US3597368A - Liquid developer for electrophotography containing yellow pigment - Google Patents
Liquid developer for electrophotography containing yellow pigment Download PDFInfo
- Publication number
- US3597368A US3597368A US751703A US3597368DA US3597368A US 3597368 A US3597368 A US 3597368A US 751703 A US751703 A US 751703A US 3597368D A US3597368D A US 3597368DA US 3597368 A US3597368 A US 3597368A
- Authority
- US
- United States
- Prior art keywords
- developer
- liquid
- liquid developer
- image
- yellow pigment
- 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
- 239000007788 liquid Substances 0.000 title abstract description 30
- 239000001052 yellow pigment Substances 0.000 title description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical class CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 abstract 1
- 239000000049 pigment Substances 0.000 description 7
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- -1 acetoacetic acid ester Chemical class 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- OSNILPMOSNGHLC-UHFFFAOYSA-N 1-[4-methoxy-3-(piperidin-1-ylmethyl)phenyl]ethanone Chemical compound COC1=CC=C(C(C)=O)C=C1CN1CCCCC1 OSNILPMOSNGHLC-UHFFFAOYSA-N 0.000 description 4
- 239000010419 fine particle Substances 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- 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
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
- 238000000576 coating method Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- MOUPNEIJQCETIW-UHFFFAOYSA-N lead chromate Chemical compound [Pb+2].[O-][Cr]([O-])(=O)=O MOUPNEIJQCETIW-UHFFFAOYSA-N 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 239000000126 substance Substances 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
- HBKBEZURJSNABK-MWJPAGEPSA-N 2,3-dihydroxypropyl (1r,4ar,4br,10ar)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylate Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(=O)OCC(O)CO HBKBEZURJSNABK-MWJPAGEPSA-N 0.000 description 1
- XWTGEDNUGUMEPF-UHFFFAOYSA-N 5,5-dichlorocyclohexa-1,3-diene Chemical compound ClC1(Cl)CC=CC=C1 XWTGEDNUGUMEPF-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/12—Developers with toner particles in liquid developer mixtures
- G03G9/122—Developers with toner particles in liquid developer mixtures characterised by the colouring agents
Definitions
- a liquid developer for developing a latent electrostatic image containing at least one of the following:
- the present invention relates to a liquid developer for the development of a latent electrostatic image and, in particular, to a liquid developer containing yellow pigment which is positivel charged and which is especially suited for the reproduction of a multicolor image.
- a liquid developer generally comprises fine charged particles of a single polarity, which are suspended in a carrier liquid having high degree of electrical insulating properties.
- the most important requirement for a liquid developer is that for the amount and polarity of the charges on the fine particles that the liquid developer remain stable over a long period of storage.
- benzidine yellow G (CI. 21095) represented by the following formula shows an unstable charge retention which can be charged negatively when dispersed in an insulative liquid Also, even if resinous coatings which are conventionally known as a means for charge control of dispersed particles is applied, the tendency to negative charging still appears when the particles are stored over an extended period.
- benzidine yellow GR (CI. 21100) prepared by introducing CH radicals into the p-position of a benzene nuclei at the opposite ends of the above formula shows an improved property in respect of the charge condition, but has an undesirable hue due to increased absorption in the green region of spectrum.
- Hansa Yellow another conventional dye, lacks transparency and where it is desired to obtain a multicolor image by over print development as described above, the underlying color is apt to be concealed.
- the conventional dye lead chromate has the defect that it is apt to be charged negatively and also lacks transparency.
- R represents a OCH OC H or a OC H radical.
- the pigment according to the present invention has several prominent features over the conventional yellow pigments in that it has almost ideal absorption characteristics. Its dispersion in many insulative liquids is easy and stable and its electrophoretic properties therein are stable. Similarly, satisfactory results can also be obtained even if resins, or oils were mixed in liquids to facilitate dispersion and to regulate the electrophoretic characteristics. Especially, when the above compounds are employed, it is simple to obtain extremely fine particles which can produce a developed image of excellent transparency so that when a yellow image comprising this pigment is superimposed on top of the images already developed, for instance, by means of cyan and magenta developers, complete mixing of color is realized Without concealing the underlying colors.
- the compound having a structure represented by the general Formula 1 or 2, for instance, in the case Where R is OCH can be obtained by the coupling of a tetrazotized product of 3,3-dichlorobenzene with O-anisidine acetoacetic acid which, in turn is synthesized from O-anisidine and acetoacetic acid ester.
- the pigments according to the present invention have an intense tendency of acquiring charges of positive polarity and therefore, even if they were mixed, for instance, with a small quantity of another pigment having a similar structure and possessing an ambiguous charging characteristic, the developing characteristics will remain stable.
- Mixtures of the pigments developed by the present in- I vention can, of course, be used as toners for liquid developers by being dispersed into an insulating liquid.
- the toner showed stable electrophoretic properties.
- resins applicable for the preparation of liquid developers one can enumerate rosin-modified phenol formaldehyde resin, pentaerythritol ester of rosin, glycerin ester of hydrogenated rosin, ethylcellulose, various alkyd resins, polyacrylic or polymethacrylic resin, polystyrene, polyketone resin and polyvinyl acetate, etc.
- the carrier liquid of the liquid developer aliphatic or alicyclic hydrocarbons such as cyclohexane, kerosene etc. and halogen-substituted saturated hydrocarbons, especially hydrocarbons containing fluorine are applicable.
- a trace of dispersing agents, surface active agents or vegetable oils can also be incorporated into the liquid developer.
- the present invention relates to a novel developer providing a yellow image, whereby the positive charges are stably maintained. Therefore, if it is applied to an electrically negative latent electrostatic image, the attractive deposition under the action of Coulombs forces takes place. When applied to an electrically positive latent image, repulsion development occurs.
- the developer of the present invention has one advantage that it can provide an especially excellent image in transparencies and therefore, when obtaining a multicolor image, it demonstrates excellent color reproducibility.
- the yellow pigment being transparent, did not cause a trailing tendency in and around the developed image and also produced very little interference background.
- a liquid developer for developing a latent electrostatic image containing fine particles comprising at'least 0;16 of the compounds selected from the group consisting o H ll wherein R is selected from the group consisting of OCH OC H and OC H as the main constituent thereof, which is positively charged and which is suspended in an electrically insulative liquid selected from the group consist: ing of aliphatic hydrocarbons, alicyclic hydrocarbons and halogen-substituted saturated hydrocarbons.
- R is References Cited OC H 5.
- R is UNITED STATES PATENTS OC H 3,361,736 1/1968 Rlbba 260-176 6.
- said 5 3,105,321 10/1963 Johllsoll 252-421 electrically insulative liquid is an aliphatic hydrocarbon. 3,053,688 9/1962 'Grelg 7.
- said 2,361,569 10/ 1944 Reynolds 260-476 insulative liquid is an alicyclic hydrocarbon.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Liquid Developers In Electrophotography (AREA)
- Developing Agents For Electrophotography (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5160067 | 1967-08-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3597368A true US3597368A (en) | 1971-08-03 |
Family
ID=12891381
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US751703A Expired - Lifetime US3597368A (en) | 1967-08-11 | 1968-08-12 | Liquid developer for electrophotography containing yellow pigment |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3597368A (en:Method) |
| BE (1) | BE719289A (en:Method) |
| FR (1) | FR1578390A (en:Method) |
| GB (1) | GB1201134A (en:Method) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3998747A (en) * | 1973-10-02 | 1976-12-21 | Canon Kabushiki Kaisha | Color toner for electrophotography |
-
1968
- 1968-08-09 GB GB38291/68A patent/GB1201134A/en not_active Expired
- 1968-08-09 BE BE719289D patent/BE719289A/xx unknown
- 1968-08-12 FR FR1578390D patent/FR1578390A/fr not_active Expired
- 1968-08-12 US US751703A patent/US3597368A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3998747A (en) * | 1973-10-02 | 1976-12-21 | Canon Kabushiki Kaisha | Color toner for electrophotography |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1797059B2 (de) | 1976-01-08 |
| GB1201134A (en) | 1970-08-05 |
| BE719289A (en:Method) | 1969-01-16 |
| DE1797059A1 (de) | 1970-12-10 |
| FR1578390A (en:Method) | 1969-08-14 |
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