EP2334777B1 - Elastan-direktfarbstoffe - Google Patents

Elastan-direktfarbstoffe Download PDF

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Publication number
EP2334777B1
EP2334777B1 EP09812689.9A EP09812689A EP2334777B1 EP 2334777 B1 EP2334777 B1 EP 2334777B1 EP 09812689 A EP09812689 A EP 09812689A EP 2334777 B1 EP2334777 B1 EP 2334777B1
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Prior art keywords
alkyl
phenyl
naptholactam
substituted
dye
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French (fr)
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EP2334777A1 (de
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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.
  • Shading dyes may be used to enhance the whiteness of garments in the laundry process.
  • WO2005/003276 WO2006/010472 and WO2008/017570 all Unilever teaches the use of specific acid azo, anthraquinone, triphenylmethane and azine dyes for shading garments.
  • WO2006/004870 WO2007/084729 Proctor and Gamble
  • co-pending EP08150172 Unilever
  • Wash loads typically consist of a range of fabrics made from different fibers, particularly cotton, polyester, nylon and elastane. Elastane containing fabrics are prone to yellow much more than other fibers due to oxidation. It would thus be desirable to have a shading dye that build up slowly on elastane fabrics over multiple washes but not on cotton or polyester. This would provide optimal whiteness over the lifetime of all garments in the wash.
  • Blue or violet cationic naptholactam dyes build up slowly on elastane fabrics over multiple washes but not on cotton or polyester when applies in domestic washing.
  • the present invention provides a laundry treatment composition comprising:
  • the present invention provides a domestic method of treating a textile, the method comprising the steps of:
  • the naptholactam dyes as used in the present invention are blue or violet.
  • the naptholactam 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.
  • R is an uncharged group selected from: C1-C8-alkyl which may be substituted by -OH, -Cl, and -F, -CN; -CONHC1-C6-alkyl; - OCOC1-C6-alkyl; -CO2C1-C6-alkyl; -OC1-C6-alkyl; and -C(O)NH2 groups; benzyl; phenyl; wherein the benzyl and phenyl may be substituted by a group selected from: -OC1-C6-alkyl, -C1-C6-alkyl and, R1 may form together with ring A at position 1 a five or six membered ring linked by a C3-C4-alkyl chain; R2 is selected from: and, wherein R3 and R4 are selected from: H; polyethers, C1-C8-alkyl which may be substituted by -OH, -Cl, and -
  • -C1-C6-alkyl is found as a terminal group it is preferred that these groups are C1 or C2 alkyl, more preferably CH3 or C2H5.
  • -C1-C6-alkyl is found as a spacer group, for example -C1-C8-alkylC(O)N(R7)2, it is preferred that these groups are C1 or C2 alkyl, more preferably methylene or ethylene spacers.
  • R1 is selected from: Methyl and Ethyl.
  • R3 and R4 are selected from: C1-C6-alkyl, hydroxyl substituted C1-C6-alkyl; chloro substituted C1-C6-alkyl; flouro substituted C1-C6-alkyl; cyano substituted C1-C6-alkyl; phenyl substituted C1-C6-alkyl; phenyl; and optionally substituted phenyl.
  • R3 and R4 are selected from: CH 3 , C 2 H 5 ; CH 2 CH 2 OH; CH 2 CH 2 CN; CH 2 CH 2 Cl; CH 2 Ph; Ph; and p-MeOPh-.
  • R7 subsistent which is present at position 3 as indicated on the A ring or rings A and B are unsubstituted.
  • the naptholactam dyes and substituents thereof may be or carry a polyether chain.
  • a polyether chain is defined as at least two repeating units that are chemically bound via the ether's oxygen.
  • 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.
  • R3 and/or R4 is a polyether chain as defined above.
  • the naptholactam dyes may be further substituted by uncharged organic groups. If the naptholactam dyes is further substituted it is preferred that the uncharged organic groups should have a total molecular weight of less than 400, preferably less than 150.
  • X- is not essential aspect of the invention and may be varied widely.
  • X- 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.
  • X- is selected from: CH 3 SO 3 - , CH 3 CO 2 - , BF 4 - , Cl - , F - , Br - , and I - .
  • naptholactam dyes suitable for use in the present invention are given below:
  • 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 water-soluble 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 tetraacetic 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%.
  • 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:
  • 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.
  • cationic naptholactams are well documented in the literature: GB1520828 (Bayer), GB987828 (Bayer) and GB1371 178 (Bayer) GB973259 (Bayer), and GB1583160 (Ciba).
  • the exemplified cationic naptholactam dyes suitable for use as given above were synthesised following these literature procedures. All were found to give blue or violet in colour in aqueous solution and when deposited on cloth gave a blue or violet hue to the cloth.
  • the following dye was synthesised from literature procedures: 0.005wt% of the dye was added to a 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 variety of white fabric types.
  • Basic Blue 159 is an azo dye as described in W02006/004870 .
  • the naptholactam dye builds up more strongly on the elastane containing fabrics than the other dyes.

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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)
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Claims (11)

  1. Wäschebehandlungszusammensetzung,
    die folgendes aufweist:
    (i) 2 bis 70 Gew.-% eines Tensids und 0,0001 bis 0,1 Gew.-% eines kationischen blauen oder violetten Naphtholactam-Farbstoffs mit der folgenden Struktur:
    Figure imgb0031
    worin
    X- ein Gegenion ist;
    R1 eine gegebenenfalls substituierte Alkylgruppe ist, die an der Position 1 eine Alkylenbrücke bilden kann;
    R2 ein Rest mit zumindest einer Benzol-Einheit ist, die direkt an ein Stickstoffatom gebunden ist, wobei die Benzol-Einheit 1 bis 4 Bindungen vom Naphtholactam entfernt und zum Naphtholactam konjugiert ist, und die Ringe A und B gegebenenfalls substituiert sind.
  2. Wäschebehandlungszusammensetzung nach Anspruch 1,
    wobei: R1 ein ungeladener Rest ist, der ausgewählt ist aus: einer C1-C8-Alkyl-, die mit -OH, -Cl und -F, -CN substituiert sein kann, -CONHC1-C6-alkyl-, -OCOC1-C6-alkyl-, -CO2C1-C6-alkyl-, -OC1-C6-alkyl- und -C(O)NH2-Gruppe; Benzyl; Phenyl; wobei das Benzyl und Phenyl mit einem Rest substituiert sein können, der ausgewählt ist aus: -OC1-C6-alkyl, -C1-C6-Alkyl, und R1 zusammen mit dem Ring A an der Position 1 einen 5- oder 6gliedrigen Ring bilden kann, der über eine C3-C4-Alkylkette gebunden ist;
    R2 ausgewählt ist aus:
    Figure imgb0032
    Figure imgb0033
     worin R3 und R4 ausgewählt sind aus: H; Polyethern, einer C1-C8-Alkyl-, die mit -OH, -Cl und -F, -CN substituiert sein kann, -CONHC1-C6-alkyl-, -OCOC1-C6-alkyl-, -CO2C1-C6-alkyl-, -OC1-C6-alkyl- und -C(O)NH2-Gruppe;
    Benzyl; Phenyl; wobei das Benzyl und Phenyl mit einem Rest substituiert sein können, der ausgewählt ist aus: -OC1-C6-alkyl, -C1-C6-Alkyl; und R3 und R4 zusammen eine Morpholingruppe bilden.
    einem Rest der Formel
    Figure imgb0034
     worin R5 ausgewählt ist aus: H, CN, -C(O)OC1-C8-alkyl; -C1-C8-Alkyl, Phenyl, Naphthyl; Phenyl-C1-C8-alkyl(O)O-C1-C8-alkyl; Naphthyl-C1-C8-alkyl(O)O-C1-C8-alkyl; und, -C1-C8-AlkylC(O)N(R7)2, wobei R7 gleich oder verschieden sein kann und ausgewählt ist aus: C1-C8-Alkyl;
    Benzyl und Phenyl,
    D zusammen mit C-N für einen 5- oder 6gliedrigen stickstoffhaltigen Ring steht, der ferner mit einem Benzolring kondensiert sein kann und C1-C8-Alkyl- und -OC1-C6-alkylgruppen aufweisen kann;
    R6 aus den Resten ausgewählt ist, die unter R3 und R4 angegeben sind,
    die Ringe A und B bis zu zwei Reste R7 aufweisen können, die unabhängig voneinander ausgewählt sind aus: H; -Br; -Cl; -F; -NO2; -CN; -SO2-benzyl; -C(O)O-C1-C8-alkyl; -C(O) -C1-C8-alkyl; -NHC(O)C1-C4-alkyl, -SO2-C1-C8-alkyl; -SO2-phenyl; -SO2-phenyl, und einer der Ringe A oder B über eine -CH2- oder -NH-Einheit an eine andere Einheit aus einem Naphtholactam-Farbstoff gebunden sein kann;
    die Alkylringe und aromatischen Ringe, außer den wie angegebenen Ringen A und B des Naphtholactam-Farbstoffs, bis zu sechs Reste R8 aufweisen können, die ausgewählt sind aus: -C1-C6-Alkyl und -OC1-C6-alkyl, die gleich oder verschieden sind.
  3. Wäschebehandlungszusammensetzung nach Anspruch 2,
    wobei R3 und R4 ausgewählt sind aus: C1-C6-Alkyl, mit Hydroxyl substituiertem C1-C6-Alkyl; mit Chlor substituiertem C1-C6- Alkyl; mit Fluor substituiertem C1-C6-Alkyl; mit Cyano substituiertem C1-C6-Alkyl; mit Phenyl substituiertem C1-C6-Alkyl; Phenyl und gegebenenfalls substituiertem Phenyl.
  4. Wäschebehandlungszusammensetzung nach einem der vorstehenden Ansprüche, wobei R1 aus Me und Ethyl ausgewählt ist.
  5. Wäschebehandlungszusammensetzung nach einem der vorstehenden Ansprüche, wobei zumindest einer der Reste R3 und R4 ausgewählt ist aus: Me, C2H5; CH2CH2OH; CH2CH2CN; CH2CH2Cl; CH2Ph; Ph und p-MeOPh- .
  6. Wäschebehandlungszusammensetzung nach einem der vorstehenden Ansprüche, wobei es einen einzigen Substituenten R7 gibt, der an der Position 3 vorliegt, wie es am Ring A angegeben ist, oder die Ringe A und B unsubstituiert sind.
  7. Wäschebehandlungszusammensetzung nach Anspruch 1,
    wobei der Naphtholactam-Farbstoff ausgewählt ist aus:
    Figure imgb0035
    Figure imgb0036
    Figure imgb0037
    Figure imgb0038
    Figure imgb0039
    Figure imgb0040
    Figure imgb0041
    Figure imgb0042
  8. Wäschebehandlungszusammensetzung nach Anspruch 1,
    wobei der Naphtholactam-Farbstoff ausgewählt ist aus:
    Figure imgb0043
  9. Wäschebehandlungszusammensetzung nach einem der vorstehenden Ansprüche, wobei die Zusammensetzung einen Aufheller aufweist, der aus der Gruppe ausgewählt ist, bestehend aus: Natrium-2-(4-styryl-3-sulfophenyl)-2H-naphthol[1,2-d]triazol, Dinatrium-4,4'-bis{[(4-anilino-6-(N-methyl-N-2-hydroxyethyl)amino-1,3,5-triazin-2-yl)]amino}stilben-2-2'disulfonat, Dinatrium-4,4'-bis{[(4-anilino-6-morpholino-1,3,5-triazin-2-yl)]amino}stilben-2-2'disulfonat und Dinatrium-4,4'-bis(2-sulfostyryl)biphenyl
  10. Verfahren zum Behandeln eines Textilerzeugnisses, das Elastanfasern aufweist, im Haushalt,
    wobei das Verfahren die folgenden Schritte aufweist:
    (i) Behandeln eines Textilerzeugnisses mit einer wässrigen Lösung eines kationischen blauen oder violetten Naphtholactam-Farbstoffs nach einem der Ansprüche 1 bis 8, wobei die wässrige Lösung 1 ppb bis 1 ppm des kationischen blauen oder violetten Naphtholactam-Farbstoffs und 0 ppb bis 1 ppm eines anderen Farbstoffs oder Pigments, ausgewählt aus Pigmenten, hydrophoben Farbstoffen und Direktfarbstoffen, und bis zu 3 g/l eines Tensids aufweist;
    (ii) gegebenenfalls Spülen des Textilerzeugnisses und
    (iii) Trocknen des Textilerzeugnisses.
  11. Verfahren zum Behandeln eines Textilerzeugnisses im Haushalt nach Anspruch 10,
    wobei die wässrige Lösung 0,1 bis 50 ppm eines Aufhellers aufweist.
EP09812689.9A 2008-09-12 2009-07-17 Elastan-direktfarbstoffe Active EP2334777B1 (de)

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EP08164266 2008-09-12
PCT/EP2009/059230 WO2010028893A1 (en) 2008-09-12 2009-07-17 Elastane substantive dyes
EP09812689.9A EP2334777B1 (de) 2008-09-12 2009-07-17 Elastan-direktfarbstoffe

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EP2334777B1 true EP2334777B1 (de) 2013-05-01

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CN (1) CN102149804B (de)
AR (1) AR077158A1 (de)
CL (1) CL2011000517A1 (de)
ES (1) ES2422555T3 (de)
MY (1) MY153978A (de)
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CN103857781A (zh) * 2011-07-21 2014-06-11 荷兰联合利华有限公司 液体洗衣组合物
FR3067600B1 (fr) * 2017-06-16 2020-09-04 Oreal Procede de coloration des fibres keratiniques mettant en œuvre au moins un colorant direct fluorescent et au moins un colorant direct benzoindolinium bleu-violet-verts

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SU665817A3 (ru) * 1975-12-19 1979-05-30 Байер Аг, (Фирма) Способ крашени или печати текстильного материала из полиакрилонитрильных, полиамидных или полиэфирных волокон катионными красител ми
DE2624791A1 (de) * 1976-06-02 1977-12-15 Bayer Ag Kationische naphtholactamfarbstoffe
ZA200904947B (en) * 2007-01-26 2010-09-29 Unilever Plc Shading composition

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CL2011000517A1 (es) 2011-08-26
AR077158A1 (es) 2011-08-10
WO2010028893A1 (en) 2010-03-18
ES2422555T3 (es) 2013-09-12
ZA201101006B (en) 2012-05-30
CN102149804B (zh) 2013-01-23
EP2334777A1 (de) 2011-06-22
MY153978A (en) 2015-04-30

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