US3814752A - 6,6'-methylenebis(2-styryl benzopyrylium salt)as sensitizers for use in electrophotographic light-sensitive materials - Google Patents
6,6'-methylenebis(2-styryl benzopyrylium salt)as sensitizers for use in electrophotographic light-sensitive materials Download PDFInfo
- Publication number
- US3814752A US3814752A US00259392A US25939272A US3814752A US 3814752 A US3814752 A US 3814752A US 00259392 A US00259392 A US 00259392A US 25939272 A US25939272 A US 25939272A US 3814752 A US3814752 A US 3814752A
- Authority
- US
- United States
- Prior art keywords
- methylenebis
- solution
- compound
- sensitizers
- perchlorate
- 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 - Lifetime
Links
- 239000000463 material Substances 0.000 title abstract description 15
- -1 2-styryl benzopyrylium salt Chemical class 0.000 title description 8
- 150000003839 salts Chemical class 0.000 abstract description 6
- 239000000243 solution Substances 0.000 description 36
- 150000001875 compounds Chemical class 0.000 description 33
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 24
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 9
- 238000009833 condensation Methods 0.000 description 8
- 230000005494 condensation Effects 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 235000019253 formic acid Nutrition 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 4
- OWPBOKWFRAIKTD-UHFFFAOYSA-N 5-[(3-formyl-4-hydroxyphenyl)methyl]-2-hydroxybenzaldehyde Chemical compound C1=C(C=O)C(O)=CC=C1CC1=CC=C(O)C(C=O)=C1 OWPBOKWFRAIKTD-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000008033 biological extinction Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- JPBGLQJDCUZXEF-UHFFFAOYSA-N chromenylium Chemical class [O+]1=CC=CC2=CC=CC=C21 JPBGLQJDCUZXEF-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- LWRSYTXEQUUTKW-UHFFFAOYSA-N 2,4-dimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(OC)=C1 LWRSYTXEQUUTKW-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- UCTUXUGXIFRVGX-UHFFFAOYSA-N 2,3,4-trimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(OC)=C1OC UCTUXUGXIFRVGX-UHFFFAOYSA-N 0.000 description 1
- VDVOJNBNSUJCSZ-UHFFFAOYSA-M 3-phenylchromenylium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C1=CC=CC=C1C1=C[O+]=C(C=CC=C2)C2=C1 VDVOJNBNSUJCSZ-UHFFFAOYSA-M 0.000 description 1
- 241000518994 Conta Species 0.000 description 1
- 229910003771 Gold(I) chloride Inorganic materials 0.000 description 1
- 239000006001 Methyl nonyl ketone Substances 0.000 description 1
- 229910020808 NaBF Inorganic materials 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- KMPQYAYAQWNLME-UHFFFAOYSA-N Undecanal Natural products CCCCCCCCCCC=O KMPQYAYAQWNLME-UHFFFAOYSA-N 0.000 description 1
- CHZWRIFDYXSVOD-UHFFFAOYSA-M chromenylium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.[O+]1=CC=CC2=CC=CC=C21 CHZWRIFDYXSVOD-UHFFFAOYSA-M 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- FDWREHZXQUYJFJ-UHFFFAOYSA-M gold monochloride Chemical compound [Cl-].[Au+] FDWREHZXQUYJFJ-UHFFFAOYSA-M 0.000 description 1
- 229960000443 hydrochloric acid Drugs 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- BGEHHAVMRVXCGR-UHFFFAOYSA-N methylundecylketone Natural products CCCCCCCCCCCCC=O BGEHHAVMRVXCGR-UHFFFAOYSA-N 0.000 description 1
- NTQLADLBRQMNQJ-UHFFFAOYSA-M pyrylium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C1=CC=[O+]C=C1 NTQLADLBRQMNQJ-UHFFFAOYSA-M 0.000 description 1
- 238000001028 reflection method Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 229910001495 sodium tetrafluoroborate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- CYIFVRUOHKNECG-UHFFFAOYSA-N tridecan-2-one Chemical compound CCCCCCCCCCCC(C)=O CYIFVRUOHKNECG-UHFFFAOYSA-N 0.000 description 1
- KYWIYKKSMDLRDC-UHFFFAOYSA-N undecan-2-one Chemical compound CCCCCCCCCC(C)=O KYWIYKKSMDLRDC-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
-
- 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
- G03G5/0664—Dyes
- G03G5/0666—Dyes containing a methine or polymethine group
- G03G5/0672—Dyes containing a methine or polymethine group containing two or more methine or polymethine groups
- G03G5/0674—Dyes containing a methine or polymethine group containing two or more methine or polymethine groups containing hetero rings
Definitions
- FIG. 6 o zra 3 4 0 7 s 9 :0 2025 z 9 R LUV) mm 0 l l l l l l l I l l V l l l l l l l A l Q 4000 3200 2400 I800 I600
- sensitizers for use in an electrophotographic light-sensitive material containing an organic photoconductor.
- the sensitizers comprise derivatives of 6,6-methylenebisbenzopyrylium salts.
- the present invention relates to sensitizers for use in electrophotographic light-sensitive materials which contain organic photoconductors such as polyvinylcarbazole.
- the sensitizers of the present invention are derivatives of 6,6-methylenebisbenzopyrylium salts having the following general formula:
- Such derivatives of 6,6 methylenebisbenzopyrylium salts are used as sensitizers for an organic photoconductors such as polyvinylcarbazole or derivatives thereof. They are preferably used in an amount of 0.1 to 2.0% by weight based on the solid content, in a light-sensitive solution.
- each light-sensitive product was allowed to stand in a dark place for several days, it was negatively charged by means of conventional corona discharge of 6 kv. and exposed to white light in contact with an image Original while illuminating the surface of the light-sensitive layer at 20 lux.
- the wave length of absorption maximum was measured by reflection method for each of Compounds No. 1 to No. 15.
- Electrophotographic light-sensitive materials were obtained following the same procedures as that of Examples 1-15 except that chlorinated polyvinylcarbazole was employed as a substitute for brominated polyvinylcarbazole.
- the electrophotographic light-sensitive materials yielded an exact reproduction of original images in the same manner as that of Examples 1-15 except that the lightsensitive materials were exposed to light for 2 seconds while illuminating the surface of the light-sensitive layer at 20 lux.
- the reaction temperature of the condensation and the cyclic condensation is preferably between 0 C. and 5 C.
- reaction solution is poured into ether to crystallize.
- reaction solution is poured into a cooled solution (concentration: 5-20%) containing acid or salt having a desired anion to crystallize.
- This compound showed wave length of absorption maximum (A at 576 111,11. and molecular extinction coefficient (e) of 1016x10 in dichloroethane.
- This compound showed wave length of absorption maximum (A at 559 my and molecular extinction coefiicient (e) of 8.79X10 in dichloroethane.
- benzopyrylium salts having C10 as an anion have been shown.
- Benzopyrylium salts having BF;- or AuCl; as an anion can be obtained by using an aqueous solution of sodium tetrafluoroborate (NaBF or chloroauric acid (HAuCl instead of an aqueous solution of perchloric acid (H010).
- a sensitizer for use in an electrophotographic lightsensitive material having the formula (I):
- a rivative isj- 6;6' methvlenebisn (4Gmethoxynaphthyii '4.
- a sensitize: afbording'tofclaim'lfwheiiein rivativ'e" is 6,6 "'methy1enebis'[2 (p"-methoxystyryl)-3'- decylbenzopyryliumperchlorate a 5.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP46044739A JPS4926634B1 (enrdf_load_stackoverflow) | 1971-06-21 | 1971-06-21 | |
| JP46050171A JPS515786B1 (enrdf_load_stackoverflow) | 1971-07-07 | 1971-07-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3814752A true US3814752A (en) | 1974-06-04 |
Family
ID=26384702
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00259392A Expired - Lifetime US3814752A (en) | 1971-06-21 | 1972-06-05 | 6,6'-methylenebis(2-styryl benzopyrylium salt)as sensitizers for use in electrophotographic light-sensitive materials |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3814752A (enrdf_load_stackoverflow) |
| DE (1) | DE2230302C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2143195B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1390429A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9663477B1 (en) | 2014-09-19 | 2017-05-30 | The United States Of America As Represented By The Secretary Of The Navy | Synthesis and structure of 3,5-diamino-2,6-di-(tert-butyl-NNO-azoxy) pyrazine as a critical intermediate in the synthesis of a novel energetic compound |
-
1972
- 1972-06-05 US US00259392A patent/US3814752A/en not_active Expired - Lifetime
- 1972-06-08 GB GB2691072A patent/GB1390429A/en not_active Expired
- 1972-06-21 FR FR727222367A patent/FR2143195B1/fr not_active Expired
- 1972-06-21 DE DE2230302A patent/DE2230302C3/de not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9663477B1 (en) | 2014-09-19 | 2017-05-30 | The United States Of America As Represented By The Secretary Of The Navy | Synthesis and structure of 3,5-diamino-2,6-di-(tert-butyl-NNO-azoxy) pyrazine as a critical intermediate in the synthesis of a novel energetic compound |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1390429A (en) | 1975-04-09 |
| FR2143195B1 (enrdf_load_stackoverflow) | 1973-07-13 |
| DE2230302A1 (de) | 1972-12-28 |
| DE2230302B2 (de) | 1974-09-05 |
| DE2230302C3 (de) | 1975-05-15 |
| FR2143195A1 (enrdf_load_stackoverflow) | 1973-02-02 |
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