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WO1997006235A1 - Compositions detergentes contenant un amine et des parfums specialement selectionnes - Google Patents

Compositions detergentes contenant un amine et des parfums specialement selectionnes Download PDF

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Publication number
WO1997006235A1
WO1997006235A1 PCT/US1996/012611 US9612611W WO9706235A1 WO 1997006235 A1 WO1997006235 A1 WO 1997006235A1 US 9612611 W US9612611 W US 9612611W WO 9706235 A1 WO9706235 A1 WO 9706235A1
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WIPO (PCT)
Prior art keywords
amine
alkyl
detergent composition
weight
detergent
Prior art date
Application number
PCT/US1996/012611
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English (en)
Inventor
Jose Maria Velazquez
Original Assignee
The Procter & Gamble Company
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Filing date
Publication date
Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to EP96926223A priority Critical patent/EP0843719A1/fr
Priority to JP50854097A priority patent/JP3886532B2/ja
Priority to US09/011,237 priority patent/US5929022A/en
Priority to BR9609985A priority patent/BR9609985A/pt
Priority to CA002228966A priority patent/CA2228966C/fr
Publication of WO1997006235A1 publication Critical patent/WO1997006235A1/fr

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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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/86—Mixtures of anionic, cationic, and non-ionic compounds
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/65—Mixtures of anionic with cationic compounds
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/04—Carboxylic acids or salts thereof
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/146—Sulfuric acid esters
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29—Sulfates of polyoxyalkylene ethers
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/40—Monoamines or polyamines; Salts thereof
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/42—Amino alcohols or amino ethers
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/521—Carboxylic amides (R1-CO-NR2R3), where R1, R2 and R3 are alkyl or alkenyl groups
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/525—Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain two or more hydroxy groups per alkyl group, e.g. R3 being a reducing sugar rest
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/72—Ethers of polyoxyalkylene glycols

Definitions

  • TECHNICAL FIELD This invention relates to laundry detergent compositions containing amine detersive surfactants and specially selected perfiime components which reduce the malodor ofthe amine.
  • a perfiime component selected to have the follwong characteristics: i) a partition coefficient value (clogP) equal to or higher than 2.0; ii) a boiling point greater than 200 °F; and i ⁇ ) a low odor detection threshold (ODT) lower than about 300 PPB; and
  • perfiime components act to reduce the malodor associated with amine surfactants.
  • the perfiime components is selected from the group consisting of dodecahydro-3a,6,6,9A-tetramethylnaphtho (2,1-B) furan, 3,3- dimethyl-5-(2,2,3 trimethyl-3 cyclopenten-l-yl)-4 pentenol, methyl lonone, cis 3 hexenyl iso butyrate, undecalactone, phenyl ethyl phenyl acetate, hexyl-ortho- hydroxybenzoate, and mixtures thereof; and
  • compositions of this invention preferably further comprise a performance enhancing amount of a detergent-compatible enzyme selected from the group consisting of protease, lipase, amylase, cellulase, peroxidase, and mixtures thereof.
  • a detergent-compatible enzyme selected from the group consisting of protease, lipase, amylase, cellulase, peroxidase, and mixtures thereof.
  • the laundry detergent compositions herein comprise an effective amount of a perfume component which acts to reduce the malodor associtated with the amine surfactant.
  • effective amount means an amount sufficient to reduce the amine- type odor of the detergent compositions.
  • the detergent compositions herein will comprise from about 0.00001% to about 5, more preferably about 0.00001% to about 2%, most preferably about 0.0001% to about 0.5%, by weight, of specially selected perfiime components.
  • the perfiime components which have been found to reduce the amine malodor are those with a low solubility in water, i.e., they have a partition coefficient value, (clogP), equal to or higher than 2.0, at standard conditions of 25°C and 760 mm Hg in a water/octanol system. Additionally the perfiime components of this invention should have a boiling point greater than 200°F.
  • the perfiime components also have a unique property of having a low odor detection threshold (ODT) lower than about 300 PPB, preferably equal to or lower than about 0.1 PPB.
  • Examples of preferred perfiime components are those selected from the group consisting of dodecahydro-3a,6,6,9A-tetramethylnaphtho (2,1-B) fiiran, 3,3- dimethyl-5-(2,2,3 trimethyl-3 cyclopenten-l-yl)-4 pentenol, methyl lonone, cis 3 hexenyl iso butyrate, undecalactone, phenyl ethyl phenyl acetate, hexyl-ortho- hydroxybenzoate, and mixtures thereof.
  • the specially selected perfiime components herein be mixed together prior to addition to the laundry detergent composition.
  • These perfume components may be combined with other perf ime ingredients before addition to the composition.
  • the perfiime containing these specially selected perfiime components is preferably sprayed onto the final granular detergent composition or mixed into the final liquid laundry detergent in a manner which does not adversely affect the perfume.
  • Amines suitable for use in the detergent compositions herein include those according to the formula:
  • Ri is a Cg-C ⁇ 2 ⁇ group
  • n is from about 2 to about 4
  • X is a bridging group which is selected from NH, CONH, COO, or O or X can be absent; and R3 and R are individually selected from H, C1-C4 alkyl, or (CH2-CH2-O(R5)) wherein R5 is H or methyl.
  • Preferred amines include the following:
  • Rj is a Cg-C ⁇ 2 alkyl group and R5 is H or CH3.
  • the amine is described by the formula: R 1 -C(O)-NH-(CH 2 ) 3 -N(CH 3 )2 wherein Rj is Cg-C ⁇ 2 alkyl.
  • Particularly preferred amines include those selected from the group consisting of octyl amine, hexyl amine, decyl amine, dodecyl amine, Cg-C ⁇ 2 bis(hydroxyethyI)amine, Cg-C ⁇ 2 bis(hydroxyisopropyl)amine, and Cg-C ⁇ 2 amido ⁇ propyl dimethyl amine, and mixtures.
  • the laundry detergent compositions of the present invention typically comprise from about 0.5% to about 10%, preferably from about 1% to about 5%, by weight of amine surfactants.
  • Non-Amine Detergent Surfactants A wide range of non-amine, secondary surfactants can be used in the detergent composition of the present invention.
  • non-amine is meant herein any detersive surfactant which does not have the unattractive "amine” malodor associated with its use in a detergent composition. Included in this definition of non-amine, therefor, is amine oxides.which do not have an amine-type odor.
  • the laundry detergent compositions of the present invention typically comprise from about 1% to about 95%, preferably from about 3% to about 40%, more preferably from about 5% to about 25%, by weight of such secondary, non- amine surfactants.
  • alkyl alkoxylated sulfate surfactants which are water soluble salts or acids of the formula RO(A) m SO3M wherein R is an unsubstituted CJO-C 2 4 alkyl or hydroxyalkyl group having a CJO-C 2 4 alkyl component, preferably a C ⁇ 2 -Cjg alkyl or hydroxyalkyl, more preferably Cj 2 -Ci5 alkyl or hydroxyalkyl, A is an ethoxy or propoxy unit, m is greater than zero, typically between about 0.5 and about 6, more preferably between about 0.5 and about 3, and M is H or a cation which can be, for example, a metal cation (e.g., sodium, potassium, lithium, calcium, magnesium, etc.), ammonium or substituted-ammonium cation.
  • R is an unsubstituted CJO-C 2 4 alkyl or hydroxyalkyl group having a CJO-C 2 4 alkyl component
  • Alkyl ethoxylated sulfates as well as alkyl propoxylated sulfates are contemplated herein.
  • Specific examples of substituted ammonium cations include ethanol-, triethanol-, methyl-, dimethyl, trimethyl ⁇ ammonium cations and quaternary ammonium cations such as tetramethyl-ammonium and dimethyl piperidinium cations and those derived from alkylamines such as ethylamine, diethylamine, triethylamine, mixtures thereof, and the like.
  • Exemplary surfactants are C ⁇ 2 -Ci5 alkyl polyethoxylate (1.0) sulfate (C ⁇ 2 -Ci5E(1.0)M), C ⁇ 2 - C15 alkyl polyethoxylate (2.25) sulfate (C ⁇ 2 -Ci5E(2.25)M), C ⁇ 2 -Cj5 alkyl polyethoxylate (3.0) sulfate (C ⁇ 2 -Cj5E(3.0)M), and C ⁇ 2 -Ci5 alkyl polyethoxylate (4.0) sulfate (C j -Ci5E(4.0)M), wherein M is conveniently selected from sodium and potassium.
  • alkyl sulfate surfactants are water soluble salts or acids of the formula ROSO3M wherein R preferably is a Cg-Cjg hydrocarbyl, preferably an alkyl or hydroxyalkyl having a Cio- i alkyl component, more preferably a C j2 -Ci 5 alkyl or hydroxyalkyl, and M is H or a cation, e.g., an alkali metal cation (e.g. sodium, potassium, lithium), or ammonium or substituted ammomum (e.g.
  • R preferably is a Cg-Cjg hydrocarbyl, preferably an alkyl or hydroxyalkyl having a Cio- i alkyl component, more preferably a C j2 -Ci 5 alkyl or hydroxyalkyl
  • M is H or a cation, e.g., an alkali metal cation (e.g. sodium, potassium, lithium), or ammoni
  • methyl-, dimethyl-, and trimethyl ammonium cations and quaternary ammonium cations such as tetramethyl-ammonium and dimethyl piperidinium cations and quaternary ammonium cations derived from alkylamines such as ethylamine, diethylamine, triethylamine, and mixtures thereof, and the like).
  • alkyl ester sulfonate surfactants including linear esters of Cg-C 2 Q carboxylic acids (i.e., fatty acids) which are sulfonated with gaseous SO3 according to "The Journal of the American Oil Chemists Society", 52 (1975), pp. 323-329.
  • Suitable starting materials would include natural fatty substances as derived from tallow, palm oil, etc.
  • alkyl ester sulfonate suifactant especially for laundry applications, comprise alkyl ester sulfonate surfactants ofthe structural formula :
  • R 3 is a Cg-C o hydrocarbyl, preferably an alkyl, or combination thereof
  • R 4 is a Ci-Cg hydrocarbyl, preferably an alkyl, or combination thereof
  • M is a cation which forms a water soluble salt with the alkyl ester sulfonate.
  • Suitable salt-forming cations include metals such as sodium, potassium, and lithium, and substituted or unsubstituted ammonium cations, such as monoethanolamine, diethanolamine, and triethanolamine.
  • R 3 is Cio-Cjg alkyl
  • R 4 is methyl, ethyl or isopropyl.
  • the methyl ester sulfonates wherein R 3 is Cjo- Ci6 alkyl.
  • anionic surfactants useful for detersive purposes can also be included in the laundry detergent compositions of the present invention.
  • These can include salts (including, for example, sodium, potassium, ammonium, and substituted ammonium salts such as mono-, di- and triethanolamine salts) of soap, Cg-C 22 primary of secondary alkanesulfonates, Cg-C 2 4 olefinsulfonates, sulfonated polycarboxylic acids prepared by sulfonation ofthe pyrolyzed product of alkaline earth metal citrates, e.g., as described in British patent specification No.
  • alkylpolyglycolethersulfates (containing up to 10 moles of ethylene oxide); alkyl glycerol sulfonates, fatty acyl glycerol sulfonates, fatty oleoyl glycerol sulfates, alkyl phenol ethylene oxide ether sulfates, paraffin sulfonates, alkyl phosphates, isethionates such as the acyl isethionates, N-acyl taurates, alkyl succinamates and sulfosuccinates, monoesters of sulfosuccinates (especially saturated and unsaturated C ⁇ 2 -Cjg monoesters) and diesters of sulfosuccinates (especially saturated and unsaturated Cg-C ⁇ 2 diesters), sulfates of alkylpolysaccharides such as the sulfates of alkylpolysaccharides such as the s
  • Resin acids and hydrogenated resin acids are also suitable, such as rosin, hydrogenated rosin, and resin acids and hydrogenated resin acids present in or derived from tall oil. Further examples are described in "Surface Active Agents and Detergents" (Vol. I and ⁇ by Schwartz, Perry and Berch). A variety of such surfactants are also generally disclosed in U.S. Patent 3,929,678, issued December 30, 1975 to Laughlin, et al. at Column 23, line 58 through Column 29, line 23 (herein inco ⁇ orated by reference).
  • One class of nonionic surfactants useful in the present invention are condensates of ethylene oxide with a hydrophobic moiety to provide a surfactant having an average hydrophilic-lipophilic balance (HLB) in the range from 8 to 17, preferably from 9.5 to 14, more preferably from 12 to 14.
  • HLB hydrophilic-lipophilic balance
  • the hydrophobic (lipophilic) moiety may be aliphatic or aromatic in nature and the length of the polyoxyethylene group which is condensed with any particular hydrophobic group can be readily adjusted to yield a water-soluble compound having the desired degree of balance between hydrophilic and hydrophobic elements.
  • Especially preferred nonionic surfactants of this type are the C9-C15 primary alcohol ethoxylates containing 3-12 moles of ethylene oxide per mole of alcohol, particularly the C ⁇ 2 -Ci5 primary alcohols containing 5-8 moles of ethylene oxide per mole of alcohol.
  • Another class of nonionic surfactants comprises alkyl polyglucoside compounds of general formula
  • RO- ⁇ nH ⁇ O) ⁇ wherein Z is a moiety derived from glucose; R is a saturated hydrophobic alkyl group that contains from 12 to 18 carbon atoms; t is from 0 to 10 and n is 2 or 3; x is from 1.3 to 4, the compounds including less than 10% unreacted fatty alcohol and less than 50% short chain alkyl polyglucosides.
  • Compounds of this type and their use in detergent are disclosed in EP-B 0 070077, 0 075 996 and 0094 118.
  • Nonionic surfactants are poly hydroxy fatty acid amide surfactants ofthe formula R 2 -C(O)-N(R-)-Z, wherein R 1 is H, or R 1 is Cj_4 hydrocarbyl, 2-hydroxy ethyl, 2-hydroxy propyl or a mixture thereof, R2 is C5.3 ⁇ hydrocarbyl, and Z is a polyhydroxyhydrocarbyl having a linear hydrocarbyl chain with at least 3 hydroxyls directly connected to the chain, or an alkoxylated derivative thereof.
  • R is methyl
  • R- ⁇ is a straight Cn.15 alkyl or alkenyl chain such as coconut alkyl or mixtures thereof
  • Z is derived from a reducing sugar such as glucose, fructose, maltose, lactose, in a reductive amination reaction.
  • compositions of the present invention may comprise amine oxide in accordance with the general formula I:
  • the structure (I) provides one long-chain moiety R!(EO)x(PO)y(BO) z and two short chain moieties, CH 2 R ⁇ R' is preferably selected from hydrogen, methyl and -CH 2 OH.
  • R 1 is a primary or branched hydrocarbyl moiety which can be saturated or unsaturated, preferably, Rl is a primary alkyl moiety.
  • Rl is a hydrocarbyl moiety having chainlength offrom about 8 to about 18.
  • R 1 may be somewhat longer, having a chainlength in the range Cj 2 -C 2 4.
  • the invention also encompasses amine oxides wherein x+y+z is different from zero, specifically x+y+z is from about 1 to about 10, R is a primary alkyl group containing 8 to about 24 carbons, preferably from about 12 to about 16 carbon atoms; in these embodiments y + z is preferably 0 and x is preferably from about 1 to about 6, more preferably from about 2 to about 4; EO represents ethyleneoxy; PO represents propyleneoxy; and BO represents butyleneoxy.
  • amine oxides can be prepared by conventional synthetic methods, e.g., by the reaction of alkylethoxysulfates with dimethylamine followed by oxidation of the ethoxylated amine with hydrogen peroxide.
  • Highly preferred amine oxides herein are solids at ambient temperature, more preferably they have melting-points in the range 30°C to 90°C.
  • Amine oxides suitable for use herein are made commercially by a number of suppliers, including Akzo Chemie, Ethyl Co ⁇ ., and Procter & Gamble. See McCutcheon's compilation and Kirk-Othmer review article for alternate amine oxide manufacturers.
  • Preferred commercially available amine oxides are the solid, dihydrate ADMOX 16 and ADMOX 18, ADMOX 12 and especially ADMOX 14 from Ethyl Co ⁇ .
  • Preferred embodiments include hexadecyldimethylamine oxide dihydrate, octadecyldimethylamine oxide dihydrate, hexadecyltris(ethyleneoxy)dimethyl-amine oxide, and tetradecyldimethylamine oxide dihydrate.
  • R' H
  • R' CH 2 OH
  • Cationic detersive surfactants suitable for use in the laundry detergent compositions of the present invention are those having one long-chain hydrocarbyl group.
  • cationic surfactants include the ammomum surfactants such as alkyldimethylammonium halogenides, and those surfactants having the formula :
  • R2 is an alkyl or alkyl benzyl group having from about 8 to about 18 carbon atoms in the alkyl chain
  • each R 3 is selected from the group consisting of -CH 2 CH 2 -, -CH 2 CH(CH 3 , -CH 2 CH(CH 2 OH)-, -CH 2 CH 2 CH 2 -, and mixtures thereof
  • each R 4 is selected from the group consisting of C1-C4 alkyl, C1-C4 hydroxyalkyl, benzyl ring structures formed by joining the two R 4 groups, -CH2CHOH- CHOHCOR 6 CHOHCH2OH wherein R 6 is any hexose or hexose polymer having a molecular weight less than about 1000, and hydrogen when y is not 0
  • R*-* is the same as R 4 or is an alkyl chain wherein the total number of carbon atoms of R 2 plus R*> is not more than about 18
  • each y is from 0 to about
  • Preferred cationic surfactants are the water-soluble quaternary ammomum compounds useful in the present composition having the formula : R 1 R 2 R3R 4 N + X- (i) wherein R ⁇ is Cg-Cig alkyl, each of R2, R3 and R4 is independently C1-C4 alkyl, C1-C4 hydroxy alkyl, benzyl, and where x has a value from 1 to 5, and X is an anion. Not more than one of R2, R3 or R4 should be benzyl.
  • the preferred alkyl chain length for K is C12-C15 particularly where the alkyl group is a mixture of chain lengths derived from coconut or palm kernel fat or is derived synthetically by olefin build up or OXO alcohols synthesis.
  • Preferred groups for R2R3 and R4 are methyl and hydroxyethyl groups and the anion X may be selected from halide, methosulphate, acetate and phosphate ions.
  • quaternary ammonium compounds of formulae (i) for use herein are: coconut trimethyl ammonium chloride or bromide; coconut methyl dihydroxyethyl ammomum chloride or bromide; decyl triethyl ammonium chloride; decyl dimethyl hydroxyethyl ammomum chloride or bromide;
  • Other cationic surfactants useful herein are also described in U.S. Patent 4,228,044, Cambre, issued October 14, 1980.
  • compositions according to the present invention may further comprise a builder system.
  • a builder system Any conventional builder system is suitable for use herein including aluminosilicate materials, silicates, polycarboxylates and fatty acids, materials such as ethylenediamine tetraacetate, metal ion sequestrants such as aminopolyphosphonates, particularly ethylenediamine tetramethylene phosphonic acid and diethylene triamine pentamethylenephosphonic acid.
  • phosphate builders can also be used herein.
  • Suitable polycarboxylates builders for use herein include citric acid, preferably in the form of a water-soluble salt, derivatives of succinic acid of the formula R- CH(COOH)CH2(COOH) wherein R is C ⁇ o-20 alkyl or alkenyl, preferably Ci2-16 > or wherein R can be substituted with hydroxyl, sulfo sulfoxyl or sulfone substituents.
  • Specific examples include lauryl succinate , myristyl succinate, palmityl succinate 2- dodecenylsuccinate, 2-tetradecenyl succinate.
  • Succinate builders are preferably used in the form of their water-soluble salts, including sodium, potassium, ammomum and alkanolammonium salts.
  • polycarboxylates are oxodisuccinates and mixtures of tartrate monosuccinic and tartrate disuccinic acid such as described in US 4,663,071.
  • suitable fatty acid builders for use herein are saturated or unsaturated Cjo-is f tty acids, as well as the corresponding soaps.
  • Preferred saturated species have from 12 to 16 carbon atoms in the alkyl chain.
  • the preferred unsaturated fatty acid is oleic acid.
  • Other preferred builder system for liquid compositions is based on dodecenyl succinic acid and citric acid.
  • Detergency builder salts are normally included in amounts of from 3% to 50% by weight ofthe composition preferably from 5% to 30% and most usually from 5% to 25% by weight.
  • Optional Detergent Ingredients may further comprise one or more enzymes which provide cleaning performance and/or fabric care benefits.
  • Said enzymes include enzymes selected from cellulases, hemicellulases, peroxidases, proteases, gluco-amylases, amylases, lipases, cutinases, pectinases, xylanases, reductases, oxidases, phenoloxidases, lipoxygenases, ligninases, pullulanases, tannases, pentosanases, malanases, ⁇ -glucanases, arabinosidases or mixtures thereof.
  • a preferred combination is a detergent composition having a cocktail of conventional applicable enzymes like protease, amylase, lipase, cutinase and/or cellulase in conjunction with the lipolytic enzyme variant D96L at a level of from 50 LU to 8500 LU per liter wash solution.
  • the cellulases usable in the present invention include both bacterial or fungal cellulase. Preferably, they will have a pH optimum of between 5 and 9.5. Suitable cellulases are disclosed in U.S. Patent 4,435,307, Barbesgoard et al, which discloses fungal cellulase produced from Humicola insolens. Suitable cellulases are also disclosed in GB-A-2.075.028; GB-A-2.095.275 and DE-OS-2.247.832.
  • cellulases examples include cellulases produced by a strain of Humicola insolens (Humicola grisea var. thermoidea), particularly the Humicola strain DSM 1800.
  • suitable cellulases are cellulases originated from Humicola insolens having a molecular weight of about 50KDa, an isoelectric point of 5.5 and containing 415 amino acids.
  • suitable cellulases are the cellulases having color care benefits. Examples of such cellulases are cellulases described in European patent application No. 91202879.2, filed November 6, 1991 (Novo).
  • Peroxidase enzymes are used in combination with oxygen sources, e.g. percarbonate, perborate, persulfate, hydrogen peroxide, etc. They are used for "solution bleaching", i.e. to prevent transfer of dyes or pigments removed from substrates during wash operations to other substrates in the wa-h solution.
  • Peroxidase enzymes are known in the art, and include, for example, horseradish peroxidase, ligninase, and haloperoxidase such as chloro- and bromo-peroxidase.
  • Peroxidase-containing detergent compositions are disclosed, for example, in PCT International Application WO 89/099813 and in European Patent application EP No. 91202882.6, filed on November 6, 1991.
  • Said cellulases and/or peroxidases are normally inco ⁇ orated in the detergent composition at levels from 0.0001% to 2% of active enzyme by weight of the detergent composition.
  • protease enzymes include those sold under the tradenames Alcalase, Savinase, Primase, Durazym, and Esperase by Novo Nordisk A/S (Denmark), those sold under the tradename Maxatase, Maxacal and Maxapem by Gist-Brocades, those sold by Genencor International, and those sold under the tradename Opticlean and Optimase by Solvay Enzymes. Also proteases described in our co-pending application USSN 08/136,797 can be included in the detergent composition of the invention. Protease enzyme may be inco ⁇ orated into the compositions in accordance with the invention at a level of from 0.0001% to 2% active enzyme by weight ofthe composition.
  • a preferred protease herein referred to as "Protease D” is a carbonyl hydrolase variant having an amino acid sequence not found in nature, which is derived from a precursor carbonyl hydrolase by substituting a different amino acid for the amino acid residue at a position in said carbonyl hydrolase equivalent to position +76, preferably also in combination with one or more amino acid residue positions equivalent to those selected from the group consisting of +99, +101, +103, +104, +107, +123, +27, +105, +109, +126, +128, +135, +156, +166, +195, +197, +204, +206, +210, +216, +217, +218, +222, +260, +265, and/or +274 according to the numbering of Bacillus amyloliquefaciens subtilisin, as described in the concurrently filed patent application of A. Baeck et al. entitled “Protease-Containing Cleaning Compositions" having U.S. Serial No. 08/3
  • Highly preferred enzymes that can be included in the detergent compositions of the present invention include lipases. It has been found that the cleaning performance on greasy soils is synergistically improved by using lipases.
  • Suitable lipase enzymes include those produced by microorganisms of the Pseudomonas group, such as Pseudomonas stutzeri ATCC 19.154, as disclosed in British Patent 1,372,034.
  • Suitable lipases include those which show a positive immunological cross-reaction with the antibody of the lipase, produced by the microorganism Pseudomonas fluorescens IAM 1057. This lipase is available from Amano Pharmaceutical Co.
  • Lipase P (Amano")
  • Lipase P (Amano)
  • Lipase P (Amano)
  • Lipase-P Lipase P
  • Highly preferred lipases are the D96L lipolytic enzyme variant of the native lipase derived from Humicola lanuginosa as described in US Serial No. 08/341,826.
  • the Humicola lanuginosa strain DSM 4106 is used.
  • This enzyme is inco ⁇ orated into the composition in accordance with the invention at a level of from 50 LU to 8500 LU per liter wash solution.
  • the variant D96L is present at a level offrom 100 LU to 7500 LU per liter of wash solution. More preferably at a level of from 150 LU to 5000 LU per liter of wash solution.
  • D96L lipolytic enzyme variant is meant the lipase variant as described in patent application WO 92 05249 viz. wherein the native lipase ex Humicola lanuginosa aspartic acid (D) residue at position 96 is changed to Leucine (L). According to this nomenclature said substitution of aspartic acid to Leucine in position 96 is shown as : D96L.
  • cutinases [EC 3.1.1.50] which can be considered as a special kind of lipase, namely lipases which do not require interfacial activation. Addition of cutinases to detergent compositions have been described in e.g. WO-A-88/09367 (Genencor).
  • the lipases and/or cutinases are normally inco ⁇ orated in the detergent composition at levels from 0.0001% to 2% of active enzyme by weight of the detergent composition.
  • Amylases (& and/or ⁇ ) can be included for removal of carbohydrate-based stains. Suitable amylases are Termamyl- ⁇ (Novo Nordisk), FungamylR and BAN- ⁇ (Novo Nordisk).
  • the above-mentioned enzymes may be of any suitable origin, such as vegetable, animal, bacterial, fimgal and yeast origin.
  • Said enzymes are normally inco ⁇ orated in the detergent composition at levels from 0.0001% to 2% of active enzyme by weight ofthe detergent composition.
  • Other suitable detergent ingredients that can be added are enzyme oxidation scavengers which are described in Copending European Patent application 92870018.6 filed on January 31, 1992. Examples of such enzyme oxidation scavengers are ethoxylated tetraethylene polyamines.
  • detergent compositions may be employed, such as soil-suspending agents, soil-release polymers, abrasives, bactericides, tarnish inhibitors, coloring agents, foam control agents, corrosion inhibitors and other perfumes.
  • Soil Release Agent Any soil release agents known to those skilled in the art can be employed in the practice of this invention.
  • Preferred polymeric soil release agents are characterized by having both hydrophilic segments, to hydrophilize the surface of hydrophobic fibers, such as polyester and nylon, and hydrophobic segments, to deposit upon hydrophobic fibers and remain adhered thereto through completion of washing and rinsing cycles and, thus, serve as an anchor for the hydrophilic segments. This can enable stains occurring subsequent to treatment with the soil release agent to be more easily cleaned in later washing procedures.
  • soil release agents will generally comprise from about 0.01% to about 10.0%, by weight, of the detergent compositions herein, typically from about 0.1% to about 5%, preferably from about 0.2% to about 3.0%.
  • the detergent compositions herein may also optionally contain one or more iron and manganese chelating agents as a builder adjunct material.
  • chelating agents can be selected from the group consisting of amino carboxylates, amino phosphonates, polyfunctionally -substituted aromatic chelating agents and mixtures thereof, all as hereinafter defined. Without intending to be bound by theory, it is believed that the benefit of these materials is due in part to their exceptional ability to remove iron and manganese ions from washing solutions by formation of soluble chelates.
  • these chelating agents will generally comprise from about 0.1% to about 10% by weight of the detergent compositions herein. More preferably chelating agents will comprise from about 0.1% to about 3.0% by weight of such compositions.
  • compositions ofthe present invention can also optionally contain water-soluble ethoxylated amines having clay soil removal and anti-redeposition properties.
  • Liquid detergent compositions which contain these compounds typically contain from about 0.01% to 5%.
  • the most preferred soil release and anti-redeposition agent is ethoxylated tetraethylenepentamine.
  • Exemplary ethoxylated amines are further described in U.S. Patent 4,597,898, VanderMeer, issued July 1, 1986, inco ⁇ orated herein by reference.
  • Another group of preferred clay soil removal/anti-redeposition agents are the cationic compounds disclosed in European Patent Application 111,965, Oh and Gosselink, published June 27, 1984, inco ⁇ orated herein by reference.
  • clay soil removal/anti-redeposition agents which can be used include the ethoxylated amine polymers disclosed in European Patent Application 111,984, Gosselink, published June 27, 1984; the zwitterionic polymers disclosed in European Patent Application 112,592, Gosselink, published July 4, 1984; and the amine oxides disclosed in U.S. Patent 4,548,744, Connor, issued October 22, 1985, all of which are inco ⁇ orated herein by reference.
  • CMC carboxymethylcellulose
  • Polymeric Dispersing Agents can advantageously be utilized in the compositions hereof. These materials can aid in calcium and magnesium hardness control. Suitable polymeric dispersing agents include polymeric polycarboxylates and polyethylene glycols, although others known in the art can also be used. The compositions hereof will generally comprise from 0% to about 5% of polymeric dispersing agent.
  • Suitable polymeric dispersing agents for use herein are described in U.S. Patent 3,308,067, Diehl, issued March 7, 1967, and European Patent Application No. 66915, published December 15, 1982, both inco ⁇ orated herein by reference.
  • Brightener Any suitable optical brighteners or other brightening or whitening agents known in the art can be inco ⁇ orated into the detergent compositions hereof.
  • the compositions hereof will generally comprise from 0% to about 5% of brightener
  • optical brighteners which may be useful in the present invention can be classified into subgroups which include, but are not necessarily limited to, derivatives of stilbene, pyrazoline, coumarin, carboxylic acid, methinecyanines, dibenzothiphene-5,5-dioxide, azoles, 5- and 6-membered-ring heterocycles, and other miscellaneous agents. Examples of such brighteners are disclosed in "The Production and Application of Fluorescent Brightening Agents", M. Zahradnik, Published by John Wiley & Sons, New York (1982), the disclosure ofwhich is inco ⁇ orated herein by reference.
  • Suds Suppressor- -Compounds known, or which become known, for reducing or suppressing the formation of suds can be inco ⁇ orated into the compositions ofthe present invention.
  • Suitable suds suppressors are described in Kirk Othmer Encyclopedia of Chemical Technology, Third Edition, Volume 7, pages 430-447 (John Wiley & Sons, Inc., 1979), U.S. Patent 2,954,347, issued September 27, 1960 to St. John, U.S. Patent 4,265,779, issued May 5, 1981 to Gandolfo et al., U.S. Patent 4,265,779, issued May 5, 1981 to Gandolfo et al. and European Patent Application No. 89307851.9, published February 7, 1990, U.S.
  • Patent 3,455,839 German Patent Application DOS 2,124,526, U.S. Patent 3,933,672, Bartolotta et al., and U.S. Patent 4,652,392, Baginski et al., issued March 24, 1987. All are inco ⁇ orated herein by reference.
  • compositions hereof will generally comprise from 0% to about 5% of suds suppressor.
  • compositions herein may also contain other perfume ingredients such as aldehydes, ketones, alcohols and esters. They have been described by Parry in Parry's Cyclopedia of Perfumarv (1925) Vol. I and II published by P. Blakiston's Son & Co.; and also by Bedoukian in Perfumary and Flavoring Synthetics (1967), published by Elsevier Publishing Company.
  • compositions hereof A wide variety of other ingredients useful in detergent compositions can be included in the compositions hereof, including other active ingredients, carriers, hydrotropes, processing aids, dyes or pigments, solvents for liquid formulations, bleaches, bleach activators, enzyme stabilizing systems, etc.
  • Liquid Compositions -
  • the laundry detergent compositions herein preferably have a pH in a 10% solution in water at 20°C of between about 5 and about 12, more preferably between about 8 and about 12 for granular compositions.
  • Liquid detergent compositions can contain water and other solvents as carriers.
  • Low molecular weight primary or secondary alcohols exemplified by methanol, ethanol, propanol, and isopropanol are suitable.
  • Monohydric alcohols are preferred for solubilizing surfactant, but polyols such as those containing from 2 to about 6 carbon atoms and from 2 to about 6 hydroxy groups (e.g., propylene glycol, ethylene glycol, glycerine, and 1,2-propanediol) can also be used.
  • Preferred liquid laundry detergent compositions hereof will preferably be formulated such that during use in aqueous cleaning operations, the wash water will have a pH of between about 6.5 and 11.0, preferably between about 7.0 and 8.5,
  • the liquid detergent compositions herein preferably have a pH in a 10% solution in water at 20°C of between about 6.5 and 11.0, preferably 7.0 to 8.5.
  • Techniques for controlling pH at recommended usage levels include the use of buffers, alkalis, acids, etc., and are well known to those skilled in the art.
  • the liquid compositions according to the present invention are in "concentrated form"; in such case, the liquid detergent compositions according to the present invention will contain a lower amount of water, compared to conventional liquid detergents.
  • the level of water is less than 50%, preferably less than 30% by weight ofthe detergent compositons.
  • Said concentrated products provide advantages to the consumer, who has a product which can be used in lower amounts and to the producer, who has lower shipping costs.
  • liquid compositions are especially effective when applied directly to soils and stains in a pretreatment step.
  • the detergent compositions of the present invention can also be used as detergent additive products. Such additive products are intended to supplement or boost the performance of conventional detergent compositions.
  • the detergent compositions according to the present invention include compositions which are to be used for cleaning of substrates, such as fabrics, fibers, hard surfaces, skin etc., for example hard surface cleaning compositions (with or without abrasives), laundry detergent compositions, automatic and non-automatic dishwashing compositions.
  • substrates such as fabrics, fibers, hard surfaces, skin etc.
  • hard surface cleaning compositions with or without abrasives
  • laundry detergent compositions automatic and non-automatic dishwashing compositions.
  • a "fresh citrus" perfume is prepared using the following c omponents
  • the perfiime can be used at a level of from about 0.01% to about 1%, by weight ofthe detergent composition.
  • the dodecahydro-3a,6,6,9A-tetramethylnaphtho (2,1-B) fiiran is substituted with an equal amount of one or more of the following perfume components: 3,3- dimethyl-5-(2,2,3 trimethyl-3 cyclopenten-l-yl)-4 pentenol, methyl lonone, cis 3 hexenyl iso butyrate, undecalactone, phenyl ethyl phenyl acetate, hexyl-ortho- hydroxybenzoate, and mixtures thereof.
  • a "fresh” perfume is prepared using the following components:
  • This perfiime is then useful in detergent compositions, particularly when amine surfactants are present.
  • the perfiime can be used at a level of from about 0.01% to about 1%, by weight ofthe detergent composition.
  • liquid detergent compositions are made :
  • Perfiime A may be substituted with an equal amount of Perfume B.
  • the CJO amidopropyldimethyl amine is substituted with an equal amount of the following amines: octyl amine, hexyl amine, decyl amine, dodecyl amine, Cg-Cj2 bis(hydroxyethyl)amine, Cg-Cj2 bis(hydroxyisopropyl)amine, and Cg, C9, CJ I or Cj2 amido-propyl dimethyl amine, and mixtures.
  • protease The following enzymes are used: protease, lipase, amylase, cellulase, peroxidase, and mixtures thereof.
  • the CJO amidopropyldimethyl amine is substituted with an equal amount ofthe following amines: octyl amine, hexyl amine, decyl amine, dodecyl amine, Cg-Cj2 bis(hydroxyethyl)amine, Cg-Cj2 bis(hydroxyisopropyl)amine, and Cg, C9, CJ J or Cj2 amido-propyl dimethyl amine, and mixtures.
  • protease The following enzymes are used: protease, lipase, amylase, cellulase, peroxidase, and mixtures thereof.
  • Perfume A may be substituted with an equal amount of Perfiime B.
  • Ingredient Example VI Example VU
  • Perfiime A may be substituted with an equal amount of Perfume B.
  • the amines are substituted with an equal amount of the following amines: hexyl amine, decyl amine, dodecyl amine, Cg-Cj 2 bis(hydroxyethyl)amine, C -Ci2 bis(hydroxyisopropyl)amine, and Cg. ⁇ i amido-propyl dimethyl amine, and mixtures.
  • the foUowing enzymes are used: protease, lipase, amylase, ceUulase, peroxidase, and mixtures thereof.
  • Perfume B may be substituted with an equal amount of Perfiime A.
  • the Cj2 bis (hydroxyethyl) amine is substituted with an equal amount of the foUowing amines: octyl amine, hexyl amine, decyl amine, dodecyl amine, Cg-Cj j bis(hydroxyethyl)amine, Cg-Cj 2 bis(hydroxyisopropyl)amine, and C .j2 amido ⁇ propyl dimethyl amine, and mixtures.
  • the foUowing enzymes are used: protease, Upase, amylase, ceUulase, peroxidase, and mixtures thereof.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)

Abstract

Compositions détergentes de blanchisserie contenant des tensioactifs à détersif amine et des parfums spécialement choisis atténuant la mauvaise odeur de l'amine. Plus spécifiquement, les parfums spécialement choisis sont choisis dans le groupe constitué de dodécahydro-3a,6,6,9A-tétraméthylnaphtho (2,1-B) furane,3,3-diméthyl-5-(2,2,3 triméthyl-3 cyclopentén-1-yl)-5 penténol, méthyl lonone, cis 3 hexényl iso butyrate, undécalactone, phényl éthyl phényl acétate, hexyl-ortho-hydroxybenzoate, et des mélanges de ces substances.
PCT/US1996/012611 1995-08-07 1996-08-01 Compositions detergentes contenant un amine et des parfums specialement selectionnes WO1997006235A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP96926223A EP0843719A1 (fr) 1995-08-07 1996-08-01 Compositions detergentes contenant un amine et des parfums specialement selectionnes
JP50854097A JP3886532B2 (ja) 1995-08-07 1996-08-01 アミンと特に選ばれた香料とを含有する洗剤組成物
US09/011,237 US5929022A (en) 1996-08-01 1996-08-01 Detergent compositions containing amine and specially selected perfumes
BR9609985A BR9609985A (pt) 1995-08-07 1996-08-01 Composições detergentes contendo amina e perfumes especialmente selecionados
CA002228966A CA2228966C (fr) 1995-08-07 1996-08-01 Compositions detergentes contenant un amine et des parfums specialement selectionnes

Applications Claiming Priority (2)

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US194895P 1995-08-07 1995-08-07
US60/001,948 1995-08-07

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WO1999021954A1 (fr) * 1997-10-29 1999-05-06 The Procter & Gamble Company Compositions pour lessives a mauvaises odeurs reduites et procedes de preparation desdites compositions
US5916862A (en) * 1995-06-20 1999-06-29 The Procter & Gamble Company Detergent compositions containing amines and anionic surfactants
WO1999055819A1 (fr) * 1998-04-23 1999-11-04 The Procter & Gamble Company Particules de parfum en inclusion et compositions detergentes contenant ces particules
EP0965326A1 (fr) * 1998-06-15 1999-12-22 The Procter & Gamble Company Compositions de parfum
WO2000055288A1 (fr) * 1999-03-15 2000-09-21 The Procter & Gamble Company Compositions de parfums masquant les mauvaises odeurs d'amines et procedes correspondants
WO2001023274A1 (fr) * 1999-09-30 2001-04-05 The Procter & Gamble Company Emballage pour detergents dote de moyens pour masquer les mauvaises odeurs d'amine
WO2001034752A1 (fr) * 1999-11-09 2001-05-17 The Procter & Gamble Company Compositions detergentes contenant un produit de reaction parfume
WO2002006437A1 (fr) * 2000-07-19 2002-01-24 The Procter & Gamble Company Compositions nettoyantes
EP1493803A1 (fr) * 2000-07-19 2005-01-05 The Procter & Gamble Company Compositions de nettoyage
US6906012B1 (en) 1999-11-09 2005-06-14 Procter & Gamble Company Detergent compositions comprising a fragrant reaction product
DE19807195B4 (de) * 1997-02-25 2010-02-04 Ecolab Inc., St. Paul Zusammensetzung und Verfahren zum Reinigen und zum Trocknen von Fahrzeugen
CN105283531A (zh) * 2013-06-12 2016-01-27 狮王株式会社 洗涤剂组合物

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JP6231378B2 (ja) * 2012-12-28 2017-11-15 花王株式会社 衣料用液体洗浄剤組成物
JP6118660B2 (ja) * 2013-06-28 2017-04-19 ライオン株式会社 食器洗い機用洗浄剤

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Cited By (18)

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Publication number Priority date Publication date Assignee Title
US5916862A (en) * 1995-06-20 1999-06-29 The Procter & Gamble Company Detergent compositions containing amines and anionic surfactants
DE19807195B4 (de) * 1997-02-25 2010-02-04 Ecolab Inc., St. Paul Zusammensetzung und Verfahren zum Reinigen und zum Trocknen von Fahrzeugen
WO1999021954A1 (fr) * 1997-10-29 1999-05-06 The Procter & Gamble Company Compositions pour lessives a mauvaises odeurs reduites et procedes de preparation desdites compositions
US6458754B1 (en) 1998-04-23 2002-10-01 The Procter & Gamble Company Encapsulated perfume particles and detergent compositions containing said particles
WO1999055819A1 (fr) * 1998-04-23 1999-11-04 The Procter & Gamble Company Particules de parfum en inclusion et compositions detergentes contenant ces particules
US6869923B1 (en) 1998-06-15 2005-03-22 Procter & Gamble Company Perfume compositions
WO1999065458A1 (fr) * 1998-06-15 1999-12-23 The Procter & Gamble Company Compositions parfumantes
EP0965326A1 (fr) * 1998-06-15 1999-12-22 The Procter & Gamble Company Compositions de parfum
WO2000055288A1 (fr) * 1999-03-15 2000-09-21 The Procter & Gamble Company Compositions de parfums masquant les mauvaises odeurs d'amines et procedes correspondants
JP2002539322A (ja) * 1999-03-15 2002-11-19 ザ、プロクター、エンド、ギャンブル、カンパニー アミンの悪臭を隠蔽する香料組成物及び方法
WO2001023274A1 (fr) * 1999-09-30 2001-04-05 The Procter & Gamble Company Emballage pour detergents dote de moyens pour masquer les mauvaises odeurs d'amine
WO2001034752A1 (fr) * 1999-11-09 2001-05-17 The Procter & Gamble Company Compositions detergentes contenant un produit de reaction parfume
US6906012B1 (en) 1999-11-09 2005-06-14 Procter & Gamble Company Detergent compositions comprising a fragrant reaction product
WO2002006437A1 (fr) * 2000-07-19 2002-01-24 The Procter & Gamble Company Compositions nettoyantes
EP1493803A1 (fr) * 2000-07-19 2005-01-05 The Procter & Gamble Company Compositions de nettoyage
CN105283531A (zh) * 2013-06-12 2016-01-27 狮王株式会社 洗涤剂组合物
EP3009497A4 (fr) * 2013-06-12 2017-03-01 Lion Corporation Composition nettoyante
US9982222B2 (en) 2013-06-12 2018-05-29 Lion Corporation Detergent composition

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CA2228966A1 (fr) 1997-02-20
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AR003210A1 (es) 1998-07-08
CA2228966C (fr) 2001-10-30
JP3886532B2 (ja) 2007-02-28

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