EP1756232A1 - Solution de colorant concentree - Google Patents

Solution de colorant concentree

Info

Publication number
EP1756232A1
EP1756232A1 EP05739802A EP05739802A EP1756232A1 EP 1756232 A1 EP1756232 A1 EP 1756232A1 EP 05739802 A EP05739802 A EP 05739802A EP 05739802 A EP05739802 A EP 05739802A EP 1756232 A1 EP1756232 A1 EP 1756232A1
Authority
EP
European Patent Office
Prior art keywords
dye
independently
formula
water
parts
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Withdrawn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
EP05739802A
Other languages
German (de)
English (en)
Inventor
Martin Oberholzer
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 EP05739802A priority Critical patent/EP1756232A1/fr
Publication of EP1756232A1 publication Critical patent/EP1756232A1/fr
Withdrawn legal-status Critical Current

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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
    • C09B67/0075—Preparations with cationic dyes
    • C09B67/0076—Preparations of cationic or basic 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
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/50—Tetrazo dyes
    • C09B35/60—Tetrazo dyes of the type
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
    • C09B29/0007—Monoazo dyes prepared by diazotising and coupling from diazotized anilines containing acid groups, e.g. CO2H, SO3H, PO3H2, OSO3H, OPO2H2; Salts thereof
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3665—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic ring with two nitrogen atoms
    • C09B29/3669—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic ring with two nitrogen atoms from a pyrimidine ring
    • C09B29/3673—Barbituric acid and derivatives thereof
    • 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
    • C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
    • C09B33/02—Disazo dyes
    • C09B33/12—Disazo dyes in which the coupling component is a heterocyclic compound
    • 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
    • C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
    • C09B33/18—Trisazo or higher polyazo dyes
    • C09B33/24—Trisazo dyes of the type
    • 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
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/50—Tetrazo dyes
    • 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
    • C09B44/00—Azo dyes containing onium groups
    • C09B44/02—Azo dyes containing onium groups containing ammonium groups not directly attached to an azo group
    • C09B44/08—Azo dyes containing onium groups containing ammonium groups not directly attached to an azo group from coupling components containing heterocyclic rings
    • 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
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/24—Disazo or polyazo compounds
    • 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
    • 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
    • D06P3/58—Material containing hydroxyl groups
    • D06P3/60—Natural or regenerated cellulose

Definitions

  • the present invention relates to a concentrated storage-stable aqueous dye solution and more particularly to a concentrated storage-stable aqueous dye solution without any solubilizer content.
  • the invention further relates to the use of the present invention's concentrated dye solution, if appropriate after dilution with water, especially for dyeing and printing paper, including card and board.
  • Pulverulent dyes must accordingly first be dissolved in mostly warm or hot water to be usable for printing and dyeing.
  • Metering systems developed for this purpose utilize weighing or volumetric methods to control the metered addition of dyes and they require stable dye solutions instead of powders and granules.
  • the solutions should possess optimum stability, so that they do not precipitate during transportation or storage. Typically, they should be stable for a prolonged period between nought and five degrees Celsius, but also at around 50°C. Similarly, frozen solutions shall be stable after pouring and should not present any stability problems during pumping. Precipitates can cause disruptions in pumping or metering systems and lead to unacceptable machine shutdowns and costly cleaning and maintenance.
  • aqueous dye solutions One problem of known aqueous dye solutions is the large amounts of added solubilizers, which lead to a high carbon content in the dyehouse or paper mill effluence. This leads to effluence of high total organic carbon (TOC) and chemical oxygen demand (COD), and hence causes high water-treating costs. It is accordingly an object of the present invention to provide a concentrated aqueous dye solution for which the dye does not have to be isolated and dried (high energy costs!) and which includes few or no solubilizers.
  • TOC total organic carbon
  • COD chemical oxygen demand
  • the concentrated aqueous dye solutions of the present invention comprise one or more cationizable dyes, an organic acid and water.
  • the present invention's concentrated aqueous dye solutions in a further preferred embodiment comprise dyes of the formula (I)
  • each A is independently -NH- or -O-
  • B is a polyvalent group or atom
  • n' and n" are natural numbers and the sum total of n' and n" is > 2
  • m is a natural number > 0,
  • CC is a group having the formula (c ) or (c 2 )
  • each R 10 is independently H; C 1-4 alkyl; C5 -6 cycloalkyl; phenyl, benzyl or phenylethyl, each R 10 ' is independently H; -OH or C 1-4 alkyl each Tx is independently H; -CN; -COOR 15 ; CONR 16 R 17 ; SO 2 NR 16 R 17 ;
  • G is H; -R ! iNHR ⁇ or -R t iNR 13 R 14 where R ⁇ is C 1-6 alkylene or C 2-6 alkenylene, R 12 and R 13 are independently H; unsubstituted C 1-6 alkyl; C 2-6 alkyl substituted by OH, CN or halogen; phenyl-C 1-3 alkyl where the phenyl radical is optionally singly, doubly or triply substituted by substituents selected from the group consisting of chlorine, C 1-4 alkyl or C ⁇ .
  • R 14 has meaning as for R 12 or R 13 or a hydrogen atom
  • R 15 is C 1-6 alkyl radical or phenyl-C 1-3 alkyl radical
  • R 16 and R 1 are independently H or a C 1-4 alkyl radical
  • R 18 is in each occurrence independently H; a C 1-4 alkyl radical; -NR 16 R 17 -(CH 2 ) 2-4 -NR 16 R 17 or -CONR 16 R 17
  • R 19 is a C ⁇ alkyl radical or a hydroxy-C 1-4 alkyl radical
  • R 20 is -S- or -O-
  • R 21 is a hydrogen atom or a C 1-4 alkyl radical
  • An " is a non-coloured anion, with the conditions that
  • the present invention's storage-stable high-concentration solutions of dyes of the formula (I) may also comprise a plurality of different dyes whose formulae come within the formula (I).
  • T t is a substituent of the formula
  • the CC group is a substituent of the formula
  • B is a group B' C[(CH 2 )o ⁇ ] ⁇ -4 or B is one of the groups -[-(CH 2 ) -O-(CH 2 ) M ] 4 C or [-(CH2) 1-3 -O-(CH 2 ) 1-3 -O-(CH 2 ) 1-3 ] 4 C or [-(CH 2 ) 1-2 -O-(CH 2 ) 1-2 -O-(CH 2 ) 1-2 -O-(CH 2 ) 1-2 ] 4 C or
  • B is particularly preferable for B to be a carbon atom.
  • the present invention's storage-stable high-concentration solutions of dyes of the formula (I) have a formula (I) dye content of up to 40% by weight of dye reckoned on the total weight of the solution.
  • Preferred dye solutions have a dye content in the range from 5% to 40% by weight of dye or a dye content in the range from 10% to 35% by weight of dye and most preferably a dye content in the range from 15% to 25% by weight of dye.
  • the level of organic acids in the present invention's storage-stable high-concentration solutions of dyes of the formula (I) is between 0.5% by weight and 25% by weight reckoned on the total weight of the solution.
  • Preferred dye solutions comprise from 1% to 15% by weight of added organic acids or from 2% to 10% by weight of added organic acids and most preferably from 3% to 7% by weight of added organic acids.
  • Preferred organic acids are acids of the formula A(-COOH) n where A is C 1-12 -alkanyl or C 1-12 -alkenyl which may each be interrupted by nitrogen atoms and or oxygen atoms and which may each be additionally substituted by hydroxyl or NR'R" (where R' and R" are independently C 1-6 -alkanyl or C 1-6 -alkenyl or C 1-6 -hydroxyalkanyl or Ci- 6 -hydroxyalkenyl, or unsubstituted phenyl or hydroxyl- or sulphur- or C 1-18 -alkanyl- or C 1-18 -alkenyl-substituted phenyl) and with n as a natural number of 1, 2 or 3.
  • acetic acid is the most preferred organic acid. These acids will be present in a partially deprotonated (dissociated) state, as would be expected from their pK value and from the pH value of the dye solution.
  • non-coloured anions examples include chlorides, bromides, sulphates, bisulphates, methosulphates, aminosulphonates, perchlorates, benzenesulphonates, oxalates, malonates, maleates, acetates, propionates, lactates, succinates, tartrates, malates, methanesulphonates and benzoates.
  • complex anions such as for example zinc chloride double salts and anions of boric acid, citric acid, glycolic acid, diglycolic acid and adipic acid or addition products of orthoboric acid with polyalcohols having at least one cis diol group.
  • anions may of course also be exchanged, for example by means of ion exchangers or customary precipitation reactions.
  • the ions can also be exchanged by diafiltration or ultrafiltration.
  • the halides chloride and bromide are particularly preferred anions and chloride is most preferred.
  • the salts of the added organic acids can likewise perform the anion function.
  • the anions are chlorides and the added organic acid is acetic acid.
  • Preferred dye solutions according to the present invention consist of up to 40% by weight of dye, from 0.5% to 25% by weight of the organic acid and, made up to 100% by weight, of water, but especially of 10% to 35% by weight of dye, from 1% to 15% by weight of the organic acid and, made up to 100% by weight, of water, with especially preferred dye solutions consisting of 15% to 25% by weight of dye, from 2% to 10% by weight of the organic acid and, made up to 100% by weight, of water.
  • Particularly preferred dye solutions according to the present invention consist of up to 40% by weight of dye as chloride, from 0.5% to 25% by weight of the organic acid and, made up to 100% by weight, of water, but especially of 10% to 35% by weight of dye as chloride, from 1% to 15% by weight of the organic acid and, made up to 100% by weight, of water, with especially preferred dye solutions consisting of 15% to 25% by weight of dye as chloride, from 2% to 10% by weight of the organic acid and, made up to 100% by weight, of water.
  • Very particularly preferred dye solutions according to the present invention consist of up to 40% by weight of dye as chloride, from 0.5% to 25% by weight of acetic acid and, made up to 100% by weight, of water, but especially of 10% to 35% by weight of dye as chloride, from 1 % to 15% by weight of acetic acid and, made up to 100% by weight, of water, with especially preferred dye solutions consisting of 15% to 25% by weight of dye as chloride, from 2% to 10% by weight of acetic acid and, made up to 100% by weight, of water.
  • the invention also provides a process for producing the invention's dye solutions which is characterized in that an aqueous solution or suspension of at least one crude cationic dye is pressed through a semipermeable membrane by applying a pressure to remove salts and synthesis by-products having molecular weights below 500 and some water.
  • the permeate is continuously or intermittently replaced or supplemented by water or buffer solution so that the volume of the batch changes only minimally, if at all.
  • the dye concentration remains constant or substantially constant.
  • the dye concentration of the permeate does not change by more than 20% in a preferred embodiment, by not more than 10 % in particularly preferred processes and by not more than 5% in very particularly preferred processes.
  • the dye solution is brought to the desired concentration by concentrating.
  • the membranes used in the process of the present invention are TFMTM membranes, for example the G10, G20, G50 or DL5 membranes from GE Osmonics Desal (GE Osmonics Inc., 5951 Clearwater Drive, Minnetonka, Minnesota 55343, United States), of which the DL5 membrane is particularly preferred.
  • the counterions of the cationic dye are exchanged, or further anions added, prior to diafiltration.
  • the newly added anions mean that the original anions are easily removable through ultrafiltration or diafiltration.
  • the counterions of the cationic functions are exchanged by halides in a particularly preferred embodiment and by chloride in a very particularly preferred embodiment.
  • the present invention further provides for the production of stable liquid formulations of anionic dyes by ultrafiltration of the aqueous solution or suspension of the crude dye.
  • Ultrafiltration or diafiltration of the reaction solution which is obtained as per the examples of WO 02/062902, although the dyestuff is not isolated, can be used to render the reaction solution free of further, undesirable additions. Free of undesirable additions is to be understood as meaning in particular that, post ultrafiltration or diafiltration, the solutions comprise less than one% by weight and preferably less than 0.5% by weight of further materials.
  • Undesirable further materials are in particular inert salts and electrolytes which, having been used to neutralize and/or salt the dye out, come from the synthesis stage and are carried along in the synthesis solution or suspension, such as alkali metal or alkaline earth metal salts, for example ammonium, magnesium chloride, magnesium sulphate, magnesium bisulphate, sodium chloride, sodium sulphate, sodium bisulphate, potassium chloride, potassium sulphate or potassium bisulphate, especially sodium chloride.
  • alkali metal or alkaline earth metal salts for example ammonium, magnesium chloride, magnesium sulphate, magnesium bisulphate, sodium chloride, sodium sulphate, sodium bisulphate, potassium chloride, potassium sulphate or potassium bisulphate, especially sodium chloride.
  • organic acid can also be added before or during the ultrafiltration or diafiltration.
  • the dye solutions of the present invention may comprise biocides.
  • biocide is suitable. But preference is given to biocides having FDA approval. Any biocide capable of controlling the growth of Gram-positive or Gram-negative bacteria, yeasts or fungi can be used in the solutions of the present invention. Suitable biocides are for example 3-thiazolone derivatives, which are for example alkylated and/or chlorinated or used as mixtures. Typically, biocides are added in an amount of up to 0.15% by weight per ready-produced composition.
  • the concentrated solutions can also be diluted again with water before they are used for dyeing.
  • the concentrated solutions can also be shaded with further dyes before use. But the concentrated solutions can also be used for shading other dyes.
  • Dyes especially useful for shading or for being shaded include all dyes which the Colour Index identifies as C.I. Basic Red or C.I. Basic Brown or C.I. Basic Blue or C.I. Basic Violet, and especially one or more of the following dyes can be used for shading: C.I. Basic Brown 23 or C.I. Basic Red 12 or C.I. Basic Blue 1 or C.I. Basic Red 14 or C.I. Basic Violet 10 or C.I. Basic Blue 26.
  • Dyes of the formula (II) and/or of the formula (III) are similarly useful for shading or for being shaded.
  • the concentrated solutions can also be used for shading brown dyes of the formula (II), or the concentrated solutions can be shaded with dyes of the formula (II).
  • the dyes of the formula (II) have the following structure:
  • R 6 ,R 7 ,R 8 orR 9 are independently H or -SO 3 H and M a or M independently have the meanings of Mi to Mio, with Mi being H, M 2 being -(CH 2 ) 3 N(CH 3 )2, M 3 being -(CH 2 )2N(CH 2 CH 3 ) 2 ,
  • Ms being M 9 being Mio being -(CH 2 ) 2 NH 2 and R a or R b independently have the meanings of R ⁇ to R 5 .
  • R ⁇ being H, + r- N, /> A R 2 being J
  • R 3 being R 4 being CN.
  • the dyes of the formula (II) are known per se and can be prepared as described in DE3715066.
  • the concentrated solutions can also be used for shading brown dyes of the formula (III), or the concentrated solutions can be shaded with dyes of the formula (III).
  • the dyes of the formula (III) have the following structure: where R ⁇ R 2 or R 3 are independently H, CH 3 , C 2 H 5 , n-C 3 H , i-C 3 H , n-C 4 H 9 , i-C 4 H 9 , sec-C 4 H 9 ,
  • R n is -C2H4-, -C3H6-, -CH(CH 3 )CH 2 - or -C 4 H 6 - Y is hydrogen or nitro, q is 1 or 2.
  • the dyes of the formula (III) are known and can be prepared as described in EP 162409 or EP1352928.
  • Shading can be effected in the ratios of 2% to 98% by weight (based on the dye) of a dye of the formula (I) and 98% to 2% by weight (based on the dye) of a shading dye, i.e. for example in the ratios 2.0 / 98.0; 2.5 / 97.5; 12.5 / 87.5; 22.5 / 77.5; 32.5 / 67.5; 42.5 / 57.5; 50.0 / 50.0; 57.5 / 42.5; 67.5 / 32.5; 77.5 / 22.5; 80.0 / 20.0; 87.5 / 12.5; 90.0 / 10.0; 95.0 / 5.0; 97.5 / 2.5; or 98.0 / 2.0.
  • the concentrated dye solutions of the present invention are used in particular, if appropriate after dilution with water, for dyeing and printing paper, including board and card, these materials being dyeable for example in the pulp, by coat or by dipping.
  • a liquid formulation can also be used for a continuous or batch dyeing process for textile materials, especially cellulose.
  • the concentrated dye solutions of the present invention can be used as a base for producing inkjet inks or other inks and combinations for the contactless printing of substrates such as paper or textiles.
  • the formulations of the present invention can also be used without further modification for the contactless printing of substrates such as paper or textiles.
  • the present invention further provides for the use of the present invention's dye preparations of anionic dyes for producing wood stains for staining solid wood or wood chippings or chipboards or wood fibre boards. Staining wood in form of beams, boards or finished objects like furniture, parts of buildings is a preferred use of the wood stains according to the invention.
  • the application of the liquid formulations according to the invention may be carried out over the whole or part of the wood's surface (to compensate for color defects in the wood or veneer).
  • the liquid formulations according to the invention may be used in water stains (main solvent water), solvent stains (ca. 30 - 95 % organic solvent), or chemical stains (which are generally water thinnable).
  • Example 2 434 parts of the amino components of Example 1 are added to a mixture of 1736 parts of ice, 781 parts of 30% HC1, 694 parts of acetic acid and 260 parts of N,N- dimethylacetamide and are diazotized with 182 parts of 4 N sodium nitrite solution. The temperature is maintained at 0 - 5°C by addition of 870 parts of ice. To the diazo solution obtained are added 3281 parts of an approximately 20% aqueous solution of 6- hydroxy-4-methyl-3- ⁇ yridonyl-3'-methylpyridinium chloride. The pH is adjusted to 3 at a temperature of 10 - 20°C by addition of 130 parts of 30% sodium hydroxide solution.
  • Hyflo-Supercel filter earth After subsequent stirring for 1 hour, 50 parts of Hyflo-Supercel filter earth are added before filtration through a porcelain suction filter with absorbent pad.
  • the clear dye solution obtained (9700 g; 8900 ml) is diafiltered in a laboratory ultrafiltration system having a DL5 membrane at 40 - 45°C and a pressure of 15 bar until the conductivity in the permeate stays constant. In the process, the volume is kept substantially constant. This required about 33 000 parts (ml) of demineralized water.
  • the pH is maintained at 4.0 - 4.5 during the ultrafiltration by addition of acetic acid.
  • the retentate is concentrated at a pressure of 12 - 15 bar to 5180 parts (g) and then admixed with 140 parts of acetic acid to obtain a solution having a total dye content of about 20% by weight, consisting of the components having the formulae (2a, 2b, 2c, 2d):
  • the dyeings obtained have excellent wet fastnesses (to plain water, alcohol, milk, soapy water, acetic acid, urine, etc.)
  • a mixture consisting of 7.7 g of 4-aminoacetanilide and 22.9 g of 3-aminoacetanilide is diazotized with sodium nitrite by known methods and to the mixture of the obtained diazonium salts 58.5 g of 6-hydroxy-4-methyl-l-(3 , -dimethylamino)propyl-3-pyridinio- 2-pyridone betaine base are added as coupling component and these are coupled by known methods at a pH of 1.8-2.2.
  • the acetylamino group is then hydrolyzed with 57.5 g of 30% hydrochloric acid by known methods and thereupon the two aminoazo compounds are diazotized with 13.8 g of sodium nitrite by known methods and the diazonium salts obtained are coupled with 11 g of resorcinol at 0-5°C.
  • This isomer mixture dyes wood-containing paper in brown shades.
  • the dye can be dissolved with glacial acetic acid and water to form a stable 20% liquid formulation.
  • the dye dyes paper in a yellow hue. The hue is No. 4 on the Colour Index Hue Indication Chart. The effluent is only minimally coloured.
  • the dyed papers can be bleached by means of hydrosulphite. The dissolved compound conforms to the formula +
  • An absorbent web of unsized paper is pulled at 40-50°C through an aqueous dye solution consisting of 95 parts of water and 5 parts of the inventive dye solution of Preparation Example 2.
  • the dye preparations of Preparation Examples 3, 4 and A1-A37 can be used for dyeing similarly to Prescriptions A to C.
  • 100 parts of freshly tanned and neutralized chrome grain leather are drummed for 30 minutes in a float of 250 parts of water at 55°C and 0.5 part of the dye preparation made according to Preparation Example 2 and are treated for a further 30 minutes in the same bath with 2 parts of anionic fatliquor based on sulphonated fish oil.
  • the leathers are conventionally dried and finished.
  • the leather obtained has a level yellow hue.
  • vegetable-retanned leathers can likewise be dyed according to known methods.
  • Dyeing can be done in a similar manner with dyes of Preparation Examples 3, 4 and Al - A37.
  • Dyeing can be done in a similar manner with dyes of Preparation Examples 3, 4 and Al - A37.
  • a dry stock containing 60% groundwood and 40% unbleached sulphite pulp is beaten with sufficient water and ground to 40 SR freeness in a hollander for the dry content to be just above 2.5% and then adjusted with water to a dry content of exactly 2.5% for the high-density pulp.
  • 200 parts of this high-density pulp are admixed with 5 parts of a 0.25% aqueous solution of the dye of Preparation Example 2, stirred for about 5 min., admixed with 2% of resin size and 4% of alum, based on dry stock, and again stirred for some minutes until homogeneous.
  • the material is diluted with about 500 parts of water to 700 parts by volume and used in a known manner to prepare sheets of paper by drainage on a sheet-former. These sheets of paper have a deep yellow colour.
  • Dyeing can be done in a similar manner with dyes of Preparation Examples 3, 4 and Al - A37.
  • An ink composition for inkjet printing consists of
  • This ink composition was then used for printing paper, papery substrates, textile fibre materials and plastic film/sheet by transferring the ink into the ink receptacle of a commercially available inkjet printer and using it to produce a single-coloured test print on the identified sheetlike materials.
  • Dyeing can be done in a similar manner with dyes of Preparation Examples 3, 4 and Al - A37.
  • a batten of coniferous wood (European spruce) and a batten of leafy wood (beech) were each cut into pieces of about 5 cm and immersed for some minutes in a diluted (10 parts water and 1 part of the dye solution according to example 2) dyestuff solution according to example 2 and after drying for ten hours light brownish batten pieces were obtained.
  • Dyeing can be done in a similar manner with dyes of Preparation Examples 3, 4 and Al - A37.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Textile Engineering (AREA)
  • Paper (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Coloring (AREA)
  • Ink Jet (AREA)
  • Ink Jet Recording Methods And Recording Media Thereof (AREA)

Abstract

L'invention concerne des solutions de colorants aqueux concentrées, contenant un ou plusieurs colorants pouvant être cationisés, un acide organique et de l'eau, ainsi que leur utilisation pour colorer et/ou imprimer des substrats organiques et pour produire des encres pour l'impression jet d'encre. (Formule I), dans laquelle chaque A est indépendamment -NH- ou -O-, B est un groupe ou un atome polyvalent, n' et n'' sont des nombres naturels dont la somme est = 2, m est un nombre naturel = 0, CC est un groupe de formule (c1) ou (c2).
EP05739802A 2004-05-26 2005-05-17 Solution de colorant concentree Withdrawn EP1756232A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP05739802A EP1756232A1 (fr) 2004-05-26 2005-05-17 Solution de colorant concentree

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP04012458 2004-05-26
PCT/IB2005/001492 WO2005116143A1 (fr) 2004-05-26 2005-05-17 Solution de colorant concentree
EP05739802A EP1756232A1 (fr) 2004-05-26 2005-05-17 Solution de colorant concentree

Publications (1)

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EP1756232A1 true EP1756232A1 (fr) 2007-02-28

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US (1) US20070251030A1 (fr)
EP (1) EP1756232A1 (fr)
JP (1) JP2008500421A (fr)
KR (1) KR20070024538A (fr)
CN (1) CN1961045A (fr)
BR (1) BRPI0511598A (fr)
NO (1) NO20065378L (fr)
TW (1) TW200613464A (fr)
WO (1) WO2005116143A1 (fr)

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KR101206593B1 (ko) * 2003-12-04 2012-11-29 클라리언트 파이넌스 (비브이아이)리미티드 염료의 농축된 수성 조성물
TWI526502B (zh) * 2009-12-25 2016-03-21 Sumitomo Chemical Co Pyridine ketone compound compounds
CN101881074A (zh) * 2010-07-01 2010-11-10 刘彬彬 一种新型环保实木复合强化地板生产工艺
US10315407B2 (en) 2010-07-01 2019-06-11 Zhejiang Lingge Wood Co., Ltd Environmental wood laminate flooring and method for forming the same

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DE2029314A1 (de) * 1970-06-13 1971-12-23 Farbwerke Hoechst AG, vormals Meister Lucius & Brüning, 6000 Frankfurt Stabile, konzentrierte Lösungen basischer Azofarbstoffe
DE3030918A1 (de) * 1980-08-16 1982-04-01 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung von loesungen kationischer azofarbstoffe
DE3418672A1 (de) * 1984-05-19 1985-11-21 Basf Ag, 6700 Ludwigshafen Basische azofarbstoffe
CH672496A5 (fr) * 1986-05-14 1989-11-30 Sandoz Ag
DE59207647D1 (de) * 1991-05-17 1997-01-23 Ciba Geigy Ag Verfahren zur Herstellung hochkonzentrierter wässriger Lösungen von kationischen Azofarbstoffen
DE19500203A1 (de) * 1994-01-14 1995-07-20 Sandoz Ag Kationisch verbrückte Tetrakisazofarbstoffe mit unterschiedlichen Kupplern, ihre Herstellung und Verwendung
US6533826B1 (en) * 1998-08-08 2003-03-18 Basf Aktiengesellschaft Method for producing aqueous solutions of cationic diarylmethane colorants and triarylmethane colorants
GB0103240D0 (en) * 2001-02-09 2001-03-28 Clariant Int Ltd Organic compounds

Non-Patent Citations (1)

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Title
See references of WO2005116143A1 *

Also Published As

Publication number Publication date
TW200613464A (en) 2006-05-01
JP2008500421A (ja) 2008-01-10
BRPI0511598A (pt) 2008-01-02
CN1961045A (zh) 2007-05-09
KR20070024538A (ko) 2007-03-02
US20070251030A1 (en) 2007-11-01
WO2005116143A1 (fr) 2005-12-08
NO20065378L (no) 2007-02-23

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