Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1991-12-09
1993-11-23
Dees, Jose G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
512 14, 512 17, 512 18, 514535, C07C22938, C07C22956, A61K 746
Patent
active
052646157
DESCRIPTION:
BRIEF SUMMARY
The invention relates to novel odorants, namely Schiff bases.
In particular, the invention is concerned with the compounds of the formula ##STR2## wherein R.sup.1 signifies CH.sub.3, C.sub.2 H.sub.5 CH(CH.sub.3).sub.2, 2,3-butylidene. total number of carbon atoms of R.sup.4, R.sup.5, R.sup.6 R.sup.7, .ltoreq.6
Accordingly, tetralins and indanes are embraced by formula I.
The compounds of formula I are distinguished by very natural notes in the direction of musk. Worthy of mentioning is in particular a frequent combination of musky and flowery notes, this combination of notes being of particular interest because of the resulting powerful body notes. Concerning the flowery notes, the orange blossom and tuberose aspects may in particular be mentioned.
They exhibit good substantivity, especially in fabric softeners and detergents.
They are not only suited in odorant compositions of the flowery, but also of many other types, especially those suited in the field of the luxury perfumery.
The compounds of formula I are obtained as the essential reaction products of a process comprising reacting a carbonyl compound of formula ##STR3## with an alkyl anthranilate of formula ##STR4##
The convenient process parameters are as follows: Lewis acids, such as BF.sub.3, etc., molecular sieves of the acid type reduced pressure, then crystallization of the residue; or utilization of the residue as such. The crystallization is effected using solvents such as heptane or ethanol, etc.
The carbonyls II can also be used in the form of their acetals of ketals, namely the derivatives of the formula ##STR5## see for example EP 0379981 (A.sub.1), formula I for the definition of the radicals and the preparation of such derivatives.
The novel Schiff bases combine with numerous known odorant ingredients of natural or synthetic origin, whereby the range of the natural raw substances can embrace not only readily-volatile, but also moderately-volatile and slightly-volatile components and that of the synthetics can embrace representatives from practically all classes of substances, as will be evident from the following compilation: (such as bergamot oil, mandarin oil, etc.), mastrix absolute, myrtle oil, palmarosa oil, patchouli oil, petitgrain oil Paraguay, wormwood oil, rhodinol, cinnamic alcohol, hydroxycitronellal, Lilial.RTM.(p-tert.butyl-.alpha.-methyl-dihydrocinnamaldehyde), methylnonylacetaldehyde, (isomethyl-.alpha.-ionone), methylionone, propionate, citronellyl acetate, citronellyl ethoxolate (citronellyl) . O--CO--CO. OC.sub.2 H.sub.5), decyl acetate, dimethylbenzylcarbinyl acetate, dimethylbenzylcarbinyl butyrate, ethyl acetoacetate, ethyl acetylacetate, hexenyl isobutyrate, linalyl acetate, methyl dihydrojasmonate, styrallyl acetate, vetiveryl acetate, etc., p-menthane-8-thiol-3-one, methyleugenol.
The Schiff bases can be used in wide limits which can range in compositions, for example, from about 0.1 (detergents)-about 20% (alcoholic solutions), without these values being, however, limiting values, as the experienced perfumer can also achieve effects with even lower concentrations or can synthesize novel complexes with even higher amounts. The preferred concentrations range between about 1 and about 10%. The compositions manufactured with I can be used for all kinds of perfumed consumer goods (eau de cologne, each de toilette, extracts, lotions, creams, shampoos, soaps, salves, powders, toothpastes, mouth washes, deodorants, detergents, fabric conditioners, tobacco, etc.).
The Schiff bases can accordingly be used in the manufacture of compositions and-as the above compilation shows-using a wide range of known odorants or odorant mixtures. In the manufacture of such compositions the known odorants referred to above can be used according to methods known to the perfumer such as e.g. from W. A. Poucher, Perfumes, Cosmetics and Soaps 2, 7th Edition, Chapman and Hall, London, 1974.
EXAMPLES
1. Method A
Into a three necked reaction flask equipped with a stirrer, a thermometer, a water trap and a condenser, 0.5 moles of aldehyde
REFERENCES:
patent: 4806363 (1989-02-01), Mookherjee et al.
patent: 4853369 (1989-08-01), Mookherjee et al.
patent: 5084440 (1992-01-01), Baudin et al.
patent: 5155095 (1992-10-01), Blanc et al.
Mar., Advanced Organic Chemistry, 3rd ed., pp. 796-797.
CA 107: 242459b (1987).
Dees Jos,e G.
Frazier B.
Givaudan Corporation
Tavares Robert F.
Vag Linda A.
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