CN1037722A - The new manufacturing method of phthalocyanine blue pigment - Google Patents
The new manufacturing method of phthalocyanine blue pigment Download PDFInfo
- Publication number
- CN1037722A CN1037722A CN88102985A CN88102985A CN1037722A CN 1037722 A CN1037722 A CN 1037722A CN 88102985 A CN88102985 A CN 88102985A CN 88102985 A CN88102985 A CN 88102985A CN 1037722 A CN1037722 A CN 1037722A
- Authority
- CN
- China
- Prior art keywords
- phthalocyanine blue
- solvent
- manufacture method
- bright
- present
- 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.)
- Pending
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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Abstract
The present invention is the method for the coming of new of phthalocyanine blue pigment, relates to the change of the crucial organic solvent of manufacture method.Phthalocyanine blue is a strong coloring force bright in colour, has good fast light, heat-resisting, anti-solvent, the pigment dyestuff of chemical resistant performance.Always use trichlorobenzene, dichlorobenzene, oil of mirbane, naphthalene, chloronaphthalene, aliphatic hydrocarbon, alkylbenzene, phenyl ether, tetraline equal solvent in the manufacture method, they have strong toxicity respectively, generate carcinogens, and to shortcomings such as thermally labile and the not bright-coloured tinting strength differences of produced phthalocyanine blue color and luster.Thereby the present invention is solvent with the bicyclohexyl has overcome above-mentioned shortcoming.
Description
The present invention is the new manufacturing method of pthalocyanine blue, relates to the change of the crucial organic solvent of manufacture method.
Pthalocyanine blue is bright in colour, strong coloring force, the pigment dyestuff with good chemical resistant performance of fast light, heat-resisting, anti-solvent.
Manufacture method always can reduce four kinds.
(1) benzene first dicarboxylic anhydride or derivatives thereof in the presence of catalyzer, or does not exist down, with urea and copper or mantoquita reaction.
(2) benzene dinitrile and copper or mantoquita reaction.
(3) an adjacent cyano group benzamide and copper or mantoquita reaction.
(4) the phthalein cyanine compound of no metal and mantoquita reaction.
Solid phase roasting method and liquid phase trichloro-benzene method, solid phase roasting method were wherein once arranged for industry is widely used, because solvent-free conduction temperature, it is even to be difficult to controlled temperature, thereby too high its urea of local temperature, phthalate anhydride decompose ammonia, carbonic acid gas is waved diffusing, not only increased raw material consumption but also polluted atmosphere, the part local temperature is low excessively, causes the not thoroughly reaction of urea and phthalate anhydride, when aftertreatment, lose, polluted time water with water.The liquid phase trichlorobenzene because the catalysis of copper causes trichlorobenzene dechlorination condensation to generate the carcinogens of polychlorobiphenyl, mixes being clipped in the pthalocyanine blue in reaction process, use and be difficult for removing thereby be unsuitable for industry.
The manufacturing of relevant pthalocyanine blue is a lot of with the patent of organic solvent in recent years.As patents such as oil of mirbane, dichlorobenzene, naphthalene, chloronaphthalene, aliphatic hydrocarbon, alkylbenzene, phenyl ether, tetralines, but the toxicity that replaces trichlorobenzene oil of mirbane, dichlorobenzene, chloronaphthalene equal solvent is not more decomposed, aliphatic hydrocarbon, alkylbenzene, phenyl ether, tetraline are to thermally labile, and the problems of making such as the not bright-coloured tinting strength difference of pthalocyanine blue color and luster.
Key in view of organic solvent in the manufacture method of pthalocyanine blue, the objective of the invention is to select a chemical property stable, be suitable for the organic solvent that distill repeatedly uses repeatedly, that toxicity is less and carried out a series of research, the organic solvent that bicyclohexyl (ten dihydro biphenyl) is made as pthalocyanine blue has been invented in research finally.
Bicyclohexyl of the present invention is the colourless liquid of fragrance, and is stable minimum to Heat stability is good, flash-point height, toxicity to acid, alkali, oxygenant, is suitable for distill repeatedly and reclaims use, has industrial value.
Manufacture method of the present invention; get phthalate anhydride or derivatives thereof and urea, mantoquita; perhaps benzene dinitrile or derivatives thereof and mantoquita are in the presence of catalyzer (as ammonium molybdate, titanium tetrachloride); or do not exist down; in the solvent of bicyclohexyl, heat 120～235 ℃ preferably 170～230 ℃, under normal pressure, perhaps add and depress reaction 2～10 hours; best 3～7 hours, yield 85～95%.
Bicyclohexyl of the present invention is the complete hydrogenation thing of biphenyl, or with the iodocyclohexane of two molecules, carries out the Woertz reaction.233～238 ℃ of the boiling points of its suitable-cisoid, anti--217～219 ℃ of transoid boiling points, use two kinds of mixture of isomers usually, usage quantity is the weight of benzene dinitrile, or 2～10 times of the weight of phthalate anhydride.
Embodiment 1
Cuprous 19 parts of 138 parts of anhydrous chlorides of rase of 113 parts of urea of phthalate anhydride, 500 parts of 0.22 part of bicyclohexyls of ammonium molybdate.Heating 185～190 ℃ of reactions stirred 3 hours, after reaction is over, the underpressure distillation reactant steams the solvent bicyclohexyl, with residue in the hot wash jar, filter, the dilute acid wash filter is also filtered the dry 100 parts of yields 89.40% of pthalocyanine blue that get purity 95～98% of washing filtering again again.
Embodiment 2
500 parts of 0.22 part of bicyclohexyls of the cuprous 18.5 parts of ammonium molybdates of 97 parts of anhydrous chlorides of rase of 109 parts of urea of Phthalimide, 190～200 ℃ of compressive reaction jar internal heating, the pressure of reaction vessel is 3kg/cm with valve regulated
2, stirring reaction 4 hours is handled to such an extent that 100 parts of yields of pthalocyanine blue are 91% by embodiment 1 after reaction is over.
Embodiment 3
500 parts of 0.6 part of bicyclohexyls of the cuprous 18.65 parts of ammonium molybdates of 95.5 parts of anhydrous chlorides of rase of benzene dinitrile, heated 200～210 ℃ of stirring reactions 7 hours, bicyclohexyl was reclaimed in distillation after reaction was over, residue is washed with the methanol cleaning after-filtration again in jar, and pickling filtration, washing and drying get 100 parts of yields 92.3% of thick pthalocyanine blue of purity 99%.
Claims (1)
1, with phthalate anhydride or derivatives thereof and urea and mantoquita, or benzene dinitrile or derivatives thereof and mantoquita, in the presence of catalyzer, reacting by heating is made in the method for pthalocyanine blue in organic solvent, and its organic solvent is a bicyclohexyl, is feature of the present invention.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN88102985A CN1037722A (en) | 1988-05-21 | 1988-05-21 | The new manufacturing method of phthalocyanine blue pigment |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN88102985A CN1037722A (en) | 1988-05-21 | 1988-05-21 | The new manufacturing method of phthalocyanine blue pigment |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1037722A true CN1037722A (en) | 1989-12-06 |
Family
ID=4832387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN88102985A Pending CN1037722A (en) | 1988-05-21 | 1988-05-21 | The new manufacturing method of phthalocyanine blue pigment |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1037722A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5393339A (en) * | 1994-05-11 | 1995-02-28 | Miles Inc. | Preparation of phthalocyanine pigments |
-
1988
- 1988-05-21 CN CN88102985A patent/CN1037722A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5393339A (en) * | 1994-05-11 | 1995-02-28 | Miles Inc. | Preparation of phthalocyanine pigments |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104031400A (en) | Preparation method of permanent violet pigment | |
| CN1037722A (en) | The new manufacturing method of phthalocyanine blue pigment | |
| CN100545165C (en) | Method for synthesizing copper phthalocyanine in ionic liquid | |
| CN101717588B (en) | Method for preparing metal cobalt phthalocyanine | |
| CN101717401B (en) | Preparing method of phthalocyaninatoaluminium chloride | |
| CN111348997A (en) | Preparation method of 2-alkyl anthraquinone | |
| CN101294005B (en) | Red naphtocyclinon solvent dye and preparation method thereof | |
| US3117158A (en) | Aminoarylsulfur pentafluorides | |
| CN1036974A (en) | N, the manufacture method of N-cyanoethyl benzylaniline dyestuff | |
| JPH02258873A (en) | Disperse dye | |
| CN115746006A (en) | Application of alcohol compound in copper phthalocyanine synthesis process | |
| CN103570734A (en) | Synthesis method of cobalt phthalocyanine diamine compound | |
| CN1312093C (en) | Anti-oxidation single component aromatic hydrocarbon solvent used in copper phthalocyanine synthesis | |
| CN110615741A (en) | Synthetic method of low-toxicity low-harm environment-friendly solvent green 3 | |
| CN105481722B (en) | Preparation method of 1, 4-diamino-2, 3-dicyanoanthraquinone | |
| CN105622569B (en) | A kind of o-hydroxy amine derivative and preparation method thereof | |
| Brătulescu | Green and conventional synthesis of sulfanilic acid | |
| Obi et al. | Synthesis of Monoazo Dyes From Halogenated Arylamines and Fastness Properties on Cotton and Nylon | |
| CN109824576B (en) | A kind of synthetic method of organic photoelectric material intermediate dimethyl indenocarbazole | |
| CN109232169A (en) | A kind of polyaryl replaces fulvalene compound and its synthetic method | |
| CN108503638B (en) | A kind of method of cobalt catalysis polyhalo imidodicarbonic diamide Dehalogenation reduction | |
| CN115960473A (en) | Method for preparing metal phthalocyanine pigment by solvent method | |
| CN110499039B (en) | Synthetic method of solvent blue 122 | |
| CN1033748C (en) | Synthesising technology for 2,4-dichlorophenyl formaldehyde | |
| CN1263727C (en) | Method of preparing 1-nitryl-2-ethyl anthraquinone |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C06 | Publication | ||
| PB01 | Publication | ||
| C01 | Deemed withdrawal of patent application (patent law 1993) | ||
| WD01 | Invention patent application deemed withdrawn after publication |