EP0237979A1 - 1-Alkyl/alkenyl-cyclohexane-1-ole as perfumes - Google Patents

Abstract

The invention describes the use of 1-alkyl / alkenyl-cyclohexan-1-ols of the general formula I <IMAGE> in which R is an alkyl group with 1 to 4 carbon atoms or an alkenyl group with 2 to 4 carbon atoms, 0 to 3 of the 10 radicals R 'is methyl and 10 to 7 of the 10 radicals R' are hydrogen, as odoriferous substances in mixtures containing active chlorine.

Description

The invention relates to the use of 1-alkyl / alkenyl-cyclohexan-1-ols as fragrances in mixtures containing active chlorine.

In many consumer goods, for example in personal care products or fabric softeners, problems regarding the stability of the fragrances used are unknown. In contrast, mixtures containing active chlorine such as machine dishwashing detergents or scouring agents destroy most fragrances, so that perfuming in the desired fragrance directions is no longer possible (see, for example, JS Jellinek: "Perfuming Products", p. 100/101, Dr. Alfred Hüthig Verlag Heidelberg, 1976). In addition, in many cases the destruction of the fragrances is associated with an undesirably high reduction in the active chlorine content.

The object of the invention was therefore to provide fragrances which are stable in mixtures containing active chlorine.

worin R eine Alkylgruppe mit 1 bis 4 Kohlenstoffatomen oder eine Alkenylgruppe mit 2 bis 4 Kohlenstoffatomen, 0 bis 3 der 10 Reste R' Methyl und 10 bis 7 der 10 Reste R' Wasserstoff bedeuten, als Riechstoffe in aktivchlorhaltigen Mischungen keine Stabilitätsprobleme auftreten.Surprisingly, it was found that when using 1-alkyl / alkenylcyclohexan-1-ols of the general formula I

wherein R is an alkyl group with 1 to 4 carbon atoms or an alkenyl group with 2 to 4 carbon atoms, 0 to 3 of the 10 radicals R 'methyl and 10 to 7 of the 10 radicals R' are hydrogen, no stability problems occur as fragrances in mixtures containing active chlorine.

worin R eine Alkylgruppe mit 1 bis 4 Kohlenstoffatomen oder eine Alkenylgruppe mit 2 bis 4 Kohlenstoffatomen, 0 bis 3 der 10 Reste R' Methyl und 10 bis 7 der 10 Reste R' Wasserstoff bedeuten, als Riechstoffe in aktivchlorhaltigen Mischungen.The invention thus relates to the use of 1-alkyl / alkenylcyclohexan-1-ols of the general formula 1

wherein R is an alkyl group with 1 to 4 carbon atoms or an alkenyl group with 2 to 4 carbon atoms, 0 to 3 of the 10 radicals R 'methyl and 10 to 7 of the 10 radicals R' are hydrogen, as fragrances in mixtures containing active chlorine.

1-ethyl- and 1,3,3,5-tetramethyl-cyclohexan-1-ol are preferably used as fragrances in mixtures containing active chlorine.

1-ethyl-cyclohexan-1-ol (Wallach in Liebigs Ann. Chem. 360, 50) and 1,3,3,5-tetramethyl-cyclohexan-1-ol (barber in Helv. Chim. Acta 23, 519 (1940 )) are known compounds and are obtained by reacting the ketones with the corresponding Grignard compounds. The smell of 1,3,3,5-tetramethyl-cyclohexan-1-ol is described as camphrig. However, neither of the two references gives information about the stability of the alcohols in mixtures containing active chlorine.

The smell of the chlorine-stable cyclohexan-1-oie can be characterized as camphorous, earthy, woody.

The cyclohexan-1-ols, which are used according to the invention in mixtures containing active chlorine, were subjected to a storage test. It was surprisingly found that no changes in odor occurred in liquid and solid mixtures containing active chlorine even after one year at room temperature.

Examples General procedure for the preparation of 1-alkyl / alkenyl-cyclohexan-1-ols

20 ml of a solution of 0.5 mol of alkyl halide in 150 ml of ether are added dropwise to 0.5 mol of magnesium shavings in 50 ml of anhydrous ether in the heated apparatus. As soon as the Grignard reagent begins to form, the remaining alkyl halide solution is added so quickly that the ether boils weakly. When the addition is complete, the mixture is heated under reflux for about 112 hours.

0.45 mol of the corresponding cyclohexanone in 100 ml of ether are added dropwise to the cooled Grignard solution with stirring and the mixture is stirred under reflux for about 1/2 hour.

For working up, the reaction mixture is cooled to 0 ° C. and carefully poured into a cold, saturated NH ₄ Cl solution (about 300 ml). The ether phase is then separated off and the aqueous phase is extracted twice with 80 ml of ether each time. The combined ethereal phases are washed with saturated sodium bicarbonate and sodium chloride solution. After drying with sodium sulfate and evaporation of the solvent, the residue is i. Vac. distilled.

• 1-Ethyl-cyclohexan-1-ol Geruch: camphrig, holzig.
• 1,3,3,5-Tetramethyl-cyclohexan-1-ol Geruch: erdig.

The following connections were made according to this manufacturing instruction:

• 1-ethyl-cyclohexan-1-ol Odor: camphorous, woody.
• 1,3,3,5-tetramethyl-cyclohexan-1-ol Odor: earthy.

Bouquet for liquid and solid mixtures containing active chlorine

• 100 parts by weight of 1-cyano-dodecane
• 150 parts by weight of 2,6-dimethylheptan-2-ol
• 100 parts by weight of 1-ethyl-cyclohexan-1-ol
• 100 parts by weight of dihydromyrcenol
• 150 parts by weight of tetrahydrolinolool
• 100 parts by weight of terpinol
• 300 parts by weight of dipropylene glycol

Claims (3)

1. Use of 1-alkyl / alkenyl-cyclohexan-1-ols of the general formula I

wherein R is an alkyl group with 1 to 4 carbon atoms or an alkenyl group with 2 to 4 carbon atoms, 0 to 3 of the 10 radicals R 'methyl and 10 to 7 of the 10 radicals R' are hydrogen, as fragrances in mixtures containing active chlorine. 2. Use of cyclohexan-1-ols according to claim 1, characterized in that R is ethyl and all radicals R 'are hydrogen. 3. Use of cyclohexan-1-ol according to claim 1, characterized in that 1, 3,3,5-tetramethyl-cyclohexan-1-ol is used as a fragrance.