WO2003070871A1 - Malodor counteracting composition - Google Patents
Malodor counteracting composition Download PDFInfo
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- 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
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- WIPO (PCT)
- Prior art keywords
- aldehyde
- saturated
- malodor
- masking
- laundry
- Prior art date
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- NOVRMYIRGSLBER-UHFFFAOYSA-N CC(C)C(OC(CC1C2)C2C2C1C=CC2)=O Chemical compound CC(C)C(OC(CC1C2)C2C2C1C=CC2)=O NOVRMYIRGSLBER-UHFFFAOYSA-N 0.000 description 1
- YKFHIJHJBUDXFP-UHFFFAOYSA-N CC(OC1C(C2)C(CCC3)C3C2C1)=O Chemical compound CC(OC1C(C2)C(CCC3)C3C2C1)=O YKFHIJHJBUDXFP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0068—Deodorant 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
Described is a composition counteracting and/or masking malodor developed during soaking and/or hand washing of laundry comprising: a malodor counteracting and/or masking effective amount of one member or a mixture of two or more members of the group consisting of: compounds of the formula (I) with the cyclopentane ring being saturated or unsaturated, and with 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 1-4 carbon atoms, Aldehyde C-11 (Undecanal), Aldehyde C-11 Inter, Aldehyde C-12 Lauric, 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 Ionone Gamma, Nonalactone Gamma, Pandanol, Rose Oxide L, and Tridecen-2-nitrile.
Description
Malodor counteracting composition
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.
According to a second aspect the invention further concerns a method for counteracting or masking malodor, in particular malodor produced during soaking and/or hand washing of laundry.
According to a third aspect 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.
In the course of a laundry process, soaking' and hand washing are very common. During the process 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.
There is a number of documents disclosing related art. US patents 4,304,679, 4,322,308, 4,289,641 and 4,663,068 relate to certain perfume compositions for detergent compositions which exhibit a deodorant action. This deodorant action is achieved through deposition of the perfume composition onto the fabric during the wash. The fabric then has the property of reducing body malodor when the fabric is subsequently worn in contact with the skin.
Further 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.
According to 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.
Thus, although a number of approaches have been made to prevent malodor development during washing of laundry, there is still a need for improved malodor counteracting and/or masking substances .
Correspondingly, according to the first aspect of the invention, there is provided a composition suitable for counteracting and/or masking malodor developed during soaking and/or hand washing of laundry comprising:
a malodor counteracting and/or masking effective amount of one member or a mixture of two or more members of the group consisting of:
- compounds of the formula
with the cyclopentane ring being saturated or unsaturated (as indicated by the dotted line), and with
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 1-4 carbon atoms
(for these compounds hereinafter also the term "methanoindene derivatives according to the present invention" is used),
Aldehyde C-11 (Undecanal)
Aldehyde C-11 Inter
Aldehyde C-12 Laurie
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.
The listed members of the group, methanoindene derivates or not, exhibit a surprisingly high malodor counteracting and/or masking effect as demonstrated in malodor reduction tests described in detail below.
In particular preferred is the use of a malodor counteracting and/or masking effective amount of one member or a mixture of two or more members of the group consisting of the following methanoindene derivatives according to the present invention:
Greenyl Acetate
tricyclo[5.2.1.0.(2,6)]dec-3-en-8-yl acetate CAS-No 5413-60-5 tricyclo[5.2.1.0.(2,6)]dec-4-en-8-yl acetate CAS-No 2500-83-6 Mixture: 54830-99-8
Vertral
D1-CHO
tricyclo[5.2.1.0.(2,6)]decane-carbaldehyde CAS-No 30772-79-3
Greenyl Propionate
tricyclo[5.2.1.0.(2,6)]dec-3-en-8-yl propanoate CAS-No 17511-60-3 / 68683-24-9 (Mixtures)
Greenyl Isobutyrate
tricyclo[5.2.1.0.(2,6)]dec-3-en-8-yl 2-methylpropanoate CAS-No 68039-39-4
Verdalia A (Greenyl methylether)
methoxy-tricyclo[5.2.1.0.(2,6)]dec-3-ene CAS-No 27135-90-6 / 53018-24-9
4-tricyclo[5.2.1.0.(2,6)]dec-8-ylidenebutanal CAS-No 30168-23-1
Fleuroxene
allyloxy-tricyclo[5.2.1.0.(2,6)]dec-3-ene CAS-No 26912-64-1
Fruitate
ethyl(1S,2R,6R,7R)-tricyclo[5.2.1.0.(2,6)]dec-4-ene-2-carboxylate CAS-No 80657-64-3
Herein, the notation/nomenclature used in the CAS database is used for certain substituents/structural units. E.g., with respect to Fleuroxene H2C=CH-CH2-O-D1 indicates that the H2C=CH-CH2-O- unit is attached at an unknown position to the ring system. Further information can be derived from the nomenclature name and/or the CAS-No stated.
Although certain methanoindene derivatives have already been mentioned in documents relating to malodor counteractant compositions the related art provided no teaching that a composition could be formulated which comprises a malodor counteracting and/or masking effective amount of said methanoindene derivatives.
EP 1 113 105 A2 (International Flavors & Fragrances Inc.) concerns a human sweat malodor counteractant composition and process for using same. It discloses certain fragrances comprising hexahydro-4,7-methanoindene-5-yl acetate, hexahydro-4,7-methanoindene-6-yl acetate and/or hexahydro-4,7- methanoinden-5-yl propionate besides a number of other organoleptically effective substances. However, 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.
Amongst the substances listed above the following non-methanoindene compounds exhibit a particularly pronounced malodor counteracting and/or masking effect (masking index = 5, see below): Aldehyde C-11 (Undecanal), Aldehyde C-11 Inter, Aldehyde C-12 Laurie, Ethyl Rosate, Galbanum Oil, Hivertal, Methyl Cresol Para, Methylacetophenone, Patchouli Oil, Undecavertol.
Amongst the group of methanoindene derivatives the following are particularly useful, due to their pronounced malodor counteracting and/or masking effect in aqueous laundry compositions: Greenyl Acetate, Vertral, Verdalia A, Dupical, Fleuroxene, Fruitate.
According to the second aspect of the present invention, a method for counteracting or masking malodor produced during soaking and/or hand washing of laundry comprises the following steps:
- preparing an aqueous detergent composition by admixing
- water and
a malodor counteracting and/or masking effective amount of a composition as described above with respect to the first aspect of the invention suitable for counteracting and/or masking malodor developed during soaking and/or hand washing of laundry,
and
- soaking and/or hand washing laundry in the prepared aqueous detergent solution such that malodor developed while soaking and/or hand washing the laundry is counteracted and/or masked.
According to the third aspect of the present invention, a laundry detergent is provided 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. For certain uses the laundry detergent preferably is a powder detergent which is water soluble.
According to the fourth aspect of the present invention a method of preparing a malodor counteracting and/or masking composition is provided comprising the step of mixing one, two or more members of the group consisting of:
compounds of the formula
with the cyclopentane ring being saturated or unsaturated (as indicated by the dotted line), and with
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
1-4 carbon atoms (methanoindene derivatives according to the present invention), Aldehyde C-11 (Undecanal), Aldehyde C-11 Inter, Aldehyde C-12 Laurie, 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, and Tridecen-2-nitrile
with
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.
According to the fifth aspect of the present invention there is provided 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.
According to the sixth aspect of the present invention a method for soaking and/or hand washing and/or machine washing of laundry is provided comprising the following steps:
Providing a laundry detergent composition according to the third aspect of the invention, and
- soaking and/or hand washing and/or machine washing of laundry in said laundry detergent composition.
With respect to the second to sixth aspect of the present invention, ie.
(i) the method for counteracting or masking malodor produced during soaking and/or hand washing of laundry,
(ii) the laundry detergent,
(iii) the method of preparing a malodor counteracting and/or masking . composition,
(iv) the method for soaking and/or hand washing and/or machine washing of laundry, and
(v) the fragrance composition
the same preferences regarding the malodor counteracting and/or masking substances hold as described above for the first aspect of the invention.
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).
With respect to the malodor counteracting and/or masking composition, there are advantageously incorporated therein at least 15% by weight of the preferred members of said group consisting of:
Methanoindene derivatives according to the present invention, Aldehyde C-11 (Undecanal), Aldehyde C-11 Inter, Aldehyde C-12 Laurie, 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.
Preferably, at least two preferred members of said group are used in combination.
Although the 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:
- Laundry products such as detergent powders, liquids, bars, tablets, fabric softeners, fabric fresheners
- 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
- Skin care products such as lotions, creams, after shaves, foot powder
- Soaps and synthetic detergents such as bars, liquids, foams, powders
The invention is further illustrated by means of the following examples without being limited thereto.
Example 1 :
The malodor counteracting and/or masking effect of materials is evaluated according to the following protocol, and a corresponding masking index is determined:
1. 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).
2. In a 3 I bucket, at 25° C a specified amount of synthetic sweat malodor (see table 2) is mixed with 1 I of wash liquor and 5 g of the pre-treated laundry detergent powder according to point 1.
3. 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.
5. For determining the masking index of the materials tested different concentrations of malodor were used according to table 3.
6. The evaluation results for a number of materials tested is listed in table 4.
Table 1
Table 3
Table 4
(1) Materials of the 4,7-Methanoidene type
Note: Throughout the specification and claims common names of substances and materials are used. Corresponding IUPAC names and CAS-Numbers are listed in table 5.
Table 5
Claims
1. Composition counteracting and/or masking malodor developed during soaking and/or hand washing of laundry comprising:
a malodor counteracting and/or masking effective amount of one member or a mixture of two or more members of the group consisting of:
- compounds of the formula 
with the cyclopentane ring being saturated or unsaturated, and with
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 1-4 carbon atoms,
- Aldehyde C-11 (Undecanal)
- Aldehyde C-11 Inter
Aldehyde C-12 Laurie
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
2. Malodor counteracting and/or masking composition according to claim 1 , comprising a malodor counteracting and/or masking effective amount of one member or a mixture of two or more members of the group consisting of
Greenyl Acetate 
tricyclo[5.2.1.0.(2,6)]dec-3-en-8-yl acetate CAS-No 5413-60-5 tricyclo[5.2.1.0.(2,6)]dec-4-en-8-yl acetate CAS-No 2500-83-6 Mixture: 54830-99-8
Vertral 
tricyclo[5.2.1.0.(2,6)]decane-carbaldehyde CAS-No 30772-79-3
Greenyl Propionate 
tricyclo[5.2.1.0.(2,6)]dec-3-en-8-yl propanoate CAS-No 17511-60-3 / 68683-24-9 (Mixtures) Greenyl Isobutyrate 
tricyclo[5.2.1.0.(2,6)]dec-3-en-8-yl 2-methylpropanoate CAS-No 68039-39-4
Verdalia A (Greenylmethylether) 
Methoxy-tricyclo[5.2.1.0.(2,6)]dec-3-ene CAS-No 27135-90-6 / 53018-24-9 
4-tricyclo[5.2.1.0.(2,6)]dec-8-ylidenebutanal CAS-No 30168-23-1
Fleuroxene 
Allyloxy-tricyclo[5.2.1.0.(2,6)]dec-3-ene CAS-No 26912-64-1 Fruitate 
ethyl(1S,2R,6R,7R)-tricyclo[5.2.1.0.(2,6)]dec-4-ene-2-carboxylate CAS-No 80657-64-3
3. Method for counteracting or masking malodor produced during soaking and/or hand washing of laundry, comprising the following steps:
preparing an aqueous detergent composition by admixing
water and
a malodor counteracting and/or masking effective amount of one member or a mixture of two or more members of the group consisting of:
compounds of the formula 
with the cyclopentane ring being saturated or unsaturated, and with
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 1-4 carbon atoms,
Aldehyde C-11 (Undecanal), Aldehyde C-11 Inter, Aldehyde C-12 Laurie, 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, and Tridecen-2-nitrile,
and
- soaking and/or hand washing laundry in the prepared aqueous detergent solution such that malodor developed while soaking and/or hand washing the laundry is counteracted and/or masked.
4. Laundry detergent, comprising a malodor counteracting and/or masking effective amount of a composition according to claim 1.
5. 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
compounds of the formula 
with the cyclopentane ring being saturated or unsaturated, and with 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 1-4 carbon atoms, Aldehyde C-11 (Undecanal), Aldehyde C-11 Inter, Aldehyde C-12 Laurie, 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, and Tridecen-2-nitrile,
with
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 malodor in a process comprising soaking and/or hand washing of laundry.
6. 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 consisting of:
compounds of the formula 
with the cyclopentane ring being saturated or unsaturated, and with 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 1 -4 carbon atoms, Aldehyde C-11 (Undecanal), Aldehyde C-11 Inter, Aldehyde C-12 Laurie, 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, and Tridecen-2-nitrile,
wherein (a) said fragrance and (b) said member or mixture of members are not the same.
7. Method for soaking and/or hand washing and/or machine washing of laundry comprising
(a) providing a laundry detergent according to claim 4
(b) soaking and/or hand washing and/or machine washing of laundry in said laundry detergent composition.
8. Use of a composition comprising a malodor counteracting and/or masking effective amount of one member or a mixture of two or more members of the group consisting of:
compounds of the formula 
with the cyclopentane ring being saturated or unsaturated, and with 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 1-4 carbon atoms, Aldehyde C-11 (Undecanal), Aldehyde C-11 Inter, Aldehyde C-12 Laurie, 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, and Tridecen-2-nitrile,
as
malodor counteracting and/or masking composition
laundry detergent '
fragrance composition
body deodorant
body antiperspirant
hair care product, or
skin care product.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02806849A EP1481049A1 (en) | 2002-02-23 | 2002-02-23 | Malodor counteracting composition |
| AU2002308301A AU2002308301A1 (en) | 2002-02-23 | 2002-02-23 | Malodor counteracting composition |
| PCT/EP2002/001924 WO2003070871A1 (en) | 2002-02-23 | 2002-02-23 | Malodor counteracting composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP2002/001924 WO2003070871A1 (en) | 2002-02-23 | 2002-02-23 | Malodor counteracting composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2003070871A1 true WO2003070871A1 (en) | 2003-08-28 |
Family
ID=27741086
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2002/001924 WO2003070871A1 (en) | 2002-02-23 | 2002-02-23 | Malodor counteracting composition |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP1481049A1 (en) |
| AU (1) | AU2002308301A1 (en) |
| WO (1) | WO2003070871A1 (en) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1591514A2 (en) * | 2004-04-30 | 2005-11-02 | Total France | Use of additives to improve the odor of hydrocarbon compositions and hydrocarbon compositions comprising such additives. |
| WO2005103214A2 (en) * | 2004-04-22 | 2005-11-03 | Quest International Services B.V. | Perfume compositions |
| WO2008026140A2 (en) * | 2006-08-28 | 2008-03-06 | Firmenich Sa | Malodor counteracting compositions and method for their use |
| EP2008637A1 (en) | 2007-06-18 | 2008-12-31 | Firmenich Sa | Malodor counteracting compositions and method for their use |
| US20130101536A1 (en) * | 2004-05-12 | 2013-04-25 | Quest International Services B.V. | Odor Reduction Compositions |
| EP2589649A1 (en) * | 2011-11-02 | 2013-05-08 | International Flavors & Fragrances Inc. | Octahydro-1H-4,7-methano-indene-5-aldehydes and their use in perfume compositions |
| US8754028B2 (en) * | 2008-12-16 | 2014-06-17 | The Procter & Gamble Company | Perfume systems |
| JP2014205642A (en) * | 2013-04-15 | 2014-10-30 | 花王株式会社 | C-S lyase inhibitor |
| EP2865739A1 (en) * | 2013-10-28 | 2015-04-29 | Symrise AG | Use of lactones |
| US9717815B2 (en) | 2014-07-30 | 2017-08-01 | Georgia-Pacific Consumer Products Lp | Air freshener dispensers, cartridges therefor, systems, and methods |
| WO2018202311A1 (en) | 2017-05-05 | 2018-11-08 | Symrise Ag | Composition for odour improvement |
| WO2019101813A1 (en) * | 2017-11-22 | 2019-05-31 | Firmenich Sa | Malodor counteracting ingredients |
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| US8754028B2 (en) * | 2008-12-16 | 2014-06-17 | The Procter & Gamble Company | Perfume systems |
| EP2589649A1 (en) * | 2011-11-02 | 2013-05-08 | International Flavors & Fragrances Inc. | Octahydro-1H-4,7-methano-indene-5-aldehydes and their use in perfume compositions |
| JP2014205642A (en) * | 2013-04-15 | 2014-10-30 | 花王株式会社 | C-S lyase inhibitor |
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| US11168283B2 (en) | 2017-11-22 | 2021-11-09 | Firmenich Sa | Malodor counteracting ingredients |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1481049A1 (en) | 2004-12-01 |
| AU2002308301A1 (en) | 2003-09-09 |
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