DE2301479C3 - Llpophile Phthalocyanine, Verfahren zu ihrer Herstellung und ihre Verwendung zur Färbung organischer Losungsmittel, von Fetten und Wachsen - Google Patents
Llpophile Phthalocyanine, Verfahren zu ihrer Herstellung und ihre Verwendung zur Färbung organischer Losungsmittel, von Fetten und WachsenInfo
- Publication number
- DE2301479C3 DE2301479C3 DE2301479A DE2301479A DE2301479C3 DE 2301479 C3 DE2301479 C3 DE 2301479C3 DE 2301479 A DE2301479 A DE 2301479A DE 2301479 A DE2301479 A DE 2301479A DE 2301479 C3 DE2301479 C3 DE 2301479C3
- Authority
- DE
- Germany
- Prior art keywords
- parts
- phthalocyanines
- fats
- diamine
- organic solvents
- 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.)
- Expired
Links
- 239000003925 fat Substances 0.000 title description 5
- 238000004040 coloring Methods 0.000 title description 4
- 238000000034 method Methods 0.000 title description 4
- 239000003960 organic solvent Substances 0.000 title description 3
- 239000001993 wax Substances 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 150000004985 diamines Chemical class 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
- 239000005642 Oleic acid Substances 0.000 description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 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 3
- -1 phthalocyanine sulfochlorides Chemical class 0.000 description 3
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 3
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229910052783 alkali metal Chemical group 0.000 description 2
- 150000001340 alkali metals Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 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 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QRMHNINBLROUSC-UHFFFAOYSA-N octadec-1-en-8-amine Chemical compound CCCCCCCCCCC(N)CCCCCC=C QRMHNINBLROUSC-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 238000005406 washing Methods 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
- C09B47/24—Obtaining compounds having —COOH or —SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
- C09B47/26—Amide radicals
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
- C10M171/007—Coloured or dyes-containing lubricant compositions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Detergent Compositions (AREA)
- Lubricants (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7201855A FR2168198B1 (OSRAM) | 1972-01-20 | 1972-01-20 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2301479A1 DE2301479A1 (de) | 1973-07-26 |
| DE2301479B2 DE2301479B2 (de) | 1978-10-19 |
| DE2301479C3 true DE2301479C3 (de) | 1979-06-13 |
Family
ID=9092179
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2301479A Expired DE2301479C3 (de) | 1972-01-20 | 1973-01-12 | Llpophile Phthalocyanine, Verfahren zu ihrer Herstellung und ihre Verwendung zur Färbung organischer Losungsmittel, von Fetten und Wachsen |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4048189A (OSRAM) |
| JP (1) | JPS4883117A (OSRAM) |
| BE (1) | BE794330A (OSRAM) |
| BR (1) | BR7300448D0 (OSRAM) |
| CH (1) | CH568367A5 (OSRAM) |
| DE (1) | DE2301479C3 (OSRAM) |
| FR (1) | FR2168198B1 (OSRAM) |
| GB (1) | GB1390292A (OSRAM) |
| IT (1) | IT976433B (OSRAM) |
| NL (1) | NL7215370A (OSRAM) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH611922A5 (OSRAM) * | 1975-07-03 | 1979-06-29 | Ciba Geigy Ag | |
| DE2617062C2 (de) * | 1976-04-17 | 1985-07-04 | Cassella Ag, 6000 Frankfurt | Wasserlösliche Hydrazone der Phthalocyaninreihe, ihre Herstellung und Verwendung |
| US4448722A (en) * | 1981-02-19 | 1984-05-15 | The Hilton-Davis Chemical Co. | Phthalocyanines |
| US5525516B1 (en) * | 1994-09-30 | 1999-11-09 | Eastman Chem Co | Method for tagging petroleum products |
| EP1476507B1 (en) * | 2002-02-13 | 2008-08-06 | FUJIFILM Imaging Colorants Limited | Compounds, compositions and uses |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2863875A (en) * | 1953-12-21 | 1958-12-09 | Bayer Ag | Process for the production of basic dyestuffs |
| FR1192858A (fr) * | 1957-03-16 | 1959-10-29 | Basf Ag | Procédé pour la préparation de colorants basiques de la série des phtalocyanines |
| US3057873A (en) * | 1959-12-10 | 1962-10-09 | Geigy Ag J R | Phthalocyanine dyestuffs |
| DE2020812B2 (de) * | 1970-04-28 | 1974-08-08 | Mita Industrial Co. Ltd., Osaka (Japan) | Elektrophotographischer Suspensionsentwickler |
-
0
- BE BE794330D patent/BE794330A/xx unknown
-
1972
- 1972-01-20 FR FR7201855A patent/FR2168198B1/fr not_active Expired
- 1972-11-14 NL NL7215370A patent/NL7215370A/xx not_active Application Discontinuation
- 1972-11-27 CH CH1724272A patent/CH568367A5/xx not_active IP Right Cessation
- 1972-12-29 IT IT71288/72A patent/IT976433B/it active
-
1973
- 1973-01-12 DE DE2301479A patent/DE2301479C3/de not_active Expired
- 1973-01-18 JP JP48008251A patent/JPS4883117A/ja active Pending
- 1973-01-18 US US05/324,715 patent/US4048189A/en not_active Expired - Lifetime
- 1973-01-19 BR BR73448A patent/BR7300448D0/pt unknown
- 1973-01-22 GB GB310973A patent/GB1390292A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US4048189A (en) | 1977-09-13 |
| DE2301479A1 (de) | 1973-07-26 |
| CH568367A5 (OSRAM) | 1975-10-31 |
| BE794330A (fr) | 1973-07-19 |
| DE2301479B2 (de) | 1978-10-19 |
| NL7215370A (OSRAM) | 1973-07-24 |
| JPS4883117A (OSRAM) | 1973-11-06 |
| FR2168198B1 (OSRAM) | 1974-10-18 |
| BR7300448D0 (pt) | 1973-12-18 |
| GB1390292A (en) | 1975-04-09 |
| FR2168198A1 (OSRAM) | 1973-08-31 |
| IT976433B (it) | 1974-08-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| EHJ | Ceased/non-payment of the annual fee |