DE1668992C3 - Azo-Metallkomplexsalze von 6-Cyanodere-Halo-Kl'-sulfo-r-naphthylazo)-2-naphthol-, Verfahren zu deren Herstellung und Verwendung zur elektrophoretischen Bilderzeugung - Google Patents
Azo-Metallkomplexsalze von 6-Cyanodere-Halo-Kl'-sulfo-r-naphthylazo)-2-naphthol-, Verfahren zu deren Herstellung und Verwendung zur elektrophoretischen BilderzeugungInfo
- Publication number
- DE1668992C3 DE1668992C3 DE1668992A DEX0000137A DE1668992C3 DE 1668992 C3 DE1668992 C3 DE 1668992C3 DE 1668992 A DE1668992 A DE 1668992A DE X0000137 A DEX0000137 A DE X0000137A DE 1668992 C3 DE1668992 C3 DE 1668992C3
- Authority
- DE
- Germany
- Prior art keywords
- pigment
- light
- particles
- naphthol
- color
- 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
- -1 Azo metal complex salts Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title description 19
- 238000003384 imaging method Methods 0.000 title description 15
- 230000008569 process Effects 0.000 title description 14
- 238000002360 preparation method Methods 0.000 title description 4
- 229950011260 betanaphthol Drugs 0.000 claims description 12
- 239000000049 pigment Substances 0.000 description 54
- 239000002245 particle Substances 0.000 description 39
- 239000000126 substance Substances 0.000 description 32
- 239000000725 suspension Substances 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 17
- 230000035945 sensitivity Effects 0.000 description 16
- 239000000243 solution Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 159000000007 calcium salts Chemical class 0.000 description 8
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 7
- 229910052791 calcium Inorganic materials 0.000 description 7
- 239000011575 calcium Substances 0.000 description 7
- 239000003086 colorant Substances 0.000 description 7
- 239000005304 optical glass Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 206010034972 Photosensitivity reaction Diseases 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000003350 kerosene Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 230000036211 photosensitivity Effects 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 5
- 239000012954 diazonium Substances 0.000 description 5
- 150000001989 diazonium salts Chemical class 0.000 description 5
- 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 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 4
- 229910052712 strontium Inorganic materials 0.000 description 4
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 4
- WKTNIBWKHNIPQR-UHFFFAOYSA-N 6-hydroxynaphthalene-2-carbonitrile Chemical compound C1=C(C#N)C=CC2=CC(O)=CC=C21 WKTNIBWKHNIPQR-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 230000005670 electromagnetic radiation Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000001023 inorganic pigment Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000012860 organic pigment Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000001052 yellow pigment Substances 0.000 description 3
- YLDFTMJPQJXGSS-UHFFFAOYSA-N 6-bromo-2-naphthol Chemical compound C1=C(Br)C=CC2=CC(O)=CC=C21 YLDFTMJPQJXGSS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
- 206010034960 Photophobia Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 159000000009 barium salts Chemical class 0.000 description 2
- 229910001864 baryta Inorganic materials 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- SRPCPRSDICCCRQ-UHFFFAOYSA-N chembl2004385 Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N=NC3=C4C=CC=CC4=CC=C3O)=CC=C21 SRPCPRSDICCCRQ-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 208000013469 light sensitivity Diseases 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- UQUSWFUNTREYGO-UHFFFAOYSA-N pyrene-1,3,6,8-tetracarbonitrile Chemical compound C1=C2C(C#N)=CC(C#N)=C(C=C3)C2=C2C3=C(C#N)C=C(C#N)C2=C1 UQUSWFUNTREYGO-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 2
- 238000012549 training Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 description 1
- NPAYBXSLOLNULX-UHFFFAOYSA-N 2-diazo-1h-naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)C(=[N+]=[N-])C=CC2=C1 NPAYBXSLOLNULX-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- WCMHZFHLWGFVCQ-UHFFFAOYSA-N [Ba].[Mn] Chemical compound [Ba].[Mn] WCMHZFHLWGFVCQ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- JWAZRIHNYRIHIV-UHFFFAOYSA-N beta-hydroxynaphthyl Natural products C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 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 1
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 235000019239 indanthrene blue RS Nutrition 0.000 description 1
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 150000002696 manganese Chemical class 0.000 description 1
- 238000013507 mapping Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 159000000008 strontium salts Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 230000000007 visual effect Effects 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
- C09B63/00—Lakes
- C09B63/005—Metal lakes of 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/16—Monoazo compounds containing chromium
-
- 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
-
- 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
- G03G5/0675—Azo dyes
- G03G5/0677—Monoazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Electrochemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Optical Filters (AREA)
- Developing Agents For Electrophotography (AREA)
- Liquid Developers In Electrophotography (AREA)
- Photoreceptors In Electrophotography (AREA)
- Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61329567A | 1967-02-01 | 1967-02-01 | |
| US4859570A | 1970-05-21 | 1970-05-21 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1668992A1 DE1668992A1 (de) | 1970-12-10 |
| DE1668992B2 DE1668992B2 (de) | 1973-09-13 |
| DE1668992C3 true DE1668992C3 (de) | 1978-09-14 |
Family
ID=26726305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1668992A Expired DE1668992C3 (de) | 1967-02-01 | 1968-01-25 | Azo-Metallkomplexsalze von 6-Cyanodere-Halo-Kl'-sulfo-r-naphthylazo)-2-naphthol-, Verfahren zu deren Herstellung und Verwendung zur elektrophoretischen Bilderzeugung |
Country Status (8)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4002603A (en) * | 1974-08-28 | 1977-01-11 | American Cyanamid Company | Polyvalent metal salts of 7-hydroxy-8-[p-(phenylazo)phenylazo]-1,3-naphthalenedisulfonic acid for dyeing fiberglass |
| US4047944A (en) * | 1976-06-01 | 1977-09-13 | Eastman Kodak Company | Electrophoretic migration imaging process with neutral density bisazo pigments |
| US4145215A (en) * | 1977-07-15 | 1979-03-20 | Eastman Kodak Company | Migration imaging process and compositions |
| CA1115578A (en) * | 1977-07-25 | 1982-01-05 | Frank G. Webster | Electrophotosensitive materials for migration imaging processes |
| JPS60120361A (ja) * | 1983-12-05 | 1985-06-27 | Canon Inc | 感光体 |
| US4681829A (en) * | 1986-09-02 | 1987-07-21 | Xerox Corporation | Single component red developer compositions |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2478768A (en) * | 1945-10-04 | 1949-08-09 | Du Pont | Manufacture of azo lakes |
| US2601668A (en) * | 1949-09-27 | 1952-06-24 | American Cyanamid Co | Stabilized barium and strontium lithol toners |
| US2601469A (en) * | 1950-09-30 | 1952-06-24 | American Cyanamid Co | Process of stabilizing calcium lithol toners |
| US2867613A (en) * | 1956-09-11 | 1959-01-06 | American Cyanamid Co | Tobias acid compositions and diazotization thereof |
| US2956879A (en) * | 1958-01-07 | 1960-10-18 | Eastman Kodak Co | Filter and absorbing dyes for use in photographic emulsions |
| US3384565A (en) * | 1964-07-23 | 1968-05-21 | Xerox Corp | Process of photoelectrophoretic color imaging |
| US3485633A (en) * | 1966-06-27 | 1969-12-23 | Xerox Corp | Electrophoretic imaging process employing metallic lakes of fluorescein derivatives as the electrically photosensitive material |
-
1967
- 1967-02-01 US US613295A patent/US3574182A/en not_active Expired - Lifetime
-
1968
- 1968-01-25 DE DE1668992A patent/DE1668992C3/de not_active Expired
- 1968-01-27 LU LU55364D patent/LU55364A1/xx unknown
- 1968-01-29 BE BE710053D patent/BE710053A/xx unknown
- 1968-01-30 NL NL6801317A patent/NL6801317A/xx unknown
- 1968-01-30 GB GB4723/68A patent/GB1197374A/en not_active Expired
- 1968-01-31 AT AT97068A patent/AT302812B/de not_active IP Right Cessation
- 1968-02-01 FR FR1556484D patent/FR1556484A/fr not_active Expired
-
1970
- 1970-05-21 US US48595A patent/US3652438A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| LU55364A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-08-21 |
| GB1197374A (en) | 1970-07-01 |
| AT302812B (de) | 1972-10-25 |
| US3652438A (en) | 1972-03-28 |
| DE1668992B2 (de) | 1973-09-13 |
| DE1668992A1 (de) | 1970-12-10 |
| BE710053A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1968-07-29 |
| US3574182A (en) | 1971-04-06 |
| NL6801317A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1968-08-02 |
| FR1556484A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-02-07 |
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