CA1159825A - Phthalocyanine pigments - Google Patents
Phthalocyanine pigmentsInfo
- Publication number
- CA1159825A CA1159825A CA000386068A CA386068A CA1159825A CA 1159825 A CA1159825 A CA 1159825A CA 000386068 A CA000386068 A CA 000386068A CA 386068 A CA386068 A CA 386068A CA 1159825 A CA1159825 A CA 1159825A
- Authority
- CA
- Canada
- Prior art keywords
- aryl
- pigment
- layer
- electrically
- alkyl
- 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 abstract description 64
- 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 abstract description 17
- 239000000463 material Substances 0.000 claims abstract description 54
- 238000003384 imaging method Methods 0.000 claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 38
- 230000008569 process Effects 0.000 claims abstract description 21
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 8
- LBGCRGLFTKVXDZ-UHFFFAOYSA-M ac1mc2aw Chemical group [Al+3].[Cl-].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 LBGCRGLFTKVXDZ-UHFFFAOYSA-M 0.000 claims abstract description 8
- 125000004171 alkoxy aryl group Chemical group 0.000 claims abstract description 8
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 8
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 8
- 239000000460 chlorine Chemical group 0.000 claims abstract description 8
- 229910052801 chlorine Chemical group 0.000 claims abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 7
- 239000000203 mixture Substances 0.000 claims description 22
- 239000007788 liquid Substances 0.000 claims description 21
- 230000005684 electric field Effects 0.000 claims description 14
- 230000005670 electromagnetic radiation Effects 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- -1 methoxyphenyl Chemical group 0.000 claims description 7
- 229920005989 resin Polymers 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- 230000003213 activating effect Effects 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000003944 tolyl group Chemical group 0.000 claims description 5
- 230000000007 visual effect Effects 0.000 claims description 5
- 238000000151 deposition Methods 0.000 claims description 2
- 238000009740 moulding (composite fabrication) Methods 0.000 claims 2
- 239000002245 particle Substances 0.000 description 25
- 235000013350 formula milk Nutrition 0.000 description 19
- 239000003086 colorant Substances 0.000 description 14
- 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 12
- 238000010521 absorption reaction Methods 0.000 description 9
- 238000011161 development Methods 0.000 description 8
- 230000018109 developmental process Effects 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000012876 carrier material Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 230000005012 migration Effects 0.000 description 3
- 238000013508 migration Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- PRAMZQXXPOLCIY-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethanesulfonic acid Chemical compound CC(=C)C(=O)OCCS(O)(=O)=O PRAMZQXXPOLCIY-UHFFFAOYSA-N 0.000 description 1
- CNPVJWYWYZMPDS-UHFFFAOYSA-N 2-methyldecane Chemical compound CCCCCCCCC(C)C CNPVJWYWYZMPDS-UHFFFAOYSA-N 0.000 description 1
- NKFIBMOQAPEKNZ-UHFFFAOYSA-N 5-amino-1h-indole-2-carboxylic acid Chemical compound NC1=CC=C2NC(C(O)=O)=CC2=C1 NKFIBMOQAPEKNZ-UHFFFAOYSA-N 0.000 description 1
- 101150034533 ATIC gene Proteins 0.000 description 1
- PLXMOAALOJOTIY-FPTXNFDTSA-N Aesculin Natural products OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)[C@H]1Oc2cc3C=CC(=O)Oc3cc2O PLXMOAALOJOTIY-FPTXNFDTSA-N 0.000 description 1
- NRZVMOKAFOFUAV-UHFFFAOYSA-K CC(C)[Ti+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O Chemical compound CC(C)[Ti+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O NRZVMOKAFOFUAV-UHFFFAOYSA-K 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 229910018557 Si O Inorganic materials 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical class C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940063655 aluminum stearate Drugs 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 239000011246 composite particle Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- QLZHNIAADXEJJP-UHFFFAOYSA-L dioxido-oxo-phenyl-$l^{5}-phosphane Chemical compound [O-]P([O-])(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-L 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- OFUAIAKLWWIPTC-UHFFFAOYSA-L magnesium;naphthalene-2-carboxylate Chemical compound [Mg+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 OFUAIAKLWWIPTC-UHFFFAOYSA-L 0.000 description 1
- 239000000696 magnetic material Substances 0.000 description 1
- SGGOJYZMTYGPCH-UHFFFAOYSA-L manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 SGGOJYZMTYGPCH-UHFFFAOYSA-L 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 125000005395 methacrylic acid group Chemical class 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N octadec-9-enoic acid Chemical compound CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 101150093826 par1 gene Proteins 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- ODNJVAVDJKOYFK-GRVYQHKQSA-L zinc;(9z,12z)-octadeca-9,12-dienoate Chemical compound [Zn+2].CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O.CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O ODNJVAVDJKOYFK-GRVYQHKQSA-L 0.000 description 1
- MXODCLTZTIFYDV-UHFFFAOYSA-L zinc;1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylate Chemical compound [Zn+2].C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C([O-])=O.C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C([O-])=O MXODCLTZTIFYDV-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/09—Colouring agents for toner particles
- G03G9/0906—Organic dyes
- G03G9/0918—Phthalocyanine dyes
-
- 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
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G17/00—Electrographic processes using patterns other than charge patterns, e.g. an electric conductivity pattern; Processes involving a migration, e.g. photoelectrophoresis, photoelectrosolography; Processes involving a selective transfer, e.g. electrophoto-adhesive processes; Apparatus essentially involving a single such process
- G03G17/04—Electrographic processes using patterns other than charge patterns, e.g. an electric conductivity pattern; Processes involving a migration, e.g. photoelectrophoresis, photoelectrosolography; Processes involving a selective transfer, e.g. electrophoto-adhesive processes; Apparatus essentially involving a single such process using photoelectrophoresis
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Molecular Biology (AREA)
- Organic Chemistry (AREA)
- Photoreceptors In Electrophotography (AREA)
- Liquid Developers In Electrophotography (AREA)
- Developing Agents For Electrophotography (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/194,200 US4311775A (en) | 1980-10-06 | 1980-10-06 | Novel phthalocyanine pigments and electrophotographic uses thereof |
| US194,200 | 1980-10-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1159825A true CA1159825A (en) | 1984-01-03 |
Family
ID=22716689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000386068A Expired CA1159825A (en) | 1980-10-06 | 1981-09-16 | Phthalocyanine pigments |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4311775A (en, 2012) |
| JP (1) | JPS5790058A (en, 2012) |
| CA (1) | CA1159825A (en, 2012) |
| DE (1) | DE3138999A1 (en, 2012) |
| FR (1) | FR2491484B1 (en, 2012) |
| GB (1) | GB2084605B (en, 2012) |
Families Citing this family (80)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58203455A (ja) * | 1982-05-21 | 1983-11-26 | Canon Inc | 静電荷現像用シアントナー及び電子写真法 |
| US4578330A (en) * | 1983-06-30 | 1986-03-25 | Eastman Kodak Company | Hydroxyaluminumphthalocyanine having reduced green absorption |
| US4555463A (en) * | 1984-08-22 | 1985-11-26 | Xerox Corporation | Photoresponsive imaging members with chloroindium phthalocyanine compositions |
| US4557989A (en) * | 1984-09-13 | 1985-12-10 | Xerox Corporation | Photoresponsive imaging members with dihydroxy metal phthalocyanine compositions |
| DE3446418A1 (de) * | 1984-12-20 | 1986-06-26 | Basf Ag, 6700 Ludwigshafen | Optisches aufzeichnungsmedium und verfahren zu seiner herstellung |
| US4732832A (en) * | 1985-12-06 | 1988-03-22 | Asahi Kasei Kogyo Kabushiki Kaisha | Electrophotographic photoconductor using aluminum phthalocyanine compound in charge generating layer |
| US4816386A (en) * | 1986-01-13 | 1989-03-28 | Toray Industries, Inc. | Near-infrared sensitive phthalocyanine-polymer compositions |
| DE68919818T2 (de) * | 1988-12-29 | 1995-05-04 | Toyo Ink Mfg Co | Optisches Aufzeichnungsmedium und Verfahren zu dessen Herstellung. |
| JP2541656B2 (ja) * | 1989-04-06 | 1996-10-09 | オリヱント化学工業株式会社 | ナフタロシアニン化合物及びその製造方法 |
| JPH04348142A (ja) * | 1991-03-29 | 1992-12-03 | Agency Of Ind Science & Technol | カラーフィルター形成用樹脂組成物 |
| JP3218770B2 (ja) * | 1993-01-14 | 2001-10-15 | 富士ゼロックス株式会社 | 電子写真感光体とそのためのフタロシアニン顔料および顔料分散液 |
| JP3077458B2 (ja) * | 1993-07-23 | 2000-08-14 | 東洋インキ製造株式会社 | アルミニウムフタロシアニン組成物の製造法 |
| US5466796A (en) * | 1994-04-26 | 1995-11-14 | Xerox Corporation | Alkoxy-bridged metallophthalocyanine dimers |
| US5456998A (en) * | 1994-04-26 | 1995-10-10 | Xerox Corporation | Photoconductive imaging members containing alkoxy-bridged metallophthalocyanine dimers |
| US5866637A (en) * | 1996-07-23 | 1999-02-02 | Ncr Corporation | Magnetic thermal transfer ribbon with non-metallic magnets |
| DE69716687T2 (de) * | 1996-08-20 | 2003-06-12 | Eastman Kodak Co., Rochester | Kuppler-Satz für Silberhalogenid-Farbbilderzeugung |
| US5738716A (en) * | 1996-08-20 | 1998-04-14 | Eastman Kodak Company | Color pigmented ink jet ink set |
| US5817805A (en) * | 1997-02-21 | 1998-10-06 | Eastman Kodak Company | Synthesis of bis(phthalocyanylalumino)tetraphenyldisiloxanes |
| GB2348433B (en) | 1999-03-31 | 2003-04-09 | Ilford Imaging Uk Ltd | Pigmented ink jet inks |
| US6152999A (en) * | 1999-04-27 | 2000-11-28 | Eastman Kodak Company | Color pigmented ink jet set |
| US6153000A (en) * | 1999-07-12 | 2000-11-28 | Eastman Kodak Company | Color pigmented ink jet ink set |
| US6764173B2 (en) | 2002-09-27 | 2004-07-20 | Eastman Kodak Company | Inkjet printing method |
| US7381755B2 (en) * | 2002-09-27 | 2008-06-03 | Eastman Kodak Company | Inkjet ink composition and ink/receiver combination |
| US6848777B2 (en) | 2002-09-27 | 2005-02-01 | Eastman Kodak Company | Aqueous inkjet ink and receiver combination |
| US6773102B2 (en) | 2002-09-27 | 2004-08-10 | Eastman Kodak Company | Inkjet printing method for an ink/receiver combination |
| US6908186B2 (en) * | 2003-03-26 | 2005-06-21 | Eastman Kodak Company | Inkjet ink composition and an ink/receiver combination |
| US7077516B2 (en) * | 2003-03-26 | 2006-07-18 | Eastman Kodak Company | Inkjet printing method |
| EP1801167A4 (en) * | 2004-09-08 | 2011-10-12 | Canon Kk | COATED FINE PARTICLES, DISPERSED FINE PARTICLES, METHOD FOR PRODUCING COATED FINE PARTICLES, INK, RECORDING METHOD AND RECORDED IMAGE |
| KR100528155B1 (ko) * | 2005-07-25 | 2005-11-15 | 씨엠에스테크놀로지(주) | 폴리 가교형 프탈로시아닌 화합물 및 이를 함유하는근적외선 흡수 잉크조성물 |
| US7973902B2 (en) * | 2006-11-10 | 2011-07-05 | Global Oled Technology Llc | Display with RGB color filter element sets |
| US7837780B2 (en) * | 2006-11-10 | 2010-11-23 | Global Oled Technology Llc | Green color filter element |
| EP1936441B1 (en) * | 2006-12-21 | 2010-03-10 | Konica Minolta Business Technologies, Inc. | Electrostatic image developing toner |
| KR100773089B1 (ko) * | 2007-04-30 | 2007-11-05 | 씨엠에스테크놀로지(주) | 감마선에 감응하는 폴리 가교형 프탈로시아닌 화합물 및 그를 포함하는 잉크 조성물 |
| US7951854B2 (en) | 2007-06-08 | 2011-05-31 | Fujifilm Corporation | Ink composition, ink set and inkjet recording method |
| JP5213382B2 (ja) | 2007-08-09 | 2013-06-19 | 富士フイルム株式会社 | 水性インク組成物、インクセット、及び画像記録方法 |
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| RU2527464C2 (ru) * | 2013-03-22 | 2014-08-27 | Федеральное государственное унитарное предприятие "Государственный научный центр "Научно-исследовательский институт органических полупродуктов и красителей" (ФГУП "ГНЦ "НИОПИК") | Способ получения фталоцианинмоно- и дифосфоновых кислот |
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| KR102423430B1 (ko) * | 2015-08-10 | 2022-07-21 | 삼성디스플레이 주식회사 | 컬러필터 및 이를 포함하는 표시장치 |
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Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3094535A (en) * | 1961-01-03 | 1963-06-18 | Malcolm E Kenney | Germanium phthalocyanines |
| US3094536A (en) * | 1961-01-03 | 1963-06-18 | Malcolm E Kenney | Silicon phthalocyanines |
| BE710350A (en, 2012) * | 1967-02-10 | 1968-08-05 | ||
| US3482972A (en) * | 1967-12-28 | 1969-12-09 | Polaroid Corp | Substituted phthalocyanine dye developers and their use in multicolor diffusion transfer processes |
| US3932454A (en) * | 1969-07-30 | 1976-01-13 | Xerox Corporation | Process of making hexagonal alpha metal-free phthalocyanine |
| US4142890A (en) * | 1977-05-20 | 1979-03-06 | Eastman Kodak Company | Photosensitive trans-epindolidione pigment for migration imaging processes |
| US4256819A (en) * | 1977-07-25 | 1981-03-17 | Eastman Kodak Company | Organic electrophotosensitive materials for migration imaging processes |
| US4131609A (en) * | 1978-02-23 | 1978-12-26 | The United States Of America As Represented By The Secretary Of The Navy | Silicon-phthalocyanine-siloxy monomers |
-
1980
- 1980-10-06 US US06/194,200 patent/US4311775A/en not_active Expired - Lifetime
-
1981
- 1981-09-16 CA CA000386068A patent/CA1159825A/en not_active Expired
- 1981-09-30 DE DE19813138999 patent/DE3138999A1/de active Granted
- 1981-10-06 JP JP56158272A patent/JPS5790058A/ja active Granted
- 1981-10-06 GB GB8130167A patent/GB2084605B/en not_active Expired
- 1981-10-06 FR FR8118759A patent/FR2491484B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2491484A1 (fr) | 1982-04-09 |
| DE3138999A1 (de) | 1982-04-22 |
| FR2491484B1 (fr) | 1987-02-20 |
| JPS5790058A (en) | 1982-06-04 |
| GB2084605A (en) | 1982-04-15 |
| US4311775A (en) | 1982-01-19 |
| GB2084605B (en) | 1984-09-26 |
| DE3138999C2 (en, 2012) | 1990-04-05 |
| JPH0245661B2 (en, 2012) | 1990-10-11 |
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