JPS6317100B2 - - Google Patents

Info

Publication number

JPS6317100B2

JPS6317100B2 JP16034179A JP16034179A JPS6317100B2 JP S6317100 B2 JPS6317100 B2 JP S6317100B2 JP 16034179 A JP16034179 A JP 16034179A JP 16034179 A JP16034179 A JP 16034179A JP S6317100 B2 JPS6317100 B2 JP S6317100B2

Authority

JP

Japan

Prior art keywords

group

formula

compound represented

compound

general formula

Prior art date

1979-12-12

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

Links

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• -1 disazo compound Chemical class 0.000 claims description 16
• 150000001875 compounds Chemical class 0.000 claims description 15
• 238000004519 manufacturing process Methods 0.000 claims description 9
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
• 229910052801 chlorine Inorganic materials 0.000 claims description 4
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
• 125000000129 anionic group Chemical group 0.000 claims description 2
• 238000005859 coupling reaction Methods 0.000 claims description 2
• 125000000524 functional group Chemical group 0.000 claims description 2
• 108091008695 photoreceptors Proteins 0.000 description 20
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
• 238000000034 method Methods 0.000 description 8
• 239000000463 material Substances 0.000 description 7
• 238000000862 absorption spectrum Methods 0.000 description 5
• BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 4
• 229910052711 selenium Inorganic materials 0.000 description 4
• 239000011669 selenium Substances 0.000 description 4
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
• 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
• 239000000243 solution Substances 0.000 description 3
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
• RLCZBUOZNFAZLK-UHFFFAOYSA-N 3-hydroxynaphthalene-2-carbonyl chloride Chemical compound C1=CC=C2C=C(C(Cl)=O)C(O)=CC2=C1 RLCZBUOZNFAZLK-UHFFFAOYSA-N 0.000 description 2
• IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 description 2
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
• 206010034972 Photosensitivity reaction Diseases 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
• XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
• CIZVQWNPBGYCGK-UHFFFAOYSA-N benzenediazonium Chemical class N#[N+]C1=CC=CC=C1 CIZVQWNPBGYCGK-UHFFFAOYSA-N 0.000 description 2
• 238000006243 chemical reaction Methods 0.000 description 2
• 239000013078 crystal Substances 0.000 description 2
• 238000000921 elemental analysis Methods 0.000 description 2
• 230000008018 melting Effects 0.000 description 2
• 238000002844 melting Methods 0.000 description 2
• 230000036211 photosensitivity Effects 0.000 description 2
• 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
• 239000002244 precipitate Substances 0.000 description 2
• 235000017281 sodium acetate Nutrition 0.000 description 2
• 239000001632 sodium acetate Substances 0.000 description 2
• WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 1
• 238000010521 absorption reaction Methods 0.000 description 1
• 125000003368 amide group Chemical group 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 229910052980 cadmium sulfide Inorganic materials 0.000 description 1
• 239000000460 chlorine Substances 0.000 description 1
• 230000001419 dependent effect Effects 0.000 description 1
• 239000012954 diazonium Substances 0.000 description 1
• IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
• 230000005496 eutectics Effects 0.000 description 1
• 230000014759 maintenance of location Effects 0.000 description 1
• 239000012046 mixed solvent Substances 0.000 description 1
• RGNFPYSMVGGFPL-UHFFFAOYSA-N naphthalene-1-diazonium Chemical class C1=CC=C2C([N+]#N)=CC=CC2=C1 RGNFPYSMVGGFPL-UHFFFAOYSA-N 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 239000000049 pigment Substances 0.000 description 1
• 239000000047 product Substances 0.000 description 1
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
• WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
• 239000011347 resin Substances 0.000 description 1
• 229920005989 resin Polymers 0.000 description 1
• 239000011787 zinc oxide Substances 0.000 description 1