WO2008141847A1 - Triphenyl methane and xanthene pigments - Google Patents

Triphenyl methane and xanthene pigments Download PDF

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Publication number
WO2008141847A1
WO2008141847A1 PCT/EP2008/052446 EP2008052446W WO2008141847A1 WO 2008141847 A1 WO2008141847 A1 WO 2008141847A1 EP 2008052446 W EP2008052446 W EP 2008052446W WO 2008141847 A1 WO2008141847 A1 WO 2008141847A1
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WO
WIPO (PCT)
Prior art keywords
pigment
hydrogen
alkyl
violet
blue
Prior art date
Application number
PCT/EP2008/052446
Other languages
English (en)
French (fr)
Inventor
Stephen Norman Batchelor
Jayne Michelle Bird
Original Assignee
Unilever Plc
Unilever N.V.
Hindustan Unilever Limited
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Unilever Plc, Unilever N.V., Hindustan Unilever Limited filed Critical Unilever Plc
Priority to BRPI0811888A priority Critical patent/BRPI0811888B1/pt
Priority to EP08717230A priority patent/EP2147090B1/de
Priority to AT08717230T priority patent/ATE492624T1/de
Priority to DE602008004135T priority patent/DE602008004135D1/de
Priority to CN200880016495XA priority patent/CN101679918B/zh
Publication of WO2008141847A1 publication Critical patent/WO2008141847A1/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/40Dyes ; 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.
  • 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:
  • A- is an inorganic heteropolyacid
  • Rl and R2 are independently selected from: hydrogen, C1-C6- alkyl and phenyl;
  • X is independently selected from the group consisting of: hydrogen, Cl-C6-alkyl and benzyl;
  • Ar is selected is hydrogen
  • Rl and R2 are as defined above;
  • R3 is hydrogen, Cl-C6-alkyl, or phenyl;
  • R 4 is hydrogen, Cl-C6-alkyl, or phenyl.
  • the Ri and R2 groups are independently selected from hydrogen, methyl and ethyl groups, preferably methyl and ethyl.
  • the Rl groups are same.
  • the Rl groups are the same and the R2 groups are the same.
  • X is selected from hydrogen and methyl, preferably hydrogen, - A -
  • the central oxygen shown with dashed bonds is optional; the triphenyl methane pigments are most preferred.
  • the Ar group is preferably
  • Y is selected from hydrogen, methyl and ethyl groups .
  • the Ar group is preferably selected from:
  • 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 Ce to C22 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 Cs to Cis 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 Cs to Cis alcohols, produced for example from tallow or coconut oil, sodium and potassium alkyl Cg to C20 benzene sulphonates, particularly sodium linear secondary alkyl Cio to Ci 5 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 Cu to Ci 5 alkyl benzene sulphonates and sodium C 12 to Cis 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 Ci6 to Cis primary alcohol sulphate together with a Ci2 to Ci5 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 C12 to C22 alkyl chain.
  • the quaternary ammonium compound has the following formula:
  • 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 C12 to C22 alkyl or alkenyl chain; R 3 and R 4 are independently selected from Ci 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 .
  • 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
  • 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
  • Pigment violet 14 is an inorganic pigment based on (Co) 3 (P0 4 ) 2
  • Example 1 Pigments were tested for shading benefit by washing cotton, polyester-cotton, polyester, nylon-elastane fabric together at room temperature, in 2. Og/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.
  • 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
  • WP woven polyester
  • WPC 65/35 woven polyester cotton

Landscapes

  • 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)
PCT/EP2008/052446 2007-05-18 2008-02-28 Triphenyl methane and xanthene pigments WO2008141847A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
BRPI0811888A BRPI0811888B1 (pt) 2007-05-18 2008-02-28 composição para lavagem de tecidos compreendendo pigmentos de trifenilmetano e xanteno, e método doméstico de tratamento de produto têxtil
EP08717230A EP2147090B1 (de) 2007-05-18 2008-02-28 Triphenylmethan- und xanthenpigmente
AT08717230T ATE492624T1 (de) 2007-05-18 2008-02-28 Triphenylmethan- und xanthenpigmente
DE602008004135T DE602008004135D1 (en) 2007-05-18 2008-02-28 Triphenylmethan- und xanthenpigmente
CN200880016495XA CN101679918B (zh) 2007-05-18 2008-02-28 三苯基甲烷和呫吨颜料

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP07108443 2007-05-18
EP07108443.8 2007-05-18

Publications (1)

Publication Number Publication Date
WO2008141847A1 true WO2008141847A1 (en) 2008-11-27

Family

ID=38512618

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2008/052446 WO2008141847A1 (en) 2007-05-18 2008-02-28 Triphenyl methane and xanthene pigments

Country Status (10)

Country Link
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)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
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

Citations (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
GB1313180A (en) * 1970-09-23 1973-04-11 Unilever Ltd Surface active liquids
GB1329086A (en) * 1969-08-29 1973-09-05 Unilever Ltd Bleaching composition
US4444592A (en) * 1981-06-02 1984-04-24 The Sherwin-Williams Company Pigment compositions and processes therefor
EP0184888A2 (de) * 1984-12-11 1986-06-18 Unilever N.V. Gefärbte Bleichmittelzusammensetzungen
EP0369500A2 (de) * 1988-10-18 1990-05-23 The Procter & Gamble Company Flüssiger, saurer Gewebeweichmacher mit Farbänderung bei Verdünnung
US5929004A (en) * 1997-10-10 1999-07-27 No Touch North America Detergent for cleaning tire wheels and cleaning method
WO2006041739A1 (en) * 2004-10-04 2006-04-20 The Procter & Gamble Company A composition with a metal-complexing dye and surfactant

Patent Citations (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
GB1329086A (en) * 1969-08-29 1973-09-05 Unilever Ltd Bleaching composition
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
EP0184888A2 (de) * 1984-12-11 1986-06-18 Unilever N.V. Gefärbte Bleichmittelzusammensetzungen
EP0369500A2 (de) * 1988-10-18 1990-05-23 The Procter & Gamble Company Flüssiger, saurer Gewebeweichmacher mit Farbänderung bei Verdünnung
US5929004A (en) * 1997-10-10 1999-07-27 No Touch North America Detergent for cleaning tire wheels and cleaning method
WO2006041739A1 (en) * 2004-10-04 2006-04-20 The Procter & Gamble Company A composition with a metal-complexing dye and surfactant

Also Published As

Publication number Publication date
CN101679918B (zh) 2012-03-28
CN101679918A (zh) 2010-03-24
EP2147090B1 (de) 2010-12-22
EP2147090A1 (de) 2010-01-27
MY147261A (en) 2012-11-30
CL2008001403A1 (es) 2009-01-16
DE602008004135D1 (en) 2011-02-03
AR066575A1 (es) 2009-08-26
BRPI0811888B1 (pt) 2017-02-14
ATE492624T1 (de) 2011-01-15
BRPI0811888A2 (pt) 2014-11-18
ES2358465T3 (es) 2011-05-10

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