Cyclic acetals and ketals and use thereof as fragrance

Abstract

The present invention relates to compounds of the formula (I) and use thereof as fragrance. In a further aspect the present invention relates to compositions and fragrance mixtures containing compounds of the formula (I) and the products perfumed with these compositions and fragrance mixtures. Further, the present invention relates to a method for intensifying an odor or several odors selected from the group consisting of fruity, floral, spicy, woody, musk and ambrette and a method for endowing hair or textile fibers with one, several or all of the notes selected from the group consisting of fruity, floral, spicy, woody, musk and ambrette with use of one or more compounds of the formula (I). ##STR00001##

Claims

1. A compound of the formula (II) or (II) ##STR00016## wherein R.sub.1 is hydrogen or C.sub.1-C.sub.3 alkyl, and R.sub.2 is hydrogen or C.sub.1-C.sub.4 alkyl, or (b) according to the formula (III) ##STR00017## wherein R.sub.1 is hydrogen or C.sub.1-C.sub.3 alkyl, and R.sub.2 hydrogen or C.sub.1-C.sub.4 alkyl and the compound is saturated or unsaturated, or (c) according to formula (IV) or (IV) ##STR00018## wherein RH or C.sub.1-C.sub.4 alkyl and RH or C.sub.1-C.sub.3 alkyl.

2. A composition comprising (i) one or more 3,6,8,8-tetramethyl-octahydro-3a,7-methano-azulen-5,6-diol ketal(s) and (ii) one or more compound(s) of the formulae (II), (II), (III), (IV) and/or (IV) according to claim 1, wherein the total content of the compounds of the formulae (II), (II), (III), (IV) and/or (IV) is greater than 40 wt. %, based on the total amount of 3,6,8,8-tetramethyl-octahydro-3a,7-methano-azulen-5,6-diol ketal(s) contained in the composition, and/or wherein the weight ratio of compound(s) of the formula (IV) to compound(s) of the formula (IV), if present, lies in the range from 4:1 to 1:10.

3. A fragrance mixture, comprising a composition according to claim 2, as well as one or more (further) compound(s) not corresponding to the fragrances of the formulae (II), (III), (IV), or (IV), wherein (i) the quantity of the compound(s) of the formulae (II), (II), (III), (IV), or (IV), is sufficient to mediate an ambergris and/or wood fragrance note, and/or (ii) the (further) fragrances not corresponding to the formulae (II), (II), (III), (IV), or (IV), mediate one, several or all of the notes fruity, floral, spicy, woody, musk and ambrette and the quantity of the compound(s) of the formula (II), (II), (III), (IV), or (IV), is sufficient to modify and/or to intensify one, several or all of the notes fruity, floral, spicy, woody, musk and ambrette, and/or (iii) the quantity of the compound(s) of the formulae (II), (II), (III), (IV), or (IV), is sufficient to impart to the fragrance mixture an impression of volume, complexity, elegance and/or naturalness, and/or (iv) the quantity of the compound(s) of the formulae (II), (II), (III), (IV), or (IV), is sufficient, in comparison to an otherwise identically constituted fragrance mixture without compounds of the formulae (II), (II), (III), (IV), or (IV), to create a more nurturing, more harmonious, higher quality and/or more natural olfactory impression.

4. A method for intensifying an odor or several odors selected from the group consisting of fruity, floral, spicy, woody, musk and ambrette, comprising the following step: (i) providing one or more fragrance(s) with one, several or all of the notes selected from the group consisting of fruity, floral, spicy, woody, musk and ambrette, and (ii) mixing said one or more fragrance(s) with (ii-ii) the composition according to claim 2 in a quantity which suffices to intensify the olfactory impression of the fragrance(s).

5. A perfumed product containing a composition, according to claim 2, in a sensorily effective quantity, wherein the product contains one or more surfactants.

6. A method for intensifying an odor, comprising incorporating a compound as claimed in claim 1 into a fragrance or fragrance mixture, means for increasing substantivity and/or retention of a fragrance mixture, or fixative.

7. A fragrance mixture, comprising one or more compound(s) of the formulae (II), (II), (III), (IV) and/or (IV) according to claim 1, as well as one or more (further) compound(s) not corresponding to the fragrances of the formulae (II), (II), (III), (IV) or (IV), wherein (i) the quantity of the compound(s) of the formulae (II), (II), (III), (IV) or (IV), is sufficient to mediate an ambergris and/or wood fragrance note, and/or (ii) the (further) fragrances not corresponding to the formulae (II), (II), (III), (IV), or (IV), mediate one, several or all of the notes fruity, floral, spicy, woody, musk and ambrette and the quantity of the compound(s) of the formula (II), (II), (III), (IV), or (IV), is sufficient to modify and/or to intensify one, several or all of the notes fruity, floral, spicy, woody, musk and ambrette, and/or (iii) the quantity of the compound(s) of the formulae (II), (II), (III), (IV), or (IV), is sufficient to impart to the fragrance mixture an impression of volume, complexity, elegance and/or naturalness, and/or (iv) the quantity of the compound(s) of the formulae (II), (II), (III), (IV), or (IV), is sufficient, in comparison to an otherwise identically constituted fragrance mixture without compounds of the formulae (II), (II), (III), (IV), or (IV), to create a more nurturing, more harmonious, higher quality and/or more natural olfactory impression.

8. The fragrance mixture, of claim 7, wherein the quantity of the compound(s) of the formulae (II), (II), (III), (IV), or (IV), lies in the range from 0.0001 to 25 wt. %, based on the total weight of the fragrance mixture.

9. The fragrance mixture of claim 7, further containing (i) one or more wood and/or ambergris fragrance(s) not corresponding to the formulae (II), (II), (III), (IV), or (IV), and/or (ii) one or more musk fragrance(s).

10. The fragrance mixture of claim 9, wherein the musk fragrance(s) is/are selected from the group consisting of macrocyclic musk fragrances, nitro musk fragrances, polycyclic musk fragrances, alicyclic musk fragrances and mixtures thereof.

11. The fragrance mixture of claim 9, wherein the weight ratio of musk fragrances to the compound(s) of the formulae (II), (II), (III), (IV) or (IV), lies in the range from 100:1 to 100,000:1.

12. A method for endowing hair or textile fibers with one, several or all of the notes selected from the group consisting of fruity, floral, spicy, woody, musk and ambrette, comprising the following steps: (i) preparing a fragrance mixture according to claim 7, wherein the (further) fragrance(s) not corresponding to the formulae (II), (II), (III), (IV), or (IV), mediate(s) one, several or all of the notes fruity, floral, spicy, woody, musk and ambrette and the quantity of the compound(s) of the formulae (II), (II), (III), (IV), or (IV), is sufficient to modify and/or to intensify one, several or all of the notes fruity, floral, spicy, woody, musk and ambrette, and (ii) applying the fragrance mixture onto the hair or the textile fibers.

13. A method for intensifying an odor or several odors selected from the group consisting of fruity, floral, spicy, woody, musk and ambrette, comprising the following step: (i) providing one or more fragrance(s) with one, several or all of the notes selected from the group consisting of fruity, floral, spicy, woody, musk and ambrette, and (ii) mixing said one or more fragrance(s) with (ii-iii) the fragrance mixture of claim 7 in a quantity which suffices to intensify the olfactory impression of the fragrance(s).

14. A perfumed product containing a fragrance mixture, according to claim 7, in a sensorily effective quantity, wherein the product contains one or more surfactants.

15. A method for intensifying an odor or several odors selected from the group consisting of fruity, floral, spicy, woody, musk and ambrette, comprising the following step: (i) providing one or more fragrance(s) with one, several or all of the notes selected from the group consisting of fruity, floral, spicy, woody, musk and ambrette, and (ii) mixing said one or more fragrance(s) with (ii-i) one or more compound(s) of the formula (II), (II), (III), (IV), or (IV), of claim 1, in a quantity which suffices to intensify the olfactory impression of the fragrance(s).

16. A perfumed product containing one or more compound(s) of the formulae (II), (II), (III), (IV), or (IV), according to claim 1, in a sensorily effective quantity, wherein the product contains one or more surfactants.

17. The perfumed product of claim 16, selected from the group consisting of detergents, cleaners, sanitary agents and toiletries, in particular for use in the field of body care, hair care, cosmetics or the household.

Description

EXAMPLES

(1) Unless otherwise stated, contents and percentages relate to the respective weight.

(2) Abbreviations Used:

(3) Dipropylene glycol (DPG), diethyl phthalate (DEP), triethyl citrate (TEC).

(4) For explanations of the product names of the fragrances, see e.g. S. Arctander, Perfume and Flavor Materials, Vol. I and II, Montclair, N. J., 1969, published by author, or H. Surburg, J. Panten, Common Fragrance and Flavor Materials, 5.sup.th. Ed., Wiley-VCH, Weinheim 2006.

(5) Cis-cedranediol, which was obtained from ()--cedrene by epoxidation and subsequent ring opening, was used. According to NMR investigation, the following structure for the diol is present:

(6) ##STR00011##

Example 1

Reaction of cis-cedranediol with 1-methoxy-propan-2-one

(7) 24 g (0.1 mol) of cis-cedranediol (26 g with a GC content of 92% were used), 127.6 g (1.45 mol) of 1-methoxy-propan-2-one, 31.8 g (0.3 mol) of trimethyl orthoformate and 0.4 g of concentrated sulfuric acid were stirred for 24 hours at 10 C. After the end of the reaction, methyl tert.-butyl ether was added, washed with a 5% sodium hydrogen carbonate solution and the low-boilers distilled off. After addition of n-hexane, unreacted cis-cedranediol crystallized out, and was removed by filtration. After concentration of the filtrate, 30.4 g of crude product were obtained. According to GC analysis, the content of the compounds of the formulae (VIII) and (IX) in the product obtained was in total 51% (corresponding to 50% of the theoretical yield). By dissolving the crude product in dipropylene glycol (DPG), a solution with a content of 10 wt. % of compounds of the formulae (VIII) and (IX) (with a ratio of (VIII):(IX)=1:2.3) was produced from this.

(8) For analytical tests, from the crude product the stereoisomeric compounds of the formulae (VIII) and (IX) were separated from one another by liquid chromatography on silica gel 60 (0.04-0.063 mm) with the eluent cyclohexane/ethyl acetate (60/1). The compound of the formula (VIII) was obtained with a purity of 99.4% and the compound of the formula (IX) with a purity of 96.9%.

(9) Compound of the formula (VIII):

(10) ##STR00012##

(11) .sup.1H-NMR (400 MHz, C.sub.6D.sub.6): 3.95 (dd, J=8.5, 7.2 Hz, 1H), 3.58 (dq, J=10.3, 0.5 Hz, 1H), 3.51 (dq, J=10.3, 0.5 Hz, 1H), 3.28 (s, 3H), 2.23 (dt, J=12.1, 1.0 Hz, 1H), 1.98 (d, J=4.5 Hz, 1H), 1.86-1.76 (m, 2H), 1.754 (q, J=0.3 Hz, 3H), 1.75-1.69 (m, 1H), 1.62 (h, J=6.9 Hz, 1H), 1.49 (s, 3H), 1.44 (ddd, J=12.3, 4.8, 2.0 Hz, 1H), 1.42-1.35 (m, 1H), 1.36-1.25 (m, 2H), 1.23-1.11 (m, 1H), 0.96 (s, 3H), 0.89 (s, 3H), 0.76 (d, J=7.1 Hz, 3H) ppm.

(12) .sup.13C-NMR (C.sub.6D.sub.6): 109.86, 85.13, 80.02, 78.58, 59.15, 58.70, 57.83, 52.53, 42.36, 42.23, 41.65, 38.91, 36.17, 31.17, 28.79, 28.19, 25.61, 25.19, 15.59 ppm.

(13) Odor: very strong ambergris, wood, reminiscent of white ambergris, very long adhesion

(14) Compound of the Formula (IX):

(15) ##STR00013##

(16) .sup.1H-NMR (400 MHz, C.sub.6D.sub.6): 3.99 (dd, J=8.9, 6.8 Hz, 1H), 3.60 (d, J=10.2 Hz, 1H), 3.57 (d, J=10.2 Hz, 1H), 3.26 (d, J=0.5, 3H), 2.23 (d, J=11.9 Hz, 1H), 1.99 (d, J=4.5 Hz, 1H), 1.81 (ddd, J=13.5, 8.9, 2.5 Hz, 1H), 1.74 (s, 3H), 1.78-1.68 (m, 2H), 1.64 (h, J=6.8 Hz, 1H), 1.52 (s, 3H), 1.42 (ddd, J=12.0, 4.6, 2.6 Hz, 1H), 1.41-1.35 (m, 1H), 1.35-1.24 (m, 2H), 1.23-1.11 (m, 1H), 0.96 (s, 3H), 0.88 (s, 3H), 0.78 (d, J=7.1 Hz, 3H) ppm.

(17) .sup.13C-NMR (C.sub.6D.sub.6): 109.85, 84.90, 79.33, 78.73, 59.15, 58.73, 57.86, 52.52, 42.38, 42.32, 41.99, 38.74, 36.24, 31.14, 28.76, 28.11, 25.93, 25.63, 15.63 ppm.

(18) Odor: weak ambergris

Example 2

Reaction of Cis-Cedranediol with Methoxyacetaldehyde Dimethyl Acetal

(19) 24 g (0.1 mol) of cis-cedranediol (26 g with a GC content of 92% were used), 127.6 g (1.45 mol) of methoxyacetaldehyde dimethyl acetal and 0.4 g of concentrated sulfuric acid were stirred for 24 hours at 10 C. After the end of the reaction, methyl tert.-butyl ether was added, washed with a 5% sodium hydrogen carbonate solution and the low-boilers distilled off. After addition of n-hexane, unreacted cis-cedranediol crystallized out, and was removed by filtration. After concentration of the filtrate, 30.4 g of crude product were obtained. According to GC analysis, the content of the compounds of the formulae (X) and (XI) in the product obtained was in total 51% (corresponding to 50% of the theoretical yield). By dissolving the crude product in dipropylene glycol (DPG), a solution with a content of 10 wt. % of compounds of the formulae (X) and (XI) (with a ratio of (X):(XI)=1:6.2) was produced from this.

(20) For analytical tests, from the crude product the stereoisomeric compounds of the formulae (X) and (XI) were separated from one another by liquid chromatography on silica gel 60 (0.04-0.063 mm) with the eluent cyclohexane/ethyl acetate (60/1). The compound of the formula (X) was obtained with a purity of 99.4% and the compound of the formula (XI) with a purity of 96.9%.

(21) Compound of the Formula (X):

(22) MS: m/z: 41 (24), 43 (20), 45 (16), 55 (21), 69 (64), 93 (17), 95 (17), 105 (50), 119 (100), 133 (58), 147 (26), 203 (86), 249 (25)

(23) ##STR00014##

(24) Odor: strong ambergris, wood

(25) Compound of the formula (XI):

(26) MS: m/z: 41 (23), 43 (19), 45 (16), 55 (23), 69 (60), 93 (17), 95 (17), 105 (49), 119 (100), 133 (57), 147 (24), 203 (83), 249 (26)

(27) ##STR00015##

(28) Odor: weak ambergris

(29) In the following perfume formulae and application examples, in each case solutions with the stated content were used, wherein the weight ratio of the compound of the formula (VIII) to the compound of the formula (IX) was 3:8 and the weight ratio of (X) to (XI) was 3:8.

(30) Perfume Oil Example according to the invention P1:

(31) TABLE-US-00002 Ref-1 P1 HEXENAL DIMETHYL ACETAL, 2,2,5-TRIMETHYL- 10 10 4- HEXADECEN-1,16-OLIDE, 7(9)Z- 15 15 CYCLOHEXADECENONE, (8E/Z)- + 140 140 CYCLOHEXADECENONE, (7E)- BUT-2-EN-1-ONE, 1-(2,6,6-TRIMETHYL- 10 10 CYCLOHEX-3-ENYL)- (E) 10% DPG ETHANEDIOL BRASSYLATE 120 120 NONADIEN-3-OL, 3,7-DIMETHYL-1,6- 30 30 PYRANOL, 2-ISOBUTYL-4-METHYL-4- 40 40 TETRAHYDRO- (E/Z) 5-HEXENYL BUTYRATE, 2-METHYL- 5 5 GERANYL ACETATE 40 40 METHYL DIHYDROJASMONATE 400 400 2-(1-(3,3-DIMETHYLCYCLOHEXYL)-ETHOXY-2- 30 30 METHYLPROPYL PROPIONATE 3Z-HEXENYL ACETATE 5 5 3Z-HEXENYL SALICYLATE 20 20 BICYCLO[4.4.0]DECENE, 3,4,10,10- 50 50 TETRAMETHYL-3-HYDROXYETHYL-1(6) CYCLOHEXANONE, 3,3,5,5-TETRAMETHYL-4-(1- 10 10 ETHOXYVINYL)- 3Z-HEXENYL METHYL CARBONATE, 10% in DPG 10 10 MANDARIN OIL 20 20 2(3H)-FURANONE, 5-HEXYL-DIHYDRO-4-METHYL- 5 5 (E/Z) PRENYL ACETATE 5 5 TRICYCLO(5.2.1.0)DECANE, 8-FORMYL- 15 15 DIOXOLE, 4H-4A,9-METHANOAZULENO(5,6-D)- 20 0 OCTAHYDRO-2,2,5,8,8,9A-HEXAMETHYL-, 1,3- (Ambrocenide), 0.1% in DPG (Compound of the formula (VIII)), 0.1% in DPG 0 20 TOTAL 1000 1000

(32) The comparative example (Ref-1) with Ambrocenide smells fresh, fruity and transparent. In perfume oil P1, the compound of the formula (VIII) imparts to the composition an elegance and more pronounced fruitiness.

(33) Perfume Oil Example According to the Invention P2:

(34) TABLE-US-00003 Ref-2 P2 UNDECALACTONE, GAMMA- 2 2 HEXADECEN-1,16-OLIDE, 7(9)Z- 10 10 CYCLOHEXADECENONE, (8E/Z)- + 100 100 CYCLOHEXADECENONE, (7E)- CARDAMOM OIL CEYLON 2 2 INDAN-4-ONE, 1,1,2,3,3-PENTAMETHYL- 15 15 TETRAHYDRO- CEDARWOOD OIL VIRGINIA 100 100 DAMASCONE, -BETA-, 10% in DPG 2 2 METHYL DIHYDROJASMONATE 210 210 BICYCLO[4.4.0]DECENE, 3,4,10,10- 300 300 TETRAMETHYL-3-HYDROXYETHYL-1(6) IRALDEIN, GAMMA- 60 60 CYCLOHEXANONE, 3,3,5,5-TETRAMETHYL- 10 10 4-(1-ETHOXYVINYL)- CYCLOPENTADECENONE, 3-METHYL-5E- 20 20 PATCHOULI OIL 5 5 PENTEN-2-OL, 3,3-DIMETHYL-5-(2,2,3- 20 20 TRIMETHYL-3-CYCLOPENTENYL)-4- PENTANOL, 3-METHYL-5-(2,2,3-TRIMETHYL- 80 80 3-CYCLOPENTENYL)-2- + HEXANOL, 6-(2,2,3-TRIME-3-CYCLOPENTENYL)-3- VANILLIN 2 2 ISOLONGIFOLANONE ETHANEDIOL KETAL 30 30 CINNAMON BARK OIL CEYLON 2 2 DIOXOLE, 4H-4A,9-METHANOAZULENO(5,6- 30 0 D)-OCTAHYDRO-2,2,5,8,8,9A-HEXAMETHYL-, 1,3-(Ambrocenide), 0.1% in DPG (Compound of the formula (VIII)), 0.1% in DPG 0 30 TOTAL 1000 1000

(35) The comparative example (Ref-2) with Ambrocenide smells floral-spicy with dry woody accents. In perfume oil P2, the spicy note is supported by the compound of the formula (VIII), so that the whole composition appears more peppery and more characterful.

(36) Perfume Oil Example According to the Invention P3:

(37) TABLE-US-00004 Ref-3 P3 HEXENAL DIMETHYL ACETAL, 2,2,5-TRIMETHYL-4- 10 10 BENZODIOXEPINONE, 7-METHYL-3,4-DIHYDRO-3- 10 10 PROPANAL, 2-METHYL-3-(4-METHOXYPHENYL)- 5 5 CITRONELLOL, BETA- 20 20 LEMON OIL 15 15 ALLYL CYCLOHEXYLOXYACETATE, 10% in DPG 10 10 DAMASCONE, TRANS-ALPHA-, 1% IN DPG 20 20 BUT-2-EN-1-ONE, 1-(2,6,6-TRIMETHYL- 5 5 CYCLOHEX-3-ENYL)-(E), 10% in DPG DECALACTONE GAMMA, 10% in DPG 15 15 ETHANEDIOL BRASSYLATE 80 80 NONADIEN-3-OL, 3,7-DIMETHYL-1,6- 70 70 PHENOL, 2-METHOXY-4-(2-PROPENYL)- 5 5 PYRANOL, 2-ISOBUTYL-4-METHYL-4-TETRAHYDRO- (E/Z) 80 80 5-HEXENYL BUTYRATE, 2-METHYL- 15 15 METHYL DIHYDROJASMONATE 250 250 PROPANAL, 2-PIPERONYL- 30 30 3Z-HEXENYL SALICYLATE 5 5 INDOLE, 10% in DPG 10 10 IRALDEIN, GAMMA- 30 30 BICYCLO[4.4.0]DECENE, 3,4,10,10-TETRAMETHYL-3- 80 80 HYDROXYETHYL-1(6) PENTADECANOLIDE, 1,15- 20 20 HEPTENAL, 2,6-DIMETHYL-5-, 10% in DPG 3 3 PYRIDINE, 4-DECYL-, 1% in DPG 2 2 CYCLOHEXENE, 2,4-DIMETHYL-1-FORMYL-3-, 10% in DPG 10 10 DIOXOLE, 4H-4A,9-METHANOAZULENO(5,6-D)- 5 0 OCTAHYDRO-2,2,5,8,8,9A-HEXAMETHYL-, 1,3- (Ambrocenide), 0.1% in DPG (Compound of the formula (X)), 0.1% in DPG 0 5 TOTAL 805 805

(38) The comparative example (Ref-3) with Ambrocenide impresses through its transparent freshness. In perfume oil P3, through the compound of the formula (X) it is achieved that the composition is perceived as more cosmetically nurturing with more volume.

(39) Perfume Oil Example According to the Invention P4:

(40) TABLE-US-00005 Ref-4 P4 NAPHTHO[2.1-B]FURAN, DODECAHYDRO-3A.6.6.9A- 5 5 TETRAMETHYL- BENZOIN SIAM ABS., 50% IN DPG 10 10 BENZYL SALICYLATE 20 20 BERGAMOT OIL 50 50 CEDRYL METHYL ETHER 40 40 CISTUS LABDANUM 35 35 CISTUS OIL SPAN., 10% in DPG 10 10 DAMASCONE, TRANS-ALPHA-, 1% in DPG 20 20 MYRCENOL, DIHYDRO- 30 30 ETHANEDIOL BRASSYLATE 120 120 METHYL BENZOATE, 2,4-DIHYDROXY-3,6-DIMETHYL-, 1% in 20 20 DPG PYRANOL, 2-ISOBUTYL-4-METHYL-4-TETRAHDRO- (E/Z) 20 20 PENTADECEN-1,15-OLIDE, (11E/Z)- + PENTADECEN-1,15- 30 30 OLIDE, 12E- METHYL DIHYDROJASMONATE 300 300 BICYCLO[4.4.0]DECENE, 3,4,10,10-TETRAMETHYL-3- 75 75 HYDROXYETHYL-1(6) ISOBUTYLQUINOLINE, 10% in DPG 3 3 CYCLOHEXANONE, 3,3,5,5-TETRAMETHYL-4-(1- 30 30 ETHOXYVINYL)- LABDANUM ABSOLUTE 20 20 LINALYL ACETATE 50 50 MANDARIN OIL 10 10 CYCLOPENTADECENONE, 3-METHYL-5E- 10 10 CLARY SAGE OIL 10 10 OLIBANUM COEUR, 50% in TEC 5 5 PATCHOULI OIL 20 20 PYRIDINE, 4-DECYL-, 1% in DPG 2 2 BUTENOL, 2-ETHYL-4-(2,2,3-TRI- 5 5 METHYL-3-CYCLOPENTENYL)-2E- VANILLIN 30 30 DIOXOLE, 20 0 4H-4A,9-METHANOAZULENO(5,6-D)-OCTAHYDRO- 2,2,5,8,8,9A-HEXAMETHYL-, 1,3-(Ambrocenide), 0.1% in DPG (Compound of the formula (X)), 0.1% in DPG 0 20 TOTAL 1000 1000

(41) The comparative example (Ref-4) with Ambrocenide impresses through a beautiful wood note. In perfume oil P4, the compound of the formula (X) imparts more volume to the composition and the tobacco note is intensified.

(42) Perfume Oil Example According to the Invention P5:

(43) TABLE-US-00006 Ref-5 P5 CYCLOHEXADECENONE, (8E/Z)- + 200 200 CYCLOHEXADECENONE, (7E)- MUGWORT OIL 10 10 BERGAMOT OIL 60 60 CEDRYL METHYL ETHER 40 40 CISTUS OIL SPAN., 10% in DPG 10 10 LEMON OIL 20 20 COUMARIN 40 40 ALLYL CYCLOHEXYLOXYACETATE, 10% in DPG 5 5 MYRCENOL, DIHYDRO- 50 50 ETHANEDIOL BRASSYLATE 120 120 METHYL BENZOATE, 20 20 2,4-DIHYDROXY-3,6-DIMETHYL-, 10% in DPG METHYL DIHYDROJASMONATE 30 30 IRALDEIN, GAMMA- 20 20 BICYCLO[4.4.0]DECENE, 120 120 3,4,10,10-TETRAMETHYL-3- HYDROXYETHYL-1(6) SPEARMINT OIL, 10% in DPG 10 10 LAVENDER OIL 10 10 LINALOOL 20 20 LINALYL ACETATE 20 20 INDENO[1.2-D]-M-DIOXIN, 90 90 2,4-DIMETHYL-TETRAHYDRO- CLARY SAGE ABSOLUTE 5 5 CLOVE FLOWER OIL 10 10 VANILLIN 20 20 DIOXOLE, 4H-4A,9-METHANOAZULENO(5,6-D)- 20 0 OCTAHYDRO-2,2,5,8,8,9A-HEXAMETHYL-, 1,3-(Ambrocenide), 0.1% in DPG (Compound of the formula (VIII)), 0 20 0.1% in DPG TOTAL 950 950

(44) The comparative example (Ref-5) with Ambrocenide has a very radiant and intense lavender effect. In perfume oil P5, through the compound of the formula (VIII), the whole composition becomes more naturally lavender-like and as a result appears higher quality with more volume.

(45) Perfume Oil Example According to the Invention P6:

(46) TABLE-US-00007 Ref-6 P6 HEXADECEN-1,16-OLIDE, 7(9)Z- 20 20 CYCLOHEXADECENONE, (8E/Z)- + 200 200 CYCLOHEXADECENONE, (7E)- INDAN-4-ONE, 20 20 1,1,2,3,3-PENTAMETHYL-TETRAHYDRO- ETHANEDIOL BRASSYLATE 150 150 5-HEXENYL BUTYRATE, 2-METHYL- 5 5 PENTADECEN-1,15-OLIDE, (11E/Z)- + 90 90 PENTADECEN-1,15-OLIDE, 12E- METHYL DIHYDROJASMONATE 210 210 BICYCLO[4.4.0]DECENE, 200 200 3,4,10,10-TETRAMETHYL-3- HYDROXYETHYL-1(6) CYCLOHEXANONE, 20 20 3,3,5,5-TETRAMETHYL-4-(1- ETHOXYVINYL)- PENTEN-2-OL, 5 5 3,3-DIMETHYL-5-(2,2,3-TRIMETHYL-3- CYCLOPENTENYL)-4- ISOLONGIFOLANONE ETHANEDIOL KETAL 70 70 DIOXOLE, 4H-4A,9-METHANOAZULENO(5,6-D)- 10 0 OCTAHYDRO-2,2,5,8,8,9A-HEXAMETHYL-, 1,3- (Ambrocenide), 0.1% in DPG (Compound of the formula (VIII)), 0 10 0.1% in DPG TOTAL 1000 1000

(47) The comparative example (Ref-6) with Ambrocenide possesses a cool transparency paired with a dry woodiness. In perfume oil P6, the compound of the formula (VIII) imparts to the whole composition a more pronounced harmony and warmth, wherein the fruitiness is intensified (pushed) as far as a beautiful plum note paired with tobacco effects.

(48) Perfume Oil Example According to the Invention P7:

(49) TABLE-US-00008 Ref-7 P7 NAPHTHO[2.1-B]FURAN, DODECAHYDRO-3A.6.6.9A- 5 5 TETRAMETHYL- BENZYL SALICYLATE 50 50 BERGAMOT OIL 50 50 COUMARIN 5 5 DAMASCONE, TRANS-ALPHA-, 1% in DPG 20 20 DECALACTONE GAMMA, 10% in DPG 15 15 ETHANEDIOL BRASSYLATE 30 30 NONADIEN-3-OL, 3,7-DIMETHYL-1,6- 60 60 3,7-DIME-1,6-NONADIEN-3-YL ACETATE 50 50 PYRANOL, 2-ISOBUTYL-4-METHYL-4-TETRAHYDRO- (E/Z) 70 70 5-HEXENYL BUTYRATE, 2-METHYL- 5 5 BICYCLO[2.2.2]OCTENE, 5 5 6-ME-8-ISOPROPYL-2(3)-(1,3- DIOXOLAN-2-YL METHYL DIHYDROJASMONATE 280 280 PROPANAL, 2-PIPERONYL- 20 20 BENZALDEHYDE, 3,4-METHYLENEDIOXY- 10 10 2-(1-(3,3-DIMETHYLCYCLOHEXYL)-ETHOXY-2- 60 60 METHYLPROPYL PROPIONATE 3Z-HEXENYL SALICYLATE 5 5 BICYCLO[4.4.0]DECENE, 3,4,10,10-TETRAME-3- 120 120 HYDROXYETHYL-1(6) PENTADECANOLIDE, 1,15- 30 30 MANDARIN OIL 20 20 CYCLOPENTADECENONE, 3-METHYL-5E- 3 3 BUTANOL, 2-METHYL-4-PHENYL-2- 10 10 PYRIDINE, 4-DECYL-, 1% in DPG 2 2 PENTEN-2-OL, 3,3-DIMETHYL-5-(2,2,3-TRIMETHYL-3- 20 20 CYCLOPENTENYL)-4- CYCLOHEXANOL, 4-(3-METHYL-BUTYL)- (E/Z) 15 15 VANILLIN 20 20 DIOXOLE, 5 0 4H-4A,9-METHANOAZULENO(5,6-D)-OCTAHYDRO- 2,2,5,8,8,9A-HEXAMETHYL-, 1,3-(Ambrocenide), 0.1% in DPG (Compound of the formula (VIII)), 0.1% in DPG 0 5 DIPROPYLENE GLYCOL 15 15 TOTAL 1000 1000

(50) Through the replacement of Ambrocenide of the comparative example (Ref-7) by the compound of the formula (VIII), the whole composition P7 has a more voluminous, more elegant and thus also higher quality effect, perfume oil P7 has a more complex effect and the coumarin note is very beautifully harmonized.

(51) Perfume Oil Example According to the Invention P8:

(52) TABLE-US-00009 Ref-8 P8 Ethyl acetoacetate 60 60 Propanal, 2-methyl-2-(4-ethylbenzyl)- 25 25 Cyclohexene, 2,4-dimethyl-1-formyl-3- (E/Z) 15 15 Hexenol Cis-3 130 130 3Z-hexenyl methyl carbonate 20 20 Allyl cyclohexyloxyacetate 25 25 Benzenemethanol, .alpha.-methyl-, 1-acetate 40 40 Linalyl acetate 80 80 Myrcenol, Dihydro- 650 650 Mandarin oil 260 260 Grapefruit oil 260 260 Hexenal dimethyl acetal, 2,2,5-trimethyl-4- 170 170 Methyl anthranilate, 10% DPG 155 155 Cardamom oil 5 5 Red Berry Extract 25 25 Nutmeg oil 20 20 Ethyl butyrate, 10% DPG 10 10 Undecalactone, gamma- 65 65 Ethyl pentanoate, 2-methyl-, 10% DPG 15 15 2-propen-1-yl heptanoate 40 40 Ethylmaltol 15 15 Benzenepropanal, alpha-methyl-4-(1,1-dimethylethyl)- 250 250 1.3-Benzodioxol-5-propanal, alpha-methyl- 200 200 Hydroxycitronellal 200 200 4-methyl-2-(2-methylpropyl)oxan-4-ol 260 260 1.6-octadien-3-ol, 3.7-dimethyl- 40 40 Nonadien-3-ol, 3,7-dimethyl-1,6- 130 130 1,1-dimethyl-2-phenylethyl butyrate 65 65 Phenylethyl alcohol 40 40 2-phenoxyethyl propionate, 2-methyl- 40 40 2-buten-1-one, 40 40 1-(2.6.6-trimethyl-2-cyclohexen-1-yl)- (E) 2-buten-1-one, 5 5 1-(2.6.6-trimethyl-1.3-cyclohexadien-1-yl)- Methyl dihydrojasmonate 390 390 3-buten-2-one, 220 220 3-methyl-4-(2.6.6-trimethyl-2-cyclohexen-1-yl)- Vanillin 230 230 Cinnamon bark oil 15 15 2H-1-benzopyran-2-one 200 200 Cyclohexanol acetate, 4-(1.1-dimethylethyl)- (Z) 50 50 Cedarwood oil 15 15 Bicyclo[4.4.0]decene, 1,500 1,500 3,4,10,10-tetramethyl-3-hydroxyethyl-1(6) Cyclododecane, (ethoxymethoxy)- 300 300 2-buten-1-ol, 130 130 2-ethyl-4-(2.2.3-trimethyl-3-cyclo- penten-1-yl)- (2E) Dioxole, 30 0 4H-4a,9-methanoazuleno(5,6-d)-octa- hydro-2,2,5,8,8,9a- hexamethyl-, 1,3-(Ambrocenide), 10.0% in DPG (Compound of the formula (X)), 10.0% in DPG 0 30 5H-3.5a-Epoxynaphth[2.1-c]oxepine, 1,200 1,200 dodecahydro-3.8.8.11a-tetramethyl- Naphtho[2.1-b]furan, 220 220 dodecahydro-3a.6.6.9a-tetramethyl- Dipropylene glycol 175 175 TOTAL 8,030 8,030

(53) The comparative example Ref-8 with Ambrocenide is characterized by the contradiction between fresh woody notes and sweet balsamic aspects. The replacement of Ambrocenide by the compound of the formula (X) imparts to the whole composition more impact, volume and character paired with velvety-powdery aspects.

(54) Perfume Oil Example According to the Invention P9:

(55) TABLE-US-00010 Ref-9 P9 Undecenal, 2,6,10-trimethyl-9- 15.00 15.00 Propanal, 2-methyl-2-(4-ethylbenzyl)- 3.00 3.00 Cis-3 hexenyl acetate 3.00 3.00 Cyclohexene, 2,4-dimethyl-1-formyl-3- (E/Z) 2.00 2.00 Tricyclo(5.2.1.0)decane, 8-formyl- 2.00 2.00 Allyl cyclohexyloxyacetate 4.00 4.00 Heptenal, 2,6-dimethyl-5- 2.00 2.00 Identoil Bergamot 45.00 45.00 Myrcenol, Dihydro- 90.00 90.00 2.6-octadienal, 3.7-dimethyl- (2E/Z) 10.00 10.00 2-pentenonitrile, 3-methyl-5-phenyl- (2E/Z) 3.00 3.00 Orange oil 30.00 30.00 Hexenal dimethyl acetal, 2,2,5-trimethyl-4- 2.00 2.00 Lavandin oil 10.00 10.00 Cardamom oil 1.00 1.00 Ethyl pentanoate, 2-methyl-, 10% DPG 10.00 10.00 Benzenepropanal, alpha-methyl-4-(1.1-dimethylethyl)- 40.00 40.00 2H-1.5-benzodioxepin-3(4H)-one, 7-methyl- 20.00 20.00 Benzenepropanol, beta.beta.3-trimethyl- 40.00 40.00 Geranium oil 2.00 2.00 3-buten-2-one, 1-(2.4.4-trimethyl-2-cyclohexen-1-yl)- (2E) 10.00 10.00 alpha-hexylcinnamaldehyde 60.00 60.00 Methyl cyclopentaneacetate, 3-oxo-2-pentyl- (E) 90.00 90.00 Propanonitrile, 3-(3-hexenyloxy)- (Z) 2.00 2.00 3-buten-2-one, 4-(2.6.6-trimethyl-1-cyclohexen-1-yl)- 5.00 5.00 Benzene, 1-methoxy-4-(1-propenyl)- (E) 10.00 10.00 Ethanone, 1-(2-benzofuranyl)- 2.00 2.00 Cyclohexanol acetate, 4-(1.1-dimethylethyl)- (Z) 30.00 30.00 Cedarwood Oil (cedarwood oil) 15.00 15.00 Cyclohexanepropanol, alpha-ethyl-2.2.6-trimethyl- (E/Z) 30.00 30.00 Bicyclo[4.4.0]decene, 100.00 100.00 3,4,10,10-tetramethyl-3-hydroxyethyl-1(6) Cyclododecane, (ethoxymethoxy)- 30.00 30.00 Patchouli oil 10.00 10.00 2-buten-1-ol, 30.00 30.00 2-ethyl-4-(2.2.3-trimethyl-3-cyclopenten-1-yl)- (2E) Methyl benzoate, 2,4-dihydroxy-3,6-dimethyl- 3.00 3.00 Tetramethyl dodecahydro-3a,6,6,9a-naphtho(2,1-b)furan 12.00 12.00 Isolongifolanone ethanediol ketal 50.00 50.00 Dioxole, 2.00 0 4H-4a,9-methanoazuleno(5,6-d)-octahydro-2,2,5,8,8,9a- hexamethyl-, 1,3-(Ambrocenide), 10.0% in DPG (Compound of the formula (X)), 10.0% in DPG 0 2.00 Pentadecanolide, 1,15- 30.00 30.00 Cyclohexadecenone, 8E/Z- 120.00 120.00 Dipropylene glycol 25.00 25.00 TOTAL 1,000.00 1,000.00

(56) The comparative example Ref-9 with Ambrocenide is a modern fougere type with a watery citrus top note and a woody base. Through the replacement of Ambrocenide by the compound of the formula (X), the white wood, as well as cedar- and sandalwood aspect, is intensified.

(57) Perfume Oil Example According to the Invention P10:

(58) TABLE-US-00011 Ref-10 P10 Undecenal, 2,6,10-trimethyl-9- 8 8 10-Undecenal 8 8 Cyclohexene, 2,4-dimethyl-1-formyl-3- (E/Z) 5 5 3Z-hexenyl methyl carbonate 8 8 Indeno[1.2-d]-1.3-dioxin, 70 70 4.4a.5.9b-tetrahydro-2.4-dimethyl- Cyclohexanol acetate, 3.3.5-trimethyl- 20 20 Orange oil 20 20 Methyl naphthyl ketone beta 5 5 Ethanone, 1-(3-methyl-2-benzofuranyl)- 2 2 2-butanone, 4-(4-hydroxyphenyl)- 1 1 Peach Base 8 8 Pyranol, 2-isobutyl-4-methyl-4-tetrahydro- (E/Z) 10 10 1.6-octadien-3-ol, 3.7-dimethyl- 90 90 2H-pyran, tetrahydro-2-methyl-2-(2-methyl-1-propenyl)- 3 3 (E/Z) 2-phenylethanol 70 70 Benzenepentanol, beta-methyl- 25 25 2.6-octadien-1-ol acetate, 3.7-dimethyl- (2E/Z) 30 30 But-2-en-1-one, 1-(2,6,6-trimethyl-cyclohex-3-enyl)- (E) 3 3 Propyl benzoate 10 10 Methyl dihydrojasmonate (E) 70 70 Amyl salicylate N/Iso 17 17 Benzyl salicylate 80 80 Cis-3 hexenyl salicylate 10 10 Hexyl benzoate, 2-hydroxy- 33 33 3-Decen-5-ol, 4-methyl- 5 5 Orris Base 5 5 3-buten-2-one, 80 80 3-methyl-4-(2.6.6-trimethyl-2-cyclohexen-1-yl)- Benzaldehyde, 3,4-methylendioxy- 10 10 Vanillin 4 4 Cinnamyl alcohol 4 4 2H-1-benzopyran-2-one 8 8 Acetylcedrene 70 70 Cyclododecane, (ethoxymethoxy)- 40 40 2-pentanone, 4-cyclohexyl-4-methyl- 8 8 Patchouli Base 37 37 Patchouli oil 33 33 Dioxole, 20 0 4H-4a,9-methanoazuleno(5,6-d)-octahydro- 2,2,5,8,8,9a-hexamethyl-, 1,3-(Ambrocenide), 1.0% in DPG Compound of the formula (VIII) 10.0% in DPG 2 Pentadecen-1,15-olide, (11E/Z)- + 40 40 pentadecen-1,15-olide, 12E- Triethyl citrate 30 48 TOTAL 1000 1000

(59) The comparative example Ref-10 with Ambrocenide is a floral Chypre type with an aldehydic top note, paired with floral heart notes and rounded off by patchouli and musk. The replacement of Ambrocenide by the compound of the formula (VIII) imparts to the whole composition a more nurturing, warmer and more voluminous character; in addition the adhesion is improved.

(60) The perfume oils P1, P2, P3, P4, P5, P6, P7, P8, P9 and P10 from the above perfume oil examples were each separately incorporated into the following formulations.

(61) The olfactory effects described above with each respective perfume oil were in each case also observed in the following formulations.

FORMULATION EXAMPLES

Example F1Washing Powder

(62) TABLE-US-00012 Material Chemical Name Function Wt. % Wt. % Sodium sodium metasilicate qsp 100 qsp 100 metasilicate pentahydrate pentahydrate Sodium sodium hydrogen alkali 15.0 15.0 hydrogen carbonate carbonate Sodium sodium carbonate bleaching 15.0 15.0 percarbonate peroxyhydrate agent Peractive AC TAED/Na activator 5.00 5.00 Blue carboxymethyl- cellulose Genapol OA-080 oxo alcohol C14-15, nonionic 3.00 3.00 8EO surfactant Texapon K12 sodium lauryl anionic 7.00 7.00 Powder sulfate 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 sulfate sodium sulfate filler 5.50 5.50 Perfume oil perfume 0.30 0.50 P1, P2, P3, (fragrance) P4, P5, P6, P7, P8, P9 or P10

Example F2General Purpose Cleaner

(63) TABLE-US-00013 Material Chemical Name Function Wt. % Wt. % Deionized water solvent qsp 100 qsp 100 water Mergal K9N 5-chloro-2- preservative 0.1 0.1 methyl-3-(2H)- isothiazolone and 2- methyl-3- (2H)- isothiazolone Trisodium trisodium complexing 3.0 3.0 citrate citrate agent dihydrate dihydrate Zetesol NL-2 fatty alcohol anionic 30.0 30.0 C12-14- surfactant sulfate, sodium Imbentin fatty alcohol nonionic 5.0 5.0 C/125/055 C12-C15, surfactant 8EO Ethanol ethanol solvent 2.0 2.0 Perfume oil perfume 0.3 0.5 P1, P2, P3, (fragrance) P4, P5, P6, P7, P8, P9 or P10

Example F3Shampoo

(64) TABLE-US-00014 Material INCI Name Wt. % Wt. % Deionized water qsp 100 qsp 100 water Plantacare sodium laureth sulfate, 20.0 20.0 PS 10 lauryl glucoside Euperlan PK glycol distearate, 6.0 6.0 771 sodium lauryl sulfate, cocamide MEA, laureth-10 Dragocid phenoxyethanol, 0.5 0.5 Liquid methylparaben, ethylparaben, butylparaben, propylparaben, isobutylparaben Sodium sodium chloride 1.4 1.4 chloride Citric acid citric acid 0.1 0.1 monohydrate crystalline Perfume oil perfume (fragrance) 0.5 0.8 P1, P2, P3, P4, P5, P6, P7, P8, P9 or P10

Example F4Shower Gel

(65) TABLE-US-00015 Material INCI Name Wt. % Wt. % Deionized water qsp 100 qsp 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 crystalline Perfume oil perfume (fragrance) 0.5 0.7 P1, P2, P3, P4, P5, P6, P7, P8, P9 or P10

Example F5Fabric Conditioner

(66) TABLE-US-00016 Material Chemical Name Function Wt. % Wt. % Deionized water solvent qsp 100 qsp 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 and 2-methyl-3-(2H)- isothiazolone Dow polydimethylsiloxane defoamant 0.30 0.30 Corning 1520 Antifoam Magnesium magnesium chloride consistency 10.00 10.00 Chloride solution agent 1% solution Perfume oil fragrance 0.55 0.75 P1, P2, P3, P4, P5, P6, P7, P8, P9 or P10

Example F6Eau De Cologne/Eau De Toilette

(67) TABLE-US-00017 Ingredients Wt. % Wt. % Perfume oil 5 10 P1, P2, P3, P4, P5, P6, P7, P8, P9 or P10 Ethanol qsp 100 qsp 100 Water 18 10

Example F7Aerosol Pump Spray

(68) TABLE-US-00018 Ingredients Wt. % Wt. % Perfume oil 1.0 1.5 P1, P2, P3, P4, P5, P6, P7, P8, P9 or P10 Ethanol qsp 100 qsp 100 Water 5.0 8.0 Alpha-tocopherol 0.20 0.20 Hydroxypropylcellulose 0.20 Rosemary extract, 0.22 soluble in ethanol Cetyl alcohol 1.00 0.50

Example F8Shampoo

(69) TABLE-US-00019 Ingredients Wt. % Wt. % Wt. % Sodium lauryl ether 12 12 12 sulfate (e.g. Texapon NSO, Cognis Germany GmbH) Cocamidopropylbetaine 2 2 2 (e.g. Dehyton K, Cognis Germany 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 propylparaben Perfume oil 0.3 0.5 0.7 P1, P2, P3, P4, P5, P6, P7, P8, P9 or P10 Water qsp 100 qsp 100 qsp 100

Example F9Detergent Powder

(70) TABLE-US-00020 Ingredients Wt. % Wt. % Wt. % Linear Na alkylbenzenesulfonate 8.8 8.8 8.8 Ethoxylated fatty alcohol 4.7 4.7 4.7 C12-18 (7 EO) Na soap 3.2 3.2 3.2 Defoamant DOW CORNING(R) 2-4248S 3.9 3.9 3.9 POWDERED ANTIFOAM, silicone oil on zeolite as support Zeolite 4A qsp 100 qsp 100 qsp 100 Na carbonate 11.6 11.6 11.6 Na salt of a copolymer of acrylic 2.4 2.4 2.4 and maleic acid (Sokalan CP5) Na silicate 3.0 3.0 3.0 Carboxymethylcellulose 1.2 1.2 1.2 Dequest 2.8 2.8 2.8 2066([[(phosphono- methyl)imino]bis[(ethylene- nitrilo)bis (methylene)]]tetrakis-phosphonic acid, sodium salt) Optical brightener 0.2 0.2 0.2 Na sulfate 6.5 6.5 6.5 Protease 0.4 0.4 0.4 Sodium perborate 21.7 21.7 21.7 tetrahydrate Perfume oil 0.25 0.35 0.5 P1, P2, P3, P4, P5, P6, P7, P8, P9 or P10 EDTA 1.0 1.0 1.0

Example F10Liquid Detergent

(71) TABLE-US-00021 Ingredients Wt. % Deionized water 39.9 Optical brightener 0.10 Coco fatty acids (C12-C18) 7.5 Potassium hydroxide 50% solution 4.3 Propan-1,2-diol 5.00 Fatty alcohols C12-C15, 8 EO 12.0 Na salt of secondary 17.0 alkylsulfonates (C13-C17) Triethanolamine 2.0 Trisodium citrate dihydrate 5.0 Dequest 3.0 2066([[(phosphono- methyl)imino]bis[(ethylene- nitrilo)bis (methylene)]]tetrakis-phosphonic acid, sodium salt) Ethanol 3.0 Enzymes 0.7 Perfume oil 0.5 P1, P2, P3, P4, P5, P6, P7, P8, P9 or P10

Example F11Liquid Detergent Concentrate

(72) TABLE-US-00022 Ingredients Wt. % Deionized water 13.4 Coco fatty acids (C12-C18) 10.0 Fatty alcohols C12-C15, 8 EO 26.0 Na salt of secondary 26.5 alkylsulfonates (C13-C17) Triethanolamine 8.5 Na salt of fatty alcohol 3.0 sulfates C12-C14 Ethanol 5.5 Urea 4.5 Enzymes 0.9 Citric acid 1.0 Perfume oil 0.7 P1, P2, P3, P4, P5, P6, P7, P8, P9 or P10
Application Technology Examples:
Example Intrinsic Adhesion: Compound of the Formula (VIII) Versus Ambrocenide:

(73) Each fragrance to be tested is dipped as a 10% solution in DPG onto coded scent strips, i.e. the fragrance to be tested is applied onto the scent strip by dipping the respective scent strip into the respective solution of the fragrance to be tested, and odor-assessed directly afterwards at the following time intervals:

(74) 1 hour; 3 hours; 10 hours; 1 day; 3 days; 10 days; 1 month; 3 months. The testers assess the odor intensity on a scale from 1=odorless to 9=very strong.

(75) Testing is continued until the mean intensity value from the testers falls below the value of 1.5 (very weak). If 50% of the testers return an intensity of 1, and thus make it clear that the fragrance dipped onto the scent strip is no longer perceived, the test is declared to be ended. In the longest case, testing is continued for 3 months.

(76) TABLE-US-00023 Compound of the formula Ambrocenide, (VIII), 10% in DPG 10% in DPG Intrinsic adhesion more than 3 months 10 days

(77) The compound of the formula (VIII) exhibits markedly longer adhesion on the scent strip than Ambrocenide.

(78) Example Substantivity on Hair: Compound of the Formula (VIIII) Versus Ambrocenide:

(79) The fragrance to be tested is incorporated in a quantity of 0.6 wt. % as a 50% solution in DPG into a shampoo formulation analogous to example F8 instead of the perfume oil used there. For each fragrance to be tested, two strands of hair are needed. In addition, as a reference, in each case one pair of hair strands is washed with the unperfumed shampoo formulation of example F8.

(80) All hair strands are washed together with neutral shampoo in a 2 L beaker (min. 2 hrs soaking). Then the hair strands are rinsed well under running water and then dried at room temperature (ca. 23 C.). 100 ml of a 20% aqueous solution is prepared from each shampoo (unperfumed mixture also). Now for each shampoo one strand pair is washed together for 2 mins in the solution. Next, these two strands are rinsed together for 20 secs under flowing, lukewarm water. Both hair strands are combed. One hair strand is wrapped wet in aluminum foil. The second hair strand is dried with a hair dryer.

(81) A tester panel assesses the prepared hair strands by smelling. The testers assess the intensity of the samples on a scale from 0 (odorless) to 6 (very strong).

(82) Order:

(83) a) freshly washed, dry hair

(84) b) freshly washed hair, wet

(85) TABLE-US-00024 Substantivity Compound of the on hair formula (VIII) Ambrocenide Wet hair 1.4 1.2 Dry hair 1.7 0.5

(86) The intensity value of the compound of the formula (VIII) on dry hair is higher compared with Ambrocenide by more than a factor of 3.

(87) Example Substantivity on Cotton: Compound of the Formula (VIII) Versus Ambrocenide:

(88) The fragrance to be tested is incorporated in a quantity of 0.5 wt. % as a 50% solution in DPG into a fabric softener formulation analogous to example F5 instead of the perfume oil used there.

(89) Cotton cloths are washed neutral at 95 C. in a washing machine and dried in air at room temperature.

(90) In each case, two identically coded cotton cloths are rinsed with 370 g of a 1% aqueous fabric softener liquor containing the respective fragrance to be tested in a pot of the Linitest machine in the fabric softener program. Next, the liquor is poured out of the individual pots, the cloths wrung pot by pot, and all cloth pairs spin-dried as a pair for 20 secs. Then one cloth from each cloth pair is shrink-wrapped wet, and one hung out to dry.

(91) A test panel assesses the prepared samples by smelling.

(92) The testers assess the intensity of the samples on a scale from 0 (odorless) to 6 (very strong)

(93) In each case they start with the unperfumed specimen and then the samples.

(94) Order:

(95) a) dry laundry

(96) b) wet laundry

(97) TABLE-US-00025 Substantivity Compound of the on cotton formula (VIII) Ambrocenide Wet laundry 1.6 1.2 Dry laundry 1.5 0.8

(98) The intensity value of the compound of the formula (VIII) on dry laundry is higher by a factor of 2 compared with Ambrocenide, and even the intensity of wet laundry is assessed higher for the compound of the formula (VIII).

(99) In addition, the dry cotton cloths were stored over a longer period and each assessed as described above after several days.

(100) TABLE-US-00026 Day 3 Compound of the formula (VIII) 2.00 Ambrocenide 1.20 Day 8 Compound of the formula (VIII) 1.79 Ambrocenide 0.93 Day 10 Compound of the formula (VIII) 1.80 Ambrocenide 1.10 Day 14 Compound of the formula (VIII) 1.69 Ambrocenide 0.92 Day 18 Compound of the formula (VIII) 1.80 Ambrocenide 0.50

(101) The intensity of the compound of the formula (VIII) even after a period of 18 days is still assessed as markedly stronger compared with Ambrocenide.