JP2018155880A - イミド安息香酸誘導体を用いた電荷制御剤及びトナー - Google Patents
イミド安息香酸誘導体を用いた電荷制御剤及びトナー Download PDFInfo
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- JP2018155880A JP2018155880A JP2017051714A JP2017051714A JP2018155880A JP 2018155880 A JP2018155880 A JP 2018155880A JP 2017051714 A JP2017051714 A JP 2017051714A JP 2017051714 A JP2017051714 A JP 2017051714A JP 2018155880 A JP2018155880 A JP 2018155880A
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- LATKICLYWYUXCN-UHFFFAOYSA-N naphthalene-1,3,6-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 LATKICLYWYUXCN-UHFFFAOYSA-N 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- WDAISVDZHKFVQP-UHFFFAOYSA-N octane-1,2,7,8-tetracarboxylic acid Chemical compound OC(=O)CC(C(O)=O)CCCCC(C(O)=O)CC(O)=O WDAISVDZHKFVQP-UHFFFAOYSA-N 0.000 description 1
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 239000004209 oxidized polyethylene wax Substances 0.000 description 1
- 235000013873 oxidized polyethylene wax Nutrition 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- HDBWAWNLGGMZRQ-UHFFFAOYSA-N p-Vinylbiphenyl Chemical compound C1=CC(C=C)=CC=C1C1=CC=CC=C1 HDBWAWNLGGMZRQ-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000019809 paraffin wax Nutrition 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 239000012165 plant wax Substances 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- 238000007639 printing Methods 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
- 239000008213 purified water Substances 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical class C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 1
- 238000000790 scattering method Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011257 shell material Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- VEALVRVVWBQVSL-UHFFFAOYSA-N strontium titanate Chemical compound [Sr+2].[O-][Ti]([O-])=O VEALVRVVWBQVSL-UHFFFAOYSA-N 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical group OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical class S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 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
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-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
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 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
- 239000011787 zinc oxide Substances 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
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Developing Agents For Electrophotography (AREA)
Abstract
Description
の形態に限定されるものではない。
尚、下記構造式では、水素原子は一部省略して記載している。
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、またはビスフェノール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。
(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、結着樹脂および架橋された結着樹脂以外の成分の酸価およ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、着色剤または磁性体などの酸価およ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)
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℃のものの組み合わせや、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。
300mlコルベンに4−アミノ安息香酸10.0g(0.073mol)を量りとり、ジメチルホルムアミド(DMF)を10ml加え、室温・窒素雰囲気下で撹拌し溶解させた。30mlのDMFに溶解させた無水マレイン酸7.85g(0.080mol)を滴下ロートよりゆっくり滴下した。室温で4時間反応させた後、反応液を氷水1Lに注加し、黄色の析出物を確認後、氷が解けるまで撹拌した。吸引濾過を行い、濾物を終夜70℃で減圧乾燥を行い、中間体17.1gを99.5%の収率で得た。
中間体10.0g(0.043mol)を1000mlコルベンに仕込み、p−トルエンスルホン酸を2g、トルエンを500ml、N−メチルピロリドンを100ml、ジメチルアセトアミドを50ml加え、110℃に昇温し7時間反応させた。反応終了後、反応液をナスフラスコに移液し、エバポレータにてオイルバス100℃、減圧の条件で溶媒が留去しなくなるまで濃縮した。濃縮液を500mlの氷水中に注加した。析出した黄色固体を吸引濾過し、濾物を終夜70℃で減圧乾燥を行い、8.8g淡黄色固体、95.3%の収率で得た。
合成例1の無水マレイン酸をcis―4―シクロヘキセン-1,2―ジカルボン酸無水物に変えた以外は同様の操作を行い、10.38g淡黄色固体、収率93.0%で得た。
合成例1の無水マレイン酸を5−ノルボルネン−2,3−ジカルボン酸無水物に変えた以外は同様の操作を行い、4.67g淡黄色固体、収率70.8%で得た。
合成例1の無水マレイン酸をexo−3,6−エポキシ―1,2,3,6―テトラヒドロフタル酸無水物に変えた以外は同様の操作を行い、4.66g淡黄色固体、収率59.6%で得た。
100mlコルベンにジメチルホルムアミド(DMF)を50ml入れ、脱気及び窒素置換を2時間行った。例示化合物2を5.0g(0.023mol)、スチレンを2.4g(0.023mol)、アゾビスイソブチロニトリル(AIBN)を0.1g(0.460mmol)を入れ撹拌、窒素下で80℃に加温し、4時間反応を行った。反応終了後、反応液をメタノール1Lに少しずつ注加し、白色固体を析出させた。吸引濾過を行い、濾物を終夜70℃で減圧乾燥を行い、5.17g白色固体、収率69.9%で得た。
100mlコルベンにDMFを50ml入れ、脱気及び窒素置換を2時間行った。例示化合物2を5.0g(0.023mol)とアクリル酸エチルを2.31g(0.023mol)、そして、AIBNを0.08g(0.37mmol)を入れ撹拌、窒素下で65℃に昇温し、32時間反応を行った。反応中、28時間目にメタクリル酸エチルを1.31g(0.012mol)とAIBNを0.08g追加した。反応終了後、反応液を濃縮し、アセトンで溶解させた。この溶液を市水800mLに少しずつ注加し、褐色固体を析出させた。吸引濾過を行い、濾物を終夜70℃で減圧乾燥を行った。乾燥品を200mLナスフラスコに入れトルエン50mLとアセトニトリル10mLを加え、65℃に昇温し分散洗浄を1時間行った。吸引濾過し、濾物を終夜70℃で減圧乾燥を行い、2.14g白色固体、収率25.3%で得た。
100mlコルベンにDMFを50ml入れ、脱気及び窒素置換を2時間行った。例示化合物2を3.90g(0.018mol)とスチレンを1.87g(0.018mol)、アクリル酸エチルを1.80g(0.018mol)、そして、AIBNを0.08g(0.49mmol)を入れ撹拌、窒素下で80℃に昇温し、6.5時間反応を行った。反応中、5.5時間目にスチレンを0.62g(0.006mol)を追加した。反応終了後、反応液をナスフラスコに移液しエバポレータで濃縮乾固させた。アセトン50mLを加えて溶解し、20%メタノール水800mLに少しずつ注加し、薄褐色固体を析出させた。吸引濾過を行い、濾物をビーカーに移して細かく粉砕し、50%メタノール水で分散洗浄を1時間行った。再度吸引濾過し、濾物を終夜80℃で減圧乾燥を行い、6.04g白色固体、収率73.7%で得た。
100mLコルベンにDMFを50mL入れ脱気及び窒素置換を2時間行った。例示化合物2を10.00g(0.046mol)とブチルビニルエーテルを4.61g(0.046mol)、そしてAIBN0.16g(0.99mmol)を入れ撹拌、窒素下で80℃に昇温し、7時間反応を行った。反応終了後、反応液を濃縮乾固し、アセトン100mLで溶解し、市水800mLに反応液を注加し、茶色固体を析出させた。吸引濾過を行い、濾物をビーカーに移して100mLのアセトンに溶解し、市水800mLに反応液を注加し、茶色固体を析出させた。吸引濾過し、濾物を終夜80℃で減圧乾燥を行った。乾燥品をトルエン200mLとアセトニトリル40mLの混合溶媒に分散させ、65℃で3時間分散洗浄を行った。吸引濾過し、濾物をヘキサンでかけ洗いし、終夜80℃で減圧乾燥を行った。10.51g白色固体、収率71.9%で得た。
上記方法で合成した電荷制御剤を以下の方法で粒子径を調整した。
電荷制御剤4gと精製水20gおよび0.65mmφジルコニアビーズ45gを50ml容量のポリプロピレン製容器に仕込んだ。ペイントコンディショナー(RED DEVIL EQUIPMENT Co.(USA)社製、Red Devil No.1400−0H)にて30分から6時間振とうし粉砕した。粉砕後金網(50メッシュ)を用いてジルコニアビーズを除去した。試料を−60℃で凍結し、凍結乾燥装置で3日間乾燥させた。粒子径をレーザー回析・散乱法(マイクロトラック粒度分布測定装置)で測定し、平均粒子径が、6μm以下となっていることを確認した。
ブローオフ帯電量測定機(TB−200型、東芝ケミカル社製)を用いて、上記合成した電荷制御剤を帯電させた後、各環境における初期帯電量及び飽和帯電量の測定を行った。 ブローオフ帯電量測定条件は以下である。
現像剤量:0.2000g±0.005g、
ブロー時間:60s、
N2ブロー圧:0.2kgf/cm2(シリコンコートF96−150)、
T/C=4%、
ボールミル回転数:110rpm。
[実施例1]
合成例1で得られた化合物を、シリコ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、F96−150)100質量部に対して0.5質量部の割合で混合して振とうし、合成例1で得られた化合物(例示化合物No.2)を帯電させる。帯電させた後、ブローオフ帯電量測定機(東芝ケミカル社製、TB−200型)を用いて、温度25℃、湿度50%の雰囲気下(NN環境下)における飽和帯電量の測定を行った。また、ノンコートキャリア((パウダーテック株式会社製、F−150)についても同様の測定を行った。帯電量測定結果を表2に示す。
実施例1と同じ方法で、合成例2〜8で得られた化合物単独での帯電量測定を行った、結果を表2に示す。
比較のために、市販の電荷制御剤(T−77:有色アゾ錯体、保土谷化学工業株式会社製)を比較化合物として、上記の測定方法で帯電性を測定した。それらの結果を表2に示す。
比較のために、市販の電荷制御剤(TN−105:白色サリチル酸錯体、保土谷化学工業株式会社製)を比較化合物として、上記の測定方法で帯電性を測定した。それらの結果を表2に示す。
[実施例9]
ポリエステル系樹脂(三菱レイヨン株式会社製、商品名FC−316、酸価9mgKOH/g)91質量部、合成例5で合成したマレイミド安息香酸誘導体(例示化合物No.17)1質量部、カーボンブラック(三菱化学株式会社製、商品名MA−100)5質量部およ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質量部を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をシリコ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F96−150)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機(東芝ケミカル社製、TB−200型)を用いて、温度25℃、湿度50%の雰囲気下(NN環境下)で帯電量を測定した。結果を表3に示す。
[実施例10]
[比較例3]
Claims (6)
- 下記一般式(1)で表されるイミド安息香酸誘導体を有効成分とすることを特徴とする負帯電性の電荷制御剤。
- 少なくとも1種の請求項1に記載の一般式(1)で表されるイミド安息香酸誘導体と、少なくとも1種のアルキニル基含有化合物との共重合反応生成物である高分子化合物を有効成分とすることを特徴とする負帯電性の電荷制御剤。
- 前記一般式(1)で表されるイミド安息香酸誘導体の含有量が、0.1ないし80モル%であることを特徴とする請求項2に記載の負帯電性の電荷制御剤。
- 前記高分子化合物の重量平均分子量(Mw)が、5000ないし100000の範囲にあることを特徴とする請求項2または請求項3に記載の負帯電性の電荷制御剤。
- 前記アルキニル基含有化合物が、スチレン、スチレン誘導体、(メタ)アクリル酸、(メタ)アクリル酸エステル、ビニルエーテル誘導体から選ばれる少なくとも1種であることを特徴とする請求項2〜請求項4に記載の負帯電性の電荷制御剤。
- 請求項1〜5の負帯電性の電荷制御剤と着色剤および結着樹脂を含有することを特徴とする負帯電性のトナー。
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