DK166588B1 - Fremgangsmaade til omdannelse af raat kobberphthalocyanin (cupc) til alfa- eller beta-pigmentformen samt hoejmolekylaert organisk materiale, male- eller farvemateriale og organiske polymerer indeholdende dette cupc-pigment - Google Patents
Fremgangsmaade til omdannelse af raat kobberphthalocyanin (cupc) til alfa- eller beta-pigmentformen samt hoejmolekylaert organisk materiale, male- eller farvemateriale og organiske polymerer indeholdende dette cupc-pigment Download PDFInfo
- Publication number
- DK166588B1 DK166588B1 DK287586A DK287586A DK166588B1 DK 166588 B1 DK166588 B1 DK 166588B1 DK 287586 A DK287586 A DK 287586A DK 287586 A DK287586 A DK 287586A DK 166588 B1 DK166588 B1 DK 166588B1
- Authority
- DK
- Denmark
- Prior art keywords
- cupc
- parts
- mixture
- process according
- crude
- Prior art date
Links
- 239000000049 pigment Substances 0.000 title claims description 46
- 238000000034 method Methods 0.000 title claims description 41
- 239000000463 material Substances 0.000 title claims description 10
- 239000003973 paint Substances 0.000 title claims description 7
- 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 3
- 238000006243 chemical reaction Methods 0.000 title description 16
- 239000011368 organic material Substances 0.000 title description 3
- 101100044618 Tetrahymena thermophila ILSA gene Proteins 0.000 title 1
- 238000002349 difference gel electrophoresis Methods 0.000 title 1
- 239000000203 mixture Substances 0.000 claims description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- 238000000227 grinding Methods 0.000 claims description 17
- -1 phenyl ester Chemical class 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
- 239000000975 dye Substances 0.000 claims description 10
- 239000002002 slurry Substances 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 10
- 239000003929 acidic solution Substances 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 7
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 6
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 125000005907 alkyl ester group Chemical group 0.000 claims description 3
- 230000003750 conditioning effect Effects 0.000 claims description 3
- 238000003801 milling Methods 0.000 claims description 3
- 229920000620 organic polymer Polymers 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- UWCORGKXLPEJDM-UHFFFAOYSA-N methyl 2,4,5-trichloro-6-cyano-3-phenoxybenzoate Chemical group ClC1=C(C#N)C(C(=O)OC)=C(Cl)C(OC=2C=CC=CC=2)=C1Cl UWCORGKXLPEJDM-UHFFFAOYSA-N 0.000 claims description 2
- 239000005416 organic matter Substances 0.000 claims description 2
- 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 claims 17
- 239000003086 colorant Substances 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 239000012065 filter cake Substances 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 239000002253 acid Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical group [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
- 229910000831 Steel Inorganic materials 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000010959 steel Substances 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical group CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 3
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 229920000180 alkyd Polymers 0.000 description 3
- 239000011609 ammonium molybdate Substances 0.000 description 3
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 3
- 235000018660 ammonium molybdate Nutrition 0.000 description 3
- 229940010552 ammonium molybdate Drugs 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 3
- 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 3
- 238000010348 incorporation Methods 0.000 description 3
- 238000003825 pressing Methods 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000004408 titanium dioxide Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical class O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- WMFHUUKYIUOHRA-UHFFFAOYSA-N (3-phenoxyphenyl)methanamine;hydrochloride Chemical compound Cl.NCC1=CC=CC(OC=2C=CC=CC=2)=C1 WMFHUUKYIUOHRA-UHFFFAOYSA-N 0.000 description 1
- YQCQRPXVCLGQGD-UHFFFAOYSA-N 2,9,16,23-tetraphenoxy-29h,31h-phthalocyanine Chemical class C=1C=C2C(N=C3NC(C4=CC=C(OC=5C=CC=CC=5)C=C43)=NC=3NC([C]4C=CC(OC=5C=CC=CC=5)=CC4=3)=NC=3N=C([C]4C=CC(OC=5C=CC=CC=5)=CC4=3)N=3)=NC=3C2=CC=1OC1=CC=CC=C1 YQCQRPXVCLGQGD-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- YMIFCOGYMQTQBP-UHFFFAOYSA-L calcium;dichloride;hydrate Chemical compound O.[Cl-].[Cl-].[Ca+2] YMIFCOGYMQTQBP-UHFFFAOYSA-L 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000012430 stability testing Methods 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction 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
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60J—WINDOWS, WINDSCREENS, NON-FIXED ROOFS, DOORS, OR SIMILAR DEVICES FOR VEHICLES; REMOVABLE EXTERNAL PROTECTIVE COVERINGS SPECIALLY ADAPTED FOR VEHICLES
- B60J1/00—Windows; Windscreens; Accessories therefor
- B60J1/02—Windows; Windscreens; Accessories therefor arranged at the vehicle front, e.g. structure of the glazing, mounting of the glazing
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B62—LAND VEHICLES FOR TRAVELLING OTHERWISE THAN ON RAILS
- B62D—MOTOR VEHICLES; TRAILERS
- B62D33/00—Superstructures for load-carrying vehicles
- B62D33/06—Drivers' cabs
- B62D33/0617—Drivers' cabs for tractors or off-the-road vehicles
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Combustion & Propulsion (AREA)
- Transportation (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8515600 | 1985-06-20 | ||
| GB858515600A GB8515600D0 (en) | 1985-06-20 | 1985-06-20 | Pigmentary copper phthalocyanine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK287586D0 DK287586D0 (da) | 1986-06-19 |
| DK287586A DK287586A (da) | 1986-12-21 |
| DK166588B1 true DK166588B1 (da) | 1993-06-14 |
Family
ID=10581034
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK287586A DK166588B1 (da) | 1985-06-20 | 1986-06-19 | Fremgangsmaade til omdannelse af raat kobberphthalocyanin (cupc) til alfa- eller beta-pigmentformen samt hoejmolekylaert organisk materiale, male- eller farvemateriale og organiske polymerer indeholdende dette cupc-pigment |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US4694078A (fr) |
| EP (1) | EP0209487B1 (fr) |
| JP (1) | JPH0730264B2 (fr) |
| KR (1) | KR940006240B1 (fr) |
| CA (1) | CA1263861A (fr) |
| DE (1) | DE3686297D1 (fr) |
| DK (1) | DK166588B1 (fr) |
| GB (1) | GB8515600D0 (fr) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5135972A (en) * | 1989-09-18 | 1992-08-04 | Milliken Research Corporation | Poly(oxyalkylene) modified phthalocyanine colorants |
| DE19745922A1 (de) * | 1997-10-17 | 1999-04-22 | Basf Ag | Verfahren zur Überführung von halogenierten Kupferphtalocyanin-Rohpigmenten in eine für die Anwendung geeignete Pigmentform |
| US6156116A (en) * | 1999-03-19 | 2000-12-05 | Air Products And Chemicals, Inc. | Conversion of crude phthalocyanine blue from red to green shade in an aqueous environment |
| JP4782259B2 (ja) * | 1999-03-31 | 2011-09-28 | 株式会社日本触媒 | 顔料分散剤およびその用途 |
| EP1130065B1 (fr) * | 2000-02-04 | 2006-03-08 | Dainichiseika Color & Chemicals Mfg. Co. Ltd. | Compositions pigmentaires, leurs procédés de préparations, colorants et articles colorés |
| US6476219B1 (en) | 2002-02-08 | 2002-11-05 | Xerox Corporation | Methods for preparing phthalocyanine compositions |
| US6472523B1 (en) | 2002-02-08 | 2002-10-29 | Xerox Corporation | Phthalocyanine compositions |
| US6726755B2 (en) | 2002-02-08 | 2004-04-27 | Xerox Corporation | Ink compositions containing phthalocyanines |
| US8168359B2 (en) * | 2008-03-10 | 2012-05-01 | Xerox Corporation | Nanosized particles of phthalocyanine pigments |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1296834A (fr) * | 1969-04-09 | 1972-11-22 | ||
| CH564525A5 (fr) * | 1972-01-17 | 1975-07-31 | Ciba Geigy Ag | |
| DE2262911B2 (de) * | 1972-12-22 | 1975-02-13 | Farbwerke Hoechst Ag Vormals Meister Lucius & Bruening, 6000 Frankfurt | Verfahren zur Herstellung von Cu-Phthalocyaninpigmenten der alpha-Modifikation |
| CA1030959A (fr) * | 1973-11-27 | 1978-05-09 | Jost Von Der Crone | Phtalocyanines halogenees et methode de fabrication |
| US4141904A (en) * | 1974-03-25 | 1979-02-27 | Produits Chimiques Ugine Kuhlmann | Process for the preparation of phthalocyanine pigments |
| FR2278739A1 (fr) * | 1974-07-19 | 1976-02-13 | Ugine Kuhlmann | Pigments de phtalocyanines stables a la cristallisation |
| GB1558663A (en) * | 1975-08-21 | 1980-01-09 | Ciba Geigy Ag | Preparation of pigmentary phtalocyanine |
| GB1544171A (en) * | 1977-02-17 | 1979-04-11 | Ciba Geigy Ag | Pigment compositions |
-
1985
- 1985-06-20 GB GB858515600A patent/GB8515600D0/en active Pending
-
1986
- 1986-06-09 US US06/871,932 patent/US4694078A/en not_active Expired - Lifetime
- 1986-06-16 EP EP86810271A patent/EP0209487B1/fr not_active Expired - Lifetime
- 1986-06-16 DE DE8686810271T patent/DE3686297D1/de not_active Expired - Lifetime
- 1986-06-18 CA CA000511898A patent/CA1263861A/fr not_active Expired
- 1986-06-19 KR KR1019860004892A patent/KR940006240B1/ko not_active Expired - Fee Related
- 1986-06-19 DK DK287586A patent/DK166588B1/da active
- 1986-06-20 JP JP61143121A patent/JPH0730264B2/ja not_active Expired - Lifetime
-
1987
- 1987-06-22 US US07/064,730 patent/US4801634A/en not_active Expired - Lifetime
- 1987-06-22 US US07/064,729 patent/US4801638A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0730264B2 (ja) | 1995-04-05 |
| US4801638A (en) | 1989-01-31 |
| GB8515600D0 (en) | 1985-07-24 |
| DK287586D0 (da) | 1986-06-19 |
| EP0209487B1 (fr) | 1992-08-05 |
| US4694078A (en) | 1987-09-15 |
| CA1263861A (fr) | 1989-12-12 |
| KR940006240B1 (ko) | 1994-07-13 |
| DK287586A (da) | 1986-12-21 |
| JPS61296071A (ja) | 1986-12-26 |
| US4801634A (en) | 1989-01-31 |
| DE3686297D1 (de) | 1992-09-10 |
| KR870000387A (ko) | 1987-02-18 |
| EP0209487A3 (en) | 1989-10-18 |
| EP0209487A2 (fr) | 1987-01-21 |
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