JP4531076B2 - 電子写真トナーの母粒子用樹脂粒子の製造方法 - Google Patents
電子写真トナーの母粒子用樹脂粒子の製造方法 Download PDFInfo
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- JP4531076B2 JP4531076B2 JP2007133098A JP2007133098A JP4531076B2 JP 4531076 B2 JP4531076 B2 JP 4531076B2 JP 2007133098 A JP2007133098 A JP 2007133098A JP 2007133098 A JP2007133098 A JP 2007133098A JP 4531076 B2 JP4531076 B2 JP 4531076B2
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- 239000007883 water-soluble azo polymerization initiator Substances 0.000 description 1
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- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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Description
この方法によれば、分散重合、シード重合法等により比較的単分散な粒子が得られやすい付加重合系樹脂のみならず、重縮合系樹脂や重付加系樹脂においても粒子径が微細かつ粒度分布がシャープな粒子を得ることが可能である。しかしながらこの方法は、製造時に水中での界面自由エネルギーを低下させたり、水中での分散安定性を付与する目的で親水性基を有する界面活性物質(界面活性剤、高分子保護コロイド、界面活性微粒子等)を使用する必要がある。該界面活性物質が樹脂粒子中または表面に残存した場合、親水性基を有する界面活性剤等の水溶性不純物を含有するため、樹脂粒子の粉体特性、電気的特性、熱的特性、化学的安定性等の性能を損ねるという欠点があった。
一方、非水媒体中における粒子形成法として、有機顔料、酸化ケイ素などの微粒子分散剤の存在下において超臨界流体中に加熱溶融させた樹脂を機械的に分散させて微粒化した後減圧して樹脂粒子を得る方法(例えば、特許文献2参照)が知られている。
また微粒子の分子量が500以下である場合、キャリアと混合する際に低分子量成分によってキャリア表面を汚染してしまう問題があった。
本発明の課題は、粒度分布がシャープであり、且つ、低温定着性に優れ、且つ耐熱保存性に優れる樹脂粒子を得ることである。
なお、上記以外は参考発明である。
本発明は、結晶化度が30〜80%、且つ融点が50〜80℃であり、且つ数平均分子量が1,200〜300,000である、樹脂成分が結晶性樹脂(a)のみからなる樹脂微粒子(A)が樹脂(b)からなる樹脂粒子(B)の表面に固着、又は樹脂微粒子(A)からなる皮膜を形成してなる樹脂粒子(C)であることを特徴とする電子写真トナーの母粒子用樹脂粒子の製造法である。
樹脂(a)の結晶化度は公知の方法により測定することができ、例えば示差走査熱量測定(DSC)やX線回折(XRD)等を用いることができる。
樹脂(a)の融点は公知の方法により測定することができ、例えば示差走査熱量測定(DSC)における吸熱ピークより求めることができる。
樹脂微粒子(A)の製法はいかなる製法であってもよい。具体例としては、(a)をジェットミル等の公知の乾式粉砕機により乾式粉砕する方法、(a)の粉末を有機溶剤中に分散し、ビーズミルやロールミル等の公知の湿式分散機により湿式粉砕する方法、(a)の溶剤溶液をスプレードライヤー等により噴霧乾燥する方法、(a)の溶剤溶液を貧溶媒添加や冷却によって過飽和させ析出させる方法、(a)の溶剤溶液を水あるいは有機溶剤中に分散する方法、(a)の前駆体を水中で乳化重合法、ソープフリー乳化重合法、シード重合法、懸濁重合法等により重合させる方法、(a)の前駆体を有機溶剤中で分散重合等により重合させる方法が挙げられる。また上記方法により非晶性樹脂(a’)の微粒子(A’)を合成した後、公知のコーティング法、シード重合法、メカノケミカル法等により、結晶性樹脂(a)を(A’)表面に形成してもよい。
樹脂微粒子(A)及び樹脂粒子(B)のいずれか一方が、少なくともその表面に酸性官能基を有し、他の一方が少なくともその表面に塩基性官能基を有することが好ましい。樹脂微粒子(A)及び樹脂粒子(B)はその内部に酸性官能基又は塩基性官能基を有していてもよい。酸性官能基としてはカルボン酸基、スルホン酸基等が挙げられる。塩基性官能基としては第1級アミノ基、第2級アミノ基、第3級アミノ基等が挙げられる。樹脂微粒子(A)及び樹脂粒子(B)は少なくともその表面に酸性官能基又は塩基性官能基を付与するために、結晶性樹脂(a)、樹脂(b)として酸性官能基又は塩基性官能基を有する樹脂を使用しても良いし、樹脂微粒子(A)及び樹脂粒子(B)にこれら官能基を付与するために表面処理しても良い。
(1−2)脂環式ビニル系炭化水素:モノ−もしくはジ−シクロアルケンおよびアルカジエン類、例えばシクロヘキセン、(ジ)シクロペンタジエン、ビニルシクロヘキセン、エチリデンビシクロヘプテン等;テルペン類、例えばピネン、リモネン、インデン等。
(1−3)芳香族ビニル系炭化水素:スチレンおよびそのハイドロカルビル(アルキル、シクロアルキル、アラルキルおよび/またはアルケニル)置換体、例えばα−メチルスチレン、ビニルトルエン、2,4−ジメチルスチレン、エチルスチレン、イソプロピルスチレン、ブチルスチレン、フェニルスチレン、シクロヘキシルスチレン、ベンジルスチレン、クロチルベンゼン、ジビニルベンゼン、ジビニルトルエン、ジビニルキシレン、トリビニルベンゼン等;およびビニルナフタレン。
(6−5)ニトロ基含有ビニル系モノマー:ニトロスチレン等。
(9−2)ビニル(チオ)エーテル、例えばビニルメチルエーテル、ビニルエチルエーテル、ビニルプロピルエーテル、ビニルブチルエーテル、ビニル2−エチルヘキシルエーテル、ビニルフェニルエーテル、ビニル2−メトキシエチルエーテル、メトキシブタジエン、ビニル2−ブトキシエチルエーテル、3,4−ジヒドロ1,2−ピラン、2−ブトキシ−2’−ビニロキシジエチルエーテル、ビニル2−エチルメルカプトエチルエーテル、アセトキシスチレン、フェノキシスチレン、(9−3)ビニルケトン、例えばビニルメチルケトン、ビニルエチルケトン、ビニルフェニルケトン;ビニルスルホン、例えばジビニルサルファイド、p−ビニルジフェニルサルファイド、ビニルエチルサルファイド、ビニルエチルスルフォン、ジビニルスルフォン、ジビニルスルフォキサイド等。
樹脂微粒子(A)が樹脂粒子(B)の表面に固着されてなるとは、(A)が単に(B)の表面に付着し容易に脱離するような場合は含まないものとする。
微粒子(A)の粒径は、樹脂粒子 (B)の粒径よりも小さい。粒径比[微粒子(A)の体積平均粒径/[樹脂粒子 (C)の体積平均粒径]の値は好ましくは0.001〜0.3、より好ましくは0.002〜0.2、さらに好ましくは0.003〜0.1、特に好ましくは0.01〜0.08である。上記範囲内であると(A)が(B)の表面に効率よく吸着するため、得られる(C)の粒度分布が狭くなる。
(C)の体積平均粒子径DVcと(C)の個数平均粒子径DNcの比DVc/DNcは、好ましくは1.0〜1.5、より好ましくは1.0〜1.4、さらに好ましくは1.0〜1.3である。1.5以下であると粉体特性(流動性、帯電均一性等)、画像の解像度が著しく向上する。
表面被覆率(%)=[(A)に覆われている部分の(B)の表面積/(A)に覆われている部分の(B)の表面積+(B)の表面が露出している部分の面積]×100
結晶化度が20〜80%、且つ融点が50〜150℃であり、且つ数平均分子量が500〜1,000,000である結晶性樹脂(a)からなる樹脂微粒子(A)が分散された液状又は超臨界状態の二酸化炭素(X)中に、樹脂(b)もしくは樹脂(b)の溶剤溶液、又は樹脂(b)の前駆体(b0)もしくはその溶剤溶液を分散させ、前駆体(b0)を分散させたときはさらに前駆体(b0)を重合させて、樹脂(b)からなる樹脂粒子(B)の表面に樹脂微粒子(A)が付着してなる樹脂粒子(C1)を形成させた後、[結晶性樹脂(a)の融点−50℃]以上に加熱することにより、樹脂粒子(B)の表面に付着した樹脂微粒子(A)を溶融させて、樹脂微粒子(A)を樹脂粒子(B)の表面に固着、又は樹脂微粒子(A)からなる皮膜を形成して樹脂粒子(C2)を形成し、溶剤を含む場合は、さらに溶剤を含む二酸化炭素を溶剤を含まない液状又は超臨界状態の二酸化炭素(X)で置換し、次いで圧力を減圧にし液状又は超臨界状態の二酸化炭素(X)を除去することにより、樹脂粒子(C)を得ることを特徴とする電子写真トナー用樹脂粒子の製造方法。
さらには、二酸化炭素に親和性を有するジメチルシロキサン基、含フッ素基と共に、樹
脂(b)に親和性を有する化学構造を有することが好ましい。
より具体的には、後述のジメチルシロキサン基を有するモノマー(あるいは反応性オリゴマー)(M1−1)、及び/又はフッ素を含有するモノマー(M1−2)と、前述の樹脂(b)を構成するモノマー(M2)との共重合体が好ましい。共重合の形態はランダム、ブロック、グラフトのいずれでもよいが、ブロックあるいはグラフトが好ましい。
(CH3 )3 SiO((CH3 )2 SiO)a Si(CH3 )2 R(但しaは、平均値で15〜45であり、Rはメタクリル基を含む有機変性基である。) Rの例としては、C3 H6 OCOC(CH3 )=CH2 が挙げられる。
また樹脂(b)が酸価を有する場合、分散安定性の観点より微粒子(A)は粒子表面にアミノ基を有することが好ましい。アミノ基は1級、2級、3級のいずれでもよく、またアミノ基を含有させる形態は特に限定されず、例えばアミノ基を有する化合物を微粒子(A)中に分散、含浸等の方法により含有させる方法、微粒子(A)を構成する成分にアミノ基を有する化合物を使用する方法、微粒子(A)表面にアミノ基含有カップリング剤等を反応させる方法、微粒子(A)表面にアミノ基含有化合物を吸着させる方法等が挙げられる。
好ましい第1の発明における分散安定剤(D)は、樹脂(b)の溶融液又は樹脂(b)の溶剤溶液を分散する温度・圧力条件における二酸化炭素(X)中へ溶解することが好ましい。
分散安定剤(D)の添加量は、分散安定性の観点から、樹脂(b)の重量に対し0.01〜50重量%が好ましく、さらに好ましくは0.02〜40重量%、特に好ましくは0.03〜30重量%である。
一般的には、樹脂(b)は加熱のみでは十分に粒子が微分散化できる粘度まで下がり難く、また加熱により樹脂(b)に熱変性等の弊害が生じる場合が多い。また樹脂(b)は低粘度である方が、粒度分布はシャープになりやすいため、溶剤(U)を用いることが好ましい。
樹脂(b)の溶剤溶液の濃度は、好ましくは10〜90%、さらに好ましくは20〜80%である。
樹脂(b)のSP値(SP値の計算方法は下記文献1による)は、通常8〜16、好ましくは9〜14である。
文献1:Polymer Engineering and Science,Feburuary,1974,Vol.14,No.2 P.147〜154
具体例としては、樹脂(b)の溶剤溶液を攪拌機や分散機等で分散する方法、樹脂(b)の溶剤溶液を(X0)中にスプレーノズルを介して噴霧して液滴を形成し、液滴中の樹脂を過飽和状態とし、樹脂粒子を析出させる方法(ASES:Aerosol Solvent Extraction Systemとして知られている)、同軸の多重管(2重管、3重管等)から樹脂溶液、(X1)等の高圧ガス、エントレーナ等をそれぞれ別の管から同時に噴出させて、液滴に外部応力を加え分裂を促進させて、粒子を得る方法(SEDS:Solution Enhanced Dispersion by Supercritical Fluidsとして知られている)、超音波を照射する方法等が挙げられる。
分散体(X1)は単一相であることが好ましい。すなわち樹脂(b)の溶剤溶液を使用する場合、(C1)が分散している液体あるいは超臨界二酸化炭素を含む相の他に、溶剤相が分離する状態は好ましくない。したがって、(X0)中に樹脂(b)の溶剤溶液を分散する場合、溶剤相が分離しないように、(X0)に対する(b)の溶剤溶液の量を設定することが好ましい。
本発明の製造方法において、液状又は超臨界状態の二酸化炭素(X)中で行う操作の温度及び圧力は、樹脂(b)が(X)中に溶解せず、且つ(b)が凝集・合一可能な範囲内で設定することが好ましい。通常、低温・低圧ほど目的分散物が(X)中に溶解しない傾向となり、高温・高圧ほど(b)が凝集・合一し易い傾向となる。(X0)、(X1)についても同様である。
分散媒としての物性値(粘度、拡散係数、誘電率、溶解度、界面張力等)を調整するために(X)中に他の物質(e)を適宜含んでよく、例えば、窒素、ヘリウム、アルゴン、空気等の不活性気体等が挙げられる。
したがって、樹脂(b)の溶剤溶液を分散して得られた分散体(X1)に、さらに液状又は超臨界状態の二酸化炭素(X)を混合して樹脂粒子(C1)から溶剤を二酸化炭素の相に抽出し、すなわち溶剤を含む二酸化炭素をさらに(X)で置換した後に圧力を減圧にすることが好ましい。
(X1)と混合する(X)の量は、樹脂粒子(C)の合一防止の観点から、(X1)の体積の1〜50倍が好ましく、さらに好ましくは1〜40倍、最も好ましくは1〜30倍である。上記のように樹脂粒子(C1)中に含有される溶剤を除去ないし減少させることにより、樹脂粒子(C1)同士が合一することを防ぐことができる。
溶剤を含む二酸化炭素をさらに(X)で置換する方法としては、樹脂粒子(C)を一旦フィルターやサイクロンで補足した後、圧力を保ちながら、溶剤が完全に除去されるまで(X)を流通させる方法が挙げられる。
流通させる(X)の量は、(X1)からの溶剤除去の観点から、(X1)の体積に対して1〜100倍が好ましく、さらに好ましくは1〜50倍、最も好ましくは1〜30倍である。
(III)レドックス系重合開始剤(III−1)非水系レドックス系重合開始剤:ヒドロペルオキシド、過酸化ジアルキル、過酸化ジアシル等の油溶性過酸化物と、第三アミン、ナフテン酸塩、メルカプタン類、有機金属化合物(トリエチルアルミニウム、トリエチルホウ素、ジエチル亜鉛等)等の油溶性還元剤とを併用(III−2)水系レドックス系重合開始剤:過硫酸塩、過酸化水素、ヒドロペルオキシド等の水溶性過酸化物と、水溶性の無機もしくは有機還元剤(2価鉄塩、亜硫酸水素ナトリウム、アルコール、ポリアミン等)とを併用等が挙げられる。
(1):反応性基含有プレポリマー(α)が有する反応性基が、活性水素化合物と反応可能な官能基(α1)であり、硬化剤(β)が活性水素基含有化合物(β1)であるという組み合わせ。
(2):反応性基含有プレポリマー(α)が有する反応性基が活性水素含有基(α2)であり、硬化剤(β)が活性水素含有基と反応可能な化合物(β2)であるという組み合わせ。
上記組合せ(1)において、活性水素化合物と反応可能な官能基(α1)としては、イソシアネート基(α1a)、ブロック化イソシアネート基(α1b)、エポキシ基(α1c)、酸無水物基(α1d)および酸ハライド基(α1e)などが挙げられる。これらのうち好ましいものは、(α1a)、(α1b)および(α1c)であり、特に好ましいものは、(α1a)および(α1b)である。ブロック化イソシアネート基(α1b)は、ブロック化剤によりブロックされたイソシアネート基のことをいう。上記ブロック化剤としては、オキシム類[アセトオキシム、メチルイソブチルケトオキシム、ジエチルケトオキシム、シクロペンタノンオキシム、シクロヘキサノンオキシム、メチルエチルケトオキシム等];ラクタム類[γ−ブチロラクタム、ε−カプロラクタム、γ−バレロラクタム等];炭素数1〜20の脂肪族アルコール類[エタノール、メタノール、オクタノール等];フェノール類[フェノール、m−クレゾール、キシレノール、ノニルフェノール等];活性メチレン化合物[アセチルアセトン、マロン酸エチル、アセト酢酸エチル等];塩基性窒素含有化合物[N,N−ジエチルヒドロキシルアミン、2−ヒドロキシピリジン、ピリジンN−オキサイド、2−メルカプトピリジン等];およびこれらの2種以上の混合物が挙げられる。これらのうち好ましいのはオキシム類であり、特に好ましいものはメチルエチルケトオキシムである。
以下実施例により本発明をさらに説明するが、本発明はこれに限定されるものではない。以下の記載において「部」は重量部、「%」は重量%を示す。
冷却管、撹拌機および窒素導入管の付いた反応槽中に、プロピレングリコール831部、テレフタル酸703部、アジピン酸47部、および縮合触媒としてテトラブトキシチタネート0.5部を入れ、180℃で窒素気流下に、生成するメタノールを留去しながら8時間反応させた。次いで230℃まで徐々に昇温しながら、窒素気流下に、生成するプロピレングリコール、水を留去しながら4時間反応させ、さらに5〜20mmHgの減圧下に反応させ、軟化点が87℃になった時点で180℃まで冷却し、さらに無水トリメリット酸24部、テトラブトキシチタネート0.5部を投入し90分反応させた後、取り出した。回収されたプロピレングリコールは442部であった。取り出した樹脂を室温まで冷却後、粉砕し粒子化し樹脂(b−1)を得た。樹脂(b−1)のMnは1900、ガラス転移温度45℃であった。
冷却管、撹拌機および窒素導入管の付いた反応槽中に、プロピレングリコール729部、テレフタル酸683569部、アジピン酸67部、無水トリメリット酸38部および縮合触媒としてテトラブトキシチタネート0.5部を入れ、180℃で窒素気流下に、生成するメタノールを留去しながら8時間反応させた。次いで230℃まで徐々に昇温しながら、窒素気流下に、生成するプロピレングリコール、水を留去しながら4時間反応させ、さらに5〜20mmHgの減圧下に反応させた。回収されたプロピレングリコールは172部であった。軟化点が160℃になった時点で取り出し、室温まで冷却後、粉砕し粒子化し樹脂(b−2)を得た。樹脂(b−2)のMnは5700、ガラス転移温度63℃であった。
温度計および撹拌機の付いたオートクレーブ反応槽中に、キシレン1020部、低分子量ポリプロピレン(三洋化成工業(株)製 ビスコール660P:軟化点 145℃)750部を入れ充分溶解し、窒素置換後、スチレン2385部、アクリロニトリル264部、アクリル酸ブチル351部、ジ−t−ブチルパーオキシヘキサヒドロテレフタレート32.5部およびキシレン570部の混合溶液を175℃で3時間で滴下し、さらにこの温度で30分間保持した。次いで脱溶剤を行い、樹脂(f−1)を得た。
攪拌装置のついた容器に、アセトン700部、製造例1で得られた樹脂1(b−1)228部、製造例2で得られた樹脂2(b−2)57部、及びカーボンブラック15部を仕込み、完全に溶解するまで攪拌し、樹脂溶液(bs−1)を得た。
攪拌機を備えたオートクレーブ内にアセトン700部、オレフィンワックス(a−1)(結晶化度78%、融点80℃、数平均分子量1200)200部、製造例3で得られた樹脂3(f−1)50部、N,Nジメチルステアリルアミン50部を仕込み、温度80℃で加熱して液が透明になるまで攪拌した後、超音波分散機(20kHz、600W、SMT社製UH−600)で超音波照射下で40℃以下に冷却して粒子を析出させ、乳白色の分散液を得た。さらに分散液をビーズミル(ダイノーミルマルチラボ:シンマルエンタープライゼス製)で粒径0.3mmのジルコニアビーズを用いて粉砕を行い、乳白色の樹脂微粒子(A−1)分散液を得た。この分散液の体積平均粒径は0.3μmであった。
ノルマルヘキサン700部、ポリカプロラクトン(a−2)(結晶化度60%、融点60℃、数平均分子量50,000、)300部を混合した後、ビーズミル(ダイノーミルマルチラボ:シンマルエンタープライゼス製)で粒径0.3mmのジルコニアビーズを用いて粉砕を行い、乳白色の樹脂微粒子(A−2)分散液を得た。この分散液の体積平均粒径は0.4μmであった。
撹拌装置、加熱冷却装置、温度計、滴下ロート、および窒素吹き込み管を備えた反応容器に、トルエン500部を仕込み、別のガラス製ビーカーに、トルエン350部、ベヘニルアクリレート(炭素数22個の直鎖アルキル基を有するアルコールのアクリレート)150部、AIBN(アゾビスイソブチロニトリル)7.5部を仕込み、20℃で撹拌、混合して単量体溶液を調製し、滴下ロートに仕込んだ。反応容器の気相部の窒素置換を行った後に密閉下80℃で2時間かけて単量体溶液を滴下し、滴下終了から2時間、85℃で熟成した後、トルエンを130℃で3時間減圧除去して、樹脂(a−3)を得た。この樹脂の結晶化度42%、融点は65℃、数平均分子量110,000であった。
製造例6において、ポリカプロラクトン(a−2)の代わりに、製造例7で得られた樹脂4(a−3)(結晶化度42%、融点65℃、数平均分子量110,000)を用いた以外は製造例6と同様にして、乳白色の樹脂微粒子(A−3)分散液を得た。この分散液の体積平均粒径は0.3μmであった。
攪拌機を備えた反応容器内にTHF700部を仕込み、反応容器内の空気を窒素置換した後、加熱して還流温度とした。次に、メタクリル酸メチル150部、メタクリル変性シリコーン(官能基等量:12,000g/mol、数平均分子量12,000、信越化学工業製:X22−2426、下記一般式(1)で示される構造を有する。)150部、アゾビスイソブチロニトリル1.5部の混合物を反応基内に2時間で適下後、還流温度で6時間熟成し、疎水性分散安定剤(D)溶液を得た。(D)の重量平均分子量は20,000であった。
図1の実験装置において、まずバルブV1、V2を閉じ、ボンベB2、ポンプP4より粒子回収槽T4に二酸化炭素(純度99.99%)を導入し、14MPa、40℃に調整した。また樹脂溶液タンクT1に樹脂溶液(bs−1)とアセトン、微粒子分散液タンクT2に樹脂微粒子(A−1)分散液と疎水性分散安定剤(D)溶液を仕込んだ。次にボンベB1、ポンプP3より二酸化炭素を分散槽T3に導入し、9MPa、40℃に調整し、さらにタンクT2、ポンプP2より樹脂微粒子(A−1)分散液を導入した。次に分散槽T3の内部を2000rpmで攪拌しながら、タンクT1、ポンプP1より樹脂溶液(bs−1)を分散槽T3内に導入した。導入後T3の内部の圧力は14MPaとなった。
樹脂溶液(bs−1) 270部
アセトン 122部
樹脂微粒子(A−1)分散液 45部
疎水性分散安定剤(D)溶液 14部
二酸化炭素 550部
なお導入した二酸化炭素の質量は、二酸化炭素の温度(40℃)、及び圧力(15MPa)
から二酸化炭素の密度を下記文献2に記載の状態式より算出し、これに分散槽T3の体積を乗じることにより算出した。
文献2:Journal of Physical and Chemical Refarence data、vol.25、P.1509〜1596
実施例1において、樹脂微粒子(A−1)分散液の代わりに、樹脂微粒子(A−2)分散液を使用したこと以外は実施例1と同様にして、樹脂粒子(C−2)を得た。
実施例2における分散槽T3への仕込み組成の質量比は次の通りである。
樹脂溶液(bs−1) 270部
アセトン 122部
樹脂微粒子(A−2)分散液 45部
疎水性分散安定剤(D)溶液 14部
二酸化炭素 550部
実施例1において、樹脂微粒子(A−1)分散液の代わりに、樹脂微粒子(A−3)分散液を使用したこと以外は実施例1と同様にして、樹脂粒子(C−3)を得た。
実施例3における分散槽T3への仕込み組成の質量比は次の通りである。
樹脂溶液(bs−1) 270部
アセトン 122部
樹脂微粒子(A−3)分散液 45部
疎水性分散安定剤(D)溶液 14部
二酸化炭素 550部
実施例1において樹脂微粒子(A−1)分散液を仕込まない以外は実施例1と同様にして、比較樹脂粒子 (C−4’)を得た。
比較例1における分散槽T3への仕込み組成の質量比は次の通りである。
樹脂溶液(bs−1) 270部
アセトン 167部
疎水性分散安定剤(D)溶液 14部
二酸化炭素 550部
撹拌棒および温度計をセットした反応容器に、水683部、メタクリル酸エチレンオキサイド付加物硫酸エステルのナトリウム塩(エレミノールRS−30、三洋化成工業製)11部、スチレン139部、メタクリル酸138部、アクリル酸ブチル184部、過硫酸アンモニウム1部を仕込み、400回転/分で15分間撹拌したところ、白色の乳濁液が得られた。加熱して、系内温度75℃まで昇温し5時間反応させた。更に、1%過硫酸アンモニウム水溶液30部加え、75℃で5時間熟成してビニル樹脂(スチレン−メタクリル酸−メタクリル酸ブチル−メタクリル酸EO付加物硫酸エステルのナトリウム塩の共重合体)の水性分散液を得た。水性分散液をLA−920で測定した体積平均粒径は、0.15μmであった。さらに水性分散液を凍結乾燥し、比較樹脂微粒子(A−5’)を得た。
実施例1において樹脂微粒子(A−1)の代わりに、T3に予め比較製造例で得られた比較樹脂微粒子(A−5’)を仕込んだ以外は実施例1と同様にして、比較樹脂粒子(C−5’)を得た。
比較例2における分散槽T3への仕込み組成の質量比は次の通りである。
樹脂溶液(bs−1) 270部
アセトン 153部
比較樹脂微粒子(A−5’) 14部
疎水性分散安定剤(D)溶液 14部
二酸化炭素 550部
比較例2において比較樹脂微粒子(A−5’)の代わりに、疎水性シリカ(RX−50、日本アエロジル製)を用いた以外は比較例2と同様にして、比較樹脂粒子(C−6’)を得た。
ノルマルヘキサン700部、ステアリン酸亜鉛(a−7)(結晶化度85%、融点130℃、分子量632)300部を混合した後、ビーズミル(ダイノーミルマルチラボ:シンマルエンタープライゼス製)で粒径0.3mmのジルコニアビーズを用いて粉砕を行い、乳白色の微粒子(A−7‘)分散液を得た。この分散液の体積平均粒径は0.3μmであった。
実施例1において、微粒子(A−1)分散液の代わりに、微粒子(A−7‘)分散液を使用したこと以外は実施例1と同様にして、樹脂粒子(C−7’)を得た。
比較例4における分散槽T3への仕込み組成の質量比は次の通りである。
樹脂溶液(bs−1) 270部
アセトン 122部
微粒子(A−7‘)分散液 45部
疎水性分散安定剤(D)溶液 14部
二酸化炭素 550部
実施例1〜3で得た樹脂粒子 (C−1)〜(C−3)、および比較例1〜4で得た樹脂粒子(C−4’)〜(C−7’)をドデシルベンゼンスルホン酸ナトリウム水溶液(濃度0.1%)に分散して(C)の体積平均粒径/個数平均粒径をコールターカウンター[マルチタイザーIII(ベックマン・コールター社製)]で測定した。
○: ブロッキングが発生しない。
△: ブロッキングが発生するが、力を加えると容易に分散する。
×: ブロッキングが発生し、力を加えても分散しない。
T2:微粒子分散液タンク
T3:分散槽(最高使用圧力20MPa、最高使用温度100℃、攪拌機つき)
T4:粒子回収槽(最高使用圧力20MPa、最高使用温度100℃)
F1:セラミックフィルター(メッシュ:0.5μm)
T5:溶剤トラップ
B1、B2:二酸化炭素ボンベ
P1、P2:溶液ポンプ
P3、P4:二酸化炭素ポンプ
V1:バルブ
V2:圧力調整バルブ
Claims (5)
- 結晶化度が30〜80%、且つ融点が50〜80℃であり、且つ数平均分子量が1,200〜300,000である、樹脂成分が脂肪族ポリエステル、アルキル(メタ)アクリレート(共)重合物、及びポリオレフィンから選ばれる結晶性樹脂(a)のみからなる樹脂微粒子(A)が分散された液状又は超臨界状態の二酸化炭素(X)中に、樹脂(b)もしくは樹脂(b)の溶剤溶液、又は樹脂(b)の前駆体(b0)もしくはその溶剤溶液を分散させ、前駆体(b0)を分散させたときはさらに前駆体(b0)を重合させて、樹脂(b)からなる樹脂粒子(B)又は溶剤含有の樹脂粒子(B)の表面に樹脂微粒子(A)が付着してなる樹脂粒子(C1)を形成させた後、[結晶性樹脂(a)の融点−50℃]以上に加熱することにより、樹脂粒子(B)の表面に付着した樹脂微粒子(A)を溶融させて、樹脂微粒子(A)を樹脂粒子(B)の表面に固着、又は樹脂微粒子(A)からなる皮膜を形成して樹脂粒子(C2)を形成し、溶剤を含む場合は、さらに溶剤を含む二酸化炭素を溶剤を含まない液状又は超臨界状態の二酸化炭素(X)で置換し、次いで圧力を減圧にし液状又は超臨界状態の二酸化炭素(X)を除去することにより、樹脂微粒子(A)が、樹脂(b)からなる樹脂粒子(B)の表面に、固着又は樹脂微粒子(A)からなる皮膜を形成してなる樹脂粒子(C)を得ることを特徴とする電子写真トナーの母粒子用樹脂粒子の製造方法。
- 樹脂粒子(C1)を形成させた後の次の工程として、樹脂粒子(C1)から溶剤を含まない液状又は超臨界状態の二酸化炭素(X)による溶剤の抽出を行うか、又は[結晶性樹脂(a)の融点−50℃]以上に加熱する工程の次の工程として、樹脂粒子(C1)から溶剤を含まない液状又は超臨界状態の二酸化炭素(X)による溶剤の抽出を行う請求項1に記載の製造方法。
- 結晶性樹脂(a)と樹脂(b)の重量比率が(0.1:99.9)〜(30:70)である請求項1又は2に記載の製造方法。
- 樹脂微粒子(A)及び樹脂粒子(B)のいずれか一方が、少なくともその表面に酸性官能基を有し、他の一方が少なくともその表面に塩基性官能基を有する請求項1〜3のいずれか1項に記載の製造方法。
- 結晶性樹脂(a)が、少なくともベヘニルアクリレートを単量体成分として含む請求項1〜4のいずれか1項に記載の製造方法。」
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