Enol Ether Pro Fragrance

Abstract

The present invention relates to enol ether compounds of formula (I) as pro-perfume compounds. In particular, the present invention relates to a method for releasing compounds which are aldehyde compounds of formula (II), formates of formula (III) and / or alcohols of formula (IV) by exposing the enol ether compounds of formula (I) to an oxidizing environment. Furthermore, the present invention relates to perfuming compositions and perfumed consumer products comprising at least one enol ether compound of formula (I).

Description

[Technical field]

[0001] The present invention relates to compounds of formula (I) as properfume compounds. In particular, the present invention relates to a method for releasing compounds which are aldehyde compounds of formula (II), formates of formula (III) and / or alcohols of formula (IV) by exposing the compounds of formula (I) to an oxidizing environment. Furthermore, the present invention relates to perfumed compositions and perfumed consumer products comprising at least one compound of formula (I).

[0002] Background technology The perfume industry is particularly interested in compositions or additives that can extend or enhance the perfume effect of at least one perfume ingredient for a certain period of time. It is particularly desirable to obtain long-lasting effects for standard perfume raw materials that are too volatile or not long-lasting enough by themselves or that only deposit in small amounts on the surfaces of the final application. Furthermore, some perfume ingredients are unstable and need to be protected against slow degradation before their use. Long-lasting perfumes are desirable for various applications, such as refined or functional perfume or cosmetic preparations. The cleaning and softening of textiles is a particular field in which it is always required to make it possible to make the effect of active substances, in particular perfumes or perfume compositions, effective for a certain period of time after cleaning, softening and drying. Indeed, it is known that many active substances that are particularly suitable for this type of application do not stick to the laundry or do not remain on the laundry when rinsed, so that the perfume effect is only short-lived and not very strong. Regarding the importance of this type of application in the perfume industry, research in this field continues, especially with the aim of finding new and more effective solutions to the problems mentioned above.

[0003] WO2019243501 discloses an enol ether that can efficiently release aryl aldehydes, formates and alcohols. However, this type of enol ether is very difficult to access, and the enol ether cannot release alkyl aldehydes.

[0004] It has surprisingly been found that the enol ether compounds according to the invention allow for an efficient preparation which allows for the release of alkyl aldehyde compounds of formula (II) while still efficiently releasing compounds which are formates of formula (III) and / or alcohols of formula (IV).

[0005] Detailed Description of the Invention Olfaction is a complex and dynamic process, and controlling the release profile of volatile fragrance compounds can maximize the impact of a fragrance formulation and enrich the sensory experience. Pro-fragrances, such as the compounds of the present invention, add a degree of control and long-lastingness to the release profile of highly volatile perfume raw materials (PRMs), such as alkyl aldehydes, a highly sought-after and important class of compounds in the perfumery field.

[0006] Without intending to be limited to a particular theory, the compounds of the present invention may achieve their effect on the olfactory properties of a perfumed composition by tethering the PRM to a molecular anchor and requiring a specific reaction mechanism to release the volatile PRM from this anchor under specific environmental conditions. In the present invention, the release of one, two or up to three PRMs is stimulated by oxidation when the pro-fragrance is exposed to oxygen in the ambient air.

[0007] As used herein, from a precursor compound, a) An aldehyde compound of formula (II) [ka] [In the formula, R 1 is C 1-8 Alkyl group, C 1-8 Alkoxy groups, hydroxy groups, carboxylic acid groups and / or C 1-4 a hydroxy group, each optionally substituted with one or more carboxylic acid ester groups, C 1-15 Alkyl group, C 2-15 Alkenyl group, C 1-15 Alkoxy group, C 2-15Alkenyloxy group, C 3-15 Cycloalkyl groups, C 5-15 Cycloalkenyl group, C 3-15 Heterocycloalkyl group, carboxylic acid group, C 1-4 Carboxylic acid ester group, C 6-10 Aryl groups and / or C 6-10 each optionally substituted with one or more aryloxy groups, 1-15 Alkyl group, C 3-15 Alkenyl group, C 3-15 Cycloalkyl groups, C 5-15 Cycloalkenyl group or C 3-14 is a heterocycloalkyl group. b) a formate of formula (III) [ka] [In the formula, R 2 C optionally containing one, two or three oxygen atoms 1-18 a hydrocarbon group, except for an ester functional group alpha to a formyloxy group. c) an alcohol of formula (IV) [ka] [In the formula, R 2 have the same meaning as defined above. by exposing a precursor compound of formula (I) to an environment which oxidizes the compound, comprising The precursor compound is a compound of formula (I) [ka] [In the formula, R 1 and R 2 has the same meaning as defined above] in the form of any one of its stereoisomers or a mixture thereof.

[0008] The first object of the present invention is to produce a fluorine-containing compound by the synthesis of a fluorine-containing compound from a precursor compound, a) An aldehyde compound of formula (II) [ka] [In the formula, R 1 is C 1-8 Alkyl group, C 1-8 Alkoxy groups, hydroxy groups, carboxylic acid groups and / or C 1-4 a hydroxy group, each optionally substituted with one or more carboxylic acid ester groups, C 1-15 Alkyl group, C 2-15 Alkenyl group, C 1-15 Alkoxy group, C 2-15 Alkenyloxy group, C 3-15 Cycloalkyl groups, C 5-15 Cycloalkenyl group, C 3-15 Heterocycloalkyl group, carboxylic acid group, C 1-4 Carboxylic acid ester group, C 6-10 Aryl groups and / or C 6-10 each optionally substituted with one or more aryloxy groups, 1-15 Alkyl group, C 3-15 Alkenyl group, C 3-15 Cycloalkyl groups, C 5-15 Cycloalkenyl group or C 3-14 is a heterocycloalkyl group. b) a formate of formula (III) [ka] [In the formula, R 2 C optionally containing one or two oxygen atoms 4-18 Hydrocarbon radicals, except for the ester functional group alpha to the formyloxy group, and R 2 does not contain an allyl functional group] c) an alcohol of formula (IV) [ka] [In the formula, R 2 have the same meaning as defined above. by exposing a precursor compound of formula (I) to an environment which oxidizes the compound, comprising The precursor compound is a compound of formula (I) [ka] [In the formula, R 1 and R 2 has the same meaning as defined above] in the form of any one of its stereoisomers or a mixture thereof.

[0009] According to any one of the embodiments of the present invention, at least one of the compounds of formula (II), formula (III) or formula (VI) is an active compound.

[0010] By "active compound", "active volatile compound", "active volatile aldehyde, formate and / or alcohol" or similar terms, it is understood that the aldehyde, formate and / or alcohol compound can provide a benefit or effect to its surrounding environment. In particular, the "active compound" is selected from the group consisting of a perfuming component, a flavoring component, a malodor neutralizing component, an antibacterial component and an insect repellent or attractant component. Thus, to be considered as an "active compound", a compound should have at least one property that makes it useful as a perfuming component, a malodor neutralizing component, a flavoring component, an antibacterial component and / or an insect repellent or attractant.

[0011] The term "perfuming ingredient" is understood as a compound used as an active ingredient in a perfuming preparation or composition to impart a pleasant effect. In other words, a compound to be considered as a perfuming ingredient must be recognized by those skilled in the art of perfumery as being able to impart or modify the odor of the composition in a positive or favorable way, and not simply having one odor. Perfuming ingredients may impart additional benefits other than modifying or imparting an odor, such as persistence, blooming, malodor neutralization, antibacterial effect, antiviral effect, microbial stability, or pest control. The term "flavor imparting ingredient" is understood as being able to impart a taste to the taster's palette. The term "malodor neutralizing ingredient" is understood as being able to reduce the perception of malodors, i.e. odors that are unpleasant or unpleasant to the human nose. The term "antimicrobial ingredient" is understood as being able to kill microorganisms or reduce or prevent their growth and / or accumulation, and includes antibacterial, antibiotic, antifungal, antiviral, and antiparasitic ingredients. The term "insect attractant or repellent" is understood to mean a compound that has a positive or negative effect on insects. Examples of insect attractant or repellent ingredients can be found in the literature or other works of similar nature, for example: AM El-Sayed, The Pherobase 2005, http: / / www.pherobase.net.

[0012] According to the above and below embodiments of the present invention, the method according to the present invention is particularly useful when the active compound is a perfuming ingredient, i.e. a perfuming aldehyde compound, a formic acid ester and / or an alcohol. "Perfuming aldehyde compound, a formic acid ester and / or an alcohol" means a compound used in the perfume industry, i.e. a compound used as an active ingredient in a perfume preparation or composition to give a pleasant effect. In other words, such aldehyde compound, a formic acid ester and / or an alcohol to be considered as a perfuming ingredient must be recognized by those skilled in the art of perfumery as being able to give or modify the odor of the composition in a positive or favorable way, and not simply having one odor. Perfuming aldehyde compound, a formic acid ester and / or an alcohol can be of natural or synthetic origin. Many of these perfuming aldehyde compounds, formates and / or alcohols are in any case cited in the literature, for example in Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, by S. Arctander, or in its latest editions, or in other works of a similar nature, as well as in the abundant patent literature in the field of perfumery.

[0013] The term "perfuming aldehyde compounds, formate esters and / or alcohols" as described herein is also referred to as "perfuming compounds".

[0014] In particular, the present invention is carried out in exactly the same manner, regardless of the exact identity of the active aldehyde compounds, formates or alcohols. Thus, even if the present invention is further described herein below with specific reference to "perfuming compounds", the following embodiments are also applicable to other active aldehyde compounds, formates and / or alcohols (i.e., the expression "perfuming" can be replaced, for example, with "flavoring", "malodor neutralizing", "antibacterial", "antimicrobial", "insect attractant" or "insect repellent").

[0015] The term "optionally" means that the particular group that is optionally substituted may or may not be substituted with the particular functional group. The term "one or more" is understood to mean substituted with 1 to 7, preferably 1 to 5, and more preferably 1 to 3 of a given functional group.

[0016] The terms "alkyl" and "alkenyl" are understood to include branched and straight chain alkyl and alkenyl groups. The terms "alkenyl" and "cycloalkenyl" are understood to include one, two or three olefinic double bonds, preferably one or two olefinic double bonds, with the proviso that cycloalkenyl groups are not aryl groups. The terms "cycloalkyl", "cycloalkenyl", "heterocycloalkyl" and "heterocyclic" are understood to include monocyclic or fused, spiro and / or bridged bicyclic or tricyclic cycloalkyl groups, cycloalkenyl groups, heterocycloalkyl groups and heterocyclic groups, preferably monocyclic cycloalkyl groups, cycloalkenyl groups and heterocycloalkyl groups. The term "alkoxy" is understood to be -OR', where R' is a straight, branched or cyclic alkyl group.

[0017] The term "aryl" is understood to include any group which contains at least one aromatic group, such as a phenyl group, an indenyl group, an indanyl group, a benzodioxolyl group, a dihydrobenzodioxinyl group, a tetrahydronaphthalenyl group or a naphthalenyl group.

[0018] With regard to "...hydrocarbon groups...", it is understood to mean that the group consists of hydrogen and carbon atoms and may be in the form of an aliphatic hydrocarbon, i.e. linear or branched, saturated hydrocarbon (e.g. alkyl group), linear or branched, unsaturated hydrocarbon (e.g. alkenyl or alkynyl group), saturated cyclic hydrocarbon (e.g. cycloalkyl) or unsaturated cyclic hydrocarbon (e.g. cycloalkenyl or cycloalkynyl), or in the form of an aromatic hydrocarbon, i.e. aryl group, or in the form of a mixture of said types of groups, e.g. a particular group may contain linear alkyl, branched alkenyl (e.g. branched alkenyl with one or more carbon-carbon double bonds), (poly)cycloalkyl and aryl moieties, unless a specific restriction to only one type is mentioned. Similarly, in all embodiments of the present invention, when it is stated that a group may be in the form of more than one type of topology (e.g. linear, cyclic or branched) and / or saturated or unsaturated (e.g. alkyl, aromatic or alkenyl), it is meant that the group may have any one of said topologies or contain moieties that are saturated or unsaturated as explained above.Similarly, in all embodiments of the present invention, when a group is in the form of one type of saturated or unsaturated (e.g. alkyl), it is meant that said group may have several moieties that are any type of topology (e.g. linear, cyclic or branched) or have different topologies.

[0019] The term "hydrocarbon radical optionally containing ..." is understood to mean that the hydrocarbon radical optionally contains one, two or three oxygen atoms in the form of an alcohol, ketone, aldehyde, ether, ester, carboxylic acid or carbonate group, which can be attached laterally to said hydrocarbon by replacing a hydrogen atom of the hydrocarbon radical or inserted into the hydrocarbon chain by replacing a carbon atom (where chemically possible) of the hydrocarbon radical. For example, the -CH2-CH2-CHOH-CH2- group denotes a C4 hydrocarbon group containing an alcohol group (substitution of a hydrogen atom), i.e. a C4 hydrocarbon group containing an oxygen atom, the -CH2-CH2-COO-CH2-CH2CH2-CH2- group denotes a C7 hydrocarbon group containing an ester group (substitution of a carbon atom / insertion into the hydrocarbon chain), i.e. a C7 hydrocarbon group containing two oxygen atoms, and similarly the -CH2-CH2-O-CH2-CH2-O-CH2-CH2- group denotes a C6 hydrocarbon group containing two ether groups, i.e. a C6 hydrocarbon group containing two oxygen atoms.

[0020] The term "alpha to the formyloxy group" is understood to mean the carbon next to the formyl group. 2 is C(R 2' )2C(=O)OR 2'' group (in the formula, R 2' and R 2'' are each independently a hydrogen atom or a C 1-17 For compounds of formula (IV), R 2 C optionally containing 1, 2 or 3 oxygen atoms 1-18 A hydrocarbon group, except for an ester functionality alpha to a hydroxy group.

[0021] With respect to the term "aryl functional group", the ordinary meaning understood by one skilled in the art is meant, namely, an optionally further substituted -CC=C- group.

[0022] For reasons of clarity, with regard to the expression "any one of its stereoisomers or a mixture thereof" or similar expressions, the usual meaning understood by a person skilled in the art is meant, i.e. that the compound of formula (I) may be a pure enantiomer or a diastereomer. In other words, the compound of formula (I) may have several stereocenters, each of which may have two different stereochemistries (e.g. R or S). The compound of formula (I) may be in the form of a pure enantiomer or even in the form of a mixture of enantiomers or diastereomers. The compound of formula (I) may be in racemic or scalemic form. Thus, the compound of formula (I) may be in the form of a stereoisomer or a composition of matter that comprises or consists of various stereoisomers.

[0023] According to any one of the above embodiments of the invention, said compound of formula (I) may be in the form of its E or Z isomer, or a mixture thereof, for example the invention includes a composition of matter consisting of one or more compounds of formula (I) having the same chemical structure, but differing by the configuration of the double bond. In particular, compound (I) may be in the form of a mixture consisting of isomers E and Z, wherein said isomer E represents at least 50% of the total mixture, or even at least 60%, or even at least 70%, or even at least 75% of the total mixture (i.e. a mixture E / Z composed of 75 / 25 to 100 / 0). Alternatively, compound (I) may be in the form of a mixture consisting of isomers E and Z, wherein said isomer Z represents at least 50% of the total mixture, or even at least 60%, or even at least 70%, or even at least 75% of the total mixture (i.e. a mixture E / Z composed of 25 / 75 to 0 / 100).

[0024] According to any one of the embodiments of the invention, the heterocycloalkyl group is a cycloalkyl containing at least one heteroatom, wherein the heteroatom represents one or more oxygen atoms.

[0025] According to any one of the embodiments of the present invention, R 1 C3-15 alkenyl, the double bond is 1 In other words, the compounds of formula (II) are not enals and the compounds of formula (I) are not dienol ethers.

[0026] According to any embodiment of the present invention, the compound of formula (I) is 18-36 Compounds, preferably C 20-36 It is a compound.

[0027] According to a particular embodiment of the present invention, R 1 is C 1-8 Alkyl group, C 1-8 a hydroxy group, each of which is optionally substituted with one or more alkoxy and / or hydroxy groups, C 1-15 Alkyl group, C 2-15 Alkenyl group, C 1-15 Alkoxy group, C 2-15 Alkenyloxy group, C 3-15 Cycloalkyl groups, C 5-15 Cycloalkenyl group, C 3-15 Heterocycloalkyl groups, C 6-10 Aryl groups and / or C 6-10 each optionally substituted with one or more aryloxy groups, 1-15 Alkyl group, C 3-15 Alkenyl group, C 3-15 Cycloalkyl groups, C 5-15 Cycloalkenyl group or C 3-14 In particular, R 1 is C 1-6 Alkyl group, C 1-6 a hydroxy group, each of which is optionally substituted with one or more alkoxy and / or hydroxy groups, C 1-10 Alkyl group, C 2-10 Alkenyl group, C 1-10 Alkoxy group, C 2-10 Alkenyloxy group, C 3-10 Cycloalkyl groups, C 5-10 Cycloalkenyl group, C 3-10 Heterocycloalkyl groups, C 6-10Aryl groups and / or C 6-10 each optionally substituted with one or more aryloxy groups, 1-12 Alkyl group, C 3-12 Alkenyl group, C 3-12 Cycloalkyl groups, C 5-12 Cycloalkenyl group or C 3-12 In particular, R 1 is a hydroxy group, C 1-4 Alkyl group and / or C 1-4 a hydroxy group, each optionally substituted with one or more alkoxy groups, C 1-4 Alkyl group, C 1-4 Alkoxy group, C 3-8 Cycloalkyl groups, C 5-8 each optionally substituted with one or more cycloalkenyl groups, C aryl groups and / or C aryloxy groups; 1-10 Alkyl group, C 3-10 Alkenyl group, C 3-11 Cycloalkyl group or C 5-11 In particular, R 1 is C 1-4 C optionally substituted with one or more alkoxy groups, 4-methoxyphenyl groups, and / or phenyl groups. 1-10 Alkyl group, C 3-10 In particular, R 1 are nonyl, decyl, undecyl, 2-undecyl, benzyl, dec-8-en-1-yl, dec-9-en-1-yl, 4-phenylbutan-2-yl, 4-(C 1-6 It may represent a 4-phenylbutan-2-yl or phenylethyl group. 1may represent a heptyl group, a nonyl group, a decyl group, a undecyl group, a 2-undecyl group, a benzyl group, a none-3-en-1-yl group, a none-8-en-1-yl group, a dec-8-en-1-yl group, a dec-9-en-1-yl group, a 4-phenylbutan-2-yl group, a 4-(tert-butyl)benzyl group, a 2-phenylpropyl-1-yl group, a 2-(4-methylcyclohex-3-en-1-yl)propyl group, a 2,6-dimethylhept-5-en-1-yl group, a 1-(4-(tert-butyl)phenyl)propan-2-yl group, a 2,4-dimethylcyclohex-3-en-1-yl group, a 2-(4,4-dimethylcyclohex-1-en-1-yl)ethyl group, a 4-phenylbutan-2-yl group or a phenylethyl group.

[0028] According to a particular embodiment of the present invention, R 1 may contain at least 5, 6 or 7 carbon atoms.

[0029] According to any one of the embodiments of the present invention, R 1 is not a 2-hexylidenecyclopentyl group.

[0030] Disclosed herein is R 2 C optionally containing 1 or 2 oxygen atoms 3-18 It may represent a hydrocarbon group. In particular, R 2 C, optionally containing one or two oxygen atoms 4-18 It may represent a hydrocarbon group.

[0031] According to any one of the embodiments of the present invention, R 2 C, optionally containing one or two oxygen atoms 5-18 It may represent a hydrocarbon group. In particular, R 2 C, optionally containing one or two oxygen atoms 6-18 It may represent a hydrocarbon group. In particular, R 2 C, optionally containing one or two oxygen atoms 6-18 may represent a hydrocarbon group, except that R 2 does not contain an aryl function. In particular, R 2 C, optionally containing one or two oxygen atoms6-18 may represent a hydrocarbon group, except that R 2 is not a benzyl group and does not contain an aryl function. 2 C, optionally containing one or two oxygen atoms 6-18 may represent a hydrocarbon group, except that R 2 is not a benzyl group or a cyclohexyl group or a 2-hydroxy-1,2-diphenylethyl group or a 1-(tert-butoxy)-7,7-dimethylbicyclo[2.2.1]heptan-2-yl group and does not contain an aryl function.

[0032] According to any one of the embodiments of the present invention, R 2 is not a benzyl group or a cyclohexyl group or a 2-hydroxy-1,2-diphenylethyl group or a 1-(tert-butoxy)-7,7-dimethylbicyclo[2.2.1]heptan-2-yl group and does not contain an aryl function.

[0033] According to any one of the embodiments of the present invention, R 2 contains at least 6 carbon atoms.

[0034] According to any one of the embodiments of the present invention, R 2 is C 1-8 Alkyl, C 1-8 a hydroxy group, each of which is optionally substituted with one or more of alkoxy, hydroxy and / or carboxylic acid; 1-15 Alkyl group, C 1-15 Alkoxy group, C 3-15 Cycloalkyl groups, C 5-15 Cycloalkenyl group, C 6-10 Aryl groups and / or C 6-10 each optionally substituted with one or more aryloxy groups, 1-18 Alkyl group, C 2-18 Alkenyl group, C 3-18 Cycloalkyl group or C 5-18 In particular, R 2 is C 1-8 Alkyl, C 1-8a hydroxy group, each of which is optionally substituted with one or more of alkoxy, hydroxy and / or carboxylic acid; 1-15 Alkyl group, C 1-15 Alkoxy group, C 3-15 Cycloalkyl groups, C 5-15 Cycloalkenyl group, C 6-10 Aryl groups and / or C 6-10 each optionally substituted with one or more aryloxy groups, 1-15 Alkyl group, C 2-15 Alkenyl group, C 3-15 Cycloalkyl group or C 5-15 In particular, R 2 is C 1-6 Alkyl group, C 1-6 a hydroxy group, each of which is optionally substituted with one or more alkoxy and / or hydroxy groups, C 1-10 Alkyl group, C 1-10 Alkoxy group, C 3-10 Cycloalkyl groups, C 5-10 Cycloalkenyl group, C 6-10 Aryl groups and / or C 6-10 each optionally substituted with one or more aryloxy groups, 1-12 Alkyl group, C 3-12 Alkenyl group, C 3-12 Cycloalkyl group or C 5-12 In particular, R 2 is a hydroxy group, C 1-4 Alkyl group and / or C 1-4 a hydroxy group, each optionally substituted with one or more alkoxy groups, C 1-4 Alkyl group, C 1-4 Alkoxy group, C 3-8 Cycloalkyl groups, C 5-8 each optionally substituted with one or more cycloalkenyl groups, C aryl groups and / or C aryloxy groups; 1-10 Alkyl group, C 3-10 Alkenyl group, C 3-11 Cycloalkyl group or C 5-11 In particular, R 2 is C 8-10Alkyl group, C with one olefinic double bond 6-10 It may represent an alkenyl group or a C2 alkyl group substituted with one phenyl group or a C6 aryloxy group. In particular, R 2 may represent an octyl group, a 2-phenoxyethyl group, a 3,7-dimethyloctyl group, an octan-2-yl group, an octan-3-yl group, a 3,7-dimethyloct-6-en-1-yl group, a (Z)-hex-3-en-1-yl group, a (Z)-oct-3-en-1-yl group or a 2-phenylethyl group. 2 may represent a 2-phenoxyethyl group or a 2-phenylethyl group.

[0035] According to any one of the embodiments of the present invention, R 2 is a hydroxy group, C 1-6 Alkyl group, C 2-6 Alkenyl group, C 1-6 Alkoxy group, C 2-6 Alkenyloxy group and / or -COOR 3 Group (where R 3 is C 1-6 Alkyl group, C 2-6 alkenyl and / or benzyl groups) 6-10 In particular, R 2 is a hydroxy group, C 1-4 Alkyl group, C 2-4 Alkenyl group, C 1-4 Alkoxy group, C 2-4 Alkenyloxy group and / or -COOR 3 Group (where R 3 is C 1-6 Alkyl group, C 2-6 In further detail, R may represent a C6 aryl optionally substituted with one or more of the following: 2 is a hydroxy group, C 1-3 Alkyl group, C 2-3 Alkenyl group, C 1-3 Alkoxy group, C 2-3 Alkenyloxy group and / or -COOR 3 Group (where R 3 is C1-6 Alkyl group, C 2-6 It may represent a C6 aryl optionally substituted with one or more of an alkenyl group and / or a benzyl group.

[0036] According to a particular embodiment, at least one of the compounds of formula (II), formula (III) and formula (IV) is an active compound. Still further, the compound of formula (II) is an active compound.

[0037] According to a particular embodiment, the aldehyde compound of formula (II) and / or the active alcohol of formula (IV) are perfuming ingredients. It is also clear to the skilled person that the compounds of formula (II), formula (III) and formula (IV) according to the invention are essentially volatile compounds.

[0038] The aldehyde compounds, formates and / or alcohols may be advantageously characterized by a vapor pressure of more than 1.0 Pa, as obtained by calculation using the software EPIwin v.3.10 (2000, available from the US Environmental Protection Agency). According to other embodiments, the vapor pressure of the ketones, formates and / or alcohols may be more than 5.0, or more than 7.0 Pa.

[0039] According to a particular embodiment, the compound of formula (I) is non-volatile. The compound of formula (I) may be advantageously characterized by a vapor pressure of less than 0.01 Pa, as obtained by calculating using the software EPIwin v.3.10 (2000, available from the United States Environmental Protection Agency). According to a preferred embodiment, the vapor pressure is less than 0.001 Pa.

[0040] According to a particular embodiment, the aldehyde compound of formula (I) is hexanal, heptanal, octanal, nonanal, decanal, undecanal, dodecanal, 2-ethylhexanal, 3,7-dimethyloctanal, 2-methyldecanal, 2-methylundecanal, 6-nonenal, 4-decenal, 5-octenal, 8-nonenal, 8-decenal, 9-decenal, 3-(3,3-dimethyl-2,3-dihydro-1H-inden-5-yl)propanal, 9-undecenal, 10-undecenal, aldehyde, 3-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)propanal, 4-dodecenal, 8-isopropyl-6-methylbicyclo[2.2.2]oct-5-ene-2-carbaldehyde, 3-(4-(tert-butyl)phenyl)propanal, 3-(4-(tert-butyl)phenyl)-2-methylpropanal, 2-methyl-4-phenylbutanal, 3-methyl-5-phenylpentanal, 4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde aldehyde, 2,4-dimethylcyclohex-3-en-1-carbaldehyde, 3-phenylbutanal, 2,6-dimethylhept-5-enal, 3-(4-methylcyclohex-3-en-1-yl)butanal, 3-(4,4-dimethylcyclohex-1-en-1-yl)propanal, 4-methyl-5-(p-tolyl)pent-4-enal, 3,7-dimethyloct-6-enal, 2-phenylpropanal, phenylacetaldehyde, 3-(benzo[d][1,3]dioxol-5-yl)-2-methyl Propanal, 5-methoxyoctahydro-1H-4,7-methanoindene-1-carbaldehyde, 6-methoxyoctahydro-1H-4,7-methanoindene-1-carbaldehyde, 3-(3-isopropylphenyl)butanal, 3-(4-isobutyl-2-methylphenyl)propanal, 3,6-dimethylcyclohex-3-ene-1-carbaldehyde, 2-((3,7-dimethyloct-6-en-1-yl)oxy)acetaldehyde, 3-(4-ethylphenyl)-2,2-dimethylpropanal, 3,5,6-Trimethylcyclohex-3-ene-1-carbaldehyde, 4-(4-methylpent-3-en-1-yl)cyclohex-3-ene-1-carbaldehyde, 3-phenylpropanal, 3-(4-isopropylphenyl)-2-methylpropanal, 8,8-dimethyl-1,2,3,4,6,7,8,8a-octahydronaphthalene-2-carbaldehyde, 2-methyl-4-(2,2,3-trimethyl ethylcyclopent-3-en-1-yl)pent-4-enal), 3,5,5-trimethylhexanal, 2,6,10-trimethyl-9-undecenal, 3-(4-methoxyphenyl)-2-methylpropanal, 7-hydroxy-3,7-dimethyloctanal, 3-(4-isopropylphenyl)propanal, 2-(4-isopropylphenyl)acetaldehyde, 2-(4-(tert- butyl)phenyl)acetaldehyde, 6-methoxy-2,6-dimethylheptanal, 2,6-dimethyl-5-heptenal, 3-(4-isopropylcyclohex-1-en-1-yl)propanal, 3-(4-isopropylcyclohexylidene)propanal, 2,4-dimethyl-3-cyclohexene-1-carbaldehyde, 3-(3-isopropylcyclohex-1-en-1-yl)propanal aldehyde, 3-(5-isopropylcyclohex-1-en-1-yl)propanal, 4-(4-methyl-3-pentenyl)-3-cyclohexene-1-carbaldehyde, 5-cyclohexyl-2,4-dimethyl-4-pentenal, 5,9-dimethyl-4-decenal, and 1-methyl-4-(4-methyl-3-pentenyl)-3-cyclohexene-1-carbaldehyde.

[0041] In particular, the aldehyde compounds of formula (II) are octanal, nonanal, decanal, undecanal, dodecanal, 2-methyldecanal, 2-methylundecanal, 2-phenylpropanal, 2-methyl-4-phenylbutanal, phenylacetaldehyde, 2-(4-(tert-butyl)phenyl)acetaldehyde, phenylacetaldehyde, 4-decenal, 4-dodecenal, 9-decenal, 9-undecenal, 10-undecenal, 2,6-dimethyl-5-heptanal, 2,4-dimethyl-3-cyclohexene-1-carbaldehyde, 3-phenylbutanal, 3-(4,4-dimethylcyclohexene-1-carbaldehyde, 4-phenylbutanal ... 1-en-1-yl)propanal, 4-(4-methylpent-3-en-1-yl)cyclohex-3-ene-1-carbaldehyde, 3-(3,3-dimethyl-2,3-dihydro-1H-inden-5-yl)propanal, 3-(4-methylcyclohex-3-en-1-yl)butanal, 3-(6,6-dimethylbicyclo[3.1.1]hept-2-en-3-yl)propanal, 8-isopropyl-6-methylbicyclo[2.2.2]oct-5-ene-2-carbaldehyde, 3-(4-(tert-butyl)phenyl)-2-methylpropanal, and 3,7-dimethyloct-6-enal.

[0042] According to a particular embodiment, the formate of formula (III) is butyl formate, pentyl formate, 2-methylbutyl formate, 3-methylbutyl formate, butan-2-yl formate, 2-methylpropyl formate, cyclohexyl formate, hexyl formate, heptyl formate, octyl formate, nonyl formate, decyl formate, undecyl formate, dodecyl formate, tridecyl formate, tetradecyl formate, 2-hexyl formate, 3-hexyl formate, 3-octyl formate, 2- Octyl formate, 3-octen-1-yl formate, benzyl formate, 9-decen-1-yl formate, 3,7-dimethyloctyl formate, 3,7-dimethyloct-6-enyl formate, 3,7-dimethyloct-7-enyl formate, 4-methoxybenzyl formate, 3-hexenyl formate, 3,5,5-trimethylhexyl formate, 2-phenylethyl formate, 2-(phenoxy)ethyl formate, 3-phenylpropyl formate, 2-phenylpropan-1-yl formate, 1-phenylethyl formate formate, 4-phenylbutanyl formate, (Z)-6-nonen-1-yl formate, bornyl formate, isobornyl formate, cedryl formate, cyclododecyl formate, decahydronaphthalen-2-yl formate, menthyl formate, 5-methyl-2-(prop-1-en-2-yl)cyclohexyl formate, 3-methyl-5-phenylpentanyl formate, (4-isopropylcyclohexyl)menthanyl formate, 2-pentyl-1-cyclopentyl formate, 5-ethyl-2-nonyl formate, (4-t ert-butyl)cyclohexyl formate, 2-methoxy-4-propylcyclohexyl formate, 3a,4,5,6,7,7a-hexahydro-1H-4,7-menthanoinden-5-yl formate, 3a,4,5,6,7,7a-hexahydro-1H-4,7-menthanoinden-6-yl formate, 1-(3,3-dimethylcyclohexyl)ethyl formate, 2-methyl-1-phenylpropan-2-yl formate, 2,6-dimethyloct-7-en-2-yl formate, 2,6-dimethyloctan-2-yl formate, 3,7-dimethyloctanyl formate, 4-cyclohexyl-2-methyl-2-butanyl formate, (2,5-dimethyl-2,3-dihydro-1H-inden-2-yl)methanyl formate, 1-((2-(tert-butyl)cyclohexyl)oxy)butan-2-yl formate, 1-((1RS,6SR)-2,2,6-trimethylcyclohexyl)hexan-3-yl formate, 2,6-dimethyl-2-heptanol, 2-methyl-4-[(1R)-2,2,3-trimethyl-3-cyclopenten-1-yl]-4-penten-1-yl formate, 2-methyl-1-phenylpropan-2-yl formate, (1RS,2SR,5RS)-2-isopropyl-5-methylcyclohexyl formate and 4-methyl-6-phenyl-2-hexanyl formate. ,

[0043] In a more specific embodiment, the formate of formula (III) is 2-phenylethyl formate, 3-hexenyl formate, octyl formate, decyl formate, 3,7-dimethyloct-6-en-1-yl formate, 3,7-dimethyloct-7-enyl formate, 2-phenoxyethyl formate, hexyl formate, benzyl formate, octan-3-yl formate, octan-2-yl formate, (1RS,2SR,5RS)-2-isopropyl-5-methyl formate, octyl ... -methylcyclohexyl formate, cyclododecyl formate, 1-(3,3-dimethylcyclohexyl)ethyl formate, 1-((2-(tert-butyl)cyclohexyl)oxy)butan-2-yl formate, 2,6-dimethyloct-7-en-2-yl formate, 3,7-dimethyloctan-3-yl formate, 2-methyl-1-phenylethylpropan-2-yl formate, and 2,6-dimethylheptan-2-yl formate.

[0044] In certain embodiments, the alcohol of formula (IV) is butanol, pentanol, 2-methylbutanol, 3-methylbutanol, butan-2-ol, 2-methylpropanol, cyclohexanol, hexanol, heptanol, octanol, nonanol, decanol, 1-undecanol, 1-dodecanol, 1-tridecanol, 1-tetradecanol, 2-hexanol, 3-hexanol, 3-octanol, 2-octanol, 3-octenol, benzyl alcohol, 9-decen-1-ol, 3,7-decen-1-ol, 3,8-decen-1-ol, 3, ... -Dimethyloctan-1-ol, 3,7-dimethyloct-6-en-1-ol, 3,7-dimethyloct-7-en-1-ol, 4-methoxybenzyl alcohol, 3-hexen-1-ol, 3,5,5-trimethylhexanol, 2-phenylethanol, 2-(phenoxy)ethanol, 3-phenylpropanol, 2-phenylpropan-1-ol, 1-phenylethan-1-ol, 4-phenylbutan-2-ol, (Z)-6-nonen-1-ol, borneol, isoborneol, cedrol , cyclododecanol, decahydronaphthalen-2-ol, menthol, 1-phenylethanol, 5-methyl-2-(prop-1-en-2-yl)cyclohex-1-ol, 3-methyl-5-phenylpentan-1-ol, (4-isopropylcyclohexyl)methanol, 2-pentyl-1-cyclopentanol, 5-ethyl-2-nonanol, 4-(tert-butyl)cyclohexan-1-ol, 2-methoxy-4-propylcyclohexan-1-ol, 3a,4,5,6,7,7a-hexahydro- 1H-4,7-menthanoinden-5-ol, 3a,4,5,6,7,7a-hexahydro-1H-4,7-menthanoinden-6-ol, 1-(3,3-dimethylcyclohexyl)ethanol, 2-methyl-1-phenylpropan-2-ol, 3,7-dimethylocta-1,6-dien-3-ol, 2,6-dimethyloct-7-en-2-ol, 2,6-dimethyloctan-2-ol, 3,7-dimethyloctan-3-ol, 4-cyclohexyl-2-methyl-2-butanol, (2,5-dimethyl-2,3-dihydro-1H-inden-2-yl)methanol, 1-((2-(tert-butyl)cyclohexyl)oxy)butan-2-ol, 1-((1RS,6SR)-2,2,6-trimethylcyclohexyl)hexan-3-ol, 2,6-dimethyl-2-heptanol, 2-methyl-4-[(1R)-2,2,3-trimethyl-3-cyclopenten-1-yl]-4-penten-1-ol, 2-methyl-1-phenylpropan-2-ol, (1RS,2SR,5RS)-2-isopropyl-5-methylcyclohexanol and 4-methyl-6-phenyl-2-hexanol.

[0045] In a more preferred embodiment, the alcohol of formula (IV) is selected from the group consisting of 1-hexanol, 1-heptanol, 1-octanol, 1-nonanol, 2-octanol, 3-octanol, 1-decanol, 1-undecanol, 1-dodecanol, benzyl alcohol, 3,7-dimethyloct-6-en-1-ol, 3,7-dimethyloct-7-en-1-ol, 3,7-dimethyloctan-1-ol, 3-hexen-1-ol, 3-octen-1-ol, 2-phenylethanol, 2-(phenoxy)ethanol, 9-decen-1-ol, 2,6-dimethyloct-7-en-2-ol, (2,5-dimethyl-2,3-dihydro-1H-inden-2-yl)methanol, and cyclododecanol.

[0046] According to a particular embodiment, the compound of formula (I) is (2-(non-1-en-1-yloxy)ethyl)benzene, (2-(undec-1-en-1-yloxy)ethyl)benzene, (2-(dodec-1-en-1-yloxy)ethyl)benzene, (2-(tridec-1-en-1-yloxy)ethyl)benzene, (2-(undeca-1,10-dien-1-yloxy)ethyl)benzene, ((3-phenethoxyallyl)benzene), (4-phenethoxybut-3-en-2-yl)benzene, (3-methyl-5-phenethoxypent-4-ene- 1-yl)benzene, 1-(octyloxy)dodec-1-ene, 1-(decyloxy)dodec-1-ene, 1-(hex-3-en-1-yloxy)dodec-1-ene, 1-((3,7-dimethyloct-6-en-1-yl)oxy)dodec-1-ene, 1-((3,7-dimethyloctyl)oxy)undec-1-ene, 1-((3,7-dimethyloct-6-en-1-yl)oxy)non-1-ene, (2-(undec-1-en-1-yloxy)ethoxy)benzene, (2-(dodec-1-en-1-yloxy)ethoxy)benzene, 1-(octan-2-yloxy)dodec-1-ene, 1-(tert-butyl)-4-(3-phenethoxyallyl)benzene, (2-((3-methylundec-1-en-1-yl)oxy)ethyl)benzene, (2-((3-methyldodec-1-en-1-yl)oxy)ethoxy)benzene, (2-((3-methyldodec-1-en-1-yl)oxy)ethyl)benzene, 1-(hex-3-en-1-yloxy)-3-methyldodec-1-ene, 3-methyl-1-(oct-3-en-1-yloxy)dodec-1-ene, 3-methyl-1- (Octyloxy)dodec-1-ene, 3-methyl-1-(octan-3-yloxy)dodec-1-ene, 1-((3,7-dimethyloct-6-en-1-yl)oxy)-3-methyldodec-1-ene, 1-((3,7-dimethyloctyl)oxy)-3-methyldodec-1-ene, (((3-methyldodec-1-en-1-yl)oxy)methyl)benzene, (2-(dodeca-1,10-dien-1-yloxy)ethyl)benzene, 1-(hex-3-en-1-yloxy)dodeca-1,10-diene, 1-(octyloxy)dodeca-1,10-diene, 1-(decyloxy)dodeca-1,10-diene, 1-((3,7-dimethyloct-6-en-1-yl)oxy)dodeca-1,10-diene, (2-(dodeca-1,11-dien-1-yloxy)ethyl)benzene, 1-(octyloxy)dodeca-1,11-diene, 1-(decyloxy)dodeca-1,11-diene, 1-(octyloxy)tridec-1-ene, 1-(decyloxy)tridec-1 Lidec-1-ene, (5-phenethoxypent-4-en-2-yl)benzene, (2-((2-(2,4-dimethylcyclohex-3-en-1-yl)vinyl)oxy)ethyl)benzene, 1,1-dimethyl-6-(4-phenethoxybut-3-en-1-yl)-2,3-dihydro-1H-indene, 5-isopropyl-2-methyl-7-(2-phenethoxyvinyl)bicyclo[2.2.2]oct-2-ene , (2-(trideca-1,5-dien-1-yloxy)ethyl)benzene, (2-(undeca-1,5-dien-1-yloxy)ethyl)benzene, 1-(tert-butyl)-4-(4-phenethoxybut-3-en-1-yl)benzene, 1-(tert-butyl)-4-(2-methyl-4-phenethoxybut-3-en-1-yl)benzene, (2-((3,7-dimethylocta-1,6-dien-1-yloxy)ethyl)benzene (2-((4,8-dimethylnona-1,7-dien-1-yl)oxy)ethyl)benzene, (2-((4-(4,4-dimethylcyclohex-1-en-1-yl)but-1-en-1-yl)oxy)ethyl)benzene and (2-((4-(4-methylcyclohex-3-en-1-yl)pent-1-en-1-yl)oxy)ethyl)benzene.

[0047] According to any one of the above embodiments, the aldehyde compound of formula (II), the formate ester of formula (III) and the alcohol of formula (IV) are released from the precursor compound of formula (I) through oxidation of the precursor compound of formula (I) under ambient conditions. Moreover, the precursor compound of formula (I) is oxidized under ambient conditions and in the absence of any catalyst. For reasons of clarity, with regard to the expression "ambient conditions" or similar expressions, the usual meaning understood by a person skilled in the art is meant, i.e., oxidation occurs at room temperature, in air, and under atmospheric pressure. In other words, the environment in which the compound is oxidized is air. Thereby, it is understood that the compound of formula (I) is oxidized in ambient air. In particular, it is understood that the compound of formula (I) does not require a pure oxygen environment, heat or a catalyst to be oxidized.

[0048] Without intending to be limited to a particular theory, the rate at which the precursor compound of formula (I) is oxidized may be faster than, equal to, or slower than the evaporation rate of the respective aldehyde compound of formula (II), the formate ester of formula (III), or the alcohol of formula (IV).

[0049] In some embodiments, the rate at which the precursor compound of formula (I) is oxidized, and thus the rate at which the individual aldehyde compound of formula (II), formate ester of formula (III), or alcohol of formula (IV) are released, enhances or prolongs the diffusion effect and / or perception of the characteristic fragrance of the at least one aldehyde compound of formula (II), at least one formate ester of formula (III) and / or at least one alcohol of formula (IV), as defined above.

[0050] In one embodiment, 100% of the compounds of formula (I) are oxidized in ambient air for a period ranging from 24 to 48 hours. Alternatively, 90% of the compounds of formula (I) are oxidized in ambient air for a period ranging from 24 to 48 hours. Alternatively, 80% of the compounds of formula (I) are oxidized in ambient air for a period ranging from 24 to 48 hours. Alternatively, 70% of the compounds of formula (I) are oxidized in ambient air for a period ranging from 24 to 48 hours. Alternatively, 60% of the compounds of formula (I) are oxidized in ambient air for a period ranging from 24 to 48 hours. Alternatively, 50% of the compounds of formula (I) are oxidized in ambient air for a period ranging from 24 to 48 hours. Alternatively, 40% of the compounds of formula (I) are oxidized in ambient air for a period ranging from 24 to 48 hours. Alternatively, 30% of the compounds of formula (I) are oxidized in ambient air for a period ranging from 24 to 48 hours. Alternatively, 20% of the compounds of formula (I) are oxidized in ambient air for a period ranging from 24 to 48 hours. Alternatively, 10% of the compounds of formula (I) are oxidized in ambient air for a period ranging from 24 to 48 hours. Alternatively, 9% of the compounds of formula (I) are oxidized in ambient air for a period ranging from 24 to 48 hours. Alternatively, 8% of the compounds of formula (I) are oxidized in ambient air for a period ranging from 24 to 48 hours. Alternatively, 7% of the compounds of formula (I) are oxidized in ambient air for a period ranging from 24 to 48 hours. Alternatively, 6% of the compounds of formula (I) are oxidized in ambient air for a period ranging from 24 to 48 hours. Alternatively, 5% of the compounds of formula (I) are oxidized in ambient air for a period ranging from 24 to 48 hours. Alternatively, 4% of the compounds of formula (I) are oxidized in ambient air for a period ranging from 24 to 48 hours. Alternatively, 3% of the compound of formula (I) is oxidized in ambient air for a period ranging from 24 to 48 hours. Alternatively, 2% of the compound of formula (I) is oxidized in ambient air for a period ranging from 24 to 48 hours. Alternatively, 1% of the compound of formula (I) is oxidized in ambient air for a period ranging from 24 to 48 hours.

[0051] The present invention also relates to a microcapsule comprising at least one compound of formula (I). In one embodiment, at least one compound of formula (I) is encapsulated in a core-shell microcapsule, where at least one compound of formula (I) is contained in a core covered by a shell. In one embodiment, the shell of the microcapsule protects the compound of formula (I) from the environment. The shell is composed of a material capable of releasing at least one compound of formula (I) and / or compounds of formula (II), (III) and / or (IV). In one embodiment, the shell is composed of a material capable of releasing the compound of formula (I) and / or compounds of formula (II), (III) and / or (IV) upon breakage of the shell and / or by diffusion through the shell. The skilled person is familiar with the processes for preparing said microcapsules. Thus, a microcapsule comprising at least one compound of formula (I) is one of the objects of the present invention.

[0052] In a preferred embodiment, encapsulation of the compound of formula (I) may provide an environment within the capsule that may oxidize all or a portion of the compound of formula (I), thereby releasing the respective aldehyde of formula (II), formate of formula (III) or alcohol of formula (IV). In a preferred embodiment, the shell of the microcapsule may act as a permeability barrier, preventing leakage of the respective aldehyde compound of formula (II), formate of formula (III) or alcohol of formula (IV) from the capsule.

[0053] According to certain embodiments, the shell of the microcapsule comprises a material selected from the group consisting of polyurea, polyurethane, polyamide, polyester, poly(meth)acrylate (i.e. polyacrylate and / or polymethacrylate), polysiloxane, polycarbonate, polysulfonamide, polymers of urea and formaldehyde, polymers of melamine and formaldehyde, polymers of melamine and urea, or polymers of melamine and glyoxal, and mixtures thereof. The shell may be hybrid, i.e. organic-inorganic, for example a hybrid shell composed of at least two types of inorganic particles that are crosslinked, or a shell resulting from a hydrolysis and condensation reaction of a polyalkoxysilane macromonomer composition.

[0054] According to certain embodiments, the core-shell microcapsules may be produced by different or more than one encapsulation method.

[0055] In preferred embodiments, the shells of the microcapsules may be selected, independently of one another, from the group of aminoplast, polyamide, polyester, polyurea and polyurethane shells and mixtures thereof.

[0056] In certain embodiments, the shell of the microcapsule comprises an aminoplast copolymer, such as melamine-formaldehyde or urea-formaldehyde or crosslinked melamine formaldehyde or melamine glioxal.

[0057] In certain embodiments, the shell of the microcapsule is polyurea-based, composed of, for example, but not limited to, an isocyanate-based monomer and an amine-containing crosslinker, such as guanidine carbonate and / or guanazole. Some polyurea microcapsules include a polyurea wall that is the reaction product of polymerization between at least one polyisocyanate containing at least two isocyanate functional groups and at least one reactant selected from the group consisting of amines (e.g., water-soluble guanidine salts and guanidine); a colloidal stabilizer or emulsifier; and an encapsulated fragrance. However, the use of amines can be omitted.

[0058] In certain embodiments, the colloidal stabilizer comprises an aqueous solution of 0.1% to 0.4% polyvinyl alcohol and 0.6% to 1% cationic copolymer of vinylpyrrolidone and quaternized vinylimidazole (all percentages defined by weight relative to the total amount of colloidal stabilizer). In certain embodiments, the emulsifier is an anionic or amphiphilic biopolymer, which may be selected from the group consisting of gum arabic, soy protein, gelatin, sodium caseinate, and mixtures thereof.

[0059] In certain embodiments, the microcapsule shell is polyurethane-based, composed of, for example, but not limited to, polyisocyanates and polyols, polyamides, polyesters, and the like.

[0060] In certain embodiments, the microcapsules have a polymeric shell resulting from complex coacervation, where the shell is possibly crosslinked.

[0061] In a particular embodiment of the core-shell microcapsules, the core-shell microcapsules comprise an oily core comprising a hydrophobic active agent, preferably at least one compound of formula (I), and a composite shell comprising a first material and a second material, wherein the first material and the second material are different, the first material being a coacervate and the second material being a polymeric material.

[0062] In certain embodiments, the mass ratio of the first material to the second material is from 50:50 to 99.9:0.1.

[0063] In a particular embodiment, the coacervate comprises a first polyelectrolyte, preferably selected from among proteins (e.g. gelatin), polypeptides or polysaccharides (e.g. chitosan), most preferably gelatin, and a second polyelectrolyte, preferably selected from alginates, cellulose derivatives, guar gum, pectinates, carrageenans, polyacrylic and methacrylic acids or xanthan gum, or even vegetable gums, such as acacia gum (e.g. gum arabic), most preferably gum arabic.

[0064] The first material of the coacervate can be chemically hardened using a suitable cross-linking agent, such as glutaraldehyde, glyoxal, formaldehyde, tannic acid or genipin, or can be enzymatically hardened using an enzyme, such as transglutaminase.

[0065] The second polymeric material may be selected from the group consisting of polyurea, polyurethane, polyamide, polyester, polyacrylate, polysiloxane, polycarbonate, polysulfonamide, polymers of urea and formaldehyde, polymers of melamine and formaldehyde, polymers of melamine and urea, or polymers of melamine and glyoxal, and mixtures thereof, preferably polyurea and / or polyurethane. The second material is preferably present in an amount of less than 3% by weight, preferably less than 1% by weight, based on the total weight of the microcapsule slurry.

[0066] The preparation of aqueous dispersions / slurries of core-shell microcapsules is well known to those skilled in the art. In certain embodiments, the microcapsule wall material may comprise any suitable resin, particularly melamine, glyoxal, polyurea, polyurethane, polyamide, polyester, and the like. Suitable resins include reaction products of aldehydes and amines, and suitable aldehydes include formaldehyde and glyoxal. Suitable amines include melamine, urea, benzoguanamine, glycoluril, and mixtures thereof. Suitable melamines include methylol melamine, methylated methylol amine, imino melamine, and mixtures thereof. Suitable ureas include dimethylol urea, methylated dimethylol urea, urea resorcinol, and mixtures thereof. Materials suitable for manufacturing are available from one or more of the following companies: Solutia Inc. (St Louis, Missouri USA), Cytec Industries (West Paterson, New Jersey USA), and Sigma-Aldrich (St. Louis, Missouri USA).

[0067] In certain embodiments of the core-shell microcapsules, the core-shell microcapsules are an oily core comprising a hydrophobic active substance, preferably at least one compound of formula (I), - optionally an inner shell composed of polymerized multifunctional monomers; - a biopolymer shell comprising proteins, wherein at least one of the proteins is crosslinked. Includes.

[0068] According to a particular embodiment, the protein is selected from the group consisting of milk proteins, caseinates such as sodium or calcium caseinate, casein, whey proteins, hydrolyzed proteins, gelatin, gluten, pea proteins, soy proteins, silk proteins and mixtures thereof, preferably sodium caseinate, most preferably sodium caseinate.

[0069] According to a particular embodiment, the proteins include sodium caseinate and globular proteins, preferably selected from the group consisting of whey proteins, beta-lactoglobulin, ovalbumin, bovine serum albumin, vegetable proteins, and mixtures thereof.

[0070] The protein is preferably a mixture of sodium caseinate and whey protein.

[0071] According to certain embodiments, the biopolymer shell comprises a cross-linked protein selected from the group consisting of sodium caseinate and / or whey protein.

[0072] According to certain embodiments, the microcapsule slurry comprises: an oily core comprising a hydrophobic active substance, preferably at least one compound of formula (I), - an inner shell composed of polymerized multifunctional monomers, preferably polyisocyanates having at least two isocyanate functional groups; - a biopolymer shell comprising proteins, wherein at least one protein is crosslinked; - Optionally at least one outer mineral layer The microcapsule comprises at least one microcapsule comprising:

[0073] According to one embodiment, the sodium caseinate and / or whey protein are cross-linked proteins.

[0074] The mass ratio of sodium caseinate to whey protein is preferably 0.01-100, preferably 0.1-10, and more preferably 0.2-5.

[0075] In certain embodiments, the microcapsules are 1) combining a perfume oil with at least one polyisocyanate having at least two isocyanate functional groups to form an oil phase; 2) dispersing or dissolving an aminoplast resin and, optionally, a stabilizer in water to form an aqueous phase; 3) preparing an oil-in-water dispersion having an average droplet size of 1-100 microns by combining an oil phase and an aqueous phase; 4) carrying out a curing step to form the walls of the microcapsules; and 5) Optionally, drying the final dispersion to obtain dried core-shell microcapsules. and wherein the aminoplast core-shell microcapsules are one shell, obtained by a process comprising:

[0076] In certain embodiments, the core-shell microcapsules are formaldehyde-free capsules. A typical process for the production of aminoplast formaldehyde-free microcapsule slurry is: 1) The following: a) a polyamine component in the form of melamine or a mixture of melamine and at least one C1-C4 compound containing two NH2 functional groups, b) Glyoxal, C 4-6 A mixture of 2,2-dialkoxy-ethanols and optionally glyoxalates, with a ratio of glyoxal / C of 1 / 1 to 10 / 1. 4-6 an aldehyde component in the form of a mixture having a molar ratio of 2,2-dialkoxy-ethanol; c) Protonic acid catalyst preparing an oligomeric composition comprising or obtained by reacting together the reaction products of 2) The droplet size is between 1 and 600 microns, and a. Oily substances, b. aqueous medium; c. at least one oligomeric composition obtained in step 1 d. at least one cross-linking agent selected from the following: i. C4~C 12Aromatic or aliphatic diisocyanates or triisocyanates and their biurets, triuret, trimers, trimethylolpropane adducts and mixtures thereof, and / or ii. Formula Q-(Oxirane-2-ylmethyl) n Dioxirane or trioxirane compounds of the formula: [wherein n is 2 or 3 and Q is a C2-C6 group optionally containing 2 to 6 nitrogen and / or oxygen atoms] e. C1-C4 compounds optionally containing two NH2 functional groups preparing an oil-in-water dispersion comprising: 3) heating the dispersion. 4) Cooling the dispersion Includes.

[0077] The method is described in more detail in WO 2013 / 068255.

[0078] In certain embodiments of the core-shell microcapsules, the core-shell microcapsules are an oily core comprising a hydrophobic active substance, preferably at least one compound of formula (I), and - below Acyl chloride a first amino compound, and A second amino compound A polyamide shell comprising or derived from The polyamide core-shell polyamide microcapsule comprises:

[0079] According to certain embodiments, the polyamide core-shell microcapsules are an oily core comprising a hydrophobic active substance, preferably at least one compound of formula (I), and A polyamide shell comprising: acyl chloride, preferably in an amount of 5-98%, preferably 20-98%, more preferably 30-85% (w / w); a first amino compound, preferably in an amount of 1 to 50% (w / w), preferably 7 to 40% (w / w), a second amino compound, preferably in an amount of 1 to 50% (w / w), preferably 2 to 25% (w / w), A stabilizer, preferably a biopolymer, preferably in an amount of 0-90%, preferably 0.1-75%, more preferably 1-70%. A polyamide shell comprising or derived from Includes.

[0080] According to certain embodiments, the polyamide core-shell microcapsules are an oily core comprising a hydrophobic active substance, preferably at least one compound of formula (I), and a polyamide shell comprising: Acyl chlorides, a first amino compound which is an amino acid, preferably an amino acid selected from the group consisting of L-lysine, L-arginine, L-histidine, L-tryptophan and / or mixtures thereof, a second amino compound selected from the group consisting of ethylenediamine, diethylenetriamine, cystamine and / or mixtures thereof, A biopolymer selected from the group consisting of casein, sodium caseinate, bovine serum albumin, whey protein, and / or mixtures thereof. or a polyamide shell obtained therefrom. Includes.

[0081] The first amino compound can be different from the second amino compound.

[0082] Typically, the method for producing polyamide-based microcapsules comprises the following steps: a) dissolving at least one acyl chloride in a hydrophobic material, preferably a fragrance, to form an oil phase; b) dispersing the oil phase obtained in step a) into an aqueous phase containing a first amino compound to form an oil-in-water emulsion; c) carrying out a curing step to form polyamide microcapsules in the form of a slurry. wherein a stabilizer is added in the oil phase and / or in the water phase and at least one second amino compound is added to the water phase before the formation of the oil-in-water emulsion and / or to the oil-in-water emulsion obtained after step b).

[0083] In certain embodiments, the shell of the microcapsule is polyurea- or polyurethane-based. Examples of polyurea-based and methods for producing polyurea-based microcapsule slurries are described, for example, in WO 2007 / 004166, EP 2300146, and EP 2579976. Typically, the method for producing a polyurea- or polyurethane-based microcapsule slurry includes the steps of: a) dissolving at least one polyisocyanate having at least two isocyanate groups in oil to form an oil phase; b) preparing an aqueous solution of an emulsifier or colloidal stabilizer to form an aqueous phase; c) adding an oil phase to an aqueous phase to form an oil-in-water dispersion having an average droplet size of 1-500 μm, preferably 5-50 μm; and d) applying conditions sufficient to induce interfacial polymerization and form microcapsules in the form of a slurry. Includes.

[0084] In a particular embodiment, the microcapsules may be in the form of a powder, in particular obtained by subjecting the microcapsule slurry to drying, such as spray drying, to provide the microcapsules as such, i.e. in the form of a powder. It is understood that any standard method known to those skilled in the art for carrying out such drying may be applied. In particular, the slurry may be spray-dried, preferably in the presence of a polymeric carrier material, such as polyvinyl acetate, polyvinyl alcohol, dextrin, natural or modified starch, gum arabic, vegetable gum, pectin, xanthan, alginate, carrageenan, or cellulose derivative, to provide the microcapsules in the form of a powder.

[0085] However, other drying methods may also be mentioned, such as extrusion, plating, spray granulation, fluidized bed or drying at room temperature using materials (carriers, desiccants) that meet the specific criteria disclosed in WO 2017 / 134179.

[0086] In another aspect, the present invention relates to a method for imparting, enhancing, improving or modifying the odor characteristics of a perfuming composition, the air surrounding the perfuming composition, a surface or a perfumed article, said method comprising adding to the composition, the air or the article, or contacting the surface with or treating the surface with an effective amount of at least one compound of formula (I) as defined above. The term "surface" as used herein may refer to the skin, hair, fabric or hard surface of a user to which the perfume composition comprising or containing at least one compound of formula (I) is applied.

[0087] In another aspect, the present invention relates to a method for enhancing or sustaining the diffusion effect of the characteristic fragrance of at least one aldehyde compound of formula (II), at least one formate ester of formula (III) and / or at least one alcohol of formula (IV) as defined above, on a surface or on the air surrounding a perfuming composition, said surface or air being treated with at least one compound (I) as defined above or with a composition or article comprising at least one compound (I), under conditions conducive to allowing the release over time of at least one aldehyde compound of formula (II), at least one formate ester of formula (III) and / or at least one alcohol of formula (IV).

[0088] Furthermore, the present invention relates to a method for producing a i) at least one compound of formula (I) as defined above, ii) at least one ingredient selected from the group consisting of a perfume carrier and a perfume base; and iii) optionally at least one flavoring adjuvant; The present invention relates to a fragrance composition comprising:

[0089] By "perfume carrier" is meant herein a material that is practically neutral from the perfume point of view, i.e. does not significantly modify the organoleptic properties of the perfuming ingredients. Said carrier may be liquid or solid.

[0090] The liquid carrier may include, but is not limited to, emulsifying systems, i.e., solvent and surfactant systems, or solvents commonly used in perfumery.A detailed description of the nature and type of solvents commonly used in perfumery cannot be exhaustive.However, it includes, but is not limited to, the most commonly used solvents, such as butylene or propylene glycol, glycerol, dipropylene glycol and its monoethers, 1,2,3-propanetriyl triacetate, dimethyl glutarate, dimethyl adipate, 1,3-diacetyloxypropan-2-yl acetate, diethyl phthalate, isopropyl myristate, Abalyn® (rosin resin, available from Eastman), benzyl benzoate, benzyl alcohol, 2-(2-ethoxyethoxy)-1-ethanol, triethyl citrate, or mixtures thereof, or naturally occurring solvents, such as glycerol, or vegetable oils, such as palm oil, sunflower oil or linseed oil. With regard to compositions comprising both a fragrance carrier and a fragrance base, other fragrance carriers which may be suitable than those mentioned above may be ethanol, water / ethanol mixtures, limonene or other terpenes, isoparaffins such as those known under the trade name Isopar® (supplier: Exxon Chemical) or glycol ethers and glycol ether esters such as those known under the trade name Dowanol® (supplier: Dow Chemical Company), or hydrogenated castor oil such as those known under the trade name Cremophor® RH 40 (supplier: BASF).

[0091] Solid carrier is meant to denote a material capable of chemically or physically binding the perfume composition or some of the components of the perfume composition. Generally, such solid carriers are used to stabilize the composition or to adjust the rate of evaporation of the composition or some of its components. The use of solid carriers is currently used in the art, and the skilled person knows how to achieve the desired effect. However, as regards non-limiting examples of solid carriers, they may include absorbent gums or polymers or inorganic materials, such as porous polymers, cyclodextrins, dextrins, maltodextrins, wood materials, organic or inorganic gels, clays, gypsum talc or zeolites.

[0092] Other non-limiting examples of solid carriers may include encapsulating materials. Examples of such materials include wall-forming and plasticizing materials such as glucose syrup, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetate, polyvinyl alcohol, proteins or pectins, vegetable gums such as gum acacia (gum arabic), urea, sodium chloride, sodium sulfate, zeolites, sodium carbonate, sodium bicarbonate, clays, talc, calcium carbonate, magnesium sulfate, gypsum, calcium sulfate, magnesium oxide, zinc oxide, titanium dioxide, calcium chloride, potassium chloride, magnesium chloride, zinc chloride, carbohydrates, sugars such as sucrose, monosaccharides, disaccharides, trisaccharides and polysaccharides and derivatives such as chitosan, starch, cellulose, carboxymethyl methylcellulose, methylcellulose, Hydroxyethylcellulose, ethylcellulose, propylcellulose, polyols / sugar alcohols such as sorbitol, maltitol, xylitol, erythritol, isomalt, polyethylene glycol (PEG), polyvinylpyrrolidine (PVP), polyvinyl alcohol, acrylamides, acrylates, polyacrylic acid and related, maleic anhydride copolymers, amine functional polymers, vinyl ethers, styrene, polystyrene sulfonates, vinyl acids, ethylene glycol-propylene glycol block copolymers, vegetable gums, acacia gum, pectin, xanthan, alginates, carrageenan, citric acid or water soluble solid acids, fatty alcohols or fatty acids and mixtures thereof, or materials cited in references such as H. Scherz, Hydrokolloide: Stabilisatoren, Dickungs- und Geliermittel in Lebensmitteln, Band 2 der Schriftenreihe Lebensmittelchemie, Lebensmittelqualitaet, Behr's Verlag GmbH & Co., Hamburg, 1996.Encapsulation is a method well known to those skilled in the art and may be carried out by using techniques such as spray drying, coagulation or even extrusion, or may consist of overcoating encapsulation, including coacervation and complex coacervation techniques.

[0093] Non-limiting examples of solid carriers may include core-shell capsules with aminoplast, polyamide, polyester, polyurea or polyurethane type resins or mixtures thereof (all of the aforementioned resins are well known to those skilled in the art) using techniques such as phase separation processes induced by polymerization, by interfacial polymerization, by coacervation, or all of the aforementioned techniques (all of the aforementioned techniques are described in the prior art), optionally in the presence of polymeric stabilizers or cationic copolymers.

[0094] The resins may be prepared by polycondensation of aldehydes (e.g., formaldehyde, 2,2-dimethoxyethanol, glyoxal, glyoxylic acid or glycolaldehyde and mixtures thereof) with amines, such as urea, benzoguanamine, glycoluril, melamine, methylolmelamine, methylated methylolmelamine, guanazole, etc., and mixtures thereof. Alternatively, preformed resins, alkylated polyamines, such as those commercially available under the trade names Urac® (supplied by Cytec Technology Corp.), Cymel® (supplied by Cytec Technology Corp.), Urecoll® or Luracoll® (supplied by BASF) may be used.

[0095] Other resins are produced by polycondensation of polyols, such as glycerol, and polyisocyanates, such as the trimer of hexamethylene diisocyanate, the trimer of isophorone diisocyanate, or xylylene diisocyanate, or the biuret of hexamethylene diisocyanate, or the trimer of xylylene diisocyanate with trimethylolpropane (known under the trade name Takenate®, supplier: Mitsui Chemicals), especially the trimer of xylylene diisocyanate with the biuret of trimethylolpropane and hexamethylene diisocyanate.

[0096] Some of the productive literature on the encapsulation of perfumes by polycondensation of amino resins, i.e. melamine-based resins, with aldehydes includes those illustrated by articles such as those published in Acta Polymerica by K. Dietrich et al. (1989, Vol. 40, pp. 243, 325 and 683, and 1990, Vol. 41, p. 91). Such literature already describes the various parameters that affect the production of such core-shell microcapsules, according to the prior art methods that are explained in more detail and exemplified in the patent literature. U.S. Pat. No. 4,396,670 (Wiggins Teape Group Limited) is a suitable early example of such literature. Since then, many other authors have enriched the literature in this field, and while it is not possible to cover here all the developments that have been published, a general knowledge of encapsulation techniques is very important. Representative recent relevant literature disclosing suitable uses of such microcapsules is, for example, the article by H. Y. Lee et al. in the Journal of Microencapsulation (2002, Vol. 19, pp. 559-569), WO 01 / 41915, or also the article by S. Bone et al. in Chimia (2011, Vol. 65, pp. 177-181).

[0097] The term "perfume base" is understood to mean a composition comprising at least one perfuming co-ingredient.

[0098] Said perfuming co-ingredient is not a compound according to the present invention.Furthermore, the term "perfuming co-ingredient" is understood as a compound that is used in perfuming preparations or compositions to provide a pleasant effect, i.e. is used mainly for the purpose of providing or adjusting odor.In other words, such co-ingredient should be recognized by those skilled in the art to be considered as perfuming co-ingredient, as it can provide or modify the odor of the composition in a positive or favorable way, and does not simply have one odor.

[0099] The nature and type of perfuming co-ingredients present in said base, which in any case will not be exhaustive, do not warrant a more detailed description here, whereby a person skilled in the art can select said base on the basis of his general knowledge and according to any use or application and the organoleptic effect desired. In general terms, these perfuming co-ingredients belong to various chemical classes: alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpene hydrocarbons, nitrogen or sulfur heterocyclic compounds and essential oils, and they may be of natural or synthetic origin.

[0100] Mention may in particular be made of the perfuming co-ingredients customarily used in perfume formulations, such as: - aldehyde components: decanal, dodecanal, 2-methyl-undecanal, 10-undecanal, octanal, nonanal and / or nonenal; - Aromatic Herbal Ingredients: Eucalyptus Oil, Camphor, Eucalyptol, 5-Methyltricyclo[6.2.1.0 2,7 ]undecane-4-one, 1-methoxy-3-hexanethiol, 2-ethyl-4,4-dimethyl-1,3-oxathiane, 2,2,7 / 8,9 / 10-tetramethylspiro[5.5]undec-8-en-1-one, menthol and / or alpha-pinene; - Balsam components: coumarin, ethyl vanillin and / or vanillin; - citrus constituents, dihydromyricenol, citral, orange oil, linalyl acetate, citronellyl nitrile, orange terpenes, limonene, 1-p-menthen-8-yl acetate and / or 1,4(8)-p-menthadiene; - Floral Ingredients: Methyl Dihydrojasmonate, Linalool, Citronellol, Phenylethanol, 3-(4-tert-butylphenyl)-2-methylpropanal, Hexyl Cinnamaldehyde, Benzyl Acetate, Benzyl Salicylate, Tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol, Beta-Ionone, Methyl 2-(Methylamino)benzoate, (E)-3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one, (1E)-1-(2,6,6-trimethyl-2- cyclohexen-1-yl)-1-penten-3-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one, (2E)-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-buten-1-one, (2E)-1-[2,6,6-trimethyl-3-cyclohexen-1-yl]-2-buten-1-one, (2E)-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one, 2,5-dimethyl-2-indanmethanol, 2,6,6-trimethyl-3-cyclohexen Cyclohexene-1-carboxylate, 3-(4,4-dimethyl-1-cyclohexen-1-yl)propanal, hexyl salicylate, 3,7-dimethyl-1,6-nonadien-3-ol, 3-(4-isopropylphenyl)-2-methylpropanal, vergyl acetate, geraniol, p-mentha-1-en-8-ol, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate, 1,1-dimethyl-2-phenylethyl acetate, 4-cyclohexyl-2-methyl-2-butanol, amyl salicylate, high cis-methyl dihydroxide Rojasmonate, 3-methyl-5-phenyl-1-pentanol, virgyl propionate, geranyl acetate, tetrahydrolinalool, cis-7-P-methanol, propyl (S)-2-(1,1-dimethylpropoxy)propanoate, 2-methoxynaphthalene, 2,2,2-trichloro-1-phenylethyl acetate, 4 / 3-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbaldehyde, amylcinnamaldehyde, 8-decen-5-olide, 4-phenyl-2-butanone, isononyl acetate, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate, vergyl isobutyrate and / or a mixture of methyl ionone isomers; - fruity ingredients: gamma-undecalactone, 2,2,5-trimethyl-5-pentylcyclopentanone, 2-methyl-4-propyl-1,3-oxathiane, 4-decanolide, ethyl 2-methyl-pentanoate, hexyl acetate, ethyl 2-methylbutanoate, gamma-nonalactone, allylheptanoate, 2-phenoxyethyl isobutyrate, ethyl 2-methyl-1,3-dioxolane-2-acetate, 3-(3,3 / 1,1-dimethyl-5-indanyl)propanal, diethyl 1,4-cyclohexanedicarboxylate, 3-methyl-2-hexen-1-yl acetate, 1-[3,3-dimethylcyclohexyl]ethyl[3-ethyl-2-oxiranyl]acetate and / or diethyl 1,4-cyclohexanedicarboxylate; - green ingredients: 2-methyl-3-hexanone (E)-oxime, 2,4-dimethyl-3-cyclohexene-1-carbaldehyde, 2-tert-butyl-1-cyclohexyl acetate, styrallyl acetate, allyl (2-methylbutoxy)acetate, 4-methyl-3-decen-5-ol, diphenyl ether, (Z)-3-hexen-1-ol and / or 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one; - Musk ingredients: 1,4-dioxa-5,17-cycloheptadecanedione, (Z)-4-cyclopentadecen-1-one, 3-methylcyclopentadecanone, 1-oxa-12-cyclohexadecen-2-one, 1-oxa-13-cyclohexadecen-2-one, (9Z)-9-cycloheptadecen-1-one, 2-{(1S)-1-[(1R)-3,3-dimethylcyclohexyl]ethoxy}-2-oxaethylpropionate, 3-methyl-5-cyclo lopentadecen-1-one, 4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]isochromene, (1S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropylpropanoate, oxacyclohexadecan-2-one and / or (1S,1'R)-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxycarbonyl]methylpropanoate; - Woody ingredients: 1-[(1RS,6SR)-2,2,6-trimethylcyclohexyl]-3-hexanol, 3,3-dimethyl-5-[(1R)-2,2,3-trimethyl-3-cyclopenten-1-yl]-4-penten-2-ol, 3,4'-dimethylspiro[oxirane-2,9'-tricyclo[6.2.1.02,7]undec[4]ene, (1-ethoxyethoxy)cyclododecane, 2,2,9,11-tetramethylspiro[5.5]undec-8-en-1-yl acetate, 1-(octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-1-ethanone, patchouli oil, terpene fraction of patchouli oil, clearwood® (source: Firmenich SA), (1'R,E)-2-ethyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-2-buten-1-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, methyl cedryl ketone, 5-(2,2,3-trimethyl-3-cyclopentenyl)-3-methylpentan-2-ol, 1-(2,3,8,8-tetramethyl-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl)ethan-1-one and / or isobornyl acetate; other ingredients (e.g. amber, powdery spicy or watery): dodecahydro-3a,6,6,9a-tetramethyl-naphtho[2,1-b]furan and any of its stereoisomers, heliotropin, anisaldehyde, eugenol, cinnamaldehyde, clove oil, 3-(1,3-benzodioxol-5-yl)-2-methylpropanal, 7-methyl-2H-1,5-benzodioxepin-3(4H)-one, 2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydro-2-naphthalenol, 1-phenylvinyl acetate, 6-methyl-7-oxa-1-thia-4-azaspiro[4.4]nonane and / or 3-(3-isopropyl-1-phenyl)butanal.

[0101] The perfume base according to the invention may be, but is not limited to, the perfuming co-ingredients mentioned above, many others of which are in any case mentioned in references, for example in Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, by S. Arctander, or in its latest editions, or in other works of a similar nature, as well as in the abundant patent literature in the field of perfumery. It is also understood that said co-ingredients may be compounds known to release various types of perfuming compounds in a controlled manner, also known as properfumes or profragrances. Non-limiting examples of suitable pro-perfumes or pro-fragrances include 4-(dodecylthio)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-butanone, 4-(dodecylthio)-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butanone, trans-3-(dodecylthio)-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-2-butanone, Linear polysiloxane copolymer of 3-(dodecylsulfonyl)-1-(2,6,6-trimethylcyclohex-3-en-1-yl)butan-1-one, 3-((3-(dimethoxy(methyl)silyl)propyl)thio)-2-methyl-5-(prop-1-en-2-yl)cyclohex-1-one, 3-(dodecylthio)-1-(6-ethyl)-1-butanone, ... 2-(dodecylthio)octan-4-one, 2-(dodecylsulfonyl)octan-4-one, 4-oxooctane-2-yl dodecanoate, 2-phenylethyloxo(phenyl)acetate, 3,7-dimethylocta-2,6-dien-1-yloxo(phenyl)acetate, ( Z)-Hex-3-en-1-yl oxo(phenyl)acetate, 3,7-dimethyl-2,6-octadien-1-yl hexadecanoate, bis(3,7-dimethylocta-2,6-dien-1-yl)succinate, (2E,6Z)-2,6-nonadienyl hexadecanoate, (2E,6Z)-2,6-nonadienyl tetradecanoate, (2E,6Z)-2,6-Nonadienyl dodecanoate, (2-((2-methylundec-1-en-1-yl)oxy)ethyl)benzene, 1-methoxy-4-(3-methyl-4-phenethoxybut-3-en-1-yl)benzene, (3-methyl-4-phenethoxybut-3-en-1-yl)benzene, 1-(((Z)-hex-3-en-1-yl)oxy)-2-methylundec-1-ene, (2-((2-methylundec-1-en-1-yl)oxy)ethoxy)benzene, 2-methyl-1-(octan-3-yloxy)undec-1 -ene, 1-methoxy-4-(1-phenethoxyprop-1-en-2-yl)benzene, 1-methyl-4-(1-phenethoxyprop-1-en-2-yl)benzene, 2-(1-phenethoxyprop-1-en-2-yl)naphthalene, (2-phenethoxyvinyl)benzene, 2-(1-((3,7-dimethyloct-6-en-1-yl)oxy)prop-1-en-2-yl)naphthalene, (2-((2-pentylcyclopentylidene)methoxy)ethyl)benzene, 4-allyl-2-methoxy-1-((2-methoxy- 2-phenylvinyl)oxy)benzene, (2-((2-heptylcyclopentylidene)methoxy)ethyl)benzene, (2-((2-methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-1-en-1-yl)oxy)ethyl)benzene, 1-methoxy-4-(2-methyl-3-phenethoxyallyl)benzene, (2-((2-isopropyl-5-methylcyclohexylidene)methoxy)ethyl)benzene, 1-isopropyl-4-methyl-2-((2-pentylcyclopentylidene)methoxy) benzene, 2-methoxy-1-((2-pentylcyclopentylidene)methoxy)-4-propylbenzene, 2-ethoxy-1-((2-methoxy-2-phenylvinyl)oxy)-4-methylbenzene, 3-methoxy-4-((2-methoxy-2-phenylvinyl)oxy)benzaldehyde, 1-isopropyl-2-((2-methoxy-2-phenylvinyl)oxy)-4-methylbenzene, 4-((2-(hexyloxy)-2-phenylvinyl)oxy)-3-methoxybenzaldehyde or mixtures thereof.

[0102] The term "perfuming adjuvant" is understood to mean an ingredient that can provide additional added effects, such as color, specific light resistance, chemical stability, etc. A detailed description of the nature and type of adjuvants commonly used in perfumed bases cannot be exhaustive, but it should be mentioned that said ingredients are well known to those skilled in the art. However, as specific, non-limiting examples, the following may be mentioned: viscosity agents (e.g. surfactants, thickeners, gelling and / or rheology modifiers), stabilizers (e.g. preservatives, antioxidants, heat / light and / or buffers or chelating agents, e.g. BHT), colorants (e.g. dyes and / or pigments), preservatives (e.g. antibacterial or antimicrobial or antifungal or anti-irritant agents), abrasives, skin cooling agents, fixatives, insect repellents, ointments, vitamins and mixtures thereof. By "fixatives", also referred to as "modifiers", is meant here an agent capable of influencing the manner in which the odor of the composition in which it is encapsulated, in particular the evaporation rate and intensity, can be perceived by the observer or user over time, compared to a similar perception in the absence of the modifier. In particular, modifiers make it possible to extend the time for which the fragrance is perceived.Non-limiting examples of suitable modifiers include methyl glucoside polyol, ethyl glucoside polyol, propyl glucoside polyol, isocetyl alcohol, PPG-3 myristyl ether, neopentyl glycol diethylhexanoate, sucrose laurate, sucrose dilaurate, sucrose myristate, sucrose palmitate, sucrose stearate, sucrose distearate, sucrose tristearate, hyaluronic acid disaccharide sodium salt, sodium hyaluronate, propylene glycol propyl ether, dicetyl ether, polyglycerin-4 ether, isoceteth-5, isoceteth-7, isoceteth-10, isoceteth-12, isoceteth-15, isoceteth-20, isoceteth-25, isoceteth-30, disodium lauroamphodipropionate, hexaethylene glycol monododecyl ether, and mixtures thereof, neopentyl glycol diisononanoate, cetearyl ethylhexanoate, panthenol ethyl ether, DL-panthenol, N-hexadecyl n-nonanoate, noctadecyl n-nonanoate, profragrance, cyclodextrin, encapsulation, and combinations thereof. Up to 20% by weight of the modifier, based on the total weight of the perfume composition, may be incorporated into the perfumed consumer product.

[0103] It is understood that a person skilled in the art is fully capable of designing the optimum formulation for the desired effect by mixing said components of the perfuming composition, simply by applying standard knowledge in the art and by trial and error methodology.

[0104] The composition of the present invention, consisting of at least one compound of formula (I) according to the present invention and at least one perfume carrier, represents a particular embodiment of the present invention and refers to a perfumed composition comprising at least one compound of formula (I) according to the present invention, at least one perfume carrier, at least one perfume base and optionally at least one perfume adjuvant.

[0105] It is useful to mention here that the possibility of having, in said composition, one or more compounds of formula (I) according to the invention or other precursors of similar type is important for the perfumer to be able to produce accords, perfumes, exhibiting the odour notes of the various compounds according to the invention, thus creating new building blocks for the purpose of creation.

[0106] For reasons of clarity, it is also understood that any mixture obtained directly from a chemical synthesis, containing the compound of the invention as a starting, intermediate or final product, such as a reaction medium without sufficient purification, is not considered as a perfuming composition according to the invention, as long as said mixture provides the compound according to the invention in a form suitable for perfuming. Unpurified reaction mixtures are therefore generally excluded from the present invention, unless expressly stated otherwise.

[0107] Furthermore, the compounds of formula (I) of the present invention may be advantageously used in all fields of modern perfumery, i.e. refined or functional perfumery, to positively impart or improve the odor of consumer products to which said compounds (I) are added.The present invention therefore also relates to perfumed consumer products comprising at least one compound of formula (I) as defined above or a perfuming composition as defined above.

[0108] For reasons of clarity, it should be noted that the term "perfumed consumer product" is understood as a consumer product that is expected to provide at least one pleasant odor effect to the surface (e.g. skin, hair, fabric, or hard surface) to which the odor effect is applied. In other words, the perfumed consumer product according to the present invention is a perfumed consumer product that comprises a functional formulation and optionally an additional active substance corresponding to the desired consumer product, such as a conditioner, detergent or air freshener, and an olfactory effective amount of at least one compound according to the present invention. For reasons of clarity, said perfumed consumer product is a non-edible product.

[0109] The nature and type of ingredients of perfumed consumer products, which in any case will not be exhaustive, do not warrant a more detailed description here, whereby a person skilled in the art can select said bases on the basis of his general knowledge and according to the nature and desired effect of the product.

[0110] In one embodiment, the perfumed consumer product is a perfume, a fabric care product, a body care product, a cosmetic formulation, a skin care product, an air care product, or a home care product.

[0111] Non-limiting examples of suitable perfumed consumer products include fine perfumes, such as fine fragrances, splashes or eau de parfums, colognes or shave or aftershave lotions; fabric care products, such as liquid or solid detergents, optionally in pod or tablet form, fabric softeners, liquid or solid scent boosters, dryer sheets, fabric refreshers, ironing water, paper, bleach, carpet cleaners, curtain care products; body care products, such as hair care products (e.g. shampoos, leave-on or rinse-off hair conditioners, hair dyes or hairsprays, color care products, hair shaping products), dental care products, disinfectants, intimate care products; cosmetic formulations (e.g. skin creams or lotions, vanishing creams or deodorants, or antiperspirants (e.g. sprays or roll-ons), depilatories, tanning or after-sun products, nail products, skin cleansing, make-up); or skin care products (perfumed soaps, mousses, oils or gels for the shower or bath, or hygiene products, or foot / hand care products); air care products, such as air fresheners or "ready to use" powdered air fresheners that may be used in residential spaces (rooms, refrigerators, cupboards, shoeboxes or cars) and / or in public spaces (hall, hotel, mall, etc.); or home care products, such as mould removers, furniture care products, wipes, dish detergents or hard surface (e.g. floor, bath, sanitary or window washing) cleaners; leather care products; car care products, such as polishes, waxes or plastic cleaners.

[0112] Typical examples of fabric detergent compositions and fabric softener compositions that may be incorporated into the compounds of the present invention are described in WO 97 / 34986, or US Pat. Nos. 4,137,180 and 5,236,615, or EP 799 885. Other typical detergent compositions and fabric softener compositions that may be used are described in books such as Ullmann's Encyclopedia of Industrial Chemistry, vol.20, Wiley-VCH, Weinheim, p. 355-540 (2012); Flick, Advanced Cleaning Product Formulations, Noye Publication, Park Ridge, New Jersey(1989); Showell, in Surfactant Science Series, vol. 71: Powdered Detergents, Marcel Dekker, New York (1988); Proceedings of the World Conference on Detergents (4th, 1998, Montreux, Switzerland), AOCS print.

[0113] According to any embodiment of the present invention, the inventive flavored consumer product is characterized by having a pH of greater than or equal to 1. In particular, the inventive flavored consumer product has a pH of 1-12 or 1-8. More particularly, the inventive flavored consumer product has a pH of 1-6.

[0114] According to a particular embodiment, the perfumed consumer product of the present invention is in the form of a personal care, home care or fabric care consumer product, in particular a personal care, home care or fabric care consumer product that contains ingredients common to shower gels, shampoos, soaps, fabric detergents or softeners and multi-purpose cleaners. The main functional ingredients of the perfumed consumer product are surfactants and / or softener ingredients that can clean and / or soften fabrics and / or textiles of various natures, such as clothing, curtain fabrics, carpets and furniture fabrics, or other household surfaces, skin or hair, and are typically used with large amounts of water or water-based solvents. Thus, these are formulations in which the amount of water is typically 50-99% by mass of the perfumed consumer product, except for soaps or solid detergents, in which the amount of water is at most 20%.

[0115] A more detailed description of such fabric cleaner and / or softener formulations is not necessary here, and many descriptions of current liquid formulations can be found in cleaner / fabric softener patents and other relevant literature, such as Louis Ho Tan Tai's textbook "Detergents et Produits de Soins Corporels, especially Chapters 1-7, Dunod, Paris, 1999", or other similar and / or more recent textbooks on the technology of liquid fabric softener and all-purpose cleaner formulations. Patent publication WO 2010 / 105873 also describes typical current ingredients other than perfumes in such liquid products, especially on pages 9-21, and is cited as an example. Of course, many other examples of liquid detergent and / or fabric softener formulations can be found in the literature. Any such liquid formulations, i.e. liquid fabric cleaners or conditioners and / or all-purpose cleaners, may be used in the compositions described herein.

[0116] According to a particular embodiment of the present invention, the perfumed consumer product of the present invention is a liquid fabric softener comprising a fabric softener active base in an amount of 85-100% by weight, based on the total weight of the perfumed consumer product. The main component of the fabric softener active base is water or a water-based solvent. The fabric softener active base may comprise dialkyl quaternary ammonium salts, dialkyl ester quaternary ammonium salts, Hamburg esterquats, triethanolamine quats, silicones, and mixtures thereof. Optionally, the fabric softener active base of the composition may further comprise a viscosity modifier in an amount of 0.05-1% by weight, based on the total weight of the liquid base, the viscosity modifier being preferably selected from the group consisting of calcium chloride.

[0117] According to a particular embodiment of the present invention, the perfumed consumer product of the present invention is an all-purpose cleaner comprising an all-purpose cleaner active base in an amount of 85-100% by weight, based on the total weight of the perfumed consumer product. The main component of the all-purpose cleaner active base is water or a water-based solvent. The all-purpose active base may comprise a linear alkylbenzene sulfonate (LAS) in an amount of 1-2%, a non-ionic surfactant in an amount of 2-4%, and an acid, such as citric acid, in an amount of 0.1-0.5%.

[0118] According to a particular embodiment of the present invention, the perfumed consumer product of the present invention is a liquid detergent comprising a liquid detergent active base in an amount of 85-100% by weight based on the total weight of the perfumed consumer product. The main component of the liquid detergent active base is water or a water-based solvent. The liquid detergent active base may comprise anionic surfactants such as alkyl benzene sulfonates (ABS), linear alkyl benzene sulfonates (LAS), secondary alkyl sulfonates (SAS), primary alcohol sulfates (PAS), lauryl ether sulfates (LES), sodium lauryl ether sulfate (SLES), methyl ester sulfonates (MES); non-ionic surfactants such as alkyl amines, alkanolamides, fatty alcohol poly(ethylene glycol) ethers, fatty alcohol ethoxylates (FAE), ethylene oxide (EO) and propylene oxide (PO) copolymers, amine oxides, alkyl polyglucosides, alkyl polyglucosamides; or mixtures thereof.

[0119] According to a particular embodiment of the present invention, the perfumed consumer product of the present invention is a solid detergent comprising a solid detergent active base in an amount of 85-100% by weight, based on the total weight of the perfumed consumer product. The solid detergent active base may comprise at least one surfactant selected from the group consisting of anionic, nonionic, cationic, zwitterionic surfactants and mixtures thereof. The surfactant in the solid detergent active base is preferably selected from the group consisting of linear alkene benzene sulfonic acids (LABS), sodium laureth sulfate, sodium lauryl ether sulfate (SLES), sodium lauryl sulfate (SLS), alpha olefin sulfonic acids (AOS), methyl ester sulfonic acids (MES), alkyl polyglycosides (APG), primary alcohol ethoxylates, in particular lauryl alcohol ethoxylates (LAE), primary alcohol sulfonic acids (PAS), soaps, and mixtures thereof. The solid detergent active base may contain further ingredients conventionally used in powder detergent consumer products, which are selected from the group consisting of bleaching agents, such as TAED (tetraacetylethylenediamine); buffers; builders, such as zeolites, sodium carbonate or mixtures thereof; soil release polymers or soil suspending polymers; granulated enzyme particles, such as cellulase, lipase, protease, mannanase, pectinase or mixtures thereof; corrosion inhibitors; antifoams; foam suppressors; dyes; fillers, such as sodium silicate, sodium sulfate or mixtures thereof; a hydrogen peroxide source, such as sodium percarbonate or sodium perborate; and mixtures thereof.

[0120] According to a particular embodiment of the present invention, the perfumed consumer product of the present invention is a shampoo or shower gel comprising a shampoo or shower gel active base in an amount of 85-100% by weight based on the total weight of the perfumed consumer product. The main component of the shampoo or shower gel active base is water or a water-based solvent. The active base of the shampoo shower gel may comprise sodium alkyl ether sulfate, ammonium alkyl ether sulfate, alkyl amphoacetic acid, cocamidopropyl betaine, cocamide MEA, alkyl glucoside and amino acid surfactant.

[0121] According to a particular embodiment of the present invention, the perfumed consumer product of the present invention is a soap bar comprising a soap active base in an amount of 85-100% by weight, based on the total weight of the perfumed consumer product. The soap bar active base may comprise a salt of a weak acid, which may typically be a fatty acid, and a salt of a strong base, such as sodium hydroxide.

[0122] The proportions of the compounds according to the invention that may be incorporated into the various said articles or compositions vary within a wide range of values, depending on the nature of the article or product to be perfumed, as well as on the desired olfactory effect and the nature of the auxiliary ingredients in a given composition, when the compounds according to the invention are mixed with perfuming auxiliary ingredients, solvents or additives commonly used in the prior art.

[0123] For example, in the case of perfumed compositions, typical concentrations range from 0.001% to 10% by weight or more of the compound of the invention relative to the weight of the composition in which it may be incorporated.In the case of perfumed consumer products, typical concentrations range from 0.0001% to 5% by weight or more of the compound of the invention relative to the weight of the composition in which it may be incorporated.

[0124] Furthermore, the present invention relates to a compound of formula (I). Thus, another object of the present invention is to provide a compound of formula (I) [ka] [In the formula, R 1 contains at least 6 carbon atoms, and 1-15 Alkyl group, C 3-15 Alkenyl group, C 3-15 Cycloalkyl groups, C 5-15 Cycloalkenyl group or C 3-14 Heterocycloalkyl groups, each optionally selected from C 1-8 Alkyl group, C 1-8 Alkoxy groups, hydroxy groups, carboxylic acid groups and / or C 1-4 Hydroxy groups substituted with one or more carboxylic acid ester groups, C 1-15 Alkyl group, C 2-15 Alkenyl group, C 1-15Alkoxy group, C 2-15 Alkenyloxy group, C 3-15 Cycloalkyl groups, C 5-15 Cycloalkenyl group, C 3-15 Heterocycloalkyl group, carboxylic acid group, C 1-4 Carboxylic acid ester group, C 6-10 Aryl groups and / or C 6-10 each optionally substituted with one or more aryloxy groups; 1-15 Alkyl group, C 3-15 Alkenyl group, C 3-15 Cycloalkyl groups, C 5-15 Cycloalkenyl group or C 3-14 heterocycloalkyl group, the heteroatoms representing one or more oxygen atoms, with the proviso that R 1 is not a 2-hexylidenecyclopentyl group; R 2 optionally containing 1 or 2 oxygen atoms, C 6-18 a hydrocarbon group, except for the ester functional group α to the oxy group, and R 2 benzyl, cyclohexyl, 2-hydroxy-1,2-diphenylethyl, or 1-(tert-butoxy)-7,7-dimethylbicyclo[2.1]heptan-2-yl, not containing an allyl function; and excluding 1-(heptyloxy)dec-1-ene, 1-(decyloxy)dec-1-ene, 1-(dodecyloxy)dodec-1-ene, (4-phenethoxybut-3-en-1-yl)benzene, and 1-((3,7-dimethyloctyl)oxy)-3,7-dimethyloct-1-ene. in the form of any one of its stereoisomers or a mixture thereof.

[0125] The term "benzyl group" is understood as the group CH2C6H4, i.e. the phenyl group is unsubstituted.

[0126] The term "cyclohexyl group" means CH 11 It is understood as a radical, i.e. the cyclohexyl radical is not substituted.

[0127] In another aspect, the present invention provides a method for producing a) An aldehyde compound of formula (II) [ka] [In the formula, R 1 is C 1-8 Alkyl group, C 1-8 Alkoxy groups, hydroxy groups, carboxylic acid groups and / or C 1-4 a hydroxy group, each optionally substituted with one or more carboxylic acid ester groups, C 1-15 Alkyl group, C 2-15 Alkenyl group, C 1-15 Alkoxy group, C 2-15 Alkenyloxy group, C 3-15 Cycloalkyl groups, C 5-15 Cycloalkenyl group, C 3-15 Heterocycloalkyl group, carboxylic acid group, C 1-4 Carboxylic acid ester group, C 6-10 Aryl groups and / or C 6-10 each optionally substituted with one or more aryloxy groups, 1-15 Alkyl group, C 3-15 Alkenyl group, C 3-15 Cycloalkyl, C 5-15 Cycloalkenyl or C 3-14 is a heterocycloalkyl group. b) a formate of formula (III) [ka] [In the formula, R 2 C optionally containing one, two or three oxygen atoms 1-18 a hydrocarbon group, except for an ester functional group alpha to a formyloxy group. c) an alcohol of formula (IV) [ka] [In the formula, R 2 have the same meaning as defined above. Use of a precursor compound of formula (I) for releasing a compound selected from the group consisting of: The precursor compound is a compound of formula (I) [ka] [In the formula, R 1 and R 2 has the same meaning as defined above] in the form of any of its stereoisomers or mixtures thereof.

[0128] In another aspect, the present invention also relates to the use of at least one compound of formula (I) as defined above for imparting, enhancing, improving or modifying the odor characteristics of a perfumed composition, the air surrounding the perfumed composition, a surface or a perfumed article, comprising adding an effective amount of at least one compound of formula (I) as defined above to the composition or article, or contacting or treating the surface with an effective amount of at least one compound of formula (I) as defined above. The term "surface" as used herein may refer to the skin, hair, fabric or hard surface of a user to which a perfume composition comprising or containing at least one compound of formula (I) is applied.

[0129] In another aspect, the present invention relates to the use of at least one compound of formula (I) as defined above to enhance or prolong the diffusion effect of at least one aldehyde compound of formula (II), at least one formate ester of formula (III) and / or at least one alcohol of formula (IV) as defined above, or to perceive their characteristic fragrance, on surfaces treated with at least one compound of formula (I) as defined above, or with a composition or article comprising at least one compound of formula (I), under conditions conducive to allowing the release of at least one aldehyde compound of formula (II), at least one formate ester of formula (III) and / or at least one active alcohol of formula (IV) over time.

[0130] The compounds of formula (I) may be prepared according to standard methods known to those skilled in the art and are described below.

[0131] Working Example The invention is described in further detail by the following examples, in which the abbreviations have their usual meaning in the art and the temperatures are given in degrees Celsius (° C.). NMR spectra were obtained at 400 MHz ( 1 H) and 100MHz ( 13 C) operating with Bruker Avance II Ultrashield 400plus or 500MHz ( 1 H) and 125.8MHz ( 13 C) operated by Bruker Avance III500 or 600MHz ( 1 H) and 151MHz ( 13 C), and the spectra were internally referenced to tetramethylsilane at 0.0 ppm. 1 H NMR signal shifts are expressed in δ ppm and coupling constants (J) are expressed in Hz with the following multiplicities: d, doublet; t, triplet; q, quartet; m, multiplet; b, broad (indicating unresolved couplings) and were interpreted using Bruker Topspin software. 13 C NMR data are expressed as chemical shifts δ ppm and hybridization from DEPT90 and DEPT135 experiments, C, quaternary; CH, methine; CH2, methylene; CH3, methyl.

[0132] Example 1 Preparation of Compounds According to Formula (I) and Comparative Compounds Compound 1. (2-(dodec-1-en-1-yloxy)ethyl)benzene: Dimethyl acetal of dodecanal (13 g, 56.4 mmol), 2-phenylethanol (17.9 g, 146 mmol) and KHSO4 (0.037 g, 0.27 mmol) were added to a 35 ml round bottom flask equipped with a distillation head and nitrogen bubbler. The mixture was heated (oil bath) at 150°C to distill the liberated alcohol for 1 h. The mixture was cooled and placed under vacuum (4 Pa) and heated (oil bath at 190°C) to distill the liberated phenylethanol and enol ether from the reaction flask. The enol ether-rich fractions were combined and after addition of Na2CO3 (0.3 g), the distillate was subjected to short-path distillation (bp 140 °C, 4 Pa) to give 6.9 g (23.9 mmol, 42% yield) of the title compound as a colorless oil (E / Z = 30:70).

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[0133] Compound 2. (2-(tridec-1-en-1-yloxy)ethyl)benzene: Dimethyl acetal of tridecanal (10 g, 40.9 mmol), 2-phenylethanol (15.0 g, 123 mmol) and KHSO4 (0.17 g, 1.24 mmol) were added to a 35 ml round bottom flask equipped with a distillation head and nitrogen bubbler. The mixture was heated (oil bath) at 140° C. and the liberated methanol was distilled from the reaction vessel. After 1 h, the reaction vessel was placed under vacuum (60 kPa) and the pressure was gradually reduced to 1.3 Pa over 3 h to allow 2-phenylethanol to distill from the flask. Following this, the title compound (3.28 g, 26.5% yield) was isolated from the reaction flask (boiling point 155° C., 1 Pa) by short path vacuum distillation as a pale yellow oil (E / Z=38:62).

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[0134] Compound 3. (2-(undeca-1,10-dien-1-yloxy)ethyl)benzene: General procedure: A mixture of aldehyde (120 mmol), 2-phenylethanol (4 equiv.), TsOH (0.025 equiv.) and toluene (100 mL) was heated at reflux for 1 h and water was removed with a Dean-Stark trap. After the mixture was cooled, it was diluted with diethyl ether and washed with saturated Na2CO3 and water. The organic phase was dried over Na2SO4, filtered and concentrated. Excess phenylethanol was removed by heating the product under vacuum (140 °C in oven, 3.3 Pa) using a Kugelrohr distillation apparatus. The obtained phenylethyl acetal (40-80 mmol) and KHSO4 (0.059 g, 0.40-0.80 mmol) were charged to a 35 ml round bottom flask equipped with a distillation head. The mixture was placed under vacuum (4 Pa) and set in a 120 °C oil bath. The oil bath was heated to 190° C. to allow the liberated phenylethanol and enol ether to flow from the flask. The enol ether-rich fractions were combined. After adding Na2CO3 (0.5 g), the distillate was subjected to short-path distillation to give the enol ether as a colorless oil.

[0135] Following this general procedure and using the phenylethyl acetal of 10-undecenal (17.1 g, 43.4 mmol), the title compound was isolated by short-path distillation (bp 137-143 °C, 4 Pa) in 70% yield (E / Z = 35:65).

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[0136] Compound 4. ((3-Phenethoxyallyl)benzene): Following the procedure described for compound 3, the title compound was isolated by bulb-to-bulb distillation using a Kugelrohr distillation apparatus (furnace 140-170 °C, 4 Pa) using phenylethyl acetal of 3-phenylpropanal (28.7 g, 79.6 mmol) in 41% yield (E / Z = 35:65).

number

[0137] Compound 5. (4-Phenethoxybut-3-en-2-yl)benzene: Following the procedure described for compound 3, phenylethyl acetal of 3-phenylbutanal (15 g, 40.1 mmol) was used and the reaction mixture was heated at 155° C. under vacuum (6.7 Pa) for 1.5 h. It was then diluted with diethyl ether and washed with saturated Na2CO3 and water. The organic phase was dried over Na2SO4, filtered and concentrated. The title compound (2.8 g, 28% yield) was isolated as a colorless oil by bulb-to-bulb distillation using a Kugelrohr distillation apparatus (oven 145-150° C., 2.7 Pa) (E / Z=52:48).

number

[0138] Compound 6. (3-Methyl-5-phenethoxypent-4-en-1-yl)benzene: Following the procedure described for compound 3, phenylethyl acetal of 3-methyl-5-phenylpentanal (13 g, 32.3 mmol) was used and the reaction mixture was heated at 155° C. (6.7 Pa) for 2 h. It was then diluted with diethyl ether and washed with saturated Na2CO3 and water. The organic phase was dried over Na2SO4, filtered and concentrated. The title compound (3.45 g, 38% yield) was isolated as a colorless oil by bulb-to-bulb distillation using a Kugelrohr distillation apparatus (oven 165° C., 2.4 Pa) (E / Z=50:50).

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[0139] Compound 7. 1-(Octyloxy)dodec-1-ene: A mixture of dodecanal dimethyl acetal (3.75 g, 16.3 mmol), octanol (8.46 g, 65.1 mmol), and KHSO4 (0.022 g, 0.163 mmol) was heated at 60 °C for 3 h and 80 °C for 5 h under vacuum (12 kPa) using a Kugelrohr distillation apparatus. The mixture was then heated at 200 °C (15.3 Pa) and the resulting enol ether and octanol were distilled from the pot. The enol ether-rich distillation fractions were combined and subjected to silica gel flash chromatography (hexane / EtOAc, 99.5:0.5) followed by bulb-to-bulb distillation (150 °C, 8 Pa) to give the title compound (1.74 g, 36% yield) as a colorless liquid (E / Z=30:70).

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[0140] Compound 8. 1-(tert-Butyl)4-(3-phenethoxyallyl)benzene: Dimethyl acetal of 3-(4-tert-butyl)phenyl)propanal (28.1 g, 119 mmol), 2-phenylethanol (29.2 g, 239 mmol) and KHSO4 (0.163 g, 1.2 mmol) were added to a 100 ml round bottom flask equipped with a distillation head and nitrogen bubbler. The mixture was heated (oil bath) at 150° C. for 1 h to distill off MeOH. The mixture was cooled and placed under vacuum (4 Pa) and heated (oil bath at 240° C.) to distill off the liberated phenylethanol and enol ether from the reaction flask. The enol ether-rich fractions were combined and subjected to short-path distillation (bp 152° C., 4 Pa) to give 12.1 g (41.1 mmol, 34% yield) of the title compound as a colorless oil (E / Z=40:60).

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[0141] Compound 9. (2-(undec-1-en-1-yloxy)ethyl)benzene: Dimethyl acetal of undecanal (8.0 g, 37.0 mmol), 2-phenylethanol (11.3 g, 92.4 mmol) and KHSO4 (0.15 g, 1.10 mmol) were added to a 35 ml round bottom flask equipped with a distillation head and nitrogen bubbler. The mixture was heated (oil bath) at 150° C. for 1.5 hours while MeOH was distilled. The mixture was allowed to cool and placed under vacuum (typically 67 Pa) and heated (oil bath at 120° C.). The vacuum was gradually reduced to allow excess 2-phenylethanol to distill from the reaction flask. Following this, the bath temperature was increased to 200° C. and the vacuum was further reduced to 2 Pa to allow the enol ether to distill from the flask once it had formed. The enol ether-rich fractions were combined and subjected to short-path distillation (bp 152° C., 4 Pa) to give 5.27 g (19.2 mmol, 52% yield) of the title compound as a colorless oil (E / Z=40:60).

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[0142] Compound 10. (2-(undec-1-en-1-yloxy)ethoxy)benzene: Following the procedure described for compound 9, starting from dimethyl acetal of undecanal (10.0 g, 46.219 mmol), 2-phenoxyethanol (16.0 g, 115.5 mmol) and KHSO4 (0.188 g, 1.38 mmol), the title compound (2.2 g, 7.6 mmol) was isolated by distillation (bp 138° C., 2.6 Pa) in 16% yield as a colorless liquid (E / Z=35:65).

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[0143] Compound 11. 1-(3,7-dimethyloctyl)oxy)undec-1-ene: Following the procedure described for compound 9, starting from dimethyl acetal of undecanal (10.0 g, 46.2 mmol), 3,7-dimethylocten-1-ol (18.3 g, 115.6 mmol) and KHSO4 (0.25 g, 1.84 mmol), the title compound (8.8 g, 7.6 mmol) was isolated by distillation (bp 140° C., 4 Pa) in 61% yield as a colorless liquid (E / Z=35:65).

number

[0144] Compound 12. (2-(dodec-1-en-1-yloxy)ethoxy)benzene: Following the procedure described for compound 9, starting from the dimethyl acetal of dodecenal (8.0 g, 34.7 mmol), 2-phenoxyethanol (12.0 g, 87 mmol) and KHSO4 (0.15 g, 1.05 mmol), the title compound (1.2 g, 3.8 mmol) was isolated by distillation (bp 125° C., 2.6 Pa) in 11% yield as a colorless liquid (E / Z=40:60).

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[0145] Compound 13. 1-(octan-2-yloxy)dodec-1-ene: Following the procedure described for compound 9, starting from dimethyl acetal of dodecenal (10.0 g, 43.4 mmol), 2-octanol (14.1 g, 108 mmol) and KHSO4 (0.18 g, 1.30 mmol), the title compound (2.0 g, 6.85 mmol) was isolated by distillation (bp 130° C., 2 Pa) in 16% yield as a colorless liquid (E / Z=30:70).

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[0146] Compound 14. (2-(non-1-en-1-yloxy)ethyl)benzene: Following the procedure described for compound 9, starting from dimethyl acetal of nonanal (10.0 g, 53.1 mmol), 2-phenylethanol (16.2 g, 132.7 mmol) and KHSO4 (0.22 g, 1.60 mmol), the title compound (4.0 g, 16.1 mmol) was isolated by distillation (bp 120° C., 2 Pa) in 30% yield as a colorless liquid (E / Z=35:65).

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[0147] Compound 15. 1-(3,7-dimethyloct-6-en-1-yl)oxy)non-1-ene: Following the procedure described for compound 9, starting from dimethyl acetal of nonanal (8.0 g, 42.5 mmol), (±)-citronellol (16.6 g, 106.2 mmol) and KHSO4 (0.18 g, 1.3 mmol), the title compound (7.0 g, 25.0 mmol) was isolated by distillation (bp 128 °C, 2 Pa) in 59% yield as a colorless liquid (E / Z = 25:75).

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[0148] Compound 16. (1-Methoxy-3-methyl)dodec-1-ene (intermediate used for the preparation of compounds 25-29): A solution of methoxymethyltriphenylphosphonium chloride (139.7 g, 407.5 mmol) and 2-methylundecanal (50 g, 271.7 mmol) in toluene (500 mL) was cooled in an ice bath. Potassium t-butoxide (48.8 g, 434.7 mmol) was added in one portion and the mixture was stirred for 30 min until the exotherm subsided. The mixture was removed from the cold bath and stirred at room temperature until all starting aldehyde was consumed (3 h). The mixture was poured into 500 mL of water and stirred for 1 h. After phase separation, the aqueous phase was extracted with EtOAc (3 x 200 mL). The organic phases were combined, dried over Na2SO4, filtered, and concentrated to a granular slurry. The slurry was washed with hexane and filtered. The filtrate was concentrated to give the crude methyl enol ether, which was fractionally distilled (bp 80° C., 2 Pa) to give 50.8 g (239 mmol, 79% yield) of the title compound as a colorless liquid (E / Z=60:40).

number

[0149] Compound 17. 1-Methoxydodeca-1,11-diene (intermediate used for the preparation of compound 30): Following the procedure described for compound 14, starting from 10-undecenal, the title compound was isolated by fractional distillation (boiling point of the crude reaction mixture (bp 80° C., 100 mtorr)) in 45% yield as a colorless liquid (E / Z=50:50).

number

[0150] Compound 18. (5E)-1-Methoxyundeca-1,5-diene (intermediate used for the preparation of compound 31): Following the procedure described for compound 14, starting from trans-4-decenal, the title compound was isolated by fractional distillation (boiling point 80° C., 26.7 Pa) in 25% yield as a colorless liquid (E / Z=60:40).

number

[0151] Compound 19. (5-Methoxypent-4-en-2-yl)benzene (intermediate used for the preparation of compound 33): Following the procedure described for compound 14, starting from 3-phenylbutanal, the title compound was isolated by fractional distillation (boiling point 70° C., 8 Pa) in 60% yield as a colorless liquid (E / Z=50:50).

number

[0152] Compound 20. (4R)-4-(5-Methoxypent-4-en-2-yl)-1-methylcyclohex-1-ene (intermediate used for the preparation of compound 34): Following the procedure described for compound 14, starting from 3-((R)-4-methylcyclohex-3-en-1-yl)butanal, the title compound was isolated by fractional distillation (boiling point 94° C., 20 Pa) in 48% yield as a colorless liquid (mixture of diastereomers, E / Z=40:60).

number

[0153] Compound 21. 1-Methoxy-4,8-dimethylnona-1,7-diene (intermediate used for the preparation of compound 32): Following the procedure described for compound 14, starting from (±)-citronellal, the title compound was isolated by fractional distillation (boiling point 70° C., 26.7 Pa) in 13% yield as a colorless liquid (E / Z=54:46).

number

[0154] Compound 22. 1-(tert-butyl)-4-(4-methoxy-2-methylbut-3-en-1-yl)benzene (intermediate used for the preparation of compound 35): Following the procedure described for compound 14, starting from 3-(4-(tert-butyl)phenyl)-2-methylpropanal, the title compound was isolated by fractional distillation (boiling point 100° C., 2 Pa) in 81% yield as a colorless liquid (E / Z=60:40).

number

[0155] Compound 23. 4-(2-Methoxyvinyl)-1,3-dimethylcyclohex-1-ene (intermediate used for the preparation of compound of formula (I)): Following the procedure described for compound 14, starting from 2,4-dimethylcyclohex-3-ene-1-carbaldehyde, the title compound was isolated by fractional distillation (boiling point 65° C., 67 Pa) in 68% yield as a colorless liquid (mixture of diastereomers, E / Z=42:58).

number

[0156] Compound 24. 1-(4-Methoxybut-3-en-1-yl)-4,4-dimethylcyclohex-1-ene (intermediate used for the preparation of compound of formula (I)): Following the procedure described for compound 14, starting from 3-(4,4-dimethylcyclohex-1-en-1-yl)propanal, the title compound was isolated by fractional distillation (boiling point 80° C., 26.7 Pa) in 23% yield as a colorless liquid (E / Z=50:50).

number

[0157] Compound 25. (2-((3-methyldodec-1-en-1-yl)oxy)ethyl)benzene: Compound 16 (8.0 g, 37.7 mmol), 2-phenylethanol (11.5 g, 94.2 mmol) and KHSO4 (0.153 g, 1.12 mmol) were added to a 35 ml round bottom flask equipped with a distillation head and vacuum pump. The mixture was heated at 150°C (oil bath) under vacuum (450 mbar) for 45 min and heated for an additional 45 min while the vacuum was reduced to 20 mbar. The mixture was cooled and placed under vacuum (typically 67 Pa) and heated (oil bath at 120°C) to distill excess phenylethanol from the reaction flask. The vacuum was gradually reduced to 2 Pa and the reaction product was distilled from the flask while the bath temperature was increased to 200°C. The enol ether-rich fractions were combined and subjected to short-path distillation (bp 140° C., 1.3 Pa) to give 5.81 g (19.2 mmol, 51% yield) of the title compound as a colorless oil (E / Z=43:57).

number

[0158] Compound 26. (2-((3-methyldodec-1-en-1-yl)oxy)ethoxy)benzene: Following the procedure described for compound 25, starting from compound 16 (8 g, 37.7 mmol) and 2-phenoxyethanol (13.0 g, 94.2 mmol), the title compound was isolated by distillation (bp 140° C., 2.7 Pa) in 47% yield as a colorless liquid (E / Z=64:36).

number

[0159] Compound 27. 1-(((Z)-hex-3-en-1-yl)oxy)-3-methyldodec-1-ene: Following the procedure described for compound 25, starting from compound 16 (8 g, 37.7 mmol) and cis-3-hexen-1-ol (9.43 g, 94.2 mmol), the title compound (8.2 g, 29.1 mmol) was isolated by distillation (bp 125° C., 2 Pa) in 77% yield as a colorless liquid (E / Z=40:60).

number

[0160] Compound 28. 3-Methyl-1-(((Z)-octen-3-en-1-yl)oxy)dodec-1-ene: Following the procedure described for compound 25, starting from compound 16 (8 g, 37.7 mmol) and cis-3-octen-1-ol (12.1 g, 94.2 mmol), the title compound (6.0 g, 19.4 mmol) was isolated by distillation (bp 135° C., 2 Pa) in 52% yield as a colorless liquid (E / Z=40:60).

number

[0161] Compound 29. 3-Methyl-1-(octan-3-yloxy)dodec-1-ene: Following the procedure described for compound 25, starting from compound 16 (8.0 g, 37.7 mmol) and 3-octanol (12.3 g, 94.2 mmol), the title compound (5.8 g, 18.7 mmol) was isolated by distillation (bp 130° C., 2 Pa) in 50% yield as a colorless liquid (mixture of diastereomers, E / Z=35:65).

number

[0162] Compound 30. (2-(dodeca-1,11-dien-1-yloxy)ethyl)benzene: Following the procedure described for compound 25, starting from compound 17 (8 g, 40.7 mmol) and 2-phenylethanol (12.4 g, 102 mmol), the title compound (3.6 g, 12.4 mmol) was isolated by distillation (bp 140° C., 2 Pa) in 31% yield as a colorless liquid (E / Z=30:70).

number

[0163] Compound 31. (2-(((5E)-undeca-1,5-dien-1-yl)oxy)ethyl)benzene: Following the procedure described for compound 25, starting from compound 18 (8 g, 43.9 mmol) and 2-phenylethanol (13.4 g, 110 mmol), the title compound (3.97 g, 14.6 mmol) was isolated by distillation (bp 135° C., 2 Pa) in 33% yield as a colorless liquid (E / Z=40:60).

number

[0164] Compound 32. (2-((4,8-Dimethylnona-1,5-dien-1-yl)oxy)ethyl)benzene: Following the procedure described for compound 25, starting from compound 21 (8 g, 43.9 mmol) and 2-phenylethanol (13.4 g, 109.7 mmol), the title compound (1.81 g, 6.64 mmol) was isolated by distillation (bp 135° C., 2 Pa) in 15% yield as a colorless liquid (E / Z=35:65).

number

[0165] Compound 33. (5-Phenethoxypent-4-en-2-yl)benzene: Following the procedure described for compound 25, starting from compound 19 (8 g, 45.4 mmol) and 2-phenylethanol (13.9 g, 113.5 mmol), the title compound (5.2 g, 19.5 mmol) was isolated by distillation (bp 138° C., 2 Pa) in 43% yield as a colorless liquid (E / Z=35:65).

number

[0166] Compound 34. (2-((4-((R)-4-methylcyclohex-3-en-1-yl)pent-1-en-1-yl)oxy)ethyl)benzene: Following the procedure described for compound 25, starting from compound 20 (8.0 g, 41.2 mmol) and 2-phenylethanol (12.6 g, 103 mmol), the title compound (3.67 g, 12.5 mmol) was isolated by distillation (bp 135° C., 2 Pa) in 31% yield as a colorless liquid (mixture of diastereomers, E / Z=40:60).

number

[0167] Compound 35. 1-(tert-butyl)4-(2-methyl-4-phenethoxybut-3-en-1-yl)benzene: Following the procedure described for compound 25, starting from compound 22 (8 g, 34.4 mmol) and 2-phenylethanol (10.5 g, 86.1 mmol), the title compound (3.19 g, 9.9 mmol) was isolated by distillation (bp 155° C., 2 Pa) in 29% yield as a colorless liquid (E / Z=44:56).

number

[0168] Compound 36. 1-Ethoxynon-1-ene (Comparative Example Corresponding to Example V of US20040013779): Diethyl acetal of nonanal (15 g, 69.3 mmol) and KHSO4 (0.19 g, 1.37 mmol) were added to a 35 ml round bottom flask equipped with a distillation head and nitrogen bubbler. The mixture was heated (oil bath) at 150° C. for 2 hours while EtOH was distilled. The mixture was allowed to cool and placed under vacuum (67 Pa) and heated (oil bath at 120° C.). The vacuum was gradually reduced to 3 Pa and the reaction mixture was distilled. The enol ether rich fractions were combined and subjected to silica gel flash chromatography (hexane / EtOAc 100:0 to 95:5) to give 1.7 g (10.0 mmol, 14% yield) of the title compound as a colorless oil (E / Z=50:50).

number

[0169] Compound 37. 1-Ethoxyundec-1-ene (Comparative Example Corresponding to Example VIII of US20040013779): Diethyl acetal of undecanal (8 g, 32.7 mmol) and KHSO4 (0.14 g, 1.0 mmol) were added to a 25 ml round bottom flask equipped with a distillation head and a vacuum pump. The mixture was heated at 150°C (oil bath) under vacuum (450 mbar) for 2 h, and the pressure was gradually reduced to 18 mbar. The vacuum was then reduced to 3.3 Pa, and the reaction mixture was distilled. The enol ether-rich fractions were combined and subjected to silica gel flash chromatography (Hexane / EtOAc 100:0 to 95:5) to give 0.8 g (4.0 mmol, 12% yield) of the title compound as a colorless oil (E / Z=45:55).

number

[0170] Compound 38. 1-Ethoxydodec-1-ene (Comparative Example Corresponding to Example X of US20040013779): Diethyl acetal of dodecanal (15 g, 58.0 mmol) and KHSO4 (0.24 g, 1.73 mmol) were added to a 35 ml round-bottom flask equipped with a distillation head and a vacuum pump. The mixture was heated at 150°C (oil bath) under vacuum (450 mbar) for 2 h, and the pressure was gradually reduced to 18 mbar. The vacuum was then reduced to 3.3 Pa, and the reaction mixture was distilled. The enol ether-rich fractions were combined and subjected to silica gel flash chromatography (Hexane / EtOAc 100:0 to 95:5) to give 1.35 g (6.3 mmol, 11% yield) of the title compound as a colorless oil (E / Z=10:90).

number

[0171] Example 2 Headspace analysis from fabric softener applications containing compounds of formula (I) of the present invention A model liquid fabric softener was prepared by mixing 12.3% by weight of TEA-esterquat (Stepantex® VL90A), 0.4% by weight of 10% aqueous calcium chloride solution, 0.04% by weight of Proxcel GXL, and 87.2% by weight of deionized water. The enol ether (0.075 mmol) was weighed into a vial and dissolved in 0.25 mL of acetone. Liquid fabric softener (4.5 g) was added to the vial and the mixture was mixed by shaking by hand. Reference samples were prepared in the same manner using 0.075 mmol of each released volatile. The fabric softener samples were rinsed with deionized water and placed into a 3 L beaker, which was filled to a total volume of 1.5 L. Three 5 g cotton swatches (approximately 12.5 × 12.5 cm, mass 270 g / m 2, Testfabrics (West Pittston, PA), item 403, was added to the beaker and stirred by hand for 3 minutes. After an additional 2 minutes, the swatches were collected and the excess water was squeezed out by hand. The swatches were hung to dry at room temperature overnight (15-16 hours). The swatches were then subjected to dynamic headspace analysis.

[0172] Each swatch was placed in a thermostated (25° C.) headspace sample cell (volume approximately 160 mL). An air sampling pump was used to pass a constant flow of air (200 mL / min) through the sampling cell and into a cartridge containing 100 mg of Tenax® (waste cartridge). Before entering the sample cell, air was drawn through a plug of activated charcoal and through a saturated NaCl solution to maintain a constant relative humidity of 75%. Headspace samples were collected after 1 and 2 hours by replacing the waste cartridge with a clean Tenax® cartridge for 15 minutes. The cartridges were thermally desorbed on a Gerstel TDU 3.5 equipped with a cryofocus at −30° C. and desorbed into an Agilent 8890 gas chromatograph equipped with a HP1 capillary column (30 m, 0.25 mm id, 0.25 μm film) and coupled to an Agilent 5977B mass spectrometer. TDU temperature settings for desorption: 40°C to 70°C (30°C / min) hold for 4 min, then heat to 260°C (400°C / min) and hold for 5 min. CIS settings (Tenax® packed liner): cryofocus at -30°C and heat to 300°C at 12°C / s and hold for 4 min (heater mode: standard). PTV inlet settings: 7.7 psi pressure in standard flow mode, total flow rate 99 ml / min, septum purge flow rate 3 ml / min. Inlet mode was set to solvent vent, purge flow to split vent was set to 95 ml / min, and vent flow was set to 50 ml / min. GC furnace temperature profile was 52°C to 110°C at 20°C / min (hold for 2 min) and ramped to 210°C (20°C / min). The amount of each fragrance volatile collected (reported as ng / L air) was determined using an external standard calibration for each chemical. At least five acetone solutions were prepared with analyte concentrations ranging from 0.05 g / L to 5 g / L. The solutions were injected (0.2 μL) onto Tenax® cartridges and desorbed as described above. Each solution was analyzed in triplicate. The calibration curve passed through the origin.

[0173] [Table 1-1] [Table 1-2] [Table 1-3]

[0174] These data show that when applied to cotton fabric from a liquid fabric softener, the compound of formula (I) releases more perfume ingredients (acetaldehyde, formate, and alcohol) than the corresponding reference sample, demonstrating that the compounds of the present invention produce the desired sustained release effect.

[0175] Example 3 Headspace analysis from liquid laundry detergent applications containing compounds of formula (I) of the present invention The pro-fragrance enol ether (0.075 mmol) was weighed into a vial and dissolved in 0.25 mL of acetone. Liquid laundry detergent (4.5 g, Tide® Simply Free and Sensitive) was added to the vial and the mixture was mixed by shaking by hand. The liquid laundry detergent was diluted in 1.0 L of deionized water in a large beaker. Three 5 g cotton swatches (approximately 12.5 × 12.5 cm, mass 270 g / m) were weighed into a vial and dissolved in 0.25 mL of acetone. 2 A 100% aqueous solution of 100% volatiles (Testfabrics, West Pittston, PA), item 403, was added to the beaker, stirred by hand for 2 minutes, and soaked in the detergent solution for an additional 13 minutes. The swatches were removed and excess liquid was squeezed out by hand. In a second beaker, the samples were placed in 500 L of deionized water and soaked by hand in portions for 2 minutes. The swatches were then individually removed and excess liquid was squeezed out by hand. Reference samples were prepared in an identical manner using 0.075 mmol of each volatile released. The fabrics were hung to dry overnight (15-16 hours) at room temperature. The swatches were then subjected to dynamic headspace analysis as described in Example 2.

[0176] [Table 2-1] [Table 2-2]

[0177] These data show that the compounds of formula (I) release more perfume ingredients (acetaldehyde, formate esters, and alcohols) when applied to cotton fabrics from a liquid laundry detergent than the corresponding reference samples, demonstrating that the compounds of the present invention produce the desired sustained release effect.

[0178] Example 4 Headspace Analysis from Fabric Softener Applications Containing Compounds of Formula (I) of the Present Invention and Comparative Compounds The use of the compounds of formula (I) to extend or enhance the perfume effect of aldehydes was compared to compounds described in US Patent Application Publication No. 2004 / 0013779. The ability of these compounds to provide sustained release profile of highly volatile perfume aldehydes was measured by dynamic headspace analysis of cotton samples rinsed with liquid fabric softener and air-dried for 16 hours. The experiment was carried out as described in Example 2, and the data is reported in Table 3.

[0179] [Table 3-1] [Table 3-2]

[0180] The above table reports the amount of perfume aldehyde (octanal, decanal or undecanal) released from the enol ether of formula (I) in comparison with the enol ethers reported in US Patent Application Publication No. 2004 / 0013779. These data show that when the liquid fabric softener is applied to cotton fabric, the compound of formula (I) releases significantly more perfume aldehyde than the comparative example. Considering both time points measured, the compound of formula (I) released at levels 30-39 times higher than octanal, 6.5-31 times higher than decanal and 16-31 times higher than undecanal. This shows that the compounds of the present invention produced the desired sustained release effect, whereas the comparative examples did not. The comparative examples produced very similar levels of aldehyde to the respective reference samples and could not find practical use as sustained release agents for perfume aldehydes to extend or enhance the perfume effect of these aldehydes.

[0181] Example 5 Hydrolysis of compounds according to formula (I) and comparative compounds The acid-catalyzed hydrolysis of compounds 1, 2, 3 and 25 was measured and compared to the hydrolysis of the enol ethers reported in WO 2019243501. Each enol ether was dissolved in a 4:1 THF / 1M HCl mixture and the percent remaining relative to an internal standard over time was measured.

[0182] To a 15 mL vial, 125 mg of the enol ether, 60 mg of hexadecane, and 10 mL of THF (purged with N2 and containing 2500 ppm BHT) were added. After mixing, 2 mL of this solution was taken with a volumetric pipette and used for the time zero measurement. 2 mL of 1 M HCl was mixed with the remaining 8 mL of THF solution. This mixture was divided into 5 mL vials (1 mL per vial). The vials were gently flushed with nitrogen and fitted with screw caps wrapped with parafilm. The vials were stored at room temperature until analysis. For analysis, 2 mL of ethyl acetate was added to the vial and mixed. After phase separation, the upper phase was collected and washed with saturated sodium carbonate (1 mL). A sample of the organic phase was analyzed by GC-FID. For the time zero sample, 0.5 mL of deionized water was added to the 2 mL taken from the original THF solution. 1 mL of this solution was added to a 5 mL vial, diluted with 2 mL of ethyl acetate and mixed. The upper phase was collected and washed with saturated sodium carbonate (1 mL), and then analyzed by GC-FID. The remaining percentage of enol ether was determined by dividing the peak area ratio of the enol ether to the internal standard by the ratio measured at time zero.

[0183] [Table 4]

[0184] The above table shows the hydrolysis rate of the enol ether of formula (I) made from 2-phenylethanol (Z)-3-hexen-1-ol and 3-octanol compared to the enol ether prepared from the same alcohol derived from the phenylacetaldehyde derivative reported in WO2019243501. The table shows that the enol ether of formula (I) is hydrolyzed more rapidly than the corresponding enol ether described in WO2019243501 when treated with 1M HCl (pH 0). Thus, the enol ether of formula (I) can release the perfume ingredient of formula (IV) at different times more quickly than the enol ether reported in WO2019243501 under conditions of use that promote hydrolytic release (e.g., humid climates).

[0185] Example 6 Manufacture of perfume oils Non-limiting examples of typical perfume oils are prepared by combining the following perfuming co-ingredients: [ka] [ka]

[0186] Example 7 Preparation of a multipurpose cleaner containing a compound of formula (I) of the present invention A typical multi-purpose cleaner formulation is shown in Table 5. A perfumed all-purpose cleaner is prepared by adding the perfume oil of Example 6 (0.3-0.8% by weight, based on the total weight of the multi-purpose cleaner) and at least one compound of formula (I) of the present invention (0.05-0.8% by weight, based on the total weight of the multi-purpose cleaner) to the unperfumed multi-purpose cleaner formulation of Table 5 with gentle shaking.

[0187] [Table 5] (1) Neodol® 91-8; Supplier: Shell Chemicals (2) Biosoft® D-40; Supplier: Stepan (3) Stepanate® SCS; Supplier: Stepan (4) Kathon® CG; Supplier: Dow Chemicals.

[0188] Example 8 Preparation of a solid detergent containing a compound of formula (I) of the present invention The model powder detergent base chassis contains sodium sulfate, sodium carbonate, sodium dodecylbenzenesulfonate, sodium silicate, zeolite, C 12-15 Contains Pareth-7, Bentonite, Perborate, TAED, Citric Acid, Sodium Acrylates / MA Copolymer, Sodium Carbonate Peroxide, Tetrasodium Etidronic Acid, Sodium Chloride, Sodium Bicarbonate, Cellulose Gum, Anilinomorpholinotriazinylaminostilbene Sulfonate Disodium, Phenylpropyl Dimethicone, Enzymes, Dyes.

[0189] A typical unperfumed model powder detergent base is made up as listed in Table 6. Perfumed solid detergents are prepared by adding the perfume oil of Example 6 (0.3-0.6% by weight, based on the total weight of the solid detergent) and at least one compound of formula (I) of the present invention (0.15% by weight, based on the total weight of the solid detergent) with gentle shaking.

[0190] [Table 6]

[0191] Example 9 Preparation of bleach-free detergent bars containing the compounds of formula (I) of the present invention A typical bleach-free powder detergent formulation contains sodium sulfate, sodium carbonate, sodium dodecylbenzenesulfonate, sodium silicate, zeolite, C 12-15It consists of Pareth-7, bentonite, citric acid, sodium acrylate / MA copolymer, sodium carbonate peroxide, tetrasodium etidronate, sodium chloride, sodium bicarbonate, cellulose gum, disodium anilinomorpholinotriazinylaminostilbene sulfonate, phenylpropyl dimethicone, enzymes, and dyes.

[0192] A typical unperfumed model powder detergent base is made up as listed in Table 7. A perfumed bleach-free detergent solid is prepared by adding the perfume oil of Example 6 (0.3-0.6% by weight based on the total weight of the bleach-free detergent solid) and at least one compound of formula (I) of the present invention (0.15% by weight based on the total weight of the bleach-free detergent solid) with gentle shaking.

[0193] [Table 7]

[0194] Example 10 Preparation of dishwashing detergent formulations containing compounds of formula (I) of the present invention A typical dish detergent formulation is shown in Table 8. Mix water, sodium hydroxide and diethanolamide. Then add linear alkylbenzene sulfonic acid. After neutralization, add remaining ingredients. Check pH (7-8) and adjust if necessary. A perfumed dish detergent is prepared by adding perfume oil of Example 6 (0.4-0.8% by weight based on the total weight of the dish detergent formulation) and at least one compound of formula (I) of the present invention (0.02-0.5% by weight based on the total weight of the dish detergent formulation) to the unperfumed dish detergent formulation of Table 8 with gentle shaking.

[0195] [Table 8] (1) Biosoft® S-118; Supplier: Stepan (2) Ninol® 40-CO; Supplier: Stepan (3) Stepanate® SXS; Supplier: Stepan (4) Tergitol® 15-S-9; Supplier: Dow Chemicals.

[0196] Example 11 Preparation of a clear isotropic shampoo formulation containing a compound of formula (I) of the present invention A typical unflavored, clear, isotropic shampoo formulation is shown in Table 9. The unflavored shampoo formulation is prepared by dispersing Polyquaternium-10 in water. The remaining ingredients of Phase A are mixed by adding them one after the other with good mixing after each addition. This premix is ​​added to the Polyquaternium-10 dispersion and mixed for an additional 5 minutes. Then, with stirring, add premixed Phase B and premixed Phase C (Monomuls® 90L-12 heated to melt in Texapon® NSO IS). With stirring, add Phase D and Phase E. The pH is adjusted to 5.5-6.0 with citric acid solution to obtain the unflavored shampoo formulation listed in Table 9. A perfumed shampoo formulation is obtained by adding the perfume oil of Example 6 (0.1-0.8% by weight, relative to the total weight of the shampoo formulation) and at least one compound of formula (I) according to the invention (0.05-0.5% by weight, relative to the total weight of the shampoo formulation) to the unperfumed shampoo formulation of Table 9, while shaking gently.

[0197] [Table 9] (1) Ucare® Polymer JR-400; Supplier: Noveon (2) Supplier: Brenntag Schweizerhall AG (3) Glydant (registered trademark); Supplier: Lonza (4) Texapon (registered trademark) NSO IS; Supplier: Cognis (5) Tego® Betain F 50; Supplier: Evonik (6) Amphotensid GB 2009;Supplier: Zschimmer & Schwarz (7) Brij® S20; Supplier: Croda (8) Monomuls® 90 L-12; Supplier: Gruenau GmbH (9) Nipagin Monosodium;Supplier: NIPA Company.

[0198] Example 12 Preparation of pearlescent shampoo formulations containing compounds of formula (I) of the present invention A typical unflavored pearlescent shampoo formulation is shown in Table 10. The unflavored shampoo formulation is prepared by dispersing tetrasodium EDTA, guar hydroxypropyltrimonium chloride, and Polyquaternium-10 in water. NaOH (10% in water, Phase B) is added once Phase A is homogenous. Then premixed Phase C is added and the mixture is heated to 75°C. Phase D ingredients are added and mixed until the mixture is homogenous. The mixture is cooled. At 45°C, Phase E is added with mixing. The final viscosity is adjusted with NaCl (25% in water) and the pH is adjusted to 5.5-6.0 with NaOH (10% in water). A perfumed pearly shampoo formulation is obtained by adding the perfume oil of Example 6 (0.1-0.8% by weight, relative to the total weight of the shampoo formulation) and at least one compound of formula (I) of the present invention (0.05-0.5% by weight, relative to the total weight of the shampoo formulation) to the unperfumed pearly shampoo formulation of Table 10, while gently shaking.

[0199] [Table 10] (1) EDETA® B Powder; Supplier: BASF (2) Jaguar® C14 S; Supplier: Rhodia (3) Ucare® Polymer JR-400; Supplier: Noveon (4) Sulfetal® LA BE; Supplier: Zschimmer & Schwarz (5) Zetesol® LA; Supplier: Zschimmer & Schwarz (6) Tego® Betain F 50; Supplier: Evoniks (7) Xiameter® MEM-1691; Supplier: Dow Corning (8) Lanette® 16; Supplier: BASF (9) Comperlan® 100; Supplier: Cognis (10) Cutina(R) AGS; Supplier: Cognis (11) Kathon® CG; Supplier: Rohm & Haas (12) D-Panthenol; Supplier: Roche.

[0200] Example 13 Preparation of Rinse-Off Hair Conditioner Formulations Containing Compounds of Formula (I) of the Invention A typical unflavored rinse-off hair conditioner formulation is shown in Table 11. An unflavored rinse-off hair conditioner formulation is prepared by mixing the ingredients of Phase A until a homogenous mixture is obtained. The Tylose® is completely dissolved. The mixture is then heated to 70-75°C. The ingredients of Phase B are combined and melted at 70-75°C. The ingredients of Phase B are then added to Phase A with good mixing and mixing is continued until the mixture is at a temperature of 60°C. The ingredients of Phase C are then added and mixing is maintained with stirring until the mixture is cooled to 40°C. The pH is adjusted with citric acid solution to pH: 3.5-4.0. A perfumed rinse-off hair conditioner formulation is obtained by adding the perfume oil of Example 6 (0.2-1.0% by weight, relative to the total weight of the conditioner formulation) and at least one compound of formula (I) of the present invention (0.05-0.5% by weight, relative to the total weight of the conditioner formulation) to an unperfumed rinse-off hair conditioner formulation of Table 11 with gentle shaking.

[0201] [Table 11] (1) Genamin® KDMP; Supplier: Clariant (2) Tylose® H10 Y G4; Supplier: Shin Etsu Co., Ltd. (3) Lanette® O; Supplier: BASF (4) Arlacel® 165; Supplier: Croda (5) Incroquat® Behenyl TMS-50-PA-(MH); Supplier: Croda (6) Brij® S20; Supplier: Croda (7) Xiameter® MEM-949; Supplier: Dow Corning (8) Supplier: Alfa Aesar.

[0202] Example 14 Preparation of structured shower gel formulations containing compounds of formula (I) of the present invention A typical unperfumed structured shower gel formulation is shown in Table 12. The perfumed structured shower gel is prepared by adding the perfume oil of Example 6 (0.1-1.5% by weight, based on the total weight of the structured shower gel) and at least one compound of formula (I) of the present invention (0.05-0.5% by weight, based on the total weight of the structured shower gel) to the unperfumed structured shower gel formulation of Table 12 with gentle shaking.

[0203] [Table 12] (1) EDETA B powder;Supplier: BASF (2) Carbopol Aqua SF-1 polymer;Supplier: Noveon (3) Zetesol AO 328 U;Supplier: Zschimmer & Schwarz (4) Tego Betain F 50; Supplier: Goldschmidt (5) Kathon® CG; Supplier: Rohm & Haas Company.

[0204] Example 15 Preparation of a transparent shower gel formulation containing a compound of formula (I) according to the present invention A typical unperfumed clear shower gel formulation is shown in Table 13. Perfumed clear shower gels are prepared by adding the perfume oil of Example 6 (0.5-1.5% by weight, based on the total weight of the clear shower gel) and at least one compound of formula (I) of the present invention (0.05-0.5% by weight, based on the total weight of the clear shower gel) to the unperfumed clear shower gel formulation of Table 13 with gentle shaking.

[0205] [Table 13]

[0206] Example 16 Preparation of a milky shower gel formulation containing a compound of formula (I) according to the present invention A typical unflavored milky shower gel formulation is shown in Table 14. The unflavored milky shower gel is prepared by adding the perfume oil of Example 6 (0.1-1.5% by weight, based on the total weight of the milky shower gel) and at least one compound of formula (I) according to the invention (0.05-0.5% by weight, based on the total weight of the milky shower gel) to the unflavored milky shower gel formulation of Table 14 with gentle shaking.

[0207] [Table 14] (1) EDETA® B powder; Supplier: BASF (2) Texapon (registered trademark) NSO IS; Supplier: Cognis (3) Merquat® 550; Supplier: Lubrizol (4) Dehyton(R) AB-30; Supplier: Cognis (5) Glucamate® LT; Supplier: Lubrizol (6) Euperlan(R) PK 3000 AM; Supplier: Cognis (7) Cremophor® RH 40; Supplier: BASF.

Claims

1. below, a) an aldehyde compound of formula (II) 【Chemistry 1】 [In the formula, R 1 is C 1-15 Alkyl group, C 3-15 Alkenyl group, C 3-15 Cycloalkyl group, C 5-15 Cycloalkenyl group or C 3-14 Heterocycloalkyl groups, such as C 1-8 Alkyl group, C 1-8 Alkoxy group, hydroxy group, carboxylic acid group and / or C 1-4 hydroxy groups, each optionally substituted with one or more carboxylic acid ester groups, C 1-15 Alkyl group, C 2-15 Alkenyl group, C 1-15 Alkoxy group, C 2-15 Alkenyloxy group, C 3-15 Cycloalkyl group, C 5-15 Cycloalkenyl group, C 3-15 Heterocycloalkyl group, carboxylic acid group, C 1-4 Carboxylic acid ester group, C 6-10 aryl group and / or C 6-10 C, each optionally substituted with one or more aryloxy groups; 1-15 Alkyl group, C 3-15 Alkenyl group, C 3-15 Cycloalkyl group, C 5-15 Cycloalkenyl group or C 3-14 a heterocycloalkyl group] b) formic acid ester of formula (III) 【Chemistry 2】 [In the formula, R 2 is a C optionally containing one or two oxygen atoms 4-18 hydrocarbon groups, except for the ester functional group alpha to the formyloxy group, and R 2 does not contain an allyl functional group] c) an alcohol of formula (IV) 【Transformation 3】 [In the formula, R 2 has the same meaning as defined above. from a precursor compound of formula (I) by exposing the precursor compound to an environment that oxidizes the precursor compound, wherein the precursor compound is of formula (I): 【Chemistry 4】 [In the formula, R 1 and R 2 has the same meaning as defined above] in the form of any of its stereoisomers or mixtures thereof.

2. The compound of formula (I) is 18-36 Compounds, preferably C 20-36 The method of claim 1 , wherein the compound is a compound.

3. R 2 C optionally containing one or two oxygen atoms 5-18 The method of claim 1 , wherein the alkyl group is a hydrocarbon group.

4. R 2 C optionally containing one or two oxygen atoms 6-18 The method of claim 3, wherein the alkyl group is a hydrocarbon group.

5. R 2 But C 1-15 Alkyl group, C 2-15 Alkenyl group, C 3-15 Cycloalkyl group or C 5-15 A cycloalkenyl group, 1-8 Alkyl, C 1-8 a hydroxy group, each optionally substituted with one or more of alkoxy, hydroxy and / or carboxylic acid, C 1-15 Alkyl group, C 1-15 Alkoxy group, C 3-15 Cycloalkyl group, C 5-15 Cycloalkenyl group, C 6-10 aryl group and / or C 6-10 C, each optionally substituted with one or more aryloxy groups; 1-15 Alkyl group, C 2-15 Alkenyl group, C 3-15 Cycloalkyl group or C 5-15 The method of claim 1 , wherein the alkyl group is a cycloalkenyl group.

6. R 1 But C 1-10 Alkyl group, C 3-10 Alkenyl group, C 3-11 Cycloalkyl group or C 5-11 A cycloalkenyl group, 1-4 Alkyl group, hydroxy group and / or C 1-4 a hydroxy group, each optionally substituted with one or more alkoxy groups; 1-4 Alkyl group, C 1-4 Alkoxy group, C 3-8 Cycloalkyl group, C 5-8 Cycloalkenyl group, C 6 aryl group and / or C 6 C, each optionally substituted with one or more aryloxy groups; 1-10 Alkyl group, C 3-10 Alkenyl group, C 3-11 Cycloalkyl group or C 5-11 The method of claim 1 , wherein the alkyl group is a cycloalkenyl group.

7. 2. The method of claim 1, wherein the compounds of formula (II), formula (III) and / or formula (IV) are perfuming ingredients.

8. 10. The method of claim 1, wherein the environment in which the compound is oxidized is air.

9. 10. A method for imparting, enhancing, improving or modifying the odor characteristics of a perfumed composition, the air surrounding a perfumed composition, a surface or a perfumed article, said method comprising adding to said composition, said air or said article, or contacting or treating said surface with an effective amount of at least one compound of formula (I) as defined in any one of claims 1 to 8.

10. A method for enhancing or prolonging the diffusion effect of the characteristic fragrance of at least one aldehyde compound of formula (II), at least one active formate ester of formula (III) and / or at least one active alcohol of formula (IV) as defined in any one of claims 1 to 8 on a surface or air surrounding a perfuming composition treated with at least one compound (I) as defined in any one of claims 1 to 8 or treated with a composition or article comprising at least one compound (I) under conditions conducive to the release over time of at least one ketone or aldehyde of formula (II), at least one formate ester of formula (III) and / or at least one alcohol of formula (IV).

11. below, i) at least one compound of formula (I) according to any one of claims 1 to 8, ii) at least one ingredient selected from the group consisting of a perfume carrier and a perfume base; and iii) optionally at least one perfume adjuvant A perfume composition comprising:

12. A scented consumer product comprising at least one compound of formula (I) as defined in any one of claims 1 to 8.

13. 13. The scented consumer product of claim 12, wherein the perfumed consumer product is a perfume, a fabric care product, a body care product, a cosmetic preparation, a skin care product, an air care product, or a home care product.

14. The perfumed consumer product may be a fine perfume, splash or eau de parfum, cologne, shave or aftershave lotion, liquid or solid detergent, optionally in pod or tablet form, fabric softener, liquid or solid scent booster, dryer sheet, fabric refresher, ironing water, paper, bleach, carpet cleaner, curtain care product, shampoo, leave-on or rinse-off hair conditioner, hair dye, color care product, hair shaping product, dental care product, disinfectant, intimate care product, hair spray 14. The perfumed consumer product of claim 13, characterized in that it is a soap, a skin cream or lotion, a vanishing cream, a deodorant or antiperspirant, a depilatory, a tanning or sunscreen or after-sun product, a nail product, skin cleanser, make-up, a scented soap, a shower or bath mousse, oil or gel, a foot / hand care product, a hygiene product, an air freshener, a "ready to use" powdered air freshener, a mold remover, a furnisher care, a wipe, a dish detergent or hard surface cleaner, a leather care product, or a car care product.

15. Formula (I) 【Transformation 5】 [In the formula, R 1 contains at least 6 carbon atoms, and C 1-15 Alkyl group, C 3-15 Alkenyl group, C 3-15 Cycloalkyl group, C 5-15 Cycloalkenyl group or C 3-14 heterocycloalkyl groups, each optionally selected from C 1-8 Alkyl group, C 1-8 Alkoxy group, hydroxy group, carboxylic acid group and / or C 1-4 a hydroxy group substituted with one or more of a carboxylic acid ester group, C 1-15 Alkyl group, C 2-15 Alkenyl group, C 1-15 Alkoxy group, C 2-15 Alkenyloxy group, C 3-15 Cycloalkyl group, C 5-15 Cycloalkenyl group, C 3-15 Heterocycloalkyl group, carboxylic acid group, C 1-4 Carboxylic acid ester group, C 6-10 aryl group and / or C 6-10 C, each optionally substituted with one or more aryloxy groups; 1-15 Alkyl group, C 3-15 Alkenyl group, C 3-15 Cycloalkyl group, C 5-15 Cycloalkenyl group or C 3-14 heterocycloalkyl groups, wherein the heteroatoms represent one or more oxygen atoms, provided that R 1 is not a 2-hexylidenecyclopentyl group; R 2 optionally containing one or two oxygen atoms, C 6-18 hydrocarbon groups, except for the ester functional group α to the oxy group, and R 2 is a benzyl group, a cyclohexyl group, a 2-hydroxy-1,2-diphenylethyl group, or a 1-(tert-butoxy)-7,7-dimethylbicyclo[2.1]heptan-2-yl group, which do not contain an allyl function; and excluding 1-(heptyloxy)dec-1-ene, 1-(decyloxy)dec-1-ene, 1-(dodecyloxy)dodec-1-ene, (4-phenethoxybut-3-en-1-yl)benzene, and 1-((3,7-dimethyloctyl)oxy)-3,7-dimethyloct-1-ene. Compounds of formula (I) in the form of any one of its stereoisomers or mixtures thereof.

16. A scented consumer product comprising the scenting composition defined in claim 11.

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