Classifications

• • 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
  • G03G5/0662—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic containing metal elements
• • 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
  • C09B26/00—Hydrazone dyes; Triazene dyes
  • C09B26/02—Hydrazone 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
  • C09B57/00—Other synthetic dyes of known constitution
  • C09B57/10—Metal complexes of organic compounds not being dyes in uncomplexed form
• • 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
  • G03G5/0557—Macromolecular bonding materials obtained otherwise than by reactions only involving carbon-to-carbon unsatured bonds
  • G03G5/056—Polyesters
• • 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
  • G03G5/0564—Polycarbonates
• • 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
  • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
  • G03G5/0622—Heterocyclic compounds
  • G03G5/0644—Heterocyclic compounds containing two or more hetero rings
  • G03G5/0661—Heterocyclic compounds containing two or more hetero rings in different ring systems, each system containing at least one hetero ring
• • 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
  • G03G5/09—Sensitisors or activators, e.g. dyestuffs
• • 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
  • G03G5/12—Recording members for multicolour processes

Definitions

• An improved photoconductive material for use in photoconductive recording elements is obtained by treating a conventional inorganic metallic photoconductive compound with a small amount of an organic chelating agent which is adapted to form with the metallic ions of the photoconductive compound a colored chelate of increased light-sensitivity relative to the untreated photoconductive compound.
• a preferred amount of the chelating compound is 0.00l-0.5% by weight of the photoconductive compound.
• suitable organic chelating agents are disclosed.
• the present invention relates to a recording and reproduction material containing a spectrally sensitized inorganic photoconductive substance and a process for sensitizing said substance.
• inorganic photoconductive substances eg the oxides, sulphides and selenides of zinc, cadmium, mercury, antimony, bismuth and lead.
• the sensitizing agents for inorganic photoconductive substances may be inorganic as Well as organic.
• organic dyestulfs such as triphenyl methane derivatives, sulphone phthaleins and cyanine dyes of various kinds.
• a first class of such compounds is represented by the following general Formula I:
• R represents a hydrogen atom, an alkyl radical e.g. an alkyl radical having from 1 to carbon atoms, and
• Each of Z and Z represents the atoms necessary for completing a nitrogen-containing five or six-membered ring.
• Said five or six-membered ring may contain in addition to the nitrogen atom one or more hetero atoms e.g. oxygen, nitrogen, selenium, or sulphur atoms to form a known heterocyclic ring such as those of the thiazole series (e.g. thiazole, 4-methylthiazole, 4-methyl-5-carbethoxythiazole, 4e'phenylthiazole, S-methylthiazole', 5- phenylthiazole, 4-(p-tolyl)thiazole, 4-(p-bromopheny1)- United States Patent 0 3,600,155 Patented Aug.
• thiazole series e.g. thiazole, 4-methylthiazole, 4-methyl-5-carbethoxythiazole, 4e'phenylthiazole, S-methylthiazole', 5- phenylthiazole, 4-
• naphtho- [2,1-d]thiazole naphtho[1,2-d]thiazole, 5-methoxynaphtho[l,2 d]thiazole, 5-ethoxynaphtho[1,2 d]thiazole, 8- methoxynaphtho[2,l d]thiazole, 7-methoxynaphtho[2,ld]thiazole), those of the thionaphtheno[7,6-d]thiazole series (e.g. 7 methoxythionaphtheno[7,6 d]thiazole), those of the thiadiazole series (e.g.
• 4-phenylthiadiazole those of the oxazole series (e.g. 4-methyloxazole, 5- methyloxazole, 4-phenyloxazole, 4,5-dipheny1oxazole, 4- ethyloxazole, 4,5-dimethyloxazole, 5-phenyloxazole, those of the benzoxazole series (e.g.
• benzoxazole 5-chlorobenzoxazole, S-methylbenzoxazole, S-phenylbenzoxazole, 6 methylbenzoxazole, 5,6 dimethylbenzoxazole, 4,6-dimethylbenzoxazole, S-methoxybenzoxazole, 6-methoxybenzoxazole, 5 -hydroxybenzoxazole, 6 -hydroxybenzoxazole), those of the naphthoxazole series (e.g. naphtho- [2,l-d]oxazole, naphtho[l,2-d]oxazole), those of the selenazole series (e.g.
• the preparation of the hydrazone compound 23 is de- H scribed by F. Lions, K. V. Martin, J. Am. Chem. Soc., 80, N 3858-65 (1958).
• a second class is represented by the following general Formula H:
• --NHN CH NO: I l melting point 239 0. s
• hydrazone compounds according to the general Formula II are prepared according to the following general preparation method:
• N s Nn-N oHUNoi compound corresponding to the following general formula:
• a fourth class is represented by the following general Formula IV:
• a fifth class is represented by the following general Formula V:
• each of R and R represents hydrogen, alkyl e.g. methyl or represent together the atoms necessary to close a homocyclic ring, e.g. a (CH;),; group, and
• EA seventh class is represented by the following general Formula VII:
• each of R and R represents alkyl e.g. methyl, aryl e.g. phenyl, or represent together the atoms necessary to close a homocyclic ring, and
• the compounds 50-55 are prepared according to B. Ohiswell, F. Lions, M. L. Tomlinson Inorg. Chem. 3 (1964) 492.
• Compound 56 is prepared analogously to the compounds 50-55.
• the sensitizing compounds are preferably used in dissolved form to sensitize the inorganic photoconductor which is normally used in dispersed form in a solution or dispersion of a binder. They may be mixed beforehand, for example dissolved in dimethylformamide with the photo conductor e.g. zinc oxide. The sensitizing compound is then adsorbed on the photoconductor grains and can complex metal ions provided by the photoconductor. The sensitized photoconductor thus treated is then mixed with a suitable binder, whereupon the whole composition can be coated on a suitable base material.
• the sensitizing compounds may also be used in complexed form as can be seen e.g. in Example 2. Thus it is not absolutely necessary to treat the photoconductive substances with the sensitizing compounds in non-complexed form, although the sensitizing treatment with the compounds in non-complexed form is preferred.
• the sensitizing compounds used in the present invention are preferably applied in combination with an acid to produce metal ions; preferably the acid compounds described in Belgian patent specification 612,102 filed Dec. 29, 1961 by Ge'vaert Photo-Producten N.V. which increases the dark resistivity of photoconductive zinc oxide are used.
• an acid to produce metal ions preferably the acid compounds described in Belgian patent specification 612,102 filed Dec. 29, 1961 by Ge'vaert Photo-Producten N.V. which increases the dark resistivity of photoconductive zinc oxide are used.
• the spectral sensitivity of photoconductive recording layers according to the present invention may be further modified by sensitizing compounds other than those described herein.
• Combinations with other optical sensitizing compounds may be applied in order to make the recording layer sensitive for the whole range of the visible spectrum, so that the recording layer becomes suitable for multicolour reproduction.
• the quantitative ratio of photoconductor to sensitizing agent may vary within wide limits and depends on the effect desired; the amount of sensitizing agent may for instance vary between 0.001 and 0.5 percent based on the weight of photoconductor.
• Representatives of sensitizing compounds which are very active can be chosen in Table 2 of Example 3 given further on. Most of these compounds sensitize in the range of 440 to 515 nm.
• the photoconductive substances are used in combination with a binding agent the electric specific resistance of which is preferably at least ohm cm.
• the quantitative ratio of photoconductive substance to binding agent may vary within wide limits.
• the ratio of binding agent to photoconductor is between 1:1 to 1:10 parts by weight.
• the thickness of the photoconductive layer may be chosen between wide limits according to the requirements of each case. Good recording and reproduction results are attained with electrophotographic layers of a thickness between 1 and 20g, and preferably between 3 and 1011.. Too thin layers possess an insufficient insulating power whereas too thick layers require long exposure times.
• Suitable binding agents for photoconductive substances of the inorganic type are e.g. described in Belgian patent specifications 612,102 filed Dec. 29, 1961 and 604,126 filed May 24, 1961 both by Gevaert Photo-Producten N.V.
• the photoconductive recording layers containing photoconductive substances sensitized according to the present invention may further contain photoconductive substances, that cannot be sensitized with the sensitizing compounds corresponding to the above cited general formula e.g. organic monomeric photoconductors described in Belgian patent specifications 585,507 filed Dec. 10, 1961, 585,555 filed Dec. 11, 1959, 587,301 filed Feb. 5, 1960, 585,450 filed Dec. 9, 1959, 587,794 filed Feb. 19, 1960, 589,239 filed Mar.
• the photoconductive recording layers or sheets sensitized according to the present invention can be prepared by any of the processes known therefor.
• the photoconductor-binder composition with a suitable solvent or dispersing liquid for the binder may be coated on a sup port by a known coating technique e.g. by spraying, by whirling, by dip-coating, or by a coating technique wherein use is made of a doctor blade.
• the supports or base materials are chosen in view of the particular exposing, recording, developing and/or transfer technique wherein the recording material is to be used.
• the support has an electric volume resistivity considerably lower than that of the recording layer.
• Suitable supports are e.g. described in Belgian patent specifications 602,794 filed Apr. 20, 1961, 612,102 filed Dec. 29, 1961 and 610,060 filed Nov. 8, 1961 all by Gevaert Photo-Producten N.V. and the US. patent specification 3,008,825 filed Nov. 20, 1957 by W. G. Van Dorn and O. A. Ullbrich.
• the photoconductive layer of an electrophotographic material optically sensitized according to the present invention can be made sensitive for recording purposes by electrically charging according to known methods.
• the material can, however, also be used in recording techniques, wherein the exposure step precedes charging; for such a technique we refer e.g. to Belgian patent specification 625,335 filed Nov. 27, 1962 by Gevaert Photo- Producten N.V.
• EXAMPLE 1 120 g. of copoly(vinyl acetate/ vinyl laurate) (/20) are dissolved in 500 cos. of toluol. To this solution are added 20 cos. of a 10% solution in ethanol of monooctylphosphate and 300 g. of photoconductive zinc oxide (prepared according to the French process) which has been dried for 30 min. on C.
• a series of recording materials are prepared in this way; among this series one material does not contain sensitizing compound and each of the other materials contains a diiferent sensitizing compound as listed hereinafter in the table.
• the different recording materials obtained are simultaneously charged with a corona discharging apparatus having a potential difference between the ground and the wires of 6000 v., the wires being connected to the negative pole of a direct current source.
• the charged materials are exposed under the same conditions with incandescent light bulbs through a grey wedge having a constant 0.1.
• the charge images obtained are simultaneously developed with a resin powder toner that contains iron filings as carrier.
• the toner is fixed by heating.
• the further processing steps occur 40 515 as described in Example 1.
• the sensitized material has a 232 general sensitivity which is 4 times as high as the sensi- 16 515 tivity of the corresponding non-sensitized material.
• the relative sensitivity 111g f dlfferent seflsltlzlng Compound and one matenal c011 values are calculated by comparing the sensitized matetalmng no sensltlzlllg p rials With the same but non-sensitized material the sensi- The sensltemetrle results represented 1n the fellowmg tivity of Which is given the relative value 1.
• the coating table 2 are also relative values, the non-sensitized material 4? and further processing steps of the recording layers are is given the value 1. 0 carried out in the same way as illustrated in Example 1.
• the sensitized composition is coated onto a glassine paper support at a ratio of g. of solid dry substance per sq. m.
• the recording layer is successively but separately exposed to a positive colour transparency through a blue, a green and a red filter while before each exposure a uniform electrostatic negative charge is applied to the recording layer by corona discharge.
• the charge images respectively obtained are developed with a developing pigment dispersed in an insulating liquid (hexane) which pigment has a colour complementary to the colour of the filter used at the exposure. A positive copy of the colour transparency is obtained in this way.
• the sensitized material has a general sensitivity which is 2.5 times as high as the sensitivity of the corresponding non-sensitized material.
• a photoconductive recording element comprising a photoconductive layer consisting essentially of photoconductive zinc oxide as the essential photoconductor thereof and a sensitizing amount of a colored chelate complex of an organic chelating agent with ions of said photoconductive zinc oxide, said chelate complex imparting increased light sensitivity to said photoconductive layer, said organic complexing agent having the following general formula:
• each of Z and Z' represents the necessary atoms for completing a fiveor six-membered ring
• R represents a hydrogen atom or an alkyl radical, said layer being free of sensitizing agents for said photoconductive compound other than said chelate complex.
• a photoconductive recording element comprising a photoconductive layer consisting essentially of photoconductive zinc oxide as the essential photoconductor thereof and a sensitizing amount of a colored chelate complex of an organic chelating agent with ions of said photoconductive zinc oxide, said chelate complex imparting increased light sensitivity to said photoconductive layer, said organic complexing agent having the following general formula:
• Z represents the atoms necessary to complete a fiveor six-membered ring, said layer being free of sensitizing agents for said photoconductive compound other than said chelate complex.
• a photoconductive recording element comprising a photoconductive layer consisting essentially of photoconductive zinc oxide as the essential photoconductor thereof and a sensitizing amount of a colored chelate complex of an organic chelating agent with ions of said photoconductive zinc oxide, said chelate complex imparting increased light sensitivity to said photoconductive layer, said organic complexing agent having the following general formula:
• Z represents the atoms necessary to complete a fiveor six-membered ring, said layer being free of sensitizing agents for said photoconductive compound other than said chelate complex.
• a photoconductive recording element comprising a photoconductive layer consisting essentially of photoconductive zinc oxide as the essential photoconductor thereof and a sensitizing amount of a colored chelate complex of an organic chelating agent with ions of said photoconductive zinc oxide, said chelate complex imparting increased light sensitivity to said photoconductive layer, said organic complexing agent having the following general formula:
• each of R and R represents hydrogen, or alkyl, or represent together the atoms necessary to close a homocyclic ring, and Z represents the atoms necessary to close a fiveor six-membered ring,
• each of R and R represents alkyl or aryl
• a photoconductive recording element comprising a Z represents the atoms necessary to close a fiveor photoconductive layer consisting essentially of photoconsix-membered ring,
• ductive zinc oxide as the essential photoconductor thereof 5 said layer being free of sensitizing agents for said photoand a sensitizing amount of a colored chelate complex conductive compound other than said chelate complex.
• organic chelating agent with ions of said photoconductive zinc oxide said chelate complex imparting in- References Cited creased light sensitivity to said photoconductive layer, UNITED STATES PATENTS gfgfi g agent havmg the 10 3,121,006 2/1964 Middleton et al 961.5 3,315,599 4/1967 Lind 96-1X R4 ⁇ /N ⁇ CHARLES E. VAN HORN, Primary Examiner F NH 15 US. 01. X.R.

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• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Spectroscopy & Molecular Physics (AREA)
• Organic Chemistry (AREA)
• Plural Heterocyclic Compounds (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Photoreceptors In Electrophotography (AREA)

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Cited By (3)

• 1965
  • 1965-04-15 GB GB16336/65A patent/GB1114301A/en not_active Expired
• 1966
  • 1966-04-14 DE DE19661522542 patent/DE1522542A1/de active Pending
  • 1966-04-15 BE BE679558D patent/BE679558A/xx unknown
  • 1966-04-15 NL NL6605083A patent/NL6605083A/xx unknown
• 1969
  • 1969-12-30 US US888131A patent/US3600165A/en not_active Expired - Lifetime

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