EP2331670B1 - Colorants cationiques à l'isothiazolium - Google Patents

Colorants cationiques à l'isothiazolium Download PDF

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Publication number
EP2331670B1
EP2331670B1 EP09780774.7A EP09780774A EP2331670B1 EP 2331670 B1 EP2331670 B1 EP 2331670B1 EP 09780774 A EP09780774 A EP 09780774A EP 2331670 B1 EP2331670 B1 EP 2331670B1
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Prior art keywords
alkyl
phenyl
composition according
detergent composition
laundry detergent
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EP09780774.7A
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German (de)
English (en)
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EP2331670A1 (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

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.
  • the present invention provides a laundry treatment composition comprising:
  • R 1 and R 2 are independently selected from H, alkyl, aryl; alkylaryl; -C1-C8-alkyl-phenyl alkylesters; polyethers; and R 1 and R 2 may be joined to form a five or six member aliphatic ring which may comprise a further hetroatom selected from oxygen and nitrogen; R 3 is selected from: H; alkyl; alkylaryl; and, aryl; and, the isothiazolium ring may be further condensed to a benzene ring, An ⁇ is a counter ion.
  • 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 isothiazolium dye, the aqueous solution comprising from 1 ppb to 1 ppm of the cationic isothiazolium 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 isothiazolium dyes as used in the present invention are blue or violet.
  • the cationic isothiazolium 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 - , BF4 - , 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.
  • 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 A may also 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 A 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 A 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.
  • 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
  • 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.
  • 5-Amino-3-methylisothiazole (Aldrich, 90%, 3.3g. 0.02M) was diazotised with nitrosyl sulphuric acid, in mixed acetic/propionic acids, and the resulting suspension of diazonium salt was added to dimethyl aniline in aqueous acetic acid. After stirring overnight at pH4 solid was collected and crystallised from n-propanol. Yield 4.1g., 78%; bronze leaflets m.p. 167-168°C.
  • Disperse dye (4.1g., 0.0166M) was added to methyl iodide (6ml., 13.68g., 0.096M) and the mixture heated under reflux for 48hr. Solid (0.4g.) was collected and the remaining reaction mixture heated under reflux for a further period of 48hr. After repeating this process several times 2.2g, (34%) of the desired product, mp 203 - 205°C, had been collected, and 2.5g., (60%) of starting disperse dye was recovered.
  • 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 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.
  • isothiazolium dye gives more colour to the cloth, as indicated by higher ⁇ E values. It also gives a true violet shade to the cloth with hue angles of 281.
  • the powder formulations A, B, C and D were made up with the isothiazolium dye of example 2 at the level indicated.
  • the powder formulations A, B, C and D were made up with the isothiazolium dye of example 2 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 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, 0.001 wt% of the isothiazolium dye of example 2, remainder minors and water.

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  • Chemical & Material Sciences (AREA)
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Claims (11)

  1. Composition de traitement du linge comprenant :
    (i) de 2 à 70 % en poids d'un tensioactif, et de 0,0001 à 0,1 % en poids d'un colorant cationique de type isothiazolium ayant la structure suivante :
    Figure imgb0015
     dans laquelle
    R1 et R2 sont indépendamment choisis parmi un atome d' H, un groupe alkyle, un groupe aryle; un groupe alkylaryle ; un groupe -C1-C8-alkyl-phényle; les alkylesters ; les polyéthers ; et R1 et R2 peuvent être liés pour former un noyau aliphatique à cinq ou six chaînons qui peut comprendre un autre hétéroatome choisi parmi l'oxygène et l'azote ;
    R3 est choisi parmi : un atome d'H ; un groupe alkyle ; un groupe alkylaryle ; et un groupe aryle ; et
    le noyau d'isothiazolium peut être en outre condensé à noyau de benzène ;
    Anθ représente un contre-ion.
  2. Composition détergente pour le linge selon la revendication 1, dans laquelle le groupe azo est en position ortho par rapport à l'azote quaternaire.
  3. Composition détergente pour le linge selon la revendication 1 ou 2, dans laquelle R1 et R2 sont choisis parmi : un atome d'H ; les polyéthers, un groupe C1-C8-alkyle qui peut être substitué par un groupe -OH, -O-C1-C8-alkyle, -Cl, et =F, -CN ; un groupe -C1-C8-alkyl-C(O)2-C1-C8-alkyle ; un groupe -C1-C8-alkyl-OC(O)-C1-C8-alkyle ; un groupe -C1-C8-alkyl-phényle ; un groupe -C1-C8-alkyl-naphtyle ; un groupe phényle ; et un groupe naphtyle, les groupes benzyle et phényle pouvant être substitués par un groupe choisi parmi : un groupe -OC1-C6-alkyle et un groupe -C1-C6-alkyle.
  4. Composition détergente pour le linge selon l'une quelconque des revendications précédentes, dans laquelle R3 est choisi parmi un atome d'H, un groupe C1-C8-alkyle, un groupe -C1-C8-alkyl-phényle ; un groupe-C1-C8-alkyl-naphtyle ; un groupe phényle ; et un groupe naphtyle.
  5. Composition détergente pour le linge selon l'une quelconque des revendications précédentes, dans laquelle le noyau A peut également porter deux groupes qui sont choisis parmi : -Br ; -Cl ; -F ; -NO2 ; -CN ; -SO2-benzyle ; -C(O)O-C1-C8-alkyle ; -OC1-C8-alkyle ; -NHC(O)C1-C4-alkyle, -SO2-C1-C8-alkyle ; et -SO2-phényle.
  6. Composition détergente pour le linge selon la revendication 3, dans laquelle R1 et R2 sont choisis parmi : -H ; -CH3 ; -C2H5 : -(CH2) 3H ; -(CH2) 4H ; -C2H4OH ; -C2H4Cl ; -C2H4CN ; -C6H5 ; -CH2C6H5 ; -C2H4OCOCH3 ; -C2H4COOCH3 ; et -C2H4OC2H4OH.
  7. Composition détergente pour le linge selon la revendication 6, dans laquelle R1 et R2 sont choisis parmi les groupes : méthyle et éthyle.
  8. Composition détergente pour le linge selon la revendication 4, dans laquelle R3 est choisi parmi les groupes méthyle, éthyle et benzyle.
  9. Composition détergente pour le linge selon l'une quelconque des revendications précédentes, dans laquelle la composition comprend un agent de fluorescence choisi dans le groupe constitué : du 2-(4-styryl-3-sulfophényl)-2H-napthol[1,2-d]triazole de sodium, du 4,4'-bis{[(4-anilino-6-(N-méthyl-N-2-hydroxyéthyl)amino-1,3,5-triazin-2-yl)]amino}stilbène-2-2'-disulfonate de disodium, du 4,4'-bis{[(4-anilino-6-morpholino-1,3,5-triazin-2-yl)]amino}stilbène-2-2'-disulfonate de disodium et du 4,4'-bis(2-sulfostyryl)biphényle de disodium.
  10. Procédé domestique de traitement d'un textile, le procédé comprenant les étapes de :
    (i) traitement d'un textile avec une solution aqueuse du colorant cationique de type isothiazolium selon l'une quelconque des revendications 1 à 8, la solution aqueuse comprenant de 1 ppb à 1 ppm de colorant cationique de type isothiazolium, 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/l à 3 g/l d'un tensioactif ; (ii) optionnellement rinçage du textile ;
    et (iii) séchage du textile.
  11. Procédé domestique de traitement d'un textile selon la revendication 10, dans lequel la solution aqueuse comprend dé 0,1 à 50 ppm d'agent de fluorescence.
EP09780774.7A 2008-09-26 2009-07-17 Colorants cationiques à l'isothiazolium Not-in-force EP2331670B1 (fr)

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EP09780774.7A EP2331670B1 (fr) 2008-09-26 2009-07-17 Colorants cationiques à l'isothiazolium

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP08165195 2008-09-26
EP09780774.7A EP2331670B1 (fr) 2008-09-26 2009-07-17 Colorants cationiques à l'isothiazolium
PCT/EP2009/059231 WO2010034534A1 (fr) 2008-09-26 2009-07-17 Colorants d’isothiazolium cationiques

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EP2331670A1 EP2331670A1 (fr) 2011-06-15
EP2331670B1 true EP2331670B1 (fr) 2013-04-17

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CN (1) CN102165054B (fr)
AR (1) AR073663A1 (fr)
BR (1) BRPI0919434A2 (fr)
CL (1) CL2011000650A1 (fr)
ES (1) ES2421898T3 (fr)
MY (1) MY156308A (fr)
WO (1) WO2010034534A1 (fr)
ZA (1) ZA201101125B (fr)

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CH660748A5 (de) * 1984-11-13 1987-06-15 Ciba Geigy Ag Kationische isothiazol-azo-verbindungen.
RU2463339C2 (ru) * 2006-01-23 2012-10-10 Милликен Энд Компани Композиция для стирки с тиазолиевым красителем

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WO2010034534A1 (fr) 2010-04-01
CN102165054B (zh) 2013-01-23
AR073663A1 (es) 2010-11-24
CL2011000650A1 (es) 2011-10-14
ZA201101125B (en) 2012-05-30
EP2331670A1 (fr) 2011-06-15
ES2421898T3 (es) 2013-09-06
MY156308A (en) 2016-01-29
BRPI0919434A2 (pt) 2015-12-15

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