US3796569A - Electrophotographic photosensitive material - Google Patents

Electrophotographic photosensitive material Download PDF

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US3796569A
US3796569A US00197754A US3796569DA US3796569A US 3796569 A US3796569 A US 3796569A US 00197754 A US00197754 A US 00197754A US 3796569D A US3796569D A US 3796569DA US 3796569 A US3796569 A US 3796569A
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vinylcarbazole
poly
dye
dialkylaminostyryl
photosensitive
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E Kondo
K Kinjo
T Yamanouchi
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Canon Inc
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Canon Inc
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    • 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
    • G03G5/07—Polymeric photoconductive materials
    • G03G5/071—Polymeric photoconductive materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • G03G5/072—Polymeric photoconductive materials obtained by reactions only involving carbon-to-carbon unsaturated bonds comprising pending monoamine groups
    • G03G5/073—Polymeric photoconductive materials obtained by reactions only involving carbon-to-carbon unsaturated bonds comprising pending monoamine groups comprising pending carbazole groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F26/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F26/06—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic 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
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0664—Dyes
    • G03G5/0666—Dyes containing a methine or polymethine group
    • G03G5/0668—Dyes containing a methine or polymethine group containing only one methine or polymethine group
    • G03G5/067—Dyes containing a methine or polymethine group containing only one methine or polymethine group containing hetero rings
    • 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
    • G03G5/07—Polymeric photoconductive materials
    • G03G5/071—Polymeric photoconductive materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • G03G5/072—Polymeric photoconductive materials obtained by reactions only involving carbon-to-carbon unsaturated bonds comprising pending monoamine groups

Definitions

  • the present invention relates to highly sensitive electrophotographic photosensitive materials mainly composed of organic photoconductive compounds.
  • Organic photoconductive compounds used as photoelectric photosensitive materials some have a considerably high sensitivity, but it is very rare that they are used in practice at present.
  • Organic photoconductive compounds have various more excellent characteristics than inorganic ocmpounds and promise various applications in the field of electrophotography. For example, it is possible only by use of organic photoconductive compounds to provide transparent photosensitive films, flexible photosensitive films or photosensitive films which are light in weight and easy to handle.
  • organic photoconductive compounds can give a photosensitive member having film shapeability, surface smoothness and selectivity of charging polarity in an electrophotographic reproduction process. These excellent properties are not expected in the case of an inorganic photoconductive compound.
  • organic photoconductive compounds have not been practically used for a photosensitive member of electrophotography in spite of their many excellent properties since their photosensitivity is low.
  • sensitizing dyes or Lewis acid are added to all of organic photoconductive compounds without exception.
  • sensitizing dye are added, their specific spectral absorptions are added to those of the organic photoconductive compounds.
  • Lewis acid is 3,796,569 Patented Mar. 12,, 1974 Ice added, the complex of doner and acceptor is formed between the organic photoconductive compound and the Lewis acid so that the new spectral sensitivity bands (C-T band) appear.
  • (A) Vinylcarbazoles poly-9-vinylcarbazole, 9-vinylcarbazole copolymer, 3-nitro-9-vinylcarbazole copolymer, nitrated poly-9-vinylcarbazole, poly-9-vinyl-3-aminocarbazole, 3 N methylamino-9-vinylcarbazole copolymer, halogen-substituted poly-vinylcarbazole, poly-3,6-dibromo-9-vinylcarbazole, 3,6 -dibromo-9-vinylcarbazole copolymer, brominated poly-9-vinylcarbazole, 3-iodo-9- vinylcarbazole copolymer, poly-3,6-diiodo-9-vinylcarbazole, poly-3-benzylideneamino-9-vinylcarbazole, poly-9- propenylcarbazole, graft copolymer of
  • Aromatic amino derivatives aminopolyphenyl, arylideneazines, N,N'-dialkyl-N,N'-dibenzylphenylenediamine, N,N,N',N'-tetrabenzyl-p-phenyldiamine, N,N'-diphenyl-p-phenylenediamine, N,N'-dinaphthyl p phenylenediamine, 4,4 -bis-dimethylaminobenzophenone, and the like.
  • (D) Heterocyclic compounds oxadiazole, 9-ethylcarbazole, 9-n-hexylcarbazole, S-aminothiazole, 1,2,4-triazole, imidazoline, oxazole, imidazole, pyrazoline, imidalizine, polyphenylenethiazole, 1,6-methoxyphenazine, a,wbis-(9-carbazole)-alkane derivative, pyrazolinopyrazoline derivatives, and the like.
  • Condensation compounds condensation ,compounds of aldehyde and aromatic amines, reaction products of secondary aromatic amines and aromatic halogenides, polypyromethanoimide, poly P phenylene-l,3,4- oxadiazole, and so on.
  • Vinylpolymers except polyvinylcarbazoles:u-alkylacrylamide polymers; polyvinylacridine, poly-[1,5-diphenyl-3- (4-vinylphenyl)-2-pyrazoline] poly (LS-diphenylpyrazoline); polyacenaphthylene; nucleus-substitutedpolyacenaphthylene; polyvinylanthracene; p'oly-2-vinyldibenzothiophene, and so on.
  • l, m and n are 0 or I and m; n.
  • oligomers examples are:
  • organic photoconductive compounds may be sensitized by the prior art sensitization methods to have a sulficiently high sensitivity, but the others are not suificiently sensitized. It is therefore desired to find out a suitable sensitization method depending upon the kinds of organic photoconductive compounds whereby they are satisfactorily utilized as the electrophotographic photosensitive materials.
  • an electrophotographic photosensitive material which comprises an organic photoconductive material selected from the group consisting of poly-9-vinylcarbazole and derivatives thereof and at least one of dialkylaminostyryl dyes having the formula:
  • R is hydrogen or loweralkyl (including loweralkenyl) and R is, similar or dissimilar, selected from the group consisting of hydrogen and loweralkyl (including loweralkenyl); R and R are, similar or dissimilar, selected from the group consisting of hydrogen and substituents having Hammetts substituent constant anot lower than 0.2, but R and R should not be simultaneously hydrogen; R is an alkyl having 6 to 12 carbon atoms; R; and R are, similar or dissimilar, loweralkyl; X is an anion; and n is 1 or 2.
  • An object of this invention is to provide an excellent method of sensitizing organic photoconductive compounds and further to provide an organic photosensitive material for electrophotography of high photosensitivity which can be practically used.
  • Another object of this invention is to provide a photosensitive film which is highly sensitive, transparent, flexible, light and of easy handling.
  • a further object of this invention is to provide a photosensitive material which is sensitive to all visible lights.
  • Another object of this invention is to provide a photosensitive material for multicolor electrophotography capable of color separation photographing by using a color separation filter.
  • a further object of this invention is to provide a stable organic photoconductor photosensitive material which potential characteristics such as surface potential, dark decay and the like are not disturbed by the addition of a sensitizing dye.
  • Another object of this invention is to provide an organic photoconductor photosensitive plate in which the compatibility of an organic photoconductor and a sensitizing dye is so excellent that there is not a fluctuation of quality upon production.
  • FIG. 1 is a graph showing a relation between log E where E is photosensitivity as defined in Example 1 below and a value;
  • FIG. 2, FIG. 3 and FIG. 4 show spectral sensitivity of some dialkylaminostyryl dyes used in this invention.
  • Dialkylaminostyryl dyes used in the present invention may be prepared by conventional methods, for example, as shown below.
  • R R R R R A and X are as defined above.
  • dialkylaminostyryl dye is particularly effective for poly-9-vinylcarbazole or derivatives thereof as a sensitizer.
  • the range sensitized by the dialkylaminostyryl, dye according to this invention widely covers Whole visible wave length, and particularly shows high response to green light.
  • the difference of the sensitizing effect therebetween is remarkable and it has been found that there is a certain rule with respect to the substituent effect.
  • sensitization elfect of dye is, in general, closely related to the chemical structure of the dye.
  • the present inventors have found that the larger the electron attractivity of substituent on the benzenoid moiety of the nucleus containing A and N in the above formula such as imidazole, oxazole, thiazole, selenazole, pyrrole and pyridine rings, the higher the sensitization effect.
  • the dialkylaminostyryl dye shows far better sensitization effect than that having unsubstituted benzenoid moiety of the nucleus containing A and N.
  • R and R are preferably lower alkyl of not higher than C
  • the sensitization effect of the substituent is approximately proportional to the Hammetts substituent constant (0'). As illustrated in FIG. 1 where the ordinate is log E where E is photosensitivity and abscissa is I-Iammetts 0' value, the relation is shown by a straight line.
  • the Hammett's value used in the present invention is higher than 0.2, preferred with from 0.2 to 0.8.
  • a particularly preferable value ranges from 0.35 to 0.8.
  • Carbon number of alkyl of R in the general formula of dialkylaminostyryl dye used in this invention remarkably affects the sensitization ability of the dialkylaminostyryl dye. This will be shown later.
  • the sensitization efiiciency is inversely proportional to the amount of aggregation absorption and carbon number of 6 or more gives particularly high sensitivity.
  • a dialkylaminostyryl dye having R of more than 12 carbon atoms cannot be easily synthesized and is obtained at low yield. Therefore, such a dialkylaminostyryl dye is not advantageous from a commercial point of view.
  • organic photoconductive compounds used in this invention are:
  • chlorinated po1y-9-vinyl carbazole (chlorine content, 2-43% by weight), for example, poly-3-chloro-9- vinylcarbazole, poly-3,6-diohloro-9-vinylcarbazole (Belgian Pat. 753,619);
  • brominated poly-9-vinylcarblazole (bromine content
  • poly-9-viny1carbazole and derivatives thereof are sensitive only to ultraviolet region, but not to visible light. Therefore, photosensitivity of non-sensitized photosensitive plate of poly-9-vinylcarbazole series for tungsten lamp is about 10 lux.sec. and is almost the same as that of non-sensitized photosensitive plate composed of a photoconductor of low molecular weight and a binder resin.
  • the photosensitive plate made of them shows photosensitivity of 2X 10 to 10 lux.sec.
  • the photosensitive plate composed of a photoconductor of low molecular weight and a binder resin sensitized according to this invention shows a photosensitivity of 5X10 to 5x10 lux.sec. Therefore, the photosensitivity obtained by this invention is about ten times that of the conventional one.
  • Chlorinated poly-9-vinylcarbazole, brominated poly-9- vinylcarbazole, and chlorinated brominated poly-9-vinylcarbazole may be prepared by reacting poly-9-vinylcarbazole with an appropriate chlorinating agent and/or brominating agent.
  • 9-(p-chloroethyl) carbazole or 9-(3- hydroxyethyl) carbazole is chlorinated or brominated followed by dehydrochlorination and dehydrating treatment to give chlorinated or brominated vinylcarbazole.
  • the resulting vinylcarbazole is homopolymerized or copolymerized to produce the halogenated poly-9-vinylcarbazoles.
  • Chlorinated poly-9-vinylcarbazole is obtained by reacting a chlorination agent such as chlorine or sulfuryl chloride with poly-9-viny1carbazole.
  • PREPARATION EXAMPLE 2 This is an example of obtaining chlorinated-brominated 9-vinylcarbazole.
  • 3-chloro-6-bromo-9-vinylcarbazole may be obtained by brominating 9-fl-chloroethylcarbazole or 9-ethylolcarbazole and then chlorinating and treating with alcoholic caustic potash.
  • 1.0 gram of 3-chloro-6-bromo-9- vinylcarbazole in 3.0 ml. of acetonitrile in a hard glass polymerization tube is exposed to a high-pressure mercury vapor lamp, and the exposing is continued for thirty minutes after gelation.
  • methanol is added and the resulting precipitate is separated by filtration, dissolved into benzene and then precipitated again by adding methanol.
  • Thiocyanated poly-9-vinylcarbazole used as an organic photoconductive compound in this invention may be prepared by the reaction of poly-9-vinylcarbazole with a thiacyanogen as described below.
  • the thiocyanated poly- 9-vinylcarbazole may be further obtained by other methods such as reaction of poly-9-vinylcarbazole with sodium thiocyanate and bromine.
  • PREPARATION EXAMPLE 3 Poly-9-vinylcarbazole (5.0 g.) is dissolved in 160 ml. of chlorobenzene, and then a chlorobenzene solution of a thiacyanogen obtained from lead thiocyanate and equivalent amount of bromine (cf. Organic Reactions, vol. 3, p. 255) is gradually added thereto with agitation at a temperature lower than C. and the reaction is carried out for 3 hours.
  • the reaction temperature is preferably low as far as the reactivity of the reagent is not deteriorated since a side reaction occurs at high temperature to form gel.
  • the reaction mixture is poured into a large amount of methanol to precipitate the polymer, washed with methanol, and dried under vacuum.
  • the polymer thus obtained is further purified by the reprecipitation from chlorobenzene-methanol. According to the above-mentioned method, the following polymers are prepared.
  • the absorption wavelengths are 2145 cm. (--CEN), 860 cm.- and 790 cm.- (benzene nucleus substituted at 1, 3 and 4 positions), so that it is considered that -SCN groups are substituted at 3 or at 3 and 6 positions of a carbazole ring.
  • poly-9-vinylcarbazole Five grams of poly-9-vinylcarbazole is dissolved into 50 cc. of pyridine and added with 6.6 grams of iodine and is agitated at C. for 3 hours. After being cooled, the mixture is poured into a large quantity of methanol to precipitate the polymer, which is filtered, dried, precipitated again and purified in pyridine-methanol solution. The polymer thus obtained is iodinated-poly-9-vinylcarbazole with an iodine content of 20.49%.
  • the resulting 3-methylcarbazole is heated in acetone together with 1.5 mole of powdered potassium hydroxide and 1.1 mole of p-chloroethyl-p-toluene sulfonate for 5 hours, then poured into water, neutralized to precipitate oily matter. The oily matter thus precipitated crystallizes upon standing. The resulting crystals are recrystallized from methanol to obtain 9-fl-chloroethyl-3-meth*ylcarbazole, which is heated with an alcoholic potassium hydroxide to produce 3-methyl-9 vinylcarbazole. The resulting 3-methyl-9-vinylcarbazole is distilled and recrystallized.
  • Chlorinated polyvinylcarbazole used in the present invention as an organic photoconductive compound is described in Japanese patent application Nos. 56,806/ 19 69 9,837/ 1970 and 53,816/ 1970.
  • dialkylaminostyryl dyes used in the present invention are:
  • the anion function of the above compounds may be exchanged with anions of other acids to form various compounds.
  • the carbon number of alkyl group of R and R does not largely affect the sensitization ability of the dialkylaminostyryl dye, but solubility thereof in solvents. In general, the more the carbon number, the higher the solubility in solvents.
  • the electrophotographic photosensitive material according to the present invention may be made into a photosensitive member by dissolving or dispersing the organic photoconductive material, the dialkylaminostyryl dye and if desired, binder, plasticizer or other additives in a solvent, coating on a conductive support and drying, or melting the above-mentioned ingredients and coating on a conductive support, or producing a self-supporting photosensitive film from a solution containing the above-mentioned ingredients by evaporating the solvent or by melting and extruding the above-mentioned ingredients.
  • the above-mentioned photosensitive material may contain, in addition to dialkylaminostyryl dye, conventional sensitizing dyes as described in, for example, Yuki Gosei Kagaku Kyokai-shi, 24, 1010-1027 (1966), such as crystal violet, malachite green, methylene blue, and the like, and further may contain chemical sensitizers, for example, Lewis acid such as picric acid, S-nitroacenaphthene, 2,4,7-trinitrofluoroenone, maleic anhydride, chloroacetic acid, and anthraquinone.
  • conventional sensitizing dyes as described in, for example, Yuki Gosei Kagaku Kyokai-shi, 24, 1010-1027 (1966), such as crystal violet, malachite green, methylene blue, and the like
  • chemical sensitizers for example, Lewis acid such as picric acid, S-nitroacenaphthene, 2,4,7-trinitrofluoroenone, maleic anhydride,
  • the above sensitizing dyes are added to the organic photoconductive material preferably in an amount of 0.01-2% by weight based on the organic photoconductive material. They may be added to a solution of the organic photoconductive material in a form of methanol, chloroform or dimethylformamide solution.
  • EXAMPLE 1 One gram of chlorinated poly-9-vinylcarbazole (chlorine content, 27.5%) was dissolved in 15 ml. of monochlorobenzene. A solution of dialkylaminostyryl dye in chloroform was added to the solution obtained above in an amount of 0.1 mole percent. The resulting solution was coated on a high grade paper processed with polyvinylalcohol by using a wire-bar and dried to produce a photosensitive paper having a photosensitive layer of about 6 microns thick.
  • the photosensitive paper thus obtained was seasoned and then charged with an electrostatic paper analyzer (supplied by Kawaguchi Denki) and exposed to measure the exposure amount necessary for decreasing the initial potential to $6 of the initial potential.
  • the result is shown in Table 2 below as photosensitivity.
  • the above-mentioned photosensitive paper was charged and the spectral sensitivity was measured by a spectral camera.
  • the peak is listed in Table 2 below as photosensitivity peak.
  • Dialkylaminostyryl dyes used in the present example are represented by the following formula:
  • dye numbers 1, 8 and 13 are not within the scope of the present invention and are given for comparison with dialkylaminostyryl dyes of the present invention.
  • the result shown in Table 2 indicates that when the substituents Y and Z are those having high electron attractivity, the sensitization effect is large.
  • Spectral sensitivity curves for dye numbers 2, 7, and 12 are shown in FIGS. 2, 3 and 4, respectively.
  • Reference numbers 1-7 in FIG. 1 correspond to dye numbers l-7 in Table 2, respectively.
  • EMMPLE 2 Two grams of poly-9-vinylcarbazole (Luvican M-l70, trade name, supplied by Badische Anilin und Soda- Fabrik) was dissolved in 15 ml. of tetrahydrofuran. mg. of 2-p-dimethylaminocinnamylidenemethyl 6 nitrobenzthiazole-n-octyl perchlorate dissolved in 2 ml. of dimethylformamide was added to the solution obtained above, and then 0.5 g. of chlorinated parafiin (chlorine content, 40%) was added thereto. The resulting solution was coated on an art paper to form a photosensitive layer of 6p. (when dried) thick and dried at 100 C. for 5 minutes.
  • the resulting photosensitive paper was subjected to an electrophotographic process in a way similar to Example 2 and good images were obtained.
  • the optimum exposure amount was lux.sec. while optimum exposure amount for a photosensitive paper containing no sensitizing dye was 150 lux.sec.
  • Chlorinated poly-9-vinylcarbazole (chlorine content, 24.8%) (2) Poly-3-bromo-6-chloro-9-vinylcarbazole 95 (3) Chlorinated brominated poly-9-vinylcarbazole (chlorine content, 13.2%; bromine content, 15.0%) (4) Cyanogenated poly-9-vinylcarbazole (nitrogen content, 9.65%) 75 (5) Thiocyanated poly-9-vinylcarbazole (sulfur content, 7.18%) 80 methyl-S-chloroindole-n-odtyl perchlorate g 0.01
  • the above ingredients were uniformly mixed to form a solution and applied to a paper treated with polyvinylalcohol to form a coating of 711. thick (when dried) and dried.
  • the photosensitive papers were charged with an electrostatic paper analyzer (supplied by Kawaguchi Denki) and exposed to a tungsten lamp and the exposure amount requiring decreasing the potential to /2 of the value of the initial potential was measured. Ratios of reciprocals of the exposure amount are listed in Table 4 below where the reciprocals for C, D and E of nonsensitized photosensitive paper are used as unit.
  • the resulting photosensitive paper was allowed to stand in a constant moistening box of RH. 60% for two days, and then charged with an electrostatic paper analyzer (supplied by Kawaguchi Denki) and exposed. The exposure amount necessary for decreasing the initial potential to /2 of the original value was measured. The result is shown in Table 5 below.
  • the dyes used in this example have the following formula:
  • An electrophotographic photosensitive material which comprises an organic photoconductive material selected from the group consisting of poly-9-vinylcarbazole and derivatives thereof and at least one of dialkylaminostyryl dyes having the formula:
  • R is hydrogen loweralkyl or loweralkenyl and R is, similar or dissimilar, selected from the group consisting of hydrogen and loweralkyl or loweralkenyl; R and R are, similar or dissimilar, selected from the group consisting of hydrogen and substituents having Hammetts substituent constant a not lower than 0.2, but R and R should not be simultaneously hydrogen; R is an alkyl having 6 to 12 carbon atoms; R, and R are, 81mllar or dissimilar, loweralkyl; X is an anion; and n is 1 or 2.
  • poly-9-vinylcarbazole derivative is selected from the group consisting of chlorinated poly-9-vinylcarbazole (chlorine content, 243% by weight), brominated poly-9 vinylcarbazole (bromine content, 17-46% by weight), chlorinated and brominated poly-9-vinylcarbazole, chlorinated and iodinated poly-9- vinylcarbazole, cyanogenated po1y-9-vinylcarbazole, thiocyanated poly-9-vinylcarbazole, poly-3-methyl-9-vinylcarbazole, and chlorinated poly-3-methyl-9-vinylcarbazole.
  • R is a member selected from the group consisting of n-hexyl, sec-hexyl, n-heptyl, n-
  • V octyl, n-dodecyl, n-nonyl and 2-ethylhexyl V octyl, n-dodecyl, n-nonyl and 2-ethylhexyl.

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3916069A (en) * 1973-04-02 1975-10-28 Minnesota Mining & Mfg Reduced styryl/cyanine dye
DE2541665A1 (de) * 1974-09-18 1976-04-08 Matsushita Electric Ind Co Ltd Farbaendernde verbindungen und ihre verwendung
US3958991A (en) * 1972-06-12 1976-05-25 Eastman Kodak Company Supersensitizing dye combination for electrophotographic composition and element
US4139274A (en) * 1974-09-18 1979-02-13 Matsushita Electric Industrial Co., Ltd. Apparatus for changing color
US4252880A (en) * 1978-04-21 1981-02-24 Hoechst Aktiengesellschaft Electrophotographic recording material
US20070024740A1 (en) * 2003-10-07 2007-02-01 Craig Strong Flexible lens mount system for rapid tilt photography
US20100150541A1 (en) * 2006-08-30 2010-06-17 Strong Craig C Movable lens systems and associated methods

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU507694B2 (en) * 1975-06-14 1980-02-21 Hoechst Aktiengesellschaft Electrophotographic reproduction
JPS5431990U (enrdf_load_stackoverflow) * 1977-08-06 1979-03-02
JPS60163047A (ja) * 1984-02-03 1985-08-24 Fuji Photo Film Co Ltd 電子写真感光体
US7354694B1 (en) * 1999-12-02 2008-04-08 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyuko Styryl dye

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3958991A (en) * 1972-06-12 1976-05-25 Eastman Kodak Company Supersensitizing dye combination for electrophotographic composition and element
US3916069A (en) * 1973-04-02 1975-10-28 Minnesota Mining & Mfg Reduced styryl/cyanine dye
DE2541665A1 (de) * 1974-09-18 1976-04-08 Matsushita Electric Ind Co Ltd Farbaendernde verbindungen und ihre verwendung
US4139274A (en) * 1974-09-18 1979-02-13 Matsushita Electric Industrial Co., Ltd. Apparatus for changing color
US4252880A (en) * 1978-04-21 1981-02-24 Hoechst Aktiengesellschaft Electrophotographic recording material
US20070024740A1 (en) * 2003-10-07 2007-02-01 Craig Strong Flexible lens mount system for rapid tilt photography
US7800680B2 (en) 2003-10-07 2010-09-21 Lensbabies, Llc Flexible lens mount system for rapid tilt photography
US20110001868A1 (en) * 2003-10-07 2011-01-06 Lensbabies, Llc Flexible lens mount system for rapid tilt photography
US8289436B2 (en) 2003-10-07 2012-10-16 Lensbaby, Llc Flexible lens mount system for rapid tilt photography
US8773571B2 (en) 2003-10-07 2014-07-08 Lensbaby, Inc. Flexible lens mount system for rapid tilt photography
US20100150541A1 (en) * 2006-08-30 2010-06-17 Strong Craig C Movable lens systems and associated methods
US8075201B2 (en) 2006-08-30 2011-12-13 Lensbaby, Llc Movable lens systems and associated methods

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DE2156886A1 (de) 1972-05-25
DE2156886C3 (enrdf_load_stackoverflow) 1975-07-31
DE2156886B2 (de) 1974-12-19
JPS492638B1 (enrdf_load_stackoverflow) 1974-01-22

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