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Copper Phthalocyanine Pigment Process

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Copper Phthalocyanine Pigment Process Patentamt 0 081 840 JEuropàischesEuropean Patent Office ® Publication number: B1 Office européen des brevets ® EUROPEAN PATENT SPECIFICATION ® Date of publication of patent spécification: 29.10.86 © Int. Ci.4: C 09 B 67/16 (à) Application number: 82111576.3 ® Dateoffiling: 14.12.82 1 (54) Copper phthalocyanine pigment process. (30) Priority: 14.12.81 US 330333 @ Proprietor: TOYO INK Manufacturing Co., Ltd. No. 3-13, Kyobashi 2-chome Chuo-ku Tokyo (JP) (§) Date of publication of application: 22.06.83 Bulletin 83/25 @ Inventor: Fitzgerald, Patrick Henry 640 Howard Avenue ® Publication ofthe grant of the patent: Pitman New Jersey 08071 (US) 29.10.86 Bulletin 86/44 ® Representative: Abitz, Walter, Dr.-lng. et al (M) Designated Contracting States: Abitz, Morf, Gritschneder, Freiherr von DE FR GB IT Wittgenstein Postfach 86 01 09 D-8000 Munchen 86 (DE) (§) References cited: GB-A-2043 094 US-A-3 051 720 US-A-4 289 698 BERICHTE DER BUNSENGESELLSCHAFT FUR PHYSIKALISCHE CHEMIE, vol. 71, no. 3, 1967, pages 239-342, Weinheim, DE., B. HONIGMANN: "Physikalische Grundlagen der anwendungstechnischen Eigenschaften von Pigmenten" The file contains technical information submitted after the application was filed and not included in this specification Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed untîl the opposition fee has been paid. (Art. 99(1 ) European patent convention). Courier Press, Leamington Spa, England. sulfonated semichloro copper phthalocyanine in the initial slurry being at least 4.5, stirring in the Background of the Invention initial slurry being at least 4.5, stirring the slurry The present invention relates to a process for while maintaining its temperature at from 50° to converting crude semichlorinated copper 85°C for from 1/2 to 4 hours, diluting the slurry phthalocyanine or crude partially sulfonated with water to less than 35 weight percent sulfuric semichlorinated copper phthalocyanine into a acid in water, stirring the diluted slurry at from 60° highly transparent pigment of high tinctorial to 95°C for from 1/2 to 4 hours and recovering strength. pigmentary grade semichloro copper phthalo- In the past crude copper phthalocyanine has cyanine or partially sulfonated semichloro copper been converted to pigmentary grade material by phthalocyanine. solvent milling as disclosed in U.S. 2,799,594 and U.S. 2,799,595 or by acid pasting as disclosed in Detailed Description U.S. 3,024,247. The products produced in this The premilling step of the present invention is manner do not exhibit high transparency, and that conventionally used for ball milling opera- encapsulation in polymers, such as disclosed in tions. Thus the charge of grinding media will U.S. 3,806,464, has been used to improve trans- occupy about half of the volume of the mill anti parency. The process of the present invention the copper phthalocyanine being ground will involves an acid treatment of a preground semi- essentially occupy the voids between these chlorinated copper phthalocyanine pigment, media. It is quite possible to increase the charge which is lower in cost than either acid pasting or with some increase in milling time. The choice of solvent milling and produces highly transparent these conditions is well within the skill of one products without the complication of added versed in this type of operation. The preferred polymeric resins. grinding media in the mill is the rod type, which The effect of contact with sulfuric acid solutions may vary in size; but it is quite possible to use of various concentrations on the crystal phase of ordinary round steel balls varying from 1/8 inch copper phthalocyanine and monochloro copper (0.32 cm) in diameter up to 1/2 inch (1.27 cm) in phthalocyanine has been described by B. Honig- diameter or more in the operation. When round mann et al Zeitschrift fur Kristallographic 122, pp balls are used there is a marked tendency for the 185-205 (1965) and B. Honigmann, Berichte der charge to cake in the mill, under some conditions, Bundesgesellschaft, 71 (1967). which tendency generally can be avoided by the U.S. 3,051,720 discloses a process for the com- addition of materials of an irregular shape, such minution of crude phthalocyanine pigment which as nails, to the charge. The use of the rod type comprises in a preferred embodiment the follow- grinding media usually avoids this caking. ing steps. A phthalocyanine is dry ground for For use in the present invention ball milling is about 6 hours in a conventional manner in a ball preferred over sand milling or salt milling. mill in the absence of any grinding aid. After the It is impossible to set up limits as to the length discharge of the dry pigment from the mill, it is of the milling cycle, since it will vary with the mill slurried in 3-4 parts of sulfuric acid of about loading and the type of mill being used. In order 65-85% concentration, and after complete wet- to establish the optimum length of time for the ting, it is allowed to stand in contact with the acid milling, it is recommended that the invention be for about one hour at about room temperature, run with variations in the milling time and the e.g. in the range of 10-30°C. The slurry is then samples evaluated for the best balance of rapidly diluted with a relatively large amount of properties such as color strength, intensity, dis- water, heated for a short time near the boiling persibility and transparency. A minimum of 4-6 point, and then filtered, washed free of soluble hours is usually required, and this may be ex- salts and dried in a conventional manner to give a tended to as much as 12-18 hours or even more pigment of superior tinctorial properties. How- on a commercial scale mill. Considerably longer ever the product of this process is not completely times are required when using a semi-works or satisfactory regarding transparency and rheo- laboratory scale mill. logical properties. After the premilling step the pigment is in the form of a highly agglomerated material of low Summary of the Invention crystallinity which is of little value as a pigment. The present invention relates to a process In accordance with the present invention after comprising premilling a crude semichloro copper the premilling step the premilled semichloro cop- phthalocyanine or a crude partially sulfonated per phthalocyanine is contacted with aqueous semichloro copper phthalocyanine, forming a sulfuric acid. In the case of semichloro copper slurry of the premilled material in an aqueous phthalocyanine the sulfuric acid concentration solution of sulfuric acid of elevated temperature should be from 50 to 60% by weight and prefer- and of 50 to 60 percent by weight strength in the ably from 55 to 59% by weight. In the case of case of semichloro copper phthalocyanine or of partially sulfonated semichloro copper phthalo- 50 to 61 percent by weight strength in the case of cyanine the sulfuric acid concentration should be partially sulfonated semichloro copper phthalo- from 50 to 61 % by weight with from 58 to 61 % by cyanine, the weight ratio of aqueous solution of weight being preferred. If an acid concentration sulfuric acid to partially sulfonated or un- below 50% is used the premilled powder is not sufficiently deaggregated and a weak, dull pro- Examples duct with a milky scatter in metallic finishes will In the following examples all "parts" are by result. If acid greater than 60% (61% in the case of weight. partially sulfonated semichloro copper phthalo- cyanine) the product will have the less desirable Example I greener weaker all phase and will be less trans- Preparation of the Mill Powders parent. Forty-eight parts of the crude copper phthalo- The weight ratio of sulfuric acid solution to pre- cyanine (as described in a or b below) was rolled milled pigment is at least 4.5 and is preferably at 70% of critical speed (critical speed is the speed 4.5-5.5 to 1. At lower levels the pigment is at which centrifugal force overcomes the force of moderately wet and does not give a stirrable gravity so that the grinding elements are retained mass. Larger amounts of sulfuric acid can be used against the outer wall of the mill) with 1000 parts but are undesirable for economic reasons. The of 5/8" (1.6 cm) x 1" (2.54 cm) steel rods for 6 acid is at an elevated temperature when added to hours and discharged through a screen. the pigment. The resulting slurry is stirred at 50° a. The crude copper phthalocyanine used to 85°C for from 1/2 to 4 hours. This slurry is then for the milling contained about 4.0% chlorine as diluted to less than 35 wt % sulfuric acid in the obtained by isolating the product of the reaction aqueous phase and stirred at 60° to 95°C for 1/2 to 4-chlorophthalic acid and phthalic anhydride with 4 hours. The pigment is then isolated in the urea and copper chloride in kerosene and in the conventional manner, such as by filtering and presence of ammonium molybdate. drying. Surfactants and/or other treating agents b. The crude copper phthalocyanine used for may be added during either stage of the process. the milling contained about 4.0% chlorine and As used herein semichloro copper phthalo- 0.27% sulfur as obtained by isolating the product cyanine means copper phthalocyanine containing of the reaction of 4-chlorophthalic acid, 4-sulfo- from 3 to 5 percent by weight chlorine.
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