DE1592998B1 - Use of certain ethers for the production of synthetic perfume compositions - Google Patents

Description

The invention relates to the use of certain xyl ethers particularly well suited, so it has surprisingly been shown over ethers for the production of synthetic perfume compositions that one can use the most diverse functions, where these ethers in a certain amount with several perfume compositions good perfume qualities also reren fragrances of synthetic or natural her- can be bestowed by being mixed with them in general future. Such perfume compositions, an ether of the general formula, can be further used or processed as such or after appropriate dilution. R ₁ - O - R ₂ However, they are usually in small amounts
other commodities or commodities, such as in which means: room sprays, soaps, detergents, cosmetic io

or deodorising preparations, or substrates, R _{1 is} a methyl or ethyl radical; and, like fabrics, fibers or paper products, incorporated in order to give them an appealing fragrance note to R ₂ an alkyl radical with 5 or 6 carbon atoms; to lend. Thus, perfume compositions are an alkenyl radical with 5 carbon atoms or of the type described, which are either simply composed of a hex-3-enyl radical or from a complex mixture

different perfume ingredients can exist, in an amount based on the total weight of the

as such or “perfumed” with them, requirement or perfume _{ingredients, from O 3} OO1 to 2, preferably

Utensils sold in stores. incorporated from 0.1 to 1.0 percent by weight.

When distilling natural lavandin oil and 20 the ethers of the given formula R ₁ - O - R ₂

subsequent gas / liquid chromatography are according to the invention in perfume compositions in

Analysis of the fractions obtained was generally only used in small amounts, since

Surprisingly, it was found that natural lavandin - even in these small amounts - is the desired one

oil causes a small amount of a previously neglected "head odor", benen connection contains. In the case of this compound 25 it was found that the through an ether of

it is methyl-n-hexyl-ether, the scent note produced by a given formula is very good.

extremely pleasant "head odor"("topnote" odor) is more pronounced when R _{2 represents} an alkenyl radical than

having. when R ₂ denotes the corresponding alkyl radical.

Was this connection after per se known The fact that by the ether of the ange methods produced, it was found that the synthetic formula gave the head odor of the synthetic perfume table produced ether can improve the same desirable compositions is surprising because Has fragrance properties. This is evident from Morel in the magazine Soap, Perfumery and point out that even a small addition of cosmetics ", 27, pp. 169 to 176 (1954) the fragrances of the Methyl-n-hexyl-ether the "head odor" qualities of the simple aliphatic ethers than for perfumery various synthetic, d. H. by mixing 35 of little or no importance and rejects natural and / or synthetic perfume ümingredien- emphasizes that the corresponding ketones or esters zien produced perfume compositions are noticeably far more suitable. That of the present invention is improved. Through this mixing together, all of the basic knowledge becomes, namely that but not the naturally occurring composition through the addition of an ether of the formula given reproduced because the naturally occurring essential odor properties of the most varied of parsons Improving oils from a mixture of füm compositions is therefore in Very large number of ingredients exist, which is a complete contradiction to the knowledge to which when compared with the relatively small number M 0 r e 1 as a result of his work on the fragrance of Ingredients in a synthetic perfume has got properties of the individual compounds. composition must not be disregarded. 45 In a particularly advantageous way the ethers

A very similar, smelling of "green leaves" to the formula given, preferably methyl-n-hexyl-

Ether, namely ethylhex-1-enylether, was already, ether, together with an ocimen, in particular

according to the teachings of the USA. patent a /? - Oeimen. The latter can be derived from the

3 061649, into a synthetic lavender perfume cis-ß-ocimen, the trans- / 9-ocimen or from a

Composition incorporated, around the lavender scent of which there are 50 mixture of the same. The best results

to come into its own in a more natural way. A disadvantage from the perfumer's point of view is achieved before

What is part of this procedure, however, is that the necessary everything in the production of synthetic lavandin

Amount of ether, namely. 3 parts ether to 50 parts oil, lavender oil or spiked lavender oil, if you

Perfume ingredients is very large. Since it is also used on preferably trans- / 3-ocimene. The Ocimene

is generally known in the relevant field, 55 can be carried out by controlled pyrolysis of -pinene or

that a perfume composition can be obtained by adding linalyl acetate by pyrolysis,

even structurally extremely closely related compounds- The ocimen is usually in a set of

genes imparted fragrance properties even with knowledge 1 to 10 percent by weight, preferably 4 to 8

the scent note of one or the other compound is not weight percent, based on the total weight of the

make the known fragrance ingredients of the composition, present,

Shafts of ethylhexenyl (l) -ether do not. Furthermore, it has proven to be advantageous to use the ethers

the slightest indication of a corresponding or similar fragrance to the specified formula in perfume compositions

properties of the use according to the invention that are used as the main perfume ingredients

Ether and especially for their usability for zien, linalool and linalyl acetate and possibly

Increase in the "head odor" of various types of borneol and camphor. A mixture of the

synthetic perfume compositions. Ether and linalool can be used for the manufacture of

Even if there are commercially available synthetic synthetic perfume compositions

According to the invention, perfume compositions are methyl-n-driven. For example, contains a synthetic

ORICHNAL INSPECTED

Lavandin oil usually has the appropriate amounts of linalool, linalyl acetate, borneol and camphor as main perfume ingredients, while a synthetic lavender oil is largely based on linalool and linalyl acetate is built up.

The synthetic perfume compositions produced using an ether of the formula given find technical application for a variety of perfumed materials. The compositions can z. B. can be used in room sprays, or they are used in soaps, detergents or deodorising preparations mixed in, including in bath salts, shampoos, and toilet waters, or they become cosmetic Incorporated preparations such as colognes, toilet waters, face creams, talcum powders, body lotions or sunscreen or men's toiletries such as shaving lotions and creams. The compositions can also be used to create substrates such as fibers, fabrics and paper products, to perfume.

As already mentioned, of the ethers of the formula given, preference is given to using methyl-n-hexyl ether. If a strongly scented compound is required, R _{2 can} expediently denote a hexylene radical, preferably a hex-3-enyl radical. In those cases in which R _{2 is} a C ₅ group, the fragrance properties are less pronounced, but still completely satisfactory from a technical point of view. The radical R ₂ is preferably straight-chain; but it can also be branched and in particular be in the form of an iso group. Although methyl ethers are preferably used (R ₁ = methyl), the corresponding ethyl ethers can also be used, especially when R _{2 is} a C ₅ isoalkenyl radical, as is the case with ethyl prenyl ether. If necessary, mixtures of these ethers can of course also be used. The ethers which can be used according to the invention include: methyln-hexyl ether; Ethyl n-hexyl ether; Methyl-cis-hex-3-enyl ether; Ethyl cis-hex-3-enyl ether; Methyl isohexyl ether; Methyl n-pentyl ether; Methyl isopentyl ether; Methyl prenyl ether; Methyl 3-methyl-but-2-enyl ether and ethyl prenyl ether.

The mixed ethers of the general formula R ₁ - O - R ₂ can be prepared without difficulty by methods known per se, e.g. B. be prepared by Williamson synthesis. The appropriate "alkyl or alkenyl halide" is reacted with sodium methylate or ethylate. The ethers of the formula given represent liquids with boiling points between 100 and 180 ° C, which can be purified by distillation. However, when stored, they easily form peroxides, so that it is convenient to store them in admixture with a peroxidation inhibitor, such an inhibitor must of course also be suitable from the point of view of the perfumer.

The following examples are intended to illustrate the use of ethers of the formula given according to the invention Illustrate the production of synthetic perfume compositions in more detail. In the examples, all mean Quantities by weight.

example 1

According to the following recipe, a perfume composition was mixed with regard to its fragrance properties largely corresponded to natural lavandin oil.

Parts by weight

Borneol Crystals 60

Camphor (refined) 30

. ₅ coumarin 5

Linalool 350

Eucalyptol 50

Ocimen 70

Sage oil 30

Turpentine 30

Linalyl acetate 370

Methyl n-hexyl ether 5

1000

Cis and trans ocimes were used in separate batches. It turned out that the under Use of trans-Ocimen mixed perfume composition was qualitatively better. Became the methylhexyl ether Replaced by ethyl prenyl ether corresponded to that obtained when the components mentioned were mixed Perfume composition also natural lavandin oil in terms of its scent note. But became the ether Replaced by ethyl amyl ketone, the "head odor" quality of the perfume composition was inferior.

Example 2

A perfume composition was mixed according to the following recipe, which is used for the production of Lavender-type toilet watering proved suitable.

Parts by weight

Coumarin 70

Ambrite Musk 50

Lavandin abrialis 100

Linalyl acetate. "... '.' 130

Amyl salicylate 30

Benzyl acetate 50

Citronellyl acetate 20

Clove stem oil 20

Geraniol 60

Geranium oil 50

Lavandin Resinoid 70

Linalool 70

Oak moss resinoid 20

sweet orange peel oil 20

Patchouli oil 30

Balsam of Peru 50

west indian sandalwood oil 50

Ocimen 10

Benzyl benzoate 90

Methyl n-hexyl ether 10

1000

Despite the presence of natural lavandin oil in the perfume composition, the presence conveyed of methyl-n-hexyl ether a completely different scent note at the first scent impression.

Example 3

A perfume composition was mixed according to the following recipe, which is used for the production of Toilet water of the "cologne" type was used. Due to the presence of the methyl n-hexyl ether the impression was given as if in the perfume composition a significant proportion of natural Lavender oil would have been mixed in.

Claims (1)

5 6 Weight rate when replacing methyl n-hexyl ether with. Methyl- Methyl- ε -naphthyl ketone 20 cis-hex-3-enyl ether gave a concentrate with Methylnonylacetaldehyde 2 similar fragrance, which at the same time has a pleasant, artificial bergamot oil 700 _& ^blunu S ^{e note} Mandarin oil 30 claims: terpene-free oil 50 Petitgrain _{"TT Λ.} ..., " Thyme oil 20 · * ■ · Use of an ether of general Yiang-Yiang-öi "::::::::::::::::::::::: 10 ^Formei: _ _ _ Benzyl benzoate 158. ,, _t K _{1 -UK 2} Methyl-n-hexyl ether 10 ^{10 wonn means:} 1000 ^ ^{1 emen} methyl or ethyl radical; and R _{2 is} an alkyl radical having 5 or 6 carbon atoms; an alkenyl radical with 5 carbon Example 4 atoms or a hex-3-enyl radical The perfume mixed from the following ingredients in one amount based on the total weight In terms of its fragrance note, the composition corresponded to the perfume ingredients, from 0.001 to 2, preferably largely a standard Fougere type. from 0.1 to 1.0 percent by weight for manufacturing Parts by weight * ^and § of synthetic perfume compositions. Coumarin 60 ²⁰ ^ " Use of an ether according to claim 1 Ambergris \\ Y ^ Y / ^ '.'. '.'. '.'. '.'. '. 50 ^{for the} production of synthetic perfume compositions Calbanum resinoid 50 nen characterized in that one additionally Geranioi 100 at least one p-Ocimen, preferably em trans- Phenyl-äthylälköhoV VZZ ^] V /. '.'. '.'. '.'. '.'. '.'. 50 ^ - Occimes used. Linaiylacetat 50 ²⁵ Use of an ether according to one of the Benzyl acetate 30 Proverbs 1 and 2 for the manufacture of synthetic Zimtaldehvd 5 perfume compositions, characterized in that Cedarwood oil 70 ^as ^ ^one major ^addition ^ ^em ether as Clove Oil '^ Y ^ V ^.'. Y. '.'. '.'. '.'. '. 20 Perfume ingredients Linalool and Linaiylacetat Geranium oil 50 ³ ° as well as possibly borneol and camphor artificial lavender oil ................. 300 ^w T ¥ ^< , ■ χ uu ■ α κ Oakmoss Resinoid 30 4 Use of an ether according to one of the following Patchouli 40 Proverbs 1 to 3 for making synthetic Petit inöi 2o perfume compositions, which in turn are part of Methyl-n-hexyl ether '.'. '.'. '.'. '.' / Y '. \\ Y.'. '.'. Y 5 ™ ^ ^{1 v} ° ⁿ Room sprays soaps, detergents or Forming deodorants or fabrics, fibers or 1000 paper products can be incorporated.