NO131174B - - Google Patents
Download PDFInfo
- Publication number
- NO131174B NO131174B NO243971A NO243971A NO131174B NO 131174 B NO131174 B NO 131174B NO 243971 A NO243971 A NO 243971A NO 243971 A NO243971 A NO 243971A NO 131174 B NO131174 B NO 131174B
- Authority
- NO
- Norway
- Prior art keywords
- phthalocyanine
- metal
- alpha
- beta
- free phthalocyanine
- Prior art date
Links
- 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 claims description 36
- 238000010586 diagram Methods 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000049 pigment Substances 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LHYQAEFVHIZFLR-UHFFFAOYSA-L 4-(4-diazonio-3-methoxyphenyl)-2-methoxybenzenediazonium;dichloride Chemical compound [Cl-].[Cl-].C1=C([N+]#N)C(OC)=CC(C=2C=C(OC)C([N+]#N)=CC=2)=C1 LHYQAEFVHIZFLR-UHFFFAOYSA-L 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 238000002083 X-ray spectrum Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000001905 inorganic group Chemical group 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003756 stirring Methods 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
- 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
- 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
- C09B67/0025—Crystal modifications; Special X-ray patterns
- C09B67/0026—Crystal modifications; Special X-ray patterns of phthalocyanine pigments
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
- G03G5/0528—Macromolecular bonding materials
- G03G5/0532—Macromolecular bonding materials obtained by reactions only involving carbon-to-carbon unsatured bonds
- G03G5/0535—Polyolefins; Polystyrenes; Waxes
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
- G03G5/0528—Macromolecular bonding materials
- G03G5/0532—Macromolecular bonding materials obtained by reactions only involving carbon-to-carbon unsatured bonds
- G03G5/0539—Halogenated polymers
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
- G03G5/0528—Macromolecular bonding materials
- G03G5/0532—Macromolecular bonding materials obtained by reactions only involving carbon-to-carbon unsatured bonds
- G03G5/0542—Polyvinylalcohol, polyallylalcohol; Derivatives thereof, e.g. polyvinylesters, polyvinylethers, polyvinylamines
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
- G03G5/0528—Macromolecular bonding materials
- G03G5/0532—Macromolecular bonding materials obtained by reactions only involving carbon-to-carbon unsatured bonds
- G03G5/0546—Polymers comprising at least one carboxyl radical, e.g. polyacrylic acid, polycrotonic acid, polymaleic acid; Derivatives thereof, e.g. their esters, salts, anhydrides, nitriles, amides
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
- G03G5/0528—Macromolecular bonding materials
- G03G5/0532—Macromolecular bonding materials obtained by reactions only involving carbon-to-carbon unsatured bonds
- G03G5/0553—Polymers derived from conjugated double bonds containing monomers, e.g. polybutadiene; Rubbers
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
- G03G5/0528—Macromolecular bonding materials
- G03G5/0557—Macromolecular bonding materials obtained otherwise than by reactions only involving carbon-to-carbon unsatured bonds
- G03G5/0567—Other polycondensates comprising oxygen atoms in the main chain; Phenol resins
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
- G03G5/0528—Macromolecular bonding materials
- G03G5/0557—Macromolecular bonding materials obtained otherwise than by reactions only involving carbon-to-carbon unsatured bonds
- G03G5/0575—Other polycondensates comprising nitrogen atoms with or without oxygen atoms in the main chain
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0664—Dyes
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0664—Dyes
- G03G5/0696—Phthalocyanines
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/08—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being inorganic
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/08—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being inorganic
- G03G5/082—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being inorganic and not being incorporated in a bonding material, e.g. vacuum deposited
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/08—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being inorganic
- G03G5/087—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being inorganic and being incorporated in an organic bonding material
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- General Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Inorganic Chemistry (AREA)
- Organic Chemistry (AREA)
- Photoreceptors In Electrophotography (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Developing Agents For Electrophotography (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
Description
I tillegg til det metallfrie ftalocyanin med en ovenfor an-gitte struktur er det kjent flere metallderivater av ftalocyanin hvor de to hydrogenatomer i midten av molekylet er erstattet av me-taller fra hvilken som helst gruppe i det periodiske system. Det er også kjent at fra to til seksten av de perifere hydrogenatomer i de fire benzenringer i ftalocyaninmolekylet kan erstattes med halogenatomer og av tallrike organiske og uorganiske grupper.
Det er kjent at ftalocyanin eksisterer i minst tre polymorfe former som det lett kan skilles mellom ved sammenlikning av deres røntgendiagrammer og/eller infrarødspektra. Pigmentets farge varierer også i samsvar med den polymorfe form, idet betaformen er grønnere enn alfa- eller gammaformene. Som angitt mer i detalj nedenfor, er det litt tvil om gammaformen virkelig er en særskilt polymorf form eller er en mindre krystallinsk form av alfa-ftalocyanin. I tillegg til disse tre kjente former som eksisterer i både metallinneholdende og metallfritt ftalocyanin er det kjent ytterligere polymorfe former av metallinneholdende ftalocyanin, nemlig en "R"-form som angitt i US-patentskrift 3.051.721, en "delta"-form som beskrevet i US-patentskrift 3.160.635 og en annen "delta"-form som beskrevet i US-patentskrift 3.150.150.
Det er nå blitt funnet at metallfritt ftalocyanin eksisterer i ytterligere en form, heretter betegnet "X"-form ftalocyanin. Som påpekt mer fullstendig nedenfor, avviker røntgenspektra og infrarødspektra for denne form betydelig fra tilsvarende spektra for de tidligere kjente former. Som beskrevet i norsk patentskrift 124.709 har "X"-formftalocyaninet anvendelighet som fotoledende materiale i elektrofotografi når det blandes med et bindemiddel og belegges på et underlag. Den resulterende elektrofotografiske plate har forbausende høy fotofølsomhet når ftalocyaninet er enten i sin helhet'"X"-form eller en blanding av "X"-form og alfa-form ftalocyanin.
Ifølge oppfinnelsen er det frembrakt et metallfritt ftalocyanin i "X"-formen som kjennetegnes ved at det har et røntgen-diagram som oppviser sterke linjer ved Braggvinkler 7,5, 9,1,
16,7, 17,3 og 22,3.
Metallfritt ftalocyanin i "X" form, fremstilles ved følgende trinn: Fremskaffing av et ftalocyanin, fjerning av forurensninger og ethvert metallatom fra ftalocyaninet og formaling av ftalocyaninet inntil dets røntgendiagram oppviser sterke linjer ved Bragg-vinkler 7,5, 9,1, 16,7, 17,3 og 22,3.
Forskjellene mellom den nye "X"-form av metallfritt ftalocyanin og de tidligere kjente alfa-, beta- og gamma-former vil bli ytterligere klargjort ved henvisning til tegningen som viser sammenliknende røntgendiagrammer for de forskjellige polymorfe former av metallfritt ftalocyanin.
Tegningen viser røntgendiagrammer for alfa-, beta- og X-form polymorfe former av prøver fremstilt på laboratoriet.
Tegningen viser et sett kurver som sammenlikner alfa-, beta-og gammaformen av metallfritt ftalocyanin, ordnet i vertikal oppstilling på linje for lettvint sammenlikning. Prøvene av hver form av ftalocyanin testet med røntgenstråling ble fremstilt på laboratoriet og analysert med samme utstyr av samme ope-ratør for derved å være sikker på samsvar mellom prøvene. Prøven som ble brukt til å frembringe kurven for alfaformen ble fremstilt av kommersielt "Monolite Fast Blue GS", en blanding av alfa og beta metallfritt ftalocyanin. Dette pigment ble helt omdannet til alfaform før testing ved løsningsmiddelsektraksjon med diklorbenzen, vasking med aceton og utfelling fra svovelsyre i isvann. Prøven av betaformen som ga kurven som er vist på tegningen, ble fremstilt ved å suspendere kommersielt "Monolite East Blue G-S" i trietylentetramin i en konsentrasjon av 1 vektdel pigment til 5 vektdeler trietylentetramin i fire dager ved 23°C. Pigmentet ble deretter vasket med metanol og tørket. "X"-formen ftalocyanin som ga kurven som vist på tegningen, ble fremstilt som følger: Kommersielt "Monolite Fast Blue G-S" ble løsningsmiddelekstrahert med diklorbenzen, deretter vasket med aceton og tørket. Pigmentet ble deretter løst i svovelsyre og utfelt i isvann. Utfellingen ble vasket med metanol og tørket. Pigmentet ble deretter omhyggelig malt i en kulemølle i sju dager, vasket med dimetyl-formamid og deretter med metanol.
Røntgendiagrammene for alfa- og betaftalocyanin, fremstilt på laboratoriet, stemmer som vist på tegningen overens med de diagrammer som er referert i litteraturen.
Som det kan sees på tegningen, avviker "X"-formen av ftalocyanin oppsiktsvekkende fra alfa- og betaformene. Spektret for "X"-formen har topper ved Bragg-vinkler 17,5 og 22,3 som ikke eksisterer for de alfa- og beta-polymorfe former. "X"-formen viser også en topp ved 9,1 som ikke er til stede for alfa-formen og som har lavere intensitet enn tilsvarende topp for beta-formen.
Videre har beta-formen topper ved omkring 26,2, 18,0, 14,1 og
7,0, og alfa-formen har topper ved omkring 26,7, 13,6 og 6,8 som ikke opptrer hos "X"-formen. I tillegg har "X"-formen topper ved 7,5 og 16.7.
Spesielle fremstillingsmåter for alfa-, beta- og X-formene av ftalocyanin er som følger:
Fremstilling av alfa metallfritt ftalocyanin.
86,7 g litiumftalocyanin ble tilsatt til 600 ml godt
omrørt konsentrert svovelsyre ved 0°C. Blandingen ble deretter omrørtved denne temperatur i to timer. Den resulterende løsning ble deretter filtrert gjennom en grov, sintret glasstrakt og tømt sakte og under omrøring i 4 liter"isvann. Etter setting i flere timer ble blandingen filtrert og filterkaken vasket til nøytralt med vann. Filterkaken ble til slutt skyllet med metanol atskillige ganger og tørket i luft. Det resulterende pulver ble deretter ekstrahert med aceton i et kontinuerlig ekstraksjonsapparat i tjuefire timer og fikk tørke i luften til dannelse av et blått pulver.
For å sikre seg mot rester av litiumsalt ble utfellingen gjentatt. Det ble oppnådd 55,4 g av et blått pulver hvis røntgen-diagram svarte til det kjente, publiserte diagram for alfa metallfritt ftalocyanin.
Fremstilling av beta metallfritt ftalocyanin.
10 g kommersielt "Monolite Fast Blue GS" ble plassert i en "Vycor" skål som ble innført i et 50 mm's glassrør egnet for opp-varming i en forbrenningsovn. Temperaturen i ovnen ble langsomt hevet til 350°C under den første 1-jjr time for å unngå at prøven ødelegges og til slutt holdt ved 350 - 430°C i de fire neste timer. En strøm av tørr nitrogen ble ledet gjennom røret under varmebehandlingen. Den behandlete prøve ble overført til et tørkeapparat for kjøling. Resultatet var 9,45 g blåsvart pulver som ga et røntgendiagram som svarte til det for beta-formen. Fremstilling av " X"- form metallfritt ftalocyanin.
En 9 grams prøve av alfa metallfritt ftalocyanin, fremstilt ved felling fra svovelsyre, og 90 g natriumklorid ble plas-
sert i en ca. 1 liters porselenkulemølle og malt i 72 timer med 70 omdreininger pr. minutt.
Det malte pulver ble fjernet manuelt fra møllen og ekstrahert med 1500 ml 1 prosentig saltsyre vad 70 -80°C i en time.
Det resulterende slam ble 'filtrert og filterkaken vasket gjentatte ganger med destillert vann for fjerning av gjenværende natriumklorid. Filterkaken ble til slutt skyllet med metanol flere ganger og tørket i luft. Resultatet ble 8,8 g blått pulver. Rønt-gendiagrammet til dette materiale kan ikke bringes i samsvar med noen av de publiserte strukturer for forskjellige polymorfe former for metallfrie ftalocyaniner, men stemmer overens med de fast-satte diagrammer for "X"-formen som vist på den medfølgende teg-ning, og følgelig må det ansees at materialet er "X"-formen av metallfritt ftalocyanin.
Selv om de mest effektive elektrofotografiske plater blir fremstilt ved blanding av "X"-formen av metallfritt pigment i harpiksbindemiddel, kan også meget gode plater fremstilles med den alfa metallfrie form, spesielt hvis denne omdannes til betaformen ved omkrystallisering i løsningsmiddel eller til "X"-formen i et belegg, som vil bli beskrevet senere. For å bestemme krystallformen til ftalocyaninpigmentet slik som det virkelig foreligger i det fotoledende lag etter at dette er tørket og her-det, blir laget skrapet av fra sitt underlag og pulverisert uten noe forsøkt på å fjerne den omgivende harpiks (sistnevnte påvirker ikke i nevneverdig grad målingen). Pulveret fylles deretter i et kapillar og forskjellige forsøk foretas med komprimerte pulverpellets. Resultatene av disse forsøk er gjengitt som angitt ovenfor (på alfa-, beta-, gamma- og "X"-formen av metallfrie ftalocyaninpigmenter).
Til alle Bragg-vinkler som er nevnt i beskrivelsen til
denne oppfinnelse ble det benyttet stråling som svarer til kobber-K-bølgelengden, 1.54050 Å. Hvis det er ønskelig, kan verdier som er målt i Bragg-vinkler regnes om til absolutte avstander (d) ved følgende likning: N-A. = 2 d sin 0, hvor N er graden av diffrak-sjon (her 2). X er røntgenstrålingens bølgelengde (her 1,54050 A), d er avstanden som fremkaller interferensfenomenet og 0 er Bragg-spredningsvinkelen.
Claims (1)
- Metallfritt ftalocyanin i "X"-form som anvendes som fotoledende materiale sammen med bindemiddel ved elektrofotografering, karakterisert ved at det har et røntgendiagram som oppviser sterke linjer ved Bragg-vinkler 7,5, 9,1, 16,7 og 22,3.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37519164A | 1964-06-15 | 1964-06-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO131174B true NO131174B (no) | 1975-01-06 |
| NO131174C NO131174C (no) | 1975-04-16 |
Family
ID=23479871
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO15846965A NO124709B (no) | 1964-06-15 | 1965-06-14 | |
| NO243971A NO131174C (no) | 1964-06-15 | 1971-06-28 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO15846965A NO124709B (no) | 1964-06-15 | 1965-06-14 |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS494338B1 (no) |
| AT (2) | AT297883B (no) |
| BE (1) | BE664883A (no) |
| CA (1) | CA950251A (no) |
| CH (1) | CH479094A (no) |
| CY (1) | CY496A (no) |
| DE (2) | DE1794329B2 (no) |
| ES (1) | ES313979A1 (no) |
| FR (1) | FR1447277A (no) |
| GB (2) | GB1116553A (no) |
| IL (2) | IL33063A (no) |
| LU (1) | LU48728A1 (no) |
| MY (1) | MY6900153A (no) |
| NL (1) | NL153339B (no) |
| NO (2) | NO124709B (no) |
| SE (2) | SE316682B (no) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3573904A (en) * | 1967-01-09 | 1971-04-06 | Xerox Corp | Combination of electrography and manifold imaging |
| JPS5364040A (en) * | 1976-11-19 | 1978-06-08 | Hitachi Ltd | Photosensitive plate for xerography |
| GB1599430A (en) * | 1977-06-27 | 1981-09-30 | Konishiroku Photo Ind | Photoconductive composition for use in the preparation of an electrophotographic material |
| JPS58166355A (ja) * | 1982-03-29 | 1983-10-01 | Toyo Ink Mfg Co Ltd | フタロシアニン系光導電体素子組成物およびこれを用いた電子写真感光体 |
| JPS58182639A (ja) * | 1982-04-20 | 1983-10-25 | Hitachi Ltd | 電子写真用感光体 |
| JPS59232348A (ja) * | 1983-06-15 | 1984-12-27 | Mita Ind Co Ltd | 積層感光体及びその製造法 |
| JPS6050539A (ja) * | 1983-08-31 | 1985-03-20 | Toyo Ink Mfg Co Ltd | 電子写真感光体 |
| DE3417951A1 (de) * | 1984-05-15 | 1985-11-21 | Hoechst Ag, 6230 Frankfurt | Elektrophotographisches aufzeichnungsmaterial |
| WO1988002880A1 (en) * | 1986-10-20 | 1988-04-21 | Konica Corporation | Photosensitive member |
| EP0458651B1 (en) * | 1990-05-25 | 1994-03-09 | Matsushita Electric Industrial Co., Ltd. | Photosensitive materials comprising organic photoconductive substances in a binder polymer having aromatic rings, OH groups and bromine joined at the aromatic ring or rings |
| DE4234922A1 (de) * | 1992-10-16 | 1994-04-21 | Basf Ag | Metallfreies Phthalocyanin der gamma-Modifikation |
| CN1926198B (zh) | 2004-03-04 | 2011-06-08 | 三菱化学株式会社 | 酞菁组合物和使用该酞菁组合物的光电导材料、电子照相感光体、电子照相感光体盒和成像装置 |
-
1965
- 1965-03-29 JP JP1786765A patent/JPS494338B1/ja active Pending
- 1965-04-12 IL IL3306365A patent/IL33063A/xx unknown
- 1965-04-12 IL IL2334265A patent/IL23342A/xx unknown
- 1965-04-30 CA CA929,519,A patent/CA950251A/en not_active Expired
- 1965-05-31 LU LU48728D patent/LU48728A1/xx unknown
- 1965-06-02 SE SE723565A patent/SE316682B/xx unknown
- 1965-06-03 BE BE664883D patent/BE664883A/xx unknown
- 1965-06-03 CH CH779565A patent/CH479094A/fr not_active IP Right Cessation
- 1965-06-04 DE DE19651794329 patent/DE1794329B2/de active Granted
- 1965-06-04 DE DE1965R0040803 patent/DE1497205C3/de not_active Expired
- 1965-06-08 FR FR19943A patent/FR1447277A/fr not_active Expired
- 1965-06-08 ES ES0313979A patent/ES313979A1/es not_active Expired
- 1965-06-10 AT AT568569A patent/AT297883B/de active
- 1965-06-10 AT AT526065A patent/AT293165B/de not_active IP Right Cessation
- 1965-06-14 NO NO15846965A patent/NO124709B/no unknown
- 1965-06-15 GB GB2243165A patent/GB1116553A/en not_active Expired
- 1965-06-15 GB GB259368A patent/GB1116554A/en not_active Expired
- 1965-06-15 NL NL6507664A patent/NL153339B/xx not_active IP Right Cessation
-
1969
- 1969-05-24 CY CY49669A patent/CY496A/xx unknown
- 1969-08-12 SE SE11202/69A patent/SE339730B/xx unknown
- 1969-12-30 MY MY6900153A patent/MY6900153A/xx unknown
-
1971
- 1971-06-28 NO NO243971A patent/NO131174C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE664883A (no) | 1965-12-03 |
| NO131174C (no) | 1975-04-16 |
| JPS494338B1 (no) | 1974-01-31 |
| GB1116553A (en) | 1968-06-06 |
| GB1116554A (en) | 1968-06-06 |
| ES313979A1 (es) | 1966-03-01 |
| CH479094A (fr) | 1969-09-30 |
| DE1497205C3 (de) | 1979-04-12 |
| LU48728A1 (no) | 1965-12-01 |
| NO124709B (no) | 1972-05-23 |
| DE1794329A1 (de) | 1971-12-30 |
| IL23342A (en) | 1970-06-17 |
| CA950251A (en) | 1974-07-02 |
| SE339730B (no) | 1971-10-18 |
| DE1497205B2 (de) | 1978-08-03 |
| DE1794329B2 (de) | 1974-05-30 |
| AT297883B (de) | 1972-04-10 |
| FR1447277A (fr) | 1966-07-29 |
| NL6507664A (no) | 1965-12-16 |
| DE1794329C3 (no) | 1975-02-06 |
| IL33063A (en) | 1970-06-17 |
| NL153339B (nl) | 1977-05-16 |
| AT293165B (de) | 1971-09-27 |
| SE316682B (no) | 1969-10-27 |
| DE1497205A1 (de) | 1969-04-30 |
| CY496A (en) | 1969-05-24 |
| MY6900153A (en) | 1969-12-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO131174B (no) | ||
| US3357989A (en) | Metal free phthalocyanine in the new x-form | |
| US3287147A (en) | Process for manufacture of quinacridone pigment compositions | |
| Ercolani et al. | Synthesis and x-ray data of a stable in air crystalline modification of chromium (II) phthalocyanine (Cr-α-Pc) | |
| US7812154B2 (en) | Method for preparing oxytitanium phthalocyanine charge generating material and apparatus for preparing the same | |
| JP2765398B2 (ja) | クロロガリウムフタロシアニン結晶の製造方法 | |
| DE3887565T2 (de) | Farbstoffe, geeignet für die Sensibilisierung photoleitfähiger Systeme. | |
| JPH08110649A (ja) | 電子写真感光体 | |
| JP4750143B2 (ja) | 特定の結晶変態を有するチタニルフタロシアニンの製造方法 | |
| US7998650B2 (en) | Method for preparing oxytitanium phthalocyanine charge generating material and the new-type oxytitanium phthalocyanine charge generating material therefrom | |
| JP4590439B2 (ja) | α型チタニルフタロシアニンの製造方法およびα型チタニルフタロシアニンを用いる電子写真感光体 | |
| DE60319081T2 (de) | µ-OXO-VERNETZTE PHTHALOCYANINVERBINDUNG MIT UNGLEICHEN METALLEN UND EIN VERFAHREN ZU DEREN SELEKTIVER HERSTELLUNG | |
| US6232466B1 (en) | Process for preparing titanyl phthalocyanine crystal by solvent treatment of amorphous or quasi-amorphous titanyl phthalocyanine | |
| Bhuchar et al. | Evaluation of colour changes of sulphamphthalein indicators: synthesis, purification and characterisation of phenol-and o-cresolsulphamphthalein | |
| JP2000219817A (ja) | μ―オキソ―アルミニウム／ガリウムフタロシアニン二量体 | |
| El-Dalsh et al. | Studies on spironolactone polymorphic forms | |
| DE60314078T2 (de) | ě-Oxo-verbrückte heterometallische Verbindung und Verfahren zu deren selektiver Herstellung | |
| Brady et al. | LXX.—The isomerism of the oximes. Part XVI. The action of ultra-violet light on aldoximes and their derivatives | |
| Silbernagel et al. | ESR studies of kerogen conversion in shale pyrolysis | |
| JPWO2019003915A1 (ja) | キサンテン系染料を含有する着色組成物、カラーフィルター用着色剤およびカラーフィルター | |
| US2699444A (en) | Preparation of phthalocyanine pigments | |
| DE1569752B2 (de) | Verfahren zur Herstellung halogenhal tiger Kobaltphthalocyaninderivate | |
| KR102685724B1 (ko) | 크산텐계 염료를 함유하는 착색 조성물, 컬러 필터용 착색제 및 컬러 필터 | |
| US2699442A (en) | Preparation of phthalocyanine pigments | |
| JP2002265810A (ja) | チタニウムフタロシアニン化合物及びその製造方法 |