CS210288B1 - Continuous method of preparation of the copper ftalocyanine - Google Patents
Continuous method of preparation of the copper ftalocyanine Download PDFInfo
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- CS210288B1 CS210288B1 CS706779A CS706779A CS210288B1 CS 210288 B1 CS210288 B1 CS 210288B1 CS 706779 A CS706779 A CS 706779A CS 706779 A CS706779 A CS 706779A CS 210288 B1 CS210288 B1 CS 210288B1
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- phthalocyanine
- copper
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- urea
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims abstract description 4
- 229910052802 copper Inorganic materials 0.000 title claims abstract description 4
- 239000010949 copper Substances 0.000 title claims abstract description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 238000011437 continuous method Methods 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 22
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000004202 carbamide Substances 0.000 claims abstract description 18
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 claims abstract description 13
- 239000011609 ammonium molybdate Substances 0.000 claims abstract description 13
- 235000018660 ammonium molybdate Nutrition 0.000 claims abstract description 13
- 229940010552 ammonium molybdate Drugs 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims abstract description 10
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 239000011261 inert gas Substances 0.000 claims abstract description 3
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 3
- SDGNNLQZAPXALR-UHFFFAOYSA-N 3-sulfophthalic acid Chemical compound OC(=O)C1=CC=CC(S(O)(=O)=O)=C1C(O)=O SDGNNLQZAPXALR-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000001408 amides Chemical class 0.000 claims abstract 2
- 150000003949 imides Chemical class 0.000 claims abstract 2
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 claims description 20
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 9
- -1 NH 4 + Inorganic materials 0.000 claims description 5
- 238000010924 continuous production Methods 0.000 claims description 5
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000005749 Copper compound Substances 0.000 claims 1
- 150000001880 copper compounds Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 13
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract description 3
- 150000003839 salts Chemical class 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- BKFXSOCDAQACQM-UHFFFAOYSA-N 3-chlorophthalic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1C(O)=O BKFXSOCDAQACQM-UHFFFAOYSA-N 0.000 abstract 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical group [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract 1
- 125000004436 sodium atom Chemical group 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 16
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 8
- 229940045803 cuprous chloride Drugs 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000049 pigment Substances 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- YNVXMRQUCCMCNZ-UHFFFAOYSA-K S(=O)(=O)([O-])C=1C=C(C(C(=O)[O-])=CC=1)C(=O)[O-].[K+].[K+].[K+] Chemical compound S(=O)(=O)([O-])C=1C=C(C(C(=O)[O-])=CC=1)C(=O)[O-].[K+].[K+].[K+] YNVXMRQUCCMCNZ-UHFFFAOYSA-K 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000001879 copper Chemical class 0.000 description 2
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- HCXVRWNMKLEOKO-UHFFFAOYSA-N 2-benzofuran-1,3-dione;urea Chemical compound NC(N)=O.C1=CC=C2C(=O)OC(=O)C2=C1 HCXVRWNMKLEOKO-UHFFFAOYSA-N 0.000 description 1
- CYMRPDYINXWJFU-UHFFFAOYSA-N 2-carbamoylbenzoic acid Chemical compound NC(=O)C1=CC=CC=C1C(O)=O CYMRPDYINXWJFU-UHFFFAOYSA-N 0.000 description 1
- DVIPPHSQIBKWSA-UHFFFAOYSA-N 4-chlorophthalic acid Chemical class OC(=O)C1=CC=C(Cl)C=C1C(O)=O DVIPPHSQIBKWSA-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- VSOYJNRFGMJBAV-UHFFFAOYSA-N N.[Mo+4] Chemical compound N.[Mo+4] VSOYJNRFGMJBAV-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000001055 blue pigment Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229940045136 urea Drugs 0.000 description 1
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
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0034—Mixtures of two or more pigments or dyes of the same type
- C09B67/0035—Mixtures of phthalocyanines
-
- 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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
-
- 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
- C09B63/00—Lakes
- C09B63/005—Metal lakes of dyes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
Vynález se týká nepřetržitého způsobu přípravy ftalocyaninu mědi vzorceThe invention relates to a continuous process for the preparation of copper phthalocyanine of the formula
CuFb-—Ri kde Fit = ftalocyanin, Rb R2 = H, Cl, SO3Me, Me = H, Na, K, NH„+, Ba, . Ca, bez použití rozpouštědel.CuFb - where Ri = Fit phthalocyanine, R b 2 = H, Cl, SO 3 Me, Me = H, Na, K, NH "+, Ba,. Ca, without the use of solvents.
Uvedený ttalocyanin mědi se používá po vhodné úpravě jako modrý ' pigment vynikajícíchstálostí.Said copper phthalocyanine is used, after suitable treatment, as a blue pigment of excellent stability.
Ftalocyanin mědi se vyrábí dvěma způsoby. Jednak kondenzací nitrilu kyseliny ftálové se solemi mědi za sucha nebo v rozpouštědle, jednak kondenzací směsi ttalanhydridu, chloridu měďného, močoviny, chloridu amonného za katalýzy molybdenanem amonným.Copper phthalocyanine is produced in two ways. On the one hand, by condensation of phthalic nitrile with copper salts in dry or solvent, on the other hand, by condensation of a mixture of ttalanhydride, cuprous chloride, urea, ammonium chloride under catalysis with ammonium molybdate.
Tento druihý způsob je rozšířenější. Kondenzace se provádí v .rozpouštědle, nejčastěji v trichilorbenzenu nebo nitrobenzenu, násadovým nebo kontinuálním způsobem. Kondenzace se .provádí též bez rozpouštědla, tzv. suchým způsobem. Z literatury jsou známy násadové způsoby, kdy se směs ftalanhydridu, močoviny, chloridu měďného a molybdenanu amonného zahřívá sama o sobě nebo· v prostředí anorganických solí, jako například síranu sodného na teplotu 200 °C. Jsou rovněž známy způsoby kontinuální, kdy směs ttalanhydridu, močoviny, chloridu měďného a molybdenanu amonného prochází šnekovým reaktorem vyhřívaným na teplotu 200 °C, nebo kdy se uvedená směs kontinuálně uvádí do horizontálního míchaného reaktoru, v němž je předložen již hotový ftalocyanin mědi vyhřátý na 200 °C, ve kterém přiváděná reakční směs reaguje na ttalocyanin mědi a po reakci je na druhé straně reaktoru kontinuálně odváděna.This second method is more widespread. The condensation is carried out in a solvent, most often in trichilorbenzene or nitrobenzene, in a batch or continuous manner. Condensation is also carried out without solvent, the so-called dry method. Batch methods are known in the literature where a mixture of phthalic anhydride, urea, cuprous chloride and ammonium molybdate is heated by itself or in an environment of inorganic salts such as sodium sulfate to a temperature of 200 ° C. Continuous processes are also known in which a mixture of ttalanhydride, urea, copper (I) chloride and ammonium molybdate is passed through a screw reactor heated to 200 ° C, or wherein said mixture is continuously fed to a horizontal stirred reactor in which the finished copper phthalocyanine ° C, in which the feed reaction mixture reacts to copper tthalocyanine and is continuously withdrawn on the other side of the reactor after the reaction.
Nevýhodou uvedených kontinuálních způsobů je, že ftalocyanin mědi podle nich vyrobený se získává v hrudkové až kusovité formě a po .zpracování na pigment nedosahuje zpravidla špičkových kvalit. Částečné zlepšení nárokuje čs. A.' O. č. 177 716 a to tak, že se směs ftalanhydridu močoviny, chloridu mědi a molybdenanu amonného homogenizuje s 5 až 30% hm. solí anorganických kyselin vybraných ze skupiny zahrnující síran sodný a draselný nebo chlorid sodný a draselný.A disadvantage of the said continuous processes is that the copper phthalocyanine produced according to them is obtained in lumpy to lumpy form and, as a rule, does not reach the highest quality after processing into pigment. A partial improvement is claimed by the MS. AND.' No. 177,716 by homogenizing a mixture of urea phthalic anhydride, copper chloride and ammonium molybdate with 5 to 30 wt. salts of inorganic acids selected from the group consisting of sodium and potassium sulfate or sodium and potassium chloride.
Nyní bylo zjištěno, že výrazného zlepšení formy a kvality kontinuálně vyráběného ftalocyaninu mědi se .dosáhne způsobem podle vynálezu.It has now been found that a significant improvement in the form and quality of the continuously produced copper phthalocyanine is achieved by the process of the invention.
Nepřetržitý způsob přípravy ftalocyaninu mědi reakcí anhydridu kyseliny ftálové, ftalaminu, ftalimidu nebo substituované kyseliny ftálové a močoviny v přítomnosti solí jednomocné nebo dvojmocné mědi při teplotě 180 až 260 °C v proudu inertního plynu v již předloženém ftalocyaninu spočívá podle vynálezu v tom, že se odpovídající směs výše uvedených .komponent uvádí do reakce tak, aby hmotový poměr předloženého ftalocyaninu mědi ku směsi reagujících komponent byl · nejméně 3 : 1. Je-li zachován tento poměr, proběhne reakce tak, že se veškerý vyrobený . ftalocyanin získá ve vyhovující sypké formě bez spečených kousků a hrudek a rovněž pigmenty z něj vyrobené vykazují lepší kvalitu. Požadovaného poměru předloženého .ftalocyaninu mědi a' směsi · reakčních komponent se ' prakticky dosahuje několika způsoby. Buď se směs komponent uvádí ' do reaktoru již smíšená s . potřebným množstvím ftalocyaninu mědi nebo se směs reakčních komponent uvádí do reaktoru šnekovým . dávkovačem tak, aby vstupovala pod hladinu v reaktoru předloženého ftalocyaninu mědi, nebo kombinací obou uvedených způsobů.A continuous process for the preparation of copper phthalocyanine by reacting phthalic anhydride, phthalamine, phthalimide or substituted phthalic acid and urea in the presence of monovalent or divalent copper salts at a temperature of 180 to 260 ° C in an inert gas stream in the present phthalocyanine the mixture of the aforementioned components is reacted so that the weight ratio of the present copper phthalocyanine to the mixture of the reacting components is at least 3: 1. If this ratio is maintained, the reaction proceeds so that all of it is produced. phthalocyanine is obtained in a convenient free-flowing form without sintered pieces and lumps, and also the pigments produced therefrom show better quality. The desired ratio of the present copper phthalocyanine to the reaction mixture mixture is practically achieved in several ways. Either the mixture of components is introduced into the reactor already mixed with the reactor. with the required amount of copper phthalocyanine or the mixture of reaction components is fed into the reactor by a screw. with a dispenser so as to enter below the level in the reactor of the present copper phthalocyanine, or a combination of both.
Níže uvedené příklady ilustrují provedení podle vynálezu.The examples below illustrate embodiments of the invention.
Příklad 1Example 1
Do horizontálního reaktoru opatřeného horizontálně uloženým, vhodně tvarovaným míchadlem, ' topným pláštěm, přepážkou, ' šnekovým dávkovačem, turniketovým odběrem produktu a přestupníkem, kterým se odvádějí vedlejší plynné zplodiny do absorpčního systému, se předloží 2 000 g surového ftalocyaninu mědi. Aparatura se naplní dusíkem a vyhřeje .na 195 °C. Poté se spustí míchadlo, turniket a šnekový dávkovač, kterým se začne nepřetržitě přivádět směs 41,88 % anhydridu kyseliny ftálové, 50,86 % močoviny, 7,12 % chloridu měďného a 0,14% molybdenanu amonného. Zároveň .se 'do aparatury přivádí .podle potřeby dusík tak, aby celý provoz probíhal v inertní atmosféře. Z turniketového odběru se začne odebírat produkt. Když ise .získají 4 000 g produktu, je všechen původně předložený ftalocyanin mědi vypuštěn a z reaktoru ' odchází produkt vyrobený z nepřetržitě přiváděné výše popsané směsi komponent. Takto vyrobený ftalocyanin mědi je v sypké formě bez spečených kousků a hrudek a dosahuje při zpracování na pigment některým z obvyklých způsobů špičkové kvality.2000 g of crude copper phthalocyanine are introduced into a horizontal reactor equipped with a horizontally placed, suitably shaped stirrer, heating mantle, baffle, screw feeder, turnstile product take-off, and a transducer to remove the by-products to the absorption system. The apparatus is filled with nitrogen and heated to 195 ° C. The mixer, turnstile and screw feeder are then started to continuously feed a mixture of 41.88% phthalic anhydride, 50.86% urea, 7.12% cuprous chloride and 0.14% ammonium molybdate. At the same time, nitrogen is fed to the apparatus as required so that the entire operation is carried out in an inert atmosphere. The product will be taken from the turnstile collection. When 4000 g of product are obtained, all of the initially introduced copper phthalocyanine is discharged and the product made from the continuously fed mixture of components described above is discharged from the reactor. The copper phthalocyanine thus produced is in a free-flowing form, free of sintered pieces and lumps, and achieves pigment processing by one of the usual top quality methods.
Příklad .2Example .2
Místo způsobu popsaného v příkladu .1, se do reaktoru uvádí směs 41,88% anhydridu ' kyseliny ftálové, 50,86% močoviny, 7,12 % chloridu měďného a 0,14 % kyseliny molybdenové při jinak stejném postupu.Instead of the method described in Example 1, a mixture of 41.88% phthalic anhydride, 50.86% urea, 7.12% cuprous chloride, and 0.14% molybdic acid was charged to the reactor in an otherwise identical manner.
Příklad 3Example 3
Místo způsobu popsaného v příkladu 1, se do reaktoru uvádí' směs 42,85 % anhydridu kyseliny ftálové, 52,05% močoviny, 4,94% chloridu měďnatého a ' 0,16% molybdenu amonného při jinak stejném postupu.Instead of the method described in Example 1, a mixture of 42.85% phthalic anhydride, 52.05% urea, 4.94% copper chloride, and 0.16% ammonium molybdenum was fed into the reactor in an otherwise identical manner.
Příklad 4Example 4
Místo způsobu popsaného v příkladu 1 se do reaktoru uvádí směs 75 % .surového ftalocyaninu mědi, 10,46% anhydridu kyseliny ftálové, 12,71 ' % ' močoviny, 1,78 % chloridu mědného a 0.,05% molybdenanu amonného při jinak stejném postupu.Instead of the process described in Example 1, a mixture of 75% crude copper phthalocyanine, 10.46% phthalic anhydride, 12.71% urea, 1.78% copper chloride and 0.55% ammonium molybdate was charged to the reactor at a different rate. same procedure.
Příklad 5Example 5
Místo způsobu popsaného v příkladu 1 se do reaktoru uvádí směs 28,6(3% .anhydridu kyseliny ftálové, 9,41% manosodné soli kyseliny . 4-c-hiiiórftálové, 55,90% močoviny, 5,93% chloridu mědného a 0,13% molybdenanu .amonného :pri jinak stejném. postupu. . Získá se tak parciálně chlorovaný ftalocyanin mědi, který je vhodnou surovinou při výrobě α-modifikace, stabilní v aromatických rozpouštědlech.Instead of the method described in Example 1, a mixture of 28.6 (3% phthalic anhydride, 9.41% mannose sodium salt, 4-c-fluorophthalic acid, 55.90% urea, 5.93% copper chloride and 0.10%) was fed to the reactor. 13% molybdate .amonného: otherwise the same. procedure.. to give partially chlorinated copper phthalocyanine, which is a suitable raw material for production of α-modification stable in aromatic solvents.
Při stejném postupu jako v příkladu 1 se do reaktoru uvádějí variantně směsi uvedené v následujících příkladech:In the same procedure as in Example 1, the mixtures of the following examples were fed into the reactor as an alternative:
Příklad 6Example 6
44,169% kyseliny ftálové, 48,39% . močoví· ny, 6,77 % chloridu mědného, 0,15 % molybdenanu amonného.44.169% phthalic acid, 48.39%. urea, 6.77% cuprous chloride, 0.15% ammonium molybdate.
Příklad 7Example 7
44,40 % amidu kyseliny ftálové, 48,65 % močoviny, 6,81 % chloridu mědnatého a 0,14% molybdenanu amonného.44.40% phthalic amide, 48.65% urea, 6.81% copper chloride and 0.14% ammonium molybdate.
Příklad 8Example 8
48,17% imidu kyseliny ftálové, 43,39%' močoviny, 8,25 % chloridu mědnatého a. 0,19% molybdenanu amonného.48.17% phthalic acid imide, 43.39% urea, 8.25% copper chloride, and 0.19% ammonium molybdate.
Příklad 9Example 9
47,78% monosodné soli ... kyseliny . ftálové, . 4'5,69% močoviny, 6,39% chloridu mědna* tého, 0,14 % molybdenanu . amonného.47.78% monosodium salt ... acid. fttal,. 4.69% urea, 6.39% copper (I) chloride, 0.14% molybdate. ammonium.
Příklad 10 .33,01% anhydridu kyseliny ftálové, 52,67% močoviny, 5,07% chloridu mědnatého, 9,14% síranu sodného bezvodého, 0,11% molybdenánu amonného.Example 10.33.01% phthalic anhydride, 52.67% urea, 5.07% copper chloride, 9.14% anhydrous sodium sulfate, 0.11% ammonium molybdate.
Příklad 11Example 11
25,9 % anhydridu Jcys^ein^y £tal(vré, 1^6»5> %' draselné soli kyseliny 4-sulfoftalové, 51,7% močoviny, 5,8% . chloridu . mědného a 0,1% molybdenu amonného.25.9% of cysyline anhydride (pure, 1-6.5% by weight of 4-sulfophthalic acid potassium salt, 51.7% urea, 5.8% copper (I) chloride and 0.1% molybdenum) ammonium.
Příklad .12Example .12
17,4% anhydridu kyseliny Katové, 855% monosodné. soli kyseliny 4-chlorftalové, 16,5% draselné soli kyseliny 4-sulfoftalové, 51,7% močoviny, 5,8% chloridu mědného a 0,1 % molybdenanu amonného.17.4% Katic anhydride, 855% monosodium. 4-chlorophthalic acid salt, 16.5% potassium 4-sulfophthalic acid salt, 51.7% urea, 5.8% copper chloride and 0.1% ammonium molybdate.
Claims (1)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS706779A CS210288B1 (en) | 1979-10-18 | 1979-10-18 | Continuous method of preparation of the copper ftalocyanine |
| GB8032679A GB2063286A (en) | 1979-10-18 | 1980-10-09 | Continuous Solvent-free Process for Producing Copper Phthalocyanines |
| FR8022006A FR2467870A1 (en) | 1979-10-18 | 1980-10-15 | PROCESS FOR THE CONTINUOUS PREPARATION OF COPPER PHTHALOCYANIN |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS706779A CS210288B1 (en) | 1979-10-18 | 1979-10-18 | Continuous method of preparation of the copper ftalocyanine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS210288B1 true CS210288B1 (en) | 1982-01-29 |
Family
ID=5419106
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS706779A CS210288B1 (en) | 1979-10-18 | 1979-10-18 | Continuous method of preparation of the copper ftalocyanine |
Country Status (3)
| Country | Link |
|---|---|
| CS (1) | CS210288B1 (en) |
| FR (1) | FR2467870A1 (en) |
| GB (1) | GB2063286A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5247088A (en) * | 1991-07-30 | 1993-09-21 | Miles Inc. | Process for the continuous preparation of perylenetetracarboxylic diimides |
| USD502726S1 (en) * | 2003-12-23 | 2005-03-08 | Sweda Company, Llc | Photo frame with calculator |
| CN119819221A (en) * | 2025-01-10 | 2025-04-15 | 安徽申兰华色材股份有限公司 | Copper phthalocyanine solid-phase method synthesis system and method |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2964532A (en) * | 1957-04-17 | 1960-12-13 | Du Pont | Production of pigments |
| US3188318A (en) * | 1958-12-30 | 1965-06-08 | Hercules Powder Co Ltd | Process for producing phthalocyanines |
-
1979
- 1979-10-18 CS CS706779A patent/CS210288B1/en unknown
-
1980
- 1980-10-09 GB GB8032679A patent/GB2063286A/en not_active Withdrawn
- 1980-10-15 FR FR8022006A patent/FR2467870A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| GB2063286A (en) | 1981-06-03 |
| FR2467870A1 (en) | 1981-04-30 |
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