EP2147090B1 - Triphenylmethan- und xanthenpigmente - Google Patents

Triphenylmethan- und xanthenpigmente Download PDF

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Publication number
EP2147090B1
EP2147090B1 EP08717230A EP08717230A EP2147090B1 EP 2147090 B1 EP2147090 B1 EP 2147090B1 EP 08717230 A EP08717230 A EP 08717230A EP 08717230 A EP08717230 A EP 08717230A EP 2147090 B1 EP2147090 B1 EP 2147090B1
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EP
European Patent Office
Prior art keywords
pigment
hydrogen
alkyl
violet
blue
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Not-in-force
Application number
EP08717230A
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English (en)
French (fr)
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EP2147090A1 (de
Inventor
Stephen Norman Batchelor
Jayne Michelle Bird
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 PLC
Unilever NV
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Unilever PLC
Unilever NV
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Publication date
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Priority to EP08717230A priority Critical patent/EP2147090B1/de
Publication of EP2147090A1 publication Critical patent/EP2147090A1/de
Application granted granted Critical
Publication of EP2147090B1 publication Critical patent/EP2147090B1/de
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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

Definitions

  • the present invention concerns the use of organic pigments in laundry compositions.
  • Colouring agents when substantive to a fabric, are normally specific to a particular fibre type, for example cotton or polyester.
  • WO 2006/032397 discloses the use of differing dye types in order to garments of differing fabrics and shade mixed garment fibres.
  • EP 0184888 discloses coloured bleaching compositions which may contain heteropolyacid salts of triphenyl methane chromophores.
  • the present invention provides laundry composition comprising between 0.00001 to 0.01 wt% of an organic pigment and 2 to 70 wt% of a surfactant, wherein the organic pigment is an inorganic heteropolyacid salt of a triphenyl methane or a xanthene moiety.
  • Organic pigments are described in 'Industrial Organic Pigments', Wiley VCH 2004 by W.Herbst and K.Hunger .
  • Dyes are organic chemicals that are soluble in their application medium.
  • Pigments are inorganic or organic particles that are insoluble in their application medium.
  • the present invention concerns pigments of the structure
  • the anion A - is an inorganic heteropolyacid.
  • the heteropolyacid is preferably selected from phosphomolybdic acid, phosphotungstic acid, phosphotungstomolybdic acid and silicomolybdic acid.
  • Preferred pigments are triphenyl methane, when O is absent, or a xanthene moiety, when O is present and bonded at dashed lines, of the following form: wherein A- is an inorganic heteropolyacid; R1 and R2 are independently selected from: hydrogen, C1-C6-alkyl and phenyl; X is independently selected from the group consisting of: hydrogen, C1-C6-alkyl and benzyl; Ar is selected from: wherein Y is hydrogen, C1-C6-alkyl or benzyl; wherein R1 and R2 are as defined above; R 1 is hydrogen, C1-C6-alkyl, or phenyl; R 4 is hydrogen, C1-C6-alkyl, or phenyl.
  • the R 1 and R 2 groups are independently selected from hydrogen, methyl and ethyl groups, preferably methyl and ethyl.
  • the R1 groups are same.
  • the R1 groups are the same and the R2 groups are the same.
  • X is selected from hydrogen and methyl, preferably hydrogen.
  • the central oxygen shown with dashed bonds is optional; the triphenyl methane pigments are most preferred.
  • the Ar group is preferably in which Y is selected from hydrogen, methyl and ethyl groups.
  • Ar group is preferably selected from: where the R 3 is selected from hydrogen, methyl or ethyl, preferably hydrogen and R 4 is selected from methyl, ethyl or phenyl.
  • R 3 is selected from hydrogen, methyl or ethyl, preferably hydrogen and R 4 is selected from methyl, ethyl or phenyl.
  • the amine substituted phenyl group is preferred rather than the naphthyl.
  • Preferred pigments are pigment violet 3, pigment violet 27, pigment violet 39, pigment violet 1, pigment violet 1:1, pigment violet 1:2, pigment blue 1, pigment blue 1:2, pigment blue 1:3 pigment blue 2, pigment blue 10, pigment blue 10:1, pigment blue 11, pigment blue 14 and pigment blue 62.
  • pigment violet 3 pigment violet 27, pigment violet 39 and pigment blue 14.
  • the laundry composition contains less than 0.00004 wt% of a blue or violet shading dye and is preferably devoid of such.
  • 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.
  • 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]trazole, 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-sulfoslyryl)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
  • OPD Chemicals Buyers Directory 80th Annual Edition, published by Schnell Publishing Co.
  • Phosphotungstomolybdic acid salt of Pigment violet 14 is an inorganic pigment based on (CO) 3 (PO 4 ) 2
  • Pigments were tested for shading benefit by washing cotton, polyester-cotton, polyester, nylon-elastane fabric together at room temperature, in 2.0g/L of a base washing powder which contained: 18% NaLAS, 73% salts (silicate, sodium tri-poly-phosphate, sulphate, carbonate), 3% minors including fluorescer and enzymes, remainder.impurities and water.
  • a liquor to cloth of with a 30:1 was used, the wash lasted for 30 mins, and were conducted with and without the addition of 500 part per billion of the pigment.
  • Pigments were added from a 0.005 wt% solution in ethanol. All pigments were used as received. Following the wash, the cloths were rinses then drying. The colour of the cloth was then assessed using a reflectometer (UV excluded for all measurements) and expressed as the ⁇ E value relative to cloth washed without pigment.
  • the pigments tested and ⁇ E values are given in the table below.

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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 (10)

  1. Waschmittel-Zusammensetzung, umfassend zwischen 0,00001 und 0,01 Gewichts-% eines organischen Pigments und 2 bis 70 Gewichts-% eines Tensids, wobei das organische Pigment ein anorganisches Heteropolysäuresalz einer Triphenylmethan- oder einer Xanthen-Gruppierung ist.
  2. Waschmittel-Zusammensetzung nach Anspruch 1, wobei die Triphenylmethan-Gruppierung, wenn O nicht vorhanden ist, oder eine Xanthen-Gruppierung, wenn O vorhanden ist und an den gestrichelten Linien gebunden ist, die folgende Formel hat:
    Figure imgb0017
     worin A- eine anorganische Heteropolysäure ist;
    R1 und R2 unabhängig ausgewählt sind aus: Wasserstoff, C1-C6-Alkyl und Phenyl;
    X unabhängig ausgewählt ist aus der Gruppe, bestehend aus: Wasserstoff, C1-C6-Alkyl und Benzyl;
    Ar ausgewählt ist:
    Figure imgb0018
     worin Y Wasserstoff,
    C1-C6-Alkyl und Benzyl ist;
    Figure imgb0019
     worin R1 und R2 wie oben definiert sind; R3 Wasserstoff, C1-C6-Alkyl oder Phenyl ist; R4 Wasserstoff, C1-C6-Alkyl oder Phenyl ist.
  3. Waschmittel-Zusammensetzung nach Anspruch 2, wobei R1 und R2 unabhängig ausgewählt sind aus: Wasserstoff, Methyl und Ethyl;
    X unabhängig ausgewählt ist aus der Gruppe, bestehend aus: Wasserstoff und Methyl;
    Ar, wenn das organische Pigment eine Xanthen-Gruppierung ist,
    Figure imgb0020
     ist, und Y aus Wasserstoff, Methyl- und Ethyl-Gruppe ausgewählt ist;
    Ar, wenn das organische Pigment eine Triphenylmethan-Gruppierung ist, aus der Gruppe, bestehend aus
    Figure imgb0021
     worin R1 und R2 wie oben definiert sind, ausgewählt ist;
    R3 aus: Wasserstoff, Methyl oder Ethyl, ausgewählt ist und
    R4 aus Methyl, Ethyl und Phenyl ausgewählt ist.
  4. Waschmittel-Zusammensetzung nach einem vorangehenden Anspruch, wobei die Substituenten R1 gleich sind und die Substituenten R2 gleich sind.
  5. Waschmittel-Zusammensetzung nach einem vorangehenden Anspruch, wobei das organische Pigment ein Triphenylmethan-Pigment ist.
  6. Waschmittel-Zusammensetzung nach Anspruch 1, wobei das organische Pigment ausgewählt ist aus der Gruppe, bestehend aus: Pigment Violet 3, Pigment Violet 27, Pigment Violet 39, Pigment Violet 1, Pigment Violet 1:1, Pigment Violet 1:2, Pigment Blue 1, Pigment Blue 1:2, Pigment Blue 1:3, Pigment Blue 2, Pigment Blue 10, Pigment Blue 10:1, Pigment Blue 11, Pigment Blue 14 und Pigment Blue 62.
  7. Waschmittel-Zusammensetzung nach Anspruch 6, wobei das organische Pigment aus der Gruppe, bestehend aus Pigment Violet 3, Pigment Violet 27, Pigment Violet 39 und Pigment Blue 14, ausgewählt ist.
  8. Waschmittel-Zusammensetzung nach einem vorangehenden Anspruch, wobei die anorganische Heteropolysäure aus der Gruppe, bestehend aus Phosphomolybdänsäure, Phosphowolframsäure, Phosphowolframatomolybdänsäure und Silicomolybdänsäure, ausgewählt ist.
  9. Verfahren zur häuslichen Behandlung einer Textilie, wobei das Verfahren die folgenden Schritte umfasst:
    (i) Behandeln einer Textilie mit einer wässrigen Lösung des Pigments, wie in einem der Ansprüche 1 bis 8 definiert, wobei die wässrige Lösung 1 ppb bis 1 ppm des Pigments und 0,2 g/l bis 3 g/l eines Tensids umfasst, und
    (ii) Spülen und Trocknen der Textilie.
  10. Verfahren nach Anspruch 9, wobei das Pigment mit 10 ppb bis 200 ppb vorliegt.
EP08717230A 2007-05-18 2008-02-28 Triphenylmethan- und xanthenpigmente Not-in-force EP2147090B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP08717230A EP2147090B1 (de) 2007-05-18 2008-02-28 Triphenylmethan- und xanthenpigmente

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP07108443 2007-05-18
PCT/EP2008/052446 WO2008141847A1 (en) 2007-05-18 2008-02-28 Triphenyl methane and xanthene pigments
EP08717230A EP2147090B1 (de) 2007-05-18 2008-02-28 Triphenylmethan- und xanthenpigmente

Publications (2)

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EP2147090A1 EP2147090A1 (de) 2010-01-27
EP2147090B1 true EP2147090B1 (de) 2010-12-22

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EP (1) EP2147090B1 (de)
CN (1) CN101679918B (de)
AR (1) AR066575A1 (de)
AT (1) ATE492624T1 (de)
BR (1) BRPI0811888B1 (de)
CL (1) CL2008001403A1 (de)
DE (1) DE602008004135D1 (de)
ES (1) ES2358465T3 (de)
MY (1) MY147261A (de)
WO (1) WO2008141847A1 (de)

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Publication number Priority date Publication date Assignee Title
CN103483861A (zh) * 2013-09-11 2014-01-01 吴江市冰心文教用品有限公司 一种蓝色耐光纺织纤维颜料

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3650831A (en) * 1969-03-10 1972-03-21 Armour Dial Inc Method of cleaning surfaces
NL134221C (de) * 1969-08-29 Unilever Nv
GB1313180A (en) * 1970-09-23 1973-04-11 Unilever Ltd Surface active liquids
US4444592A (en) * 1981-06-02 1984-04-24 The Sherwin-Williams Company Pigment compositions and processes therefor
GB8431256D0 (en) * 1984-12-11 1985-01-23 Unilever Plc Coloured bleaching compositions
US4863620A (en) * 1988-10-18 1989-09-05 The Procter & Gamble Company Acidic liquid fabric softener with yellow color that changes to blue upon dilution
US5929004A (en) * 1997-10-10 1999-07-27 No Touch North America Detergent for cleaning tire wheels and cleaning method
ES2324676T3 (es) * 2004-10-04 2009-08-12 The Procter And Gamble Company Composicion con un tinte formador de complejos con metales y un tensioactivo.

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BRPI0811888A2 (pt) 2014-11-18
DE602008004135D1 (en) 2011-02-03
WO2008141847A1 (en) 2008-11-27
EP2147090A1 (de) 2010-01-27
CN101679918B (zh) 2012-03-28
ES2358465T3 (es) 2011-05-10
CN101679918A (zh) 2010-03-24
MY147261A (en) 2012-11-30
BRPI0811888B1 (pt) 2017-02-14
CL2008001403A1 (es) 2009-01-16
ATE492624T1 (de) 2011-01-15
AR066575A1 (es) 2009-08-26

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