DE1161532B - Verfahren zur Herstellung von stark rotstichigem Kupferphthalocyanin - Google Patents
Verfahren zur Herstellung von stark rotstichigem KupferphthalocyaninInfo
- Publication number
- DE1161532B DE1161532B DEJ19446A DEJ0019446A DE1161532B DE 1161532 B DE1161532 B DE 1161532B DE J19446 A DEJ19446 A DE J19446A DE J0019446 A DEJ0019446 A DE J0019446A DE 1161532 B DE1161532 B DE 1161532B
- Authority
- DE
- Germany
- Prior art keywords
- copper phthalocyanine
- crystal form
- parts
- crystal
- benzene
- 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
- 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 title claims description 34
- 238000000034 method Methods 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000013078 crystal Substances 0.000 claims description 60
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 42
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000004094 surface-active agent Substances 0.000 claims description 10
- 239000000047 product Substances 0.000 description 13
- 238000002441 X-ray diffraction Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 238000001228 spectrum Methods 0.000 description 10
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
- 239000000839 emulsion Substances 0.000 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 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000002083 X-ray spectrum Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 description 1
- SAIFDOHAMXQQHH-UHFFFAOYSA-N C(S(=O)(=O)OC1=CC=CC2=CC=CC=C12)S(=O)(=O)OC1=CC=CC2=CC=CC=C12.[Na].[Na] Chemical compound C(S(=O)(=O)OC1=CC=CC2=CC=CC=C12)S(=O)(=O)OC1=CC=CC2=CC=CC=C12.[Na].[Na] SAIFDOHAMXQQHH-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 229940073769 methyl oleate Drugs 0.000 description 1
- 101150101567 pat-2 gene Proteins 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- -1 polyethyleneoxy Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000002966 varnish Substances 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
- C09B67/0032—Treatment of phthalocyanine 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
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
- C09B67/0016—Influencing the physical properties by treatment with a liquid, e.g. solvents 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
- 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
- C09B67/0025—Crystal modifications; Special X-ray patterns
- C09B67/0026—Crystal modifications; Special X-ray patterns of phthalocyanine pigments
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Coloring (AREA)
- Photoreceptors In Electrophotography (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5936/60A GB912526A (en) | 1960-02-19 | 1960-02-19 | Novel crystal form of copper phthalocyanine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1161532B true DE1161532B (de) | 1964-01-23 |
Family
ID=61562955
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEJ19446A Pending DE1161532B (de) | 1960-02-19 | 1961-02-17 | Verfahren zur Herstellung von stark rotstichigem Kupferphthalocyanin |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3150150A (en:Method) |
| CH (1) | CH411189A (en:Method) |
| DE (1) | DE1161532B (en:Method) |
| FR (1) | FR1281104A (en:Method) |
| GB (1) | GB912526A (en:Method) |
| NL (1) | NL261374A (en:Method) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3713857A (en) * | 1971-02-25 | 1973-01-30 | Sun Chemical Corp | Phthalocyanine pigments |
| JPS5284231A (en) * | 1976-01-01 | 1977-07-13 | Nippon Shokubai Kagaku Kogyo Co Ltd | Rho type copper phthalocyanine |
| FR2417531A1 (fr) * | 1978-02-21 | 1979-09-14 | Ugine Kuhlmann | Nouveau procede de preparation de pigments de phtalocyanine |
| US4451654A (en) * | 1981-03-05 | 1984-05-29 | Basf Aktiengesellschaft | Conditioning of finely divided crude organic pigments |
| JP2782765B2 (ja) * | 1988-04-15 | 1998-08-06 | 日本電気株式会社 | フタロシアニン結晶の製造方法 |
| US5139592A (en) * | 1988-07-13 | 1992-08-18 | Minnesota Mining And Manufacturing Company | Low gravity enhanced growth of phthalocyanine polymorphs and films |
| US6506244B1 (en) | 1999-08-03 | 2003-01-14 | Ciba Specialty Chemicals Corporation | Stable polymorphic copper-free phthalocyanine pigment |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH200683A (de) * | 1936-07-23 | 1938-10-31 | Ig Farbenindustrie Ag | Verfahren zur Verbesserung organischer Körperfarben. |
| DE861301C (de) * | 1950-03-01 | 1952-12-29 | Ciba Geigy | Verfahren zur Herstellung von farbstarkem, metallfreiem Phthalocyanin der ª‰-Form |
| DE950799C (de) * | 1952-04-12 | 1956-10-18 | Basf Ag | Verfahren zur Herstellung von Pigmentfarbstoffen |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2699444A (en) * | 1952-01-08 | 1955-01-11 | American Cyanamid Co | Preparation of phthalocyanine pigments |
| US3051721A (en) * | 1959-01-13 | 1962-08-28 | American Cyanamid Co | Pigmentary copper phthalocyanine in the "r" form and its preparation |
-
1960
- 1960-02-19 GB GB5936/60A patent/GB912526A/en not_active Expired
-
1961
- 1961-02-10 US US88266A patent/US3150150A/en not_active Expired - Lifetime
- 1961-02-17 CH CH193861A patent/CH411189A/de unknown
- 1961-02-17 NL NL261374A patent/NL261374A/xx unknown
- 1961-02-17 DE DEJ19446A patent/DE1161532B/de active Pending
- 1961-02-20 FR FR853305A patent/FR1281104A/fr not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH200683A (de) * | 1936-07-23 | 1938-10-31 | Ig Farbenindustrie Ag | Verfahren zur Verbesserung organischer Körperfarben. |
| DE861301C (de) * | 1950-03-01 | 1952-12-29 | Ciba Geigy | Verfahren zur Herstellung von farbstarkem, metallfreiem Phthalocyanin der ª‰-Form |
| DE950799C (de) * | 1952-04-12 | 1956-10-18 | Basf Ag | Verfahren zur Herstellung von Pigmentfarbstoffen |
Also Published As
| Publication number | Publication date |
|---|---|
| GB912526A (en) | 1962-12-12 |
| US3150150A (en) | 1964-09-22 |
| FR1281104A (fr) | 1962-01-08 |
| CH411189A (de) | 1966-04-15 |
| NL261374A (en:Method) | 1964-05-25 |
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