GB1046058A - Electrophotographic materials - Google Patents

Electrophotographic materials

Info

Publication number
GB1046058A
GB1046058A GB25103/65A GB2510365A GB1046058A GB 1046058 A GB1046058 A GB 1046058A GB 25103/65 A GB25103/65 A GB 25103/65A GB 2510365 A GB2510365 A GB 2510365A GB 1046058 A GB1046058 A GB 1046058A
Authority
GB
United Kingdom
Prior art keywords
carbazole
bromination
vinyl
vinyl carbazole
solution
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
GB25103/65A
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.)
Panasonic Holdings Corp
Original Assignee
Matsushita Electric Industrial 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 Matsushita Electric Industrial Co Ltd filed Critical Matsushita Electric Industrial Co Ltd
Publication of GB1046058A publication Critical patent/GB1046058A/en
Expired legal-status Critical Current

Links

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
    • G03G5/07—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
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
    • 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
    • C08F26/12—N-Vinyl-carbazole
    • 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
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/18—Introducing halogen atoms or halogen-containing groups
    • C08F8/20—Halogenation

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Photoreceptors In Electrophotography (AREA)

Abstract

3,6-dibromo-9-vinyl carbazole is obtained by bromination of 9-b -chloroethyl carbazole followed by dehydrohalogenation. The bromination is carried out using a mixture of potassium bromide and potassium bromate in acetic acid solution. The intermediate product 3,6-di-bromo carbazole precipitates out, is recrystallized and isolated in the form of white needle crystals having a m. pt. of 156-157 DEG C. The hydrohalogenation is carried out by adding a solution of potassium hydroxide in methanol to a solution of the intermediate in ethanol and refluxing.ALSO:Polymers containing the recurring units represented by the general formula <FORM:1046058/C3/1> in which X represents a member selected from hydrogen and bromine is obtained by the polymerization or copolymerization of 3,6-dibromo-9-vinyl carbazole, or by the bromination of poly-9-vinyl carbazole with N-bromo succimide. Specified comonomers include styrene, 9-vinyl carbazole and 1-vinyl naphthalene. Compositions of the above polymer are used as photosensitive materials for use in electrophotography (see Division H1). The compositions comprise solutions of the polymer, together with dye-stuffs, plasticizers and sensitizers.
GB25103/65A 1964-06-18 1965-06-14 Electrophotographic materials Expired GB1046058A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP3490864 1964-06-18
JP3491064 1964-06-18
JP5887164 1964-10-13

Publications (1)

Publication Number Publication Date
GB1046058A true GB1046058A (en) 1966-10-19

Family

ID=27288571

Family Applications (1)

Application Number Title Priority Date Filing Date
GB25103/65A Expired GB1046058A (en) 1964-06-18 1965-06-14 Electrophotographic materials

Country Status (3)

Country Link
US (1) US3421891A (en)
DE (1) DE1497183B2 (en)
GB (1) GB1046058A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5014527B1 (en) * 1970-04-09 1975-05-28

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3485624A (en) * 1966-06-07 1969-12-23 Eastman Kodak Co Photoconductive properties of poly-n-vinyl carbazole
US3765883A (en) * 1970-02-04 1973-10-16 Canon Kk Organic photoconductors sensitized with free radical liberators and organometallic compounds
US3847607A (en) * 1970-02-04 1974-11-12 Canon Kk Organic photoconductors sensitized by free radical liberators and organometallic compounds
JPS492630B1 (en) * 1970-03-09 1974-01-22
US3917482A (en) * 1970-11-09 1975-11-04 Canon Kk Photoconductive polymers of thiocyano-substituted-9-vinylcarbazoles
JPS4927705B1 (en) * 1970-12-16 1974-07-19
JPS4943896B2 (en) * 1971-10-06 1974-11-25
US4042388A (en) * 1972-03-15 1977-08-16 Canon Kabushiki Kaisha Process for the preparation of sensitized material for electrophotography
NL168059C (en) * 1972-09-15 1982-02-16 Oce Van Der Grinten Nv ELECTROPHOTOGRAPHIC DONOR ACCEPTOR COMPLEX CONTAINING REPRODUCTION ELEMENT, AND METHOD FOR PREPARING A PHOTOGRAPHIC PREPARATION.
JPS5135147B2 (en) * 1972-11-06 1976-09-30
US3791824A (en) * 1973-02-20 1974-02-12 Ibm Conjugated polymers in electrophotography
US3937631A (en) * 1973-12-26 1976-02-10 Scm Corporation Electrophotographic members including polyvinylcarbazoles and plasticizers therefore
US4105446A (en) * 1975-01-21 1978-08-08 Fuji Xerox Co., Ltd. Organic photoconductive coating compositions containing tricyanovinyl compounds for electrophotography
JPS561945A (en) * 1979-06-19 1981-01-10 Fuji Photo Film Co Ltd Photoconductive composition and electrophotographic material using it
NL7906932A (en) * 1979-09-18 1981-03-20 Philips Nv NEGATIVE RESIST MATERIAL, RESIST MATERIAL CARRIER AND METHOD FOR APPLYING A LAYER BY PATTERN.
US4308329A (en) * 1979-11-02 1981-12-29 Xerox Corporation Manifold imaging method and materials
JPS56143438A (en) * 1980-04-10 1981-11-09 Mita Ind Co Ltd Improvement of electrophotographic sensitive layer

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL231103A (en) * 1957-09-07
US3240594A (en) * 1959-02-26 1966-03-15 Gevaert Photo Producten Electrophotographic material
US3155503A (en) * 1959-02-26 1964-11-03 Gevaert Photo Prod Nv Electrophotographic material
LU38672A1 (en) * 1959-05-30
US3341472A (en) * 1963-08-26 1967-09-12 Ibm Photoconductors and method of making the same

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5014527B1 (en) * 1970-04-09 1975-05-28

Also Published As

Publication number Publication date
DE1497183A1 (en) 1969-05-22
DE1497183B2 (en) 1970-11-05
US3421891A (en) 1969-01-14

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