JPH0429250A - Manufacture of electrostatic charge image developing toner - Google Patents
Manufacture of electrostatic charge image developing tonerInfo
- Publication number
- JPH0429250A JPH0429250A JP2136142A JP13614290A JPH0429250A JP H0429250 A JPH0429250 A JP H0429250A JP 2136142 A JP2136142 A JP 2136142A JP 13614290 A JP13614290 A JP 13614290A JP H0429250 A JPH0429250 A JP H0429250A
- Authority
- JP
- Japan
- Prior art keywords
- toner
- parts
- polymer particles
- image
- monomer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
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- 239000000203 mixture Substances 0.000 claims abstract description 24
- 239000006185 dispersion Substances 0.000 claims abstract description 19
- 229920000642 polymer Polymers 0.000 claims abstract description 19
- 239000006087 Silane Coupling Agent Substances 0.000 claims abstract description 17
- 239000003381 stabilizer Substances 0.000 claims abstract description 17
- 239000003086 colorant Substances 0.000 claims abstract description 15
- 239000010419 fine particle Substances 0.000 claims abstract description 8
- 239000002612 dispersion medium Substances 0.000 claims abstract description 7
- 239000000843 powder Substances 0.000 abstract description 12
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- 239000003505 polymerization initiator Substances 0.000 abstract description 7
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- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 229910000077 silane Inorganic materials 0.000 abstract 1
- 238000000034 method Methods 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
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- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 7
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
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- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
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- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
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- 238000004581 coalescence Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
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- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
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- 230000002401 inhibitory effect Effects 0.000 description 2
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000696 magnetic material Substances 0.000 description 2
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- 229910000859 α-Fe Inorganic materials 0.000 description 2
- QLLUAUADIMPKIH-UHFFFAOYSA-N 1,2-bis(ethenyl)naphthalene Chemical compound C1=CC=CC2=C(C=C)C(C=C)=CC=C21 QLLUAUADIMPKIH-UHFFFAOYSA-N 0.000 description 1
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- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
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- TZJQCUDHKUWEFU-UHFFFAOYSA-N 2,2-dimethylpentanenitrile Chemical compound CCCC(C)(C)C#N TZJQCUDHKUWEFU-UHFFFAOYSA-N 0.000 description 1
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- OLQFXOWPTQTLDP-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCO OLQFXOWPTQTLDP-UHFFFAOYSA-N 0.000 description 1
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- 239000011651 chromium Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000000368 destabilizing effect Effects 0.000 description 1
- YSCOODQOCWOXNL-UHFFFAOYSA-N diethylamino 2-methylprop-2-enoate Chemical compound CCN(CC)OC(=O)C(C)=C YSCOODQOCWOXNL-UHFFFAOYSA-N 0.000 description 1
- YCMOBGSVZYLYBZ-UHFFFAOYSA-L disodium 5-[[4-[4-[(2-amino-8-hydroxy-6-sulfonatonaphthalen-1-yl)diazenyl]phenyl]phenyl]diazenyl]-2-hydroxybenzoate Chemical compound NC1=CC=C2C=C(C=C(O)C2=C1N=NC1=CC=C(C=C1)C1=CC=C(C=C1)N=NC1=CC=C(O)C(=C1)C(=O)O[Na])S(=O)(=O)O[Na] YCMOBGSVZYLYBZ-UHFFFAOYSA-L 0.000 description 1
- NHOGGUYTANYCGQ-UHFFFAOYSA-N ethenoxybenzene Chemical compound C=COC1=CC=CC=C1 NHOGGUYTANYCGQ-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- PLYDMIIYRWUYBP-UHFFFAOYSA-N ethyl 4-[[2-chloro-4-[3-chloro-4-[(3-ethoxycarbonyl-5-oxo-1-phenyl-4h-pyrazol-4-yl)diazenyl]phenyl]phenyl]diazenyl]-5-oxo-1-phenyl-4h-pyrazole-3-carboxylate Chemical compound CCOC(=O)C1=NN(C=2C=CC=CC=2)C(=O)C1N=NC(C(=C1)Cl)=CC=C1C(C=C1Cl)=CC=C1N=NC(C(=N1)C(=O)OCC)C(=O)N1C1=CC=CC=C1 PLYDMIIYRWUYBP-UHFFFAOYSA-N 0.000 description 1
- PSYUBHDPOIZRST-UHFFFAOYSA-N ethyl pyruvate Chemical compound CCOC(=O)C(O)=C PSYUBHDPOIZRST-UHFFFAOYSA-N 0.000 description 1
- 230000005294 ferromagnetic effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000006232 furnace black Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 1
- SMTJKYKQUOBAMY-UHFFFAOYSA-N hydrogen peroxide;iron(2+) Chemical compound [Fe+2].OO SMTJKYKQUOBAMY-UHFFFAOYSA-N 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 1
- 229910000157 magnesium phosphate Inorganic materials 0.000 description 1
- 239000004137 magnesium phosphate Substances 0.000 description 1
- 229960002261 magnesium phosphate Drugs 0.000 description 1
- 235000010994 magnesium phosphates Nutrition 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- FDZZZRQASAIRJF-UHFFFAOYSA-M malachite green Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 FDZZZRQASAIRJF-UHFFFAOYSA-M 0.000 description 1
- 229940107698 malachite green Drugs 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000434 metal complex dye Substances 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
- VENDXQNWODZJGB-UHFFFAOYSA-N n-(4-amino-5-methoxy-2-methylphenyl)benzamide Chemical compound C1=C(N)C(OC)=CC(NC(=O)C=2C=CC=CC=2)=C1C VENDXQNWODZJGB-UHFFFAOYSA-N 0.000 description 1
- 125000005609 naphthenate group Chemical class 0.000 description 1
- CTIQLGJVGNGFEW-UHFFFAOYSA-L naphthol yellow S Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C([O-])=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 CTIQLGJVGNGFEW-UHFFFAOYSA-L 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229920001778 nylon Polymers 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
- 239000003921 oil Substances 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
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-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
- 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
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002961 polybutylene succinate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 235000012739 red 2G Nutrition 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 150000003839 salts Chemical class 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
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- IXNUVCLIRYUKFB-UHFFFAOYSA-M sodium;3-[[4-[[4-(diethylamino)-2-methylphenyl]-[4-[ethyl-[(3-sulfonatophenyl)methyl]azaniumylidene]cyclohexa-2,5-dien-1-ylidene]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].CC1=CC(N(CC)CC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC=1C=C(C=CC=1)S([O-])(=O)=O)=C(C=C1)C=CC1=[N+](CC)CC1=CC=CC(S([O-])(=O)=O)=C1 IXNUVCLIRYUKFB-UHFFFAOYSA-M 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- FKVXIGHJGBQFIH-UHFFFAOYSA-K trisodium 5-amino-3-[[4-[4-[(7-amino-1-hydroxy-3-sulfonatonaphthalen-2-yl)diazenyl]phenyl]phenyl]diazenyl]-4-hydroxynaphthalene-2,7-disulfonate Chemical compound C1=CC(=CC=C1C2=CC=C(C=C2)N=NC3=C(C=C4C=CC(=CC4=C3[O-])N)S(=O)(=O)O)N=NC5=C(C6=C(C=C(C=C6C=C5S(=O)(=O)O)S(=O)(=O)[O-])N)[O-].[Na+].[Na+].[Na+] FKVXIGHJGBQFIH-UHFFFAOYSA-K 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
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
Landscapes
- Developing Agents For Electrophotography (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、静電荷潜像を現像するためのトナの製造方法
に関する。特に単量体組成物を分散媒中で重合すること
により、直接球形トナーが得られる重合法トナーの製造
方法に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a method for manufacturing a toner for developing an electrostatic latent image. In particular, the present invention relates to a method for producing a polymerized toner in which a spherical toner is directly obtained by polymerizing a monomer composition in a dispersion medium.
［従来の技術］
電気的または磁気的潜像を現像１２て画像を形成し、記
録する種々のプロセスの一つとして電子写真法が知られ
ている。この電子写真法では、一般に光導電性物質を利
用し、種々の手段で感光体上に電気的潜像を形成し、次
いでこの潜像をトナーを用いて現像し、トナー画像を形
成する。得られたトナー画像はそのまま定着するか、あ
るいは紙などに転写した後、加熱、加圧等の手段により
定着され、複写物となる。トナーを用いて現像する方法
としては、パウダークラウド法やタッチダウン法または
磁気ブラシ現像法など種々の方法が提案され、それぞれ
の画像形成プロセスに適した方法が採用されている。[Prior Art] Electrophotography is known as one of various processes for forming and recording images by developing 12 electrical or magnetic latent images. Electrophotography generally utilizes a photoconductive material to form an electrical latent image on a photoreceptor by various means, and then develops the latent image with toner to form a toner image. The obtained toner image is fixed as it is, or after being transferred to paper or the like, it is fixed by heating, pressure, or other means to form a copy. Various methods have been proposed for developing with toner, such as a powder cloud method, a touchdown method, and a magnetic brush development method, and methods suitable for each image forming process are adopted.
従来、これらの目的に用いるトナーは、一般に熱可塑性
樹脂中に磁性体あるいは染・顔料からなる着色剤を溶融
混練し、着色剤を樹脂中に均一に分散させた後、粉砕、
分級することにより、所定の粒径分布を持つトナーとし
て製造されてきた。Conventionally, toners used for these purposes are generally produced by melt-kneading a coloring agent made of a magnetic material or dye/pigment in a thermoplastic resin, uniformly dispersing the colorant in the resin, and then pulverizing and kneading the colorant.
By classifying toner, toner having a predetermined particle size distribution has been manufactured.
また、トナーに必要な特性を賦与するために、必要に応
じて種々の添加剤が混合されてきた。例えばトナーの摩
擦帯電性を調節するために金属錯塩染料が、またヒート
ロール定着時のオフセットを防止するためにワックス等
が添加される。Additionally, various additives have been mixed as necessary to impart necessary properties to the toner. For example, a metal complex dye is added to adjust the triboelectric charging properties of the toner, and a wax or the like is added to prevent offset during heat roll fixing.
この混練−粉砕によるトナーの製造方法は、優れた特性
のトナーを製造できるが、ある種の制限があった。すな
わち、粉砕されやすい、換言すると脆性の高い樹脂を使
用する必要があった。脆性の高い樹脂を用いたトナーを
実際の現像に供すると、現像のストレスによりさらに微
粉化され、選択現像やトナースペントと呼ばれる劣化を
生じやすくなる。Although this toner production method using kneading and pulverization can produce toner with excellent characteristics, it has certain limitations. That is, it was necessary to use a resin that is easily crushed, in other words, highly brittle. When a toner using a highly brittle resin is subjected to actual development, the stress of development causes it to become further finely powdered, making it more likely to cause deterioration called selective development or toner spent.
また、この混練−粉砕法においては、着色剤等の固体微
粒子を樹脂中に完全に均一に分散させることは困難であ
り、分散の度合いによってはトナの組成に分布が生じ、
トナー現像特性の変動をきたす場合もある。In addition, in this kneading-pulverization method, it is difficult to completely uniformly disperse solid particles such as colorants in the resin, and depending on the degree of dispersion, the composition of the toner may vary.
It may also cause variations in toner development characteristics.
さらに、一般にトナーにより形成した画像の解像度、ベ
タ部の稠密性、階調再現性はトナーの特性、特にその粒
子径に依存する割合が大きく、粒子径が小さいほど高品
質の画像が得られることが知られている。そのため最近
の高画質複写機、プリンタは小粒径トナーを使用してい
る例が多い。Furthermore, in general, the resolution, density of solid areas, and gradation reproducibility of images formed with toner largely depend on the characteristics of the toner, especially its particle size, and the smaller the particle size, the higher the quality of the image obtained. It has been known. For this reason, many recent high-quality copying machines and printers use toner with small particle diameters.
しかしながら、混練−粉砕法によって製造された小粒径
トナーは、トナーの形状が不定形であるため流動性が悪
いという不都合があった。流動性を向上させるために、
シリカ微粉末などの流動性改質剤を多量に添加すると、
流動性は向上するものの、感光体を傷つけたり、湿度に
よる帯電量の変動が大きくなるなど別の不都合を生ずる
。However, the small particle diameter toner produced by the kneading-pulverization method has a disadvantage of poor fluidity because the shape of the toner is irregular. To improve liquidity,
Adding a large amount of fluidity modifier such as fine silica powder will
Although fluidity is improved, other inconveniences occur, such as damage to the photoreceptor and increased fluctuations in the amount of charge due to humidity.
そこで、これらの混練−粉砕法の問題点を解決するため
、懸濁重合法によるトナーの製造方法が提案されている
。Therefore, in order to solve the problems of these kneading-pulverizing methods, a toner manufacturing method using a suspension polymerization method has been proposed.
［発明が解決しようとする問題点］
懸濁重合法においては、重合性単量体および着色剤、必
要に応じて重合開始剤、架橋剤、帯電制御剤、その他の
添加剤を溶解または分散させた単量体組成物を、懸濁安
定剤をふくむ水相中に、撹拌下に加えて造粒し、重合さ
せてトナー粒子を形成している。[Problems to be solved by the invention] In the suspension polymerization method, polymerizable monomers, colorants, and if necessary, polymerization initiators, crosslinking agents, charge control agents, and other additives are dissolved or dispersed. The monomer composition is added to an aqueous phase containing a suspension stabilizer under stirring, granulated, and polymerized to form toner particles.
この懸濁重合法は、粉砕工程を全く含まないため、トナ
ーに高い脆性を必−要とすることがなく、また粉砕法で
生じた、トナー破断面への着色剤等の露出がないため好
ましいトナー製造法である。This suspension polymerization method is preferable because it does not include any pulverization process, so the toner does not require high brittleness, and there is no exposure of coloring agents, etc. to the toner fracture surface that occurs in the pulverization method. This is a toner manufacturing method.
さらに、５ミクロンから１０ミクロンの粒子径を持つ、
小粒径トナーも容易に得られ、得られたトナーの形状も
球形であって、流動性に優れている等各種の利点がある
。Furthermore, it has a particle size of 5 microns to 10 microns,
A toner with a small particle size can also be easily obtained, and the obtained toner has various advantages such as a spherical shape and excellent fluidity.
しかしながら、懸濁重合では千ツマー液滴の分散安定剤
として用いられる、難水溶性無機微粉末やポリビニルア
ルコールやカルボキシメチルセルロースなどの水溶性高
分子を比較的多量に使用するため、生成した重合粒子表
面にはこれらの分散安定剤が存在する。この分散安定剤
は、通常の洗浄工程では完全に除去することができず、
さらに水との親和性が高いため得られたトナーの帯電性
が不安定になりやすい。特に、高温高湿度時に帯電能力
の低下が著しくなるという問題があった。However, in suspension polymerization, relatively large amounts of poorly water-soluble inorganic fine powder and water-soluble polymers such as polyvinyl alcohol and carboxymethylcellulose are used as dispersion stabilizers for the 1,000-meter droplets. These dispersion stabilizers are present in This dispersion stabilizer cannot be completely removed by normal washing processes,
Furthermore, since it has a high affinity with water, the charging properties of the obtained toner tend to be unstable. In particular, there was a problem in that the charging ability deteriorated significantly at high temperatures and high humidity.
潜像を現像する方法に用いられるトナーには、記録信号
を忠実に可視化すべく種々の特性をコントロールするこ
とが要求されるが、これらの特性のなかでも帯電量のコ
ントロールは特に重要な問題の一つである。すなわち、
粒子径が一定であっても、親水性物質が表面に露出した
トナーは、個々の粒子の持つ帯電量に変動を生じ、帯電
量分布が広くなりやすい。このような帯電量分布のブロ
ードなトナーを用いて画像形成を行なった場合には、ト
ナーの飛散や画像上のかぶり、にじみ等により画質が低
下し、またトナーの現像特性がバラつくことによってト
ナーの耐久性が劣化するという問題を生ずる。The toner used in the method of developing a latent image is required to control various properties in order to faithfully visualize the recorded signal, but among these properties, controlling the amount of charge is a particularly important issue. There is one. That is,
Even if the particle size is constant, a toner in which a hydrophilic substance is exposed on the surface causes fluctuations in the amount of charge held by each particle, and tends to have a wide charge amount distribution. When forming images using toner with such a broad charge distribution, the image quality deteriorates due to toner scattering, fogging, and blurring on the image, and the toner develops due to variations in toner development characteristics. The problem arises that the durability of the material deteriorates.
従来、この懸濁重合法において上記トナーの、帯電特性
を向上するために各種の方法が提案されている。たとえ
ば、特開昭５６−１６１４０２号公報における疎水変性
剤により処理した難水溶性金属炭酸塩を分散安定剤に用
い、重合後、希酸によって金属炭酸塩を溶解除去する方
法。特開昭５９−１２３８５１号公報における無機系分
散剤によって重合の後、その重合体をアルカリ処理する
ことにより、無機系分散剤を溶解除去する方法がある。Conventionally, various methods have been proposed for improving the charging characteristics of the toner in this suspension polymerization method. For example, the method disclosed in JP-A-56-161402 uses a poorly water-soluble metal carbonate treated with a hydrophobic modifier as a dispersion stabilizer, and after polymerization, the metal carbonate is dissolved and removed with a dilute acid. There is a method disclosed in JP-A-59-123851 in which after polymerization with an inorganic dispersant, the polymer is treated with an alkali to dissolve and remove the inorganic dispersant.
しかし、前者の場合予め金属炭酸塩を疎水化する工程が
必要であり、重合体を希酸で処理した後、多量の水で水
洗することが必要であり煩雑である。また後者ではアル
カリ処理後の重合粒子表面からアルカリ成分を除去する
ことがきわめて困難であり、得られたトナーの帯電性は
必ずしも安定ではなかった。一方、特公平１−５３７８
８号公報では、シランカップリング剤を反応させた無機
微粒子分散安定剤を使用し、さらに生成した粒子をシラ
ンカップリング剤で処理している。この方法ではシャー
プな粒度分布とある程度良好な現像特性を持つトナーが
得られるものの、シランカップリング剤の種類や割合に
よっては重合禁止や分散状態の不安定化という不都合が
あった。However, in the former case, a step of hydrophobizing the metal carbonate is required in advance, and after the polymer is treated with a dilute acid, it is necessary to wash the polymer with a large amount of water, which is complicated. In addition, in the latter case, it was extremely difficult to remove the alkali component from the surface of the polymer particles after the alkali treatment, and the chargeability of the resulting toner was not necessarily stable. On the other hand, Tokuko 1-5378
In Publication No. 8, an inorganic fine particle dispersion stabilizer reacted with a silane coupling agent is used, and the generated particles are further treated with the silane coupling agent. Although this method yields a toner with a sharp particle size distribution and reasonably good development properties, it has the disadvantage of inhibiting polymerization and destabilizing the dispersion state depending on the type and proportion of the silane coupling agent.
本発明の目的は、トナー表面に残留した分散安定剤が疎
水化され、帯電安定性の優れたトナーとその製造方法を
提供することにある。An object of the present invention is to provide a toner in which the dispersion stabilizer remaining on the surface of the toner is made hydrophobic and has excellent charging stability, and a method for producing the toner.
本発明の他の目的は、着色剤や極性物質がトナー表面に
露出することなく、狭い帯電量分布を有し、帯電量の湿
度依存性がきわめて少ないトナーおよび製造方法を提供
することにある。Another object of the present invention is to provide a toner and a manufacturing method that have a narrow charge amount distribution without exposing the colorant or polar substance on the toner surface, and have extremely low humidity dependence of the charge amount.
［問題点を解決するための手段］
本発明は、少なくともラジカル重合性単量体と着色剤を
含む単量体組成物を、無機微粒子分散安定剤を含む分散
媒中で重合し、生成した重合体粒子を重合反応性シラン
カップリング剤で処理することを特徴とする。[Means for Solving the Problems] The present invention involves polymerizing a monomer composition containing at least a radically polymerizable monomer and a colorant in a dispersion medium containing an inorganic fine particle dispersion stabilizer. It is characterized in that the combined particles are treated with a polymerization-reactive silane coupling agent.
［作用コ
本発明は、重合体粒子を含む系に重合反応性シランカッ
プリング剤と望ましくは重合開始剤を添加することによ
って、得られた重合体粒子表面に残存する分散安定剤を
覆い疎水化処理することが特徴である。重合体粒子表面
を重合反応性シランカップリング剤で疎水化処理するこ
とにより、分散安定剤として使用した難水溶性無機微粉
末が重合体粒子表面に残留しても、トナーの帯電特性に
悪影響を及ぼさなくなる。シランカップリング剤は重合
途中、換言すれば、重合体粒子の合一が起こらなくなる
程度に重合反応が進行した後か、または重合反応停止後
に添加することが好ましい。[Function] In the present invention, by adding a polymerization-reactive silane coupling agent and preferably a polymerization initiator to a system containing polymer particles, the dispersion stabilizer remaining on the surface of the obtained polymer particles is covered and made hydrophobic. It is characterized by processing. By hydrophobicizing the surface of the polymer particles with a polymerization-reactive silane coupling agent, even if the poorly water-soluble inorganic fine powder used as a dispersion stabilizer remains on the surface of the polymer particles, it will not have an adverse effect on the charging characteristics of the toner. It will no longer affect you. The silane coupling agent is preferably added during the polymerization, in other words, after the polymerization reaction has progressed to such an extent that coalescence of the polymer particles no longer occurs, or after the polymerization reaction has been terminated.
これにより、シランカップリング剤による重合禁止作用
や、分散安定性の破壊は起こらない。この疎水化処理後
は、通常の濾過、水洗、乾燥工程によりトナーが得られ
る。This prevents the silane coupling agent from inhibiting polymerization or destroying dispersion stability. After this hydrophobization treatment, a toner can be obtained through ordinary filtration, water washing, and drying steps.
重合反応性シランカップリング剤は、トリメトキシシリ
ル基の他に重合反応性を官能基を有する公知の材料を使
用できる。すなわち、γ−メタクリロキシプロピルトリ
メトキシシラン、Ｎ−β−（Ｎ−ビニルベンジルアミノ
エチル）−７−アミツプロビルトリメトキシシラン・塩
酸塩、７−メルカプトトリメトキシシラン、γ−グリシ
ドキシプロビルトリメトキシシラン、ビニルトリアセト
キシシラン、ビニルトリメトキシシラン、γ−メルカプ
トプロピルメチルジメトキシシラン等が使用できる。た
だし、トナー表面にはシランカップリング剤の疎水基が
露出するため、目的とするトナーの帯電系列に合ったシ
ランカップリング剤を使用することが好ましい。シラン
カップリング剤の添加量としては、全重合体量に対し、
０．１重量％以上１０重量％以下であることが好ましい
。As the polymerization-reactive silane coupling agent, known materials having polymerization-reactive functional groups in addition to trimethoxysilyl groups can be used. Namely, γ-methacryloxypropyltrimethoxysilane, N-β-(N-vinylbenzylaminoethyl)-7-amituprobyltrimethoxysilane hydrochloride, 7-mercaptotrimethoxysilane, γ-glycidoxypropyl Viltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane, γ-mercaptopropylmethyldimethoxysilane, etc. can be used. However, since the hydrophobic group of the silane coupling agent is exposed on the toner surface, it is preferable to use a silane coupling agent that matches the charging series of the intended toner. The amount of silane coupling agent added is based on the total amount of polymer.
It is preferably 0.1% by weight or more and 10% by weight or less.
重合体粒子表面に結合した重合反応性シランカップリン
グ剤を重合させるには、公知の重合開始剤を使用するこ
とができる。すなわち、過硫酸カリウム、過硫酸アンモ
ニウム、アゾビスイソブチロニトリル、過酸化水素−鉄
（ＩＩ）塩、過硫酸カリウム−亜硫酸水素ナトリウム、
過酸化ベンゾイル−亜硫酸水素ナトリウム、クメンヒド
ロペルオキシド−鉄（ｎ）塩などの水溶性、レドックス
開始剤が使用できる。A known polymerization initiator can be used to polymerize the polymerization-reactive silane coupling agent bonded to the surface of the polymer particles. Namely, potassium persulfate, ammonium persulfate, azobisisobutyronitrile, hydrogen peroxide-iron(II) salt, potassium persulfate-sodium bisulfite,
Water-soluble, redox initiators such as benzoyl peroxide-sodium bisulfite, cumene hydroperoxide-iron(n) salt can be used.
本発明に使用する重合性単量体はラジカル重合性のもの
であり、生成した重合体がトナーの要求される熱特性と
静電気特性を有するよう一種または二種以上を組合せて
使用される。このような単量体の例としては、モノビニ
ル芳香族単量体、アクリル系単量体、ビニルエステル系
単量体、ビニルエーテル系単量体、ジオレフィン系単量
体、モノオレフィン系単量体などがある。The polymerizable monomers used in the present invention are radically polymerizable, and one or more monomers are used in combination so that the resulting polymer has the thermal properties and electrostatic properties required for the toner. Examples of such monomers include monovinyl aromatic monomers, acrylic monomers, vinyl ester monomers, vinyl ether monomers, diolefin monomers, and monoolefin monomers. and so on.
モノビニル単量体としては、スチレン、０−メチルスチ
レン、ｍ−メチルスチレン、ｐ−メチルスチレン、ｐ−
メトキシスチレン、ｐ−フェニルスチレン、ｐ−グロロ
スチレン、ｐ−エチルスチレン、ｐ−ｎ−ブチルスチレ
ン、ｐ−ｔｅｒｔ−プチルスチレン、ｐ−ｎ−ヘキシル
スチレン、ｐ−ｎ−オクチルスチレン、ｐ−ｎ−ノニル
スチレン、ｐ−ｎ−デシルスチレン、ｐ−ｎ−ドデシル
スチレン、２，４−ジメチルスチレン、３．４ジクロロ
スチレン等のスチレンとその誘導体が挙げられる。Monovinyl monomers include styrene, 0-methylstyrene, m-methylstyrene, p-methylstyrene, p-
Methoxystyrene, p-phenylstyrene, p-glolostyrene, p-ethylstyrene, p-n-butylstyrene, p-tert-butylstyrene, p-n-hexylstyrene, p-n-octylstyrene, p-n-nonyl Examples include styrene and derivatives thereof such as styrene, p-n-decylstyrene, p-n-dodecylstyrene, 2,4-dimethylstyrene, and 3.4-dichlorostyrene.
アクリル系単量体としては、アクリル酸、メタクリル酸
、アクリル酸メチル、アクリル酸エチル、アクリル酸ブ
チル、アクリル酸−２−エチルヘキシル、アクリル酸シ
クロヘキシル、アクリル酸フェニル、メタクリル酸メチ
ル、メタクリル酸エチル、メタクリル酸ブチル、メタク
リル酸ヘキシル、メタクリ酸−２−エチルヘキシル、β
−ヒドロキシアクリル酸エチル、γ−アミノアクリル酸
プロピル、メタクリル酸ステアリル、メタクリル酸ジメ
チルアミノエチル、メタクリル酸ジエチルアミノエチル
などがある。Acrylic monomers include acrylic acid, methacrylic acid, methyl acrylate, ethyl acrylate, butyl acrylate, 2-ethylhexyl acrylate, cyclohexyl acrylate, phenyl acrylate, methyl methacrylate, ethyl methacrylate, and methacrylate. Butyl methacrylate, hexyl methacrylate, 2-ethylhexyl methacrylate, β
-Ethyl hydroxyacrylate, γ-aminopropyl acrylate, stearyl methacrylate, dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate, and the like.
ビニルエステル系単量体としては、酢酸ビニル、プロピ
オン酸ビニル、ベンジェ酸ビニルなど、ビニルエーテル
系単量体としては、ビニルメチルエーテル、ビニルエチ
ルエーテル、ビニルイソブチルエーテル、ビニルフェニ
ルエーテルなどがある。Examples of vinyl ester monomers include vinyl acetate, vinyl propionate, and vinyl benzoate; examples of vinyl ether monomers include vinyl methyl ether, vinyl ethyl ether, vinyl isobutyl ether, and vinyl phenyl ether.
ジオレフィン系単量体としては、例えばブタジェン、イ
ソプレン、クロロプレンなど、モノオレフィン系単量体
としてはエチレン、プロピレン、イソブチレン、ブテン
−１、ペンテン−１，４−メチルペンテン−１などが挙
げられる。Examples of diolefin monomers include butadiene, isoprene, and chloroprene, and examples of monoolefin monomers include ethylene, propylene, isobutylene, butene-1, pentene-1,4-methylpentene-1, and the like.
また、重合速度や懸濁重合中の粒子の粘度を調節し、目
的とする粒子径および粒度分布を有する粒子を製造する
ために、あるいは得られたトナーの耐オフセット性を改
善するため、−分子中に不飽和結合を二個以上有する架
橋性単量体を共重合させてもよい。架橋性単量体として
は、ジビニルベンゼン、ジビニルナフタレン、ジビニル
エーテル、ジエチレングリコールメタクリレート、エチ
レングリコールジメタクリレート、ポリエチレングリコ
ールジメタクリレート、フタル酸ジアリルなどが挙げら
れる。これらの架橋性単量体を重合性単量体に対して共
重合させる割合は、単量体全量に対して０． ２〜２重
量％であることが好ましい。架橋性単量体の使用量が単
量体全量の０． ２重量％未満であると、重合中に粒子
の合一が起こり易く粒子径分布が広くなる。また、トナ
ーの耐オフセット性も低い。逆に、架橋性単量体の量が
単量体全量の２重量％を越えると、トナーの軟化点が上
昇し、定着性が悪くなるという不都合を生じる。In addition, in order to adjust the polymerization rate and the viscosity of particles during suspension polymerization to produce particles with a desired particle size and particle size distribution, or to improve the offset resistance of the obtained toner, - A crosslinkable monomer having two or more unsaturated bonds therein may be copolymerized. Examples of the crosslinkable monomer include divinylbenzene, divinylnaphthalene, divinyl ether, diethylene glycol methacrylate, ethylene glycol dimethacrylate, polyethylene glycol dimethacrylate, diallyl phthalate, and the like. The ratio of copolymerization of these crosslinkable monomers to the polymerizable monomers is 0. Preferably, it is 2 to 2% by weight. The amount of crosslinking monomer used is 0.0% of the total amount of monomers. When the amount is less than 2% by weight, coalescence of particles tends to occur during polymerization, resulting in a wide particle size distribution. Further, the offset resistance of the toner is also low. On the other hand, if the amount of the crosslinkable monomer exceeds 2% by weight of the total amount of monomers, the softening point of the toner increases, resulting in a disadvantage that the fixing properties deteriorate.
以上に述べたように、架橋性単量体を重合性単量体と共
重合することにより、トナー粒子径分布の調節およびト
ナーの熱定着特性の最適化を行うことができる。トナー
の粒子径が均一であると、粉体流動性が向上するため、
現像ムラが少なくなること、現像装置中の機械的ストレ
スに起因するトナー耐久性の劣化が少なくなる等の効果
がある。As described above, by copolymerizing a crosslinkable monomer with a polymerizable monomer, it is possible to adjust the toner particle size distribution and optimize the heat fixing characteristics of the toner. If the particle size of the toner is uniform, the powder fluidity will improve, so
There are effects such as less uneven development and less deterioration of toner durability due to mechanical stress in the developing device.
また、重合性単量体並びに架橋性単量体に着色剤などの
個体微粒子をポリエステル系分散剤を用いて分散させる
ことにより、分散性が著しく向上する。その結果、トナ
ー表面に露出した着色剤や極性化合物の量が飛踊的に低
減し、特に高湿度環境下での帯電特性の劣化と、それに
伴うトナーの飛散、かぶりを防止することができる。Further, by dispersing solid fine particles such as a colorant in the polymerizable monomer and crosslinkable monomer using a polyester dispersant, the dispersibility is significantly improved. As a result, the amount of colorant and polar compound exposed on the toner surface is dramatically reduced, making it possible to prevent deterioration of charging characteristics, especially in a high humidity environment, and the resulting toner scattering and fogging.
着色剤としては、公知の染料および顔料が使用できる。As the colorant, known dyes and pigments can be used.
例えば、染料は、ニグロシン染料、Ｃ，Ｉ。For example, the dye may be nigrosine dye, C,I.
ダイレクトレッド１、Ｃ，１，ダレクトレッド４、Ｃ０
１、アシッドレッド１、Ｃ，１，ベーシックレッド１、
Ｃ，１，ソルベントレッド、Ｃ，１，バットレッド、Ｃ
，ｌ。Direct Red 1, C, 1, Direct Red 4, C0
1, Acid Red 1, C, 1, Basic Red 1,
C,1,Solvent Red,C,1,Bat Red,C
,l.
ダイレクトブルー１、Ｃ，１，ダイレクトブルー２、Ｃ
，１，アシッドブルー１５、Ｃ，１，ベーシックブルー
３、Ｃ，１，ソルベントブルー、Ｃ，１，ダイレクトグ
リーン６、Ｃ，］、ソルベントレッドなどがある。顔料
としては、ファーネスブラック、アセチレンブラック、
カドミウムイエロー、ハシザイエローＧ、ナフトールイ
エローＳ、ピラゾロンレッド、パーマネントレッド４Ｒ
、モリブデンオレンジ、ファストバイオレットＢ、フタ
ロシアニンブルー、マラカイトグリーン、フタロシアニ
ングリーンなどが挙げられる。これらの着色剤は、充分
な濃度の可視像が形成されるにふされしい割合で含有さ
れることが必要であり、通常単量体組成物全量に対し、
２〜２０重量％の割合とされる。Direct Blue 1, C, 1, Direct Blue 2, C
, 1, Acid Blue 15, C, 1, Basic Blue 3, C, 1, Solvent Blue, C, 1, Direct Green 6, C,], Solvent Red, etc. Pigments include furnace black, acetylene black,
Cadmium Yellow, Hashiza Yellow G, Naphthol Yellow S, Pyrazolone Red, Permanent Red 4R
, molybdenum orange, fast violet B, phthalocyanine blue, malachite green, phthalocyanine green, etc. These colorants need to be contained in a proportion suitable for forming a visible image of sufficient concentration, and are usually contained in a proportion appropriate to the total amount of the monomer composition.
The proportion is 2 to 20% by weight.
トナーを磁性トナーとして用いるために、単量体組成物
中に磁性体微粒子を添加することも可能である。このよ
うな磁性体としては、鉄、コバルト、ニッケルなどの強
磁性金属の粉末、またはこれらにクロム、マンガン、銅
、亜鉛、アルミニウム、希土類元素などを加えた合金、
その酸化物であるマグネタイト、フェライトの微粉末が
用いられる。これらの磁性体の添加量はトナーの全重量
に対して、２０〜７０重量％が好ましい。In order to use the toner as a magnetic toner, it is also possible to add magnetic fine particles to the monomer composition. Examples of such magnetic materials include powders of ferromagnetic metals such as iron, cobalt, and nickel, or alloys of these with chromium, manganese, copper, zinc, aluminum, rare earth elements, etc.
Fine powder of magnetite and ferrite, which are oxides thereof, is used. The amount of these magnetic substances added is preferably 20 to 70% by weight based on the total weight of the toner.
重合開始剤としては、公知の重合開始剤を一種または二
種以上組合せて使用することができる。As the polymerization initiator, one or a combination of two or more known polymerization initiators can be used.
例えば、過硫酸カリウム、２−２′ −アゾビスイソ
ブチロニトリル、２−２′−アゾビス（２，４ジメチル
）バレロニトリル、２−２“ −アゾビス４−メトキシ
−２，４−ジメチルバレロニトリル、ベンゾイルパーオ
キサイド、２，４−ジクロロパーオキサイド、イソプロ
ピルバーオキシカボネート、クメンハイドロパーオキサ
イド、ラウロイルパーオキサイドまたはレドックス系開
始剤などを使用して重合を行なうことができる。これら
の重合開始剤の使用量は、単量体組成物の約０゜１〜５
重量％であることが好ましい。また、生成するトナーの
分子量を調節するため、ｔｅｒｔ−ブチルメルカプタン
、ｔｅｒｔ−ドデシルメルカプタンなどの分子量調節剤
をこれらの重合開始剤と同時に使用しても良い。For example, potassium persulfate, 2-2'-azobisisobutyronitrile, 2-2'-azobis(2,4dimethyl)valeronitrile, 2-2"-azobis4-methoxy-2,4-dimethylvaleronitrile. Polymerization can be carried out using benzoyl peroxide, 2,4-dichloroperoxide, isopropyl peroxide, cumene hydroperoxide, lauroyl peroxide, or a redox initiator. The amount used is approximately 0°1 to 5% of the monomer composition.
Preferably, it is % by weight. Furthermore, in order to adjust the molecular weight of the toner produced, a molecular weight regulator such as tert-butyl mercaptan or tert-dodecyl mercaptan may be used simultaneously with these polymerization initiators.
上記の千ツマー組成物を、機械式や超音波式のホモジナ
イザーにより水中に懸濁させて、重合する際、水中での
懸濁状態を安定化させるために、ゼラチン、カルボキシ
メチルセルロース、澱粉、ポリビニルアルコールなどの
水溶性高分子、界面活性剤、−炭酸カルシウム、炭酸マ
グネシウム、リン酸マグネシウム、硫酸バリウム、シリ
カ、アルミナなどの難水溶性無機塩類の微粒子を分散安
定剤として使用することが一般的である。これらの分散
安定剤は、単量体に対し、０．０１〜１０重量％の割合
で用いることが好ましい。When the above-mentioned composition is suspended in water using a mechanical or ultrasonic homogenizer and polymerized, gelatin, carboxymethylcellulose, starch, polyvinyl alcohol, etc. are used to stabilize the suspended state in water. It is common to use water-soluble polymers such as surfactants, fine particles of poorly water-soluble inorganic salts such as calcium carbonate, magnesium carbonate, magnesium phosphate, barium sulfate, silica, and alumina as dispersion stabilizers. . These dispersion stabilizers are preferably used in an amount of 0.01 to 10% by weight based on the monomer.
本発明において、上述した成分以外に必要に応じて、帯
電制御剤、流動性改質剤、クリーニング剤、オフセット
防止剤、充填剤などの添加剤を添加しても良い。In the present invention, in addition to the above-mentioned components, additives such as a charge control agent, a fluidity modifier, a cleaning agent, an anti-offset agent, and a filler may be added as necessary.
帯電制御剤としては、ニグロシン、四級化アンモニウム
塩、ポリアルキルアミド、モリブデン酸キレート顔料、
モノアゾ染料の金属錯体、ナフテン酸金属塩、サリチル
酸金属錯体などがある。As the charge control agent, nigrosine, quaternized ammonium salt, polyalkylamide, molybdate chelate pigment,
Examples include metal complexes of monoazo dyes, metal naphthenates, and metal complexes of salicylate.
流動性改質剤としては、疏水性シリカ、酸化チタン、ポ
リビニリデンフルオライド、金属石鹸などの微粉末が、
クリーニング助剤としては、ステアリン酸亜鉛、ステア
リン酸カルシウム、ステアリン酸マグネシウム、ポリメ
チルメタクリレート、ナイロン、ポリ四フッ化エチレン
、シリコンカーバイドなどの微粉末を用いることができ
る。これらの添加剤は、千ツマー組成物中に混合分散さ
せて用いるか、または、得られたトナー粒子の表面に添
加しても良い。As fluidity modifiers, fine powders such as hydrophobic silica, titanium oxide, polyvinylidene fluoride, and metal soap are used.
As cleaning aids, fine powders of zinc stearate, calcium stearate, magnesium stearate, polymethyl methacrylate, nylon, polytetrafluoroethylene, silicon carbide, and the like can be used. These additives may be used by being mixed and dispersed in the toner composition, or may be added to the surface of the obtained toner particles.
（実施例）
以下、実施例を用いて本発明の内容をさらに詳細に説明
する。なお、実施例および比較例中の部は重量部を表わ
す。(Example) Hereinafter, the content of the present invention will be explained in more detail using Examples. In addition, parts in Examples and Comparative Examples represent parts by weight.
（実施例１）
スチレン７８部、ｎ−ブチルメタクリレート２０部、メ
チルメタクリレート２部、ジビニルベンゼン０． ５部
、ｔ−ラウリルメルカプタン０．２部、アゾビスイソブ
チロニトリル２部、カーボンブラック（三菱化成工業製
ＭＡ−１００）８部、ポリエステル系分散剤（ポリへキ
サメチレンアジペート） １． ０部、帯電制御剤（
オリエント化学製ボントロンＳ−３４）１部、ポリエチ
レン（三井石油化学製ハイワックス２００Ｐ）２部をボ
ールミルに入れ２時間混合し、千ツマー組成混合物を得
た。(Example 1) 78 parts of styrene, 20 parts of n-butyl methacrylate, 2 parts of methyl methacrylate, 0.0 parts of divinylbenzene. 5 parts, t-lauryl mercaptan 0.2 parts, azobisisobutyronitrile 2 parts, carbon black (Mitsubishi Chemical Corporation MA-100) 8 parts, polyester dispersant (polyhexamethylene adipate) 1. 0 parts, charge control agent (
1 part of Orient Chemical's Bontron S-34) and 2 parts of polyethylene (Mitsui Petrochemical's Hiwax 200P) were placed in a ball mill and mixed for 2 hours to obtain a 100% composition mixture.
次に、容器にイオン交換水１０００部と微粉末シリカ（
日本アエロジル製アエロジル＃ ３００）１０部を入れ
、ホモジナイザー（日本特殊機化工業製ホモミキサー）
で撹拌し、分散媒中に上記のモノマー組成混合物を加え
、６０００ｒｐｍで１０分間分分散粒した。反応容器を
窒素置換した後、パドル撹拌翼を備えた撹拌装置に変更
し、２２Ｏｒｐｍで撹拌を続けながら７０℃に昇温し、
７時間反応させた。反応系の温度を５０℃に下げた後、
γ−メタクリロキシプロピルトリメトキシシラン（トー
レシリコーン製５Ｚ６０３０）５部、過硫酸カリウム０
．５部を加えて３時間撹拌した。得られた重合物を濾過
、水洗を行なった後脱水し、４０℃で１２時間減圧乾燥
を行った。この■・ナー乾燥粉末１００部に対し疎水性
シリカ（日本アエロジル族Ｒ９７２）０．５部をヘンシ
ェルミキサーにより混合し、トナー１を得た。得られた
トナーの粒子径をコールタ−カウンターで測定したとこ
ろ、体積平均粒径が８．５μｍ、個数平均粒径が６．９
ＡＬｍであり、４〜１６μｍの範囲の粒子が９５％以上
含まれており、分級操作は不要であった。Next, put 1000 parts of ion-exchanged water and fine powdered silica (
Add 10 parts of Aerosil #300 manufactured by Nippon Aerosil and use a homogenizer (Homomixer manufactured by Nippon Tokushu Kika Kogyo).
The above monomer composition mixture was added to the dispersion medium, and the mixture was dispersed for 10 minutes at 6000 rpm. After purging the reaction vessel with nitrogen, the stirring device was changed to a stirring device equipped with a paddle stirring blade, and the temperature was raised to 70°C while stirring at 22 Orpm.
The reaction was allowed to proceed for 7 hours. After lowering the temperature of the reaction system to 50°C,
5 parts of γ-methacryloxypropyltrimethoxysilane (Toray Silicone 5Z6030), 0 potassium persulfate
．． 5 parts were added and stirred for 3 hours. The obtained polymer was filtered, washed with water, dehydrated, and dried under reduced pressure at 40° C. for 12 hours. Toner 1 was obtained by mixing 0.5 parts of hydrophobic silica (Japan Aerosil Group R972) with 100 parts of this dry toner powder using a Henschel mixer. When the particle size of the obtained toner was measured using a Coulter counter, the volume average particle size was 8.5 μm, and the number average particle size was 6.9.
ALm, containing 95% or more of particles in the range of 4 to 16 μm, and no classification operation was necessary.
このトナー４部とコーテッドフェライトキャリア（日立
金属製ＫＢＮ−Ｃ１００） １００部とを混合して現像
剤を調製し、市販複写機（リコー製ＦＴ４０８０）を用
いて現像したところ、最高画像濃度１．４１（○、Ｄ、
）で、ブラシマークやかぶりのない、解像度、階調性、
ベタ部の緻密性の良好な高品位の画像が得られた。ブロ
ーオフ帯電量を測定すると−２６，３（μＣ／ｇ）であ
った。また、３５℃８０％ＲＨの高湿度環境下に８時間
放置した後でも、帯電量−２１，５（μＣ／ｇ）と変化
が少なく、通常環境下と同様の良好な画像が得られた。A developer was prepared by mixing 4 parts of this toner and 100 parts of coated ferrite carrier (KBN-C100 manufactured by Hitachi Metals), and developed using a commercially available copying machine (FT4080 manufactured by Ricoh). The maximum image density was 1.41. (○, D,
), with no brush marks or fog, resolution, gradation,
A high-quality image with good density in solid areas was obtained. When the blow-off charge amount was measured, it was -26.3 (μC/g). Further, even after being left in a high humidity environment at 35° C. and 80% RH for 8 hours, the charge amount remained -21.5 (μC/g), which showed little change, and a good image similar to that under a normal environment was obtained.
さらに１０，０００枚複写後も画質の変化はほとんどな
かった。また、感光体のクリーニング性も良好であり、
オフセットによる定着ローラーの汚れもなかった。Furthermore, there was almost no change in image quality even after copying 10,000 sheets. In addition, the photoreceptor has good cleaning properties,
There was no dirt on the fixing roller due to offset.
（実施例２）
スチレン９２部、２−エチルへキシルアクリレート８部
、ジビニルベンゼン０．１ｆｉｉｌ、アゾビス２．４−
ジメチルバレロニトリル１部、カーボンブラック（三菱
化成工業族ＭＡ−６００）１部、ポリエステル系分散剤
（ＩＣＩ製ハイパーマーＬＰ５）０．５部、マグネタイ
ト（関東電化製ＷＢＣ−１００）４０部、帯電制御剤（
採土ケ谷化学製アイゼンスビロンブラックＴＲＨ）Ｏ，
Ｊｌｌ、ポリプロピレン２部をアトライターで２時間混
合分散させた。(Example 2) 92 parts of styrene, 8 parts of 2-ethylhexyl acrylate, 0.1 fiil of divinylbenzene, 2.4 parts of azobis
1 part of dimethylvaleronitrile, 1 part of carbon black (Mitsubishi Chemical Corporation MA-600), 0.5 part of polyester dispersant (Hypermar LP5 manufactured by ICI), 40 parts of magnetite (WBC-100 manufactured by Kanto Denka), charge control Agent (
Odugaya Chemical Eisen Subiron Black TRH) O,
2 parts of polypropylene were mixed and dispersed for 2 hours using an attritor.
得られた千ツマー組成混合物を実施例１と同様の方法で
、水中に分散し重合した。重合後さらにビニルトリメト
キシシラン（トーμ・シリコーン製５Ｚ６３００）１０
部、過硫酸カリウム０．５部、亜硫酸水素ナトリウム０
． ５部を加え２時間撹拌した。続いて実施例１と同様
の方法で濾過、水洗、乾燥を行いトナー２を得た。得ら
れたトナー２は、体積平均粒径が１０．２μｍ、個数平
均粒が７．５μｍであり、４〜１６μｍの範囲の粒子が
９５％以上含まれており、分級操作は不要であった。The resulting mixture was dispersed in water and polymerized in the same manner as in Example 1. After polymerization, add vinyltrimethoxysilane (5Z6300 manufactured by Tomu Silicone) 10
parts, potassium persulfate 0.5 parts, sodium bisulfite 0
．． 5 parts were added and stirred for 2 hours. Subsequently, filtration, washing with water, and drying were performed in the same manner as in Example 1 to obtain Toner 2. The obtained toner 2 had a volume average particle diameter of 10.2 μm, a number average particle size of 7.5 μm, and contained 95% or more of particles in the range of 4 to 16 μm, and no classification operation was necessary.
このトナーを用いてプリンタ（日本電気製ＰＣ−ＰＲ６
０１）により画像評価を行なったところ、画像濃度１．
３８ （０，Ｄ、 ）で、がぶりのない高品位の画像が
得られた。また、３５℃８ｏ％ＲＨの高湿度環境下でも
、通常環境下と同様の良好な画像が得られた。さらに１
０，０００枚プリント後も画質の変化はほとんどながっ
た。また、感光体のクリーニング性も良好であり、オフ
セットによる定着ローラーの汚れもながった。Using this toner, a printer (NEC PC-PR6)
01), the image density was 1.
38 (0, D, ), a high-quality image without blur was obtained. Furthermore, even under a high humidity environment of 35° C. and 80% RH, good images similar to those under a normal environment were obtained. 1 more
There was almost no change in image quality even after printing 0,000 sheets. Additionally, the photoreceptor had good cleaning properties, and the fixing roller was free from stains due to offset.
（実施例３）
スチレン８０部、ジエチルアミノメタクリレート１５ｓ
、メチルメタクリレート４ｓ、ジビニルベンゼン０．５
部、ｔ−ラウリルメルカプタン０゜５部、ラウリルパー
オキサイド１部、カーボンブラックル（三菱化成工業族
＃３０）７部、ポリエステル系分散剤（ポリテトラメチ
レンサクシネート）１部、帯電制御剤（オリエント化学
製オイルブラックＢＹ）２部をボールミルで２時間分散
混合した８
次に、容器にイオン交換水１０００部と微粉末シリカ（
日本アエロジル製アエロジル＃ ２００）１０部を入れ
、ホモジナイザー（日本特殊機化工業製ホモミキサー）
で撹拌し、分散媒中に上記のモノマー組成混合物を加え
、６０００ｒｐｍて１０分間分分散粒した。反応容器を
窒素置換した後、パドル撹拌翼を備えた撹拌装置に変更
し、２２０ｒｐｍで撹拌を続けながら７０℃に昇温し、
７時間反応させた。次いで、アゾビスイソブチロニトリ
ル０． １部を溶解させたＮ−β−（Ｎ−ビニルベンジ
ルアミノエチル）−γ−アミノプロピルトリメトキシシ
ラン・塩酸塩２部を反応系に加え、３時間撹拌した。得
られた重合物を、濾過、水洗を行なった後脱水し、４０
℃で１２時間減圧乾燥を行ないトナー３を得た。得られ
たトナーの粒子径をコールタ−カウンターで測定したと
ころ、体積平均粒径が７．５μｍ、個数平均粒径が６．
３μｍであり、４〜１６μｍの範囲の粒子が９５％以上
含まれており、分級操作は不要であった。(Example 3) 80 parts of styrene, 15s of diethylaminomethacrylate
, methyl methacrylate 4s, divinylbenzene 0.5
0.5 parts of t-lauryl mercaptan, 1 part of lauryl peroxide, 7 parts of carbon blackle (Mitsubishi Chemical Group #30), 1 part of polyester dispersant (polytetramethylene succinate), charge control agent (Orient 2 parts of chemical oil black BY) were dispersed and mixed in a ball mill for 2 hours.Next, in a container, 1000 parts of ion exchange water and fine powder silica (
Add 10 parts of Aerosil #200 manufactured by Nippon Aerosil and place in a homogenizer (Homomixer manufactured by Nippon Tokushu Kika Kogyo).
The above monomer composition mixture was added to the dispersion medium, and the mixture was dispersed for 10 minutes at 6000 rpm. After purging the reaction vessel with nitrogen, the stirring device was changed to a stirring device equipped with a paddle stirring blade, and the temperature was raised to 70°C while stirring at 220 rpm.
The reaction was allowed to proceed for 7 hours. Then, azobisisobutyronitrile 0. 2 parts of N-β-(N-vinylbenzylaminoethyl)-γ-aminopropyltrimethoxysilane hydrochloride in which 1 part was dissolved was added to the reaction system, and the mixture was stirred for 3 hours. The obtained polymer was filtered, washed with water, and then dehydrated.
Toner 3 was obtained by drying under reduced pressure at .degree. C. for 12 hours. When the particle size of the obtained toner was measured using a Coulter counter, the volume average particle size was 7.5 μm, and the number average particle size was 6.5 μm.
3 μm, and contained 95% or more of particles in the range of 4 to 16 μm, so no classification operation was necessary.
このトナー４部と鉄粉キャリア（日本鉄粉製ＴＳＳＶ３
００）１００部とを混合して現像剤を調製し、市販複写
機（シャープ製５Ｆ７２００）を用いて現像したところ
、最高画像濃度１．５１（０，Ｄ、）で、ブラシマーク
やかぶりのない、解像度、階調性、ベタ部の緻密性の良
好な高品位の画像が得られた。ブローオフ帯電量は＋１
８゜２（μＣ／ ｇ ）であった。また、３５℃８０％
ＲＨの高湿度環境下でも、通常環境下と同様の良好な画
像が得られ、さらに１０，０００枚複写後も画質の変化
はほとんどなかった。また、感光体のクリーニング性も
良好であり、オフセットによる定着ローラーの汚れもな
かった。4 parts of this toner and iron powder carrier (TSSV3 made by Nippon Iron Powder)
When a developer was prepared by mixing 100 parts of 00) and developed using a commercially available copying machine (Sharp 5F7200), the maximum image density was 1.51 (0, D,), with no brush marks or fog. A high-quality image with good resolution, gradation, and solid area density was obtained. Blow-off charge amount is +1
It was 8°2 (μC/g). Also, 35℃80%
Even under the high humidity environment of RH, good images similar to those under the normal environment were obtained, and there was almost no change in image quality even after copying 10,000 sheets. Furthermore, the cleaning performance of the photoreceptor was good, and there was no staining of the fixing roller due to offset.
（比較例１）
実施例１のシランカップリング剤γ−メタクリロキシプ
ロピルトリメトキシシラン、過硫酸カリウムを加えない
他は、実施例１と同様の組成および方法を用いてトナー
を製造し、トナー４を得た。(Comparative Example 1) A toner was produced using the same composition and method as in Example 1, except that the silane coupling agent γ-methacryloxypropyltrimethoxysilane and potassium persulfate of Example 1 were not added. I got it.
実施例１と同様の方法で市販複写機により画像評価を行
なったが、得られた画像は最高画像濃度が０．８５ （
０，Ｄ、）と低く、著しいかぶりを生じており、実用的
レベルに達していなかった。ブローオフ帯電量の値は、
−１３，３（μＣ／ｇ）であった。Image evaluation was performed using a commercially available copying machine in the same manner as in Example 1, and the obtained image had a maximum image density of 0.85 (
0, D, ), and significant fogging occurred, which did not reach a practical level. The value of blow-off charge amount is
-13.3 (μC/g).
（比較例２）
実施例１のシランカップリング剤γ−メタクリロキシプ
ロピルトリメトキシシラン５部に代えて、メチルトリメ
トキシシラン５部を添加した他は実施例１と同様の組成
、方法によりトナー５を作成した。(Comparative Example 2) Toner 5 was prepared using the same composition and method as in Example 1, except that 5 parts of methyltrimethoxysilane was added in place of 5 parts of γ-methacryloxypropyltrimethoxysilane, the silane coupling agent, in Example 1. It was created.
このトナーを実施例１と同様の方法で画像評価を行なっ
たところ、初期画像は画像濃度１．３５でかぶりやにじ
みがなく良好であったが、３５℃８０％ＲＨの環境下で
はややかぶりを生じた。また、２０００枚を越える複写
枚数では画像濃度が１゜０以下に低下した。When this toner was subjected to image evaluation in the same manner as in Example 1, the initial image had an image density of 1.35 and was good with no fogging or bleeding, but slight fogging was observed in an environment of 35°C and 80% RH. occured. Further, when the number of copies exceeded 2000, the image density decreased to 1.0 or less.
［発明の効果コ
本発明の静電荷像現像用トナーの製造方法は、以上記述
のような構成および作用であり、懸濁重合によるトナー
製造方法において、トナーの帯電性が安定で、画像濃度
が高くかぶりのない鮮明な画像を与えるトナーを製造方
法を提供できる。[Effects of the Invention] The method for producing a toner for developing an electrostatic image according to the present invention has the structure and operation as described above, and in the method for producing a toner by suspension polymerization, the chargeability of the toner is stable and the image density is high. It is possible to provide a method for producing a toner that gives a clear image without high fogging.
Claims (1)
組成物を、無機微粒子分散安定剤を含む分散媒中で重合
し、生成した重合体粒子を重合反応性シランカップリン
グ剤で処理することを特徴とする静電荷像現像用トナー
の製造方法。A monomer composition containing at least a radically polymerizable monomer and a colorant is polymerized in a dispersion medium containing an inorganic fine particle dispersion stabilizer, and the resulting polymer particles are treated with a polymerization-reactive silane coupling agent. A method for producing a toner for developing an electrostatic image, characterized by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2136142A JPH0429250A (en) | 1990-05-25 | 1990-05-25 | Manufacture of electrostatic charge image developing toner |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2136142A JPH0429250A (en) | 1990-05-25 | 1990-05-25 | Manufacture of electrostatic charge image developing toner |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0429250A true JPH0429250A (en) | 1992-01-31 |
Family
ID=15168291
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2136142A Pending JPH0429250A (en) | 1990-05-25 | 1990-05-25 | Manufacture of electrostatic charge image developing toner |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0429250A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010245742A (en) * | 2009-04-03 | 2010-10-28 | Toyota Central R&D Labs Inc | Antenna device |
| JP2017134164A (en) * | 2016-01-26 | 2017-08-03 | キヤノン株式会社 | Method for manufacturing toner particle |
-
1990
- 1990-05-25 JP JP2136142A patent/JPH0429250A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010245742A (en) * | 2009-04-03 | 2010-10-28 | Toyota Central R&D Labs Inc | Antenna device |
| JP2017134164A (en) * | 2016-01-26 | 2017-08-03 | キヤノン株式会社 | Method for manufacturing toner particle |
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