US3352670A - Supersensitizers for optically sensitized photoconductive layers - Google Patents
Supersensitizers for optically sensitized photoconductive layers Download PDFInfo
- Publication number
- US3352670A US3352670A US344811A US34481164A US3352670A US 3352670 A US3352670 A US 3352670A US 344811 A US344811 A US 344811A US 34481164 A US34481164 A US 34481164A US 3352670 A US3352670 A US 3352670A
- Authority
- US
- United States
- Prior art keywords
- photoconductive
- supersensitizers
- zinc oxide
- optically sensitized
- photoconductive layers
- 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
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 20
- 239000011787 zinc oxide Substances 0.000 claims description 10
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims description 5
- 239000008139 complexing agent Substances 0.000 claims description 4
- 150000002894 organic compounds Chemical class 0.000 claims description 4
- 230000006872 improvement Effects 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000975 dye Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000002877 alkyl aryl group Chemical group 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 230000035945 sensitivity Effects 0.000 description 6
- 230000001235 sensitizing effect Effects 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 150000001448 anilines Chemical class 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 206010070834 Sensitisation Diseases 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 230000008313 sensitization Effects 0.000 description 2
- -1 silver halide Chemical class 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000012546 transfer Methods 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
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- YDIYEOMDOWUDTJ-UHFFFAOYSA-N 4-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=C(C(O)=O)C=C1 YDIYEOMDOWUDTJ-UHFFFAOYSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000000498 ball milling Methods 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 239000011101 paper laminate Substances 0.000 description 1
- GVKCHTBDSMQENH-UHFFFAOYSA-L phloxine B Chemical compound [Na+].[Na+].[O-]C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 GVKCHTBDSMQENH-UHFFFAOYSA-L 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
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
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/062—Acyclic or carbocyclic compounds containing non-metal elements other than hydrogen, halogen, oxygen or nitrogen
-
- 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
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
-
- 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
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
- G03G5/0614—Amines
- G03G5/06142—Amines arylamine
-
- 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
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
- G03G5/0614—Amines
- G03G5/06142—Amines arylamine
- G03G5/06144—Amines arylamine diamine
Definitions
- R is selected from the group consisting of hydrogen, alkyl, alkaryl and aryl; and n is selected from Oand 1.
- This invention relates to the optical sensitization of photoconductive materials and to methods of increasing the effectiveness of optical sensitizing dyes in photoconductive compositions useful injmage recording.
- this'invention relates to additives which may be incorporated into photoconductive zinc oxide systems with optical sensitizers to produce a supersensitizing effect.
- Photoconductive copysheets used in electrolytic electrophotography such as those described in US. Patent'Nos. 3,010,883 and 3,010,884, are desirably sensitized to improve and extend their spectral response and efficiency.
- electrostatic printing such as described in U.S. Patent Nos. 3,052,539 and 3,052,540
- the photoconductive sheets or coatings can also be dye sensitized. Because of the desirability of obtaining a white sheet color, the concentration of sensitizing dye is nor- .mallymaintained at minimum levels consistent with im 'proved spectral response.
- supersensitization may be considered as the increase in sensitivity which is obtained by the addition of certain materials, not necessarily sensitizers per se, to a sensitized system and which is not the result of a mere additive effect.
- supersensitization may be considered to be an exception to the general rule that the admixture of sensitizing dyes tends to reduce the overall sensitivity below that level provided by the respective components used individually.
- Another object of this invention is to provide increased speed of response in a photoconductive zinc oxide copysheet without objectionable sheet coloration.
- Still another object of this invention is to provide photoconductive copysheets suitable for use in electrolytic electrophotography having increased speed and sensitivity Without substantial increase in overall dark conductivity.
- a dye sensitized photoconductive layer of a photoconductive copysheet an organic compound which is a complexing agent for zinc ion and which contains the radical form a 5 or 6 membered heterocyclic ring (e.g. morpholino, piperidino, piperazino, etc, and Y is where R is hydrogen, alkyl, alkaryl or aryl (including the substituted derivatives thereof) and n is 0 or 1.
- an organic compound which is a complexing agent for zinc ion and which contains the radical form a 5 or 6 membered heterocyclic ring (e.g. morpholino, piperidino, piperazino, etc, and Y is where R is hydrogen, alkyl, alkaryl or aryl (including the substituted derivatives thereof) and n is 0 or 1.
- N,N-dimethylaniline have essentially no supersensitizing value when used in conjunction with inorganic photoconductive materials (e.g., zinc oxide, cadmium sulfide, indium oxide, etc), particularly as compared to the highly eifective ring substituted anilines such as p-dimethylaminobenzaldehyde and p-dimethylaminobenzoic acid.
- the s-upersensitizers of this invention may generally be used in amounts ranging from about 0.000l% to about 1.5% by weight of the photoconductive material, preferably from 0.0001% to about 1.5% by weight.
- the preferred supersensitizers are not optical sensitizers per se for photoconductive zinc oxide.
- a dispersion is prepared by ball milling for several hours a mixture of 2867 grams of powdered zinc oxide (U.S.P. 12), 2821 grams of toluene, milliliters of methanol and 2026 grams of a 30 weight percent solution of styrene-butadiene copolymer (30/70 mol ratio respectively) in toluene.
- the test compound is dissolved in a suitable solvent, e.g. methanol, to make a 2 weight percent solution, and 3.1 cubic centimeters of the resulting solution is added to 200 grams of the dispersion. After thorough mixing the sample is allowed to stand at room conditions for about 24 hours.
- a 3.5 milliliter quantity of the following sensitizing dye mixture is then added 'before coating:
- optical sensitizing dyes eig. cyanines, xanthenes, merocyanines, diand tri-phenyl methanes
- cyanines, xanthenes, merocyanines, diand tri-phenyl methanes can be used, since the supersensitizers of this invention have not been paper laminate, to provide a dry coating thickness of about 0.7 mil.
- the coated substrate is then exposed with a standard light spectrogram source through a calibrated step wedge or a continuous grey wedge. and electroiytically developed in a known manner.
- a control sample in which the test compound is omitted is prepared, exposed and electrolytically developed with the same procedure and under the same conditions. Visual examination and comparison of the developed samples will indicate whether the test compound performs, a supersensitizin'g function in the photoconductive layer.
- the amount of optical dye sensitizers included in the photoconductive layer along with the organic binder and photoconductor powder can be reduced, thereby improving sheet color.
- Essentially white or otf-white copysheets are most desired in electrolytic electrophotography.
- photoconductive material of r a supersensitizer in said layer comprising a organic compound which is a complexing agent for zinc ion and which contains the radical where R and R tare selected from the group consisting of hydrogen, alkyl, alkaryl, and atoms necessary to form a heterocyclic ring having from 5 to 6 members;
- Y is a radical selected from the group consisting of where R is selected from the group consisting of hydrogen, alkyl, alkaryl and aryl; and n is selected from and 1.
- a light sensitive recording element having an optically sensitized photoconductive zinc oxide layer and being suitable for use in electrolytic electrophotography, the improvement which comprises from about 0.0001% to about 1.5% by weight of zinc oxide of a supersensitizer in said layer comprising an organic compound which is a complexing agent for zinc ion and which contains the radical Ra Y- where R and R are selected from the group consisting of hydrogen, alkyl, alkaryl, and atoms necessary to form a heterocyclic ring having from 5 to 6 members; Y is a radical selected from the group consisting of s II c.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
- Indole Compounds (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US344811A US3352670A (en) | 1964-02-14 | 1964-02-14 | Supersensitizers for optically sensitized photoconductive layers |
| GB2811/65A GB1087273A (en) | 1964-02-14 | 1965-01-21 | Electrophotography |
| DE19651497177 DE1497177A1 (de) | 1964-02-14 | 1965-02-12 | Supersensibilisiertes lichtempfindliches Wiedergabematerial |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US344811A US3352670A (en) | 1964-02-14 | 1964-02-14 | Supersensitizers for optically sensitized photoconductive layers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3352670A true US3352670A (en) | 1967-11-14 |
Family
ID=23352145
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US344811A Expired - Lifetime US3352670A (en) | 1964-02-14 | 1964-02-14 | Supersensitizers for optically sensitized photoconductive layers |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3352670A (enExample) |
| DE (1) | DE1497177A1 (enExample) |
| GB (1) | GB1087273A (enExample) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3469979A (en) * | 1965-11-26 | 1969-09-30 | Dennison Mfg Co | Electrophotographic recording element with increased speed |
| US3635706A (en) * | 1965-05-29 | 1972-01-18 | Agfa Gevaert Ag | Sensitized electrophotographic layers |
| US3844782A (en) * | 1965-10-15 | 1974-10-29 | Agfa Gevaert Ag | Heterocyclic dye sensitised electrophotographic material |
| US4043813A (en) * | 1973-06-06 | 1977-08-23 | Bell & Howell Company | Photoconductive particles of zinc oxide |
| EP0058839A1 (en) * | 1981-02-23 | 1982-09-01 | Minnesota Mining And Manufacturing Company | Sensitized organic electron donor compounds |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3197307A (en) * | 1964-09-22 | 1965-07-27 | Eastman Kodak Co | Surface modification of zinc oxide and electrophotographic member therefrom |
| US3265497A (en) * | 1961-04-29 | 1966-08-09 | Renker Belipa G M B H Fa | Electrophotographic material |
| US3271143A (en) * | 1964-01-06 | 1966-09-06 | Minnesota Mining & Mfg | Photoconductor sheet material |
| US3271144A (en) * | 1964-09-08 | 1966-09-06 | Minnesota Mining & Mfg | Supersensitized zinc oxide |
-
1964
- 1964-02-14 US US344811A patent/US3352670A/en not_active Expired - Lifetime
-
1965
- 1965-01-21 GB GB2811/65A patent/GB1087273A/en not_active Expired
- 1965-02-12 DE DE19651497177 patent/DE1497177A1/de active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3265497A (en) * | 1961-04-29 | 1966-08-09 | Renker Belipa G M B H Fa | Electrophotographic material |
| US3271143A (en) * | 1964-01-06 | 1966-09-06 | Minnesota Mining & Mfg | Photoconductor sheet material |
| US3271144A (en) * | 1964-09-08 | 1966-09-06 | Minnesota Mining & Mfg | Supersensitized zinc oxide |
| US3197307A (en) * | 1964-09-22 | 1965-07-27 | Eastman Kodak Co | Surface modification of zinc oxide and electrophotographic member therefrom |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3635706A (en) * | 1965-05-29 | 1972-01-18 | Agfa Gevaert Ag | Sensitized electrophotographic layers |
| US3844782A (en) * | 1965-10-15 | 1974-10-29 | Agfa Gevaert Ag | Heterocyclic dye sensitised electrophotographic material |
| US3469979A (en) * | 1965-11-26 | 1969-09-30 | Dennison Mfg Co | Electrophotographic recording element with increased speed |
| US4043813A (en) * | 1973-06-06 | 1977-08-23 | Bell & Howell Company | Photoconductive particles of zinc oxide |
| EP0058839A1 (en) * | 1981-02-23 | 1982-09-01 | Minnesota Mining And Manufacturing Company | Sensitized organic electron donor compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1497177A1 (de) | 1969-03-27 |
| DE1497177B2 (enExample) | 1970-01-08 |
| GB1087273A (en) | 1967-10-18 |
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