CA1037473A - PROCESS FOR PREPARING COPPER PHTHALOCYANINE PIGMENTS OF THE .alpha.-MODIFICATION - Google Patents
PROCESS FOR PREPARING COPPER PHTHALOCYANINE PIGMENTS OF THE .alpha.-MODIFICATIONInfo
- Publication number
- CA1037473A CA1037473A CA226,228A CA226228A CA1037473A CA 1037473 A CA1037473 A CA 1037473A CA 226228 A CA226228 A CA 226228A CA 1037473 A CA1037473 A CA 1037473A
- Authority
- CA
- Canada
- Prior art keywords
- alpha
- copper phthalocyanine
- cupc
- water
- ang
- 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
- 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 abstract description 5
- 239000000049 pigment Substances 0.000 title abstract description 26
- 238000012986 modification Methods 0.000 title abstract description 13
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 27
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims abstract description 11
- 239000007788 liquid Substances 0.000 claims abstract description 5
- 239000012736 aqueous medium Substances 0.000 claims abstract description 3
- JVTCNOASZYIKTG-UHFFFAOYSA-N stk329495 Chemical compound [Cu].[N-]1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)[N-]3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 JVTCNOASZYIKTG-UHFFFAOYSA-N 0.000 claims abstract 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 12
- 239000007900 aqueous suspension Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- -1 heterocyclic organic compound Chemical class 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 238000001556 precipitation Methods 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 150000002596 lactones Chemical class 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 238000010586 diagram Methods 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims 1
- 150000001983 dialkylethers Chemical class 0.000 claims 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 1
- 229960004756 ethanol Drugs 0.000 claims 1
- 235000019441 ethanol Nutrition 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 150000003951 lactams Chemical class 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 230000001172 regenerating effect Effects 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 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 abstract description 2
- 150000001491 aromatic compounds Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].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 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 239000011324 bead Substances 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 239000006259 organic additive Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- GHPYJLCQYMAXGG-WCCKRBBISA-N (2R)-2-amino-3-(2-boronoethylsulfanyl)propanoic acid hydrochloride Chemical compound Cl.N[C@@H](CSCCB(O)O)C(O)=O GHPYJLCQYMAXGG-WCCKRBBISA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
- 101150002998 LCAT gene Proteins 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 1
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 1
- 241000219498 Alnus glutinosa Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- DIWRORZWFLOCLC-UHFFFAOYSA-N Lorazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1Cl DIWRORZWFLOCLC-UHFFFAOYSA-N 0.000 description 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
- 244000166490 Tetrameles nudiflora Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- DQSGVVGOPRWTKI-QVFAWCHISA-N atazanavir sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C([C@H](NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)[C@@H](O)CN(CC=1C=CC(=CC=1)C=1N=CC=CC=1)NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)C1=CC=CC=C1 DQSGVVGOPRWTKI-QVFAWCHISA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010981 drying operation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000010626 work up procedure 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Optical Filters (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2421804A DE2421804C2 (de) | 1974-05-06 | 1974-05-06 | Verfahren zur Herstellung von farbstarken Kupferphthalocyaninpigmenten der α-Modifikation und deren Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1037473A true CA1037473A (en) | 1978-08-29 |
Family
ID=5914747
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA226,228A Expired CA1037473A (en) | 1974-05-06 | 1975-05-05 | PROCESS FOR PREPARING COPPER PHTHALOCYANINE PIGMENTS OF THE .alpha.-MODIFICATION |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4056534A (en, 2012) |
| JP (1) | JPS50150727A (en, 2012) |
| BE (1) | BE828775A (en, 2012) |
| BR (1) | BR7502712A (en, 2012) |
| CA (1) | CA1037473A (en, 2012) |
| CH (1) | CH578039A5 (en, 2012) |
| DE (1) | DE2421804C2 (en, 2012) |
| DK (1) | DK141054C (en, 2012) |
| FR (1) | FR2270305B1 (en, 2012) |
| GB (1) | GB1492224A (en, 2012) |
| IN (1) | IN143112B (en, 2012) |
| IT (1) | IT1037820B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2417531A1 (fr) * | 1978-02-21 | 1979-09-14 | Ugine Kuhlmann | Nouveau procede de preparation de pigments de phtalocyanine |
| DE3636428A1 (de) * | 1986-10-25 | 1988-05-05 | Basf Ag | Verfahren zur herstellung von farbstarken polyhalogenkupferphthalocyaninpigmenten |
| US4879380A (en) * | 1988-05-05 | 1989-11-07 | Basf Corp. | Process for conditioning crude polyhalogenated pigments using a heterocyclic organic solvent |
| EP0574790B1 (de) * | 1992-06-18 | 1998-05-13 | Clariant GmbH | Verfahren zur Herstellung von Pigmentzubereitungen auf Basis von Phthalocyaninpigmenten |
| DE59308597D1 (de) * | 1992-06-18 | 1998-07-02 | Clariant Gmbh | Verfahren zur Herstellung von Kupferphthalocyaninpigmentzubereitungen der alpha-Phase |
| DE10257498A1 (de) * | 2002-12-10 | 2004-07-01 | Clariant Gmbh | Verfahren zur Herstellung von Phthalocyaninpigmentzubereitungen |
| DE102004059863A1 (de) * | 2004-12-11 | 2006-06-14 | Clariant Gmbh | Verfahren zur Behandlung von Phthalocyaninpigmenten für wetter- und lichtechte Einfärbung von Kunststoffen |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB600911A (en) * | 1943-03-12 | 1948-04-22 | American Cyanamid Co | Solvent stable phthalocyanine pigments |
| GB703507A (en) * | 1951-10-16 | 1954-02-03 | Gen Aniline & Film Corp | Process for producing non-crystallizing copper phthalocyanines |
| DE1127323B (de) * | 1953-08-29 | 1962-04-12 | Basf Ag | Loesungsmittelstabile Mischung von Kupferphthalocyaninpigmentfarbstoffen der ª-Form |
| US3004986A (en) * | 1957-02-08 | 1961-10-17 | Standard Ultramarine & Color C | Phthalocyanine pigments |
| DE1136303B (de) * | 1960-05-11 | 1962-09-13 | Bayer Ag | Verfahren zur Herstellung einer farbstarken ª‡-Modifikation des Cu-Phthalocyanins |
| US3014917A (en) * | 1960-10-07 | 1961-12-26 | Du Pont | Preparation of crystal stable copper phthalocyanine |
| DE1187219B (de) * | 1961-02-16 | 1965-02-18 | Siegle & Co G M B H G | Verfahren zur Herstellung eines gruenstichigen, farbstarken Kupferphthalocyanins deralpha-Modifikation, das kristallisations- und flockungsbestaendig ist |
| GB1096192A (en) * | 1964-02-24 | 1967-12-20 | Ici Ltd | Milling process for producing ª‡-form copper phthalocyanine pigments |
| GB1140836A (en) * | 1966-02-22 | 1969-01-22 | Geigy Uk Ltd | Treatment of phthalocyanine pigments |
| US3801591A (en) * | 1972-06-12 | 1974-04-02 | Du Pont | Production of phthalocyanine pigment |
-
1974
- 1974-05-06 DE DE2421804A patent/DE2421804C2/de not_active Expired
-
1975
- 1975-04-24 GB GB17046/75A patent/GB1492224A/en not_active Expired
- 1975-04-25 IN IN828/CAL/1975A patent/IN143112B/en unknown
- 1975-05-02 CH CH566375A patent/CH578039A5/xx not_active IP Right Cessation
- 1975-05-02 IT IT22968/75A patent/IT1037820B/it active
- 1975-05-02 JP JP50052640A patent/JPS50150727A/ja active Pending
- 1975-05-05 FR FR7513908A patent/FR2270305B1/fr not_active Expired
- 1975-05-05 BR BR3462/75A patent/BR7502712A/pt unknown
- 1975-05-05 DK DK196075A patent/DK141054C/da not_active IP Right Cessation
- 1975-05-05 US US05/574,759 patent/US4056534A/en not_active Expired - Lifetime
- 1975-05-05 CA CA226,228A patent/CA1037473A/en not_active Expired
- 1975-05-06 BE BE156098A patent/BE828775A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH578039A5 (en, 2012) | 1976-07-30 |
| JPS50150727A (en, 2012) | 1975-12-03 |
| FR2270305B1 (en, 2012) | 1979-08-24 |
| US4056534A (en) | 1977-11-01 |
| DK141054C (da) | 1980-06-23 |
| IT1037820B (it) | 1979-11-20 |
| DE2421804C2 (de) | 1983-11-10 |
| DE2421804A1 (de) | 1975-12-04 |
| FR2270305A1 (en, 2012) | 1975-12-05 |
| IN143112B (en, 2012) | 1977-10-01 |
| DK141054B (da) | 1979-12-31 |
| GB1492224A (en) | 1977-11-16 |
| BE828775A (fr) | 1975-11-06 |
| BR7502712A (pt) | 1976-03-16 |
| DK196075A (da) | 1975-11-07 |
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