JPWO2012102137A1 - 電荷制御剤及びそれを用いたトナー - Google Patents
電荷制御剤及びそれを用いたトナー Download PDFInfo
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- JPWO2012102137A1 JPWO2012102137A1 JP2012554736A JP2012554736A JPWO2012102137A1 JP WO2012102137 A1 JPWO2012102137 A1 JP WO2012102137A1 JP 2012554736 A JP2012554736 A JP 2012554736A JP 2012554736 A JP2012554736 A JP 2012554736A JP WO2012102137 A1 JPWO2012102137 A1 JP WO2012102137A1
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- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- CAPIMQICDAJXSB-UHFFFAOYSA-N trichloro(1-chloroethyl)silane Chemical compound CC(Cl)[Si](Cl)(Cl)Cl CAPIMQICDAJXSB-UHFFFAOYSA-N 0.000 description 1
- FLPXNJHYVOVLSD-UHFFFAOYSA-N trichloro(2-chloroethyl)silane Chemical compound ClCC[Si](Cl)(Cl)Cl FLPXNJHYVOVLSD-UHFFFAOYSA-N 0.000 description 1
- ULIAPOFMBCCSPE-UHFFFAOYSA-N tridecan-7-one Chemical compound CCCCCCC(=O)CCCCCC ULIAPOFMBCCSPE-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- XYJRNCYWTVGEEG-UHFFFAOYSA-N trimethoxy(2-methylpropyl)silane Chemical compound CO[Si](OC)(OC)CC(C)C XYJRNCYWTVGEEG-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- KHOQXNHADJBILQ-UHFFFAOYSA-N trimethyl(sulfanyl)silane Chemical compound C[Si](C)(C)S KHOQXNHADJBILQ-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 229940096522 trimethylolpropane triacrylate Drugs 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- GRPURDFRFHUDSP-UHFFFAOYSA-N tris(prop-2-enyl) benzene-1,2,4-tricarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C(C(=O)OCC=C)=C1 GRPURDFRFHUDSP-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000001060 yellow colorant Substances 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
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- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract
Description
また、一般式(1)中のR1及びR2で表される「置換基を有していてもよい炭素原子数5〜10のシクロアルキル基」としては、「置換基を有していてもよい炭素原子数5〜6のシクロアルキル基」が好ましく、これらは「無置換」であることがより好ましい。
一般式(1)中のR3〜R8で表される「置換基を有していてもよい炭素原子数5〜10のシクロアルキル基」としては、「置換基を有していてもよい炭素原子数5〜6のシクロアルキル基」が好ましく、これらは「無置換」であることがより好ましい。
一般式(1)中のR3〜R8で表される「置換基を有していてもよい炭素原子数2〜6の直鎖状若しくは分岐状のアルケニル基」としては、「置換基を有していてもよい炭素原子数2〜4の直鎖状若しくは分岐状のアルケニル基」が好ましく、これらは「無置換」であることがより好ましい。
一般式(1)中のR3〜R8で表される「置換基を有していてもよい炭素原子数5〜10のシクロアルキルオキシ基」としては、「置換基を有していてもよい炭素原子数5〜6のシクロアルキルオキシ基」が好ましく、これらは「無置換」であることがより好ましい。
ここで、合成されるヒダントイン誘導体は、縮合反応によって生じる二重結合の幾何異性において、E体、Z体又はE体とZ体の混合物として生成する。
なお、下記構造式では、水素原子は省略して記載している。また、下記構造式において、二重結合の幾何異性は一方のみを記載しているが、E体、Z体又はE体とZ体の混合物、のいずれであってもよい。
2価のアルコール成分としては、エチレングリコール、プロピレングリコール、1,3−ブタンジオール、1,4−ブタンジオール、2,3−ブタンジオール、ジエチレングリコール、トリエチレングリコール、1,5−ペンタンジオール、1,6−へキサンジオール、ネオペンチルグリコール、2−エチル−1,3−ヘキサンジオール、水素化ビスフェノールA、又はビスフェノールAにエチレンオキシド、プロピレンオキシドなどの環状エーテルが重合して得られるジオールなどがあげられる。
また、水酸基価は、30mgKOH/g以下であることが好ましく、10mgKOH/g〜25mgKOH/gが更に好ましい。
本実施形態において、非晶性のポリエステル樹脂と結晶性のポリエステル樹脂の2種以上を混合して用いてもよい。この場合、それぞれの相溶性を考慮に入れて材料を選択するのが好ましい。
非晶性のポリエステル樹脂は多価カルボン酸成分、好ましくは芳香族多価カルボン酸と多価アルコール成分とから合成されるものが好適に用いられる。
結晶性のポリエステル樹脂は2価カルボン酸成分、好ましくは脂肪族ジカルボン酸と2価アルコール成分とから合成されるものが好適に用いられる。
また、ポリエステル系重合体、ビニル重合体とその他の結着樹脂を併用する場合、全体の結着樹脂の酸価が0.1mgKOH/g〜50mgKOH/gである樹脂を60質量%以上有するものが好ましい。
(1)試料は予め結着樹脂(重合体成分)以外の添加物を除去して使用するか、結着樹脂及び架橋された結着樹脂以外の成分の酸価及び含有量を予め求めておく。試料の粉砕品0.5〜2.0gを精秤し、重合体成分の重さをWgとする。例えば、トナーから結着樹脂の酸価を測定する場合は、着色剤又は磁性体などの酸価及び含有量を別途測定しておき、計算により結着樹脂の酸価を求める。
(2)300(ml)のビーカーに試料を入れ、トルエン/エタノール(体積比4/1)の混合液150(ml)を加え溶解する。
(3)0.1mol/LのKOHのエタノール溶液を用いて、電位差滴定装置を用いて滴定する。
(4)この時のKOH溶液の使用量をS(ml)とし、同時にブランクを測定し、この時のKOH溶液の使用量をB(ml)とし、以下の式(1)で算出する。ただしfはKOH濃度のファクターである。
酸価(mgKOH/g)=[(S−B)×f×5.61]/W (1)
本実施形態の重合トナーにおいて、軟化点が80から140℃の範囲内である結着樹脂が好適に用いられる。結着樹脂の軟化点が80℃未満であると、定着後及び保管時のトナー及びトナーの画像安定性が悪化する場合がある。一方、軟化点が140℃を超えると、低温定着性が悪化してしまう場合がある。
前記顔料を単独で使用しても構わないが、染料と顔料と併用してその鮮明度を向上させた方がフルカラー画像の画質の点からより好ましい。
前記の着色剤の使用量は、結着樹脂100量部に対して、0.1〜20質量部とするのが好ましい。
可塑化作用を有するワックスとしては、例えば融点の低いワックス、又は分子の構造上に分岐のあるもの、若しくは極性基を有する構造のワックスがあげられる。離型作用を有するワックスとしては、融点の高いワックス、分子の構造では、直鎖構造のワックス、又は、官能基を有さない無極性のワックスがあげられる。使用例としては、2種以上の異なるワックスの融点の差が10℃〜100℃となる組み合わせ、及び、ポリオレフィンとグラフト変性ポリオレフィンの組み合わせなどがあげられる。
また、粒径均一性が高い(体積平均粒径/個数平均粒径が1.00〜1.30)ことが望ましい。
本実施形態に係るトナーは、粉砕型トナーの場合の形状係数(SF−1)の平均値が100〜400が好ましく、形状係数2(SF−2)の平均値が100〜350が好ましい。
SF−1=((ML2×π)/4A)×100
(式中、MLは粒子の最大長、Aは一粒子の投影面積を示す。)
SF−2=(PM2/4Aπ)×100
(式中、PMは粒子の周囲長、Aは一粒子の投影面積を示す。)。
本実施形態に係るトナーのDSC測定において観測される吸熱ピークにおいて70〜120℃の領域に最大ピークのピークトップ温度があることが好ましい。
窒素置換した反応容器に、1−メチルヒダントイン6.85g(60ミリモル)、ベンズアルデヒド6.1ml(60ミリモル)、酢酸ナトリウム14.77g(180ミリモル)、酢酸100mlを加え、攪拌しながら96時間加熱還流した。室温まで放冷した後、水500mlを入れた反応容器に反応溶液を加え、室温で30分攪拌した。析出する粗製物をろ過によって採取し、水で洗浄した後、60℃で減圧乾燥することによって、5−ベンジリデン−1−メチルヒダントイン(例示化合物2)の淡黄色結晶1.79g(収率14.8%)を得た。
δ(ppm)=11.34(1H)、7.92−7.94(2H)、7.31−7.38(3H)、6.42(1H)、3.09(3H)。
窒素置換した反応容器に、1−メチルヒダントイン22.82g(200ミリモル)、4−tert−ブチルベンズアルデヒド32.45g(200ミリモル)、酢酸ナトリウム49.82g(600ミリモル)、プロピオン酸300mlを加え、攪拌しながら100時間加熱還流した。室温まで放冷した後、水1500mlを入れた反応容器に反応溶液を加え、室温で1時間攪拌した。析出する粗製物をろ過によって採取し、水で洗浄した後、60℃で減圧乾燥することによって、5−(4−tert−ブチルベンジリデン)−1−メチルヒダントイン(例示化合物3)の淡橙色結晶29.26g(収率56.6%)を得た。
δ(ppm)=11.32(1H)、7.33−7.89(4H)、6.37−6.62(1H)、2.85−3.08(3H)、1.29(9H)。
窒素置換した反応容器に、1−メチルヒダントイン17.12g(150ミリモル)、4−メチルベンズアルデヒド18.02g(150ミリモル)、酢酸ナトリウム37.36g(450ミリモル)、プロピオン酸200mlを加え、攪拌しながら76時間攪拌した。室温まで放冷した後、水500mlを入れた反応容器に反応溶液を加え、室温で1時間攪拌した。析出する粗製物をろ過によって採取し、水で洗浄し、さらにメタノールで洗浄した後、60℃で減圧乾燥することによって、5−(4−メチルベンジリデン)−1−メチルヒダントイン(例示化合物4)の淡橙色結晶19.58g(収率60.36%)を得た。
δ(ppm)=11.33(1H)、7.17−7.87(4H)、6.36−6.6.62(1H)、2.82−3.34(3H)、2.32(3H)。
窒素置換した反応容器に、1−メチルヒダントイン17.12g(150ミリモル)、3−メチルベンズアルデヒド18.02g(150ミリモル)、酢酸ナトリウム24.91g(300ミリモル)、プロピオン酸75mlを加え、攪拌しながら100時間加熱還流した。室温まで放冷した後、水250mlを入れた反応容器に反応溶液を加え、室温で1時間攪拌した。析出する粗製物をろ過によって採取し、水で洗浄し、さらにメタノールで洗浄した後、60℃で減圧乾燥することによって、5−(3−メチルベンジリデン)−1−メチルヒダントイン(例示化合物5)の淡橙色結晶9.37g(収率28.9%)を得た。
δ(ppm)=11.31(1H)、7.12−7.79(4H)、6.35(1H)、3.08(3H)、2.31(3H)。
窒素置換した反応容器に、1−メチルヒダントイン17.12g(150ミリモル)、2−メチルベンズアルデヒド18.02g(150ミリモル)、酢酸ナトリウム24.91g(300ミリモル)、プロピオン酸75mlを加え、攪拌しながら100時間加熱還流した。室温まで放冷した後、水250mlを入れた反応容器に反応溶液を加え、室温で1時間攪拌した。析出する粗製物をろ過によって採取し、水で洗浄し、さらにメタノールで洗浄した後、60℃で減圧乾燥することによって、5−(2−メチルベンジリデン)−1−メチルヒダントイン(例示化合物6)の淡橙色結晶20.1g(収率62.0%)を得た。
δ(ppm)=11.31(1H)、7.11−7.92(4H)、6.39−6.61(1H)、2.63−3.10(3H)、2.27−2.30(3H)。
窒素置換した反応容器に、1−メチルヒダントイン22.82g(200ミリモル)、4−クロロベンズアルデヒド28.11g(200ミリモル)、ピペリジン19.8ml(200ミリモル)、酢酸11.5ml(200ミリモル)、n−ブタノール40mlを加え、攪拌しながら48時間加熱還流した。室温まで放冷した後、析出する粗製物をろ過によって採取した。メタノールで洗浄し、さらに水で洗浄した後、60℃で減圧乾燥することによって、5−(4−クロロベンジリデン)−1−メチルヒダントイン(例示化合物7)の淡黄色結晶32.65g(収率69.0%)を得た。
δ(ppm)=11.33(1H)、7.94−7.96(2H)、7.41−7.43(2H)、6.37(1H)、3.08(3H)。
窒素置換した反応容器に、1−メチルヒダントイン17.12g(150ミリモル)、3−クロロベンズアルデヒド21.09g(150ミリモル)、ピペリジン14.8ml(150ミリモル)、酢酸8.6ml(150ミリモル)、n−ブタノール40mlを加え、攪拌しながら48時間加熱還流した。室温まで放冷した後、析出する粗製物をろ過によって採取した。エタノールで洗浄し、さらに水で洗浄した後、60℃で減圧乾燥することによって、5−(3−クロロベンジリデン)−1−メチルヒダントイン(例示化合物8)の淡黄色結晶13.86g(収率39.0%)を得た。
δ(ppm)=11.41(1H)、8.11(1H)、7.81−7.83(1H)、7.35−7、42(2H)、6.40(1H)、3.08(3H)。
窒素置換した反応容器に、1−メチルヒダントイン17.12g(150ミリモル)、2−クロロベンズアルデヒド21.09g(150ミリモル)、ピペリジン14.8ml(150ミリモル)、酢酸8.6ml(150ミリモル)、n−ブタノール40mlを加え、攪拌しながら48時間加熱還流した。室温まで放冷した後、析出する粗製物をろ過によって採取した。メタノールで洗浄し、さらに水で洗浄した後、60℃で減圧乾燥することによって、5−(2−クロロベンジリデン)−1−メチルヒダントイン(例示化合物9)の淡黄色結晶20.76g(収率58.5%)を得た。
δ(ppm)=11.36(1H)、7.83−7.85(1H)、7.47−7.49(1H)、7.29−7、34(2H)、6.35(1H)、3.09(3H)。
窒素置換した反応容器に、1−メチルヒダントイン17.12g(150ミリモル)、4−メトキシベンズアルデヒド20.42g(150ミリモル)、ピペリジン14.8ml(150ミリモル)、酢酸8.6ml(150ミリモル)、n−ブタノール40mlを加え、攪拌しながら72時間加熱還流した。室温まで放冷した後、析出する粗製物をろ過によって採取した。メタノールで洗浄し、さらに水で洗浄した後、60℃で減圧乾燥することによって、5−(4−メトキシベンジリデン)−1−メチルヒダントイン(例示化合物10)の淡黄色結晶29.84g(収率70.5%)を得た。
δ(ppm)=11.28(1H)、7.99−8.01(2H)、6.94−6.95(2H)、6.36(1H)、3.81(3H)、3.07(3H)。
窒素置換した反応容器に、1−メチルヒダントイン17.12g(150ミリモル)、3−メトキシベンズアルデヒド20.42g(150ミリモル)、ピペリジン14.8ml(150ミリモル)、酢酸8.6ml(150ミリモル)、n−ブタノール40mlを加え、攪拌しながら96時間加熱還流した。室温まで放冷した後、析出する粗製物をろ過によって採取した。メタノールで洗浄し、さらに水で洗浄した後、60℃で減圧乾燥することによって、5−(3−メトキシベンジリデン)−1−メチルヒダントイン(例示化合物11)の淡黄色結晶14.02g(収率40.2%)を得た。
δ(ppm)=11.37(1H)、7.73(1H)、7.45−7.47(1H)、7.27−7.29(1H)、6.89−6.90(1H)、6.38(1H)、3.77(3H)、3.08(3H)。
窒素置換した反応容器に、ヒダントイン10.0g(100ミリモル)、ベンズアルデヒド11.1ml(110ミリモル)、ピペリジン9.9ml(150ミリモル)、酢酸5.7ml(150ミリモル)、n−ブタノール20mlを加え、攪拌しながら6時間加熱還流した。室温まで放冷した後、析出する粗製物をろ過によって採取した。メタノールで洗浄し、さらに水で洗浄した後、60℃で減圧乾燥することによって、5−ベンジリデンヒダントイン(例示化合物12)の淡黄色結晶10.02g(収率53.2%)を得た。
δ(ppm)=11.31(2H)、7.62−7.63(2H)、7.40−7.42(2H)、7.32−7.35(1H)、6.42(1H)。
窒素置換した反応容器に、ヒダントイン15.03g(150ミリモル)、2−メチルベンズアルデヒド18.02g(150ミリモル)、ピペリジン14.82ml(150ミリモル)、酢酸8.6ml(150ミリモル)、n−ブタノール40mlを加え、攪拌しながら24時間加熱還流した。室温まで放冷した後、析出する粗製物をろ過によって採取した。メタノールで洗浄し、さらに水で洗浄した後、60℃で減圧乾燥することによって、5−(2−メチルベンジリデン)ヒダントイン(例示化合物13)の淡黄色結晶20.8g(収率68.5%)を得た。
δ(ppm)=11.34(2H)、7.52−7.53(1H)、7.21−7.26(3H)、6.48(1H)、2.33(3H)。
窒素置換した反応容器に、ヒダントイン15.03g(150ミリモル)、3−メチルベンズアルデヒド18.02g(150ミリモル)、ピペリジン14.82ml(150ミリモル)、酢酸8.6ml(150ミリモル)、n−ブタノール40mlを加え、攪拌しながら48時間加熱還流した。室温まで放冷した後、析出する粗製物をろ過によって採取した。メタノールで洗浄し、さらに水で洗浄した後、60℃で減圧乾燥することによって、5−(2−メチルベンジリデン)ヒダントイン(例示化合物14)の淡黄色結晶16.6g(収率54.7%)を得た。
δ(ppm)=11.32(2H)、7.47(1H)、7.37−7.39(1H)、7.27−7.30(1H)、7.14−7.15(1H)、6.37(1H)、2.33(3H)。
窒素置換した反応容器に、ヒダントイン15.03g(150ミリモル)、4−tert-ブチルベンズアルデヒド24.34g(150ミリモル)、ピペリジン14.82ml(150ミリモル)、酢酸8.6ml(150ミリモル)、n−ブタノール40mlを加え、攪拌しながら24時間加熱還流した。室温まで放冷した後、析出する粗製物をろ過によって採取した。メタノールで洗浄し、さらに水で洗浄した後、60℃で減圧乾燥することによって、5−(4−tert-ブチルベンジリデン)ヒダントイン(例示化合物15)の淡黄色結晶25.33g(収率69.1%)を得た。
δ(ppm)=11.33(2H)、7.55−7.56(2H)、7.41−7.42(2H)、6.40(1H)、1.29(9H)。
窒素置換した反応容器に、ヒダントイン11.3g(113ミリモル)、トルエン500mlを加えて加熱した。還流下、N,N−ジメチルアセトアミドジメチルアセタール45.0g(338ミリモル)のトルエン(50ml)溶液を滴下し、さらに攪拌しながら3時間加熱還流した。室温まで放冷した後、析出する不溶物をろ過によって採取した。トルエンで洗浄した後、60℃で減圧乾燥することによって、3−メチルヒダントイン8.4g(収率68.4%)を得た。
δ(ppm)=10.77(1H)、7.64−7.65(2H)、7.34−7.41(3H)、6.53(1H)、2.96(3H)。
合成実施例15で合成した、3−メチルヒダントイン4.0g(35.1ミリモル)、4−メチルベンズアルデヒド4.2g(35.1ミリモル)、ピペリジン3.0g(35.1ミリモル)、酢酸2.1g(35.1ミリモル)、n−ブタノール30mlを窒素置換した反応容器に加え、攪拌しながら12時間加熱還流した。室温まで放冷した後、析出する粗製物をろ過によって採取した。メタノールで洗浄し、さらに水で洗浄した後、60℃で減圧乾燥することによって、5−(4−メチルベンジリデン)−3−メチルヒダントイン(例示化合物17)の淡黄色結晶6.1g(収率80.5%)を得た。
δ(ppm)=10.71(1H)、7.54−7.55(2H)、7.22−7.23(2H)、6.50(1H)、2.96(3H)、2.35(3H)。
合成実施例15で合成した、3−メチルヒダントイン4.0g(35.1ミリモル)、4−tert−ブチルベンズアルデヒド5.7g(35.1ミリモル)、ピペリジン3.0g(35.1ミリモル)、酢酸2.1g(35.1ミリモル)、n−ブタノール30mlを窒素置換した反応容器に加え、攪拌しながら50時間加熱還流した。室温まで放冷した後、析出する粗製物をろ過によって採取した。メタノールで洗浄し、さらに水で洗浄した後、60℃で減圧乾燥することによって、5−(4−tert−ブチルベンジリデン)−3−メチルヒダントイン(例示化合物18)の淡黄色結晶6.2g(収率68.1%)を得た。
δ(ppm)=10.70(1H)、7.57−7.59(2H)、7.42−7.43(2H)、6.51(1H)、2.96(3H)、1.29(9H)。
合成実施例15で合成した、3−メチルヒダントイン4.0g(35.1ミリモル)、4−クロロベンズアルデヒド4.9g(35.1ミリモル)、ピペリジン3.0g(35.1ミリモル)、酢酸2.1g(35.1ミリモル)、n−ブタノール30mlを窒素置換した反応容器に加え、攪拌しながら42時間加熱還流した。室温まで放冷した後、析出する粗製物をろ過によって採取した。メタノールで洗浄し、さらに水で洗浄した後、60℃で減圧乾燥することによって、5−(4−クロロベンジリデン)−3−メチルヒダントイン(例示化合物19)の淡黄色結晶5.6g(収率67.5%)を得た。
δ(ppm)=10.83(1H)、7.65−7.67(2H)、7.45−7.47(2H)、6.50(1H)、2.96(3H)。
(非磁性トナー1の製造)
スチレン−アクリレート系共重合体樹脂(三井化学株式会社製、商品名CPR−100、酸価0.1mgKOH/g)91部、合成実施例14で合成したヒダントイン誘導体(例示化合物15)1部、カーボンブラック(三菱化学株式会社製、商品名MA−100)5部及び低分子量ポリプロピレン(三洋化成株式会社製、商品名ビスコール550P)3部を130℃の加熱混合装置(2軸押出混練機)によって溶融混合した。冷却した混合物をハンマーミルで粗粉砕した後、ジェットミルで微粉砕し、分級して体積平均粒径9±0.5μmの非磁性トナー1を得た。
非磁性トナー1をノンコート系のフェライトキャリア(パウダーテック株式会社製F−150)と4対100質量部(トナー:キャリア)の割合で混合振とうしてトナーを負に帯電させた後、ブローオフ粉体帯電量測定装置で帯電量を測定した。その結果、−35.8μc/gであった。
(非磁性トナー2の製造及び評価)
合成実施例14で合成したヒダントイン誘導体(例示化合物15)を合成実施例12で合成したヒダントイン誘導体(例示化合物13)に代えたこと以外は、実施例19と同様の方法で非磁性トナー2を調製し、ブローオフ粉体帯電量測定装置によって帯電量を評価した。その結果、ノンコート系のフェライトキャリア(パウダーテック株式会社製F−150)と混合した場合の帯電量は−34.5μc/gであった。同様に、シリコンコート系のフェライトキャリアー(パウダーテック社製F96−150)と混合した場合の帯電量は−24.3μc/gであった。
(比較非磁性トナーの製造と評価)
合成実施例14で合成したヒダントイン誘導体(例示化合物15)を3,5−tert−ブチルサリチル酸と亜鉛の塩に代えたこと以外は、実施例19と同様の方法で比較非磁性トナーを調製し、ブローオフ粉体帯電量測定装置によって帯電量を評価した。その結果、ノンコート系のフェライトキャリア(パウダーテック株式会社製F−150)と混合した場合の帯電量は−23.0μc/gであった。同様に、シリコンコート系のフェライトキャリアー(パウダーテック社製F96−150)と混合した場合の帯電量は−15.0μc/gであった。
(樹脂分散液の調製)
ポリエステル樹脂(三菱レイヨン株式会社製、DIACRON ER−561)80部、酢酸エチル320部、イソプロピルアルコール32部を混合し、ホモジナイザー(株式会社美粒製、泡レスミキサー NGM−0.5TB)を用いて、5000〜10000rpmで攪拌しながら0.1質量%のアンモニア水を適量滴下して転相乳化させ、さらにエバポレーターで減圧しながら脱溶剤を行って、樹脂分散液を得た。この分散液における樹脂粒子の体積平均粒径は0.2μmであった(樹脂粒子濃度はイオン交換水で調整して20質量%とした)。
ドデシルベンゼンスルホン酸ナトリウム0.2部、ソルボンT-20(東邦化学工業株式会社製)0.2部、イオン交換水17.6部を混合溶解し、さらに合成実施例14で合成したヒダントイン誘導体(例示化合物15)2.0部、ジルコニアビーズ(ビーズの粒子径0.65mmφ、15ml相当量)を加えて、ペイントコンディショナー(UNION N.J.(USA)社製、Red Devil No.5400−5L)で3時間分散させた。篩いを用いてジルコニアビーズを除き、イオン交換水で調整して10質量%の電荷制御剤分散液とした。
温度計、pH計、攪拌機を備えた反応容器に前記樹脂分散液125部、20質量%のドデシルベンゼンスルホン酸ナトリウム水溶液1.0部、イオン交換水125部を加え、液温を30℃に制御しながら、回転数150rpmで30分撹拌した。1質量%の硝酸水溶液を添加してpHを3.0に調整し、さらに5分間撹拌した。ホモジナイザー(IKAジャパン社製、ウルトラタラックスT−25)で分散させながら、ポリ塩化アルミニウム0.125部を加え、液温を50℃まで昇温させた後、さらに30分間分散させた。前記樹脂分散液62.5部、前記電荷制御剤分散液4.0部を加えた後、1質量%の硝酸水溶液を添加してpHを3.0に調整し、さらに30分間分散した。攪拌機を用いて400〜700rpmで撹拌しながら、5質量%の水酸化ナトリウム水溶液8.0部を加え、トナーの体積平均粒子径が9.5μmとなるまで撹拌を継続した。液温を75℃まで昇温させた後、さらに2時間撹拌し、体積平均粒子径が6.0μmとなり、粒子形状が球形化したことを確認した後、氷水を用いて急速冷却させた。ろ過によって採取し、イオン交換水で分散洗浄を行った。分散洗浄は、分散後のろ液の電気伝導度が20μS/cm以下となるまで繰り返した。その後、40℃の乾燥機で乾燥してトナー粒子を得た。
得られたトナーを166メッシュ(目開き90μm)の篩いで篩分して評価用トナーとした。
得られた評価用トナー2部、シリコンコート系のフェライトキャリアー(パウダーテック社製F96−150)100部の割合で混合して振とうし、トナーを負に帯電させた後、ブローオフ粉体帯電量測定装置で温度25℃、湿度50%の雰囲気下で飽和帯電量の測定を行った。その結果、飽和帯電量は−41.2μC/gであった。
比較のために、電荷制御剤分散液を加える操作を省略したこと以外は、実施例21と同様の条件でトナーを作製し、飽和帯電量測定を行った。その結果、飽和帯電量は−20.5μC/gであった。
すなわち本発明の一般式(1)で表されるヒダントイン誘導体を有効成分として含有する電荷制御剤を用いることによって重合トナーに高い帯電性能を付与することができる。
Claims (5)
- 下記一般式(1)で表されるヒダントイン誘導体の1種又は2種以上を有効成分として含有する電荷制御剤。
- 下記一般式(2)で表されるヒダントイン誘導体の1種又は2種以上を有効成分として含有する電荷制御剤。
- 下記一般式(3)で表されるヒダントイン誘導体の1種又は2種以上を有効成分として含有する電荷制御剤。
- 請求項1〜3のいずれか一項に記載の電荷制御剤、着色剤及び結着樹脂を含有する、トナー。
- 請求項1〜3のいずれか一項に記載の電荷制御剤、着色剤及び結着樹脂を含有する、重合トナー。
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JP5893571B2 JP5893571B2 (ja) | 2016-03-23 |
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JP2012554736A Active JP5893571B2 (ja) | 2011-01-27 | 2012-01-17 | 電荷制御剤及びそれを用いたトナー |
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US (1) | US20130266895A1 (ja) |
EP (1) | EP2669741A4 (ja) |
JP (1) | JP5893571B2 (ja) |
KR (1) | KR101883517B1 (ja) |
CN (1) | CN103348290A (ja) |
WO (1) | WO2012102137A1 (ja) |
Families Citing this family (3)
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JP6435615B2 (ja) * | 2014-03-14 | 2018-12-12 | 株式会社リコー | 静電荷像現像用トナーの製造方法 |
US9804516B2 (en) * | 2015-05-12 | 2017-10-31 | Ricoh Company, Ltd. | Toner, developer, image forming apparatus, and process cartridge |
DE102018112373A1 (de) | 2017-05-24 | 2019-02-21 | Hodogaya Chemical Co., Ltd. | Ladungskontrollmittel mit makromolekularen Verbindungen sowie Toner |
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KR101417790B1 (ko) | 2006-04-13 | 2014-07-15 | 호도가야 가가쿠 고교 가부시키가이샤 | 산화형 혼합 환형 페놀 황화물, 이것을 사용한 전하 제어제 및 토너 |
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-
2012
- 2012-01-17 KR KR1020137021982A patent/KR101883517B1/ko active IP Right Grant
- 2012-01-17 CN CN2012800064182A patent/CN103348290A/zh active Pending
- 2012-01-17 EP EP12739281.9A patent/EP2669741A4/en not_active Withdrawn
- 2012-01-17 US US13/885,731 patent/US20130266895A1/en not_active Abandoned
- 2012-01-17 WO PCT/JP2012/050858 patent/WO2012102137A1/ja active Application Filing
- 2012-01-17 JP JP2012554736A patent/JP5893571B2/ja active Active
Also Published As
Publication number | Publication date |
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KR101883517B1 (ko) | 2018-07-30 |
EP2669741A1 (en) | 2013-12-04 |
CN103348290A (zh) | 2013-10-09 |
US20130266895A1 (en) | 2013-10-10 |
KR20140005986A (ko) | 2014-01-15 |
WO2012102137A1 (ja) | 2012-08-02 |
JP5893571B2 (ja) | 2016-03-23 |
EP2669741A4 (en) | 2016-05-11 |
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