CA1073880A - PROCESS FOR THE PREPARATION OF EASILY DISPERSIBLE PHTHALOCYANINE PIGMENTS OF THE .beta.-MODIFICATION - Google Patents
PROCESS FOR THE PREPARATION OF EASILY DISPERSIBLE PHTHALOCYANINE PIGMENTS OF THE .beta.-MODIFICATIONInfo
- Publication number
- CA1073880A CA1073880A CA233,796A CA233796A CA1073880A CA 1073880 A CA1073880 A CA 1073880A CA 233796 A CA233796 A CA 233796A CA 1073880 A CA1073880 A CA 1073880A
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- carbon atoms
- parts
- cupc
- sulfamoyl
- 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
- 238000012986 modification Methods 0.000 title claims abstract description 51
- 239000000049 pigment Substances 0.000 title claims description 111
- 238000000034 method Methods 0.000 title claims description 46
- 230000008569 process Effects 0.000 title claims description 28
- 238000002360 preparation method Methods 0.000 title claims description 10
- 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 description 5
- -1 phthalocyanine radical Chemical class 0.000 claims abstract description 47
- 238000009826 distribution Methods 0.000 claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 238000005189 flocculation Methods 0.000 claims abstract description 9
- 230000016615 flocculation Effects 0.000 claims abstract description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 41
- 238000000227 grinding Methods 0.000 claims description 36
- 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 29
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 239000011324 bead Substances 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 21
- 239000004922 lacquer Substances 0.000 claims description 11
- 230000008707 rearrangement Effects 0.000 claims description 11
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
- 125000002130 sulfonic acid ester group Chemical group 0.000 claims description 4
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910052788 barium Inorganic materials 0.000 claims description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 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 abstract description 39
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 15
- 229910052802 copper Inorganic materials 0.000 abstract description 15
- 239000010949 copper Substances 0.000 abstract description 15
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- 239000000203 mixture Substances 0.000 description 33
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 32
- 239000000725 suspension Substances 0.000 description 24
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 238000004043 dyeing Methods 0.000 description 18
- 229960004592 isopropanol Drugs 0.000 description 16
- 239000000654 additive Substances 0.000 description 15
- 239000012065 filter cake Substances 0.000 description 15
- 239000011521 glass Substances 0.000 description 15
- 229910052573 porcelain Inorganic materials 0.000 description 15
- 210000003298 dental enamel Anatomy 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 230000000996 additive effect Effects 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 239000000975 dye Substances 0.000 description 10
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 10
- 239000013078 crystal Substances 0.000 description 8
- 230000007935 neutral effect Effects 0.000 description 7
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 239000013065 commercial product Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000001256 steam distillation Methods 0.000 description 3
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MNSGOOCAMMSKGI-UHFFFAOYSA-N N-(hydroxymethyl)phthalimide Chemical compound C1=CC=C2C(=O)N(CO)C(=O)C2=C1 MNSGOOCAMMSKGI-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical group CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 159000000009 barium salts Chemical class 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 239000011044 quartzite Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 241001072332 Monia Species 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 1
- 229940010552 ammonium molybdate Drugs 0.000 description 1
- 235000018660 ammonium molybdate Nutrition 0.000 description 1
- 239000011609 ammonium molybdate Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000010297 mechanical methods and process Methods 0.000 description 1
- 230000005226 mechanical processes and functions Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation 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
-
- 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
-
- 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)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742439983 DE2439983C3 (de) | 1974-08-21 | Verfahren zur Herstellung von leicht dispergierbaren Phthalocyaninpigmenten der beta-modifikation und deren Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1073880A true CA1073880A (en) | 1980-03-18 |
Family
ID=5923674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA233,796A Expired CA1073880A (en) | 1974-08-21 | 1975-08-20 | PROCESS FOR THE PREPARATION OF EASILY DISPERSIBLE PHTHALOCYANINE PIGMENTS OF THE .beta.-MODIFICATION |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS5147024A (en)) |
| AU (1) | AU8414475A (en)) |
| BE (1) | BE832622A (en)) |
| BR (1) | BR7505311A (en)) |
| CA (1) | CA1073880A (en)) |
| CH (1) | CH586740A5 (en)) |
| DK (1) | DK374875A (en)) |
| FR (1) | FR2282455A1 (en)) |
| GB (1) | GB1502884A (en)) |
| IN (1) | IN143503B (en)) |
| IT (1) | IT1041858B (en)) |
| NL (1) | NL7509758A (en)) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5492563A (en) * | 1994-04-21 | 1996-02-20 | Hoechst Ag | Fine division in the preparation of copper phthalocyanine pigments |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2905114C2 (de) * | 1979-02-10 | 1981-03-19 | Basf Ag, 6700 Ludwigshafen | Pigmentzubereitungen |
| DE3061493D1 (en) * | 1979-06-01 | 1983-02-03 | Ciba Geigy Ag | Process for manufacturing copper phthalocyanine-blue pigment compositions |
| EP0042816B1 (de) * | 1980-06-19 | 1984-04-18 | Ciba-Geigy Ag | Verfahren zur Herstellung von Pigmentlegierungen |
| JPS59102958A (ja) * | 1982-12-03 | 1984-06-14 | Sumitomo Chem Co Ltd | 銅フタロシアニン顔料の製造法 |
| JPS59155467A (ja) * | 1983-02-25 | 1984-09-04 | Toyo Ink Mfg Co Ltd | 銅フタロシアニン顔料の製造方法 |
| JPS60188470A (ja) * | 1984-03-08 | 1985-09-25 | Sumitomo Chem Co Ltd | 銅フタロシアニン顔料の製造法 |
| JPS60195161A (ja) * | 1984-03-16 | 1985-10-03 | サン・ケミカル・コ−ポレ−シヨン | フタロシアニン顔料の条件づけ方法及び製品 |
| JPS61163978A (ja) * | 1985-01-11 | 1986-07-24 | バスフ・コーポレイション | フタロシアニン分散材の製造方法 |
| GB9007924D0 (en) * | 1990-04-07 | 1990-06-06 | Ciba Geigy Ag | Production of pigments |
| US5284511A (en) * | 1993-04-12 | 1994-02-08 | Miles Inc. | Conditioning process for phthalocyanine pigments |
| US5534055A (en) | 1994-08-24 | 1996-07-09 | Bayer Corporation | Process for alpha-phase metal phthalocyanine pigments |
| US5728204A (en) * | 1996-01-31 | 1998-03-17 | Bayer Corporation | Preparation of phthalocyanine-containing waterborne coating systems |
| GB9818824D0 (en) * | 1998-08-29 | 1998-10-21 | Ciba Geigy Ag | Pigment compositions containing substituited amido phthalocyanine derivatives |
| TW588091B (en) | 1998-08-29 | 2004-05-21 | Ciba Sc Holding Ag | Pigment compositions containing substituted amido phthalocyanine derivatives |
| US6440207B1 (en) | 2000-03-03 | 2002-08-27 | Bayer Corporation | Method for preparing organic pigments |
| CA2455047A1 (en) | 2001-08-23 | 2003-03-06 | E.I. Du Pont De Nemours And Company | Method of producing stabilized organic pigment particles and device therefor |
| EP2057234B1 (en) | 2006-08-18 | 2014-10-08 | Sun Chemical Corporation | Pu-coated pigments |
| WO2009060573A1 (ja) * | 2007-11-07 | 2009-05-14 | Nippon Kayaku Kabushiki Kaisha | 水溶性ナフタロシアニン色素及びこれを含有する水系インク |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2238243A (en) * | 1939-12-28 | 1941-04-15 | Du Pont | Liquid coating composition |
| DE1223086B (de) * | 1961-05-18 | 1966-08-18 | Basf Ag | Flockungsbestaendige und loesungsmittelechte Phthalocyaninpigmentgemische |
| FR1353759A (fr) * | 1962-03-14 | 1964-02-28 | Ici Ltd | Fabrication de compositions de pigments |
| JPS4933326A (en)) * | 1972-08-05 | 1974-03-27 |
-
1975
- 1975-08-07 GB GB33013/75A patent/GB1502884A/en not_active Expired
- 1975-08-15 NL NL7509758A patent/NL7509758A/xx unknown
- 1975-08-18 CH CH1075175A patent/CH586740A5/xx not_active IP Right Cessation
- 1975-08-19 IT IT26421/75A patent/IT1041858B/it active
- 1975-08-19 IN IN1616/CAL/1975A patent/IN143503B/en unknown
- 1975-08-20 FR FR7525734A patent/FR2282455A1/fr active Granted
- 1975-08-20 JP JP50100237A patent/JPS5147024A/ja active Pending
- 1975-08-20 BR BR7505311*A patent/BR7505311A/pt unknown
- 1975-08-20 AU AU84144/75A patent/AU8414475A/en not_active Expired
- 1975-08-20 DK DK374875A patent/DK374875A/da not_active Application Discontinuation
- 1975-08-20 CA CA233,796A patent/CA1073880A/en not_active Expired
- 1975-08-21 BE BE159360A patent/BE832622A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5492563A (en) * | 1994-04-21 | 1996-02-20 | Hoechst Ag | Fine division in the preparation of copper phthalocyanine pigments |
Also Published As
| Publication number | Publication date |
|---|---|
| DK374875A (da) | 1976-02-22 |
| BR7505311A (pt) | 1976-08-03 |
| DE2439983A1 (de) | 1976-03-04 |
| JPS5147024A (en)) | 1976-04-22 |
| GB1502884A (en) | 1978-03-08 |
| AU8414475A (en) | 1977-02-24 |
| BE832622A (fr) | 1976-02-23 |
| DE2439983B2 (de) | 1976-11-18 |
| IT1041858B (it) | 1980-01-10 |
| FR2282455A1 (fr) | 1976-03-19 |
| CH586740A5 (en)) | 1977-04-15 |
| FR2282455B1 (en)) | 1979-03-16 |
| NL7509758A (nl) | 1976-02-24 |
| IN143503B (en)) | 1977-12-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1073880A (en) | PROCESS FOR THE PREPARATION OF EASILY DISPERSIBLE PHTHALOCYANINE PIGMENTS OF THE .beta.-MODIFICATION | |
| US4310359A (en) | Pigment compositions | |
| KR100218024B1 (ko) | 페릴렌 화합물의 내부 염, 그의 제조방법 및 용도 | |
| US4317682A (en) | Pigment compositions and use thereof | |
| US4135944A (en) | Pigment composition | |
| US6471766B2 (en) | Pigment dispersants and pigment compositions containing the same | |
| DE69813541T2 (de) | Thiazin-indigo pigmente, diese enthaltende feste lösungen und ihre herstellung | |
| US3763182A (en) | Method for producing metal phthalocyanine type pigment | |
| US4133695A (en) | Pigment composition | |
| US5662739A (en) | Use of fatty acid taurides for the dispersion of polycyclic pigments | |
| JP3055365B2 (ja) | ２，５−ジ（アリールアミノ）−３，６−ジヒドロテレフタル酸ジアルキルエステル類の製造法およびこれを中間体とするキナクリドン類の製造法 | |
| CA1088255A (en) | Pigment compositions | |
| CA1080907A (en) | Pigment compositions | |
| EP0266219B1 (en) | Process for producing copper phthalocyanine pigment | |
| US4055440A (en) | Pigment compositions | |
| US4194921A (en) | Pigment compositions and process for dust free pigment beads | |
| US5393339A (en) | Preparation of phthalocyanine pigments | |
| CA1037472A (en) | PROCESS FOR PREPARING COPPER PHTHALOCYANINE PIGMENTS OF THE .alpha.-MODIFICATION | |
| EP1083176B1 (en) | Catalyzed oxidation process for preparing quinacridone pigments using a polyalkylene glycol medium | |
| US4171309A (en) | Process for the preparation of a solvent-stable, red-shade copper phthalocyanine pigment composition | |
| EP0456609A1 (en) | Fluorescent yellow 1,2,3,4-tetrachloro-11H-isoindolo-[2,1-a]-benzimidazol-11-one pigments | |
| JPS6259147B2 (en)) | ||
| US6926768B2 (en) | Treatment of high performance pigments | |
| CN100513491C (zh) | 包括不对称取代的组分的喹吖啶酮颜料组合物 | |
| US10287435B2 (en) | Preparation of Pigment Red 149 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |