EP2137265A2 - Procede de mise en forme de pigments organiques - Google Patents

Procede de mise en forme de pigments organiques

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Publication number
EP2137265A2
EP2137265A2 EP08736136A EP08736136A EP2137265A2 EP 2137265 A2 EP2137265 A2 EP 2137265A2 EP 08736136 A EP08736136 A EP 08736136A EP 08736136 A EP08736136 A EP 08736136A EP 2137265 A2 EP2137265 A2 EP 2137265A2
Authority
EP
European Patent Office
Prior art keywords
pigment
acid
crystallization
crystallization modifier
solution
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Withdrawn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
EP08736136A
Other languages
German (de)
English (en)
Inventor
Joachim Jesse
Benno Sens
Andres Carlos Garcia Espino
Richard Van Gelder
Matthias KLÜGLEIN
Ines Pietsch
Wolfgang Best
Rainer Henning
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
Priority to EP08736136A priority Critical patent/EP2137265A2/fr
Publication of EP2137265A2 publication Critical patent/EP2137265A2/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Withdrawn legal-status Critical Current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
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
    • 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
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0002—Grinding; Milling with solid grinding or milling assistants
    • 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
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0017—Influencing the physical properties by treatment with an acid, H2SO4
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0034—Mixtures of two or more pigments or dyes of the same 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
    • 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
    • C09B67/006—Preparation of organic pigments
    • 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
    • C09B67/0084—Dispersions of dyes
    • C09B67/0085—Non common dispersing agents
    • C09B67/0086—Non common dispersing agents anionic dispersing agents
    • 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
    • C09B67/0084—Dispersions of dyes
    • C09B67/0085—Non common dispersing agents
    • C09B67/009—Non common dispersing agents polymeric dispersing agent

Definitions

  • the invention relates to a process for the formation of organic pigments using condensation products based on hydroxyarylsulfonic acids or hydroxydiarylsulfone compounds as crystallization modifiers, the resulting organic pigments themselves and the use of the condensation products as crystallization modifiers for the formation of organic pigments.
  • Organic pigments often accumulate in the synthesis in coarsely crystalline form with very heterogeneous particle size distribution.
  • the crude pigments are therefore usually subjected to a formation.
  • a grinding of the crude pigment and subsequent recrystallization of the millbase in an organic solvent is known, or the grinding is carried out as a wet grinding in aqueous suspension in high-speed stirred ball mills.
  • the methods described achieve particle size reduction and thus an improvement in the coloristic properties of the pigments, sometimes with a high expenditure of time, it is difficult to control the particle size of the pigments obtained, and the pigments are frequently used in a number of applications. For example, as a colorant for paints and in ink-jet inks, insufficient, because too broad particle size distribution on.
  • WO 02/00643 discloses a process for the formation of quinophthalone crude pigments, in which the crude pigment obtained in the synthesis is subjected to milling in the absence of grinding aids and the resulting millbase is subsequently treated in the presence of a quinophthalone derivative in an organic solvent or a mixed organic solvent and water crystallize.
  • derivatives which are mentioned are sulfonic acid derivatives of quinophthalone pigments.
  • WO 2004/048482 discloses a process for the formation of organic pigments, in which the pigment is dissolved in concentrated sulfuric acid and the sulfuric acid solution is mixed with water in the presence of a condensation product of naphthalenesulfonic acid and formaldehyde as crystallization modifier.
  • the crystallization modifier Tor is added to the sulfuric acid pigment solution or it is generated in this by reacting 1- and 2-naphthalenesulfonic acid with formaldehyde in situ.
  • the object of the invention is to provide further advantageous processes for the formation of organic pigments, which give pigments with very good coloristic properties.
  • the object is achieved by a process for forming ("finishing") an organic pigment, in which the pigment is dissolved or dispersed in an aqueous solvent or a mineral acid and crystallized from the solution or dispersion, the pigment in the presence of a crystallization modifier and then the Isolated pigment as a solid, which is characterized in that the crystallization modifier a sulfonate containing condensation product of at least one Hydroxyarylsulfonkla and / or at least one HydroxydiarylsulfonENS and at least one aliphatic aldehyde having 1 to 6 carbon atoms, optionally urea and optionally an alkali metal sulfite, or a mixture of such condensation products.
  • the crystallization modifier a sulfonate containing condensation product of at least one Hydroxyarylsulfonklare and / or at least one Hydroxydiarylsulfonharm and at least one aliphatic aldehyde having 1 to 6 carbon atoms
  • Crystallization or crystallization in the sense of the present invention is not only the precipitation of the pigment as a solid from its solution, but also the "finishing" of the pigment, which is accompanied by a partial recrystallization of the pigment.
  • the crystallization modifier may be a condensation product of one or more different hydroxyarylsulfonic acids and one or more different aliphatic aldehydes of 1 to 6 carbon atoms. Generally, with 0.25 to 4 moles of aliphatic aldehyde is condensed per mole of hydroxyaryl units present. If urea is used, it is generally used in amounts of from 0.25 to 4 mol of urea per mole of hydroxyaryl units present. In addition to hydroxyarylsulfonic acid, one or more different hydroxydiarylsulfone compounds can be condensed in the condensation product.
  • the preparation of the condensation product can furthermore be carried out in the presence of an alkali metal sulfite, preferably sodium sulfite, with further sulfonate groups being introduced into the condensation product in addition to the sulfonate groups introduced by the hydroxyarylsulfonic acid.
  • an alkali metal sulfite preferably sodium sulfite
  • the crystallization modifier may be a condensation product of one or more different hydroxydiarylsulfone compounds, one or more different aliphatic aldehydes having 1 to 6 carbon atoms and an alkali metal sulfite, preferably sodium sulfite.
  • the sulfonate groups are here introduced as Alkylsulfonat phenomenon in the condensation product.
  • the hydroxydiarylsulfone compound is reacted with 0.5 to 5 mol of the aliphatic aldehyde and 0.4 to 2 mol of the alkali metal sulfite per mole of hydroxydiarylsulfone compound.
  • Suitable hydroxyarylsulfonic acids which can be used to prepare the crystallization modifiers used according to the invention are, for example, hydroxyphenylsulfonic acids or hydroxynaphthylsulfonic acids. These may also have several hydroxyl groups.
  • Preferred hydroxyarylsulfonic acid is phenolsulfonic acid.
  • Suitable hydroxydiarylsulfone compounds which can be used for the preparation of the condensation products used according to the invention are, for example, dihydroxydiphenylsulfones or, more generally, polyhydroxydiphenylsulfones and dihydroxydinaphthylsulfones or, more generally, polyhydroxydinaphthylsulfones.
  • Preferred hydroxydiarylsulfone compound is dihydroxydiphenylsulfone (DHDPS).
  • hydroxyarylsulfonic acids and hydroxydiarylsulfones are prepared by sulfonation of the corresponding hydroxyaryl compounds, for example of naphthols, phenol or polyphenols, with concentrated sulfuric acid or oleum.
  • mixtures of hydroxyarylsulfonic acids and hydroxydiarylsulfones are formed.
  • a crystallization modifier which is obtainable by treating phenol with concentrated sulfuric acid, with an oleic acid having a content of from 20 to 65% by weight or with a mixture of sulfuric acid and oleum Molar ratio of total sulfuric acid, calculated as SO 3 , to phenol from 0.7: 1 to 1, 5: 1, at a temperature of 100 to 180 0 C to a mixture containing phenolsulfonic acid, dihydroxydiphenylsulfone and sulfuric acid react, or by mixing the individual Components produces a corresponding mixture, and then at 40 to 90 0 C per mole of phenol units present with 0.5 to 4 mol of an aliphatic aldehyde having 1 to 6 carbon atoms, preferably formaldehyde, and - optionally - with 0.25 to 4 mol Urea condenses.
  • a crystallization modifier which is obtainable by reacting dihydroxydiphenylsulfone with 0.5 to 5 mol of an aliquot of - A -
  • aldehyde having 1 to 6 carbon atoms, preferably formaldehyde, and 0.4 to 2 moles of sodium sulfite per mole of dihydroxydiphenyl sulfone at a temperature of 90 to 180 0 C react.
  • the condensation products generally act as crystallization inhibitors.
  • the condensation product containing sulfonate groups can be isolated, for example by precipitation of the condensation product by addition of a water-miscible liquid in which the condensation product is insoluble, or by evaporation of the liquid reaction medium, for example by spray drying.
  • the organic pigment is dissolved or dispersed in an aqueous solvent or in a mineral acid and allowed to crystallize from the solution or dispersion in the presence of the crystallization modifier.
  • the pigment is dissolved in concentrated sulfuric acid and allowed to crystallize by mixing the solution with an aqueous diluent.
  • the crystallization modifier may be contained both in the sulfuric acid solution of the pigment and in the aqueous diluent.
  • the mixing takes place by combining the sulfuric acid pigment solution and the aqueous diluent by means of a mixing nozzle.
  • Aqueous diluent here is generally water which may contain the crystallization modifier.
  • the crystallization can also be effected by pouring the sulfuric acid pigment solution into water, preferably ice-water.
  • the concentration of the pigment in the concentrated sulfuric acid is 1 to 30% by weight.
  • the crystallization modifier is generally present in amounts of from 0.1 to 30% by weight, based on the pigment.
  • the volume of the aqueous diluent is generally 1 to 12 times the volume of the sulfuric acid pigment solution.
  • the crystallization modifier is generated in situ in the sulfuric acid solution of the pigment.
  • the crystallized organic pigment is allowed to mature in the presence of a surfactant.
  • the surfactant may already be added to the aqueous diluent or added after the crystallization step to the pigment suspension, generally as an aqueous solution.
  • the ripening of the crystallized organic pigment is generally carried out by stirring the pigment suspension at temperatures generally from 40 to 100 ° C. over a period of from 0.5 to 5 hours. This leads to the growth of larger pigment particles at the expense of smaller pigment particles and / or to a smoothing / healing of the crystal surface of the pigment particles.
  • Suitable surfactants are the anionic, cationic, nonionic and amphoteric surfactants mentioned below.
  • the pigment is dispersed in dilute aqueous sulfuric acid and swollen in the presence of the crystallization modifier. It is advantageous to grind the pigment together with the crystallization modifier before swelling, for example in a stirred ball mill. It is particularly advantageous to mill the pigment together with the crystallization modifier and a surface-active agent, in particular a synthetic and / or natural resin such as rosin, hydrogenated, partially hydrogenated, disproportionated, dimensêtm or polymerized Kolophorium before swelling. The swelling results in the growth of larger pigment particles at the expense of smaller pigment particles and / or in a smoothing / healing of the crystal surfaces of the pigment particles.
  • Suitable dilute sulfuric acid generally has a concentration of 50 to 85, preferably 60 to 85 wt .-% on.
  • the swelling of the pigment in the dilute aqueous sulfuric acid in the presence of the crystallization modifier is generally carried out at temperatures of 15 to 90 0 C over a period of generally 0.5 to 24 hours. The optimum swelling conditions can be determined for each type of pigment in preliminary tests. Then it is diluted with water. This is generally to the Sulfuric acid pigment dispersion 2 to 6 times added to water. Subsequently, stirring is generally continued for 0.5 to 2 hours.
  • the swelling of the pigment may also be carried out as an aftertreatment step, preferably with the pigment obtained by the above-described method of precipitation with an aqueous diluent and isolated as a solid.
  • the pigment obtained, for example, by precipitation is dispersed in water and crystallized in the presence of the crystallization modifier and an additive which increases the solubility of the pigment.
  • an organic solvent is added as the solubility enhancing additive. Suitable organic solvents are, for example, xylenes, glycols, alcohols, THF, acetone, NMP, DMF and nitrobenzene. These are, based on the aqueous pigment suspension, generally in an amount of 0.1 to 50 wt .-% added.
  • the amount of crystallization modifier is generally 0.1 to 30 wt .-%, based on the aqueous pigment suspension (without organic solvent).
  • the suspension is stirred in the presence of the organic solvent at temperatures in the range of 15 ° C. to the boiling point and then the organic solvent is distilled off.
  • the process can also be carried out without solvent under elevated pressure. In this case, a controlled by the crystallization modifier crystal growth of the pigment by Ostwald ripening takes place.
  • the step can also be carried out as an aftertreatment step, for example with the pigment obtained by the above-described method of precipitation with an aqueous diluent and isolated as a solid.
  • the pigment crystallized in the presence of the crystallization modifier is subsequently isolated as a solid by filtration of the aqueous suspension.
  • a solution of the pigment in concentrated sulfuric acid is prepared and mixed with water, preferably using a mixing nozzle.
  • the suspension is stirred, generally at a temperature in the range of 15 to 90 0 C over a period of 0.5 to 8 hours, the pigment is filtered off and preferably washed with water.
  • the resulting pigment is suspended in water and allowed to crystallize in the presence of crystallization modifier and solubility enhancing additive.
  • Suitable dispersants are, for example, sulfonic acid-containing pigment derivatives such as copper phthalocyaninesulfonic acid.
  • Suitable pigments which can be formed by the process according to the invention are, for example, azo, azomethine, methine, anthraquinone, phthalocyanine, perinone, perylene, diketopyrrolopyrrole, thioindigo, thiazine indigo, dioxazine, iminoisoindoline , Iminoisoindolinone, quinacridone, flavanthrone, indanthrone, anthrapyrimidine and quinophthalone pigments.
  • Preferred pigments are phthalocyanines, perylenes, quinacridones, indanthrones, quinaphthalones, dioxazines and diketopyrroles, particular preference is given to phthalocyanines, perylenes and indanthrones.
  • pigments of the type Cl. Pigment Red 179 are preferred. These can be prepared by various methods. Thus, perylene-3,4,9,10-tetracarboxylic diimide with a methylating agent to Cl. Pigment Red 179 be methylated or perylenetetracarboxylic anhydride with methylamine to Cl. Pigment Red 179 to be condensed. The latter is preferably used. However, it is also possible to use mixtures of the pigments prepared by these two methods. It is also possible to use pigment derivatives prepared by these methods or mixtures thereof.
  • the crystallization modifier used according to the invention is generally present during crystallization in amounts of from 0.1 to 30% by weight, preferably from 0.3 to 25% by weight, more preferably from 1 to 22% by weight, based on the pigment suspension , in front. In some cases it may be advantageous to use besides other crystallization modifiers, dispersants, surfactants or special polymers. Examples of further crystallization modifiers are imidazolemethyl or pyrazolemethylquinacridone pigment sulfonic acids.
  • surfactants examples include anionic surfactants such as alkylbenzenesulfonates or alkylnaphthalenesulfonates or alkylsulfosuccinates, cationic surfactants such as quaternary ammonium salts, for example benzyltributylammonium chloride, or nonionic or amphoteric surfactants such as polyoxyethylene surfactants and alkyl or amidopropyl betaines.
  • anionic surfactants such as alkylbenzenesulfonates or alkylnaphthalenesulfonates or alkylsulfosuccinates
  • cationic surfactants such as quaternary ammonium salts, for example benzyltributylammonium chloride
  • nonionic or amphoteric surfactants such as polyoxyethylene surfactants and alkyl or amidopropyl betaines.
  • Suitable special polymers are, for example, homo- and copolymers of maleic acid, polyacrylic acid, polymethacrylic acid, polyurethanes, polyvinyl alcohol, polyvinylpyrrolidone or cellulose derivatives.
  • the pigment isolated as a solid is mixed with a pigment synergist.
  • a pigment synergist is generally a sulfonate or carbonate group-containing derivative of an organic pigment or its salt, or a basic derivative of the aforementioned pigments.
  • the pigment synergist is a derivative of the pigment with which the Synergist is mixed.
  • the pigment synergist is used in amounts of 0.1 to 15% by weight, preferably 0.5 to 10% by weight, based on the finished pigment formulation.
  • the average particle size of the formed pigments is generally in the range of 10 to 400 nm, preferably 20 to 200 nm.
  • the pigments formed by the process according to the invention may contain the crystallization modifier on the surface of the pigment particles.
  • the subject matter therefore also includes pigment preparations comprising particles of an organic pigment with a superficial coverage of the pigment particles with the crystallization modifier used according to the invention.
  • the pigment preparations may contain, in addition to the already mentioned pigment synergists, further additives, generally in amounts of up to 15% by weight.
  • Further additives are, for example, wetting agents, surfactants, antifoams, antioxidants, UV absorbers, stabilizers, plasticizers and texturizing aids. These additives can be added already during the forming step.
  • the pigment preparations are used for dyeing and coating natural and synthetic materials.
  • the testing of the pigment preparations according to the invention takes place in an aqueous lacquer system.
  • a water tinting paste is first prepared based on a water-dilutable polyurethane resin.
  • 100 g of the polyurethane resin dispersion described in Example 1.3 of WO-A-92/15405, 30 g of the pigment preparation and 50 g of water are suspended, adjusted to a pH of 8 with dimethylethanolamine and placed in a ball mill (loading with 1.0%).
  • this water tinting paste (15% strength by weight based on pigment) are added to 225 g of a polyurethane-based compounding varnish (described in Example 3 of WO-A 92/15405). After adding 7.5 g of water with aminoethanol becomes a pH set by 8. The resulting suspension is stirred for 15 minutes with a propeller stirrer at 1000 rpm.
  • Crystallization Modifier K1 is prepared according to Example 2 of DE-A 101 40 551.
  • aqueous solution of sodium hydroxide By adding a little 20 wt .-% aqueous solution of sodium hydroxide is adjusted in the reaction mixture, a pH of 8 to 8.5 a. Subsequently, the pressure reactor is closed and the reaction mixture is heated to 115 0 C with stirring. After a short time at this temperature the reaction starts. The temperature of the reaction mixture rise to 150 to 160 0 C and the pressure in the pressure reactor to 4 to 5 bar (pressure) at. By external heating, the temperature of the reaction mixture is maintained at 160 0 C. After stirring the reaction mixture for 3 hours at 160 ° C., the reaction mixture is cooled to room temperature and mixed with 400 kg of sodium bisulfate. The resulting solution has a solids content of about 46 wt .-%.
  • Example 2 50 parts of the pigment preparation from Example 2 are ground together with 2.5 parts of a perfluoro-containing perylene compound prepared according to EP 0 636 666 A2 (derivative (b2) from page 7, line 27 of EP 0 636 666 A2).
  • the metallic coating containing the pigment preparation is even more transparent and yellower than that according to Example 2.
  • Example 2 50 parts of the pigment preparation from Example 2 are ground together with 3.75 parts of a sulfonic acid-containing perylene compound (prepared according to Example 3 of EP 0 486 531 B1).
  • the metallic finish of this pigment preparation is even more transparent and yellower than that according to Example 2.
  • a pigment preparation is obtained which, in an aqueous coating system based on a water-dilutable polyurethane resin, gives a strongly colored and transparent coating having a yellowish red hue.
  • the metallic finish is strong and brilliant.
  • Example 5 50 parts of the pigment preparation from Example 5 are ground together with 3.75 parts of a sulfonic acid-containing perylene compound (prepared according to Example 3 of EP 0 486 531 B1). The metallic finish of this pigment preparation is even more transparent and yellower than that according to Example 5.
  • the aqueous coating system based on a water-dilutable polyurethane resin has a lower viscosity than that of Example 6.
  • a pigment preparation is obtained which, in an aqueous coating system based on a water-dilutable polyurethane resin, gives a strongly colored and transparent coating having a yellowish red hue.
  • the metallic finish is strong and brilliant.
  • Example 8 100 parts of the pigment preparation from Example 8 are used together with 5 parts of a sulfonic acid-containing perylene compound (prepared according to Example 3 of EP 0 486 531 B1) ground. There is obtained a preparation with high transparency, which has a much more yellowish hue in aqueous metallic paints than the pigment preparation according to Example 8.
  • the preparation has a much higher transparency and a yellower hue than a corresponding preparation prepared without the crystallization inhibitor.
  • the mixture is diluted with 2 l of ice water, stirred for 30 min, filtered, washed neutral and ground together with 3.75 parts of a sulfonic acid-containing perylene compound (prepared according to Example 3 of EP 0 486 531 B1).
  • the preparation has a much higher transparency and a yellower hue than a corresponding preparation prepared without the crystallization inhibitor.
  • the mixture is diluted with 2 l of ice water, stirred for 30 min, filtered, washed neutral and ground together with 3.75 parts of a sulfonic acid-containing perylene compound (prepared according to Example 3 of EP 0 486 531 B1).
  • the pigment preparation of Example 12 has a higher transparency and a yellower and more chromatic hue than that of Example 1. With excellent rheological properties it is moreover readily dispersible in water-dilutable coating systems. Due to the high transparency, the pigment of Example 12 is particularly suitable for the pigmentation of metallic paints.
  • a solution of 80 g of indanthrone PB 60 in 987 g of 96 wt .-% sulfuric acid is stirred for two hours and while heated to 25 0 C.
  • This solution is combined with a 0.3 wt.% Aqueous solution of K1 in a ratio of 2.5 parts of K1 solution to one part of pigment solution via a mixing nozzle.
  • the temperature rises to DA at 60 0 C.
  • the mixture is then stirred at 60 0 C for 30 minutes.
  • the suspension is filtered, washed with deionized water until ⁇ 100 ⁇ S, then dried in a drying oven at 80 0 C under vacuum.
  • the coffee grinder is ground for 20 seconds at maximum speed.
  • the resulting pigment has a high transparency and a good flop behavior, ie a low viewing angle-dependent hue shift.
  • a pigment solution prepared as in Example 12 is mixed with 2.5 parts of water over a mixing nozzle together. The temperature rises to 60 0 C. The mixture is then stirred at 60 0 C for 30 minutes. The suspension is filtered and the filter cake is washed with demineralized water to ⁇ 100 ⁇ S. Subsequently, the filter cake is stirred up again in demineralized water and 10 wt .-% K1, based on the pigment was added. The suspension is charged in a jacketed reactor, heated to 60 0 C within one hour. At the temperature, 20 g of p-xylene is added and stirred for two hours. The mixture is then distilled off at 100 0 C xylene. Then the suspension is filtered off, the filter cake washed with a little water and dried at 80 0 C in a vacuum oven. The pigment has a high transparency and a high chroma.
  • Example 12 In the pigment solution prepared as in Example 12, 4 g of Cu phthalocyanine is added. This solution is then run with 2.5 parts of water through a mixing nozzle together. The temperature rises to 60 0 C. The mixture is then stirred at 60 0 C for 30 minutes. The suspension is filtered and the filter cake is washed with demineralized water to ⁇ 100 ⁇ S. Subsequently, the filter cake is stirred up again in demineralized water and 10 wt .-% K1, based on the pigment added. The suspension is introduced into a jacketed reactor and heated to 60 0 C within one hour. At the temperature, 20 g of p-xylene is added and stirred for two hours. The mixture is then distilled off at 100 0 C xylene.
  • the pigment has a high transparency and a high chroma.
  • the preparation of the crystallization modifier K2 is carried out according to Example 1 of DE-A 101 40 551.
  • 40 kmol heated to 60 0 C phenol are added within 1 hour with 40 kmol oleum with an SO ß content of 24 wt .-%.
  • the resulting mixture is heated to 160 0 C and stirred for 4 hours at this temperature.
  • the mixture is then allowed to cool to 80 0 C and 25 kmol urea are stirred as a 68 wt .-% solution and then metered within 1, 5 hours 40 kmol formaldehyde as a 30 wt .-% aqueous solution.
  • the resulting mixture is then mixed with about 34 kmol NaOH in the form of a 50 wt .-% aqueous solution, wherein a pH of 4.5 sets.
  • dihydroxydiphenylsulfone 10 wt .-%, based on the dry weight.
  • Example 16 50 parts of the pigment preparation from Example 16 are milled with 3.75 parts of the perylene compound containing sulfonic acid groups prepared according to Example 3 of EP 0 486 531 B1.
  • a pigment preparation is obtained which, in an aqueous coating system based on a water-dilutable polyurethane resin, gives a strongly colored and transparent coating having a yellowish red hue.
  • the metallic finish is strong and brilliant.

Abstract

L'invention concerne un procédé de mise en forme d'un pigment organique, dans lequel le pigment est dissous ou dispersé dans un solvant aqueux ou un acide minéral et est amené à cristalliser à partir de la solution ou de la dispersion en présence d'un modificateur de cristallisation et isolé ensuite sous forme de matières solides, le modificateur de cristallisation étant un produit de condensation présentant des groupes sulfonate constitué d'au moins un acide hydroxyarylsulfonique et/ou au moins un composé hydroxydiarylsulfonique et au moins un aldéhyde aliphatique ayant 1 à 6 atomes de C, de manière optionnelle de l'urée et éventuellement un sulfite alcalin, ou un mélange de ce type de produits de condensation.
EP08736136A 2007-04-13 2008-04-11 Procede de mise en forme de pigments organiques Withdrawn EP2137265A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP08736136A EP2137265A2 (fr) 2007-04-13 2008-04-11 Procede de mise en forme de pigments organiques

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP07106104 2007-04-13
EP08736136A EP2137265A2 (fr) 2007-04-13 2008-04-11 Procede de mise en forme de pigments organiques
PCT/EP2008/054425 WO2008125628A2 (fr) 2007-04-13 2008-04-11 Procédé de mise en forme de pigments organiques

Publications (1)

Publication Number Publication Date
EP2137265A2 true EP2137265A2 (fr) 2009-12-30

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP08736136A Withdrawn EP2137265A2 (fr) 2007-04-13 2008-04-11 Procede de mise en forme de pigments organiques

Country Status (6)

Country Link
US (1) US20100043672A1 (fr)
EP (1) EP2137265A2 (fr)
JP (1) JP2010523783A (fr)
KR (1) KR20100016078A (fr)
CN (1) CN101657508A (fr)
WO (1) WO2008125628A2 (fr)

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EP2185652B1 (fr) * 2007-08-03 2010-12-01 Basf Se Procede de formation de pigments organiques
KR101659645B1 (ko) 2013-10-02 2016-09-26 롯데첨단소재(주) 방향족 탄산에스테르의 제조방법
KR101752952B1 (ko) 2014-04-30 2017-07-04 롯데첨단소재(주) 유기금속화합물을 이용한 탄산에스테르의 제조방법
CN107815716B (zh) * 2017-09-12 2019-09-20 广东长盈精密技术有限公司 对工件的表面进行处理的方法
CN115011138B (zh) * 2022-05-18 2023-11-17 宁夏彩妍科技有限公司 液晶显示屏用颜料红177的生产方法及生产系统

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Also Published As

Publication number Publication date
JP2010523783A (ja) 2010-07-15
WO2008125628A2 (fr) 2008-10-23
KR20100016078A (ko) 2010-02-12
WO2008125628A3 (fr) 2009-04-09
US20100043672A1 (en) 2010-02-25
CN101657508A (zh) 2010-02-24

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