EP1713866A1 - Composition liquide aqueuse contenant des colorants reactifs - Google Patents

Composition liquide aqueuse contenant des colorants reactifs

Info

Publication number
EP1713866A1
EP1713866A1 EP05702199A EP05702199A EP1713866A1 EP 1713866 A1 EP1713866 A1 EP 1713866A1 EP 05702199 A EP05702199 A EP 05702199A EP 05702199 A EP05702199 A EP 05702199A EP 1713866 A1 EP1713866 A1 EP 1713866A1
Authority
EP
European Patent Office
Prior art keywords
reactive
solution
alkyl
group
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Withdrawn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
EP05702199A
Other languages
German (de)
English (en)
Inventor
Ludwig Hasemann
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.)
Clariant Finance BVI Ltd
Original Assignee
Clariant International Ltd
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 Clariant International Ltd filed Critical Clariant International Ltd
Priority to EP05702199A priority Critical patent/EP1713866A1/fr
Publication of EP1713866A1 publication Critical patent/EP1713866A1/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Withdrawn legal-status Critical Current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
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0072—Preparations with anionic dyes or reactive dyes
    • C09B67/0073—Preparations of acid or reactive dyes in liquid form
    • 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
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0083—Solutions of dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes

Definitions

  • Aqueous Liquid Composition Comprising Reactive Dyes
  • the present invention relates to an aqueous liquid composition comprising a reactive dye having high storage stability.
  • An aqueous liquid dye composition is now noticeable, because it makes no dust when handled and has no pollution problem on an operation environment, it requires no dissolving process to contribute to a labour- and energy-saving, and moreover it is suitable for the automatic weighing system.
  • an aqueous liquid dye composition with no problem from industrial point of view has been required eagerly to be developed.
  • a reactive dye-containing aqueous liquid composition can be prepared relatively easily, when the reactive dye has a high water solubility.
  • the reactive dye has a high water solubility.
  • the reactive dye-containing aqueous liquid composition prepared in such a manner is rather stable at ambient temperature. From industrial of view, however, it is usually left at a relatively low temperature such as 0 °C or lower, or a relatively high temperature such as 40 °C or higher through manufacture, custody, transportation including shipping, storage and the like.
  • a storage stability at a relatively low or high temperature is a serious problem from industrial point of view.
  • the reactive dye is, as known, subject to chemical change, i.e. hydrolysis. Therefore, storage for a long period of time at a relatively high temperature causes troubles such that dyeing or printing in any known manner only gives dyed or printed products of a color different from that expected.
  • Liquid compositions of reactive dyestuffs in particular, lose their reactivity to cellulose fibre by a hydrolysis of their reactive groups (spontaneous decomposition), so that troubles derived from reduction of the dye exaustion by fibre are frequently experienced. Consequently, on preparing liquid compositions of reactive dyestuffs, buffers to maintain a certain pH value and/or chelating agents to prevent influences of alkaline earth metal ions such as calcium ion and magnesium ion, may be added.
  • phosphates such as sodium phosphate, potassium phosphate are often used.
  • phosphates When phosphates are used for preparation of liquid compositions of reactive dyestuffs, they are not so much able to inhibit the decomposition of reactive groups of reactive dyestuffs, and after the liquid compositions thus obtained are stored for a long term, the phosphates tend to crystalize out. Moreover, use of phosphates is, in itself, unfavorable from point of view of environment pollution.
  • Usual additives to improve the solubility such as N-methyl pyrrolidone, ⁇ -caprolactam may promote the decomposition of the reactive group.
  • liquid formulations comprising reactive dyestuffs and an alkali metal polyacrylates or methacrylates with number average degree of polymerization not exceeding 1000 and 2-(2-Diethylaminoethoxy) ethanol do not cause to decompose the reactive groups of the reactive dyestuffs, and exhibit extremely high storage-stability to aging.
  • Desirable reactive dyestuffs to obtain the liquid compositions of the present invention are reactive dyestuffs having one or two triazinyl group(s) which carry one or two chlorine atom(s) or which carry one or two chlorine atom(s) respectively as a reactive group(s).
  • the present invention is not limited thereby and may be applied to any reactive-dyestuffs provided for the above-mentioned conditions.
  • Preferred dyestuffs according to the according to the invention bear at least one reactive group and are compounds of the formula formula (I)
  • Chromophore is the radical of a monoazo dye of the formula
  • C 2 -C 4 alkanoylamino, ureido, halogen, carboxyl and sulfo, or the Chromophore is the radical of a polyazo, metal complex azo, anthraquinone, formazan, phthalocyanine or dioxazine dye;
  • Y is chlorine or fluorine
  • X is -NR 1 R 2 wherein, Ri is H; C 1-6 alkyl; substituted C 1-6 alkyl or C ⁇ _ 6 alkyl, which is interrupted by one or more atoms from the group consisting of O, N and S; R 2 is H; C 1-6 alkyl; substituted C 1-6 alkyl; C 1-6 alkyl, which is interrupted by one or more atoms from the group consisting of O, N and S or phenyl which is substituted by one or more carboxy, sulfo, C M alkyl and/or Ci ⁇ alkoxy; or Ri and R 2 together with the nitrogen atom form a 5, 6 or 7 membered heterocyclic ring which optionally can contain more than one heteroatom from the group consisting of N, O and S and which may be additionally substituted by a C 1-2 alkyl-OH group;
  • the alkyl groups may be linear or branched. Preferred substituents for the alkyl groups are -OH, -COOH, -CN, halogen, -COOC 1-2 alkyl, -SO 3 H, -CONH 2 , -NH 2 , C 1-2 alkoxy and/or NO 2 .
  • Y is Chlorine;
  • X is -NRiR 2 wherein, Ri is H; unsubstituted C ⁇ - alkyl; C 1-4 -alkyl which is monosubstituted or disubstituted by -COOH, -CONH 2 , -SO 3 H or -OH;
  • R 2 is H; unsubstituted C 1-2 alkyl; C 1-4 -alkyl which is monosubstituted or disubstituted by -COOH, -CONH 2 , -SO 3 H or -OH or phenyl which is substituted by one or more carboxy, sulfo, and/or C 1-4 alkoxy; or Ri and R 2 together with the nitrogen atom form a 6 membered hetero-cyclic ring which optionally can contain more than one hetero-atom from the group consisting of N, O and S and which may be additionally substituted by a C 1-2 alkyl-OH group;
  • a ring wherein Ri and R 2 together with the nitrogen atom form a 6 membered hetero-cyclic ring in the substiuent of the formula -NRiR 2 which optionally can contain more than one hetero-atom is for example morpholino.
  • Preferred dyestuffs have one triazinyl group which carries one chlorine atom as a reactive group. More preferred dyestuffs are dystuffs according to the formula (I) or (II) or (III) or
  • the number average degree of polymerization of alkali metal polyacrylates or polymethacrylates used according to the present invention does not exceed 1000, preferably 100, and more preferably, is from 15 to 50.
  • the acrylic acid and/or methacrylic acid may be copolymerized with copolymerizable monomer such as maleic acid and succinic acid in such small quantities as not cancel the effect according to this invention.
  • the percentage of copolymerizable monomer other than acrylic acid and/or methacrylic acid is less than 50%, more preferred less than 20%, and most preferred less than 5% of the total amount of monomers.
  • alkali metal in alkali metal polyacrylates or polymethacrylates sodium, potassium or lithium is mentioned and sodium salts thereof are usually employed.
  • the preferred polyacrylate and/or polymetacrylate are those which are completely neutralized by prefference with alkali hydroxide, more preferred with sodium hydroxide.
  • a mixture of the alkali metal polyacrylates and the alkali metal polymethacrylates may be also used and a mixture of two or more of reactive dyestuffs may be also used.
  • 2-(2-Diethylaminoethoxy)ethanol is added to the dyestuff solution in order to improve the solubility.
  • the combination of the polyacrylate as mentioned above and the 2-(2-Diethylaminoethoxy)ethanol gives improved chemical and physical stability to the dyestuff composition.
  • liquid compositions comprise 0.1 to 5.0% by weight, preferably 0.5 to 3.0% by weight of the alkali metal polyacrylates and/or polymethacrylates, 5 to 60% by weight, preferably 10 to 40% by weight of a reactive dyestuff and 35 to 90% by weight of water.
  • composition comprises 0.1 to 5.0% by weight, preferably 0.5 to 3.0% by weight of the 2-(2-Diethylaminoethoxy)ethanol.
  • the liquid compositions of this invention maybe prepared by adding the alkali polyacrylates or polymethacrylates and the 2-(2-Diethylaminoethoxy)ethanol and water, and, if necessarily, also other additives to a reaction mixture containing reactive dyestuffs, or filter-cake obtained by filtration continued on salting-out.
  • reaction solutions containing reactive dyestuffs or reactive dyestuff filter-cakes obtained by salting-out may be used after desalting and concentrating reaction solutions by passing them through separation membranes such as cellulose acetate membrane or polybenzimidazolone membrane (PBIL).
  • separation membranes such as cellulose acetate membrane or polybenzimidazolone membrane (PBIL).
  • PBIL polybenzimidazolone membrane
  • the fiber-reactive dyestuff formulation according to the invention is useful for dyeing or printing or Inkjet printing hydroxy-group-containing or nitrogen-containing organic substrates.
  • Preferred substrates are leather and fibrous materials which comprise natural or synthetic polyamides and, particularly, natural or regenerated cellulose such as cotton, viscose and spun rayon or papery products.
  • the preferred substrates are textile materials comprising cotton. Further preferred substrates are paper or papery products or card-board.
  • Dyeing or printing may be carried out in accordance with known methods conventional in the fiber-reactive dyestuff field.
  • the exhaust-dyeing method is used at temperatures within the range of from 40 to 100°C, more preferably 50 to 80°C.
  • the padding method is used, for example pad-steam, pad-thermofix, pad-dry, pad-batch, pad-jig and pad-roll.
  • printing may be carried out using ink-jet printing methods.
  • fiber-reactive dyestuff formulation according to the invention may be used as or converted into a ink-jet printing ink.
  • the fiber-reactive dyestuff formulation according to the invention may be brought to the desired strength for example by dilution.
  • the ink composition and the printing pastes of the invention may further include as auxiliaries additional components which are normally used in inkjet inks or printing pastes, for example buffers, viscosity improvers, surface tension improvers, fixation accelerants, biozides, corrosion inhibitors, levelling agents, drying agents, humefactants, ink penetration additives, light stabilisers, UN absorbers, optical brighteners, coagulation reducers, ionic or nonionic surfactants and conducting salts.
  • auxiliaries additional components which are normally used in inkjet inks or printing pastes, for example buffers, viscosity improvers, surface tension improvers, fixation accelerants, biozides, corrosion inhibitors, levelling agents, drying agents, humefactants, ink penetration additives, light stabilisers, UN absorbers, optical brighteners, coagulation reducers, ionic or nonionic surfactants and conducting salts.
  • buffers for example buffers, viscosity improvers, surface tension improve
  • Example 1 930 g press cake consisting essentially of the rective dye of the formula (I)
  • solution A which may be diluted with auxiliaries and water in order to obtain the desired strength.
  • the sample showed precipitations after one week at 0-5°C.
  • comparative example 2 To 350 ml of the above mentioned solution (solution A) 2,29 g SOKOLAN 20 (trademark of BASF) (which is equivalent to 5,1 g solution of SOKOLAN 20; 0,5 weight-%), 2,29 g N-Methylpyrrolidone (0,5 weight-%) and 0.69 g PROXEL GXL (0,15 weight-%) were added. The adjustment of the pH value was not necessary. The obtained solution was set to the standard by adding demineralized water. The sample clearly showed precipitations after three weeks at 0-5°C.
  • solution B which may be diluted with auxiliaries and water in order to obtain the desired strength.
  • comparative example 6 To 265 ml of the above obtained dyestuff solution (solution B) were added 11,46 g SOKOLAN 25 CL GR (Trademark of BASF) ( 3,0 weight-%) and 0,57 g PROXEL GXL (0,15 weight-%). The solution is stirred. The adjustment of the pH value was not necessary. This solution may be brought to the desired strengh by adding water. The sample clearly showed precipitations after two weeks at 0-5°C.
  • comparative example 8 To 265 ml of the above obtained dyestuff solution (solution B) were added 11,46 g SOKOLAN 25 CL GR (Trademark of BASF) ( 3,0 weight-%) and 11,46 g Caprolactame (3% weight-%) and 0,57 g PROXEL GXL (0,15 weight-%). The solution is stirred. The adjustment of the pH value was not necessary. This solution maybe brought to the desired strengh by adding water.
  • solution C which may be diluted with auxiliaries and water in order to obtain the desired strength.
  • SOKOLAN 20 (Trademark of BASF) (which is equal to 11,58 g solution of SOKOLAN 20; 1,0 weight-%) and 0,78 g PROXEL GXL (0,15 weight-%).
  • the solution is stirred. The adjustment of the pH value was not necessary. This solution may be brought to the desired strengh by adding water. The sample clearly showed precipitations after two weeks at 0-5°C.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Coloring (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

Une composition liquide aqueuse comprenant un colorant réactif et des polyacrylates ou méthacrylates métalliques alcalins ayant un degré moyen de polymérisation ne dépassant pas 1 000 et 2-(2-diéthylaminoéthoxy)éthanol ayant une forte stabilité au stockage.
EP05702199A 2004-01-23 2005-01-06 Composition liquide aqueuse contenant des colorants reactifs Withdrawn EP1713866A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP05702199A EP1713866A1 (fr) 2004-01-23 2005-01-06 Composition liquide aqueuse contenant des colorants reactifs

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP04001502 2004-01-23
EP05702199A EP1713866A1 (fr) 2004-01-23 2005-01-06 Composition liquide aqueuse contenant des colorants reactifs
PCT/IB2005/000028 WO2005080509A1 (fr) 2004-01-23 2005-01-06 Composition liquide aqueuse comprenant des colorants

Publications (1)

Publication Number Publication Date
EP1713866A1 true EP1713866A1 (fr) 2006-10-25

Family

ID=34878153

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05702199A Withdrawn EP1713866A1 (fr) 2004-01-23 2005-01-06 Composition liquide aqueuse contenant des colorants reactifs

Country Status (4)

Country Link
EP (1) EP1713866A1 (fr)
CN (1) CN1910242A (fr)
BR (1) BRPI0507084A (fr)
WO (1) WO2005080509A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115594992B (zh) * 2022-10-25 2023-05-12 浙江迎丰科技股份有限公司 一种高稳定性液态活性染料的制备方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61204276A (ja) * 1985-03-07 1986-09-10 Nippon Kayaku Co Ltd 反応性染料の安定な液状組成物
JPH0658521B2 (ja) * 1986-06-24 1994-08-03 富士写真フイルム株式会社 カラ−現像液組成物
EP0369940B1 (fr) * 1988-11-15 1995-05-31 Ciba-Geigy Ag Solutions concentrées de colorants
DE4400322A1 (de) * 1994-01-07 1995-07-13 Bayer Ag Farbstoffpräparationen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2005080509A1 *

Also Published As

Publication number Publication date
CN1910242A (zh) 2007-02-07
WO2005080509A1 (fr) 2005-09-01
BRPI0507084A (pt) 2007-06-19

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