WO2006122887A2 - 1-phenoxy-2-propanol as a formulating aid for dyes - Google Patents

1-phenoxy-2-propanol as a formulating aid for dyes Download PDF

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Publication number
WO2006122887A2
WO2006122887A2 PCT/EP2006/062107 EP2006062107W WO2006122887A2 WO 2006122887 A2 WO2006122887 A2 WO 2006122887A2 EP 2006062107 W EP2006062107 W EP 2006062107W WO 2006122887 A2 WO2006122887 A2 WO 2006122887A2
Authority
WO
WIPO (PCT)
Prior art keywords
dye
dyes
weight
phenoxy
propanol
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.)
Ceased
Application number
PCT/EP2006/062107
Other languages
English (en)
French (fr)
Other versions
WO2006122887A3 (en
Inventor
Holger Lautenbach
Adolf Käser
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.)
BASF Schweiz AG
Original Assignee
Ciba Spezialitaetenchemie Holding AG
Ciba SC Holding AG
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 Ciba Spezialitaetenchemie Holding AG, Ciba SC Holding AG filed Critical Ciba Spezialitaetenchemie Holding AG
Priority to JP2008511672A priority Critical patent/JP5245047B2/ja
Priority to CN200680017074XA priority patent/CN101175826B/zh
Priority to KR1020077029578A priority patent/KR101299076B1/ko
Priority to CA2607985A priority patent/CA2607985C/en
Priority to US11/919,102 priority patent/US7976586B2/en
Priority to BRPI0610814-8A priority patent/BRPI0610814A2/pt
Priority to MX2007014411A priority patent/MX2007014411A/es
Priority to AU2006248986A priority patent/AU2006248986B2/en
Priority to AT06755058T priority patent/ATE519821T1/de
Priority to EP06755058A priority patent/EP1888693B1/en
Publication of WO2006122887A2 publication Critical patent/WO2006122887A2/en
Publication of WO2006122887A3 publication Critical patent/WO2006122887A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • DTEXTILES; PAPER
    • D21PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21HPULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D21H21/28Colorants ; Pigments or opacifying agents
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0072Preparations with anionic dyes or reactive dyes
    • C09B67/0073Preparations of acid or reactive dyes in liquid form
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0075Preparations with cationic dyes
    • C09B67/0076Preparations of cationic or basic dyes in liquid form
    • DTEXTILES; PAPER
    • D21PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21HPULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H3/00Paper or cardboard prepared by adding substances to the pulp or to the formed web on the paper-making machine and by applying substances to finished paper or cardboard (on the paper-making machine), also when the intention is to impregnate at least a part of the paper body
    • D21H3/82Paper or cardboard prepared by adding substances to the pulp or to the formed web on the paper-making machine and by applying substances to finished paper or cardboard (on the paper-making machine), also when the intention is to impregnate at least a part of the paper body by adding insoluble coloured substances, e.g. powders, fibres, pieces of metal, for obtaining different colours in the paper fancy papers; substances characterised by their physical appearance, e.g. form, rather than by their chemical constitution

Definitions

  • the instant invention relates to storage stable, concentrated aqueous solutions of direct dyes, both anionic dyes and cationic or basic dyes, a process for their preparation and the use thereof for dyeing paper.
  • benzyl alcohol would appear to be the additive of choice for the preparation of storage stable aqueous formulations of anionic dyes, one clear disadvantage is the undesirable odor of benzyl alcohol, even if utilized in relatively small quantities.
  • the invention relates to an aqueous dye solution comprising a) 5 to 30%, preferably 10 to 25%, by weight of an anionic or cationic direct dye, b) 0.1 to 10%, preferably 0.5 to 5% and, most preferably, 0.5 to 3% by weight of 1- phenoxy-2-propanol, c) 0 to 20% by weight of an inorganic or an organic acid, d) 0 to 20% by weight of further additives and e) water to complete to 100%.
  • these direct dyes are preferably selected from dyes containing at least one sulfonic acid and/or carboxylic acid group and are derived from the following dye classes: metal-free or metallic monoazo, disazo and polyazo dyes, pyrazolone, thioxanthone, oxazine, stilbene, formazan, anthraquinone, nitro, methine, triphenylmethane, xanthone, naphthazarine, styryl, azastyryl, naphthoperinone, quinophthalone, and phthalocyanine dyes.
  • anionic direct dyes are listed in the Colour Index International, Fourth Edition Online (url: http:/www.colour-index.org) and may be selected from C.I. Direct Yellows 1-177, C.I. Direct Oranges 1-122, C.I. Direct Reds 1-277, C.I. Direct Violets 1-108 and C.I. Direct Blues 1-313.
  • these cationic direct dyes are basic dyes.
  • these so-called basic dyes are selected from the following classes: acridine, anthraquinone, azine, azomethine, azostyryl, mono-, bis- and polyazo, benzimidazole, benzothiazole, cyanine, di- and triaryl methane, ketone imine, methane and polymethine, naphthostyryl, nitro, oxazine and dioxazine, phthalocyanine, quinoline, quinophthalone, thiazine, thiazole and xanthene derivatives.
  • Typical examples of cationic direct dyes are listed in the Colour Index International, Fourth Edition Online (url: http:/www.colour-index.org) and may be selected from C.I. Basic Yellows 1-108, C.I. Basic Oranges 1-69, C.I. Basic Reds 1-118, C.I. Basic Violets 1-51 and C.I. Basic Blues 1-164.
  • the invention is especially useful for solutions of specific dyes, such as C.I. Basic Yellow 99 and 106, C.I. Basic Red 111, C.I. Basic Blue 100 and 153, C.I. Direct Yellow 11 , 50 and 84, C.I. Direct Orange 29 and 102, C.I. Direct Red 23, 80, 81, 239, 254 and 262, C.I. Direct Violet 9, 35 and 51 and C.I. Direct Blue 75, 86, 87, 199, 290 and 301.
  • composition of the invention contains an organic or inorganic acid
  • those acids particularly suited may be selected from, for example, hydrochloric acid, sulphuric acid, phosphoric acid, formic acid, acetic acid, propionic acid, glycol ic acid, gluconic acid, methanesulphonic acid, citric acid, succinic acid, lactic acid, glutamic acid, adipic acid or mandelic acid. Any of these acids may be used alone or in an acid mixture, although formic acid is most preferred.
  • an acid to the composition of the invention is optional, preferably the acid is present in an amount of between 1 and 20% by weight, most preferably between 1 and 5%, based on the total weight of the composition.
  • the dye solutions according to the invention may, in addition, contain further additives as component d), such as water-soluble organic solubilizers, examples of which are urea, formamide, ⁇ -caprolactam, sugars, such as dextrine, maltose or lactose, carboxycelluloses, such as xanthan, dimethylformamide, 1,2-diaminopropane, 2-(4-aminophenyl)-6- methylbenzothiazole 7-sulphonic acid and salts thereof and polyhydric alcohols such as ethylene glycol or glycerol, ⁇ -caprolactam and 2-(4-aminophenyl)-6-methylbenzothiazole 7- sulphonic acid and salts thereof being preferred.
  • Further additives which may be present in the solutions of the invention are, for example, hydrotropic agents, viscosity regulators, dispersing agents, microbicides, particularly fungicides, and pH adjusting agents.
  • acids, bases or buffers which are conventional and are usually used for the pH adjustment of dye formulations, for example mineral acids, such as hydrochloric acid, sulphuric acid or phosphoric acid, low molecular weight aliphatic carboxylic acids, for example having from 1 to 6 carbon atoms, such as formic acid, acetic acid, lactic acid or citric acid, or bases, such as alkali metal hydroxides or carbonates, or also aliphatic low molecular weight amines, such as those which can be used for the corresponding salt formation of the above mentioned acid groups, for example, ammonia, diethanolamine, triethanolamine or N-methyldiethanolamine.
  • buffers it is possible to employ, for example, mono- or disodium phosphate, sodium acetate or ammonium sulphate.
  • the pH of the concentrated dye solutions can thus be adjusted as required, depending upon the particular dye in question.
  • the pH of the solutions generally lies within the range of from 3 to 11, whereby, in the case of cationic dyes, a range of from 4 to 6 is preferred, whilst, in the case of anionic dyes, a pH value of between 6 and 8 is preferable.
  • the aqueous solutions also contain known products as are usually employed for protection against the harmful effect of microorganisms, principally products which inhibit the growth of microorganisms or also microbicides, particularly fungicides. These may be employed in low concentrations, for example, in the range of from 0.01 to 1%, especially from 0.05 to 0.5%.
  • additives to the composition of the invention is optional, preferably they are present in an amount of between 1 and 20% by weight, most preferably between 1 and 10%, based on the total weight of the composition.
  • the solutions of the invention are preferably, essentially free from other solvents, in particular alcohols, other than 1-phenoxy-2-propanol.
  • the invention relates to a process for the preparation of a dye solution, which process comprises stirring the dye with a mixture of water, 1-phenoxy-2-propanol and, if desired, components c) and d), as described above, at a temperature between room temperature and 9O 0 C, preferably between 30 and 6O 0 C and, if necessary, filtering.
  • the dyes can be employed in the form of corresponding dry dyes, as occur in blended commercial forms, or, preferably, as moist or also dried filter cakes or also as solutions which have previously been subjected to purification by micro- or ultra filtration.
  • the anionic dyes are present in the form of readily water-soluble salts.
  • suitable salts are alkali metal salts such as lithium potassium or, especially, sodium salts or ammonium salts, mono-, di-, tri- or tetraCrC 4 alkyl ammonium salts or C 2 - C 4 hydroxyalkyl ammonium salts or mixtures thereof.
  • the counter ion should be such as to ensure sufficient water solubility.
  • Preferred salts in this case are, for example, halogenides, especially chlorides, sulphates, methosulphates and, in particular lower aliphatic carboxylates such as formates, acetates and lactates.
  • the formulation of the invention is suitable for dyeing natural or synthetic materials, in particular cellulosic materials in any desirable shade.
  • the formulations are suitable for dyeing paper and paperboard.
  • the invention relates to the use of the solutions for the dyeing of paper, by treating the paper with a liquid composition as defined previously.
  • the liquid preparation is used, optionally after dilution with water, for the dyeing of paper or paperboard, whereby these materials can be dyed, for example, in the pulp, by brushing or immersion or by applying to the paper surface by coating or spraying or for application in a continuous dyeing process, whereby the paper or paperboard which has been dyed with the liquid composition of the invention constitutes a still further aspect of the invention.
  • Stable formulations are also obtained from salt-containing filter cakes of the dye, whereby the viscosity of the solutions increases slightly.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Paper (AREA)
  • Coloring (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/EP2006/062107 2005-05-18 2006-05-08 1-phenoxy-2-propanol as a formulating aid for dyes Ceased WO2006122887A2 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
JP2008511672A JP5245047B2 (ja) 2005-05-18 2006-05-08 染料用配合促進剤としての1−フェノキシ−2−プロパノール
CN200680017074XA CN101175826B (zh) 2005-05-18 2006-05-08 作为染料配方助剂的1-苯氧基-2-丙醇
KR1020077029578A KR101299076B1 (ko) 2005-05-18 2006-05-08 염료용 제형 조제로서의 1-페녹시-2-프로판올
CA2607985A CA2607985C (en) 2005-05-18 2006-05-08 1-phenoxy-2-propanol as a formulating aid for dyes
US11/919,102 US7976586B2 (en) 2005-05-18 2006-05-08 1-phenoxy-2-propanol as a formulating aid for dyes
BRPI0610814-8A BRPI0610814A2 (pt) 2005-05-18 2006-05-08 1-fenóxi-2-propanol como um auxiliar de formulação para corantes
MX2007014411A MX2007014411A (es) 2005-05-18 2006-05-08 1-fenoxi-2-propanol como un adyuvante de formulacion para tintes.
AU2006248986A AU2006248986B2 (en) 2005-05-18 2006-05-08 1-phenoxy-2-propanol as a formulating aid for dyes
AT06755058T ATE519821T1 (de) 2005-05-18 2006-05-08 Papierfärben mittels einer wässrigen farbstofflösung
EP06755058A EP1888693B1 (en) 2005-05-18 2006-05-08 Dyeing of paper with an aqueous dye solution

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP05104146.5 2005-05-18
EP05104146 2005-05-18

Publications (2)

Publication Number Publication Date
WO2006122887A2 true WO2006122887A2 (en) 2006-11-23
WO2006122887A3 WO2006122887A3 (en) 2007-01-18

Family

ID=37072950

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2006/062107 Ceased WO2006122887A2 (en) 2005-05-18 2006-05-08 1-phenoxy-2-propanol as a formulating aid for dyes

Country Status (15)

Country Link
US (1) US7976586B2 (enExample)
EP (1) EP1888693B1 (enExample)
JP (1) JP5245047B2 (enExample)
KR (1) KR101299076B1 (enExample)
CN (1) CN101175826B (enExample)
AT (1) ATE519821T1 (enExample)
AU (1) AU2006248986B2 (enExample)
BR (1) BRPI0610814A2 (enExample)
CA (1) CA2607985C (enExample)
ES (1) ES2368858T3 (enExample)
MX (1) MX2007014411A (enExample)
MY (1) MY150678A (enExample)
TW (1) TWI417348B (enExample)
WO (1) WO2006122887A2 (enExample)
ZA (1) ZA200709173B (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013048736A1 (en) 2011-09-29 2013-04-04 Dow Global Technologies Llc Formulations having benzoate dye carriers for meta-aramid articles

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BRPI0610829A2 (pt) * 2005-05-18 2010-07-27 Ciba Sc Holding Ag soluções aquosas de corantes diretos
JP2012233033A (ja) * 2011-04-28 2012-11-29 Sumitomo Chemical Co Ltd 染料用塩
CN103015231B (zh) * 2013-01-22 2015-11-25 武汉纺织大学 一种利用有机溶剂与水互溶的染液对纺织品染色的方法
CN113389070B (zh) * 2021-06-30 2023-04-21 嘉兴市富达化学纤维厂 用于再生尼龙染色的匀染剂及其制备方法和应用
CA3262589A1 (en) * 2022-07-28 2024-02-01 Dow Global Technologies Llc LOW VOC IONIC SOLVENTS USED AS DYE CARTONES FOR ARAMID FIBERS

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH503091A (de) 1969-11-05 1971-02-15 Ciba Geigy Ag Konzentrierte saure Lösung von kationischen Cyclammoniumgruppen aufweisenden Farbstoffen der Benzo-1,2-Pyranreihe
JPH04122933A (ja) 1990-09-14 1992-04-23 Konica Corp 水なし平版印刷版用染色液
JP2000229820A (ja) 1999-02-08 2000-08-22 Hoyu Co Ltd 酸性染毛料組成物
EP1235881B1 (en) 1999-11-24 2004-02-18 Clariant Finance (BVI) Limited Dye compositions, their production and their use

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EP0369940B1 (de) 1988-11-15 1995-05-31 Ciba-Geigy Ag Konzentrierte Farbstofflösungen
ES2087273T3 (es) 1990-04-03 1996-07-16 Ciba Geigy Ag Soluciones concentradas de colorante.
DE4030915A1 (de) 1990-09-29 1992-04-02 Basf Ag Konzentrierte waessrige loesungen von 2-phenylbenzthiazolazofarbstoffen
DE4202527A1 (de) 1992-01-30 1993-08-05 Bayer Ag Farbstoffmischungen
DE4240981A1 (de) 1992-12-05 1994-06-09 Basf Ag Verdoppelte Azofarbstoffe
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ES2185549T3 (es) 1999-09-27 2003-05-01 Ciba Sc Holding Ag Tintas de color rojo carmesi (magenta) que contienen colorantes azoicos de complejo de cobre basados en acidos 1-naftol-di- o -trisulfonicos.
AU2001239217A1 (en) 2000-03-17 2001-09-24 Novozymes A/S Method for dyeing dry hair
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FR2817468B1 (fr) 2000-12-04 2005-05-06 Oreal Composition destinee a la teinture d'oxydation des fibres keratiniques comprenant de la gylcerine et un polyol different de la glycerine dans un rapport donne
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH503091A (de) 1969-11-05 1971-02-15 Ciba Geigy Ag Konzentrierte saure Lösung von kationischen Cyclammoniumgruppen aufweisenden Farbstoffen der Benzo-1,2-Pyranreihe
JPH04122933A (ja) 1990-09-14 1992-04-23 Konica Corp 水なし平版印刷版用染色液
JP2000229820A (ja) 1999-02-08 2000-08-22 Hoyu Co Ltd 酸性染毛料組成物
EP1235881B1 (en) 1999-11-24 2004-02-18 Clariant Finance (BVI) Limited Dye compositions, their production and their use

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013048736A1 (en) 2011-09-29 2013-04-04 Dow Global Technologies Llc Formulations having benzoate dye carriers for meta-aramid articles
US10106926B2 (en) 2011-09-29 2018-10-23 Dow Global Technologies Llc Formulations having benzoate dye carriers for meta-aramid articles

Also Published As

Publication number Publication date
TWI417348B (zh) 2013-12-01
KR20080026110A (ko) 2008-03-24
KR101299076B1 (ko) 2013-08-27
MX2007014411A (es) 2008-02-11
CN101175826B (zh) 2013-03-27
MY150678A (en) 2014-02-28
US20080307588A1 (en) 2008-12-18
AU2006248986B2 (en) 2011-08-11
CA2607985C (en) 2013-11-05
EP1888693A2 (en) 2008-02-20
CA2607985A1 (en) 2006-11-23
TW200704723A (en) 2007-02-01
JP2008545817A (ja) 2008-12-18
ATE519821T1 (de) 2011-08-15
ZA200709173B (en) 2009-12-30
WO2006122887A3 (en) 2007-01-18
ES2368858T3 (es) 2011-11-23
US7976586B2 (en) 2011-07-12
AU2006248986A1 (en) 2006-11-23
JP5245047B2 (ja) 2013-07-24
CN101175826A (zh) 2008-05-07
BRPI0610814A2 (pt) 2010-07-27
EP1888693B1 (en) 2011-08-10

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