4-ethyl-octene-2/3-nitrile as a fragrance

Abstract

The present invention primarily relates to the use of 4-ethyl-octen-2-nitrile and/or 4-ethyl-octen-3-nitrile as fragrance. The invention further relates to novel fragrance compositions comprising 4-ethyl-octen-2/3-nitrile, perfumed products comprising 4-ethyl-octen-2/3-nitrile as well as diverse methods for imparting, modifying and/or enhancing certain scents.

Claims

1. A fragrance composition comprising one or more compound(s) of formula (I) ##STR00006## and one or more further fragrance(s), wherein the weight ratio of the total amount of compound(s) of formula (I) to the total weight of further fragrance(s) is from 1:1000 to 1:0.1.

2. The fragrance composition according to claim 1, wherein the total amount of compound(s) of formula (I) is from 0.0001 to 99.9 wt.-%, relative to the total weight of the fragrance composition.

3. The fragrance composition according to claim 1, wherein the total amount of compound(s) of formula (I) is a sensorially effective amount.

4. The fragrance composition according to claim 1, wherein the one or more further fragrance(s) impart, modify and/or enhance one or more scents selected from the group consisting of green, nitrile, herbaceous, fresh, fruity, flowery, rosy, woody, sweet, earthy, fatty, metallic, balsam, iris, and carrot scents.

5. A perfumed product comprising: (i) a fragrance composition according to claim 1, and (ii) one or more further component(s).

6. A perfumed product according to claim 5, wherein the product is selected from the group consisting of washing and cleaning agents, hygiene or care products, cosmetics and home care products, products of decorative cosmetics, candles, lamp oils, joss sticks, insecticides, repellents, and propellants.

7. A perfumed product according claim 5, wherein the total amount of compound(s) of formula (I) is from 0.00001 to 10 wt.-%, relative to the total weight of the product.

8. A method for perfuming a product comprising: (a) providing a fragrance composition according to claim 1, and (b) adding the fragrance composition to the product in a sensorially effective amount.

9. A method for perfuming hair, skin, textile fibers, surfaces and/or room air comprising: (a) providing a fragrance composition according to claim 1, and (b) adding the fragrance composition to the hair, skin, textile fibers, surfaces and/or room air in a sensorially effective amount.

10. The method according to claim 9, wherein the fragrance composition comprises a surfactant.

11. The method according to claim 9, wherein the weight ratio of the total amount of compound(s) of formula (I) to the total amount of further fragrance(s) is from 1:1000 to 1:0.5.

12. The fragrance composition according to claim 1, wherein the weight ratio of the total amount of compound(s) of formula (I) to the total weight of further fragrance(s) is from 1:1000 to 1:0.5.

13. The fragrance composition according to claim 1, wherein the total amount of compound(s) of formula (I) is from 0.01 to 99 wt.-%, relative to the total weight of the fragrance composition.

14. The fragrance composition according to claim 1, wherein the total amount of compound(s) of formula (I) in the fragrance composition is sufficient for imparting and/or enhancing one or more scents selected from the group consisting of the scents green, nitrile, herbaceous, fresh, fruity, flowery, rosy, woody, sweet, earthy, fatty, metallic, balm, iris, and carrot scents.

15. The fragrance composition according to claim 1, wherein the total amount of compound(s) of formula (I) is sufficient for imparting and/or enhancing one or more scents selected from the group consisting of green, nitrile, rosy, iris, and carrot scents.

16. The fragrance composition according to claim 1, wherein the total amount of compound(s) of formula (I) in the fragrance composition is sufficient for imparting and/or enhancing one or more scents selected from the group consisting of rosy with iris and carrot scents.

17. The fragrance composition according to claim 1, wherein the one or more further fragrance(s) impart, modify and/or enhance one or more scents selected from the group consisting of green, nitrile, herbaceous, fresh, fruity, flowery, rosy, woody, sweet, earthy, fatty, metallic, balsam, iris, and carrot scents.

18. The fragrance composition according to claim 1, wherein the one or more further fragrance(s) impart, modify and/or enhance one or more scents selected from the group consisting of woody, fruity, and flowery scents.

19. The fragrance composition according to claim 1, wherein the one or more further fragrance(s) impart, modify and/or enhance one or more scents selected from the group consisting of fruity and flowery scents.

Description

EXAMPLE 1: PRODUCTION OF 4-ETHYL-OCTEN-2/3-NITRILE

(1) 254 g of 2-ethyl hexanal, 38 g of ammonium acetate and 46 g acetic acid were provided in 520 g toluene in a 1000 ml agitator with water separator. Subsequently, 189 g cyano acetic acid were added at room temperature in portions and while stirring. Thereafter, it was refluxed for 14 h at the water separator and washed with 10% sulphuric acid, 5% sodium hydroxide or, respectively, water after cooling. The organic phase was reduced and the raw product (280 g) was fractionated distilled at a 40 cm vigreux-column in vacuum.

(2) Yield: 190 g (63.9% of theory) boiling point: 80-85 C./0.8 mbar

(3) GC-analysis (20m DB-WAX, inner diameter 0.18 m/60-9-220 C. programmed temperature vaporising injector)

(4) The product consists of 4 isomers, 4.5% (E/Z) 4-ethyl-octen-2-nitrile and 95.5% (E/Z) 4-ethyl-octen-3-nitrile.

(5) (E/Z) 4-ethyl-octen-2-nitrile

(6) MS: m/z (%)=150(2), 136(7), 122(14), 110(38), 97(54), 80(100), 70(48), 55(78), 41(89)

(7) MS: m/z (%)=150(2), 136(5), 122(12), 110(27), 97(51), 80(67), 70(65), 56(100), 41(94) (E/Z) 4-ethyl-octen-3-nitrile

(8) MS: m/z (%)=151(2), 136(2), 122(4), 110(26), 94(32), 81(23), 69(100), 55(21), 41(43)

(9) MS: m/z (%)=151(2), 136(2), 122(5), 110(25), 94(32), 81(22), 69(100), 55(21), 41(42)

EXAMPLE 1A: PRODUCTION OF 4-ETHYL-OCTEN-2/3-NITRILE

(10) 254 g of 2-ethyl hexanal and 189 g of cyano acetic acid were provided in 500 ml cyclohexane in a 1000 ml agitator with water separator and dropping funnel. Afterwards, 65 g of 3-picolin were added while stirring and boiling. Subsequently, it was refluxed for 26 h at the water separator and washed with 10% sulphuric acid, 5% sodium hydroxide or, respectively, water after cooling. The organic phase was reduced and the raw product (250 g) was obtained. The raw product consists of 4 isomers, 16.5% (E/Z) 4-ethyl-octen-2-nitrile and 63.9% (E/Z) 4-ethyl-octen-3-nitrile.

(11) The raw product is fractionated distilled at a canned-column in vacuum.

(12) Yield of the product: 37.5 g (E/Z) 4-ethyl-octen-2-nitrile (95.4%)

(13) Boiling point.: 75-80 C./0.8 mbar

(14) GC-analysis (20 m DB-WAX, inner diameter 0.18 m/60-9-220 C. programmed temperature vaporising injector)

EXAMPLE 2: PERFUME COMPOSITION (FRAGRANCE COMPOSITION)

(15) TABLE-US-00001 AMAROCIT 10% DPG 6 AMBRETTOLIDE 2 AMBRINOL S 10% DPG 6 BENZOIN OLIFFAC TYPE BASE 8 CASSIS 345B TYPE BASE W/O MYRCENE 10 DECALACTON DELTA 10% DPG 3 DIHYDROIONON BETA 6 DIHYDROJASMON 10% DPG 3.5 DIHYDROMYRCENOL 6 DIPROPYLENE GLYCOL 63 EBANOL 10% DPG 6 ETHYLENE BRASSYLAT 80 ETHYLLINALOOL 10 ETHYLMALTOL 10% DPG 1 FLOROSA BM/PYRANOL 5 GLOBALIDE 18 GLOBANONE 12 HEDION 140 HELIONAL 10 HELIOTROPIN/PIPERONAL 3 HEXYL ACETATE 3 IONON ALPHA 30 IRISNITRIL 1% DPG 4 IRON ALPHA 10% DPG 3 ISO E SUPER 80 KOAVONE 6 LACTOJASMONE 1 MACROLIDE SUPRA 10 MENTHANYL ACETATE 10 METHYLHEPTENON-6,5,2 10% DPG 2 MUSCENONE 1 MYSORE ACETAT 15 OCTAHYDROCUMARIN 1.5 ORANGENOEL 5X 1 PENTYL ACETATE N 1% DPG 10 PHENOXANOL 25 SANDALORE 15 SANDRANOL 20 TERPINYLACETAT 20 TETRAHYDROLINALOOL 30 VANILLIN 8 YSAMBER K 6 DIPROPYLENE GLYCOL 300

(16) According to the perfumers, this perfume composition becomes more dry, powdery, complemented and harmonic by the addition of 0.5 wt.-% of a compound of formula (Ia) or (Ib) or, respectively, a mixture of (Ia) and (Ib), wherein a clear iris-violet and rose scent occurs and the woody and flowery aspects are enhanced. The combination or, respectively, use according to the invention provides an own character to the composition and connects the different olfactory elements.

EXAMPLE 3: PERFUME COMPOSITION (FRAGRANCE COMPOSITION)

(17) TABLE-US-00002 AMBERWOOD F 30 AMBRA CORE 70 AMBROCENIDE 10 DPG 10% DPG 10 AMBROXIDE 10 AMYLSALICYLATE N 3 BERGAMOTT ECO ESSENCE 15 CARDAMOMENOEL GUATEMALA 2 CEDAR WOOD OIL VIRGINIA 10 CHOCOLAT NOIR 0.1% DPG 10 CUMARIN 10 DAMASCENON 10% DPG 5 DIPROPYLENE GLYCOL 449 GLOBALIDE 100 HEDION 20 HELIOTROPIN/PIPERONAL 3 HEXENYLSALICYLATE CIS-3 8 IONON BETA 3 ISO E SUPER NON DISCOLORING 200 LINALOOL 5 RED BERRIES EXTRACT 2 SANDALORE 5 SANDRANOL 2 TIMBEROL 10 VANILLIN 10 DIPROPYLENE GLYCOL 8

(18) According to the perfumers, this perfume composition arises by the addition of 2 wt.-% of a compound of formula (Ia) or (Ib) or, respectively, a mixture of (Ia) and (Ib) 10% in DPG. The impression of floweriness is enhanced. The composition appears more woody, more complemented and more harmonic, wherein an authentic scent occurs.

EXAMPLE 4: PERFUME COMPOSITION (FRAGRANCE COMPOSITION)

(19) TABLE-US-00003 ACETYL PYRAZINE-2/1% IN TEC 1% DPG 4 AMBROXIDE 15 BOISIRIS 60 CEDRENE 5 CETONE ALPHA 5 DIPROPYLENE GLYCOL 25 ETHYLVANILLIN 10% DPG 5 GLOBALIDE 45 HEDION HC/70 300 IONON BETA 15 IONON BETA NAT. 15 IRISNITRIL 0.1% DPG 20 ISO E SUPER 100 ISORALDEIN 70 35 LAIT CHAUD 1 NEROLIDOL 30 NONENAL TRANS-2 0.1% DPG 5 VELVIONE 15

(20) According to the perfumers, this perfume composition improves by the addition of 5 wt.-% of a compound of formula (Ia) or (Ib) or, respectively, a mixture of (Ia) and (Ib) 1% in DPG. The flowery impression is enhanced. The composition appears more woody, more complemented and more harmonic, wherein an authentic scent occurs.

EXAMPLE 5: SHAMPOO

(21) The product to be used according to the invention of Example 1 or, respectively, 1a was added in a dose of 0.5 wt.-% to a shampoo base with the following composition:

(22) TABLE-US-00004 Sodium laurylether sulfate 12% (e.g. Texapon NSO, Fa. Cognis Deutschland GmbH) Cocamidopropylbetain .sup.2% (z.B. Dehyton K, Fa. Cognis Deutschland GmbH) Sodium chloride 1.4% Citric acid 1.3% Phenoxyethanol, methyl-, ethyl-, butyl-, 0.5% and propyl parabene Water 82.8%

(23) The pH value of the shampoo base was approximately 6. 100 mL of a 20 wt.-% aqueous shampoo solution were obtained therefrom. In this shampoo solution, 2 hair strands were washed together for 2 minutes and subsequently rinsed for 20 seconds at running lukewarm water. One hair strand was wrapped wet in aluminium foil and the second strand was dried with a hair dryer. Both hair strains were evaluated for their smell by a panel.

(24) The description of the odour of both hair strains was as follows: strongly green, nitrile, rosy with iris and carrot scents.

EXAMPLE 6: CONDITIONER

(25) The perfume composition of Example 2 was (after addition of 0.5 wt.-% of the product of Example 1 or, respectively, 1a) added in a dose of 0.5 wt.-% in a conditioner base with the following composition:

(26) TABLE-US-00005 Quarternary Ammonium methosulfate (Esterquat), approx. 90% 5.5% (e.g. Rewoquat WE 18, Witco Surfactants GmbH) Alkyl dimethyl benzyl ammonium chloride, approx. 50% 0.2% (e.g. Preventol R50, Bayer AG) Dye solution, approx. 1% 0.3% Water 94.0%

(27) The pH value of the conditioner base was in a range of 2 to 3. Two cloth rags were rinsed with 370 g of a 1% aqueous conditioner solution based on the conditioner base comprising 0.5 wt.-% of the perfume composition of Example 2 in a linetest machine in the conditioner programme for 30 minutes at 20 C. The rags were sealed wet and hung for drying. Subsequently, both rags were evaluated for their smell by a panel.

(28) The description of the odour of both cloth rags was as follows: more dry, more powdery, more complemented and more harmonic with a clear iris-violet and rose scent.

EXAMPLE 7: WASHING POWDER

(29) The perfume oil composition of Example 3 was (after addition of 0.5 wt.-% of the product of Example 1 or, respectively, 1a 10% in DPG) added in a dose of 0.4 wt.-% in a washing powder base of the following composition:

(30) TABLE-US-00006 Linear Na-Alkylbenzol sulfonate 8.8% Ethoxylated Fat alcohol C12-18 (7 EO) 4.7% Na-Soap 3.2% Defoamer DOW CORNING 2-4248S 3.9% POWDERED ANTIFOAM, silicone oil on zeolith as carrier Zeolith 4A 28.3% Na-carbonate 11.6% Na-Salt of a co-polymer of acryl and maleic acid 2.4% (Sokalan CP5) Na-silicate 3.0% Carboxymethyl cellulose 1.2% Dequest 2066 2.8% ([[(Phosphonomethyl)imino]bis[(ethylennitrilo)bis (methylen)]]tetrakis-phosphonic acid, sodium salt) Optical brightener 0.2% Na-sulfate 6.5% Protease 0.4% Sodium perborate-tetrahydrate 22.0% TAED 1.0%

(31) Two cloth rags were washed with 370 g of a 1% aqueous washing powder brine based on the washing powder base comprising 0.4 wt.-% of the perfume oil composition of Example 3 (the pH value of the washing powder brine is clearly in the alkaline range) in a linetest machine in the main washing programme for 45 minutes at 60 C. The rags were first washed for 5 minutes with cold water, wringed out and subsequently skidded for 20 seconds. One rag was sealed wet, one was and hung for drying. Subsequently, both rags were evaluated for their smell by a panel.

(32) The description of the odour was each: a nice flowery scent with woody undertone is noticed. The perfume composition appears complemented, harmonic, with an authentic scent.