EP1740658A1 - Pigments de naphtol-as ultra-purs - Google Patents

Pigments de naphtol-as ultra-purs

Info

Publication number
EP1740658A1
EP1740658A1 EP05716543A EP05716543A EP1740658A1 EP 1740658 A1 EP1740658 A1 EP 1740658A1 EP 05716543 A EP05716543 A EP 05716543A EP 05716543 A EP05716543 A EP 05716543A EP 1740658 A1 EP1740658 A1 EP 1740658A1
Authority
EP
European Patent Office
Prior art keywords
pigment
naphthol
inks
hydrogen
ppm
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Withdrawn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
EP05716543A
Other languages
German (de)
English (en)
Inventor
Ulrike Rohr
Rüdiger BAUR
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 Produkte Deutschland GmbH
Original Assignee
Clariant Produkte Deutschland GmbH
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 Produkte Deutschland GmbH filed Critical Clariant Produkte Deutschland GmbH
Publication of EP1740658A1 publication Critical patent/EP1740658A1/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Withdrawn legal-status Critical Current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
    • C09B67/0096—Purification; Precipitation; Filtration
    • 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
    • C09B41/00—Special methods of performing the coupling reaction
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/0093—Microreactors, e.g. miniaturised or microfabricated reactors
    • 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
    • C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
    • C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
    • C09B29/20—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series
    • 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
    • C09B41/00—Special methods of performing the coupling reaction
    • C09B41/006—Special methods of performing the coupling reaction characterised by process features
    • 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
    • C09B67/0079—Azoic dyestuff preparations
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00783—Laminate assemblies, i.e. the reactor comprising a stack of plates
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00873—Heat exchange

Definitions

  • the present invention is in the field of azo pigments.
  • Naphthol AS pigments are of particular technical interest because they usually achieve high color strengths and cover the magenta area of the process color set. They also have good lightfastness.
  • Naphthol AS pigments are conventionally produced in a batch process.
  • a common feature of these processes is the need for precise control and compliance with the process parameters: for example, temperature, time, mixing and colorant concentration and the suspension concentration are decisive for the yield, the coloristic properties and the fastness of the pigments obtained and their
  • the object of the present invention was to provide naphthol AS pigments with a significantly reduced content of undesired secondary components.
  • the invention relates to naphthol AS pigments of the formula (IV)
  • Xi is hydrogen, halogen, nitro, carbamoyl, phenylcarbamoyl, sulfamoyl, phenylsulfamoyl, CrC 4 alkylsulfamoyl or di (-C 4 ) alkylsulfamoyl;
  • X 2 is hydrogen or halogen
  • Y is hydrogen, halogen, nitro, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or CC 4 - alkoxycarbonyl;
  • Z is phenyl, naphthyl, benzimidazolonyl, phenyl or phenyl substituted by halogen, nitro, C 1 -C 4 -alkyl and / or C 1 -C 4 alkoxy, with a maximum content of the secondary components (1) to (5) below, defined by the following limits:
  • naphthol AS pigments of the formula (IV) preference is given to naphthol AS pigments of the formula (IV) with a content of secondary component 1 of at most 80 ppm, in particular of at most 60 ppm.
  • Naphthol AS pigments are preferred for the purposes of the present invention.
  • Naphthol AS pigments are preferred for the purposes of the present invention.
  • Naphthol AS pigments are preferred for the purposes of the present invention.
  • the secondary components (1) to (5) can arise in the following way: (1): by cleavage of the diazo compound used; (2): by cleaving the amide bond of the coupler used; (3): from the diazo compound and the amine (1) released as described above; (4): from the diazo compound and the amine (2) released as described above; (5): is an unconverted coupler.
  • Y is hydrogen, methoxy, methoxycarbonyl, methyl or chlorine;
  • Xi is in the 5-position and has the meaning hydrogen, chlorine, nitro, carbamoyl, phenylcarbamoyl, sulfamoyl, phenylsulfamoyl, methylsulfamoyl or dimethylsulfamoyl;
  • X 2 is at the 4-position and is hydrogen or chlorine
  • Z is a phenyl substituted by chlorine, nitro, CrC 2 alkyl and / or CrC 2 alkoxy.
  • the pigments C.I. are particularly preferred. Pigment Red 146, 147, 176, 184, 185, 269.
  • the invention also relates to a process for producing such high-purity naphthol AS pigments, characterized in that (a) at least the azo coupling is carried out in a microreactor,
  • Step (c) can also be carried out before step (b). In some cases it may also be possible that the desired degree of purity is already achieved by one of the steps (b) or (c).
  • WO 01/59013 A1 The devices described in WO 01/59013 A1 can be used as microreactors.
  • a microreactor is made up of a plurality of platelets stacked on top of one another and connected to one another, on the surfaces of which there are micromechanically produced structures which, in their interaction, form reaction spaces in order to carry out chemical reactions.
  • the flow rates of the material flows are limited in terms of equipment, for example due to the pressures which arise depending on the geometric design of the microreactor. It is desirable for the reaction to proceed to completion in the microreactor, but a residence zone can also follow in order to create a residence time which may be required.
  • the flow rates are expediently between 0.05 and 5 l / min, preferably between 0.05 and 500 ml / min, particularly preferably between 0.05 and 250 ml / min, and in particular between 0.1 and 100 ml / min.
  • the microreaction system is operated continuously, the amounts of fluid mixed in each case being in the micro ( ⁇ l) to milliliter (ml) range.
  • the dimensions of the microstructured areas within the reactor are decisive for the production of naphthol AS pigment in this microreaction system. These must be selected to be large enough that particulate matter in particular can pass through without problems and so that the channels do not become blocked.
  • the smallest clear width of the microstructures should be about ten times larger than the diameter of the largest pigment particles. Furthermore, appropriate geometrical design must ensure that there are no dead water zones, such as dead ends or sharp corners, in which pigment particles can sediment, for example. Continuous paths with round corners are therefore preferred.
  • the structures must be small enough to take advantage of the inherent advantages of microreaction technology, namely excellent temperature control, laminar flow, diffusive mixing and low internal reaction volume.
  • the clear width of the solution- or suspension-carrying channels is expediently 5 to 10000 ⁇ m, preferably 5 to 2000 ⁇ m, particularly preferably 10 to 800 ⁇ m, in particular 20 to 700 ⁇ m.
  • the clear width of the heat exchanger channels depends primarily on the clear width of the liquid or suspension channels and is expediently less than or equal to 10000 ⁇ m, preferably less than or equal to 2000 ⁇ m, in particular less than or equal to 800 ⁇ m.
  • the lower limit of the clear width of the heat exchanger channels is not critical and is limited at most by the pressure increase of the heat exchanger liquid to be pumped and by the need for optimal heat supply or removal.
  • the dimensions of the microreaction system used are: Heat exchanger structures: channel width about 600 ⁇ m, channel height: about 250 ⁇ m; Mixer and dwell time: channel width approx. 600 ⁇ m, channel height approx. 500 ⁇ m.
  • the microreactor is preferably charged with all heat exchanger fluids and reactants from above.
  • the removal of the product and the heat exchanger fluids is preferably also carried out upwards.
  • third and fourth liquids involved in the reaction e.g. buffer solutions
  • the possible addition of third and fourth liquids involved in the reaction is realized via a T-branch located directly in front of the reactor, i.e. one reactant each can be mixed with the buffer solution in advance.
  • the required concentrations and flows are preferably checked using precision piston pumps and a computer-controlled control system.
  • the reaction temperature is monitored via integrated sensors and monitored and controlled with the help of the regulation and a thermostat / cryostat.
  • feedstocks can also be prepared beforehand in micromixers or in upstream mixing zones. Feedstocks can also be metered in downstream mixing zones or in downstream micromixers or reactors.
  • the system used here is made of stainless steel; other materials such as glass, ceramics, silicon, plastics or other metals can also be used.
  • the diazotization can also be carried out in the microreactor. Both stages can also be carried out in series-connected microreactors.
  • the reactants are expediently fed to the microreactor as aqueous solutions or suspensions and preferably in stoichiometric / equivalent amounts.
  • the azo coupling reaction is preferably carried out in aqueous solution or suspension, but it is also possible to use organic solvents, if appropriate in a mixture with water, for example alcohols having 1 to 10 carbon atoms, such as, for example, methanol, ethanol, n-propanol, isopropanol, butanols, such as n-butanol, sec-butanol, tert-butanol, pentanols, such as n-pentanol, 2-methyl-2-butanol, hexanols, such as 2-methyl-2-pentanol, 3-methyl-3-pentanol, 2- Methyl 2-hexanol, 3-ethyl-3-pentanol, octanols such as 2,4,4-trimethyl-2-pentanol, cyclohexanol; or glycols, such as ethylene glycol, diethylene glycol, propylene glycol, diprop
  • the auxiliaries used in the conventional processes such as, for example, surfactants, pigmentary and non-pigmentary dispersants, fillers, adjusting agents, resins, waxes, defoamers, anti-dusting agents, extenders, colorants for shading, preservatives, drying retardants, additives for controlling the rheology, wetting agents , Antioxidants, UV absorbers, light stabilizers, or a combination thereof.
  • the auxiliaries can be added at any time before, during or after the reaction in the microreactor, all at once or in several portions.
  • the auxiliaries can be added, for example, directly to the solutions or suspensions of the reactants, but also during the reaction in liquid, dissolved or suspended form.
  • the total amount of auxiliaries added can be 0 to 40% by weight, preferably 1 to 30% by weight, particularly preferably 2.5 to 25% by weight, based on the naphthol AS pigment.
  • Suitable surfactants are anionic or anionic, cationic or cationic and nonionic substances or mixtures of these agents. Examples of surfactants, pigmentary and non-pigmentary dispersants which can be used for the process according to the invention are given in EP-A-1 195 411.
  • buffer solutions can also be added, preferably of organic acids and their salts, such as formic acid / formate buffer, acetic acid / acetate buffer, citric acid / citrate buffer; or of inorganic acids and their salts, such as phosphoric acid / phosphate buffer or carbonic acid / bicarbonate or carbonate buffer.
  • organic acids and their salts such as formic acid / formate buffer, acetic acid / acetate buffer, citric acid / citrate buffer
  • inorganic acids and their salts such as phosphoric acid / phosphate buffer or carbonic acid / bicarbonate or carbonate buffer.
  • the solvent washing according to the invention comprises the absorption of the naphthol AS pigment produced in step (a), either directly from the microreactor or after intermediate insulation, for example as a press cake (approx. 5 to 30% by weight solids content), in one of the organic solvents mentioned.
  • Preferred solvents are C3-C 4 alcohols, glycol ethers and chlorinated benzenes, such as butoxyethanol, ortho-dichlorobenzene, isobutanol, isopropanol, or a mixture thereof. It is also possible to use a pigment suspension treated according to (c).
  • the amount of solvent is preferably 1 to 30% by volume, in particular 5 to 15% by volume, based on the volume of the pigment suspension, or 1 to 10 times the amount by weight of solvent, based on the weight of the
  • the mixture of pigment suspension or press cake and solvent is preferably at a temperature between 10 and 50 ° C, in particular between 20 and 45 ° C, and preferably for 0.1 to 2 hours, in particular 0.25 to 1 hours, and preferably at normal pressure touched.
  • an inline dispersing machine equipped with appropriate dispersing tools, can also be used in the pumping around of the reservoir.
  • a dispersing machine firstly ensures intensive mixing of the suspension in the storage vessel, but at the same time it also has a deagglomerating effect, so that any inclusions are exposed.
  • the solvent-treated pigment suspension is then filtered and washed or fed to membrane purification (c).
  • Membrane purification
  • the membrane purification according to the invention comprises passing an azo colorant suspension obtained from step (a) or from (b) through a membrane system which is designed in such a way that the naphthol AS pigment is retained as completely as possible by the membrane.
  • Water or an organic solvent, optionally in a mixture with water, is particularly suitable as the liquid medium.
  • the solids concentration in the suspension is advantageously 1 to 10% by weight, preferably 2 to 5% by weight, based on the total weight of the suspension.
  • the driving force for the transmembrane mass transfer is a pressure difference between the two sides of the membrane.
  • the pressure difference is advantageously 0.5 to 5 bar, preferably 1 to 2 bar.
  • the pressure is measured, for example, by suitable pumps, e.g. Piston pumps.
  • Static membrane modules such as tube or plate modules, or dynamic membrane modules are preferably used.
  • the temperature is advantageously 0 to 100 ° C, in particular 20 to 80 ° C.
  • the membrane purification can also be carried out as diafiltration.
  • the retentate i.e. the azo pigment, returned to the original container and the water or solvent content kept constant by water make-up.
  • Step (a) significantly reduces the content of triazene and mixed triazene, ie mostly to below the detection limit of 50 ppm, but mostly there is still more than 100 ppm of free aromatic amine H 2 N-Ar and of unreacted coupling component, ie naphthol.
  • Step (b) or (c) preferably through the combination of (b) and (c), surprisingly succeeds in lowering the free amine and naphthol content often below the respective detection limit of 25 ppm or 100 ppm.
  • inorganic salts are also retained.
  • the high-purity naphthol AS pig ducks according to the invention are used in particular for coloring electrophotographic toners and developers, such as e.g. One- or two-component powder toners (also called one- or two-component developers), magnetic toners, liquid toners, latex toners, polymerization toners and special toners, powder coatings, inkjet inks and color filters as well as colorants for electronic inks (“electronic inks” or “e- inks ”) or” electronic paper “(" e-paper ").
  • electrophotographic toners and developers such as e.g. One- or two-component powder toners (also called one- or two-component developers), magnetic toners, liquid toners, latex toners, polymerization toners and special toners, powder coatings, inkjet inks and color filters as well as colorants for electronic inks (“electronic inks” or “e- inks ”)
  • Toner particles can also be used for cosmetic and pharmaceutical applications, e.g. for coating tablets.
  • Typical toner binders are polymerization, polyaddition and polycondensation resins, such as styrene, styrene-acrylate, styrene-butadiene, acrylate,
  • Polyester phenol epoxy resins, polysulfones, polyurethanes, individually or in
  • Waxes or flow aids can contain or modified with these additives afterwards.
  • the naphthol AS pigments according to the invention can of course also be used quite generally for pigmenting high molecular weight organic materials of natural or synthetic origin, for example plastics, resins, lacquers, paints, electrophotographic toners and developers, electret materials, color filters and also inks, printing inks and seeds.
  • High molecular weight organic materials that can be pigmented with the naphthol AS pigments according to the invention are, for example
  • Cellulose compounds such as cellulose ethers and esters such as ethyl cellulose, nitrocellulose, cellulose acetates or cellulose butyrates, natural binders such as fatty acids, fatty oils, resins and their Conversion products, or synthetic resins, such as polycondensates, polyadducts, polymers and copolymers, such as, for example, aminoplasts, in particular urea and melamine formaldehyde resins, alkyd resins, acrylic resins, phenoplasts and phenolic resins, such as novolaks or resols, resin resins, polyvinylyls, such as polyvinyl alcohols, polyvinyl ether acetates, polyvinyl acetates , Polycarbonates, polyolefins, such as polystyrene, polyvinyl chloride, polyethylene or polypropylene, poly (meth) acrylates and their copolymers, such as polyacrylic acid esters or polyacryl
  • the naphthol AS pigments according to the invention are used in an amount of 0.05 to 30% by weight, preferably 0.1 to 15% by weight.
  • This crude can be used to produce color concentrates in liquid or solid form in concentrations of 5 to 99% by weight, alone or optionally in a mixture with other crudes or finished pigments.
  • the invention furthermore relates to the use of the colorant preparation described as a colorant for printing inks, in particular for inkjet inks.
  • Ink-jet inks are understood to mean both inks on an aqueous (including microemulsion inks) and non-aqueous (“solvent-based”) basis, UV-curable inks and those inks which work according to the hot-melt process.
  • Ink-jet Solvent-based inks essentially contain 0.5 to 30% by weight, preferably 1 to 15% by weight, of one or more of the naphthol AS pigments according to the invention, 70 to 95% by weight of an organic solvent or solvent mixture and / or a hydrotropic compound.
  • the solvent-based ink-jet inks can contain carrier materials and binders which are soluble in the "solvent", such as, for example Polyolefins, natural and synthetic rubber, polyvinyl chloride, vinyl chloride / vinyl acetate copolymers, polyvinyl butyrals, wax / latex systems or combinations of these compounds.
  • the solvent-based ink jet inks can also contain other additives, such as Wetting agents, degassers / defoamers, preservatives and antioxidants.
  • Microemulsion inks are based on organic solvents, water and possibly an additional substance that acts as an interface mediator (surfactant).
  • Microemulsion inks contain 0.5 to 30% by weight, preferably 1 to 15% by weight, of the naphthol AS pigments according to the invention, 0.5 to 95% by weight of water and 0.5 to 95% by weight of organic solvents and / or interfacial agents.
  • UV-curable inks essentially contain 0.5 to 30% by weight of one or more of the naphthol AS pigments according to the invention, 0.5 to 95% by weight of water, 0.5 to 95% by weight of an organic solvent or Solvent mixture, 0.5 to 50 wt .-% of a radiation-curable binder and optionally 0 to 10 wt .-% of a photoinitiator.
  • Hot-melt inks are mostly based on waxes, fatty acids, fatty alcohols or sulfonamides, which are solid at room temperature and become liquid when heated, the preferred melting range being between approx. 60 and approx. 140 ° C.
  • Hot melt ink jet inks essentially consist of 20 to 90% by weight of wax and 1 to 10% by weight of one or more of the naphthol AS pigments according to the invention. Furthermore, 0 to 20% by weight of an additional polymer (as a "dye dissolver"), 0 to 5% by weight of dispersant, 0 to 20% by weight of viscosity modifier, 0 to 20% by weight of plasticizer, 0 to 10% by weight % Stickiness additive, 0 to 10% by weight transparency stabilizer (prevents, for example, the crystallization of the wax) and 0 to 2% by weight antioxidant.
  • an additional polymer as a "dye dissolver”
  • dispersant 0 to 20% by weight of viscosity modifier
  • plasticizer 0 to 20% by weight of plasticizer
  • Stickiness additive 0 to 10% by weight
  • transparency stabilizer prevents, for example, the crystallization of the wax
  • the printing inks according to the invention in particular ink-jet inks, can be produced by adding the Naphthol AS pigment into the microemulsion medium, into the non-aqueous medium or into the medium for producing the UV-curable ink or into the wax for producing a hot - Melt ink jet ink is dispersed.
  • the printing inks obtained are then advantageously filtered for ink-jet applications (e.g. using a 1 ⁇ m filter).
  • the naphthol AS pigments according to the invention are also used as colorants for color filters, both for additive and for subtractive color production, and as colorants for electronic inks (“electronic inks” or “e-inks”) or “electronic paper” ( "E-paper”) suitable.
  • electronic inks electronic inks
  • E-paper electronic paper
  • color filters both reflective and transparent color filters, pigments in the form of a paste or as pigmented photoresists in suitable binders (acrylates, acrylic esters, polyimides, polyvinyl alcohols, epoxies, polyesters, melamines, gelatins, caseins) are applied to the respective LCD Components (e.g.
  • the pigmented color filters can also be applied by ink jet printing processes or other suitable printing processes.
  • Example 1 C.I. Pigment Red 269
  • a buffer for the anis base diazonium salt solution 1884 g of water / ice are introduced, 502 g of acetic acid and 614 g of sodium hydroxide solution are added, and the temperature is kept at room temperature after the addition of 1 kg of water.
  • Azo coupling in the microreactor The anis base diazonium salt solution and the naphthol AS solution are pumped into the respective reactant inputs of the microreactor (type: Cytos from CPC-Systems / Frankfurt) at a flow rate of 8 ml / min.
  • the educt solutions are shortly before the reactor inputs diluted with an acetic acid / acetate buffer prepared according to a2).
  • the buffer solution is also pumped into the feed lines of the microreactor by means of calibrated piston pumps via a T-branch at a flow rate of 6 ml / min.
  • a thermostat is connected to the heat exchanger circuit of the microreactor, which sets the desired reaction temperature from 20 ° C to 35 ° C.
  • the pigment suspension obtained from the microreactor is mixed with an amount of butoxyethanol such that the entire slurry contains about 10% by volume of butoxyethanol.
  • the slurry is stirred at a temperature of about 45 ° C for 30 minutes, filtered off and washed with water. After taking the sample, the colorant-solvent-water suspension is subjected to the following membrane purification.
  • a ceramic multi-channel microfiltration membrane with a nominal separation limit of the separation-selective layer of 60 nm and a membrane area of 0.09 m 2 is used.
  • About 15 kg of the colorant suspension with a pigment content of about 2% by weight are placed in a temperature-controlled storage container.
  • the membrane is subjected to a pressure of about 1.5 bar at ambient temperature on the retentate side.
  • the mass of permeate removed is discontinuously replaced by demineralized water.
  • the exchange volume ie volume of demineralized water supplied / volume of pigment suspension used
  • the permeate flow is approximately 200 l / (m 2 * h * bar).
  • the initial chloride ion content is reduced from 2.5% after 10 hours of diafiltration to 920 ppm and the sulfate content from the initial 0.3% to 30 ppm.
  • Table 2 shows a comparison of the typical secondary component contents of the conventional batch pigment with the secondary component contents of the pigment from a synthesis in the microreactor [step a)] with subsequent solvent washing [step b)] and membrane purification [step c)].
  • Table 1 shows the values for the detection limit of the secondary components under consideration. The measurement accuracy of the chosen analysis method is approximately ⁇ 5 ppm.
  • Table 2 Comparison of the secondary component contents in the pigment from batch synthesis or microreactor synthesis with subsequent solvent washing and membrane purification.
  • Example 2 C.I. Pigment Red 146
  • Steps a) - d) were carried out analogously to Example 1.
  • the pigment obtained after step c) had an anise base, chloromethoxyaniline, anise base triazene and Naphtol AS content below the respective detection limit.
  • Example 3 Cl Pigment Red 147
  • Steps a) - d) were carried out analogously to Example 1.
  • the pigment obtained after step c) had an anise base, chloromethoxyaniline, anise base triazene and Naphtol AS content below the respective detection limit.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Paints Or Removers (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

L'invention concerne des pigments de naphtol-AS ultra-purs représentés par la formule (IV), dont la teneur maximale en constituants secondaires (1) à (5) est définie par les limites maximales indiquées dans le tableau.
EP05716543A 2004-04-22 2005-04-06 Pigments de naphtol-as ultra-purs Withdrawn EP1740658A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004019560A DE102004019560A1 (de) 2004-04-22 2004-04-22 Hochreine Naphthol AS-Pigmente
PCT/EP2005/003598 WO2005105928A1 (fr) 2004-04-22 2005-04-06 Pigments de naphtol-as ultra-purs

Publications (1)

Publication Number Publication Date
EP1740658A1 true EP1740658A1 (fr) 2007-01-10

Family

ID=34962425

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05716543A Withdrawn EP1740658A1 (fr) 2004-04-22 2005-04-06 Pigments de naphtol-as ultra-purs

Country Status (9)

Country Link
US (1) US20070240618A1 (fr)
EP (1) EP1740658A1 (fr)
JP (1) JP2007533802A (fr)
KR (1) KR20060135896A (fr)
CN (1) CN1946811A (fr)
BR (1) BRPI0510073A (fr)
CA (1) CA2563812A1 (fr)
DE (1) DE102004019560A1 (fr)
WO (1) WO2005105928A1 (fr)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5134794B2 (ja) * 2006-08-22 2013-01-30 東京色材工業株式会社 変異原性の低減されたナフトール系アゾ顔料組成物およびその製造方法
JP2010195909A (ja) * 2009-02-25 2010-09-09 Toyo Ink Mfg Co Ltd 顔料組成物およびインクジェット印刷用インキ
KR102116438B1 (ko) * 2012-05-21 2020-05-29 토요잉크Sc홀딩스주식회사 컬러 필터용 착색 조성물 및 컬러 필터
KR102116437B1 (ko) * 2012-05-21 2020-05-29 토요잉크Sc홀딩스주식회사 안료 조성물, 그 제조 방법, 착색 조성물, 및 컬러 필터
JP5327399B1 (ja) * 2012-05-21 2013-10-30 東洋インキＳｃホールディングス株式会社 顔料組成物とその製造方法、それを用いた着色組成物、カラーフィルタ
JP6246120B2 (ja) 2012-06-26 2017-12-13 保土谷化学工業株式会社 カラーフィルター用キサンテン系色素並びに該色素を用いたカラーフィルター
KR102560580B1 (ko) 2015-03-24 2023-07-26 호도가야 가가쿠 고교 가부시키가이샤 크산텐계 염료를 함유하는 청색계 착색 조성물, 컬러 필터용 착색제 및 컬러 필터
WO2016159037A1 (fr) * 2015-03-31 2016-10-06 東洋インキＳｃホールディングス株式会社 Encre magenta pour enregistrement à jet d'encre
JP6481526B2 (ja) * 2015-06-19 2019-03-13 富士ゼロックス株式会社 静電荷像現像用トナー、静電荷像現像剤、トナーカートリッジ、プロセスカートリッジ、画像形成装置及び画像形成方法
DE102015211829A1 (de) 2015-06-25 2016-12-29 Clariant International Ltd Verwendung von neuen Naphthol AS-Pigment-Mischungen in Printing-Materialien
DE102015211827A1 (de) * 2015-06-25 2016-12-29 Clariant International Ltd Neue Naphthol AS-Pigmente
EP3181642A1 (fr) 2015-12-14 2017-06-21 Cappelle Pigments nv Procédé de fabrication de pigments azoïques
CN105524484B (zh) * 2016-01-14 2018-04-10 上虞市新利化工有限公司 一种c.i.颜料红176的制备方法
JP6065149B1 (ja) * 2016-06-01 2017-01-25 コニカミノルタ株式会社 静電荷像現像用トナー
JP6763213B2 (ja) * 2016-06-29 2020-09-30 Dic株式会社 新規アゾ化合物
JP7109943B2 (ja) * 2017-03-27 2022-08-01 キヤノン株式会社 顔料分散体、トナーの製造方法、水性インク及びトリアゾ化合物
CN110997822B (zh) 2017-06-29 2023-01-03 保土谷化学工业株式会社 含有呫吨系染料的着色组合物、滤色器用着色剂和滤色器
DK3434737T3 (da) 2017-07-26 2023-03-27 Evonik Operations Gmbh Modificerede pigmenter og deres anvendelse
JP6368844B1 (ja) 2017-08-25 2018-08-01 東洋インキＳｃホールディングス株式会社 アゾ顔料、カラーフィルタ用着色剤、着組成物およびカラーフィルタ
TWI805622B (zh) 2017-10-24 2023-06-21 日商保土谷化學工業股份有限公司 含有包含二苯并哌喃系陽離子染料及有機陰離子之成鹽化合物之著色組合物、彩色濾光片用著色劑及彩色濾光片
US11549018B2 (en) * 2017-12-01 2023-01-10 Sanyo Color Works, Ltd. Pigment composition
US10599060B2 (en) 2017-12-06 2020-03-24 Canon Kabushiki Kaisha Toner
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
CN110511593B (zh) 2018-05-21 2022-07-08 东洋油墨Sc控股株式会社 偶氮颜料、彩色滤光片及用于其的着色剂与着色组合物、以及包含其的显示装置与摄像元件
JP2020148822A (ja) * 2019-03-11 2020-09-17 富士ゼロックス株式会社 静電荷像現像用トナー、静電荷像現像剤、トナーカートリッジ、プロセスカートリッジ、画像形成装置及び画像形成方法
CN112048215A (zh) 2019-06-05 2020-12-08 株式会社理光 墨水以及印刷方法
CN111039812B (zh) * 2020-01-13 2023-01-06 泰安岳海新材料股份有限公司 一种微通道连续法制备色酚as-ol的方法
CN111607247A (zh) * 2020-06-16 2020-09-01 杭州百合科莱恩颜料有限公司 一种混晶型色酚as有机颜料及其制备方法

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2533603A1 (de) * 1975-07-26 1977-02-10 Bayer Ag Herstellung von azofarbstoffen unter zerkleinerung
US4159264A (en) * 1975-08-09 1979-06-26 Ciba-Geigy Corporation Automatic control of azo coupling processes in the manufacture of azo pigments
GB2021132B (en) * 1978-02-14 1982-07-21 Ici Ltd Azo coupling process
GB2014597A (en) * 1978-02-14 1979-08-30 Ici Ltd Continuous Coupling Process
CH655125A5 (de) * 1983-09-21 1986-03-27 Ciba Geigy Ag Verfahren zur herstellung von azofarbstoffpraeparaten.
CH660494B (fr) * 1984-12-12 1987-04-30
DE3926466C2 (de) * 1989-08-10 1996-12-19 Christoph Dipl Ing Caesar Mikroreaktor zur Durchführung chemischer Reaktionen von zwei chemischen Stoffen mit starker Wärmetönung
WO2001059013A1 (fr) * 2000-02-09 2001-08-16 Clariant International Ltd Procede de production de colorants azoiques dans des microreacteurs
US6432192B1 (en) * 2000-02-23 2002-08-13 Flint Ink Corporation Process for manufacturing pigments
DE10049200A1 (de) * 2000-10-05 2002-04-11 Clariant Gmbh Verfahren zur Herstellung von Azofarbmitteln
DE10143189A1 (de) * 2001-09-04 2003-03-20 Clariant Gmbh Verfahren und Vorrichtung zur prozeßbegleitenden Reinigung von Mikro-und Minireaktoren
JP2003162097A (ja) * 2001-11-26 2003-06-06 Kyocera Mita Corp 正帯電マゼンタトナー
JP3963795B2 (ja) * 2002-07-09 2007-08-22 大日精化工業株式会社 トナー
JP3891280B2 (ja) * 2002-07-26 2007-03-14 日本ゼオン株式会社 マゼンタトナー
JP2004070005A (ja) * 2002-08-06 2004-03-04 Kao Corp レッドトナー
JP2004117649A (ja) * 2002-09-25 2004-04-15 Dainippon Ink & Chem Inc 赤色トナー

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2005105928A1 *

Also Published As

Publication number Publication date
WO2005105928A1 (fr) 2005-11-10
CA2563812A1 (fr) 2005-11-10
JP2007533802A (ja) 2007-11-22
US20070240618A1 (en) 2007-10-18
BRPI0510073A (pt) 2007-10-16
DE102004019560A1 (de) 2005-11-10
CN1946811A (zh) 2007-04-11
KR20060135896A (ko) 2006-12-29

Similar Documents

Publication Publication Date Title
EP1740658A1 (fr) Pigments de naphtol-as ultra-purs
WO2005105927A1 (fr) Procede de fabrication de colorants azo ultra-purs
EP1257602B1 (fr) Procede de production de colorants azoiques dans des microreacteurs
EP1167461B1 (fr) Procédé de conditionnement de pigments organiques
EP1195411A1 (fr) Procédé pour la préparation de colorants azoiques
EP1882019B1 (fr) Pigment azoique a fines particules et procede de realisation associe
EP1664203B1 (fr) Compositions pigmentaires contenant des pigments organiques et des pigments inorganiques
EP1558682A1 (fr) Procede et dispositif pour mettre en oeuvre des procedes chimiques et physiques
DE10353127A1 (de) Pigmentzusammensetzungen aus gelbem Disazopigment und organischem Pigment
EP1694778B1 (fr) Preparations pigmentaires monoazo a base de pigment jaune c.i. 74
EP2228410B1 (fr) Pigment rouge C.I. 112 doté d'une aptitude à la dispersion améliorée
DE10227527A1 (de) Verfahren zur Herstellung von Disazopigmenten
WO2016206925A1 (fr) Nouveaux pigments de naphtol as
EP1417264B1 (fr) Nouveaux pigments azoiques
DE10161609A1 (de) Verfahren zur Herstellung feinteiliger Azofarbmittelpräparationen für den Ink-Jet-Druck

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20061122

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU MC NL PL PT RO SE SI SK TR

RIN1 Information on inventor provided before grant (corrected)

Inventor name: ROHR, ULRIKE

Inventor name: BAUR, RUEDIGER

DAX Request for extension of the european patent (deleted)
17Q First examination report despatched

Effective date: 20100429

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN

18W Application withdrawn

Effective date: 20100819