EP1756231A1 - Procede pour produire des ajustages de liquides de colorants azo basiques - Google Patents

Procede pour produire des ajustages de liquides de colorants azo basiques

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Publication number
EP1756231A1
EP1756231A1 EP05746248A EP05746248A EP1756231A1 EP 1756231 A1 EP1756231 A1 EP 1756231A1 EP 05746248 A EP05746248 A EP 05746248A EP 05746248 A EP05746248 A EP 05746248A EP 1756231 A1 EP1756231 A1 EP 1756231A1
Authority
EP
European Patent Office
Prior art keywords
acid
phenylenediamine
azo dyes
diazotization
basic azo
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Withdrawn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
EP05746248A
Other languages
German (de)
English (en)
Inventor
Michael Schmitt
Jürgen DECKER
Helmut Reichelt
Gerd Rollar
Armin Diefenbacher
Hartwig Voss
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 EP1756231A1 publication Critical patent/EP1756231A1/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Withdrawn legal-status Critical Current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
    • C09B37/00—Azo dyes prepared by coupling the diazotised amine with itself
    • 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
    • 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
    • C09B67/0096—Purification; Precipitation; Filtration

Definitions

  • the present invention relates to a new process for the preparation of liquid formulations of basic azo dyes from optionally substituted phenylenediamine by diazotization and coupling in acidic solution.
  • DE-A-37 13 617 teaches the preparation of liquid formulations of basic azo dyes from optionally substituted m-phenylenediamine by reaction with 0.76 to 0.95 mol of nitrite based on 1 mol of m-phenylenediamine and subsequent heating of the reaction mixture. Dyes produced in this way are characterized by good bath exhaustion. However, the problem of storage stability remains unsolved here.
  • DE-A-37 13618 describes the subsequent reaction with 0.1 to 1.2 moles of formic acid and thermal aftertreatment of the reaction mixture of diazotization of m-phenylenediamine with neopentyl glycol dinitrite and coupling onto itself. This procedure leads to dyes which occur during dyeing do not blush with acid in paper. However, the use of an organic nitrite is also problematic here.
  • liquid adjustments of basic azo dyes from a phenylenediamine I which can still be substituted by alkyl or alkoxy, can be advantageously obtained by diazotization and coupling in acidic solution if the phenylenediamine I in the presence of at least two organic acids comprising at least one first Acid (A) with a pk A value of ⁇ 4.0 and at least one second Acid (B) with a pK A value ⁇ 4.1 diazotized with sodium nitrite, and after the end
  • Coupling performs a nanofiltration.
  • the dye solution is desalted and, if necessary, concentrated by the nanofiltration. Surprisingly, it was found that the crude dye solutions obtained according to the invention can be desalted by means of nanofiltration without there being unacceptable losses of dye. In addition, the dyes produced by the process according to the invention are notable for good storage stability.
  • the starting product for the azo dyes is phenylenediamine I, which is optionally substituted by dC-alkyl or dC 4 -alkoxy.
  • Phenylene diamine which is unsubstituted or substituted by a methyl or methoxy group is preferably used.
  • Suitable acids (A) with a pk A value of 4,0 4.0 are methanesulfonic acid and preferably formic acid.
  • Suitable acids (B) with a pK A value 4 4.1 are, for example, C 2 -C -alkanoic acids, which may optionally be substituted appropriately. Propionic acid and especially acetic acid are particularly preferred.
  • the solution medium can also contain water or other water-soluble solvents such as alkanols, glycols, glycol ethers, amides or esters, e.g. B. methanol, ethanol, propanol, isopropanol, ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, ethylene glycol monoethyl, propyl or butyl ether, N, N-dimethylformamide, N-methylpyrrolidone or gamma-butyrolactone.
  • water is preferably the only solvent medium.
  • the solvent medium used for the diazotization and coupling advantageously contains about 3 to 30% by weight, preferably 10 to 25% by weight, of organic acid and the balance water.
  • the proportions of the reactants and solvents are expediently chosen so that the basic solutions prepared according to the invention Azo dyes have about 4 to 10% by weight of dye before nanofiltration. After desalting and concentration by means of nanofiltration, liquid formulations with a dye content of approx. 12-25% by weight are usually obtained.
  • the process according to the invention is expediently carried out in such a way that the mixture of the two acids (A) and (B) is initially introduced, or one or all of the acids (A) or (B) are preferably metered in completely or partially. It is possible to present the majority of the stronger acid (A) in order to keep the pH as low as possible at the beginning of the diazotization. According to a preferred variant, at least 80 mol% of acid (A), based on the total amount of acid at the start of the diazotization, is present in the reaction mixture at the start of the diazotization. Also preferred is a variant in which the proportion of acid (A) is 20 to 50 mol% based on the total amount of acid used (A + B).
  • a process is particularly preferred which combines both variants, that is to say one begins with a reaction mixture comprising at least 80 mol% of acid (A) and the acid fraction of acid (A) is from 20 to 50 mol%, based on the total amount of acid used.
  • This acid ratio which changes in the course of the reaction, is achieved by portionwise or continuous metering in of acid (B).
  • the most advantageous acid gradient can be determined by simple experiments by varying the rate of metering.
  • the phenylenediamine I is preferably dissolved in the acid (B) and metered in at the same time with a usually aqueous solution of the diazotizing agent. During the reaction, the pH of the mixture rises, whereby the coupling reaction can finally proceed completely. If necessary, part of the amount of acid (A) or (B) can also be metered in independently of phenylenediamine I.
  • a solution of the optionally substituted phenylenediamine I in acid (B) is preferably metered into the reaction mixture in parallel and thus at the same time as the diazotizing agent, generally with its own feed.
  • the sodium nitrite and the phenylenediamine are added at a temperature in the range from -10 to +25 ° C., preferably at 0 to 15 ° C.
  • the reaction mixture is, according to a preferred variant, stirred at from 30 ° C. to 50 ° C. for a period of from 0.5 to 5 hours and then optionally heated to a temperature from 60 ° C. to the boiling point of the reaction mixture.
  • the dyes produced by the process according to the invention are generally not uniform dyes, but rather mixtures of mono-, Bis and polyazo dyes, since the diamines used as the starting product and their secondary products are not only simple but can also be diazotized and coupled several times.
  • the main components have the following formula:
  • R is hydrogen, C 1 -C 4 -alkyl or dd-alkoxy and X is the counterion of an acid, usually the organic acid serving as solvent.
  • Similar products such as dyes obtained by the process according to the invention, are e.g. known under the trade names Bismarckbraun G and R or Vesuvin or also described in EP-A-36 553. They are used for dyeing paper, especially waste paper, or leather, or for dyeing anionically modified fibers, for example acrylonitrile polymers. By mixing with other basic dyes, other colors, e.g. B. Black can be set.
  • the process according to the invention generally gives a crude dye solution whose dye content is 4 to 10% by weight. Such a solution can be nanofiltered directly. If a concentrated dye solution is present, it can be advantageous to dilute the mixture with water to a 4 to 8% by weight dye solution in order to achieve higher flow rates during filtration and thus to increase the space-time yield.
  • the mixture is desalted and concentrated by separating off the permeate.
  • membranes in the membrane separation unit used according to the invention are used.
  • the transmembrane pressures are 1 to 50 bar at temperatures up to 100 ° C.
  • the separating layers of the membranes that can be used can consist of organic polymers, ceramics, metal, carbon or combinations thereof and must be stable in the reaction medium and at the process temperature. For mechanical reasons, they are Separating layers are generally applied to a single- or multi-layer porous substructure, which consists of the same or at least one different material as the separating layer. Examples are separating layers made of ceramic and substructures made of metal, ceramic or carbon, separating layers made of carbon and substructures made of metal ceramic or carbon, separating layers made of polymers and substructures made of polymer, metal, ceramic or ceramic on metal. Polysulfone, polyether sulfone, polydimethylsiloxane (PDMS), polyether ether ketone, polyamide, polyimide are used as polymeric separating layers, for example.
  • Inorganic membranes in particular membranes with ceramic separation layers, are particularly preferred. In comparison to membranes with polymeric separating layers, these membranes achieve a better salt passage and a higher permeate flow.
  • ⁇ -Al 2 O 3 , ZrO 2 , TiO 2 , SiC or mixed ceramic materials are used as ceramic separating layers.
  • the membranes are usually used in pressure-resistant housings, which allow the separation between retentate (dye-rich residue) and permeate (low-dye filtrate) under the pressure conditions required for the separation.
  • the membranes can be designed in flat, tubular, multi-channel element, capillary or winding geometry, for which the corresponding pressure housing, which allows a separation between retentate and the permeate, is available.
  • a membrane element can contain several channels.
  • several of these elements can be combined into one module in one housing.
  • the overflow speed in the module is between 0.2 and 10 m / s depending on the module geometry. Typical values are 0.2 to 0.4 m / s for a winding geometry and 1 to 6 m / s for a tube geometry.
  • the nanofiltration for desalination is preferably carried out partly as diafiltration.
  • a diafiltration is characterized in that the permeate drawn off is replaced in whole or in part by a suitable diafiltration medium.
  • the permeate is preferably replaced by an aqueous acid solution in order to keep the pH constant.
  • the permeate can be replaced either in portions or continuously.
  • the diafiltration step achieves a total permeate quantity which is 1 to 10 times the quantity circulated Dye solution corresponds to the amount of inorganic Reduce salts to ⁇ 10% by weight based on the 100% dye. After nanofiltration, one usually has 12 to 25% by weight dye solutions.
  • solutions of the basic azo dyes obtained by the process according to the invention can be used directly as a liquid formulation.
  • solubilizing additives are added to the dye solutions.
  • additives are, for example, water-miscible organic solvents such as dC 4 -alkanols, for example methanol, ethanol, propanol, isopropanol, butanol, isobutanol, sec-butanol or tert-butanol, carboxamides, such as N, N-dimethylformamide or N, N -Dimethylacetamide, ketones or keto alcohols, such as acetone, methyl ethyl ketone or 2-methyl-2-hydroxypentan-4-one, ethers, such as tetrahydrofuran or dioxane, mono-, oligo- or polyalkylene glycols or -thioglycols which have C -C 6 -alkylene units , such as ethylene glycol, 1, 2- or 1,3-propylene glycol, 1, 2- or 1, 4-butylene glycol, neopen
  • Suitable solubilizing additives are also lactams, such as caprolactam, pyrrolidin-2-one or N-methylpyrrolidin-2-one, urea, cyclic ureas, such as 1,3-dimethylimidazolidin-2-one or 1,3-dimethylhexahydropyrimid-2-one and , Polyvinylamides, polyvinyl acetates, polyvinyl alcohols, polyvinyl pyrrolidones, polysiloxanes or copolymers of the respective monomers. Likewise, oligomers of ethylene oxide or propylene oxide or derivatives of these oligomers can be used.
  • Preferred solubilizing additives are ureas, mono, di- or triethanolamine, caprolactam, mono-, di- or trialkylene glycols which have C 2 -C 5 -alkylene units and / or oligo- and polyalkylene glycols with ethylene and / or propylene units and their dC 4 -Alkyl ether and dC -alkyl ester.
  • Ethylene glycol, 1, 2- or 1, 3-propylene glycol, neopentyl glycol, butyl diglycol, alkylpolyethylene glycols (MW 200-500), ureas and caprolactam are very particularly preferred.
  • Preferred liquid formulations essentially contain 10 to 30% by weight of basic azo dyes (based on the dye without counterion)
  • liquid formulations which essentially contain 10 to 30% by weight of basic azo dyes and 1 to 30% by weight, preferably 1 to 10% by weight, of solubilizing additives, especially ethylene glycol, 1, 2- or 1,3-propylene glycol, neopentyl glycol , Butyl diglycol, alkyl polyethylene glycols (MW 200 - 600), ureas and / or caprolactam.
  • solubilizing additives especially ethylene glycol, 1, 2- or 1,3-propylene glycol, neopentyl glycol , Butyl diglycol, alkyl polyethylene glycols (MW 200 - 600), ureas and / or caprolactam.
  • the liquid formulations obtained according to the invention are notable for excellent storage stability.
  • the liquid formulations are suitable, inter alia, for dyeing and printing cellulosic fiber materials such as wood-containing and wood-free paper pulps.
  • liquid formulations of basic azo dyes are obtained which enable the direct production of dyebaths by merely diluting them with water.
  • the liquid formulations have a low salt content.
  • the process according to the invention avoids the isolation of solids and enables the production of low-salt, stable liquid formulations.
  • the solution was first diafiltered.
  • the permeate removed was replaced by continuous, level-controlled addition of an aqueous acetic acid solution as the diafiltration medium.
  • a total of 3.9 times the amount of raw dye solution originally used was removed as permeate.
  • the concentration of the dye was 7.1% by weight.
  • the concentration of formate and acetate was 0.6% and 5.0% by weight.
  • the remaining retentate was then concentrated on the same membrane by a factor of 2.2 under identical conditions. After the concentration, the concentration of the dye was 15.5% by weight.
  • the concentration of formate and acetate was 1.1% and 7.2% by weight.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé pour produire des ajustements de liquides de colorants azo basiques à partir de phénylènediamine I, qui peut être substituée par alkyle ou alcoxy, par diazotisation ou couplage dans une solution acide. La phénylènediamine est diazotée en présence d'au moins deux acides organiques comprenant au moins un premier acide (A) présentant une valeur pkA inférieure ou égale à 4,0 et au moins un second acide (B) présentant une valeur pKA supérieure ou égale à 4,1 avec du nitrure de sodium, puis un nanofiltrage est effectué à la fin du couplage.
EP05746248A 2004-05-19 2005-05-18 Procede pour produire des ajustages de liquides de colorants azo basiques Withdrawn EP1756231A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004025444A DE102004025444A1 (de) 2004-05-19 2004-05-19 Verfahren zur Herstellung von Flüssigeinstellungen basischer Azofarbstoffe
PCT/EP2005/005393 WO2005113682A1 (fr) 2004-05-19 2005-05-18 Procede pour produire des ajustages de liquides de colorants azo basiques

Publications (1)

Publication Number Publication Date
EP1756231A1 true EP1756231A1 (fr) 2007-02-28

Family

ID=34969533

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05746248A Withdrawn EP1756231A1 (fr) 2004-05-19 2005-05-18 Procede pour produire des ajustages de liquides de colorants azo basiques

Country Status (6)

Country Link
US (1) US20070213514A1 (fr)
EP (1) EP1756231A1 (fr)
CN (1) CN1957044A (fr)
DE (1) DE102004025444A1 (fr)
MX (1) MXPA06013154A (fr)
WO (1) WO2005113682A1 (fr)

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Also Published As

Publication number Publication date
US20070213514A1 (en) 2007-09-13
MXPA06013154A (es) 2007-02-14
DE102004025444A1 (de) 2005-12-15
WO2005113682A1 (fr) 2005-12-01
CN1957044A (zh) 2007-05-02

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