JPS63301967A - Electrostatic charge image developing liquid developer - Google Patents
Electrostatic charge image developing liquid developerInfo
- Publication number
- JPS63301967A JPS63301967A JP62139300A JP13930087A JPS63301967A JP S63301967 A JPS63301967 A JP S63301967A JP 62139300 A JP62139300 A JP 62139300A JP 13930087 A JP13930087 A JP 13930087A JP S63301967 A JPS63301967 A JP S63301967A
- Authority
- JP
- Japan
- Prior art keywords
- weight
- monomers
- vinyl
- parts
- liquid developer
- 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.)
- Pending
Links
- 239000007788 liquid Substances 0.000 title claims abstract description 15
- 239000000178 monomer Substances 0.000 claims abstract description 22
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 9
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 8
- 229920000642 polymer Polymers 0.000 claims abstract description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims abstract description 3
- 239000002245 particle Substances 0.000 claims abstract description 3
- 239000003431 cross linking reagent Substances 0.000 claims description 2
- 239000011347 resin Substances 0.000 abstract description 18
- 229920005989 resin Polymers 0.000 abstract description 18
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract description 16
- -1 ethylene, propylene, vinylnaphthalene Chemical class 0.000 abstract description 12
- 229920001577 copolymer Polymers 0.000 abstract description 9
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 3
- QLLUAUADIMPKIH-UHFFFAOYSA-N 1,2-bis(ethenyl)naphthalene Chemical compound C1=CC=CC2=C(C=C)C(C=C)=CC=C21 QLLUAUADIMPKIH-UHFFFAOYSA-N 0.000 abstract description 2
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 description 9
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- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
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- LTGPFZWZZNUIIK-LURJTMIESA-N Lysol Chemical compound NCCCC[C@H](N)CO LTGPFZWZZNUIIK-LURJTMIESA-N 0.000 description 2
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- 238000004132 cross linking Methods 0.000 description 2
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- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical compound C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 2
- QBZIEGUIYWGBMY-FUZXWUMZSA-N (5Z)-5-hydroxyimino-6-oxonaphthalene-2-sulfonic acid iron Chemical compound [Fe].O\N=C1/C(=O)C=Cc2cc(ccc12)S(O)(=O)=O.O\N=C1/C(=O)C=Cc2cc(ccc12)S(O)(=O)=O.O\N=C1/C(=O)C=Cc2cc(ccc12)S(O)(=O)=O QBZIEGUIYWGBMY-FUZXWUMZSA-N 0.000 description 1
- BJQFWAQRPATHTR-UHFFFAOYSA-N 1,2-dichloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1Cl BJQFWAQRPATHTR-UHFFFAOYSA-N 0.000 description 1
- VDYWHVQKENANGY-UHFFFAOYSA-N 1,3-Butyleneglycol dimethacrylate Chemical compound CC(=C)C(=O)OC(C)CCOC(=O)C(C)=C VDYWHVQKENANGY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QOVCUELHTLHMEN-UHFFFAOYSA-N 1-butyl-4-ethenylbenzene Chemical compound CCCCC1=CC=C(C=C)C=C1 QOVCUELHTLHMEN-UHFFFAOYSA-N 0.000 description 1
- DMADTXMQLFQQII-UHFFFAOYSA-N 1-decyl-4-ethenylbenzene Chemical compound CCCCCCCCCCC1=CC=C(C=C)C=C1 DMADTXMQLFQQII-UHFFFAOYSA-N 0.000 description 1
- WJNKJKGZKFOLOJ-UHFFFAOYSA-N 1-dodecyl-4-ethenylbenzene Chemical compound CCCCCCCCCCCCC1=CC=C(C=C)C=C1 WJNKJKGZKFOLOJ-UHFFFAOYSA-N 0.000 description 1
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
- OEVVKKAVYQFQNV-UHFFFAOYSA-N 1-ethenyl-2,4-dimethylbenzene Chemical compound CC1=CC=C(C=C)C(C)=C1 OEVVKKAVYQFQNV-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- WHFHDVDXYKOSKI-UHFFFAOYSA-N 1-ethenyl-4-ethylbenzene Chemical compound CCC1=CC=C(C=C)C=C1 WHFHDVDXYKOSKI-UHFFFAOYSA-N 0.000 description 1
- LCNAQVGAHQVWIN-UHFFFAOYSA-N 1-ethenyl-4-hexylbenzene Chemical compound CCCCCCC1=CC=C(C=C)C=C1 LCNAQVGAHQVWIN-UHFFFAOYSA-N 0.000 description 1
- LUWBJDCKJAZYKZ-UHFFFAOYSA-N 1-ethenyl-4-nonylbenzene Chemical compound CCCCCCCCCC1=CC=C(C=C)C=C1 LUWBJDCKJAZYKZ-UHFFFAOYSA-N 0.000 description 1
- HLRQDIVVLOCZPH-UHFFFAOYSA-N 1-ethenyl-4-octylbenzene Chemical compound CCCCCCCCC1=CC=C(C=C)C=C1 HLRQDIVVLOCZPH-UHFFFAOYSA-N 0.000 description 1
- RCSKFKICHQAKEZ-UHFFFAOYSA-N 1-ethenylindole Chemical compound C1=CC=C2N(C=C)C=CC2=C1 RCSKFKICHQAKEZ-UHFFFAOYSA-N 0.000 description 1
- CTXUTPWZJZHRJC-UHFFFAOYSA-N 1-ethenylpyrrole Chemical compound C=CN1C=CC=C1 CTXUTPWZJZHRJC-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical class C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- OLQFXOWPTQTLDP-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCO OLQFXOWPTQTLDP-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
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- 235000010187 litholrubine BK Nutrition 0.000 description 1
- 229940107698 malachite green Drugs 0.000 description 1
- FDZZZRQASAIRJF-UHFFFAOYSA-M malachite green Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 FDZZZRQASAIRJF-UHFFFAOYSA-M 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 239000012170 montan wax Substances 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- JMXROTHPANUTOJ-UHFFFAOYSA-H naphthol green b Chemical compound [Na+].[Na+].[Na+].[Fe+3].C1=C(S([O-])(=O)=O)C=CC2=C(N=O)C([O-])=CC=C21.C1=C(S([O-])(=O)=O)C=CC2=C(N=O)C([O-])=CC=C21.C1=C(S([O-])(=O)=O)C=CC2=C(N=O)C([O-])=CC=C21 JMXROTHPANUTOJ-UHFFFAOYSA-H 0.000 description 1
- PYUYQYBDJFMFTH-WMMMYUQOSA-N naphthol red Chemical compound CCOC1=CC=CC=C1NC(=O)C(C1=O)=CC2=CC=CC=C2\C1=N\NC1=CC=C(C(N)=O)C=C1 PYUYQYBDJFMFTH-WMMMYUQOSA-N 0.000 description 1
- CTIQLGJVGNGFEW-UHFFFAOYSA-L naphthol yellow S Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C([O-])=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 CTIQLGJVGNGFEW-UHFFFAOYSA-L 0.000 description 1
- HILCQVNWWOARMT-UHFFFAOYSA-N non-1-en-3-one Chemical compound CCCCCCC(=O)C=C HILCQVNWWOARMT-UHFFFAOYSA-N 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- HDBWAWNLGGMZRQ-UHFFFAOYSA-N p-Vinylbiphenyl Chemical compound C1=CC(C=C)=CC=C1C1=CC=CC=C1 HDBWAWNLGGMZRQ-UHFFFAOYSA-N 0.000 description 1
- 235000012736 patent blue V Nutrition 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical class OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000003348 petrochemical agent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 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 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229960000834 vinyl ether Drugs 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 235000019235 yellow 2G Nutrition 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
- G03G9/13—Developers with toner particles in liquid developer mixtures characterised by polymer components
- G03G9/131—Developers with toner particles in liquid developer mixtures characterised by polymer components obtained by reactions only involving carbon-to-carbon unsaturated bonds
Abstract
Description
【発明の詳細な説明】
〔技術分野〕
本発明は、電子写真、静電記録、静電印刷等に用いられ
る液体現像剤に関する。DETAILED DESCRIPTION OF THE INVENTION [Technical Field] The present invention relates to a liquid developer used in electrophotography, electrostatic recording, electrostatic printing, etc.
トナー類の定着方式としては、電熱ヒータによる加熱雰
囲気中を通過させるオープン定着方式、少くとも一方が
加熱ロールである一対のロール間を通過させる熱ロール
定着方式、あるいは、一対の剛性ロール間を常温で通過
させる圧力定着方式等が知られている。The fixing method for toners is an open fixing method in which the toner is passed through a heated atmosphere using an electric heater, a heated roll fixing method in which the toner is passed between a pair of rolls, at least one of which is a heated roll, or a toner is passed between a pair of rigid rolls at room temperature. A pressure fixing method in which the image is passed through is known.
液体現像剤を使用した複写機は、はとんどすべてオープ
ン定着を使用していた。Almost all copiers that used liquid developers used open fixing.
これらの定着方式のうち、熱ロール定着方式は、加熱ロ
ールの表面と被定着基体上のトナー像保持面が圧接触す
るため、トナー像を被定着基体上に融着する際の熱効率
が極めて高く、迅速に定着することができるので、特に
高速度複写を目的とする画像形成装置には、極めて好適
である。Among these fixing methods, the heat roll fixing method has extremely high thermal efficiency when fusing the toner image onto the fixing substrate because the surface of the heating roll and the toner image holding surface on the fixing substrate come into pressure contact. Since it can be fixed quickly, it is particularly suitable for image forming apparatuses intended for high-speed copying.
そして、熱ロール定着方式では、加熱ロール表面にトナ
ーが加熱溶融状態で圧接触するため、トナーの一部がロ
ール表面に付着して再び被定着基体上に付着し画像を汚
す、いわゆるオフセット現象をおこし易い欠点がある。In the heat roll fixing method, the toner is heated and molten and pressure-contacted to the surface of the heat roll, which causes a so-called offset phenomenon in which a portion of the toner adheres to the roll surface and then re-adheres to the substrate to be fixed, staining the image. There are drawbacks that can easily occur.
本発明は、熱効率が高く、高速定着可能な熱ロール定着
方式を用いた時、オフセット現像を発生しない新規な液
体現像剤を提供することを目的とするものである。SUMMARY OF THE INVENTION An object of the present invention is to provide a novel liquid developer that does not cause offset development when using a hot roll fixing system that has high thermal efficiency and is capable of high-speed fixing.
一般に、液体現像剤を熱定着すると、担体液が存在する
ため、トナー粒子が相体液に溶解、膨潤するため、トナ
一層の凝集力が低下し、いわゆる″ホットオフセット′
″が生じやすい傾向にある。Generally, when a liquid developer is thermally fixed, the presence of a carrier liquid causes the toner particles to dissolve and swell in the carrier liquid, resulting in a further decrease in the cohesive force of the toner, resulting in a so-called "hot offset."
” tends to occur easily.
本発明においては、上記欠点を解決するために架橋剤単
量体を含有するビニル系単量体による重合体より成る樹
脂を使用することを特徴とする。In order to solve the above-mentioned drawbacks, the present invention is characterized by using a resin made of a polymer of vinyl monomers containing a crosslinking monomer.
本発明においてバインダー樹脂として用いる重量体を得
るためのビニル系単量体としては、例えばスチレン、０
−メチルスチレン、ｍ−メチルスチレン、ｐ−メチルス
チレン、α−メチルスチレン、Ｐ−エチルスチレン、２
，４−ジメチルスチレン、ｐ−ｎ−ブチルスチレン、ｐ
−ｔａｒｔ−ブチルスチレン、ｐ−ｎ−へキシルスチレ
ン、ｐ−ｎ−オクチルスチレン、ｐ−ｎ−ノニルスチレ
ン、ｐ−ｎ−デシルスチレン、ｐ−ｎ−ドデシルスチレ
ン、ｐ−メトキシスチレン、Ｐ−フェニルスチレン、ｐ
−クロルスチレン、３，４−ジクロルスチレン等のスチ
レン単量体を好ましいものとして挙げることができる。Examples of the vinyl monomer for obtaining the heavy body used as the binder resin in the present invention include styrene, 0
-Methylstyrene, m-methylstyrene, p-methylstyrene, α-methylstyrene, P-ethylstyrene, 2
, 4-dimethylstyrene, p-n-butylstyrene, p
-tart-butylstyrene, p-n-hexylstyrene, p-n-octylstyrene, p-n-nonylstyrene, p-n-decylstyrene, p-n-dodecylstyrene, p-methoxystyrene, P-phenyl styrene, p
Styrene monomers such as -chlorostyrene and 3,4-dichlorostyrene can be mentioned as preferred.
このほか、例えばエチレン、プロピレン、ブチレン、イ
ソブチレン等のエチレン不飽和モノオレフィン類；塩化
ビニル、塩化ビニリデン、臭化ビニル、弗化ビニル等の
ハロゲン化ビニル類；酢酸ビニル、プロピオン酸ビニル
、ベンジェ酸ビニル、酪酸ビニル等のビニルエステル類
；アクリル酸メチル、アクリル酸エチル、アクリル酸ｎ
−ブチル、アクリル酸イソブチル、アクリル酸プロピル
、アクリル酸ｎ−オクチル、アクリル酸ドデシル、アク
リル酸ラウリル、アクリル酸２−エチルヘキシル、アク
リル酸ステアリル、アクリル酸２−クロルエチル、アク
リル酸フェニル、α−クロルアクリル酸メチル、メタア
クリル酸メチル、メタアクリル酸ｎ−ブチル、メタアク
リル酸イソブチル、メタアクリル酸ｎ−オクチル、メタ
アクリル酸ドデシル、メタアクリル酸ラウリル、メタア
クリル酸２−エチルヘキシル、メタアクリル酸ステアリ
ル、メタアクリル酸フエニル、メタアクリル酸ジメチル
アミノエチル等のα−メチレン脂肪族モノカルボン酸エ
ステル類；アクリロニトリル、メタアクリロニトリル、
アクリルアミド等のアクリル酸もしくはメタアクリル酸
誘導体；ビニルメチルエーテル、ビニルエチルエーテル
、ビニルイソブチルエーテル等のビニルエーテル類；ビ
ニルメチルケトン、ビニルへキシルケトン、メチルイソ
プロペニルケトン等のビニルケトン類；Ｎ−ビニルピロ
ール、Ｎ−ビニルカルバゾール、Ｎ−ビニルインドール
、Ｎ−ビニルピロリドン等のＮ−ビニル化合物；ビニル
ナフタレン類、その他を挙げることができる。これらの
単量体は単独で或いは複数のものを組合せて用いること
ででき、又重合して共重合体を与える組合せとすること
もできる。In addition, for example, ethylenically unsaturated monoolefins such as ethylene, propylene, butylene, and isobutylene; vinyl halides such as vinyl chloride, vinylidene chloride, vinyl bromide, and vinyl fluoride; vinyl acetate, vinyl propionate, and vinyl benzoate. , vinyl esters such as vinyl butyrate; methyl acrylate, ethyl acrylate, acrylic acid n
-Butyl, isobutyl acrylate, propyl acrylate, n-octyl acrylate, dodecyl acrylate, lauryl acrylate, 2-ethylhexyl acrylate, stearyl acrylate, 2-chloroethyl acrylate, phenyl acrylate, α-chloroacrylic acid Methyl, methyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, n-octyl methacrylate, dodecyl methacrylate, lauryl methacrylate, 2-ethylhexyl methacrylate, stearyl methacrylate, methacrylate α-methylene aliphatic monocarboxylic acid esters such as phenyl acid and dimethylaminoethyl methacrylate; acrylonitrile, methacrylonitrile,
Acrylic acid or methacrylic acid derivatives such as acrylamide; Vinyl ethers such as vinyl methyl ether, vinyl ethyl ether, and vinyl isobutyl ether; Vinyl ketones such as vinyl methyl ketone, vinyl hexyl ketone, and methyl isopropenyl ketone; N-vinylpyrrole, N - N-vinyl compounds such as vinylcarbazole, N-vinylindole, N-vinylpyrrolidone; vinylnaphthalenes, and others. These monomers can be used alone or in combination, or can be polymerized to form a copolymer.
以上の如き単量体と共に用いられる架橋剤単量体は、主
に重合性の二重結合を２個以上含在する化合物であり、
例えばジビニルベンゼン、ジビニルナフタレン及びそれ
らの誘導体のような芳香族ジビニル化合物、例えばジエ
チレング＝４−
リコール、ジエチレングリコールメタアクリレート、ト
リエチレングリコールメタアクリレート、トリメチロー
ルプロパントリアクリレート、アクリルメタアクリレー
ト、ｔ−ブチルアミノエチルメタアクリレート、テトラ
メチレングリコールジメタアクリレート、１，３−ブタ
ンジオールジメタアクリレート、エチレングリコールジ
メタアクリレート、テトラメチロールメタンテトラアク
リレート等のジエチレン性カルボン酸エステル、 Ｎ、
Ｎ−ジビニルアニリン、ジビニルエーテル、ジビニルス
ルフィド、ジビニルスルホン等のすべてのジビニル化合
物、及び３種以上のビニル酸を有する化合物を単独で又
は混合して用いることができる。これら架橋剤単量体の
全単量体に対する割合は０．００５重量％以上で通常は
２０重量％以下、好ましくは０．１〜５重量％の領域内
である。この割合が０．００５重量％未満では得られる
重合体の分子量が高くならず、トナーはオフセット発生
温度の低いものとなる。The crosslinking agent monomer used together with the above monomers is a compound mainly containing two or more polymerizable double bonds,
Aromatic divinyl compounds such as divinylbenzene, divinylnaphthalene and their derivatives, such as diethylene glycol, diethylene glycol methacrylate, triethylene glycol methacrylate, trimethylolpropane triacrylate, acrylic methacrylate, t-butylaminoethyl Diethylene carboxylic acid esters such as methacrylate, tetramethylene glycol dimethacrylate, 1,3-butanediol dimethacrylate, ethylene glycol dimethacrylate, tetramethylolmethanetetraacrylate, N,
All divinyl compounds such as N-divinylaniline, divinyl ether, divinyl sulfide, and divinyl sulfone, and compounds having three or more types of vinyl acids can be used alone or in combination. The proportion of these crosslinking monomers to the total monomers is 0.005% by weight or more and usually 20% by weight or less, preferably 0.1 to 5% by weight. If this proportion is less than 0.005% by weight, the molecular weight of the obtained polymer will not be high, and the toner will have a low offset generation temperature.
この割合が大きくなると最低定着温度が上昇するように
なるが２０重量％が限界ということではなく、例えば連
鎖移動剤等を用いれば上記の割合を２０重量％より大き
くすることも可能である。As this ratio increases, the minimum fixing temperature will rise, but 20% by weight is not the limit; for example, if a chain transfer agent or the like is used, it is possible to increase the above ratio above 20% by weight.
本発明に使用できる着色材としては、プリンテックスＶ
、プリンテックスＵ、プリンテックスＧ、スペシャルブ
ラック１５、スペシャルブラック４、スペシャルブラッ
ク４−Ｂ（以上デグサ社製）、三菱＃４４、＃３０、Ｍ
Ｒ−１１、ＭＡ−１００（以上三菱化成社製）、ラー
ベン１０３５、ラーベン１２５２、ニュースペクトラ■
（以上コロンビアカーボン社製）、リーガル４００，６
００、ブラックパール９００．１１００．１３００、モ
ガールしく以上キャボット社製）などの無機顔料および
フタロシアニンブルー、フタロシアニングリーン、スカ
イブルー、ローダミンレーキ、マラカイトグリーンレー
キ、メチルバイオレットレーキ、ピーコックブルーレー
キ、ナフトールグリーンＢ、ナフトールグリーンＹ、ナ
フトールイエローＳ、ナフトールレッド、リソールファ
ーストイエロー２Ｇ、パーマネントレッド４Ｒ、ブリリ
アントファストスカーレット、ハンザイエロー、ベンジ
ジンイエロー、リソールレッド、レーキレッドＣ、レー
キレッドＤ、ブリリアントカーミン６Ｂ、パーマネント
レッドＦ５Ｒ、ビグメントスカーレット３Ｂインジゴ、
チオインジゴオイルピンクおよびボルドー１０Ｂなどの
有機顔料があげられる。As a coloring material that can be used in the present invention, Printex V
, Printex U, Printex G, Special Black 15, Special Black 4, Special Black 4-B (manufactured by Degussa), Mitsubishi #44, #30, M
R-11, MA-100 (manufactured by Mitsubishi Kasei Corporation), Raven 1035, Raven 1252, New Spectra■
(manufactured by Columbia Carbon), Regal 400,6
00, Black Pearl 900.1100.1300, Mogaru Shikori (manufactured by Cabot), and inorganic pigments such as phthalocyanine blue, phthalocyanine green, sky blue, rhodamine lake, malachite green lake, methyl violet lake, peacock blue lake, naphthol green B, Naphthol Green Y, Naphthol Yellow S, Naphthol Red, Lysol Fast Yellow 2G, Permanent Red 4R, Brilliant Fast Scarlet, Hansa Yellow, Benzidine Yellow, Lysol Red, Lake Red C, Lake Red D, Brilliant Carmine 6B, Permanent Red F5R, Gumento Scarlet 3B Indigo,
Examples include organic pigments such as Thioindigo Oil Pink and Bordeaux 10B.
以上の顔料を前記樹脂と、二本ロール、ニーダ−フラッ
シャ−などで混線、粉砕し、顔料を処理することができ
る。また、前記樹脂とともに下記の樹脂を使用しても良
い。The pigment can be treated by mixing and crushing the above pigment with the resin using a two-roll machine, a kneader flasher, or the like. Further, the following resins may be used together with the above resins.
イーストマンケミカル（Ｅａｓｔｍａｎ Ｃｈｅｍｉｃ
ａｌ）社Ｎ−１０，Ｎ−１１，Ｎ−１２，Ｎ−１４，Ｎ
−３４，Ｎ−４５，Ｃ−１０゜Ｃ−１３，Ｃ−１５，Ｃ
−１６，Ｅ−１０，Ｅ−１１，Ｅ−１２，Ｅ−１４゜Ｅ
−１５゜
三井石油化学社
１１０Ｐ、 ２２０Ｐ、 ２２０ＭＰ、 ８２０ＭＰ、
４１０ＭＰ、 ２１０ＭＰ、 ３１０ＭＰ。Eastman Chemical
al) Company N-10, N-11, N-12, N-14, N
-34, N-45, C-10°C-13, C-15, C
-16,E-10,E-11,E-12,E-14゜E
-15゜Mitsui Petrochemicals 110P, 220P, 220MP, 820MP,
410MP, 210MP, 310MP.
４０５ＭＰ、 ２００Ｐ、 ４２０２Ｅ、 ４０５３Ｅ
三洋化成社
１３１Ｐ、 １５１Ｐ、 １６１Ｐ、 １７１Ｐ、 Ｅ
３００． Ｅ２５０Ｐサゾール社
Ｈｌ、 Ｈ２，Ａｌ、 Ａ２． Ａ３． Ａ４バスフ（
ＢＡＳＦ）社
ＯＡ ＷＡＸ、 Ａ ＷＡＸ
ペトロライト（Ｐｅｔｒｏｌｉｔｅ）社バｌｚ ｍｌ
（ＢＡＲＥＣＯ）５００、バＬ／ ｍｌ （ＢＡＲＥＣ
Ｏ） ２０００゜Ｅ−７３０，Ｅ−２０１８，Ｅ−２０
２０，Ｅ−１０４０、ペトロナバ（Ｐｅｔｒｏｎａｂａ
）Ｃ、ペトロナバ（Ｐｅｔｒｏｎａｂａ）Ｃ−３６、ペ
トロナバ（Ｐｅｔｒｏｎａｂａ）Ｃ−４００，ペトロナ
バ（Ｐｅｔｒｏｎａｂａ）ヘキスト（Ｈｏｅｃｈｓｔ）
社
ＰＨ５８０，ＰＥ１３０． ＰＥＤ１２１． ＰＥＤ１
３６． ＰＥＤ１５３゜ＰＥＤ５２１． ＰＥＤ５２２
． ＰＥＤ５３４ユニオンカーバイド社
ＤＹＮＩ、 ＤＹＮＦ、 ＤＹＮＩ（、ＤＹＮＪ、 Ｄ
ＹＮＫモンサンド社
オルシン（ＯＲＵＺＯＮ）８０５．７０５．５０デュポ
ン社
アラトン（ＡＬＡＴＨＯＮ）３．１０．１２．１４．１
６．２０．２２．２３アライドケミ力ル社
ＡＣポリエチレン６、６Ａ、 ６１５
三井ポリケミ力ル社
エバフレックス１５０．２１０．２２０．２５０．２６
０゜３１０、３６０．４１０．４２０．４５０．４６０
．５５０．５６０などの合成ポリエチレン、ポリプロピ
レン及びその変成したもの、カルナバワックス、モンタ
ンワックス、キャンデリラワックス、シュガーケーンワ
ックス、オーリキュリーワックス、密蝋、木蝋、ヌカ蝋
などの天然ワックス、エステルガム、硬化ロジンなどの
天然樹脂、天然樹脂変成マレイン酸樹脂、天然樹脂変成
フェノール樹脂、天然樹脂変成ポリエステル樹脂、天然
樹脂変成ペンタエリスリトール樹脂、エポキシ樹脂など
の天然樹脂変成硬化樹脂。405MP, 200P, 4202E, 4053E
Sanyo Chemical Co., Ltd. 131P, 151P, 161P, 171P, E
300. E250P Sasol Hl, H2, Al, A2. A3. A4 bass (
BASF) company OA WAX, A WAX Petrolite company balz ml
(BARECO) 500, BAREC
O) 2000°E-730, E-2018, E-20
20, E-1040, Petronaba
) C, Petronaba C-36, Petronaba C-400, Petronaba Hoechst
Company PH580, PE130. PED121. PED1
36. PED153°PED521. PED522
．． PED534 Union Carbide DYNI, DYNF, DYNI(, DYNJ, D
YNK Monsando ORUZON 805.705.50 DuPont ALATHON 3.10.12.14.1
6.20.22.23 Allied Chemical Co., Ltd. AC polyethylene 6, 6A, 615 Mitsui Polychemical Co., Ltd. Evaflex 150.210.220.250.26
0°310, 360.410.420.450.460
．． Synthetic polyethylene such as 550.560, polypropylene and its modified products, natural waxes such as carnauba wax, montan wax, candelilla wax, sugar cane wax, auriculie wax, beeswax, wood wax, bran wax, ester gum, hardened rosin Natural resins such as natural resins, natural resins modified maleic acid resins, natural resins modified phenolic resins, natural resins modified polyester resins, natural resins modified pentaerythritol resins, epoxy resins and other natural resins modified curing resins.
本発明の分散用樹脂としては、
一般式
であられされるビニルモノマーＡと
一般式
Ｒ８
で表わされるビニル千ツマ−及びビニルピリジン、ビニ
ルピロリドン、エチレングリコールジメタクリレート、
スチレン、ジビニルベンゼン、ビニルトルエンより選ば
れるモノマーＢの各一種づつもしくは、数種の共重合体
、グラフト共重合体が使用される。The dispersing resin of the present invention includes vinyl monomer A represented by the general formula, vinyl monomer represented by the general formula R8, vinyl pyridine, vinyl pyrrolidone, ethylene glycol dimethacrylate,
Each type of monomer B selected from styrene, divinylbenzene, and vinyltoluene, or several types of copolymers and graft copolymers are used.
分散用樹脂の使用量は本発明の特徴とする樹脂成分１重
量部に対し、通常０．１〜３重量部、好ましくは０．５
〜１．５重量部の割合で使用する。The amount of the dispersing resin used is usually 0.1 to 3 parts by weight, preferably 0.5 parts by weight, per 1 part by weight of the resin component that is a feature of the present invention.
It is used in a proportion of ~1.5 parts by weight.
又、トナー組成物中に存在しうる全樹脂成分は、液体成
分１００重量部に対し、５〜１００重量部好ましくは５
〜２０重量部である。Further, the total amount of resin components that may be present in the toner composition is 5 to 100 parts by weight, preferably 5 to 100 parts by weight, based on 100 parts by weight of the liquid component.
~20 parts by weight.
担体液としては、シクロヘキサン、ｎ−ヘキサン、ｎ−
へブタン、ｎ−ノナン、ｎ−オクタン、イソオクタン、
イソドデカン、リグロイン及びそれらの混合物等の石油
系脂肪族炭化水素（市販品としてエッソスタンダード石
油社製アイソパーＥ、Ｇ、Ｈ，Ｌ、にやシェル石油社製
シェルゾール７１、ツルペッツ１５０等がある）が使用
される。As the carrier liquid, cyclohexane, n-hexane, n-
Hebutane, n-nonane, n-octane, isooctane,
Petroleum-based aliphatic hydrocarbons such as isododecane, ligroin, and mixtures thereof (commercially available products include Isopar E, G, H, and L manufactured by Esso Standard Oil Co., Ltd.; Shellsol 71 manufactured by Niya Shell Oil Co., Ltd. and Tsurupez 150, etc.) used.
これらの着色材、樹脂、担体液をボールミル、キティー
ミル、ディスクミル、ピンミル、振動ミルなどの分散機
に投入、分散、混線を行う。These coloring materials, resins, and carrier liquids are introduced into a dispersing machine such as a ball mill, Kitty mill, disk mill, pin mill, or vibration mill, and are dispersed and mixed.
製造例１
スチレンとアクリル酸ｎ−ブチルとエチレングリコール
ジメタアクリレートとの重量割合を８０：２０：１とし
た重合性組成物を２，２−アゾビス−（２，４−ジメチ
ルバレロニトリル）を開始剤として、通常の懸濁重合法
により重合せしめて得られる軟化点が１３５℃の架橋共
重合体。Production Example 1 A polymerizable composition containing styrene, n-butyl acrylate, and ethylene glycol dimethacrylate in a weight ratio of 80:20:1 was prepared from 2,2-azobis-(2,4-dimethylvaleronitrile). As an agent, a crosslinked copolymer having a softening point of 135° C. is obtained by polymerization using a normal suspension polymerization method.
製造例２
スチレンとアクリル酸ｎ−ブチルとエチレングリコール
ジメタアクリレートとを８５ ： １５ ：０．５の重
量割合で含有する重合性組成物を２，２−アゾビス−（
２，４−ジメチルバレロニトリル）を開始剤として、通
常の懸濁重合法により重合せしめて得られる軟化点が１
３４℃の架橋共重合体。Production Example 2 A polymerizable composition containing styrene, n-butyl acrylate, and ethylene glycol dimethacrylate in a weight ratio of 85:15:0.5 was prepared using 2,2-azobis-(
2,4-dimethylvaleronitrile) as an initiator and a softening point of 1.
Crosslinked copolymer at 34°C.
製造例３
スチレンとアクリル酸ｎ−ブチルとエチレングリコール
ジメタアクリレートとα−メチルスチレンとの重量割合
を８０：２０：５ニアとした重合性組成物を製造例１の
樹脂と同様にして得られる軟化点が１４０℃の架橋共重
合体。Production Example 3 A polymerizable composition containing styrene, n-butyl acrylate, ethylene glycol dimethacrylate, and α-methylstyrene in a weight ratio of 80:20:5 is obtained in the same manner as the resin of Production Example 1. A crosslinked copolymer with a softening point of 140°C.
製造例４
スチレンとアクリル酸ｎ−ブチルとトリメチロールプロ
パントリアクリレートを８０ ： ２０ ：０．５の重
量割合で含有する重合性組成物を２，２−アゾビス−（
２，４−ジメチルバレロニトリル）を開始剤として、通
常の懸濁重合法により重合せしめて得られる軟化点が１
３８℃の架橋共重合体。Production Example 4 2,2-Azobis-(
2,4-dimethylvaleronitrile) as an initiator and a softening point of 1.
Crosslinked copolymer at 38°C.
１２一
実施例１
製造例１の樹脂 ７０重量部Ｐ
ｒ１ｎｔｅｘ （デグサ社カーボンブラック）３０重
量部を二本ロールで混線後粉砕した。121 Example 1 Resin of Production Example 1 70 parts by weight P
30 parts by weight of r1ntex (carbon black manufactured by Degussa) was mixed with two rolls and then ground.
前記粉砕物 ５０重量部ア
イソパーＨ（ＥＸＸＳＯＮ社）２００重量部をボールミ
ルに入れ２４時間分散後、さらにアイソパーＨを３００
重量部加え、１時間分散し、これを濃縮トナーとした。50 parts by weight of the pulverized product 200 parts by weight of Isopar H (EXXSON) were placed in a ball mill and dispersed for 24 hours, and then 300 parts by weight of Isopar H was added.
Parts by weight were added and dispersed for 1 hour to obtain a concentrated toner.
これを２００ｇとりアイソパーＨ１Ωに希釈、現像剤と
した。200 g of this was diluted to Isopar H1Ω and used as a developer.
実施例２
製造例２の樹脂 ５７重量部２５０ｐ
（三洋化成ポリエチレン） ８重量部ＭＡ６０（三
菱化成カーボンブラック）３５重量部をフラッシャ−で
混練後粉砕した。Example 2 Resin of Production Example 2 57 parts by weight 250p
(Sanyo Kasei Polyethylene) 8 parts by weight MA60 (Mitsubishi Kasei Carbon Black) 35 parts by weight were kneaded in a flasher and then pulverized.
前記粉砕物 ６０重量部共
重合体アイソパーＨ１０％溶液 ２００重量部ア
イソパーＨ１００重量部
以下実施例１と同様に実施した。The above pulverized product: 60 parts by weight 10% solution of copolymer Isopar H: 200 parts by weight Below 100 parts by weight Isopar H The same procedure as in Example 1 was carried out.
実施例３
製造例３の樹脂 ６０重量部ＡＣ４０
０Ａ（アライドケミカル社）１０重量部リーガル４００
（キャボット社）３０重量部をフラッシャ−で混練粉砕
した。以下実施例１と同様に実施した。Example 3 Resin of Production Example 3 60 parts by weight AC40
0A (Allied Chemical Company) 10 parts by weight Regal 400
(Cabot) 30 parts by weight were kneaded and pulverized using a flasher. The following steps were carried out in the same manner as in Example 1.
比較例
スチレンとアクリル酸ｎ−ブチル共重合体５０重量部Ｐ
ＲＩＮＴＥＸ Ｖ ４０
重量部をフラッシャ−で混練粉砕した後、実施例１に同
じリコー製ＣＴ５０８５で定着ヒーターｏｆｆで画像を
出した後、定着試験機で非オフセット領域を調べた。結
果を下表に示す。Comparative Example Styrene and n-butyl acrylate copolymer 50 parts by weight P
RINTEX V 40
After kneading and pulverizing parts by weight using a flasher, an image was produced using the same Ricoh CT5085 as used in Example 1 with the fixing heater turned off, and non-offset areas were examined using a fixing tester. The results are shown in the table below.
以上の結果より明らかなとおり、本発明によりオフセッ
ト現象を示さない熱ローラ定着可能な広範囲の温度中が
得られ、熱ローラ定着が可能であることがわかる。As is clear from the above results, according to the present invention, it is possible to obtain a wide range of temperatures in which hot roller fixing is possible without an offset phenomenon, and it is understood that hot roller fixing is possible.
本発明現像剤によりオフセット現象が生ずることなく熱
ローラ定着が可能となり、高速定着が容易となった。The developer of the present invention enables hot roller fixing without causing an offset phenomenon, and facilitates high-speed fixing.
又、本発明の液体現像剤はフラッシュ定着法によっても
、ニジミ等のないシャープネスの高い定着を行ない得る
ものである。Further, the liquid developer of the present invention can also be used to perform fixing with high sharpness without bleeding or the like even by a flash fixing method.
Claims (1)
子を分散してなる静電写真用液体現像剤において、全単
量体に対して０．００５重量％以上の架橋剤単量体を含
有するビニル系単量体による重合体を含有することを特
徴とする静電写真用液体現像剤。1. In an electrostatographic liquid developer in which toner particles are dispersed in a carrier liquid containing an aliphatic hydrocarbon as a main component, 0.005% by weight or more of a crosslinking agent monomer based on the total monomers. 1. A liquid developer for electrostatic photography, comprising a polymer made of a vinyl monomer containing:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62139300A JPS63301967A (en) | 1987-06-02 | 1987-06-02 | Electrostatic charge image developing liquid developer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62139300A JPS63301967A (en) | 1987-06-02 | 1987-06-02 | Electrostatic charge image developing liquid developer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63301967A true JPS63301967A (en) | 1988-12-08 |
Family
ID=15242072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62139300A Pending JPS63301967A (en) | 1987-06-02 | 1987-06-02 | Electrostatic charge image developing liquid developer |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63301967A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0695974A1 (en) | 1994-07-18 | 1996-02-07 | Nippon Paint Company Limited | Liquid developer and method of preparing the same |
| EP0965891A2 (en) * | 1998-06-18 | 1999-12-22 | Canon Kabushiki Kaisha | Image forming method |
| US6692881B2 (en) | 2001-05-30 | 2004-02-17 | Ricoh Company Limited | Recording liquid and image forming method using the recording liquid |
-
1987
- 1987-06-02 JP JP62139300A patent/JPS63301967A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0695974A1 (en) | 1994-07-18 | 1996-02-07 | Nippon Paint Company Limited | Liquid developer and method of preparing the same |
| EP0965891A2 (en) * | 1998-06-18 | 1999-12-22 | Canon Kabushiki Kaisha | Image forming method |
| EP0965891A3 (en) * | 1998-06-18 | 2000-12-06 | Canon Kabushiki Kaisha | Image forming method |
| US6692881B2 (en) | 2001-05-30 | 2004-02-17 | Ricoh Company Limited | Recording liquid and image forming method using the recording liquid |
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