EP0889934A1 - Compositions stables de colorants - Google Patents

Compositions stables de colorants

Info

Publication number
EP0889934A1
EP0889934A1 EP97908205A EP97908205A EP0889934A1 EP 0889934 A1 EP0889934 A1 EP 0889934A1 EP 97908205 A EP97908205 A EP 97908205A EP 97908205 A EP97908205 A EP 97908205A EP 0889934 A1 EP0889934 A1 EP 0889934A1
Authority
EP
European Patent Office
Prior art keywords
colorant compositions
compositions according
substituted
pigments
weight
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.)
Withdrawn
Application number
EP97908205A
Other languages
German (de)
English (en)
Inventor
Matthias Wiesenfeldt
Johannes Peter Dix
Rudolf Paulus
Manfred Herrmann
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 SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Publication of EP0889934A1 publication Critical patent/EP0889934A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing 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
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing 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
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/32—Material containing basic nitrogen containing amide groups leather skins
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/32—Material containing basic nitrogen containing amide groups leather skins
    • D06P3/3206—Material containing basic nitrogen containing amide groups leather skins using acid dyes
    • D06P3/3226—Material containing basic nitrogen containing amide groups leather skins using acid dyes dis-polyazo
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/52—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
    • D06P1/5207—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • D06P1/525—Polymers of unsaturated carboxylic acids or functional derivatives thereof
    • D06P1/5257—(Meth)acrylic acid

Definitions

  • the present invention relates to stable aqueous colorant compositions containing at least one anionic dye and at least one pigment and a polyanionic thickener.
  • the invention furthermore relates to the use of these colorant compositions for dyeing leather and a process for dyeing leather using the colorant compositions.
  • Aqueous colorant compositions e.g. Colorant liquors for leather dyeing, which contain pigments and anionic dyes, have been known for a long time. These dye liquors are usually produced by mixing solid or liquid pigment and dye preparations with water immediately before the leather is dyed. Such aqueous colorant compositions are described, for example, in EP-B1-0 377 409 and EP-A2-0 344 555.
  • the disadvantage of this method is that an additional mixing process must take place before each coloring. This mixing process requires complex metering devices and harbors the risk of varying colorant compositions and thus poorly reproducible dyeing results.
  • finished aqueous mixtures of water, suspended pigments and anionic dyes were made.
  • the use of these colorant compositions is made more difficult by the fact that the aqueous pigment suspensions are not stable in storage.
  • the known colorant compositions show sedimentation during storage or tend to spontaneous crystallization, which leads to
  • the colorant compositions are known, the thixotropic additives by corresponding behavior (for example, N Trupocor ® Black liquid, manufacturer Trumpler). Such compositions are stable in storage, but are difficult to handle and lead, for example, to problems in automatic metering systems.
  • the object of the present invention was therefore to find aqueous colorant compositions which overcome these disadvantages, have good storage stability and enable unproblematic handling and metering.
  • the colorant compositions according to the invention preferably contain
  • the colorant compositions particularly preferably contain
  • Colorant compositions containing are very particularly preferred
  • the colorant composition generally contains water as the diluent, but other water-miscible solvents may also be present in the diluent.
  • solvents are alcohols such as methanol, ethanol, n-propanol or isopropanol or glycols such as ethylene glycol, diethylene glycol or propylene glycol.
  • the colorant compositions according to the invention preferably contain acid dyes of the general formula I as anionic dyes
  • R 1 , R 2 are hydroxy, amino or hydrogen, one of the radicals
  • R 3 , R 4 are hydrogen or SO 3 H, one of the radicals being SO 3 H,
  • R 5 is a substituted or unsubstituted phenyl - or
  • R 6 is a substituted phenyl or naphthyl radical, at least one substituent being an amino or hydroxyl group and one radical
  • aromatic rings can be substituted, for example by sulfo, C 1 -C 4 alkyl and / or C 1 -C 4 alkoxy groups.
  • R 1 and R 2 are preferably hydroxy or amino, R 1 amino and R 2 hydroxy are particularly preferred.
  • R 3 and R 4 are preferably SO 3 H radicals which are preferably in the o-position to the diazo group.
  • Suitable radicals R 5 are, for example, substituted naphthyl or phenyl radicals, preferably substituted phenyl radicals.
  • the aromatic ring systems can be single or multiple, for example 1- to
  • substituents are nitro, cyano, halogen such as chlorine or bromine, SO 3 H, hydroxy, ammo, C 1 -C 4 alkylanu.no or dialkylammo, N-morpholmo, anilino, toluidino or C 1 -C 4 alkyl Consider, with the nitro group being preferred.
  • a particularly preferred radical R 5 is p-nitrophenyl.
  • a substituent for the phenyl or naphthyl radicals R 5 is a radical of the formula
  • Suitable substituents for the substituted phenyl or naphthyl radicals R 6 are the radicals mentioned for the corresponding substituents of R 5 . In addition to amino and
  • Preferred bridge members A are
  • phenylene rings of the bridge members are preferably unsubstituted.
  • C 1 -C 4 alkyl or alkoxy substituents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec. Butyl and tert-butyl or the corresponding alkoxy radicals are generally suitable.
  • acid dyes of the formula II come as constituents of the colorant compositions according to the invention
  • B is a substituted phenylene or naphthylene radical, one substituent being a hydroxy group in the o-position to the diazo group and
  • R 7 is hydrogen or a radical which can be substituted, for example with hydroxy, amino,
  • phenylene or naphthylene radicals are suitable as radicals B.
  • the substituents can come from the group of the radicals mentioned as substituents on the phenyl or naphthyl radicals R 5 .
  • a further p-position hydroxyl group and the N-acetylamino group are preferred.
  • C 1 -C 4 alkyl substituents of the phenyldiazo and naphthyldiazo radicals R 7 are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl.
  • the C 1 -C 4 alkoxy substituents and the C 1 -C 4 alkylamino and di-C 1 -C 4 alkylamino substituents can contain the same alkyl radicals.
  • Preferred radicals R 7 are hydrogen,
  • Dyes of the formulas I and II are generally known, for example from JF Feeman in Venkataraman, "The Chemistry of Synthetic Dyes", Vol. VIII, p. 37 ff, Academic Press 1978, or can be prepared in a manner known per se.
  • the colorant compositions according to the invention preferably contain dyes and pigments of the same color, brown tones and black, in particular black, being preferred. Both inorganic and organic pigments are suitable as pigments which can be contained in the colorant compositions according to the invention.
  • Inorganic pigments that serve as colorants in the process according to the invention are preferably carbon blacks for black colorant compositions and preferably iron oxides for brown ones.
  • Organic pigments which serve as colorants in the process according to the invention are, for example, those from the class of the monoazo pigments (for example products which are derived from acetoacetic acid derivatives or from ⁇ -naphthol derivatives), lacquered monoazo dyes, such as lacquered ⁇ -oxynaphthoic acid dyes, disazo pigments, condensed disazo pigments , Isoindoline derivatives,
  • naphthalene or perylene tetracarboxylic acid Derivatives of naphthalene or perylene tetracarboxylic acid, anthraquinone pigments, thioindigo derivatives, azomethine derivatives, quinacridones, dioxazines, pyrazoloquinazolones, phthalocyanine pigments or lacquered basic dyes, such as lacquered triarylmethane dyes.
  • Examples include the inorganic pigments Pigment Yellow 42 (CI 77 492), Pigment White 6 (CI 77 891), Pigment Blue 27 (CI 77 510), Pigment Blue 29 (CI 77 007), or Pigment Black 7 (CI 77 266) as well as the organic pigments Pigment Yellow 1 (CI 11 680), Pigment Yellow 3 (CI 11 710), Pigment Yellow 16 (CI 20 040), Pigment Yellow 17 (CI 21 705, Pigment Yellow 42 (CI 77 492), Pigment Yellow 74 (CI 11 741), Pigment Yellow 83 (CI 21 108), Pigment Yellow 106, Pigment Yellow 108 (CI 68 240), Pigment Yellow 113, Pigment Yellow 117, Pigment Yellow 126, Pigment Yellow 139, Pigment Yellow 185, Pigment Orange 5 (CI 12 075), Pigment Orange 13 (CI 21 110),
  • Pigment Orange 34 (CI 21 115), Pigment Orange 36 (CI 11 780), Pigment Orange 43 (CI 71 105), Pigment Orange 67, Pigment Red 3 (CI 12 120), Pigment Red 48: 1 (CI 15 865: 1), Pigment Red 48: 4 (15 865: 4), Pigment Red 101 (CI 77 491), Pigment Red 112
  • the colorant compositions according to the invention contain a polyanionic thickener as a further essential component.
  • Polyanionic thickener is understood to mean a water-soluble polymer which carries negatively charged groups at neutral or alkaline pH and, in this charged state, causes thickening of aqueous solutions and suspensions.
  • Ionic derivatives of various polymers such as cellulose, e.g. Carboxymethyl cellulose or polymers or copolymers of acrylic acid and methacrylic acid. Polymers or copolymers with sulfonic acid or phosphonic acid groups can also serve as thickeners.
  • the properties of the colorant compositions can be influenced in a targeted manner by combining different thickeners.
  • Preferred thickeners are aqueous dispersions of copolymers of ethyl acrylate, acrylic acid and methacrylic acid, in particular in the form of their ammonium salts. These thickeners show their greatest thickening potential at pH values above pH 7.5. In the uncharged state, i.e. at pH values between 2 and 3, however, the preferred thickeners have a low viscosity of approximately 1 to 10 mPa-s (at 23 ° C.).
  • the colorant composition can also contain further additives. In addition to additives that are commonly used in colorant compositions, are special
  • Oxalkylated amines and oxyalkylated alcohols are suitable.
  • Oxalkylated amines which can be present in the colorant compositions according to the invention and which generally have at least 20 carbon atoms are to be understood as secondary or tertiary amines which have hydrocarbon radicals which are saturated or unsaturated, at least one of these radicals being interrupted by one or more oxygen atoms is.
  • the hydrocarbon radicals are straight-chain, branched or cyclic and optionally interrupted by one or more imino groups and / or substituted by one or more, for example 1 to 5, hydroxyl groups.
  • the preparation of these oxyalkylated amines and preferred structures are described in German patent application DE-A-3818183.
  • the oxyalkylated amines result in better color-through.
  • concentration of the oxalkylated amines in the colorant compositions depends on the later use.
  • the proportion is preferably chosen so that the amines are each present in an amount of 0.1 to 5% by weight, preferably 0.3 to 3% by weight, in particular 0.3 to 2% by weight on the wet weight of the leather to be dyed.
  • Oxalkylated alcohols which can be used in the process according to the invention are understood to mean those alcohols which have a hydrocarbon radical which is saturated or unsaturated and is interrupted by one or more oxygen atoms.
  • the hydrocarbon radical is straight-chain, branched or cyclic and optionally substituted by hydroxyl groups.
  • the colorant compositions according to the invention are particularly suitable for dyeing cotton, wool, polyamides and leather.
  • the use of the colorant composition for dyeing leather is particularly preferred.
  • the process for dyeing leather according to the invention is advantageously carried out by first pretreating the leather to be dyed, e.g. subject to retanning, neutralization and / or Walke.
  • the leather pretreated in this way is then removed by means of a pull-out method known per se, using a
  • the leather is dyed in an aqueous solution with a liquor ratio of 1: 1.5 to 1:20, preferably 1: 2 to 1:10 and a temperature of, for example, 20 to 100 ° C., preferably 40 to 60 ° C. depending on the type of leather to be dyed, for example 0.25 to 15% by weight, preferably 1.0 to 10% by weight, based on the weight of the leather, of the respective colorant composition.
  • the dyeing time also depends on the type of leather to be dyed, but is generally, for example, 20 to 180 minutes. If necessary, other generally customary additives, for example wetting agents, leveling agents, color deepening agents and / or degreasing agents, can be added to the dye bath before, during or after the dyeing.
  • the presence of the above-mentioned oxyalkylated amines and / or alcohols is particularly advantageous.
  • acidification can advantageously be carried out, for example with formic acid.
  • the dyeing process is then ended after a short exposure time.
  • the dyed leather is finished in a manner known per se.
  • the dyeing process according to the invention is for all types of leather, e.g. Grain and suede, chrome leather, retanned leather or suede from goat, sheep, beef and pork are suitable. Uniform deep, well-covering dyeings with good general fastness properties are obtained.
  • the colorant composition could be used in an automatic dosing system without any problems.
  • the other colorant preparations were prepared in an analogous manner:
  • the colorant compositions were stored at 20 ° C for 1 month. No sedimentation or serum separation was observed.
  • the colorant composition could be used in an automatic dosing system without any problems.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Compositions stables aqueuses de colorants, renfermant au moins un colorant anionique et au moins un pigment et un épaississant polyanionique. Ces compositions de colorants peuvent être utilisées pour la teinture du cuir.
EP97908205A 1996-03-26 1997-03-10 Compositions stables de colorants Withdrawn EP0889934A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19611870 1996-03-26
DE19611870 1996-03-26
PCT/EP1997/001204 WO1997035927A1 (fr) 1996-03-26 1997-03-10 Compositions stables de colorants

Publications (1)

Publication Number Publication Date
EP0889934A1 true EP0889934A1 (fr) 1999-01-13

Family

ID=7789432

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97908205A Withdrawn EP0889934A1 (fr) 1996-03-26 1997-03-10 Compositions stables de colorants

Country Status (5)

Country Link
US (1) US6080209A (fr)
EP (1) EP0889934A1 (fr)
KR (1) KR20000004920A (fr)
CN (1) CN1214715A (fr)
WO (1) WO1997035927A1 (fr)

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EP1047739B1 (fr) 1998-05-28 2009-11-04 Sun Chemical Corporation Dispersions de pigment aqueuses a base d'un colorant
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US6491750B1 (en) * 2000-03-30 2002-12-10 Behr Process Corporation Paint colorant product and method
KR20020061853A (ko) * 2001-01-18 2002-07-25 최낙완 직물지 후염처리 장치 및 방법
US6812278B2 (en) * 2001-02-28 2004-11-02 Rohm And Haas Company Method of improving viscosity stability upon addition of an aqueous tinting composition
BR0309630A (pt) * 2002-04-29 2005-03-08 Ciba Sc Holding Ag Composições e métodos para provisão de reologia aperfeiçoada a tintas para impressão e tintas para pintura à base de pigmento
CA2646126A1 (fr) * 2006-05-16 2007-11-22 Clariant Finance (Bvi) Limited Colorants acides
CN102250492A (zh) * 2011-03-11 2011-11-23 郭长虹 多功能染色剂及其配制方法以及本剂对织物染色补色方法
CN103421349B (zh) * 2013-09-04 2016-05-11 北京泛博化学股份有限公司 一种染料及其制备方法
CN103483857A (zh) * 2013-09-18 2014-01-01 吴江市冰心文教用品有限公司 一种颜料蓝27乳液的制备方法
CN106307760A (zh) * 2016-08-17 2017-01-11 安徽兴源塑料包装有限公司 一种塑料花卉
EP3395912B1 (fr) * 2017-04-28 2019-09-11 Stahl International B.V. Compositions de coloration de cuir soluble dans l'eau présentant une solidité à la lumière et une stabilité à la migration dans pvc
JP7283887B2 (ja) * 2018-01-16 2023-05-30 保土谷化学工業株式会社 キサンテン系カチオン染料とアニオン染料からなる造塩化合物を含有する着色組成物、カラーフィルター用着色剤およびカラーフィルター

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Also Published As

Publication number Publication date
CN1214715A (zh) 1999-04-21
US6080209A (en) 2000-06-27
WO1997035927A1 (fr) 1997-10-02
KR20000004920A (ko) 2000-01-25

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