GB874634A - Improvements in photographic reproduction - Google Patents

Improvements in photographic reproduction

Info

Publication number
GB874634A
GB874634A GB27749/59A GB2774959A GB874634A GB 874634 A GB874634 A GB 874634A GB 27749/59 A GB27749/59 A GB 27749/59A GB 2774959 A GB2774959 A GB 2774959A GB 874634 A GB874634 A GB 874634A
Authority
GB
United Kingdom
Prior art keywords
phenyl
resins
alkyl
amino
substituted
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
GB27749/59A
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.)
Kalle GmbH and Co KG
Original Assignee
Kalle GmbH and Co KG
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 Kalle GmbH and Co KG filed Critical Kalle GmbH and Co KG
Publication of GB874634A publication Critical patent/GB874634A/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
    • G03G5/0627Heterocyclic compounds containing one hetero ring being five-membered
    • G03G5/0631Heterocyclic compounds containing one hetero ring being five-membered containing two hetero atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D263/00Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/32Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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

Abstract

Photoconductive resinous compositions comprise one or more di- or tri-phenyl-oxazoles of the general formula: <FORM:0874634/IV (a)/1> wherein R is aminophenyl or dialkyl aminophenyl, R1 is phenyl or substituted phenyl, R2 is H, alkyl, alkenyl or a heterocyclic radical, R3 and R4 are phenyl, aminophenyl or dialkylaminophenyl, and R5 is H or alkyl, together with a resin, and optionally a dyestuff, as in Specification 853,880. Many suitable oxazoles are listed. A solvent, e.g. benzene, acetone, methylene chloride or ethylene glycol monomethyl ether, is usually present. Resins used in the examples include aldehyde-ketone resins, an abietic acid -pentaerythritol resin modified glycerol-maleic acid resin, a zinc modified natural resin, after chlorinated P.V.C. and coumarone resin.ALSO:The preparation is described of aminophenyl-azoles of the following four formulae <FORM:0874634/IV (b)/1> or <FORM:0874634/IV (b)/2> or <FORM:0874634/IV (b)/3> or <FORM:0874634/IV (b)/4> where R is amino phenyl or dialkylaminophenyl, R1 is phenyl or substituted phenyl, R2 is H, alkyl, alkenyl or a heterocyclic radical, R3 and R4 are phenyl or substituted phenyl (at least one being substituted by amino or dialkylamino), and R5 is H or alkyl. Compounds (I) are made by ring-closing a -benzoylamino-alkyl phenyl ketones (appropriately substituted) with sulphuric acid, or by condensing benzaldehydes with benzaldehyde cyanohydrins in the presence of ethereal hydrogen chloride. In examples R is p-aminophenyl, p-dimethylaminophenyl or p-diethylaminophenyl, R1 is phenyl or p-chlorophenyl, and R5 is H or methyl. Compounds (II) are prepared by melting together benzamide and R-substituted phenacyl bromides. Compounds (III) are obtained by condensing R2CN with appropriately substituted benzoins in the presence or sulphuric or polyphosphoric acid. In examples R is p-dialkylaminophenyl (alkyl=methyl, ethyl, propyl or butyl), R1 is o- or p-chlorophenyl, and R2 is H, methyl, ethyl, propyl, vinyl or pyridyl. Compounds (IV) are made in the same way as (III). In examples R1 is phenyl or chlorophenyl (all 3 isomers), R3 is phenyl, chlorophenyl (all 3 isomers), m-aminophenyl, p-dimethylaminophenyl, p-diethylaminophenyl or p-dipropylaminophenyl, and R4 is phenyl or p-dialkylaminophenyl (alkyl=methyl, ethyl, propyl or butyl). 2-Phenyl-4-(p-diethylaminophenyl)- oxazole is prepared by melting together benzamide and p-nitro-phenacyl bromide to give 2-phenyl-4-(p-nitrophenyl)-oxazole, catalytically reducing this to the p-amino compound and treating the latter with ethyl phosphate. Acylamino-ketones are made by reacting p-dimethylamino-benzoyl chloride with o -amino-acetophenone, p-chloro-o -amino-acetophenone and a -amino-propiophenone respectively.ALSO:A coating composition for electrophotographic plates comprises a natural or synthetic resin and a photoconductive di- or tri-phenyloxazole, in which at least one of the phenyl groups is substituted by amino or dialkylamino. Specified resins include balsam resins, phenol resins, resins modified with colophony, cellulose ethers, polyvinyl, polyacrylic and polystyrene resins, isobutylene polymers, polyesters, phenol-, urea- and melamine-formaldehyde resins, aldehyde resins, ketone resins, polyamides and polyurethanes. A sensitising dyestuff or chlorophyll may be present. Specified solvents are methanol, methylene chloride, glycol monomethyl ether, acetone, methyl ethyl ketone, benzene and toluene. The support may be metal (e.g. aluminium), glass or a resin. Application may be by roller coating or spraying.
GB27749/59A 1958-08-20 1959-08-13 Improvements in photographic reproduction Expired GB874634A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEK35572A DE1120875B (en) 1958-08-20 1958-08-20 Material for electrophotographic reproduction

Publications (1)

Publication Number Publication Date
GB874634A true GB874634A (en) 1961-08-10

Family

ID=7220394

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27749/59A Expired GB874634A (en) 1958-08-20 1959-08-13 Improvements in photographic reproduction

Country Status (8)

Country Link
US (1) US3257203A (en)
BE (1) BE581861A (en)
CH (1) CH379280A (en)
DE (1) DE1120875B (en)
ES (1) ES251855A1 (en)
FR (1) FR1232805A (en)
GB (1) GB874634A (en)
NL (2) NL242505A (en)

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US4892799A (en) * 1987-03-04 1990-01-09 Hoechst Aktiengesellschaft 4-chlorooxazole derivatives and processes for their preparation and use
US8765746B2 (en) 2010-10-13 2014-07-01 Millennium Pharmaceuticals, Inc. Heteroaryls and uses thereof
US8796268B2 (en) 2010-08-11 2014-08-05 Millennium Pharmaceuticals, Inc. Heteroaryls and uses thereof
US8796314B2 (en) 2009-01-30 2014-08-05 Millennium Pharmaceuticals, Inc. Heteroaryls and uses thereof
US8859768B2 (en) 2010-08-11 2014-10-14 Millennium Pharmaceuticals, Inc. Heteroaryls and uses thereof
US9029411B2 (en) 2008-01-25 2015-05-12 Millennium Pharmaceuticals, Inc. Thiophenes and uses thereof
US9062038B2 (en) 2010-08-11 2015-06-23 Millennium Pharmaceuticals, Inc. Heteroaryls and uses thereof
US9090601B2 (en) 2009-01-30 2015-07-28 Millennium Pharmaceuticals, Inc. Thiazole derivatives
US9139589B2 (en) 2009-01-30 2015-09-22 Millennium Pharmaceuticals, Inc. Heteroaryls and uses thereof

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US3257203A (en) 1966-06-21
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BE581861A (en)
ES251855A1 (en) 1960-03-16
DE1120875B (en) 1961-12-28

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