CN117396586A - 1, 4-butanediol mono-or diesters as fragrance chemicals - Google Patents

Abstract

The present invention relates to: r of formula (I) ¹ ‑O‑(CH ₂ ) ₄ ‑O‑C(＝O)‑R ² Use of 1, 4-butanediol mono-or diesters or mixtures of different compounds (I) as aromatic chemicals, wherein R ¹ Is hydrogen or-C (=O) -R ³ The method comprises the steps of carrying out a first treatment on the surface of the And R is ² And R is ³ Independently C ₁ ‑C ₂ -an alkyl group; their use for modifying and/or enhancing the fragrance of a composition; compositions comprising such 1, 4-butanediol mono-and/or diesters; for preparing a aromatizing composition using the 1, 4-butanediol mono-and/or diesterIs a method of (2).

Description

1, 4-butanediol mono-or diesters as fragrance chemicals

The present invention relates to the use of 1, 4-butanediol mono-or diesters of formula (I) or mixtures thereof as fragrance chemicals, their use for modifying and/or enhancing the fragrance of compositions, compositions comprising such 1, 4-butanediol mono-and/or diesters of formula (I), and methods for preparing fragrance compositions using the 1, 4-butanediol mono-and/or diesters.

Background

Aroma chemicals, especially perfumes, are of great interest in particular in the field of cosmetics and cleaning and laundry compositions. Fragrances of natural origin are mostly expensive, the availability of which is often limited and whose content, purity etc. vary due to fluctuations in environmental conditions. To circumvent these undesirable factors, it is therefore of great interest to produce synthetic substances with sensory properties similar to more expensive natural fragrances or with novel and interesting sensory properties.

Although a large number of fragrance chemicals already exist, there is a continuing need for new components in order to be able to meet the numerous characteristics desired for a very diverse field of application. These include firstly sensory properties, i.e. the compounds should have favourable odour (olfactory) or taste properties. In addition, the aroma chemicals should also have additional positive secondary properties, such as for example an effective preparation process, possibly providing better sensory properties due to synergistic effects with other aroma chemicals, higher stability over a wide composition range and higher extensibility and/or better durability under certain application conditions.

However, since even small changes in chemical structure cause large changes in sensory properties such as smell and also taste, it is extremely difficult to purposely find substances having certain sensory properties such as a certain smell. Thus, finding new fragrances and flavours is in most cases difficult and laborious without knowing even if in fact a substance with the desired odour and/or taste will be found.

DE 886304B describes the preparation of various 1, 4-butanediol esters, such as 1, 4-butanediol diacetate or dibutyrate, by reacting tetrahydrofuran with carboxylic acids in the presence of esterification catalysts. Esters are said to be useful as solvents, plasticizers, intermediate compounds, starting compounds for plastics or perfumes and pharmaceutical compositions. However, this document does not describe any olfactory properties of the ester itself.

DE-A-2525893 describes a process for preparing cellulose acetate fiber rods suitable for cigarette filters, in which 1, 4-butanediol diacetate is used as plasticizer. 1, 4-butanediol diacetate is characterized by being odorless and nontoxic and not compromising cigarette flavor or smoke aroma.

CN 103642260 relates to a deodorizing material containing glass fiber, methacrylic acid, cotton fiber, charcoal powder, polyester fiber and diacetate such as 1, 4-butanediol diacetate. The material is characterized by being odorless.

Semi-preparative reverse phase liquid chromatography fractionation of wine extracts and other alcoholic beverages is described by Ferriera et al in J.chromatogrj.J.chromatography J. 1999,864,77-88. One of the many isolated fractions of Chardonnay wine contains acetaldehyde, ethyl lactate, furfural, ethyl 3-hydroxybutyrate, methylthiopropanol, 1, 4-butanediol diacetate, and diethyl malate; its aroma is described as a yeast extract, moist, weak. 1, 4-butanediol diacetate is not specifically described as having a fragrance.

A gas chromatographic study of volatiles of wine comparing grape and antifungal grape varieties is described by Rapp et al in Vitis [ grape vine ],1989,28,21-29. Among many other materials, 1, 4-butanediol monoacetate was identified as a component of these volatiles. However, it is not described as having a specific fragrance.

The volatile and non-volatile components of Hami melon are described in M.G. Moshonas et al in Lebensm-Wiss. U. -technology [ food science and technology ]1993,26,577-589. Among many other things, 1, 4-butanediol diacetate was identified as a volatile. However, it is not specifically described as having fragrance.

CN 104824121A relates to a spray-coating antistaling agent for turkey meat surface. This comprises in particular 2, 3-diacetyl and BDO diacetate.

WO 2011/101352 relates to a liquid mixture comprising a) a polyol, a polyol ether having at least one unetherified hydroxyl group or a polyalkylene ether having at least one unetherified terminal hydroxyl group, b) 1, 3-bis (caprolactam-1-yl) butane and c) diacetoxybutane, which mimics the dissolution profile of a specific graft copolymer.

It is an object of the present invention to provide novel fragrance chemicals. Furthermore, these materials should be combinable with other fragrance chemicals, allowing for the creation of novel and advantageous sensory attributes. Furthermore, the preparation of these new aroma chemicals should be easy and efficient to allow for their rapid, economical and environmentally friendly manufacture. It is a particular object to provide aroma chemicals with a reduced carbon footprint, in particular aroma chemicals that are at least partially available from renewable resources. Another specific object is to provide a fragrance chemical having a fruity fragrance, preferably having a fruity and sweet fragrance.

These and further objects are achieved by the esters of the formula (I) or mixtures thereof, i.e. different compounds (I), more precisely mixtures of two or more different compounds (I), as shown below.

Disclosure of Invention

The invention relates to the use of 1, 4-butanediol mono-and/or diesters of formula (I) or mixtures of two or more different 1, 4-butanediol mono-and/or diesters of formula (I) as fragrance chemicals

R ¹ -O-(CH ₂ ) ₄ -O-C(＝O)-R ² (I)

Wherein the method comprises the steps of

R ¹ Selected from hydrogen and-C (=o) -R ³ A group of; and is also provided with

R ² And R is ³ Independently of one another C ₁ -C ₂ -an alkyl group.

Thus, unexpectedly and contrary to what is suggested in the prior art, 1, 4-butanediol diacetate is not odorless at all, but has a very pleasant fragrance. Its fragrance is not prominent but easily perceived. The same applies to the other esters (I).

Furthermore, the present invention relates to the use of 1, 4-butanediol mono-or diesters of formula (I) or mixtures of different 1, 4-butanediol mono-and/or diesters of formula (I) for modifying and/or enhancing the fragrance of a composition; in particular for modifying and/or enhancing the flavour impact of the composition; in particular for modifying the fragrance characteristics of a perfuming ready-to-use composition.

Furthermore, the present invention relates to the use of 1, 4-butanediol mono-or di-esters of formula (I) or a mixture of different 1, 4-butanediol mono-and/or di-esters of formula (I) for imparting fragrance to a composition, preferably for imparting fragrance to a personal care or home care composition, alternatively preferably for imparting fragrance to a composition, alternatively preferably for imparting fruit taste or sweet taste or combined fruit taste and sweet fragrance to a composition, more preferably for imparting fruit taste or sweet taste or combined fruit taste and sweet fragrance to a composition, in particular for imparting fruit taste or sweet taste or combined fruit taste and sweet fragrance to a personal care or home care composition.

The invention also relates to a composition comprising a 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I), and at least one further component selected from the group consisting of an aromatic chemical, a non-aromatic chemical carrier, an antioxidant and a deodorant active agent different from compound (I).

The invention further relates to a process for preparing a fragrance chemical composition, in particular a perfuming ready-to-use composition, comprising incorporating into the composition a 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I), or comprising mixing simultaneously or consecutively a 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) with other components of the composition or with a preformed mixture of a part of other components of the composition.

The invention also relates to a method for imparting fragrance, preferably flavour, to a composition by incorporating 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) into the composition, or by mixing a 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) with other components of the composition or with a preformed mixture of a part of other components of the composition, simultaneously or consecutively.

Furthermore, the present invention relates to a method of modifying and/or enhancing the fragrance of a composition; preferably for modifying and/or enhancing the fragrance effect of the composition; a method for modifying the fragrance characteristics of a fragrance composition, in particular a perfuming ready-to-use composition, comprising incorporating into the composition, in particular a ready-to-use composition, at least one compound of formula (I), or comprising mixing simultaneously or consecutively a mixture of 1, 4-butanediol mono-and/or diester of formula (I) or of a different 1, 4-butanediol mono-and/or diester of formula (I) with the other components of the composition or with a preformed mixture of a part of the other components of the composition.

Detailed Description

Definition:

in the context of the present invention, the term "fragrance" refers to sensory properties and includes odors and/or flavors.

The term "fragrance chemical" means a substance used to obtain a fragrance effect (the term "fragrance effect" is used interchangeably herein with the term "note") and includes its use to obtain an olfactory and/or flavoring effect. The term "olfactory effect" or "scent effect" means a scent effect without any positive or negative judgment, whereas the term "fragrance effect" or "scent effect" (used interchangeably herein) as used herein relates to a generally perceived pleasant scent effect. Thus, "fragrance" or "aroma" refers to an aroma chemical that primarily causes a pleasant odor effect. Flavor means an aroma chemical that causes a taste effect.

The term "fragrance attribute" means the overall fragrance effect of the fragrance chemical and is composed of the individual fragrance effects of the fragrance chemical.

The term "fragrance composition", as used herein, refers to a composition that causes fragrance. The term fragrance composition comprises "odour composition" and/or "flavour composition". The odour composition is a composition that mainly causes odour effects, whereas the flavour composition is a composition that mainly causes taste effects.

The term "odour composition" comprises "flavour composition" or "fragrance composition" (used interchangeably herein) which mainly gives rise to a generally perceived pleasant odour effect.

"pleasant smell", "pleasant smell effect", "pleasant smell property", "pleasant feeling smell effect" and similar terms are all pleasurable expressions describing the delicacy and clarity of the smell effect delivered by the fragrance chemical. The more general expression "favorable sensory properties" or "favorable sensory properties" describes the delicacy and clarity of the sensory effect delivered by the fragrance chemical. For the purposes of the present invention, the terms "sensory" and "feel" relate to olfactory or flavoring characteristics. "nice" and "clear" are terms familiar to those skilled in the art (perfumers). Nice is generally referred to as a spontaneously induced, positively perceived, pleasant sensory effect. However, "good" is not necessarily synonymous with "sweet" in taste. "good" may also be musk or sandalwood odors. "clarity" generally refers to a spontaneously induced sensory effect that, for the same test panel, causes reproducible recall of the same specific thing. For example, the substance may have a spontaneous reminiscent of an "apple" scent: the scent will then be clearly "apple". If this apple smell is very pleasant, because it reminds for example a sweet, fully ripe apple, the smell will be referred to as "delicately". However, the smell of typical sour apples may also be clear. This substance has particularly advantageous sensory properties if both reactions are produced when the substance is smelled, in this example a good and clear apple smell.

The term "malodorous substance" refers to a substance or aroma chemical that exhibits a strong odor effect. A strong odour effect is understood to mean those properties of the aroma chemical which are clearly perceived even at very low gas space concentrations.

The intensity may be determined by a threshold determination. The threshold is the concentration of the substance in the relevant gas space at which the odor effect is just still perceivable by the representative test panel, although it is no longer necessary to define the odor effect. The class of substances which may be the most strongly odorous, i.e. which have a very low odor threshold, is the thiol, the threshold of which is usually ppb/m ³ Within the range.

The term "persistence" describes the evaporation behavior of a fragrance chemical over time. The permanence may be determined, for example, by applying a fragrance chemical to the test strip and by subsequent olfactory assessment of the odor effect of the test strip. For fragrance chemicals with high permanence, the time span over which the panel can still recognize the fragrance effect is long.

The term "substantivity" describes the interaction of an aroma chemical with a surface (such as, for example, skin or textile), especially after subsequent treatment of the surface (such as, for example, washing). Fastness can be determined, for example, by washing textiles with textile detergent compositions comprising fragrance chemicals and subsequently evaluating the textile directly after washing (wet textiles) for smell and evaluating dry textiles after prolonged storage.

The term "stability" describes the behavior of a fragrance chemical upon contact with oxygen, light, and/or other substances. Fragrance chemicals having high stability retain their fragrance attributes over a long period of time, preferably in a variety of compositions and under a variety of storage conditions.

In order to impart a durable fragrance effect to the composition or to a surface treated with the composition, the durability, firmness and stability of the fragrance chemicals in the composition should preferably be high.

The terms "booster" or "boost" are used herein to describe the effect of enhancing and/or modifying the fragrance of a fragrance chemical or composition. The term "enhancement" includes improvements in the aesthetic and/or clarity properties of the fragrance and/or improvements in the intensity. The term "modification" includes a change in the fragrance properties.

The accelerator action is particularly desirable in flavour compositions, for example in deodorants, air fresheners or in the flavouring sector in chewing gums, when applications featuring previous conditioning are required, in which the odour is to be transferred particularly rapidly and strongly.

The terms "compound" and "substance" are synonymously used throughout the present invention.

In the context of the present invention, the expression "C" is used ₁ -C ₂ -alkyl "refers to methyl and ethyl.

The 1, 4-butanediol monoester of formula (I) is a compound (I) wherein R ¹ Is hydrogen. The 1, 4-butanediol diester of formula (I) is a compound (I) wherein R ¹ is-C (=O) -R ³ 。

If in the following the compound of formula (I) is defined as a specific, defined compound (instead of a mixture of different compounds I), this means that the compound contains less than 0.1% by weight of other compounds I relative to the total weight of the specific, defined compound I and optionally one or more other compounds I.

In mixtures containing different compounds (I), these are indicated in the radical R ¹ Definition of (1), group R ² Is different in definition or both. Thus, the mixture may for example contain monoesters derived from different carboxylic acids, diesters derived from different carboxylic acids, both mono-and diesters derived from the same carboxylic acid, and both mono-and diesters derived from different formic acids. "derived from" in this context relates only to R ² -C (=o) -or R ³ -theoretical source of C (=o) -groups (if present); not of practical synthetic origin. Preferably, the compounds (I) in the mixture differ only in the monoester (R ¹ =h) or diester (R ¹ ＝-C(＝O)-R ³ ) Both derived from the same carboxylic acid (i.e. R ² The same in the mono-and diesters; and R is ² ＝R ³ )。

Where applicable, the following comments made regarding the preferred definitions of the variables are valid, individually and preferably in combination with each other, regarding the compounds of formula (I) as defined herein, as well as regarding the compositions, uses and methods of the invention as defined herein.

Example of the invention (E.x)

General and preferred embodiments E.x are summarized in the following non-exhaustive list. Further preferred embodiments will become apparent from the following paragraphs of this list.

E.1. Use of 1, 4-butanediol mono-or diesters of formula (I) or mixtures of two or more different 1, 4-butanediol mono-and/or diesters of formula (I) as fragrance chemicals

R ¹ -O-(CH ₂ ) ₄ -O-C(＝O)-R ² (I)

Wherein the method comprises the steps of

R ¹ Selected from hydrogen and-C (=o) -R ³ A group of; and is also provided with

R ² And R is ³ Independently of one another C ₁ -C ₂ -an alkyl group.

E.2. The use according to embodiment e.1, wherein,

using 1, 4-butanediol diester (i.e. R ¹ is-C (=O) -R ³ And R is ² And R is ³ Both are C ₁ -C ₂ -alkyl); or (b)

Using 1, 4-butanediol diester (i.e. R ¹ is-C (=O) -R ³ And R is ² And R is ³ Both are C ₁ -C ₂ Alkyl) and 1, 4-butanediol monoester (i.e., R ¹ Is hydrogen and R ² Is C ₁ -C ₂ -alkyl).

E.3. The use according to embodiment e.2, wherein,

Using 1, 4-butanediol diester (i.e. R ¹ is-C (=O) -R ³ And R is ² And R is ³ Both are C ₁ -C ₂ -alkyl); wherein R is ² And R is ³ Is identical (i.e., the 1, 4-butanediol diester is 1, 4-butanediol diacetate or 1, 4-butanediol dipropionate); or (b)

Using 1, 4-butanediol diester (i.e. R ¹ is-C (=O) -R ³ And R is ² And R is ³ Both are C ₁ -C ₂ Alkyl) and 1, 4-butanediol monoester (i.e., R ¹ Is hydrogen and R ² Is C ₁ -C ₂ -alkyl); wherein R in the diester ² And R is ³ R in monoester ² Is identical (i.e., the mixture is a mixture of 1, 4-butanediol diacetate and 1, 4-butanediol monoacetate, or a mixture of 1, 4-butanediol dipropionate and 1, 4-butanediol monopropionate).

E.4. The use according to any of the preceding embodiments, wherein,

R ¹ is hydrogen or-C (=O) -CH ₃ The method comprises the steps of carrying out a first treatment on the surface of the And is also provided with

R ² Is methyl.

E.5. The 1, 4-butanediol diacetate of example E.4 (i.e., compound (I) wherein R ¹ is-C (=O) -R ³ And R is ² And R is ³ Methyl).

E.6. The 1, 4-butanediol diacetate of example E.4 (i.e., compound (I) wherein R ¹ is-C (=O) -R ³ And R is ² And R is ³ Methyl) and 1, 4-butanediol monoacetate (i.e., compound (I), wherein R ¹ Is H and R ² Methyl) is provided.

E.7. The use according to any of embodiments e.1 to e.3, wherein,

R ¹ is hydrogen or-C (=O) -CH ₂ CH ₃ The method comprises the steps of carrying out a first treatment on the surface of the And is also provided with

R ² Is ethyl.

E.8. 1, 4-butanediol dipropionate according to example E.7 (i.e., compound (I), wherein R ¹ is-C (=O) -R ³ And R is ² And R is ³ Ethyl).

E.9. 1, 4-butanediol dipropionate according to example E.7 (i.e.chemical combinationCompound (I), wherein R ¹ is-C (=O) -R ³ And R is ² And R is ³ Is ethyl) and 1, 4-butanediol monopropionate (i.e., compound (I), wherein R ¹ Is H and R ² Ethyl) is provided.

E.10. The use of any one of embodiments e.2 to E.4, e.6, e.7 and E.9, wherein the mixture contains 1, 4-butanediol monoester in an amount of 0.1% to 99% by weight relative to the total weight of the 1, 4-butanediol diester and the 1, 4-butanediol monoester.

E.11. The use according to embodiment e.10, wherein the mixture contains 1, 4-butanediol monoester in an amount of 0.1% to <50% by weight relative to the total weight of the 1, 4-butanediol diester and the 1, 4-butanediol monoester.

E.12. The use according to embodiment e.11, wherein the mixture contains 1, 4-butanediol monoester in an amount of 0.1 to 30% by weight relative to the total weight of the 1, 4-butanediol diester and the 1, 4-butanediol monoester.

E.13. The use according to embodiment e.12, wherein the mixture contains 1, 4-butanediol monoester in an amount of 0.1% to 20% by weight relative to the total weight of the 1, 4-butanediol diester and the 1, 4-butanediol monoester.

E.14. The use according to embodiment e.13, wherein the mixture contains 1, 4-butanediol monoester in an amount of 0.1 to 10% by weight relative to the total weight of the 1, 4-butanediol diester and the 1, 4-butanediol monoester.

E.15. The use according to embodiment e.14, wherein the mixture contains 1, 4-butanediol monoester in an amount of 0.1 to 5% by weight relative to the total weight of the 1, 4-butanediol diester and the 1, 4-butanediol monoester.

E.16. The use according to embodiment e.15, wherein the mixture contains 1, 4-butanediol monoester in an amount of 0.1 to 2% by weight relative to the total weight of the 1, 4-butanediol diester and the 1, 4-butanediol monoester.

E.17. The use according to embodiment e.16, wherein the mixture contains 1, 4-butanediol monoester in an amount of 0.1% to 1% by weight relative to the total weight of the 1, 4-butanediol diester and the 1, 4-butanediol monoester.

E.18. The use according to embodiment e.17, wherein the mixture contains 1, 4-butanediol monoester in an amount of 0.1% to 0.5% by weight relative to the total weight of the 1, 4-butanediol diester and the 1, 4-butanediol monoester.

E.19. The use according to any of the preceding embodiments, wherein the 1, 4-butanediol mono-or diester of formula (I) is derived from 1, 4-butanediol obtained from renewable sources.

E.20. The use according to example E.19, wherein the 1, 4-butanediol mono-or diester of formula (I) is derived from 1, 4-butanediol obtained from a renewable source and carboxylic acid R obtained from a renewable source ² -C (=o) OH and R ³ -C (=o) OH, if R ¹ is-C (=O) -R ³ 。

E.21. The use according to any of embodiments E.19 or E.20, wherein the 1, 4-butanediol ester ¹⁴ The C isotope is at a detectable level.

E.22. The use according to any of embodiments e.19 to e.21, wherein, in the 1, 4-butanediol, ¹² c isotope and method for producing the same ¹⁴ The molar ratio of the C isotope is less than 2×10 ¹² :1。

E.23. The use according to any of embodiments E.19 to E.22, wherein, in the 1, 4-butanediol mono-or diester of formula (I), ¹² c isotope and method for producing the same ¹⁴ The molar ratio of C isotope is less than 3×10 ¹² :1。

E.24. The use according to any of the preceding embodiments as a fragrance.

E.25. Use of a 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) as defined in any of embodiments e.1 to e.23 for modifying and/or enhancing the fragrance of a composition.

E.26. The use according to example e.25 for modifying and/or enhancing the flavour effect of a composition.

E.27. The use according to example e.26 for modifying the fragrance profile of a perfuming ready-to-use composition.

E.28. Use of 1, 4-butanediol mono-or diesters of formula (I) or mixtures of different 1, 4-butanediol mono-and/or diesters of formula (I) as defined in any of examples e.1 to e.23 for imparting a fruity or sweet taste or a combined fruity and sweet olfactory note.

E.29. Use of 1, 4-butanediol diacetate or of a mixture of 1, 4-butanediol diacetate and 1, 4-butanediol monoacetate according to example e.28, which preferably contains 0.1 to 0.5% by weight or 0.1 to 1% by weight or 0.1 to 2% by weight or 0.1 to 5% by weight or 0.1 to 10% by weight or 0.1 to 20% by weight of 1, 4-butanediol monoacetate relative to the total weight of 1, 4-butanediol diacetate and 1, 4-butanediol monoacetate, for imparting one of the following olfactory notes: red fruit, raspberry, blueberry, sweet; or any combination thereof.

E.30. Use of 1, 4-butanediol dipropionate or of a mixture of 1, 4-butanediol dipropionate and 1, 4-butanediol monopropionate according to example e.28, preferably containing 0.1% to 0.5% by weight or 0.1% to 1% by weight or 0.1% to 2% by weight or 0.1% to 5% by weight or 0.1% to 10% by weight of 1, 4-butanediol monopropionate relative to the total weight of 1, 4-butanediol dipropionate and 1, 4-butanediol monopropionate, for imparting one of the following olfactory notes: red fruit, raspberry, blueberry, sweet; or any combination thereof.

E.31. The use according to any of the preceding embodiments in a composition selected from the group consisting of perfume compositions, body care compositions, products for oral or dental hygiene, hygiene products, cleaning compositions, textile detergent compositions, compositions for fragrance dispensers, food products, food supplements, pharmaceutical compositions and crop protection compositions, preferably selected from the group consisting of perfume compositions, body care compositions, products for oral or dental hygiene, hygiene products, cleaning compositions, textile detergent compositions, compositions for fragrance dispensers and crop protection compositions, and in particular selected from the group consisting of body care compositions, products for oral or dental hygiene, hygiene products, cleaning compositions, textile detergent compositions, compositions for fragrance dispensers.

E.32. Use of a 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) as defined in any of embodiments e.1 to e.23 for imparting fragrance to a composition.

E.33. The use according to example 32 for imparting a fragrance to a composition.

E.34. The use according to example 33 for imparting fragrance to a personal care or home care composition.

E.35. The use according to example 32 for imparting a fruity or sweet taste or a combined fruity and sweet aroma to a composition.

E.36. The use of embodiment 35 for imparting a fruity or sweet taste or a combined fruity and sweet aroma to a composition.

E.37. The use of embodiment 36 for imparting a fruity or sweet taste or a combined fruity and sweet fragrance to a personal care or home care composition.

E.38. A composition comprising a 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) as defined in any of embodiments e.1 to e.23, and at least one additional component selected from the group consisting of an aromatic chemical, a non-aromatic chemical carrier, an antioxidant and a deodorant active agent different from compound (I).

E.39. The composition of embodiment e.38, wherein the composition is not an alcoholic beverage, fruit juice, fruit or seed.

E.40. The composition of embodiment e.38, wherein the composition does not comprise diacetyl;

E.41. The composition of example e.38, wherein the composition does not comprise 1, 3-bis (caprolactam-1-yl) butane.

E.42. The composition of embodiment e.38, wherein the composition is not an alcoholic beverage, fruit juice, fruit, or seed, wherein the composition does not comprise diacetyl; and wherein the composition does not comprise 1, 3-bis (caprolactam-1-yl) butane.

E.43. The composition of any of embodiments e.38-42, wherein the at least one additional component is selected from the group consisting of fragrance chemicals other than compound (I), surfactants, oil components, solvents, antioxidants, and deodorant actives.

E.44. The composition according to embodiment e.43, wherein where the non-aromatic chemical carriers comprise one or more solvents selected from the group consisting of ethanol, isopropanol, dipropylene glycol (DPG), propylene glycol, 1, 2-butanediol, glycerol, diethylene glycol monoethyl ether, diethyl phthalate (DEP), isopropyl myristate (IPM), triethyl citrate (TEC), benzyl benzoate, and mixtures thereof.

E.45. The composition of example e.44, wherein the solvents are selected from the group consisting of isopropanol, dipropylene glycol (DPG), propylene glycol, 1, 2-butanediol, diethylene glycol monoethyl ether, diethyl phthalate (DEP), isopropyl myristate (IPM), triethyl citrate (TEC), benzyl benzoate, and mixtures thereof.

E.46. The composition of example e.45, wherein the solvents are selected from the group consisting of isopropyl alcohol, isopropyl myristate (IPM), triethyl citrate (TEC), benzyl benzoate, and mixtures thereof.

E.47. The composition according to any one of embodiments e.38 to e.46, wherein the fragrance chemicals different from compound (I) are selected from the group consisting of: geranyl acetate (3, 7-dimethyl-2, 6-octadien-1 yl acetate), alpha-hexyl cinnamaldehyde, 2-phenoxyethyl isobutyrate (Phenilate) ¹ ) Dihydromyrcenol (2, 6-dimethyl-7-octen-2-ol), methyl dihydrojasmonate (preferably having a cis isomer content of more than 60 wt.%) (Hedione ⁹ ，Hedione HC ⁹ ) 4,6,7, 8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta [ g ]]Benzopyran (Galaxoid) ³ ) Tetrahydrolinalool (3, 7-dimethyl)Octyl-3-ol), ethyl linalool, benzyl salicylate, 2-methyl-3- (4-tert-butylphenyl) propanal (Lyseral) ² ) Cinnamyl alcohol, 4, 7-methano-3 a,4,5,6,7 a-hexahydro-5-indenyl ester acetate and/or 4, 7-methano-3 a,4,5,6,7 a-hexahydro-6-indenyl ester acetate (herbafloat ¹ ) Citronellol, citronellyl acetate, tetrahydrogeraniol, vanillin, linalyl acetate, storyl acetate (1-phenylethyl acetate), octahydro-2, 3, 8-tetramethyl-2-naphthaleneethanone and/or 2-acetyl-1,2,3,4,6,7,8-octahydro-2, 3, 8-tetramethylnaphthalene (Iso E Super) ³ ) Hexyl salicylate, 4-tert-butylcyclohexyl acetate (Oryclone) ¹ ) 2-tert-butylcyclohexyl acetate (Agrumex HC) ¹ ) Alpha-ionone (4- (2, 6-trimethyl-2-cyclohexen-1-yl) -3-buten-2-one), alpha-n-methyl ionone (n-alpha-methylionone), alpha-isomethyl ionone, coumarin, terpineol acetate, 2-phenylethyl alcohol, 4- (4-hydroxy-4-methylpentyl) -3-cyclohexenecarboxaldehyde (Lyral) ³ ) Alpha-amyl cinnamic aldehyde, ethylene glycol brassylate, (E) -and/or (Z) -3-methylcyclopenta-5-enone (Muscenon) ⁹ ) 15-pentadec-11-enolide and/or 15-pentadec-12-enolide (Globalide) ¹ ) 15-cyclopentadecanolide (Macrolide) ¹ ) 1-5,6,7, 8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphtyl) ethanone (Tonalid ¹⁰ ) 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol (Florol) ⁹ ) 2-ethyl-4- (2, 3-trimethyl-3-cyclopenten-1-yl) -2-buten-1-ol (Sandolen) ¹ ) Cis-3-hexenyl acetate, trans-2/cis-6-nonyldienol, 2, 4-dimethyl-3-cyclohexenecarboxaldehyde (Vertocitral) ¹ ) 2,4, 7-Tetramethylooct-6-en-3-one (Claritone) ¹ ) 2, 6-dimethyl-5-heptene-1-aldehyde (Melonal) ² ) Borneol, 3- (3-isopropylphenyl) butanal (Florrydral) ² ) 2-methyl-3- (3, 4-methylenedioxyphenyl) propanal (Helional) ³ ) 3- (4-ethylphenyl) -2, 2-dimethylpropionaldehyde (Florazon) ¹ ) 7-methyl-2H-1, 5-benzodioxepan-3 (4H) -one (Calone), 3, 5-trimethylcyclohexyl acetate (preferably having a cis isomer content of 70wt.% or more), 2, 5-trimethyl-1, 2,3, 4a,5,6, 7-octahydronaphthalen-2-ol (Ambrinol S) ¹ ) 3- (4-tert-butylphenyl) -propanal (Bourgeonal) ⁴ ) 2-methyl Ethyl valerate (Manzanate) ⁴ ) Ethoxymethoxy cyclododecane (Amberwood) ¹ ) 2, 4-dimethyl-4, 4a,5,9 b-tetrahydroindeno [1,2-d ]][1,3]Dioxin (Magnolan) ¹ ) (2-tert-butylcyclohexyl) acetate (Verdox) ³ ) 3- [5, 6-trimethylbicyclo [2.2.1]]Hept-2-yl]Cyclohexan-1-ol (Sandela) ⁴ ) Menthone, isomenthone, carvone, camphor, beta-ionone, beta-n-methyl ionone, beta-isomethyl ionone, alpha-iris ketone, alpha-damascone, beta-damascone, delta-damascone, acetylated cedar wood oil, and mixtures thereof.

E.48. The composition according to embodiment e.47, wherein the fragrance chemicals different from compound (I) are selected from the group consisting of: geranyl acetate, α -hexylcinnamaldehyde, 2-phenoxyethyl isobutyrate, dihydromyrcenol, methyl dihydrojasmonate (preferably having a cis isomer content of more than 60 wt.%), 4,6,7, 8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta [ g ] benzopyran, tetrahydrolinalool, ethyl linalool, benzyl salicylate, 2-methyl-3- (4-tert-butylphenyl) propanal, cinnamyl alcohol, 4, 7-methano-3 a acetate, 4,5,6,7 a-hexahydro-5-indenyl ester, 4, 7-methano-3 a acetate, 4,5,6,7 a-hexahydro-6-indenyl ester, citronellyl acetate, tetrahydrogeraniol, linalyl acetate, storax acetate, octahydro-2, 3, 8-tetramethyl-2-naphthaleneethanone, 2-acetyl-1,2,3,4,6,7,8-octahydro-2, 3, 8-tetramethylnaphthalene, hexyl salicylate, 4-tert-butylcyclohexyl acetate, 2-tert-butylcyclohexyl acetate, alpha-ionone, alpha-n-methylionone, alpha-isomethylionone, coumarin, terpineyl acetate, 4- (4-hydroxy-4-methylpentyl) -3-cyclohexene aldehyde, alpha-amyl cinnamic aldehyde, ethylene glycol brassylate, (E) -3-methylcyclopentadec-5-enone, (Z) -3-methylcyclopentadec-5-enone, 15-pentadec-11-enolide, 15-pentadec-12-enolide, 15-cyclopentadecolide, 1- (5, 6,7, 8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthyl) ethanone, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, 2-ethyl-4- (2, 3-trimethyl-3-cyclopenten-1-yl) -2-buten-1-ol, cis-3-hexenyl acetate, trans-2/cis-6-nonylenol, 2, 4-dimethyl-3-cyclohexenecarboxaldehyde, 2,4, 7-tetramethyloct-6-en-3-one, 2, 6-dimethyl-5-hepten-1-aldehyde, borneol, 3- (3-isopropylphenyl) butanal 2-methyl-3- (3, 4-methylenedioxyphenyl) propanal, 3- (4-ethylphenyl) -2, 2-dimethylpropionaldehyde, 7-methyl-2H-1, 5-benzodioxepan-3 (4H) -one, 3, 5-trimethylcyclohexyl acetate (preferably having a cis isomer content of 70wt.% or more), 2, 5-trimethyl-1, 2,3, 4a,5,6, 7-octahydronaphthalen-2-ol, 3- (4-tert-butylphenyl) -propanal, ethyl 2-methylpentanoate, ethoxymethoxycyclododecane, 2, 4-dimethyl-4, 4a,5,9 b-tetrahydroindeno [1,2-d ] [1,3] dioxin, (2-tert-butylcyclohexyl) acetate, 3- [5, 6-trimethylbicyclo [2.2.1] hept-2-yl ] cyclohex-1-ol, menthone, isomenthone, carvone, β -n-methylionone, β -isomethylionone, α -irisone, α -damascone, β -damascone, δ -damascone, acetylated cedar wood oil, and mixtures thereof.

E.49. The composition of any one of embodiments e.38 to e.48, selected from the group consisting of a perfume composition, a body care composition, a product for oral or dental hygiene, a hygiene product, a cleaning composition, a textile detergent composition, a composition for fragrance dispenser, a food product, a food supplement, a pharmaceutical composition, and a crop protection composition.

E.50. The composition of example e.49 selected from the group consisting of perfume compositions, body care compositions, products for oral or dental hygiene, hygiene products, cleaning compositions, textile detergent compositions, compositions for fragrance dispensers, and crop protection compositions.

E.51. A process for preparing a fragrance chemical composition, which comprises incorporating into the composition a 1, 4-butanediol mono-or diester of formula (I) as defined in any one of examples e.1 to e.23 or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I).

E.52. A process for the preparation of a fragrance chemical composition which comprises mixing 1, 4-butanediol mono-or diester of formula (I) as defined in any one of examples e.1 to e.23 or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) simultaneously or continuously with the other components of the composition or with a preformed mixture of a part of the other components of the composition.

E.53. The method according to any of examples e.51 or e.52 for preparing a perfuming composition.

E.54. The method according to example e.53 for preparing a perfuming ready-to-use composition.

E.55. A method for imparting fragrance to a composition by incorporating 1, 4-butanediol mono-or diester of formula (I) as defined in any one of examples e.1 to e.23 or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) into the composition or by mixing 1, 4-butanediol mono-or diester of formula (I) as defined in any one of examples e.1 to e.23 or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) simultaneously or continuously with other components of the composition or with a preformed mixture of a part of other components of the composition.

E.56. The method of example e.55, for imparting a fragrance to a composition.

E.57. The method of any one of embodiments e.55 or e.56 for imparting a fruity or sweet taste or a combined fruity and sweet aroma, preferably a fragrance, to a composition.

E.58. The method of any one of embodiments e.55 to e.57 for imparting fragrance to a personal care or home care composition.

E.59. A method of modifying and/or enhancing the fragrance of a composition, which method comprises incorporating into the composition a 1, 4-butanediol mono-or diester of formula (I) as defined in any of examples e.1 to e.23 or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I), or comprises mixing simultaneously or continuously a 1, 4-butanediol mono-or diester of formula (I) as defined in any of examples e.1 to e.23 or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) with other components of the composition or with a preformed mixture of a part of other components of the composition.

E.60. The method according to example e.59 for modifying and/or enhancing the flavour effect of a perfuming composition, which comprises incorporating into the perfuming composition a 1, 4-butanediol mono-or diester of formula (I) as defined in any of examples e.1 to e.23, or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I), or a mixture of 1, 4-butanediol mono-or diester of formula (I) as defined in any of examples e.1 to e.23, or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I), simultaneously or consecutively admixed with other components of the composition or with a preformed mixture of a part of other components of the composition.

E.61. A method according to example e.60 for modifying and/or enhancing the flavour effect of a perfuming ready-to-use composition, the method comprising incorporating into the ready-to-use composition a 1, 4-butanediol mono-or diester of formula (I) as defined in any one of examples e.1 to e.23, or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I).

E.62. The method of any one of embodiments e.60 or e.61 for modifying the fragrance profile of a perfuming composition.

The companies from which the above-listed aromatic chemical compounds identified by trade names and indices can be obtained are listed below.

In a preferred embodiment, 1, 4-butanediol diesters are used, i.e. wherein R ¹ is-C (=O) -R ³ Compound (I) of (a). In such diesters, R ² And R is ³ Preferably the same, however for practical reasons (simpler synthesis and purification), but also to make it easier and more economical to provide a reproducible fragrance effect.

In another preferred embodiment, 1, 4-butanediol diester (i.e., wherein R ¹ is-C (=O) -R ³ Compound (I) of (c) and 1, 4-butanediol monoester (i.e., wherein R) ¹ A compound (I) which is hydrogen). In such mixtures, R in the diester is likewise preferred ² And R is ³ R in monoester ² Are identical; i.e., the mono-and diesters are derived from the same (and only one) carboxylic acid.

More preferably, R ¹ Is hydrogen or-C (=O) -CH ₃ The method comprises the steps of carrying out a first treatment on the surface of the And R is ² Is methyl.

Thus, in a more preferred embodiment, 1, 4-butanediol diacetate is used.

In another more preferred embodiment, a mixture of 1, 4-butanediol diacetate and 1, 4-butanediol monoacetate is used.

In another preferred embodiment, R ¹ Is hydrogen or-C (=O) -CH ₂ CH ₃ The method comprises the steps of carrying out a first treatment on the surface of the And R is ² Is ethyl. Thus, in a preferred embodiment, 1, 4-butanediol dipropionate is used. In another preferred embodiment, a mixture of 1, 4-butanediol dipropionate and 1, 4-butanediol monopropionate is used.

However, 1, 4-butanediol diacetate and mixtures of 1, 4-butanediol diacetate and 1, 4-butanediol monoacetate are more preferred.

If a mixture containing 1, 4-butanediol diester and 1, 4-butanediol monoester is used, for example a mixture of the above preferred 1, 4-butanediol diacetate and 1, 4-butanediol monoacetate or a mixture of 1, 4-butanediol dipropionate and 1, 4-butanediol monopropionate, the mixture contains 1, 4-butanediol monoester in an amount of preferably 0.1 to 99% by weight. However, since the diesters generally have a more intense odour and are less polar, which brings advantages in the formulation, it is preferred that the diesters are the main components in the mono-/diester mixture, i.e. are present in an amount of more than 50% by weight relative to the total weight of the 1, 4-butanediol diester and 1, 4-butanediol monoester. Thus, more preferably, the mixture contains 1, 4-butanediol monoester in an amount of 0.1% to <50% by weight, for example 0.1% to 30% by weight; more preferably from 0.1 to 20% by weight, even more preferably from 0.1 to 10% by weight, in particular from 0.1 to 5% by weight, more in particular from 0.1 to 2% by weight, in particular from 0.1 to 1% by weight and very in particular from 0.1 to 0.5% by weight, relative to the total weight of 1, 4-butanediol diester and 1, 4-butanediol monoester.

The 1, 4-butanediol mono-and diesters of the formula (I) are known substances and are commercially availableOr can be prepared by standard procedures, for example by reacting 1, 4-butanediol with acetic acid and/or propionic acid (R ² -C(＝O)OH/R ³ C (=o) OH), or a more active derivative thereof, such as an acid halide (e.g. chloride or bromide), anhydride or active ester thereof, under typical esterification conditions, if desired with removal of the formed reaction water (if such an acid is used) or the formed acid (if an anhydride is used) to increase the reaction rate, or with neutralization (if an acid halide is used).

The esterification may be carried out in the presence of an esterification catalyst; this is especially indicated if such carboxylic acids are used. Suitable esterification catalysts are well known in the art and are, for example, metal-based catalysts, for example iron, cadmium, cobalt, lead, zinc, antimony, magnesium, titanium and tin catalysts in the form of metals, metal oxides or metal salts, such as metal alkoxides; or acids, for example mineral acids, such as sulfuric acid, hydrochloric acid or phosphoric acid; organic sulfonic acids, such as methanesulfonic acid or p-toluenesulfonic acid or strongly acidic cation exchange resins.

The term "strongly acidic cation exchanger" refers to a cation exchanger in the h+ form having strongly acidic groups. The strongly acidic group is typically a sulfonic acid group; they are typically bound to a polymer matrix, which may be, for example, gelatinous and/or macroporous. Styrene (co) polymers containing sulfonic acid groups are preferred, in particular styrene-divinylbenzene copolymers containing sulfonic acid groups. Commercial examples of such cation exchangers are (Lanxess) Lan Cheng Gongsi),(Blatt (The Purolite Company)), -j>(Dow chemical Co., ltd. (Dow Chemical Company)),>(Rongohas Corp (Rohm and Haas Company))),(Rogowski Corp.). Preferred strong acid cation exchangers are:K 1221、K 1461、K 2431、K 2620、K 2621、K 2629、K 2649、FPC 22、FPC 23、IR 120、131、15、31、35、36、39、46、70、SGC650、C100H、C150H、50X8、red and +.>NR-50. Alternatively, the cation exchanger may be a perfluorinated ion exchange resin, e.g. as +.>And (3) selling trademarks.

The esterification may be carried out in the presence of a base; this is especially indicated if carboxylic acid halides are used. Suitable bases are, for example, organic bases, such as tertiary amines, for example trimethylamine, triethylamine, tripropylamine, ethyldiisopropylamine, etc., or basic N-heterocycles, such as morpholine, pyridine, lutidine, DMAP, DABCO, DBU or DBN.

For the preparation of the diesters, 1, 4-butanediol is typically reacted with at least two equivalents, for example 2 to 4 moles of acetic acid (or derivative thereof) and/or propionic acid (or derivative thereof) or mixtures thereof per mole of 1, 4-butanediol.

To prepare the monoester, 1, 4-butanediol is typically reacted with up to one equivalent of acetic acid (or derivative thereof) and/or propionic acid (or derivative thereof) or mixtures thereof per mole of 1, 4-butanediol. Even with these molar ratios, the diesters are in most cases still formed with monoesters. Thus, if a pure monoester or a mixture with fewer diesters is desired, a separation step is required. The separation may be carried out by conventional means such as distillation, extraction or chromatography.

The reaction may be carried out in a solvent or in a pure state.

After the reaction is completed, the esterification product may be isolated by conventional means, if desired after neutralization (especially if an acid halide or anhydride is used as starting material or if an excess of acid is used) and/or removal of the catalyst (especially if the catalyst is solid, such as one of the metal-based catalysts or ion exchange resins described above), for example by distillation, extraction or chromatography. The isolated product may then be further purified if desired.

1, 4-butanediol is a commercially available commodity substance and can be prepared, for example, from acetylene and formaldehyde via Lei Peifa (Reppe process) and subsequent hydrogenation of the intermediate 2-butyne-1, 4-diol, or from maleic anhydride via the Davy process.

In a preferred embodiment, however, the 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) is derived from a renewable source. More specifically, at least the alcohol portion of the ester (i.e., 1, 4-butanediol) is derived from a renewable source. More preferably, the alcohol moiety of the ester (i.e., 1, 4-butanediol) and the carboxylic acid moiety of the ester (i.e., R ² -C (=o) -moiety and R ³ -C(＝O) -moiety (if R ¹ is-C (=O) -R ³ And if R ² ≠R ³ ) Both derived from renewable sources.

1, 4-butanediol prepared from renewable sources is commercially available. Known processes start, for example, with furfural (furan-2-aldehyde), which in turn is obtained from carbohydrates, such as pentoses contained in many plant materials (most commonly using agricultural byproducts like bagasse and corn cobs), which are dehydrated with sulfuric acid. The production of wood pulp by the magnesium bisulphite process also produces a large amount of furfural. Furfural can be converted to furan, which can be hydrogenated and ring-opened to 1, 4-butanediol. Alternatively, succinic acid or polyhydroxybutyric acid obtained from a fermentation process may be hydrogenated to 1, 4-butanediol directly or via gamma-butyrolactone and THF. Succinic acid may be obtained from fermentation of biomass (using, for example, various strains), for example from sugar (e.g., sucrose, raffinose, fructose, glucose, galactose, lactose, mannose, xylose, arabinose) or glycerol (in turn obtained from vegetable/animal oils or fats). 1, 4-butanediol can also be obtained by direct fermentation of the sugar.

R ² -C (=o) -moiety and R ³ The carboxylic acids on which the-C (=o) -moiety, if present, is based are present in large amounts in nature. For example, acetic acid may be obtained from the oxidation of ethanol, which may in turn be obtained from the fermentation of any sugar-or starch-containing crop, such as fruits and cereals.

The source of 1, 4-butanediol or esters thereof from renewable sources can be verified, for example, by radiocarbon dating. The radiocarbon years are based on the following facts: radioactive carbon [ ] ¹⁴ C) Is constantly generated in the earth's atmosphere by the interaction of cosmic rays with atmospheric nitrogen: cosmic rays produce neutrons in the atmosphere, which may strike nitrogen-14 # ¹⁴ N) atoms. Upon release of protons, these in turn decay into ¹⁴ C. The obtained product ¹⁴ C combines with atmospheric oxygen to form radioactive carbon dioxide which enters the plant by photosynthesis, then into the herbivore feeding the plant and finally into the complete biosphere by the carnivore feeding the herbivore. Carbon exchange with the environment of animals or plants after their deathStop and then follow ¹⁴ C undergoes a radioactive decay to a point where, ¹⁴ the amount of C starts to decrease.

Thus, measuring 1, 4-butanediol or 1, 4-butanediol ester in a sample ¹⁴ The amount of C is an indicator of its origin: in 1, 4-butanediol wherein the 1, 4-butanediol is derived from a renewable source, ¹⁴ the amount of C will be the same as or not substantially lower than the amount found in the present organism.

In general, the number of the devices used in the system, ¹² c isotope and method for producing the same ¹⁴ The molar ratio of the C isotopes is used as an indicator. In the case of an organism in which a biological material is present, ¹² C isotope and method for producing the same ¹⁴ The molar ratio of the C isotope is about 1X 10 ¹² 1 (more precisely 1X 10) ¹² :1.25)。

Thus, if at least a portion of a 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) is derived from a renewable source, then the 1, 4-butanediol ester ¹⁴ The content of the C isotope will be at a detectable level. Suitable for determination of ¹⁴ Methods of content of C isotopes are known in the art and provide generally comparable results. For example, a method according to ASTM D6866-21 may be used; this method was developed specifically for determining the bio-based/bio-derived carbon content in biological products. However, other methods are also suitable. ¹⁴ The level of detection of the available methods of C isotope content is such that it allows radiocarbon dating between about 300 and 60000 years before the present time, which is very remote from the age of fossil carbon sources. Thus, any detected ¹⁴ The C isotopes are indicators of renewable sources of 1, 4-butanediol esters.

In a preferred embodiment, the 1, 4-butanediol ester ¹² C isotope and method for producing the same ¹⁴ The molar ratio of C isotope is less than 3×10 ¹² 1, i.e. it is from about 1X 10 ¹² 1 (more precisely from 1X 10) ¹² 1.25) to less than 3X 10 ¹² :1。

In another preferred embodiment, the esters are based on 1, 4-butanediol ¹² C isotope and method for producing the same ¹⁴ The molar ratio of the C isotope is less than 2×10 ¹² 1, i.e. it is from about 1X 10 ¹² 1 (more precisely from 1X 10) ¹² 1.25) to less than 2X 10 ¹² :1。

In a further preferred embodiment, the 1, 4-butanediol mono-or diester of formula (I) or the mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) is derived from para-C ₁ "exhaust gas" (e.g. CO) ₂ Or methane) that would otherwise be released to the atmosphere. For example, CO ₂ Can be separated from a power plant or factory and converted into valuable products, such as acetic acid, which can be used to synthesize the 1, 4-butanediol mono-or diester of formula (I) of the present invention. Alternatively, separated CO ₂ May be reacted with acetylene to form acetylene dicarboxylic acid which is then hydrogenated to 1, 4-butanediol (typically, the triple bond is hydrogenated, the resulting succinic acid or alkali metal succinate is esterified with methanol to dimethyl succinate and which is then hydrogenated to 1, 4-butanediol). In yet another embodiment, 1, 4-butanediol may typically be produced from acetylene and formaldehyde, wherein formaldehyde is derived from the separated CO ₂ Is directly reduced or separated into CO ₂ Obtained via a reduction-oxidation sequence of methanol, or from isolated methane via oxidation of methanol. For example, methane may be separated from stables of ruminants, as well as from biomass combustion and power plants.

Alternatively, the 1, 4-butanediol mono-and diesters of formula (I) can be prepared by reacting acetic acid and/or propionic acid with a compound X- (CH) ₂ ) ₄ Y is prepared by reaction, where X represents a leaving group selected from halogens such as Cl, br, I and sulfonates such as tosylate, mesylate, triflate or perfluorobutanesulfonate, and Y has the same meaning as X (for the preparation of the diester) or is a protected OH group (for example protected by one of the usual silyl protecting groups, such as TMS, TES, TBDMS, TIPS or TBDPS; for the preparation of the monoester), typically in the presence of a base, such that the acetate or propionate is the actual nucleophile. Suitable bases are those listed above. Alternatively, instead of acetic acid and/or propionic acid, acetate and/or propionate are used and no further base is used, typically alkali metal acetate and/or propionate, e.g. sodium acetate or ethyl acetatePotassium acid and/or sodium or potassium propionate. If Y is a protected OH group, the compound is deprotected after the esterification reaction is complete, for example with HF or pyridinium hydrofluoric acid. Compound X- (CH) ₂ ) ₄ Y is commercially available or can be prepared by standard reactions. They can be obtained, for example, from 1, 4-butanediol and thus also from renewable sources or from para-C ₁ Waste gas upgrading utilization is available.

Preferably, 1, 4-butanediol mono-or diesters of formula (I) or mixtures of two or more different 1, 4-butanediol mono-or diesters of formula (I) are used to impart an olfactory effect. In particular, 1, 4-butanediol mono-or diesters of the formula (I) or mixtures of two or more different 1, 4-butanediol mono-or diesters of the formula (I) are used as fragrances.

In particular, 1, 4-butanediol mono-or diesters of formula (I) or mixtures of two or more different 1, 4-butanediol mono-or diesters of formula (I) are used to impart a fruity or sweet taste or a combined fruity and sweet olfactory note.

In particular, 1, 4-butanediol diacetate or a mixture of 1, 4-butanediol diacetate and 1, 4-butanediol monoacetate containing 0.1 to 20% by weight, for example 0.1 to 10% by weight or 0.1 to 5% by weight or 0.1 to 2% by weight or 0.1 to 1% by weight or 0.1 to 0.5% by weight of 1, 4-butanediol monoacetate relative to the total weight of 1, 4-butanediol diacetate and 1, 4-butanediol monoacetate is used to impart one of the following olfactory notes: red fruit, raspberry, blueberry, sweet; or any combination thereof. The fruity effect increases with increasing monoacetate content.

In particular, 1, 4-butanediol dipropionate or a mixture of 1, 4-butanediol dipropionate and 1, 4-butanediol monopropionate is used to impart one of the following olfactory notes, the mixture containing 0.1 to 10% by weight, preferably 0.1 to 5% by weight, in particular 0.1 to 3% by weight, of 1, 4-butanediol monopropionate relative to the total weight of 1, 4-butanediol dipropionate and 1, 4-butanediol monopropionate: red fruit, raspberry, blueberry, sweet; or any combination thereof.

The 1, 4-butanediol mono-or diester of formula (I) or a mixture of two or more different 1, 4-butanediol mono-or diesters of formula (I) is generally used in ready-to-use compositions, in particular in perfuming ready-to-use compositions. "perfuming ready-to-use composition", as used herein, refers to a ready-to-use composition that mainly causes a pleasant odor effect.

The 1, 4-butanediol mono-or diester of formula (I) or the mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) is also used to modify and/or enhance the fragrance of the composition; in particular for modifying and/or enhancing the flavour impact of the composition; in particular for modifying the fragrance characteristics of a perfuming ready-to-use composition.

A perfuming ready-to-use composition is, for example, a composition used in personal care, home care, industrial applications, as well as in other applications, such as a pharmaceutical composition or a crop protection composition. Of these, personal care and home care compositions are preferred.

Personal care compositions include body care compositions, products for oral or dental hygiene, and hygiene products for the human body.

Personal care compositions are used to clean, launder, disinfect, nourish, scrub, protect or beautify the human body (and thus also include cosmetics). Examples are creams, emulsions, ointments, other o/w or w/o emulsions, liquid or gel soaps, body washes, shampoos, cosmetics and other decorative cosmetics, and compositions for wet wipes (e.g. for cleaning diaper areas). More specific examples are skin washing and cleansing preparations in the form of soaps, synthetic detergents, washing gels, soap-free detergents or washing pastes, bath preparations such as foam baths, emulsions, oils, shower preparations; skin care formulations, such as skin care emulsions, multiple emulsions, powders, sprays or skin care oils; cosmetic preparations, for example face cosmetics in the form of day creams or powder creams, face powder (loose or compacted), rouge or cream cosmetics, eye care preparations, for example eye shadow preparations, mascaras, eyeliners, eye creams or eye repair creams; lip care formulations, such as lipstick, lip gloss, lip pencil, nail care formulations, such as nail polish, nail polish remover, nail hardener or cuticle remover; foot care formulations, such as foot baths, foot powders, foot creams or ointments, special deodorants and antiperspirant or cocoon removal formulations; photoprotective formulations, such as sun-protection emulsions, creams or oils, sun-protection creams or coolness-protection agents (tropicals), pre-tanning formulations or after-sun formulations; skin tanning preparations, such as self-tanning creams; de-pigmenting preparations, such as preparations for bleaching the skin or skin whitening preparations; insect repellents, such as insect repellent oils, emulsions, sprays or sticks; deodorants such as deodorant sprays, deodorant aerosols, pump-action sprays, deodorant gels, sticks or beads, and also deodorant aerosols or sticks which are free of water; antiperspirant agents, such as antiperspirant sticks, creams or beads; formulations for cleansing and caring for stained skin, such as synthetic detergents (solid or liquid), peeling or scrubbing preparations or peeling masks; depilatory preparations in chemical form (depilatory), for example liquid depilatory preparations, depilatory preparations in cream-or paste-form, depilatory preparations in gel form or aerosol foam; shaving preparations, such as shaving soaps, foaming shave creams, foamless shave creams, foams and gels, pre-shave preparations for dry shaving, after-shave lotions or after-shave creams; perfume preparations, such as perfumes (colognes, eau de toilette, eau de parviflora, heavy-duty fragrances (parfum de toilette), fragrances), perfume oils or balms; cosmetic hair treatment preparations, for example shampoo preparations in the form of shampoos and conditioners, hair care preparations, for example pretreatment preparations, hair tonic, styling creams, styling gels, hair tonic, hair restoration packs, preparations for deep hair restoration, for example permanent waving (hot, mild, cold) waving preparations, hair straightening preparations, liquid hair fixative preparations, hair foams, hair sprays, bleaching preparations, for example hydrogen peroxide solutions, lightening shampoos, bleaching creams, bleaching powders, bleaching creams or oils, temporary, semi-permanent or permanent hair dyes, preparations containing autoxidisable dyes, or natural hair dyes such as henna or chamomile; anti-dandruff formulations in the form of shampoos, conditioners, hair tonics, styling creams or gels or restoration packs; oral care formulations, such as (dental) creams, gels, mouthwashes and sprays; disinfectant for oral cavity or skin. Additional examples are given below.

Examples of home care compositions are dishwashing compositions, laundry compositions (e.g., laundry detergents, fabric softeners, rinse compositions, bleach compositions, detergent compositions, etc.), surface cleaning compositions (also known as hard surface cleaners; e.g., glass, floor, counter, bathtub (bathroom), toilet bowl, sink, kitchen, appliance, and furniture cleaning compositions; multipurpose cleaners; sanitary cleaners), non-cosmetic deodorants (e.g., air and/or surface deodorants), disinfectants (e.g., spray air disinfectants, and spray, liquid and paste/gel surface disinfectants), surface protection and/or polishing compositions, carpet washes, soil release agents, and compositions for wet wipes (e.g., for cleaning floors, furniture, bathroom surfaces, etc.).

Compositions in industrial applications are, for example, compositions for cleaning or sanitizing on an industrial scale (also known as industrial and institutional cleaning or I & I cleaning) or cleaning-in-place (CIP) compositions (CIP is a process for automatically cleaning the interior surfaces of pipes, containers, equipment, filters, and related fittings, etc., without large disassembly).

Crop protection compositions, which are also commonly referred to as plant protection compositions, are compositions that are effective against a variety of harmful microorganisms, harmful invertebrate pests, or agricultural-related undesired plants (e.g., harmful fungi, harmful invertebrate pests such as insect pests, arachnids, nematodes or molluscs, and weeds that cause damage to agricultural plants, plant propagation material such as seeds, or harvested crops). Examples of crop protection compositions are fungicidal, insecticidal, acaricidal, nematicidal, molluscicidal or herbicidal compositions. The term also includes plant growth regulating compositions. Plant growth regulators are plant protection products for influencing plant growth and are used, for example, to increase the stability of cereals by shortening the stem length, thereby reducing or preventing lodging, to improve rooting of cuttings, to reduce plant height in horticulture, to prevent potato germination, etc. In addition, the term includes compositions used in the protection of materials against various harmful microorganisms and invertebrate pests, such as compositions for treating wood or the surroundings of wood materials against termites or compositions for treating mosquito nets against harmful insects such as anopheles mosquitoes, and the like.

Preferably, the 1, 4-butanediol mono-or diester of formula (I) or a mixture of two or more different 1, 4-butanediol mono-or diesters of formula (I) is used in a composition selected from the group consisting of perfume compositions, body care compositions (including cosmetic compositions), products for oral and dental hygiene, hygiene products (including dishwashing compositions), textile detergent compositions, compositions for fragrance dispensers, food products, food supplements, pharmaceutical compositions and crop protection compositions; and is preferably selected from the group consisting of perfume compositions, body care compositions, products for oral or dental hygiene, hygiene products, cleaning compositions, textile detergent compositions, compositions for fragrance dispensers and crop protection compositions.

In particular, 1, 4-butanediol mono-or diesters of formula (I) or mixtures of two or more different 1, 4-butanediol mono-or diesters of formula (I) are used to impart fruity or sweet or combined fruity and sweet olfactory notes to the above listed compositions.

In particular, 1, 4-butanediol diacetate or a mixture of 1, 4-butanediol diacetate and 1, 4-butanediol monoacetate containing 0.1% to 20% by weight, for example 0.1% to 10% by weight or 0.1% to 5% by weight or 0.1% to 2% by weight or 0.1% to 1% by weight or 0.1% to 0.5% by weight of 1, 4-butanediol monoacetate relative to the total weight of 1, 4-butanediol diacetate and 1, 4-butanediol monoacetate is used to impart one of the olfactory notes to the compositions listed above: red fruit, raspberry, blueberry, sweet; or any combination thereof. The fruity effect increases with increasing monoacetate content.

In particular, 1, 4-butanediol dipropionate or a mixture of 1, 4-butanediol dipropionate and 1, 4-butanediol monopropionate is used to impart one of the following olfactory notes to the above-listed compositions, the mixture containing 0.1% to 10% by weight, preferably 0.1% to 5% by weight, in particular 0.1% to 3% by weight, of 1, 4-butanediol monopropionate relative to the total weight of 1, 4-butanediol dipropionate and 1, 4-butanediol monopropionate: red fruit, raspberry, blueberry, sweet; or any combination thereof.

Details of the above listed compositions are given below.

In addition to the olfactory properties, 1, 4-butanediol mono-or diesters of the formula (I) or mixtures of two or more different 1, 4-butanediol mono-or diesters of the formula (I) exhibit advantageous secondary properties.

For example, they may provide better sensory attributes due to synergistic effects with other fragrances, meaning that they may provide an accelerator effect for other fragrances. They are therefore suitable as accelerators for other fragrances.

Thus, another aspect of the invention relates to the use of a 1, 4-butanediol mono-or diester of formula (I) or a mixture of two or more different 1, 4-butanediol mono-or diesters of formula (I) for modifying the fragrance characteristics of a perfuming composition; and more particularly to the use as an accelerator for other fragrances.

By accelerator action is meant that the substance enhances and strengthens the overall effect of the mixture in the perfume formulation. In the peppermint series, for example, menthyl methyl ethers are known to enhance the flavour or taste mixture of peppermint oil and to bring about a significantly more intense and complex sensation, particularly in the front, although the ether itself is a pure substance, without generating a particularly intense odour at all. In the context of a fragrance application, the term "fragrance",(methyl dihydrojasmonate) as a pure substance exhibits only a light jasmine note and as an odor enhancer enhances the diffusion, freshness and volume of the perfume composition. The accelerator action is particularly desirable when applications featuring previous adjustments are required, in which the odor effect is to be transferred particularly rapidly and strongly, for example in deodorants, air fresheners or in the flavoring part of chewing gums.

To achieve such accelerator action, the 1, 4-butanediol mono-or diester of formula (I) or a mixture of two or more different 1, 4-butanediol mono-or diesters of formula (I) is generally used in an amount of from 0.1 to 20% by weight, preferably in an amount of from 0.5 to 10% by weight, in particular in an amount of from 0.6 to 5% by weight, based on the total weight of the perfume mixture.

Furthermore, the 1, 4-butanediol mono-or diester of formula (I) or a mixture of two or more different 1, 4-butanediol mono-or diesters of formula (I) may have a further positive effect on the compositions in which they are used. For example, they may enhance the overall properties of the compositions into which they are incorporated, such as stability (e.g., formulation stability), extensibility, or permanence of the compositions.

Another embodiment of the present invention relates to a process for preparing a fragrance chemical composition, in particular a perfuming composition, especially a perfuming ready-to-use composition, comprising incorporating a 1, 4-butanediol mono-or diester of formula (I) or a mixture of two or more different 1, 4-butanediol mono-or diesters of formula (I) into a target composition, e.g. a ready-to-use composition, yielding a fragrance chemical composition, especially a perfuming ready-to-use composition. Alternatively, the present invention relates to a process for preparing a fragrance chemical composition, in particular a perfuming ready-to-use composition, comprising mixing a 1, 4-butanediol mono-or diester of formula (I) or a mixture of two or more different 1, 4-butanediol mono-or diesters of formula (I) with at least one fragrance chemical different from compound (I) and/or with at least one non-fragrance chemical carrier and/or with at least one antioxidant and/or with at least one deodorant active agent. Suitable and preferred fragrance chemicals, non-fragrance chemical carriers, antioxidants and deodorant actives other than compound (I) are described below. Alternatively, the present invention relates to a process for preparing a fragrance chemical composition, in particular a perfuming composition, especially a perfuming ready-to-use composition, comprising mixing a 1, 4-butanediol mono-or diester of formula (I) or a mixture of two or more different 1, 4-butanediol mono-and/or diesters of formula (I), simultaneously or consecutively with the other components of the composition or with a preformed mixture of parts of the other components of the composition.

For example, the process may be carried out by mixing a 1, 4-butanediol mono-or diester of formula (I) as defined above or a mixture of two or more different 1, 4-butanediol mono-or diesters of formula (I), and at least one further component selected from the group consisting of aromatic chemicals, non-aromatic chemical carriers, antioxidants and deodorant actives different from compound (I).

The invention also relates to a method for modifying the fragrance characteristics of a fragrance chemical composition, in particular a perfuming ready-to-use composition, comprising incorporating into the fragrance chemical composition, in particular a perfuming ready-to-use composition, a 1, 4-butanediol mono-or diester of formula (I) or a mixture of two or more different 1, 4-butanediol mono-or diesters of formula (I). Alternatively, the present invention relates to a process for modifying the fragrance characteristics of a fragrance chemical composition, in particular a perfuming composition, especially a perfuming ready-to-use composition, comprising mixing a 1, 4-butanediol mono-or diester of formula (I) or a mixture of two or more different 1, 4-butanediol mono-and/or diesters of formula (I), simultaneously or consecutively with the other components of the composition or with a preformed mixture of parts of the other components of the composition.

In particular, the present invention relates to a process for preparing a perfume composition, a body care composition, a product for oral and dental hygiene, a hygiene product, a cleaning composition, a textile detergent composition, a composition for fragrance dispensers, a food product, a food supplement, a pharmaceutical composition or a crop protection composition, which process comprises including a 1, 4-butanediol mono-or diester of formula (I) as defined above or a mixture of two or more different 1, 4-butanediol mono-or diesters of formula (I) in a perfume composition, a body care composition, a product for oral and dental hygiene, a hygiene product, a cleaning composition, a textile detergent composition, a composition for fragrance dispensers, a food product, a food supplement, a pharmaceutical composition or a crop protection composition. Alternatively, the present invention relates to a process for preparing a perfume composition, a body care composition, a product for oral and dental hygiene, a hygiene product, a cleaning composition, a textile detergent composition, a composition for fragrance dispensers, a food product, a food supplement, a pharmaceutical composition or a crop protection composition, which comprises mixing 1, 4-butanediol mono-or diester of formula (I) or a mixture of two or more different 1, 4-butanediol mono-and/or diesters of formula (I) simultaneously or continuously with other components of the composition or with a preformed mixture of a part of other components of the composition.

In a specific embodiment, the present invention relates to a method for imparting a fruity or sweet or combined fruity and sweet note to a perfume composition, a body care composition, a product for oral and dental hygiene, a hygiene product, a cleaning composition, a textile detergent composition, a composition for fragrance dispensers, a food product, a food supplement, a pharmaceutical composition or a crop protection composition, the method comprising including a 1, 4-butanediol mono-or diester of formula (I) or a mixture of two or more different 1, 4-butanediol mono-or diesters of formula (I) in a perfume composition, a body care composition, a product for oral and dental hygiene, a hygiene product, a cleaning composition, a textile detergent composition, a composition for fragrance dispensers, a food product, a food supplement, a pharmaceutical composition or a crop protection composition. Alternatively, the present invention relates to a method for imparting a fruity or sweet taste or combined fruity and sweet note to a perfume composition, a body care composition, a product for oral and dental hygiene, a hygiene product, a cleaning composition, a textile detergent composition, a composition for fragrance dispensers, a food product, a food supplement, a pharmaceutical composition or a crop protection composition, the method comprising mixing 1, 4-butanediol mono-or diester of formula (I) or a mixture of two or more different 1, 4-butanediol mono-and/or diesters of formula (I) with other components of the composition or with a preformed mixture of a part of other components of the composition simultaneously or consecutively.

In a specific embodiment, the present invention relates to a method for imparting one of the following olfactory notes to a perfume composition, a body care composition, a product for oral and dental hygiene, a hygiene product, a cleaning composition, a textile detergent composition, a composition for fragrance dispenser, a food product, a food supplement, a pharmaceutical composition or a crop protection composition: red fruit, raspberry, blueberry, sweet; or any combination thereof, the method comprising including 1, 4-butanediol diacetate or a mixture of 1, 4-butanediol diacetate and 1, 4-butanediol monoacetate in a perfume composition, body care composition, product for oral and dental hygiene, hygiene product, cleaning composition, textile detergent composition, composition for fragrance dispenser, food supplement, pharmaceutical composition or crop protection composition, the mixture containing 0.1% to 20% by weight, for example 0.1% to 10% by weight or 0.1% to 5% by weight or 0.1% to 2% by weight or 0.1% to 1% by weight or 0.1% to 0.5% by weight 1, 4-butanediol monoacetate relative to the total weight of 1, 4-butanediol diacetate and 1, 4-butanediol monoacetate. The fruity effect increases with increasing monoacetate content.

In another specific embodiment, the present invention relates to a method for imparting one of the following olfactory notes to a perfume composition, a body care composition, a product for oral and dental hygiene, a hygiene product, a cleaning composition, a textile detergent composition, a composition for fragrance dispenser, a food product, a food supplement, a pharmaceutical composition or a crop protection composition: red fruit, raspberry, blueberry, sweet; or any combination thereof, comprising a 1, 4-butanediol dipropionate or a mixture of 1, 4-butanediol dipropionate and 1, 4-butanediol monopropionate in a perfume composition, a body care composition, a product for oral and dental hygiene, a hygiene product, a cleaning composition, a textile detergent composition, a composition for fragrance dispensers, a food supplement, a pharmaceutical composition or a crop protection composition, the mixture comprising 0.1% to 10% by weight, preferably 0.1% to 5% by weight, in particular 0.1% to 3% by weight, of 1, 4-butanediol monopropionate relative to the total weight of 1, 4-butanediol dipropionate and 1, 4-butanediol monopropionate.

Composition and method for producing the same

Furthermore, the present invention relates to a composition comprising 1, 4-butanediol mono-or diester of formula (I) as defined above or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I), and at least one further component selected from the group consisting of aromatic chemicals other than compound (I), non-aromatic chemical carriers, antioxidants and deodorant actives.

The non-aromatic chemical carrier, antioxidant and deodorant active are of course also different from compound (I).

Fragrance chemicals, non-fragrance chemical carriers, antioxidants and deodorant actives other than compound (I) are different from the direct precursors from which the 1, 4-butanediol mono-or diester of formula (I) is prepared; i.e. they are neither 1, 4-butanediol nor any acid R ² -C (=o) OH or R ³ -C (=o) OH or an acid derivative thereof (such as the corresponding anhydride, acyl halide or active acid ester), nor is compound X- (CH) ₂ ) ₄ -Y。

The non-aromatic chemical carrier is in particular selected from the group consisting of surfactants, oil components (emollients) and solvents.

Thus, in a preferred embodiment, the composition comprises 1, 4-butanediol mono-or diester of formula (I) as defined above or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I), and at least one further component selected from the group consisting of fragrance chemicals other than compound (I), surfactants, oil components, solvents, antioxidants and deodorant actives.

The pleasant fragrance, low volatility and excellent solubility make compound (I) a suitable component in compositions in which a pleasant fragrance is desired.

Thus, the composition is preferably a fragrance chemical composition, more preferably an odor composition and especially a fragrance composition.

An embodiment of the invention relates to a composition comprising a 1, 4-butanediol mono-or diester of formula (I) as defined above or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) and at least one further component selected from the group consisting of an oil component, a solvent, an antioxidant and a deodorant active agent.

One embodiment of the present invention relates to a composition comprising a 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) and at least one fragrance chemical.

One embodiment of the present invention relates to a composition comprising a 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) and at least one non-aromatic chemical carrier.

One embodiment of the present invention relates to a composition comprising a 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) and at least one surfactant.

One embodiment of the invention relates to a composition comprising a 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) and at least one oil component.

One embodiment of the invention relates to a composition comprising a 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) and at least one solvent.

One embodiment of the invention relates to a composition comprising a 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) and at least one antioxidant.

One embodiment of the present invention relates to a composition comprising a 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) and at least one deodorant active agent.

The 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) may preferably be used in the fragrance composition. In a preferred embodiment, the fragrance composition is an odor composition, i.e. a composition that causes an odor effect, and in particular a fragrance composition, i.e. a composition that causes a pleasant odor.

The composition according to the present invention may be selected from, but is not limited to, the group consisting of perfume compositions, body care compositions (including cosmetic compositions), products for oral and dental hygiene, hygiene products, cleaning compositions (including dishwashing compositions), textile detergent compositions, compositions for fragrance dispensers, food products, food supplements, pharmaceutical compositions and crop protection compositions. Preferably, the composition according to the invention is not an alcoholic beverage (and in particular not wine), a fruit juice (and in particular not a grape juice which has not been fermented to wine in a fermented state), a fruit (such as wine grape, melon or pineapple) or a seed; furthermore, the composition does not comprise diacetyl; and does not contain 1, 3-bis (caprolactam-1-yl) butane.

Preferably, the composition according to the invention is selected from the group consisting of perfume compositions, body care compositions (including cosmetic compositions), products for oral and dental hygiene, hygiene products, cleaning compositions (including dishwashing compositions), textile detergent compositions, compositions for fragrance dispensers and crop protection compositions.

Aromatic chemicals (other than compounds (I))

Due to the physical properties of the compounds (I), the combination of compounds has particularly good, almost universal solvent properties for and in fragrance compositions such as especially fragrance chemicals and other conventional ingredients in fragrance compositions. Thus, 1, 4-butanediol mono-or diesters of formula (I) or mixtures of different 1, 4-butanediol mono-and/or diesters of formula (I) are well combinable with fragrance chemicals other than compound (I), in particular allowing the production of fragrance compositions (preferably fragrance compositions) with novel advantageous sensory attributes. In particular, as already explained above, the combination may promote sensory attributes of a fragrance chemical (e.g. like perfume), wherein the fragrance chemical is different from compound (I).

The composition of the present invention may comprise at least one fragrance chemical different from the compound (I). The at least one fragrance chemical may be, for example, 1, 2, 3, 4, 5, 6, 7, 8 or more fragrance chemicals selected from the group consisting of:

geranyl acetate (3, 7-dimethyl-2, 6-octadien-1 yl acetate), alpha-hexyl cinnamaldehyde, 2-phenoxyethyl isobutyrate (Phenilate) ¹ ) Dihydromyrcenol (2, 6-dimethyl-7-octen-2-ol), methyl dihydrojasmonate (preferably having a cis isomer content of more than 60 wt.%) (Hedione ⁹ ，Hedione HC ⁹ ) 4,6,7, 8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta [ g ]]Benzopyran (Galaxoid) ³ ) Tetrahydrolinalool (3, 7-dimethyloctan-3-ol), ethyl linalool, benzyl salicylate, 2-methyl-3- (4-tert-butylphenyl) propanal (Lyseral) ² ) Cinnamyl alcohol, 4, 7-methano-3 a,4,5,6,7 a-hexahydro-5-indenyl ester acetate and/or 4, 7-methano-3 a,4,5,6,7 a-hexahydro-6-indenyl ester acetate (herbafloat ¹ ) Citronellol, citronellyl acetate, tetrahydrogeraniol, vanillin, linalyl acetate, storyl acetate (1-phenylethyl acetate), octahydro-2, 3, 8-tetramethyl-2-naphthaleneethanone and/or 2-acetyl-1,2,3,4,6,7,8-octahydro-2, 3, 8-tetramethylnaphthalene (Iso E Super) ³ ) Hexyl salicylate, 4-tert-butylcyclohexyl acetate (Oryclone) ¹ ) 2-tert-butylcyclohexyl acetate (Agrumex HC) ¹ ) Alpha-ionone (4- (2, 6-trimethyl-2-cyclohexen-1-yl) -3-buten-2-one), alpha-n-methyl ionone, alpha-isomethyl ionone, coumarin, terpineol acetate, 2-phenylethyl alcohol, 4- (4-hydroxy-4-methylpentyl) -3-cyclohexenecarboxaldehyde (Lyral) ³ ) Alpha-amyl cinnamic aldehyde, ethylene glycol brassylate, (E) -and/or (Z) -3-methylcyclopenta-5-enone (Muscenon) ⁹ ) 15-pentadec-11-enolide and/or 15-pentadec-12-enolide (Globalide) ¹ ) 15-cyclopentadecanolide (Macrolide) ¹ ) 1- (5, 6,7, 8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphtyl) ethanone (Tonalid) ¹⁰ ) 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol (Florol) ⁹ ) 2-ethyl-4- (2, 3-trimethyl-3-cyclopenten-1-yl) -2-buten-1-ol (Sandolen) ¹ ) Cis-3-hexenyl acetate, trans-2/cis-6-nonyldienol, 2, 4-dimethyl-3-cyclohexenemethyl acetateAldehyde (Vertocitral) ¹ ) 2,4, 7-Tetramethylooct-6-en-3-one (Claritone) ¹ ) 2, 6-dimethyl-5-heptene-1-aldehyde (Melonal) ² ) Borneol, 3- (3-isopropylphenyl) butanal (Florrydral) ² ) 2-methyl-3- (3, 4-methylenedioxyphenyl) propanal (Helional) ³ ) 3- (4-ethylphenyl) -2, 2-dimethylpropionaldehyde (Florazon) ¹ ) 7-methyl-2H-1, 5-benzodioxepan-3 (4H) -one (Calone), 3, 5-trimethylcyclohexyl acetate (preferably having a cis isomer content of 70wt.% or more), 2, 5-trimethyl-1, 2,3, 4a,5,6, 7-octahydronaphthalen-2-ol (Ambrinol S) ¹ ) 3- (4-tert-butylphenyl) -propanal (Bourgeonal) ⁴ ) 2-methyl Ethyl valerate (Manzanate) ⁴ ) Ethoxymethoxy cyclododecane (Amberwood) ¹ ) 2, 4-dimethyl-4, 4a,5,9 b-tetrahydroindeno [1,2-d ]][1,3]Dioxin (Magnolan) ¹ ) (2-tert-butylcyclohexyl) acetate (Verdox) ³ ) And 3- [5, 6-trimethylbicyclo [2.2.1 ]]Hept-2-yl]Cyclohexan-1-ol (Sandela) ⁴ ). In the context of the present invention, the above-mentioned one or more aroma chemicals are therefore preferably combined with a compound of formula (I) or a mixture of different compounds (I) as described above.

Trade names are given above, these referring to the following sources:

¹ trade name of german dexin company (Symrise GmbH);

² trade name of BASF company (BASF SE);

³ american International essence and perfume Co., ltd (International Flavors)&The trade name of fragrans inc., USA);

⁴ swiss patent Hua Du, division (Givaudan AG, switzerland);

⁹ trade names of swiss finmei company (Firmenich s.a., switzerland);

¹⁰ the Netherlands, PFW aromatic chemicals company (PFW Aroma Chemicals b.v.).

The preferred embodiment of the present invention relates to a composition comprising 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) and at least one fragrance chemical selected from the group consisting of methyl benzoate, benzyl acetate, geranyl acetate, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol and linalool.

Another embodiment of the invention relates to a composition comprising 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) and 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol.

Another embodiment of the invention relates to a composition comprising 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) and methyl benzoate.

The preferred embodiment of the present invention relates to a composition comprising 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) and at least one additional fragrance chemical selected from the group consisting of ethyl vanillin, 2, 5-dimethyl-4-hydroxy-2H-furan-3-one (furanone) or 3-hydroxy-2-methyl-4H-pyran-4-one (maltol).

The preferred embodiment of the present invention relates to a composition comprising 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) and at least one further fragrance chemical selected from the group consisting of: geranyl acetate, α -hexylcinnamaldehyde, 2-phenoxyethyl isobutyrate, dihydromyrcenol, methyl dihydrojasmonate (preferably having a cis isomer content of more than 60 wt.%), 4,6,7, 8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta [ g ] benzopyran, tetrahydrolinalool, ethyl linalool, benzyl salicylate, 2-methyl-3- (4-tert-butylphenyl) propanal, cinnamyl alcohol, 4, 7-methano-3 a acetate, 4,5,6,7 a-hexahydro-5-indenyl ester, 4, 7-methano-3 a acetate, 4,5,6,7 a-hexahydro-6-indenyl ester, citronellyl acetate, tetrahydrogeraniol, linalyl acetate, storax acetate, octahydro-2, 3, 8-tetramethyl-2-naphthaleneethanone, 2-acetyl-1,2,3,4,6,7,8-octahydro-2, 3, 8-tetramethylnaphthalene, hexyl salicylate, 4-tert-butylcyclohexyl acetate, 2-tert-butylcyclohexyl acetate, alpha-ionone, alpha-n-methylionone, alpha-isomethylionone, coumarin, terpineyl acetate, 4- (4-hydroxy-4-methylpentyl) -3-cyclohexene aldehyde, alpha-amyl cinnamic aldehyde, ethylene glycol brassylate, (E) -3-methylcyclopentadec-5-enone, (Z) -3-methylcyclopentadec-5-enone, 15-pentadec-11-enolide, 15-pentadec-12-enolide, 15-cyclopentadecolide, 1- (5, 6,7, 8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthyl) ethanone, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, 2-ethyl-4- (2, 3-trimethyl-3-cyclopenten-1-yl) -2-buten-1-ol, cis-3-hexenyl acetate, trans-2/cis-6-nonylenol, 2, 4-dimethyl-3-cyclohexenecarboxaldehyde, 2,4, 7-tetramethyloct-6-en-3-one, 2, 6-dimethyl-5-hepten-1-aldehyde, borneol, 3- (3-isopropylphenyl) butanal 2-methyl-3- (3, 4-methylenedioxyphenyl) propanal, 3- (4-ethylphenyl) -2, 2-dimethylpropionaldehyde, 7-methyl-2H-1, 5-benzodioxepan-3 (4H) -one, 3, 5-trimethylcyclohexyl acetate (preferably having a cis isomer content of 70wt.% or more), 2, 5-trimethyl-1, 2,3, 4a,5,6, 7-octahydronaphthalen-2-ol, 3- (4-tert-butylphenyl) -propanal, ethyl 2-methylpentanoate, ethoxymethoxycyclododecane, 2, 4-dimethyl-4, 4a,5,9 b-tetrahydroindeno [1,2-d ] [1,3] dioxin, (2-tert-butylcyclohexyl) acetate, 3- [5, 6-trimethylbicyclo [2.2.1] hept-2-yl ] cyclohex-1-ol, menthone, isomenthone, carvone, β -n-methylionone, β -isomethylionone, α -irisone, α -damascone, β -damascone, δ -damascone, acetylated cedar wood oil, and mixtures thereof.

Additional fragrance chemicals with which 1, 4-butanediol mono-or diesters of formula (I) or mixtures of different 1, 4-butanediol mono-and/or diesters of formula (I) can be combined to give compositions according to the invention can be found, for example, in S.arctander, perfume and Flavor Chemicals [ perfume and fragrance chemicals ], volumes I and II, montreley, new Jersey, 1969, from publications or K.Bauer, D.Garbe and H.Surburg, common Fragrance and Flavor Materials [ common fragrance and fragrance materials ], 4 th edition, willivcH publishing, wei Yinhai m 2001. Specifically, there may be mentioned:

extracts from natural sources, e.g. essential oils, condensed fats, absolute oils, resins, balms, tinctures, e.g. such as

An ambergris tincture; ami tree oil; angelica sinensis seed oil; root oil is obtained; fennel seed oil; valerian oil; basil oil; net oil of sphagnum; laurel oil; mugwort oil; benzoin resin; bergamot oil; beeswax net oil; birch tar; bitter almond oil; peppermint oil; leaf oil is withered; a card Lu Wayou; juniper oil; calamus oil; camphor oil; ylang oil; cardamon oil; chenopodium kansui oil; cinnamon oil; cinnamon absolute; a beaver essential oil; cedar leaf oil; cedar wood oil; a cistus oil; citronella oil; lemon oil; copal balsam; copaiba oil; coriander oil; radix aucklandiae root oil; cumin oil; filigree oil; artemisia oil; dill leaf oil; dill seed oil; eaf eau de toilette absolute; purifying oak moss; elemene oil; tarragon oil; eucalyptus citriodora oil; eucalyptus oil; fennel oil; pine needle oil; white pine oil; white pine resin; geranium oil; grapefruit oil; guaiac wood oil; an ancient canola balsam; ancient rutin oil; clean oil of helichrysum; wax chrysanthemum oil; ginger oil; iris root absolute oil; iris root oil; jasmine absolute; calamus oil; lan Chunhuang chrysanthemum oil; roman chamomile oil; carrot seed oil; chenopodium kansui oil; pine needle oil; spearmint oil; carum carvi oil; rice oil; rice absolute; a rice resin; clear lavender absolute oil; eye-catching lavender oil; lavender absolute; lavender oil; lemon grass oil; radix angelicae pubescentis oil; distilling the lime oil; squeezing lime oil; linalool oil; litsea cubeba oil; laurel leaf oil; nutmeg oil; marjoram oil; orange oil; oil of cortex Cinnamomi Japonici; mimosa pudica absolute; musk seed oil; musk tincture; sclareum oil; nutmeg kernel oil; myrrh absolute; myrrh oil; myrtle oil; clove leaf oil; clove flower oil; orange flower oil; olibanum absolute; cream oil; bisabolol oil; neroli absolute; orange oil; oregano oil; rose grass oil; patchouli oil; perilla oil; peruvian balsam oil; parsley leaf oil; parsley seed oil; orange leaf oil; peppermint oil; pepper oil; sweet pepper oil; pine tree oil; peppermint oil; absolute rose oil; rose wood oil; rose oil; rosemary oil; darma sage oil; spanish sage oil; sandalwood oil; celery seed oil; lavender oil; octagonal oil; storax oil; tagetes oil; fir oil; tea tree oil; turpentine oil; thyme oil; rouge balsam; bean oil; tuberose absolute oil; herb extracts; violet leaf absolute; vervain oil; vetiver oil; juniper berry oil; alcohol residue; artemisia absinthium oil; wintergreen oil; achyranthes bidentata oil; musk cat oil; cinnamon leaf oil; cinnamon bark oil, fractions thereof, or fractions thereof;

Various fragrances from the following group: hydrocarbons such as, for example, 3-carene; alpha-pinene; beta-pinene; alpha terpinene; gamma terpinene; p-cymene; myrrh alkene; camphene; caryophyllene; cedrene; farnesene; limonene; longifolene; myrcene; ocimene is used; orange alkene; (E, Z) -1,3, 5-undecatriene; styrene; diphenyl methane;

aliphatic alcohols, such as, for example, hexanol; octanol; 3-octanol; 2, 6-dimethylheptanol; 2-methyl-2-heptanol; 2-methyl-2-octanol; (E) -2-hexenol; (E) -and (Z) -3-hexenol; 1-octen-3-ol; a mixture of 3,4,5, 6-pentamethyl-3/4-hepten-2-ol and 3,5,6,6-tetramethyl-4-methylenehept-2-ol; (E, Z) -2, 6-nondienol; 3, 7-dimethyl-7-methoxyoctan-2-ol; 9-decenol; 10-undecenol; 4-methyl-3-decen-5-ol;

aliphatic aldehydes and acetals thereof, such as, for example, hexanal; heptanal; octanal; nonanal; decanal; undecalaldehyde; dodecanal; tridecyl aldehyde; 2-methyl octanal; 2-methylnonanal; (E) -2-hexenal; (Z) -4-heptenal; 2, 6-dimethyl-5-heptenal; 10-undecenal; (E) -4-decenal; 2-dodecenal; 2,6, 10-trimethyl-9-undecenal; 2,6, 10-trimethyl-5, 9-undecadienal; heptanal diethyl acetal; 1, 1-dimethoxy-2, 5-trimethyl-4-hexene; citronelloxyacetaldehyde; (E/Z) -1- (1-methoxypropoxy) -hex-3-ene; aliphatic ketones and oximes thereof, such as, for example, 2-heptanone; 2-octanone; 3-octanone; 2-nonone; 5-methyl-3-heptanone; 5-methyl-3-heptanone oxime; 2,4, 7-tetramethyl-6-octen-3-one; 6-methyl-5-hepten-2-one;

Aliphatic sulfur-containing compounds such as, for example, 3-methylthiohexanol; 3-methylthiohexyl acetate; 3-mercaptohexanol; 3-mercaptohexyl acetate; 3-mercaptohexyl butyrate; 3-acetylthio hexyl acetate; 1-menthene-8-thiol;

aliphatic nitriles such as, for example, 2-nonenenitrile; 2-undecylenenitrile; 2-tridecenonitrile; 3, 12-tridecadienenitrile; 3, 7-dimethyl-2, 6-octadienenitrile; 3, 7-dimethyl-6-octenenitrile;

esters of aliphatic carboxylic acids, such as, for example, (E) -and (Z) -3-hexenyl formate; ethyl acetoacetate; isoamyl acetate; hexyl acetate; 3, 5-trimethylhexyl acetate; acetic acid 3-methyl-2-butenyl ester; acetic acid (E) -2-hexenyl ester; acetic acid (E) -and (Z) -3-hexenyl esters; octyl acetate; 3-octyl acetate; acetic acid 1-octen-3-yl ester; ethyl butyrate; butyl butyrate; isoamyl butyrate; hexyl butyrate; isobutyric acid (E) -and (Z) -3-hexenyl esters; hexyl crotonate; ethyl isovalerate; 2-methylpentanoic acid ethyl ester; ethyl caproate; allyl caproate; ethyl heptanoate; allyl heptanoate; ethyl octanoate; (E, Z) -ethyl 2, 4-decadienoate; 2-Xin Guisuan methyl ester; 2-nonynoic acid methyl ester; allyl 2-isopentyloxy acetate; methyl-3, 7-dimethyl-2, 6-octadienoic acid ester; 4-methyl-2-pentyl crotonate;

Acyclic terpene alcohols, such as, for example, geraniol; nerol; linalool; lavender alcohol; nerolidol; farnesol; tetrahydrolinalool; 2, 6-dimethyl-7-octen-2-ol; 2, 6-dimethyloctan-2-ol; 2-methyl-6-methylene-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 formate, acetate, propionate, isobutyrate, butyrate, isovalerate, valerate, caproate, crotonate, tiglate and 3-methyl-2-butenoate thereof;

acyclic terpene aldehydes and ketones, such as, for example, geranial; neral; citronellal; 7-hydroxy-3, 7-dimethyloctanal; 7-methoxy-3, 7-dimethyloctanal; 2,6, 10-trimethyl-9-undecenal; geranylacetone; dimethyl-and diethyl acetals of geranial, neral, 7-hydroxy-3, 7-dimethyloctanal; cyclic terpene alcohols such as, for example, menthol; isopulegol; alpha terpineol; terpin-4-ol; menthan-8-ol; menthan-1-ol; menthan-7-ol; borneol; isoborneol; oxidizing linalool; nopol; cedrol; ambroxol; vetiveryl alcohol; guaiacol; and formate, acetate, propionate, isobutyrate, butyrate, isovalerate, valerate, caproate, crotonate, tiglate and 3-methyl-2-butenoate thereof;

Cyclic terpene aldehydes and ketones, such as, for example, menthone; isomenthone; 8-mercaptomenthan-3-one; carvone; camphor; fennel ketone; alpha-ionone; beta-ionone; alpha-n-methyl ionone; beta-n-methyl ionone; alpha-isoamyl ionone; beta-isomethyl ionone; alpha-irone; alpha-damascone; beta-damascone; beta-damascenone; delta-damascone; gamma-damascone; 1- (2, 4-trimethyl-2-cyclohexen-1-yl) -2-buten-1-one; 1,3,4,6,7,8 a-hexahydro-1, 5-tetramethyl-2H-2, 4 a-methanonaphthalen-8 (5H) -one; 2-methyl-4- (2, 6-trimethyl-1-cyclohexen-1-yl) -2-butenal; nocardomethyl; dihydro nocardione; 4,6, 8-megastigmatrien-3-one; alpha-sweet orange aldehyde; beta-sweet orange aldehyde; acetylated cedar wood oil (methyl cedrone);

cyclic alcohols such as, for example, 4-tert-butylcyclohexanol; 3, 5-trimethylcyclohexanol; 3-isobornyl cyclohexanol; 2,6, 9-trimethyl-Z2, Z5, E9-cyclododecatriene-1-ol; 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol;

alicyclic alcohols such as, for example, α -3, 3-trimethylcyclohexylmethanol; 1- (4-isopropylcyclohexyl) ethanol; 2-methyl-4- (2, 3-trimethyl-3-cyclopent-1-yl) butanol; 2-methyl-4- (2, 3-trimethyl-3-cyclopent-1-yl) -2-buten-1-ol; 2-ethyl-4- (2, 3-trimethyl-3-cyclopent-1-yl) -2-buten-1-ol; 3-methyl-5- (2, 3-trimethyl-3-cyclopent-1-yl) pentan-2-ol; 3-methyl-5- (2, 3-trimethyl-3-cyclopent-1-yl) -4-penten-2-ol; 3, 3-dimethyl-5- (2, 3-trimethyl-3-cyclopent-1-yl) -4-penten-2-ol; 1- (2, 6-trimethylcyclohexyl) pentan-3-ol; 1- (2, 6-trimethylcyclohexyl) hexan-3-ol;

Cyclic and alicyclic ethers such as, for example, eucalyptol; methyl cedar ether; cyclododecyl methyl ether; 1, 1-dimethoxy cyclododecane; (ethoxymethoxy) cyclododecane; alpha-cedrene epoxide; 3a,6, 9 a-tetramethyldodecahydronaphtho [2,1-b ] furan; 3 a-ethyl-6, 9 a-trimethyldodecahydronaphtho [2,1-b ] furan; 1,5, 9-trimethyl-13-oxabicyclo- [10.1.0] tridec-4, 8-diene; rose ether; 2- (2, 4-dimethyl-3-cyclohexen-1-yl) -5-methyl-5- (1-methylpropyl) -1, 3-dioxane;

cyclic and macrocyclic ketones such as, for example, 4-t-butylcyclohexanone; 2, 5-trimethyl-5-pentylcyclopentanone; 2-heptyl cyclopentanone; 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-cyclopentadecanone; 3-methyl-5-cyclopentadecanone; 3-methylcyclopentadecanone; 4- (1-ethoxyvinyl) -3, 5-tetramethylcyclohexanone; 4-t-amyl cyclohexanone; 5-cyclohexadecen-1-one; 6, 7-dihydro-1, 2, 3-pentamethyl-4 (5H) -indenone; 8-cyclohexadecen-1-one; 7-cyclohexadecen-1-one; (7/8) -cyclohexadecen-1-one; 9-cycloheptadecen-1-one; cyclopentadecanone; a cyclohexadecone;

Alicyclic aldehydes such as, for example, 2, 4-dimethyl-3-cyclohexene-formaldehyde; 2-methyl-4- (2, 6-trimethylcyclohexen-1-yl) -2-butenal; 4- (4-hydroxy-4-methylpentyl) -3-cyclohexene carbaldehyde; 4- (4-methyl-3-penten-1-yl) -3-cyclohexene carbaldehyde;

alicyclic ketones such as, for example, 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-tetramethyl-1, 2,3,4,5,6,7, 8-octahydro-2-naphthylmethyl 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-amyl cyclohexyl acetate; 4-tert-amyl cyclohexyl acetate; 3, 5-trimethylcyclohexyl acetate; decahydro-2-naphthyl acetate; 2-cyclopentyl crotonate; acetic acid 3-pentylthetrahydro-2H-pyran-4-yl ester; decahydro-2, 5,8 a-tetramethyl-2-naphthyl acetate; acetic acid 4, 7-methano-3 a,4,5,6,7 a-hexahydro-5 or 6-indenyl esters; propionic acid 4, 7-methano-3 a,4,5,6,7 a-hexahydro-5 or 6-indenyl ester; isobutyric acid 4, 7-methano-3 a,4,5,6,7 a-hexahydro-5 or 6-indenyl esters; acetic acid 4, 7-methanooctahydro-5 or 6-indenyl esters;

Esters of cycloaliphatic alcohols such as, for example, 1-cyclohexylethyl crotonate;

esters of alicyclic carboxylic acids such as, for example, allyl 3-cyclohexylpropionate; cyclohexyloxy allyl acetate; cis-and trans-methyl dihydrojasmonate; cis-and trans-methyl jasmonates; methyl 2-hexyl-3-oxocyclopentanecarboxylate; 2-ethyl-6, 6-dimethyl-2-cyclohexenecarboxylic acid ethyl ester; 2,3,6,6-tetramethyl-2-cyclohexenecarboxylic acid ethyl ester; 2-methyl-1, 3-dioxolane-2-acetic acid ethyl ester;

araliphatic alcohols, such as, for example, benzyl alcohol; 1-phenylethanol, 2-phenylethanol, 3-phenylpropanol; 2-phenylpropanol; 2-phenoxyethanol; 2, 2-dimethyl-3-phenylpropanol; 2, 2-dimethyl-3- (3-methylphenyl) propanol; 1, 1-dimethyl-2-phenylethanol; 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, for example, benzyl acetate; benzyl propionate; benzyl isobutyrate; benzyl isovalerate; 2-phenylethyl acetate; 2-phenylethyl propionate; 2-phenylethyl isobutyrate; 2-phenylethyl isovalerate; acetic acid 1-phenylethyl ester; alpha-trichloromethyl benzyl acetate; alpha, alpha-dimethylphenylethyl acetate; butyric acid α, α -dimethylphenylethyl ester; cinnamyl acetate; 2-phenoxyethyl isobutyrate; acetic acid 4-methoxybenzyl ester;

Araliphatic ethers such as, for example, 2-phenylethylmethyl ether; 2-phenylethyl isoamyl ether; 2-phenylethyl 1-ethoxyethyl ether; phenylacetaldehyde dimethyl acetal; phenylacetaldehyde diethyl acetal; hydrogenating the atropine dimethyl acetal; phenylacetaldehyde glycerol acetal; 2,4, 6-trimethyl-4-phenyl-1, 3-dioxane; 4,4a,5,9 b-tetrahydroindeno [1,2-d ] -m-dioxin; 4,4a,5,9 b-tetrahydro-2, 4-dimethylindeno [1,2-d ] -m-dioxin;

aromatic and araliphatic aldehydes, such as, for example, benzaldehyde; phenylacetaldehyde; 3-phenylpropionaldehyde; hydrogenating the atropaldehyde; 4-methylbenzaldehyde; 4-methylbenzaldehyde; 3- (4-ethylphenyl) -2, 2-dimethylpropionaldehyde; 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-butylcinnamaldehyde; alpha-amyl cinnamic aldehyde; 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, for example, acetophenone; 4-methylacetophenone; 4-methoxyacetophenone; 4-tert-butyl-2, 6-dimethyl acetophenone; 4-phenyl-2-butanone; 4- (4-hydroxyphenyl) -2-butanone; 1- (2-naphthyl) 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-indanyl methyl 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-naphthacenedione;

aromatic and araliphatic carboxylic acids and esters thereof, such as, for example, benzoic acid; phenyl acetic acid; methyl benzoate; ethyl benzoate; hexyl benzoate; benzyl benzoate; methyl phenylacetate; ethyl phenylacetate; geranyl phenylacetate; phenyl ethyl phenylacetate; methyl cinnamate; ethyl cinnamate; benzyl cinnamate; phenyl ethyl cinnamate; cinnamic acid cinnamate; allyl phenoxyacetate; methyl salicylate; isoamyl salicylate; hexyl salicylate; cyclohexyl salicylate; cis-3-hexenyl salicylate; benzyl salicylate; phenyl ethyl salicylate; 2, 4-dihydroxy-3, 6-dimethylbenzoic acid methyl ester; 3-phenylglycidic acid ethyl ester; 3-methyl-3-phenylglycidic acid ethyl ester;

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-t-butyl acetophenone; cinnamonitrile; 3-methyl-5-phenyl-2-pentenenitrile; 3-methyl-5-phenylpentanenitrile; methyl anthranilate; methyl-N-methyl anthranilate; schiff base of methyl anthranilate with 7-hydroxy-3, 7-dimethyloctanal, 2-methyl-3- (4-tert-butylphenyl) propanal or 2, 4-dimethyl-3-cyclohexene-formaldehyde; 6-isopropylquinoline; 6-isobutylquinoline; 6-sec-butylquinoline; 2- (3-phenylpropyl) pyridine; an indole; skatole; 2-methoxy-3-isopropylpyrazine; 2-isobutyl-3-methoxypyrazine;

phenols, phenyl ethers and phenyl esters, such as, for example, estragole; anethole; eugenol; eugenol methyl ether; isoeugenol; isoeugenol methyl ether; thymol; carvacrol; diphenyl ether; beta-naphthylmethyl ether; beta-naphthylethyl ether; beta-naphthylisobutyl ether; 1, 4-dimethoxybenzene; eugenol acetate; 2-methoxy-4-methylphenol; 2-ethoxy-5- (1-propenyl) phenol; p-cresol phenylacetate;

heterocyclic compounds such as, for example, 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, for example, 1, 4-octanolactone; 3-methyl-1, 4-octanolactone; 1, 4-nonanolactone; 1, 4-decalactone; 8-decene-1, 4-olide; 1, 4-undecalactone; 1, 4-dodecalactone; 1, 5-decalactone; 1, 5-dodecalactone; 4-methyl-1, 4-decalactone; 1, 15-pentadecanolide; cis-and trans-11-pentadecene-1, 15-olide; cis-and trans-12-pentadecene-1, 15-olide; 1, 16-hexadecanolide; 9-hexadecene-1, 16-lactone; 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.

Non-aromatic chemical carrier

Another embodiment of the invention is directed to a composition comprising a 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) and at least one non-aromatic chemical carrier.

The at least one non-aromatic chemical carrier may be a compound, a mixture of compounds, or other additive that has no or no significant sensory properties. The non-aromatic chemical carrier may be used to dilute and/or immobilize the compound (I) as defined above and optionally at least one aromatic chemical, or any other component if included in the composition.

Another embodiment of the present invention is directed to a composition comprising 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) and at least one non-aromatic chemical carrier selected from the group consisting of solvent, surfactant and oil components.

According to a preferred embodiment of the invention, the non-aromatic chemical carrier is selected from the group consisting of solvents, surfactants and oil components listed below.

One embodiment of the invention relates to a composition comprising a 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) as described herein and at least one solvent.

In the context of the present invention, a "solvent" is used to dilute any further component of one or more compounds (I) and/or compositions used according to the invention, without having its own fragrance.

The one or more solvents may be present in the composition in an amount of 0.01 to 99wt.%, based on the composition. In a preferred embodiment of the present invention, the composition comprises 0.1 to 90wt.%, preferably 0.5 to 80wt.% of one or more solvents, based on the total weight of the composition. The amount of the one or more solvents may be selected according to the composition. In one embodiment of the invention, the composition comprises 0.05 to 10wt.%, preferably 0.1 to 5wt.%, more preferably 0.2 to 3wt.%, based on the total weight of the composition. In one embodiment of the present invention, the composition comprises 20 to 70wt.%, preferably 25 to 50wt.% of one or more solvents, based on the total weight of the composition.

Preferred solvents are ethanol, isopropanol, dipropylene glycol (DPG), propylene glycol, 1, 2-butanediol, glycerol, diethylene glycol monoethyl ether, diethyl phthalate (DEP), isopropyl myristate (IPM), triethyl citrate (TEC) and Benzyl Benzoate (BB).

Particularly preferred solvents are selected from the group consisting of ethanol, propylene glycol, dipropylene glycol, triethyl citrate, benzyl benzoate and isopropyl myristate.

In a preferred embodiment of the invention, the solvent is selected from the group consisting of ethanol, isopropanol, diethylene glycol monoethyl ether, glycerol, propylene glycol, 1, 2-butanediol, dipropylene glycol, triethyl citrate and isopropyl myristate.

In a specific embodiment of the present invention, the solvent is selected from the group consisting of isopropanol, dipropylene glycol (DPG), propylene glycol, 1, 2-butanediol, diethylene glycol monoethyl ether, diethyl phthalate (DEP), isopropyl myristate (IPM), triethyl citrate (TEC), benzyl benzoate, and mixtures thereof. More specifically, the solvent is selected from the group consisting of isopropyl alcohol, isopropyl myristate (IPM), triethyl citrate (TEC), benzyl benzoate, and mixtures thereof.

According to another embodiment, 1, 4-butanediol mono-or diesters of formula (I) or mixtures of different 1, 4-butanediol mono-and/or diesters of formula (I) are used according to the invention in surfactant-containing compositions. The 1, 4-butanediol mono-or diesters of formula (I) or mixtures of different 1, 4-butanediol mono-and/or diesters of formula (I) can be used in particular for providing odor, preferably fragrance effects to surfactant-containing compositions, such as, for example, cleaners, in particular laundry care products and multipurpose cleaners, due to their unique fragrance properties and their fastness, permanence and stability. It may be preferred to impart a long lasting clean note to the surfactant-containing composition.

Thus, one embodiment of the present invention relates to a composition comprising a 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) and at least one surfactant.

The one or more surfactants may be selected from anionic, nonionic, cationic and/or amphoteric or zwitterionic surfactants. Surfactant-containing compositions, such as, for example, body washes, foam baths, shampoos, and the like, preferably contain at least one anionic surfactant.

The composition according to the invention generally contains one or more surfactants in the form of aggregates in an amount of 0 to 40wt.%, preferably 0 to 20wt.%, more preferably 0.1 to 15wt.%, and in particular 0.1 to 10wt.%, based on the total weight of the composition. Typical examples of nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers and mixed formals, optionally partially oxidized alkyl (alkenyl) oligoglycosides or glucuronic acid derivatives, fatty acid-N-alkyl glucamides, protein hydrolysates (in particular wheat-based plant products), polyol fatty acid esters, sugar esters, sorbitan esters, polysorbates and amine oxides. If the nonionic surfactants contain polyglycol ether chains, they may have a conventional homolog distribution, but they preferably have a narrow range of homolog distributions.

Zwitterionic surfactants are surface-active compounds which contain at least one quaternary ammonium group and at least one-COO group in the molecule ^(-) or-SO ₃ ^(-) A group. Particularly suitable zwitterionic surfactants are the so-called betaines, such as N-alkyl-N, N-dimethylglycinates, for example cocoalkyl dimethyl glycinate, N-acylaminopropyl-N, N-dimethylglycinate, for example cocoamidopropyl dimethyl glycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethyl imidazoline, containing from 8 to 18 carbon atoms in the alkyl or acyl groups, and cocoamidoethyl hydroxyethyl carboxymethyl glycinate. Fatty acid amide derivatives known under the CTFA name of cocamidopropyl betaine are particularly preferred.

Amphoteric surfactants are also suitable, in particular as cosurfactants. Amphoteric surfactants are surface-active compounds which are in addition to C in the molecule ₈ To C ₁₈ Alkyl or acyl radicals containing, in addition to the alkyl or acyl radicals, at least one free amino radical and at least one-COOH-or-SO-radical ₃ H-groups and are capable of forming internal salts. Examples of suitable amphoteric surfactants are N-alkyl glycine, N-alkyl propionic acid, N-alkyl aminobutyric acid, N-alkylIminodipropionic acid, N-hydroxyethyl-N-alkylamidopropylglycine, N-alkyltaurine, N-alkyl sarcosine, 2-alkylaminopropionic acid and alkylaminoacetic acid, which contain about 8 to 18 carbon atoms in the alkyl group. Particularly preferred amphoteric surfactants are N-cocoalkyl amino propionate, cocoyl amino ethyl amino propionate and acyl sarcosines.

Anionic surfactants are characterized by a water-soluble anionic group (such as, for example, carboxylate, sulfate, sulfonate or phosphate) and a lipophilic group. Dermatologically safe anionic surfactants are known to many practitioners from related textbooks and are commercially available. They contain, in particular, linear C, alkyl sulfates, alkyl ether carboxylates, acyl isethionates, acyl sarcosinates in the form of their alkali metal, ammonium or alkanolammonium salts ₁₂ -C ₁₈ Acyl taurates and sulfosuccinates of alkyl or acyl groups and acyl glutamates in the form of their alkali metal or ammonium salts.

Particularly suitable cationic surfactants are quaternary ammonium compounds, preferably ammonium halides, more particularly chlorides and bromides, such as alkyl trimethyl ammonium chloride, dialkyl dimethyl ammonium chloride and trialkyl methyl ammonium chloride, for example cetyl trimethyl ammonium chloride, stearyl trimethyl ammonium chloride, distearyl dimethyl ammonium chloride, lauryl dimethyl benzyl ammonium chloride and tricetyl methyl ammonium chloride. Furthermore, readily biodegradable quaternary ester compounds, such as, for example, dialkyl ammonium methylsulfate and methyl hydroxyalkyl dialkoxyalkyl ammonium methylsulfate sold under the name stepntexe and the corresponding The series of products can be used as cationic surfactants. "esterquat" is generally understood to be a quaternized fatty acid triethanolamine ester salt. They can provide specific softness to the composition. They are known substances prepared by methods related to organic chemistry. Other cationic surfactants suitable for use in accordance with the present invention are quaternized protein hydrolysates.

One embodiment of the invention relates to a composition comprising a 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) and at least one oil component.

The oil component is typically present in an amount of 0.1 to 80wt.%, preferably 0.5 to 70wt.%, more preferably 1 to 60wt.%, even more preferably 1 to 50wt.%, in particular 1 to 40wt.%, more in particular 5 to 25wt.% and especially 5 to 15wt.%, based on the total weight of the composition.

The oil component may be selected for example from guerbet alcohols and other additional esters based on fatty alcohols containing 6 to 18, preferably 8 to 10 carbon atoms, such as myristyl myristate, myristyl palmitate, myristyl stearate, myristyl isostearate, myristyl oleate, myristyl behenate, myristyl erucate, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl isostearate, cetyl oleate, cetyl behenate, cetyl erudate, stearyl myristate, stearyl palmitate, stearyl stearate, stearyl isostearate, stearyl erudate, isostearate, stearyl myristate, isostearyl palmitate, isostearyl stearate, isostearyl isostearate, isostearyl oleate, oleyl isostearate, oleyl myristate, oleyl palmitate, oleyl stearate, oleyl isostearate, oleyl oleate, oleyl behenate, oleyl erucate, behenyl palmitate, behenyl stearate, stearyl isostearate, behenate, erucic acid mustard, stearyl palmitate, stearyl isostearate, erucic acid mustard, stearyl myristate, stearyl myristyl stearate, and stearyl erucic acid. Also suitable is C ₁₈ -C ₃₈ Alkyl-hydroxycarboxylic acids with straight-chain or branched C ₆ -C ₂₂ Esters of fatty alcohols, more particularly dioctyl malate, esters of linear and/or branched fatty acids with polyols, such as propylene glycol, dimer diols or trimer triols, based on C ₆ -C ₁₀ Triglyceride of fatty acid, liquid C-based ₆ -C ₁₈ Mixtures of mono-, di-and triglycerides of fatty acids, C ₆ -C ₂₂ Esters of fatty alcohols and/or Guerbet alcohols with aromatic carboxylic acids, more particularly benzoic acid, esters of dicarboxylic acids with polyols containing 2 to 10 carbon atoms and 2 to 6 hydroxyl groups, vegetable oils, branched primary alcohols, substituted cyclohexane, straight-chain and branched C ₆ -C ₂₂ Fatty alcohol carbonates, such as, for example, dioctyl carbonateCC), based on guerbet carbonates of fatty alcohols containing 6 to 18, preferably 8 to 10 carbon atoms, benzoic acid with linear and/or branched C ₆ To C ₂₂ Esters of alcohols (e.g.)>TN), each alkyl group containing a linear or branched, symmetrical or asymmetrical dialkyl ether of 6 to 22 carbon atoms, such as, for example, dioctyl ether (>OE), ring-opening products of epoxidized fatty acid esters with polyols and hydrocarbons or mixtures thereof.

Antioxidant agent

One embodiment of the invention relates to a composition comprising a 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) and at least one antioxidant.

Antioxidants can inhibit or prevent undesirable changes in the composition to be protected caused by oxygen effects and other oxidation processes. The role of antioxidants in most cases includes as radical scavengers for the radicals generated in the autoxidation process.

The antioxidants may for example be selected from the group consisting of

Amino acids (e.g., glycine, alanine, arginine, serine, threonine, histidine, tyrosine, tryptophan) and derivatives thereof,

imidazole (e.g. urocanic acid) and derivatives thereof,

peptides, e.g. D, L-carnosine, D-carnosine, L-carnosine (=beta-alanyl-L-histidine) and derivatives thereof

Carotenoids, carotenes (e.g. alpha-carotene, beta-carotene, lycopene, lutein) or derivatives thereof,

chlorogenic acid and its derivatives, and the use thereof,

lipoic acid and its derivatives (e.g. dihydrolipoic acid),

golden thioglucose, propylthiouracil and other thiols (e.g. thioredoxin, glutathione, cysteine, cystine, cystamine and its glycosyl groups, N-acetyl, methyl, ethyl, propyl, pentyl, butyl and lauryl groups, palmitoyl, oleyl, gamma-linolenyl, cholesteryl and glyceryl esters) and salts thereof,

Dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionate and derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) thereof,

sulfoximine compounds (e.g., sulfoximine, homocysteine sulfoximine, sulfoximine sulfone, penta-, hexa-, heptthionine)

(metal) chelators (e.g., alpha-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin),

alpha-hydroxy acids (e.g. citric acid, lactic acid, malic acid),

humic acid, bile extract, bilirubin, biliverdin, boldine (=alkaloid from the plant boldo tree, boldo extract,

EDTA, EGTA and derivatives thereof,

unsaturated fatty acids and derivatives thereof (e.g., gamma-linolenic acid, linoleic acid, oleic acid),

folic acid and its derivatives, and the use thereof,

ubiquinone and ubiquinol and derivatives thereof,

vitamin C and derivatives (e.g. ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl acetate),

tocopherols and derivatives (e.g. vitamin E acetate),

vitamin a and derivatives (e.g. vitamin a palmitate),

benzoin gum, rutin acid and coniferyl alcohol benzoate of its derivatives, alpha-glycosylrutin, ferulic acid, furfuryl glucose alcohol,

Butyl Hydroxy Toluene (BHT), butyl Hydroxy Anisol (BHA)

Nordihydroguaiaretic acid, trihydroxybenzene butanone, uric acid and derivatives thereof, mannose and derivatives thereof,

superoxide dismutase

Zinc and its derivatives (e.g. ZnO, znSO 4),

selenium and derivatives thereof (e.g. selenomethionine)

Stilbene and derivatives thereof (e.g. oxidized stilbene, trans-oxidized stilbene)

In a preferred embodiment, the antioxidant is selected from the group consisting of pentaerythritol, tetra-di-tert-butylhydroxyhydrocinnamate, nordihydroguaiaretic acid, ferulic acid, resveratrol, propyl gallate, butylhydroxytoluene (BHT), butylhydroxyanisole (BHA), ascorbyl palmitate, and tocopherol.

The composition according to the invention may comprise antioxidants in an amount of 0.001 to 25wt. -%, preferably 0.005 to 10wt. -%, preferably 0.01 to 8wt. -%, preferably 0.025 to 7wt. -%, preferably 0.05 to 5wt. -%, based on the total weight of the composition.

Deodorant active agent

One embodiment of the present invention relates to a composition comprising a 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) and at least one deodorant active agent.

The 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) may be used to impart a clean, long lasting fragrance to deodorant compositions and skin treated with such compositions.

Deodorant compositions (deodorants and antiperspirants) counteract, mask or eliminate body odor. Body odor is formed by the action of skin bacteria on apocrine sweat, which results in the formation of degradation products of unpleasant odors.

In a preferred embodiment of the present invention, the at least one deodorant active agent is selected from the group consisting of antiperspirant, esterase inhibitors and antimicrobial agents.

Suitable antiperspirant agents may be selected from the group consisting of salts of aluminium, zirconium or zinc. Examples are aluminum chloride, aluminum chloride hydrate, aluminum dichloride hydrate, aluminum sesquichloride hydrate and complex compounds thereof (e.g., with 1, 2-propanediol), aluminum hydroxy allantoin, aluminum chloride tartrate, aluminum zirconium trichloride hydrate, aluminum zirconium tetrachloride hydrate, aluminum zirconium pentachloride hydrate and complex compounds thereof (e.g., with amino acids such as glycine). Preference is given to using aluminum chloride hydrate, aluminum zirconium tetrachloride hydrate, aluminum zirconium pentachloride hydrate and complex compounds thereof.

In a preferred embodiment of the present invention, the composition comprises at least one antiperspirant selected from the group consisting of aluminum chloride, aluminum chloride hydrate, aluminum dichloride hydrate, aluminum sesquichloride hydrate, aluminum hydroxyallantoin, aluminum chloride tartrate, aluminum zirconium trichloride hydrate, aluminum zirconium tetrachloride hydrate, and aluminum zirconium pentachloride hydrate.

The composition according to the invention may comprise an antiperspirant in an amount of 1 to 50, preferably 5 to 30 and more particularly 10 to 25wt. -% based on the solids content of the composition.

When sweat is present in the underarm area, extracellular enzymes-esterases, mainly proteases and/or lipases, are formed by bacteria and break down esters present in the sweat, releasing odors during the process. Suitable esterase inhibitors are, for example, trialkyl citrates, such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate and in particular triethyl citrate. Esterase inhibitors inhibit enzyme activity and thereby reduce odor formation. The free acid may be released by cleavage of the citrate and reduce the pH of the skin to the point where the enzyme is deactivated by acylation. Other esterase inhibitors are sterol sulfates or phosphates, such as for example lanosterol, cholesterol, campesterol, stigmasterol and sitosterol sulfates or phosphates, dicarboxylic acids and esters thereof, such as glutaric acid, monoethyl glutarate, diethyl glutarate, adipic acid, monoethyl adipate, diethyl adipate, malonic acid and diethyl malonate, hydroxycarboxylic acids and esters thereof, such as for example citric acid, malic acid, tartaric acid or diethyl tartrate, and zinc glycinate.

In a preferred embodiment of the invention, the composition comprises at least one esterase inhibitor selected from the group consisting of trimethyl citrate, tripropyl citrate, triisopropyl citrate, triethyl citrate, lanosterol, cholesterol, campesterol, stigmasterol, sitosterol sulfate, sitosterol phosphate, glutaric acid, monoethyl glutarate, diethyl glutarate, adipic acid, monoethyl adipate, diethyl adipate, malonic acid, diethyl malonate, citric acid, malic acid, tartaric acid, diethyl tartrate and zinc glycinate.

The composition according to the invention may comprise an esterase inhibitor in an amount of 0.01 to 20, preferably 0.1 to 10 and more particularly 0.5 to 5wt. -% based on the solids content of the composition.

The term "antimicrobial" as used herein includes substances having bactericidal and/or bacteriostatic properties. Typically, these substances act on gram-positive bacteria such as, for example, 4-hydroxybenzoic acid and salts and esters thereof, N- (4-chlorophenyl) -N ' - (3, 4-dichlorophenyl) -urea, 2, 4' -trichloro-2 ' -hydroxydiphenyl ether (triclosan), 4-chloro-3, 5-dimethylphenol, 2' -methylene-bis- (6-bromo-4-chlorophenol), 3-methyl-4- (1-methylethyl) -phenol, 2-benzyl-4-chlorophenol, 3- (4-chlorophenoxy) -propane-1, 2-diol, 3-iodo-2-propynylbutyl carbamate, chlorhexidine, 3, 4' -trichlorocarbanilide (TTC), phenoxyethanol, glycerol Monocaprylate (GML), diglycerol Monocaprylate (DMC), salicylic acid-N-alkylamides such as, for example, salicylic acid-N-octylamide or salicylic acid-N-decylamide.

In preferred embodiments, the antimicrobial agent is selected from the group consisting of chitosan, phenoxyethanol, 5-chloro-2- (2, 4-dichlorophenoxy) -phenol, 4-hydroxybenzoic acid and salts and esters thereof, N- (4-chlorophenyl) -N ' - (3, 4-dichlorophenyl) -urea, 2, 4' -trichloro-2 ' -hydroxydiphenyl ether (triclosan), 4-chloro-3, 5-dimethylphenol, 2' -methylene-bis- (6-bromo-4-chlorophenol), 3-methyl-4- (1-methylethyl) -phenol, 2-benzyl-4-chlorophenol, 3- (4-chlorophenoxy) -propane-1, 2-diol, 3-iodo-2-propynylbutyl carbamate, chlorhexidine, 3, 4' -trichlorocarbanilide (TTC), phenoxyethanol, glycerol Monocaprylate (GML), diglycerol Monocaprylate (DMC), salicylic acid-N-alkylamide.

The composition according to the invention may comprise an antibacterial agent in an amount of 0.01 to 5wt.% and preferably 0.1 to 2 wt.%, based on the solids content of the composition.

The composition according to the invention may further comprise one or more substances, such as for example: preservatives, abrasives, anti-acne agents, anti-skin aging agents, anti-cellulite agents, anti-dandruff agents, anti-inflammatory agents, anti-irritants, irritation reducing agents, astringents, antiperspirants, bactericides, antistatic agents, binders, buffering agents, carrier materials, chelating agents, cell stimulating agents, conditioning agents, depilatories, emulsifiers, enzymes, essential oils, fibers, film formers, and anti-irritants fixatives, foam formers, foam stabilizers, foam-preventing substances, foam promoters, fungicides, gelling agents, gel formers, hair conditioners, hair styling agents, hair conditioning compositions, hair slipping agent, moisturizing agent, bleaching agent, reinforcing agent, detergent, optical brightening agent, impregnating agent, antifouling agent, friction reducing agent, lubricant moisturizing creams, ointments, sunscreens, plasticizers, masking agents, polishing agents, luminescent agents, polymers, powders, proteins, fatting agents, exfoliating agents, silicones, skin soothing agents, skin cleansing agents, skin care agents, skin healing agents, skin lightening agents, skin protectants, skin softeners, coolants, skin coolants, warmers, skin warmers, stabilizers, UV absorbers, UV filters, fabric softeners, suspending agents, skin tanning agents, thickeners, vitamins, waxes, fats, phospholipids, saturated fatty acids, mono-or polyunsaturated fatty acids, alpha-hydroxy acids, polyhydroxy fatty acids, liquefying agents, dyes, color fixatives, pigments, corrosion inhibitors, polyols, electrolytes, or silicone derivatives.

The 1, 4-butanediol mono-or diesters of formula (I) or mixtures of different 1, 4-butanediol mono-and/or diesters of formula (I) as described herein can be used in a wide variety of compositions, preferably in fragrance compositions, more preferably in fragrance compositions. The olfactory and physical properties of compound (I), such as solubility in conventional solvents and compatibility with the other conventional ingredients of such compositions, emphasize the particular applicability of the combination for the purpose of use and composition.

Suitable compositions are, for example, perfume compositions, body care compositions (including cosmetic compositions), products for oral and dental hygiene, hygiene products, cleaning compositions (including dishwashing compositions), textile detergent compositions, compositions for fragrance dispensers, foods, food supplements, pharmaceutical compositions and crop protection compositions.

The perfume composition may be selected from the group consisting of a fine fragrance, an air freshener in liquid form, in gel form or in a form applied to a solid carrier, an aerosol spray, a fragrance cleanser, a perfume candle, and an oil, such as a lamp oil or an oil for massage.

Examples of fine fragrances are perfume extracts, light fragrances, colognes, solid fragrances and concentrated fragrances.

Body care compositions include cosmetic compositions, and may be selected from the group consisting of after-shave, pre-shave products, cologne sprays (splacer), solid and liquid soaps, shower gels, shampoos, shaving soaps, shaving foams, bath oils, oil-in-water, water-in-oil and water-in-oil cosmetic creams such as, for example, skin creams and emulsions, face creams and emulsions, sun creams and emulsions, post-sun creams and emulsions, hand creams and emulsions, foot creams and emulsions, hair loss creams and emulsions, after-shave creams and emulsions, tanning creams and emulsions, hair care products such as, for example, hair sprays, hair gels, hair styling emulsions, hair conditioners, shampoos, permanent and semi-permanent hair colorants, hair styling compositions such as cold wave and hair smoothing compositions, hair tonic, hair creams and lotions, deodorants and antiperspirants such as, for example, underarm sprays, running beads, deodorant sticks and deodorant creams; decorative cosmetic products such as, for example, eyeliners, eye shadows, nail polish, foundations, lipsticks, and mascaras. Additional examples are given above.

The product for oral and dental hygiene may be selected from the group consisting of toothpastes, dental floss, mouthwashes, breath fresheners, dental foams, tooth gels and dental polishing strips.

The sanitary product may be selected from the group consisting of fragrances, insecticides, insect repellents, propellants, rust removers, fragranced fresh wipes, armpit pads, baby diapers, sanitary napkins, toilet paper, cosmetic napkins, toilet paper, dishwashing agents and deodorants.

Cleaning compositions, such as, for example, cleaners for solid surfaces, may be selected from the group consisting of perfumed acidic, alkaline and neutral cleaners, such as, for example, floor cleaners, window cleaners, dishwashing compositions for hand and machine dishwashing applications, bath and hygiene cleaners, scrubbing milk, solid and liquid toilet cleaners, powder and foam carpet cleaners, waxes and polishes, such as furniture polishes, floor waxes, shoe polishes, disinfectants, surface disinfectants and sanitation cleaners, brake cleaners, pipe cleaners, scale removers, grill and oven cleaners, algae and moss removers, mold removers, facade cleaners.

The textile detergent composition may be selected from the group consisting of liquid detergents, powder detergents, laundry pretreaters (such as bleach, soaking agents and soil release agents), fabric softeners, washing soaps, washing tablets.

By food product is meant raw, cooked or processed edible substances, ice, beverages or ingredients, or chewing gum, soft candy, jelly and candy, intended or intended for all or part of human consumption.

A food supplement is a product intended for ingestion that contains dietary ingredients intended to add further nutritional value to the diet. The dietary component may be one or any combination of the following: vitamins, minerals, herbs or other vegetable preparations, amino acids, dietary substances, concentrates, metabolites, ingredients or extracts for supplementing the diet by increasing total dietary intake. The food supplement may be present in various forms such as tablets, capsules, soft gels, soft capsules, liquids or powders.

Pharmaceutical compositions include compositions intended for diagnosis, cure, mitigation, treatment or prevention of disease, as well as articles of manufacture (other than food) intended to affect the structure or any function of the body of a human or other animal.

Crop protection compositions include compositions intended for the management of plant diseases, weeds and other pests (vertebrates and invertebrates) that destroy agricultural crops and forestry. More detailed definitions are given above.

Preferably, the compositions of the present invention are perfume compositions, body care compositions (including cosmetic compositions), products for oral and dental hygiene, hygiene products, cleaning compositions (including dishwashing compositions), textile detergent compositions, compositions for fragrance dispensers or crop protection compositions.

In particular, the compositions of the present invention are personal care or home care compositions, such as body care compositions (including cosmetic compositions), cleaning compositions (including dishwashing compositions) or textile detergent compositions.

The composition according to the invention may further comprise one or more substances, such as for example: preservatives, abrasives, anti-acne agents, anti-skin aging agents, antibacterial agents, anti-cellulite agents, antidandruff agents, anti-inflammatory agents, anti-irritants, irritation-reducing agents, antimicrobial agents, antioxidants, astringents, antiperspirants, bactericides, antistatic agents, adhesives, buffers, carrier materials, chelating agents, cellular stimulants, cleaning agents, care agents, depilatories, surface-active substances, deodorants, antiperspirants, emulsifiers, enzymes, essential oils, fibers, film formers, fixatives, foam formers, foam stabilizers, foam-preventing substances, foam boosters, fungicides, gelling agents, gel formers, hair conditioning agents, hair smoothing agents, moisturizing substances, bleaching agents, enhancing agents, detergents, optical brighteners impregnating agents, anti-soiling agents, friction reducers, lubricants, moisturizing creams, ointments, sunscreens, plasticizers, masking agents, polishing agents, lightening agents, polymers, powders, proteins, fatliquoring agents, exfoliating agents, silicones, skin soothing agents, skin cleansing agents, skin care agents, skin healing agents, skin lightening agents, skin protectants, skin softeners, cooling agents, skin coolants, warmers, skin warmth retention agents, stabilizers, UV absorbers, UV filters, fabric softeners, suspending agents, skin tanning agents, thickeners, vitamins, waxes, fats, phospholipids, saturated fatty acids, mono-or polyunsaturated fatty acids, alpha-hydroxy acids, polyhydroxy fatty acids, liquefying agents, dyes, color fixatives, pigments, corrosion inhibitors, polyols, electrolytes, or silicone derivatives.

In a preferred embodiment, the composition of the invention is a home care composition, in particular a dishwashing composition, a laundry composition or a surface cleaning composition. Such compositions comprise at least one surfactant and typically at least one of the following components: sequestering agents, enzymes, foaming agents, foam stabilizers, antimicrobial agents, pH adjusting agents (acids or bases), and if the composition is liquid or gel-like, water and optionally also organic solvents.

By way of example only, such a composition may comprise

(a) 0.1% to 40% by weight relative to the total weight of the composition of one or more surfactants;

(b) 0.01 to 5% by weight of one or more 1, 4-butanediol mono-or diesters of formula (I) as defined above;

(c) 0% to 15% by weight, relative to the total weight of the composition, of at least one organic solvent;

(d) 0% to 6% by weight relative to the total weight of the composition of at least one enzyme;

(e) 0% to 20% by weight, relative to the total weight of the composition, of at least one sequestering agent;

(f) 0% to 8% by weight, relative to the total weight of the composition, of at least one defoamer and/or foam stabilizer;

(g) Optionally a pH adjuster; in an amount suitable to obtain the desired pH;

(h) 0% to 50% by weight relative to the total weight of the composition of a further additive;

(i) Optionally water, adds up to 100%.

Suitable surfactants of component (a) correspond to those listed above. They may be nonionic, anionic, cationic, zwitterionic or amphoteric. Typically, a mixture of two or more surfactants is used.

Suitable solvents for component (C) are, for example, C ₂ -C ₃ Alkanols (e.g. ethanol, n-propanol, isopropanol), C ₂ -C ₃ Alkylene glycols (e.g. ethylene glycol, propylene glycol), C ₂ -C ₃ C of the alkanediol ₁ -C ₄ Alkyl monoethers (e.g., ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol mono-n-butyl ether (also known as butylene glycol), propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, and propylene glycol mono-n-butyl ether), polyether polyols (e.g., polyethylene glycol, polypropylene glycol), C of polyether polyols ₁ -C ₃ Alkyl monoethers (e.g. polyethylene glycol monomethyl ether, polyethylene glycol monoethyl ether, polyethylene glycol mono-n-propyl ether, polyethylene glycol mono-n-butyl ether), optionally substituted with one or more C' s ₁ -C ₁₂ Alkyl substituted 5-, 6-or 7-membered lactones (e.g., gamma-butyrolactone, gamma-valerolactone, gamma-octanolactone, gamma-valerolactone, delta-decanolide, delta-dodecalactone and epsilon-caprolactone); can be one or more C ₁ -C ₁₂ Alkyl-substituted 5-, 6-or 7-membered cyclic carbonates (e.g. ethylene carbonate, propylene carbonate and butylene carbonate, which may bear one or more C's) ₁ -C ₁₂ -an alkyl substituent); aliphatic esters (e.g., ethyl acetate, propyl acetate, butyl acetate, methyl propionate, and ethyl propionate), carboxamides (e.g., N-dimethylformamide, N-diethylformamide, and N, N-dimethylacetamide), or mixtures thereof.

Suitable enzymes of component (d) are those typically used in laundry, dish washing or surface cleaning compositions, such as hydrolases, e.g. proteases, esterases, glucosidases, lipases, dnases, amylases, cellulases, mannanases, other glycosyl hydrolases and mixtures of the foregoing enzymes. All of these hydrolases help to solubilize and remove soils from protein, grease or starch containing stains/residues. For bleaching, oxidoreductases may also be used.

Sequestering agents of component (e), also known as builders, building agents, framework materials, complexing agents, chelates, chelating agents or softening agents, bind alkaline earth metals and other water-soluble metal salts without precipitation. They help to break up the soil, disperse the soil components, help to separate the soil and in some cases have a washing effect on their own. Many sequestering agents are multifunctional, meaning that these materials have additional functions, such as dispersing activity or anti-ash properties. Suitable sequestering agents may be organic or inorganic in nature. Examples are aluminosilicates, carbonates, phosphates and polyphosphates, polycarboxylic acids, polycarboxylates, hydroxycarboxylic acids, phosphonic acids such as hydroxyalkyl phosphonic acids, phosphonates, aminopolycarboxylic acids and salts thereof, and polymeric compounds containing carboxylic acid groups and salts thereof. More specific examples of inorganic sequestering agents are crystalline or amorphous aluminosilicates having ion exchange properties, such as zeolites; di-or phyllosilicates; carbonates and bicarbonates, typically in the form of their alkali, alkaline earth or ammonium salts; alkali metal orthophosphates and/or polyphosphates, such as pentasodium triphosphate. More specific examples of organic sequestering agents are C ₄ -C ₃₀ Di-, tri-and tetracarboxylic acids, e.g. succinic acid, propane tricarboxylic acid, butane tetracarboxylic acid, cyclopentane tetracarboxylic acid and having C ₂ -C ₂₀ -alkyl-and alkenyl succinic acids of alkyl or alkenyl groups; hydroxycarboxylic acids and polyhydroxycarboxylic acids (sugar acids), such as malic acid, tartaric acid, gluconic acid, mucic acid, lactic acid, glutaric acid, citric acid, tartronic acid, glucoheptonic acid, lactobionic acid and sucrose mono-, di-and tricarboxylic acids; phosphonic acids, such as hydroxyalkyl phosphonic acids or amino phosphonic acids and salts thereof; polyaspartic acid and salts thereof; polymeric compounds containing carboxylic acid groups, such as acrylic acid homopolymers; oligomeric maleic acid, and the like.

The defoamers and/or foam stabilizers of component (f) are, for example, soaps, waxes and silicone oils.

Component (A)(g) The pH regulator of (2) is an acid, a base and a buffer system. The acid may be inorganic or organic. Suitable mineral acids are, for example, sulfuric acid, hydrochloric acid and phosphoric acid. Suitable organic acids are, for example, aliphatic, saturated, unsubstituted C ₁ -C ₆ Mono-, di-and tri-carboxylic acids, such as formic acid, acetic acid, propionic acid, oxalic acid, succinic acid and glutaric acid; aliphatic, saturated C with one or more OH groups ₁ -C ₆ Mono-, di-and tri-carboxylic acids such as lactic acid, tartaric acid and citric acid; aliphatic, unsaturated C ₁ -C ₆ -mono-, di-and tri-carboxylic acids such as sorbic acid; aromatic carboxylic acids such as benzoic acid, salicylic acid and mandelic acid; and sulfonic acids such as methanesulfonic acid or toluenesulfonic acid. Organic acids are mainly used to adjust the pH of the composition, but some of them, such as di-and tricarboxylic acids, may also be used as sequestering agents. Suitable bases are in particular inorganic bases, such as carbonates mentioned in the context of sequestering agents, for example sodium carbonate or potassium carbonate; additional alkali and alkaline earth metal hydroxides, such as NaOH or KOH. Suitable buffers are typical systems such as hydrogen phosphate/dihydrogen phosphate buffers, carbonate/bicarbonate buffers, acetic acid/acetate buffers or Tris buffers. Furthermore, most of the above acids, which are weak and whose anions are not strong salts, also have buffering capacity.

Examples of further additives (h) are antimicrobial agents (including preservatives), perfumes other than (b), hydrotropes, enzyme stabilizers, bleaching agents, corrosion inhibitors, dyes, thickeners, activity enhancers and inorganic salts.

If the composition is liquid or gel-like, it must contain water, typically in an amount of 10% to 99.89% by weight relative to the total weight of the composition. In liquid ready-to-use compositions (i.e. compositions in which the ready-to-use composition is used as such and does not require any further dilution or addition of further substances), the amount of water is typically in the range of 30% to 99.89% by weight, typically 40% to 99% by weight, relative to the total weight of the composition.

In a specific embodiment, the home care composition is a refill concentrate. Refill concentrates contain all the ingredients of the final ready-to-use product except for the substantial absence ("substantial" considering the fact that some ingredients may contain some residual water) or the presence of water in amounts well below those of the final ready-to-use product. The end user simply fills the refill concentrate into the appropriate container and adds the indicated amount of water.

Such refill concentrates preferably comprise:

(a) 1% to 60% by weight relative to the total weight of the composition of one or more surfactants;

(b) 0.02 to 10% by weight of one or more 1, 4-butanediol mono-or diesters of formula (I) as defined above;

(c) 0% to 30% by weight, relative to the total weight of the composition, of at least one organic solvent;

(d) 0% to 10% by weight relative to the total weight of the composition of at least one enzyme;

(e) 0% to 10% by weight, relative to the total weight of the composition, of at least one sequestering agent;

(f) 0% to 10% by weight, relative to the total weight of the composition, of at least one defoamer and/or foam stabilizer;

(g) Optionally a pH adjuster; in an amount suitable to obtain the desired pH;

(h) 0% to 50% by weight relative to the total weight of the composition of a further additive; and

(i) 0% to 20% by weight of water relative to the total weight of the composition;

wherein components (a) to (i) add up to 100% by weight.

In another preferred embodiment, the composition of the present invention is a personal care composition. The personal care compositions may be so used for hygienic or cosmetic use. Examples of suitable personal care compositions are given above.

Suitable personal care compositions may exist in a wide variety of forms, for example as liquid formulations of W/O, O/W, O/W/O, W/O/W or PIT emulsions and various microemulsions; in the form of a non-emulsified water-based liquid, in the form of a gel, in the form of an oil, cream, emulsion or emulsion, in the form of a spray (a propellant gas spray or a pump spray) or an aerosol, in the form of a foam, in the form of a paste, in the form of a wet wipe (e.g. for cleaning diaper areas). The personal care composition may be, for example, a cream, gel, emulsion, alcohol and water/alcohol solution, emulsion, wax/fat composition, or ointment. The ingredients typically present in such personal care compositions and their amounts vary depending on the particular formulation. Examples of such ingredients are solvents, surfactants, emulsifiers, rheology modifiers (typically thickeners), conditioning agents, emollients, skin care ingredients, lubricants, fillers, antioxidants, dermatologically active ingredients, fragrances and water.

Formulations intended primarily for cleansing, such as soaps, body washes and shampoos, contain at least one or more surfactants, usually anionic, optionally in combination with such surfactants in zwitterionic form; and water. In addition, they generally contain at least one of the following components: emulsifiers, sequestering agents, fragrances, pH adjusters (typically organic acids and/or inorganic bases), inorganic salts (principally NaCl), dyes, pigments, preservatives, pearlescers, opacifiers, viscosity modifiers, conditioning agents, natural hair nutrients, dermatological active ingredients.

Of particular interest are shampoo formulations in the form of shampoos. Furthermore, especially interesting are body washes. Shampoo and body washes typically contain water and at least one anionic surfactant.

Suitable anionic surfactants are mainly all those described above which are cosmetically acceptable. The total amount of anionic surfactant in the shampoo and body wash compositions typically ranges from 0.5% to 45% by weight, for example from 1.5% to 35% by weight, preferably from 2% to 20% by weight, based on the total weight of the composition. In shampoos and body washes, it is useful to use surfactants, which are good foam formers. In addition, the shampoo or body wash composition may include nonionic, amphoteric, and/or cationic cosurfactants that help impart aesthetic, tactile, combing, physical, or cleansing properties to the composition. Suitable nonionic, amphoteric/zwitterionic and cationic surfactants are those described above. The total amount of nonionic surfactant in the shampoo or body wash composition typically ranges from 0.5% to 15% by weight, preferably from 2% to 10% by weight, the total amount of amphoteric or zwitterionic surfactant in the shampoo or body wash composition typically ranges from 0.5% to 15% by weight, preferably from 1% to 10% by weight, and the total amount of cationic surfactant in the shampoo or body wash composition typically ranges from 0.05% to 1% by weight, more preferably from 0.08% to 0.5% by weight, based on the total weight of the composition. The total amount of surfactant (including any cosurfactants and/or any emulsifiers) in the shampoo or body wash composition is typically from 1% to 50% by weight, preferably from 2% to 40% by weight, more preferably from 10% to 25% by weight, based on the total weight of the composition.

In shampoo or body wash compositions, the 1, 4-butanediol mono-or diester of formula (I) is typically present in an amount of from 0.01% to 5% by weight, preferably from 0.01% to 2% by weight, in particular from 0.01% to 1% by weight, based on the total weight of the composition.

If the shampoo or body wash composition is liquid or gel-like, it contains water; typically in an amount of from 30% to 98% by weight, preferably from 50% to 90% by weight, relative to the total weight of the composition.

Other components which may be present in the shampoo or body wash are, for example, suspending agents, such as polyacrylic acid, crosslinked polymers of acrylic acid, copolymers of acrylic acid with hydrophobic monomers, copolymers of carboxylic acid-containing monomers and acrylic esters, crosslinked copolymers of acrylic acid and acrylic esters, heteropolysaccharide gums and crystalline long chain acyl derivatives, the latter preferably being selected from the group consisting of ethylene glycol stearates, alkanolamides of fatty acids having from 16 to 22 carbon atoms and mixtures thereof; perfumes, dyes and pigments other than 1, 4-butanediol mono-and diacetate, pH regulators, preservatives, pearlizing or opacifying agents, viscosity modifiers and salts such as NaCl; in shampoos, there are also conditioning agents, natural hair nutrients or dermatologically active ingredients, such as vegetable preparations, fruit extracts, caffeine, panthenol, sugar derivatives, amino acids such as hydrolyzed keratin or glycine, vegetable or hydrogenated vegetable oils.

The 1, 4-butanediol mono-or diester of formula (I) or the mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) can be included in the composition simply by mixing them directly with an alkaline composition which is only free of this compound(s). Alternatively, the 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) may be mixed simultaneously or continuously with the other components of the composition or with a preformed mixture of a portion of the other components.

The 1, 4-butanediol mono-or diester of formula (I) or the mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) may be entrapped with entrapment materials in earlier steps, for example polymers, capsules, microcapsules and nanocapsules, liposomes, film formers, absorbents (such as carbon or zeolites), cyclic oligosaccharides and mixtures thereof, or may be chemically bound to a substrate suitable for releasing compound (I) upon application of an external stimulus such as light, enzymes, etc., and then mixed with the composition.

The 1, 4-butanediol mono-or diesters of the formula (I) according to the invention or the mixtures of different 1, 4-butanediol mono-and/or diesters of the formula (I) and the compositions comprising these compounds can also be in the form of microcapsules, spray-dried, inclusion complexes or extruded products. With regard to a more targeted release of fragrance, the properties can be further optimized by means of so-called "coating" with suitable materials, for which purpose preferably waxy synthetic substances such as, for example, polyvinyl alcohol are used.

Microencapsulation can be carried out, for example, by means of a so-called coacervation process with the aid of a capsule material, for example made of polyurethane-based substances or soft gelatin. Spray-dried perfume oils may be produced, for example, by spray-drying emulsions or dispersions comprising 1, 4-butanediol mono-or diesters of formula (I) or mixtures of different 1, 4-butanediol mono-and/or diesters of formula (I), or the compositions of the invention described herein, wherein carrier materials that may be used are modified starches, proteins, dextrins and vegetable gums. The inclusion complex may be prepared, for example, by introducing a dispersion of the flavour composition and cyclodextrin or urea derivative into a suitable solvent, for example water. The extruded product may be produced by melting a compound of formula (I), or a mixture of different compounds (I), or a composition of the invention as described herein, with a suitable waxy substance and by extrusion and subsequent solidification, optionally in a suitable solvent such as isopropanol.

In general, the total amount of one or more 1, 4-butanediol mono-or diesters of formula (I) in the composition according to the invention is typically suitable for the particular intended use or application and can therefore vary within wide limits. Typically, conventional standard commercial quantities for fragrance are used.

The composition according to the invention may comprise a total amount of compounds of formula (I) of from 0.001% to 99.9% by weight, preferably from 0.01% to 90% by weight, more preferably from 0.01% to 80% by weight, in particular from 0.01% to 60% by weight, more in particular from 0.01% to 40% by weight, for example from 0.01% to 10% by weight or from 0.01% to 15% by weight or from 0.01% to 5% by weight or from 0.05% to 5% by weight, based on the total weight of the composition.

In one embodiment of the invention, the composition comprises a total amount of compounds of formula (I) of from 0.001 to 10% by weight or from 0.001 to 5% by weight, preferably from 0.01 to 2% by weight or from 0.05 to 5% by weight, based on the total weight of the composition.

The compounds of formula (I) not only have a pleasant fragrance, in particular a flavour; they are also readily available. In particular, they can be readily treated with reduced CO ₂ Footprint production, e.g. by using renewable sources and/or by isolating potentially dangerous C from industrial or agricultural processes ₁ Gases (e.g. CO ₂ Or methane) that would otherwise be released to the atmosphere.

The following examples serve as further illustrations of the invention.

Examples

Abbreviations:

MTBE methyl tert-butyl ether

1. Preparation example

1.1 Preparation of 1, 4-butanediol diacetate

25g (0.28 mol) of 1, 4-butanediol are reacted with 57g (0.56 mol) of acetic anhydride and 400mgNR50 (acidic ion exchanger) are mixed. The mixture was stirred at room temperature for 24h. The reaction mixture was then diluted with 200ml of water and stirred for a further 10min. The mixture was treated with 75ml NaHCO ₃ Slowly neutralized to pH 8 and then extracted with MTBE. The MTBE phase was treated with MgSO ₄ The solvent was dried and evaporated. The reaction product was distilled at 3 mbar and 94 ℃.

The product contained 0.3% monoester and 99.6% diester (GC area).

1.2 preparation of higher purity 1, 4-butanediol diacetate

Example 1.1 was repeated. The product was then subjected to column chromatography on silica as a further purification step to produce a product containing <0.05% monoester (i.e. 1, 4-butanediol monoacetate) and >99.9% diester (i.e. 1, 4-butanediol diacetate).

1.3 Preparation of 1, 4-butanediol monoacetate

50g (0.56 mol) of 1, 4-butanediol are reacted with 28g (0.27 mol) of acetic anhydride, 0.5g of acetic acid and 400mgNR50 (acidic ion exchanger) are mixed. The mixture was stirred at room temperature for 24h. The reaction mixture was then diluted with 100ml of water and stirred for a further 10min. The mixture was treated with 55g NaHCO ₃ Slowly neutralized to pH 8 and then extracted with MTBE. The MTBE phase was treated with MgSO ₄ The solvent was dried and evaporated. According to GC analysis, the crude mixture contained 56.8% monoacetate and 27.2% diacetate. The reaction product was distilled at 3 mbar. The 1, 4-butanediol monoacetate obtained had a purity (GC) of 92.4% (5.6% 1, 4-butanediol diacetate, 1.7% 1, 4-butanediol).

1.4 Preparation of a 99:1 mixture of 1, 4-butanediol diacetate and 1, 4-butanediol monoacetate

The 1, 4-butanediol diacetate of example 1.1 and the 1, 4-butanediol monoacetate of example 1.3 were mixed to produce a 99:1 weight ratio of 1, 4-butanediol diacetate to 1, 4-butanediol monoacetate mixture.

1.5 Preparation of a 98:2 mixture of 1, 4-butanediol diacetate and 1, 4-butanediol monoacetate

The 1, 4-butanediol diacetate of example 1.1 and the 1, 4-butanediol monoacetate of example 1.3 were mixed to produce a 98:2 weight ratio of 1, 4-butanediol diacetate to 1, 4-butanediol monoacetate mixture.

1.6 Preparation of a 95:5 mixture of 1, 4-butanediol diacetate and 1, 4-butanediol monoacetate

The 1, 4-butanediol diacetate of example 1.1 and the 1, 4-butanediol monoacetate of example 1.3 were mixed to produce a mixture of 1, 4-butanediol diacetate and 1, 4-butanediol monoacetate in a weight ratio of 95:5.

1.7 Preparation of a 90:10 mixture of 1, 4-butanediol diacetate and 1, 4-butanediol monoacetate

The 1, 4-butanediol diacetate of example 1.1 and the 1, 4-butanediol monoacetate of example 1.3 were mixed to produce a mixture of 1, 4-butanediol diacetate and 1, 4-butanediol monoacetate in a weight ratio of 90:10.

1.8 Preparation of an 80:20 mixture of 1, 4-butanediol diacetate and 1, 4-butanediol monoacetate

The 1, 4-butanediol diacetate of example 1.1 and the 1, 4-butanediol monoacetate of example 1.3 were mixed to produce a mixture of 1, 4-butanediol diacetate and 1, 4-butanediol monoacetate in a weight ratio of 80:20.

1.9 Preparation of 1, 4-butanediol dipropionate

18g (0.2 mol) of 1, 4-butanediol are reacted with 52g (0.4 mol) of propionic anhydride and 1gNR50 (acidic ion exchanger) are mixed. The mixture was stirred at room temperature for 72h. The reaction mixture was then diluted with 100ml of water and stirred for a further 10min. The mixture was treated with 60g NaHCO ₃ Slowly neutralized to pH 8 and then extracted with MTBE. The MTBE phase was treated with MgSO ₄ The solvent was dried and evaporated. The mixture was distilled at 25 mbar (165 ℃). The 1, 4-butanediol dipropionate obtained had a purity (GC) of 97.3% (2.6% monopropionate).

2. Olfactory test

To test the quality and intensity of the odor of the compound (I) of the present invention, an aroma bar test was performed.

For this purpose, the absorbent strip is immersed in a solution containing 1 to 10% by weight of a triethyl citrate solution of the compound (I) to be tested. After evaporation of the solvent (about 30 seconds), the fragrance effect was evaluated olfactively by a trained panel of perfumers.

The results of the fragrance test are summarized below.

Results of fragrance test.

The product of example 1.1:

red fruit, raspberry, sweet taste, blueberry

The product of example 1.2:

red fruit, raspberry, sweet taste, blueberry

The products of examples 1.4 to 1.8:

the same aroma notes as the product of example 1.1, but with a more fruity effect that increases with increasing monoacetate content. In the case of 1.6 to 1.8, the fruity effect is very clear. However, as the monoacetate content increases, the fragrance becomes weaker.

The product of example 1.9:

the same aroma notes as the product of example 1.1, but lighter

Sales products and advantageous flavour compositions

"solution A" is the undiluted product of example 1.1.

"solution B" is the undiluted product of example 1.2.

"solution C" is the undiluted product of example 1.4.

"solution D" is the undiluted product of example 1.5.

"solution E" is the undiluted product of example 1.6.

"solution F" is the undiluted product of example 1.7.

"solution G" is the undiluted product of example 1.8.

"solution H" is the undiluted product of example 1.9.

I. Advantageous flavour compositions:

solution a as described above was formulated into a composition according to table 2. The amounts given in table 2 are in weight units in grams.

Table 2: fragrance compositions 1A and 1B

Solution a as described above was formulated into a composition according to table 3. The amounts given in table 3 are in weight units in grams.

Table 3: fragrance compositions 2A and 2B

Flavour composition 3 corresponds to flavour composition 1A, wherein solution a is replaced by the same amount of solution B. Flavour composition 4 corresponds to flavour composition 1B, wherein solution a is replaced by the same amount of solution B. Flavour composition 5 corresponds to flavour composition 2A, wherein solution a is replaced by the same amount of solution B. Flavour composition 6 corresponds to flavour composition 2B, wherein solution a is replaced by the same amount of solution B.

Flavour composition 7 corresponds to flavour composition 1A, wherein solution a is replaced by the same amount of solution C. Flavour composition 8 corresponds to flavour composition 1B, wherein solution a is replaced by the same amount of solution C. Flavour composition 9 corresponds to flavour composition 2A, wherein solution a is replaced by the same amount of solution C. Flavour composition 10 corresponds to flavour composition 2B, wherein solution a is replaced by the same amount of solution C.

Flavour composition 11 corresponds to flavour composition 1A, wherein solution a is replaced by the same amount of solution D. Flavour composition 12 corresponds to flavour composition 1B, wherein solution a is replaced by the same amount of solution D. Flavour composition 13 corresponds to flavour composition 2A, wherein solution a is replaced by the same amount of solution D. Flavour composition 14 corresponds to flavour composition 2B, wherein solution a is replaced by the same amount of solution D.

Flavour composition 15 corresponds to flavour composition 1A, wherein solution a is replaced by the same amount of solution E. Flavour composition 16 corresponds to flavour composition 1B, wherein solution a is replaced by the same amount of solution E. Flavour composition 17 corresponds to flavour composition 2A, wherein solution a is replaced by the same amount of solution E. Flavour composition 18 corresponds to flavour composition 2B, wherein solution a is replaced by the same amount of solution E.

Flavour composition 19 corresponds to flavour composition 1A, wherein solution a is replaced by the same amount of solution F. Flavour composition 20 corresponds to flavour composition 1B, wherein solution a is replaced by the same amount of solution F. Flavour composition 21 corresponds to flavour composition 2A, wherein solution a is replaced by the same amount of solution F. Flavour composition 22 corresponds to flavour composition 2B, wherein solution a is replaced by the same amount of solution F.

Flavour composition 23 corresponds to flavour composition 1A, wherein solution a is replaced by the same amount of solution G. Flavour composition 24 corresponds to flavour composition 1B, wherein solution a is replaced by the same amount of solution G. Flavour composition 25 corresponds to flavour composition 2A, wherein solution a is replaced by the same amount of solution G. Flavour composition 26 corresponds to flavour composition 2B, wherein solution a is replaced by the same amount of solution G.

Flavour composition 27 corresponds to flavour composition 1A, wherein solution a is replaced by the same amount of solution H. Flavour composition 28 corresponds to flavour composition 1B, wherein solution a is replaced by the same amount of solution H. Flavour composition 29 corresponds to flavour composition 2A, wherein solution a is replaced by the same amount of solution H. Flavour composition 30 corresponds to flavour composition 2B, wherein solution a is replaced by the same amount of solution H.

The compositions according to tables 2 and 3, i.e. 1A, 1B, 2A and 2B and the flavour compositions 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 and 30 may be included in various compositions selected from the group consisting of: deodorant pump sprays, cleansing hair conditioners, cleansing gels, foam bath concentrates, hair gels, self-foaming body washes, sprayable sun care emulsions, sprayable sun protection emulsions, skin cleansing gels, 2-phase oil foam baths, shampoos, shower gels, water-alcohol AP/deodorant pump sprays, aerosols, water/alcohol AP/deodorant running beads, "off-bed" style gels, shave foams, sensitive skin baby shampoos, sensitive skin body washes, sensitive scalp gloss enhancing shampoos, deodorant sticks, baby wipes, after-shave balms, facial gels, facial day care creams, facial washes, body milks, sun care SPF50+, sprayable emulsions, hand dishwashing cleaners-conventional, hand dishwashing cleaners-concentrates, sanitary cleaners-concentrates, multipurpose cleaners, antimicrobial fabric softeners, detergent compositions, powder detergent compositions, and liquid detergent compositions.

Those skilled in the art may be familiar with various general formulations for the above products.

Compositions 1A, 1B, 2A, 2B, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 and 30 may be numbered, for example, at pages 6 to 46 under the heading New Aroma Chemicals [ novel fragrance chemical ], ip.com of tables 1 to D13: the specific formulation disclosed in IPCOM000258614D, wherein "fragrance composition 1A" is replaced by the same amount of composition 1A, 1B, 2A, 2B, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30.

Advantageous flavour compositions

II.1 perfume formulations for various uses

A base formulation of the ingredients listed in the table below was prepared. DPG is dipropylene glycol.

To this base formulation was added 2.5% by weight of the product of example 1.1. The resulting fragrance formulations were subjected to the following olfactory evaluation by a trained panel of perfumers:

the product-based formulation of example 1.1 adds its own effects and features, imparting a red fruit note to the perfume formulation and making it better, stronger, more natural, intense and greener.

II.2 perfume formulations for various uses

A base formulation of the ingredients listed in the table below was prepared. DPG is dipropylene glycol.

The basic preparation has green, light fruit taste, slightly tropical sweet taste, jasmine and rose fragrance, and woody and musk aftertaste.

To this base formulation, 100 parts by weight of the product of example 1.1 was added. According to the trained panel of perfumers, the resulting perfume formulations are characterized by a more fruity and sweet taste, a more raspberry taste, and a more pronounced musk note. Thus, the product of example 1.1 also acts as a musk note enhancer.

II.3 perfume formulations intended for use in dishwashing formulations

A base formulation for the ingredients listed in the table below was prepared for use in a dishwashing formulation.

To this base formulation was added 500 parts by weight of the product of example 1.1. The resulting fragrance formulations were subjected to the following olfactory evaluation by a trained panel of perfumers:

the product-based formulation of example 1.1 was supplemented with red fruit, strawberry, sweet note.

II.4 fragrance formulations intended for use in rattan aromatherapy

A formulation of the ingredients listed in the table below was prepared for use in rattan aromatherapy (an aroma dispenser in which the aroma is dispensed by slow evaporation supported by rattan).

The resulting flavor formulation was evaluated olfactively by a trained panel of perfumers as being more sweet and fruity than the product without example 1.1.

II.5 fragrance formulations intended for use in body washes

A base formulation for the ingredients listed in the table below in the body wash was prepared.

The resulting flavor formulations were evaluated as tropical fruit blends by a trained panel of perfumers in olfaction, with a variety of fruit flavors on floral, musk basis, including watermelon, kiwi, pineapple, passion fruit, and grapefruit.

A similar formulation was prepared but containing 50 parts by weight DPG instead of the product of example 1.1. The fresh and bright tropical fruit blend is characterized by having obvious watermelon and floral musk bottom flavoring.

Comparison of the two blends shows that the product of example 1.1 introduces a more natural effect and increases various tropical notes, especially towards the pineapple. Watermelon is still present, but it is better balanced and other fruits become better perceived. Thus, the product of example 1.1 also acts as some flavor enhancer.

II.6 perfume formulations intended for use in body washes

A base formulation for the ingredients listed in the table below in the body wash was prepared.

The resulting fragrance formulation was evaluated as a fresh, bright lavender fragrance by the olfactory evaluation of a trained panel of perfumers, with a dominant natural effect in the modern atmosphere provided by wood, musk and citrus elements.

A similar formulation was prepared but containing 50 parts by weight DPG instead of the product of example 1.1. It is characterized by classical lavender fragrance, modernized with dihydromyrcenol and Iso E Super and fresh citrus taste in the front tone.

Comparison of the two blends shows that the product of example 1.1 elicits a front note and provides a more natural feel by virtue of its fruity note highlighting the ketone notes of lavender and lavender.

Instant compositions

III.1 shampoo or body wash

Shampoo or body wash formulations were prepared by mixing the following components in the given proportions:

the body wash/shampoo formulation had a pleasant fruity flavour of the flavour set out in example ii.5.

A similar formulation containing 1% of the fragrance composition from example ii.6 instead of the fragrance composition from example ii.5 has a pleasant lavender fragrance of the notes listed in example ii.6.

The similar formulation containing 0.1% 1, 4-butanediol diacetate of example 1.1 instead of the fragrance composition from example II.5 well masks the unpleasant odor of the base formulation (i.e., the shampoo or body wash formulation without fragrance thereon). The formulation containing 0.1% 1, 4-butanediol diacetate of example 1.1 instead of the flavor composition from example ii.5 had a unique fruity flavor.

III.2 laundry detergent formulations

Laundry detergent formulations were prepared by mixing the following components in the given proportions:

the resulting clear and yellowish formulation with pH 8.1 has a pleasant fruity flavour with the flavour set out in example ii.1.

The similar formulation containing 0.5% 1, 4-butanediol diacetate of example 1.1 instead of the fragrance composition from example II.1 well masks the unpleasant odor of the base formulation (i.e., the laundry detergent formulation without perfume thereon). Increasing the amount of 1, 4-butanediol diacetate of example 1.1 (but still below 1%) produced a unique fruity aroma.

Claims (22)

1. Use of 1, 4-butanediol mono-or diesters of formula (I) or mixtures of two or more different 1, 4-butanediol mono-and/or diesters of formula (I) as fragrance chemicals

R ¹ -O-(CH ₂ ) ₄ -O-C(＝O)-R ² (I)

Wherein the method comprises the steps of

R ¹ Selected from hydrogen and-C (=o) -R ³ A group of; and is also provided with

R ² And R is ³ Independently of one another C ₁ -C ₂ -an alkyl group.

2. The use according to claim 1, wherein,

1, 4-butanediol diester is used, wherein R ¹ is-C (=O) -R ³ And R is ² And R is ³ Both are C ₁ -C ₂ -an alkyl group; wherein preferably R ² And R is ³ Are identical; or (b)

The following mixtures were used: 1, 4-butanediol diester, wherein R ¹ is-C (=O) -R ³ And R is ² And R is ³ Both are C ₁ -C ₂ -alkyl, and 1, 4-butanediol monoester, wherein R ¹ Is hydrogen and R ² Is C ₁ -C ₂ -an alkyl group; wherein, preferablyR in the diester ² And R is ³ R in the monoester ² Are identical.

3. Use according to any one of the preceding claims, wherein,

R ¹ is hydrogen or-C (=O) -CH ₃ The method comprises the steps of carrying out a first treatment on the surface of the And is also provided with

R ² Is methyl.

4. Use of 1, 4-butanediol diacetate according to claim 3.

5. Use of a mixture of 1, 4-butanediol diacetate and 1, 4-butanediol monoacetate according to claim 3.

6. Use of 1, 4-butanediol dipropionate according to claim 3.

7. Use of a mixture of 1, 4-butanediol dipropionate and 1, 4-butanediol monopropionate according to claim 3.

8. Use according to any one of claims 2, 3, 5 and 7, wherein the mixture contains the 1, 4-butanediol monoester in an amount of 0.01 to 99% by weight, preferably 0.1 to 20% by weight, relative to the total weight of the 1, 4-butanediol diester and the 1, 4-butanediol monoester.

9. Use according to claim 8, wherein the mixture contains the 1, 4-butanediol monoester in an amount of 0.1 to 10% by weight, in particular 0.1 to 5% by weight, more in particular 0.1 to 2% by weight, in particular 0.1 to 1% by weight and very in particular 0.1 to 0.5% by weight relative to the total weight of the 1, 4-butanediol diester and the 1, 4-butanediol monoester.

10. Use according to any one of the preceding claims, wherein the 1, 4-butanediol mono-and of formula (I)And/or the diester is derived from 1, 4-butanediol obtained from renewable sources, wherein in the 1, 4-butanediol mono-and/or diester of formula (I), ¹² c isotope and method for producing the same ¹⁴ The molar ratio of C isotopes is preferably less than 3X 10 ¹² 1, a step of; wherein preferably the 1, 4-butanediol mono-and/or diester of formula (I) is derived from 1, 4-butanediol obtained from a renewable source and carboxylic acid R obtained from a renewable source ² -C (=o) OH and R ³ -C (=o) OH, if R ¹ is-C (=O) -R ³ 。

11. Use according to any one of the preceding claims as a fragrance.

12. Use of a 1, 4-butanediol mono-or diester of formula (I) or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) as defined in any one of claims 1 to 10 for modifying and/or enhancing the fragrance of a composition; in particular for modifying and/or enhancing the flavour impact of the composition; in particular for modifying the fragrance characteristics of a perfuming ready-to-use composition.

13. Use of 1, 4-butanediol mono-or diesters of formula (I) or mixtures of different 1, 4-butanediol mono-and/or diesters of formula (I) as defined in any one of claims 1 to 10 for imparting a fruity or sweet taste or a combined fruity and sweet olfactory note;

And in particular 1, 4-butanediol diacetate or a mixture of 1, 4-butanediol diacetate and 1, 4-butanediol monoacetate containing 0.1 to 20% by weight, relative to the total weight of 1, 4-butanediol diacetate and 1, 4-butanediol monoacetate, or 1, 4-butanediol dipropionate or a mixture of 1, 4-butanediol dipropionate and 1, 4-butanediol monopropionate containing 0.1 to 10% by weight, in particular 0.1 to 3% by weight, relative to the total weight of 1, 4-propanediol dipropionate and 1, 4-butanediol monopropionate), for imparting one of the following olfactory notes: red fruit, raspberry, blueberry, sweet; or any combination thereof.

14. Use according to any one of the preceding claims in a composition selected from the group consisting of perfume compositions, body care compositions, products for oral or dental hygiene, hygiene products, cleaning compositions, textile detergent compositions, compositions for fragrance dispensers, food products, food supplements, pharmaceutical compositions and crop protection compositions, preferably selected from the group consisting of perfume compositions, body care compositions, products for oral or dental hygiene, hygiene products, cleaning compositions, textile detergent compositions, compositions for fragrance dispensers and crop protection compositions.

15. A composition comprising a 1, 4-butanediol mono-or diester of formula (I) as defined in any one of claims 1 to 10 or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I), and at least one further component selected from the group consisting of an aromatic chemical other than compound (I), a non-aromatic chemical carrier, an antioxidant and a deodorant active; and in particular selected from the group consisting of aromatic chemicals other than compound (I), surfactants, oil components, solvents, antioxidants and deodorant actives;

wherein the composition is not an alcoholic beverage, juice, fruit or seed, wherein the composition does not comprise diacetyl; and wherein the composition does not comprise 1, 3-bis (caprolactam-1-yl) butane.

16. The composition according to claim 15, wherein where the non-aromatic chemical carriers comprise one or more solvents selected from the group consisting of ethanol, isopropanol, dipropylene glycol (DPG), propylene glycol, 1, 2-butanediol, glycerol, diethylene glycol monoethyl ether, diethyl phthalate (DEP), isopropyl myristate (IPM), triethyl citrate (TEC), benzyl benzoate, and mixtures thereof.

17. The composition according to claim 16, wherein the solvents are selected from the group consisting of isopropanol, dipropylene glycol (DPG), propylene glycol, 1, 2-butanediol, diethylene glycol monoethyl ether, diethyl phthalate (DEP), isopropyl myristate (IPM), triethyl citrate (TEC), benzyl benzoate, and mixtures thereof.

18. The composition according to claim 17, wherein the solvents are selected from the group consisting of isopropyl alcohol, isopropyl myristate (IPM), triethyl citrate (TEC), benzyl benzoate, and mixtures thereof.

19. The composition according to any one of claims 15 to 18, wherein the aroma chemicals different from compound (I) are selected from the group consisting of: geranyl acetate, α -hexylcinnamaldehyde, 2-phenoxyethyl isobutyrate, dihydromyrcenol, methyl dihydrojasmonate (preferably having a cis isomer content of more than 60 wt.%), 4,6,7, 8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta [ g ] benzopyran, tetrahydrolinalool, ethyl linalool, benzyl salicylate, 2-methyl-3- (4-tert-butylphenyl) propanal, cinnamyl alcohol, 4, 7-methano-3 a,4,5,6,7 a-hexahydro-5-indenyl ester of acetic acid, 4, 7-methano-3 a,4,5,6,7 a-hexahydro-6-indenyl ester of acetic acid, citronellol, citronellyl acetate, tetrahydrogeraniol, vanillin, linalool acetate, linalyl acetate storax acetate, octahydro-2, 3, 8-tetramethyl-2-naphtalenoethyl, 2-acetyl-1,2,3,4,6,7,8-octahydro-2, 3, 8-tetramethylnaphthalene, hexyl salicylate, 4-tert-butylcyclohexyl acetate, 2-tert-butylcyclohexyl acetate, alpha-ionone, alpha-n-methylionone, alpha-isomethyl ionone, coumarin, terpineol acetate, 2-phenylethanol, 4- (4-hydroxy-4-methylpentyl) -3-cyclohexene carbaldehyde, alpha-amyl cinnamaldehyde, ethylene brassylate, (E) -3-methylcyclopentadec-5-enone, (Z) -3-methylcyclopentadec-5-enone, 15-pentadec-11-enolide, 15-pentadec-12-enolide, 15-cyclopentadecanolide, 1- (5, 6,7, 8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthyl) ethanone, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, 2-ethyl-4- (2, 3-trimethyl-3-cyclopenten-1-yl) -2-buten-1-ol, cis-3-hexenyl acetate, trans-2/cis-6-nonylenol, 2, 4-dimethyl-3-cyclohexenecarboxaldehyde, 2,4, 7-tetramethyloct-6-en-3-one, 2, 6-dimethyl-5-hepten-1-al, borneol 3- (3-isopropylphenyl) butanal, 2-methyl-3- (3, 4-methylenedioxyphenyl) propanal, 3- (4-ethylphenyl) -2, 2-dimethylpropionaldehyde, 7-methyl-2H-1, 5-benzodioxepan-3 (4H) -one, 3, 5-trimethylcyclohexyl acetate (preferably having a cis isomer content of 70wt.% or more), 2, 5-trimethyl-1, 2,3, 4a,5,6, 7-octahydronaphthalene-2-ol, 3- (4-tert-butylphenyl) -propanal, ethyl 2-methylpentanoate, ethoxymethoxycyclododecane, 2, 4-dimethyl-4, 4a,5,9 b-tetrahydroindeno [1,2-d ] [1,3] dioxin, 2-t-butylcyclohexyl acetate, 3- [5, 6-trimethylbicyclo [2.2.1] hept-2-yl ] cyclohex-1-ol, menthone, isomenthone, carvone, camphor, beta-ionone, beta-n-methyl ionone, beta-isomethyl ionone, alpha-irone, alpha-damascone, beta-damascone, delta-damascone, acetylated cedar wood oil, and mixtures thereof.

20. The composition according to any one of claims 15 to 17, selected from the group consisting of perfume compositions, body care compositions, products for oral or dental hygiene, hygiene products, cleaning compositions, textile detergent compositions, compositions for fragrance dispensers and crop protection compositions.

21. A process for preparing a fragrance chemical composition, in particular a perfuming composition, especially a perfuming ready-to-use composition, which comprises incorporating into said composition a 1, 4-butanediol mono-or diester of formula (I) as defined in any one of claims 1 to 10, or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I); or mixing 1, 4-butanediol mono-or di-esters of formula (I) as defined in any one of claims 1 to 10 or a mixture of different 1, 4-butanediol mono-and/or di-esters of formula (I) simultaneously or continuously with the other components of the composition or with a preformed mixture of a part of the other components of the composition.

22. A process for imparting a fragrance, preferably flavour, to a composition, which process comprises incorporating into the composition a 1, 4-butanediol mono-or diester of formula (I) as defined in any one of claims 1 to 10 or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I); or comprises mixing 1, 4-butanediol mono-or diester of formula (I) as defined in any one of claims 1 to 10 or a mixture of different 1, 4-butanediol mono-and/or diesters of formula (I) simultaneously or continuously with the other components of the composition or with a preformed mixture of a part of the other components of the composition.