EP1987124B1 - Composition d'entretien liquide pour azurage - Google Patents

Composition d'entretien liquide pour azurage Download PDF

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Publication number
EP1987124B1
EP1987124B1 EP07711505.3A EP07711505A EP1987124B1 EP 1987124 B1 EP1987124 B1 EP 1987124B1 EP 07711505 A EP07711505 A EP 07711505A EP 1987124 B1 EP1987124 B1 EP 1987124B1
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EP
European Patent Office
Prior art keywords
liquid detergent
surfactant
detergent formulation
laundry liquid
formulation according
Prior art date
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EP07711505.3A
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German (de)
English (en)
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EP1987124A1 (fr
Inventor
Stephen Norman Batchelor
Jayne Michelle Bird
Carol Meacock
Dawn Rigby
Jacqueline Willaims
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Unilever Global IP Ltd
Unilever IP Holdings BV
Original Assignee
Unilever PLC
Unilever NV
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Application filed by Unilever PLC, Unilever NV filed Critical Unilever PLC
Priority to EP07711505.3A priority Critical patent/EP1987124B1/fr
Publication of EP1987124A1 publication Critical patent/EP1987124A1/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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/40—Dyes ; Pigments
    • C11D3/42—Brightening agents ; Blueing agents
    • 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
    • C11D1/83—Mixtures of non-ionic with anionic 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
    • C11D3/40—Dyes ; Pigments
    • 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
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic 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
    • C11D1/02—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
    • C11D1/66—Non-ionic compounds
    • C11D1/72—Ethers of polyoxyalkylene glycols

Definitions

  • the present invention concerns azo dyes in a laundry liquid composition and reducing precipitation thereof.
  • the dyes are diverse in structure and consequently diverse chemical and physical properties. For example, some dyes are cationic and precipitate with anionic compounds such as surfactants; some dyes are readily hydrolysed and decompose rapidly in water; some dyes readily aggregate and precipitate from solution, some dyes selectively bind to other organic and biological materials. There is also wide variance in the light stability of the dyes.
  • solvent blue 58 (1,4-bis(2-ethylhexylamino)-anthraquinone) may be used in a liquid formulation containing linear alkylbenzene sulphonate and non-ionic surfactants.
  • solvent blue 58 a hydrophobic anthraquinone dye containing a C8 chain at levels of 0.005 to 0.025 wt % in a laundry liquid formulation.
  • the long alkyl chain i.e. the C8, helps to solubilise the dye in the liquid formulation.
  • the long chain effectively interacts with the alkyl chains of the surfactant reducing precipitation of the dye over time.
  • the formulation also contains a hydrotrope to solubilise the dye.
  • Solvent blue 58 is of the following structure:
  • Hydrophobic dyes i.e. dyes which contain no charged solubilising groups, have extremely low water solubilities. These solubilities are not predictable. Such dyes are found in the groups of disperse and solvent dyes.
  • the water solubility of the mono-azo dye disperse blue 79:1 is reported to be 0,0052 mg/L at 25 °C, IUCLID data set 201-14540B. Therefore stabilising such compounds in domestic liquid detergent solutions at the high levels (>0.000001% which corresponding to 0.01mg/L. Even if the compound may be dissolved into the solution using surfactants, the solutions are typically unstable with time and the dye precipitates out of solution.
  • US 4 800 037 discloses a process for making a heavy duty liquid detergent composition comprising a dye.
  • the present invention provides an aqueous laundry liquid detergent formulation comprising:
  • Treatment is preferably carried out in the domestic context, at temperature between 10 to 60 °C, preferably 15 to 40 °C.
  • the water present in the aqueous laundry liquid detergent formulation is preferably at a level of at least 40 wt%.
  • the selected anionic surfactant is present in 99 wt% excess of the total anionic surfactant content.
  • ratio of anionic surfactant to non-ionic surfactant is in the range from 0.75 to 1:1.
  • the dye level is in the range from 0.0002 to 0.004%.
  • the liquid composition of the invention comprises from 10 to 50 wt%, preferably from 12 to 25 % by weight of a surfactant mixture.
  • Linear alkyl benzene sulphonates salts (LAS), particularly C 11 -C 18 alkylbenzene sulphonates in the form of the sodium salt.
  • Alkyl sulphate surfactants are either primary or secondary.
  • Alkyl sulphates have the general formula ROSO 3 M wherein R is preferably a C 10 -C 24 hydrocarbyl, preferably an alkyl straight or branched chain or hydroxyalkyl having a C 10 -C 20 alkyl component, more preferably a C 12 -C 18 alkyl or hydroxyalkyl, and M is hydrogen or a water soluble cation, e.g., an alkali metal cation (e.g., sodium potassium, lithium). Particularly preferred is sodium dodecyl sulphate (SDS).
  • SDS sodium dodecyl sulphate
  • Alkyl ethoxylated sulphate surfactants are another category of preferred anionic surfactant. These surfactants are water soluble salts or acids typically of the formula RO(A)mSO 3 M wherein R is an unsubstituted C 10 -C 24 alkyl or hydroxyalkyl group having a C 10 -C 24 alkyl component, preferably a C 12 -C 20 alkyl or hydroxyalkyl, more preferably C 12 -C 18 alkyl or hydroxyalkyl, A is an ethoxy, m is greater than zero, typically between about 1 and 6, more preferably between 1 and 3, and M is hydrogen or a water soluble 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 C 10 -C 24 alkyl or hydroxyalkyl group having a C 10 -C 24
  • Exemplary surfactants are C 12 -C 18 alkyl polyethoxylate (1.0) sulphate, C 12 - C 18 alkyl polyethoxylate (2.25) sulphate, C 12 -C 18 alkyl polyethoxylate (3.0) sulphate, and C 12 -C 18 alkyl polyethoxylate (4.0) sulphate wherein M is conveniently selected from sodium and potassium.
  • propoxylated sulphates may also be used.
  • Sodium lauryl ether sulphates are most preferred with one to three ethoxy groups.
  • Other non-ionic surfactant may be selected from C 6 -C 12 alkyl phenol alkoxylates (especially ethoxylates and mixed ethoxy/propoxy), block alkylene oxide condensate of C 6 to C 12 alkyl phenols, alkylene oxide condensates of C 9 -C 22 alkanols and ethylene oxide/propylene oxide block polymers (PluronicTM-BASF Corp.) .
  • minor surfactants include cationics, soaps, betaines, alkylpolyglycosides, N-methyl glucomides. It is preferred that the minor surfactants are present at levels below 3 wt%.
  • Typical dye suppliers may be found in the colour index, and include Clariant, Dystar, Ciba & BASF.
  • Hydrophobic dyes are defined as organic compounds with a maximum extinction coefficient greater than 1000 L/mol/cm in the wavelength range cf 400 to 750 nm and that are uncharged in aqueous solution at a pH in the range from 7 to 11.
  • the hydrophobic dyes are devoid of polar solubilising groups.
  • the hydrophobic dye does not contain any sulphonic acid, carboxylic acid, or quaternary ammonium groups.
  • hydrophobic dyes are found in the classes of solvent and disperse dyes.
  • Shading of white garments may be done with any colour depending on consumer preference.
  • Blue and Violet are particularly preferred shades and consequently preferred dyes or mixtures of dyes are ones that give a blue or violet shade on white polyester.
  • the dye(s) have a peak absorption wavelength of from 550nm to 650nm, preferably from 570nm to 630nm.
  • D is selected from the group consisting of: azothiophenes, azobenzothiazoles and azopyridones.
  • Preferred aryl are -C6H5 and C10H7.
  • composition may also comprise between 0.0001 to 0.1 wt % of one or more other dyes selected from cotton substantive shading dyes of group consisting of: hydrolysed reactive dye; acid dye; and direct dye.
  • one or more other dyes selected from cotton substantive shading dyes of group consisting of: hydrolysed reactive dye; acid dye; and direct dye.
  • Example of preferred acid dyes are: acid blue 62, 40 and 290.
  • the aqueous liquid detergent formulation has a pH-value between 6 and 12, more preferably between 7 and 10, even more preferably between 7.5 and 9.5.
  • a pH jump system i.e. a system that increase the pH-value to above 7.5 on dilution with water, is beneficial for the cleaning performance of said composition.
  • the liquid detergent composition of the invention may additionally comprise builders, solvents, perfumes, sequestrants, polymers, preservatives, fluorescers, dyes, biocides, buffers, salts.
  • Suitable detergency builders as optional, but preferred, ingredients may also be present, as found in WO-00/34427 .
  • One salt of particular interest is citrate, because of its additional builder and bleaching characteristics.
  • the liquid formulation of the present invention preferably comprises between 0.001 to 3% by weight of a perfume composition, more preferably between 0.1 to 2% by weight of a perfume composition.
  • Said perfume composition preferably comprises at least 0.01% by weight based on the liquid composition of a perfume component selected from terpenes, ketones, aldehydes and mixtures thereof.
  • the perfume composition may fully consist of the perfume component but generally the perfume composition is a complex mixture of perfumes of various differing perfume classifications.
  • the perfume composition preferably comprises 0.1 to 2% by weight of the perfume component.
  • the liquid detergent composition of the invention preferably comprise between 0.001 to 2% by weight of an antioxidant.
  • the antioxidant is present at a concentration in the range 0.01 to 0.08% by weight.
  • Anti-oxidants are substances as described in Kirk-Othmers (Vol 3, pg 424 ) and in Uhlmans Encyclopedia (Vol 3, pg 91 ).
  • An example of a preferred antioxidant is BHT.
  • the laundry treatment composition most preferably comprises a fluorescent agent(optical brightener).
  • fluorescent agents are well known and many such fluorescent agents are available commercially. Usually, these fluorescent agents are supplied and used in the form of their alkali metal salts, for example, the sodium salts.
  • the total amount of the fluorescent agent or agents used in laundry treatment composition is generally from 0.005 to 2 wt %, more preferably 0.01 to 0.1 wt %.
  • Preferred classes of fluorescer are: Di-styryl biphenyl compounds, e.g. Tinopal (Trade Mark) CBS-X, Di-amine stilbene di-sulphonic acid compounds, e.g.
  • Preferred fluorescers are: sodium 2 (4-styryl-3-sulfophenyl)-2 H- naphthol [1, 2- d ]triazole, disodium 4,4'-bis ⁇ [(4-anilino-6-(N methyl- N -2 hydroxyethyl) amino 1,3,5-Triazin-2-yl)]amino ⁇ stilbeno-2-2'disulfonate, disodium 4,4'-bis[(4-anilino-6-morpholino-1,3, 5-triazin-2-yl) amino] stilbene-2-2' disulfonate, and disodium 4,4'-bis(2-sulfostyryl)blphenyl.
  • Model Liquid detergent composition were created containing 15% total surfactant and 0.0004% of the dye disperse blue 79:1.
  • the surfactants were chosen from LAS, SDS, SLES(lEO), SLES(3EO), and two non-ionic surfactants: non-ionic NI(7EO)- Neodol 25-7 which is a mixture of 12 to 15 carbon chain length alcohols with about 7 ethylene oxide groups per molecule and NI(9EO) - Neodol 25-9, a C12-13 mixture with about 9 moles of ethylene oxide.
  • the dye was added from a concentrated mix in the corresponding non-ionic of the formulation.
  • the detergents were left for 7 days then the UV-VIS spectrum measured using a 5cm cell.
  • the optical density at 590nm was recorded (maximum of the dye) and 750nm where there is negligible absorbance from the dye.
  • the base surfactant has negligible absorbance at 590 and 750nm.
  • the 750nm was made to measure scattering from dye particles that were not fully dissolved. These measurements are referred to as day 0.
  • % dye 7 100 * OD 590 nm , day 7 ⁇ OD 750 nm , day 7 OD 590 nm , day 0 ⁇ OD 750 nm , day 0
  • the 750nm subtraction corrects for scattering effects.
  • UV-VIS spectra were measured on the day of creation and again after 7 days.
  • Mix (ii) and (iii) were stable with 94 and 98% dye after 7 days whilst mix (i) was unstable with 85% dye after 7 days.

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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)

Claims (9)

  1. Formulation de détergent liquide de lessive aqueuse comprenant :
    (a) 0,000001 à 0,01 % en masse d'un colorant azo hydrophobe bleu ou violet ;
    (b) de 10 à 50 % en masse d'un mélange de tensioactifs, le mélange de tensioactifs comprenant : (i) un tensioactif non-ionique ; et (ii) un tensioactif anionique choisi dans le groupe consistant en : benzènesulfonate d'alkyle linéaire, sulfate d'alkyle, et sulfate éthoxylé d'alkyle, et ,
    (c) les auxiliaires de reste jusqu'à 100 % en masse,
    dans laquelle le rapport de tensioactif anionique à tensioactif non-ionique se trouve dans l'intervalle de rapport massique de 0,5 à 1,5:1 et un des tensioactifs anioniques choisis est présent dans un excès de 85 % en masse de la teneur totale en tensioactif anionique, et le colorant hydrophobe est un composé organique avec un coefficient d'extinction maximum supérieur à 1 000 L/mol/cm dans l'intervalle de longueur d'onde de 400 à 750 nm et est non-chargé dans une solution aqueuse à un pH dans l'intervalle de 7 à 11, dans laquelle le colorant azo hydrophobe est choisi parmi des colorants mono-azo de la forme :
    Figure imgb0007
     dans laquelle R3 est -CH2CH2R5 et R4 est -CH2CH2R6 et R5 et R6 sont indépendamment choisis dans le groupe consistant en : H, -CN, -OH, -C6H5, -OCOR7 et -COOR7,
    et R7 est indépendamment choisi parmi : un groupe aryle et alkyle, et D est un groupe aromatique ou hétéroaromatique.
  2. Formulation de détergent liquide de lessive aqueuse selon la revendication 1, dans laquelle en ce qui concerne le tensioactif anionique choisi il est présent dans un excès de 99 % en masse de la teneur totale en tensioactif anionique.
  3. Formulation de détergent liquide de lessive aqueuse selon l'une quelconque des revendications précédentes, dans laquelle le rapport massique de tensioactif anionique à tensioactif non-ionique se trouve dans l'intervalle de 0,75 à 1:1.
  4. Formulation de détergent liquide de lessive aqueuse selon l'une quelconque des revendications précédentes, dans laquelle le non-ionique est un éthoxylate d'alcool, le sulfate éthoxylé d'alkyle est un lauryléthersulfate de sodium, et le sulfate d'alkyle est le dodécylsulfate de sodium.
  5. Formulation de détergent liquide de lessive aqueuse selon l'une quelconque des revendications précédentes, dans laquelle le non-ionique est choisi parmi un éthoxylate d'alcool contenant une chaîne carbonée de 12 à 15 atomes de carbone et de 7 à 9 groupes oxyde d'éthylène.
  6. Formulation de détergent liquide de lessive aqueuse selon l'une quelconque des revendications précédentes, dans laquelle l'éthoxylate d'alcool contient 9 groupes oxyde d'éthylène.
  7. Formulation de détergent liquide de lessive aqueuse selon l'une quelconque des revendications précédentes, dans laquelle la teneur en colorant se trouve dans l'intervalle de 0,0002 à 0,004 % en masse.
  8. Formulation de détergent liquide de lessive aqueuse selon l'une quelconque des revendications précédentes, dans laquelle le mélange de tensioactif est présent dans l'intervalle de 12 à 25 % en masse.
  9. Formulation de détergent liquide de lessive aqueuse selon l'une quelconque des revendications précédentes, dans laquelle un tensioactif différent de celui défini dans la revendication 1 est présent à une teneur inférieure à 3 % en masse.
EP07711505.3A 2006-02-24 2007-02-07 Composition d'entretien liquide pour azurage Active EP1987124B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP07711505.3A EP1987124B1 (fr) 2006-02-24 2007-02-07 Composition d'entretien liquide pour azurage

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP06250980 2006-02-24
EP07711505.3A EP1987124B1 (fr) 2006-02-24 2007-02-07 Composition d'entretien liquide pour azurage
PCT/EP2007/001167 WO2007096067A1 (fr) 2006-02-24 2007-02-07 Composition d'entretien liquide pour azurage

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EP1987124A1 EP1987124A1 (fr) 2008-11-05
EP1987124B1 true EP1987124B1 (fr) 2018-09-05

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EP07711505.3A Active EP1987124B1 (fr) 2006-02-24 2007-02-07 Composition d'entretien liquide pour azurage
EP07703401A Withdrawn EP1987123A1 (fr) 2006-02-24 2007-02-07 Composition d'entretien liquide pour l'azurage

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AR (1) AR059606A1 (fr)
WO (2) WO2007096067A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2169040B1 (fr) 2008-09-30 2012-04-11 The Procter & Gamble Company Compositions détergentes liquides démontrant un effet à deux couleurs ou plus
EP2169041A1 (fr) 2008-09-30 2010-03-31 The Procter and Gamble Company Compositions détergentes liquides démontrant un effet à deux couleurs ou plus
EP2354214B2 (fr) † 2010-01-06 2022-06-08 Unilever IP Holdings B.V. Taux d'agent tensioactif dans des formulations de colorants
ES2491104T3 (es) * 2010-04-29 2014-09-05 Unilever N.V. Colorantes azoicos bis heterocíclicos
CN103562370B (zh) 2011-05-26 2016-08-17 荷兰联合利华有限公司 洗衣液组合物
WO2013189615A1 (fr) * 2012-06-21 2013-12-27 Unilever Plc Détergent de lessive liquide

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3958928A (en) 1975-05-05 1976-05-25 Lever Brothers Company Reduced-staining colorant system for liquid laundry detergents
US4800037A (en) 1987-06-05 1989-01-24 Lever Brothers Company Process for making a heavy duty liquid detergent composition
WO2006045375A1 (fr) 2004-09-23 2006-05-04 Unilever Plc Compositions de traitement de linge

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2034563A1 (en) * 1970-07-11 1972-01-27 Henkel & Cie GmbH, 4000 Dusseldorf Coloured detergent compsns - contg nitro-alkanols as dye stabilisers
JPS5438605B2 (fr) * 1974-06-07 1979-11-22
SK53294A3 (en) * 1993-05-07 1995-04-12 Albright & Wilson Concentrated aqueous mixture containing surface active matter and its use
AR049538A1 (es) * 2004-06-29 2006-08-09 Procter & Gamble Composiciones de detergentes para lavanderia con colorante entonador eficiente
AR049537A1 (es) * 2004-06-29 2006-08-09 Procter & Gamble Composiciones de detergentes para lavanderia con colorante entonador

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3958928A (en) 1975-05-05 1976-05-25 Lever Brothers Company Reduced-staining colorant system for liquid laundry detergents
US4800037A (en) 1987-06-05 1989-01-24 Lever Brothers Company Process for making a heavy duty liquid detergent composition
WO2006045375A1 (fr) 2004-09-23 2006-05-04 Unilever Plc Compositions de traitement de linge

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
"Kirk-Othmer Encyclopedia of Chemical Technology", vol. 8, 1993, article KIRK-OTHMER: "Dyes and dye intermediates", pages: 542 - 554
article HUNGER, pages: 36, 134 - 139, 295 - 297
O ANNEN: "Replacement of disperse anthraquinone dyes", ANNEN, REV.PROG. COLORATION, vol. 17, pages 72 - 85, XP055628601

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WO2007096067A1 (fr) 2007-08-30
AR059606A1 (es) 2008-04-16
EP1987123A1 (fr) 2008-11-05
EP1987124A1 (fr) 2008-11-05
WO2007096068A1 (fr) 2007-08-30

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