WO2003070871A1 - Composition pour lutter contre les mauvaises odeurs - Google Patents

Composition pour lutter contre les mauvaises odeurs Download PDF

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Publication number
WO2003070871A1
WO2003070871A1 PCT/EP2002/001924 EP0201924W WO03070871A1 WO 2003070871 A1 WO2003070871 A1 WO 2003070871A1 EP 0201924 W EP0201924 W EP 0201924W WO 03070871 A1 WO03070871 A1 WO 03070871A1
Authority
WO
WIPO (PCT)
Prior art keywords
aldehyde
saturated
malodor
masking
laundry
Prior art date
Application number
PCT/EP2002/001924
Other languages
English (en)
Inventor
Wolfgang Neugebauer
Noubar Khoren Hagop
Original Assignee
Symrise Gmbh & Co. Kg
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Symrise Gmbh & Co. Kg filed Critical Symrise Gmbh & Co. Kg
Priority to EP02806849A priority Critical patent/EP1481049A1/fr
Priority to AU2002308301A priority patent/AU2002308301A1/en
Priority to PCT/EP2002/001924 priority patent/WO2003070871A1/fr
Publication of WO2003070871A1 publication Critical patent/WO2003070871A1/fr

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50Perfumes
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005Other compounding ingredients characterised by their effect
    • C11D3/0068Deodorant compositions

Definitions

  • the present invention according to a first aspect concerns a malodor counteracting and/or masking composition, which is in particular effective against malodor developed during soaking and/or hand washing laundry.
  • the invention further concerns a method for counteracting or masking malodor, in particular malodor produced during soaking and/or hand washing of laundry.
  • the invention concerns a laundry detergent comprising a malodor counteracting and/or masking composition.
  • Further aspects of the invention concern a method of preparing a malodor counteracting and/or masking composition, a fragrance composition comprising a malodor counteracting and/or masking composition, and a method for soaking and/or hand washing and/or machine washing of laundry.
  • soaking ' and hand washing are very common.
  • perceivable malodors are generated and/or set free through complex interaction between fabrics, dirt (eg. sweat) and wash liquor.
  • the present invention provides methods and substances for reducing the perception of these malodors which are generated during soaking and hand washing of laundry.
  • malodor counteracting compositions are disclosed in WO 00/27442, US 4,187,251 and US 4,310,512, according to which a perception of a malodor is decreased while reducing or not contributing to the overall perceived odor level.
  • These malodor counteractant compositions are inter alia meant to be included in cloths deodorants as used for washing machine applications such as in detergent, powders, liquids or fabric softeners.
  • WO 00/1360 unpleasant sulphurous body odors are reduced by treating fabric with laundry products containing specific perfume compositions.
  • These compositions contain at least 15% defined aldehydes and at least 30% of one of five categories of hydroxylic materials, ketones, esthers, esters and nitriles.
  • EP 483 426 A1 teaches a deodorant composition for controlling malodor from perspiration comprising a thiol heterocyclic compound.
  • the deodorant composition can be applied to fabric through a laundry product.
  • WO 01/16265 discloses a method of reducing odor on fabrics in a wash or rinse solution.
  • the odor control agent is selected from the group consisting of uncomplexed cyclodextrin, odor blocker, specified aldehydes, flavonoid, metallic salt, and mixtures thereof. To be effective however, a high amount of cyclodextrin is required.
  • composition suitable for counteracting and/or masking malodor developed during soaking and/or hand washing of laundry comprising:
  • R1 a hydrogen atom or a linear or branched, saturated or unsaturated alkanoate, aldehydic, or alkoxy radical having 1-4 carbon atoms,
  • R2 a hydrogen atom or a linear, saturated alkylcarboxylate radical having 1-4 carbon atoms
  • Verdalia A Greenyl methylether
  • the notation/nomenclature used in the CAS database is used for certain substituents/structural units.
  • EP 1 113 105 A2 comprises no teaching that said methanoindene derivatives are effective on its own and thus could be incorporated into a malodor or masking composition in an (individually) malodor counteracting and/or masking effective amount. Accordingly, said methanoindene derivatives are not characterized as essential ingredients of the malodor maskant compositions disclosed in EP 1 113 105 A2.
  • WO 99/57233 discloses a perfume composition comprising at least 5% (by weight of the perfume composition) of a so-called "class 4"-substance which can be ethyl tricyclo[5.2.1.0(2,6)]decane-2-carboxylate (Fruitate). Besides said class 4 component at least 17% of a class 3 and at least 20% of a class 6 component are present. Thus, WO 99/57233 does not disclose a malodor counteracting and/or masking composition comprising a malodor counteracting and/or masking effective amount of a methanoindene derivative as stated above. To the contrary, according to WO 99/57233 only a combination of components chosen from class 3 plus class 4 plus class 6 is useful.
  • a method for counteracting or masking malodor produced during soaking and/or hand washing of laundry comprises the following steps:
  • a laundry detergent which comprises a malodor counteracting and/or masking effective amount of a composition as described above with respect to the first aspect of the present invention.
  • Such laundry detergent is of particular use in laundry processes which comprise soaking and/or hand washing of laundry, however, it can also be useful in other types of laundry processes like e.g. machine washing.
  • the laundry detergent preferably is a powder detergent which is water soluble.
  • a method of preparing a malodor counteracting and/or masking composition comprising the step of mixing one, two or more members of the group consisting of:
  • R1 a hydrogen atom or a linear or branched, saturated or unsaturated alkanoate, aldehydic, or alkoxy radical having 1-4 carbon atoms, and, independently thereof,
  • R2 a hydrogen atom or a linear, saturated alkylcarboxylate radical having
  • a solvent or a dispersion agent and/or other additives such that the total amount of said member(s) of said group is sufficient for counteracting and/or masking a malodor in a process comprising soaking and/or hand washing of laundry.
  • a fragrance composition comprising (a) a sensorically effective amount of a fragrance material and (b) a malodor counteracting and/or masking effective amount of one member or a mixture of two or more members of the group defined above with respect to the first aspect of the present invention, wherein (a) said fragrance and (b) said member or mixture of members are not the same.
  • the fragrance composition of the present invention is particularly useful for providing laundry with a fragrance which is (at least almost) unaffected by malodor normally- produced during soaking and/or hand washing.
  • the malodor counteracting and/or masking substance may or may not contribute to the overall sensoric appearance of the laundry.
  • a method for soaking and/or hand washing and/or machine washing of laundry comprising the following steps:
  • the present invention allows for a significant reduction of adverse malodor when (a) a sample of laundry treated with the malodor counteracting and/or masking composition of the present invention (or a corresponding laundry detergent) is compared with (b) a control laundry treated with a composition not comprising any malodor counteracting and/or masking substances (e.g. pure water or a laundry detergent without malodor counteracting substances).
  • a sample of laundry treated with the malodor counteracting and/or masking composition of the present invention or a corresponding laundry detergent
  • a control laundry treated with a composition not comprising any malodor counteracting and/or masking substances e.g. pure water or a laundry detergent without malodor counteracting substances.
  • Methanoindene derivatives according to the present invention, Aldehyde C-11 (Undecanal), Aldehyde C-11 Inter, Aldehyde C-12 Erasmus, Ethyl Rosate, Galbanum Oil, Hivertal, Methyl Cresol Para, Methylacetophenone, Patchouli Oil, Undecavertol, Aldehyde C-11 Lenic, Allyl Cyclohexyl Propinate, Ambrettolide, Amyl Salicylate, Damascone Delta, Dihydromyrcenol, Ethylvanillin, Florazon, Irisnitrile, Methyl lonone Gamma, Nonalactone Gamma, Pandanol, Rose Oxide L, Tridecen-2-nitrile, and mixtures thereof.
  • At least two preferred members of said group are used in combination.
  • compositions according to the present invention are of particular use in the field of soaking and hand washing of laundry, they can also be advantageously used in a variety of other fields. Some preferred applications are listed as follows:
  • Household products such as hard surface cleaners, disinfectants, air fresheners
  • Body deodorants and antiperspirants such as aerosols, liquids, solids, powders - Hair care products such as shampoo, conditioners, hair sprays, hair colours and dyes, permanent waves, hair straightener, hair oil, creams, lotions
  • the malodor counteracting and/or masking effect of materials is evaluated according to the following protocol, and a corresponding masking index is determined:
  • An unperfumed water-soluble laundry detergent powder (composition see table 1 below) is dosed (pre-treated) with 0.1% of test material (comprising one or more members of said malodor counteracting and/or masking substances) or 0.2% to 0.5% of finished fragrance (comprising one or more members of said malodor counteracting and/or masking substances and further fragrance for perfuming the laundry detergent and/or laundry).
  • a white cotton towel (30 x 30 cm, prewashed with unperfumed laundry powder) is added to the resultant mixture according to point 2, and the mixture containing the towel is stirred for 1 min in the bucket. 4. The bucket is then capped and allowed to equilibrate (15 min). The panelists (see below for further information) then evaluate the headspace and the soaked towel for malodor perception. They are provided with a sample of malodor in wash liquor as reference. The results of these evaluations are expressed in terms of yes (malodor perceivable) or no (malodor not perceivable). A test material or finished fragrance is considered to be malodor masking if less than 33% of the panelists are able to perceive the malodor both in the headspace and on the towel.
  • the malodor perception is assessed by a panel of 15 to 20 individuals (panelists), who have been screened for their olfactory acuity and are trained in the method of evaluation.

Abstract

L'invention porte sur une composition permettant de lutter contre les mauvaises odeurs et/ou de les masquer, mauvaises odeurs qui se sont développées pendant le trempage et/ou le lavage du linge à la main. Cette composition comprend: une quantité effective, luttant contre les odeurs et/ou les masquant, d'un élément ou d'un mélange d'au moins deux éléments du groupe comprenant des composés de formule (I) avec le noyau cyclopentane saturé ou insaturé, et avec R1 = un atome d'hydrogène ou un alcanoate linéaire ou ramifié, saturé ou insaturé, un radical aldéhyde ou alcoxy possédant de 1 à 4 atomes de carbone et, indépendamment de celui-ci, R2 = un atome d'hydrogène ou un radical alkylcarboxylate linéaire, saturé possédant de 1 à 4 atomes de carbone. Comme exemple de composés selon l'invention, on mentionne : Aldéhyde C-11 (Undecanal), Aldéhyde C-11 Inter, Aldéhyde C-12 Lauric, Ethyl Rosate, Galbanum Oil, Hivertal, Méthyl Cresol Para, Méthylacetophénone, Patchouli Oil, Undecavertol, Aldéhyde C-11 Lenic, Allyl Cyclohexyl Propinate, Ambrettolide, Amyl Salicylate, Damascone Delta, Dihydromyrcenol, Ethylvanillin, Florazon, Irisnitrile, Méthyl Ionone Gamma, Nonalactone Gamma, Pandanol, Rose Oxide L et Tridecen-2-nitrile.
PCT/EP2002/001924 2002-02-23 2002-02-23 Composition pour lutter contre les mauvaises odeurs WO2003070871A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP02806849A EP1481049A1 (fr) 2002-02-23 2002-02-23 Composition pour lutter contre les mauvaises odeurs
AU2002308301A AU2002308301A1 (en) 2002-02-23 2002-02-23 Malodor counteracting composition
PCT/EP2002/001924 WO2003070871A1 (fr) 2002-02-23 2002-02-23 Composition pour lutter contre les mauvaises odeurs

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2002/001924 WO2003070871A1 (fr) 2002-02-23 2002-02-23 Composition pour lutter contre les mauvaises odeurs

Publications (1)

Publication Number Publication Date
WO2003070871A1 true WO2003070871A1 (fr) 2003-08-28

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2002/001924 WO2003070871A1 (fr) 2002-02-23 2002-02-23 Composition pour lutter contre les mauvaises odeurs

Country Status (3)

Country Link
EP (1) EP1481049A1 (fr)
AU (1) AU2002308301A1 (fr)
WO (1) WO2003070871A1 (fr)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1591514A2 (fr) * 2004-04-30 2005-11-02 Total France Utilisation d'additifs pour améliorer l'odeur de compositions d'hydrocarbures et compositions d'hydrocarbures comprenant de tels additifs
WO2005103214A2 (fr) * 2004-04-22 2005-11-03 Quest International Services B.V. Compositions de parfum
WO2008026140A2 (fr) * 2006-08-28 2008-03-06 Firmenich Sa Compositions neutralisant les mauvaises odeurs et procédé d'utilisation
EP2008637A1 (fr) 2007-06-18 2008-12-31 Firmenich Sa Compositions d'annihilation malodorantes et leur procédé d'utilisation
US20130101536A1 (en) * 2004-05-12 2013-04-25 Quest International Services B.V. Odor Reduction Compositions
EP2589649A1 (fr) * 2011-11-02 2013-05-08 International Flavors & Fragrances Inc. Octahydro-1H-4,7-méthano-indène-5-aldehydes et leur utilisation dans des compositions de parfum
US8754028B2 (en) * 2008-12-16 2014-06-17 The Procter & Gamble Company Perfume systems
JP2014205642A (ja) * 2013-04-15 2014-10-30 花王株式会社 C−sリアーゼ阻害剤
EP2865739A1 (fr) * 2013-10-28 2015-04-29 Symrise AG Utilisation de lactones
US9717815B2 (en) 2014-07-30 2017-08-01 Georgia-Pacific Consumer Products Lp Air freshener dispensers, cartridges therefor, systems, and methods
WO2018202311A1 (fr) 2017-05-05 2018-11-08 Symrise Ag Mélange de substances pour l'amélioration de l'odeur
WO2019101813A1 (fr) * 2017-11-22 2019-05-31 Firmenich Sa Ingrédients pour supprimer les mauvaises odeurs

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3890370A (en) * 1971-08-17 1975-06-17 Firmenich & Cie Process for preparing 2,6,6-trimethyl 1-alkoxycarbonyl-2,4-cyclohexadienes
US4411828A (en) * 1980-03-14 1983-10-25 Kao Corporation Fragrant tricyclic carboxylates
US5492887A (en) * 1991-04-12 1996-02-20 Dragoco Gerberding & Co. Gmbh 8-exo-formyl-2,6-exo-tricyclo(5.2.1.02,6)decane, method of preparing it and use of the same
US5780404A (en) * 1996-02-26 1998-07-14 The Procter & Gamble Company Detergent compositions containing enduring perfume
WO1998056429A1 (fr) * 1997-06-09 1998-12-17 The Procter & Gamble Company Compositions ameliorees de cyclodextrine non complexee pour eliminer les odeurs
EP0908455A1 (fr) * 1997-10-09 1999-04-14 Givaudan-Roure (International) S.A. Macrocycles
EP0955035A1 (fr) * 1998-03-31 1999-11-10 Shiseido Company Limited Composition pour la prévention des odeurs corporelles
WO2000001357A1 (fr) * 1998-07-07 2000-01-13 Quest International B.V. Procede permettant de reduire ou de prevenir les mauvaises odeurs
US6140295A (en) * 1989-09-29 2000-10-31 Unilever Patent Holdings B.V. Perfumed laundry detergents containing lipase
EP1072673A2 (fr) * 1999-07-20 2001-01-31 The Procter & Gamble Company Compositions parfumantes
US6242413B1 (en) * 1998-06-03 2001-06-05 Givaudan Roure (International) S.A. Bicyclic aldehyde and ketone odorants

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3890370A (en) * 1971-08-17 1975-06-17 Firmenich & Cie Process for preparing 2,6,6-trimethyl 1-alkoxycarbonyl-2,4-cyclohexadienes
US4411828A (en) * 1980-03-14 1983-10-25 Kao Corporation Fragrant tricyclic carboxylates
US6140295A (en) * 1989-09-29 2000-10-31 Unilever Patent Holdings B.V. Perfumed laundry detergents containing lipase
US5492887A (en) * 1991-04-12 1996-02-20 Dragoco Gerberding & Co. Gmbh 8-exo-formyl-2,6-exo-tricyclo(5.2.1.02,6)decane, method of preparing it and use of the same
US5780404A (en) * 1996-02-26 1998-07-14 The Procter & Gamble Company Detergent compositions containing enduring perfume
WO1998056429A1 (fr) * 1997-06-09 1998-12-17 The Procter & Gamble Company Compositions ameliorees de cyclodextrine non complexee pour eliminer les odeurs
EP0908455A1 (fr) * 1997-10-09 1999-04-14 Givaudan-Roure (International) S.A. Macrocycles
EP0955035A1 (fr) * 1998-03-31 1999-11-10 Shiseido Company Limited Composition pour la prévention des odeurs corporelles
US6242413B1 (en) * 1998-06-03 2001-06-05 Givaudan Roure (International) S.A. Bicyclic aldehyde and ketone odorants
WO2000001357A1 (fr) * 1998-07-07 2000-01-13 Quest International B.V. Procede permettant de reduire ou de prevenir les mauvaises odeurs
EP1072673A2 (fr) * 1999-07-20 2001-01-31 The Procter & Gamble Company Compositions parfumantes

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005103214A2 (fr) * 2004-04-22 2005-11-03 Quest International Services B.V. Compositions de parfum
WO2005103214A3 (fr) * 2004-04-22 2006-03-02 Quest Int Serv Bv Compositions de parfum
US7781392B2 (en) 2004-04-22 2010-08-24 Quest International Services B.V. Perfume compositions
FR2869621A1 (fr) * 2004-04-30 2005-11-04 Total France Sa Utilisation d'additifs pour ameliorer l'odeur de compositions d'hydrocarbures et compositions d'hydrocarbures comprenant de tels additifs
EP1591514A3 (fr) * 2004-04-30 2008-04-09 Total France Utilisation d'additifs pour améliorer l'odeur de compositions d'hydrocarbures et compositions d'hydrocarbures comprenant de tels additifs
EP1591514A2 (fr) * 2004-04-30 2005-11-02 Total France Utilisation d'additifs pour améliorer l'odeur de compositions d'hydrocarbures et compositions d'hydrocarbures comprenant de tels additifs
US20130101536A1 (en) * 2004-05-12 2013-04-25 Quest International Services B.V. Odor Reduction Compositions
WO2008026140A2 (fr) * 2006-08-28 2008-03-06 Firmenich Sa Compositions neutralisant les mauvaises odeurs et procédé d'utilisation
WO2008026140A3 (fr) * 2006-08-28 2008-07-10 Firmenich & Cie Compositions neutralisant les mauvaises odeurs et procédé d'utilisation
US8772354B2 (en) 2007-06-18 2014-07-08 Firmenich Sa Malodor counteracting compositions and method for their use
EP2008637A1 (fr) 2007-06-18 2008-12-31 Firmenich Sa Compositions d'annihilation malodorantes et leur procédé d'utilisation
US8754028B2 (en) * 2008-12-16 2014-06-17 The Procter & Gamble Company Perfume systems
EP2589649A1 (fr) * 2011-11-02 2013-05-08 International Flavors & Fragrances Inc. Octahydro-1H-4,7-méthano-indène-5-aldehydes et leur utilisation dans des compositions de parfum
JP2014205642A (ja) * 2013-04-15 2014-10-30 花王株式会社 C−sリアーゼ阻害剤
EP2865739A1 (fr) * 2013-10-28 2015-04-29 Symrise AG Utilisation de lactones
WO2015062997A1 (fr) * 2013-10-28 2015-05-07 Symrise Ag Utilisation de lactones
US10059908B2 (en) 2013-10-28 2018-08-28 Symrise Ag Use of lactones as odor masking agents
US9717815B2 (en) 2014-07-30 2017-08-01 Georgia-Pacific Consumer Products Lp Air freshener dispensers, cartridges therefor, systems, and methods
US10391193B2 (en) 2014-07-30 2019-08-27 Gpcp Ip Holdings Llc Air freshener dispensers, cartridges therefor, systems, and methods
WO2018202311A1 (fr) 2017-05-05 2018-11-08 Symrise Ag Mélange de substances pour l'amélioration de l'odeur
WO2019101813A1 (fr) * 2017-11-22 2019-05-31 Firmenich Sa Ingrédients pour supprimer les mauvaises odeurs
US11168283B2 (en) 2017-11-22 2021-11-09 Firmenich Sa Malodor counteracting ingredients

Also Published As

Publication number Publication date
AU2002308301A1 (en) 2003-09-09
EP1481049A1 (fr) 2004-12-01

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