrate Complexing agent 3.0 3.0 citrate dihydrate dihydrat Zetesol NL-2 Fatty alcohol C12- Anionic surfactant 30.0 30.0 14-sulfate, sodium Imbentin Fatty alcohol Nonionic surfactant 5.0 5.0 C/125/055 C12-C15, 8EO Ethanol Ethanol Solvent 2.0 2.0 Perfume oil P1, Perfume (fragrance) 0.3 0.5 P2, P3, P4, resp. P5

Example F3Shampoo

[0117]

TABLE-US-00009 Material INCI name Weight % Weight % Deionized Water Ad 100 Ad 100 water Plantacare Sodium laureth sulfate, 20.0 20.0 PS 10 lauryl glucoside Euperlan PK Glycol distearate, 771 sodium lauryl sulfate, 6.0 6.0 cocamide MEA, laureth-10 Dragocid liquid Phenoxyethanol, 0.5 0.5 methylparaben, ethylparaben, butylparaben, propylparaben, isobutylparaben Sodium Sodium chloride 1.4 1.4 chloride Citric acid Citric acid 0.1 0.1 monohydrate cristalline Perfume oil P1, Perfume (fragrance) 0.5 0.8 P2, P3, P4, resp. P5

Example F4Shower Gel

[0118]

TABLE-US-00010 Material INCI name Weight % Weight % Deionized Water Ad 100 Ad 100 water Plantacare Sodium laureth sulfate, 20.0 20.0 PS 10 lauryl glucoside Dragocid Phenoxyethanol, 0.5 0.5 liquid methylparaben, ethylparaben, butylparaben, propylparaben, isobutylparaben Sodium Sodium chloride 1.4 1.4 chloride Citric acid Citric acid 1.3 1.3 monohydrate cristalline Perfume oil P1, Perfume (fragrance) 0.5 0.7 P2, P3, P4, resp. P5

Example F5Fabric Softener

[0119]

TABLE-US-00011 Weight Weight Material Chemical name Function % % Deionized Water Solvent Ad 100 Ad 100 water Rewoquat Dialkylesterammonium- Cationic 16.6 16.6 WE 18 ethosulfate surfactant Mergal K9N 5-Chloro-2-methyl-3- Preservative 0.10 0.10 (2H)-isothiazolone und 2-methyl-3-(2H)- isothiazolone Dow Corning Polydimethyl siloxane Defoamer 0.30 0.30 1520 Antifoam Magnesium Magnesium chloride consistency 10.00 10.00 chloride 1% solution agent solution Perfume oil Fragrance 0.55 0.75 P1, P2, P3, P4, resp. P5

Example F6Eau De Cologne/Eau De Toilette

[0120]

TABLE-US-00012 Ingredients Weight % Weight % Perfume oil P1, P2, 5 10 P3, P4, resp. P5 Ethanol Ad 100 Ad 100 Water 18 10

Example F7Aerosol Pump Spray

[0121]

TABLE-US-00013 Ingredients Weight % Weight % Perfume oil P1, P2, P3, P4, resp. P5 1.0 1.5 Ethanol Ad 100 Ad 100 Water 5.0 8.0 Alpha tocopherol 0.20 0.20 Hydroxypropyl cellulose 0.20 Rosemary extract, soluble in ethanol 0.22 Cetyl alcohol 1.00 0.50

Example F8Shampoo

[0122]

TABLE-US-00014 Ingredients Weight % Weight % Weight % Sodium lauryl ether sulfate 12 12 12 (e.g. Texapon NSO, Cognis Deutschland GmbH) Cocamidopropyl betaine 2 2 2 (e.g. Dehyton K, Cognis Deutschland GmbH) Sodium chloride 1.4 1.4 1.4 Citric acid 1.3 1.3 1.3 Phenoxyethanol, methyl-, 0.5 0.5 0.5 ethyl-, butyl-and propylparabene Perfume oil P1, P2, P3, 0.3 0.5 0.7 P4, resp. P5 Water Ad 100 Ad 100 Ad 100

Example F9Laundry Detergent Powder

[0123]

TABLE-US-00015 Weight Weight Ingredients Weight % % Linear sodium alkylbenzene sulfonate 8.8 8.8 8.8 Ethoxylated fatty alcohol C12-18 (7 EO) 4.7 4.7 4.7 Na-Soap 3.2 3.2 3.2 Defoamer DOW CORNING(R) 2-4248S 3.9 3.9 3.9 POWDERED ANTIFOAM, Silicone oil on zeolite as carrier material Zeolite 4A Ad 100 Ad 100 Ad 100 Sodium carbonate 11.6 11.6 11.6 Sodium salt of a copolymer of acrylic 2.4 2.4 2.4 acid and maleic acid (Sokalan CP5) Sodium silicate 3.0 3.0 3.0 Carboxymethyl cellulose 1.2 1.2 1.2 Dequest 2.8 2.8 2.8 2066([[(phosphonomethyl)imino]bis[(ethylene nitrilo)bis (methylene)]]tetrakis-phosphonic acid, sodium salt) Optical brightener 0.2 0.2 0.2 Sodium sulfate 6.5 6.5 6.5 Protease 0.4 0.4 0.4 Sodium perborate tetrahydrate 21.7 21.7 21.7 Perfume oil P1, P2, P3, P4, resp. P5 0.25 0.35 0.5 EDTA 1.0 1.0 1.0

Example F10Liquid Laundry Detergent

[0124]

TABLE-US-00016 Ingredients Weight % Deionized water 39.9 Optical brightener 0.10 Coconut fatty acids (C12-C18) 7.5 Potassium hydroxide 50% solution 4.3 Propane-1,2-diol 5.00 Fatty alcohols C12-C15, 8EO 12.0 Sodium salt of secondary alkyl sulfonates (C13-C17) 17.0 Triethanolamine 2.0 Trisodium citrate dihydrate 5.0 Dequest 3.0 2066([[(phosphonomethyl)imino]bis[(ethylene nitrilo)bis (methylene)]]tetrakis-phosphonic acid, sodium salt) Ethanol 3.0 Enzymes 0.7 Perfume oil P1, P2, P3, P4, resp. P5 0.5

Example F11Liquid Laundry Detergent Concentrate

[0125]

TABLE-US-00017 Ingredients Weight % Deionized water 13.4 Coconut fatty acids (C12-C18) 10.0 Fatty alcoholsC12-C15, 8 EO 26.0 Sodium salt of secondary alkyl sulfonates (C13-C17) 26.5 Triethanolamine 8.5 Sodium salt of fatty alcohol sulphatesC12-C14 3.0 Ethanol 5.5 Urea 4.5 Enzymes 0.9 Citric acid 1.0 Perfume oil P1, P2, P3, P4, resp. P5 0.7

8. Further Perfume Oil Examples

[0126] A.

TABLE-US-00018 AGRUMEX LC 5 ALDEHYDE C14 SOG 1 ALDEHYDE C18 SOG. 10% DPG 1 ALLYLHEPTYLAT 10% DPG 1 AMBERWOOD F 10% DPG 5 AMBROXIDE 3 ANISALDEHYDE FG 1.5 BENZYL ACETATE 10% DPG 3 BENZYL SALICYLATE 30 BUTYL ACETATE 10% DPG 1 CABREUVA OIL 2 CEDAR WOOD OIL VIRGINIA 20 CITRONELLOL 950 8 CUMARIN 10 CYCLOGALBANAT 10% DPG 2 DAMASCON ALPHA 10% DPG 5 DAMASCONE DELTA 10% DPG 3 DECALACTON GAMMA 2 DIMETHYL BENZYL CARBINYL 2 BUTYRATE DIPROPYLEN GLYCOL 12.5 ETHYLCAPRONAT 10% DPG 2 ETHYLENE BRASSYLATE 45 ETHYLLINALOOL 22 ETHYLVANILLIN 5 EUGENOL NAT. 1 FLOROSA 66 GALAXOLID 50% IN DPG 120 HEDION 135 HELIOTROPIN/PIPERONAL 4 HEXENOL CIS-3 10% DPG 2 HEXENYL ACETATE CIS-3 10% DPG 2 HEXENYL SALICYLAT CIS-3 4 HEXYL ACETATE 10% DPG 1 HEXYL ISOBUTYRATE 10% DPG 1 HEXYL SALICYLATE 4 INDOFLOR CRIST. 3 IONON BETA 6 IRALDEIN GAMMA COEUR 262654 50 ISO E SUPER 200 ISOAMYL ACETATE 10% BB 1 ISOEUGENOL ACETATE 3 CRESOL METHYL ETHER PARA 1 LEAFOVERT 10% DPG 5 LINALOOL 20 MACROLIDE SUPRA 15 MANZANATE 10% DPG 1 METHYL BENZOATE 10% DPG 1 PERANAT 6 PEPPERMINT OIL PIP. CRYSTAL 5 WHIT 10% DPG PHENIRAT 2.5 PHENYLETHYL ALCOHOL 10% DPG 5 PHENYLETHYL ISOBUTYRATE 3 10% DPG POLYSANTOL 10% DPG 2 ROSE OXIDE HIGH CIS 10% DPG 1 SANDRANOL 25 STYROLYL ACETATE 1.5 TERPIN OIL ALPHA 30 CINNAMIC ALDEHYDE 10% DPG 1

[0127] By adding 1% of tricyclo[5.2.1.0]-decane-8-ethyl ether, the mixture becomes stronger, greener, fresher and the mixture gets a natural overall impression.

[0128] B.

TABLE-US-00019 AGRUMEX LC 120 ALDEHYDE C14 SOG 30 ALLYLCYCLOHEXYL PROPIONATE 10 ALLYLHEPTYLAT 40 BENZYL ALCOHOL DD 40 CITRAL 95 17 CITRONELLOL 950 4 DAMASCENONE 10% DPG 2 DAMASCON BETA 0.5 DAMASCONE DELTA 10 DECALACTONE GAMMA 5 DIPROPYLENE GLYCOL 281.5 DYNASCONE 10% DPG 2 ETHYLBUTYRATE 4 ETHYLMALTOL 10 ETHYLMETHYLBUTYRATE-2 20 FRAMBINON 5 GERANIOL SUPRA 25 HEDION 5 HERBAFLORATE 15 HEXYL ACETATE 2 HEXYL ISOBUTYRATE 10 HEXYL CINNAMIC ALDEHYDE ALPHA 35 IONON BETA 65 JASMAPRUNATE 20 LINALOOL 110 LINALYL ACETATE 10 MANZANATE 7 METHYLMETHYL BUTYRATE-2 5 STYROLYL ACETATE 30 THIOMENTHANONE-8,3/1% IN TEC 10% DPG 15 UNDECAVERTOL/GIV 25 VERTOCITRAL 20

[0129] By adding 1% of tricyclo[5.2.1.0]-decane-8-ethyl ether, the mixture becomes stronger, fresher and more radiant, and the composition has a fuller top note.

[0130] C.

TABLE-US-00020 AGRUMEX HC 110 ALDEHYDE C18 SO-CALLED 5 ALLYL CYCLOHEXYL PROPIONATE 10 APRIFLOREN 20 BENZALDEHYDE DD 2 BENZYL BUTYRATE 10 CINNAMIC ALDEHYDE 5 CITRONELLOL 950 15 CLARITONE 15 COUMARONE 2 DAMASCENONE 10% DPG 5 DIETHYL MALONATE 95 DIMETHYL BENZYL CARBINYL ACETATE 20 DIMETHYL BENZYL CARBINYL BUTYRATE 50 DOWANOL DPM 260 ETHYL BUTYRATE 1 ETHYL MALTOL 2 ETHYL VANILLIN 2 FILBERTONE 1% DPG 5 FLOROPAL 4 GLOBALIDE 4 HEXENYL ACETATE CIS-3 1 HEXENYL BUTYRATE CIS-3 1 HEXYL ACETATE 25 ISOAMYL BUTYRATE 5 JASMAPRUNAT 8 LINALOOL 60 MAGNOLAN 6 MANZANATE 10 MELONAL 1 METHYL OCTIN CARBONATE 10% DPG 1 PARMANYL 10% DPG 4 RASPBERRY AROMABASE 15 ROSE OXIDE HIGH CIS 10% DPG 4 STYRALYL ACETATE 5 VERTACETAL COEUR 2 VERTOCITRAL 10

[0131] By adding 1% of tricyclo[5.2.1.0]-decane-8-ethyl ether, the mixture becomes rounder, fresher and has more natural aspects.

9. Exemplary Instructions for Producing Tricyclo[5.2.1.0]Decane-8-Ethyl Ether

[0132] Stage 1: Addition of ethanol to dicyclopentadiene

##STR00007##

[0133] 53 g Amberlyst 15 dry and 120 g ethanol are placed in a 500 ml three-necked flask with stirrer, contact thermometer, mushroom heating hood, dropping funnel. 160 g (1.21 mol) Dicyclopentadiene is then added while stirring at RT and stirred for 8-9 h at 80 C. After cooling to RT, the catalyst is filtered off and it is washed with ethanol. The mixture is alkalified with solid soda and concentrated. The residue is distilled at the ball tube (boiling range: 60-90 C./1.5 mbar). 180 g distillate is obtained.

[0134] Stage 2: Hydrogenation

[0135] 180 g of the 1st stage in 700 g ethanol are hydrogenated with 10 g palladium 5% on A-carbon at 10 bar and 75 C. When the reaction is complete, the catalyst is filtered off and it is concentrated. The raw yield of 180 g is distilled at a 40 cm M.F.K. Yield 165 g corresponds to 79.6% percent of theory. The product comprises the following isomers:

[0136] Isomer 11.9%

[0137] Isomer II 83.0%

[0138] Isomer III 0.3%

[0139] Isomer IV 12.3%

##STR00008##

[0140] MS: m/z (%)=180 (2-5), 134(100), 119(55-60), 106(31-34), 91(23-24), 79(31-33), 67(22-30), 41(15-19)