US3868251A - Organic photoconductive composition containing chlorinated paraffin - Google Patents
Organic photoconductive composition containing chlorinated paraffin Download PDFInfo
- Publication number
- US3868251A US3868251A US381746A US38174673A US3868251A US 3868251 A US3868251 A US 3868251A US 381746 A US381746 A US 381746A US 38174673 A US38174673 A US 38174673A US 3868251 A US3868251 A US 3868251A
- Authority
- US
- United States
- Prior art keywords
- chlorinated paraffin
- weight
- parts
- poly
- photoconductive composition
- 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
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- 239000012188 paraffin wax Substances 0.000 title claims abstract description 39
- 239000000203 mixture Substances 0.000 title claims abstract description 30
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 8
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000007857 hydrazones Chemical class 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims description 4
- 150000003852 triazoles Chemical class 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 206010016256 fatigue Diseases 0.000 description 22
- 239000000463 material Substances 0.000 description 14
- 230000006866 deterioration Effects 0.000 description 12
- 230000009467 reduction Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 206010034972 Photosensitivity reaction Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 230000036211 photosensitivity Effects 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- VHQGURIJMFPBKS-UHFFFAOYSA-N 2,4,7-trinitrofluoren-9-one Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C2C3=CC=C([N+](=O)[O-])C=C3C(=O)C2=C1 VHQGURIJMFPBKS-UHFFFAOYSA-N 0.000 description 1
- WDMUXYQIMRDWRC-UHFFFAOYSA-N 2-hydroxy-3,4-dinitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C([N+]([O-])=O)=C1O WDMUXYQIMRDWRC-UHFFFAOYSA-N 0.000 description 1
- QKUNKVYPGIOQNP-UHFFFAOYSA-N 4,8,11,14,17,21-hexachlorotetracosane Chemical compound CCCC(Cl)CCCC(Cl)CCC(Cl)CCC(Cl)CCC(Cl)CCCC(Cl)CCC QKUNKVYPGIOQNP-UHFFFAOYSA-N 0.000 description 1
- ODPOAESBSUKMHD-UHFFFAOYSA-L 6,7-dihydrodipyrido[1,2-b:1',2'-e]pyrazine-5,8-diium;dibromide Chemical compound [Br-].[Br-].C1=CC=[N+]2CC[N+]3=CC=CC=C3C2=C1 ODPOAESBSUKMHD-UHFFFAOYSA-L 0.000 description 1
- 241000861718 Chloris <Aves> Species 0.000 description 1
- 239000001836 Dioctyl sodium sulphosuccinate Substances 0.000 description 1
- 239000005630 Diquat Substances 0.000 description 1
- 241000156978 Erebia Species 0.000 description 1
- 239000000020 Nitrocellulose Substances 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
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 230000002265 prevention Effects 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
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Images
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
- G03G5/09—Sensitisors or activators, e.g. dyestuffs
-
- 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
- G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
Definitions
- An organic photosensitive material for use in electrophotography which consists essentially of a polymeric organic photoconductor, examples of which include poly-N-vinylcarbazole, chargetransfer molecular complexes such as poly-N- vinylcarbazole-tetrachloro-p-benzoquinone and poly- N-vinylcarbazole-tetracyanoquinodimethane, poly-N- vinylcarbazole derivatives such as nitrated poly-N- vinylcarbazole, polyvinylanthracene, and polyacenaphthylene; and monomeric organic photoconductors such -as anthracene, pyrazoline, oxazole, triazole and hydrazone.
- polymeric organic photoconductor examples of which include poly-N-vinylcarbazole, chargetransfer molecular complexes such as poly-N- vinylcarbazole-tetrachloro-p-benzoquinone and poly- N-vin
- This type of organic photosensitive material has many advantages over known inorganic photosensitive material consisting essentially of selenium or zinc oxide, etc. in easy sensitization, transparency, good film formation,high flexibility, light weight, and low manufacturing cost. Hence there is a growing interest in its practical applications.
- an object of this invention to provide an organic photoconductive composition for use in electrophotography which can always perform a pre determined function without deterioration in characteristics due to the fatigue caused when used repeatedly in an electrophotographic copying, such as a toner or a charge transfer copying and when used as a photosensitive material for a photosensitive paper.
- a photoconductive composition for use in electrophotography comprising 100 parts by weight of an organic photoconductor and to 50 parts by weight of chlori nated paraffin.
- FIGS. 1 and 2 show characteristic curves of built-up voltage vs charge time for a photosensitive plate con-' sisting of an organic photoconductor for use in electrophotography to explain the characteristics of the photoconductor.
- the organic photoconductive composition of this invention can be prepared by mixing 100 parts by weight of organic photoconductor, about 0.1 to 20 parts by weight of chemical sensitizer, about 0.02 to 4 parts by weight of optical sensitizer and 20 to 50 parts by weight of chlorinated paraffin.
- composition may be dissolved in a suitable solvent such as chlorobenzene, toluene, benzene, methylene chloride or the like and uniformly stirred to form a photosensitive material.
- a suitable solvent such as chlorobenzene, toluene, benzene, methylene chloride or the like and uniformly stirred to form a photosensitive material.
- Organic photoconductor which has been found to be suitable for the composition of the invention is, for example, poly-N-vinylcarbazole, charge-transfer molecular complexes such as poly-N-vinylcarbazoletetrachloro-p-benzoquinone or poly-N-vinylcarbazoletetracyanoquinodimethane, poly-N-vinylcarzole derivatives such as nitrated poly-N-vinylcarbazole, polyvinylanthracene, polyacenaphthylene, anthracene, pyrazoline, oxazole, triazole, or hydrazone.
- a chemical sensitizer and/or an optical sensitizer may be added to these photoconductors.
- Various kinds of additives may also be added to improve other properties of the photosensitive material.
- a suitable polymer such as polymethylmethacrylate, polycarbonate, cellulose nitrate or cellulose acetate is preferably added as a binder to provide film formation.
- chlorinated paraffin Prefered examples of chlorinated paraffin are Adekacizer-E-4l0, Adekacizer-E-450, Adekacizer-E-480, Adekacizer-E-SOO, Adekacizer-E-52O (trade names of chlorinated paraffins manufactured by Adeka-Argus Chemical Co., Ltd., containing 41 to 52% by weight of chlorine); Enpara K-45, Enpara K-SO, Enpara K-65 (trade names of chlorinated paraffins produced by Ajinomoto Kabushiki Kaisha, containing 40 to 65% by weight of chlorine); and Monocizer-W-40, Monocizer- W-45, Monocizer-W-SO (trade names of chlorinated paraffins by Dainippon Ink and Chemicals, Inc.)
- chlorinated paraffins contain about eight to 18 carbon atoms, in either liquid or solid state depending on the chlorine content. Taking into account the compatibility with the organic photoconductor, chlorinated paraffin in liquid state containing 40 to 65% by weight of chlorine is most preferred. A mixture of two or more kinds of chlorinated paraffin may also be used.
- the amounts of chlorinated paraffin to be mixed with the organic photoconductor should be within the range of 20 to parts by weight against 100 parts by weight of the organic photoconductor. This is because the addition of chlorinated paraffin not exceeding 20 parts by weight cannot prevent the occurrence of fatigue failure or deterioration, while the addition of chlorinated paraffin exceeding 50 parts by weight causes a marked reduction in photosensitivity and a considerable decrease in the built-up voltage, although the occurrence of fatigue failure or deterioration may be prevented effec tively. It has been experimentally confirmed that the addition of chlorinated paraffin exceeding the upper and lower limits were unsuitable for practical applications to photoconductors for use in electrophotography.
- the organic photoconductive composition for electrophotography obtained by mixing an organic photoconductor with a predetermined amount of chlorinated paraffin can prevent or suppress the occurrence of fatigue failure or deterioration, thus performing the desired functions in use as a photosensitive material.
- chlorinated paraffin Although the operating mechanism of chlorinated paraffin is unknown, it has been found that a photosensitive material containing an organic photoconductor as a main component will suffer in practice negligibly little fatigue failure or deterioration due to electric charge or light exposure by adding chlorinated paraffin. Even when repeatedly used as a photosensitive material for a toner or a charge transfer copying the composition of the invention can always perform a predetermined function as a photosensitive material. Even when applied to a photosensitive paper, it can obtain a clear image without causing a reduction in its image density due to room-light exposure fatigue failure or deterioration.
- EXAMPLE 1 A charge-transfer reaction was carried out between poly-N-vinylcarbazole and tetr'achloro-p-benzoquinone in a weight ratio of 121.27 to obtain a charge-transfer molecular complex.
- Adekacizer-E-4l0 was added to each part at the rate indicated in Table l with respect to 100 parts of the charge-transfer molecular complex.
- the Adekacizer-E-4l0 is a trade name of chlorinated paraffin manufactured by Adeka- Argus Chemical Co., Ltd., containing 41% by weight of chlorine.
- Each solution was coated on aluminium plate substrates to form, when the solution is dried, seven photosensitive plate samples having a film thickness ranging between 5 and 6 [.trn.
- Table 1 Amount of chlorinated Fatigue index (7:) due to FIG. 1 shows the results of measuring the electrophotographic characteristic curves of Sample 1 by a paper analyzer (rotation-speed ofa sample turntable: 13 rpm; corona charging voltage: -5,000V: light source tungsten-filament lamp; illumination: 9 lux.).
- the curves (a), (b) and (c) in FIG. 1 indicate the results obtained when light of 0, 1,000 and 4,000 lux.sec., respectively, are irradiated over the surface of the sample prior to measurement. It is clear from FIG 1 that a sample with no addition of chlorinated paraffin suffered much fatigue (deterioration in initial built-up voltage and reduction in saturation voltage).
- the fatigue index due to light exposure is defined by (1 0 val 0x 10 where V built-up voltage of a sample subjected to light exposure of 4,000 lux.sec. prior to measurement, and V built-up voltage of a sample when subjected to no previous light exposure.
- Example 2 The process of Example I was essentially repeated except that Adakacizer-E-4l0 was replaced with AdekaciZer-ESZO (trade name of chlorinated paraffin manufactured by Adeka-Argus Chemical Co., Ltd., containing 52% by weight of chlorine). Samples 8 to 14 having the compositions shown in Table 2 were thus obtained.
- the fatigue index due to light exposure is defined by 0 VRIVO) X loo EXAMPLE 3
- a mixture of 100 parts of poly-N-vinylcarbazole, parts of 2, 4, 7-trinitrofluorenone (a chemical sensitizer), and 30 parts of Enpara K-45 (trade name of chlorinated paraffin produced by Ajinomoto Kabushiki Kaisha, containing 45% by weight of chlorine) was dissolved in 1,800 parts of tetrahydrofuran to prepare a photosensitive solution.
- the surface of an aluminium plate support was coated with this solution and then dried to produce a sample of photosensitive plate.
- the fatigue indexes of the sample due to light exposure were measured as in Example 1.
- Related results were 2% in l min. and 0% in 3 min., whereas the corresponding fatigue indexes in a control experiment with no addition of chlorinated paraffin were 33% (l min.) and (3 min.).
- Example 4 The process of Example 3 was substantially repeated except that poly-N-vinylcarbazole was replaced with polyacenaphthylcne.
- the measured fatigue indexes of the sample due to light exposure were 1% 1 minute later and 2% 3 minutes later.
- a photoconductive composition for use in electrophotography comprising 100 parts by weight of an organic photoconductor and 20 to 50 parts by weight of chlorinated paraffin will suffer practically no fatigue failure or deterioration due to electric charge or light exposure. Accordingly, the composition of the invention will always display a predetermined function, even when repeatedly used as a photosensitive material in a toner or a charge transfer copying.
- a photoconductive composition for use in electrophotography comprising parts by weight of an organic photoconductor and 20 to 50 parts by weight of chlorinated paraffin wherein said chlorinated paraffin contains 40 to 65% by weight of chlorine and wherein said chlorinated paraffin contains eight to 18 carbon atoms.
- a photoconductive composition for use in electrophotography comprising 100 parts by weight of an organic photoconductor and 20 to 50 parts by weight of chlorinated paraffin wherein said chlorinated paraffin contains 40 to 65% by weight of chlorine and wherein said chlorinated paraffin contains eight to 18 carbon atoms, wherein said organic photoconductor is one member selected from the group consisting of poly-N- vinylcarbazole, charge-transfer molecular complexes. poly-N-vinylcarbazole derivatives, polyvinylanthracene, polyacenaphthylene, anthracene, pyrazoline, oxazole, triazole and hydrazone.
- the photoconductive composition according to claim 2 wherein said charge-transfer molecular complex is selected from the group consisting of poly-N- vinylcarbzaole-tetrachloro-p-benzoquinone and poly- N-vinylcarbazole-tetracyanoquinodimethane.
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP47075131A JPS4934327A (enrdf_load_stackoverflow) | 1972-07-28 | 1972-07-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3868251A true US3868251A (en) | 1975-02-25 |
Family
ID=13567320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US381746A Expired - Lifetime US3868251A (en) | 1972-07-28 | 1973-07-23 | Organic photoconductive composition containing chlorinated paraffin |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3868251A (enrdf_load_stackoverflow) |
| JP (1) | JPS4934327A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5545499A (en) * | 1995-07-07 | 1996-08-13 | Lexmark International, Inc. | Electrophotographic photoconductor having improved cycling stability and oil resistance |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5076513U (enrdf_load_stackoverflow) * | 1973-11-16 | 1975-07-03 | ||
| JPS53129013U (enrdf_load_stackoverflow) * | 1977-03-22 | 1978-10-13 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3287114A (en) * | 1961-07-24 | 1966-11-22 | Azoplate Corp | Process for the sensitization of photoconductors |
| US3533787A (en) * | 1967-07-31 | 1970-10-13 | Eastman Kodak Co | Photoconductive elements containing polymeric binders of nuclear substituted vinyl haloarylates |
| US3652269A (en) * | 1968-08-27 | 1972-03-28 | Eastman Kodak Co | Photoconductive elements containing halogenated polyethylene binders |
| US3718463A (en) * | 1971-06-22 | 1973-02-27 | Monsanto Co | Photoconductive coating compositions using a poly(vinyl-halobenzal)binder |
-
1972
- 1972-07-28 JP JP47075131A patent/JPS4934327A/ja active Pending
-
1973
- 1973-07-23 US US381746A patent/US3868251A/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3287114A (en) * | 1961-07-24 | 1966-11-22 | Azoplate Corp | Process for the sensitization of photoconductors |
| US3533787A (en) * | 1967-07-31 | 1970-10-13 | Eastman Kodak Co | Photoconductive elements containing polymeric binders of nuclear substituted vinyl haloarylates |
| US3652269A (en) * | 1968-08-27 | 1972-03-28 | Eastman Kodak Co | Photoconductive elements containing halogenated polyethylene binders |
| US3718463A (en) * | 1971-06-22 | 1973-02-27 | Monsanto Co | Photoconductive coating compositions using a poly(vinyl-halobenzal)binder |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5545499A (en) * | 1995-07-07 | 1996-08-13 | Lexmark International, Inc. | Electrophotographic photoconductor having improved cycling stability and oil resistance |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4934327A (enrdf_load_stackoverflow) | 1974-03-29 |
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