DE1120875B - Material fuer elektrophotographische Reproduktion - Google Patents
Material fuer elektrophotographische ReproduktionInfo
- Publication number
- DE1120875B DE1120875B DEK35572A DEK0035572A DE1120875B DE 1120875 B DE1120875 B DE 1120875B DE K35572 A DEK35572 A DE K35572A DE K0035572 A DEK0035572 A DE K0035572A DE 1120875 B DE1120875 B DE 1120875B
- Authority
- DE
- Germany
- Prior art keywords
- oxazole
- formula
- phenyl
- chlorophenyl
- sulfuric acid
- 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.)
- Pending
Links
- 239000000463 material Substances 0.000 title claims description 12
- -1 aminophenyl groups Chemical group 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 9
- 150000002916 oxazoles Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000000084 colloidal system Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000006104 solid solution Substances 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 52
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- 235000019441 ethanol Nutrition 0.000 description 34
- 238000009833 condensation Methods 0.000 description 32
- 230000005494 condensation Effects 0.000 description 32
- 239000010410 layer Substances 0.000 description 32
- 239000013078 crystal Substances 0.000 description 31
- 229920005989 resin Polymers 0.000 description 31
- 239000011347 resin Substances 0.000 description 31
- 238000002844 melting Methods 0.000 description 30
- 230000008018 melting Effects 0.000 description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 23
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 244000028419 Styrax benzoin Species 0.000 description 13
- 235000000126 Styrax benzoin Nutrition 0.000 description 13
- 235000008411 Sumatra benzointree Nutrition 0.000 description 13
- 235000019382 gum benzoic Nutrition 0.000 description 13
- 229960002130 benzoin Drugs 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 239000011888 foil Substances 0.000 description 10
- 239000000155 melt Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000000975 dye Substances 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- ODISVHPYJICALC-UHFFFAOYSA-N 1-(2-aminophenyl)-2-hydroxy-2-phenylethanone Chemical compound NC1=CC=CC=C1C(=O)C(O)C1=CC=CC=C1 ODISVHPYJICALC-UHFFFAOYSA-N 0.000 description 6
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 6
- DMZJGPXZLVUMIN-UHFFFAOYSA-N 5-(2-chlorophenyl)-1,3-oxazole Chemical compound ClC1=CC=CC=C1C1=CN=CO1 DMZJGPXZLVUMIN-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- ALAPJBJCAPZHNC-UHFFFAOYSA-N 1-[4-(diethylamino)phenyl]-2-hydroxy-2-phenylethanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C(O)C1=CC=CC=C1 ALAPJBJCAPZHNC-UHFFFAOYSA-N 0.000 description 5
- JYMNQRQQBJIMCV-UHFFFAOYSA-N 4-(dimethylamino)benzonitrile Chemical compound CN(C)C1=CC=C(C#N)C=C1 JYMNQRQQBJIMCV-UHFFFAOYSA-N 0.000 description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- SOLBSNQBVLAREX-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]-2-hydroxy-2-phenylethanone Chemical group C1=CC(N(C)C)=CC=C1C(=O)C(O)C1=CC=CC=C1 SOLBSNQBVLAREX-UHFFFAOYSA-N 0.000 description 4
- GJNGXPDXRVXSEH-UHFFFAOYSA-N 4-chlorobenzonitrile Chemical compound ClC1=CC=C(C#N)C=C1 GJNGXPDXRVXSEH-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 230000035515 penetration Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 230000033458 reproduction Effects 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 229920003002 synthetic resin Polymers 0.000 description 4
- 239000000057 synthetic resin Substances 0.000 description 4
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 3
- CRLIFCWONWOOPQ-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-[4-(dimethylamino)phenyl]-2-hydroxyethanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C(O)C1=CC=C(Cl)C=C1 CRLIFCWONWOOPQ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- NHWQMJMIYICNBP-UHFFFAOYSA-N 2-chlorobenzonitrile Chemical compound ClC1=CC=CC=C1C#N NHWQMJMIYICNBP-UHFFFAOYSA-N 0.000 description 3
- YPYPBEGIASEWKA-UHFFFAOYSA-N 5-phenyl-1,3-oxazole Chemical compound O1C=NC=C1C1=CC=CC=C1 YPYPBEGIASEWKA-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical class NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 3
- 239000004071 soot Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- CNRNYORZJGVOSY-UHFFFAOYSA-N 2,5-diphenyl-1,3-oxazole Chemical class C=1N=C(C=2C=CC=CC=2)OC=1C1=CC=CC=C1 CNRNYORZJGVOSY-UHFFFAOYSA-N 0.000 description 2
- PJKPHOIIYXTDIA-UHFFFAOYSA-N 5-(4-chlorophenyl)-1,3-oxazole Chemical compound C1=CC(Cl)=CC=C1C1=CN=CO1 PJKPHOIIYXTDIA-UHFFFAOYSA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- 239000004801 Chlorinated PVC Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229920000457 chlorinated polyvinyl chloride Polymers 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- NNICRUQPODTGRU-UHFFFAOYSA-N mandelonitrile Chemical compound N#CC(O)C1=CC=CC=C1 NNICRUQPODTGRU-UHFFFAOYSA-N 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- UTYAVHBVIUGHOZ-UHFFFAOYSA-N n,n-dimethyl-4-(5-phenyl-1,3-oxazol-2-yl)aniline Chemical compound C1=CC(N(C)C)=CC=C1C1=NC=C(C=2C=CC=CC=2)O1 UTYAVHBVIUGHOZ-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 2
- 230000011514 reflex Effects 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 2
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- VUPXKQHLZATXTR-UHFFFAOYSA-N 2,4-diphenyl-1,3-oxazole Chemical compound C=1OC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 VUPXKQHLZATXTR-UHFFFAOYSA-N 0.000 description 1
- MLHWGXAMPAHBDG-UHFFFAOYSA-N 2-(2-chlorophenyl)-1-[4-(dibutylamino)phenyl]-2-hydroxyethanone Chemical compound ClC1=C(C(C(C2=CC=C(C=C2)N(CCCC)CCCC)=O)O)C=CC=C1 MLHWGXAMPAHBDG-UHFFFAOYSA-N 0.000 description 1
- SGPAMTJJOZTJLD-UHFFFAOYSA-N 2-(2-chlorophenyl)-1-[4-(diethylamino)phenyl]-2-hydroxyethanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C(O)C1=CC=CC=C1Cl SGPAMTJJOZTJLD-UHFFFAOYSA-N 0.000 description 1
- MDDZERLNZSGENP-UHFFFAOYSA-N 2-(2-chlorophenyl)-1-[4-(dimethylamino)phenyl]-2-hydroxyethanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C(O)C1=CC=CC=C1Cl MDDZERLNZSGENP-UHFFFAOYSA-N 0.000 description 1
- CZWWMFTTWBYZAX-UHFFFAOYSA-N 2-(3-chlorophenyl)-1-[4-(dimethylamino)phenyl]-2-hydroxyethanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C(O)C1=CC=CC(Cl)=C1 CZWWMFTTWBYZAX-UHFFFAOYSA-N 0.000 description 1
- TWAOVIVEUFBAHK-UHFFFAOYSA-N 2-(dimethylamino)benzoyl chloride Chemical compound CN(C)C1=CC=CC=C1C(Cl)=O TWAOVIVEUFBAHK-UHFFFAOYSA-N 0.000 description 1
- SHIBMGQAICRHTE-UHFFFAOYSA-N 2-(methylamino)benzonitrile Chemical compound CNC1=CC=CC=C1C#N SHIBMGQAICRHTE-UHFFFAOYSA-N 0.000 description 1
- KIIOPQYCYPGLIF-UHFFFAOYSA-N 2-(propylamino)benzonitrile Chemical compound CCCNC1=CC=CC=C1C#N KIIOPQYCYPGLIF-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- IOOMXAQUNPWDLL-UHFFFAOYSA-N 2-[6-(diethylamino)-3-(diethyliminiumyl)-3h-xanthen-9-yl]-5-sulfobenzene-1-sulfonate Chemical compound C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S(O)(=O)=O)C=C1S([O-])(=O)=O IOOMXAQUNPWDLL-UHFFFAOYSA-N 0.000 description 1
- YSFIWHBTOIARNJ-UHFFFAOYSA-N 2-hydroxy-1-[2-(methylamino)phenyl]-2-phenylethanone Chemical compound CNC1=CC=CC=C1C(=O)C(O)C1=CC=CC=C1 YSFIWHBTOIARNJ-UHFFFAOYSA-N 0.000 description 1
- RQCBPOPQTLHDFC-UHFFFAOYSA-N 2-phenyl-1,3-oxazole Chemical class C1=COC(C=2C=CC=CC=2)=N1 RQCBPOPQTLHDFC-UHFFFAOYSA-N 0.000 description 1
- KKAJSJJFBSOMGS-UHFFFAOYSA-N 3,6-diamino-10-methylacridinium chloride Chemical compound [Cl-].C1=C(N)C=C2[N+](C)=C(C=C(N)C=C3)C3=CC2=C1 KKAJSJJFBSOMGS-UHFFFAOYSA-N 0.000 description 1
- HGZXQCCQZLSOPP-UHFFFAOYSA-N 3-amino-1-phenylpropan-1-one Chemical compound NCCC(=O)C1=CC=CC=C1 HGZXQCCQZLSOPP-UHFFFAOYSA-N 0.000 description 1
- WBUOVKBZJOIOAE-UHFFFAOYSA-N 3-chlorobenzonitrile Chemical compound ClC1=CC=CC(C#N)=C1 WBUOVKBZJOIOAE-UHFFFAOYSA-N 0.000 description 1
- ODKHOKLXMBWVOQ-UHFFFAOYSA-N 4,5-diphenyl-1,3-oxazole Chemical class O1C=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 ODKHOKLXMBWVOQ-UHFFFAOYSA-N 0.000 description 1
- MLEBCZSWVARRML-UHFFFAOYSA-N 4-(2,5-diphenyl-1,3-oxazol-4-yl)-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C1=C(C=2C=CC=CC=2)OC(C=2C=CC=CC=2)=N1 MLEBCZSWVARRML-UHFFFAOYSA-N 0.000 description 1
- FATMRNKHKKKOLC-UHFFFAOYSA-N 4-(2,5-diphenyl-1,3-oxazol-4-yl)-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C1=C(C=2C=CC=CC=2)OC(C=2C=CC=CC=2)=N1 FATMRNKHKKKOLC-UHFFFAOYSA-N 0.000 description 1
- KEEOEAJGZJOICF-UHFFFAOYSA-N 4-(4,5-diphenyl-1,3-oxazol-2-yl)-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)O1 KEEOEAJGZJOICF-UHFFFAOYSA-N 0.000 description 1
- STSISQMFQWBGLZ-UHFFFAOYSA-N 4-(4-nitrophenyl)-1,3-oxazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=COC=N1 STSISQMFQWBGLZ-UHFFFAOYSA-N 0.000 description 1
- MNFZZNNFORDXSV-UHFFFAOYSA-N 4-(diethylamino)benzaldehyde Chemical compound CCN(CC)C1=CC=C(C=O)C=C1 MNFZZNNFORDXSV-UHFFFAOYSA-N 0.000 description 1
- JCYPECIVGRXBMO-UHFFFAOYSA-N 4-(dimethylamino)azobenzene Chemical compound C1=CC(N(C)C)=CC=C1N=NC1=CC=CC=C1 JCYPECIVGRXBMO-UHFFFAOYSA-N 0.000 description 1
- QUVXUKJGBDJPDP-UHFFFAOYSA-N 4-[2-(2-chlorophenyl)-5-phenyl-1,3-oxazol-4-yl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C1=C(C=2C=CC=CC=2)OC(C=2C(=CC=CC=2)Cl)=N1 QUVXUKJGBDJPDP-UHFFFAOYSA-N 0.000 description 1
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- UUKFSMLWMXTUKH-UHFFFAOYSA-N 4-[2-[4-(dimethylamino)phenyl]-5-phenyl-1,3-oxazol-4-yl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C1=NC(C=2C=CC(=CC=2)N(C)C)=C(C=2C=CC=CC=2)O1 UUKFSMLWMXTUKH-UHFFFAOYSA-N 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
- AXMCIYLNKNGNOT-UHFFFAOYSA-M sodium;3-[[4-[(4-dimethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)-[4-[ethyl-[(3-sulfonatophenyl)methyl]amino]phenyl]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 AXMCIYLNKNGNOT-UHFFFAOYSA-M 0.000 description 1
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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
- G03G5/0622—Heterocyclic compounds
- G03G5/0624—Heterocyclic compounds containing one hetero ring
- G03G5/0627—Heterocyclic compounds containing one hetero ring being five-membered
- G03G5/0631—Heterocyclic compounds containing one hetero ring being five-membered containing two hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic 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
- C07D263/32—Heterocyclic 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL126440D NL126440C (OSRAM) | 1958-08-20 | ||
| BE581861D BE581861A (OSRAM) | 1958-08-20 | ||
| NL242505D NL242505A (OSRAM) | 1958-08-20 | ||
| DEK35572A DE1120875B (de) | 1958-08-20 | 1958-08-20 | Material fuer elektrophotographische Reproduktion |
| CH7694459A CH379280A (de) | 1958-08-20 | 1959-08-13 | Material für elektrophotographische Reproduktion |
| GB27749/59A GB874634A (en) | 1958-08-20 | 1959-08-13 | Improvements in photographic reproduction |
| FR803023A FR1232805A (fr) | 1958-08-20 | 1959-08-18 | Matériel pour la reproduction électrophotographique |
| US834417A US3257203A (en) | 1958-08-20 | 1959-08-18 | Electrophotographic reproduction material |
| ES0251855A ES251855A1 (es) | 1958-08-20 | 1959-08-20 | Un procedimiento de fabricacion de un material para reproduccion electrofotografica |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK35572A DE1120875B (de) | 1958-08-20 | 1958-08-20 | Material fuer elektrophotographische Reproduktion |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1120875B true DE1120875B (de) | 1961-12-28 |
Family
ID=7220394
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEK35572A Pending DE1120875B (de) | 1958-08-20 | 1958-08-20 | Material fuer elektrophotographische Reproduktion |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3257203A (OSRAM) |
| BE (1) | BE581861A (OSRAM) |
| CH (1) | CH379280A (OSRAM) |
| DE (1) | DE1120875B (OSRAM) |
| ES (1) | ES251855A1 (OSRAM) |
| FR (1) | FR1232805A (OSRAM) |
| GB (1) | GB874634A (OSRAM) |
| NL (2) | NL242505A (OSRAM) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1254467B (de) * | 1962-12-18 | 1967-11-16 | Kalle Ag | Photoleitfaehige Schichten |
| DE2336094A1 (de) * | 1973-07-16 | 1975-02-06 | Hoechst Ag | Elektrophotographisches aufzeichungsmaterial |
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| US2341009A (en) * | 1936-03-19 | 1944-02-08 | Richards Chemical Works | Method of improving brightness of fibrous materials |
| US2176516A (en) * | 1936-06-12 | 1939-10-17 | Agfa Ansco Corp | Polarizing layer |
| FR1008598A (fr) * | 1948-04-30 | 1952-05-19 | Onera (Off Nat Aerospatiale) | Procédé pour l'enregistrement graphique ou l'inscription dirccte en matériaux pour la mise en oeuvre de ce procédé |
| US2663636A (en) * | 1949-05-25 | 1953-12-22 | Haloid Co | Electrophotographic plate and method of producing same |
| GB669590A (en) * | 1949-06-03 | 1952-04-02 | Ilford Ltd | Improvements in or relating to a process for improving the whiteness of colour materials |
| US2726246A (en) * | 1951-05-02 | 1955-12-06 | Cassella Farbwerke Mainkur Ag | Fluorescent heterocyclic compounds and process for their manufacture |
| US2709702A (en) * | 1951-10-12 | 1955-05-31 | Gen Aniline & Film Corp | Fluorescent agents |
| US2704286A (en) * | 1954-05-07 | 1955-03-15 | Du Pont | Fluorescent whitening agents |
| BE553516A (OSRAM) * | 1955-12-19 |
-
0
- NL NL126440D patent/NL126440C/xx active
- NL NL242505D patent/NL242505A/xx unknown
- BE BE581861D patent/BE581861A/xx unknown
-
1958
- 1958-08-20 DE DEK35572A patent/DE1120875B/de active Pending
-
1959
- 1959-08-13 GB GB27749/59A patent/GB874634A/en not_active Expired
- 1959-08-13 CH CH7694459A patent/CH379280A/de unknown
- 1959-08-18 US US834417A patent/US3257203A/en not_active Expired - Lifetime
- 1959-08-18 FR FR803023A patent/FR1232805A/fr not_active Expired
- 1959-08-20 ES ES0251855A patent/ES251855A1/es not_active Expired
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1254467B (de) * | 1962-12-18 | 1967-11-16 | Kalle Ag | Photoleitfaehige Schichten |
| DE2336094A1 (de) * | 1973-07-16 | 1975-02-06 | Hoechst Ag | Elektrophotographisches aufzeichungsmaterial |
| DE2935481A1 (de) * | 1978-09-04 | 1980-04-03 | Hitachi Ltd | Elektrophotographische platte |
| US4388391A (en) | 1980-02-15 | 1983-06-14 | Hoechst Aktiengesellschaft | Process for the manufacture of a lithographic printing form by electrophotography |
| US4739053A (en) * | 1983-02-09 | 1988-04-19 | Basf Aktiengesellschaft | 2H-v-triazolo[4-5-d]pyrimidines |
| US4528256A (en) * | 1983-04-15 | 1985-07-09 | Hoechst Aktiengesellschaft | Electrophotographic recording material with condensation product |
| US4533612A (en) * | 1983-04-27 | 1985-08-06 | Basf Aktiengesellschaft | Electrophotographic recording materials containing special charge carrier-transporting compounds |
| US4556621A (en) * | 1983-07-05 | 1985-12-03 | Basf Aktiengesellschaft | Electrophotographic recording material containing a metal-1,3-diketone complex |
| US4559285A (en) * | 1983-07-05 | 1985-12-17 | Basf Aktiengesellschaft | Electrophotographic recording materials containing a metal acetylacetonate |
| EP1515191A2 (en) | 2003-09-05 | 2005-03-16 | Xerox Corporation | Dual charge transport layer and photoconductive imaging member including the same |
Also Published As
| Publication number | Publication date |
|---|---|
| US3257203A (en) | 1966-06-21 |
| CH379280A (de) | 1964-06-30 |
| ES251855A1 (es) | 1960-03-16 |
| FR1232805A (fr) | 1960-10-12 |
| BE581861A (OSRAM) | |
| NL242505A (OSRAM) | |
| NL126440C (OSRAM) | |
| GB874634A (en) | 1961-08-10 |
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