EP3999620A1

EP3999620A1 - Fragrance mixture containing 1,3-propanediol

Info

Publication number: EP3999620A1
Application number: EP20739420.6A
Authority: EP
Inventors: Bernd HÖLSCHER; Julia AMOS
Original assignee: Symrise AG
Current assignee: Symrise AG
Priority date: 2019-07-16
Filing date: 2020-07-16
Publication date: 2022-05-25
Also published as: US20220273537A1; WO2021008696A1; WO2021009315A1

Abstract

The invention relates to non-aqueous fragrance mixtures comprising 1,3-Propanediol and one or more fragrance substance(s), in particular from the group of fragrance alcohols with green notes and/or the group of fragrance alcohols with floral notes, to a method for producing the fragrance mixtures, to a method for modifying the sensory properties of a fragrance substance, to the use of 1,3- Propanediol for modifying sensory properties of a fragrance in a fragrance mixture and for producing a fragrance mixture, to the use of the fragrance mixtures for producing perfumed products, perfumed products containing the fragrance mixtures in a sensory effective amount and to a method for producing the fragrance mixtures.

Description

Fragrance mixtures containing 1,3-propanediol

Field of invention

The invention is in the field of fragrances and relates to non-aqueous fragrance mixtures with modified sensory properties, a method for producing the fragrance mixtures, a method for modifying the sensory properties of a fragrance, the use of 1,3-propanediol to modify sensory Properties of a fragrance in a fragrance mixture and for the production of a fragrance mixture, the use of the fragrance mixtures for the production of perfumed products, perfumed products which contain the fragrance mixtures in a sensorially effective amount, as well as a method for producing the fragrance mixtures.

In principle, there is a constant need on the part of the perfume industry and in the manufacture of perfumed products to enhance (emphasize / emphasize) pleasant olfactory aspects of fragrances and to mask or reduce unpleasant odorous aspects. In particular, floral fragrances, i.e. fragrances with a floral note, play an important role in perfumery. It is desirable, on the one hand, to particularly emphasize their natural freshness and / or radiance and, on the other hand, to suppress their greasy, metallic and / or technical notes.

[0003] The reduction of unpleasant smells is a problem that is difficult to deal with and solve in terms of composition. Above all, the special nature of a respective unpleasant odor severely limits the possible uses. Often unpleasant odors can be reduced at best by combining them with a specially developed perfume oil, which itself has its own, very specific type of scent. The unpleasant smell impressions are often only masked with the help of fragrant smells of a (different) substance. Numerous proposals for eliminating unpleasant odors can be found in the literature, as shown by way of example below.

[0005] WO 01/43784 A2 and US 2003 068295 A1 describe the use of certain esters, in particular isomenthyl esters such as isomenthyl acetate, as odor-neutralizing substances for reducing unpleasant odors of various types.

WO 2016/164205 A1 discloses aqueous multilamellar composition for the delivery of a hydrophobic substance which comprises 50 to 80% by weight phenylethyl alcohol and / or phenylpropyl alcohol and optionally 10 to 20% by weight 1,3-propanediol. 1,3-Propanediol is used there as a solubilizer.

EP 2 822 401 and EP 3 440 942 A1 relate to foods and beverages which comprise 1,3-propanediol for modifying aroma. The amount of 1,3-propanediol used is 0.01 to 5% by weight or 0.1 to 2% by weight.

US 2007 0241306 A1 discloses numerous biodegradable

Compositions comprising 1,3-propanediol.

EP 2 926 673 A1 relates to mixtures of substances comprising terpene, 1,3-propanediol and active ingredients such as rebaudiosides and steviosides. 1,3-Propanediol is used in these mixtures in an amount of 20 to 80% by weight.

[0010] Previous (odor) substances or (odor) substance mixtures which aim to improve the odor of products often have an unsatisfactory odor reduction in unpleasant smells. The methods known in the prior art for reducing unpleasant odors often have the disadvantage that the (odorous) substances or (odorous) substance mixtures used have to be used in considerable quantities, which can lead to costs and application problems.

Substances or substances that are able to increase the intensity of pleasant smells and / or of are therefore of considerable advantage masking, reducing or even completely eliminating unpleasant odors without being of a noteworthy odorous perfumery intensity or without being of an appreciable odorous perfumery intensity itself in the concentration to be used for the purpose of odor intensification and / or odor reduction.

In the case of perfume alcohols, which play an important role in perfumery, this applies in particular to their natural freshness and flowery appearance on the one hand and their musty, artificial and metallic notes.

The use of the above-mentioned substances or substances should also be such that they can be used for scenting or perfuming any scent direction.

Advantageously, these substances or substances should come from natural or sustainably produced raw materials and, in addition to the properties listed above, have other positive properties such as an antibacterial effect.

[0015] There is even more a need for substances or substances which do not have any adverse health effects.

In the perfumery sector, for example in the preparation or preparation of odorant mixtures, 1,2-propanediol (propylene glycol) or dipropylene glycol were predominantly used as common solvents in the past.

The compound 1, 3-propanediol is known from the prior art. In the perfumery sector, 1,3-propanediol has so far not found any use worth mentioning. In particular, the specification of certain quantitative ratios in the production of fragrance mixtures is not known, and certainly not an olfactory effect when combined with any fragrance (s). [0018] It was therefore the primary object of the present invention to provide alternative or improved substances or substances, for example additives or solvents, for modifying sensory properties of fragrances in non-aqueous fragrance mixtures. These should also be accessible from natural sources.

Such substances should preferably meet one, several or preferably all of the following requirements:

easy accessibility, i.e. production from natural and sustainably produced raw materials,

high effectiveness in low concentration, preferably with an intrinsic odor that is imperceptible or hardly perceptible in low concentrations,

extensive or complete colorlessness,

high stability in various mixtures or preparations, whereby in particular no discoloration and / or separation and / or turbidity should occur,

inert behavior,

no toxic and / or allergenic effects on humans.

Furthermore, the present invention should provide new, advantageous non-aqueous fragrance mixtures, in particular perfume oils, which contain such substances, and a method for producing such fragrance mixtures.

Such odorant mixtures should preferably be suitable for scenting or perfuming certain products.

Furthermore, correspondingly perfumed products which contain such a non-aqueous fragrance mixture, as well as a method for producing such perfumed products should be specified. [0023] Further objects on which the present invention is based emerge from the following statements and the attached claims.

Summary of the invention

A first aspect of the invention relates to a non-aqueous

Fragrance mixture, preferably a perfume oil, comprising or consisting of

(i)> 10% by weight 1,3-propanediol; and

(ii) one or more fragrance (s) from the group of fragrance alcohols, preferably from the group of fragrance alcohols with green odor notes and / or the group of odorant alcohols with flowery odor notes.

In a second aspect, the present invention relates to a method for producing a non-aqueous fragrance mixture, which comprises the following steps:

Providing 1,3-propanediol;

Providing a fragrance alcohol or a plurality of fragrance alcohols from the group of fragrance alcohols, preferably from the group of fragrance alcohols with green notes and / or the group of fragrance alcohols with floral notes.

Bringing into contact and mixing an effective amount of> 10% by weight of 1,3-propanediol with the one fragrance alcohol or the several fragrance alcohols to obtain the non-aqueous fragrance mixture.

The third subject matter of the present invention is a method for modifying the sensory properties of a fragrance alcohol or several fragrance alcohols, which comprises the following steps:

Mixing of a fragrance alcohol or several fragrance alcohols with an effective amount of> 10% by weight of 1,3-propanediol

to highlight a pleasant odor note or all pleasant odor notes of a fragrance alcohol or several fragrance alcohols or to emphasize

preferably to emphasize or emphasize the pleasant smell note or all pleasant smell notes more charisma, natural freshness or flowery odor note (s) of an odorant alcohol or several odoriferous alcohols;

and or

to mask or reduce an unpleasant odor note or all unpleasant odor notes of a fragrance alcohol or several fragrance alcohols,

preferably to mask or reduce the unpleasant odor note or all unpleasant odor notes musty, greasy, technical or metallic odor note (s) of an odorant alcohol or several odorant alcohols.

In a fourth aspect, the present invention relates to the use of 1,3-propanediol in an effective amount for modifying the sensory properties of a fragrance alcohol or more fragrance alcohols, in particular

for emphasizing or intensifying a pleasant odor note or all pleasant odor notes of a fragrance alcohol or several fragrance alcohols;

and or

for masking or reducing an unpleasant odor note or all unpleasant odor notes of a fragrance alcohol or several fragrance alcohols.

Fifth object of the present invention is the use of 1, 3-propanediol for freezing a non-aqueous odorant mixture, comprising or consisting of

(i)> 10% by weight 1,3-propanediol; and

(ii) one or more fragrance (s) from the group of fragrance alcohols, preferably from the group of fragrance alcohols with green odor notes and / or the group of odorant alcohols with flowery odor notes. In a sixth aspect, the present invention relates to the use of the non-aqueous fragrance mixture or fragrance mixture according to the invention in a sensorially effective amount for modifying an odor note in a perfumed product or for producing a perfumed product.

In a further aspect, the present invention relates to a perfumed product which comprises a sensorially effective amount of the non-aqueous fragrance mixture or fragrance mixture according to the invention.

Finally, in a further aspect, the present invention relates to a method for producing a perfumed product, which comprises the following steps:

(a1) providing the fragrance mixture according to the invention,

(b1) providing a further component or several further components of the perfumed product to be produced, and

(c1) bringing into contact or mixing a sensorially effective amount of the fragrance mixture provided in step (a1) with the further component (s) provided in step (b1) to obtain the perfumed product;

the amount of 1,3-propanediol (i) being> 10% by weight, based on the total weight of the fragrance mixture

to emphasize or intensify a pleasant odor note or all pleasant odor notes of the fragrance alcohol (s) of the fragrance mixture (ii),

preferably to emphasize or accentuate the charisma, natural freshness or the flowery odor notes of the one odorant alcohol or of the several odorant alcohols (ii) of the odorant mixture;

and or

to mask or to mask an unpleasant odor note or all unpleasant odor notes of the one fragrance alcohol or of the several fragrance alcohols (ii) of the fragrance mixture Reduce,

preferably to mask or reduce the musty, fatty, technical or metallic odor notes of the one odorous substance alcohol or of the several odorous substance alcohols;

or

(a2) providing a fragrance alcohol or several fragrance alcohols (ii) of the fragrance mixture according to the invention,

(b2) providing a further component or several further components of the perfumed product to be manufactured,

(c2) mixing a sensorially effective amount of the one or more fragrance alcohols provided in step (a2) with the further component (s) provided in step (b2) to obtain a mixture, and

(d2) Bringing the mixture obtained in step (c2) into contact with 1,3-propanediol, the amount of 1,3-propanediol being> 10% by weight, based on the total weight of the fragrance mixture

to emphasize or emphasize a pleasant odor note or all pleasant odor notes of the one fragrance alcohol or the several fragrance alcohols (ii),

preferably the charisma, natural freshness or the flowery odor notes of one or more fragrance alcohols

To emphasize or emphasize fragrance alcohols (ii);

and or

to mask or reduce an unpleasant odor note or all unpleasant odor notes of the one olfactory alcohol or the several odorous substance alcohols (ii),

preferably the musty, fatty, technical or metallic odor notes of one or more odorous substance alcohol

To mask or reduce fragrance alcohols (ii).

These and other aspects, features, and advantages of the present invention will become apparent to those skilled in the art from a study of the following detailed description and claims. Each feature can be selected one aspect of the invention can be used or substituted for another aspect of the invention. Furthermore, it goes without saying that the examples contained in the present application describe and illustrate the invention, but do not limit it, and that in particular the present invention is not limited to these examples.

Unless otherwise stated, all percentages are% by weight. Numerical examples given in the form “from x to y” include the stated values. If several preferred numerical ranges are given in this format, it is understood that all ranges resulting from the combination of the various endpoints are also recorded.

Detailed description of the invention

In a first aspect, the present invention relates to a non-aqueous fragrance mixture, preferably a perfume oil, comprising or consisting of

(i)> 10% by weight 1,3-propanediol; and

(ii) one or more odorant (s) from the group of odorant alcohols, in particular from the group of odorant alcohols with green odor notes and / or the group of odorant alcohols with flowery odor notes.

The odorant mixture according to the invention is a non-aqueous odorant mixture. The term “non-aqueous” fragrance mixture in the context of the present invention is understood to mean a fragrance mixture which is characterized in that it has a water content of less than approximately 1% by weight or is completely anhydrous. In the following description, the term “fragrance mixture” is always understood to mean a non-aqueous fragrance mixture, even if this is not explicitly stated.

The first component (i) of the fragrance mixture according to the invention is 1,3-propanediol. 1,3-Propanediol consists of the basic structure of propane, at the terminal positions of which there is a flydroxy group. 1, 3-propanediol belongs to the group of dihydric alcohols, the diols. It is a colorless, hygroscopic liquid with only a weak or no odor of its own.

1, 3-Propanediol can be produced either by chemical synthesis or by microorganisms biotechnologically from corn or from glycerol, which is obtained as a by-product of the transesterification of vegetable oils in the production of biodiesel from rapeseed oil. As a result, it is a sustainably produced product that is easily accessible.

In perfumery, 1,3-propanediol has so far not found any noteworthy use, in particular not as a solvent in the preparation and production of odorant mixtures.

In the perfumery sector, for example in the preparation or production of fragrance mixtures, 1,2-propanediol or dipropylene glycol were predominantly used as common solvents in the past.

1,2-Propanediol is a clear, colorless, almost odorless and strongly hygroscopic liquid. 1,2-Propanediol is used because of its dissolving and emulsifying properties, among other things, as a carrier or as a carrier solvent for dyes, flavors, emulsifiers, etc. or is used in cosmetic products such as skin creams, toothpaste, mouthwashes and deodorants mainly as a solvent or humectant.

Industrially, 1,2-propanediol is produced synthetically by hydrolysis of propylene oxide. Depending on the manufacturer, either a high-temperature process without catalysis at 200 to 220 ° C or a catalytic process at 150 to 180 ° C in the presence of an ion exchange resin or no amounts of sulfuric acid or alkalis is used. The disadvantage of 1,2-propanediol as a solvent is that it forms acetals with fragrances with aldehyde functionality. The formation of acetal causes a change and thus a deterioration in the odor profile. Dipropylene glycol (DPG) is obtained as a by-product in the production of 1,2-propanediol. Dipropylene glycol is a colorless, hygroscopic, viscous, odorless and not very volatile liquid. Dipropylene glycol, as an isomer mixture of three structural isomers, is used either as a solvent for odor-sensitive applications such as flavors or as a humectant for a variety of cosmetic applications.

Both solvents are not made from natural raw materials.

Compared to 1,2-propanediol or dipropylene glycol (DPG), 1,3-propanediol is distinguished by the fact that it can be obtained from natural or sustainably produced raw materials.

In addition to its primary sensory properties, 1,3-propanediol has additional positive secondary properties. These secondary properties include: high stability under certain application conditions, for example in alkaline media, e.g. washing powder, fabric softeners, soaps, shampoos, etc. Furthermore, it has been shown that 1,3-propanediol is less reactive and therefore inert compared to 1,2-propanediol compared to odorous substances, whereby in combination with one or more odorous substance (s) the odor profile is not adversely changed, for example through the breakdown of odorous substances or through the formation of by-products. Furthermore, 1,3-propanediol shows an antibacterial effect.

It was also surprising that 1,3-propanediol of the fragrance mixture according to the invention can be permanently and stably incorporated into a large number of different formulations.

The second component (ii) of the fragrance mixture according to the invention is a single fragrance or a mixture of two, three, four, five, six, seven, eight, nine or more different fragrances from the group of fragrance alcohols. The fragrance alcohols used according to the invention are compounds with C6 to C11 carbon atoms which have an OH group functionality.

Such odorant alcohols represent a very important odorant group in perfumery and are known in principle to the person skilled in the art. A description of the odor properties of the odorant alcohols can be found, inter alia, in the specialist book "S. Arctander: Perfume and Flavor Materials, Volumes I and II, Montclair, N. J., 1969, self-published". Examples of fragrance alcohols are disclosed in "H. Surburg, J. Panten: Common Fragrance and Flavor Materials, 6th Edition, Wiley-VCFI, Weinheim, 2016". The relevant disclosure in both literature sources is fully incorporated by specific reference in the present application accepted.

The perfume alcohols are distinguished either by a flowery, soft or sweet fragrance and often form the basis for floral fragrance compositions or are distinguished by a fresh, green or metallic fragrance. The terms “flowery”, “fresh”, “green”, “metallic” are standard terms from the classification system of basic odors or smell qualities and the fragrance or odorous substance area, as defined in the standard literature cited above.

Surprisingly, the presence of 1,3-propanediol in a fragrance mixture according to the invention has the effect that certain olfactory aspects of one or more fragrance alcohols are modified, i.e. emphasized or emphasized and / or masked or reduced.

Surprisingly, 1, 3-propanediol in a fragrance mixture has the effect that in particular the positive, ie pleasant odor notes, such as radiance, natural freshness or the flowery odor notes of a fragrance alcohol or all fragrance alcohols emphasize or emphasize, ie intensify, and / or the negative ones , ie unpleasant odor notes such as musty, fatty, technical or metallic odor notes of a fragrance alcohol or all odorant alcohols are masked or reduced.

With regard to the terms “highlighting” or “emphasizing”, in the context of the present application an intensification of the intensity of a positive, pleasant smell is understood, in particular of smells or smell notes of the type more charisma, natural freshness, flowery smell notes and / or the like Odors as opposed to being overlaid / covered by another dominant odor note.

According to a preferred aspect of the present invention, 1, 3-propanediol is particularly suitable for masking or reducing, especially for reducing, one or more unpleasant odor notes of an odorous substance alcohol or several odorous substance alcohols.

With regard to the term "masking" it should be noted in the context of the present invention that a particular form of odor change is meant, namely the neutralization of an unpleasant odor, for example, as opposed to overlaying / covering up by another dominant odor note.

With regard to the term "reduce" it should be noted that a particular form of odor change is meant, namely the weakening of the intensity of an unpleasant odor, for example, in contrast to an overlaying / covering by another dominant odor note. In the context of the present application, a reduction in unpleasant odor notes is understood to mean a partial or complete reduction, ie elimination, of unpleasant odors by a certain substance or a certain mixture of substances, in particular odors or odor notes of the musty, greasy, technical, metallic type and / or similar smells.

The 1,3-propanediol to be used according to the invention is advantageously easily accessible or can be prepared, has a high level of effectiveness even in low concentrations, in particular in concentrations at which 1,3-propanediol has none or at least only has a barely perceptible odor of its own, is largely or completely colorless, is inert to odorous substances, so that in combination with one or more odorous substance (s) the odor profile is not adversely affected, has a high stability in different mixtures or preparations and has no toxic and / or allergenic effects on humans.

In addition, 1,3-propanediol has an antibacterial effect, a property which gives the resulting products microbial stability and thus durability.

1,3-Propanediol also has the advantage that when it is used, in particular a use according to the invention, it can be combined with different fragrances and customary components of a fragrance mixture in order to perfume products with any fragrance. Consequently, the present invention can offer consumers a wide range of types of fragrance.

The substances with an unpleasant smell mentioned here can also have further, generally not unpleasant sensory qualities, including olfactory qualities. In the context of the present description, substances that have an unpleasant smell are generally understood to be those that cause one or more unpleasant odor impressions or notes, be it as a primary odor or as a secondary / subordinate odor note. In particular, the unpleasant-smelling substances described herein can also be those fragrances that are primarily perceived as pleasant-smelling substances, but also have an unpleasant metallic, greasy and / or technical odor note, which according to the invention should preferably be reduced.

The same applies analogously to the pleasantly smelling substances described herein. In the context of the present text, substances with a pleasant smell are generally understood to mean substances that produce one or more pleasant odor impressions or odor notes, be it as a primary odor or as a secondary / subordinate odor note. As a result, in the context of the present invention, for example, both an unpleasant odor note of a certain (unpleasant smelling) substance can be masked or reduced, and a pleasant odor note of the same (also pleasantly smelling) substance can be enhanced.

The one, several or all of the odorant alcohol (s) whose odorous properties are improved according to the invention by using 1,3-propanediol is preferably a odorant alcohol with a green odor note or a odorant alcohol with a floral odor note.

In principle, such a fragrance mixture according to the invention is preferred in which the one, the several or all of the unpleasant and / or pleasant-smelling fragrance alcohol (s) with a green odor note is / are selected from the group consisting of fragrance alcohols with a molecular weight in the range from 100 g / mol to 190 g / mol, preferably in the range from 100 g / mol to 158 g / mol.

In a preferred variant, the invention relates to a fragrance mixture, preferably a perfume oil, in which the one fragrance alcohol or several fragrance alcohols with a green odor note is / are selected from the group consisting of C6 alcohol, C7- Alcohol, (Z) -3-hexenol (cis-3-hexenol), (E) -2-hexenol (trans-2-hexenol), (E / Z) -3-hexenol and (Z) -4-hexenol ( cis-4-hexenol) as listed in Table 1 below:

Table 1

Particularly preferred is a fragrance mixture, preferably a perfume oil, in which the one or more fragrance alcohols with a green odor note is / are selected from the group consisting of C6 alcohol, C7 alcohol, (Z) -3-hexenol (cis -3-hexenol) and (Z) -4-hexenol (cis -4-hexenol).

Alternatively preferred is such a fragrance mixture according to the invention, Preferably a perfume oil, in which the one, the several or all of the unpleasant and / or pleasant smelling, odorant alcohol (s) with a floral odor note is / are selected from the group consisting of odoriferous alcohols with a molecular weight in the range of 120 g / mol to 200 g / mol, preferably in the range from 122 to 168 g / mol.

In a preferred variant, the invention relates to a fragrance mixture in which the one or more fragrance alcohols with a floral odor note is / are selected from the group consisting of phenylethyl alcohol, linalool, citronellol, geraniol, nerol, ethyllinalool, tetrahydrolinalool , Dihydromyrcenol, C8 alcohol, C9 alcohol, C10 alcohol, alpha-terpineol and tetrahydromyrcenol, as listed in Table 2 below:

Table 2

Particularly preferred is a fragrance mixture, preferably a perfume oil, in which the one or more fragrance alcohols with a floral odor note is / are selected from the group consisting of phenylethyl alcohol, linalool, citronellol, geraniol, nerol, ethyllinalool , Tetrahydrolinalool, dihydromyrcenol and tetrahydromyrcenol.

Even more preferred is a fragrance mixture, preferably a perfume oil, in which the one or more fragrance alcohols is / are selected from the group of fragrance alcohols with green odor notes and from the group of odorant alcohols with flowery odor notes. In a further preferred variant, the one fragrance alcohol or the several fragrance alcohols are selected from the group of fragrance alcohols with green odor notes, which consists of C6 alcohol, C7 alcohol, (Z) -3-hexenol (cis-3- Hexenol), (E) -2-hexenol (trans-2-hexenol), (E / Z) -3-hexenol and (Z) -4-hexenol (cis-4-hexenol), and / or from the group of Fragrance alcohols with floral odor notes, which consists of phenylethyl alcohol, linalool, citronellol, geraniol, nerol, ethyllinalool, tetrahydrolinalool, dihydromyrcenol, C8 alcohol, C9 alcohol, C10 alcohol, alpha-terpineol and tetrahydromyrcenol.

The person skilled in the art will determine the proportion of component (i), i.e. the proportion of 1,3-propanediol, in a fragrance mixture according to the invention, preferably a perfume oil. choose so that the desired effect of emphasizing or highlighting and / or masking or reducing one odor note or several odor notes of the one odorous substance alcohol or the several odorous substance alcohols is achieved. At the same time, he will take care not to use too large amounts of component (i), i.e. 1,3-propanediol, which could dominate the overall sensory impression of a fragrance mixture. On the other hand, he will not only provide such a small amount of component (i), ie of 1,3-propanediol, that highlighting or emphasizing and / or masking or reducing olfactory aspects of one or more odorant alcohols is not or hardly can be felt.

The 1, 3-propanediol used according to the invention has the advantage that when it is used, in particular the use according to the invention, it is effective even in such low concentrations for the purposes of the present invention at which no or at least no perceptible inherent odor is imparted becomes. In this way, 1,3-propanediol can be combined with different fragrances and, if necessary, further constituents of a perfume oil in order to produce particularly advantageous fragrance mixtures or to perfume products with any fragrance.

In principle, preference is given to such a fragrance mixture in which 1, 3- Propanediol is used in an effective amount which is sufficient to emphasize or emphasize a pleasant odor note or all pleasant odor notes of the one fragrance alcohol or the several fragrance alcohols, and / or to emphasize an unpleasant odor note or all unpleasant odor notes of the one odorant alcohol or alcohol. to mask or reduce the multiple odoriferous alcohols.

A sensorially effective amount is to be understood as meaning a proportion of 1,3-propanediol which is sufficient to achieve the above effects, ie highlighting and / or accentuating a pleasant odor note and / or masking and / or reducing an unpleasant odor note to effect the fragrance mixture.

Advantageously, the effective amount of 1,3-propanediol is particularly suitable for emphasizing or emphasizing the natural freshness, the charisma or the floral odor note (s) of the one or more odorant alcohols in the odorant mixture and / or the fatty ones To mask or reduce technical or metallic odor notes of the one odorant alcohol or of the several odorant alcohols in the odorant mixture.

In order to achieve the sensory effects described above, the 1,3-propanediol is added to the fragrance mixture according to the invention in an amount of> 10% by weight. 1,3-Propanediol is preferably added to the fragrance mixture according to the invention in an amount of> 10% by weight to 90% by weight. 1,3-Propanediol is even more preferably added to the fragrance mixture according to the invention in an amount of 20% by weight to 80% by weight. 1,3-Propanediol is even more preferably added to the fragrance mixture in an amount of 30% by weight to 70% by weight. Even more preferably, 1,3-propanediol is added to the fragrance mixture in an amount of 40% by weight to 60% by weight. Most preferably, 1,3-propanediol is added to the fragrance mixture in an amount of> 50% by weight. All quantitative data are based on the total weight of the fragrance mixture. Surprisingly, the sensory properties of the one fragrance alcohol or of the several fragrance alcohols are positively influenced by combination with 1,3-propanediol in an amount of> 10% by weight. In general, the higher the odor alcohol content, the higher the impact and radiation. From a fragrance alcohol content of 20% by weight, the odor is less greasy and, from a fragrance alcohol content of 40% by weight, increasingly flowery. In addition, predominantly natural odorant mixtures can be achieved from 50% by weight.

As a comparison of 10% solutions of the perfume alcohols in 1,3-propanediol with 10% solutions of the perfume alcohols in dipropylene glycol shows, the perfume alcohols in a 1,3-propanediol solution are stronger and with less unpleasant side notes perceived as being in a dipropylene glycol solution. The solutions in 1,3-propanediol appear more flowery and natural. In individual cases, the sensory impression is shifted in the direction of more natural, fresher, more charisma, less musty, less artificial and less metallic, whereby in individual cases further sensory influences were observed in the presence of 1,3-propanediol. Detailed odor descriptions can be found in Example 1, Table 3 below.

By varying the 1,3-propanediol concentration in the fragrance mixture according to the invention, for example by increasing or decreasing the 1,3-propanediol content, the sensory properties of the fragrance mixture and thus the sensory profile of the fragrance mixture can be adjusted or varied . The 1,3-propanediol content in the fragrance mixture is preferably set to 90% by weight, 80% by weight, 70% by weight, 60% by weight, 50% by weight, 40% by weight, 30% by weight, 20% by weight and> 10% by weight are set.

Depending on the 1,3-propanedilage content, the sensory profile of the fragrance mixture according to the invention can be enhanced in favor of flowery, natural, fresh, etc. notes and, on the other hand, the less unpleasant secondary notes can be suppressed. For example, the odorant alcohol linalool results in a 90% concentration of 1,3-propanediol in a juicy, fruity sensory evaluation, in an 80% concentration of 1,3-propanediol in a clearer, brighter sensory evaluation, in the case of a 60% concentration Concentration 1, 3-propanediol in one slightly floral, fresher sensory rating and in a 40% concentration 1,3-propanediol in a floral clean sensory rating. Detailed odor descriptions depending on the 1,3-propanediol concentration can be found in Example 2, Table 4 below.

The variation of the 1,3-propanediol concentration in the fragrance mixture also has the advantage that fragrance mixtures can be produced whose natural or renewal content can be increased by the 1,3-propanediol content.

According to the present invention, fragrance mixtures are even more preferred which comprise either two, three, four, five or more different fragrance alcohols from the group of fragrance alcohols with green odor notes defined above and / or two, three, four, five or more different ones Fragrance alcohols from the group of fragrance alcohols defined above with floral odor notes include, most preferably fragrance alcohols selected from the group of odorant alcohols with green odor notes, which consists of C6 alcohol, C7 alcohol, (Z) -3-hexenol (cis-3- Hexenol), (E) -2-hexenol (trans-2-hexenol), (E / Z) -3-hexenol and (Z) -4-hexenol (cis-4-hexenol), and / or from the group of Fragrance alcohol with floral odor notes, which consists of phenylethyl alcohol, linalool, citronellol, geraniol, nerol, ethyllinalool, tetrahydrolinalool, dihydromyrcenol, C8 alcohol, C9 alcohol, C10 alcohol, alpha-terpineol and tetrahydromyrcenol.

Preferably, fragrance (s) from the group of fragrance alcohols, in particular from the group of fragrance alcohols with green notes and / or the group of fragrance alcohols with floral notes, is / are in the fragrance mixture in a concentration of <90% by weight contain. The one or more fragrances are preferably from the group of fragrance alcohols, in particular from the group of fragrance alcohols with green notes and / or the group of fragrance alcohols with floral notes, in the fragrance mixture in a concentration of 10 to <90 % By weight, in particular from 11 to 90% by weight. The one or more fragrances from the group of the fragrance alcohols, in particular from the group of the fragrance alcohols, is / are even more preferred with green notes and / or the group of fragrance alcohols with floral notes, contained in the fragrance mixture in a concentration of 20 to 80% by weight. Even more preferred is / are the one or more fragrances from the group of the fragrance alcohols, in particular from the group of the fragrance alcohols with green notes and / or the group of the fragrance alcohols with floral notes, in the fragrance mixture in a concentration of 30 to 70% by weight. Even more preferred is / are the one or more fragrance (s) from the group of fragrance alcohols, in particular from the group of fragrance alcohols with green notes and / or the group of fragrance alcohols with floral notes, in the fragrance mixture in a concentration of 40 to 60% by weight. Most preferred is / are the one or more fragrance (s) from the group of fragrance alcohols, in particular from the group of fragrance alcohols with green notes and / or the group of fragrance alcohols with floral notes, in the fragrance mixture in a concentration of <50 wt .-%, in particular <51% by weight. All quantitative data are based on the total weight of the fragrance mixture.

In the context of the present invention, a fragrance mixture is particularly preferred in which the ratio of 1,3-propanediol to the total amount of fragrance alcohol (s) is 50:50, preferably 40:60, even more preferably 20:80 and most preferably 10:90, or in particular in the fragrance mixture according to the invention, the ratio of 1,3-propanediol to the total amount of fragrance alcohol (s) with a green odor note is 50:50, preferably 40:60, even more preferably 20:80 and most preferably 10: 90, or in particular in the fragrance mixture according to the invention the ratio of 1,3-propanediol to the total amount of fragrance alcohol (s) with a floral odor note is 50:50, preferably 40:60, even more preferably 20:80 and most preferably 10:90.

In an alternatively preferred embodiment of the present invention, the components (i) and (ii) are contained in the fragrance mixture in an amount of together 1 to 100% by weight, preferably in an amount of together 10 to 90% by weight. %, more preferably in an amount of 20 to 80 and most preferably in an amount of 40 to 60% by weight, based on the total weight of the fragrance mixture.

Quantitative ratios particularly preferred according to the invention also result from the statements described below and in particular from the accompanying examples.

Fragrance mixtures according to the invention are usually liquid at 25 ° C. and 1013 hPa and are generally homogeneous solutions.

In addition to the particular olfactory advantages, the outstanding material properties of the fragrance mixture according to the invention, such as solubility in conventional cosmetic solvents, compatibility with other components of such products and the toxicological harmlessness of the fragrance mixture according to the invention, which make it particularly suitable for the purposes described below, should also be mentioned underline.

In addition to components (i) and (ii) as described above, an odorant mixture according to the invention can preferably contain one or more other (customary) active ingredients or functional ingredients, and one or more other ingredients that do not meet the above criteria (i) Corresponding solvents or fragrances not corresponding to the above criteria of component (ii), which make the total 100% by weight in the fragrance mixture, preferably in the perfume oil.

Fragrance mixtures according to the invention, in particular perfume oils, can be used for perfuming in liquid form, undiluted or diluted with a solvent. Suitable and preferred solvents for this are in particular ethanol, glycerol, 1,2-propylene glycol, 1,2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate and triacetin. These odorant mixtures can contain up to 90% by weight, preferably about 5 to about 70% by weight, even more preferably about 10 to about 50% by weight and particularly preferably about 15 to about 25% by weight contain the solvents mentioned.

In a preferred alternative, the fragrance mixtures according to the invention, in particular perfume oils, comprise synthetic or natural, preferably tasteless and odorless, carrier substances, in particular carrier oils, which contain the fragrances in highly concentrated form and optionally perfume solvents and / or auxiliaries.

In addition, the fragrance mixtures according to the invention, preferably perfume oils, are adsorbed on a carrier substance which ensures both a fine distribution of the fragrances contained therein in the product and a controlled release during use. Such carriers can be porous inorganic materials such as light sulfate, silica gels, zeolites, plasters, clays, clay granules, aerated concrete, etc. or organic materials such as wood, cellulose-based substances, sugar, dextrins (e.g. maltodextrin) or plastics such as PVC, polyvinyl acetates or polyurethanes. The combination of fragrance mixture according to the invention and carrier material represents an exemplary product according to the invention.

In an alternative preferred embodiment, the fragrance mixtures according to the invention, preferably perfume oils, are in microencapsulated or spray-dried form or as inclusion complexes or as extrusion products in order to be added in this form, for example, to a product to be perfumed.

The microencapsulation of the fragrance mixtures according to the invention, preferably perfume oils, can be carried out, for example, by the so-called coacervation process with the aid of capsule materials, for example made of polyurethane-like substances or soft gelatine. The spray-dried fragrance or flavoring compositions can be produced, for example, by spray drying an emulsion or dispersion containing the fragrance mixture according to the invention, with preferably modified starches, Proteins, dextrin, and vegetable gums can be used. Inclusion complexes can be produced, for example, by introducing dispersions of a fragrance mixture according to the invention and cyclodextrins or urea derivatives into a suitable solvent, for example water. Extrusion products can be obtained by fusing a fragrance mixture according to the invention, preferably a perfume oil, with a suitable waxy substance and by extrusion with subsequent solidification, optionally in a suitable solvent, for example isopropanol.

If necessary, the properties of odorant mixture preparations modified in this way can be further optimized by so-called "coating" with suitable materials with a view to a more targeted release of fragrances, for which purpose waxy plastics such as polyvinyl alcohol are preferably used. The resulting products, which comprise the fragrance mixture according to the invention, preferably perfume oils, in turn represent products according to the invention.

Examples of further additional fragrances, which can in principle advantageously be used as a component of a fragrance mixture according to the invention, in particular a perfume oil, can be found, for example, in “S. Arctander, Perfume and Flavor Chemicals, Volumes I and II, Montclair, N. J., 1969, self-published "or" H. Surburg and J. Panten, Common Fragrance and Flavor Materials, 6th Edition, Wiley-VCH, Weinheim, 2016 “and in particular the further fragrances explicitly mentioned in US 2008/0070825 that are not already part of the constituents (ii) of the fragrance mixture according to the invention , preferably a perfume oil.

Usually, fragrances are not used in binary or ternary mixtures, but as a component of sophisticated complex mixtures which can contain two, three, four, five, ten, but preferably a much higher number of fragrances in sometimes very small amounts to result in a particularly rounded odor profile.

In a preferred development of the present invention, the described odorant mixture therefore contains any number of additional ones Fragrances which do not come under the definition of the fragrance alcohols (ii) according to the invention and which are selected from the group formed by: (1) hydrocarbons; (2) aliphatic alcohols; (3) aliphatic aldehydes and their acetals; (4) aliphatic ketones and their oximes; (5) aliphatic sulfur-containing compounds; (6) aliphatic nitriles; (7) esters of aliphatic carboxylic acids; (8) acyclic terpene alcohols; (9) acyclic terpene aldehydes and ketones; (10) cyclic terpene alcohols; (11) cyclic terpene aldehydes and ketones; (12) cyclic alcohols; (13) cycloaliphatic alcohols; (14) cyclic and cycloaliphatic ethers; (15) cyclic and macrocyclic ketones; (16) cycloaliphatic aldehydes; (17) cycloaliphatic ketones; (18) esters of cyclic alcohols; (19) esters of cycloaliphatic alcohols; (20) esters of cycloaliphatic carboxylic acids; (21) araliphatic alcohols; (22) esters of araliphatic alcohols and aliphatic carboxylic acids; (23) araliphatic ethers; (24) aromatic and araliphatic aldehydes; (25) aromatic and araliphatic ketones; (26) aromatic and araliphatic carboxylic acids and their esters; (27) nitrogen-containing aromatic compounds; (28) phenols, phenyl ethers, and phenyl esters; (29) heterocyclic compounds; (30) lactones; as well as their mixtures.

The following fragrances may be mentioned in detail:

Extracts from natural raw materials: This group stands for essential oils, concretes, absolutes, resins, resinoids, balms, tinctures such. B. Ambré Tint; Amyris oil; Angelica seed oil; Angelica root oil; Anise oil; Valerian oil; Basil oil; Tree moss absolute; Bay oil; Mugwort oil; Benzoeresine; Bergamot oil; Beeswax absolute; Birch tar oil; Bitter almond oil; Savory oil; Bucco leaf oil; Cabreuva oil; Cade oil; Calamus oil; Camphor oil; Cananga oil; Cardamom oil; Cascarilla oil; Cassia oil; Cassie absolute; Castoreum absolute; Cedar leaf oil; Cedarwood oil; Cistus oil; Citronella oil; Lemon oil; Copaiva balsam; Copaiva balsam oil; Coriander oil; Costus root oil; Cumin oil; Cyprus oil; Davana oil; Dill herb oil; Dill seed oil; Eau de brouts absolute; Oakmoss absolute; Eggs iöl; Tarragon oil; Eucalyptus citriodora oil; Eucalyptus oil; Fennel oil; Spruce needle oil; Galbanum oil; Galbanum resin; Geranium oil; Grapefruit oil; Guaiac wood oil; Gurjun balm; Gurjun balm oil; Helichrysum absolute; Helichrysum oil; Ginger oil; Orris root absolute; Orris root oil; Jasmine absolute; Calamus oil; Chamomile oil blue; Roman chamomile oil; Carrot seed oil; Cascarilla oil; Pine needle oil; Spearmint oil; Caraway seed oil; Labdanum oil; Labdanum absolute; Labdanum resin; Lavandin absolute; Lavandin oil; Lavender absolute; Lavender oil; Lemongrass oil; Lovage oil; Distilled lime oil; Pressed lime oil; Linaloe oil; Litsea cubeba oil; Bay leaf oil; Mace oil; Marjoram oil; Mandarin oil; Massoirinden oil; Mimosa absolute; Musk seed oil; Musk tincture; Muscatel sage oil; Nutmeg oil; Myrrh absolute; Myrrh oil; Myrtle oil; Clove leaf oil; Clove blossom oil; Neroli oil; Olibanum absolute; Olibanum oil; Opopanax oil; Orange blossom absolute; Orange oil; Origanum oil; Palmarosa oil; Patchouli oil; Perilla oil; Balsam oil of Peru; Parsley leaf oil; Parsley seed oil; Petitgrain oil; Peppermint oil; Pepper oil; Allspice oil; Pine oil; Poley oil; Rose absolute; Rosewood oil; Rose oil; Rosemary oil; Dalmatian sage oil; Spanish sage oil; Sandalwood oil; Celery seed oil; Spiclavender oil; Star anise oil; Styrax oil; Marigold oil; Pine needle oil; Tea tree oil; Turpentine oil; Thyme oil; Tolu balsam; Tonka absolute; Tuberose absolute; Vanilla extract; Violet leaf absolute; Verbena oil; Vetiver oil; Juniper berry oil; Wine yeast oil; Wormwood oil; Wintergreen oil; Ylang oil; Hyssop oil; Civet absolute; Cinnamon leaf oil; Cinnamon bark oil and fractions thereof or ingredients isolated from it.

Individual fragrances: Individual fragrances can be divided into a large number of classes, namely:

Hydrocarbons such as 3-carene; a-pinene; ß-pinene; a-terpinene; g-terpinene; p-cymene; Bisabolene; Camphene; Caryophyllene; Cedren; Ferns; Limonene; Longifolene; Myrcene; Ocimen; Valencene; (E, Z) -1, 3,5-undecatriene; Styrene; Diphenylmethane;

Aliphatic alcohols such as, for example, 3-octanol; 2,6-dimethylheptanol; 2-methyl-2-heptanol; 2-methyl-2-octanol; 1-octen-3-ol; Mixture of 3,4,5,6,6-pentamethyl-3/4-hepten-2-ol and 3,5,6,6-tetramethyl-4-methyleneheptan-2-ol; (E, Z) -2,6-nonadienol; 3,7-dimethyl-7-methoxyoctan-2-ol; 9-decenol; 10-undecenol; 4-methyl-3-decen-5-ol; Aliphatic aldehydes and their acetals, such as, for example, hexanal; Heptanal; Octanal; Nonanal; Decanal; Undecanal; Dodecanal; Tridecanal; 2-methyloctanal; 2-methylnonanal; EJ-2-hexenal; (ZJ-4-heptenal; 2,6-dimethyl-5-heptenal; 10-undecenal; (EJ-4-decenal; 2-dodecenal; 2,6,10-trimethyl-9-undecenal; 2,6,10- Trimethyl-5,9-undecadienal; heptanaldiethylacetal; 1,1-dimethoxy-2,2,5-trimethyl-4-hexene; citronellyloxyacetaldehyde; 1- (1-methoxy-propoxy) - (E / Z) -3-hexene;

Aliphatic ketones and their oximes such as 2-heptanone; 2-octanone; 3-octanone; 2-nonanone; 5-methyl-3-heptanone; 5-methyl-3-heptanone oxime; 2, 4,4,7-tetramethyl-6-octen-3-one; 6-methyl-5-hepten-2-one;

Aliphatic sulfur-containing compounds such as 3-methylthio-hexanol; 3-methylthiohexyl acetate; 3-mercaptohexanol; 3-mercaptohexyl acetate; 3-mercapto hexyl butyrate; 3-acetylthiohexyl acetate; 1-menthen-8-thiol;

Aliphatic nitriles such as 2-nonenoic acid nitrile; 2-undecenoic acid nitrile; 2-tridecenoic acid nitrile; 3,12-tridecadienoic acid nitrile; 3,7-dimethyl-2,6-octadiene-acid nitrile;

3.7-dimethyl-6-octenonitrile;

Esters of aliphatic carboxylic acids such as (E) - and (Z) - 3-hexenyl formate; Ethyl acetoacetate; Isoamyl acetate; Hexyl acetate; 3,5,5-trimethylhexyl acetate; 3-methyl-2-butenyl acetate; (EJ-2-hexenyl acetate; (E) - and (Z) - 3-hexenyl acetate; octyl acetate; 3-octyl acetate; 1-octen-3-yl acetate; ethyl butyrate; butyl butyrate,; isoamyl butyrate; hexyl butyrate; (E) - and (ZJ -3-hexenyl isobutyrate; hexyl crotonate; ethyl isovalerate; ethyl 2-methylpentanoate; ethyl hexanoate; allyl hexanoate; ethyl heptanoate; allyl heptanoate; ethyl octanoate; ethyl (E, Z) -2,4-decadienoate; methyl 2-octinate; -noninate; allyl-2-isoamyloxyacetate; methyl-

3.7-dimethyl-2,6-octadienoate; 4-methyl-2-pentyl-crotonate;

Acyclic terpene alcohols such as. B. Lavadulol; Nerolidol; Farnesol; Tetrahydrogeraniol; 2,6-dimethyl-7-octen-2-ol; 2,6-dimethyloctan-2-ol; 2-methyl-6-methylen-7-octen-2-ol; 2,6-dimethyl-5,7-octadien-2-ol; 2,6-dimethyl-3,5-octadien-2-ol; 3,7-dimethyl-4,6-octadien-3-ol; 3,7-dimethyl-1,5,7-octatrien-3-ol 2,6-dimethyl- 2,5,7-octatrien-1-ol; and their formates, acetates, propionates, isobutyrates, butyrates, isovalerianates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates;

Acyclic terpene aldehydes and ketones such. B. Geranial; Neral; Citronellal; 7-hydroxy-3,7-dimethyloctanal; 7-methoxy-3,7-dimethyloctanal; 2,6,10-trimethyl-9-undecenal; Geranylacetone; as well as the dimethyl and diethyl acetals of geranial, neral, 7-hydroxy-3,7-dimethyloctanal;

Cyclic terpene alcohols such as. B. menthol; Isopulegol; Terpinenol-4; Menthan-8-ol; Menthan-1-ol; Menthan-7-ol; Borneol; Isoborneol; Linalool oxide; Nopoly; Cedrol; Ambrinol; Vetiverol; Guajol; and their formates, acetates, propionates, isobutyrates, butyrates, isovalerianates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates;

Cyclic terpene aldehydes and ketones such. B. menthone; Isomenthone; 8-mercaptomenthan-3-one; Carvone; Camphor; Fenchone; alpha-ionon; beta-ionon; alpha-n-methylionone; beta-n-methylionone; alpha-isomethylionone; beta-isomethylionone; alpha-lron; alpha damascone; beta damascone; beta-damascenone; delta damascone; gamma damascone; 1 - (2,4,4-trimethyl-2-cyclohexen-1-yl) -2-buten-1-one; 1, 3,4,6,7,8a-hexahydro-1, 1, 5,5-tetramethyl-2H-2,4a-methanonaphthalen-8 (5H) -one; 2-methyl-4- (2,6, 6-trimethyl-1-cyclohexen-1 -yl) -2-butenal; Nootkatone;

Dihydronootkatone; 4,6,8-megastigmatrien-3-one; alpha-sinensal; beta-sinensal; acetylated cedarwood oil (methyl cedryl ketone);

Cyclic alcohols such as 4-tert-butylcyclohexanol; 3,3,5-trimethylcyclohexanol; 3-isocamphylcyclohexanol; 2,6,9-trimethyl-Z2, Z5, E9-cyclododecatrien-1-ol; 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol;

Cycloaliphatic alcohols such as alpha, 3,3-

Trimethylcyclohexylmethanol; 1- (4-isopropylcyclohexyl) ethanol; 2-methyl-4- (2,2,3-trimethyl-3-cyclopent-1 -yl) butanol; 2-methyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) -2-buten-1-ol; 2-ethyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) -2-buten-1-ol; 3-methyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) -pentan-2-ol; 3-methyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) -4-penten-2-ol; 3,3-dimethyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) -4-penten-2-ol; 1 - (2,2,6-trimethylcyclohexyl) pentan-3-ol; 1 - (2.2.6-

Trimethylcyclohexyl) hexan-3-ol;

Cyclic and cycloaliphatic ethers such as cineole; Cedryl methyl ether; Cyclododecyl methyl ether; 1,1-dimethoxycyclododecane;

(Ethoxymethoxy) cyclododecane; alpha cedrene epoxide; 3a, 6, 6,9a-

Tetramethyldodecahydronaphtho [2, 1 -b] furan; 3a-ethyl-6,6,9a-trimethyldodecahydronaphtho [2, 1 -b] furan; 1,5,9-trimethyl-13-oxabicyclo [10.1 .0] trideca-4,8-diene; Rose oxide; 2- (2,4-dimethyl-3-cyclohexen-1-yl) -5-methyl-5- (1-methylpropyl) -1,3-dioxane;

Cyclic and macrocyclic ketones such as 4-tert-butylcyclohexanone; 2,2,5-trimethyl-5-pentylcyclopentanone; 2-heptylcyclopentanone; 2-

Pentylcyclopentanone; 2-hydroxy-3-methyl-2-cyclopenten-1-one; 3-methyl-cis-2-penten-1-yl-2-cyclopenten-1-one; 3-methyl-2-pentyl-2-cyclopenten-1-one; 3-methyl-4-cyclopentadecenone; 3-methyl-5-cyclopentadecenone; 3-methylcyclopentadecanone; 4- (1-ethoxyvinyl) -3,3,5,5-tetramethylcyclohexanone; 4-tert-pentylcyclohexanone; 5-cyclohexadecen-1-one; 6,7-dihydro-1,1,2,3,3-pentamethyl-4 (5H) -indanone; 8-cyclohexadecen-1-one; 9-cycloheptadecen-1-one; Cyclopentadecanone;

Cyclohexadecanone;

Cycloaliphatic aldehydes such as 2,4-dimethyl-3-cyclohexenecarbaldehyde;

2-methyl-4- (2,2,6-trimethyl-cyclohexen-1 -yl) -2-butenal; 4- (4-hydroxy-4-methylpentyl) -

3-cyclohexenecarbaldehyde; 4- (4-methyl-3-penten-1-yl) -3-cyclohexenecarbaldehyde;

Cycloaliphatic ketones such as. B. 1 - (3,3-Dimethylcyclohexyl) -4-penten-1-one; 2,2-dimethyl-1 - (2,4-dimethyl-3-cyclohexen-1 -yl) -1-propanone; 1 - (5,5-dimethyl-1-cyclohexen-1 -yl) -4-penten-1-one; 2,3,8,8-tetramethyl-1, 2,3,4,5,6,7,8-octahydro-2-naphthalenyl methyl ketone; Methyl 2,6,10-trimethyl-2,5,9-cyclododecatrienyl ketone; tert-butyl- (2,4-dimethyl-3-cyclohexen-1-yl) ketone; Esters of cyclic alcohols such as, for example, 2-tert-butylcyclohexyl acetate; 4-tert-butylcyclohexyl acetate; 2-tert-pentylcyclohexyl acetate; 4-tert-pentylcyclohexyl acetate; 3,3,5-trimethylcyclohexyl acetate; Decahydro-2-naphthyl acetate; 2-cyclopentylcyclopentyl crotonate; 3-pentyl tetrahydro-2H-pyran-4-ylacetate; Decahydro-2,5,5,8a-tetramethyl-2-naphthyl acetate; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5 or 6-indenyl acetate; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5 or 6-indenyl propionate; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5, or 6-indenyl isobutyrate; 4,7-methanooctahydro-5 or 6-indenyl acetate;

Esters of cycloaliphatic alcohols such as. B.1 -cyclohexylethyl crotonate;

Esters of cycloaliphatic carboxylic acids such as. B. allyl 3-cyclohexyl propionate; Allylcyclohexyloxyacetate; cis and trans methyl dihydrojasmonate; cis and trans methyl jasmonate; Methyl 2-hexyl-3-oxocyclopentanecarboxylate; Ethyl 2-ethyl-6,6-dimethyl-2-cyclohexenecarboxylate; Ethyl 2,3,6,6-tetramethyl-2-cyclohexene carboxylate; Ethyl 2-methyl-1,3-dioxolane-2-acetate;

Araliphatic alcohols such as benzyl alcohol; 3-phenylpropanol; 2-phenylpropanol; 2-phenoxyethanol; 2,2-dimethyl-3-phenylpropanol; 2,2-dimethyl-3- (3-methylphenyl) propanol; 1,1-dimethyl-2-phenylethyl alcohol; 1,1-dimethyl-3-phenylpropanol; 1-ethyl-1-methyl-3-phenylpropanol; 2-methyl-5-phenylpentanol; 3-methyl-5-phenylpentanol; 3-phenyl-2-propen-1-ol; 4-methoxybenzyl alcohol; 1 - (4-isopropylphenyl) ethanol;

Esters of araliphatic alcohols and aliphatic carboxylic acids such as benzyl acetate; Benzyl propionate; Benzyl isobutyrate; Benzyl isovalerate; 2-phenylethyl acetate; 2-phenylethyl propionate; 2-phenylethyl isobutyrate; 2-phenylethyl isovalerate; 1-phenylethyl acetate; alpha-trichloromethylbenzyl acetate; alpha, alpha-dimethylphenylethyl acetate; alpha, alpha-dimethylphenylethyl butyrate; Cinnamyl acetate; 2-phenoxyethyl isobutyrate; 4-methoxybenzyl acetate;

Araliphatic ethers such as, for example, 2-phenylethyl methyl ether; 2-phenylethyl isoamyl ether; 2-phenylethyl-1-ethoxyethyl ether; Phenylacetaldehyde dimethyl acetal; Phenylacetaldehyde diethyl acetal;

Hydratropaaldehyde dimethyl acetal; Phenylacetaldehyde glycerol acetal; 2,4,6-trimethyl-4-phenyl-1,3-dioxane; 4,4a, 5,9b-tetrahydroindeno [1,2-d] -m-dioxin; 4,4a, 5, 9b-tetrahydro-2,4-dimethylindeno [1,2-d] -m-dioxin;

Aromatic and araliphatic aldehydes such as. B. benzaldehyde; Phenylacetaldehyde; 3-phenylpropanal; Hydratropaaldehyde; 4-methylbenzaldehyde; 4-methylphenylacetaldehyde; 3- (4-ethylphenyl) -2,2-dimethylpropanal; 2-methyl-3- (4-isopropylphenyl) propanal; 2-methyl-3- (4-tert-butylphenyl) propanal; 2-methyl-3- (4-isobutylphenyl) propanal; 3- (4-tert-butylphenyl) propanal; Cinnamaldehyde; alpha-butyl cinnamaldehyde; alpha-amylcinnamaldehyde; alpha-hexyl cinnamaldehyde; 3-methyl-5-phenylpentanal; 4-methoxybenzaldehyde; 4-hydroxy-3-methoxybenzaldehyde; 4-hydroxy-3-ethoxybenzaldehyde; 3,4-methylenedioxybenzaldehyde; 3,4-dimethoxybenzaldehyde; 2-methyl-3- (4-methoxyphenyl) propanal; 2-methyl-3- (4-methylenedioxyphenyl) propanal;

Aromatic and araliphatic ketones such as acetophenone; 4-methylacetophenone; 4-methoxyacetophenone; 4-tert-butyl-2,6-dimethylacetophenone; 4-phenyl-2-butanone; 4- (4-hydroxyphenyl) -2-butanone; 1 - (2-naphthalenyl) ethanone; 2-benzofuranylethanone; (3-methyl-2-benzofuranyl) ethanone; Benzophenone; 1, 1, 2, 3,3,6-hexamethyl-5-indanyl methyl ketone; 6-tert-butyl-1,1-dimethyl-4-indanylmethyl ketone; 1 - [2,3-dihydro-1,1,2,6-tetramethyl-3- (1-methylethyl) -1H-5-indenyl] ethanone; 5 ‘, 6‘, 7 ‘, 8‘-tetrahydro-3‘, 5 ‘, 5‘, 6 ‘, 8‘, 8‘-hexamethyl-2-acetonaphthone;

Aromatic and araliphatic carboxylic acids and their esters, such as, for example, benzoic acid; Phenylacetic acid; Methyl benzoate; Ethyl benzoate; Hexyl benzoate; Benzyl benzoate; Methylphenyl acetate; Ethyl phenyl acetate; Geranyl phenyl acetate; Phenylethyl phenyl acetate; Methylcinnmat; Ethyl cinnamate; Benzyl cinnamate; Phenylethyl cinnamate; Cinnamyl cinnamate; Allyl phenoxyacetate; Methyl salicylate; Isoamyl salicylate; Hexyl salicylate; Cyclohexyl salicylate; Cis-3-hexenyl salicylate; Benzyl salicylate; Phenylethyl salicylate; Methyl 2,4-dihydroxy-3,6-dimethylbenzoate; Ethyl 3-phenyl glycidate; Ethyl 3-methyl-3-phenyl glycidate; Nitrogen-containing aromatic compounds such as, for example, 2,4,6-trinitro-1,3-dimethyl-5-tert-butylbenzene; 3,5-dinitro-2,6-dimethyl-4-tert-butyl acetophenone;

Cinnamonitrile; 3-methyl-5-phenyl-2-pentenoic acid nitrile; 3-methyl-5-phenylpentanoic acid nitrile; Methyl anthranilate; Methyl N-methyl anthranilate; Schiff bases of methyl anthranilate with 7-hydroxy-3,7-dimethyloctanal, 2-methyl-3- (4-tert-butylphenyl) propanal or 2,4-dimethyl-3-cyclohexenecarbaldehyde; 6- isopropylquinoline; 6-isobutylquinoline; 6-sec-butylquinoline; 2- (3-phenylpropyl) pyridine; Indole; Skatole; 2-methoxy-3-isopropylpyrazine; 2-isobutyl-3-methoxypyrazine;

Phenols, phenyl ethers and phenyl esters such as estragole; Anethole; Eugenol; Eugenyl methyl ether; Isoeugenol; Isoeugenyl methyl ether; Thymol; Carvacrol; Diphenyl ether; beta-naphthyl methyl ether; beta-naphthyl ethyl ether; beta-naphthyl isobutyl ether; 1,4-dimethoxybenzene; Eugenyl acetate; 2-methoxy-4-methylphenol; 2-ethoxy-5- (1-propenyl) phenol; p-cresylphenyl acetate;

Heterocyclic compounds such as 2,5-dimethyl-4-hydroxy-2H-furan-3-one; 2-ethyl-4-hydroxy-5-methyl-2H-furan-3-one; 3-hydroxy-2-methyl-4H-pyran-4-one; 2-ethyl-3-hydroxy-4H-pyran-4-one;

Lactones such as 1,4-octanolide; 3-methyl-1,4-octanolide; 1,4-nonanolide; 1,4-decanolide; 8-decen-1,4-olide; 1, 4-undecanolide; 1,4-dodecanolide; 1,5-decanolide; 1,5-dodecanolide; 4-methyl-1,4-decanolide; 1, 15-pentadecanolide; cis- and trans-11-pentadecen-1, 15-olide; cis- and trans-12-pentadecen-1, 15-olide; 1, 16-hexadecanolide; 9-hexadecen-1, 16-olide; 10-oxa-1, 16-hexadecanolide; 11-oxa-1, 16-hexadecanolide; 12-oxa-1, 16-hexadecanolide; Ethylene 1, 12-dodecanedioate; Ethylene 1,13-tridecanedioate; Coumarin; 2,3-dihydrocoumarin; Octahydrocoumarin; and any mixtures of the aforementioned fragrances.

In a second aspect, the present invention relates to a method for producing a fragrance mixture. In the method according to the invention, components (i) and (ii) of the fragrance mixture are first provided and then brought into contact with one another and mixed to obtain the non-aqueous fragrance mixture according to the invention. With regard to constituents (i) and (ii), their preferred or alternative embodiments, their mixing and quantity ratios and their advantageous effects, reference is made to the above detailed description in connection with the fragrance mixture according to the invention, which is relevant for the method according to the invention according to the second aspect of the invention is also valid.

In the method according to the invention for producing the fragrance mixture according to the invention, the 1,3-propanediol is added to the fragrance alcohol or to the several fragrance alcohols in an amount of> 10% by weight. 1,3-Propanediol is preferably added in an amount of> 10% by weight to 90% by weight. 1,3-Propanediol is even more preferably added in an amount of 20% by weight to 80% by weight. Even more preferably, 1,3-propanediol is added to the odorant mixture in an amount of 30% by weight to 70% by weight. 1,3-Propanediol is even more preferably added to the fragrance mixture in an amount of 40% by weight to 60% by weight. Most preferably, 1,3-propanediol is added to the odorant mixture in an amount of> 50% by weight. All quantitative data are based on the total weight of the fragrance mixture.

In a further preferred variant of the method according to the invention, which results in a fragrance mixture according to the invention, preferably a perfume oil, the ratio of 1,3-propanediol to the total amount of fragrance alcohol (s) is 50:50, preferably 40:60 more preferably 20:80 and most preferably 10:90, or in particular in the fragrance mixture according to the invention the ratio of 1,3-propanediol to the total amount of fragrance alcohol (s) with a green odor note 50:50, preferably 40:60, is even more preferred 20:80 and most preferably 10:90, or in particular, in the fragrance mixture according to the invention, the ratio of 1,3-propanediol to the total amount of fragrance alcohol (s) with a floral odor note is 50:50, preferably 40:60, even more preferably 20: 80 and most preferably 10:90.

In an alternative preferred variant of the method according to the present invention, components (i) and (ii) in the fragrance mixture are preferably a perfume oil, in an amount of together 1 to 100% by weight, preferably in an amount of together 10 to 90% by weight, even more preferably in an amount of 20 to 80 and most preferably in an amount of 40 to 60% by weight, based on the total weight of the fragrance mixture.

According to a third aspect, the present invention relates to a method for modifying the sensory properties of a fragrance alcohol or a plurality of fragrance alcohols, which method comprises the following steps:

to emphasize or intensify a pleasant odor note or all the pleasant odor notes of a fragrance alcohol or several fragrance alcohols;

and or

to mask or reduce an unpleasant odor note or all unpleasant odor notes of a fragrance alcohol or several fragrance alcohols.

Surprisingly, with the method according to the third aspect of the present invention using 1,3-propanediol, the sensory properties of one or more fragrance alcohols

Modify fragrance alcohols.

In particular, a pleasant odor note or all pleasant odor notes, for example more charisma, natural freshness or flowery odor note (s) of a fragrance alcohol or several fragrance alcohols, can be emphasized or intensified with the aforementioned method, if 1,3-propanediol is in an effective amount as described above is used.

In an analogous manner, an unpleasant odor note or all unpleasant odor notes, for example musty, greasy, technical or metallic, can preferably be obtained with the aforementioned method Odor note (s) of a perfume alcohol or several perfume alcohols mask or reduce if 1,3-propanediol is used in an effective amount, as described above.

The one, more or all of the odorant alcohol (s) whose olfactory properties are improved according to the invention by using 1,3-propanediol is preferably one or more odorant alcohol (s) with a green odor note or one or more odorant alcohol (s) with a floral odor note.

In principle, preferred is / are the one, the several or all of the unpleasant and / or pleasant-smelling fragrance alcohol (s) with a green odor note selected from the group consisting of fragrance alcohols with a molecular weight in the range from 100 g / mol to 190 g / mol, preferably in the range from 100 g / mol to 158 g / mol.

In a preferred variant, the one fragrance alcohol or the several fragrance alcohols with green odor notes are selected from the group consisting of C6 alcohol, C7 alcohol, (Z) -3-hexenol (cis-3-hexenol), ( E) -2-hexenol (trans-2-hexenol), (E / Z) -3-hexenol and (Z) -4-hexenol (cis-4-hexenol).

Alternatively preferred is / are the one, the several or all of the unpleasant and / or pleasant smelling fragrance alcohol (s) with a floral odor note selected from the group consisting of fragrance alcohols with a molecular weight in the range from 120 g / mol to 200 g / mol, preferably in the range from 122 to 168 g / mol.

In a preferred variant, the one odorant alcohol or the several odorant alcohols with a floral odor note are selected from the group consisting of phenylethyl alcohol, linalool, citronellol, geraniol, nerol, ethyllinalool, tetrahydrolinalool, dihydromyrcenol, C8 alcohol, C9 alcohol, C10 alcohol, alpha-terpineol, and tetrahydromyrcenol.

Even more preferred are either two, three, four, five or more various fragrance alcohols selected from the group of fragrance alcohols with a green odor note, which consists of C6 alcohol, C7 alcohol, (Z) -3-hexenol (cis- 3-hexenol), (E) -2-hexenol (trans-2- Hexenol), (E / Z) -3-hexenol and (Z) -4-hexenol (cis-4-hexenol), and / or from the group of odoriferous alcohols with a floral odor note, which consists of phenylethyl alcohol, linalool, citronellol, geraniol , Nerol, ethyllinalool, tetrahydrolinalool, dihydromyrcenol, C8 alcohol, C9 alcohol, C10 alcohol, alpha-terpineol and tetrahydromyrcenol.

With regard to constituents (i) and (ii), their preferred or alternative embodiments and their mixing and quantitative ratios and their advantageous effects, reference is made to the above detailed description in connection with the fragrance mixture according to the invention, which is relevant for the method according to the invention according to the third aspect of the invention also applies.

Surprisingly, the sensory properties of the one fragrance alcohol or of the several fragrance alcohols are positively influenced by combination with an effective amount of> 10% by weight of 1,3-propanediol.

The sensory properties of the one fragrance alcohol or of the several fragrance alcohols are preferably influenced even more positively if 1,3-propanediol is used in an amount of> 10% by weight to 90% by weight. Most preferably, the sensory properties of the one odorous substance alcohol or of the several odorous substance alcohols are positively influenced if 1,3-propanediol is used in an amount of 20% by weight to 80% by weight. Even more preferably, the sensory properties of the one fragrance alcohol or of the several fragrance alcohols are positively influenced if

1,3-Propanediol is used in an amount of 30% by weight to 70% by weight. Even more preferably, the sensory properties of the one fragrance alcohol or of the several fragrance alcohols are positively influenced if

1,3-propanediol is used in an amount of 40% by weight to 60% by weight. Most preferably, the sensory properties of the one odorous substance alcohol or of the several odorous substance alcohols are positively influenced if

1, 3-propanediol is used in an amount of> 50% by weight. All quantitative data are based on the total weight of the fragrance mixture. In individual cases, the sensory impression is shifted in the direction of more natural, fresher, more charismatic, less musty, less artificial and less metallic, with further sensory influences also being observed in the presence of 1,3-propanediol in individual cases.

The modification of the sensory properties of the perfume alcohols according to the invention as a function of the 1,3-propanediol concentration can be seen by way of example from Table 4 below.

Particularly advantageous effects, ie the highlighting or accentuation of pleasant odor notes of an odorous substance alcohol or the masking or reduction of unpleasant odor notes of a odorous substance alcohol, are achieved if in the method according to the invention for modifying the sensory properties of a odorous substance alcohol or several odorous alcohols according to the third aspect of the invention, the ratio of 1,3-propanediol to the total amount of odoriferous alcohol (s) is 50:50, preferably 40:60, even more preferably 20:80 and most preferably 10:90, or in particular the ratio of 1, 3-propanediol to the total amount of odorant alcohol (s) with a green odor note is 50:50, preferably 40:60, even more preferably 20:80 and most preferably 10:90, or in particular the ratio of 1,3-propanediol to the total amount Fragrance alcohol (s) with a floral odor note 50:50, preferably 40:60, even more preferably 20:80 and am most preferably 10:90.

In a further aspect, the present invention also relates to the use of> 10% by weight of 1,3-propanediol for modifying the sensory properties of an odorous substance alcohol or a plurality of odorous substance alcohols, in particular

and or for masking or reducing an unpleasant odor note or all unpleasant odor notes of a fragrance alcohol or several fragrance alcohols.

Surprisingly, the presence of 1,3-propanediol has the effect that certain olfactory aspects of the one odorous substance alcohol or of the several odorous substance alcohols are modified, i.e. emphasized or emphasized and / or masked or reduced.

Surprisingly, the use of 1,3-propanediol in combination with one or more fragrance alcohol (s) has the particular effect that the positive, ie pleasant odor notes, such as charisma, natural freshness or the flowery odor notes of a fragrance alcohol or all odor alcohols are emphasized or emphasized, ie intensified, and / or the negative, ie unpleasant odor notes such as musty, fatty, technical or metallic odor notes are masked or reduced.

With regard to the terms “highlighting” or “emphasizing” or “masking” or “reducing”, reference is made to the above explanations in connection with the fragrance mixture according to the invention, which in connection with the use of 1,3-propanediol for Modifying the sensory properties of a fragrance alcohol is equally valid, so that repetition is not necessary.

The 1,3-propanediol to be used according to the invention is also advantageously easily accessible or producible, has a high level of effectiveness even in low concentrations, in particular in concentrations at which 1,3-propanediol has no or at least only a barely perceptible inherent odor has, is largely or completely colorless, has a high stability in different mixtures or preparations and has no toxic and / or allergenic effect on humans. In addition, 1,3-propanediol has an antibacterial effect, a property which gives the resulting products microbial stability and thus durability.

1,3-Propanediol also has the advantage that when it is used, in particular a use according to the invention, it can be combined with different fragrances and customary constituents of a fragrance mixture in order to perfume products with any fragrance direction. Consequently, the present invention can offer consumers a wide range of types of fragrance.

According to a preferred variant of the present invention, 1,3-propanediol is particularly suitable for masking or reducing, especially for reducing, one or more unpleasant odor notes of a fragrance alcohol or a number of fragrance alcohols. The unpleasant-smelling substances mentioned here can also have other, usually not unpleasant sensory qualities, including olfactory qualities. In the context of the present description, substances that have an unpleasant smell are generally understood to be those that cause one or more unpleasant odor impressions or notes, be it as a primary odor or as a secondary / subordinate odor note. In particular, the unpleasant-smelling substances described herein can also be those fragrances that are primarily perceived as pleasant-smelling substances, but also have an unpleasant metallic, greasy and / or technical odor note, which according to the invention should preferably be reduced.

The same applies analogously to the pleasantly smelling substances described herein. In the context of the present text, substances with a pleasant smell are generally understood to mean substances that produce one or more pleasant odor impressions or odor notes, be it as a primary odor or as a secondary / subordinate odor note.

As a result, in the context of the present invention, for example, both an unpleasant odor note of a certain (unpleasant smelling) odorous substance alcohol and a pleasant one can be masked or reduced Odor note of the same (also pleasantly smelling) odorant alcohol are enhanced.

The one, more or all of the odorant alcohol (s) whose odorous properties are improved according to the invention by using 1,3-propanediol is preferably one or more odorant alcohol (s) with a green odor note or one or more odorant alcohol (s) with a floral odor note.

In principle, preference is / are given to the one, the several or all of the unpleasant and / or pleasant-smelling fragrance alcohol (s) with a green odor note selected from the group consisting of fragrance alcohols with a molecular weight in the range from 100 g / mol to 190 g / mol, preferably in the range from 100 g / mol to 158 g / mol.

In a preferred variant, the one fragrance alcohol or the several fragrance alcohols with a green odor note are selected from the group consisting of C6 alcohol, C7 alcohol, (Z) -3-hexenol (cis-3-hexenol), (E. ) -2-hexenol (trans-2-hexenol), (E / Z) -3-hexenol and (Z) -4-hexenol (cis-4-hexenol).

Alternatively preferred is / are the one which contains several or all of the unpleasant and / or pleasantly smelling fragrance alcohol (s) with a floral odor note selected from the group consisting of fragrance alcohols with a molecular weight in the range from 120 g / mol to 200 g / mol, preferably in the range from 122 to 168 g / mol.

In a preferred variant, the one or more odorant alcohols are or are selected from the group consisting of phenylethyl alcohol, linalool, citronellol, geraniol, nerol, ethyllinalool, tetrahydrolinalool, dihydromyrcenol, C8 alcohol, C9 alcohol, C10 -Alcohol, alpha-terpineol and tetrahydromyrcenol.

Even more preferred are either two, three, four, five or more various fragrance alcohols selected from the group of fragrance alcohols with a green odor note, which consists of C6 alcohol, C7 alcohol, (Z) -3-hexenol (cis- 3-hexenol), (E) -2-hexenol (trans-2- Hexenol), (E / Z) -3-hexenol and (Z) -4-hexenol (cis-4-hexenol), and / or from the group of odoriferous alcohols with a floral odor note, which consists of phenylethyl alcohol, linalool, citronellol, geraniol , Nerol, ethyllinalool, tetrahydrolinalool, dihydromyrcenol, C8 alcohol, C9 alcohol, C10 alcohol, alpha-terpineol and terahydromyrcenol.

Surprisingly, the sensory properties of the one fragrance alcohol or of the several fragrance alcohols are positively influenced by combination with an effective amount of 1,3-propanediol. In individual cases, the sensory impression is shifted in the direction of more natural, fresher, more charisma, less musty, less artificial and less metallic, whereby in individual cases further sensory influences were also observed in the presence of 1,3-propanediol.

Even more preferred are two, three, four, five or more different odorant alcohols from the group of odorant alcohols with green odor notes and / or with two, three, four, five or more different odorant alcohols from the group of odorant alcohols with flowery odor notes include.

In the use according to the invention according to the fourth aspect, the person skilled in the art will select the proportion of 1,3-propanediol so that the desired effect of emphasizing or highlighting and / or masking or reducing one odor note or several odor notes of the fragrance / the fragrance is reached. At the same time, he will take care not to use too large amounts of component (i), ie 1,3-propanediol, which could dominate the overall sensory impression of a fragrance mixture. On the other hand, it will not only provide such a small amount of component (i), ie of 1, 3-propanediol, that emphasizing or highlighting and / or masking or reducing olfactory aspects of the one odorous substance alcohol or the several odorous substance alcohols is not or can hardly be felt. A use is also particularly suitable for the purposes of the present invention, where the amount of 1,3-propanediol used for emphasizing or highlighting and / or for masking or reducing is not sufficient to impart an intrinsic odor. The 1,3-propanediol used according to the invention has the advantage that when it is used, in particular when used according to the invention, it is effective for the purposes of the present invention even in such low concentrations that no or at least no perceptible intrinsic odor is imparted. In this way, 1,3-propanediol can be combined with different fragrances and, if necessary, further constituents of a perfume oil in order to produce particularly advantageous fragrance mixtures or to perfume products with any fragrance.

In principle, preference is given to such a use of 1,3-propanediol in an effective amount which is sufficient to emphasize or intensify a pleasant odor note or all pleasant odor notes of the one or more odorous substances and / or to to mask or reduce an unpleasant odor note or all of the unpleasant odor notes of the one fragrance alcohol or the several fragrance alcohols.

A sensorially effective amount is to be understood as meaning a proportion of 1,3-propanediol which is sufficient to achieve the above effects, ie highlighting or accentuating a pleasant odor note and / or masking or an unpleasant odor note in the fragrance mixture cause.

Advantageously, the effective amount of 1,3-propanediol is particularly suitable to emphasize or bring out the natural freshness, the charisma or the flowery odor note (s) of the one or more fragrances in the fragrance mixture and / or the to mask or reduce greasy, technical or metallic odor notes of the one or more odorous substances in the odorous substance mixture. Surprisingly, the above-described positive sensory properties of the one or more fragrance alcohols are emphasized and the negative sensory properties of the one or more fragrance alcohols described above are masked or reduced by combining with an effective amount of> 10 wt. % 1,3-propanediol.

The above-described sensory properties of one or more fragrance alcohols are preferably emphasized, masked or suppressed when 1,3-propanediol is used in an amount of> 10% by weight to 90% by weight. The above-described sensory properties of one or more fragrance alcohols are modified even more preferably when 1,3-propanediol is used in an amount of 20% by weight to 80% by weight. The above-described sensory properties of one or more fragrance alcohols are modified even more preferably when 1,3-propanediol is used in an amount of 30% by weight to 70% by weight. The above-described sensory properties of the one fragrance alcohol or of the several fragrance alcohols are even more preferably modified if 1,3-propanediol is used in an amount of 40% by weight to 60% by weight. Most preferably, the previously described sensory properties of the one odorant alcohol or of the plurality of odorant alcohols are modified when 1,3-propanediol is used in an amount of> 50% by weight. All quantitative data are based on the total weight of the fragrance mixture.

Particularly advantageous effects, ie the highlighting or accentuation of pleasant odor notes of a fragrance alcohol or the masking or reduction of unpleasant odor notes of a fragrance alcohol, are achieved if the quantity ratio of 1,3-propanediol in the use according to the invention according to the fourth aspect to the total amount of perfume alcohol (s) is 40:60, preferably 20:80 and particularly preferably 10:90, or in particular the ratio of 1,3-propanediol to the total amount of perfume alcohol (s) with a green odor note 40:60, preferably 20: 80 and particularly preferably 10:90, or in particular the ratio of 1,3-propanediol to the total amount Fragrance alcohol (s) with a floral odor note is 40:60, preferably 20:80 and particularly preferably 10:90.

On the basis of the advantageous effects described above, the present invention therefore relates, according to a fifth aspect, to the use of 1,3-propanediol for producing a non-aqueous fragrance mixture, comprising or consisting of

(i)> 10% by weight 1,3-propanediol; and

Surprisingly, by using a sufficient or effective amount of 1,3-propanediol, a fragrance mixture, preferably a perfume oil, can be produced, whereby the sensory properties of a fragrance alcohol or several fragrance alcohols can be modified.

In particular, by using an effective amount of 1,3-propanediol, a fragrance mixture can be produced, whereby a pleasant odor note or all pleasant odor notes of an odorous substance alcohol can be emphasized or intensified. For example, the odorant mixture can be modified in such a way that the charisma, natural freshness or flowery odor note (s) of the odorant alcohol or odoriferous alcohols are emphasized or intensified when 1,3-propanediol is used in an effective amount.

In an analogous manner, with the use according to the invention of an effective amount of 1,3-propanediol, a fragrance mixture can be produced, whereby in particular an unpleasant odor note or all unpleasant odor notes of a fragrance alcohol, for example musty, greasy, technical or metallic odor note (s) a fragrance alcohol or several fragrance alcohols, masked or reduced. The use of 1,3-propanediol thus enables the production of a fragrance mixture which comprises one or more fragrance alcohol (s) in which the pleasant odor notes are increased and the unpleasant odor notes are reduced. Advantageously, the use of 1,3-propanediol allows the production of a fragrance mixture that comprises one or more fragrance alcohol (s) that has more charisma or more natural freshness or in which the flowery odor notes are emphasized while at the same time greasy, technical or metallic odor notes are reduced.

The one, several or all of the odorant alcohol (s) whose odorous properties are improved according to the invention by using 1,3-propanediol are preferably one or more odorant alcohol (s) with a green odor note or one or more odorant alcohol (s) with a floral odor note.

Basically preferred is / are the one, the several or all of the unpleasant and / or pleasant-smelling, fragrance alcohol (s) with a green odor note selected from the group consisting of fragrance alcohols with a molecular weight in the range from 100 g / mol to 190 g / mol, preferably in the range from 100 g / mol to 158 g / mol.

In a preferred variant, the one or more fragrance alcohols with a green odor note is selected from the group consisting of C6 alcohol, C7 alcohol, (Z) -3-hexenol (cis-3-hexenol), (E. ) -2-hexenol (trans-2-hexenol), (E / Z) -3-hexenol and (Z) -4-hexenol (cis-4-hexenol).

Alternatively preferred is / are the one that contains several or all of the unpleasant and / or pleasantly smelling perfume alcohol (s) with a floral odor note selected from the group consisting of perfume alcohols with a molecular weight in the range from 120 g / mol to 200 g / mol, preferably in the range from 122 to 168 g / mol.

In a preferred variant, one is or are odoriferous alcohol several fragrance alcohols with a floral odor note selected from the group consisting of phenylethyl alcohol, linalool, citronellol, geraniol, nerol, ethyllinalool, tetrahydrolinalool, dihydromyrcenol, C8 alcohol, C9 alcohol, C10 alcohol, alpha-terpineol and tetrahydromyrcenol.

Even more preferred are either two, three, four, five or more different fragrance alcohols selected from the group of fragrance alcohols with a green odor note, which consists of C6 alcohol, C7 alcohol, (Z) -3-hexenol (cis- 3-hexenol), (E) -2-hexenol (trans-2-hexenol), (E / Z) -3-hexenol and (Z) -4-hexenol (cis-4-hexenol), and / or from the Group of odoriferous alcohols with a floral odor note, which consists of phenylethyl alcohol, linalool, citronellol, geraniol, nerol, ethyllinalool, tetrahydrolinalool, dihydromyrcenol, C8 alcohol, C9 alcohol, C10 alcohol, alpha-terpineol and tetrahydromyrcenol.

With regard to constituents (i) and (ii), their preferred or alternative embodiments and their mixing and quantity ratios and their advantageous effects, reference is made to the above detailed description in connection with the fragrance mixture according to the invention, which is for the use according to the invention according to the fifth aspect of the invention is also valid, so that repetition is not necessary. The 1,3-propanediol is used in the inventive use for producing a non-aqueous fragrance mixture in an amount of> 10% by weight. When used according to the invention, 1,3-propanediol is preferably used in an amount of> 10% by weight to 90% by weight. In the use according to the invention, 1,3-propanediol is even more preferably used in an amount of 20% by weight to 80% by weight. In the use according to the invention, 1,3-propanediol is even more preferably used in an amount of 30% by weight to 70% by weight. In the use according to the invention, 1,3-propanediol is even more preferably used in an amount of 40% by weight to 60% by weight. In the use according to the invention, 1,3-propanediol is most preferably used in an amount of> 50% by weight. All quantitative data are based on the total weight of the fragrance mixture.

Particularly advantageous effects, ie the highlighting or accentuation of pleasant odor notes of a fragrance alcohol or the masking or reduction of unpleasant odor notes of a fragrance alcohol, are achieved when using 1,3-propanediol to produce a fragrance mixture according to the fifth Aspect the quantitative ratio of 1,3-propanediol to the total amount of odorant alcohol (s) is 50:50, preferably 40:60, even more preferably 20:80 and most preferably 10:90, or in particular the quantitative ratio of 1,3-propanediol to the total amount of odorant alcohol (s) with a green odor note is 50:50, preferably 40:60, even more preferably 20:80 and most preferably 10:90, or in particular the ratio of 1,3-propanediol to the total amount of odoriferous alcohol (s ) with a floral odor note is 50:50, preferably 40:60, even more preferably 20:80 and most preferably 10:90.

Another aspect of the invention relates to the use of the fragrance mixture or fragrance mixture according to the invention in a sensory effective amount for imparting, modifying or enhancing the sensory properties or an odor note of a perfumed product or for producing a perfumed product. Due to its advantageous primary, ie olfactory, and secondary properties, as described above, the fragrance mixture according to the invention is ideal for perfuming or scenting, ie for imparting, modifying or enhancing the sensory properties of a perfumed product or for producing one perfumed product.

In order to effectively convey, modify or enhance the sensory properties, the odorous substance mixture must be used in a sensory effective amount.

Perfuming is understood to mean imparting a sensory olfactory impression, i.e. an olfactory effect or an additional olfactory effect. Perfuming a product in the narrower sense must be distinguished from a reduction in an unpleasant odor (as described above) and can occur in addition to such a reduction.

In the context of the present application, the term “sensory effective amount” means that the fragrance mixture or fragrance mixture is used in such a sufficient amount that the product resulting therefrom reveals the sensory properties of the fragrance mixture according to the invention during operation or use .

With regard to the fragrance mixture, its preferred or alternative embodiments, its components (i) and (ii), their mixing and quantity ratios and their advantageous effects, reference is made to the above detailed description in connection with the fragrance mixture according to the invention according to the first aspect referenced for the use of the fragrance mixture according to the invention for conveying, modifying or enhancing the sensory properties of a perfumed product or for Manufacture of a perfumed product is equally valid, so that a repetition is not necessary.

According to a further aspect, the present invention relates to a perfumed product which contains the inventive fragrance mixture or fragrance mixture, preferably the perfume oil, in a sensorially effective amount.

The perfumed products, such as cosmetic agents, application agents or detergents and cleaning agents or their further components or compositions, are preferably those as described in paragraphs [0074] to [0204] of WO 2018/114073 A1 will be described in detail. This disclosure is incorporated into the present application in its entirety by specific reference.

In the production of the perfumed products, the fragrance mixtures or fragrance mixtures according to the invention are used for perfuming in liquid form, undiluted or diluted with a solvent. Suitable solvents are e.g. B. ethanol, isopropyl alcohol, diethylene glycol monoethyl ether, glycerine, propylene glycol, 1,2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, etc.

These odorant mixtures can contain up to 90% by weight, preferably about 5 to about 70% by weight, in particular about 10 to about 50% by weight and particularly preferably about 15 to about 25% by weight of the above Contain solvents.

In the preparation of the perfumed products, the fragrance mixtures according to the invention are preferably combined with further constituents. Preferred further components are selected from the group consisting of:

Preservatives, preferably those mentioned in US 2006/0089413, abrasives, anti-acne agents and agents for reducing sebum, preferably those in WO 2008/046791 mentioned, anti-aging agents, preferably those in WO

2005/123101, antibacterial agents, anti-cellulite agents, anti-dandruff agents, preferably the anti-inflammatory agents mentioned in WO 2008/046795, anti-irritant agents, anti-irritants (anti-inflammatory, anti-irritant and anti-irritant agents), preferably those in WO 2007/042472 and US 2006/0089413 mentioned, antimicrobial agents, preferably the antioxidants mentioned in WO 2005/123101, preferably those in WO

2005/123101, astringents, antiseptic agents, antistatic agents, binders, buffers, carrier materials, preferably the chelating agents mentioned in WO 2005/123101, preferably the cell stimulants, cleaning agents, care agents, depilatories, surface-active substances mentioned in WO 2005/123101 , deodorants and antiperspirants, preferably those mentioned in WO 2005/123101, plasticizers, emulsifiers, preferably those in WO

2005/123101 named, enzymes, essential oils, preferably those in US

2008/0070825 mentioned, insect repellents, preferably the fibers, film formers, fixators, foam formers, foam stabilizers, substances to prevent foaming, foam boosters, fungicides, gelling agents and gel forming agents mentioned in WO 2005/123101, preferably those in WO 2005 / 123101 named, hair care products, hair shaping agents, hair straighteners, moisture regulators (moisturizing, moisturizing and / or moisturizing substances), preferably the osmolytes mentioned in WO 2005/123101, preferably the compatible solutes mentioned in WO 2005/123101, preferably those in WO 01 / 76572 and WO 02/15686 mentioned, bleaching agents, strengthening agents, stain-removing agents, optically brightening agents, impregnating agents, dirt-repellent agents, friction-reducing agents, lubricants, moisturizers, ointments, opacifying agents, plasticizing agents, covering agents, polishes, gloss agents, polymers preferably in WO 2008/046676 gena nnten, powders, proteins and protein hydrolyzates, preferably those mentioned in WO 2005/123101 and WO 2008/046676, refatting agents, abrasive agents, skin soothing agents, skin cleansing agents, skin care agents, skin repair agents, preferably containing cholesterol and / or fatty acids and / or ceramides and / or pseudoceramides, preferably those mentioned in WO 2006/053912, Skin lightening agents, preferably the skin-protecting agents, skin-softening agents, skin-cooling agents mentioned in WO 2007/110415, preferably the skin-warming agents mentioned in WO 2005/123101, preferably the stabilizers, UV-absorbing agents and UV agents mentioned in WO 2005/123101 Filters, preferably the benzylidene-beta-dicarbonyl compounds mentioned in WO 2005/123101, preferably the alpha-benzoylcinnamic acid nitriles mentioned in WO 2005/107692, preferably the AhR receptor antagonists mentioned in WO 2006/015954, preferably those in WO 2007 / 128723 and WO 2007/060256, detergents, fabric softeners, suspending agents, skin tanning agents, preferably those mentioned in WO 2006/045760, thickeners, vitamins, preferably the oils, waxes and fats mentioned in WO 2005/123101, preferably those in WO 2005/123101 named, phospholipids, preferably the fatty acids named in WO 2005/123101 (saturated fatty acids, mono- or polyunsaturated fats acids, α-hydroxy acids, polyhydroxy fatty acids), preferably the liquefiers, dyes and color protecting agents mentioned in WO 2005/123101 and pigments, preferably those mentioned in WO 2005/123101, anti-corrosives, aromas and flavorings, preferably those in S. Arctander, Perfume and Flavor Chemicals, Eigenverlag, Montclair, NJ, 1969 and Surburg, Panten, Common Fragrance and Flavor Materials, 6th Edition, Wiley-VCH, Weinheim, 2016, in particular the other fragrances explicitly mentioned in US 2008/0070825 that are not already Components of the fragrance mixture according to the invention are perfume oil, alcohols and polyols, preferably the surfactants mentioned in WO 2005/123101, preferably the animal extracts, yeast extracts, algae or microalgae extracts, electrolytes, liquefiers, organic solvents mentioned in WO 2005/123101, preferably those mentioned in WO 2005/123101, or silicones and silicone derivatives, preferably those mentioned in WO 2008/046676.

For some applications, it is also advantageous to use the fragrance mixtures according to the invention adsorbed on a carrier, which ensures both a fine distribution of the fragrances in the product and a controlled release during use. Such carriers can be porous inorganic materials such as light sulfate, silica gels, zeolites, plasters, clays, clay granules, Aerated concrete, etc. or organic materials such as wood, cellulose-based substances, sugar or plastics such as PVC, polyvinyl acetates or polyurethanes.

For other applications it is advantageous to use the fragrance mixture or fragrance mixture of the invention in microencapsulation, spray-dried, as an inclusion complex or as an extrusion product and to add it in this form to the (pre-) product to be perfumed.

If necessary, the properties of the compositions modified in this way can be further optimized by so-called "coating" with suitable materials with regard to a more targeted release of fragrances, for which purpose waxy plastics such as polyvinyl alcohol are preferably used. The resulting products in turn represent products according to the invention.

With regard to the aforementioned application form of the fragrance mixtures according to the invention, reference is made to the above description in connection with the fragrance mixture according to the first aspect of the present invention, which is also valid for the preparation of the perfumed products, so that repetition is not necessary.

In a preferred variant of the present invention, the perfumed products which are perfumed or scented with the fragrance mixture according to the invention are selected from the group consisting of: perfume extracts, eau de perfumes, eau de toilettes, aftershave lotions, eau de colognes, pre-shave products, splash colognes, perfumed

Refreshing wipes, acidic, alkaline and neutral cleaning agents, such as floor cleaners, window glass cleaners, dishwashing detergents, bathroom and sanitary cleaners, scouring milk, solid and liquid toilet cleaners, powder and foam carpet cleaners, liquid detergents, powder detergents, laundry pretreatment agents such as bleach, soaking agents and stain removers, fabric softeners, laundry soap, washing tablets, disinfectants, surface disinfectants, air fresheners in liquid, gel-like or solid carrier form, aerosol sprays, waxes and polishes, such as furniture polishes, floor waxes, shoe polishes, personal care products such as solid and liquid soaps, shower gels, shampoos, shaving soaps, shaving foams, bath oils, cosmetic emulsions of the oil-in-water, water-in-oil and water-in-oil-in-water types, such as skin creams and skin lotions , Face creams and lotions, sunscreen creams and lotions, aftersun creams and lotions, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, aftershave creams and lotions, tanning creams and lotions, hair care products such as , Hair gels, hair lotions, hair conditioners, permanent and semi-permanent hair dyes, hair shaping agents such as cold waves and hair straighteners, hair lotions, hair creams and lotions, deodorants and antiperspirants, such as underarm sprays, roll-ons, deodorant sticks, deodorant creams, decorative cosmetics, candles, lamp oils Incense sticks, insecticides, repellents and fuels.

Particularly preferred perfumed products which contain the fragrance mixture according to the invention are selected from the group consisting of:

Eau de perfumes, eau de toilettes, aftershave, eau de colognes, pre-shave products, splash colognes;

acidic, alkaline and neutral detergents, especially in the household sector, preferably floor cleaners, window glass cleaners, dishwashing detergents, bathroom and sanitary cleaners, scouring milk, solid and liquid toilet cleaners, powder and foam carpet cleaners, liquid detergents, powder detergents, fabric softeners, surface disinfectants, especially re for hard surfaces (hard surface cleaner);

Body care products, preferably solid and liquid soaps, shower gels, sham poos, shaving soaps, shaving foams;

cosmetic emulsions of the oil-in-water, water-in-oil and water-in-oil-in-water types, preferably skin creams and lotions, face creams and lotions, sun protection creams and lotions, After-sun creams and lotions, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, after-shave creams and lotions, skin tanning creams and lotions, skin lightening creams and lotions; Hair care products, preferably hair sprays, hair gels, setting hair lotions, hair conditioners, permanent and semi-permanent hair dyes, hair lotions, hair creams and lotions;

Deodorants and antiperspirants, preferably underarm sprays, roll-ons (preferably as an alcoholic or non-alcoholic solution, as a gel or (micro) emulsion, deodorant sticks (deodorant sticks), deodorant creams.

Particularly preferred perfumed products according to the invention are laundry detergents and cleaning agents, hygiene or care products, in particular in the field of body and hair care, cosmetics and household.

In a preferred variant, the present invention relates to perfumed products which contain the fragrance mixture according to the invention, the 1,3-propanediol and one or more fragrance (s) from the group of fragrance alcohols, preferably from the group of fragrance alcohols with green notes and / or from the group of odoriferous alcohols with floral notes, in amounts from about 0.01 to about 10% by weight, preferably in amounts from about 0.1 to about 5% by weight and particularly preferably from about 0.25 to about 3% by weight, based in each case on the total weight of the perfumed product.

The detergents and cleaning agents containing the fragrance mixture according to the invention (abbreviated as WSR agents) in the context of the present invention can be in solid form as powders, granules, tablets and the like, but also in liquid, gel or paste form. It is preferably a detergent that is suitable for both manual and machine washing, especially textiles. It can also be detergents or cleaning agents for the industrial sector or for the household sector. Cleaning agents can also be used to clean hard surfaces, for example. It can be, for example, dishwashing detergents that are used for manual or machine cleaning of dishes. It can also be common industrial or household cleaners with which hard surfaces such as furniture surfaces, tiles, wall and floor coverings are cleaned. In addition to crockery, all the others come as hard surfaces hard surfaces, in particular made of glass, ceramic, plastic or metal, in household and commercial use.

The WSR agents can contain other commercially available ingredients, such as surfactants, builders, bleaches, bleach activators, thickeners, enzymes, electrolytes, pH adjusters, dyes and fragrances, foam inhibitors, anti-redeposition agents, optical brighteners,

Graying inhibitors, anti-crease agents, antimicrobial agents, preservatives, antioxidants, antistatic agents, UV adsorbers,

Heavy metal complexing agents and the like.

Finally, the present invention also relates to a method for producing a perfumed product which comprises the following steps: (a1) providing the fragrance mixture according to the invention,

(c1) Bringing into contact or mixing a sensorially effective amount of the fragrance mixture provided in step (a1) with the further component (s) provided in step (b1) to obtain the perfumed product.

The amount of 1,3-propanediol (i) in the fragrance mixture is> 10% by weight

to emphasize or emphasize a pleasant odor note or all pleasant odor notes of the one fragrance alcohol or the several fragrance alcohols (ii) of the fragrance mixture,

and or

to mask or reduce an unpleasant odor note or all unpleasant odor notes of the one odorant or of the several odorants (ii) of the odorant mixture.

In a preferred variant of the method, the amount of 1,3-propanediol (i), as defined above, in the fragrance mixture is sufficient to reduce the to emphasize or emphasize pleasant smell note or all pleasant smell notes more charisma, natural freshness or flowery odor note (s) of the one fragrance alcohol or of the several fragrance alcohols (ii) of the fragrance mixture; and / or to mask or reduce the unpleasant odor note or all unpleasant odor notes musty, fatty, technical or metallic odor note (s) of the one odorant alcohol or of the several odorant alcohols (ii) of the odorant mixture.

An alternative variant of the process for producing a perfumed product comprises the following steps:

(c2) mixing a sensorially effective amount of the odorant alcohol or odoriferous alcohols (ii) provided in step (a2) with the further constituent (s) provided in step (b2) to obtain a mixture, and

(d2) Bringing the mixture obtained in step (c2) into contact with 1,3-propanediol in an amount of> 10% by weight.

The amount of 1,3-propanediol (i) in the fragrance mixture is sufficient to

to emphasize or intensify a pleasant odor note or all pleasant odor notes of the one fragrance alcohol or the several fragrance alcohols (ii) of the fragrance mixture,

and or

to mask or reduce an unpleasant odor note or all of the unpleasant odor notes of the one fragrance alcohol or of the several fragrance alcohols (ii) of the fragrance mixture. In a preferred variant of the method, the amount of 1,3-propanediol (i), as defined above, in the fragrance mixture is sufficient to give the pleasant odor note or all pleasant odor notes more radiance, natural freshness or flowery odor note (n ) to emphasize or intensify the one or more fragrance alcohols (ii) of the fragrance mixture; and / or to mask or reduce the unpleasant odor note or all unpleasant odor notes musty, fatty, technical or metallic odor note (s) of the one odorant alcohol or of the several odorant alcohols (ii) of the odorant mixture.

The present invention will now be described and illustrated in more detail by means of further examples, the present invention not being restricted to these examples.

Examples

Example 1

Sensory evaluation of 10% solutions of the perfume alcohols in 1,3-propanediol in comparison with 10% solutions of the perfume alcohol in dipropylene glycol (DPG)

For an explanation of the product names of the fragrances, see, for example, S. Arctander, Perfume and Flavor Materials, Volumes I and II, Montclair, NJ, 1969, Eigenverlag or H. Surburg, J. Panten, “Common Fragrance and Flavor Materials”, 6 2nd edition, Wiley-VCH, Weinheim, 2016.

The sensory evaluation was carried out as follows: The odor was evaluated by eight test persons trained in sensory control. For this purpose, the above test solutions were filled into closed jars. The samples were coded, tested in a randomized sequence and with the exclusion of disturbing influences such as color, noise and foreign odors in a sensor room. Two odor strips were each immersed in two test solutions and evaluated in pairs. Each test person noted their olfactory perception. The final result for a sample was then determined by matching / parallel terms.

Table 3

The 10% solutions of the perfume alcohols in 1,3-propanediol were perceived more strongly and with less unpleasant side notes than the 10% solutions of the perfume alcohols in DPG. The solutions in 1,3-propanediol appear more flowery and natural and have more volume.

Example 2 Sensory evaluation of 10%, 20%, 40% and 60% solutions of the odorant alcohols in 1,3-propanediol

For an explanation of the product names of the fragrances see, for example, S. Arctander, Perfume and Flavor Materials, Volumes I and II, Montclair, NJ, 1969, self-published or H. Surburg, J. Panten, “Common Fragrance and Flavor Materials”, 6 2nd edition, Wiley-VCH, Weinheim, 2016.

Table 4

The solutions of the abovementioned odoriferous alcohols are perceived more strongly and with less unpleasant side notes depending on the concentration of 1,3-propanediol. By varying the 1,3-propanediol concentration in the fragrance mixture according to the invention, for example by increasing or decreasing the 1,3-propanediol content, the sensory properties of the fragrance mixture and thus the sensory profile of the fragrance mixture can be adjusted or varied.

Example 3

Composition of perfume oil mixtures

Table 5: Chord Rose

Table 6: Chord Freesia

Example 4

Sensory evaluation of solutions of the perfume oil mixtures according to Example 3 in 1,3-propanediol and in DPG in comparison

Table 7: Composition of the solutions

The sensory evaluation was carried out as follows: The odor was evaluated by eight test persons trained in sensory control. For this purpose, the above solutions were filled into closed glasses. The samples were coded, tested in a randomized sequence and with the exclusion of disturbing influences such as color, noise and foreign odors in a sensor room. Two odor strips were each immersed in two test solutions and evaluated in pairs. Each test person noted their olfactory perception. The final result for a sample was then determined by matching / parallel terms. In comparison to solution A, solution B smells much more cosmetic, rosier, sweeter and has more impact.

Compared to solution C, solution D smells much stronger, greener and more watery.

Compared to solution, solution F smells livelier, greener, rounder and has more volume.

Compared to solution G, solution H smells stronger, livelier, more flowery and fresher.

Claims

1. Non-aqueous fragrance mixture, preferably perfume oil, comprising or consisting of

(i)> 10% by weight 1,3-propanediol; and

(ii) one or more odorant (s) from the group of odorant alcohols, in particular from the group of odoriferous alcohols with green notes and / or the group of odoriferous alcohols with floral notes.

2. Fragrance mixture according to claim 1, wherein the fragrances from the group of fragrance alcohols with green notes each have a molecular weight in the range from 100 to 190 g / mol and / or wherein the fragrances from the group of fragrance alcohols with flowery notes each have a molecular weight in the range from 120 to 200 g / mol.

3. Fragrance mixture according to claim 1 or 2, wherein the one or more fragrance alcohols with green notes is / are selected from the group consisting of C6 alcohol, C7 alcohol, (Z) -3-hexenol (cis-3 - Hexenol), (E) -2-hexenol (trans-2-hexenol), (E / Z) -3-hexenol and (Z) -4-hexenol (cis-4-hexenol), and / or in which one Fragrance alcohol and / or the several fragrance alcohols with floral notes is / are selected from the group consisting of phenylethyl alcohol, linalool, citronellol, geraniol, nerol, ethyllinalool, tetrahydrolinalool, dihydromyrcenol, C8 alcohol, C9 alcohol, C10 alcohol, alpha -Terpineol and Tetrahydromyrcenol.

4. Fragrance mixture according to one of claims 1 to 3, wherein the amount of 1, 3-propanediol in the fragrance mixture is sufficient to

to emphasize or emphasize a pleasant odor note or all pleasant odor notes of the one odorous substance alcohol or of the several odorous substance alcohols,

in particular the pleasant odor note or all pleasant odor notes more radiance, natural freshness and flowery To emphasize or emphasize the odor note (s) of the one odorous substance alcohol or of the several odorous substance alcohols;

and or

in order to mask or reduce an unpleasant odor note or all unpleasant odor notes of the one or more fragrance alcohols,

in particular to mask or reduce the unpleasant odor note or all unpleasant odor notes musty, greasy, technical or metallic odor note (s) of the one odorous substance alcohol or of the several odorous substance alcohols.

5. Fragrance mixture according to one of the preceding claims 1 to 4, wherein the quantitative ratio of 1, 3-propanediol to the total amount

Fragrance alcohol (s) is 50:50, in particular 10:90.

6. Fragrance mixture according to one of claims 1 to 5, wherein the fragrance mixture contains one or more further fragrance (s) which is / are selected from the group consisting of:

(1) hydrocarbons;

(2) Aliphatic alcohols

(3) Aliphatic aldehydes and their acetals

(4) Aliphatic ketones and their oximes

(5) Aliphatic sulfur-containing compounds

(6) Aliphatic nitriles

(7) Esters of aliphatic carboxylic acids

(8) Acyclic terpene alcohols

(9) acyclic terpene aldehydes and ketones;

(10) cyclic terpene alcohols;

(11) Cyclic terpene aldehydes and ketones

(12) cyclic alcohols;

(13) cycloaliphatic alcohols;

(14) cyclic and cycloaliphatic ethers;

(15) cyclic and macrocyclic ketones;

(16) cycloaliphatic aldehydes;

(17) cycloaliphatic ketones;

(18) esters of cyclic alcohols;

(19) esters of cycloaliphatic alcohols;

(20) esters of cycloaliphatic carboxylic acids;

(21) araliphatic alcohols;

(22) esters of araliphatic alcohols and aliphatic carboxylic acids;

(23) araliphatic ethers;

(24) aromatic and araliphatic aldehydes;

(25) aromatic and araliphatic ketones;

(26) Aromatic and araliphatic carboxylic acids and their esters;

(27) nitrogen-containing aromatic compounds;

(28) phenols, phenyl ethers, and phenyl esters;

(29) heterocyclic compounds;

(30) lactones;

and mixtures of the aforementioned fragrances.

7. A method for producing a non-aqueous fragrance mixture, which comprises the following steps:

Providing 1,3-propanediol;

Providing a fragrance alcohol or a plurality of fragrance alcohols from the group of fragrance alcohols, in particular from the group of fragrance alcohols with green notes and / or the group of fragrance alcohols with floral notes.

Bringing into contact and mixing an effective amount of> 10% by weight of 1,3-propanediol with the fragrance alcohol or the several fragrance alcohols to obtain the non-aqueous fragrance mixture.

8. A method for modifying the sensory properties of a fragrance alcohol or several fragrance alcohols, which comprises the following steps:

Mixing of a fragrance alcohol or several fragrance alcohols with an effective amount of> 10% by weight of 1,3-propanediol to emphasize or emphasize a pleasant odor note or all pleasant odor notes of a fragrance alcohol or several fragrance alcohols,

in particular to emphasize or emphasize the pleasant smell note or all pleasant smell notes more charisma, natural freshness or flowery smell note (s) of an odorant alcohol or several odoriferous alcohols;

and or

in particular to mask or reduce the unpleasant odor note or all unpleasant odor notes musty, greasy, technical or metallic odor note (s) of an odorous substance alcohol or several odorous substance alcohols.

9. The method according to claim 7 or 8, wherein the one or more fragrance alcohols with green notes is selected from the group consisting of C6 alcohol, C7 alcohol, (Z) -3-hexenol (cis- 3-hexenol), (E) -2-hexenol (trans-2-hexenol), (E / Z) -3-hexenol and (Z) -4-hexenol (cis-4-hexenol), and / or in which the one or more perfume alcohols with floral notes is / are selected from the group consisting of phenylethyl alcohol, linalool, citronellol, geraniol, nerol, ethyllinalool, tetrahydrolinalool, dihydromyrcenol, C8 alcohol, C9 alcohol, C10 alcohol, alpha- Terpineol and tetrahydromyrcenol.

10. The method according to any one of claims 7 to 9, in which the quantitative ratio of 1,3-propanediol to the total amount of odorant alcohol (s) is 50:50, in particular 10:90.

11. Use of 1,3-propanediol in an effective amount for modifying the sensory properties of a fragrance alcohol or several fragrance alcohols, in particular to emphasize or accentuate a pleasant odor note or all pleasant odor notes of a fragrance alcohol or several fragrance alcohols;

and or

12. Use of 1,3-propanediol for the production of a non-aqueous fragrance mixture, comprising or consisting of

(i)> 10% by weight 1,3-propanediol; and

13. Use according to claim 11 or 12, in which the one or more fragrance alcohols with green notes is / are selected from the group consisting of C6 alcohol, C7 alcohol, (Z) -3-hexenol (cis- 3-hexenol), (E) -2-hexenol (trans-2-hexenol), (E / Z) -3-hexenol and (Z) -4-hexenol (cis-4-hexenol), and / or in the the one or more perfume alcohols with floral notes is / are selected from the group consisting of phenylethyl alcohol, linalool, citronellol, geraniol, nerol, ethyllinalool, tetrahydrolinalool, dihydromyrcenol, C8 alcohol, C9 alcohol, C10 alcohol, alpha -Terpineol and Tetrahydromyrcenol.

14. Use according to one of claims 11 to 13, in which the ratio of 1,3-propanediol to the total amount of odorant alcohol (s) is 50:50, in particular 10:90.

15. Use of the fragrance mixture according to any one of claims 1 to 6 in a sensorially effective amount for imparting, modifying or enhancing an odor note of a perfumed product or for producing one perfumed product.

16. Perfumed product containing a sensorially effective amount of the fragrance mixture according to one of claims 1 to 6.

17. Perfumed product according to claim 16, selected from the group consisting of: perfume extracts, eau de perfumes, eau de toilettes, aftershave lotions, eau de colognes, pre-shave products, splash colognes, scented refreshing tissues, sour, alkaline and neutral cleaning agents, such as floor cleaners, window glass cleaners, dishwashing detergents, bathroom and sanitary cleaners, scouring milk, solid and liquid toilet cleaners, powder and foam carpet cleaners, liquid detergents, powder detergents, laundry pretreatment agents such as bleach, soaking agents and stain removers Fabric softeners, laundry soap, washing tablets, disinfectants, surface disinfectants, air fresheners in liquid, gel-like or solid carrier form, aerosol sprays, waxes and polishes, such as furniture polishes, floor waxes, shoe creams, personal care products such as solid and liquid soaps, shower gels, Shaving Soaps, R Asian foams, bath oils, cosmetic emulsions of the oil-in-water, water-in-oil and water-in-oil-in-water types such as skin creams and skin lotions, face creams and lotions, sun protection creams and lotions, Aftersun creams and lotions, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, aftershave creams and lotions, tanning creams and lotions, hair care products such as, for example, hair sprays, hair gels, hair lotions, hair conditioners, permanent hair rinses, permanent hair conditioners Hair shaping agents such as cold waves and hair straighteners, hair lotions, hair creams and lotions, deodorants and antiperspirants, such as, for example, armpit sprays, roll-ons, deodorant sticks, deodorant creams, decorative cosmetics products, candles, lamp oils, incense sticks, insecticides, repellants and fuels.

18. A method for making a perfumed product according to any one of Claims 16 or 17, comprising the following steps:

(a1) providing the fragrance mixture according to one of claims 1 to

6,

(c1) bringing into contact or mixing a sensorially effective amount of the fragrance mixture provided in step (a1) with the further constituent (s) provided in step (b1) to obtain the perfumed product;

the amount of 1,3-propanediol (i) in the odorant mixture being> 10% by weight

a pleasant odor note or all the pleasant odor notes of the one fragrance alcohol or of the several fragrance alcohols (ii)

To emphasize or emphasize the fragrance mixture,

especially the pleasant odor note or all pleasant ones

Odor notes more radiance, natural freshness or flowery

Odor note (s) of one or more odorant alcohol

To emphasize or accentuate fragrance alcohols (ii) of the fragrance mixture;

and or

to mask or reduce an unpleasant odor note or all unpleasant odor notes of the one fragrance alcohol or of the several fragrance alcohols (ii) of the fragrance mixture,

in particular the unpleasant odor note or all unpleasant odor notes musty, fat, technical or metallic odor note (s) of one or more odorous substance alcohol

To mask or reduce fragrance alcohols (ii) of the fragrance mixture;

or

(a2) Provision of a fragrance / several fragrances (ii) the

Fragrance mixture according to one of Claims 1 to 6,

(b2) Provision of a further component or several more Components of the perfumed product to be manufactured,

(c2) Mixing a sensorially effective amount of the one or more fragrance alcohols provided in step (a2)

Fragrance alcohols (ii) with the further component (s) provided in step (b2) to obtain a mixture, and

(d2) bringing the mixture obtained in step (c2) into contact with 1,3-propanediol,

wherein the amount of 1, 3-propanediol is> 10 wt .-% to

To emphasize or emphasize the fragrance mixture,

especially the pleasant odor note or all pleasant ones

Odor notes more radiance, natural freshness or flowery

Odor note (s) of one or more odorant alcohol

To emphasize or accentuate fragrance alcohols (ii) of the fragrance mixture;

and or

To mask or reduce fragrance alcohols (ii) of the fragrance mixture.