Compounds for imparting long-lasting floral and fruity scents

Abstract

The present invention relates to the field of perfumery. The present invention relates to a compound of formula (I) capable of imparting a long-lasting or persistent scent, particularly a floral and / or fruity scent, to an environment. Furthermore, the present invention relates to a method for imparting a long-lasting scent, particularly a fresh green, floral and / or fruity scent, to surfaces such as hard surfaces, fabrics, skin or hair. Furthermore, the present invention relates to the use of the compound in perfumery, as well as to a perfumed composition or perfumed article comprising the compound of the present invention.

Description

[Technical Field]

[0001] Technical Field The present invention relates to the field of perfumery. The present invention relates to compounds of formula (I) that can impart a long-lasting or persistent scent, particularly a fresh green, floral and / or fruity scent, to an environment. Furthermore, the present invention relates to a method for imparting a long-lasting scent, particularly a fresh green, floral and / or fruity scent, to surfaces such as hard surfaces, fabrics, skin or hair. Furthermore, the present invention relates to the use of the compounds in perfumery, as well as to perfumed compositions or perfumed articles comprising the compounds of the present invention.

[0002] Conventional technology Consumers often associate the effectiveness of a perfumed article with the longevity or persistence of the fragrance perception. Perfumes are composed of many different volatile compounds that adhere to a surface and evaporate from there to produce a scent. Perfumes, for example, as fine fragrances or various cleaning and cleaning agents, are applied to surfaces such as hard surfaces, fabrics, skin, or hair through perfume compositions or perfumed consumer articles. Due to the high volatility of the fragrances that make up a perfume, the scent released from the scented surface can only be perceived for a limited time. In particular, the so-called top notes of a perfume evaporate very quickly. Top notes are the most volatile compounds in a composition and represent the freshness of a perfume. Top notes typically include citrus, flowery, green, and fruity notes, among others, and floral and fruity notes are particularly highly valued by consumers. Several classes of floral and fruity notes are used in perfumery. Typical examples of fruity notes are those resembling blackcurrant, blackcurrant, and exotic fruits, as well as red berries such as raspberry or strawberry.

[0003] Consumers are looking for fragrances that are stable for their intended use, while also providing long-lasting or persistent fragrance for hours and even days after application. Long-lasting floral and fruity notes are particularly desirable.

[0004] It is therefore an object of the present invention to provide a system capable of delivering long-lasting or persistent scents to an environment, particularly floral and / or fruity scents, but also other scents such as fresh, green, and minty scents. Yet another object of the present invention is to find a method for imparting long-lasting scents, particularly fresh, green, floral, and / or fruity scents, to surfaces such as hard surfaces, fabrics, skin, or hair by application of a perfumed composition or a perfumed article.

[0005] Detailed Description of the Invention The inventors have now discovered that several specific compounds can be advantageously utilized to impart a long-lasting or persistent perfume effect, particularly fresh green, floral and / or fruity odor notes, into an environment from a given surface, and are therefore useful as ingredients in perfumed compositions or perfumed articles.

[0006] Thus, a first aspect of the present invention provides a compound of formula [ka] [In the formula, R 1 and R 1’ represent, independently of each other, a hydrogen atom or a methyl group; or both R 1 and / or both R 1’ when taken together represent a divalent C3-C8 hydrocarbon group; R 2 and R 2’ are each independently a hydrogen atom or a C1-C 12 represents a hydrocarbon group, R 3 and R 3’ are each independently a hydrogen atom or a C1-C16 represents a hydrocarbon group; R 1 and R 3 and / or R 1’ and R 3’ together form the divalent C2 to C 12 capable of being attached to a hydrocarbon group, Q is a divalent C2-C optionally containing 1 to 8 ether groups and / or 1 or 2 functional groups selected from the group consisting of alcohols, ketones, aldehydes, esters, thioethers, carboxylic acids, alkali carboxylates, amines, amides, carbamates, nitriles, or thiols. 22 represents a hydrocarbon group; and Each X is independently a group of formula (i) to (iii) [ka] wherein the wavy lines indicate the positions of the bonds between carbons 2 and 2′ and X, and the slash indicates the position of the bond between X and Q, with the proviso that the slash is not directly attached to the heteroatom or carbonyl functionality of Q.

[0007] A "hydrocarbon group" is understood to mean that said group consists of hydrogen and carbon atoms and may be in the form of an aliphatic hydrocarbon, i.e., a linear or branched, saturated hydrocarbon (e.g., an alkyl group), a linear or branched, unsaturated hydrocarbon (e.g., an alkenyl or alkynyl group), a saturated cyclic hydrocarbon (e.g., a cycloalkyl) or an unsaturated cyclic hydrocarbon (e.g., a cycloalkenyl or cycloalkynyl), or may be in the form of an aromatic hydrocarbon, i.e., an aryl group, or even a mixture of the above types of groups; for example, a particular group may contain linear alkyl, branched alkenyl (e.g., having one or more carbon-carbon double bonds), (poly)cycloalkyl and aryl moieties, unless specifically stated to be limited to only one type. Similarly, in all embodiments of the present invention, when a group is described as being 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), this also means that the group can contain moieties having any one of the above topologies or moieties that are saturated or unsaturated, as described above. Similarly, in all embodiments of the present invention, when a group is described as being in the form of one type of saturated or unsaturated (e.g., alkyl), this means that the group can be in any type of topology (e.g., linear, cyclic, or branched), or have multiple moieties with different topologies.

[0008] The terms "hydrocarbon group optionally comprising ..." and "hydrocarbon group optionally substituted with ..." are understood to mean that the hydrocarbon group optionally contains an alcohol, ketone, aldehyde, ether, thioether, ester, carboxylic acid, alkyl carboxylate, amine, amide, carbamate, nitrile, or thiol group. These groups can either be attached laterally to the hydrocarbon group by replacing a hydrogen atom of the hydrocarbon group, or inserted into the hydrocarbon chain by replacing a carbon atom of the hydrocarbon group (where chemically possible). For example, the -CH2-CH2-CHOH-CH2- group represents a C4 hydrocarbon group containing an alcohol group (substitution of a hydrogen atom), the -CH2-CH2-COO-CH2-CH2-OCO-CH2-CH2- group represents a C6 hydrocarbon group containing two ester groups (substitution of a carbon atom / insertion into the hydrocarbon chain), and similarly, the -CH2-CH2-O-CH2-CH2-O-CH2-CH2- group represents a C6 hydrocarbon group containing two ether groups.

[0009] In one embodiment of the present invention, the two X groups attached to Q are separated from each other by at least four carbon atoms.

[0010] The term "two X groups bonded to Q are separated from each other by at least four carbon atoms" means that there are at least four different carbon atoms of Q between one X group and the second X group. These four carbon atoms can be part of any substituted or unsubstituted hydrocarbon group, provided that the shortest path to travel from one X group to the other X group passes through at least four different carbon atoms of Q.

[0011] In a preferred embodiment, the two X groups attached to Q are separated from each other by at least 5, preferably 6, carbon atoms.

[0012] According to an optional embodiment of the present invention, all R in formula (I) 1 and R 1’ , R 2 and R 2’ , and R3 and R 3’ may be different, preferably R 1 and R 1’ , R 2 and R 2’ , and R 3 and R 3’ are pairwise equivalent.

[0013] As used herein, "R 1 and R 1’ The expression "independently represents ..." is used to express the (two) R 1 and (two) R 1’ each independently of the other represents the indicated substituent, i.e., a hydrogen atom or a methyl group; or both R 1 and / or both R 1’ taken together are understood to represent a divalent C3-C8 hydrocarbon radical. In other words, R alpha to the carbonyl group 1 can be a hydrogen atom or a methyl group, while R 2 geminal R 1 may independently be hydrogen or a methyl group, and R alpha to the carbonyl group 1’ can be a hydrogen atom or a methyl group, while R 2’ geminal R 1’ may independently be hydrogen or a methyl group; or both R 1 and / or both R 1’ when taken together represent a divalent C3-C8 hydrocarbon group. In certain embodiments, both R 1 represents a hydrogen atom or a methyl group, and independently, both R 1’ represents a hydrogen atom or a methyl group; or both R 1 and / or both R 1’ when taken together represent a divalent C3 to C8 hydrocarbon group.

[0014] According to any embodiment of the present invention, R 1 and R 1’may each independently preferably represent a hydrogen atom or a methyl group, and preferably R 1 and R 1’ may each independently be a hydrogen atom.

[0015] According to any embodiment of the present invention, R 2 and R 2’ are each independently preferably C1 to C 12 Hydrocarbon groups, even more preferably C1-C 10 may represent a hydrocarbon group, preferably R 2 and R 2’ are each independently a methyl group, an ethyl group, a C6 to C 10 an alkyl or alkenyl group, or a C5-C optionally substituted with 1-3 C1-C3 alkyl or C2-C3 alkenyl groups; 10 It can be a cycloalkyl group or a cycloalkenyl group, preferably R 2 and R 2’ are each independently a methyl group, an ethyl group, or a C6 to C 10 It may be an alkyl or alkenyl group, and even more preferably, R 2 and R 2’ may each independently be a methyl group.

[0016] According to a particular embodiment, both R 1 and / or both R 1’ together represent a divalent C3-C8 hydrocarbon group, or R 2 geminal R 1 , and R 3 , and / or R 2 geminal R 1’ , and R 3’ But together, the divalent C2~C 12 If it can be bonded to a hydrocarbon group, R 2 and / or R 2’ may each independently preferably represent a hydrogen atom. 2 and / or R 2’may each independently not represent a hydrogen atom if at least one molecule to be released does not contain a ring; i.e., both R 1 and / or both R 1’ together, or R 2 geminal R 1 , and R 3 , and / or R 2 geminal R 1’ , and R 3’ together form a ring.

[0017] According to any embodiment of the present invention, R 3 and R 3’ are each independently preferably a hydrogen atom or a C1 to C 10 may represent a hydrocarbon group, R 3 and R 3’ may each independently represent a C1 to C9 hydrocarbon group, and even more preferably, R 3 and R 3’ may each independently represent a C4 hydrocarbon group, most preferably R 3 and R 3’ may each independently represent an n-butyl group.

[0018] According to any embodiment of the present invention, R 1 and R 3 and / or R 1’ and R 3’ taken together may preferably represent a divalent C2-C6 hydrocarbon group.

[0019] According to an optional embodiment of the present invention, both R 1 and / or both R 1’ When combined, C 5~8 Cycloalkyl group or C 5~8 cycloalkenyl groups, each of which may optionally contain 1 to 3 C 1~8 Alkyl group or C 1~8 It is substituted by an alkenyl group.

[0020] 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. The terms "cycloalkyl" and "cycloalkenyl" are understood to include monocyclic or fused, spiro, and / or bridged bicyclic or tricyclic cycloalkyl and cycloalkenyl groups, preferably monocyclic cycloalkyl and cycloalkenyl groups.

[0021] According to any embodiment of the present invention, Q is preferably a divalent C4-C aryl group optionally containing 1 to 8 ether groups and / or having one or two functional groups selected from the group consisting of alcohols, ketones, aldehydes, esters, carboxylic acids, amines, amides or carbamates. 22 , preferably C4 to C 18 , more preferably C5 to C 18 Preferably, Q is a divalent C2-C alkyl group, optionally containing 1 to 6 ether groups and / or having one or two functional groups selected from the group consisting of alcohols, esters, carboxylic acids, amines or carbamates. 18 , preferably C4 to C 18 , more preferably C5 to C 18 Preferably, Q is a divalent C3-C6 alkyl or alkenyl group, optionally having 1 to 4 ether groups. 16 , preferably C4 to C 16 , more preferably C5 to C 16 , a divalent C4-C alkyl or alkenyl group, optionally having 1 to 4 ether groups. 12 More preferably, Q is a divalent C2-C alkyl group. 16 , preferably C4 to C 16 , more preferably C5 to C 16 Alkyl, C2-C 16 , preferably C4 to C 16 , more preferably C5 to C16 Alkenyl or C4-C 16 It may represent a mono-, di-, tri- or tetraoxoalkyl group.

[0022] According to certain embodiments, Q may represent a divalent butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, 3-oxapentyl, 3,6-dioxaoctyl, 3,6,9-trioxaundecyl, 3,6,9,12-tetraoxatetradecyl, and even more preferably, Q may represent a divalent hexyl, octyl, decyl, dodecyl, 3-oxapentyl, 3,6-dioxaoctyl, 3,6,9-trioxaundecyl, or 3,6,9,12-tetraoxatetradecyl group, and even more preferably, Q may represent a divalent 3,6-dioxaoctyl group.

[0023] According to any embodiment of the present invention, each X may represent the same group, preferably selected from among formulae (i) to (iii).

[0024] According to any embodiment of the present invention, preferably each X may independently represent a group of formula (i) or (ii), most preferably a group of formula (i).

[0025] According to a particular embodiment, R 1 and R 1’ may represent a hydrogen atom or a methyl group, R 2 and R 2’ may represent a methyl or ethyl group, R 3 and R 3’ is a hydrogen atom or C1-C 10 may represent a hydrocarbon group, R 1 and R 3 and / or R 1’ and R 3’ may, when taken together, represent a divalent C2-C6 hydrocarbon radical, X may represent a radical of formula (i) and / or (ii), and Q may represent a divalent C2-C6 hydrocarbon radical, optionally containing 1 to 4 ether groups and / or having 1 or 2 functional groups selected from the group consisting of esters, alcohols, amines, or carbamates. 16, preferably C4 to C 18 It may represent an alkyl or alkenyl group.

[0026] In certain embodiments of the present invention, the following compounds are excluded from the compounds of formula (I): 3,3'-(ethane-1,2-diylbis(sulfanediyl))dipropanal, 3,3'-(propane-1,3-diylbis(sulfanediyl))dipropanal, 3,3'-(butane-1,4-diylbis(sulfanediyl))dipropanal, 3,3'-((oxybis(ethane-2,1-diyl))bis(sulfanediyl))dipropanal, ethane-1,2-diylbis(2-((3-oxopropyl)thio)acetate), 3,3'-(butane- 1,4-diyldisulfonyl)dipropanal, 4,4'-(ethane-1,2-diylbis(sulfanediyl))bis(butan-2-one), 4,4'-(propane-1,3-diylbis(sulfanediyl))bis(butan-2-one), 4,4'-(butane-1,4-diyldisulfonyl)bis(butan-2-one), 4,4'-(propane-2,2-diylbis(sulfanediyl))bis(butan-2-one), 4,4'-(propane-2,2-diylbis(sulfanediyl))bis(4-methylpentan-2-one), 4,4'-(propane 4,4'-(pentane-2,2-diylbis(sulfanediyl))bis(4-methylhexan-2-one), 4,4'-(butane-2,2-diylbis(sulfanediyl))bis(4-methylpentan-2-one), 4,4'-(pentane-3,3-diylbis(sulfanediyl))bis(4-methylpentan-2-one), 4,4'-(pentane-2,2-diylbis(sulfanediyl))bis(4-methylpentan-2-one), 4,4'-(heptane-3,3-diylbis(sulfanediyl))bis(4-methylpentan-2-one), 1,1'-(propane 1,1'-(heptane-3,3-diylbis(sulfanediyl))bis(hex-5-en-3-one), 1,1'-(propane-2,2-diylbis(sulfanediyl))bis(hept-5-en-3-one), 3,3'-(propane-2,2-diylbis(sulfanediyl))bis(1-cyclohexylpropan-1-one), 3,3'-(hexane-2,2-diylbis(sulfanediyl))bis(1-cyclohexylpropan-1-one), 5,5'-(propane-2,2-diylbis(sulfanediyl))bis(1-cyclohexylpentan-3-one), 3,3'-(propane-2,2-diylbis(sulfanediyl))bis(1-phenylpropan-1-one), 3,3'-(propane-2,2-diylbis(sulfanediyl))bis(1-(naphthalen-2-yl)propan-1-one), 3,3'-(propane-2,2-diylbis(sulfanediyl))bis(1,3-diphenylpropan-1-one), 4,4'-(methylenebis(sulfanediyl))bis(4-phenylpropan-1-one) 3,3'-(propane-2,2-diylbis(sulfanediyl))bis(1,3-diphenylbutan-1-one, 3,3'-(propane-2,2-diylbis(sulfanediyl))bis(1-(p-tolyl)propan-1-one), 3,3'-(propane-2,2-diylbis(sulfanediyl))bis(1-(3,5-dimethylphenyl)propan-1-one), 3,3'-(propane-2,2-diylbis(sulfanediyl))dipropanal, 3,3'-(propane-2,2-diylbis(sulfanediyl))bis(1-(p-tolyl)propan-1-one) ))dibutanal, 3,3'-(propane-2,2-diylbis(sulfanediyl))bis(3-phenylpropanal), 4,4'-((phenylmethylene)bis(sulfanediyl))bis(butan-2-one), 4,4'-((phenylmethylene)bis(sulfanediyl))bis(4-methylpentan-2-one), 3,3'-(butane-1,1-diylbis(sulfanediyl))dipropanal, 3,3'-((phenylmethylene)bis(sulfanediyl))bis(3-phenylpropanal), 4,4'-(butane-1,1-di bis(4-methylpentan-2-one), 3,3'-(ethane-1,2-diylbis(sulfanediyl))bis(cyclopentan-1-one), 3,3'-(propane-1,3-diylbis(sulfanediyl))bis(cyclopentan-1-one), 3,3'-(ethane-1,2-diylbis(sulfanediyl))bis(cyclohexan-1-one), 3,3'-((propane-1,3-diylbis(sulfanediyl))bis(methylene))bis(cyclohexan-1-one), 4,4'-(naphthalene-1,5-diylbis(sulfanediyl))bis(butan-2-one), 3,3'-(propane-2,2-diylbis(sulfanediyl))bis(1-cyclohexylpropan-1-one), 4,4'-(1,3-phenylenebis(sulfanediyl))bis(4-phenylbutan-2-one), 3,3'-(ethane-1,2-diylbis(sulfanediyl))bis(1,3-diphenyl phenylpropan-1-one), 2,3-bis((2-(4-methyl-2-oxocyclohexyl)propan-2-yl)thio)naphthalene-1,4-dione, 4,4'-(methylenebis(4,1-phenylenesulfonyl))bis(4-methylpentan-2-one) and 4,4'-([1,1'-biphenyl]-4,4'-disulfonyl)bis(4-methylpentan-2-one). In particular, the following compounds are excluded from the compounds of formula (I): 4,4'-(methylenebis(4,1-phenylenesulfonyl))bis(4-methylpentan-2-one) and 4,4'-([1,1'-biphenyl]-4,4'-disulfonyl)bis(4-methylpentan-2-one).

[0027] In certain embodiments of the present invention, the following compound is excluded from formula (I): ethane-1,2-diylbis(2-((4-oxooctan-2-yl)thio)acetate).

[0028] In certain embodiments of the present invention, the following compounds are excluded from formula (I): 2~20 Alkyl-1,2-diylbis(2-((4-oxooctan-2-yl)thio)acetate), C 2~20 Alkyl-1,2-diylbis(2-((4-oxooctan-2-yl)sulfinyl)acetate) and / or C 2~20 Alkyl-1,2-diylbis(2-((4-oxooctan-2-yl)sulfonyl)acetate).

[0029] According to one embodiment, the compound of formula (I) may be a homodimer or a heterodimer. A homodimer is herein understood to mean that the two substituents attached to X (and not including Q) have the same chemical structure. A heterodimer is herein understood to mean that the two substituents attached to X (and not including Q) have different chemical structures. In other words, R 3 C(=O)CHR 1 CR 2 R 1 Groups and R 3’ C(=O)CHR 1’ CR 2’ R 1’ The groups may be the same or different and are homodimers or heterodimers, respectively.

[0030] According to any embodiment of the present invention, the compound of formula (I) preferably has the formula [ka] [In the formula, R 1 , R 2 , R 3 , X and Q have the same meaning as in formula (I), and even more preferably the compound of formula (I) is a compound of formula [ka] wherein X and Q have the same meanings as given for the compounds of formula (I).

[0031] According to any one of the above embodiments, the compound of formula (I) has an alkyl group size of C4 to C 22 Between C4 and C 18 Between C5 and C6, and more preferably 16Varying between 2,2'-(alkane-α,ω-diylbis(sulfanediyl))bis(octan-4-one), e.g., 2,2'-(hexane-1,6-diylbis(sulfanediyl))bis(octan-4-one), 2,2'-(heptane-1,7-diylbis(sulfanediyl))bis(octan-4-one), 2,2'-(octane-1,8-diylbis(sulfanediyl))bis(octan-4-one), 2,2 '-(nonane-1,9-diylbis(sulfanediyl))bis(octan-4-one), 2,2'-(decane-1,10-diylbis(sulfanediyl))bis(octan-4-one), 2,2'-(undecane-1,11-diylbis(sulfanediyl))bis(octan-4-one), or 2,2'-(dodecane-1,12-diylbis(sulfanediyl))bis(octan-4-one), alkyl groups of size C4 to C 22 Between C4 and C 18 Between C4 and C6, and more preferably 12 and the alkyl group contains 1 to 4 ether groups, such as 2,2'-(oxaalkane-α,ω-diylbis(sulfanediyl))bis(octan-4-one), e.g., 2,2'-(3-oxapentane-1,5-diylbis(sulfanediyl))bis(octan-4-one), 2,2'-(3,6-dioxaoctane-1,8-diylbis(sulfanediyl))bis(octan-4-one), 2,2'-(3,6,9-trioxaundecane-1,11-diylbis(sulfanediyl))bis(octan-4-one) or 2,2'-(3,6,9,12-tetraoxatetradecane-1,14-diylbis(sulfanediyl))bis(octan-4-one), where the alkyl group size varies between C4 and C 22 Between C4 and C 18 Between C5 and C6, and more preferably 162,2'-(alkane-α,ω-diyldisulfonyl)bis(octan-4-one), e.g., 2,2'-(hexane-1,6-diyldisulfonyl)bis(octan-4-one), 2,2'-(heptane-1,7-diyldisulfonyl)bis(octan-4-one), 2,2'-(octane-1,8-diyldisulfonyl)bis(octan-4-one), 2,2' -(nonane-1,9-diyldisulfonyl)bis(octan-4-one), 2,2'-(decane-1,10-diyldisulfonyl)bis(octan-4-one), 2,2'-(undecane-1,11-diyldisulfonyl)bis(octan-4-one), or 2,2'-(dodecane-1,12-diyldisulfonyl)bis(octan-4-one), or alkyl groups with sizes of C4 to C 22 Between C4 and C 16 Between C4 and C6, and more preferably 12 and the alkyl group contains 1 to 4 ether groups, such as 2,2'-(oxaalkane-α,ω-diyldisulfonyl)bis(octan-4-one), for example 2,2'-(3-oxapentane-1,5-diyldisulfonyl)bis(octan-4-one), 2,2'-(3,6-dioxaoctane-1,8-diyldisulfonyl)bis(octan-4-one), 2,2'-(3,6,9-trioxaundecane-1,11-diyldisulfonyl)bis(octan-4-one) or 2,2'-(3,6,9,12-tetraoxatetradecane-1,14-diyldisulfonyl)bis(octan-4-one).

[0032] According to any embodiment of the present invention, the compound of formula (I) preferably has the formula [ka] [In the formula, R 1 , R 2 , R 3 , X and Q have the same meaning as in formula (I), and the dotted line represents the position of a single or double bond; and even more preferably, the compound of formula (I) is a compound of formula [ka] [In the formula, R 1 , X and Q have the same meaning as indicated for compounds of formula (I), and the dotted line represents the position of a single or double bond.

[0033] According to any one of the above embodiments, the compound of formula (I) has an alkyl group size of C4 to C 22 Between C4 and C 18 Between C5 and C6, and more preferably 163,3'-(alkane-α,ω-diylbis(sulfanediyl))bis(1-(2,6,6-trimethylcyclohex-1-, 2-, or 3-en-1-yl)butan-1-one), 3,3'-(alkane-α,ω-diylbis(sulfanediyl))bis(1-(6-ethyl-2,6-dimethylcyclohex-3-en-1-yl)butan-1-one), 3,3'-(alkane-α,ω-diylbis(sulfanediyl))bis(2-methyl-1-(2,6,6-trimethylcyclohex-1-, 2-, or 3-en-1-yl)butan-1-one), 3,3'-(hexane-1,6-diylbis(sulfanediyl))bis(1-(2,6,6-trimethylcyclohex-1,3-dien-1-yl)butan-1-one), or 3,3'-(alkane-α,ω-diylbis(sulfanediyl))bis(1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)butan-1-one), for example 3,3'-(hexane-1,6-diylbis(sulfanediyl))bis(1-(2,6,6-trimethylcyclohex-1-, 2- or 3-en-1-yl)butan-1-one), 3,3'-(hexane-1,6-diylbis(sulfanediyl))bis(1-(6-ethyl-2,6-dimethylcyclohex- 3,3'-(hexane-1,6-diylbis(sulfanediyl))bis(2-methyl-1-(2,6,6-trimethylcyclohex-1-, 2- or 3-en-1-yl)butan-1-one), 3,3'-(hexane-1,6-diylbis(sulfanediyl))bis(1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)butan-1-one), 3,3'-(heptane-1,7-diylbis(sulfanediyl))bis(1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)butan-1-one) cyclohex-1-, 2-, or 3-en-1-yl)butan-1-one), 3,3'-(octane-1,8-diylbis(sulfanediyl))bis(1-(2,6,6-trimethylcyclohex-1-, 2-, or 3-en-1-yl)butan-1-one), 3,3'-(nonane-1,9-diylbis(sulfanediyl))bis(1-(2,6,6-trimethylcyclohex-1-, 2-, or 3-en-1-yl)butan-1-one), 3,3'-(decane-1,10-diylbis(sulfanediyl))bis(1-(2,6,6-trimethylcyclohex-1-, 2-, or 3-en-1-yl)butan-1-one), 3,3'-(undecane-1,11-diylbis(sulfanediyl))bis(1-(2,6,6-trimethylcyclohex-1-, 2-, or 3-en-1-yl)butan-1-one), or 3,3'-(dodecane-1,12-diylbis(sulfanediyl))bis(1-(2,6,6-trimethylcyclohex-1-, 2-, or 3-en-1-yl)butan-1-one), alkyl groups ranging in size from C4 to C, 22 Between C4 and C 16 Between C4 and C6, and more preferably 12and the alkyl group contains 1 to 4 ether groups, such as 3,3'-(oxaalkane-α,ω-diylbis(sulfanediyl))bis(1-(2,6,6-trimethylcyclohex-1-, 2-, or 3-en-1-yl)butan-1-one), 3,3'-(oxaalkane-α,ω-diylbis(sulfanediyl))bis(1-(6-ethyl-2,6-dimethylcyclohex-3-en-1-yl)butan-1-one), 3,3'-(oxaalkane-α,ω-diylbis(sulfanediyl))bis(2-methyl-1-(2,6 ,6-trimethylcyclohex-1-, 2- or 3-en-1-yl)butan-1-one) or 3,3'-(oxaalkane-α,ω-diylbis(sulfanediyl))bis(1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)butan-1-one), for example, 3,3'-(3-oxapentane-1,5-diylbis(sulfanediyl))bis(1-(2,6,6-trimethylcyclohex-1-, 2- or 3-en-1-yl)butan-1-one), 3,3'-(3,6-dioxaoctane-1,8-diylbis bis(sulfanediyl))bis(1-(2,6,6-trimethylcyclohex-1-, 2-, or 3-en-1-yl)butan-1-one), 3,3'-(3,6-dioxaoctane-1,8-diylbis(sulfanediyl))bis(1-(6-ethyl-2,6-dimethylcyclohex-3-en-1-yl)butan-1-one), 3,3'-(3,6-dioxaoctane-1,8-diylbis(sulfanediyl))bis(2-methyl-1-(2,6,6-trimethylcyclohex-1-, 2-, or 3-en-1-yl)butan-1-one ), 3,3'-(3,6-dioxaoctane-1,8-diylbis(sulfanediyl))bis(1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)butan-1-one), 3,3'-(3,6,9-trioxaundecane-1,11-diylbis(sulfanediyl))bis(1-(2,6,6-trimethylcyclohex-1-, 2-, or 3-en-1-yl)butan-1-one), or 3,3'-(3,6,9,12-tetraoxatetradecane-1,14-diylbis(sulfanediyl))bis(1-(2,6,6-trimethylcyclohex-1-, 2-, or 3-en-1-yl)butan-1-one), alkyl groups of size C4 to C, 22 Between C4 and C 18 Between C5 and C6, and more preferably 163,3'-(alkane-α,ω-diyldisulfonyl)bis(1-(2,6,6-trimethylcyclohex-1-, 2-, or 3-en-1-yl)butan-1-one), 3,3'-(alkane-α,ω-diyldisulfonyl)bis(1-(6-ethyl-2,6-dimethylcyclohex-3-en-1-yl)butan-1-one), 3,3'-(alkane-α,ω-diyldisulfonyl)bis(2-methyl-1-(2,6,6-trimethylcyclohex-1-, 2-, or 3-en-1-yl)butan-1-one) or are 3,3'-(alkane-α,ω-diyldisulfonyl)bis(1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)butan-1-one), for example, 3,3'-(hexane-1,6-diyldisulfonyl)bis(1-(2,6,6-trimethylcyclohex-1-, 2- or 3-en-1-yl)butan-1-one), 3,3'-(hexane-1,6-diyldisulfonyl)bis(1-(6-ethyl-2,6-dimethylcyclohex-3-en-1-yl)butan-1-one), 3,3'-(hexane-1,6-diyldisulfonyl)bis(1-(6-ethyl-2,6-dimethylcyclohex-3-en-1-yl)butan-1-one), 3,3'-(hexane-1,6-diyldisulfonyl)bis(1-(2,6,6-trimethylcyclohex-1-, 2-, or 3-en-1-yl)butan-1-one), 3,3'-(heptane-1,7-diyldisulfonyl)bis(1-(2,6,6-trimethylcyclohex-1-, 2-, or 3-en-1-yl)butan-1-one), 3,3'-(octane-1,8-diyldisulfonyl) Bis(1-(2,6,6-trimethylcyclohex-1-, 2-, or 3-en-1-yl)butan-1-one), 3,3'-(nonane-1,9-diyldisulfonyl)bis(1-(2,6,6-trimethylcyclohex-1-, 2-, or 3-en-1-yl)butan-1-one), 3,3'-(decane-1,10-diyldisulfonyl)bis(1-(2,6,6-trimethylcyclohex-1-, 2-, or 3-en-1-yl)butan-1-one), 3,3'-(undecane-1,11-diyldisulfonyl)bis(1-(2,6,6-trimethylcyclohex-1-, 2-, or 3-en-1-yl)butan-1-one) or 3,3'-(dodecan-1,12-diyldisulfonyl)bis(1-(2,6,6-trimethylcyclohex-1-, 2-, or 3-en-1-yl)butan-1-one), or alkyl groups in size C4 to C, 22 Between C4 and C 16 Between C4 and C6, and more preferably 12and the alkyl group contains 1 to 4 ether groups, such as 3,3'-(oxaalkane-α,ω-diyldisulfonyl)bis(1-(2,6,6-trimethylcyclohex-1-, 2-, or 3-en-1-yl)butan-1-one), 3,3'-(oxaalkane-α,ω-diyldisulfonyl)bis(1-(6-ethyl-2,6-dimethylcyclohex-3-en-1-yl)butan-1-one), 3,3'-(oxaalkane-α,ω-diyldisulfonyl)bis(2-methyl-1-(2,6,6-trimethylcyclohex-1-, 2-, or 3-en-1-yl)butan-1-one), 3,3'-(oxaalkane-α,ω-diyldisulfonyl)bis(1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)butan-1-one), for example, 3,3'-(3-oxapentane-1,5-diyldisulfonyl)bis(1-(2,6,6-trimethylcyclohexa-1,2- or 3-en-1-yl)butan-1-one), 3,3'-(3,6-dioxaoctane-1,8-diyldisulfonyl)bis(1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)butan-1-one), trimethylcyclohex-1-, 2-, or 3-en-1-yl)butan-1-one), 3,3'-(3,6-dioxaoctane-1,8-diyldisulfonyl)bis(1-(6-ethyl-2,6-dimethylcyclohex-3-en-1-yl)butan-1-one), 3,3'-(3,6-dioxaoctane-1,8-diyldisulfonyl)bis(2-methyl-1-(2,6,6-trimethylcyclohex-1-, 2-, or 3-en-1-yl)butan-1-one), 3,3'-(3,6-dioxaoctane-1,8-diyldisulfonyl)bis(2-methyl-1-(2,6,6-trimethylcyclohex-1-, 2-, or 3-en-1-yl)butan-1-one). 3,3'-(3,6,9-trioxaundecane-1,11-diyldisulfonyl)bis(1-(2,6,6-trimethylcyclohex-1,2- or 3-en-1-yl)butan-1-one), 3,3'-(3,6,9,12-tetraoxatetradecane-1,14-diyldisulfonyl)bis(1-(2,6,6-trimethylcyclohex-1,2- or 3-en-1-yl)butan-1-one).

[0034] According to any embodiment of the present invention, the compound of formula (I) preferably has the formula [ka] [In the formula, R 1 , R 2 , R 3 and Q has the same meaning as in formula (I), and even more preferably the compound of formula (I) is a compound of formula [ka] wherein Q has the same meaning as given for the compounds of formula (I).

[0035] According to any one of the above embodiments, the compound of formula (I) has an alkyl group size of C4 to C 22 Between C4 and C 18 Between C5 and C6, and more preferably 16 Varying between, 4,4'-(alkane-α,ω-diylbis(sulfanediyl))bis(4-methylpentan-2-one), e.g., 4,4'-(hexane-1,6-diylbis(sulfanediyl))bis(4-methylpentan-2-one), 4,4'-(heptane-1,7-diylbis(sulfanediyl))bis(4-methylpentan-2-one), 4,4'-(octane-1,8-diylbis(sulfanediyl))bis(4-methylpentan-2-one), 4,4' -(nonane-1,9-diylbis(sulfanediyl))bis(4-methylpentan-2-one), 4,4'-(decane-1,10-diylbis(sulfanediyl))bis(4-methylpentan-2-one), 4,4'-(undecane-1,11-diylbis(sulfanediyl))bis(4-methylpentan-2-one), or 4,4'-(dodecane-1,12-diylbis(sulfanediyl))bis(4-methylpentan-2-one), or alkyl groups with sizes of C4 to C 22 Between C4 and C 16 Between C4 and C6, and more preferably 12and the alkyl group contains 1 to 4 ether groups, such as 4,4'-(oxaalkane-α,ω-diylbis(sulfanediyl))bis(4-methylpentan-2-one), for example, 4,4'-(3-oxapentane-1,5-diylbis(sulfanediyl))bis(4-methylpentan-2-one), 4,4'-(3,6-dioxaoctane-1,8-diylbis(sulfanediyl))bis(4-methylpentan-2-one), 4,4'-(3,6,9-trioxaundecane-1,11-diylbis(sulfanediyl))bis(4-methylpentan-2-one), or 4,4'-(3,6,9,12-tetraoxatetradecane-1,14-diylbis(sulfanediyl))bis(4-methylpentan-2-one).

[0036] Compounds according to formula (I) can slowly produce, over time, an α,β-unsaturated aldehyde or ketone of formula (II). Additionally, as a side reaction, compounds according to formula (I) can produce thiols of formula (II'), particularly when X is of formula (i). In formulas (II) and (II'), each R 1(’) is R 1 or R 1’ R 2(’) is R 2 or R 2’ R 3(’) is R 3 or R 3’ all have the same meaning as in formula (I), except that within the same molecule of (II) or (II'), all R 1(’) , R 2(’) and R 3(’) is R 1 , R 2 Or R 3 , or R 1’ , R 2’ Or R 3’ It represents one of the following. [ka]

[0037] The compounds of formula (I) are nonvolatile and substantially odorless. At the same time, they are relatively stable in perfume compositions or perfumed articles. When exposed to a surface under environmental conditions, compounds (II) and / or (II') are believed to be formed by reaction with ambient humidity. The formation of these compounds may also be triggered by the presence of oxygen in the air, changes in pH, exposure to light, especially UV-A light, the presence of enzymes, or elevated temperatures, or by other mechanisms, or a combination of multiple mechanisms.

[0038] The non-volatile and substantially odorless compound is advantageously characterized by a vapor pressure of less than 2.0 Pa, as calculated using the software EPIwin v. 3.10 (2000, available from the U.S. Environmental Protection Agency). Preferably, the vapor pressure is less than 0.2 Pa, even more preferably less than 0.02 Pa.

[0039] Although it is not possible to provide an exhaustive list of compounds of formula (II) or (II') produced from compounds of formula (I) of the present invention, preferred, non-limiting examples include: 1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one (alpha-damascone), 1-(2,6,6-trimethylcyclohex-1-en-1-yl)but-2-en-1-one (beta-damascone), 1-(2,2-dimethyl-6-methylenecyclohex-2 ... 1-(2,6,6-trimethylcyclohex-3-en-1-yl)but-2-en-1-one (gamma-damascone), 1-(2,6,6-trimethylcyclohex-3-en-1-yl)but-2-en-1-one (delta-damascone), 1-(6-ethyl-2,6-dimethylcyclohex-3-en-1-yl)2-buten-1-one, 2-methyl-1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one, 2-methyl-1-(2,6,6-trimethylcyclohex-1-en-1-yl)but-2-en ionone, 1-(2,2-dimethyl-6-methylenecyclohexyl)-2-methylbut-2-en-1-one, 2-methyl-1-(2,6,6-trimethylcyclohex-3-en-1-yl)but-2-en-1-one, 4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one (alpha-ionone), 4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one (beta-ionone), 4-(2,2-dimethyl 1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one, 1-(2,2,3,6-tetramethylcyclohexyl)but-2-en-1-one, 4-(2,2,3,6-tetramethylcyclohexyl)but-3-en-2-one, 1-(5,5-dimethylcyclohex-1-en-1-yl)pent-4-en-1-one, 3-methyl-5-propyl-2-cyclohexen-1-one, 3-mercapto-3-methyl-5-propylcyclohexan-1-one, 3-methylcyclohex-2-en-1-one, 3-mercapto-3-methylcyclohexan-1-one, 3-methylcyclopent-2-en-1-one, 3-mercapto-3-methylcyclopentan-1-one, 2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one (carvone), 5-methyl-2-(propan-2-ylidene)cyclohexan-1-one (pulegone), 2-(2-mercaptopropan-2-yl)-5-methylcyclohexan-1-one, 1-(3,3-dimethyl- 1-cyclohexen-1-yl)-4-penten-1-one, 1-(5-ethyl-5-methylcyclohex-1-en-1-yl)pent-4-en-1-one, 3,7-dimethylocta-2,6-dienal (citral), oct-2-en-4-one, 2-mercaptooctan-4-one, 5-methylhex-4-en-3-one, 5-mercapto-5-methylhexan-3-one, 4-methylpent-3-en-2-one, 4-mercapto-4-methylpentan-2-one, 3-methylpent-3-en-2-one, 4-mercapto-3-methylpentan-2-one, 3-methylbut-2-enal, 3-mercapto-3-methylbutanal, but-2-enal or 3-mercaptobutanal and / or mixtures thereof.

[0040] Compounds of formula (I) in which X is of formula (i) can be synthesized by 1,4-addition reaction of compounds of formula HX-Q-XH with α,β-unsaturated aldehydes or ketones of formula (II), where all symbols have the meanings as indicated in formula (I). Compounds of formula (I) in which X is of structure (ii) or (iii) can then be obtained in a second step from compounds of formula (I) in which X is of formula (i) by (partial) oxidation.

[0041] Compounds of formula (I) can be prepared using either one or two different α,β-unsaturated aldehydes or ketones of formula (II). When two different α,β-unsaturated aldehydes or ketones are used, different R 1 , R 2 , R 3 Groups and R 1’ , R 2’ , R 3’ A compound of formula (I) having a group is obtained. Preferably, only one α,β-unsaturated aldehyde or ketone of formula (II) is reacted with a compound of formula HX-Q-XH.

[0042] Compounds of formula (I) in which X is of formula (i) can be synthesized from 1 molar equivalent of a compound of formula HX-Q-XH and 2 molar equivalents of one or more α,β-unsaturated aldehydes or ketones of formula (II). Alternatively, compounds of formula (I) can be synthesized from 1 molar equivalent of a compound of formula HX-Q-XH and less than 2 molar equivalents of one or more α,β-unsaturated aldehydes or ketones of formula (II). Preferably, compounds of formula (I) are synthesized using a slight molar excess of one or more α,β-unsaturated aldehydes or ketones of formula (II) relative to the compound of formula HX-Q-XH. Preferably, 2.5 or more molar equivalents of one or more α,β-unsaturated aldehydes or ketones of formula (II) relative to the compound of formula HX-Q-XH are used, even more preferably 2.2 molar equivalents are used, and most preferably 2.1 molar equivalents are used. Thus, the final compound of formula (I) may contain some remaining compounds of formula (II).

[0043] Compounds of formula (I), where X is of formula (i), can be optionally synthesized from compounds of formula HX-Q-XH and one or more α,β-unsaturated aldehydes or ketones of formula (II) in the presence of a base acting as a catalyst. Preferably, the base used in the conversion is 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The reaction can be carried out in the presence or absence of a solvent.

[0044] Compounds of formula (I) in which X is of formula (ii) or (iii) are preferably prepared by oxidation of the corresponding compound of formula (I) in which X is of formula (i). For the preparation of compounds of formula (I) in which X is of formula (ii), oxone (2KHSO5 / KHSO4 / K2SO4) may be used as the oxidizing agent.

[0045] Although it is not possible to provide an exhaustive list of compounds of formula HX-Q-XH that may be used in the synthesis of the compounds of the invention, preferred, non-limiting examples include 1,4-butanedithiol, 1,5-pentanedithiol, 1,6-hexaneedithiol, 1,7-heptanedithiol, 1,8-octanedithiol, 1,9-nonanedithiol, 1,10-decanedithiol, 1,11-undecanedithiol, 1,12-dodecanedithiol, 1,5-dimercapto-3-oxapentane, 1,8-dimercapto-3,6-dioxaoctane, 1,11-dimercapto-3,6,9-trioxaundecane or 1,14-dimercapto-3,6,9,12-tetraoxatetradecane.

[0046] Although it is not possible to provide an exhaustive list of compounds of formula (II) that may be used in the synthesis of the compounds of the present invention, preferred, non-limiting examples include: 1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one (alpha-damascone), 1-(2,6,6-trimethylcyclohex-1-en-1-yl)but-2-en-1-one (beta-damascone), 1-(2,2-dimethyl-6-methylenecyclohexyl)but-2-en-1-one (gamma-damascone), 1-(2 ,6,6-trimethylcyclohex-3-en-1-yl)but-2-en-1-one (delta-damascone), 1-(6-ethyl-2,6-dimethylcyclohex-3-en-1-yl)2-buten-1-one, 2-methyl-1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one, 2-methyl-1-(2,6,6-trimethylcyclohex-1-en-1-yl)but-2-en-1-one, 1-(2,2-dimethyl-6-methylenecyclohexyl)-2-methylbut-2-en-1-one, 2- Methyl-1-(2,6,6-trimethylcyclohex-3-en-1-yl)but-2-en-1-one, 3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one, 1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-penten-3-one, 4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one (alpha-ionone), 4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one (beta-ionone) ionone), 4-(2,2-dimethyl-6-methylenecyclohexyl)but-3-en-2-one (gamma-ionone), 4-(2,6,6-trimethylcyclohex-3-en-1-yl)but-3-en-2-one (delta-ionone), 1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one, 1-(2,2,3,6-tetramethylcyclohexyl)but-2-en-1-one, 4-(2,2,3,6-tetramethylcyclohexyl)but-3-en-2-one, 1-(3,3- and 5,5-dimethylcyclohex-1-en-1-yl)pent-4-en-1-one, 3-methyl-5-propyl-2-cyclohexen-1-one, 3-methylcyclohex-2-en-1-one, 3-methylcyclopent-2-en-1-one, 2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one (carvone), 5-methyl-2-(propan-2-ylidene)cyclohexan-1-one (pulegone), 1-(3,3-di Methyl-1-cyclohexen-1-yl)-4-penten-1-one, 1-(5-ethyl-5-methylcyclohex-1-en-1-yl)pent-4-en-1-one, 3,7-dimethylocta-2,6-dienal (citral), oct-2-en-4-one, 5-methylhex-4-en-3-one, 4-methylpent-3-en-2-one, 3-methylpent-3-en-2-one, 3-methylbut-2-enal or but-2-enal.

[0047] The α,β-unsaturated aldehyde or ketone of formula (II) produced from or used in the synthesis of a compound of formula (I) can be in the (E) form, the (Z) form, or a mixture thereof.

[0048] Compounds of formula (I) may be obtained and used as mixtures of several different compounds of formula (I) and / or with one or more compounds of formula (II), or may be further purified according to standard methods known to those skilled in the art.

[0049] The mixture of compounds (I) and (II) comprises at least 70% compound (I), preferably more than 80% compound (I), even more preferably more than 90% compound (I), and most preferably more than 95% compound (I).

[0050] Also, a compound of formula (I) is obtained, [ka] and are also part of the present invention, in which all symbols have the same meaning as indicated in formula (I).

[0051] The mixture of compounds (I) and (III) comprises at least 30% compound (I), preferably more than 50% compound (I), even more preferably more than 75% compound (I), even more preferably more than 90% compound (I), and most preferably more than 95% compound (I).

[0052] As mentioned above, the present invention relates to the use of a compound of formula (I) as a perfuming ingredient for imparting a long-lasting fragrance, particularly a floral and fruity fragrance, to an environment. In other words, the present invention relates to a method for imparting, enhancing, improving or modifying the fragrance, particularly a floral and fruity fragrance, of a perfumed composition or a perfumed article, which comprises adding an effective amount of at least one compound of formula (I) to said composition or article. In addition, the "use of a compound of formula (I)" in this specification should be understood to mean the use of any composition containing a compound of formula (I) and which can be advantageously used in the perfume industry.

[0053] By "perfuming ingredient" herein is meant a compound used in a perfuming preparation or composition to impart a hedonic effect. In other words, to be considered a perfuming ingredient, such a perfuming ingredient must not only have an odor, but must also be recognized by those skilled in the art as being able to impart or modify the odor of the composition in a positive or pleasant way.

[0054] The expression "floral and fruity scents" or "floral and fruity notes" should be understood as scents that evoke floral, for example rose, fruity olfactory impressions, especially red berry notes, for example raspberry or strawberry notes, fruity-floral notes, for example cassis, blackcurrant, and exotic fruit notes. "Fresh" scents can be associated not only with fruity and floral scents, but also with citrus and green notes, such as "green" scents that evoke the scent of freshly cut grass. "Fresh green" scents can also have herbal and minty notes.

[0055] To clarify, long-lasting effect is typically achieved when a certain compound releases more fragrance into the environment after a certain time, for example, after several hours or several days, than a reference compound that imparts the same type of fragrance.Therefore, the expression "long-lasting floral and fruity notes" when referring to the compound of formula (I) of the present invention should be understood as the increase in the duration of floral and fruity scent perception (the release of the compound in an atmosphere that gives floral and fruity olfactory impression) compared with one of the molecules that have such impression alone, for example, after several hours (6 hours or 8 hours) or several days (1 day or 3 days), measured under the same conditions.

[0056] The above composition, which can actually be advantageously used as a perfuming ingredient, is also an object of the present invention.

[0057] Therefore, another aspect of the present invention is a perfuming composition comprising: i) at least one compound of the invention as defined above as perfuming ingredient; ii) at least one ingredient selected from the group consisting of a fragrance carrier and a fragrance base; and iii) optionally at least one perfume adjuvant A fragrance composition comprising:

[0058] By "perfume carrier" is meant herein a material that is substantially neutral from the perfume point of view, i.e., that does not significantly alter the organoleptic properties of the perfuming ingredients. Such carriers can be liquid or solid.

[0059] By "perfume carrier" is meant herein a material that is substantially neutral from the perfume point of view, i.e., that does not significantly alter the organoleptic properties of the perfuming ingredients. Such carriers can be liquid or solid.

[0060] The liquid carrier can be, by way of non-limiting example, emulsifying system, i.e., solvent and surfactant system, or solvents commonly used in perfumery.The detailed description of the nature and type of solvents commonly used in perfumery is not exhaustive.However, by way of non-limiting example, solvents such as butylene or propylene glycol, glycerol, dipropylene glycol and its monoether, 1,2,3-propanetriyl triacetate, dimethyl glutarate, dimethyl adipate 1,3-diacetyloxypropan-2-yl acetate, diethyl phthalate, isopropyl myristate, benzyl benzoate, benzyl alcohol, 2-(2-ethoxyethoxy)-1-ethanol, tri-ethyl citrate or their mixtures are the most commonly used. For compositions containing both a perfume carrier and a perfume base, other suitable perfume carriers than those specified above may also be ethanol, water / ethanol mixtures, limonene or other terpenes, isoparaffins such as those known under the trademark Isopar® (manufacturer: Exxon Chemical), or glycol ethers and glycol ether esters such as those known under the trademark Dowanol® (manufacturer: Dow Chemical Company), or hydrogenated castor oil such as those known under the trademark Cremophor® RH 40 (manufacturer: BASF).

[0061] Solid carrier refers to a material that can chemically or physically bind the fragrance composition or some components of the fragrance composition.Generally, such solid carriers are used to stabilize the composition or control the evaporation rate of the composition or some components.The use of solid carriers is currently used in the art, and those skilled in the art know how to achieve the desired effect.However, non-limiting examples of solid carriers can include absorbent gums or polymers or inorganic materials, such as porous polymers, cyclodextrins, wood materials, organic or inorganic gels, clays, gypsum talc, or zeolites.

[0062] Other non-limiting examples of solid carriers can include encapsulating materials.Examples of such materials can include wall-forming and plasticizing materials, such as monosaccharides, disaccharides or trisaccharides, natural or modified starch, hydrocolloids, cellulose derivatives, polyvinyl acetate, polyvinyl alcohol, protein or pectin, or the materials cited in further references, for example, H. Scherz, Hydrokolloides: 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 can be carried out by using techniques such as spray drying, coagulation or even extrusion; or can be comprised of coating encapsulation, including coacervation and complex coacervation techniques.

[0063] Non-limiting examples of solid carriers include core-shell capsules comprising resins of the aminoplast, polyamide, polyester, polyurea or polyurethane type or mixtures thereof (all of which are well known to those skilled in the art) using techniques such as polymerization, interfacial polymerization, coacervation or phase separation processes induced by these together, optionally in the presence of polymeric stabilizers or cationic copolymers (all of which are described in the prior art).

[0064] The resins can be produced by polycondensation of aldehydes (e.g., formaldehyde, 2,2-dimethoxyethanal, glyoxal, glyoxylic acid, or glycolaldehyde, and mixtures thereof) with amines such as urea, benzoguanamine, glycoluril, melamine, methylolmelamine, methylated methylolmelamine, guanazole, and mixtures thereof. Alternatively, preformed resin alkylolated polyamines, such as those commercially available under the trademarks Urac® (manufactured by Cytec Technology Corp.), Cymel® (manufactured by Cytec Technology Corp.), Urecoll®, or Luracoll® (manufactured by BASF), can be used.

[0065] Other resins are produced by polycondensation of 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 and trimethylolpropane (known under the trade name Takenate®, manufactured by Mitsui Chemicals), among others the trimer of xylylene diisocyanate and trimethylolpropane and the biuret of hexamethylene diisocyanate, with polyols, such as glycerol.

[0066] Some influential publications on the encapsulation of perfumes by polycondensation of amino resins, i.e., melamine-based resins, with aldehydes, include those typified by articles such as those published by K. Dietrich et al. in Acta Polymerica, Vol. 40, pp. 243, 325, and 683 (1989) and Vol. 41, p. 91 (1990). Such articles already describe the various parameters affecting the production of such core-shell microcapsules, following prior art methods further illustrated in the patent literature. U.S. Patent No. 4,396,670 to Wiggins Teape Group Limited is an early and relevant example of the latter. Since then, many other authors have enriched the literature in this field, and while it is impossible to cover all the developments published here, a general knowledge of encapsulation technology is highly valuable. Recent relevant publications disclosing the suitable use of such microcapsules are represented, for example, by the article by K. Bruyninckx and M. Dusselier, ACS Sustainable Chemistry & Engineering, 2019, Vol. 7, pp. 8041-8054.

[0067] By "perfume base" herein is meant a composition that includes at least one perfuming co-ingredient.

[0068] The perfuming co-ingredient is not of formula (I). Furthermore, as used herein, "perfuming co-ingredient" refers to a compound that is used in a perfuming preparation or composition in addition to the perfuming ingredient of formula (I) and that imparts a pleasant effect to the perfuming ingredient of formula (I), etc. In other words, to be considered a perfuming ingredient, such an adjunct ingredient must not only have a scent, but must also be recognized by those skilled in the art as being able to impart or modify the scent of the composition in a positive or pleasant way.

[0069] In particular, perfuming co-ingredients that may be used in the perfuming preparations or compositions according to the invention include, by way of non-limiting example: a) natural or nature-identical ingredients and natural extracts, preferably those obtained from red berries such as strawberries and raspberries; b) ingredients with strawberry notes, such as oct-2-en-4-one, 2,5-dimethyl-4-hydroxy-2H-furan-3-one (Furaneol®), 5-ethyl-4-hydroxy-2-methyl-3(2H)-furanone, 2,5-dimethyl-4-oxo-4,5-dihydrofuran-3-yl acetate, ethyl 3-methyl-3-phenyloxirane-2-carboxylate (Strawberry Pure®), ethyl 3-phenyloxirane-2-carboxylate, methyl 2-acetamidobenzoate or 3-phenylpropyl 3-methylbutanoate, 2-methyl-4-oxo-4H-pyran-3-ylpropionate, 2-methylpent-2-enoic acid or (2S,5S)-2-(tert-butyl)-5-methyl-2-propyltetrahydrofuran (Dihydrocassyrane®); c) ingredients with raspberry notes, such as 4-(4-methoxyphenyl)butan-2-one (raspberry ketone); d) ingredients with other fruity notes, such as ethyl butyrate, ethyl 2-methylbutanoate, ethyl 2-methyl-pentanoate, gamma-nonalactone, gamma-undecalactone, hexyl acetate, allyl heptanoate, allyl 3-cyclohexylpropanoate, 2-phenoxyethyl isobutyrate, 2,2,5-trimethyl-5-pentylcyclopentanone, 2-methyl-4-propyl-1,3-oxathiane , 4-decanolide, 5-heptyldihydrofuran-2(3H)-one, 3-methyl-2-hexen-yl acetate, 1-(3,3-dimethylcyclohexyl)ethyl (3-ethyl-2-oxiranyl)acetate, ethyl 2-(2-methyl-1,3-dioxolan-2-yl)acetate (Fructone®) or diethyl cyclohexane-1,4-dicarboxylate (Fructalate®); e) ingredients with caramel notes such as 2-ethyl-3-hydroxy-4H-pyran-4-one; f) ingredients with citrus notes such as 1-methyl-4-(1-methylethenyl)-cyclohexene (limonene), 2,6-dimethyl-7-octen-2-ol (dihydromyrcenol), 1,5-dimethyl-1-vinyl-4-hexenyl acetate (linalyl acetate), 3,7-dimethyl-6-octenenitrile, 1-p-menthen-8-yl acetate or 1,4(8)-p-menthadiene; g) ingredients containing flowery citrus notes, such as methyl 2-(3-oxo-2-pentylcyclopentyl)acetate (Hedione®); h) 3,7-dimethylocta-1,6-dien-3-ol (linalool), 3,7-dimethyl-3-octanol, 3,7-dimethyl-6-octen-1-ol (citronellol), 3,7-dimethyl-2,6-octadien-1-ol (geraniol, nerol), 2-phenylethanol, 3-methylbutyl-2-hydroxybenzoate, pentyl 2-hydroxybenzoate, 1-(6-ethyl-2,6-dimethylcyclohex-3-en-1-yl)-2-buten-1-one, hexyl 2-hydroxybenzoate, benzyl 2-hydroxybenzoate or cyclohexyl 2-hydroxybenzoate, 3-(4-tert-butylphenyl)-2-methylpropanal, 2-pentyl-3-phenyl-2-propenyl nal, 2-hexyl-3-phenyl-2-propenal, benzyl acetate, tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol, methyl 2-(methylamino)benzoate, 2,5-dimethyl-2-indanemethanol, 2,6,6-trimethyl-3-cyclohexene-1-carboxylate, 3-(4,4-dimethyl-1-cyclohexen-1-yl)propanal, 3,7-dimethyl-1,6-nonadien-3-ol, 3-(4-isopropylphenyl)-2-methylpropanal, tricyclo[5.2.1.0(2,6)]dec-3- and 4-en-8-yl acetate, tricyclo[5.2.1.0(2,6)]dec-3- and 4-en-8-yl propionate, tricyclo[5.2.1.0(2,6)]dec-3- and 4-en-8-yl 2-methylpropanoate, p-mentha-1-en-8-ol, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate, 1,1-dimethyl-2-phenylethyl acetate, 3,7-dimethyl-2,6-octadienyl acetate, 7-methyloctyl acetate, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate, 4-cyclohexyl-2-methyl-2-butadiene Ingredients containing flowery notes such as ethanol, 3-methyl-5-phenyl-1-pentanol, cis-7-p-menthanol, 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, 8-decen-5-olide or 4-phenyl-2-butanone; i) ingredients with flowery-woody notes, such as 1-(octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-1-ethanone (Iso E Super®, mixture of isomers); j) ingredients with a green note such as (Z)-hex-3-en-1-ol, (Z)-hex-3-en-1-yl acetate, (Z)-hex-3-en-1-yl butyrate, (Z)-hex-3-en-1-yl benzoate, (Z)-hex-3-en-1-yl 2-hydroxybenzoate, 2-methyl-3-hexanone (E)-oxime, 2,4-dimethyl-3-cyclohexene-1-carbaldehyde, 2-tert-butyl-1-cyclohexyl acetate, 1-phenylethyl acetate, allyl (2-methylbutoxy) acetate, 4-methyl-3-decen-5-ol or diphenyl ether; k) 1,4-dioxa-5,17-cycloheptadecanedione, (Z)-4-cyclopentadecen-1-one, (9Z)-9-cycloheptadecen-1-one, 2-{1S)-1-[(1R)-3,3-dimethylcyclohexyl]ethoxy}-2-oxoethylpropionate 3-methyl-5-cyclopentadecen-1-one, [1-(3',3'-dimethyl-1'-cyclohexyl)ethoxycarbonyl]methylpropanoate, 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethyl-cyclopenta-g-2-benzopyran Ingredients with musk notes such as oxacyclohexadecan-2-one (Exaltolide®), oxacyclohexadec-12 and / or 13-en-2-one (Habanolide®), 3-methylcyclopentadecan-1-one (Muscone®), (Z)-3-methylcyclopentadec-5-en-1-one (Muscenone®) or 2-(1-(3,3-dimethylcyclohexyl)ethoxy)-2-methylpropylpropionate (Helvetolide®).

[0070] In an alternative embodiment, perfuming co-ingredients that may be used in the perfuming preparations or compositions according to the invention include, by way of non-limiting example, 1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one (alpha-damascone), 1-(2,6,6-trimethylcyclohex-1-en-1-yl)but-2-en-1-one (beta-damascone), 1-(2,2-dimethyl-6-methylenecyclohexyl)but-2-en-1-one (gamma-damascone), 1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one (gamma-damascone), 1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one (alpha-damascone), 1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one (beta-damascone), 1-(2,2-dimethyl-6-methylenecyclohexyl)but-2-en-1-one (gamma-damascone), 1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one (alpha-damascone), 1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one (beta ...gamma-damascone), 1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one (be Trimethylcyclohex-3-en-1-yl)but-2-en-1-one (delta-damascone), 2-methyl-1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one, 2-methyl-1-(2,6,6-trimethylcyclohex-1-en-1-yl)but-2-en-1-one, 1-(2,2-dimethyl-6-methylenecyclohexyl)-2-methylbut-2-en-1-one, 2-methyl-1-(2,6,6-trimethylcyclohex-3-en-1-yl)but-2-en-1-one 1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-penten-3-one, 4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one (alpha-ionone), 4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one (beta-ionone), 4-(2,2-dimethyl- -6-methylenecyclohexyl)but-3-en-2-one (gamma-ionone), 4-(2,6,6-trimethylcyclohex-3-en-1-yl)but-3-en-2-one (delta-ionone), 1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one, 1-(2,2,3,6-tetramethylcyclohexyl)but-2-en-1-one, 4-(2,2,3,6-tetramethylcyclohexyl)but-3-en-2-one, 1-(3,3- and 5,5-dimethylcyclohex-1-en-1-yl)pent-4-en-1-one, 3-methyl-5-propyl-2-cyclohexen-1-one, 3-mercapto-3-methyl-5-propylcyclohexan-1-one, 3-methylcyclohex-2-en-1-one, 3-mercapto-3-methylcyclohexan-1-one, 3-methylcyclopent-2-en-1-one, 3-mercapto-3-methylcyclopentan-1-one, 2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one (carvone), 5-methyl-2-(propan-2-ylidene)cyclohexan-1-one (pulegone), 2-(2-mercaptopropan-2-yl)-5-methylcyclohexan-1-one, 1-(3,3-di Examples of such methyl 1-cyclohexen-1-yl)-4-penten-1-one include 1-(5-ethyl-5-methylcyclohex-1-en-1-yl)pent-4-en-1-one, 3,7-dimethylocta-2,6-dienal (citral), oct-2-en-4-one, 2-mercaptooctan-4-one, 5-methylhex-4-en-3-one, 5-mercapto-5-methylhexan-3-one, 4-methylpent-3-en-2-one, 4-mercapto-4-methylpentan-2-one, 3-methylpent-3-en-2-one, 4-mercapto-3-methylpentan-2-one, 3-methylbut-2-enal, 3-mercapto-3-methylbutanal, but-2-enal, and 3-mercaptobutanal.

[0071] Furthermore, those skilled in the art can select other perfuming co-ingredients based on their general knowledge and in accordance with the intended use or application and the desired organoleptic effect to be achieved. The nature and types of these other perfuming co-ingredients will not be described in further detail herein, and would not be exhaustive in any case. Generally speaking, these perfuming co-ingredients belong to various chemical classes, such as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogen- or sulfur-containing heterocyclic compounds, and essential oils, and the perfuming co-ingredients may be of natural or synthetic origin. Many of these co-ingredients are listed in reference texts, such as S. Arctander's book "Perfume and Flavor Chemicals," 1969, Montclair, New Jersey, USA, or its more recent editions or other works of similar content, as well as in the abundant patent literature in the field of perfumery. It is also understood that the co-ingredients may be compounds known to release various types of perfuming compounds in a controlled manner, or may be encapsulated fragrances.

[0072] The term "perfuming adjuvant" is understood to mean an ingredient that can provide additional benefits such as color, specific light resistance, chemical stability, etc. A detailed description of the nature and type of adjuvants commonly used in perfume bases is not exhaustive, but it should be mentioned that the ingredients are well known to those skilled in the art. However, specific, non-limiting examples include viscosity agents (e.g., surfactants, thickeners, gelling and / or rheology modifiers), stabilizers (e.g., preservatives, antioxidants, heat / light and / or buffering agents or chelating agents, e.g., BHT), colorants (e.g., dyes and / or pigments), preservatives (e.g., antibacterial or bactericidal or antifungal or anti-irritant agents), abrasives, skin cooling agents, fixatives, insect repellents, ointments, vitamins, and mixtures thereof.

[0073] It will be understood that a person skilled in the art can perfectly design the optimum formulation for the desired effect by mixing the above-mentioned components of the perfume composition, by simply applying standard knowledge in the art, as well as by trial and error methods.

[0074] Other suitable perfumery adjuvants for use in any combination with the compounds according to the invention include tertiary amines, especially those with high water solubility such as triethanolamine, methyldiethanolamine, dimethylethanolamine, alkyldiethanolamines and ethoxylated alkyldiethanolamines.

[0075] A particular embodiment of the fragrance composition of the present invention is a fragrance composition of the formula [ka] and optionally further comprising (in addition to the above composition) at least one compound selected from the group consisting of isothiazolones where: R 4 and R 5 represent, separately and independently of one another, a hydrogen atom, a halogen atom, preferably chlorine, a C1-C4 linear or branched alkyl group, an amino group or a benzylamino group; or alternatively, R 4 and R 5 together represent a phenyl or pyridine ring which may be substituted with 1 to 4 C1-C4 linear or branched alkyl or alkenyl groups and / or 1 to 2 halogen atoms, preferably chlorine atoms; and R 6 represents a hydrogen atom, an alkali metal atom, in particular Na or K, a phenyl or benzyl group which may be substituted with one or two halogen atoms, and / or one or two methyl, trifluoromethyl, methoxy or amino groups, amine groups, or a C1-C8 unsaturated, linear, branched or cyclic hydrocarbon group which may be substituted with one or two nitrogen, oxygen or halogen atoms.

[0076] According to a particular embodiment of the present invention, the compound of formula (IV) above is R 4 and R 5 separately and independently of one another represent a hydrogen atom, a chlorine atom or a methyl group, or alternatively, R 4 and R 5 together represent a phenyl ring, and R 6 represents a hydrogen atom or a methyl group.

[0077] According to a particular embodiment of the present invention, the compound of formula (IV) above is selected from the group of isothiazolones consisting of 1,2-benzisothiazol-3(2H)-one, 4- or 5-chloro-2-methylisothiazol-3(2H)-one or 2-methylisothiazol-3(2H)-one, more preferably 5-chloro-2-methylisothiazol-3(2H)-one or 1,2-benzisothiazol-3(2H)-one, most preferably 1,2-benzisothiazol-3(2H)-one.

[0078] According to a particular embodiment of the present invention, the compound of formula (IV) is present in the composition of the present invention in a concentration by weight of 0.0% to 5% relative to the total weight of the composition. According to a more preferred embodiment of the present invention, the concentration of the compound of formula (IV) is comprised between 0.001 and 3%, preferably between 0.005 and 0.1%, of the total weight.

[0079] The compositions of the present invention, consisting of at least one compound of formula (I) and at least one perfume carrier, represent a particular embodiment of the present invention, as well as perfume compositions comprising at least one compound of formula (I), at least one perfume carrier, at least one perfume base, and optionally at least one perfume adjuvant.

[0080] It is useful to mention here that in the above compositions, in addition to the compounds of formula (I), there is the possibility of using other compounds of similar or different nature that are capable of generating other fragrances, since this allows the perfumer to prepare accords, perfumes with the olfactory notes of the various compounds of the invention, and to create new components for creative purposes.

[0081] For the sake of clarity, it is also understood that any mixture resulting directly from a chemical synthesis, e.g., a reaction medium without appropriate purification, which may involve a compound of the invention as a starting product, intermediate or final product, cannot be considered a perfuming composition according to the invention, unless the mixture provides the compound of the invention in a form suitable for perfumery. Thus, unless otherwise specified, unpurified reaction mixtures are generally excluded from the present invention.

[0082] Furthermore, the compounds of formula (I) of the present invention may also be advantageously used in all areas of modern perfumery, i.e., fine or functional perfumery, to positively impart a long-lasting or persistent strawberry aroma to consumer products to which said compounds (I) are added.

[0083] Therefore, another aspect of the present invention relates to perfumed consumer products comprising as perfuming ingredient at least one compound of formula (I) or perfuming composition as defined above.

[0084] The compounds of the present invention may be added as such or as part of the perfuming composition of the present invention.

[0085] For clarity, it should be mentioned that "perfumed consumer product" means a consumer product that is expected to deliver at least a pleasant fragrance effect to the surface to which it is applied (e.g., skin, hair, textile, or hard surface). In other words, the perfumed consumer product according to the present invention is a perfumed consumer product that comprises a functional formulation, as well as any additional benefit agent corresponding to the desired consumer product, for example, a conditioner, a detergent, or an air freshener, and an olfactory-effective amount of at least one compound of the present invention. For clarity, the perfumed consumer product is a non-edible product.

[0086] The nature and type of ingredients of perfumed consumer products will not be described in further detail herein and cannot in any way be exhaustive, but those skilled in the art can select them based on their general knowledge and according to the nature of the product and the desired effect.

[0087] As used herein, "consumer product" means baby care, personal care, fabric and home care, family care, feminine care, health care, beauty care, and the like, generally products that are intended to be used or consumed in the manner in which they are sold.

[0088] Non-limiting examples of suitable perfumed consumer products include perfumes, such as fine perfumes, colognes or aftershave lotions; fabric care products, such as liquid or solid detergents or Unidose detergents (e.g. powder tablets, liquid Unidose or multi-chamber Unidose detergents), fabric softeners, fabric deodorants, ironing water, paper, bleach, carpet cleaners or curtain care products; body care products, such as hair care products (e.g. shampoos, colouring preparations or hairsprays, colour care products or hair styling products), dental care products, disinfectants, intimate care products, cosmetic preparations (e.g. skin creams or lotions, vanishing creams or deodorants or antiperspirants (e.g. sprays or roll-ons), hair removal products, tanning products, sunscreen or after-sun products, nail products, skin cleansing products or cosmetics), skin care products (e.g., scented soaps, shower or bath mousses, oils or gels, hygiene products or foot / hand care products); air care products, such as air fresheners or "ready-to-use" powdered air fresheners, which may be used in domestic spaces (rooms, refrigerators, cupboards, shoes or cars) and / or public spaces (hall, hotel, mall, etc.); or home care products, such as mold removers, furniture care products, wipes, dishwashing detergents or hard surface (e.g., floor, bathroom, hygiene or window) cleaners, leather care products; car care products, such as polishes, waxes or plastic cleaners.

[0089] Preferred perfumed compositions or perfumed articles are perfumes, fabric or hard surface cleaners, hair care products, and fabric softeners or fragrances.

[0090] Typical examples of fabric detergent or softener compositions that can incorporate the compounds of the present invention are described in International Publication No. 97 / 34986, or U.S. Patent Nos. 4,137,180 and 5,236,615, or European Patent Application Publication No. 799885. Other typical detergent and softener compositions that can be used are described in papers such as Ullmann's Encyclopedia of Industrial Chemistry, Vol. 20, Wiley-VCH, Weinheim, pp. 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.

[0091] Some of the above-mentioned consumer product bases may be aggressive media for the compounds of the invention, and it may be necessary to protect the compounds of the invention from premature degradation, for example by encapsulating them or by chemically binding them to another chemical suitable for releasing the components of the invention upon a suitable external stimulus, such as enzymes, light, heat, oxidation or a change in pH.

[0092] The proportions in which the compounds according to the invention can be incorporated into the various aforementioned articles or compositions vary within a wide range of values, depending not only on the nature of the article to be perfumed and the desired sensory effect, but also on the nature of the co-ingredients in a given base, if the compounds according to the invention are mixed with perfuming co-ingredients, solvents or additives commonly used in the art.

[0093] For example, in perfume compositions, typical concentrations of the compounds of the invention are on the order of 0.001% to 10% by weight, or more, based on the weight of the composition in which they are incorporated. Lower concentrations, for example, on the order of 0.01% to 2% or 5% by weight, can be used when these compounds are incorporated into perfumed articles, the percentages being relative to the weight of the article.

[0094] As described above, the present invention relates to a method for imparting long-lasting or persistent floral and fruity scents to surfaces, such as hard surfaces, fabrics, skin, or hair. Perfume ingredients that impart floral and fruity scents to the environment by evaporation from the surface typically do not last long or are not persistent. As outlined above, one reason for this is their relatively high volatility, which ensures efficient evaporation after surface application. Another reason for this is that, quite often, only small amounts of these compounds are efficiently deposited on the surface. This is particularly true when they are applied to surfaces via perfume compositions or perfumed articles that are rinsed after application. This rinsing process also washes away a large amount of the perfume that would otherwise remain on the surface. Examples of this case are cleaning and cleaning agents, such as hard surface cleaners, detergents, and shower gel shampoos, which are rinsed off after application. Furthermore, the perfuming of a surface by contacting a perfuming composition or a perfumed article with the surface, which deposits the perfume on the surface through a partition equilibrium between the perfuming composition or the perfumed article and the corresponding surface, can be inefficient for perfume deposition. An example of this case is a conditioner or surface fragrance, such as a fragrance softener, which is removed or dried after contacting the object. The compound of formula (I) according to the present invention is suitable for enhancing the deposition of perfume, thereby imparting long-lasting floral and fruity scents to surfaces such as hard surfaces, fabrics, skin, or hair.

[0095] Therefore, another aspect of the present invention relates to a method for imparting a long-lasting or persistent fruity and floral scent to a surface, such as a hard surface, fabric, skin or hair, by adding at least one compound of formula (I) to a perfumed composition or perfumed article and applying the same to the corresponding target surface.

[0096] The present invention also relates to microcapsules 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, wherein at least one compound of formula (I) is contained in a core surrounded by a shell. In one embodiment, the shell of the microcapsule protects the compound of formula (I) from the environment. The shell is made of a material capable of releasing at least one compound of formula (I). In one embodiment, the shell is made of a material capable of releasing the compound of formula (I) upon shell rupture and / or by diffusion through the shell. Those skilled in the art are familiar with methods for producing such microcapsules.

[0097] The nature of the polymeric shell from the microcapsules of the present invention can vary. By way of non-limiting example, the shell can be aminoplast-based, polyamide-based, polyester-based, polyurea-based or polyurethane-based.

[0098] According to one embodiment, the shell is a biopolymer-based shell comprising a protein.

[0099] The shell may also be a hybrid, i.e., organic-inorganic, hybrid shell composed of at least two types of crosslinked inorganic particles, or may even be a shell resulting from the hydrolysis and condensation reaction of a polyalkoxysilane macromonomer composition.

[0100] According to one embodiment, the shell comprises an aminoplast copolymer such as melamine-formaldehyde or urea-formaldehyde or crosslinked melamine formaldehyde or melamine glioxal.

[0101] According to another embodiment, the microcapsules have a polymer shell resulting from complex coacervation, wherein the shell may be crosslinked.

[0102] According to another embodiment, the shell is polyurea-based, for example, but not limited to, made from an isocyanate-based monomer and an amine-containing crosslinker, such as guanidine carbonate and / or guanazole. Preferred 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 is optional.

[0103] According to a particular embodiment, the colloidal stabilizer comprises an aqueous solution of between 0.1% and 0.4% polyvinyl alcohol, between 0.6% and 1% cationic copolymer of vinylpyrrolidone and quaternized vinylimidazole (all percentages defined by weight relative to the total weight of the colloidal stabilizer). According to another embodiment, the emulsifier is an anionic or amphiphilic biopolymer, preferably selected from the group consisting of gum arabic, soy protein, gelatin, sodium caseinate and / or mixtures thereof.

[0104] The preparation of aqueous dispersions / slurries of core-shell microcapsules is well known to those skilled in the art. In one aspect, the microcapsule wall material can comprise any suitable resin, including 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 methylolmelamine, methylated methylolmelamine, iminomelamine, and mixtures thereof. Suitable ureas include dimethylolurea, methylated dimethylolurea, urea-resorcinol, and mixtures thereof. Suitable materials for manufacturing can be obtained from one or more of the following companies: Solutia Inc. (St. Louis, Missouri, USA), Cytec Industries (West Paterson, New Jersey, USA), Sigma-Aldrich (St. Louis, Missouri, USA).

[0105] According to certain embodiments, the core-shell microcapsules are formaldehyde-free capsules. A typical method for producing a formaldehyde-free aminoplast microcapsule slurry includes: 1) a process for producing an oligomeric composition, a) a polyamine component in the form of melamine or in the form of a mixture of melamine with at least one C1-C4 compound containing two NH2 functional groups; b) Glyoxal and C 4~6 and optionally a glyoxalate, wherein the ratio of glyoxal / C is between 1 / 1 and 10 / 1. 4~6 an aldehyde component having a molar ratio of 2,2-dialkoxy-ethanal of c) Protonic acid catalyst preparing an oligomeric composition comprising or obtained by reacting together the reaction products of 2) preparing an oil-in-water dispersion, the droplet size being between 1 and 600 μm; i. oil; ii.Aqueous medium iii. at least one oligomeric composition obtained in step 1; iv. at least one cross-linking agent, A) C4~C 12 Aromatic or aliphatic diisocyanates or triisocyanates, and their biuret, triuret, trimer, trimethylolpropane adducts and mixtures thereof; and / or B) Formula Q-(oxiran-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] at least one cross-linking agent selected from the group consisting of v. Optionally, a C1-C4 compound containing two NH2 functional groups preparing an oil-in-water dispersion comprising: 3) heating the dispersion; 4) cooling the dispersion Includes:

[0106] This method is described in more detail in WO 2013 / 068255, the contents of which are incorporated by reference.

[0107] According to another embodiment, the shell of the microcapsules is polyurea-based or polyurethane-based. Examples of methods for producing polyurea-based and polyurethane-based microcapsule slurries are described in, for example, WO 2007 / 004166, EP 2300146, and EP 2579976, the contents of which are also incorporated by reference. Typically, the method for producing a polyurea- or polyurethane-based microcapsule slurry comprises the following steps: 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, the average droplet size being between 1 and 500 μm, preferably between 5 and 50 μm; d) applying conditions sufficient to induce interfacial polymerization to form microcapsules in the form of a slurry. Includes:

[0108] In another embodiment, the capsule may be a granule in which the hydrophobic component; ie, the polymer of the present invention, is dispersed or adsorbed in a matrix or carrier that is a water-soluble material.

[0109] In some embodiments, the water-soluble matrix or carrier is a monomeric, oligomeric, or polymeric carrier material, or a mixture of two or more thereof. Oligomeric carriers are carriers in which 2 to 10 monomeric units are covalently linked. For example, when the oligomeric carrier is a carbohydrate, the oligomeric carrier can be sucrose, lactose, raffinose, maltose, trehalose, or fructooligosaccharide.

[0110] Examples of monomeric carrier materials are glucose, fructose, mannose, galactose, arabinose, fucose, sorbitol, mannitol.

[0111] The polymeric carrier has more than 10 covalently linked monomer units.

[0112] The carrier may be a polymeric carrier material. Non-limiting examples of polymeric carrier materials include urea, polyvinyl acetate, polyvinyl alcohol, dextrin, maltodextrin, glucose syrup, natural or modified starch, polysaccharides, carbohydrates, chitosan, gum arabic, polyethylene glycol (PEG), polyvinylpyrrolidone, acrylamide, acrylate, methacrylate, polyacrylic acid and related structures, maleic anhydride copolymers, amine-functional polymers, polyvinylbenzyl chloride, vinyl ethers, styrene, polystyrene sulfonate, vinyl acid, ethylene glycol-propylene glycol block copolymers, vegetable gums, acacia gum, pectin, xanthan, alginic acid, carrageenan, cellulose or cellulose derivatives such as carboxymethylmethylcellulose, methylcellulose, ethylcellulose, propylcellulose or hydroxyethylcellulose, polyols / sugar alcohols such as sorbitol, maltitol, xylitol, erythritol, and isomalt, PVP, citric acid or any water-soluble solid acid, fatty alcohol or fatty acid, and mixtures thereof.

[0113] According to a particular embodiment, the water-soluble polymer comprises maltodextrin having a dextrose equivalent (DE) between 3 and 20, preferably between 10 and 18.

[0114] According to one embodiment, the water soluble polymer comprises maltodextrin 18DE and / or maltodextrin 10DE.

[0115] According to a particular embodiment, the water soluble polymer comprises maltodextrin 10DE.

[0116] According to one embodiment, the carrier is an inorganic material selected from the group consisting of sodium chloride, sodium sulfate, sodium acetate, zeolite, sodium carbonate, sodium bicarbonate, clay, talc, calcium carbonate, magnesium sulfate, gypsum, calcium sulfate, magnesium oxide, zinc oxide, titanium dioxide, calcium chloride, potassium chloride, magnesium chloride, zinc chloride.

[0117] According to a particular embodiment, the solid carrier is sodium chloride and / or urea.

[0118] According to a particular embodiment, the solid carrier is sodium chloride.

[0119] According to certain embodiments, the solid carrier is a mixture of clay and PEG, preferably the mixture comprises 0-30% clay and 20-80% PEG, preferably 1-30% clay and 20-80% PEG, based on the total weight of the carrier.

[0120] According to a particular embodiment, the solid support is a mixture of sodium acetate and PEG, preferably the mixture comprises 0-80% sodium acetate and 0-50% PEG, preferably 1-80% sodium acetate and 1-50% PEG.

[0121] The molecular weight of PEG is preferably above 1000 g / mol, preferably between 1000 and 8000 g / mol.

[0122] Examples of microcapsules suitable for use in the present invention include, but are not limited to, the microcapsules disclosed in International Patent Application Publication No. WO 2007 / 026307. Further examples include the microcapsules disclosed in International Patent Application Publication No. WO 2014 / 029695. Additional examples include the microcapsules disclosed in International Patent Application Publication No. WO 2006 / 006003. Additional examples include the microcapsules disclosed in International Patent Application Publication No. WO 2006 / 018964. Additional examples include the microcapsules disclosed in International Patent Application Publication No. WO 2007 / 096790. Additional examples include the microcapsules disclosed in International Patent Application Publication No. WO 2009 / 153695. Additional examples include the microcapsules disclosed in European Patent No. EP 2379047.

[0123] Examples of methods for encapsulating compounds of Formula (I) include, but are not limited to, the microcapsules disclosed in International Patent Application Publication No. WO 2007 / 026307. Further examples include the microcapsules disclosed in International Patent Application Publication No. WO 2014 / 029695. Additional examples include the microcapsules disclosed in International Patent Application Publication No. WO 2006 / 006003. Additional examples include the microcapsules disclosed in International Patent Application Publication No. WO 2006 / 018964. Additional examples include the microcapsules disclosed in International Patent Application Publication No. WO 2007 / 096790. Additional examples include the microcapsules disclosed in International Patent Application Publication No. WO 2009 / 153695. Additional examples include the microcapsules disclosed in European Patent No. EP 2379047.

[0124] The compounds of formula (I) may also release flavoring components. Thus, a further aspect of the present invention is a method for imparting, enhancing, improving, or modifying the flavor characteristics of a flavoring composition or a flavored product, comprising adding to the composition or product an effective amount of at least one compound of formula (I) as defined above. A flavoring composition or flavored consumer product comprising at least one compound of formula (I) is also part of the present invention.

[0125] Example The invention will now be described in further detail by the following examples, in which abbreviations have their usual meaning in the art and temperatures are given in degrees Celsius (°C). NMR spectral data were obtained at 500 MHz in CDCl3 unless otherwise stated. 1 About H, and at 125.8MHz 13 C were recorded on a Bruker AMX 500 spectrometer, chemical displacements δ are given in ppm relative to Si(CH3)4 as standard, and coupling constants J are expressed in Hz (br. = broad peak). Reactions were carried out in standard glassware under N2. Unless otherwise stated, commercially available reagents and solvents were used without further purification.

[0126] Although specific conformations or configurations are shown for some compounds, this is not meant to limit the use of these compounds to the depicted isomers, and all possible conformational or configurational isomers are expected to have similar effects according to the present invention.

[0127] Example 1 Preparation of compounds according to formula (I) and / or (III) which impart long-lasting floral and fruity odors (a) Synthesis of (±)-3,3'-(3,6-dioxaoctane-1,8-diylbis(sulfanediyl))bis(1-(2,6,6-trimethylcyclohex-3-en-1-yl)butan-1-one) (Compound 1), (±)-3,14-dimethyl-1-(2,6,6-trimethylcyclohex-3-en-1-yl)-7,10-dioxa-4,13-dithiaicosane-1,16-dione (Compound 2), and (±)-2,2'-(3,6-dioxaoctane-1,8-diylbis(sulfanediyl))bis(octan-4-one) (Compound 3) (E)-trans-1-(2,6,6-trimethylcyclohex-3-en-1-yl)but-2-en-1-one (trans-delta-damascone, 2.00 g, 10.4 mmol), (E)-2-octen-4-one (1.30 g, 10.4 mmol), and 1,8-dimercapto-3,6-dioxaoctane (2.00 g, 8.4 mmol) were stirred at room temperature for 18 days. After column chromatography (SiO2, n-heptane / ethyl acetate 9:1 to n-heptane / ethyl acetate 4:1) under high vacuum for 1 hour, concentration, and drying afforded 0.79 g (13%) of compound 1, 0.64 g (12%) of compound 2, and 0.64 g (14%) of compound 3. These compounds were obtained as a mixture of stereoisomers. The three compounds can be used directly as a mixture or individually after separation. [Table 1]

[0128] Alternatively, compound 1 was prepared by slowly adding 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 0.79 g, 5.2 mmol) to a solution of trans-delta-damascone (21.00 g, 109.4 mmol) and 1,8-dimercapto-3,6-dioxaoctane (10.00 g, 52.1 mmol) in tetrahydrofuran (THF, 100 mL). After stirring at room temperature for 18 h, n-heptane (100 mL) was added, and the mixture was treated with aqueous HCl (10%, 100 mL) and washed with saturated aqueous NaCl (2 × 100 mL). The organic layer was dried (NaSO), filtered, and concentrated. Remaining volatiles were removed by bulb-to-bulb distillation (120 °C, 0.08 mbar, 2 h) to give 27.87 g (99%) of compound 1.

[0129] Alternatively, compound 3 was prepared by stirring (E)-2-octen-4-one (31.6 g, 250.4 mmol) and 1,8-dimercapto-3,6-dioxaoctane (2,2'-(ethylenedioxy)diethanethiol, 21.8 g, 113.7 mmol) at room temperature for 28 days. Remaining volatiles were removed by bulb-to-bulb distillation (100 °C, 0.04 mbar) to give 51.28 g (quantity) of compound 3.

[0130] (b) Synthesis of (±)-2,2'-(3,6-dioxaoctane-1,8-diylbis(sulfanediyl))bis(octan-4-one) (Compound 3) and (±)-2-((2-(2-(2-mercaptoethoxy)ethoxy)ethyl)thio)octan-4-one (Compound 4) (E)-2-Octen-4-one (3.75 g, 29.7 mmol) and 1,8-dimercapto-3,6-dioxaoctane (3.61 g, 19.8 mmol) were stirred at room temperature for 9 days. Column chromatography (SiO2, n-heptane / ethyl acetate 4:1 and n-heptane / ethyl acetate 3:2) afforded 1.37 g of a mixture of compound 3 and compound 4 in a 35:65 ratio. These compounds can be used directly as a mixture. Further reverse-phase column chromatography (RP Vydac 218TP C18, 7:3 and 6:4 water / acetonitrile) afforded 0.89 g of compound 4. [Table 2]

[0131] (c) Synthesis of (±)-3,3'-(3,6-dioxaoctane-1,8-diyldisulfonyl)bis(1-(2,6,6-trimethylcyclohex-3-en-1-yl)butan-1-one) (Compound 5) A solution of oxone (2KHSO5 / KHSO4 / K2SO4, 64.1 g, 421.4 mmol, 9.8 equiv.) in water (220 mL) was added dropwise to a stirred solution of (±)-3,3'-(3,6-dioxaoctane-1,8-diylbis(sulfanediyl))bis(1-(2,6,6-trimethylcyclohex-3-en-1-yl)butan-1-one) (compound 1, 24.4 g, 43.0 mmol) in methanol (330 mL), which was cooled to 1 °C in an ice bath. After addition, the ice bath was removed, and the suspension was stirred for 18 h. The reaction mixture was extracted with ethyl acetate (350 mL) and washed with saturated aqueous NaCl (200 mL), deionized water (200 mL), saturated aqueous NaHCO3 (200 mL), and saturated aqueous NaCl (200 mL). The aqueous phases were each re-extracted with ethyl acetate (250 mL). The combined organic phases were dried (NaSO), filtered, and concentrated. Drying under high vacuum (0.51 mbar) at 50° C. for 5 hours gave 25.05 g (81%) of compound 5 as a mixture of two diastereoisomers (approximately 1.5:1), which could be used as is. Column chromatography of 1.0 g (SiO, n-heptane / ethyl acetate 9:1, then 8:2, then 7:1, then 1:1) gave 0.49 g (45%) of an analytically pure sample. [Table 3]

[0132] (d) Synthesis of (±)-2,2'-(3,6-dioxaoctane-1,8-diyldisulfonyl)bis(octan-4-one) (Compound 6) An aqueous solution (400 mL) of oxone (2KHSO5 / KHSO4 / K2SO4, 103.0 g, 676.5 mmol, 9.8 equiv.) was added dropwise to a mechanically stirred solution (500 mL) of (±)-2,2'-(3,6-dioxaoctane-1,8-diylbis(sulfanediyl))bis(octan-4-one) (compound 3, 30.0 g, 69.0 mmol) in methanol, which was cooled to 1 °C in an ice bath. After addition, the ice bath was removed and the suspension was stirred for 18 h. The reaction mixture was filtered through a sintered glass filter and rinsed with water (100 mL). The residue was taken up in ethyl acetate (300 mL) and washed with demineralized water (200 mL), a saturated aqueous solution of NaHCO3 (200 mL), and a saturated aqueous solution of NaCl (200 mL). The aqueous phases were each re-extracted with ethyl acetate (200 mL). The combined organic phases were dried (Na2SO4), filtered, and concentrated. Drying under high vacuum (0.61 mbar) for 2 hours gave 16.3 g of a pair of diastereoisomers in a 3:1 ratio. The mother liquor obtained by filtration through sintered glass was concentrated to remove as much methanol as possible. The remaining aqueous phase was extracted with ethyl acetate (2 x 200 mL). The organic phase was washed with demineralized water (200 mL), saturated aqueous NaHCO3 (200 mL), and saturated aqueous NaCl (200 mL), then dried (Na2SO4), filtered, and concentrated. Drying under high vacuum (0.61 mbar) for 2 hours gave 17.4 g of a slightly yellow oil as the same pair of diastereoisomers in a 1:3 ratio, which slowly crystallized. The two product fractions were recombined to give compound 6 as a mixture of diastereoisomers in approximately a 1:1 ratio. [Table 4]

[0133] (e) Synthesis of (±)-2,2'-(hexane-1,6-diylbis(sulfanediyl))bis(octan-4-one) (Compound 7) (E)-2-octen-4-one (9.2 g, 73.2 mmol) and 1,6-hexanedithiol (5.0 g, 33.3 mmol) were stirred at room temperature for 48 days. The reaction mixture was heated at 50° C. under high vacuum (0.61 mbar) for 1 hour to remove remaining volatiles, yielding 12.6 g of crude compound as a slightly yellow oil. Column chromatography on 2.0 g (SiO 2 , n-heptane / ethyl acetate 9:1) afforded 1.38 g (65%) of compound 7. [Table 5]

[0134] (f) Synthesis of (±)-2,2'-(hexane-1,6-diyldisulfonyl)bis(octan-4-one) (compound 8) An aqueous solution (45 mL) of oxone (2KHSO5 / KHSO4 / K2SO4, 18.5 g, 121.7 mmol, 9.8 equiv.) was added dropwise to a stirred solution (75 mL) of (±)-2,2'-(hexane-1,6-diylbis(sulfanediyl))bis(octan-4-one) (compound 7, 5.0 g, 12.4 mmol) in methanol, which was cooled to 1 °C in an ice bath. After addition, the ice bath was removed, and the suspension was stirred for 18 h. The reaction mixture was extracted with ethyl acetate (200 mL) and washed with a saturated aqueous solution of NaCl (100 mL), deionized water (100 mL), a saturated aqueous solution of NaHCO3 (100 mL), and a saturated aqueous solution of NaCl (100 mL). The aqueous phase was re-extracted with ethyl acetate (150 mL). The combined organic phase was dried (Na2SO4), filtered, and concentrated. Drying under high vacuum (0.61 mbar) for 2 hours gave 4.73 g (81%) of compound 8. [Table 6]

[0135] (g) Synthesis of 4,4'-(3,6-dioxaoctane-1,8-diylbis(sulfanediyl))bis(4-methylpentan-2-one) (Compound 9) DBU (0.87 g, 5.7 mmol) was slowly added to a solution of 4-methyl-3-penten-2-one (12.30 g, 125.5 mmol) and 1,8-dimercapto-3,6-dioxaoctane (10.40 g, 57.1 mmol) in THF (50 mL). After stirring at room temperature for 3 days, n-heptane (50 mL) was added. The mixture was treated with aqueous HCl (10%, 50 mL) and washed with saturated aqueous NaCl (2 × 50 mL). The organic layer was dried (NaSO), filtered, and concentrated. Remaining volatiles were removed by bulb-to-bulb distillation (90 °C, 0.05 mbar, 2 h) to give 17.90 g (83%) of compound 9. [Table 7]

[0136] (h) Synthesis of 4-((6-mercaptohexyl)thio)-4-methylpentan-2-one (Compound 10) and 4,4'-(hexane-1,6-diylbis(sulfanediyl))bis(4-methylpentan-2-one) (Compound 11) DBU (0.52 g, 3.4 mmol) was slowly added to a solution of 4-methyl-3-penten-2-one (5.00 g, 51.0 mmol) and 1,6-hexanedithiol (10.00 g, 52.1 mmol) in THF (50 mL). After stirring at room temperature for 18 h, n-heptane (50 mL) was added, and the mixture was treated with aqueous HCl (10%, 50 mL) and washed with saturated aqueous NaCl (2 × 50 mL). The organic layer was dried (NaSO), filtered, and concentrated. These compounds can be used directly as a mixture. Column chromatography (SiO, n-heptane / ethyl acetate 9:1) afforded 2.61 g (31%) of compound 10 and 6.43 g (55%) of compound 11. [Table 8]

[0137] (i) Synthesis of 3-((6-mercaptohexyl)thio)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)butan-1-one (Compound 12), 3,3'-(hexane-1,6-diylbis(sulfanediyl))bis(1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)butan-1-one) (Compound 13), 4-methyl-4-((6-((4-oxo-4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)butan-2-yl)thio)hexyl)thio)pentan-2-one (Compound 14), and 4-((6-mercaptohexyl)thio)-4-methylpentan-2-one (Compound 10) (E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one (3.81 g, 20.0 mmol), 4-methyl-3-penten-2-one (1.96 g, 20.0 mmol), and 1,6-hexanedithiol (3.01 g, 20.0 mmol) were stirred at room temperature for 30 days. Column chromatography (SiO2, n-heptane to n-heptane / ethyl acetate 95:5) afforded 0.44 g of a mixture of 1,6-hexanedithiol and compound 12 (approximately 55:45), 0.85 g of a mixture of compound 12 and compound 13 (approximately 34:66), and 0.03 g of compound 13. Further, elution (n-heptane / ethyl acetate 9:1 to 1:1) gave 0.13 g of a mixture of Compound 14 and Compound 10 (approximately 50:50). [Table 9]

[0138] (j) Synthesis of (3R,3'R)-6,6'-((decane-1,10-diylbis(sulfanediyl))bis(propane-2,2-diyl))bis(3-methylcyclohexan-1-one) (Compound 15) DBU (0.26 g, 1.7 mmol) was slowly added to a solution of (R)-5-methyl-2-(propan-2-ylidene)cyclohexan-1-one (5.60 g, 36.8 mmol) and 1,10-decanedithiol (3.45 g, 16.7 mmol) in THF (50 mL). After stirring at room temperature for 18 h, n-heptane (50 mL) was added, and the mixture was treated with aqueous HCl (10%, 50 mL) and washed with saturated aqueous NaCl (2 × 50 mL). The organic layer was dried (NaSO), filtered, and concentrated to give 8.93 g of crude compound. Column chromatography on 3.0 g (SiO, n-heptane / ethyl acetate 95:5) afforded 0.31 g (10%) of compound 15 as a mixture of isomers (approximately 2:1). [Table 10]

[0139] Example 2 Performance of Model Surface Cleaners Containing Compounds of Formula (I) of the Invention - Comparison of Fragrance Release from Monomeric and Dimeric Structures Compound 11 (76.8 mg) was dissolved in 2-propanol (0.2 mL). An aqueous solution of sodium lauryl ether sulfate (SLES 10%) was then added to a volume of 5 g, forming a simplified model surface cleaner formulation. An aliquot (90 mg) of this solution was spread onto a glass plate (2.5 × 7.5 cm) and allowed to dry for 24 hours. The glass plate was then placed in a homemade headspace cell (internal volume approximately 625 mL), and a continuous airflow (approximately 200 mL / min) was drawn through the sampling cell. The airflow was passed through activated carbon and saturated aqueous NaCl to ensure a constant humidity of 75%. Volatiles were then adsorbed alternately onto used Tenax® cartridges for 15 minutes and clean Tenax® cartridges for another 15 minutes over a 3-hour (180-minute) period, resulting in a total of six data points. The spent cartridge was discarded, and the other cartridge was desorbed (280°C for 10 min) on a Markes TD 100-XR desorber. Volatiles were injected into an Agilent Technologies 7890A gas chromatograph equipped with a Supelco SPB1 capillary column (30 m, 0.25 mm i.d., 0.25 μm film thickness) connected to an Agilent 5975C inert MSD mass spectrometer. The volatiles were eluted with a flow of He at 0.9 mL / min using a temperature gradient running from 40°C (1 min) to 180°C at 10°C / min and then to 260°C at 30°C / min. Headspace concentrations (ng / L in air) were determined by external standard calibration using various concentrations of 4-methylpent-3-en-2-one as the fragrance released in ethanol. Each calibration solution (0.2 μL) was injected onto a clean Tenax® cartridge, which was desorbed and analyzed under the same conditions.

[0140] Similar experiments were carried out using 4-(dodecylthio)-4-methylpentan-2-one as a reference compound, the synthesis of which is described in the prior art (J.R. Stephens, J.J. Hydock, M.P. Kleinholz, J. Am. Chem. Soc., 1951, 73, 4050).

[0141] The average headspace concentration (average value of six data points) obtained from two measurements is shown in Table 1. [Table 11]

[0142] Thus, "dimeric" compounds according to formula (I) (where Q is a divalent hydrocarbon group) are more efficient at releasing fragrance ingredients than the corresponding "monomeric" analogs from the prior art (where Q is a monovalent hydrocarbon group).

[0143] Example 3 Performance of fabric softener bases containing compounds of formula (I) of the present invention The development of long-lasting fresh green, floral and fruity fragrance from compounds of formula (I) of the present invention was tested in a fabric softening surfactant emulsion having the following final composition: Stepantex® VL90A (manufacturer: Stepan) 12.21% by weight Calcium chloride (10% aqueous solution) 0.40% by weight Proxel® GXL (manufacturer: Avecia) 0.04% by weight Water 87.35% by weight

[0144] In a flask, a solution (0.1 mL) of one of the compounds of formula (I) of the present invention described in Example 1 in ethanol (10 mL) was added to fabric softener (0.07 g) (in an amount that would release a total of 0.05 mmol of the given fragrance) and diluted with cold demineralized tap water (23 g). The sample was vigorously shaken (10 times). Next, approximately 5.1 g of a cotton sheet (EMPA cotton test cloth No. 221, manufacturer: Eidgenoessische Materialpruefanstalt) pre-washed with unscented detergent powder and cut into a sheet of approximately 15 x 15 cm was added, stirred manually for 3 minutes, allowed to stand for 2 minutes, and then squeezed out by hand and weighed (approximately 10.0 g) to obtain a constant amount of residual water. A standard sample (0.1 mL) consisting of an equimolar amount of unmodified fragrance (0.05 mmol) in ethanol (10 mL) was added to 0.07 g of fabric softener in 23 g of water and analyzed in the same manner. Cotton sheets were line-dried for one or three days before analysis. For measurements, the sheets were placed in a headspace sampling cell (internal volume approximately 165 mL), which was thermostated at 25°C and exposed to a constant air flow of approximately 200 mL / min. The air was filtered through activated carbon and drawn through a saturated solution of NaCl (to ensure a constant air humidity of approximately 75%). The system was equilibrated for 15 minutes while volatiles were adsorbed onto a used Tenax® cartridge (filled with 100 mg of Tenax® TA adsorption resin). The volatiles were then adsorbed onto a clean Tenax® cartridge for 15 minutes and then onto a used Tenax® cartridge for 45 minutes, seven times in succession. The spent cartridge was discarded, and the other cartridge was desorbed on a Perkin Elmer TurboMatrix 350 desorber coupled to an Agilent Technologies 7890A gas chromatograph equipped with an HP-1 capillary column (30 m, 0.25 mm internal diameter, 0.25 μm film thickness) and an Agilent 5975C inert MSD mass spectrometer. Volatiles were eluted with helium (1 mL / min) using a temperature gradient from 60 °C (hold for 1 min) to 200 °C running at 10 °C / min.Alternatively, the cartridges were desorbed using a Perkin Elmer TurboMatrix desorption device connected to an Agilent Technologies 7890A gas chromatograph equipped with an HP-1 capillary column (30 m, 0.32 mm internal diameter, 0.25 μm film thickness) and a flame ionization detector. Volatiles were eluted with helium (1 mL / min) using a temperature gradient running from 80°C to 220°C at 10°C / min. Headspace concentrations (ng / L in air) were determined by external standard calibration. Solutions of fragrance to be released in ethanol at different concentrations were injected (0.2 μL) onto clean Tenax® cartridges, which were desorbed and analyzed under the same conditions. The results obtained for fragrance evaporation on dry cotton after 1 and 3 days of line drying after a total sampling time of 150 minutes are summarized in Table 2. All data are the average of at least two measurements. [Table 12-1] [Table 12-2]

[0145] The compound of formula (I) released a greater amount of fresh green, floral and fruity scent into the headspace above the dry cotton than the standard sample with unmodified fragrance. Thus, the compound of formula (I) according to the present invention can impart a long-lasting fresh green, floral and fruity scent to the cotton surface.

[0146] Example 4 Perfume oil production A non-limiting example of a typical perfume oil is prepared by mixing the following perfuming co-ingredients: [Table 13-1] [Table 13-2]

[0147] Example 5 Preparation of liquid detergent formulations containing compounds of formula (I) of the present invention Typical unscented liquid detergent formulations are listed in Table 3. Perfumed liquid detergents are prepared by adding perfume oil (0.3-0.8% by weight, based on the total weight of the liquid detergent) and at least one compound of formula (I) of the present invention (0.05-1.0% by weight, based on the total weight of the liquid detergent) to the unscented liquid detergent formulations of Table 3 with gentle shaking. [Table 14]

[0148] Example 6 Preparation of general-purpose detergent formulations containing compounds of formula (I) of the present invention Typical general-purpose detergent formulations are listed in Table 4. A perfumed general-purpose detergent is prepared by adding perfume oil (0.3-0.8 wt. %, based on the total weight of the general-purpose detergent) and at least one compound of formula (I) of the present invention (0.05-0.8 wt. %, based on the total weight of the general-purpose detergent) to the unscented general-purpose detergent formulation of Table 4 with gentle shaking. [Table 15]

[0149] Example 7 Preparation of clear isotropic shampoo formulations containing compounds of formula (I) of the present invention A typical unscented, clear, isotropic shampoo formulation is listed in Table 5. An unscented shampoo formulation is prepared by dispersing Polyquaternium-10 in water. The remaining ingredients of Phase A are mixed separately by adding them in sequence, with thorough mixing after each combination. This premix is ​​added to the Polyquaternium-10 dispersion and mixed for an additional 5 minutes. Next, premixed Phase B and premixed Phase C are added with stirring (Monomuls® 90L-12 is heated to dissolve in Texapon® NSO IS). Phases D and E are added with stirring. The pH is adjusted to 5.5-6.0 with citric acid solution to yield the unscented shampoo formulation listed in Table 5. [Table 16]

[0150] A perfume oil (0.1-0.8% by weight, based on the total weight of the unscented shampoo formulation) and at least one compound of formula (I) (0.05-0.5% by weight, based on the total weight of the unscented shampoo formulation) are added to the unscented shampoo formulations listed in Table 5 with gentle shaking to obtain scented shampoo formulations.

[0151] Example 8 Preparation of pearlescent shampoo formulations containing compounds of formula (I) of the present invention A typical fragrance-free pearlescent shampoo formulation is listed in Table 6. An unscented shampoo formulation is prepared by dispersing tetrasodium EDTA, guar hydroxypropyltrimonium chloride, and polyquaternium-10 in water. Once Phase A is homogeneous, NaOH (10% aqueous solution, Phase B) is added. The premixed Phase C is then added, and the mixture is heated to 75°C. The ingredients of Phase D are added and mixed until the mixture is homogeneous. The mixture is cooled. At 45°C, the ingredients of Phase E are added with mixing. The final viscosity is adjusted with NaCl (25% aqueous solution), and a pH of 5.5-6.0 is adjusted with NaOH (10% aqueous solution). [Table 17]

[0152] A perfume oil (0.1-0.8% by weight, based on the total weight of the unscented shampoo formulation) and at least one compound of formula (I) (0.05-0.5% by weight, based on the total weight of the unscented shampoo formulation) are added to the unscented pearlescent shampoo formulations listed in Table 6 with gentle shaking to obtain a scented pearlescent shampoo formulation.

[0153] Example 9 Preparation of rinse-off hair conditioner formulations containing compounds of formula (I) of the present invention A typical unscented rinse-off hair conditioner formulation is listed in Table 7. An unscented rinse-off hair conditioner formulation is prepared by mixing the ingredients in Phase A until a uniform mixture is obtained. The Tylose® is completely dissolved. The mixture is then heated to 70-75°C. The ingredients in Phase B are combined and melted at 70-75°C. The ingredients in Phase B are then added to Phase A with good agitation, and mixing is continued until the temperature of the mixture reaches 60°C. The ingredients in Phase C are then added with agitation, and mixing is continued until the mixture has cooled to 40°C. The pH is adjusted to 3.5-4.0 with citric acid solution. [Table 18]

[0154] A perfume oil (0.2-1.0 wt. %, based on the total weight of the unscented conditioner formulation) and at least one compound of formula (I) (0.05-0.5 wt. %, based on the total weight of the unscented conditioner formulation) are added to an unscented rinse-off hair conditioner formulation listed in Table 7 with gentle shaking to obtain a perfumed rinse-off hair conditioner formulation.

[0155] Example 10 Preparation of structured shower gel formulations containing compounds of formula (I) of the present invention Typical unscented structured shower gel formulations are listed in Table 8. Perfumed structured shower gels are produced by adding perfume oil (0.1-1.5 wt. %, 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 wt. %, based on the total weight of the structured shower gel) to the unscented structured shower gel formulation of Table 8 with gentle shaking. [Table 19]

[0156] Example 11 Preparation of clear shower gel formulations containing compounds of formula (I) of the present invention Typical unscented clear shower gel formulations are listed in Table 9. A scented clear shower gel is prepared by adding perfume oil (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 unscented clear shower gel formulation of Table 9 with gentle shaking. [Table 20]

[0157] Example 12 Preparation of a milky shower gel formulation containing a compound of formula (I) of the present invention Typical unscented milky shower gel formulations are listed in Table 10. Perfumed milky shower gels are prepared by adding perfume oil (0.1-1.5% by weight, based on the total weight of the milky 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 milky shower gel) to the unscented milky shower gel formulations of Table 10 with gentle shaking. [Table 21]

[0158] Example 13 Preparation of anhydrous antiperspirant spray formulations containing compounds of formula (I) of the present invention A typical fragrance-free anhydrous antiperspirant spray formulation is listed in Table 11. The anhydrous antiperspirant spray formulation is prepared using a high-speed mixer. Silica and quaternium-18-hectorite are added to a mixture of isopropyl myristate and cyclomethicone. Once fully swollen, aluminum chlorohydrate is added in small portions with stirring until the mixture is homogeneous and lump-free. [Table 22]

[0159] Next, perfume oil (0.85% by weight, based on the total weight of the antiperspirant spray formulation) and at least one compound of formula (I) of the present invention (0.15% by weight, based on the total weight of the antiperspirant spray formulation) are added to the unscented antiperspirant spray formulation of Table 11 to obtain a scented formulation.

[0160] Example 14 Preparation of deodorant spray emulsion formulations containing compounds of formula (I) of the present invention A typical deodorant spray emulsion formulation is prepared by mixing and dissolving all ingredients according to the order shown in Table 12. Next, perfume oil (1.35% by weight, based on the total weight of the deodorant spray formulation) and at least one compound of formula (I) of the present invention (0.10-0.20% by weight, based on the total weight of the deodorant spray formulation) are added with gentle shaking. An aerosol can is then filled and the propellant is added by compression. Aerosol filling: 40% active solution, 60% propane / butane (2.5 bar). [Table 23]

[0161] Example 15 Preparation of deodorant stick formulations containing compounds of formula (I) of the present invention A typical deodorant stick formulation is obtained by weighing all ingredients of Part A (Table 13) and heating to 70-75°C. Once the other Part A ingredients are mixed and heated, Ceteareth-25 is added. Stearic acid is added when Ceteareth-25 is dissolved. Part B is prepared by dissolving triclosan in 1,2-propylene glycol (Table 13). Evaporated water is replaced. Part B is then poured into Part A while mixing slowly. [Table 24]

[0162] A perfume oil (0.85% by weight, based on the total weight of the deodorant stick formulation) and at least one compound of formula (I) of the present invention (0.10-0.20% by weight, based on the total weight of the deodorant stick formulation) are added with gentle shaking. For storage, the bucket is placed in a plastic bag and sealed after cooling. The mold is filled at approximately 70°C.

[0163] Example 16 Preparation of deodorant roll-on formulations containing compounds of formula (I) of the present invention A typical fragrance-free deodorant roll-on formulation is listed in Table 14. Part A is prepared by sprinkling hydroxyethyl cellulose in small amounts into water and rapidly stirring with a turbine until the hydroxyethyl cellulose is completely swollen and forms a clear gel. Part B is slowly poured into Part A while continuing to stir until the entire mixture is homogeneous. Part C is then added. [Table 25]

[0164] A perfume oil (0.85% by weight, based on the total weight of the deodorant stick formulation) and at least one compound of formula (I) of the present invention (0.10-0.20% by weight, based on the total weight of the deodorant stick formulation) are added with gentle shaking to obtain a perfumed deodorant roll-on formulation.

[0165] Example 17 Preparation of a day cream base O / W emulsion containing a compound of formula (I) of the present invention A typical day cream base O / W emulsion formulation containing a compound of formula (I) of the present invention is listed in Table 15. Phases A and B are heated separately to 70-75°C, then phase A is added to phase B and a vacuum is applied. The mixture is stirred and cooled to 55°C for 15 minutes. After cooling to room temperature, phenoxyethanol (and) piroctone olamine (part C) are added when a temperature of 45°C is reached. The mixture is stirred for 5 minutes, after which sodium carbomer (part D), perfume oil, and at least one compound of formula (I) of the present invention (part E) are added. The mixture is stirred for 3 minutes, and then stirring is stopped for 15 minutes. When the temperature of the mixture reaches 30°C, stirring is continued for another 15 minutes until the cream is homogeneous, glossy, and lump-free. If necessary, adjust the pH to 6.70-7.20 with Glydant®, Phenoni® p or Nipaguard® PO5 or to 6.30-7.00 with Nikkoguard®. [Table 26]

[0166] Example 18 Preparation of Hand Dishwashing Formulations Containing Compounds of Formula (I) of the Invention A typical unscented hand dishwashing detergent formulation is listed in Table 16. The unscented hand dishwashing detergent is prepared by mixing sodium hydroxide and diethanolamide with water. Linear alkylbenzene sulfonic acid is then added. After neutralization, the remaining ingredients are added and the pH is adjusted to 7-8 as needed. [Table 27]

[0167] A perfume oil (0.85% by weight based on the total weight of the hand dishwashing formulation) and at least one compound of formula (I) of the present invention (0.10-0.20% by weight based on the total weight of the dishwashing formulation) are added with gentle shaking to obtain a perfumed hand dishwashing formulation.

Claims

1. formula 【Chemical 1】 [In the formula, R １ and R １’ represent, independently of each other, a hydrogen atom or a methyl group; or both R １ and / or both R １’ When taken together, they form a divalent C ３ ~C ８ represents a hydrocarbon group, R ２ represents a hydrogen atom, a methyl group, or an ethyl group; R ２’ represents a methyl group or an ethyl group, R ３ and R ３’ are each independently a hydrogen atom or C １ ~C １６ represents a hydrocarbon group; or R １ and R ３ and / or R １’ and R ３’ When taken together, they form a divalent C ２ ~C １２ represents a hydrocarbon group, Q represents a divalent butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, 3-oxapentyl, 3,6-dioxaoctyl, 3,6,9-trioxaundecyl, or 3,6,9,12-tetraoxatetradecyl; and Each X is independently a group of formula (i) to (iii) 【Chemistry 2】 wherein the wavy line indicates the position of the bond between carbon 2 or 2' and X, and the slash indicates the position of the bond between X and Q, with the proviso that the slash is not directly bonded to the heteroatom Q, and the two X groups bonded to Q are separated from each other by at least four carbon atoms, but 4,4'-(methylenebis(4,1-phenylenesulfonyl))bis(4-methylpentan-2-one) and 4,4'-([1,1'-biphenyl]-4,4'-disulfonyl)bis(4-methylpentan-2-one) are excluded.

2. R １ and R １’ represents a hydrogen atom or a methyl group; R ２ and R ２’ represents a methyl group or an ethyl group, R ３ and R ３’ is a hydrogen atom or C １ ~C １０ represents a hydrocarbon group; or R １ and R ３ and / or R １’ and R ３’ When combined, the divalent C ２ ~C ６ represents a hydrocarbon group, X represents a group of formula (i) and / or (ii), and 2. The compound of claim 1, wherein Q represents a divalent butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, 3-oxapentyl, 3,6-dioxaoctyl, 3,6,9-trioxaundecyl, or 3,6,9,12-tetraoxatetradecyl.

3. The compound of formula (I) is of the formula 【Chemistry 3】 [In the formula, R １ , R ２ , R ３ 3. The compound according to claim 1, wherein X and Q have the same meanings as defined in any one of claims 1 to 2.

4. The compound of formula (I) is of the formula 【Chemistry 4】 4. The compound according to any one of claims 1 to 3, which is a compound of the formula: wherein X and Q have the same meanings as defined in any one of claims 1 to 2.

5. The compound of formula (I) is of the formula 【Chemistry 5】 [In the formula, R １ , R ２ , R ３ 3. The compound according to claim 1, wherein X and Q have the same meanings as defined in claim 1, and the dotted line represents the position of a single or double bond.

6. The compound of formula (I) is of the formula 【Chemistry 6】 [In the formula, R １ , X and Q have the same meanings as defined in any one of claims 1 to 2, and the dotted line represents the position of a single or double bond.

7. The compound of formula (I) is of the formula 【Chemistry 7】 [In the formula, R １ , R ２ , R ３ and Q has the same meaning as defined in any one of claims 1 to 2.

8. The compound of formula (I) is of the formula 【Chemistry 8】 8. A compound according to any one of claims 1, 2 and 7, which is a compound of the formula: wherein Q has the same meaning as defined in any one of claims 1 to 2.

9. 10. Use of a compound of formula (I) according to any one of claims 1 to 8 as a perfuming ingredient for imparting a long-lasting fresh green, floral and / or fruity scent to an environment.

10. A method for imparting, enhancing, improving or modifying the fresh green, floral and / or fruity scent characteristics of a perfumed composition or a perfumed article, comprising adding to said composition or article an effective amount of at least one compound of formula (I) as defined in any one of claims 1 to 8.

11. A fragrance composition comprising: i) at least one compound of formula (I) as defined in any one of claims 1 to 8 as perfuming ingredient; 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 fragrance composition comprising:

12. A scented consumer product comprising, as a perfuming ingredient, at least one compound of formula (I) as defined in any one of claims 1 to 8 or a perfuming composition as defined in claim 11.

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

14. A method for imparting a long-lasting or persistent fresh green, floral and / or fruity scent to a surface by adding at least one compound of formula (I) according to any one of claims 1 to 8 to a perfumed composition or a perfumed article and applying the same to the corresponding target surface.

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