JP6543116B2 - 色素化合物、トナー及び該トナーの製造方法 - Google Patents
色素化合物、トナー及び該トナーの製造方法 Download PDFInfo
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- JP6543116B2 JP6543116B2 JP2015133453A JP2015133453A JP6543116B2 JP 6543116 B2 JP6543116 B2 JP 6543116B2 JP 2015133453 A JP2015133453 A JP 2015133453A JP 2015133453 A JP2015133453 A JP 2015133453A JP 6543116 B2 JP6543116 B2 JP 6543116B2
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- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 238000010298 pulverizing process Methods 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
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- 238000004062 sedimentation Methods 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229940067741 sodium octyl sulfate Drugs 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 229940080350 sodium stearate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 229960000776 sodium tetradecyl sulfate Drugs 0.000 description 1
- WFRKJMRGXGWHBM-UHFFFAOYSA-M sodium;octyl sulfate Chemical compound [Na+].CCCCCCCCOS([O-])(=O)=O WFRKJMRGXGWHBM-UHFFFAOYSA-M 0.000 description 1
- SMECTXYFLVLAJE-UHFFFAOYSA-M sodium;pentadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCOS([O-])(=O)=O SMECTXYFLVLAJE-UHFFFAOYSA-M 0.000 description 1
- UPUIQOIQVMNQAP-UHFFFAOYSA-M sodium;tetradecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCOS([O-])(=O)=O UPUIQOIQVMNQAP-UHFFFAOYSA-M 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
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- 125000002130 sulfonic acid ester group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- XLKZJJVNBQCVIX-UHFFFAOYSA-N tetradecane-1,14-diol Chemical compound OCCCCCCCCCCCCCCO XLKZJJVNBQCVIX-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 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
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- KQBSGRWMSNFIPG-UHFFFAOYSA-N trioxane Chemical compound C1COOOC1 KQBSGRWMSNFIPG-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- ZRQNRTRXAVFCMB-UHFFFAOYSA-N tris(2,4,5-trioxa-1-stanna-3-borabicyclo[1.1.1]pentan-1-yl) borate Chemical compound [Sn+4].[Sn+4].[Sn+4].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-] ZRQNRTRXAVFCMB-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
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000001392 ultraviolet--visible--near infrared spectroscopy Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000012178 vegetable wax Substances 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
- 239000000080 wetting agent Substances 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/09—Colouring agents for toner particles
- G03G9/0906—Organic dyes
- G03G9/0922—Formazane dyes; Nitro and Nitroso dyes; Quinone imides; Azomethine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Developing Agents For Electrophotography (AREA)
Description
しかしながら、イエロー、マゼンタ、シアンそれぞれのカラートナーが形成する画像における色再現領域は、コンピューターディスプレイ画面上の色再現領域を完全にカバーできていないのが現状である。その技術的な障壁は、コンピューターディスプレイ画面が透過光による加色法で視認されるのに対し、カラートナーを用いて電子写真法によって形成される画像は反射光による減色法で視認されるという原理の違いにも起因する。近年、カラートナー用着色材として、モニターの色再現性をよりよくするため、彩度・明度の高い染料を用いる例が報告されている。
例えば、キサンテン染料(特許文献1、2参照)やメチン染料(特許文献3、4参照)を用いたトナーが報告されている。一般的に染料系の着色剤は透明性に優れている分、カバーリング力をあげるために、ある程度の色材量を必要とする。しかしながら色材量を多くすることで、染料本来の透明性、発色性が損なわれるため、1グラムあたりの発色団の吸光度の強度が強い染料開発が求められている。
一方で、高速化・小型化・高画質化などの要求に答える形で懸濁重合法で製造されたトナーが市場から注目されている(非特許文献1参照)。
すなわち本発明は、下記一般式(1)で表される構造を有する色素化合物を提供する。
本発明者らは、前記した従来技術の課題を解決すべく鋭意検討を行った。その結果、結着樹脂、ワックス及び着色剤を含有するトナーであって、着色剤として、下記一般式(1)で表される構造を有する色素化合物を含有することでカバーリング力の高いトナーを提供できることを見出した。カバーリング力を高める要因として、ピリドン環のN−N結合基およびカルボン酸アミド基にアセチル基をそれぞれ有していることが考えられる。
一般式(1)中、R3が一般式(2)または一般式(3)で表わされる構造を有することが好ましい。
一般式(2)中、R7は水素原子、アルキル基、アルコキシ基を表す。R8またはR9は独立してアルキル基を表す。前記一般式(3)中、R10乃至R14はそれぞれ独立してアルキル基、アルコキシ基を表す。*は、結合部位を表す。]
一般式(1)中、R1におけるアルキル基としては、特に限定されるものではないが、メチル基、エチル基、n−プロピル基、iso−プロピル基、n−ブチル基、sec−ブチル基、tert−ブチル基、オクチル基、ドデシル基、ノナデシル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、メチルシクロヘキシル基、2−エチルプロピル基、2−エチルヘキシル基、シクロヘキセニルエチル基などの飽和、または不飽和の直鎖状、分岐状、または、環状の炭素数1乃至20個の1級乃至3級のアルキル基が挙げられる。
一般式(1)中、R1におけるアラルキル基としては、特に限定されるものではないが、ベンジル基、トリメチルベンジル基、ジメチルベンジル基等が挙げられる。
R7〜R14におけるアルキル基としては、特に限定されるものではないが、例えば、メチル基、エチル基、n−プロピル基、iso−プロピル基、n−ブチル基等の炭素数1〜4個のアルキル基が挙げられる。
R7〜R14におけるアルコキシ基としては、特に限定されるものではないが、例えば、メトキシ基、エトキシ基、プロポキシル基、ブトキシ基、ヘキシルオキシ基等のアルコキシ基が挙げられる。
本発明のトナーに用いる結着樹脂としては、特に限定されるものではないが、例えば、熱可塑性樹脂などを挙げることができる。
ワックスとは、トナー定着時のオフセットを防止する目的で使用される材料を意味する。
本発明のトナーにおける着色剤としては、一般式(1)で表わされる色素化合物を用いるが、一般式(1)で表わされる色素化合物を単独で用いても良く、2種以上を混合して用いても良い。また、必要に応じて他の色素化合物を併用することができる。
本発明のトナーにおいては、必要に応じて荷電制御剤を混合して用いることも可能である。これにより、現像システムに応じた最適な摩擦帯電量のコントロールが可能となる。
本発明のトナーにおいては、流動化剤として無機微粉体を添加してもよい。無機微粉体としては、シリカ、酸化チタン、アルミナまたはそれらの複酸化物や、これらを表面処理したものなどの微粉体が使用できる。
本発明のトナーに用いられる色素分散体について説明する。
本発明のトナーは懸濁重合法によって製造することができる。懸濁重合法トナーの製造方法について説明する。まず、一般式(1)で表される色素化合物を含む着色剤、重合性単量体、ワックス成分および重合開始剤などを混合して重合性単量体組成物を調製する。次に、該重合性単量体組成物を水系媒体中に分散して重合性単量体組成物の粒子を造粒する。そして、水系媒体中にて重合性単量体組成物の粒子中の重合性単量体を重合させてトナー粒子を得る。
本発明のトナーは、懸濁造粒法によっても製造することができる。懸濁造粒法の製造工程では加熱工程を有さないため、低融点ワックスを用いた場合に起こる樹脂とワックス成分の相溶化を抑制し、相溶化に起因するトナーのガラス転移温度の低下を防止することができる。また、懸濁造粒法は、結着樹脂の選択肢が広く、一般的に定着性に有利とされるポリエステル樹脂を主成分にすることが容易である。そのため、懸濁重合法を適用できない樹脂組成のトナーを製造する場合に有利な製造方法である。
本発明のトナーは粉砕法によっても製造することができる。粉砕法トナーは、混合機、熱混練機、分級機など、当該事業者には公知の製造装置を用いて製造することができる。
本発明のトナーは乳化凝集法によっても製造することもできる。乳化凝集法トナーの製造方法について説明する。まず、各種分散液を調整する。この時、必要に応じてワックス分散液、樹脂粒子分散液、一般式(1)で表される色素化合物を含有する着色剤粒子分散液、その他トナー成分を混合して調製してもよい。これらの混合液を凝集し凝集体粒子を形成する工程(凝集工程)、並びに、該凝集体粒子を加熱し融合する工程(融合工程)、洗浄工程、乾燥工程を経て、乳化凝集法トナーを得ることができる。
界面活性剤の具体例としては、これらに限定されるものではないが、ポリビニルアルコール、メチルセルロース、カルボキシメチルセルロース、ポリアクリル酸ナトリウムの如き水溶性高分子;ドデシルベンゼンスルホン酸ナトリウム、オクタデシル硫酸ナトリウム、オレイン酸ナトリウム、ラウリル酸ナトリウム、ステアリン酸カリウムの如きアニオン性界面活性剤;ラウリルアミンアセテート、ラウリルトリメチルアンモニウムクロライドの如きカチオン性界面活性剤;ラウリルジメチルアミンオキサイドの如き両性イオン性界面活性剤;ポリオキシエチレンアルキルエーテル、ポリオキシエチレンアルキルフェニルエーテル、ポリオキシエチレンアルキルアミンの如きノニオン性界面活性剤;リン酸三カルシウム、水酸化アルミニウム、硫酸カルシウム、炭酸カルシウム、炭酸バリウムの如き無機化合物が挙げられる。なお、これらは単独で用いても良く、また、必要に応じて2種以上を組み合せて用いてもよい。
凝集体粒子を形成させる方法としては、特に限定されるものではないが、pH調整剤、凝集剤、安定剤などを前記混合液中に添加・混合し、温度、機械的動力(撹拌)などを適宜加える方法が好適に例示できる。
融合工程では、前記凝集体粒子を加熱して融合することでトナー粒子を形成する。加熱の温度としては、凝集体粒子に含まれる樹脂のガラス転移温度(Tg)から樹脂の分解温度の間であればよい。例えば、凝集工程と同様の撹拌下で、界面活性剤の添加やpH調整などにより、凝集の進行を止め、樹脂粒子の樹脂のガラス転移温度以上の温度に加熱することにより凝集体粒子を融合・合一させる。加熱の時間としては、融合が十分に進む程度でよく、具体的には10分間乃至10時間程度行えばよい。
乳化凝集法においては、融合工程後に得られたトナー粒子を適切な条件で洗浄、濾過、乾燥などすることにより、トナー粒子を得る。この場合、トナーとして十分な帯電特性、信頼性を確保するために、前記トナー粒子を十分に洗浄することが好ましい。
乾燥工程には、通常の振動型流動乾燥法、スプレードライ法、凍結乾燥法、フラッシュジェット法など、公知の方法を利用することができる。トナー粒子の乾燥後の含水分率は、1.5質量%以下であることが好ましく、より好ましくは1.0質量%以下である。
以下、液体現像剤の製造方法について説明する。
濃硫酸 5mL、酢酸15mL を加え氷冷下撹拌する。0〜5℃を保持しながら 15mmolの中間体(1)を徐々に添加する。さらに同温度で35mmolのt−BuOHを滴下する。滴下後溶液を0〜5℃で保持しながら 1時間 撹拌し、その後徐々に液温を室温に戻す。
反応終了後、水500mL中に反応液を注ぎ込み、析出した沈殿を濾過後、クロロホルムで抽出し、炭酸水素ナトリウム溶液 で洗浄する。有機層を硫酸ナトリウムで乾燥し、減圧下濃縮後、残渣に無水酢酸30mLを加え150℃、アルゴン雰囲気下3時間撹拌した。反応溶液を法令した後、メタノール50mLを加え、室温にて1時間撹拌した後減圧下濃縮した。得られた残渣をカラムクロマトグラフィーにより精製(展開溶媒:酢酸エチル/ヘプタン)した。4.8gの化合物(1)を得た。
[1]MALDI−TOF−MSによる質量分析:m/z=864.383(M)
合成例1において、ピリドン化合物(1)およびアルデヒド化合物(1)をそれぞれ対応するピリドン化合物およびアルデヒド化合物に変更した以外は、合成例1と同様な操作で、化合物(15)、(17)、(24)を得た。
[化合物(15)についての分析結果]
[1]MALDI−TOF−MSによる質量分析:m/z=837.457(M)
[化合物(17)についての分析結果]
[1]MALDI−TOF−MSによる質量分析:m/z=837.329(M)
[化合物(24)についての分析結果]
[1]MALDI−TOF−MSによる質量分析:m/z=704.561(M)
以下に記載する方法で本発明のトナー及び比較用トナーを製造した。
本発明の色素化合物である前記化合物(1)6部、スチレン120部の混合物をアトライター(日本コークス工業(株)製)により3時間分散させて色素分散体(1)を得た。
・スチレン単量体 46.0部
・n−ブチルアクリレート単量体 34.0部
・サリチル酸アルミニウム化合物 2.0部
(オリエント化学工業(株)製 ボントロンE−88)
・樹脂 10.0部
(プロピレンオキサイド変性ビスフェノールAとイソフタル酸との重縮合物、ガラス転移温度Tg=65℃、重量平均分子量Mw=10000、数平均分子量Mn=6000)
・エステルワックス 25.0部
(DSC測定における最大吸熱ピークのピーク温度=70℃、Mn=704)
・ジビニルベンゼン単量体 0.10部
前記混合物を60℃に加温し、T.K.ホモミキサーを用いて5000rpmにて均一に溶解・分散した。これに重合開始剤である2,2’−アゾビス(2,4−ジメチルバレロニトリル)10部を溶解し、重合性単量体組成物を調製した。
実施例1において、化合物(1)を化合物(15)、(17)、(24)に各々変更した以外は実施例1と同様にして本発明のトナー(2)乃至(4)を得た。
実施例1において、化合物(1)6部を用いる代わりに、化合物(1)3部とC.I.Pigment Red 122(クラリアントジャパン(株)製、商品名「Toner Magenta E」)3部の2種を用いることに変更した以外は、実施例1と同様にして本発明のトナー(5)を得た。
実施例1において、化合物(1)6部を用いる代わりに、化合物(24)3部とC.I.Pigment Red 122(クラリアントジャパン(株)製、商品名「Toner Magenta E」)3部の2種を用いることに変更した以外は、実施例1と同様にして本発明のトナー(6)を得た。
実施例1において、化合物(1)を下記比較化合物(1)、(2)に各々変更した以外は実施例1と同様にして比較用トナー(1)、(2)を得た。
スチレン82.6部、アクリル酸n−ブチル9.2部、アクリル酸1.3部、ヘキサンジオールアクリレート0.4部、n−ラウリルメルカプタン3.2部を混合し溶解させた。この溶液にネオゲンRK(第一工業製薬(株)製)1.5部のイオン交換水150部の水溶液を添加して、分散させた。さらに10分間ゆっくりと撹拌しながら、過硫酸カリウム0.15部のイオン交換水10部の水溶液を添加した。窒素置換した後、温度70℃で6時間乳化重合を行った。重合終了後、反応液を室温まで冷却し、イオン交換水を添加することで固形分濃度が12.5質量%、体積基準のメジアン径が0.2μmの樹脂粒子分散液を得た。
実施例7において、化合物(1)を化合物(15)、(17)、(24)に各々変更した以外は実施例7と同様の操作で本発明のトナー(8)乃至(10)を得た。
実施例7において、化合物(1)50部を用いる代わりに、化合物(1)25部とC.I.Pigment Red 122(クラリアントジャパン(株)製、商品名「Toner Magenta E」)25部の2種を用いることに変更した以外は、実施例7と同様にして本発明のトナー(11)を得た。
実施例7において、化合物(1)を比較化合物(1)、(2)に各々変更した以外は実施例7と同様にして比較用トナー(3)、(4)を得た。
結着樹脂(ポリエステル樹脂):100部(Tg55℃、酸価20mgKOH/g、水酸基価16mgKOH/g、ピークトップ分子量Mp=4500、数平均分子量Mn=2300、重量平均分子量Mw=38000)、本発明の色素化合物である前記化合物(1):3部、1,4−ジ−t−ブチルサリチル酸アルミニウム化合物:0.5部、パラフィンワックス(最大吸熱ピーク温度78℃):5部を、ヘンシェルミキサー(FM−75J型、三井鉱山(株)製)でよく混合した後、温度130℃に設定した2軸混練機(PCM−45型、池貝鉄鋼(株)製)にて60kg/hrのFeed量で混練(吐出時の混練物温度は約150℃)した。得られた混練物を冷却し、ハンマーミルで粗砕した後、機械式粉砕機(T−250:フロイント・ターボ(株)製)にて20kg/hrのFeed量で微粉砕した。 さらに得られたトナー微粉砕物を、コアンダ効果を利用した多分割分級機により分級することで、トナー母粒子(12)を得た。
実施例12において、化合物(1)を化合物(15)、(17)、(24)に各々変更した以外は実施例12と同様の方法で本発明のトナー(13)乃至(15)を得た。
実施例12において、化合物(1)3部を用いる代わりに、化合物(1)1.5部とC.I.Pigment Red 122(クラリアントジャパン(株)製、商品名「Toner Magenta E」)1.5部の2種を用いることに変更した以外は、実施例12と同様にして本発明のトナー(16)を得た。
実施例12において、化合物(1)3部を用いる代わりに、化合物(24)1.5部とC.I.Pigment Red 122(クラリアントジャパン(株)製、商品名「Toner Magenta E」)1.5部の2種を用いることに変更した以外は、実施例12と同様にして本発明のトナー(17)を得た。
実施例10において、化合物(1)を比較化合物(1)、(2)に各々変更した以外は実施例10と同様にして比較用トナー(5)、(6)を得た。
前記トナー粒子の評価を以下のように行った。なお、評価結果については後述の表1に示した。
トナー粒子の重量平均粒径D4、及び個数平均粒径D1の測定
前記トナーの個数平均粒径(D1)及び重量平均粒径(D4)はコールター法による粒度分布解析にて測定した。測定装置として、コールターカウンターTA−IIあるいはコールターマルチサイザーII(ベックマン・コールター(株)製)を用い、該装置の操作マニュアルに従い測定した。電解液としては、1級塩化ナトリウムを用いて、約1%塩化ナトリウム水溶液を調製した。例えば、ISOTON−II(コールターサイエンティフィックジャパン(株)製)が使用できる。具体的な測定方法としては、前記電解水溶液100乃至150mL中に、分散剤として界面活性剤(好ましくはアルキルベンゼンスルホン酸塩)を、0.1乃至5mL加え、さらに測定試料(トナー粒子)を2乃至20mg加える。試料を懸濁した電解液は、超音波分散器で約1乃至3分間分散処理を行う。得られた分散処理液について、100μmのアパーチャーを装着した前記測定装置を用いて、2.00μm以上のトナーの体積、個数を測定し、トナーの体積分布と個数分布とを算出する。得られたデータを用いて、トナー粒子の個数分布から求めた個数平均粒径(D1)と、トナー粒子の体積分布から求めたトナー粒子の重量平均粒径(D4)(各チャンネルの中央値をチャンネル毎の代表値とする)及びD4/D1を求めた。
A:D4/D1が1.30未満(粒度分布が非常に良い)
B:D4/D1が1.30以上1.35未満(粒度分布が良い)
C:D4/D1が1.35以上(粒度分布が悪い)
2cm2のガラス基板上に0.5gのトナーを均一に敷き詰め、BIG HEATER(井元製作所製)で160℃、1kgの条件で熱プレスを行い、発色性評価用サンプルを作製した。
[トナーのカバーリング力評価]
得られた発色性評価用サンプルに関して、UVスペクトル測定(UV−3600、UV−VIS−NIR SPECTROPHOTOMETER、(株)島津製作所製)を行いカバーリング力の評価を行った。本発明におけるカバーリング力とは、染料1グラムあたりの吸光度を指標とした。染料のカバーリング力は、1グラム当たりの発色団の吸光度×発色団の数で決まる。1グラムあたりの吸光度が高いほど、少ない発色団の数、すなわち低濃度でも高着色となり、カバーリング力が向上される。
評価は以下の基準に従った。20mgのサンプルを100mLの溶媒に溶かして調製した溶液の吸収スペクトルを測定し、1g換算しアブソーバンスで比較した。アブソーバンスが110以上であればカバーリング力が非常に高いと判断した。
A:アブソーバンスが110以上(カバーリング力が非常に高い)
B:アブソーバンスが105以上110未満である。(カバーリング力が高い)
C:アブソーバンスが105未満(カバーリング力が高くない)
Claims (3)
- 請求項1または2に記載の色素化合物を含有することを特徴とするトナー。
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