EP2331669B1 - Colorants de pyridine et pyridazine cationiques - Google Patents

Colorants de pyridine et pyridazine cationiques Download PDF

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Publication number
EP2331669B1
EP2331669B1 EP09782877.6A EP09782877A EP2331669B1 EP 2331669 B1 EP2331669 B1 EP 2331669B1 EP 09782877 A EP09782877 A EP 09782877A EP 2331669 B1 EP2331669 B1 EP 2331669B1
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Prior art keywords
alkyl
phenyl
composition according
detergent composition
laundry detergent
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EP09782877.6A
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German (de)
English (en)
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EP2331669A1 (fr
Inventor
Stephen Norman Batchelor
Jayne Michelle Bird
Susan Barbara Joyce
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Unilever PLC
Unilever NV
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Unilever PLC
Unilever NV
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    • 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/40—Dyes ; Pigments
    • C11D3/42—Brightening agents ; Blueing agents

Definitions

  • the present invention relates to the delivery of dyes to fabrics.
  • WO 2007/084729 discloses the use of thiazolium dyes in Laundry formulations as a shading agent that does not build up over multiple washes.
  • WO 2007/087252 discloses the use of thiazolium dyes in Laundry formulations as a shading agent that does not build up over multiple washes.
  • GB1491930 discloses cationic pyridine based mono-azo dyestuffs in composition for hair dyeing.
  • the present invention provides a laundry treatment composition comprising:
  • the C-N N-phenyl(B)-para-NR1R2 group as given indicates ortho substitution of the azo group to the quaternary nitrogen in the structure.
  • the present invention provides a domestic method of treating a textile, the method comprising the steps of: (i) treating a textile with an aqueous solution of the cationic pyridine/pyridazine dye, the aqueous solution comprising from 1 ppb to 1 ppm of the cationic pyridine/pyridazine dye, and from 0 ppb to 1 ppm of another dye or pigment selected from: pigments, hydrophobic dyes and direct dyes; and, from 0.0 g/L to 3 g/L of a surfactant; (ii) optionally rinsing the textile; and, (iii) drying the textile.
  • the aqueous solution comprises 0.1 to 50 ppm of fluorescer.
  • the textile to be laundered is composed of cotton, polyester, nylon or elastane fibres.
  • the cationic pyridine/pyridazine dyes as used in the present invention are blue or violet.
  • the cationic pyridine/pyridazine dyes gives a blue or violet colour to a white cloth with a hue angle of 240 to 345, more preferably 260 to 320, most preferably 270 to 300.
  • the white cloth used is bleached non-mercerised woven cotton sheeting.
  • the aromatic rings and R 1 , R 2 and R 3 of the dye may be further substituted by suitable uncharged organic groups.
  • the suitable uncharged organic groups individually should have a molecular weight of less than 400, preferably less than 150.
  • the uncharged organic groups are selected from methyl, ethyl, NHCOCH 3 , CH 3 O, C 2 H 5 O, HO, amine, Cl, F, Br, I, NO 2 , CH 3 SO 2 , C 2 H 5 SO 2 , CN, CONH 2 .
  • any aromatic ring in the cationic pyridine/pyridazine dye is not substituted directly by OH, i.e., a phenolic moiety should not be present.
  • a polyether chain is defined as at least two repeating units that are chemically bound via the ether's oxygen.
  • the polyether chain may be branched or linear.
  • Preferred polyether chains are selected from ethylene oxides or propylene oxides. Where an alkyl and/or polyether chain is present the chain preferably has a molecular weight of less than 1000, more preferably less than 400, even more preferably less than 200.
  • R1 and/or R2 is a polyether chain as defined above.
  • Example of polyether groups are (CH 2 CH 2 O) 4 H,(CH 2 CH 2 CH 2 O) 3 H, (CH 2 C(CH 3 )HO) 3 H, (CH 2 CH 2 O) 2 (CH 2 C(CH 2 O(CH 2 CH 2 O) 2 H) 2 H and those described in WO2008/087497 .
  • An- is a counter ion.
  • An- is not essential aspect of the invention and may be varied widely.
  • An- may be an anion such as RCOO - , BPh 4 - , ClO 4 - , BF 4 - , PF 6 - , RSO 3 - , RSO 4 - , SO 4 2- , NO 3 - , F - , Cl - , Br - , or I - , with R being hydrogen, optionally substituted alkyl or optionally substituted aryl.
  • An- is selected from: CH 3 SO 3 - , CH 3 CO 2 - , BF 4 - , Cl - , F - , Br - , and I - .
  • the aliphatic ring is a morpholine or piperidine ring.
  • the azo group is preferably ortho to the quanternary nitrogen.
  • the A ring When A is further condensed to a benzene ring, the A ring forms an extended aromatic ring system of the form: or or
  • R 1 and R 2 are selected from: H; polyethers, C1-C8-alkyl which may be substituted by -OH, O-C1-C8-alkyl, -Cl, and -F, -CN; -C1-C8-alkyl-C(O)2-C1-C8-alkyl; -C1-C8-alkyl-OC(O)-C1-C8-alkyl;-C1-C8-alkyl-phenyl; -C1-C8-alkyl-naphthyl; phenyl; and, naphthyl, wherein the benzyl and phenyl may be substituted by a group selected from: -OC1-C6-alkyl, -C1-C6-alkyl.
  • R 1 and R 2 are selected from: -H; -CH 3 ; -C 2 H 5 ; -(CH 2 ) 3 H; -(CH 2 ) 4 H;-C 2 H 4 OH; -C 2 H 4 Cl; -C 2 H 4 CN; -C 6 H 5 ; -CH 2 C 6 H 5 ; -C 2 H 4 OCOCH 3 ; -C 2 H 4 COOCH 3 ; and, -C 2 H 4 OC 2 H 4 OH.
  • Most preferred groups for R 1 and R 2 are methyl or ethyl.
  • R 3 is selected from: H, C1-C8-alkyl, -C1-C8-alkyl-phenyl; -C1-C8-alkyl-naphthyl; phenyl; and, naphthyl. More preferably, R 3 is selected from methyl, ethyl and benzyl. Most preferred groups for R 3 are methyl or ethyl.
  • Ring B may carry up to two groups that are selected from: -Br; -Cl; -F; -NO 2 ; -CN; -SO2-benzyl; -C(O)O-C1-C8-alkyl; -OC1-C8-alkyl; -NHC(O)C1-C4-alkyl, -SO2-C1-C8-alkyl; and -SO2-phenyl. More preferably -Br; -Cl; -F; -OC1-C4-alkyl and-NHC(O)C1-C4-alkyl. When the B ring is further substituted this is preferably ortho and/or meta to the -NR 1 R 2 amine group.
  • one is preferably ortho and the other meta to the -NR 1 R 2 amine group and on opposite sides of the ring (i.e. in the 2, 5 positions).
  • the most preferred substituents for the B ring are selected from methyl, Cl, NHCOCH 3 , CH 3 O and C 2 H 5 O.
  • Deposition of the dye onto polyester may be increased by increasing the number of hydrophobic organic groups on the dye.
  • Hydrophobic organic groups are groups which increase the calculate logP of the dye in comparison to a H substituent.
  • the dyes are granulated with an acidic binder as described in WO2007/039042 (Unilever ). This reduced degradation due to alkaline hydrolysis on storage.
  • the composition comprises between 2 to 70 wt% of a surfactant, most preferably 10 to 30 wt %.
  • a surfactant most preferably 10 to 30 wt %.
  • the nonionic and anionic surfactants of the surfactant system may be chosen from the surfactants described " Surface Active Agents" Vol. 1, by Schwartz & Perry, Interscience 1949 , Vol. 2 by Schwartz, Perry & Berch, Interscience 1958, in the current edition of "McCutcheon's Emulsifiers and Detergents” published by Manufacturing Confectioners Company or in " Tenside-Taschenbuch", H. Stache, 2nd Edn., Carl Hauser Verlag, 1981 .
  • the surfactants used are saturated.
  • Suitable nonionic detergent compounds which may be used include, in particular, the reaction products of compounds having a hydrophobic group and a reactive hydrogen atom, for example, aliphatic alcohols, acids, amides or alkyl phenols with alkylene oxides, especially ethylene oxide either alone or with propylene oxide.
  • Specific nonionic detergent compounds are C 6 to C 22 alkyl phenol-ethylene oxide condensates, generally 5 to 25 EO, i.e. 5 to 25 units of ethylene oxide per molecule, and the condensation products of aliphatic C 8 to C 18 primary or secondary linear or branched alcohols with ethylene oxide, generally 5 to 40 EO.
  • Suitable anionic detergent compounds which may be used are usually watersoluble alkali metal salts of organic sulphates and sulphonates having alkyl radicals containing from about 8 to about 22 carbon atoms, the term alkyl being used to include the alkyl portion of higher acyl radicals.
  • suitable synthetic anionic detergent compounds are sodium and potassium alkyl sulphates, especially those obtained by sulphating higher C 8 to C 18 alcohols, produced for example from tallow or coconut oil, sodium and potassium alkyl C 9 to C 20 benzene sulphonates, particularly sodium linear secondary alkyl C 10 to C 15 benzene sulphonates; and sodium alkyl glyceryl ether sulphates, especially those ethers of the higher alcohols derived from tallow or coconut oil and synthetic alcohols derived from petroleum.
  • the preferred anionic detergent compounds are sodium C 11 to C 15 alkyl benzene sulphonates and sodium C 12 to C 18 alkyl sulphates.
  • surfactants such as those described in EP-A-328 177 (Unilever ), which show resistance to salting-out, the alkyl polyglycoside surfactants described in EP-A-070 074 , and alkyl monoglycosides.
  • Preferred surfactant systems are mixtures of anionic with nonionic detergent active materials, in particular the groups and examples of anionic and nonionic surfactants pointed out in EP-A-346 995 (Unilever ).
  • surfactant system that is a mixture of an alkali metal salt of a C 16 to C 18 primary alcohol sulphate together with a C 12 to C 15 primary alcohol 3 to 7 EO ethoxylate.
  • the nonionic detergent is preferably present in amounts greater than 10%, e.g. 25 to 90 wt % of the surfactant system.
  • Anionic surfactants can be present for example in amounts in the range from about 5% to about 40 wt % of the surfactant system.
  • the surfactant may be a cationic such that the formulation is a fabric conditioner.
  • the present invention When the present invention is used as a fabric conditioner it needs to contain a cationic compound.
  • the quaternary ammonium compound is a quaternary ammonium compound having at least one C 12 to C 22 alkyl chain.
  • the quaternary ammonium compound has the following formula: in which R 1 is a C 12 to C 22 alkyl or alkenyl chain; R 2 , R 3 and R 4 are independently selected from C 1 to C 4 alkyl chains and X- is a compatible anion.
  • R 1 is a C 12 to C 22 alkyl or alkenyl chain; R 2 , R 3 and R 4 are independently selected from C 1 to C 4 alkyl chains and X- is a compatible anion.
  • a preferred compound of this type is the quaternary ammonium compound cetyl trimethyl quaternary ammonium bromide.
  • a second class of materials for use with the present invention are the quaternary ammonium of the above structure in which R 1 and R 2 are independently selected from C 12 to C 22 alkyl or alkenyl chain; R 3 and R 4 are independently selected from C 1 to C 4 alkyl chains and X- is a compatible anion.
  • the ratio of cationic to nonionic surfactant is from 1:100 to 50:50, more preferably 1:50 to 20:50.
  • the cationic compound may be present from 1.5 wt % to 50 wt % of the total weight of the composition.
  • the cationic compound may be present from 2 wt % to 25 wt %, a more preferred composition range is from 5 wt % to 20 wt %.
  • the softening material is preferably present in an amount of from 2 to 60% by weight of the total composition, more preferably from 2 to 40%, most preferably from 3 to 30% by weight.
  • the composition optionally comprises a silicone.
  • Builder materials may be selected from 1) calcium sequestrant materials, 2) precipitating materials, 3) calcium ion-exchange materials and 4) mixtures thereof.
  • calcium sequestrant builder materials examples include alkali metal polyphosphates, such as sodium tripolyphosphate and organic sequestrants, such as ethylene diamine tetra-acetic acid.
  • precipitating builder materials include sodium orthophosphate and sodium carbonate.
  • the laundry treatment composition comprises sodium carbonate in the range from 5 to 50 wt%, most preferably 10 to 35 wt%.
  • the aqueous wash solution when used with granular laundry treatment composition, preferably comprises 0.1 to 4 g/L of sodium carbonate.
  • Examples of calcium ion-exchange builder materials include the various types of water-insoluble crystalline or amorphous aluminosilicates, of which zeolites are the best known representatives, e.g. zeolite A, zeolite B (also known as zeolite P), zeolite C, zeolite X, zeolite Y and also the zeolite P-type as described in EP-A-0,384,070 .
  • zeolites are the best known representatives, e.g. zeolite A, zeolite B (also known as zeolite P), zeolite C, zeolite X, zeolite Y and also the zeolite P-type as described in EP-A-0,384,070 .
  • composition may also contain 0-65 % of a builder or complexing agent such as ethylenediaminetetraacetic acid, diethylenetriamine-pentaacetic acid, alkyl- or alkenylsuccinic acid, nitrilotriacetic acid or the other builders mentioned below.
  • a builder or complexing agent such as ethylenediaminetetraacetic acid, diethylenetriamine-pentaacetic acid, alkyl- or alkenylsuccinic acid, nitrilotriacetic acid or the other builders mentioned below.
  • Many builders are also bleach-stabilising agents by virtue of their ability to complex metal ions.
  • Zeolite and carbonate are preferred builders.
  • the composition may contain as builder a crystalline aluminosilicate, preferably an alkali metal aluminosilicate, more preferably a sodium aluminosilicate. This is typically present at a level of less than 15%w.
  • Aluminosilicates are materials having the general formula: 0.8-1.5 M 2 O. Al 2 O 3 . 0.8-6 SiO 2 where M is a monovalent cation, preferably sodium. These materials contain some bound water and are required to have a calcium ion exchange capacity of at least 50 mg CaO/g.
  • the preferred sodium aluminosilicates contain 1.5-3.5 SiO 2 units in the formula above. They can be prepared readily by reaction between sodium silicate and sodium aluminate, as amply described in the literature.
  • the ratio of surfactants to alumuminosilicate (where present) is preferably greater than 5:2, more preferably greater than 3:1.
  • phosphate builders may be used.
  • 'phosphate' embraces diphosphate, triphosphate, and phosphonate species.
  • Other forms of builder include silicates, such as soluble silicates, metasilicates, layered silicates (e.g. SKS-6 from Hoechst).
  • the laundry detergent formulation is a non-phosphate built laundry detergent formulation, i.e., contains less than 1 wt% of phosphate.
  • the composition may comprise one or more enzymes, which provide cleaning performance, fabric care and/or sanitation benefits.
  • the composition 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 the 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)-2H-napthol[1,2-d]triazole, disodium 4,4'-bis ⁇ [(4-anilino-6-(N methyl-N-2 hydroxyethyl) amino 1,3,5-triazin-2-yl)]amino ⁇ stilbene-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)biphenyl.
  • the composition comprises a perfume.
  • the perfume is preferably in the range from 0.001 to 3 wt %, most preferably 0.1 to 1 wt %.
  • CTFA Cosmetic, Toiletry and Fragrance Association
  • Many suitable examples of perfumes are provided in the CTFA (Cosmetic, Toiletry and Fragrance Association) 1992 International Buyers Guide, published by CFTA Publications and OPD 1993 Chemicals Buyers Directory 80th Annual Edition, published by Schnell Publishing Co .
  • compositions of the present invention it is envisaged that there will be four or more, preferably five or more, more preferably six or more or even seven or more different perfume components.
  • top notes are defined by Poucher (Journal of the Society of Cosmetic Chemists 6(2):80 [1955 ]).
  • Preferred top-notes are selected from citrus oils, linalool, linalyl acetate, lavender, dihydromyrcenol, rose oxide and cis-3-hexanol.
  • Perfume and top note may be used to cue the whiteness benefit of the invention.
  • the laundry treatment composition does not contain a peroxygen bleach, e.g., sodium percarbonate, sodium perborate, and peracid.
  • a peroxygen bleach e.g., sodium percarbonate, sodium perborate, and peracid.
  • the composition may comprise one or more polymers.
  • polymers are carboxymethylcellulose, poly (ethylene glycol), poly(vinyl alcohol), polycarboxylates such as polyacrylates, maleic/acrylic acid copolymers and lauryl methacrylate/acrylic acid copolymers.
  • Polymers present to prevent dye deposition for example poly(vinylpyrrolidone), poly(vinylpyridine-N-oxide), and poly(vinylimidazole), are preferably absent from the formulation.
  • the dyes listed below were added to a washing powder such that when 4g/L of the powder was dissolved in water the optical density at the lambda max of the dye in the range 400-700nm was 1 at 5cm. In this manner the same amount of colour was added to each powder.
  • the washing powder contained 20% LAS surfactant, 30% Na 2 CO 3 , 40% NaCl, remainder minors included calcite and fluorescer and moisture.
  • the washing powder was used to wash a 1:1:1 mixture of white woven cotton cloth, white polyester cloth and white nylon-elastane cloth. This simulates the mixed fabric types found in domestic wash loads. Washes were conducted in 26° French Hard water at 293K with a liquor to cloth ratio of 30:1.
  • the dyes of the current invention gave more colour to the cloth as indicated by their larger ⁇ E values.
  • the powder formulations A, B, C and D were made up with the three pyridine/pyridazine of example 3 at the level indicated.
  • the powder formulations A, B, C and D were made up with the three pyridine/pyridazine of example 3 at the level indicated.
  • NI(7EO) refers to R-(OCH 2 CH 2 ) n OH, where R is an alkyl chain of C12 to C15, and n is 7.
  • NaLAS linear alkyl benzene sulphonate (LAS) and (SLES(3EO)) is C 12 -C 18 alkyl polyethoxylate (3.0) sulphate.
  • Na Alkyl sulphate is PAS.
  • a three rinse conditioner formulation for use in the rinse stage of the wash was also created. It contained 13.7wt% N,N-di(tallowoyloxyethyl)-N,N-dimethylammonium chloride, 1.5wt% perfume, 0.001wt% of the three pyridine/pyridazine of example 3, remainder minors and water.

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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)
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  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Claims (11)

  1. Composition de traitement de la lessive comprenant :
    (i) de 2 à 70 % en poids d'un tensioactif, de 0,005 à 2 % en poids d'un agent fluorescent, et de 0,0001 à 0,1 % en poids d'un colorant cationique pyridine / pyridazine bleu ou violet de structure suivante :
    Figure imgb0019
     dans laquelle
    X est choisi parmi : N ; CH ; et C-N=N-phényl (B) - para-NR1R2 ;
    R1 et R2 sont choisis, indépendamment, parmi H, alkyle, aryle ; alkylaryle ; les alkylesters ; les polyéthers ; et R1 et R2 peuvent être rassemblés pour former un cycle aliphatique à cinq ou six chaînons qui peut comprendre un autre hétéroatome choisi parmi l'oxygène et l'azote ;
    R3 est choisi parmi : H ; alkyle ; alkylaryle ; et aryle ; et
    le cycle A peut être en outre condensé à un cycle benzène ; et Anθ est un contre-ion.
  2. Composition de détergente pour la lessive selon la revendication 1, dans laquelle le groupe azo est en position ortho par rapport à l'azote quaternaire.
  3. Composition détergente pour la lessive selon la revendication 1 ou 2, dans laquelle R1 et R2 sont choisis parmi : H ; les polyéthers, un groupe alkyle en C1-C8 pouvant être substitué par -OH, O-alkyle en C1-C8, -Cl et -F, -CN ; -alkyle en C1-C8-C (O)2-alkyle en C1-C8 ; -alkyle en C1-C8-OC(O)-alkyle en C1-C8 ; -alkyle en C1-C8-phényle ; -alkyle en C1-C8-naphtyle ; phényle ; et naphtyle, où le benzyle et le phényle peuvent être substitués par un groupe choisi parmi -O-alkyle en C1-C6, -alkyle en C1-C6.
  4. Composition détergente pour la lessive selon l'une quelconque des revendications précédentes, dans laquelle R3 est choisi parmi : H, alkyle en C1-C8, -alkyle en C1-C8-phényle ; -alkyle en C1-C8-naphtyle ; phényle ; et naphtyle.
  5. Composition détergente pour la lessive selon l'une quelconque des revendications précédentes, dans laquelle le cycle B comporte jusqu'à deux groupes qui sont choisis parmi : -Br ; -Cl ; -F ; -NO2 ; -CN ; -SO2-benzyle ; -C(O)O-alkyle en C1-C8 ; -O-alkyle en C1-C8 ; -NHC(O)-alkyle en C1-C4 ; -SO2-alkyle en C1-C8 ; et -SO2-phényle.
  6. Composition détergente pour la lessive selon la revendication 3, dans laquelle R1 et R2 sont choisis parmi : H ; -CH3 ; -C2H8; - (CH2)3H ; -(CH2)4H ; -C2H4OH ; -C2H4Cl; -C2H4CN ; -C6H5 ; -CH2C6H5 ; -C2H4OCOCH3 ; -C2H4OCOCH3 ; -C2H4COOCH3 ; et -C2H4OC2H4OH.
  7. Composition détergente pour la lessive selon la revendication 6, dans laquelle R1 et R2 sont choisis parmi : méthyle et éthyle.
  8. Composition détergente pour la lessive selon la revendication 4, dans laquelle R3 est choisi parmi méthyle, éthyle et benzyle.
  9. Composition détergente pour la lessive selon l'une quelconque des revendications précédentes, dans laquelle le fluorescent est choisi dans le groupe constitué par le 2(4-styryl-3-sulfophényl)-2H-naphtol[1,2-d]triazole de sodium, le 2-2'-disulfonate de 4,4'-bis{[(4-anilino-6-(N-méthyl-N-2-hydroxyéthyl)amino-1,3,5-triazin-2-yl)]amino}stilbène disodique, le 2-2'-disulfonate de 4,4'-bis{[(4-anilino-6-morpholino-1,3,5-triazin-2-yl)]amino}stilbène disodique, et le 4,4'-bis(2-sulfostyryl)biphényle disodique.
  10. Procédé domestique de traitement d'un textile, ledit procédé comprenant les étapes consistant à :
    (i) traiter un textile avec une solution aqueuse du colorant cationique pyridine / pyridazine tel que défini selon l'une quelconque des revendications 1 à 8, la solution aqueuse comprenant de 1 ppb à 1 ppm du colorant cationique pyridine / pyridazine, et de 0 ppb à 1 ppm d'un autre colorant ou pigment choisi parmi : les pigments, les colorants hydrophobes et les colorants directs ; et de 0, 0 g/litre à 3 g/litre d'un tensioactif ;
    (ii) éventuellement rincer le textile ; et
    (iii) sécher le textile.
  11. Procédé domestique de traitement d'un textile selon la revendication 10, dans lequel la solution aqueuse comprend 0,1 à 50 ppm d'un fluorescent.
EP09782877.6A 2008-09-23 2009-09-10 Colorants de pyridine et pyridazine cationiques Not-in-force EP2331669B1 (fr)

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EP08164876 2008-09-23
PCT/EP2009/061761 WO2010034623A1 (fr) 2008-09-23 2009-09-10 Colorants de pyridine et pyridazine cationiques
EP09782877.6A EP2331669B1 (fr) 2008-09-23 2009-09-10 Colorants de pyridine et pyridazine cationiques

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CN (1) CN102159698B (fr)
AR (1) AR073649A1 (fr)
CL (1) CL2011000620A1 (fr)
ES (1) ES2450393T3 (fr)
MY (1) MY153959A (fr)
WO (1) WO2010034623A1 (fr)
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EP3000848B1 (fr) * 2013-05-23 2017-10-25 Keio University Composé permettant de générer une seconde harmonique de lumière, composition colorante permettant de générer la seconde harmonique de lumière, et procédé d'examen de cellules
WO2016041679A1 (fr) * 2014-09-18 2016-03-24 Unilever Plc Composition de blanchiment
CN106661503B (zh) * 2014-09-18 2019-01-29 荷兰联合利华有限公司 增白组合物

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US5888252A (en) * 1993-11-30 1999-03-30 Ciba Specialty Chemicals Corporation Processes for dyeing keratin-containing fibres with cationicazo dyes
FR2778845B1 (fr) * 1998-05-25 2001-05-04 Oreal Composition de teinture pour fibres keratiniques avec un colorant direct cationique et un polymere substantif
FR2782450B1 (fr) * 1998-08-19 2004-08-27 Oreal Composition de teinture pour fibres keratiniques avec un colorant direct cationique et un agent tensio-actif anionique
FR2782451B1 (fr) * 1998-08-19 2004-04-09 Oreal Composition de teinture pour fibres keratiniques avec un colorant direct cationique et un sel d'ammonium quaternaire
US20070191246A1 (en) * 2006-01-23 2007-08-16 Sivik Mark R Laundry care compositions with thiazolium dye

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CL2011000620A1 (es) 2011-09-23
MY153959A (en) 2015-04-30
ZA201101402B (en) 2012-05-30
ES2450393T3 (es) 2014-03-24
WO2010034623A1 (fr) 2010-04-01
CN102159698A (zh) 2011-08-17
EP2331669A1 (fr) 2011-06-15
AR073649A1 (es) 2010-11-24
CN102159698B (zh) 2013-04-24

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