JPH0316023B2 - - Google Patents
Info
- Publication number
- JPH0316023B2 JPH0316023B2 JP59247634A JP24763484A JPH0316023B2 JP H0316023 B2 JPH0316023 B2 JP H0316023B2 JP 59247634 A JP59247634 A JP 59247634A JP 24763484 A JP24763484 A JP 24763484A JP H0316023 B2 JPH0316023 B2 JP H0316023B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- parts
- component
- fixing
- group
- 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
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- 240000005220 Bischofia javanica Species 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 8
- 239000000178 monomer Substances 0.000 claims description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 7
- 239000011230 binding agent Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000008065 acid anhydrides Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
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- URMOYRZATJTSJV-UHFFFAOYSA-N 2-(10-methylundec-1-enyl)butanedioic acid Chemical compound CC(C)CCCCCCCC=CC(C(O)=O)CC(O)=O URMOYRZATJTSJV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FPOGSOBFOIGXPR-UHFFFAOYSA-N 2-octylbutanedioic acid Chemical compound CCCCCCCCC(C(O)=O)CC(O)=O FPOGSOBFOIGXPR-UHFFFAOYSA-N 0.000 description 2
- UQGSHTCAJPRGCF-UHFFFAOYSA-N 3-hept-1-enyl-4-methylhexane-1,2,5,6-tetracarboxylic acid Chemical compound CCCCCC=CC(C(CC(O)=O)C(O)=O)C(C)C(CC(O)=O)C(O)=O UQGSHTCAJPRGCF-UHFFFAOYSA-N 0.000 description 2
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- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
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- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
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- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
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- 238000011161 development Methods 0.000 description 2
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- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 2
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- 238000010298 pulverizing process Methods 0.000 description 2
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- 229910001220 stainless steel Inorganic materials 0.000 description 2
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- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- BJQFWAQRPATHTR-UHFFFAOYSA-N 1,2-dichloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1Cl BJQFWAQRPATHTR-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
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-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
- 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
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-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
- QEDJMOONZLUIMC-UHFFFAOYSA-N 1-tert-butyl-4-ethenylbenzene Chemical compound CC(C)(C)C1=CC=C(C=C)C=C1 QEDJMOONZLUIMC-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- LIDLDSRSPKIEQI-UHFFFAOYSA-N 2-(10-methylundecyl)butanedioic acid Chemical compound CC(C)CCCCCCCCCC(C(O)=O)CC(O)=O LIDLDSRSPKIEQI-UHFFFAOYSA-N 0.000 description 1
- KHWCPXGTAVKMNS-UHFFFAOYSA-N 2-(2-methylprop-1-enyl)butanedioic acid Chemical compound CC(C)=CC(C(O)=O)CC(O)=O KHWCPXGTAVKMNS-UHFFFAOYSA-N 0.000 description 1
- PIYZBBVETVKTQT-UHFFFAOYSA-N 2-(2-methylpropyl)butanedioic acid Chemical compound CC(C)CC(C(O)=O)CC(O)=O PIYZBBVETVKTQT-UHFFFAOYSA-N 0.000 description 1
- QWPXQVDMKQUGJX-UHFFFAOYSA-N 2-(6-methylhept-1-enyl)butanedioic acid Chemical compound CC(C)CCCC=CC(C(O)=O)CC(O)=O QWPXQVDMKQUGJX-UHFFFAOYSA-N 0.000 description 1
- JTWBYEWVFCYRSF-UHFFFAOYSA-N 2-(6-methylheptyl)butanedioic acid Chemical compound CC(C)CCCCCC(C(O)=O)CC(O)=O JTWBYEWVFCYRSF-UHFFFAOYSA-N 0.000 description 1
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 description 1
- WHBAYNMEIXUTJV-UHFFFAOYSA-N 2-chloroethyl prop-2-enoate Chemical compound ClCCOC(=O)C=C WHBAYNMEIXUTJV-UHFFFAOYSA-N 0.000 description 1
- QDCPNGVVOWVKJG-UHFFFAOYSA-N 2-dodec-1-enylbutanedioic acid Chemical compound CCCCCCCCCCC=CC(C(O)=O)CC(O)=O QDCPNGVVOWVKJG-UHFFFAOYSA-N 0.000 description 1
- YLAXZGYLWOGCBF-UHFFFAOYSA-N 2-dodecylbutanedioic acid Chemical compound CCCCCCCCCCCCC(C(O)=O)CC(O)=O YLAXZGYLWOGCBF-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- YXYJVFYWCLAXHO-UHFFFAOYSA-N 2-methoxyethyl 2-methylprop-2-enoate Chemical compound COCCOC(=O)C(C)=C YXYJVFYWCLAXHO-UHFFFAOYSA-N 0.000 description 1
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- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 1
- NQSLZEHVGKWKAY-UHFFFAOYSA-N 6-methylheptyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C(C)=C NQSLZEHVGKWKAY-UHFFFAOYSA-N 0.000 description 1
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- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
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- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
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- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
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- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- G03G9/087—Binders for toner particles
- G03G9/08702—Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- G03G9/08726—Polymers of unsaturated acids or derivatives thereof
- G03G9/08733—Polymers of unsaturated polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
-
- 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
- G03G9/087—Binders for toner particles
- G03G9/08702—Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- G03G9/08706—Polymers of alkenyl-aromatic compounds
- G03G9/08708—Copolymers of styrene
- G03G9/08711—Copolymers of styrene with esters of acrylic or methacrylic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Developing Agents For Electrophotography (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
〔産業上の利用分野〕
本発明は、電子写真、静電記録、静電印刷など
における静電荷像を現像する為の現像剤組成物に
関するものである。
〔従来の技術及び問題点〕
従来電子写真法としては、米国特許第2297691
号、第2357809号明細書等に記載されている如く、
光導電性絶縁層を一様に帯電させ、次いでその層
を露光せしめ、その露光された部分上の電荷を消
散させる事によつて電気的な潜像を形成し、更に
該潜像にトナーと呼ばれる着色された電荷をもつ
た微粉末を付着せしめる事によつて可視化させ
(現像工程)、得られた可視像を転写紙等の転写材
に転写せしめた後(転写工程)、加熱、圧力或い
はその他適当な定着法によつて永久定着せしめる
(定着工程)工程からなる。
この様にトナーは単に現像工程のみならず、転
写工程、定着工程の各工程に於て要求される機能
を備えていなければならない。
一般にトナーは現像装置内で機械的動作中に受
ける剪断力、衝撃力による機械的な摩擦力を受
け、数千枚乃至数万枚コピーする間に劣化する。
この様なトナーの劣化を防ぐには機械的な摩擦力
に耐えうる分子量の大きな強靭な樹脂を用いれば
良いが、これらの樹脂は一般に軟化点が高く、非
接触定着方式であるオーブン定着、赤外線による
ラジアント定着では熱効率が悪い為に定着が充分
に行なわれず、又、接触定着方式で熱効率が良い
為、広く用いられているヒートローラー定着方式
に於ても、充分に定着させる為ヒートローラーの
温度を高くする必要が生じ、定着装置の劣化、紙
のカール、消費エネルギーの増大等の弊害を招く
ばかりでなく、この様な樹脂を使用すると微粉化
してトナーを製造する際、製造効率が著しく低下
する。その為、バインダー樹脂(結着樹脂)の重
合度、更には軟化点も余り高いものは用いる事が
できない。一方ヒートローラー定着方式は加熱ロ
ーラー表面と被定着シートのトナー像面が圧接触
する為、熱効率が著しく良く、低速から高速に至
るまで広く使用されているが、加熱ローラー面と
トナー像面が接触する際、トナーが加熱ローラー
表面に付着して後続の転写紙等に転写される、所
謂オフセツト現像が生じ易い。この現象を防止す
る為、加熱ローラー表面を弗素系樹脂等の離型性
の優れた材料で加工するが、更に加熱ローラー表
面にシリコーンオイル等の離型剤を塗布してオフ
セツト現象を完全に防止している。
しかしながら、シリコーンオイル等を塗布する
方式は、定着装置が大きくなりコスト高となるば
かりでなく複雑になる為トラブルの原因にもなり
易く好ましいものではない。
又特公昭55−6895号、特開昭56−98202号公報
に記載の如く、バインダー樹脂の分子量分布幅を
広くする事によりオフセツト現象を改良する方法
もあるが、樹脂の重合度が高くなり定着温度も高
くする必要がある。
更に改良された方法として、特公昭57−493号、
特開昭50−44836号、特開昭57−37353号公報記載
の如く、樹脂を非対称化、架橋化せしめる事によ
つてオフセツト現象を改善する方法があるが定着
点は改善されていない。
一般に、最低定着温度は冷間オフセツトと熱間
オフセツトの間にある為、使用可能温度領域は、
最低定着温度と熱間オフセツトとの間となり、最
低定着温度をできるだけ下げる事、最低熱間ホツ
トオフセツト温度をできるだけ上げる事により使
用定着温度を下げる事ができると共に使用可能温
度領域を広げる事ができ、省エネルギー化、高速
定着化、紙のカールを防ぐ事ができる。又両面コ
ピーがトラブルなくできる為複写機のインテリジ
エント化、定着装置の温度コントロールの精度、
許容幅の緩和等数々の利点がある。
その為、常に定着性、耐オフセツト性の良い樹
脂、トナーが望まれている。
一般に樹脂としてはポリエステル系樹脂とスチ
レン系樹脂とがよく用いられており、経済的には
スチレン系樹脂を用いたいところであるが、スチ
レン系樹脂は本質的に最低定着温度が高く、樹脂
組成、ワツクス類の添加による改良にも自ずと限
界があつた。
本発明はこれらの要求を満たす為になされたも
のであり、その目的はヒートローラー定着方式に
於てオフセツト防止液を塗布する事なくオフセツ
トが防止され、かつより低い定着温度で定着でき
る現像剤を提供する事にある。
本発明の他の目的は、ヒートローラー定着方式
に於てオフセツト防止剤を添加する事なくオフセ
ツトが防止され、かつより低い定着温度で定着で
きる現像剤を提供する事にある。
本発明の他の目的は、流動性が良く、ブロツキ
ングの生じないかつ寿命の長い(劣化し難い)現
像剤を提供する事にある。
本発明の他の目的は、現像剤製造時に混練性、
粉砕性の良い現像剤を提供する事にある。
〔問題点を解決するための手段〕
本発明者等は上記の目的を達成するため鋭意研
究の結果本発明に到達した。
即ち、本発明は結着樹脂と着色剤とを主成分と
する電子写真用現像剤組成物において、該結着樹
脂の主成分が、(イ)スチレン及び/もしくはスチレ
ン誘導体と、(ロ)メタクリル酸、アクリル酸および
これらのエステルから選ばれる1以上の単量体と
を重合するに際し、(ハ)炭素原子数が7〜40の2価
以上のカルボン酸を反応せしめて得られる重合体
であつて、(ロ)の成分が少なふくとも一種類の(ニ)ヒ
ドロキシル基もしくはエポキシ基を有するアクリ
ル酸もしくはメタクリル酸のエステルを(ハ)の成分
に対し等モル以上含有するものであり、且つ、(ハ)
の成分の含量が単量体全量に対して0.05〜10重量
%であることを特徴とする電子写真用現像剤組成
物に係るものである。
本発明の電子写真用現像剤組成物として、好ま
しいものは結着樹脂の高化式フローテスター軟化
点が100〜160℃、ガラス転移温度が50℃以上のも
のであり、さらに好ましいものは上記(ハ)の化合物
が下記一般式で表わされる酸又はその酸無水物又
はその低級アルキルエステルのものである。
(式中Rは炭素数3以上の側鎖を1個以上有す
る炭素数5〜30のアルキル基、アルケニル基、ア
ルキレン基又はアルケニレン基であり、nは0又
は1の整数である)
本発明において(ハ)の成分は重合前に(ロ)の成分と
反応させておいてもよいし、又、(イ)の成分と(ロ)の
成分の重合後に反応させてもよいし、重合中に反
応させてもよい。重合反応は主として一般公知の
ビニル重合が進行し、その際過酸化物又はアゾ化
合物である重合開始剤が用いられ、適宜使用する
モノマーや開始剤等にあわせて反応条件が選択さ
れる。
本発明における(イ)のスチレンもしくはスチレン
誘導体としては例えばスチレン、o−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−tert−ブチルスチレン、p−n−ヘキ
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−フエニルスチレン、p−クロルスチレ
ン、3,4−ジクロルスチレンその他を挙げるこ
とができる。
(イ)の成分の割合は実施例に例示した如く単量体
全量の75〜90重量%好ましい。
(ロ)のメタクリル酸、アクリル酸もしくはそのエ
ステルとしては、例えばアクリル酸、アクリル酸
メチル、アクリル酸エチル、アクリル酸n−プロ
ピル、アクリル酸イソプロピル、アクリル酸n−
ブチル、アクリル酸イソブチル、アクリル酸tert
−ブチル、アクリル酸アミル、アクリル酸シクロ
ヘキシル、アクリル酸n−オクチル、アクリル酸
イソオクチル、アクリル酸デシル、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、アクリル酸メトキシエチル、ア
クリル酸2−ヒドロキシエチル、アクリル酸ヒド
ロキシプロピル、アクリル酸グリシジル、アクリ
ル酸2−クロルエチル、アクリル酸フエニル、α
−クロルアクリル酸メチル、メタクリル酸、メタ
クリル酸メチル、メタクリル酸エチル、メタクリ
ル酸n−プロピル、メタクリル酸イソプロピル、
メタクリル酸n−ブチル、メタクリル酸イソブチ
ル、メタクリル酸tert−ブチル、メタクリル酸ア
ミル、メタクリル酸シクロヘキシル、メタクリル
酸n−オクチル、メタクリル酸イソオクチル、メ
タクリル酸デシル、メタクリル酸ラウリル、メタ
クリル酸2−エチルヘキシル、メタクリル酸ステ
アリル、メタクリル酸メトキシエチル、メタクリ
ル酸2−ヒドロキシエチル、メタクリル酸ヒドロ
キシプロピル、メタクリル酸グリシジル、メタク
リル酸フエニル、メタクリル酸ジメチルアミノエ
チル、メタクリル酸ジエチルアミノエチルその他
を挙げることができる。
上記(ロ)の成分中アクリル酸ヒドロキシエチル、
アクリル酸ヒドロキシプロピル、アクリル酸グリ
シジル、メタクリル酸2−ヒドロキシエチル及び
メタクリル酸グリシジルは上記(ニ)の成分であるヒ
ドロキシル基もしくはエポキシ基を有するアクリ
ル酸もしくはメタクリル酸のエステルとして上記
(ハ)の成分に対し等モル以上となる量で含有され
る。本発明に於いてはこれらの(ニ)の成分のヒドロ
キシル基又はエポキシ基に上記(ハ)の成分が反応し
てエステル結合を作り、重合反応で生成する樹脂
中に長鎖のソフトゼグメントを導入し、又エステ
ルによる分子間架橋を生成するものと推定され
る。
(ハ)の成分はマレイン酸等2価の不飽和カルボン
酸と不飽和炭化水素の反応、もしくはその後の水
素添加反応等、公知方法により容易に得られる。
(ハ)の内2価の成分としては、例えばイソブテニル
コハク酸、n−ドデセニルコハク酸、イソドデセ
ニルコハク酸、n−オクテニルコハク酸、イソオ
クテニルコハク酸、イソブチルコハク酸、n−ド
デシルコハク酸、イソドデシルコハク酸、n−オ
クチルコハク酸、イソオクチルコハク酸、及びそ
れらの酸無水物又は低級アルキルエステルその他
が挙げられる。4価の成分としては、
(1) 4−ネオペンチリデニル−1,2,6,7−
ヘプタンテトラカルボン酸
(2) 4−ネオペンチル−1,2,6,7−ヘプテ
ン(4)−テトラカルボン酸
(3) 3−メチル−4−ヘプテニル−1,2,5,
6−ヘキサンテトラカルボン酸
(4) 3−メチル−3−ヘプチル−5−メチル−
1,2,6,7−ヘプテン(4)−テトラカルボン
酸
(5) 3−ノニル−4−メチリデニル−1,2,
5,6−ヘキサンテトラカルボン酸
(6) 3−デシリデニル−1,2,5,6−ヘキサ
ンテトラカルボン酸
(7) 3−ノニル−1,2,6,7−ヘプテン(4)−
テトラカルボン酸
(8) 3−デセニル−1,2,5,6−ヘキサンテ
トラカルボン酸
(9) 3−ブチル−3−エチレニル−1,2,5,
6−ヘキサンテトラカルボン酸
(10) 3−メチル−4−ブチリデニル−1,2,
6,7−ヘプタンテトラカルボン酸
(11) 3−メチル−4−ブチル−1,2,6,7−
ヘプテン(4)−テトラカルボン酸
(12) 3−メチル−5−オクチル−1,2,6,7
−ヘプテン(4)−テトラカルボン酸
等が挙げられる。これらの化合物の構造式を以下
に示す。尚、便宜上すべて酸無水物の形で示し
た。
[Industrial Application Field] The present invention relates to a developer composition for developing electrostatic images in electrophotography, electrostatic recording, electrostatic printing, and the like. [Prior art and problems] As a conventional electrophotographic method, US Patent No. 2297691
As stated in the specification of No. 2357809, etc.
An electrical latent image is formed by uniformly charging the photoconductive insulating layer, then exposing the layer to light and dissipating the charge on the exposed portions, and then applying toner to the latent image. After the visible image is transferred to a transfer material such as transfer paper (transfer process), heat and pressure are applied. Alternatively, it consists of a step of permanently fixing (fixing step) by another suitable fixing method. As described above, the toner must have the functions required not only in the development process but also in each process such as the transfer process and the fixing process. Generally, toner is subjected to mechanical frictional force due to shearing force and impact force during mechanical operation in a developing device, and deteriorates while copying several thousand to tens of thousands of sheets.
To prevent such toner deterioration, it is best to use a strong resin with a large molecular weight that can withstand mechanical friction, but these resins generally have a high softening point and are suitable for non-contact fixing methods such as oven fixing and infrared fixing. With radiant fixing, the thermal efficiency is poor, so fixing is not sufficient.Also, with the contact fixing method, which has good thermal efficiency, even in the widely used heat roller fixing method, the temperature of the heat roller must be adjusted to ensure sufficient fixing. This not only causes problems such as deterioration of the fixing device, curling of paper, and increased energy consumption, but also causes a significant drop in production efficiency when producing toner by pulverizing such resins. do. Therefore, it is not possible to use a binder resin whose polymerization degree and even softening point are too high. On the other hand, in the heat roller fixing method, the heating roller surface and the toner image surface of the sheet to be fixed are in pressure contact, so the thermal efficiency is extremely high and it is widely used from low speeds to high speeds. When doing so, so-called offset development is likely to occur, in which the toner adheres to the surface of the heating roller and is transferred to subsequent transfer paper or the like. To prevent this phenomenon, the surface of the heating roller is treated with a material with excellent mold release properties such as fluorine-based resin, and in addition, a mold release agent such as silicone oil is applied to the surface of the heating roller to completely prevent the offset phenomenon. are doing. However, the method of applying silicone oil or the like is not preferable because it not only increases the size of the fixing device and increases the cost, but also makes it complicated, which can easily cause trouble. Furthermore, as described in Japanese Patent Publication No. 55-6895 and Japanese Patent Application Laid-Open No. 56-98202, there is a method to improve the offset phenomenon by widening the molecular weight distribution width of the binder resin, but the degree of polymerization of the resin increases and the fixation becomes difficult. The temperature also needs to be high. As a further improved method, Special Publication No. 57-493,
As described in JP-A-50-44836 and JP-A-57-37353, there is a method of improving the offset phenomenon by making the resin asymmetrical and crosslinking, but the fixing point has not been improved. Generally, the minimum fusing temperature is between cold offset and hot offset, so the usable temperature range is
It is between the minimum fixing temperature and hot offset, and by lowering the minimum fixing temperature as much as possible and raising the minimum hot offset temperature as much as possible, it is possible to lower the usable fixing temperature and expand the usable temperature range, which saves energy. , high-speed fixing, and prevents paper from curling. In addition, since double-sided copying can be performed without trouble, copying machines have become more intelligent, and the temperature control of the fixing device has become more accurate.
There are many advantages such as relaxing the tolerance range. Therefore, resins and toners with good fixing properties and offset resistance are always desired. In general, polyester resins and styrene resins are often used as resins, and it is desirable to use styrene resins economically, but styrene resins inherently have a high minimum fixing temperature, and the resin composition and wax Improvements made through the addition of compounds naturally had their limits. The present invention was made to meet these demands, and its purpose is to provide a developer that can prevent offset without applying an anti-offset liquid in a heat roller fixing system and that can fix at a lower fixing temperature. It is about providing. Another object of the present invention is to provide a developer which can prevent offset without adding an offset preventive agent in a heat roller fixing system and which can be fixed at a lower fixing temperature. Another object of the present invention is to provide a developer that has good fluidity, does not cause blocking, and has a long life (hard to deteriorate). Another object of the present invention is to improve kneading properties during developer production.
The objective is to provide a developer with good pulverizability. [Means for Solving the Problems] In order to achieve the above-mentioned object, the present inventors conducted intensive research and arrived at the present invention. That is, the present invention provides an electrophotographic developer composition containing a binder resin and a colorant as main components, wherein the main components of the binder resin are (a) styrene and/or a styrene derivative, and (b) methacrylate. When polymerizing with one or more monomers selected from acids, acrylic acid and esters thereof, (c) a polymer obtained by reacting a divalent or higher carboxylic acid having 7 to 40 carbon atoms; Component (B) contains at least one ester of acrylic acid or methacrylic acid having a small amount of (di)hydroxyl group or epoxy group in an amount equal to or more than the amount of component (C), and (c)
This relates to an electrophotographic developer composition characterized in that the content of the component is 0.05 to 10% by weight based on the total amount of monomers. The electrophotographic developer composition of the present invention is preferably one in which the binder resin has a softening point on a Koka type flow tester of 100 to 160°C and a glass transition temperature of 50°C or higher, and more preferable is one described above ( The compound c) is an acid represented by the following general formula, an acid anhydride thereof, or a lower alkyl ester thereof. (In the formula, R is an alkyl group, alkenyl group, alkylene group, or alkenylene group having 5 to 30 carbon atoms and having one or more side chains having 3 or more carbon atoms, and n is an integer of 0 or 1) In the present invention Component (C) may be reacted with component (B) before polymerization, or may be reacted after polymerization of component (A) and component (B), or during polymerization. It may be reacted. The polymerization reaction mainly proceeds by generally known vinyl polymerization, in which case a polymerization initiator such as a peroxide or an azo compound is used, and reaction conditions are appropriately selected depending on the monomers, initiator, etc. used. Examples of styrene or styrene derivatives (a) in the present invention include styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, α-methylstyrene, p-ethylstyrene,
2,4-dimethylstyrene, p-n-butylstyrene, p-tert-butylstyrene, p-n-hexylstyrene, p-n-octylstyrene, p-
n-nonylstyrene, p-n-decylstyrene,
Examples include p-n-dodecylstyrene, p-methoxystyrene, p-phenylstyrene, p-chlorostyrene, 3,4-dichlorostyrene, and others. The proportion of component (a) is preferably 75 to 90% by weight of the total amount of monomers, as exemplified in the examples. Examples of (b) methacrylic acid, acrylic acid or ester thereof include acrylic acid, methyl acrylate, ethyl acrylate, n-propyl acrylate, isopropyl acrylate, n-acrylate
Butyl, isobutyl acrylate, tert acrylate
-Butyl, amyl acrylate, cyclohexyl acrylate, n-octyl acrylate, isooctyl acrylate, decyl acrylate, lauryl acrylate, 2-ethylhexyl acrylate, stearyl acrylate, methoxyethyl acrylate, 2-hydroxyethyl acrylate , hydroxypropyl acrylate, glycidyl acrylate, 2-chloroethyl acrylate, phenyl acrylate, α
- Methyl chloroacrylate, methacrylic acid, methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, isopropyl methacrylate,
n-butyl methacrylate, isobutyl methacrylate, tert-butyl methacrylate, amyl methacrylate, cyclohexyl methacrylate, n-octyl methacrylate, isooctyl methacrylate, decyl methacrylate, lauryl methacrylate, 2-ethylhexyl methacrylate, methacrylic acid Examples include stearyl, methoxyethyl methacrylate, 2-hydroxyethyl methacrylate, hydroxypropyl methacrylate, glycidyl methacrylate, phenyl methacrylate, dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate, and others. Hydroxyethyl acrylate in the component (b) above,
Hydroxypropyl acrylate, glycidyl acrylate, 2-hydroxyethyl methacrylate, and glycidyl methacrylate are the above-mentioned esters of acrylic acid or methacrylic acid having a hydroxyl group or an epoxy group, which is the component (d) above.
It is contained in an amount equal to or more than the mole of component (c). In the present invention, the component (c) above reacts with the hydroxyl group or epoxy group of the component (d) to form an ester bond, and a long chain soft segment is created in the resin produced by the polymerization reaction. It is presumed that the esters are introduced and intermolecular crosslinks are generated by the esters. Component (iii) can be easily obtained by a known method such as a reaction between a divalent unsaturated carboxylic acid such as maleic acid and an unsaturated hydrocarbon, or a subsequent hydrogenation reaction.
Examples of the divalent component (c) include isobutenylsuccinic acid, n-dodecenylsuccinic acid, isododecenylsuccinic acid, n-octenylsuccinic acid, isooctenylsuccinic acid, isobutylsuccinic acid, n-dodecylsuccinic acid, Examples include isododecylsuccinic acid, n-octylsuccinic acid, isooctylsuccinic acid, and acid anhydrides or lower alkyl esters thereof. As tetravalent components, (1) 4-neopentylidenyl-1,2,6,7-
Heptanetetracarboxylic acid (2) 4-Neopentyl-1,2,6,7-heptene (4)-tetracarboxylic acid (3) 3-Methyl-4-heptenyl-1,2,5,
6-hexanetetracarboxylic acid (4) 3-methyl-3-heptyl-5-methyl-
1,2,6,7-heptene(4)-tetracarboxylic acid(5) 3-nonyl-4-methylidenyl-1,2,
5,6-hexanetetracarboxylic acid (6) 3-decylidenyl-1,2,5,6-hexanetetracarboxylic acid (7) 3-nonyl-1,2,6,7-heptene (4)-
Tetracarboxylic acid (8) 3-decenyl-1,2,5,6-hexanetetracarboxylic acid (9) 3-butyl-3-ethylenyl-1,2,5,
6-hexanetetracarboxylic acid (10) 3-methyl-4-butylidenyl-1,2,
6,7-heptanetetracarboxylic acid (11) 3-methyl-4-butyl-1,2,6,7-
Heptene(4)-tetracarboxylic acid(12) 3-methyl-5-octyl-1,2,6,7
-heptene(4)-tetracarboxylic acid and the like. The structural formulas of these compounds are shown below. For convenience, all are shown in the form of acid anhydrides.
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
以下に発明の実施例について述べるが、本発明
はこれらの例に限定されるものではない。尚、実
施例に示す組成割合はすべて重量部で表わすもの
である。
実施例 1
撹拌装置、窒素導入管、温度計、還流用冷却
管、及び滴下ロートを備えた反応器にキシレン
500部インドデシルコハク酸27部、及びアクリル
酸2−ヒドロキシエチル11.5部を仕込み、温度を
80℃に調節し、同温度にて窒素気流下、1時間撹
拌する。窒素気流下にてスチレン820部、アクリ
ル酸2−エチルヘキシル130部、アクリル酸2−
ヒドロキシエチル11.5部及び過酸化ベンゾイル10
部の混合液を4時間かけて滴下重合する。滴下終
了後10時間同温度にて熟成後、210℃まで徐々に
昇温させながら2mmHgまで減圧し、キシレンを
留去し溶融した樹脂をステンレススチールバツト
中へ取り出し、放冷、粉砕し粉末状の樹脂(高化
式フローテスター軟化点125.2℃、Tg60.3℃)を
得た。この軟化点は高化式フローテスター(島津
製作所製)を用いて1cm3の試料を昇温速度6℃/
分で加熱しながら、プランジヤーにより20Kg/cm3
の荷重を与え、直径1mm、長さ1mmのノズルを押
し出すようにし、これにより当該フローテスター
のプランジヤー降下量−温度曲度を描き、そのs
字曲線の高さをhとするときh/2に対応する温
度を軟化点としたものである。
該樹脂93部及びカーボンブラツク(キヤボツト
社製リーガル400R)7部をボールミルで混合後、
熱ロールを用いて混練し、冷却後ハンマーミルで
粗紛砕し、さらにジエツトミルで微粉砕し分級
後、平均粒径13.5μのトナーを得た。得られたト
ナーをキヤリアー鉄粉(日本鉄粉社製;EFV20
0/300)と混合し、ブローオフ測定機にて帯電量
を測定すると−19μc/gであつた。
該トナー91gをキヤリアー鉄粉1209gと混合し
現像剤を調製し、市販の電子写真複写機(感光体
はアモルフアスセレン、定着ローラーは直径が60
mm、回転速度は255mm/秒、定着装置中のヒート
ローラー温度を可変にしオイル塗布装置を除去し
たもの)にて画像出しを行なつたところ、地汚
れ、にじみ、黒ベタ部の抜け等のない鮮明な画像
が得られた。
定着温度を140℃〜220℃にコントロールし画像
の定着性、オフセツト性を評価したところ、145
℃にて充分に定着し、ホツトオフセツトは発生し
なかつた。5万枚まで画像出しを行なつたところ
地かぶり、黒ベタ部の抜けは認められず鮮明な画
像が得られた。
ここでの最低定着温度とは底面が15mm×7.5mm
の砂消しゴムに500gの荷重を載せ、定着機を通
して定着された画像の上を5往復こすり、こする
前後でマクベス社の反射濃度計にて光学反射密度
を測定し、以下の定義による定着率が70%を越え
る際の定着ローラーの温度をいう。
定着率=こすつた後の像濃度/こする前の像濃度
実施例 2
実施例1の反応器にキシレン500部、3−デセ
ニル−1,2,5,6−ヘキサンテトラカルボン
酸20部、及びメタクリル酸2−ヒドロキシエチル
6部を仕込み、温度を80℃に調節し、同温度にて
窒素気流下1時間撹拌する。窒素気流下にてα−
メチルスチレン890部、アクリル酸ブチル74部、
メタクリル酸2−ヒドロキシエチル10部及び過酸
化ラウロイル15部の混合液を4時間かけて滴下重
合する。滴下終了後、同温度にて10時間熟成後、
210℃まで徐々に昇温させながら2mmHgまで減圧
し、キシレンを留去し溶融した樹脂をステンレス
スチールバツト中へ取り出し、放冷、紛砕し、粉
末状樹脂(高化式フローテスター軟化点121.0℃、
Tg61.2℃)を得た。
該樹脂93部及びカーボンブラツク(キヤボツト
社製リーガル400R)7部をボールミルにて混合
後、混練、紛砕、分級し、平均粒径13.3μのトナ
ーを得た。得られたトナーの帯電量は−21μc/
gであつた。
該トナー91gをキヤリアー鉄粉1209gと混合し
現像剤を調製し実施例1と同じ評価機にて画像出
しを行なつたところ地汚れ、にじみ、黒ベタ部の
抜けのない鮮明な画像が得られた。定着装置の定
着温度をコントロールし画像の定着性、オフセツ
ト性を評価したところ150℃にて定着しホツトオ
フセツトは発生しなかつた。5万枚まで画像出し
を行なつたところ地かぶり、黒ベタ部の抜けは認
められず鮮明な画像が得られた。
実施例 3
実施例1の反応器で、キシレン500部、イソド
デセニルコハク酸30部、メタクリル酸グリシジル
15部、スチレン780部、メタクリル酸メチル35部、
アクリル酸ブチル140部及びα,α′−アゾビスジ
メチルワレロニトリル20部を用いて、実施例1と
同様の操作にて、粉末状の樹脂(高化式フローテ
スター軟化点126.4℃Tg63.1℃)を得た。
該樹脂93部及びカーボンブラツク(キヤボツト
社製リーガル400R)7部をボールミルにて混合
後、混練、粉砕、分級し、平均粒径12.9μのトナ
ーを得た。得られたトナーの帯電量−18μc/g
であつた。
該トナー91gをキヤリアー鉄粉1209gと混合
し、現像剤を調製し、実施例1と同じ評価機にて
画像出しを行なつたところ地汚れ、にじみ、黒ベ
タ部の抜けのない鮮明な画像が得られた。定着装
置の定着温度をコントロールし、画像の定着性、
オフセツト性を評価したところ、146℃にて定着
し、ホツトオフセツトは発生しなかつた。5万枚
まで画像出しを行なつたところ、地かぶり、黒ベ
タ部の抜けは認められず鮮明な画像が得られた。
実施例 4
実施例1の反応器で、キシレン500部、オクチ
ルコハク酸40部、スチレン820部、メタクリル酸
ジメチルアミノエチル20部、メタクリル酸グリシ
ジル20部、メタクリル酸ラウリル100部及びα,
α′−アゾビスイソブチロニトリル15部を用いて、
実施例1と同様の操作にて、粉末状の樹脂(高化
式フローテスター軟化点124.5℃、Tg60.5)を得
た。
該樹脂93部及びカーボンブラツク(キヤボール
社製リーガル400R)7部をボールミルにて混合
後、混練、粉砕、分級し、平均粒径13.0μのトナ
ーを得た。得られたトナーの帯電量は+20μc/
gであつた。
該トナー91gをキヤリア鉄粉1209gと混合し現
像剤を調製し、市販の電子写真複写機(感光体は
有機光導体、定着ローラーは直径が60mm、回転速
度は255mm/秒、定着装置中のヒートローラー温
度を可変にし、オイル塗布装置を除去したもの)
にて画像出しを行なつたところ、地汚れ、にじ
み、黒ベタ部の抜け等のない鮮明な画像が得られ
た。定着装置の定着温度をコントロールし、画像
の定着性、オフセツト性を評価したところ、149
℃にて定着し、ホツトオフセツトは発生しなかつ
た。5万枚まで画像出しを行なつたところ、地か
ぶり、黒ベタ部の抜けは認められず鮮明な画像が
得られた。
比較的 1
実施例1の反応器を用いて80℃、500部のキシ
レン中にスチレン830部、アクリル酸2−エチル
ヘキシル170部及び過酸化ベンゾイル15部の混合
液を4時間かけて滴下後、同温度にて10時間熟成
させた。その後実施例1の方法でキシレンを留去
し、抜出し粉砕後粉末状樹脂(高化式フローテス
ター軟化点130.5℃、Tg62.0℃)を得た。該樹脂
を用いて実施例1と全く同じ操作によりトナー
(帯電量は−18μc/gであつた)を作り、現像剤
を調製し、実施例1と同じ評価機を用て画像出し
を行なつたところ地汚れ、にじみ、黒ベタ部の抜
けのない鮮明な画像が得られた。定着装置の定着
温度を140℃〜220℃にコントロールし画像の定着
性、オフセツト性を評価したところ、175℃にて
定着したが140〜220℃まで全ての温度でオフセツ
トが発生した。
比較例 2
実施例1の反応器を用いて80℃、500部のキシ
レン中にスチレン850部、アクリル酸n−ブチル
140部、ジビニルベンゼン15部及び過酸化ラウロ
イル15部の混合液を4時間かけ滴下し、同温度に
て、10時間熟成後、実施例1の方法でキシレンを
留去し、抜出し粉砕後、粉末状樹脂(高化式フロ
ーテスター軟化点131.0℃、Tg62.2℃)を得た。
該樹脂を用いて実施例1と全く同じ操作によりト
ナー(帯電量は−18.5μc/gであつた)を作り現
像剤を調製し、実施例1と同じ評価機を用いて画
像出しを行なつたところ地汚れ、にじみ、黒ベタ
部の抜けのない鮮明な画像が得られた。定着装置
の定着温度をコントロールし、画像の定着性、オ
フセツト性を評価したところ、140℃から220℃ま
でホツトオフセツトは発生しなかつたが、定着温
度は195℃であつた。
Examples of the invention will be described below, but the invention is not limited to these examples. It should be noted that all composition ratios shown in Examples are expressed in parts by weight. Example 1 Xylene was added to a reactor equipped with a stirring device, a nitrogen inlet tube, a thermometer, a reflux condenser tube, and a dropping funnel.
500 parts of indodecyl succinic acid and 11.5 parts of 2-hydroxyethyl acrylate were charged, and the temperature was lowered.
Adjust the temperature to 80°C, and stir at the same temperature for 1 hour under a nitrogen stream. 820 parts of styrene, 130 parts of 2-ethylhexyl acrylate, 2-acrylic acid under a nitrogen stream
11.5 parts of hydroxyethyl and 10 parts of benzoyl peroxide
The mixed solution of 1 part was polymerized dropwise over 4 hours. After aging at the same temperature for 10 hours after the dropwise addition, the temperature was gradually raised to 210°C while the pressure was reduced to 2 mmHg, the xylene was distilled off, and the molten resin was taken out into a stainless steel vat, left to cool, and pulverized to form a powder. A resin (Koka flow tester softening point: 125.2°C, Tg: 60.3°C) was obtained. This softening point was determined using a 1cm3 sample using a Koka type flow tester (manufactured by Shimadzu Corporation) at a heating rate of 6℃/
20Kg/cm 3 by plunger while heating in minutes.
By applying a load of
When the height of the curve is h, the temperature corresponding to h/2 is defined as the softening point. After mixing 93 parts of the resin and 7 parts of carbon black (Regal 400R manufactured by Kabot Corporation) in a ball mill,
The mixture was kneaded using hot rolls, cooled, coarsely pulverized using a hammer mill, further finely pulverized using a jet mill, and classified to obtain a toner having an average particle size of 13.5 μm. The obtained toner was mixed with carrier iron powder (manufactured by Nippon Tetsuko Co., Ltd.; EFV20).
0/300) and measured the amount of charge using a blow-off measuring device, it was -19 μc/g. A developer was prepared by mixing 91 g of the toner with 1209 g of carrier iron powder, and a commercially available electrophotographic copying machine (the photoreceptor is amorphous selenium, the fixing roller has a diameter of 60 mm)
mm, rotation speed is 255 mm/sec, the temperature of the heat roller in the fixing device is variable and the oil application device is removed), and there was no background smearing, bleeding, or missing black solid areas. A clear image was obtained. When the fixing temperature was controlled between 140℃ and 220℃ and the image fixation and offset properties were evaluated, the result was 145.
It was sufficiently fixed at ℃, and no hot offset occurred. When images were printed up to 50,000 sheets, clear images were obtained with no background fogging or missing solid black areas. The minimum fixing temperature here is 15mm x 7.5mm on the bottom.
A load of 500 g was placed on a sand eraser, and the image fixed through the fixing machine was rubbed back and forth 5 times. The optical reflection density was measured using a Macbeth reflection densitometer before and after rubbing, and the fixing rate was determined by the following definition. This refers to the temperature of the fixing roller when it exceeds 70%. Fixing rate = Image density after rubbing / Image density before rubbing Example 2 In the reactor of Example 1, 500 parts of xylene, 20 parts of 3-decenyl-1,2,5,6-hexanetetracarboxylic acid, and 6 parts of 2-hydroxyethyl methacrylate was charged, the temperature was adjusted to 80°C, and the mixture was stirred at the same temperature for 1 hour under a nitrogen stream. α− under nitrogen flow
890 parts of methylstyrene, 74 parts of butyl acrylate,
A mixture of 10 parts of 2-hydroxyethyl methacrylate and 15 parts of lauroyl peroxide is dropwise polymerized over 4 hours. After completion of dripping, after aging at the same temperature for 10 hours,
While gradually raising the temperature to 210℃, the pressure was reduced to 2mmHg, xylene was distilled off, the molten resin was taken out into a stainless steel vat, allowed to cool, pulverized, and powdered resin (Koka flow tester softening point 121.0℃) ,
Tg61.2℃) was obtained. 93 parts of the resin and 7 parts of carbon black (Regal 400R, manufactured by Kayabot Co., Ltd.) were mixed in a ball mill, then kneaded, crushed, and classified to obtain a toner having an average particle size of 13.3 μm. The amount of charge of the obtained toner was -21μc/
It was hot at g. A developer was prepared by mixing 91 g of the toner with 1209 g of carrier iron powder, and an image was produced using the same evaluation machine as in Example 1. A clear image was obtained with no background smudges, bleeding, or missing solid black areas. Ta. When the fixing temperature of the fixing device was controlled and the image fixability and offset properties were evaluated, the image was fixed at 150° C. and no hot offset occurred. When images were printed up to 50,000 sheets, clear images were obtained with no background fogging or missing solid black areas. Example 3 In the reactor of Example 1, 500 parts of xylene, 30 parts of isododecenylsuccinic acid, and glycidyl methacrylate were added.
15 parts, 780 parts of styrene, 35 parts of methyl methacrylate,
Using 140 parts of butyl acrylate and 20 parts of α,α'-azobisdimethylvaleronitrile, a powdered resin (Koka flow tester softening point 126.4°C Tg 63.1) was prepared in the same manner as in Example 1. °C) was obtained. 93 parts of the resin and 7 parts of carbon black (Regal 400R, manufactured by Kabot Corporation) were mixed in a ball mill, then kneaded, pulverized, and classified to obtain a toner having an average particle size of 12.9 μm. Charge amount of the obtained toner - 18μc/g
It was hot. A developer was prepared by mixing 91 g of the toner with 1209 g of carrier iron powder, and an image was produced using the same evaluation machine as in Example 1. A clear image was obtained without background smearing, bleeding, or missing black solid areas. Obtained. Controls the fixing temperature of the fixing device to improve image fixability,
When the offset property was evaluated, it was fixed at 146°C and no hot offset occurred. When images were printed up to 50,000 sheets, clear images were obtained with no background fogging or missing solid black areas. Example 4 In the reactor of Example 1, 500 parts of xylene, 40 parts of octylsuccinic acid, 820 parts of styrene, 20 parts of dimethylaminoethyl methacrylate, 20 parts of glycidyl methacrylate, 100 parts of lauryl methacrylate, and α,
Using 15 parts of α′-azobisisobutyronitrile,
A powdered resin (softening point of Koka flow tester: 124.5°C, Tg: 60.5) was obtained in the same manner as in Example 1. 93 parts of the resin and 7 parts of carbon black (Regal 400R, manufactured by Kyaboru Co., Ltd.) were mixed in a ball mill, then kneaded, pulverized, and classified to obtain a toner with an average particle size of 13.0 μm. The amount of charge of the obtained toner is +20μc/
It was hot at g. A developer was prepared by mixing 91 g of the toner with 1209 g of carrier iron powder, and a commercially available electrophotographic copying machine (the photoreceptor is an organic photoconductor, the fixing roller has a diameter of 60 mm, the rotation speed is 255 mm/sec, and the heat in the fixing device) (Roller temperature variable and oil applicator removed)
When the image was produced using the following method, a clear image was obtained with no background smudges, smearing, or missing solid black areas. When we controlled the fixing temperature of the fixing device and evaluated the image fixing and offset properties, we found that the result was 149.
It was fixed at ℃ and no hot offset occurred. When images were printed up to 50,000 sheets, clear images were obtained with no background fogging or missing solid black areas. Comparatively 1 Using the reactor of Example 1, a mixture of 830 parts of styrene, 170 parts of 2-ethylhexyl acrylate, and 15 parts of benzoyl peroxide was added dropwise to 500 parts of xylene at 80°C over 4 hours, and then the same solution was added. Aged for 10 hours at temperature. Thereafter, xylene was distilled off by the method of Example 1, and a powdered resin (softening point: 130.5° C., Tg: 62.0° C. using a Koka flow tester) was obtained after extraction and pulverization. A toner (charge amount was -18 μc/g) was made using the resin in exactly the same manner as in Example 1, a developer was prepared, and an image was produced using the same evaluation machine as in Example 1. Clear images were obtained with no background smudges, smearing, or missing solid black areas. When the fixing temperature of the fixing device was controlled at 140 DEG C. to 220 DEG C. and the image fixability and offset properties were evaluated, the image was fixed at 175 DEG C., but offset occurred at all temperatures from 140 DEG C. to 220 DEG C. Comparative Example 2 Using the reactor of Example 1, 850 parts of styrene and n-butyl acrylate were mixed in 500 parts of xylene at 80°C.
A mixed solution of 140 parts of divinylbenzene, 15 parts of divinylbenzene, and 15 parts of lauroyl peroxide was added dropwise over 4 hours, and after aging at the same temperature for 10 hours, the xylene was distilled off using the method of Example 1, extracted, and pulverized to form a powder. A resin (softening point: 131.0°C, Tg: 62.2°C using Koka flow tester) was obtained.
A toner (charge amount was -18.5 μc/g) was prepared using the resin in exactly the same manner as in Example 1, a developer was prepared, and an image was produced using the same evaluation machine as in Example 1. Clear images were obtained with no background smudges, smearing, or missing solid black areas. When the fixing temperature of the fixing device was controlled and the image fixability and offset properties were evaluated, no hot offset occurred from 140°C to 220°C, but the fixing temperature was 195°C.
Claims (1)
用現像剤組成物において、該結着樹脂の主成分
が、 (イ) スチレン及び/もしくはスチレン誘導体
と、 (ロ) メタクリル酸、アクリル酸及びこれらのエ
ステルから選ばれる1以上の単量体とを重合
するに際し、 (ハ) 下記の一般式で表わされる炭素原子数が7
〜40のカルボン酸もしくはその酸無水物もし
くはその低級アルキルエステル (式中Rは炭素原子数3以上の側鎖を1個
以上有する炭素原子数5〜30のアルキル基、
アルキレン基、アルケニレン基、又はアルケ
ニル基を表わし、nは0又は1の整数であ
る) を反応せしめて得られる重合体であつて、 1) 上記(ロ)の成分中には少なくとも1種類の(ニ)
ヒドロキシル基もしくはエポキシル基を有する
アクリル酸もしくはメタクリル酸のエステルが
上記(ハ)の成分に対し等モル以上となる量で含有
され、 2) 上記(イ)の成分の含量が単量体全量に対して
75〜90重量%であり、 3) 上記(ハ)の成分の含量が単量体全量に対し
0.05〜100重量% であることを特徴とする電子写真用現像剤組成
物。 2 樹脂の高化式フローテスターによる軟化温度
が100〜160℃であり、ガラスス転移温度が50℃以
上である特許請求の範囲第1項記載の電子写真用
現像剤組成物。[Scope of Claims] 1. An electrophotographic developer composition containing a binder resin and a colorant as main components, wherein the main components of the binder resin are (a) styrene and/or a styrene derivative; ) When polymerizing with one or more monomers selected from methacrylic acid, acrylic acid and esters thereof, (c) a monomer having 7 carbon atoms represented by the following general formula;
~40 carboxylic acids or their acid anhydrides or their lower alkyl esters (In the formula, R is an alkyl group having 5 to 30 carbon atoms having one or more side chains having 3 or more carbon atoms,
(representing an alkylene group, an alkenylene group, or an alkenyl group, and n is an integer of 0 or 1), wherein 1) the component (b) above contains at least one type of ( D)
An ester of acrylic acid or methacrylic acid having a hydroxyl group or an epoxyl group is contained in an amount equal to or more than the mole of the component (c) above, and 2) the content of the component (a) above is based on the total amount of monomers. hand
75 to 90% by weight, and 3) The content of the component (c) above is based on the total amount of monomers.
An electrophotographic developer composition characterized in that the content is 0.05 to 100% by weight. 2. The electrophotographic developer composition according to claim 1, wherein the resin has a softening temperature of 100 to 160°C as measured by a Koka type flow tester and a glass transition temperature of 50°C or higher.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP59247634A JPS61124965A (en) | 1984-11-22 | 1984-11-22 | Electrophotographic developing composition |
DE8585308476T DE3570446D1 (en) | 1984-11-22 | 1985-11-21 | Resin binder for toner composition |
EP85308476A EP0186307B1 (en) | 1984-11-22 | 1985-11-21 | Resin binder for toner composition |
US07/204,953 US5154999A (en) | 1984-11-22 | 1988-06-09 | Resin binder for toner composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP59247634A JPS61124965A (en) | 1984-11-22 | 1984-11-22 | Electrophotographic developing composition |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS61124965A JPS61124965A (en) | 1986-06-12 |
JPH0316023B2 true JPH0316023B2 (en) | 1991-03-04 |
Family
ID=17166419
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP59247634A Granted JPS61124965A (en) | 1984-11-22 | 1984-11-22 | Electrophotographic developing composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS61124965A (en) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5396839A (en) * | 1977-02-04 | 1978-08-24 | Mitsui Toatsu Chemicals | Resin composition for toner for electrophotography |
JPS5512903A (en) * | 1978-07-03 | 1980-01-29 | Mitsui Toatsu Chem Inc | Toner binder for electro photography |
JPS59166965A (en) * | 1983-03-11 | 1984-09-20 | Hitachi Chem Co Ltd | Toner for developing electrostatic latent image |
-
1984
- 1984-11-22 JP JP59247634A patent/JPS61124965A/en active Granted
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5396839A (en) * | 1977-02-04 | 1978-08-24 | Mitsui Toatsu Chemicals | Resin composition for toner for electrophotography |
JPS5512903A (en) * | 1978-07-03 | 1980-01-29 | Mitsui Toatsu Chem Inc | Toner binder for electro photography |
JPS59166965A (en) * | 1983-03-11 | 1984-09-20 | Hitachi Chem Co Ltd | Toner for developing electrostatic latent image |
Also Published As
Publication number | Publication date |
---|---|
JPS61124965A (en) | 1986-06-12 |
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