DE2637861A1 - Verfahren zur herstellung von polyhalogen-metallphthalocyaninen - Google Patents
Verfahren zur herstellung von polyhalogen-metallphthalocyaninenInfo
- Publication number
- DE2637861A1 DE2637861A1 DE19762637861 DE2637861A DE2637861A1 DE 2637861 A1 DE2637861 A1 DE 2637861A1 DE 19762637861 DE19762637861 DE 19762637861 DE 2637861 A DE2637861 A DE 2637861A DE 2637861 A1 DE2637861 A1 DE 2637861A1
- Authority
- DE
- Germany
- Prior art keywords
- parts
- weight
- amount
- titanium tetrachloride
- aluminum chloride
- 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- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 27
- 229910052751 metal Inorganic materials 0.000 title claims description 19
- 239000002184 metal Substances 0.000 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 50
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 31
- 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 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 16
- 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 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 150000004820 halides Chemical class 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 239000011574 phosphorus Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 230000031709 bromination Effects 0.000 claims description 2
- 238000005893 bromination reaction Methods 0.000 claims description 2
- 238000005660 chlorination reaction Methods 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 238000003756 stirring Methods 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- -1 sulphuryl Chemical group 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 230000026030 halogenation Effects 0.000 description 3
- 238000005658 halogenation reaction Methods 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- HUVXQFBFIFIDDU-UHFFFAOYSA-N aluminum phthalocyanine Chemical compound [Al+3].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 HUVXQFBFIFIDDU-UHFFFAOYSA-N 0.000 description 1
- 229940007424 antimony trisulfide Drugs 0.000 description 1
- NVWBARWTDVQPJD-UHFFFAOYSA-N antimony(3+);trisulfide Chemical compound [S-2].[S-2].[S-2].[Sb+3].[Sb+3] NVWBARWTDVQPJD-UHFFFAOYSA-N 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000001056 green pigment Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical class ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
- C09B47/10—Obtaining compounds having halogen atoms directly bound to the phthalocyanine skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3594775A GB1496256A (en) | 1975-09-01 | 1975-09-01 | Halogenation of metal phthalocyanines |
| GB4635975 | 1975-11-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2637861A1 true DE2637861A1 (de) | 1977-03-10 |
Family
ID=26262920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762637861 Withdrawn DE2637861A1 (de) | 1975-09-01 | 1976-08-23 | Verfahren zur herstellung von polyhalogen-metallphthalocyaninen |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5229819A (enrdf_load_stackoverflow) |
| AU (1) | AU497471B2 (enrdf_load_stackoverflow) |
| CH (1) | CH601441A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2637861A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2322180A1 (enrdf_load_stackoverflow) |
| IT (1) | IT1065823B (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0155780A3 (en) * | 1984-03-21 | 1985-12-04 | Imperial Chemical Industries Plc | Infra-red absorber |
| US5137798A (en) * | 1984-12-18 | 1992-08-11 | Imperial Chemical Industries Plc | A pit-forming optical recording media and process for producing the same |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0794611B2 (ja) * | 1988-01-29 | 1995-10-11 | 東洋インキ製造株式会社 | ハロゲン化銅フタロシアニンの製造方法 |
| JP2629071B2 (ja) * | 1990-11-09 | 1997-07-09 | 東洋インキ製造株式会社 | ポリハロゲン化フタロシアニンの製造方法 |
| JP5145649B2 (ja) * | 2006-04-25 | 2013-02-20 | 東洋インキＳｃホールディングス株式会社 | 塩素化臭素化フタロシアニン骨格含有化合物の組成物、該組成物の製造方法及び該組成物を用いた顔料分散インキ及びカラーフィルタ |
| KR102360691B1 (ko) | 2015-06-04 | 2022-02-08 | 썬 케미칼 코포레이션 | 염화된 구리 프탈로시아닌 안료 |
-
1976
- 1976-08-13 AU AU16818/76A patent/AU497471B2/en not_active Expired
- 1976-08-23 DE DE19762637861 patent/DE2637861A1/de not_active Withdrawn
- 1976-08-30 IT IT2667076A patent/IT1065823B/it active
- 1976-08-31 FR FR7626255A patent/FR2322180A1/fr active Granted
- 1976-08-31 CH CH1102476A patent/CH601441A5/xx not_active IP Right Cessation
- 1976-09-01 JP JP10541576A patent/JPS5229819A/ja active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0155780A3 (en) * | 1984-03-21 | 1985-12-04 | Imperial Chemical Industries Plc | Infra-red absorber |
| US4606859A (en) * | 1984-03-21 | 1986-08-19 | Imperial Chemical Industries Plc | Infra-red absorber |
| US5137798A (en) * | 1984-12-18 | 1992-08-11 | Imperial Chemical Industries Plc | A pit-forming optical recording media and process for producing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2322180A1 (fr) | 1977-03-25 |
| AU497471B2 (en) | 1978-12-14 |
| FR2322180B1 (enrdf_load_stackoverflow) | 1980-05-09 |
| CH601441A5 (enrdf_load_stackoverflow) | 1978-07-14 |
| JPS5229819A (en) | 1977-03-07 |
| AU1681876A (en) | 1978-02-16 |
| IT1065823B (it) | 1985-03-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |