JP2019003009A - 複合樹脂 - Google Patents
複合樹脂 Download PDFInfo
- Publication number
- JP2019003009A JP2019003009A JP2017117102A JP2017117102A JP2019003009A JP 2019003009 A JP2019003009 A JP 2019003009A JP 2017117102 A JP2017117102 A JP 2017117102A JP 2017117102 A JP2017117102 A JP 2017117102A JP 2019003009 A JP2019003009 A JP 2019003009A
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- JP
- Japan
- Prior art keywords
- group
- composite resin
- nitrogen
- compound
- polymer
- Prior art date
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- Granted
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- 239000001257 hydrogen Substances 0.000 claims abstract description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 48
- 125000000524 functional group Chemical group 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims description 55
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
- 239000000126 substance Substances 0.000 claims description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
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- 125000003118 aryl group Chemical group 0.000 claims description 7
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- 125000005616 oxoacid group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
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- 230000033001 locomotion Effects 0.000 description 5
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- 125000005033 thiopyranyl group Chemical group 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- QWWZNXBOJLOHGI-HNQUOIGGSA-N trans-3-Octenedioic acid Chemical compound OC(=O)CCC\C=C\CC(O)=O QWWZNXBOJLOHGI-HNQUOIGGSA-N 0.000 description 1
- YHGNXQAFNHCBTK-OWOJBTEDSA-N trans-3-hexenedioic acid Chemical compound OC(=O)C\C=C\CC(O)=O YHGNXQAFNHCBTK-OWOJBTEDSA-N 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 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
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Developing Agents For Electrophotography (AREA)
Abstract
Description
<窒素含有基を有する高分子(高分子)>
窒素含有基を有する高分子は、窒素含有基を有する重量平均分子量が1,000以上の有機化合物をいう。窒素含有基を有する高分子は、窒素原子を含むものであれば特に制限されず、窒素含有基の窒素原子は、高分子の主鎖に含まれていてもよいし、側鎖に含まれていてもよい。液晶性化合物と水素結合を形成しやすいという観点からは、高分子は、側鎖に窒素含有基を含んでいると好ましい。
液晶性化合物は、上記高分子が有する窒素含有基と水素結合を形成する官能基を有し、かつ、光照射により異性化する(光異性化する)液晶性化合物である。この水素結合は、光照射により切断されうる比較的弱い結合である。また、「光照射により異性化する(光異性化する)」とは、具体的には、光(好ましくは紫外光、より好ましくは300nm以上400nm未満の波長を有する紫外光)の照射により、E型(トランス体)からZ型(シス体)へ、またはZ型(シス体)からE型(トランス体)へ異性化することをいう。さらに、「液晶性」とは、液晶相を呈することを意味する。
Xは、CHまたは窒素原子であり、
Y1およびY2は、それぞれ独立して、前記窒素含有基を有する高分子中の窒素含有基と水素結合を形成しうる基であり、
ArおよびAr’は、それぞれ独立して、置換または非置換のフェニレン基または2価の複素環基であり、
R1〜R8は、それぞれ独立して、水素原子、ハロゲン原子、ヒドロキシ基、チオール基、シアノ基、または置換もしくは非置換のアルキル基、アルケニル基、アルコキシ基、アミノ基、アリール基もしくは複素環基であり、互いに連結して環状構造を形成してもよく、
nおよびmは、それぞれ独立して、3以上10以下の整数である。
本発明の複合樹脂の製造方法は、特に制限されない。たとえば、窒素含有基を有する高分子と液晶性化合物とを溶媒中で混合した後、乾燥等により溶媒を除去することにより、複合樹脂を得ることができる。該溶液を、ガラス基板等の基板上に塗布し、乾燥して溶媒を除去すれば、フィルム状の複合樹脂を得ることができる。
本発明の複合樹脂は、電子写真用トナーや、光照射により液化と固化とを繰り返す光制御接着剤等に好適に用いられうる。中でも、画像形成時における省エネルギー化や、操作性向上等のメリットが得られることから、電子写真用トナーに用いられることが好ましい。すなわち、本発明は、上記複合樹脂を含む電子写真用トナーをも提供する。
本発明に係るトナーは、結着樹脂を含んでもよい。かような結着樹脂は、一般にトナーを構成する結着樹脂として用いられている樹脂を制限なく用いることができる。具体的には、たとえば、スチレン樹脂、アクリル樹脂、スチレンアクリル樹脂、ポリエステル樹脂、シリコーン樹脂、オレフィン樹脂、アミド樹脂、およびエポキシ樹脂などが挙げられる。これら結着樹脂は、単独でもまたは2種以上組み合わせても用いることができる。
本発明でいうスチレンアクリル樹脂とは、少なくともスチレン単量体と(メタ)アクリル酸エステル単量体とを用いて、重合を行うことにより形成されるものである。ここで、スチレン単量体とは、CH2=CH−C6H5の構造式で表されるスチレンの他、スチレン構造中に公知の側鎖や官能基を有する構造のものも含まれる。
エチレン、プロピレン、イソブチレン等
(2)ビニルエステル類
プロピオン酸ビニル、酢酸ビニル、ベンゾエ酸ビニル等
(3)ビニルエーテル類
ビニルメチルエーテル、ビニルエチルエーテル等
(4)ビニルケトン類
ビニルメチルケトン、ビニルエチルケトン、ビニルヘキシルケトン等
(5)N−ビニル化合物類
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
(6)その他
ビニルナフタレン、ビニルピリジン等のビニル化合物類、アクリロニトリル、メタクリロニトリル、アクリルアミド等のアクリル酸あるいはメタクリル酸誘導体等。
ポリエステル樹脂は、2価以上のカルボン酸(多価カルボン酸成分)と、2価以上のアルコール(多価アルコール成分)との重縮合反応によって得られる公知のポリエステル樹脂である。なお、ポリエステル樹脂は、非晶性であってもよいし結晶性であってもよい。
本発明に係るトナーは着色剤を含有してもよい。着色剤としては、一般に知られている染料および顔料を用いることができる。
本発明に係るトナーは、離型剤を含有してもよい。使用される離型剤は、特に限定されるものではなく、公知の種々のワックスを用いることができる。ワックスとしては、低分子量ポリプロピレン、ポリエチレン、または酸化型の低分子量ポリプロピレン、ポリエチレンなどのポリオレフィン、パラフィン、合成エステルワックスなどが挙げられ、特に、低融点および低粘度であることから、合成エステルワックスを用いることが好ましく、合成エステルワックスとしてベヘン酸ベヘニル、グリセリントリベヘネート、ペンタエリスリトールテトラベヘネートなどを用いることが特に好ましい。
本発明に係るトナーは、荷電制御剤を含有してもよい。使用される荷電制御剤は、摩擦帯電により正または負の帯電を与えることのできる物質であり、かつ無色のものであれば特に限定されず、公知の種々の正帯電性の荷電制御剤および負帯電性の荷電制御剤を用いることができる。
トナーの流動性、帯電性、クリーニング性等を改良するために、トナー粒子に、いわゆる後処理剤である流動化剤、クリーニング助剤等の外添剤を添加して本発明に係るトナーを構成してもよい。
トナーの平均粒径は、体積基準のメジアン径(D50)で4〜10μmであることが好ましく、6〜9μmであることがより好ましい。体積基準のメジアン径(D50)が上記の範囲にあることにより、転写効率が高くなりハーフトーンの画質が向上し、細線やドット等の画質が向上する。
本発明に係るトナーの製造方法は特に制限されない。たとえば、複合樹脂のみでトナーとする場合は、上記の製造方法により得られた複合樹脂を、ハンマーミル、フェザーミル、カウンタージェットミルなどの装置を用いて粉砕した後、スピンエアーシーブ、クラッシール、マイクロンクラッシファイアーなどの乾式分級機を用いて所望の粒径になるように分級することを含む製造方法が好ましい。
(1A)結着樹脂粒子の分散液を調製する結着樹脂粒子分散液調製工程
(1B)着色剤粒子の分散液を調製する着色剤粒子分散液調製工程
(1C)複合樹脂粒子の分散液を調製する複合樹脂粒子分散液調製工程
(2)結着樹脂粒子、着色剤粒子および複合樹脂粒子が存在している水系媒体中に、凝集剤を添加し、塩析を進行させると同時に凝集・融着を行い、会合粒子を形成する会合工程
(3)会合粒子の形状制御をすることによりトナー粒子を形成する熟成工程
(4)水系媒体からトナー粒子を濾別し、当該トナー粒子から界面活性剤等を除去する濾過、洗浄工程
(5)洗浄処理されたトナー粒子を乾燥する乾燥工程
(6)乾燥処理されたトナー粒子に外添剤を添加する外添剤添加工程
の各工程を含むことが好ましい。以下、(1A)〜(1C)の工程について説明する。
本工程では、従来公知の乳化重合などにより樹脂粒子を形成し、この樹脂粒子を凝集、融着させて結着樹脂粒子を形成する。一例として、結着樹脂を構成する重合性単量体を水系媒体中へ投入、分散させ、重合開始剤によりこれら重合性単量体を重合させることにより、結着樹脂粒子の分散液を作製する。
この着色剤粒子分散液調製工程は、着色剤を水系媒体中に微粒子状に分散させて着色剤粒子の分散液を調製する工程である。
この複合樹脂粒子分散液調製工程は、複合樹脂を水系媒体中に微粒子状に分散させて複合樹脂粒子の分散液を調製する工程である。複合樹脂粒子分散液を調製するにあたり、まず、複合樹脂乳化液を調製する。複合樹脂乳化液の調製方法としては、たとえば、有機溶媒に複合樹脂を溶解させた複合樹脂液を得た後、該複合樹脂液を水系媒体中で乳化させる方法が挙げられる。
本工程で用いられる有機溶媒は、本発明の複合樹脂を溶解させることができれば特に制限されず使用することができる。具体的には、酢酸エチル、酢酸ブチルなどのエステル類、ジエチルエーテル、ジイソプロピルエーテル、テトラヒドロフランなどのエーテル類、アセトン、メチルエチルケトンなどのケトン類、ヘキサン、ヘプタンなどの飽和炭化水素類、ジクロロメタン、ジクロロエタン、四塩化炭素などのハロゲン化炭化水素類が挙げられる。
本工程で用いられる水系媒体は、水、または水を主成分として、アルコール類、グリコール類などの水溶性溶媒や、界面活性剤、分散剤などの任意成分が配合されている水系媒体などが挙げられる。水系媒体は、好ましくは水と界面活性剤とを混合したものが用いられる。
本発明に係るトナーは、たとえば磁性体を含有させて一成分磁性トナーとして使用する場合、いわゆるキャリアと混合して二成分現像剤として使用する場合、非磁性トナーを単独で使用する場合などが考えられ、いずれも好適に使用することができる。
本発明に係るトナーは、電子写真方式の公知の種々の画像形成方法において用いることができる。たとえば、モノクロの画像形成方法やフルカラーの画像形成方法に用いることができる。フルカラーの画像形成方法では、イエロー、マゼンタ、シアン、およびブラックの各々に係る4種類のカラー現像装置と、1つの感光体とにより構成される4サイクル方式の画像形成方法や、各色に係るカラー現像装置および感光体を有する画像形成ユニットを、それぞれ色別に搭載するタンデム方式の画像形成方法など、いずれの画像形成方法にも適用することができる。
図3は、画像形成装置100における照射部40の概略構成図である。
<窒素含有基を有する高分子の準備>
重量平均分子量が35,000であるポリ(2−ビニルピリジン)(アルドリッチ社製)を準備した。
ポリ(2−ビニルピリジン) 500mg、および液晶性化合物1 30mg(高分子に対して6質量%)を、クロロホルム2mlに溶解し、得られた溶液をガラス基板にスピンコート法で塗布した後風乾し(乾燥時間2時間)、フィルム状の複合樹脂1(厚さ20μm)を得た。
ポリ(2−ビニルピリジン)の代わりに、重量平均分子量が約20,000であるスチレン−4−ビニルピリジン共重合体(アルドリッチ社製)を用いたこと以外は、実施例1と同様の方法で、フィルム状の複合樹脂2(厚さ20μm)を得た。
ポリ(2−ビニルピリジン)の代わりに、重量平均分子量が1,000以上である熱可塑性ポリウレタンエラストマーを用いたこと以外は、実施例1と同様の方法で、フィルム状の複合樹脂3(厚さ20μm)を得た。
ポリ(2−ビニルピリジン)の代わりに、重量平均分子量が約30,000であるナイロン66(アルドリッチ社製)を用いたこと以外は、実施例1と同様の方法で、フィルム状の複合樹脂4(厚さ20μm)を得た。
液晶性化合物1の代わりに、下記の方法で合成した液晶性化合物2を用いたこと以外は、実施例2と同様の方法で、フィルム状の複合樹脂5(厚さ20μm)を得た。
液晶性化合物1の代わりに、下記の方法で合成した液晶性化合物3を用いたこと以外は、実施例2と同様の方法で、フィルム状の複合樹脂6(厚さ20μm)を得た。
液晶性化合物1の代わりに、下記の方法で合成した液晶性化合物4を用いたこと以外は、実施例2と同様の方法で、フィルム状の複合樹脂7(厚さ20μm)を得た。
液晶性化合物1の代わりに、下記の方法で合成した液晶性化合物5を用いたこと以外は、実施例2と同様の方法で、フィルム状の複合樹脂8(厚さ21μm)を得た。
実施例2において、用いた液晶性化合物1の添加量を5mg(高分子に対して1質量%)に変更したこと以外は、実施例2と同様の方法で、フィルム状の複合樹脂9(厚さ19μm)を得た。
実施例2において、用いた液晶性化合物1の添加量を100mg(高分子に対して20質量%)に変更したこと以外は、実施例2と同様の方法で、フィルム状の複合樹脂10(厚さ22μm)を得た。
液晶性化合物1を添加しなかったこと以外は、実施例2と同様の方法で、フィルム状の比較樹脂1(厚さ18μm)を得た。
ポリ(2−ビニルピリジン)の代わりに、重量平均分子量が50,000であるポリスチレン(和光純薬工業株式会社製)を用いたこと以外は、実施例1と同様の方法で、比較複合樹脂2(厚さ18μm)を得た。
液晶性化合物1の代わりに、下記の方法で合成した液晶性化合物101を用いたこと以外は、実施例2と同様の方法で、フィルム状の比較複合樹脂3(厚さ20μm)を得た。
<ガラス転移温度(Tg)>
上記実施例および比較例で作製したフィルム状の複合樹脂または樹脂のガラス転移温度を、示差走査熱量計を用いて、以下のように測定した。測定機器としては、「ダイヤモンドDSC」(株式会社パーキンエルマージャパン製)を用いた。大気圧、常温(25℃)での紫外光照射前のTg(常態Tg)の測定は、紫外光照射前の各フィルムを2mm角に切りだし測定用パンに封入して、リファレンスは空のアルミニウム製パンを使用した。測定条件としては、測定温度0℃〜150℃、昇温速度10℃/分、降温速度10℃/分で、Heat−cool−Heatの温度制御で行い、その2nd.Heatにおけるデータをもとに解析を行い、第1の吸熱ピークの立ち上がり前のベースラインの延長線と、第1のピークの立ち上がり部分からピーク頂点までの間で最大傾斜を示す接線とを引き、その交点をガラス転移温度(Tg)とした。
紫外光および可視光照射後に、各樹脂フィルムを1cm角に切りだし上質紙A(コニカミノルタ株式会社製、Jペーパー)上に設置した。このサンプルを、上記で測定した常態Tgより10℃高い温度で加熱しつつ、紫外光(波長369nm、ランプの照度100mW/cm2)を10分間照射した後、室温(25℃)で可視光(波長499nm、ランプの照度100mW/cm2)を10分間照射し、さらに上質紙B(コニカミノルタ株式会社製、Jペーパー)を重ね、樹脂フィルムの部分を0.5MPaで加圧し、添加した化合物(液晶性化合物)の上質紙Bへの移動の有無を顕微鏡にて目視で確認した。下記表1中、○は化合物(液晶性化合物)の上質紙Bへの移動が無かったことを、×は化合物(液晶性化合物)の上質紙Bへの移動があったことをそれぞれ表し、○であれば、トナーとしての耐久性に優れていると言える。
2 帯電器、
3 露光器、
4 現像部、
5 転写部、
6 除電部
7 用紙搬送系、
8 クリーニング部、
9 圧着部、
10 画像形成部、
11 給紙部、
12 搬送ローラー、
13 搬送ベルト、
14 排紙部、
15 手差し給紙部、
16 トレイ、
17 温湿度計、
20 画像処理部、
24 用紙反転部、
40 照射部、
40a 第1照射部、
40b 第2照射部、
50 転写ローラー、
71 画像読取装置、
72 自動原稿送り装置、
85 ブレード、
90 制御部、
91、92 加圧部材、
100 画像形成装置、
d 原稿、
S 記録用紙。
Claims (7)
- 窒素含有基を有する高分子と;前記窒素含有基と水素結合を形成する官能基を有し、光照射により異性化する液晶性化合物と;が水素結合を形成してなる複合樹脂であって、前記水素結合は光照射により切断されうる結合である、複合樹脂。
- 前記液晶性化合物は、下記化学式(1)で表される化合物である、請求項1に記載の複合樹脂:
Xは、CHまたは窒素原子であり、
Y1およびY2は、それぞれ独立して、前記窒素含有基を有する高分子中の窒素含有基と水素結合を形成しうる基であり、
ArおよびAr’は、それぞれ独立して、置換または非置換のフェニレン基または2価の複素環基であり、
R1〜R8は、それぞれ独立して、水素原子、ハロゲン原子、ヒドロキシ基、チオール基、シアノ基、または置換もしくは非置換のアルキル基、アルケニル基、アルコキシ基、アミノ基、アリール基もしくは複素環基であり、互いに連結して環状構造を形成してもよく、
nおよびmは、それぞれ独立して、3以上10以下の整数である。 - 前記Y1およびY2は、それぞれ独立して、オキソ酸基である、請求項2に記載の複合樹脂。
- 前記液晶性化合物の分子量は、1000未満である、請求項1〜3のいずれか1項に記載の複合樹脂。
- 前記高分子は、窒素原子を有する複素環基を有する、請求項1〜4のいずれか1項に記載の複合樹脂。
- 請求項1〜5のいずれか1項に記載の複合樹脂を含む、電子写真用トナー。
- 記録媒体上に請求項6に記載の電子写真用トナーからなるトナー像を形成する工程と、
前記トナー像に対して、300nm以上400nm未満の波長を有する光を照射して前記トナー像を軟化させる工程と、
軟化した前記トナー像に対して、400nm以上800nm以下の波長を有する光を照射して前記トナー像を固化させ記録媒体に定着させる工程と、
を含む、画像形成方法。
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