JP4806596B2 - トナー及びその製造方法、現像剤、画像形成方法並びにトナー収納容器 - Google Patents
トナー及びその製造方法、現像剤、画像形成方法並びにトナー収納容器 Download PDFInfo
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- JP4806596B2 JP4806596B2 JP2006186942A JP2006186942A JP4806596B2 JP 4806596 B2 JP4806596 B2 JP 4806596B2 JP 2006186942 A JP2006186942 A JP 2006186942A JP 2006186942 A JP2006186942 A JP 2006186942A JP 4806596 B2 JP4806596 B2 JP 4806596B2
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- 150000007524 organic acids Chemical class 0.000 description 1
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- 239000011574 phosphorus Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
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- WLJVNTCWHIRURA-UHFFFAOYSA-M pimelate(1-) Chemical compound OC(=O)CCCCCC([O-])=O WLJVNTCWHIRURA-UHFFFAOYSA-M 0.000 description 1
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- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
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- 229920000223 polyglycerol Polymers 0.000 description 1
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- QPMDWIOUHQWKHV-ODZAUARKSA-M potassium;(z)-4-hydroxy-4-oxobut-2-enoate Chemical compound [K+].OC(=O)\C=C/C([O-])=O QPMDWIOUHQWKHV-ODZAUARKSA-M 0.000 description 1
- LLLCSBYSPJHDJX-UHFFFAOYSA-M potassium;2-methylprop-2-enoate Chemical compound [K+].CC(=C)C([O-])=O LLLCSBYSPJHDJX-UHFFFAOYSA-M 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
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- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 description 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 1
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- 238000000197 pyrolysis Methods 0.000 description 1
- 235000012752 quinoline yellow Nutrition 0.000 description 1
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- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
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- 239000000376 reactant Substances 0.000 description 1
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- 239000008165 rice bran oil Substances 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
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- ZIWRUEGECALFST-UHFFFAOYSA-M sodium 4-(4-dodecoxysulfonylphenoxy)benzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCOS(=O)(=O)c1ccc(Oc2ccc(cc2)S([O-])(=O)=O)cc1 ZIWRUEGECALFST-UHFFFAOYSA-M 0.000 description 1
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- HWCHICTXVOMIIF-UHFFFAOYSA-M sodium;3-(dodecylamino)propanoate Chemical compound [Na+].CCCCCCCCCCCCNCCC([O-])=O HWCHICTXVOMIIF-UHFFFAOYSA-M 0.000 description 1
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- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical class CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
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- SZEMGTQCPRNXEG-UHFFFAOYSA-M trimethyl(octadecyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C SZEMGTQCPRNXEG-UHFFFAOYSA-M 0.000 description 1
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- 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
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- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
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- 229910000859 α-Fe Inorganic materials 0.000 description 1
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Description
請求項9に記載の発明は、トナーの製造方法において、ポリエステル樹脂を含む組成物を有機溶媒中に溶解又は分散させて第一の液を調製する工程と、該第一の液を、樹脂粒子を含む水性溶媒中に乳化又は分散させて第二の液を調製する工程を有し、該ポリエステル樹脂は、2個以上6個以下の水酸基を有するポリオール並びに水酸基及び/又はカルボキシル基を有するポリエステル樹脂からなる群より選択される一種以上の化合物と環状エステルを開環重合することにより得られ、該環状エステルは、L−ラクチド、D−ラクチド、DL−ラクチド及びラセミラクチドからなる群より選択される一種以上であることを特徴とする。これにより、透明性が高い画像を得ることが可能なトナーの製造方法を提供することができる。
請求項10に記載の発明は、請求項9に記載のトナーの製造方法において、前記組成物は、1級アミノ基を有する化合物と、該1級アミノ基と反応可能な官能基を有するポリエステルプレポリマーをさらに含み、該ポリエステルプレポリマーは、2個以上6個以下の水酸基を有するポリオール並びに水酸基及び/又はカルボキシル基を有するポリエステル樹脂からなる群より選択される一種以上の化合物と環状エステルを開環重合することにより得られるポリエステル樹脂と、前記1級アミノ基と反応可能な官能基を有する化合物を反応させることにより得られ、該環状エステルは、L−ラクチド、D−ラクチド、DL−ラクチド及びラセミラクチドからなる群より選択される一種以上であることを特徴とする。これにより、耐オフセット性を向上させることができる。
請求項11に記載の発明は、請求項10に記載のトナーの製造方法において、前記ポリエステルプレポリマーに対する前記ポリエステル樹脂の重量比が5/95以上80/20以下であることを特徴とする。これにより、耐ホットオフセット性と定着下限温度の向上の両立をはかることができる。
請求項12に記載の発明は、請求項9乃至11のいずれか一項に記載のトナーの製造方法において、前記樹脂粒子は、体積平均粒径が5nm以上2μm以下であることを特徴とする。これにより、粒径分布の狭いトナーを得ることができる。
(1)ビニル炭化水素:
(1−1)脂肪族ビニル炭化水素:
炭素数2〜12のアルケン(例えば、エチレン、プロピレン、ブテン、イソブチレン、ペンテン、ヘプテン、ジイソブチレン、オクテン、ドデセン、オクタデセン、炭素数3〜24のα−オレフィン等);炭素数4〜12のアルカジエン(例えば、ブタジエン、イソプレン、1,4−ペンタジエン、1,6−ヘキサジエン等)。
(1−2)脂環式ビニル炭化水素:
炭素数6〜15のシクロアルケン又はジシクロアルケン(例えば、シクロヘキセン、ビニルシクロヘキセン、エチリデンビシクロヘプテン等);炭素数5〜12のシクロアルカジエン又はジシクロアルカジエン(例えば、(ジ)シクロペンタジエン等);テルペン(例えば、ピネン、リモネン、インデン等)等。
(1−3)芳香族ビニル炭化水素:
スチレン;スチレンのハイドロカルビル(炭素数1〜24のアルキル、シクロアルキル、アラルキル及び/又はアルケニル)置換体(例えば、α−メチルスチレン、ビニルトルエン、2,4−ジメチルスチレン、エチルスチレン、ブチルスチレン、フェニルスチレン、シクロヘキシルスチレン、ベンジルスチレン、クロチルベンゼン、ジビニルベンゼン等);ビニルナフタレン等。
(2)カルボキシル基を有するビニルモノマー及びその塩:
炭素数3〜30の不飽和モノカルボン酸(例えば、(メタ)アクリル酸(アクリル酸及び/又はメタクリル酸を表す。以下同様の表現を用いる)、クロトン酸、イソクロトン酸、桂皮酸等);炭素数3〜30の不飽和ジカルボン酸又はその無水物(例えば、(無水)マレイン酸、フマル酸、イタコン酸、(無水)シトラコン酸、メサコン酸等);炭素数3〜30の不飽和ジカルボン酸のモノアルキル(炭素数1〜24)エステル(例えば、マレイン酸モノメチル、マレイン酸モノオクタデシル、フマル酸モノエチル、イタコン酸モノブチル等)等。
(3)スルホ基を有するビニルモノマー及びその塩:
炭素数2〜14のアルケンスルホン酸(例えば、ビニルスルホン酸、(メタ)アリルスルホン酸、メチルビニルスルホン酸等);スチレンスルホン酸及びアルキル(炭素数2〜24)誘導体(例えば、α−メチルスチレンスルホン酸等;炭素数5〜18のスルホ(ヒドロキシ)アルキル(メタ)アクリレート(例えば、スルホプロピル(メタ)アクリレート、2−ヒドロキシ−3−(メタ)アクリロキシプロピルスルホン酸等);炭素数5〜18のスルホ(ヒドロキシ)アルキル(メタ)アクリルアミド(例えば、2−(メタ)アクリロイルアミノ−2,2−ジメチルエタンスルホン酸、2−(メタ)アクリルアミド−2−メチルプロパンスルホン酸);アルキル(炭素数3〜18)アリルスルホコハク酸(例えば、プロピルアリルスルホコハク酸、ブチルアリルスルホコハク酸);ポリ(n=2〜30)オキシアルキレン(オキシエチレン、オキシプロピレン、オキシブチレン:単独、ランダム、ブロックでもよい)モノ(メタ)アクリレートの硫酸エステル(例えば、ポリ(n=5〜15)オキシエチレンモノメタクリレート硫酸エステル等);下記一般式(1−1)〜(1−3)
で表される化合物;これらの塩等が挙げられる。
(4)ホスホノ基を有するビニルモノマー及びその塩:
(メタ)アクリロイルオキシアルキルリン酸モノエステル(アルキル基の炭素数1〜24)(例えば、2−ヒドロキシエチル(メタ)アクリロイルホスフェート、フェニル−2−アクリロイルオキシエチルホスフェート等)、(メタ)アクリロイルオキシアルキルホスホン酸(アルキル基の炭素数1〜24)(例えば、2−アクリロイルオキシエチルホスホン酸等)。
(5)ヒドロキシル基を有するビニルモノマー:
ヒドロキシスチレン、N−メチロール(メタ)アクリルアミド、ヒドロキシエチル(メタ)アクリレート、ヒドロキシプロピル(メタ)アクリレート、ポリエチレングリコールモノ(メタ)アクリレート、(メタ)アリルアルコール、クロチルアルコール、イソクロチルアルコール、1−ブテン−3−オール、プロパルギルアルコール、2−ヒドロキシエチルプロペニルエーテル、ショ糖アリルエーテル等。
(6)含窒素ビニルモノマー:
(6−1)アミノ基を有するビニルモノマー:
アミノエチル(メタ)アクリレート、ジメチルアミノエチル(メタ)アクリレート、ジエチルアミノエチル(メタ)アクリレート、t−ブチルアミノエチルメタクリレート、N−アミノエチル(メタ)アクリルアミド、(メタ)アリルアミン、モルホリノエチル(メタ)アクリレート、4−ビニルピリジン、2−ビニルピリジン、クロチルアミン、N,N−ジメチルアミノスチレン、α−アセトアミノアクリル酸メチル、ビニルイミダゾール、N−ビニルピロール、N−ビニルチオピロリドン、N−アリールフェニレンジアミン、アミノカルバゾール、これらの塩等。
(6−2)アミド基を有するビニルモノマー:
(メタ)アクリルアミド、N−メチル(メタ)アクリルアミド、N−ブチルアクリルアミド、ジアセトンアクリルアミド、N−メチロール(メタ)アクリルアミド、N,N’−メチレンビス(メタ)アクリルアミド、桂皮酸アミド、N,N−ジメチルアクリルアミド等。
(6−3)炭素数3〜10のニトリル基を有するビニルモノマー:
(メタ)アクリロニトリル、シアノスチレン、シアノアクリレート等。
(6−4)4級アンモニウムカチオンからなる基を有するビニルモノマー:
ジメチルアミノエチル(メタ)アクリレート、ジエチルアミノエチル(メタ)アクリレート、ジメチルアミノエチル(メタ)アクリルアミド、ジエチルアミノエチル(メタ)アクリルアミド等の3級アミノ基を有するビニルモノマーの4級化物(塩化メチル、ジメチル硫酸、塩化ベンジル、ジメチルカーボネート等の4級化剤を用いて4級化したもの。例えば、ジメチルジアリルアンモニウムクロリド、トリメチルアリルアンモニウムクロリド等)。
(6−5)炭素数8〜12のニトロ基を有するビニル系モノマー:
ニトロスチレン等。
(7)炭素数6〜18のエポキシ基を有するビニルモノマー:
グルシジル(メタ)アクリレート、テトラヒドロフルフリル(メタ)アクリレート、p−ビニルフェニルフェニルオキシド等。
(8)炭素数2〜16のハロゲン基を有するビニルモノマー:
塩化ビニル、臭化ビニル、塩化ビニリデン、塩化アリル、クロロスチレン、ブロモスチレン、ジクロロスチレン、クロロメチルスチレン、テトラフルオロスチレン、クロロプレン等。
(9)ビニルエステル、ビニル(チオ)エーテル、ビニルケトン、ビニルスルホン:
(9−1)炭素数4〜16のビニルエステル:
酢酸ビニル、プロピオン酸ビニル、酪酸ビニル、ジアリルフタレート、ジアリルアジペート、イソプロペニルアセテート、ビニルメタクリレート、シクロヘキシルメタクリレート、ベンジルメタクリレート、フェニル(メタ)アクリレート、ビニルメトキシアセテート、安息香酸ビニル、炭素数1〜50のアルキル基を有するアルキル(メタ)アクリレート(メチル(メタ)アクリレート、エチル(メタ)アクリレート、ブチル(メタ)アクリレート、ドデシル(メタ)アクリレート、ヘプタデシル(メタ)アクリレート等)、ジアルキルフマレート(2個のアルキル基は、炭素数2〜8の直鎖、分枝鎖又は脂環式の基である)、ジアルキルマレエート(2個のアルキル基は、炭素数2〜8の直鎖、分枝鎖又は脂環式の基である)、ポリ(メタ)アリルオキシアルカン類(ジアリルオキシエタン、トリアリルオキシエタン、テトラアリルオキシプロパン等)等、ポリアルキレングリコール鎖を有するビニル系モノマー(ポリエチレングリコール(分子量300)モノ(メタ)アクリレート、ポリプロピレングリコール(分子量500)モノアクリレート、メチルアルコールエチレンオキシド(以下、エチレンオキシドをEOと記載する)10モル付加物(メタ)アクリレート、ラウリルアルコールEO30モル付加物(メタ)アクリレート等)、ポリ(メタ)アクリレート類(多価アルコール類のポリ(メタ)アクリレート:エチレングリコールジ(メタ)アクリレート、プロピレングリコールジ(メタ)アクリレート、ポリエチレングリコールジ(メタ)アクリレート等)等。
(9−2)炭素数3〜16のビニル(チオ)エーテル:
ビニルメチルエーテル、ビニルエチルエーテル、ビニルブチルエーテル、ビニル2−エチルヘキシルエーテル、ビニルフェニルエーテル、ビニル2−メトキシエチルエーテル、メトキシブタジエン、フェノキシスチレン等。
(9−3)炭素数4〜12のビニルケトン:
ビニルメチルケトン、ビニルエチルケトン、ビニルフェニルケトン等。
(9−4)炭素数2〜16のビニルスルホン:
ジビニルスルフィド、p−ビニルジフェニルスルフィド、ビニルエチルスルフィド、ビニルエチルスルホン、ジビニルスルホン、ジビニルスルホキシド等。
(10)その他のビニル系モノマー:
イソシアナトエチル(メタ)アクリレート、m−イソプロペニル−α,α−ジメチルベンジルイソシアネート等。
−NHR’
で示される2級アミノ基(R’は、アルキル基、例えば、メチル基、エチル基等の炭素数1〜4の低級アルキル基)で置換されたもの(例えば、4,4’−ジ(メチルアミノ)ジフェニルメタン、1−メチル−2−メチルアミノ−4−アミノベンゼン等)、ポリアミドポリアミン(ジカルボン酸(ダイマー酸等)と過剰(カルボン酸1モル当たり2モル以上)のポリアミン(アルキレンジアミン、ポリアルキレンポリアミン等)との縮合により得られる低分子量ポリアミドポリアミン等)、ポリエーテルポリアミン(ポリエーテルポリオール(ポリアルキレングリコール等)のシアノエチル化物の水素化物等)が挙げられる。
〔1〕ビニル系樹脂の場合において、モノマーを出発原料として、懸濁重合法、乳化重合法、シード重合法、分散重合法等の重合反応により、直接、樹脂粒子の水性分散液を製造する方法
〔2〕ポリエステル樹脂、ポリウレタン樹脂、エポキシ樹脂等の重付加又は縮合系樹脂の場合において、前駆体(モノマー、オリゴマー等)又はその溶液を適当な分散剤存在下で水性媒体中に分散させ、その後に加熱したり、硬化剤を加えたりして硬化させて樹脂粒子の水性樹脂分散液を製造する方法
〔3〕ポリエステル樹脂、ポリウレタン樹脂、エポキシ樹脂等の重付加又は縮合系樹脂の場合において、前駆体(モノマー、オリゴマー等)又はその溶液(液体であることが好ましい。加熱により液状化してもよい)中に適当な乳化剤を溶解させた後、水を加えて転相乳化する方法
〔4〕予め重合反応(付加重合、開環重合、重付加、付加縮合、縮合重合等いずれの重合反応様式であってもよい)により合成した樹脂を機械回転式、ジェット式等の微粉砕機を用いて粉砕し、次いで、分級することによって樹脂粒子を得た後、適当な分散剤存在下で水中に分散させる方法
〔5〕予め重合反応(付加重合、開環重合、重付加、付加縮合、縮合重合等いずれの重合反応様式であってもよい)により合成した樹脂の溶液を霧状に噴霧することにより樹脂粒子を得た後、樹脂粒子を適当な分散剤存在下で水中に分散させる方法
〔6〕予め重合反応(付加重合、開環重合、重付加、付加縮合、縮合重合等いずれの重合反応様式であってもよい)により合成した樹脂の溶液に貧溶剤を添加する又は予め加熱溶解させた樹脂の溶液を冷却することにより樹脂粒子を析出させ、次いで、溶剤を除去して樹脂粒子を得た後、樹脂粒子を適当な分散剤存在下で水中に分散させる方法
〔7〕予め重合反応(付加重合、開環重合、重付加、付加縮合、縮合重合等いずれの重合反応様式であってもよい)により合成した樹脂の溶液を、適当な分散剤存在下で水性媒体中に分散させ、これを加熱、減圧等によって溶剤を除去する方法
〔8〕予め重合反応(付加重合、開環重合、重付加、付加縮合、縮合重合等いずれの重合反応様式であってもよい)により合成した樹脂の溶液中に適当な乳化剤を溶解させた後、水を加えて転相乳化する方法
上記〔1〕〜〔8〕の方法において、併用する乳化剤又は分散剤としては、公知の界面活性剤(S)、水溶性ポリマー(T)等を用いることができる。また、乳化又は分散の助剤として有機溶媒(U)、可塑剤(V)等を併用することができる。
〔1〕反応性基を有するプレポリマー(α)が有する反応性基が、活性水素基に対する反応性を有する官能基(α1)であり、硬化剤(β)が活性水素基を有する化合物(β1)であるという組み合わせ。
〔2〕反応性基を有するプレポリマー(α)が有する反応性基が活性水素基(α2)であり、硬化剤(β)が活性水素基に対する反応性を有する化合物(β2)であるという組み合わせ。
〔1〕二以上の構成成分のうちの一つを過剰に用いることで構成成分の官能基を末端に残存させる方法
〔2〕二以上の構成成分のうちの一つを過剰に用いることで構成成分の官能基を末端に残存させ、さらに残存した官能基に対する反応性を有する官能基を有する化合物を反応させる方法
〔2〕の具体例としては、〔1〕で得られたプレポリマーに、ポリイソシアネートを反応させることでイソシアネート基を有するプレポリマーが得られ、ブロック化ポリイソシアネートを反応させることでブロック化イソシアネート基を有するプレポリマーが得られ、ポリエポキシドを反応させることでエポキシ基を有するプレポリマーが得られ、ポリ酸無水物を反応させることで酸無水物基を有するプレポリマーが得られる。
(ただし、Nは、0.1NKOHアルコール溶液のファクター)
なお、酸価を測定する装置は、以下の通りである。
使用電極:DG113−SC(メトラー・トレド社製)
解析ソフト:LabX Light Version 1.00.000
装置の校正:トルエン120mlとエタノール30mlの混合溶媒を使用
測定温度:23℃
また、測定条件は、以下の通りである。
Speed[%]:25
Time[s]:15
EQP titration
Titrant/Sensor
Titrant:CH3ONa
Concentration[mol/L]:0.1
Sensor:DG115
Unit of measurement:mV
Predispensing:to volume
Volume[mL]:1.0
Wait time[s]:0
Titrant addition:Dynamic
dE(set)[mV]:8.0
dV(min)[mL]:0.03
dV(max)[mL]:0.5
Measure mode:Equilibrium controlled
dE[mV]:0.5
dt[s]:1.0
t(min)[s]:2.0
t(max)[s]:20.0
Recognition
Threshold:100.0
Steepest jump only:No
Range:No
Tendency:None
Termination
at maximum volume[mL]:10.0
at potential:No
at slope:No
after number EQPs:Yes
n=1
comb.termination conditions:No
Evaluation
Procedure:Standard
Potential1:No
Potential2:No
Stop for reevaluation:No
次に、樹脂のガラス転移点(Tg)の測定方法について概説する。Tgを測定する装置として、TG−DSCシステムTAS−100(理学電機社製)を使用する。まず、試料約10mgを入れたアルミ製試料容器をホルダユニットに載せ、電気炉中にセットする。次に、室温から昇温速度10℃/分で150℃まで加熱した後、150℃で10分間放置し、室温まで試料を冷却して10分間放置する。さらに、窒素雰囲気下で昇温速度10℃/分で再度150℃まで加熱してDSC測定を行った。Tgは、TAS−100システム中の解析システムを用いて、Tg近傍の吸熱カーブの接線とベースラインとの接点から算出される。
図1に、本発明の現像方法に用いられる画像形成装置の一例を示す。図1に示す画像形成装置は、複写装置本体100、複写装置本体100を載せる給紙テーブル200、複写装置本体100上に取り付けるスキャナ300、さらにその上に取り付ける原稿自動搬送装置(ADF)400を有する。
(エポキシ樹脂粒子分散液の作製)
撹拌棒及び温度計をセットした反応容器に、スチレン化フェノールポリエチレンオキシド付加物エレミノールHB−12(三洋化成工業社製)47部及びビスフェノールAジグリシジルエーテルのエピコート828(油化シェル社製)232部を投入し、均一に溶解させた。攪拌下、反応容器に水を滴下した。水を31部投入したところで、系が乳白色に乳化した。さらに、水を224部滴下し、乳濁液(1)を得た。加熱して、系内温度を70℃まで昇温させた後、エチレンジアミン20部と水446部を混合した液を、系内温度を70℃に維持したまま、2時間かけて滴下した。滴下後、70℃で5時間、90℃で5時間反応・熟成してアミン硬化エポキシ樹脂水性分散液(樹脂粒子分散液A1)を得た。樹脂粒子分散液A1をレーザー式粒度分布測定装置LA−920(堀場製作所製)で測定した体積平均粒径は、0.81μmであった。また、樹脂粒子分散液A1の一部を遠心分離し、さらに水を加えて遠心分離する工程を2回繰り返した後、乾燥して樹脂分を単離した。得られた樹脂分のTg(DSCで測定、以下Tgについて同様)は、120℃であった。
(スチレン−メタクリル酸共重合体樹脂粒子分散液の作製)
撹拌棒及び温度計をセットした反応容器に、水683部、メタクリル酸エチレンオキサイド付加物硫酸エステルのナトリウム塩エレミノールRS−30(三洋化成工業社製)11部、スチレン139部、メタクリル酸138部及び過硫酸アンモニウム1部を仕込み、400rpmで15分間撹拌したところ、白色の乳濁液が得られた。加熱して、系内温度を75℃まで昇温させ、5時間反応させた。さらに、1%過硫酸アンモニウム水溶液30部を加え、75℃で5時間熟成してビニル系樹脂(スチレン−メタクリル酸−メタクリル酸エチレンオキサイド付加物硫酸エステルのナトリウム塩の共重合体)の水性分散液(樹脂粒子分散液A2)を得た。樹脂粒子分散液A2をLA−920で測定した体積平均粒径は、0.15μmであった。次に、樹脂粒子分散液A2の一部を乾燥して樹脂分を単離した。得られた樹脂分のTgは、154℃であった。
(ポリエステル樹脂溶液の作製)
冷却管、撹拌機及び窒素導入管をセットした反応容器中に、ビスフェノールAエチレンオキシド2モル付加物220部、ビスフェノールAプロピレンオキシド3モル付加物561部、テレフタル酸218部、アジピン酸48部及びジブチルスズオキシド2部を仕込み、常圧下、230℃で8時間反応させ、さらに10〜15mmHgの減圧下、5時聞反応させた後、反応容器に無水トリメリット酸45部を入れ、常圧、180℃で2時間反応させ、ポリエステル1を得た。ポリエステル1は、数平均分子量2500、重量平均分子量6700、Tg43℃、酸価25mgKOH/gであった。1000部のポリエステル1を酢酸エチル2000部に溶解、混合し、ポリエステル樹脂溶液1を得た。このとき、樹脂溶液は薄く白濁していた。
(環状エステルを用いたポリエステル樹脂溶液の作製1)
冷却管、撹拌機及び窒素導入管をセットした反応容器中に、グリセリン9部、L−ラクチド288部及びジブチルスズオキシド2部を仕込み、常圧下、160℃で6時間開環重合し、数平均分子量3000のポリエステル2を得た。ポリエステル2−1は、重量平均分子量6300、Tg49℃、酸価8mgKOH/gであった。1000部のポリエステル2−1を酢酸エチル2000部に溶解、混合し、ポリエステル樹脂溶液2−1を得た。このとき、樹脂溶液は薄く白濁していた。
(環状エステルを用いたポリエステル樹脂溶液の作製2)
冷却管、撹拌機及び窒素導入管をセットした反応容器中に、1,2−プロピレングリコール701部(18.8モル)、テレフタル酸ジメチル716部(7.5モル)、アジピン酸180部(2.5モル)及びテトラブトキシチタネート3部を仕込み、180℃で窒素気流下、生成するメタノールを留去しながら、8時間反応させた。次に、230℃まで徐々に昇温しながら、4時間反応させ、さらに、5〜20mmHgの減圧下で反応させ、軟化点が150℃になった時点で取り出した。回収された1,2−プロピレングリコールは、316部(8.5モル)であった。取り出した樹脂を室温まで冷却させた後、粉砕し、粒子化し、ポリエステルaを得た。ポリエステルaは、数平均分子量2000、水酸基価43mgKOH/g、酸価19mgKOH/gであった。なお、括弧内のモル数は、相対的なモル比を意味する。
(環状エステルを用いたポリエステル樹脂溶液の作製3)
冷却管、撹拌機及び窒素導入管をセットした反応容器中に、ヒマシ油ポリオールHS3P−255(豊国製油社製)15部、L−ラクチド500部及びテレフタル酸チタン1部を仕込み、常圧下、160℃で6時間開環重合し、ポリエステル2−3を得た。1000部のポリエステル2−3を酢酸エチル2000部に溶解、混合し、ポリエステル樹脂溶液2−3を得た。このとき、樹脂溶液は極薄く白濁していた。
(環状エステルを用いたポリエステル樹脂溶液の作製4)
冷却管、撹拌機及び窒素導入管をセットした反応容器中に、100部のポリエステルa、L−ラクチド400部、ラセミラクチド100部及びテレフタル酸チタン1部を仕込み、常圧下、160℃で6時間開環重合し、ポリエステル2−4を得た。1000部のポリエステル2−4を酢酸エチル2000部に溶解、混合し、ポリエステル樹脂溶液2−4を得た。このとき、樹脂溶液は透明であった。
(環状エステルを用いたポリエステル樹脂溶液の作製5)
冷却管、撹拌機及び窒素導入管をセットした反応容器中に、100部のポリエステルa、D−ラクチド400部、ラセミラクチド100部及びテレフタル酸チタン1部を仕込み、常圧下、160℃で6時間開環重合し、ポリエステル2−5を得た。1000部のポリエステル2−5を酢酸エチル2000部に溶解、混合し、ポリエステル樹脂溶液2−5を得た。このとき、樹脂溶液は透明であった。
(環状エステルを用いたポリエステル樹脂溶液の作製6)
冷却管、撹拌機及び窒素導入管をセットした反応容器中に、ヒマシ油ポリオールHS3P−255(豊国製油社製)15部、L−ラクチド400部、ラセミラクチド100部及びテレフタル酸チタン1部を仕込み、常圧下、160℃で6時間開環重合し、ポリエステル2−6を得た。1000部のポリエステル2−6を酢酸エチル2000部に溶解、混合し、ポリエステル樹脂溶液2−6を得た。このとき、樹脂溶液は透明であった。
(ポリエステルプレポリマーの合成)
撹拌棒及び温度計をセットした反応容器に、水酸基価が56mgKOH/gのポリエステル樹脂(ビスフェノールAのEO2モル付加物及びテレフタル酸を脱水縮合して合成)2000部を仕込み、3mmHgの減圧下、110℃に加熱して1時間脱水を行った。次に、イソホロンジイソシアネート(IPDI)457部を投入し、110℃で10時間反応を行い、末端にイソシアネート基を有するポリエステルプレポリマー1を得た。ポリエステルプレポリマー1の遊離イソシアネート含量は3.6%であった。
(環状エステルを用いたポリエステルプレポリマーの合成)
撹拌棒及び温度計をセットした反応容器に、水酸基価が56mgKOH/gのポリエステルジオール(エチレングリコール6部及びL−ラクチド200部を、常圧下、160℃で8時間開環重合して合成)2000部を仕込み、3mmHgの減圧下、110℃に加熱して1時間脱水を行った。次に、イソホロンジイソシアネート(IPDI)457部を投入し、110℃で10時間反応を行い、末端にイソシアネート基を有するポリエステルプレポリマー2を得た。ポリエステルプレポリマー2の遊離イソシアネート含量は3.6%、Tg65℃、酸価15mgKOH/gであった。
(硬化剤の合成)
撹拌棒及び温度計をセットした反応容器に、エチレンジアミン50部及びメチルイソブチルケトン(MIBK)50部を仕込み、50℃で5時間反応を行い、ケチミン化合物(硬化剤1)を得た。
(実施例1−1)
ビーカーに、240部のポリエステル樹脂溶液2−1、トリメチロールプロパントリベヘネート(離型剤;融点58℃、溶融粘度24cps)20部及び銅フタロシアニン(着色剤)4部を入れ、TK式ホモミキサー(特殊機化社製)を用いて、50℃、12000rpmで撹拌し、均一に分散させて着色剤分散液1を得た。
(実施例1−2)
ポリエステル樹脂溶液2−1の代わりに、ポリエステル樹脂溶液2−2を用いた以外は、実施例1−1と同様にトナーを得た。
(実施例1−3)
ポリエステル樹脂溶液2−1の代わりに、ポリエステル樹脂溶液2−3を用いた以外は、実施例1−1と同様にトナーを得た。
(実施例1−4)
ポリエステル樹脂溶液2−1の代わりに、ポリエステル樹脂溶液2−4を用いた以外は、実施例1−1と同様にトナーを得た。
(実施例1−5)
ポリエステル樹脂溶液2−1の代わりに、ポリエステル樹脂溶液2−5を用いた以外は、実施例1−1と同様にトナーを得た。
(実施例1−6)
ポリエステル樹脂溶液2−1の代わりに、ポリエステル樹脂溶液2−6を用いた以外は、実施例1−1と同様にトナーを得た。
(実施例2)
ビーカーに、500部の樹脂粒子分散液2を入れ、50℃まで昇温させ、TK式ホモミキサーを用いて12000rpmで撹拌しながら、214部の着色剤分散液1(実施例1−1参照)を投入し、10分間撹拌した。次に、この混合液を撹拌棒及び温度計付きのコルベンに移し、昇温して酢酸エチルを留去し、着色粒子分散液を得た。
(実施例3)
ビーカーに、240部のポリエステル樹脂溶液2−1、20部のポリエステルプレポリマー2、酢酸エチル40部、トリメチロールプロパントリベヘネート20部及び銅フタロシアニン4部を入れ、TK式ホモミキサーを用いて、50℃、12000rpmで撹拌し、均一に分散させて着色剤分散液2を得た。
(比較例1)
ポリエステル樹脂溶液2−1の代わりに、ポリエステル樹脂溶液1を用いた以外は、実施例2−1と同様にしてトナーを得た。
(比較例2)
ポリエステル樹脂溶液2−1及びポリエステルプレポリマー2の代わりに、それぞれポリエステル樹脂溶液1及びポリエステルプレポリマー1を用いた以外は、実施例3と同様にしてトナーを得た。
(平均粒子径、粒度分布の測定)
粒度測定器マルチサイザーIII(コールターエレクトロニクス社製)を用い、アパーチャー径100μmで、実施例及び比較例で得られたトナーの粒度分布を測定し、体積平均粒径D4及び個数平均粒径D1を求めた。
(定着性の測定)
トナー7重量部及びシリコーン樹脂を被覆した平均粒子径が40μmの銅−亜鉛フェライトキャリア93重量部を攪拌混合することにより、現像剤を調製した。imagio Neo C285(リコー社製)を用いて、ベタ画像で1.0±0.1mg/cm2のトナーが現像されるように調整し、定着ベルトの温度を変化させて、普通紙及び厚紙で、それぞれオフセットの発生しない定着上限温度及び定着下限温度を測定した。なお、定着下限温度は、得られた定着画像をパットで擦った後の画像濃度の残存率が70%以上となる定着ベルトの温度とした。このとき、普通紙及び厚紙としては、それぞれタイプ6200(リコー社製)及び複写印刷用紙<135>(NBSリコー社製)を用いた。
(画像透明性)
上記の単色画像サンプルを、定着ベルトの温度を160℃にして、OHPシートのタイプPPC−DX(リコー製)に現像したサンプルのヘイズ度を、直読ヘイズ度コンピューターHGM−2DP型(スガ試験機株式会社製)を用いて測定した。ヘイズ度は、曇り度とも言われ、トナーの透明性を示す尺度として測定され、値が低い程、透明性が高く、OHPシートを用いた場合の発色性が良好となる。ヘイズ度の値は、30%以下であることが好ましく、20%以下が特に好ましい。
4 現像装置
6 クリーニング装置
10 中間転写ベルト
16 支持ローラ
17 クリーニング装置
18 画像形成手段
20 タンデム画像形成装置
21 露光装置
22 二次転写装置
24 二次転写ベルト
25 定着装置
28 反転装置
32 コンタクトガラス
33 第一走行体
34 第二走行体
35 結像レンズ
36 読み取りセンサ
40 感光体(潜像担持体)
43 ペーパーバンク
44 給紙カセット
45 分離ローラ
46 給紙路
47 搬送ローラ
48 給紙路
49 レジストローラ
50 給紙ローラ
51 手差しトレイ
52 分離ローラ
55 切換爪
56 排出ローラ
57 排紙トレイ
62 一次転写装置
100 複写装置本体
200 給紙テーブル
300 スキャナ
400 原稿自動搬送装置
500 トナー収納容器
600、700 エアーポンプ
800 トナー搬送用チューブ
Claims (18)
- ポリエステル樹脂を含む着色粒子を有するトナーであって、
該ポリエステル樹脂は、2個以上6個以下の水酸基を有するポリオール並びに水酸基及び/又はカルボキシル基を有するポリエステル樹脂からなる群より選択される一種以上の化合物と環状エステルを開環重合することにより得られ、
該環状エステルは、L−ラクチド、D−ラクチド、DL−ラクチド及びラセミラクチドからなる群より選択される一種以上であることを特徴とするトナー。 - 前記着色粒子は、1級アミノ基を有する化合物と、該1級アミノ基と反応可能な官能基を有するポリエステルプレポリマーを反応させることにより得られる樹脂をさらに含み、
該ポリエステルプレポリマーは、2個以上6個以下の水酸基を有するポリオール並びに水酸基及び/又はカルボキシル基を有するポリエステル樹脂からなる群より選択される一種以上の化合物と環状エステルを開環重合することにより得られるポリエステル樹脂と、前記1級アミノ基と反応可能な官能基を有する化合物を反応させることにより得られ、
該環状エステルは、L−ラクチド、D−ラクチド、DL−ラクチド及びラセミラクチドからなる群より選択される一種以上であることを特徴とする請求項1に記載のトナー。 - 前記1級アミノ基と反応可能な官能基は、イソシアネート基及び/又はブロック化イソシアネート基であることを特徴とする請求項2に記載のトナー。
- 前記着色粒子の表面に樹脂粒子が付着していることを特徴とする請求項1乃至3のいずれか一項に記載のトナー。
- 前記樹脂粒子は、ビニル系樹脂を含むことを特徴とする請求項4に記載のトナー。
- 体積平均粒径が4μm以上8μm以下であることを特徴とする請求項1乃至5のいずれか一項に記載のトナー。
- 数平均粒径に対する体積平均粒径の比が1.00以上1.25以下であることを特徴とする請求項1乃至6のいずれか一項に記載のトナー。
- 平均円形度が0.94以上0.96以下であることを特徴とする請求項1乃至7のいずれか一項に記載のトナー。
- ポリエステル樹脂を含む組成物を有機溶媒中に溶解又は分散させて第一の液を調製する工程と、
該第一の液を、樹脂粒子を含む水性溶媒中に乳化又は分散させて第二の液を調製する工程を有し、
該ポリエステル樹脂は、2個以上6個以下の水酸基を有するポリオール並びに水酸基及び/又はカルボキシル基を有するポリエステル樹脂からなる群より選択される一種以上の化合物と環状エステルを開環重合することにより得られ、
該環状エステルは、L−ラクチド、D−ラクチド、DL−ラクチド及びラセミラクチドからなる群より選択される一種以上であることを特徴とするトナーの製造方法。 - 前記組成物は、1級アミノ基を有する化合物と、該1級アミノ基と反応可能な官能基を有するポリエステルプレポリマーをさらに含み、
該ポリエステルプレポリマーは、2個以上6個以下の水酸基を有するポリオール並びに水酸基及び/又はカルボキシル基を有するポリエステル樹脂からなる群より選択される一種以上の化合物と環状エステルを開環重合することにより得られるポリエステル樹脂と、前記1級アミノ基と反応可能な官能基を有する化合物を反応させることにより得られ、
該環状エステルは、L−ラクチド、D−ラクチド、DL−ラクチド及びラセミラクチドからなる群より選択される一種以上であることを特徴とする請求項9に記載のトナーの製造方法。 - 前記ポリエステルプレポリマーに対する前記ポリエステル樹脂の重量比が5/95以上80/20以下であることを特徴とする請求項10に記載のトナーの製造方法。
- 前記樹脂粒子は、体積平均粒径が5nm以上2μm以下であることを特徴とする請求項9乃至11のいずれか一項に記載のトナーの製造方法。
- 減圧及び加熱の少なくとも一方の手段を用いて、前記第二の液に含まれる前記有機溶媒を除去して着色粒子が分散されている第三の液を調製する工程をさらに有することを特徴とする請求項9乃至12のいずれか一項に記載のトナーの製造方法。
- 前記第三の液を濾過する工程をさらに有することを特徴とする請求項13に記載のトナーの製造方法。
- 前記着色粒子の表面に付着している前記樹脂粒子を脱離させる工程をさらに有することを特徴とする請求項13又は14に記載のトナーの製造方法。
- 請求項1乃至8のいずれか一項に記載のトナー及びキャリアを含有することを特徴とする現像剤。
- 請求項1乃至8のいずれか一項に記載のトナーを用いて画像を形成することを特徴とする画像形成方法。
- 請求項1乃至8のいずれか一項に記載のトナーが収納されていることを特徴とするトナー収納容器。
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JP5054600B2 (ja) * | 2007-06-27 | 2012-10-24 | 株式会社リコー | トナー及びその製造方法、並びに現像剤、現像剤入り容器、プロセスカートリッジ、画像形成方法、及び画像形成装置 |
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JP5494922B2 (ja) | 2009-06-10 | 2014-05-21 | 株式会社リコー | トナー、現像剤、トナー入り容器、プロセスカートリッジ、画像形成方法及び画像形成装置 |
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