GB930988A - Improvements in and relating to electrophotographic reproduction materials - Google Patents

Improvements in and relating to electrophotographic reproduction materials

Info

Publication number
GB930988A
GB930988A GB2130858A GB2130858A GB930988A GB 930988 A GB930988 A GB 930988A GB 2130858 A GB2130858 A GB 2130858A GB 2130858 A GB2130858 A GB 2130858A GB 930988 A GB930988 A GB 930988A
Authority
GB
United Kingdom
Prior art keywords
aryl
dimethylaminophenyl
aralkyl
acyl
alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB2130858A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ozalid Co Ltd
Original Assignee
Ozalid Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Ozalid Co Ltd filed Critical Ozalid Co Ltd
Priority to GB2130858A priority Critical patent/GB930988A/en
Publication of GB930988A publication Critical patent/GB930988A/en
Expired legal-status Critical Current

Links

Classifications

    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02Charge-receiving layers
    • G03G5/04Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0622Heterocyclic compounds
    • G03G5/0624Heterocyclic compounds containing one hetero ring
    • G03G5/0635Heterocyclic compounds containing one hetero ring being six-membered
    • G03G5/0637Heterocyclic compounds containing one hetero ring being six-membered containing one hetero atom
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02Charge-receiving layers
    • G03G5/04Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601Acyclic or carbocyclic compounds
    • G03G5/0612Acyclic or carbocyclic compounds containing nitrogen
    • G03G5/0616Hydrazines; Hydrazones
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02Charge-receiving layers
    • G03G5/04Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601Acyclic or carbocyclic compounds
    • G03G5/0618Acyclic or carbocyclic compounds containing oxygen and nitrogen
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02Charge-receiving layers
    • G03G5/04Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0622Heterocyclic compounds
    • G03G5/0644Heterocyclic compounds containing two or more hetero rings
    • G03G5/0661Heterocyclic compounds containing two or more hetero rings in different ring systems, each system containing at least one hetero ring

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A coating composition for electrophotographic plates comprises a natural or synthetic resin and a photoconductive hydrazone of the formula R1R2C=N.NR3R4, in which the R symbols represent H, alkyl, aralkyl, cycloalkyl, acyl, aryl or heterocyclic aromatic groups, of which R1 and R2 may be joined to form a ring. A sensitizing dyestuff or chlorophyll may be present, and in one example sulphosalicylic acid is added. Specified solvents are water, ethanol, glycol monomethyl ether, methyl ethyl ketone and toluene, depending on the nature of the resin of which many types are listed. The support may be metal, (e.g. aluminium), glass or a resin.ALSO:The Specification describes photoconductive resinous compositions as in Specification 853,880 but with the photoconductor there specified replaced by a hydrazone of the formula R1R2C=N.NR3R4, in which the R symbols represent H, alkyl, aralkyl, cycloalkyl, acyl, aryl or heterocyclic aromatic groups, of which R1 and R2 may be joined to form a ring. Particularly suitable are those in which R3 is acyl and R4 is H, especially the benzoyl, substituted benzoyl and pyridoyl hydrazones of aromatic and heterocyclic aldehydes. Many suitable compounds of the above formula are mentioned, alone or in admixture with one another. The sensitizing dyestuffs mentioned in Specification 853,880 may also be present, and in example sulphosalicylic acid is added.ALSO:Acyl - hydrazones of the formula R1R2C=N-NH-CO-R are prepared by heating carboxylic acid hydrazides with aldehydes, ketones or quinones in an organic solvent, e.g. ethanol; R is H, alkyl, aralkyl, aryl or a heterocyclic aromatic radical (or may be an alkylene group, giving a bis-compound), R1 is H, alkyl, or aryl, and R2 is aralkyl, aryl or a heterocyclic aromatic radical; R1 and R2 may be joined to form a ring. In examples R is H, heptadecyl, benzyl, phenyl, tolyl, hydroxyphenyl, methoxyphenyl, aminophenyl, methylaminophenyl, methylphenylamino - phenyl, dimethylaminophenyl, diethylaminophenyl, benzylaminophenyl, diphenylyl, naphthyl, hydroxynaphthyl, aminonaphthyl and pyridyl, or RCO is an adipic acid residue; R1 is H, methyl and dimethylaminophenyl; R2 is phenyl, methoxyphenyl, dimethylaminophenyl, diethylaminophenyl, dibenzyl-aminophenyl, methylenedioxyphenyl, 2 - chloro-4-dimethylaminophenyl, nitrophenyl, naphthyl, anthracyl, anthraquinonyl, styryl, fluorenyl, furyl, pyridyl, quinolyl, methylcarbazolyl and ethylcarbazolyl. R1R2CO may also be phenanthraquinone.
GB2130858A 1958-07-03 1958-07-03 Improvements in and relating to electrophotographic reproduction materials Expired GB930988A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2130858A GB930988A (en) 1958-07-03 1958-07-03 Improvements in and relating to electrophotographic reproduction materials

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2130858A GB930988A (en) 1958-07-03 1958-07-03 Improvements in and relating to electrophotographic reproduction materials

Publications (1)

Publication Number Publication Date
GB930988A true GB930988A (en) 1963-07-10

Family

ID=10160690

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2130858A Expired GB930988A (en) 1958-07-03 1958-07-03 Improvements in and relating to electrophotographic reproduction materials

Country Status (1)

Country Link
GB (1) GB930988A (en)

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USB337787I5 (en) * 1973-03-05 1975-01-28
US4150987A (en) * 1977-10-17 1979-04-24 International Business Machines Corporation Hydrazone containing charge transport element and photoconductive process of using same
DE2919791A1 (en) * 1978-05-17 1979-11-22 Mitsubishi Chem Ind ELECTROPHOTOGRAPHIC PLATE
FR2437645A1 (en) * 1978-09-29 1980-04-25 Ricoh Kk ELECTROPHOTOGRAPHIC PHOTOCONDUCTOR
FR2438858A1 (en) * 1978-10-13 1980-05-09 Ricoh Kk ELECTROPHOTOGRAPHIC ELEMENT CONTAINING PHENYLHYDRAZONES
EP0013172A2 (en) * 1978-12-21 1980-07-09 Ricoh Company, Ltd Electrophotographic elements
US4269922A (en) * 1979-03-12 1981-05-26 Xerox Corporation Positive toners containing long chain hydrazinium compounds
US4297426A (en) * 1979-05-28 1981-10-27 Ricoh Co., Ltd. Electrophotographic element with carbazole hydrazone or anile charge transport compounds
US4332948A (en) 1979-05-25 1982-06-01 Ricoh Company, Ltd. Novel hydrazone compounds and process for preparing the same
DE3150265A1 (en) * 1980-12-19 1982-08-26 Fuji Photo Film Co., Ltd., Minami-Ashigara, Kanagawa ELECTROPHOTOGRAPHICALLY SENSITIVE MATERIALS
US4388393A (en) * 1980-03-13 1983-06-14 Ricoh Co., Ltd. Hydrazone compound, with hydroxyethyl group in charge transfer layer
US4399207A (en) 1981-07-31 1983-08-16 Canon Kabushiki Kaisha Electrophotographic photosensitive member with hydrazone compound
US4413045A (en) 1981-05-26 1983-11-01 Canon Kabushiki Kaisha Multilayer electrophotographic photosensitive member comprises disazo charge generator layer, hydrazone transport layer
US4418133A (en) 1981-03-27 1983-11-29 Canon Kabushiki Kaisha Disazo photoconductive material and electrophotographic photosensitive member having disazo pigment layer
US4423129A (en) 1980-12-17 1983-12-27 Canon Kabushiki Kaisha Electrophotographic member having layer containing methylidenyl hydrazone compound
EP0096989A2 (en) * 1982-05-26 1983-12-28 Toray Industries, Inc. Electrophotographic photosensitive material
US4446217A (en) * 1981-02-03 1984-05-01 Canon Kabushiki Kaisha Electrophotographic photosensitive member having a hydrazone containing layer
US4456671A (en) * 1981-12-23 1984-06-26 Canon Kabushiki Kaisha Electrophotographic photosensitive member having a photosensitive layer containing a hydrazone compound
US4487824A (en) * 1982-05-17 1984-12-11 Canon Kabushiki Kaisha Electrophotographic photosensitive member containing a halogen substituted hydrazone
US4554231A (en) * 1980-09-26 1985-11-19 Canon Kabushiki Kaisha Electrophotographic photosensitive member
EP1530093A2 (en) * 2003-10-31 2005-05-11 Samsung Electronics Co., Ltd. Organophotoreceptor with charge transport material with a hydrazone group linked to a heterocyclic group
WO2016094307A1 (en) * 2014-12-08 2016-06-16 The Research Foundation For The State University Of New York Anti-fungals targeting the synthesis of fungal shingolipids

Cited By (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3923506A (en) * 1973-03-05 1975-12-02 Xerox Corp Photoelectric and electrophotographic pigments comprising derivatives of condensed polycyclic aromatic hydrocarbon aldehydes
USB337787I5 (en) * 1973-03-05 1975-01-28
US4150987A (en) * 1977-10-17 1979-04-24 International Business Machines Corporation Hydrazone containing charge transport element and photoconductive process of using same
EP0001599A1 (en) * 1977-10-17 1979-05-02 International Business Machines Corporation Electrophotographic recording material and its application in a copying process
US4278747A (en) 1978-05-17 1981-07-14 Mitsubishi Chemical Industries Limited Electrophotographic plate comprising a conductive substrate and a photosensitive layer containing an organic photoconductor layer composed of a hydrazone compound
DE2919791A1 (en) * 1978-05-17 1979-11-22 Mitsubishi Chem Ind ELECTROPHOTOGRAPHIC PLATE
FR2426281A1 (en) * 1978-05-17 1979-12-14 Mitsubishi Chem Ind ELECTROPHOTOGRAPHIC PLATE
FR2437645A1 (en) * 1978-09-29 1980-04-25 Ricoh Kk ELECTROPHOTOGRAPHIC PHOTOCONDUCTOR
US4365014A (en) * 1978-09-29 1982-12-21 Ricoh Company, Limited Electrophotographic photoconductor
FR2438858A1 (en) * 1978-10-13 1980-05-09 Ricoh Kk ELECTROPHOTOGRAPHIC ELEMENT CONTAINING PHENYLHYDRAZONES
US4338388A (en) * 1978-10-13 1982-07-06 Ricoh Company, Limited Electrophotographic element with a phenyhydrazone charge transport layer
EP0013172A2 (en) * 1978-12-21 1980-07-09 Ricoh Company, Ltd Electrophotographic elements
EP0013172A3 (en) * 1978-12-21 1980-08-06 Ricoh Company, Ltd Electrophotographic elements
US4269922A (en) * 1979-03-12 1981-05-26 Xerox Corporation Positive toners containing long chain hydrazinium compounds
US4332948A (en) 1979-05-25 1982-06-01 Ricoh Company, Ltd. Novel hydrazone compounds and process for preparing the same
US4297426A (en) * 1979-05-28 1981-10-27 Ricoh Co., Ltd. Electrophotographic element with carbazole hydrazone or anile charge transport compounds
US4388393A (en) * 1980-03-13 1983-06-14 Ricoh Co., Ltd. Hydrazone compound, with hydroxyethyl group in charge transfer layer
US4554231A (en) * 1980-09-26 1985-11-19 Canon Kabushiki Kaisha Electrophotographic photosensitive member
US4423129A (en) 1980-12-17 1983-12-27 Canon Kabushiki Kaisha Electrophotographic member having layer containing methylidenyl hydrazone compound
DE3150265A1 (en) * 1980-12-19 1982-08-26 Fuji Photo Film Co., Ltd., Minami-Ashigara, Kanagawa ELECTROPHOTOGRAPHICALLY SENSITIVE MATERIALS
US4396694A (en) * 1980-12-19 1983-08-02 Fuji Photo Film Co., Ltd. Organic electrophotographic sensitive materials
US4446217A (en) * 1981-02-03 1984-05-01 Canon Kabushiki Kaisha Electrophotographic photosensitive member having a hydrazone containing layer
US4418133A (en) 1981-03-27 1983-11-29 Canon Kabushiki Kaisha Disazo photoconductive material and electrophotographic photosensitive member having disazo pigment layer
US4413045A (en) 1981-05-26 1983-11-01 Canon Kabushiki Kaisha Multilayer electrophotographic photosensitive member comprises disazo charge generator layer, hydrazone transport layer
US4399207A (en) 1981-07-31 1983-08-16 Canon Kabushiki Kaisha Electrophotographic photosensitive member with hydrazone compound
US4456671A (en) * 1981-12-23 1984-06-26 Canon Kabushiki Kaisha Electrophotographic photosensitive member having a photosensitive layer containing a hydrazone compound
US4487824A (en) * 1982-05-17 1984-12-11 Canon Kabushiki Kaisha Electrophotographic photosensitive member containing a halogen substituted hydrazone
EP0096989A2 (en) * 1982-05-26 1983-12-28 Toray Industries, Inc. Electrophotographic photosensitive material
EP0096989A3 (en) * 1982-05-26 1984-11-14 Toray Industries, Inc. Electrophotographic photosensitive material
EP1530093A2 (en) * 2003-10-31 2005-05-11 Samsung Electronics Co., Ltd. Organophotoreceptor with charge transport material with a hydrazone group linked to a heterocyclic group
EP1530093A3 (en) * 2003-10-31 2005-10-05 Samsung Electronics Co., Ltd. Organophotoreceptor with charge transport material with a hydrazone group linked to a heterocyclic group
US7169520B2 (en) 2003-10-31 2007-01-30 Samsung Electronics Co., Ltd Organophotoreceptor with charge transport material with a hydrazone group linked to a heterocyclic group
WO2016094307A1 (en) * 2014-12-08 2016-06-16 The Research Foundation For The State University Of New York Anti-fungals targeting the synthesis of fungal shingolipids
US11390580B2 (en) 2014-12-08 2022-07-19 The Research Foundation For The State University Of New York Anti-fungals targeting the synthesis of fungal shingolipids

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