JP4795981B2 - 電荷制御剤等として使用されるモノアゾ鉄錯体化合物 - Google Patents
電荷制御剤等として使用されるモノアゾ鉄錯体化合物 Download PDFInfo
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- JP4795981B2 JP4795981B2 JP2007020087A JP2007020087A JP4795981B2 JP 4795981 B2 JP4795981 B2 JP 4795981B2 JP 2007020087 A JP2007020087 A JP 2007020087A JP 2007020087 A JP2007020087 A JP 2007020087A JP 4795981 B2 JP4795981 B2 JP 4795981B2
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- -1 Monoazo iron complex compounds Chemical class 0.000 title claims description 103
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
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- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
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- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 5
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- 230000001932 seasonal effect Effects 0.000 description 1
- 239000011257 shell material Substances 0.000 description 1
- 229910000077 silane Inorganic materials 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
- 239000000344 soap Substances 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- VEALVRVVWBQVSL-UHFFFAOYSA-N strontium titanate Chemical compound [Sr+2].[O-][Ti]([O-])=O VEALVRVVWBQVSL-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- JIYXDFNAPHIAFH-UHFFFAOYSA-N tert-butyl 3-tert-butylperoxycarbonylbenzoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC(C(=O)OC(C)(C)C)=C1 JIYXDFNAPHIAFH-UHFFFAOYSA-N 0.000 description 1
- JZFHXRUVMKEOFG-UHFFFAOYSA-N tert-butyl dodecaneperoxoate Chemical compound CCCCCCCCCCCC(=O)OOC(C)(C)C JZFHXRUVMKEOFG-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000010409 thin film 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
- 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
- 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
- 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
- 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
- KJPJZBYFYBYKPK-UHFFFAOYSA-N vat yellow 1 Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3N=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1N=C4C=C5 KJPJZBYFYBYKPK-UHFFFAOYSA-N 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
- 229960000834 vinyl ether Drugs 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
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011787 zinc oxide 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
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Description
式[1]中、A1、A2、B1、B2は、相互に独立して、H、炭素数が1〜4のアルキル基又はハロゲン原子を示す。ハロゲン原子は塩素が好ましい。Jは、H、アルカリ金属、NH4、又は炭素数が3〜8のアルキルアンモニウムを示し、これらは2種以上であってもよい。アルキルアンモニウムは、窒素原子に同一又は異なったアルキル基が1〜4個結合したものでもよい。X1、X2は、相互に独立して、H、アルキル基、ハロゲン原子を示し、Y1、Y2は相互に独立して、H、炭素数が1〜4のアルキル基、又は炭素数が1〜4のアルキル基若しくはハロゲン原子で置換されたフェニル基又は無置換のフェニル基を示す。ただし、A1、A2、B1、B2、X1、X2、Y1、Y2が同時に水素の場合を除く。
式[2]中、Jは、H、Na、NH4、又は炭素数が3〜8のアルキルアンモニウムを示し、これらは2種以上であってもよい。アルキルアンモニウムは、窒素原子に同一又は異なったアルキル基が1〜4個結合したものでもよい。X1、X2は相互に独立して、H、アルキル基、又はハロゲン原子を示し、Z1、Z2は、相互に独立して、H、炭素数1〜4のアルキル基、又は塩素原子を示す。
式[3]中、Jは、H、Na、NH4、又は炭素数が3〜8のアルキルアンモニウムを示し、これらの2種以上であってもよい。アルキルアンモニウムは、窒素原子に同一又は異なったアルキル基が1〜4個結合したものでもよい。
式[4]中、Jは、H、Na、NH4、又は炭素数が3〜8のアルキルアンモニウムを示し、これらの2種以上であってもよい。アルキルアンモニウムは、窒素原子に同一又は異なったアルキル基が1〜4個結合したものでもよい。
7.電荷制御剤の体積平均粒径が0.1〜20μmである、上記6に記載の電荷制御剤。
8.少なくとも上記1乃至5のいずれか1項記載のモノアゾ鉄錯体化合物、着色剤及び結着樹脂を含有するトナー。
9.モノアゾ鉄錯体化合物が、結着樹脂100質量部当り0.1〜10質量部、トナー粒子に内添されている、上記8記載のトナー。
10.モノアゾ鉄錯体化合物が、結着樹脂100質量部当り0.2〜5質量部、トナー粒子に内添されている、上記8記載のトナー。
11.結着樹脂は、酸価が0.1〜100mgKOH/gである、上記8乃至10のいずれか1項記載のトナー。
12.着色剤は、磁性体である、上記8乃至11のいずれか1項記載のトナー。
13.磁性体は、磁性酸化鉄である、上記12記載のトナー。
14.磁性体は、結着樹脂100質量部当り10〜200質量部含有されている、上記12又は13記載のトナー。
15.着色剤は、非磁性の着色剤であり、結着樹脂100質量部当り0.1〜20質量部含有されている、上記8乃至11のいずれか1項記載のトナー。
16.ワックスが更に含有されている、上記8乃至15のいずれか1項記載のトナー。
17.ワックスは融点が70℃〜140℃である、上記16記載のトナー。
18.ワックスは、結着樹脂100質量部当り0.2〜20質量部含有されている、上記16又は17記載のトナー。
19.トナーの体積平均粒径は、2〜15μmである、上記8乃至18のいずれか1項記載のトナー。
20.トナーの体積平均粒径は、3〜12μmである、上記8乃至18のいずれか1項記載のトナー。
21.上記8乃至20のいずれか1項記載の負帯電性トナーから成る1成分系現像剤。
22.負帯電性トナー及びキャリアを有する2成分系現像剤において、該トナーは、少なくとも結着樹脂、着色剤及びモノアゾ鉄錯体化合物を含有しており、該モノアゾ鉄錯体化合物は、上記1乃至5のいずれか1項記載のモノアゾ鉄錯体化合物である2成分系現像剤。
23.モノアゾ鉄錯体化合物が、結着樹脂100質量部当り0.1〜10質量部、トナー粒子に内添されている、上記22記載の2成分系現像剤。
24.モノアゾ鉄錯体化合物が、結着樹脂100質量部当り0.2〜5質量部、トナー粒子に内添されている、上記22記載の2成分系現像剤。
25.トナーは、スチレン−アクリル系樹脂を結着樹脂として含有している、上記22乃至24のいずれか1項記載の2成分系現像剤。
26.結着樹脂は、酸価が0.1〜100mgKOH/gである、上記25に記載の2成分系現像剤。
27.結着樹脂は、酸価が0.1〜50mgKOH/gである、上記25に記載の2成分系現像剤。
28.結着樹脂は、ガラス転移点(Tg)が35〜80℃である、上記22乃至27のいずれか1項記載の2成分系現像剤。
29.ワックスが更に含有されている、上記22乃至28のいずれか1項記載の2成分系現像剤。
30.ワックスは融点が70℃〜140℃である、上記29記載のトナー。
31.ワックスは、結着樹脂100質量部当り0.2〜20質量部含有されている、上記29又は30記載のトナー。
32.トナーの体積平均粒径は、2〜15μmである、上記22乃至31のいずれか1項記載の2成分系現像剤。
33.トナーの体積平均粒径は、3〜12μmである、上記22乃至31のいずれか1項記載の2成分系現像剤。
34.キャリアは、樹脂コートキャリアである、上記22乃至33のいずれか1項記載の2成分系現像剤。
35.樹脂コートキャリアは、キャリアコア粒子及び該キャリアコア粒子表面を被覆(コート)する樹脂である被覆材からなり、該被覆(コート)材は、ポリテトラフルオロエチレン、モノクロロトリフルオロエチレン重合体、ポリフッ化ビニリデン、シリコーン樹脂、ポリエステル、スチレン系樹脂、アクリル系樹脂、ポリアミド、ポリビニルブチラール、アミノアクリレート樹脂から選択される1種以上の樹脂を有している上記34記載の2成分系現像剤。
当該電荷制御剤を含有するトナーは、1成分あるいは2成分いずれの現像方式においても、画像濃度、カブリ濃度、ドット再現性あるいは、細線再現性等の画像特性評価に対して、優れた画像を得ることができる。
本発明のモノアゾ鉄錯体化合物を含有したトナーは、高湿あるいは低湿環境下においても帯電特性の変動が少なく、安定した現像特性を保持できる。
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、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等の環状エーテルが重合して得られるジオール等が挙げられる。
本発明において、結着樹脂の分子量分布は、THFを溶媒としたゲルパーミエーションクロマトグラフィー(GPC)により測定される。
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0.1〜50mgKOH/gを有する樹脂を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、着色剤又は磁性体等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のファクターである。
酸価(mgKOH/g)=[(S−B)×f×5.61]/W (1)
上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。
上記の着色剤の使用量は結着樹脂100量部に対して、0.1〜20質量部が好ましい。
樹脂コートキャリアにおいて、キャリアコアの表面を少なくとも樹脂被覆剤で被覆する方法としては、樹脂を溶剤中に溶解若しくは懸濁せしめて塗布したキャリアコアに付着せしめる方法、あるいは単に粉体状態で混合する方法が適用できる。樹脂コートキャリアに対して樹脂被覆材の割合は、適宜決定すればよいが、樹脂コートキャリアに対し好ましくは0.01〜5質量%、より好ましくは0.1〜1質量%がよい。
可塑化作用を有するワックスの種類としては、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や極性基を有する構造のものであり、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、直鎖構造のものや、官能基を有さない無極性のものが挙げられる。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℃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等が挙げられる。
重合トナーを製造する際に使用する分散剤としては、例えば無機系酸化物としては、リン酸三カルシウム、リン酸マグネシウム、リン酸アルミニウム、リン酸亜鉛、炭酸カルシウム、炭酸マグネシウム、水酸化アルミニウム、メタケイ酸カルシウム、硫酸カルシウム、硫酸バリウム、ベントナイト、シリカ、アルミナ等が挙げられる。有機系化合物としては、例えばポリビニルアルコール、ゼラチン、メチルセルロース、メチルヒドロキシプロピルセルロース、エチルセルロース、カルボキシメチルセルロースのナトリウム塩、デンプン等が使用されている。これらの分散剤は、重合性単量体100質量部に対して0.2〜2.0質量部を使用することが好ましい。
本発明のトナーは、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。)
本発明のトナーの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。
4−クロロ−2−アミノフェノール10部を水76.5部、及び35%塩酸15.2部に加え、冷却下で攪拌溶解した。内温10℃以下で水24.6部に溶解させた亜硝酸ナトリウム13.6部を前記塩酸水溶液に滴下し、適宜砕氷10部を加えながら5〜10℃を維持した。滴下終了後、10℃で2時間攪拌し反応させた。スルファミン酸0.2部を加え10分反応させた後、ヨウ化カリウムでんぷん紙により過剰に亜硝酸が残存していないことを確認し、ジアゾ溶液を調製した。
なお、赤外吸収スペクトルについては錠剤法(KBr)によって測定した。以下同様な方法で赤外吸収スペクトルの測定を行った。
4−クロロ−2−アミノフェノール10部を、水76.5部、及び35%塩酸15.2部に加え、冷却下で攪拌溶解した。内温10℃以下で水24.6部に溶解させた亜硝酸ナトリウム13.6部を前記塩酸水溶液に滴下し、適宜砕氷10部を加えながら5〜10℃を維持した。滴下終了後、10℃で2時間攪拌し反応させた。スルファミン酸0.2部を加え10分反応させた後、ヨウ化カリウムでんぷん紙により過剰に亜硝酸が残存していないことを確認し、ジアゾ溶液を調製した。
得られた化合物を赤外吸収スペクトル、可視部吸収スペクトル、元素分析(C,H,N)、原子吸光分析、マススペクトルより、化合物No.2の化合物であることを確認した。
4−クロロ−2−アミノフェノール10部、水76.5部、及び35%塩酸15.2部を加え、冷却下で攪拌溶解した。内温10℃以下で水24.6部に溶解させた亜硝酸ナトリウム13.6部を滴下し、適宜砕氷10部を加えながら5〜10℃を維持した。滴下終了後、10℃で2時間攪拌し反応させた。スルファミン酸0.2部を加え10分反応させた後、ヨウ化カリウムでんぷん紙により過剰に亜硝酸が残存していないことを確認し、ジアゾ溶液を調製した。
4−クロロ−2−アミノフェノール10部、水76.5部、及び35%塩酸15.2部を加え、冷却下で攪拌溶解した。内温10℃以下で水24.6部に溶解させた亜硝酸ナトリウム13.6部を滴下し、適宣砕氷10部を加えながら5〜10℃を維持した。滴下終了後、10℃で2時間攪拌し反応させた。スルファミン酸0.2gを加え、10分反応させた後、ヨウ化カリウムでんぷん紙により過剰に亜硝酸ナトリウムが残存していないことを確認し、ジアゾ溶液を調製した。
次に3−メチル−1−フェニル−5−ピラゾロン12.0部、水87部、25%水酸化ナトリウム12.1部、炭酸ナトリウム4.9部及びブタノール104.6部を添加し、室温で攪拌溶解した。そこに上記ジアゾ溶液を注加し、20〜22℃で4時間攪拌しカップリング反応を行った。4時間後、レゾルシンとの反応が無いことを確認し反応終了とした。水30.4部を加えた後十分に攪拌し、静置してから下部水層を分液した。更に水92.8部、25%水酸化ナトリウム8.7部を加え攪拌洗浄し、下部水層を分液した。
水42.2部、サリチル酸5.9部、ブタノール24.6部、及び15%炭酸ナトリウム48.5部を上記反応液に添加し攪拌した。38%塩化第二鉄水溶液15.1部と15%炭酸ナトリウム18.0部を注加し、酢酸でpHを4.5に調整した。内温を30℃に昇温後、8時間攪拌し錯体化反応を行った。8時間後、TLCで原料のスポットが消失したことを確認し反応終了とした。攪拌停止後、静置して下部水層を分液した。更に水189.9部を加え攪拌洗浄し、下部水層を分液した。濾過後、水253部でケーキを洗浄した。60℃真空乾燥の後、恒量に達したことを確認し、目的化合物24.2部を得た。
得られた化合物を赤外吸収スペクトル、可使部吸収スペクトル、元素分析(C、H、N)、原子吸光分析、マススペクトルより、化合物No.4の化合物であることを確認した。
化合物21は、製造例2の硫酸アンモニウムの量を半分にした以外は製造例2と同様な方法で製造し、化合物21を得た。
既知の電荷制御剤である、以下の構造を有する鉄アゾ錯体(保土谷化学工業社製、商品名:T-77)。下式中、a+b+cは1である。
既知の電荷制御剤である、以下の構造を有するクロムアゾ錯体(保土谷化学工業社製、商品名:T-95)。
0.5モルの水酸化ナトリウムと水に対して、3,5−ジ−tert−ブチルサリチル酸を0.4モル加え、加熱し溶解した。この溶液にAl2(SO4)30.1モルの水溶液を加え反応させた。50℃で3時間反応させた後、析出した白色結晶を濾取した。これを水洗して減圧にて40℃で24時間乾燥した。得られた反応物は目的とするアルミニウム原子に対し、3,5−ジ−tert−ブチルサリチル酸が2原子結合する化合物であった。
スチレンーアクリル系共重合体樹脂(酸価0.1mgkOH/g) 91部
(三井化学社製、商品名CPR−100)
製造例1で得られた化合物 1部
カーボンブラック(三菱化学社製、商品名MA−100) 5部
低分子量ポリプロピレン(三洋化成社製、商品名ビスコール550P)
3部
(qmax−q)/(qmax-q0)=exp(-t/τ)
ここで、qmaxは飽和帯電量、q0は初期帯電量(ここでは帯電時間10秒のとき)、tが各測定時間であり、そのときの帯電量がqである。
帯電立ち上がりのよいものは、時定数がより小さな値となる。時定数の単位は秒である。
「製造例1で得られた化合物」の代わりに、表1及び表2中の化合物No.2〜22をそれぞれ使用した以外は添加量を含めて実施例1と同様の方法で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る帯電量、時定数、環境安定性を評価し、それぞれ実施例2〜実施例22として結果を表3に示した。
「製造例1で得られた化合物」の代わりに、比較電荷制御剤1、比較電荷制御剤2及び比較製造例3の化合物をそれぞれ使用した以外は添加量を含めて実施例1と同様の方法で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る帯電量、時定数、環境安定性を評価し、それぞれ比較例1〜3として、結果を表3に示した。
実施例1〜4と比較例1〜3で使用した非磁性トナーと、シリコンコート系のフェライトキャリア(パウダーテック社製、F96−100、)とを4:100部の割合で混合した現像剤を用い、非磁性2成分現像方式による画像特性評価を行った。画像特性評価に用いる画像形成装置は市販の非磁性2成分現像方式複写機を改良し、感光体表面電位、現像ローラー印加電圧、転写電圧、定着温度が任意に制御できるようにしてあり、初期画像で印字が最良となるよう各条件を設定した。印刷はトナーを連続補給しながら、テストチャート印刷を開始してからそれぞれ10枚目(初期画像)、5千枚連続印刷後、2万枚連続印刷後の画像をサンプリングし、画像特性評価し、それぞれ実施例23〜26、比較例4〜6とした。
スチレンーアクリル系共重合体樹脂(酸価0.1mgkOH/g) 100部
(三井化学社製、商品名CPR−100、)
製造例1で得られた化合物 2部
磁性酸化鉄 (チタン工業社製、商品名BL−200) 90部
低分子量ポリプロピレン (三洋化成社製、商品名ビスコール550P)
3部
上記混合物を130℃の加熱混合装置(2軸押出混練機)により溶融混合し、冷却した混合物をハンマーミルで粗粉砕した。更にジェットミルで微粉砕した後、分級して体積平均粒径9±0.5μmの磁性トナーを得た。
「製造例1で得られた化合物」の代わりに、それぞれ、「製造例2で得られた化合物」、「製造例3で得られた化合物」及び「製造例4で得られた化合物」を使用した他は、添加量を含めて実施例27と同様にして磁性トナーを調製し、これらをそれぞれ、実施例28、実施例29及び実施例30とした。
「製造例1で得られた化合物」の代わりに、それぞれ、比較電荷制御剤1、比較電荷制御剤2、比較製造例3で得られた化合物を使用した他は、添加量を含めて実施例27と同様にして磁性トナーを調整し、これらをそれぞれ比較例7〜9とした。
実施例27〜30と比較例7〜9で製造した磁性トナーを用い、磁性1成分現像方式による画像特性評価を行った。
本実施例で適用される画像形成装置は市販の磁性1成分現像方式プリンター(解像度600dpi)を改造し、感光体表面電位、現像ローラー印加電圧、転写電圧、定着温度が任意に制御できるようにしてあり、初期画像で印字が最良となるよう各条件を設定した。
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