JP4956549B2 - トナー用樹脂組成物および該樹脂組成物を用いたトナー - Google Patents
トナー用樹脂組成物および該樹脂組成物を用いたトナー Download PDFInfo
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- JP4956549B2 JP4956549B2 JP2008546868A JP2008546868A JP4956549B2 JP 4956549 B2 JP4956549 B2 JP 4956549B2 JP 2008546868 A JP2008546868 A JP 2008546868A JP 2008546868 A JP2008546868 A JP 2008546868A JP 4956549 B2 JP4956549 B2 JP 4956549B2
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- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
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- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-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
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 229940051201 quinoline yellow Drugs 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 235000012752 quinoline yellow Nutrition 0.000 description 1
- 239000004172 quinoline yellow Substances 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 230000035484 reaction time Effects 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
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- 238000003860 storage Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
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- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
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- 230000000007 visual effect Effects 0.000 description 1
- XOSXWYQMOYSSKB-LDKJGXKFSA-L water blue Chemical compound CC1=CC(/C(\C(C=C2)=CC=C2NC(C=C2)=CC=C2S([O-])(=O)=O)=C(\C=C2)/C=C/C\2=N\C(C=C2)=CC=C2S([O-])(=O)=O)=CC(S(O)(=O)=O)=C1N.[Na+].[Na+] XOSXWYQMOYSSKB-LDKJGXKFSA-L 0.000 description 1
Classifications
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- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
- C08G18/6225—Polymers of esters of acrylic or methacrylic acid
- C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
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- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7621—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y10S525/91—Polymer from ethylenic monomers only, having terminal unsaturation
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
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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)
- Manufacturing & Machinery (AREA)
- Engineering & Computer Science (AREA)
- Developing Agents For Electrophotography (AREA)
- Polyurethanes Or Polyureas (AREA)
Description
すなわち、本発明は、活性水素基を含有し、ピーク分子量(Mp)が3万以上、200万以下であるスチレン系重合体(A)と、カルボキシル基を含有し、ピーク分子量(Mp)が2,000以上、2万以下であるスチレン系重合体(B)と、イソシアネート基を有する架橋性化合物(C)とを反応させて得られる樹脂(D)を含むトナー用樹脂組成物に関するものである。
また、本発明は、前記(A)中の活性水素基数と前記(C)中のイソシアネート基数の比が、2:1〜10:1である、トナー用樹脂組成物に関するものである。
さらに、本発明は、前記(A)中の活性水素基が水酸基である、トナー用樹脂組成物に関するものである。
また、本発明は、フローテスターによる1/2流出温度(Tm)が115℃以上135℃以下である、トナー用樹脂組成物に関するものである。
さらに、本発明は、前記(A)中の活性水素基数が、前記(A)100g当たり0.01モル以上0.2モル以下である、トナー用樹脂組成物に関するものである。
また、本発明は、前記(B)のガラス転移温度(Tg)が40℃以上75℃以下である、トナー用樹脂組成物に関するものである。
さらに、本発明は、ゲル分率が0.1質量%以上3.0質量%以下である、トナー用樹脂組成物に関するものである。
また、本発明は、前記樹脂(D)が、前記(A)と前記(B)との混合物を含む液体に前記(C)を添加して、反応させることにより得られたものである、トナー用樹脂組成物に関するものである。
さらに、本発明は、天然ワックスまたは融点60℃以上145℃以下のポリオレフィンワックスの少なくとも一つを含み、前記ワックスを前記樹脂(D)に対して0.1質量%以上10質量%以下で含む、トナー用樹脂組成物に関するものである。
さらに、本発明は、本発明のトナー用樹脂組成物と少なくとも着色剤とを含むトナーに関するものである。
更に、前記の各種ポリイソシアネート類をビウレット変性、アロファネート変性、イソシアヌレート変性、ウレタン変性などの種々の変性を行った変性ポリイソシアネート類も使用することが可能である。中でも芳香族ジイソシアネートは反応性に富み、また安価であるので、最も好適に使用し得るポリイソシアネートの1つである。
活性水素基の数が上記範囲内である場合、適切な量のゲル分が得られ、さらに定着性と耐オフセット性のバランスに優れたものとすることができる。
また、上記範囲内で高分子量および低分子量のスチレン系重合体を併用することにより、互いの特性を損なうことなく、耐オフセット性および定着性のバランスに優れたトナー用樹脂組成物を得ることができる。
上記ポリオレフィンワックスに相当するものの具体的商品名としては、三井化学社製ハイワックス800P、400P、200P、100P、720P、420P、320P、405MP、320MP、4051E、2203A、1140H、NL800、NP055、NP105、NP505、NP805等を例示することができるが、これに限定されるものではない。
検出器; SHODEX RI−71S型屈折率測定装置(昭和電工製)
溶剤; テトラヒドロフラン
カラム; KF−G 1本、KF−807L 3本、KF800D 1本を直列に連結。
(カラムは何れも昭和電工製)
流速; 1.0 ml/分
試料; 0.25質量%THF溶液
なお、測定の信憑性は上記の測定条件で行ったNBS706ポリスチレン試料(Mw=288,000、Mn=137,000、Mw/Mn=2.11)のMw/Mnが、2.11±0.10となることにより確認し得る。
樹脂(A)と樹脂(B)とを合わせて60gをバッチ・ニーダー(ラボプラストミル;東洋精機製作所製)に供給し175℃*150回転数で混練する。更に架橋剤(C)を注入してニーダーのトルクを測定する。架橋剤を注入してからトルクが平衡するまでの時間を反応速度とする。
上記反応速度をもとに、下記の規定で生産性を評価した。
◎: 反応速度≦90秒
○: 90秒<反応速度≦240秒
△: 240秒<反応速度≦300秒
×: 300秒<反応速度
市販の電子写真複写機を改造した複写機にて未定着画像を作成した。その後、この未定着画像を市販の複写機の定着部を改造した熱ローラー定着装置を用いて定着させた。熱ロールの定着速度は200mm/secとし、熱ローラーの温度を5℃ずつ変化させてトナーの定着を行った。得られた定着画像を砂消しゴム(トンボ鉛筆社製)により、0.5kgfの荷重をかけ、10回摩擦させ、この摩擦試験前後の画像濃度をマクベス式反射濃度計により測定した。各温度での画像濃度の変化率が60%以上となった最低の定着温度をもって最低定着温度とした。この最低定着温度を基に、下記の規定で定着性を評価した。なお、ここに用いた熱ローラー定着装置はシリコーンオイル供給機構を有しないものである。また、環境条件は、常温常圧(温度22℃、相対湿度55%)とした。
○: 最低定着温度≦135℃
△: 135℃<最低定着温度≦150℃
×: 150℃<最低定着温度
耐オフセット性の評価は、上記最低定着温度の測定に準じて行った。すなわち、上記複写機にて未定着画像を作成した後、トナー像を転写して上述の熱ローラー定着装置により定着処理を行い、次いで白紙の転写紙を同様の条件下で当該熱ローラー定着装置に送って転写紙上にトナー汚れが生ずるか否かを目視観察する操作を行った。この際、前記熱ローラー定着装置の熱ローラーの設定温度を順次上昇させた状態で目視観察を繰り返し、トナーによる汚れの生じた最低の設定温度をもってオフセット発生温度とした。このオフセット発生温度をもとに、下記の規定で耐オフセット性を評価した。また、環境条件は、常温常圧(温度22℃、相対湿度55%)とした。
(コールドオフセット評価)
○: コールドオフセット発生温度≦135℃
△: 135℃<コールドオフセット発生温度≦149℃
×: 149℃<コールドオフセット発生温度、または全温度オフセット発生
(ホットオフセット評価)
○: ホットオフセット発生温度≦220℃/190mm/s、またはオフセットが発生しない
△: 220℃<ホットオフセット発生温度≦161℃、全速度
×: 161℃<ホットオフセット発生温度、または全温度オフセット発生
本実施例におけるゲル成分の含有率は、以下のように測定された値をもって定義する。樹脂2.5gと酢酸エチル47.5gを100mlサンプル管に投入した。このサンプル管を回転数50rpm、22℃、12時間攪拌後、22℃で12時間静置し、静置後、サンプル管の上澄み液5gを150℃、1時間で乾燥させた後の重量を秤量し(Xg)、以下の式に従って計算した。
ゲル分率(%)=((2.5/50 − X/5)/(2.5/50))×100
スチレン 73部、アクリル酸n−ブチル 24.5部、ヒドロキシエチルメタクリレート 2.5部を窒素置換したフラスコに仕込み、内温120℃に昇温後同温度に保ち、バルク重合を10時間行った。この時の重合率は51%であった。ついで、キシレン 30部を加え、予め混合溶解しておいたジブチルパーオキサイド 0.1部、キシレン 50部を130℃に保ちながら8時間かけて連続添加した。更に1,1'−ビス(t−ブチルパーオキシ)−3,3,5−トリメチルシクロヘキサンを0.2部加えて2時間反応を継続した。その後更に1,1−ビス(t−ブチルパーオキシ)−3,3,5トリメチルシクロヘキサンを0.5部加えて2時間保持を行うことにより、高分子量体(A)として、ピーク分子量(Mp)が200,000のスチレン系重合体A1を得た。
スチレン 92.5部、アクリル酸n−ブチル 6.5部、メタクリル酸 1.0部とキシレン溶媒 75部からなる溶液にスチレン 100部当たり3部のジ−t−ブチルパーオキサイドを均一に溶解した。かかる溶液を、内温190℃内圧 6kg/cm2に保持した5Lの反応器に750ml/時間で連続的に供給して重合し低分子量体(B)として、ピーク分子量(Mp)が5,000のスチレン系重合体B1を得た。
スチレン系重合体A1 30部、スチレン系重合体B1 70部をヘンシェルミキサーにて混合後、2軸混練機(KEXN S−40型、栗本鉄工所製)にて2軸混錬機吐出部樹脂温度175℃の条件下、トリレンジイソシアネート(TDI)を供給し、混練反応させた。その後、冷却・粉砕して樹脂1を得た。この樹脂の物性を表3に示す。
表1および2に記載の成分を用いて実施例1と同様にして、樹脂2〜7を得た。この樹脂の物性を表3に示す。
表1および2に記載の成分を用いて実施例1と同様にして、樹脂8〜10を得た。この樹脂の物性を表3に示す。
実施例1により得られた樹脂に、カーボンブラック(REGAL 330R;CABOT社製)1.0部、帯電調整剤(T−77;保土谷化学社製)1.0部、ポリプロピレンワックス(ハイワックスNP105;三井化学製)2.5部をヘンシェルミキサーで予備混合した。その後、2軸混練機(PCM30;池貝鉄工株式会社製)を用い、120℃に設定して混練して冷却後、ハンマーミルにて粗粉砕した。その後、ジェット粉砕機(IDS2型;日本ニューマチック社製)にて微粉砕し、次いで気流分級して平均粒径8.5μm(5μm以下3質量%、20μm以上2質量%)トナー粒子を得た。次いで、上記トナー100部に対して、疎水性シリカ(R−972、アエロジル社製)を0.1部となる割合で外部から添加し、混合してトナーを得た。得られたトナーの評価結果を表4に示した。
実施例2〜7で得た樹脂2〜7を用いた以外は、実施例8と同様の方法でトナーを得た。得られたトナーの評価結果を表4に示した。
比較例1〜3で得た樹脂8〜10を用いた以外は、実施例8と同様の方法でトナーを得た。得られたトナーの評価結果を表4に示した。
表1および2に記載の成分を用いて実施例1と同様にして、互いに類似組成だがカルボキシル基の有無の違いを有する樹脂11および12を得た。この樹脂の物性を表3に示す。
一方、本発明のトナー用樹脂組成物およびトナーは、定着性、耐オフセット性および生産性のバランスに優れたものとなっている。
Claims (11)
- 活性水素基を含有し、ピーク分子量(Mp)が3万以上、200万以下であるスチレン系重合体(A)と、カルボキシル基を含有し、ピーク分子量(Mp)が2,000以上、2万以下であるスチレン系重合体(B)と、イソシアネート基を有する架橋性化合物(C)とを反応させて得られる樹脂(D)を含むトナー用樹脂組成物。
- 前記(A)中の活性水素基数と前記(C)中のイソシアネート基数の比が、2:1〜10:1である、請求項1に記載のトナー用樹脂組成物。
- 前記(A)中の活性水素基が水酸基である、請求項1又は2に記載のトナー用樹脂組成物。
- フローテスターによる1/2流出温度(Tm)が115℃以上135℃以下である、請求項1乃至3のいずれかに記載のトナー用樹脂組成物。
- 前記(A)中の活性水素基数が、前記(A)100g当たり0.01モル以上0.2モル以下である、請求項1乃至4のいずれかに記載のトナー用樹脂組成物。
- 前記(B)のガラス転移温度(Tg)が40℃以上75℃以下である、請求項1乃至5のいずれかに記載のトナー用樹脂組成物。
- ゲル分率が0.1質量%以上3.0質量%以下である、請求項1乃至6のいずれかに記載のトナー用樹脂組成物。
- 前記樹脂(D)が、前記(A)と前記(B)との混合物を含む液体に前記(C)を添加して、反応させることにより得られたものである、請求項1乃至7のいずれかに記載のトナー用樹脂組成物。
- 天然ワックスまたは融点60℃以上145℃以下のポリオレフィンワックスの少なくとも一つをさらに含み、前記ワックスを前記樹脂(D)に対して0.1質量%以上10質量%以下で含む、請求項1乃至8のいずれかに記載のトナー用樹脂組成物。
- 天然ワックスまたは融点60℃以上145℃以下のポリオレフィンワックスの少なくとも一つをさらに含み、前記ワックスを前記樹脂(D)に対して0.1質量%以上10質量%以下で含む、請求項2に記載のトナー用樹脂組成物。
- 請求項1乃至10のいずれかに記載のトナー用樹脂組成物と少なくとも着色剤とを含むトナー。
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JP2008546868A JP4956549B2 (ja) | 2006-11-29 | 2007-10-29 | トナー用樹脂組成物および該樹脂組成物を用いたトナー |
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JP2008546868A JP4956549B2 (ja) | 2006-11-29 | 2007-10-29 | トナー用樹脂組成物および該樹脂組成物を用いたトナー |
PCT/JP2007/001178 WO2008065736A1 (fr) | 2006-11-29 | 2007-10-29 | Composition de résine pour toner, et toner utilisant la composition de résine |
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US (1) | US8163454B2 (ja) |
EP (1) | EP2088472B1 (ja) |
JP (1) | JP4956549B2 (ja) |
KR (1) | KR101032223B1 (ja) |
CA (1) | CA2671119C (ja) |
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WO (1) | WO2008065736A1 (ja) |
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JPH0769632B2 (ja) * | 1987-03-09 | 1995-07-31 | 積水化学工業株式会社 | トナ−用樹脂の製造方法 |
BE1006371A4 (nl) * | 1991-12-16 | 1994-08-02 | Wetenschappelijk En Tech Ct Vo | Vegetatie-remmend produkt voor aanplant. |
JPH06258869A (ja) * | 1993-03-09 | 1994-09-16 | Dainippon Ink & Chem Inc | トナーおよびその製造方法 |
JP2748085B2 (ja) * | 1993-08-30 | 1998-05-06 | 株式会社巴川製紙所 | 電子写真用トナー |
JPH07168397A (ja) * | 1993-12-13 | 1995-07-04 | Tomoegawa Paper Co Ltd | トナー用樹脂組成物およびそれを用いた電子写真用トナー |
JPH0915906A (ja) * | 1995-06-29 | 1997-01-17 | Bando Chem Ind Ltd | 静電潜像現像用トナーの製造方法 |
JP3066020B2 (ja) * | 1998-07-03 | 2000-07-17 | 三洋化成工業株式会社 | 電子写真用トナ―バインダ― |
JP4323013B2 (ja) | 1998-07-22 | 2009-09-02 | 三洋化成工業株式会社 | 電子写真用トナーバインダー組成物及びトナー組成物 |
TWI227384B (en) | 2000-10-12 | 2005-02-01 | Mitsui Chemicals Inc | A toner binder for electrophotography and toner for electrophotography |
EP1564600B1 (en) * | 2002-08-08 | 2010-10-06 | Mitsui Chemicals, Inc. | Binder resin for toner and toner |
JP4047693B2 (ja) | 2002-10-15 | 2008-02-13 | 三井化学株式会社 | トナー用バインダー樹脂及び該樹脂を用いた静電荷現像用電子写真トナー |
US20060251980A1 (en) * | 2003-05-29 | 2006-11-09 | Mitsui Chemicals, Inc. | Binder resin for toner and toner for electrophotography |
US7306888B2 (en) * | 2004-06-30 | 2007-12-11 | Samsung Electronics Company | Dry electrophotographic toners comprising amphipathic copolymers having acidic functionality |
JP4267533B2 (ja) | 2004-07-22 | 2009-05-27 | 三井化学株式会社 | トナー用バインダー樹脂及び該樹脂を用いた静電荷現像用電子写真トナー |
JP4910294B2 (ja) * | 2005-02-17 | 2012-04-04 | 大日本印刷株式会社 | カラーフィルタ基板および液晶表示パネル |
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2007
- 2007-10-29 KR KR1020097013415A patent/KR101032223B1/ko not_active IP Right Cessation
- 2007-10-29 EP EP07827957.7A patent/EP2088472B1/en not_active Not-in-force
- 2007-10-29 JP JP2008546868A patent/JP4956549B2/ja active Active
- 2007-10-29 US US12/514,128 patent/US8163454B2/en not_active Expired - Fee Related
- 2007-10-29 CA CA2671119A patent/CA2671119C/en not_active Expired - Fee Related
- 2007-10-29 WO PCT/JP2007/001178 patent/WO2008065736A1/ja active Application Filing
- 2007-11-02 TW TW096141587A patent/TW200836028A/zh unknown
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JPWO2008065736A1 (ja) | 2010-03-04 |
WO2008065736A1 (fr) | 2008-06-05 |
US20100003611A1 (en) | 2010-01-07 |
TW200836028A (en) | 2008-09-01 |
EP2088472A1 (en) | 2009-08-12 |
CA2671119A1 (en) | 2008-06-05 |
KR101032223B1 (ko) | 2011-05-02 |
US8163454B2 (en) | 2012-04-24 |
CA2671119C (en) | 2011-11-29 |
EP2088472B1 (en) | 2013-10-02 |
KR20090083955A (ko) | 2009-08-04 |
EP2088472A4 (en) | 2010-09-08 |
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