WO2007143873A1 - Fragrance compounds - Google Patents

Fragrance compounds Download PDF

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Publication number
WO2007143873A1
WO2007143873A1 PCT/CH2007/000294 CH2007000294W WO2007143873A1 WO 2007143873 A1 WO2007143873 A1 WO 2007143873A1 CH 2007000294 W CH2007000294 W CH 2007000294W WO 2007143873 A1 WO2007143873 A1 WO 2007143873A1
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WO
WIPO (PCT)
Prior art keywords
nitrogen
oxygen
dimethyl
methyl
enal
Prior art date
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Ceased
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PCT/CH2007/000294
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English (en)
French (fr)
Inventor
Felix Flachsmann
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Givaudan SA
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Givaudan SA
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Filing date
Publication date
Application filed by Givaudan SA filed Critical Givaudan SA
Priority to US12/304,224 priority Critical patent/US8575386B2/en
Priority to BRPI0713765A priority patent/BRPI0713765B1/pt
Priority to MX2008015444A priority patent/MX2008015444A/es
Priority to CN2007800223934A priority patent/CN101472874B/zh
Priority to ES07720191T priority patent/ES2394222T3/es
Priority to JP2009514609A priority patent/JP5415260B2/ja
Priority to EP07720191A priority patent/EP2032516B1/en
Publication of WO2007143873A1 publication Critical patent/WO2007143873A1/en
Anticipated expiration legal-status Critical
Priority to US15/185,226 priority patent/US9585362B2/en
Ceased legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01K—ANIMAL HUSBANDRY; AVICULTURE; APICULTURE; PISCICULTURE; FISHING; REARING OR BREEDING ANIMALS, NOT OTHERWISE PROVIDED FOR; NEW BREEDS OF ANIMALS
    • A01K1/00—Housing animals; Equipment therefor
    • A01K1/015—Floor coverings, e.g. bedding-down sheets ; Stable floors
    • A01K1/0152—Litter
    • A01K1/0155—Litter comprising organic material
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01K—ANIMAL HUSBANDRY; AVICULTURE; APICULTURE; PISCICULTURE; FISHING; REARING OR BREEDING ANIMALS, NOT OTHERWISE PROVIDED FOR; NEW BREEDS OF ANIMALS
    • A01K1/00—Housing animals; Equipment therefor
    • A01K1/015—Floor coverings, e.g. bedding-down sheets ; Stable floors
    • A01K1/0152—Litter
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/09—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/12—Ketones containing more than one keto group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/203—Unsaturated compounds containing keto groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/602—Dicarboxylic acid esters having at least two carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0007—Aliphatic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0007—Aliphatic compounds
    • C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0007—Aliphatic compounds
    • C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
    • C11B9/0019—Aliphatic compounds containing oxygen as the only heteroatom carbocylic acids; Salts or esters thereof
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2072—Aldehydes-ketones
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2093—Esters; Carbonates
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/32—Amides; Substituted amides
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • C11D3/502—Protected perfumes
    • C11D3/507—Compounds releasing perfumes by thermal or chemical activation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Definitions

  • This invention relates to the provision of fragrance and to a process and compounds for achieving this.
  • fragrance by the addition of inherently fragrant substances to products is well known and widely used.
  • An alternative method of providing fragrance is by the use of a precursor, that is, a substance that is not itself fragrant, but which, in particular circumstances, for example exposure to light, pH change and enzymatic activity, will break down to give at least one fragrant substance.
  • the invention therefore provides a method of providing a fragrant odour to an application, comprising the addition thereto of at least one compound of the formula I
  • X and Y are independently selected from the group consisting of -CR 1 R 2 R 3 , -NR 4 R 5 and -OR 6 , wherein R 1 to R 5 are selected from H and essentially hydrocarbon moieties that optionally comprise at least one oxygen, nitrogen or silicon atom, and R 6 is selected from essentially hydrocarbon moieties that optionally comprise at least one oxygen, nitrogen or silicon atom; and
  • A is an essentially hydrocarbon moiety that optionally comprises at least one oxygen, sulphur, nitrogen or silicon atom, with the proviso that the compound A-CHO is a fragrant aldehyde.
  • the invention additionally provides use of a compound of Formula I as hereinabove defined as a precursor of a fragrance.
  • essentially hydrocarbon moieties that optionally comprise at least one oxygen, nitrogen or silicon atom (and, in the case of A, also at least one sulphur atom) is meant that the moieties X, Y and A are at least predominantly hydrocarbon in nature, that is, that the moieties will comprise mainly carbon and hydrogen, and that the number of carbon atoms present on a given moiety is greater than that of any oxygen, nitrogen and silicon (and, in the case of A, sulphur) atoms present.
  • there is present one oxygen atom there must be present at least two carbon atoms on the moiety.
  • oxygen, nitrogen, sulphur and silicon atoms may either form part of the otherwise hydrocarbon chain, or they may be linked to carbon atoms on the chain, either directly (for example, a carbonyl group oxygen or a hydroxyl group) or as part of a substituent (for example, a nitrile group).
  • the wavy bond to the hydrogen means that the arrangement at the ethylenic double bond may be either in the E- or the Z- configuration.
  • one or other isomer may be preferred, but this is not usually the case.
  • stereogenic units such as chiral centres or substituted double bonds, which result in there existing several different stereoisomers. In some cases, these can result in odours of different strengths or even characters, and these can be separated by conventional techniques, if desired. However, this adds to the complexity (and therefore the expense), and it is generally preferred to leave the compounds as a mixture of stereoisomers.
  • A is defined by the requirement that A-CHO is a fragrant aldehyde. Such molecules are well known to the art. Examples of fragrant aldehydes from which the moiety A may be derived include, but are not limited to, the following:
  • X and Y are independently selected from the following moieties:
  • R 6 is C 1 -C 20 alkyl, linear or branched, optionally containing oxygen, nitrogen or silicium atoms, such as methyl, ethyl, propyl, butyl, isobutyl, 2-ethylhexyl, tert.- butyl; or cyclopentyl, cyclohexyl; or C 3 -C 1O alkenyl, linear or branched, such as propenyl, isopropenyl, isobutenyl; or C 6 -C 8 aryl, such as phenyl or naphtyl; and
  • R 4 and R 5 are, independently of each other, H; C 1 -C 20 alkyl, linear or branched, such as methyl, ethyl, propyl, butyl, isobutyl, 2-ethylhexyl, optionally containing oxygen or nitrogen atoms; or cyclopentyl, cyclohexyl; alternatively NR 4 R 5 form together a 3-, 5- or 6-membered ring.
  • A is selected from the group consisting Of C 7 -C 17 linear or branched alkyl, cycloalkyl, alkylcycloalkyl or cycloalkylalkyl, C 7 -C 15 linear or branched alkenyl, and C 6 -C 10 aryl.
  • One way of preparing the compounds is via a Knoevenagel condensation, in which a fragrant aldehyde is reacted with a suitable 1,3-dicarbonyl compound in the presence of a suitable catalyst, such as secondary amines, for example, piperidine, pyrrolidine, dimethylamine, diethylamine, or ammonium salts, for example, ammonium acetate and ethylene diamine diacetate.
  • a suitable catalyst such as secondary amines, for example, piperidine, pyrrolidine, dimethylamine, diethylamine, or ammonium salts, for example, ammonium acetate and ethylene diamine diacetate.
  • a suitable catalyst such as secondary amines, for example, piperidine, pyrrolidine, dimethylamine, diethylamine, or ammonium salts, for example, ammonium acetate and ethylene diamine diacetate.
  • 1,3-dicarbonyl compounds include ethyl 3-oxobutanoate, ethyl 3-oxo-3-phenylpropanoate, benzyl 3-oxobutanoate, diethyl malonate, dimethyl malonate, diisopropyl malonate, dibenzyl malonate, l-(4-tert-butylphenyl)-3-(4- methoxyphenyl)-propane-l,3-dione (ParsolTM 1789) and ethyl l-(3,3- dimethylcyclohexyl) ethyl malonate (Musk compositionTM, (IFF)).
  • 1,3-dicarbonyl compounds include ethyl 3-oxobutanoate, ethyl 3-oxo-3-phenylpropanoate, benzyl 3-oxobutanoate, diethyl malonate, dimethyl malonate, diisopropyl
  • X and Y are the same and are selected from a) -OR 6 , wherein R 6 is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, benzyl; or b) phenyl, methyl, ethyl, propyl, isopropyl, butyl, isobutyl ; or
  • X and Y are different, and are selected according to the following table:
  • A is selected from branched or linear C 7 -C 15 alkyl and C 7 -C 15 alkenyl moieties, these optionally comprising oxygen atoms present as ether, hydroxyl, carbonyl or ester moieties. All of the compounds of formula I hereinabove described have in common the fact that, on exposure to moisture, either liquid water applied to the compounds or to a support on which they have been deposited, or water vapour in the atmosphere, they release a fragrant aldehyde.
  • the compound may be chosen from a very wide variety of such materials.
  • they can be chosen such that the compound, once separated from the fragrant aldehyde, performs a desired function.
  • the compound itself may have fragrant characteristics, either as a fragrant material in its own right, or as a modifier for the fragrant aldehyde, or other fragrant material also present in a composition in which the compound useful in the invention is used.
  • Another possibility is that it may enhance substantivity or stability in a given application.
  • a third possibility is that it perform an entirely independent function in a composition.
  • it may act as a sunscreen, thus, for example, supplying a cosmetic composition simultaneously with a fragrance and a protective function.
  • the skilled person will readily comprehend that there are many other possible uses, and will be able to tailor the 1,3- dicarbonyl compound appropriately to perform any such function.
  • the invention is useful for providing a fragrant odour to an application where release of the odour is desired at some particular time point and is caused by the presence of moisture.
  • "Application" in the context of this invention means any use in which such an effect is desired. Examples include laundry use (release in a wash liquor, in a dryer or on laundry post-drying), use in hard surface cleaners, cosmetics, protective creams, personal care products, such as hair care products, skin creams and lotions, fine fragrances and air-care products, such as air fresheners.
  • the compounds may be combined with any other suitable free fragrance material.
  • they may be combined with free fragrance aldehydes, so that the free fragrance delivers an immediate impact and the compounds of the invention provide a lasting fragrance.
  • the compounds of the present invention the strong floral-fresh impact of many fragrant aldehydes, which by themselves are not substantive, can be prolonged in many applications where such long-lasting freshness is desired, without having to overdose the aldehydes in the perfume. This opens new possibilities for fragrance creation.
  • the compounds for use in this invention may be incorporated into commercial products in conventional proportions and by art-recognised methods.
  • Commercial products include washing and laundry detergents, fabric softeners and conditioners, personal care products, such as hair and skin care preparations, soaps and lotions. They may be incorporated directly into such compositions, or they may be added in conjunction with a carrier, such as microcapsules, adsorbed on to suitable particulate matter or spray-dried.
  • the compounds need not be made in a manufacturing plant and shipped to the user, but they may be made in situ. They can thus be made simply and easily on site and then added directly to the composition in which their presence is desired. This confers a considerable versatility, in that it allows a user to make a desired compound on the spot, without waiting for a delivery.
  • the invention therefore also provides a process of manufacturing a fragranced composition, in which the fragrance is gradually released on exposure to moisture, comprising the steps of
  • Conditions allowing a Knoevenagel condensation to take place in situ include also thermal dehydration methods such as spray-drying.
  • the mixture of a compound of formula II, together with one or several fragrant aldehydes and a base are formulated into an aqueous emulsion, containing optional carrier materials and surfactants.
  • This emulsion is then spray-dried, thereby producing solid particles containing products of formula I.
  • Piperidine (0.10 ml, 0.5 mol%) is added to a mixture of octanal (25.6 g, 0.20 mol) and ethyl benzoylacetate (38.4 g, 0.20 mol) at 5 0 C.
  • the resulting solution is warmed to room temperature and stirred for 24 h, during which a fine emulsion is formed.
  • the mixture is diluted with methyl t-butyl ether and the organic layer washed with 2 N aq. HCl-solution, water and brine, then dried over MgSO 4 .
  • the product contains ca. 15% of 2-(l-hydroxy-ethylidene)-dec-3-enoic acid 2-(2- methoxy-ethoxy)-ethyl ester.
  • the starting material, 3-oxo-butyric acid 2-(2-methoxy- ethoxy)-ethyl ester is prepared as follows:
  • Ethyl acetoacetate (39.0 g, 0.30 mol) and diethyleneglycol monomethyl ether (36.0 g, 0.30 mol) are heated to 11O 0 C (oil bath temperature) and tetraisopropyl orthotitanate (0.60 ml, 2.0 mmol, 0.7 mol%) is added. The temperature is further increased to 150 0 C. After 30 min methanol (5 g) is distilling off and collected. The temperature is maintained for further 8 h while lowering the pressure in the apparatus to 800 mbar. After cooling to room temperature, the residue is distilled at 65-120 0 C / 0.06 mbar to isolate 30.5 g of product containing ca.
  • the towels washed with the liquid detergent base comprising a compound according to the invention exhibit a strong 2-methylundecanal note, whereas the towels washed with base containing the free aldehyde are almost weak to odourless.
  • the towels washed with 2-acetyl-5-(3-isopropylphenyl)hex-2-enoate exhibit a strong Florhydral note after 1 day on the dry towel, whereas the towel washed with free Florhydral has only a very weak smell.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Environmental Sciences (AREA)
  • Biodiversity & Conservation Biology (AREA)
  • Animal Husbandry (AREA)
  • Zoology (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Fats And Perfumes (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cosmetics (AREA)
PCT/CH2007/000294 2006-06-15 2007-06-13 Fragrance compounds Ceased WO2007143873A1 (en)

Priority Applications (8)

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US12/304,224 US8575386B2 (en) 2006-06-15 2007-06-13 Fragrance compounds
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WO2020125921A1 (en) 2018-12-17 2020-06-25 Givaudan Sa Fragrance process
WO2020188079A1 (en) 2019-03-20 2020-09-24 Firmenich Sa Encapsulated pro-perfume compounds
WO2020260598A1 (en) 2019-06-27 2020-12-30 Firmenich Sa Perfumed consumer products
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US8617528B2 (en) 2010-12-06 2013-12-31 Sytheon Ltd. Compositions and methods for stabilizing ingredients using 2,4-pentanedione compounds
WO2012078544A3 (en) * 2010-12-06 2012-08-02 Sytheon Ltd. Benzylidene substituted 2,4-pentanedione compounds and use thereof as stabilizers
USRE49502E1 (en) 2014-11-10 2023-04-25 Givaudan Sa Phenyl based compounds substituted with aldehyde moieties and their use in perfumery
WO2018096176A1 (en) * 2016-11-28 2018-05-31 Givaudan Sa Precursor compounds for fragrant aldehydes
US11359161B2 (en) 2018-03-02 2022-06-14 Givaudan Sa Thioether precursors for fragrant ketones and aldehydes
WO2020125922A1 (en) 2018-12-17 2020-06-25 Givaudan Sa A method of countering malodour in a washing machine comprising the addition of a fragrance precursor
WO2020125921A1 (en) 2018-12-17 2020-06-25 Givaudan Sa Fragrance process
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US12024690B2 (en) 2018-12-17 2024-07-02 Givaudan Sa Method of countering malodour in a washing machine comprising the addition of a fragrance precursor accord comprising 4-(dodecylthio)-4-methylpentan-2-one
WO2020188079A1 (en) 2019-03-20 2020-09-24 Firmenich Sa Encapsulated pro-perfume compounds
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WO2025003204A1 (en) 2023-06-27 2025-01-02 Givaudan Sa Organic compounds and their use for generating a fragrant alcohol
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