DE2157555C3 - Phthalocyaninpigmentgemische, Verfahren zur Stabilisierung von Phthalocyaninen und Verwendung der Phthalocyaninpigmentgemische - Google Patents
Phthalocyaninpigmentgemische, Verfahren zur Stabilisierung von Phthalocyaninen und Verwendung der PhthalocyaninpigmentgemischeInfo
- Publication number
- DE2157555C3 DE2157555C3 DE2157555A DE2157555A DE2157555C3 DE 2157555 C3 DE2157555 C3 DE 2157555C3 DE 2157555 A DE2157555 A DE 2157555A DE 2157555 A DE2157555 A DE 2157555A DE 2157555 C3 DE2157555 C3 DE 2157555C3
- Authority
- DE
- Germany
- Prior art keywords
- phthalocyanine
- weight
- parts
- phthalocyanine pigment
- pigment mixtures
- 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
- 239000000049 pigment Substances 0.000 title claims description 29
- 239000000203 mixture Substances 0.000 title claims description 22
- 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 title claims description 21
- 238000000034 method Methods 0.000 title claims description 5
- 230000000087 stabilizing effect Effects 0.000 title claims description 5
- 230000008569 process Effects 0.000 title 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 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000003973 paint Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 5
- 239000000976 ink Substances 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims description 2
- 229920003023 plastic Polymers 0.000 claims description 2
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000013078 crystal Substances 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 238000005189 flocculation Methods 0.000 description 4
- 230000016615 flocculation Effects 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- LUTAOOYCLLVACD-UHFFFAOYSA-N C1=CC(C)=CC=C1NC[Cu](CNC=1C=CC(C)=CC=1)CNC1=CC=C(C)C=C1 Chemical compound C1=CC(C)=CC=C1NC[Cu](CNC=1C=CC(C)=CC=1)CNC1=CC=C(C)C=C1 LUTAOOYCLLVACD-UHFFFAOYSA-N 0.000 description 3
- MYAHQEOHRAECPK-UHFFFAOYSA-N CC1=C(NC[Cu](CNC2=C(C=CC=C2C)C)CNC2=C(C=CC=C2C)C)C(=CC=C1)C Chemical compound CC1=C(NC[Cu](CNC2=C(C=CC=C2C)C)CNC2=C(C=CC=C2C)C)C(=CC=C1)C MYAHQEOHRAECPK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- GJCYDDVFBVFNAS-UHFFFAOYSA-N CC1=CC(C)=CC(C)=C1NC[Cu](CNC=1C(=CC(C)=CC=1C)C)CNC1=C(C)C=C(C)C=C1C Chemical compound CC1=CC(C)=CC(C)=C1NC[Cu](CNC=1C(=CC(C)=CC=1C)C)CNC1=C(C)C=C(C)C=C1C GJCYDDVFBVFNAS-UHFFFAOYSA-N 0.000 description 2
- QNZVAXYDDSNSCP-UHFFFAOYSA-N ClC[Cu](CCl)CCl Chemical compound ClC[Cu](CCl)CCl QNZVAXYDDSNSCP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 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 1
- KWVPRPSXBZNOHS-UHFFFAOYSA-N 2,4,6-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C(C)=C1 KWVPRPSXBZNOHS-UHFFFAOYSA-N 0.000 description 1
- OYMYFDBEFRDYCL-UHFFFAOYSA-N CC(NC1=CC=CC=C1)[Cu](C(C)NC1=CC=CC=C1)C(C)NC1=CC=CC=C1 Chemical compound CC(NC1=CC=CC=C1)[Cu](C(C)NC1=CC=CC=C1)C(C)NC1=CC=CC=C1 OYMYFDBEFRDYCL-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 238000007265 chloromethylation reaction Methods 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- -1 methylphenylamino Chemical class 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 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
- C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
- C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
- C09B68/44—Non-ionic groups, e.g. halogen, OH or SH
- C09B68/446—Amines or polyamines, e.g. aminopropyl, 1,3,4,-triamino-pentyl or polyethylene imine
-
- 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
- C09B47/12—Obtaining compounds having alkyl radicals, or alkyl radicals substituted by hetero atoms, bound to the phthalocyanine skeleton
-
- 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
- C09B47/12—Obtaining compounds having alkyl radicals, or alkyl radicals substituted by hetero atoms, bound to the phthalocyanine skeleton
- C09B47/16—Obtaining compounds having alkyl radicals, or alkyl radicals substituted by hetero atoms, bound to the phthalocyanine skeleton having alkyl radicals substituted by nitrogen atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7041759A FR2114245A5 (US08197722-20120612-C00042.png) | 1970-11-20 | 1970-11-20 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2157555A1 DE2157555A1 (de) | 1972-05-25 |
| DE2157555B2 DE2157555B2 (de) | 1980-10-30 |
| DE2157555C3 true DE2157555C3 (de) | 1981-07-30 |
Family
ID=9064480
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2157555A Expired DE2157555C3 (de) | 1970-11-20 | 1971-11-19 | Phthalocyaninpigmentgemische, Verfahren zur Stabilisierung von Phthalocyaninen und Verwendung der Phthalocyaninpigmentgemische |
Country Status (12)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4141904A (en) * | 1974-03-25 | 1979-02-27 | Produits Chimiques Ugine Kuhlmann | Process for the preparation of phthalocyanine pigments |
| FR2278741A1 (fr) * | 1974-07-19 | 1976-02-13 | Ugine Kuhlmann | Pigments de phtalocyanine stables a la cristallisation |
| FR2278740A1 (fr) * | 1974-07-19 | 1976-02-13 | Ugine Kuhlmann | Pigments de phtalocyanine stables a la cristallisation |
| FR2278739A1 (fr) * | 1974-07-19 | 1976-02-13 | Ugine Kuhlmann | Pigments de phtalocyanines stables a la cristallisation |
| GB9110260D0 (en) * | 1991-05-11 | 1991-07-03 | Ciba Geigy Ag | Pigment compositions |
| JP3129030B2 (ja) * | 1993-06-04 | 2001-01-29 | 東洋インキ製造株式会社 | 銅フタロシアニン顔料組成物の製造方法 |
| US7077896B2 (en) * | 2003-06-13 | 2006-07-18 | Toyo Ink Mfg. Co., Ltd. | Pigment composition and use thereof in plastic |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA758485A (en) * | 1967-05-09 | Black William | Manufacture of pigment compositions | |
| FR1332175A (US08197722-20120612-C00042.png) * | 1961-06-20 | 1963-12-16 | ||
| FR1353759A (fr) * | 1962-03-14 | 1964-02-28 | Ici Ltd | Fabrication de compositions de pigments |
| FR1570578A (US08197722-20120612-C00042.png) * | 1968-03-29 | 1969-06-13 | ||
| CH528579A (de) * | 1969-08-13 | 1972-09-30 | Ciba Geigy Ag | Verfahren zur Herstellung von Pigmentzusammensetzungen |
-
1970
- 1970-11-20 FR FR7041759A patent/FR2114245A5/fr not_active Expired
-
1971
- 1971-10-21 BE BE774289A patent/BE774289A/xx unknown
- 1971-11-09 CH CH1627271A patent/CH538529A/fr not_active IP Right Cessation
- 1971-11-09 NL NL7115367A patent/NL7115367A/xx not_active Application Discontinuation
- 1971-11-10 DK DK551171AA patent/DK131507B/da not_active IP Right Cessation
- 1971-11-12 ES ES396964A patent/ES396964A1/es not_active Expired
- 1971-11-19 IT IT70788/71A patent/IT942893B/it active
- 1971-11-19 DE DE2157555A patent/DE2157555C3/de not_active Expired
- 1971-11-19 JP JP9298071A patent/JPS5527583B1/ja active Pending
- 1971-11-19 BR BR7725/71A patent/BR7107725D0/pt unknown
- 1971-11-22 US US00201201A patent/US3767442A/en not_active Expired - Lifetime
- 1971-11-22 GB GB5406571A patent/GB1374596A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT942893B (it) | 1973-04-02 |
| CH538529A (fr) | 1973-06-30 |
| DE2157555B2 (de) | 1980-10-30 |
| BR7107725D0 (pt) | 1973-02-20 |
| DK131507C (US08197722-20120612-C00042.png) | 1975-12-22 |
| ES396964A1 (es) | 1974-06-16 |
| US3767442A (en) | 1973-10-23 |
| FR2114245A5 (US08197722-20120612-C00042.png) | 1972-06-30 |
| GB1374596A (en) | 1974-11-20 |
| BE774289A (fr) | 1972-04-21 |
| JPS5527583B1 (US08197722-20120612-C00042.png) | 1980-07-22 |
| DE2157555A1 (de) | 1972-05-25 |
| NL7115367A (US08197722-20120612-C00042.png) | 1972-05-24 |
| DK131507B (da) | 1975-07-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OGA | New person/name/address of the applicant | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |