JP2005220282A - ビシナル置換型官能基含有エチレン系共重合体及びその用途 - Google Patents
ビシナル置換型官能基含有エチレン系共重合体及びその用途 Download PDFInfo
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- JP2005220282A JP2005220282A JP2004031626A JP2004031626A JP2005220282A JP 2005220282 A JP2005220282 A JP 2005220282A JP 2004031626 A JP2004031626 A JP 2004031626A JP 2004031626 A JP2004031626 A JP 2004031626A JP 2005220282 A JP2005220282 A JP 2005220282A
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- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
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- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
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- ZCBSOTLLNBJIEK-UHFFFAOYSA-N silane titanium Chemical compound [SiH4].[Ti] ZCBSOTLLNBJIEK-UHFFFAOYSA-N 0.000 description 1
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- BAZAXWOYCMUHIX-UHFFFAOYSA-M sodium perchlorate Chemical compound [Na+].[O-]Cl(=O)(=O)=O BAZAXWOYCMUHIX-UHFFFAOYSA-M 0.000 description 1
- 229910001488 sodium perchlorate Inorganic materials 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
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- 238000001179 sorption measurement Methods 0.000 description 1
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- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical group [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
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- 150000003460 sulfonic acids Chemical class 0.000 description 1
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- 150000003866 tertiary ammonium salts Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- GLBZKFGGCHCGAG-UHFFFAOYSA-M tetrakis[[tris(dimethylamino)-$l^{5}-phosphanylidene]amino]phosphanium;hydroxide Chemical compound [OH-].CN(C)P(N(C)C)(N(C)C)=N[P+](N=P(N(C)C)(N(C)C)N(C)C)(N=P(N(C)C)(N(C)C)N(C)C)N=P(N(C)C)(N(C)C)N(C)C GLBZKFGGCHCGAG-UHFFFAOYSA-M 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 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
- 229910052718 tin Inorganic materials 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
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- 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
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- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
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- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
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- 239000000984 vat dye Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Developing Agents For Electrophotography (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
【解決手段】
[1]エチレンと少なくとも1種のジエンを含む共重合体であって、ジエンに由来する繰り返し単位の全部または一部が一般式(Ia)及び一般式(Ib)から選ばれる少なくとも1種で示される構造であるビシナル置換型官能基含有エチレン系共重合体。
【化1】
(式中、*は重合体中での結合位置を表し、Q1〜Q7は水素原子またはアルキル基を表し、Aは単結合等を表し、X、Yは一方がポリアルキレングリコール基等を表し、他方は一般式(II)〜(IV)で示される基等を表す。)
【化2】
(式中、Eは酸素原子等を表し、R1は水素原子等を表す)
【化3】
(式中、R2,R3は水素原子等を表す)
【化4】
(式中、R4〜R6は水素原子等を表す)。
[2]前記[1]記載の重合体を含むトナー用離型剤、顔料分散剤、塩化ビニル樹脂用滑剤、帯電防止剤に関するものである。
【選択図】なし
Description
[1]エチレンと少なくとも1種のジエンからなる共重合体、またはエチレンと少なくとも1種のジエン及び少なくとも1種の炭素数3〜20のα−オレフィンからなる共重合体であって、ジエンに由来する繰り返し単位の全部または一部が一般式(Ia)及び一般式(Ib)から選ばれる少なくとも1種で示される構造であるビシナル置換型官能基含有エチレン系共重合体、
[2]前記[1]記載のビシナル置換型官能基含有エチレン系共重合体を含むトナー用離型剤、顔料分散剤、塩化ビニル樹脂用滑剤、帯電防止剤に関するものである。
本発明に係る重合体の製造に用いられる一般式(P)または(Q)で表されるノルボルネン系ジエンとしては、例えば、エチリデンノルボルネン、ビニルノルボルネン、5−メチレン−2−ノルボルネン、5−プロペニル−2−ノルボルネン、ジシクロペンタジエン、5−シクロヘキシリデン−2−ノルボルネン等を挙げることができる。これらのなかでは、ビニルノルボルネン、エチリデンノルボルネン、ジシクロペンタジエンが好ましい。
本発明に係る重合体の中間原料である重合体(A)は、ゲルパーミエーションクロマトグラフィー(以下GPCと略す)で測定した重量平均分子量(Mw)は400〜500000が好ましく、より好ましくは800〜200000、更に好ましくは1000〜100000である。
1分子あたりの不飽和基含有量は、Mn×M/14,000により得ることができる。1,000炭素あたりの不飽和基数Mは、1.4〜140個が好ましく、より好ましくは2.8〜35個、更に好ましくは4〜30個である。
(1)サリチルアルドイミン配位子を有する遷移金属化合物を重合触媒として用いる重合方法(例えば、特開2001−2731号公報)
(2)チタン化合物と有機アルミニウム化合物とからなるチタン系触媒を用いる重合方法
(3)バナジウム化合物と有機アルミニウム化合物とからなるバナジウム系触媒を用いる重合方法(特開平11−5818)
(4)ジルコノセンなどのメタロセン化合物と有機アルミニウムオキシ化合物(アルミノキサン)とからなるチーグラー型触媒を用いる重合方法
一般式(Ia)、一般式(Ib)のQ1〜Q7のアルキル基としては、直鎖、分岐または環状の炭素数1〜18のアルキル基が好ましい。アルキル基としては、例えばメチル基、エチル基、n-プロピル基、イソプロピル基、n-ブチル基、イソブチル基、sec-ブチル基、tert-ブチル基、n-ペンチル基、ネオペンチル基、n-へキシル基、n-ヘプチル基、n-オクチル基、n-デシル基、n-テトラデシル基、n-オクタデシル基、シクロプロパン、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、シクロオクチル基、シクロプロピルメチル基、シクロペンチルメチル基、シクロヘキシルメチル基等が挙げられる。
で表される基である。ここで、ポリアルキレングリコール基には一般式(T)中、nが1の場合も包含される。
で表される基である。ここで、ポリアルキレングリコール基には一般式(U)中、nが1の場合も包含される。
一般式(Ia)、一般式(Ib)のX、Yのアシルオキシ基としては、炭素数2〜15のアシルオキシ基が好ましく、ヘテロ原子を含む官能基が結合していてもよい。アシルオキシ基としては、例えば、アセトキシ基、プロピオニルオキシ基、3−カルボキシプロピオニルオキシ基、3−カルボキシ−2−プロペノイルオキシ基、アクリロイルオキシ基、メタクリロイルオキシ基、ヘキサノイルオキシ基、オクタノイルオキシ基、ベンゾイルオキシ基、4−トリフルオロメチルベンゾイルオキシ基、3−ニトロベンゾイルオキシ基、2−カルボキシベンゾイルオキシ基、ナフトイルオキシ基、パーフルオロヘプタノイルオキシ基、パーフルオロオクタノイルオキシ基等を挙げることができる。
-O−CO−O-
-O−CR9R10−O-
-O−CO−CHL-
(Lは水素原子、シアノ基、エステル基、カルボキシル基を表し、R9〜R10は水素原子、アルキル基を表す)
この場合のLのエステル基としては、炭素数2〜20のアルコキシカルボニル基またはアリールオキシカルボニル基が好ましい。エステル基の具体例としては、一般式(Ia)または一般式(Ib)のX、Y、一般式(IV)のR4〜R6と同様のものが挙げられる。
本発明のビシナル置換型官能基含有エチレン系共重合体は、重合体(A)のジエンに由来する繰り返し単位を変性することにより官能基を導入する(以下、官能基化という)。具体的には、重合体(A)のジエンに由来する繰り返し単位の二重結合をエポキシ化したエポキシ基含有重合体(B)から製造することができ、該二重結合のエポキシ化は一般的な方法で行うことができる(US5252677)。また、重合体(A)の分子量は、重合触媒の種類、エチレンまたはα-オレフィンの圧力等の反応条件により、調節することができる。
なお、1H-NMRについては、測定サンプル管中で重合体を、ロック溶媒と溶媒を兼ねた重水素化-1,1,2,2-テトラクロロエタンに完全に溶解させた後、120℃において測定した。ケミカルシフトは、重水素化-1,1,2,2-テトラクロロエタンのピークを5.92ppmとして、他のピークのケミカルシフト値を決定した。
Fc(%)=SC/(SC+SD)×Ep(%)
[(1a)X、Yの一方が水酸基で、他方が一般式(II)で示される基である重合体の製造方法]
原料となるエポキシ基含有重合体(B)に、酸または塩基触媒存在下、一般式(VI)
で示される化合物(以下、反応剤Aと表記する)を反応させることにより、X、Yの一方が水酸基で、他方が一般式(II)で示される基である重合体を得ることができる。
原料となるエポキシ基含有重合体(B)に、一般式(VII)
で示される化合物を反応させることにより、X、Yの一方が水酸基で、他方が一般式(III)で示される基である重合体を得ることができる。反応は、酸または塩基触媒を共存させてもよい。
反応方法は、(1a)の場合と同様に行うことができるが、酸、塩基触媒の非存在下でも反応は進行する。
原料となるエポキシ基含有重合体(B)に、一般式(VIII)
で示される有機金属化合物を反応させることにより、X、Yの一方が水酸基で、他方が一般式(IV)で示される基である重合体を得ることができる。
これらの有機金属化合物の製造は、一般的な方法を用いる事ができる。
反応溶媒とその使用量については(1a)と同様である。
原料となるエポキシ基含有重合体(B)にシアノ化剤を反応させることにより、X、Yの一方が水酸基で、他方がシアノ基の重合体が得られる。
反応溶媒とその使用量については(1a)と同様である。
一般式(Ia)または一般式(Ib)においてXまたはYの一方が水酸基のビシナル置換型官能基含有エチレン系共重合体(以下、重合体Dと表記する)を原料とし、該水酸基にエポキシ化合物を反応させることにより、一般式(Ia)または一般式(Ib)においてX、Yの一方がポリエチレングリコール基である重合体を得ることができる。
触媒であるP=N結合を有する化合物の使用量は、重合速度、経済性等の点から、原料の重合体Dの1モルに対して1×10−4〜5×10−1モルが好ましい。より好ましくは5×10−4〜1×10−1モル、更に好ましくは1×10−3〜1×10−2モルである。
前記重合体Dを原料とし、該水酸基等をアシル化することにより、一般式(Ia)または一般式(Ib)においてX、Yの一方がアシルオキシ基である重合体を得ることができる。アシル化は、重合体Dと、対応する酸ハロゲン化物あるいは酸無水物を塩基触媒存在下反応させる一般的な方法で実施できる。
[(4a)−X−Y−で表される2価の基が -O−CO−O- である重合体の製造方法]
原料となるエポキシ基含有重合体(B)に触媒存在下、二酸化炭素を反応させることにより、−X−Y−で表される2価の基が -O−CO−O- である重合体を得ることができる。
反応は、液相、気相、液−気混合相の何れでも行うことができる。更に常圧、加圧、減圧の何れの状態で実施する事も可能である。反応効率の面から液相反応で行うことが好ましい。
反応温度は特に限定はされないが、好ましくは0〜250℃、更に好ましくは50〜200℃の範囲である。
反応時間は特に限定されないが、好ましくは数分から30時間程度であり、更に好ましくは0.5〜15時間程度である。
カーボネート化においては、塩基触媒および溶媒を共存させても良い。塩基触媒とその使用量、反応溶媒とその使用量は(1a)と同様である。
原料のエポキシ基含有重合体(B)のエポキシ基とカルボニル化合物を、触媒存在下、反応させることにより、−X−Y−で表される2価の基が-O−CR9R10−O- である重合体を得ることができる。ここで用いられるカルボニル化合物としては、該構造に対応するR9R10C=Oで表されるカルボニル化合物であり、例えばホルムアルデヒド、アセトアルデヒド、プロピオンアルデヒド、ベンズアルデヒド、アセトン、メチルエチルケトン、イソブチルメチルケトン、アセトフェノン、ベンゾフェノン、γ-ブチロラクトン、δ-バレロラクトンを挙げることができる。カルボニル化合物の使用量は、原料のエポキシ基含有重合体(B)1モルに対し、1〜100モルが好ましく、より好ましくは1.1〜50モル、更に好ましくは1.2〜20モルの範囲である。
本反応で使用できる触媒としては、例えば塩基触媒およびベンジルピリジニウム塩を挙げることができる。塩基触媒とその使用量は(1a)と同様である。
本反応は無溶媒で行うことが可能であるが、溶媒を使用することも可能である。使用できる溶媒とその使用量は(1a)と同様である。
また、−X−Y−で表される2価の基が-O−CR9R10−O- である重合体は、前記重合体Eの水酸基をR9R10C=Oで表されるカルボニル化合物によりアセタール化することによっても合成できる。反応は、アルコールによるカルボニル化合物のアセタール化反応の一般的な方法により行うことができる。
一般式(Ia)または一般式(Ib)において、X、Yの一方が水酸基であり、他方が一般式(X)
で示される基であるビシナル置換型官能基含有エチレン系共重合体(重合体Fと表す)を、(1c)の方法により合成し、該重合体を酸または塩基触媒存在下、加熱することにより、−X−Y−で表される2価の基が -O−CO−CHL- である重合体を得ることができる。
酸または塩基触媒とその使用量、反応溶媒とその使用量は(1a)と同様である。
[トナー用離型剤]
本発明に係る重合体はトナー用離型剤として好適であり、定着ロールへの耐オフセット性を付与する。具体的には、画像鮮明性を向上させる。この離型剤は、結着樹脂(a)および着色剤(b)、ならびに必要に応じて帯電制御剤などとともに静電荷像現像用のトナーの成分として用いられる。この離型剤として用いるビシナル置換型官能基含有エチレン系共重合体の基となる重合体(A)の重量平均分子量は、500ないし5000の範囲が好ましく、より好ましくは800ないし3000の範囲である。
本発明に係る重合体は顔料分散剤として好適であり、各種顔料との濡れに優れ、持続性を向上させる。具体的には、高濃度のマスターバッチを可能にさせる。この分散剤は、顔料と混合し、次に被着色樹脂と混合した後、押出機により混練および造粒し、ドライカラー、カラーコンパウンドまたはマスターバッチとして使用される。上記顔料分散剤の配合割合は、顔料100重量部に対して通常25ないし200重量部、好ましくは50ないし150重量部の範囲である。
本発明に係る重合体は塩化ビニル樹脂用滑剤として好適であり、滑剤のバランスに優れ、持続性がある。具体的には、生産性を向上させ、消費電力の節減に繋がる。本発明の滑剤を用いたポリ塩化ビニル組成物において、滑剤の配合割合はポリ塩化ビニル100重量部に対し、0.05重量部ないし5重量部の範囲で、好ましくは0.1重量部ないし3重量部である。また、滑剤として用いられるビシナル置換型官能基含有エチレン系共重合体の基となる重合体(A)の重量平均分子量は、400ないし10000の範囲が好ましく、より好ましくは500ないし5000の範囲である。
本発明に係る重合体は帯電防止剤として好適であり、熱可塑性樹脂に少量添加することにより帯電防止性を有し、かつ相溶性も良いために成形時に金型汚染やロール汚染が発生せず、機械的強度にも優れる熱可塑性樹脂が得られる。
熱可塑性樹脂としては、例えば、ポリオレフィン樹脂、ポリスチレン樹脂、アクリル樹脂、ゴム状(共)重合体などのビニル樹脂、ポリアミド樹脂、ポリエステル樹脂、ポリアセタール樹脂、ポリカーボネート樹脂、熱可塑性ポリウレタン樹脂、フッ素樹脂及びこれらの2種以上の混合物が挙げられる。
また、帯電防止剤を含む樹脂組成物には、種々の用途に応じ、該組成物の特性を阻害しない範囲で他の樹脂用添加剤を任意に添加することができる。他の樹脂用添加剤としては、顔料、染料、充填剤(有機及び/若しくは無機フィラー)、核剤、ガラス繊維、滑剤、可塑剤、離型剤、酸化防止剤、難燃剤、紫外線吸収剤及び抗菌剤等が挙げられる。
本発明の帯電防止剤を含む樹脂組成物からなる成形品は、優れた機械的強度及び帯電防止性を有すると共に、良好な塗装性及び印刷性を有する。
本発明に係る重合体は、ワックスなどの公知の低分子量ポリエチレンが用いられる用途に広く利用することができる。この際には、必要に応じて種々の添加剤を添加して用いることもできる。
たとえば本発明に係る重合体を塗料改質剤として用いると、塗膜表面を改質することができる。たとえば艶消し効果に優れ、塗膜の耐摩耗性を向上させることができ、木工塗料に高級感を付与することができ、耐久性を向上させることができる。
本発明に係る重合体はクレヨン、ローソクなどの天然ワックスへの配合剤として好適であり、表面硬度および軟化点を向上させることができる。
本発明に係る重合体は樹脂成形用離型剤として好適であり、熱可塑性樹脂あるいは熱硬化性樹脂に離型性を付与して成形サイクルを向上させることができる
本発明に係る重合体はゴムとの相溶性に優れており、ゴムに離型性を付与し、粘度調整をするゴム加工助剤として好適である。ゴム加工助剤として用いたときにはフィラーおよび顔料の分散性を向上させ、ゴムに離型性、流動性を付与するのでゴム成形時の成形サイクル、押出特性を向上させることができる。
本発明に係る重合体はインキ用耐摩耗性向上剤として好適であり、耐摩耗性向上剤として用いたときには、インキ表面の耐摩耗性、耐熱性を向上させることができる。
本発明に係る重合体は繊維加工助剤として好適であり、繊維を樹脂加工する際に繊維加工助剤として用いたときには、繊維に柔軟性、滑性を付与することができる。
本発明に係る重合体は電気絶縁剤として好適であり、たとえばフィルムコンデンサーの電気絶縁性、耐熱的を向上させることができる。
本発明に係る重合体はポリオレフィンフィルムの防曇剤として好適であり、樹脂との相溶性に優れ、樹脂表面へのブリードアウトを抑制する。具体的にはフィルムに防曇効果を付与すると共に耐久性を向上させる。末端にポリアルキレングリコール基を含有するものが効果の点で有利である。
[エチレン系重合体の製造]
充分に窒素置換した内容積2リットルのステンレス製オートクレーブにヘキサン 1000ml、ビニルノルボルネン(5−vinylbicyclo[2,2,1]hept−2−ene)50mlを装入し、水素を0.3MPa(ゲージ圧)となるまで導入した。次いで、系内の温度を150℃に昇温した後、トリイソブチルアルミニウム0.3ミリモル、トリフェニルカルベニウムテトラキス(ペンタフルオロフェニル)ボレート0.004ミリモル、(t−ブチルアミド)ジメチル(テトラメチル−η5−シクロペンタジエニル)シランチタンジクロライド(シグマアルドリッチ社製)0.02ミリモルをエチレンで圧入することにより重合を開始した。その後、エチレンのみを連続的に供給することにより全圧を2.9MPa(ゲージ圧)に保ち、150℃で20分間重合を行った。少量のエタノールを系内に添加することにより重合を停止した後、未反応のエチレンおよびビニルノルボルネンをパージした。得られたポリマー溶液を、100℃減圧下で一晩乾燥し、エチレン系重合体(A−1)を得た。エチレン系重合体(A−1)の物性は、以下の通り。
不飽和基数M:11.8個、
ビニルノルボルネン含有量:10.3質量%(不飽和基含有量(平均)=1.1個/分子)、
密度:956kg/m3、
融点:117℃、
針入硬度:1以下、
Mn:1,300、
Mw:3,700、
Mw/Mn:2.8
[エポキシ基含有重合体の製造]
500mlセパラブルフラスコにエチレン系重合体(A−1) 100gとトルエン300g、NaWO4 0.85g(2.6mmol)、CH3(nC8H17)3NHSO4 0.60g(1.3mmol)、りん酸 0.11g(1.3 mmol)を仕込み、撹拌しながら30分間加熱還流し、重合物を完全に溶融させた。内温を90℃にした後、30%過酸化水素水 37g(326mmol)を3時間かけて滴下した後、内温90〜92℃で3時間撹拌した。その後、90℃に保ったまま25%チオ硫酸ナトリウム水溶液34.4g(54.4mmol)を添加し、30分撹拌した。過酸化物試験紙で反応系内の過酸化物が完全に分解されたことを確認した。内温90℃でジオキサン200gを加え、生成物を晶析させ、固体をろ取しジオキサンで洗浄した。得られた固体を室温で、50%メタノール水溶液中で撹拌、固体をろ取しメタノールで洗浄した。更に当該固体をメタノール400g中で撹拌して、ろ取しメタノールで洗浄した。室温、1〜2hPaの減圧下乾燥させることにより、エポキシ基含有重合体(B−1)の白色固体96.3gを得た(収率99%、転化率100%)。エポキシ基含有重合体(B−1)の物性は、以下の通り。
エポキシ基含有率(Ep):100%
密度:991kg/m3、
融点:116℃、
針入硬度:1以下、
Mn:1,500、
Mw:5,000、
Mw/Mn:3.3
官能基含有率Fc:100%
1H-NMR δ(C2D2Cl4) 0.88 (t, J = 6.9 Hz, 末端メチル基), 0.93-2.25 (m), 3.22-3.41 (m, 酸素原子のα位), 3.43-3.70 (m, 酸素原子のα位)
融点 (Tm) = 115℃
官能基含有率Fc:100%
1H-NMR δ(C2D2Cl4) 0.88 (t, J = 6.6 Hz, 末端メチル基), 0.92-2.18 (m), 3.22-3.72 (m, 酸素原子のα位)
融点 (Tm) = 116℃
官能基含有率Fc:100%
1H-NMR δ(C2D2Cl4) 0.88 (t, J = 6.9 Hz, 末端メチル基), 0.92-2.40 (m), 2.45-3.18 (m, 窒素原子のα位), 3.40-3.90 (m, 酸素原子のα位)
融点 (Tm) = 115℃
Claims (5)
- エチレンと少なくとも1種のジエンからなる共重合体、またはエチレンと少なくとも1種のジエン及び少なくとも1種の炭素数3〜20のα−オレフィンからなる共重合体であって、ジエンに由来する繰り返し単位の全部または一部が一般式(Ia)及び一般式(Ib)から選ばれる少なくとも1種で示される構造であるビシナル置換型官能基含有エチレン系共重合体。
(式(Ia)及び(Ib)中、*は重合体中での結合位置を表し、Q1〜Q7は水素原子またはアルキル基を表し、Q3とQ7は結合して環を形成しても良く、またQ6、Q7が結合して環を形成しても良い。Aは単結合またはアルキレン基を表し、X、Yは、一方が水酸基、ポリアルキレングリコール基またはアシルオキシ基を表し、他方は一般式(II)、一般式(III)、一般式(IV)のいずれかで示される基、シアノ基、カルボキシル基、エステル基またはアミド基を表し、XとYは互いに結合して環を形成していてもよい。)
- 請求項1記載のビシナル置換型官能基含有エチレン系共重合体を含むトナー用離型剤。
- 請求項1記載のビシナル置換型官能基含有エチレン系共重合体を含む顔料分散剤。
- 請求項1記載のビシナル置換型官能基含有エチレン系共重合体を含む塩化ビニル樹脂用滑剤。
- 請求項1記載のビシナル置換型官能基含有エチレン系共重合体を含む帯電防止剤。
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JP2020033438A (ja) * | 2018-08-29 | 2020-03-05 | 株式会社三栄興業 | 官能基化シクロオレフィンポリマー |
CN116814990A (zh) * | 2023-08-31 | 2023-09-29 | 中国科学院过程工程研究所 | 利用疏水性低共熔溶剂萃取分离钒砷溶液中钒的方法 |
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CN104169809A (zh) * | 2012-03-28 | 2014-11-26 | 三井化学株式会社 | 电子照相用调色剂 |
JP5800987B2 (ja) * | 2012-03-28 | 2015-10-28 | 三井化学株式会社 | 電子写真用トナー |
EP2833207A4 (en) * | 2012-03-28 | 2015-11-25 | Mitsui Chemicals Inc | ELECTROPHOTOGRAPHIC TONER |
US9323166B2 (en) | 2012-03-28 | 2016-04-26 | Mitsui Chemicals, Inc. | Electrophotographic toner |
TWI574127B (zh) * | 2012-03-28 | 2017-03-11 | Mitsui Chemicals Inc | Electronic photographic toner |
JP2020033438A (ja) * | 2018-08-29 | 2020-03-05 | 株式会社三栄興業 | 官能基化シクロオレフィンポリマー |
JP7168200B2 (ja) | 2018-08-29 | 2022-11-09 | 株式会社三栄興業 | 官能基化シクロオレフィンポリマー |
CN116814990A (zh) * | 2023-08-31 | 2023-09-29 | 中国科学院过程工程研究所 | 利用疏水性低共熔溶剂萃取分离钒砷溶液中钒的方法 |
CN116814990B (zh) * | 2023-08-31 | 2023-11-10 | 中国科学院过程工程研究所 | 利用疏水性低共熔溶剂萃取分离钒砷溶液中钒的方法 |
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