JPH01573A - Color toner for developing electrostatic latent images - Google Patents
Color toner for developing electrostatic latent imagesInfo
- Publication number
- JPH01573A JPH01573A JP63-5341A JP534188A JPH01573A JP H01573 A JPH01573 A JP H01573A JP 534188 A JP534188 A JP 534188A JP H01573 A JPH01573 A JP H01573A
- Authority
- JP
- Japan
- Prior art keywords
- toner
- weight
- parts
- manufactured
- acrylate
- 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
- 239000003795 chemical substances by application Substances 0.000 claims description 48
- 239000011162 core material Substances 0.000 claims description 29
- 239000000178 monomer Substances 0.000 claims description 28
- 239000003086 colorant Substances 0.000 claims description 25
- 229920005992 thermoplastic resin Polymers 0.000 claims description 21
- 239000011347 resin Substances 0.000 claims description 16
- 229920005989 resin Polymers 0.000 claims description 16
- 125000000524 functional group Chemical group 0.000 claims description 11
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 239000002245 particle Substances 0.000 description 47
- -1 phenothiazine compound Chemical class 0.000 description 34
- 239000000126 substance Substances 0.000 description 32
- 238000000034 method Methods 0.000 description 23
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 22
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 16
- 230000009477 glass transition Effects 0.000 description 16
- 239000000975 dye Substances 0.000 description 15
- 239000000463 material Substances 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 229920006026 co-polymeric resin Polymers 0.000 description 10
- 239000000049 pigment Substances 0.000 description 10
- 238000005259 measurement Methods 0.000 description 9
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 9
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- 238000009826 distribution Methods 0.000 description 7
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000002344 surface layer Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000011651 chromium Substances 0.000 description 6
- 239000012798 spherical particle Substances 0.000 description 6
- IYHIFXGFKVJNBB-UHFFFAOYSA-N 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonic acid Chemical compound C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S(O)(=O)=O IYHIFXGFKVJNBB-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
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- 238000011088 calibration curve Methods 0.000 description 5
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- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 5
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 229910052804 chromium Inorganic materials 0.000 description 4
- 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 4
- 239000000428 dust Substances 0.000 description 4
- 210000003746 feather Anatomy 0.000 description 4
- YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 238000010298 pulverizing process Methods 0.000 description 4
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 244000215068 Acacia senegal Species 0.000 description 3
- 229920000084 Gum arabic Polymers 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 239000000205 acacia gum Substances 0.000 description 3
- 235000010489 acacia gum Nutrition 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000009396 hybridization Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000001054 red pigment Substances 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- OSNILPMOSNGHLC-UHFFFAOYSA-N 1-[4-methoxy-3-(piperidin-1-ylmethyl)phenyl]ethanone Chemical compound COC1=CC=C(C(C)=O)C=C1CN1CCCCC1 OSNILPMOSNGHLC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 2
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- GTRGJJDVSJFNTE-UHFFFAOYSA-N chembl2009633 Chemical compound OC1=CC=C2C=C(S(O)(=O)=O)C=CC2=C1N=NC1=CC=CC=C1 GTRGJJDVSJFNTE-UHFFFAOYSA-N 0.000 description 2
- 239000008119 colloidal silica Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-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
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 235000019239 indanthrene blue RS Nutrition 0.000 description 2
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 108091008695 photoreceptors Proteins 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
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- 238000002798 spectrophotometry method Methods 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 0.000 description 2
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- 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
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 1
- DMADTXMQLFQQII-UHFFFAOYSA-N 1-decyl-4-ethenylbenzene Chemical compound CCCCCCCCCCC1=CC=C(C=C)C=C1 DMADTXMQLFQQII-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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- VBHXIMACZBQHPX-UHFFFAOYSA-N 2,2,2-trifluoroethyl prop-2-enoate Chemical compound FC(F)(F)COC(=O)C=C VBHXIMACZBQHPX-UHFFFAOYSA-N 0.000 description 1
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- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
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- QTSNFLIDNYOATQ-UHFFFAOYSA-N 2-[(4-chloro-2-nitrophenyl)diazenyl]-n-(2-chlorophenyl)-3-oxobutanamide Chemical compound C=1C=CC=C(Cl)C=1NC(=O)C(C(=O)C)N=NC1=CC=C(Cl)C=C1[N+]([O-])=O QTSNFLIDNYOATQ-UHFFFAOYSA-N 0.000 description 1
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- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 description 1
- LQZFGPJGXVFSTR-UHFFFAOYSA-N 2-[[2-chloro-4-[3-chloro-4-[[1-(2-methylanilino)-1,3-dioxobutan-2-yl]diazenyl]phenyl]phenyl]diazenyl]-n-(2-methylphenyl)-3-oxobutanamide Chemical compound C=1C=CC=C(C)C=1NC(=O)C(C(=O)C)N=NC(C(=C1)Cl)=CC=C1C(C=C1Cl)=CC=C1N=NC(C(C)=O)C(=O)NC1=CC=CC=C1C LQZFGPJGXVFSTR-UHFFFAOYSA-N 0.000 description 1
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- 239000005083 Zinc sulfide Substances 0.000 description 1
- ULQMPOIOSDXIGC-UHFFFAOYSA-N [2,2-dimethyl-3-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)(C)COC(=O)C(C)=C ULQMPOIOSDXIGC-UHFFFAOYSA-N 0.000 description 1
- JUDXBRVLWDGRBC-UHFFFAOYSA-N [2-(hydroxymethyl)-3-(2-methylprop-2-enoyloxy)-2-(2-methylprop-2-enoyloxymethyl)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)(COC(=O)C(C)=C)COC(=O)C(C)=C JUDXBRVLWDGRBC-UHFFFAOYSA-N 0.000 description 1
- AUNAPVYQLLNFOI-UHFFFAOYSA-L [Pb++].[Pb++].[Pb++].[O-]S([O-])(=O)=O.[O-][Cr]([O-])(=O)=O.[O-][Mo]([O-])(=O)=O Chemical compound [Pb++].[Pb++].[Pb++].[O-]S([O-])(=O)=O.[O-][Cr]([O-])(=O)=O.[O-][Mo]([O-])(=O)=O AUNAPVYQLLNFOI-UHFFFAOYSA-L 0.000 description 1
- HZEWFHLRYVTOIW-UHFFFAOYSA-N [Ti].[Ni] Chemical compound [Ti].[Ni] HZEWFHLRYVTOIW-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000006230 acetylene black Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- AOADSHDCARXSGL-ZMIIQOOPSA-M alkali blue 4B Chemical compound CC1=CC(/C(\C(C=C2)=CC=C2NC2=CC=CC=C2S([O-])(=O)=O)=C(\C=C2)/C=C/C\2=N\C2=CC=CC=C2)=CC=C1N.[Na+] AOADSHDCARXSGL-ZMIIQOOPSA-M 0.000 description 1
- 125000005526 alkyl sulfate group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- QDHUQRBYCVAWEN-UHFFFAOYSA-N amino prop-2-enoate Chemical class NOC(=O)C=C QDHUQRBYCVAWEN-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- GHPGOEFPKIHBNM-UHFFFAOYSA-N antimony(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Sb+3].[Sb+3] GHPGOEFPKIHBNM-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 1
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001055 blue pigment Substances 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- CJOBVZJTOIVNNF-UHFFFAOYSA-N cadmium sulfide Chemical compound [Cd]=S CJOBVZJTOIVNNF-UHFFFAOYSA-N 0.000 description 1
- ZYCAIJWJKAGBLN-UHFFFAOYSA-N cadmium(2+);mercury(2+);disulfide Chemical compound [S-2].[S-2].[Cd+2].[Hg+2] ZYCAIJWJKAGBLN-UHFFFAOYSA-N 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000006231 channel black Substances 0.000 description 1
- HBHZKFOUIUMKHV-UHFFFAOYSA-N chembl1982121 Chemical compound OC1=CC=C2C=CC=CC2=C1N=NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HBHZKFOUIUMKHV-UHFFFAOYSA-N 0.000 description 1
- PZTQVMXMKVTIRC-UHFFFAOYSA-L chembl2028348 Chemical compound [Ca+2].[O-]S(=O)(=O)C1=CC(C)=CC=C1N=NC1=C(O)C(C([O-])=O)=CC2=CC=CC=C12 PZTQVMXMKVTIRC-UHFFFAOYSA-L 0.000 description 1
- ZLFVRXUOSPRRKQ-UHFFFAOYSA-N chembl2138372 Chemical compound [O-][N+](=O)C1=CC(C)=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 ZLFVRXUOSPRRKQ-UHFFFAOYSA-N 0.000 description 1
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- RTVSUIOGXLXKNM-UHFFFAOYSA-N dec-1-enylbenzene Chemical compound CCCCCCCCC=CC1=CC=CC=C1 RTVSUIOGXLXKNM-UHFFFAOYSA-N 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- ZDLVUKNLGUZMAS-UHFFFAOYSA-N dibutyl hydrogen phosphate;ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C.CCCCOP(O)(=O)OCCCC ZDLVUKNLGUZMAS-UHFFFAOYSA-N 0.000 description 1
- BCJAMGWKHPTZEU-UHFFFAOYSA-N dibutyl hydrogen phosphate;ethyl prop-2-enoate Chemical compound CCOC(=O)C=C.CCCCOP(O)(=O)OCCCC BCJAMGWKHPTZEU-UHFFFAOYSA-N 0.000 description 1
- ZWDKULOBXUJNPU-UHFFFAOYSA-N diethyl hydrogen phosphate;ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C.CCOP(O)(=O)OCC ZWDKULOBXUJNPU-UHFFFAOYSA-N 0.000 description 1
- VFAWCJZNIUIZOC-UHFFFAOYSA-N diethyl hydrogen phosphate;ethyl prop-2-enoate Chemical compound CCOC(=O)C=C.CCOP(O)(=O)OCC VFAWCJZNIUIZOC-UHFFFAOYSA-N 0.000 description 1
- ZKHFUIIZFCSYQB-UHFFFAOYSA-N dimethyl hydrogen phosphate;ethyl prop-2-enoate Chemical compound CCOC(=O)C=C.COP(O)(=O)OC ZKHFUIIZFCSYQB-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- GFJVXXWOPWLRNU-UHFFFAOYSA-N ethenyl formate Chemical compound C=COC=O GFJVXXWOPWLRNU-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-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
- 238000001125 extrusion Methods 0.000 description 1
- FPVGTPBMTFTMRT-NSKUCRDLSA-L fast yellow Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-NSKUCRDLSA-L 0.000 description 1
- 235000019233 fast yellow AB Nutrition 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000006232 furnace black Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000001056 green pigment Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- PBZROIMXDZTJDF-UHFFFAOYSA-N hepta-1,6-dien-4-one Chemical compound C=CCC(=O)CC=C PBZROIMXDZTJDF-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 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
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 235000010187 litholrubine BK Nutrition 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229940107698 malachite green Drugs 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
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000002794 monomerizing effect Effects 0.000 description 1
- 229910001000 nickel titanium Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- HILCQVNWWOARMT-UHFFFAOYSA-N non-1-en-3-one Chemical compound CCCCCCC(=O)C=C HILCQVNWWOARMT-UHFFFAOYSA-N 0.000 description 1
- LKEDKQWWISEKSW-UHFFFAOYSA-N nonyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCOC(=O)C(C)=C LKEDKQWWISEKSW-UHFFFAOYSA-N 0.000 description 1
- MDYPDLBFDATSCF-UHFFFAOYSA-N nonyl prop-2-enoate Chemical compound CCCCCCCCCOC(=O)C=C MDYPDLBFDATSCF-UHFFFAOYSA-N 0.000 description 1
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 239000001053 orange pigment Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 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
- 235000012736 patent blue V Nutrition 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- GYDSPAVLTMAXHT-UHFFFAOYSA-N pentyl 2-methylprop-2-enoate Chemical compound CCCCCOC(=O)C(C)=C GYDSPAVLTMAXHT-UHFFFAOYSA-N 0.000 description 1
- ULDDEWDFUNBUCM-UHFFFAOYSA-N pentyl prop-2-enoate Chemical compound CCCCCOC(=O)C=C ULDDEWDFUNBUCM-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
- 238000005375 photometry Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920005650 polypropylene glycol diacrylate Polymers 0.000 description 1
- 229920005651 polypropylene glycol dimethacrylate Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000001057 purple pigment Substances 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 235000012752 quinoline yellow Nutrition 0.000 description 1
- 239000004172 quinoline yellow Substances 0.000 description 1
- 229940051201 quinoline yellow Drugs 0.000 description 1
- 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
- 230000001105 regulatory effect Effects 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- KVMUSGMZFRRCAS-UHFFFAOYSA-N sodium;5-oxo-1-(4-sulfophenyl)-4-[(4-sulfophenyl)diazenyl]-4h-pyrazole-3-carboxylic acid Chemical compound [Na+].OC(=O)C1=NN(C=2C=CC(=CC=2)S(O)(=O)=O)C(=O)C1N=NC1=CC=C(S(O)(=O)=O)C=C1 KVMUSGMZFRRCAS-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 229920005792 styrene-acrylic resin Polymers 0.000 description 1
- 150000003457 sulfones Chemical group 0.000 description 1
- 125000002130 sulfonic acid ester group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
- JEVGKYBUANQAKG-UHFFFAOYSA-N victoria blue R Chemical compound [Cl-].C12=CC=CC=C2C(=[NH+]CC)C=CC1=C(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 JEVGKYBUANQAKG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229960000834 vinyl ether Drugs 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】 本発明は、静電潜像現像用のカラートナーに関する。[Detailed description of the invention] The present invention relates to a color toner for developing electrostatic latent images.
従来の技術
静電潜像の現像は感光体上に形成された静電潜像に対し
、摩擦帯電されたトナーを静電的に吸着させることによ
り行なわれている。2. Description of the Related Art Development of an electrostatic latent image is carried out by electrostatically adhering triboelectrically charged toner to the electrostatic latent image formed on a photoreceptor.
従来よりトナーに荷電を与える方法とし工、二成分現像
方式では一般にキャリアといわれる物質と混合・撹拌し
荷電を付与することが知られている。また、−成分現像
方式でも、現像スリーブやトナー規制ブレード、又は感
光体などとの接触により荷電を付与することが知られて
いる。いずれの方法によっても、トナーに均一な荷電が
与えられていなければ、現像及び転写の際に問題が生じ
る。このために、従来、トナーへの荷電の付与は、キャ
リアまたはブレード材などの摩擦帯電系列とは逆の摩擦
帯電系列を有する荷電付与剤をトナーの内部に入れるこ
とにより行われてきた。たとえば、熱可塑性の樹脂や着
色剤と共に荷電付与剤を混合・混練した後、粉砕・分級
してトナー粒子を得る粉砕法トナー、あるいは、モノマ
ーに着色剤、荷電付与剤を分散し、これを重合して得ら
れる懸濁重合トナー、あるいは、着色剤とワックスなど
の低軟化点物質や定着用樹脂を含んだ液体などと荷電付
与剤の回りを、これらよりも軟化点の高い壁材（カプセ
ル役）でくるんだカプセルトナー、また、特開昭６１−
２４０３６８号公報において、微小球状樹脂とバインダ
ー用樹脂および着色剤を、球状樹脂の軟化点より低く、
かつバインダー用樹脂の軟化点より高い温度で混合・撹
拌し、溶融したバインダー用樹脂によって球状樹脂表面
に着色剤を付着させる方法が、特開昭５９−３７５５３
号公報において、樹脂の表面に着色剤を付着させる方法
が挙げられている。Conventionally, it has been known that toner is charged by mixing and stirring it with a substance called a carrier in a two-component development method. Furthermore, in the -component development method, it is known that charge is imparted by contact with a developing sleeve, a toner regulating blade, a photoreceptor, or the like. Regardless of the method used, if the toner is not uniformly charged, problems occur during development and transfer. For this reason, toner has conventionally been charged with a charge by introducing a charge imparting agent having a triboelectric charging series opposite to that of a carrier or a blade material into the toner. For example, a pulverization method toner in which a charge imparting agent is mixed and kneaded with a thermoplastic resin and a coloring agent, and then crushed and classified to obtain toner particles, or a toner produced by a pulverization method in which toner particles are obtained by mixing and kneading a charge imparting agent with a thermoplastic resin and a coloring agent, or a toner produced by dispersing a coloring agent and a charge imparting agent in a monomer and polymerizing the resulting toner particles. The suspension polymerized toner obtained by ) wrapped capsule toner, also JP-A-61-
In JP 240368, the microspherical resin, the binder resin, and the colorant are lower than the softening point of the spherical resin,
A method of mixing and stirring at a temperature higher than the softening point of the binder resin and attaching a coloring agent to the surface of the spherical resin using the molten binder resin is disclosed in JP-A-59-37553.
In the publication, a method of attaching a coloring agent to the surface of a resin is mentioned.
従来の製造方法による粉砕法トナー、懸濁重合トナー、
カプセルトナーなどは、いずれもトナー粒子の内部に荷
電付与剤が存在し表面には添加量のうち極くわずかしか
存在しない。そのために、トナーの帯電量の分布が広く
なり、またそれに伴ないトナーの飛散、カブリなどの問
題が生じる。Pulverization method toner, suspension polymerization toner,
In all capsule toners, a charge imparting agent is present inside the toner particles, and only a small amount of the charge imparting agent is present on the surface. Therefore, the distribution of the amount of charge on the toner becomes wide, and problems such as toner scattering and fogging occur accordingly.
また、粉砕法トナーあるいは、カプセルトナー等におい
ては、トナーの各組成物が均一分散されているかどうか
により、トナーの帯電量分布のバラツキの度合いが変わ
ってくる。この為、トナー各組成物を各トナーにおいて
均一分散させることが重要な課題となっている。Furthermore, in the case of a pulverized toner, a capsule toner, or the like, the degree of variation in the charge amount distribution of the toner changes depending on whether each component of the toner is uniformly dispersed. Therefore, it is an important issue to uniformly disperse each toner composition in each toner.
特開昭６１−２１０３６８号公報に挙げられているトナ
ーも、トナーの表面を低軟化点のバインダー用樹脂でコ
ートするため、前述した従来の製造方法によるトナーと
同様の問題が生じる。また、特開昭５９−３７５５３号
公報のトナーでは、トナー表面のみ着色剤を付着させる
ため、少量の着色剤ではＩＤが不足し、また大量に着色
剤を添加すると、トナーより着色剤が剥離しキャリア表
面にスペント化したり、現像剤中に混入して耐刷性を劣
化させたりする問題が生じる。The toner disclosed in Japanese Unexamined Patent Publication No. 61-210368 also has the same problems as the toner manufactured by the conventional manufacturing method described above because the surface of the toner is coated with a binder resin having a low softening point. Furthermore, in the toner disclosed in JP-A-59-37553, since the colorant is attached only to the surface of the toner, ID is insufficient if a small amount of colorant is added, and if a large amount of colorant is added, the colorant peels off from the toner. Problems arise in that they become spent on the surface of the carrier or get mixed into the developer, deteriorating printing durability.
特に、カラートナーに使用を考えた場合従来黒トナーに
使用されてきた有彩色の荷電付与剤は、通常の粉砕法、
Ｘブレードライ法で製造する場合、充分な帯電量を得る
為には、ある量販上添加しなければならず、その場合画
像上色のにごりが発生し、満足なカラー画像が得られて
いない。In particular, when considering the use in color toners, the chromatic charge imparting agents conventionally used in black toners can be
In the case of manufacturing by the X-blade drying method, in order to obtain a sufficient amount of charge, it is necessary to add it for certain mass sales purposes, and in this case, color clouding occurs on the image, making it impossible to obtain a satisfactory color image.
また近年、カラートナー用荷電付与剤として特開昭５９
−２０４８５１で示されるフェノチアジン化合物の様に
無色あるいは淡色の荷電付与剤を用いることが検討され
ているが、耐環境性、帯電の立ち上がりあるいは耐刷時
における帯電性の不安定さ等に問題がありトナー諸物性
を満足させるまでには至っていない。In addition, in recent years, as a charge imparting agent for color toners, JP-A-59
The use of colorless or light-colored charge-imparting agents such as the phenothiazine compound shown by -204851 has been considered, but there are problems with environmental resistance, charging buildup, and instability of charging properties during printing. The various physical properties of the toner have not yet been satisfied.
また、荷電性の改良に有用であるアミノ基等の極性基を
樹脂の官能基として導入するカラートナーも知られてい
る（例えば特開昭６０−３６４８号公報）が、やはり耐
環境性、帯電の立ち上がり、あるいは耐刷時における帯
電性の不安定さ等に問題があり、トナー諸物性を満足さ
仕るまでには至っていない。Color toners are also known in which a polar group such as an amino group, which is useful for improving chargeability, is introduced as a functional group in the resin (for example, Japanese Patent Application Laid-Open No. 60-3648); There are problems with the start-up of the toner, instability of charging properties during printing, etc., and the various physical properties of the toner have not yet been achieved.
発明が解決しようとする問題点
本発明は上記問題点を解消し、トナー飛散およびトナー
こぼれが少なく、長期荷電安定性および耐環境性に優れ
、しかも帯電の立ち上がりが速く安定した静電荷現像用
カラートナーを得ることを目的とする。さらには、にご
りのない鮮明なカラー画像特性に優れたトナーを提供す
ることを目的とする。Problems to be Solved by the Invention The present invention solves the above-mentioned problems and provides a color for electrostatic charge development that has less toner scattering and toner spillage, has excellent long-term charge stability and environmental resistance, and has a fast and stable charge build-up. The purpose is to obtain toner. A further object of the present invention is to provide a toner with excellent color image characteristics that are clear and free from clouding.
問題点を解決するための手段
本発明は少なくとも熱可塑性樹脂、着色剤および荷電付
与剤よりなる静電潜像現像用カラートナーにおいて、少
なくとも熱可塑性樹脂と着色剤よりなるトナー芯材と、
該芯材表面に固着した０゜０３〜１ｗｔ％の荷電付与剤
よりなることを特徴とする静電潜像現像用カラートナー
。さらに本発明は少なくとも熱可塑性樹脂、着色剤およ
び荷電付与剤よりなる静電潜像現像用カラートナーにお
いて、少なくとも含窒素極性官能基あるいは含弗素極性
官能基を有する単量体成分を含有する樹脂および着色剤
よりなるトナー芯材と、該芯材表面に固着した。、ｏ
ｏ ｓ〜１ｗｔ％の荷電付与剤とからなることを特徴と
する静電潜像現像用カラートナー。Means for Solving the Problems The present invention provides a color toner for developing electrostatic latent images comprising at least a thermoplastic resin, a coloring agent, and a charge imparting agent, and a toner core comprising at least a thermoplastic resin and a coloring agent;
A color toner for developing electrostatic latent images, comprising 0.03 to 1 wt% of a charge imparting agent fixed to the surface of the core material. Furthermore, the present invention provides a color toner for developing electrostatic latent images comprising at least a thermoplastic resin, a colorant, and a charge imparting agent, and a resin containing a monomer component having at least a nitrogen-containing polar functional group or a fluorine-containing polar functional group; A toner core material made of a colorant was fixed to the surface of the core material. ,o
A color toner for developing an electrostatic latent image, comprising a charge imparting agent of os to 1 wt%.
本発明のカラートナーは少なくとも熱可塑性樹脂および
着色剤を含有するトナー芯材と該芯材表面に固着した荷
電付与剤からなる。The color toner of the present invention comprises a toner core material containing at least a thermoplastic resin and a colorant, and a charge imparting agent fixed to the surface of the core material.
本発明のカラートナーは、前記芯材表面に正または負の
荷電付与剤を電気的に付着させ、次いでその表層部に局
所的に熱を加えて前記荷電付与剤を固定処理することに
より得られる。The color toner of the present invention is obtained by electrically adhering a positive or negative charge imparting agent to the surface of the core material, and then fixing the charge imparting agent by locally applying heat to the surface layer thereof. .
本発明に使用できる熱可塑性樹脂としては、通常トナー
に汎用されているものであれば特に限定されるものでな
く、例えば以下に示すビニル系モノマー、アクリル系モ
ノマー、メタクリル系モノマー等の単官能性モノマーあ
るいは多官能性モノマーの１種あるいは２種以上から調
製可能である。The thermoplastic resin that can be used in the present invention is not particularly limited as long as it is commonly used in toners, and includes monofunctional monomers such as vinyl monomers, acrylic monomers, and methacrylic monomers shown below. It can be prepared from one or more monomers or polyfunctional monomers.
その他にも熱可塑性樹脂としてはポリエステル、エポキ
シ、ポリエーテル、ポリカーボネート、ポリ酸無水物、
ポリウレタン、ポリエチレン、ポリプロピレン、などの
ポリオレフィン、ポリアミド、などが用いられる。Other thermoplastic resins include polyester, epoxy, polyether, polycarbonate, polyacid anhydride,
Polyolefins such as polyurethane, polyethylene, polypropylene, polyamides, etc. are used.
単官能性モノマーとしては、スチレン、α−メチルスチ
レン、０−メチルスチレン、１−メチルスチレン、ｐ−
メチルスチレン、ｐ−エチルスチレン、２．４−ジメチ
ルスチレン、ｐ ｎ−ブチルスチレン、Ｊ） ｔｅｒ
ｔ−ブチルスチレン、ｐ−ｎ−へキシルスチレン、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、ｐ−
メトキシスチレン、ｐ−フェニルスチレンなどのスチレ
ン系モノマー；メチルアクリレート、エチルアクリレー
ト、ｎ−プロピルアクリレート、１ｓｏ−プロピルアク
リレート、ｎ−ブチルアクリレート、１ｓｏ−ブチルア
クリレート、ｔｅｒｔ−ブチルアクリレート、ｎ−アミ
ルアクリレート、ｎ−へキシルアクリレート、２−エチ
ルへキシルアクリレート、ｎ−オクチルアクリレート、
ｎ−ノニルアクリレート、シクロへキシルアクリレート
、ベンジルアクリレート、ジメチルフォスフェートエチ
ルアクリレート、ジエチルフォスフェートエチルアクリ
レート、ジブチルフォスフェートエチルアクリレート、
２−ベンゾイルオキシエチルアクリレートなどのアクリ
ル系モノマー；メチルメタクリレート、エチルメタクリ
レ−Ｆ、ｎ−プロビルメタクリレート、１ｓｏ−プロピ
ルメタクリレート、ｎ−ブチルメタクリレート、１ｓｏ
−ブチルメタクリレート、ｔｅｒｔ−ブチルメタクリレ
ート、ｎ−アミルメタクリレート、ｎ−へキシルメタク
リレート、２−エチルへキシルメタクリレート、ｎ−オ
クチルメタクリレート、ｎ−ノニルメタクリレート、ジ
エチルフォスフェートエチルメタクリレート、ジブチル
フォスフェートエチルメタクリレートなどのメタクリレ
ート系モノマー；メチレン脂肪族モノカルボン酸エステ
ル類：酢酸ビニル、プロピオン酸ビニル、ベンジェ酸ビ
ニル、酪酸ビニル、安息香酸ビニル、ギ酸ビニル等のビ
ニルエステル類、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等のビニルエーテ
ル類、ビニルメチルケトン、ビニルへキシルケトン、メ
チルイソプロピルケトン等のビニルケトン類などのビニ
ル系モノマ−；が挙げられる。Examples of monofunctional monomers include styrene, α-methylstyrene, 0-methylstyrene, 1-methylstyrene, p-
Methylstyrene, p-ethylstyrene, 2,4-dimethylstyrene, pn-butylstyrene, J) ter
t-butylstyrene, p-n-hexylstyrene, p
n-octylstyrene, p-n-nonylstyrene, p-
n-decylstyrene, p-n-dodecylstyrene, p-
Styrenic monomers such as methoxystyrene and p-phenylstyrene; methyl acrylate, ethyl acrylate, n-propyl acrylate, 1so-propyl acrylate, n-butyl acrylate, 1so-butyl acrylate, tert-butyl acrylate, n-amyl acrylate, n -hexyl acrylate, 2-ethylhexyl acrylate, n-octyl acrylate,
n-nonyl acrylate, cyclohexyl acrylate, benzyl acrylate, dimethyl phosphate ethyl acrylate, diethyl phosphate ethyl acrylate, dibutyl phosphate ethyl acrylate,
Acrylic monomers such as 2-benzoyloxyethyl acrylate; methyl methacrylate, ethyl methacrylate-F, n-propyl methacrylate, 1so-propyl methacrylate, n-butyl methacrylate, 1so
-butyl methacrylate, tert-butyl methacrylate, n-amyl methacrylate, n-hexyl methacrylate, 2-ethylhexyl methacrylate, n-octyl methacrylate, n-nonyl methacrylate, diethyl phosphate ethyl methacrylate, dibutyl phosphate ethyl methacrylate, etc. Methacrylate monomer; methylene aliphatic monocarboxylic acid esters: vinyl esters such as vinyl acetate, vinyl propionate, vinyl benzoate, vinyl butyrate, vinyl benzoate, vinyl formate, vinyl methyl ether, vinyl ethyl ether, vinyl isobutyl ether and vinyl monomers such as vinyl ethers such as, vinyl ketones such as vinyl methyl ketone, vinyl hexyl ketone, and methyl isopropyl ketone.
多官能性モノマーとしては、ジエチレングリコールジア
クリレート、トリエチレングリコールジアクリレート、
テトラエチレングリコールジアクリレート、ポリエチレ
ングリコールジアクリレート、１．６−ヘキサンジオー
ルジアクリレート、ネオペンチルグリコールジアクリレ
ート、トリプロピレングリコールジアクリレート、ポリ
プロピレングリコールジアクリレート、２，２−ビス［
４−（アクリロキシ・ジェトキシ）フェニル］プロパン
、トリメチロールプロパントリアクリレート、テトラメ
チロールメタンテトラアクリレート、エチレングリコー
ルジメタクリレート、ジエチレングリコールジメタクリ
レート、トリエチレングリコールジメタクリレート、テ
トラ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、１．３−ブチレングリ
コールジメタクリレート、１．６−ヘキサンジオールジ
アクリレート、ネオペンチルグリコールジメータクリレ
ート、ポリプロピレングリコールジメタクリレート、２
．２’−ビス［４−（メタクリロキシ・ジェトキシ）フ
ェニル］プロパン、２．２−ビス［４−（メタクリロキ
シ・ポリエトキシ）フェニルコプロパン、トリメチロー
ルプロパントリメタクリレート、テトラメチロールメタ
ントリメタクリレート、ジビニルベンゼン、ジビニルナ
フタリン、ジビニルエーテル等を挙げることができる。Examples of polyfunctional monomers include diethylene glycol diacrylate, triethylene glycol diacrylate,
Tetraethylene glycol diacrylate, polyethylene glycol diacrylate, 1,6-hexanediol diacrylate, neopentyl glycol diacrylate, tripropylene glycol diacrylate, polypropylene glycol diacrylate, 2,2-bis[
4-(acryloxy-jethoxy)phenyl]propane, trimethylolpropane triacrylate, tetramethylolmethanetetraacrylate, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, polyethylene glycol dimethacrylate, 1 .3-Butylene glycol dimethacrylate, 1,6-hexanediol diacrylate, neopentyl glycol dimethacrylate, polypropylene glycol dimethacrylate, 2
．． 2'-bis[4-(methacryloxy-jetoxy)phenyl]propane, 2,2-bis[4-(methacryloxy-polyethoxy)phenylcopropane, trimethylolpropane trimethacrylate, tetramethylolmethane trimethacrylate, divinylbenzene, divinylnaphthalene , divinyl ether and the like.
前記単官能性モノマーを単独であるいは、２Ｗ以上組み
合わせて、また、単官能性モノマーと多官能性モノマー
を組み合わせて使用することができる。The above monofunctional monomers can be used alone or in combination of 2W or more, or a monofunctional monomer and a polyfunctional monomer can be used in combination.
熱可塑性樹脂は、上記単官能性モノマーあるいは多官能
性モノマーと含窒素極性官能基あるいはフッ素を有する
モノマー成分との共重合により調製することも可能であ
る。The thermoplastic resin can also be prepared by copolymerizing the above-mentioned monofunctional monomer or polyfunctional monomer with a monomer component having a nitrogen-containing polar functional group or fluorine.
また、熱可塑性樹脂は、上記単官能性モノマーあるいは
多官能性モノマーの重合体と含窒素極性官能基を有する
モノマーあるいは含フツ素モノマーの重合体とのブレン
ド物であってもよい。Further, the thermoplastic resin may be a blend of a polymer of the above monofunctional monomer or polyfunctional monomer and a monomer having a nitrogen-containing polar functional group or a polymer of a fluorine-containing monomer.
以上のように極性基を有する熱可塑性樹脂からトナー芯
材が構成される場合は、樹脂自体が帯電制御の働きをす
るため芯材表面に固着させる荷電付与剤はより少ない量
で本発明の目的を達成することができる。As described above, when the toner core material is composed of a thermoplastic resin having a polar group, the resin itself functions to control charging, so the amount of the charge imparting agent fixed to the surface of the core material can be reduced to achieve the object of the present invention. can be achieved.
含窒素極性官能基は正荷電制御に有効で含窒素極性官能
基を有するモノマーとしては、下記−数式［１］
％式％［］
［式中、Ｒｏは水素またはメチル基、Ｒ３およびＲ５は
水素または炭素数１〜２０のアルキル基、Ｘは酸素原子
または窒素原子、Ｑはアルキレン基またはアリーレン基
を示す。］
で表わされる。The nitrogen-containing polar functional group is effective for positive charge control, and the monomer having the nitrogen-containing polar functional group has the following formula [1] % formula % [] [where Ro is hydrogen or a methyl group, R3 and R5 are hydrogen or an alkyl group having 1 to 20 carbon atoms, X represents an oxygen atom or a nitrogen atom, and Q represents an alkylene group or an arylene group. ] It is expressed as .
アミノ（メタ）アクリル系モノマーの代表例としてはＮ
、Ｎ−ジメチルアミノメチル（メタ）アクリレート、Ｎ
、Ｎ−ノエチルアミノメチル（メタ）アクリレート、Ｎ
、Ｎ−ジメチルアミノエチル（メタ）アクリレート、Ｎ
、Ｎ−ジエチルアミノエチル（メタ）アクリレート、Ｎ
、Ｎ−ツメチルアミノプロピル（メタ）アクリレート、
Ｎ、Ｎ−ジメチルアミノブチル（メタ）アクリレート、
ｐ−Ｎ、Ｎ−ジメチルアミノフェニル（メタ）アクリレ
ート、］１）−Ｎ、Ｎ−ジエチルアミノフェニル（メタ
）アクリレート、ｐ−Ｎ、Ｎ−ジプロピルアミノフェニ
ル（メタ）アクリレート、１）−Ｎ、Ｎ−ジブチルアミ
ノフェニル（メタ）アクリレート、ｐ−Ｎ−ラウリルア
ミノフェニル（メタ）アクリレート、ｐ−Ｎ−ステアリ
ルアミノフェニル（メタ）アクリレート、ｐ−Ｎ、Ｎ−
ジメチルアミノベンジル（メタ）アクリレート、１）−
Ｎ。A typical example of amino(meth)acrylic monomer is N
, N-dimethylaminomethyl (meth)acrylate, N
, N-noethylaminomethyl (meth)acrylate, N
, N-dimethylaminoethyl (meth)acrylate, N
, N-diethylaminoethyl (meth)acrylate, N
, N-tumethylaminopropyl (meth)acrylate,
N,N-dimethylaminobutyl (meth)acrylate,
p-N,N-dimethylaminophenyl (meth)acrylate, ]1)-N,N-diethylaminophenyl (meth)acrylate, p-N,N-dipropylaminophenyl (meth)acrylate, 1)-N,N -dibutylaminophenyl (meth)acrylate, p-N-laurylaminophenyl (meth)acrylate, p-N-stearylaminophenyl (meth)acrylate, p-N,N-
Dimethylaminobenzyl (meth)acrylate, 1)-
N.
Ｎ−ジエチルアミノベンジル（メタ）アクリレート、ｐ
”Ｎ、Ｎ−ジプロピルアミノベンジル（メタ）アクリレ
ート、ｐ−Ｎ、Ｎ−ジブチルアミノベンジル（メタ）ア
クリレート、ｐ−Ｎ−ラウリルアミノベンジル（メタ）
アクリレート、ｐ−Ｎ−ステアリルアミノベンジル（メ
タ）アクリレート等が例示される。N-diethylaminobenzyl (meth)acrylate, p
"N,N-dipropylaminobenzyl (meth)acrylate, p-N,N-dibutylaminobenzyl (meth)acrylate, p-N-laurylaminobenzyl (meth)
Examples include acrylate, p-N-stearylaminobenzyl (meth)acrylate, and the like.
さらに、Ｎ、Ｎ−ジメチルアミノエチル（メタ）アクリ
ルアミド、Ｎ、Ｎ−ジエチルアミノエチル（メタ）アク
リルアミド、Ｎ、Ｎ−ジメチルアミノプロピル（メタ）
アクリルアミド、Ｎ、Ｎ−ジエチルアミノプロピル（メ
タ）アクリルアミド、ｐ−Ｎ、Ｎ−ジメチルアミノフェ
ニル（メタ）アクリルアミド、ｐＮ、Ｎ−ジエチルアミ
ノフェニル（メタ）アクリルアミド、ｐ−Ｎ、Ｎ−ジプ
ロピルアミノフェニル（メタ）アクリルアミド、ｐ−Ｎ
、Ｎ−ジブチルアミノフェニル（メタ）アクリルアミド
、１）−Ｎ−ラウリルアミノフェニル（メタ）アクリル
アミド、ｐ−Ｎ−ステアリルアミノフェニル（メタ）ア
クリルアミド、ｐ−Ｎ、Ｎ−ジメチルアミノベンジル（
メタ）アクリルアミド、Ｉ）−Ｎ、Ｎ−ジエチルアミノ
ベンジル（メタ）アクリルアミド、Ｉ）−Ｎ、Ｎ−ジプ
ロピルアミノベンジル（メタ）アクリルアミド、ｐ−Ｎ
。Additionally, N,N-dimethylaminoethyl (meth)acrylamide, N,N-diethylaminoethyl (meth)acrylamide, N,N-dimethylaminopropyl (meth)
Acrylamide, N,N-diethylaminopropyl (meth)acrylamide, p-N,N-dimethylaminophenyl (meth)acrylamide, pN,N-diethylaminophenyl (meth)acrylamide, p-N,N-dipropylaminophenyl (meth) ) acrylamide, p-N
, N-dibutylaminophenyl (meth)acrylamide, 1)-N-laurylaminophenyl (meth)acrylamide, p-N-stearylaminophenyl (meth)acrylamide, p-N,N-dimethylaminobenzyl (
meth)acrylamide, I) -N,N-diethylaminobenzyl (meth)acrylamide, I) -N,N-dipropylaminobenzyl (meth)acrylamide, p-N
.
Ｎ−ジブチルアミノベンジル（メタ）アクリルアミド、
ｐ−Ｎ−ラウリルアミノベンジル（メタ）アクリルアミ
ド、Ｐ−Ｎ−ステアリルアミノベンジル（メタ）アクリ
ルアミド等が例示される。N-dibutylaminobenzyl (meth)acrylamide,
Examples include p-N-laurylaminobenzyl (meth)acrylamide and P-N-stearylaminobenzyl (meth)acrylamide.
フッ素原子は負荷電制御に有効でフッ素含有モノマーと
しては特に制限はないが、２，２．２−トリフルオロエ
チルアクリレート、２，２，３．３−テトラフルオロプ
ロピルアクリレート、２，２，３゜３．４，４，５．５
−オクタフルオロアミルアクリレート、Ｉ Ｈ，Ｉ Ｈ
，２Ｈ，２Ｈ−へブタデカフルオロデシルアクリレート
などのフルオロアルキルアクリレート又はメタクリレー
トが好ましい。 このほかトリフルオロクロルエチレ
ン、フッ化ビニリデン、３フツ化エチレン、４フツ化エ
チレン、トリフルオロプロピレン、ヘキサフルオロプロ
ペン、ヘキサフルオロプロピレンなどの使用が可能であ
る。Fluorine atoms are effective for controlling negative charge, and there are no particular restrictions on the fluorine-containing monomers, including 2,2,2-trifluoroethyl acrylate, 2,2,3,3-tetrafluoropropyl acrylate, and 2,2,3゜. 3.4,4,5.5
-Octafluoroamyl acrylate, I H, I H
, 2H, 2H-hebutadecafluorodecyl acrylate or methacrylates are preferred. In addition, trifluorochloroethylene, vinylidene fluoride, trifluoroethylene, tetrafluoroethylene, trifluoropropylene, hexafluoropropene, hexafluoropropylene, and the like can be used.
本発明に使用しうる着色剤としては、具体的には、黄色
顔料では、
黄鉛、亜鉛黄、カドミウムエロー、黄色酸化鉄、ミネラ
ルファストイエロー、ニッケルチタンエロー、ネーブル
スエロー、ナフトールエローＳ１ハンザ−イエローＧ１
ハンザ−イエロー１０Ｇ、ベンジジンエローＧ１ベンジ
ジンエローＧＲ，キノリンエローレーキ、パーマネント
エロー、ＮＣＧ１タートラジンレーキ等がある。Specific examples of colorants that can be used in the present invention include yellow pigments such as yellow lead, zinc yellow, cadmium yellow, yellow iron oxide, mineral fast yellow, nickel titanium yellow, navel yellow, and naphthol yellow S1 Hansa. Yellow G1
There are Hansa Yellow 10G, Benzidine Yellow G1, Benzidine Yellow GR, Quinoline Yellow Lake, Permanent Yellow, NCG1 Tartrazine Lake, etc.
橙色顔料では、
赤口黄鉛、モリブデンオレンジ、パーマネントオレンジ
ＧＴＲ，ピラゾロンオレンジ、パルカンオレンジ、イン
ダスレンブリリアントオレンジＲＫ１ベンジジンオレン
ジＧ１インダンスレンブリリアントオレンジＧＫ等：
赤色顔料では、
ベンガラ、カドミウムレッド、鉛丹、硫化水銀カドミウ
ム、パーマネントレッド４Ｒ，リソールレッド、ピラゾ
ロンレッド、ウオッチングレッド、カルシューム塩、レ
ーキレッドＤ１ブリリアントカーミン６Ｂ、エオシンレ
ーキ、ローダミンレーキＢ１アリザリンレーキ、ブリリ
アントカーミノ３Ｂ等；
紫色顔料では、
マンガン紫、ファストバイオレットＢ１メチルバイオレ
ットレーキ等：
青色顔料では、
紺青、コバルトブルー、アルカリブルーレーキ、ビクト
リアブルーレーキ、フタロシアニンブルー、無金属フタ
ロシアニンブルー、フタロシアニンブル一部分塩素化物
、ファストスカイブルー、インダスレンプルーＢＣ等が
ある。Orange pigments include red yellow lead, molybdenum orange, permanent orange GTR, pyrazolone orange, palkan orange, indanthrene brilliant orange RK1, benzidine orange G1, indanthrene brilliant orange GK, etc.; red pigments include red pigment, cadmium red, red lead, Cadmium mercury sulfide, Permanent Red 4R, Lysol Red, Pyrazolone Red, Watching Red, Calcium Salt, Lake Red D1 Brilliant Carmine 6B, Eosin Lake, Rhodamine Lake B1 Alizarin Lake, Brilliant Carmino 3B, etc.; Purple pigments include Manganese Purple, Fast Violet B1 Methyl Violet Lake, etc.: Blue pigments include navy blue, cobalt blue, alkali blue lake, Victoria blue lake, phthalocyanine blue, metal-free phthalocyanine blue, partially chlorinated phthalocyanine blue, fast sky blue, industhrene blue BC, etc. .
緑色顔料では、
クロムグリーン、酸化クロム、ピグメントグリーンＢ１
マラカイトグリーンレーキ、ファナルイ二ローグリーン
Ｇ等；
白色顔料では、
亜鉛華、酸化チタン、アンチモン白、硫化亜鉛がある。Green pigments include chrome green, chromium oxide, and pigment green B1.
Malachite Green Lake, Fanal Ijiro Green G, etc.; White pigments include zinc white, titanium oxide, antimony white, and zinc sulfide.
また必要に応じて黒色顔料としてファーネスブラック、
チャンネルブラック、アセチレンブラック等のカーボン
ブラック、あるいは活性炭、非磁性フェライト等を他の
着色剤と組み合わせて用いることができる。Furnace black can also be used as a black pigment if necessary.
Carbon black such as channel black and acetylene black, activated carbon, non-magnetic ferrite, etc. can be used in combination with other colorants.
体質顔料では、
パライト粉、炭酸バリウム、クレー、シリカ、ホワイト
カーボン、タルク、アルミナホワイト等を挙げることが
でき、１種または２種以上混合して使用してもよく、い
ずれも無公害で高い着色力があれば有機、無機を問わず
、これらに限定されるものではない。Extender pigments include pallite powder, barium carbonate, clay, silica, white carbon, talc, alumina white, etc., and they may be used alone or in combination of two or more, and all of them are non-polluting and highly pigmented. As long as there is power, it can be organic or inorganic, but is not limited to these.
本発明に使用しうる荷電付与剤は、トナー芯材と摩擦帯
電して正または負の荷電を与えるものであれば無機物、
有機物を問わず何でもよい。The charge imparting agent that can be used in the present invention includes inorganic materials as long as they are triboelectrically charged with the toner core material and impart a positive or negative charge.
Any organic matter is fine.
正荷電付与剤の例としては、ニグロシン系染料、下記−
数式［■］：
［但し、式中Ｒ８、Ｒ８、Ｒ８およびＲ３は同一または
異なるアルキル基、アリール基、またはいずれかの２個
が合して複素環基を構成する基、Ｘはハロゲン、スルホ
ン酸基、スルホン酸エステル基、硫酸エステル基または
アルキル硫酸エステル基を示す］で示される第４級アン
モニウム化合物、特開昭５９−７８３６４号公報、特開
昭５９−１３６７４６号公報、特開昭５９−１１４５４
６号公報、および特開昭５９−１２３８５０号公報等に
記載されている荷電付与剤、またアミノアクリレートな
どの共重合体（たとえばスチレン、ジエチルアミノエチ
ルメタクリレート共重合体など）が使用可能である。Examples of positive charge imparting agents include nigrosine dyes and the following -
Numerical formula [■]: [However, in the formula, R8, R8, R8 and R3 are the same or different alkyl groups, aryl groups, or a group in which any two of them combine to form a heterocyclic group, and X is a halogen or a sulfone. Acid group, sulfonic acid ester group, sulfuric ester group or alkyl sulfate group] Quaternary ammonium compounds represented by JP-A-59-78364, JP-A-59-136746, JP-A-59 -11454
Charge imparting agents described in JP-A No. 6 and JP-A-59-123850, and copolymers of amino acrylates (for example, styrene, diethylaminoethyl methacrylate copolymers, etc.) can be used.
特に、正の荷電付与剤としてはニグロシン染料が好まし
い。ニグロシン染料としては、ボントロンＮ−０１，Ｎ
−０２、Ｎ−０４、Ｎ−０５、Ｎ−０７、Ｎ−０９、Ｎ
−１０、Ｎ−１３（オリエント化学工業社製）等が商業
的に人手可能である。In particular, nigrosine dye is preferred as the positive charge imparting agent. As the nigrosine dye, Bontron N-01,N
-02, N-04, N-05, N-07, N-09, N
-10, N-13 (manufactured by Orient Kagaku Kogyo Co., Ltd.), etc. can be commercially produced manually.
また、負荷電付与剤の例としてはＣｒ、Ｇｏ、Ｆｅ１Ａ
Ｉ２等の金属のキレート化した染料やカヤチャージＮ−
１、Ｎ−２、Ｎ−３（日本化薬社製）等が使用可能であ
る。In addition, examples of negative charge imparting agents include Cr, Go, Fe1A
Metal chelated dyes such as I2 and Kaya Charge N-
1, N-2, N-3 (manufactured by Nippon Kayaku Co., Ltd.), etc. can be used.
上記金属のキレート化した染料としては、ボントロン５
−３２．５−３３．５−３４．５−３５．５−３７．５
−３８．５−４０．５−４４、Ｅ−８１、Ｅ−８２、Ｅ
−８４、Ｅ−８５（オリエント化学工業社製）、アイゼ
ンスピロンブラックＴＲＨ，ＢＨＨ（保土谷化学工業社
製）、カヤセットブラックＴ−２，００４（日本化薬社
製）、特開昭５９−７８３６１号公報、特開昭５９−８
８７４４号公報、特開昭５９−２２８２．５９号公報な
どに記載の染料が用いられる。As the above-mentioned metal chelated dye, Bontron 5
-32.5-33.5-34.5-35.5-37.5
-38.5-40.5-44, E-81, E-82, E
-84, E-85 (manufactured by Orient Chemical Industry Co., Ltd.), Eisenspiron Black TRH, BHH (manufactured by Hodogaya Chemical Industry Co., Ltd.), Kayaset Black T-2,004 (manufactured by Nippon Kayaku Co., Ltd.), JP-A-59 -78361 Publication, JP-A-59-8
Dyes described in JP-A-8744, JP-A-59-2282.59, etc. are used.
本発明に用いられるトナー芯材としては、従来公知の方
法で得られるものであれば何でも良く、特に制限はない
。すなわち、熱可塑性樹脂、着色剤および／または荷電
付与剤などを混合・混練したあと粉砕・分級して得られ
た粉砕法トナー、懸濁重合によって得られた球型トナー
、芯を殻でくるんだカプセルトナーなどがあるが、荷電
付与剤を固着でき、均一な荷電を有するものであれば何
でも良く、特に限定されるものではない。The toner core material used in the present invention is not particularly limited and may be any material as long as it can be obtained by a conventionally known method. In other words, pulverized toner obtained by mixing and kneading thermoplastic resin, coloring agent, and/or charge-imparting agent, and then pulverizing and classifying, spherical toner obtained by suspension polymerization, and spherical toner obtained by wrapping the core in a shell. There are capsule toners and the like, but any toner may be used as long as it can fix a charge imparting agent and has a uniform charge, and is not particularly limited.
本発明に用いられる芯材の粒径は、平均粒径４〜２０μ
ｌのものが使用可能である。実用上使用可能な荷電付与
剤の粒径は、０．０２μＩ１１〜１０μｍ１好ましくは
０．１μｆｆｉ〜３μｍである。一般に、大粒径の荷電
付与剤は、実効−欠粒径１μｍ以下の小粒子が凝集した
ものであり、大粒径の荷電付与剤を用いた場合でも、静
電気的に荷電付与剤を芯材に付着させる工程で機械的ス
トレスを受けて大粒径のものが解砕されるので、芯材表
面には小粒径の荷電付与剤が付着する。トナー芯材表面
に付着させる荷電付与剤の量は本発明で述べる測定方法
により最終的なカラートナー表面上に露出している量で
決定される。The particle size of the core material used in the present invention is an average particle size of 4 to 20μ.
1 can be used. The particle size of the charge imparting agent that can be used practically is 0.02 μm to 10 μm, preferably 0.1 μffi to 3 μm. Generally, a large particle size charge imparting agent is an agglomeration of small particles with an effective particle diameter of 1 μm or less, and even when a large particle size charge imparting agent is used, the charge imparting agent is electrostatically attached to the core material. In the step of adhering to the core material, large particles are crushed due to mechanical stress, so that small particle-sized charge imparting agents are attached to the surface of the core material. The amount of the charge imparting agent attached to the surface of the toner core material is determined by the amount exposed on the final color toner surface by the measuring method described in the present invention.
表面に固着させる荷電付与剤の量はトナー芯材を構成す
る熱可塑性樹脂が、含窒素極性官能基あるいはフッ素原
子を含有しない場合は、トナー重量の０，０３ｗｔ％〜
ｌｖｔ％、好ましくは、０．１〜０ 、８ ｗｔ％であ
る。０．ＯＬｗｔ％より少ないと帯電の立ち上がりが悪
くなり、帯電量が不足する。１ｗｔ％より多いとカラー
画像（特に黄色）の濁りが発生し、鮮明なカラー画像が
得られなくなる。If the thermoplastic resin constituting the toner core material does not contain a nitrogen-containing polar functional group or a fluorine atom, the amount of the charge-imparting agent fixed on the surface is 0.03 wt% to 0.03 wt% of the toner weight.
lvt%, preferably 0.1 to 0.8 wt%. 0. When the amount is less than OLwt%, the charge rise will be slow and the amount of charge will be insufficient. If the amount is more than 1 wt%, color images (especially yellow) become cloudy, making it impossible to obtain clear color images.
トナー芯材を構成する熱可塑性樹脂が含窒素極性官能基
あるいはフッ素原子を含有する場合は、それらの含有量
にもよるが、表面に固着させる荷電付与剤の量は、トナ
ー重量の０．００５ｗｔ％〜１ｗｔ％、好ましくは０．
０５〜０．８ｗｔ％でよく、上記の熱可塑性樹脂が荷電
付与機能がない場合に比べより少ない使用量でも有効で
ある。使用量が０．００５ｗｔ％より少ないとトナーの
帯電の立ち上がりが悪く、帯電量が不足する。１ｗｔ％
より多いとカラー画像上に濁りが発生する。When the thermoplastic resin constituting the toner core material contains a nitrogen-containing polar functional group or a fluorine atom, the amount of charge imparting agent fixed to the surface is 0.005wt of the toner weight, depending on the content thereof. % to 1 wt%, preferably 0.
The amount may be 0.05 to 0.8 wt%, and even a smaller amount is effective than when the thermoplastic resin does not have a charge imparting function. If the amount used is less than 0.005 wt %, charging of the toner will be slow and the amount of charging will be insufficient. 1wt%
If the amount is more than that, turbidity will appear on the color image.
カラートナー芯材表面に正または負の荷電付与剤を付着
させる方法としては、通常のヘンシェルミキサー、スー
パーミキサーなどの様に、回転用の羽根がついている槽
の中にトナー芯材と荷電付与剤を入れ、回転させること
でお互いに摩擦帯電してトナー芯材の回りに荷電付与剤
を付着させる方法がある。トナー芯材表面に荷電付与剤
を付着させる方法としては、これ以外のどの様な方法で
も良い。A method for attaching a positive or negative charge imparting agent to the surface of a color toner core material is to place the toner core material and charge imparting agent in a tank equipped with rotating blades, such as in a normal Henschel mixer or super mixer. There is a method of attaching a charge imparting agent around the toner core material by frictionally charging each other by inserting and rotating the toner core material. Any other method may be used for attaching the charge imparting agent to the surface of the toner core material.
荷電付与剤の付着したトナー表層部を局所加熱する方法
として、特開昭６０−１１７２５８号公報にある様な瞬
間加熱装置、ハイブリダイザ−（奈良機械製作所社製）
、ヘンシェルミキサー、オングミル（ホソカワミクロン
社製）などの撹拌装置の中に入れて撹拌し表面の発熱を
促す方法、マイクロウェーブなどによる加熱などの種々
の装置を用いることができるが、方法・装置・手段には
拘らずどのような方法を用いても良い。As a method of locally heating the surface layer of the toner to which the charge imparting agent has adhered, an instant heating device and a hybridizer (manufactured by Nara Kikai Seisakusho Co., Ltd.) as described in JP-A-60-117258 are used.
Various devices can be used, such as a method of stirring the material in a stirring device such as a Henschel mixer or an Ong Mill (manufactured by Hosokawa Micron Corporation) to promote heat generation on the surface, heating with microwaves, etc., but methods, devices, and means. Any method may be used regardless of the method.
また、スパイラーフロー（フロイント産業社製）等の装
置により、荷電付与剤の付着した表層部の一部を少量の
有機溶剤により溶解もしくは膨潤させて荷電付与剤をト
ナー表層部に固定化しても良い。Alternatively, the charge imparting agent may be fixed on the surface layer of the toner by dissolving or swelling a portion of the surface layer to which the charge imparting agent is attached with a small amount of organic solvent using a device such as Spiral Flow (manufactured by Freund Sangyo Co., Ltd.). .
以下、実施例を挙げて本発明を説明する。The present invention will be explained below with reference to Examples.
熱可塑性樹脂の合成例
１ｇの４つロコルベンに、スチレン（Ｓｔ）４９４９、
ジメヂルアミノエチルメタクリレート（ＤＭＡＭ）３９
．３９、トルエン２７０ｇおよびアゾビスイソブヂロニ
トリル（ＡＩ ＢＮ）２．７ｙを加え、溶解した後、窒
素気流下で８０℃で６時間反応させ、重合を行った。次
に、トルエンを留去した後１８０〜１９０℃で４０〜５
０ｍｍＨｇに減圧し、揮発分を完全に除去した。得られ
た重合物は、無色透明の固体で、ガラス転移点（Ｔｇ）
は８１’Ｃ、アミン価は２５であった。Synthesis example of thermoplastic resin 1 g of 4 locolbens, styrene (St) 4949,
Dimedylaminoethyl methacrylate (DMAM) 39
．． 39, 270 g of toluene and 2.7 y of azobisisobutyronitrile (AI BN) were added and dissolved, and then reacted at 80° C. for 6 hours under a nitrogen stream to perform polymerization. Next, after distilling off toluene, 40 to 5
The pressure was reduced to 0 mmHg to completely remove volatile components. The obtained polymer is a colorless and transparent solid with a glass transition point (Tg)
was 81'C, and the amine value was 25.
以下、同様にして下記の表−１に示す熱可塑性樹脂（参
考例１〜７）を得た。Thereafter, thermoplastic resins (Reference Examples 1 to 7) shown in Table 1 below were obtained in the same manner.
（以下、余白）
表−１
実施例
トナー（１−１１）の調製
スチレン−アクリル共重合樹脂
（軟化点（Ｔａｇ）：１３５℃、ガラス転移点（Ｔｇ）
：５８℃）：１００重量部
銅フタロシアニン顔料
（大日精化社製） ＝ ６重量部ビスコ
ール５５０Ｐ
（三洋化成工業社製） ： ５重量部上記の材料
をボールミルで十分に混合した後１３０℃に熱した３本
ロール上で混練した。混練物を放置冷却後、フェザ−ミ
ルで粗粉砕した後、ジェット気流を用いた微粉砕機で粉
砕し、さらに風力分級して平均粒径１３μｍの絶縁性ト
ナーｉを得た。(Hereinafter, blank spaces) Table 1 Preparation of Example Toner (1-11) Styrene-acrylic copolymer resin (softening point (Tag): 135°C, glass transition point (Tg)
: 58°C): 100 parts by weight Copper phthalocyanine pigment (manufactured by Dainichiseika Chemical Co., Ltd.) = 6 parts by weight Viscoel 550P (manufactured by Sanyo Chemical Industries, Ltd.): 5 parts by weight The above materials were thoroughly mixed in a ball mill and then heated to 130°C. The mixture was kneaded on three rolls. The kneaded material was allowed to cool and then coarsely pulverized with a feather mill, pulverized with a pulverizer using a jet stream, and further classified with air to obtain an insulating toner i having an average particle size of 13 μm.
上記のトナー１１００重量部とニグロシン（ボントロン
Ｎ−０１：オリエント化学工業社製）０．４重量部を１
０ｅヘンシルミキサーに入れ１５００ｒｐＩ１１の回転
数で２分間撹拌し、トナーｉの表面にニグロシンを付着
させた。次に１２０℃に加熱した気流内に粒子を分散し
て、約１〜３秒間瞬間加熱してトナーの表層部を局部的
に熱溶融し、ニグロシンをトナー表面に固着させ正荷電
性トナーｉを得た。1100 parts by weight of the above toner and 0.4 parts by weight of Nigrosine (Bontron N-01: manufactured by Orient Chemical Industry Co., Ltd.) were added to 1 part by weight.
The toner was placed in a Henshil mixer and stirred for 2 minutes at a rotational speed of 1500 rpm to adhere nigrosine to the surface of toner i. Next, the particles are dispersed in an air stream heated to 120°C and instantaneously heated for about 1 to 3 seconds to locally melt the surface layer of the toner, fixing nigrosine to the toner surface and creating positively charged toner i. Obtained.
同様の方法で絶縁性トナーｉにボントロンＮ−０１を表
２に示した重量部添加して正荷電性トナー２〜７を得た
。In the same manner, Bontron N-01 was added in the weight parts shown in Table 2 to the insulating toner i to obtain positively charged toners 2 to 7.
また、絶縁性トナーｉにスピロンブラックＴＲＨ（保土
谷化学工業社製のＣｒ含金の油溶性染料）を表１に示し
た重量部添加して負荷電性トナー１８〜１１を得た。Further, Spiron black TRH (Cr-containing oil-soluble dye manufactured by Hodogaya Chemical Industry Co., Ltd.) was added in the weight parts shown in Table 1 to the insulating toner i to obtain negatively charged toners 18 to 11.
表２
ポリエステル樹脂
（軟化点（Ｔｍ）：１２ｓ℃、ガラス転移点（Ｔｇ）７
６８℃、酸価（ＡＶ）：２３）
：１００重量部
Ｆａｓｔｏｇｅｎ Ｇｒｅｅｎ Ｓ（三菱化成工業
社製） ： ７重量部ビスコールＴＳ−２０
０
（工注化成工業社製） ： ２重量部上記の
材料をボールミルで十分に混合した後、１３５℃に熱し
た３本ロール上で混練した。混練物を放置冷却後、フェ
ザ−ミルで粗粉砕した後、ジェット気流を用いた微粉砕
機で粉砕し、さらに風力分級して平均粒径１１，５μｍ
の絶縁性トナー１１を得た。Table 2 Polyester resin (softening point (Tm): 12s°C, glass transition point (Tg) 7
68°C, acid value (AV): 23): 100 parts by weight Fastogen Green S (manufactured by Mitsubishi Chemical Industries, Ltd.): 7 parts by weight Viscoel TS-20
0 (manufactured by Kochu Kasei Kogyo Co., Ltd.): 2 parts by weight The above materials were thoroughly mixed in a ball mill, and then kneaded on three rolls heated to 135°C. After cooling the kneaded material, it was roughly pulverized with a feather mill, then pulverized with a fine pulverizer using a jet stream, and further classified by air to obtain an average particle size of 11.5 μm.
Insulating toner 11 was obtained.
上記のトナーｉｉ １００重量部とニグロシンベースＥ
Ｘ（オリエント化学工業社製）、またはボントロンＳ−
３４（オリエント化学工業社製）をトナーの調製（１）
と同様の方法で表３に示した添加部数添加してトナー１
２と１３を得た。100 parts by weight of the above toner II and nigrosine base E
X (manufactured by Orient Chemical Industry Co., Ltd.) or Bontron S-
34 (manufactured by Orient Chemical Industry Co., Ltd.) toner preparation (1)
Toner 1 was prepared by adding the parts shown in Table 3 in the same manner as above.
I got 2 and 13.
表３
着色剤として銅フタロシアニンの代わりにＳ ｙｌＩｕ
ｌｅｒ Ｆ ａｓｔ Ｙ ｅｌｌｏｗ ５ ＣＦ
（大日本インキ化学工業社製） 二 ８重量部とする
以外は、トナー１の製造方法と同様の方法で平均粒径１
３μｍのトナー１４を得た。Table 3 SylIu instead of copper phthalocyanine as colorant
ler F ast Y yellow 5 CF
(manufactured by Dainippon Ink & Chemicals) 2. Average particle size 1.
A toner 14 of 3 μm was obtained.
また、ボントロンＮ−０１の添加量を表４に示した量と
する以外はトナー１４と同様にトナー１５〜１７を調製
した。Further, Toners 15 to 17 were prepared in the same manner as Toner 14 except that the amount of Bontron N-01 added was as shown in Table 4.
表４
着色剤として銅フタロシアニンの代わりにレーキレッド
Ｃ（大日精化工業社製）：４重量部カーボンブラックＭ
Ａ＃８
（三菱化成工業社製） ：１重量部とする
以外は、トナー１の製造方法と同様の方法で平均粒径１
３μｍのトナー１８を得た。Table 4 Lake Red C (manufactured by Dainichiseika Kagyo Co., Ltd.) instead of copper phthalocyanine as a coloring agent: 4 parts by weight Carbon black M
A#8 (manufactured by Mitsubishi Chemical Industries, Ltd.): An average particle size of 1 was produced in the same manner as toner 1 except that the amount was 1 part by weight.
Toner 18 of 3 μm was obtained.
トナー（１９）の調製
スチレン ：６０重量部ｎ−ブチ
ルメタクリレート ＝３５重量部メタクリル酸
： ５重量部２．２−アゾビス−（２
，４−
ジメチルバレロニトリル）：０゜５重量部低分子量酸化
型ポリプロピレン
［ビスコールＴＳ−２００４
（工注化成工業社製） ： ３重量部レーキ
レッドＣ（大日精化工業社製）
：５重量部
上記材料をサンドスターラーにより充分に混合して、重
合性組成物を調製した。この重合性組成物を濃度３重量
％のアラビアゴム水溶液中に撹拌機ｒＴ −Ｋオートホ
モミクサー」（特殊機化工業社製）により回転数３００
Ｏｒｐｍで撹拌しながら、温度６０℃で６時間重合反
応させ、さらに温度を８０℃に上昇し重合反応させた。Preparation of toner (19) Styrene: 60 parts by weight n-butyl methacrylate = 35 parts by weight methacrylic acid
: 5 parts by weight 2.2-azobis-(2
, 4-dimethylvaleronitrile): 0.5 parts by weight Low molecular weight oxidized polypropylene [Viscol TS-2004 (manufactured by Kochu Kasei Kogyo Co., Ltd.): 3 parts by weight Lake Red C (manufactured by Dainichiseika Kogyo Co., Ltd.): 5 parts by weight The above materials were thoroughly mixed using a sand stirrer to prepare a polymerizable composition. This polymerizable composition was added to an aqueous gum arabic solution with a concentration of 3% by weight using a stirrer rT-K Auto Homo Mixer (manufactured by Tokushu Kika Kogyo Co., Ltd.) at a rotation speed of 300.
The polymerization reaction was carried out at a temperature of 60° C. for 6 hours while stirring with Orpm, and the temperature was further raised to 80° C. to carry out a polymerization reaction.
重合反応終了後、反応系を冷却して５回水洗後、ろ過し
乾燥して球状粒子を得た。。After the polymerization reaction was completed, the reaction system was cooled, washed with water five times, filtered and dried to obtain spherical particles. .
得られた球状粒子の平均粒径１１．８μ１１軟化点（Ｔ
ｎ＋）は１４１℃、ガラス転移点（Ｔｇ）は６１℃であ
った。The average particle diameter of the obtained spherical particles was 11.8μ11, the softening point (T
n+) was 141°C, and the glass transition point (Tg) was 61°C.
得られた球状粒子をトナーｉｉｉとする。The obtained spherical particles are referred to as toner iii.
トナーｉｉｉ １００重量部と荷電付与剤ニグロシン系
染料ボントロンＮ−０１（オリエント化学工業社製）０
．５重量部を用いトナーｌの製造方法と同様の方法でト
ナー１９を得た。Toner III 100 parts by weight and charge imparting agent nigrosine dye Bontron N-01 (manufactured by Orient Chemical Industry Co., Ltd.) 0
．． Toner 19 was obtained using 5 parts by weight in the same manner as toner 1.
トナー（２０）の調製
ニグロシンベースＥＸ（オリエント化学工業社製）３景
気部を加えること以外はトナー１９の調製と同様の方法
で平均粒径１２．θμｍ１軟化点（Ｔｍ）１４１’ｃ、
ガラス転移点（Ｔｇ）６１’Ｃのトナー２０を得た。Preparation of toner (20) An average particle size of 12.0 was prepared in the same manner as toner 19, except that 3 parts of Nigrosine Base EX (manufactured by Orient Chemical Industry Co., Ltd.) was added. θμm1 Softening point (Tm) 141'c,
Toner 20 having a glass transition point (Tg) of 61'C was obtained.
トナー（２Ｉ）の調製
前記で得られた平均粒径１３μｍの絶縁性トナー１ｌｏ
ｏ重量部とニグロシン（ボントロンＮ−０１：オリエン
ト化学工業社製）０．５重量部を奈良機械ハイブリダイ
ゼーションシステムＮＨ３−１型（奈良機械製作所社製
）の０．Ｍ、ダイザ−を用い、ｌ ５００ ｒｐｍの回
転数で２分間混合撹拌し、絶縁性トナー１粒子の表面に
ニグロシンを付着させた。次に同じハイブリダイゼーシ
ョンシステムのハイブリダイザ−を用い、９０００ ｒ
ｐｍで３分間の処理を行いニグロシンを絶縁性トナーｉ
の表面に固着させトナー２１を得た。Preparation of toner (2I) 1 lo of the insulating toner with an average particle size of 13 μm obtained above.
0.0 parts by weight and 0.5 parts by weight of nigrosine (Bontron N-01: manufactured by Orient Chemical Industry Co., Ltd.) were added to 0.5 parts by weight of Nara Kikai Hybridization System NH3-1 type (manufactured by Nara Kikai Seisakusho Co., Ltd.). The mixture was mixed and stirred for 2 minutes at a rotational speed of 1500 rpm using a dizer, thereby adhering nigrosine to the surface of one particle of the insulating toner. Next, using the hybridizer of the same hybridization system, 9000 r
pm treatment for 3 minutes to convert nigrosine into insulating toner i.
toner 21 was obtained.
トナー（２２）の調製
シード重合法により得られた単分散球状のスチレン系ポ
リマー粒子（平均粒径８μｍ、ガラス転移点５４℃、軟
化点１２８℃）１００重量部と銅フタロシアニン顔料（
大日精化工業社製）６重量部を奈良機械ハイブリダイゼ
ーションシステムＮＨＳ−１型（奈良機械製作所社製）
のハイブリダイザ−で処理（９０００ｒｐｍ、 、３分
間）し、銅フタロシアニン顔料をポリマー粒子表面に固
定化した。Preparation of toner (22) 100 parts by weight of monodisperse spherical styrene polymer particles (average particle size 8 μm, glass transition point 54°C, softening point 128°C) obtained by seed polymerization method and copper phthalocyanine pigment (
6 parts by weight of Nara Kikai Hybridization System NHS-1 (manufactured by Nara Kikai Seisakusho Co., Ltd.)
The polymer particles were treated with a hybridizer (9000 rpm, 3 minutes) to immobilize the copper phthalocyanine pigment on the surface of the polymer particles.
上記顔料を処理したポリマー粒子１００重量部とＰＭＭ
Ａ微粒子ＭＰ−１４５１（綜研化学社製、ガラス転移点
１２５℃）１０重量部を上記と同様の処理によりＰＭＭ
Ａ樹脂コート層を設けた。さらにここで得られたポリマ
ー粒子１００重量部に対し正の荷電制御剤ニグロシン（
ボントロンＮ−０１：オリエント化学工業社製）０．５
重量部を上記と同様の処理を行うことにより、ニグロシ
ンが表面に固着した平均粒径９μｍのトナー（２２）を
得た。100 parts by weight of polymer particles treated with the above pigment and PMM
10 parts by weight of A fine particles MP-1451 (manufactured by Soken Kagaku Co., Ltd., glass transition temperature: 125°C) was processed into PMM by the same treatment as above.
A resin coat layer was provided. Furthermore, the positive charge control agent nigrosine (
Bontron N-01: Orient Chemical Industry Co., Ltd.) 0.5
By subjecting the weight part to the same treatment as above, a toner (22) having an average particle size of 9 μm and having nigrosine adhered to the surface was obtained.
スチレン−アクリル共重合樹脂
（軟化点（Ｔｍ）；１３５℃、ガラス転移点（Ｔｇ）；
５ｇ℃）１００重量部
ニグロシン系染料ボントロンＮ−０ｆ
（オリエント化学工業社製） １重量部上記成
分をトルエン溶媒中で高剪断撹拌により均一分散した後
、芯材として絶縁性トナーｉを加えスプレードライ法に
より噴霧乾燥し絶縁性トナー表面に上記成分をコートし
、平均粒径Ｉ４μｍのトナー（２３）を得た。Styrene-acrylic copolymer resin (softening point (Tm); 135°C, glass transition point (Tg);
5g°C) 100 parts by weight Nigrosine dye Bontron N-0f (manufactured by Orient Chemical Industry Co., Ltd.) 1 part by weight After uniformly dispersing the above components in a toluene solvent by high-shear stirring, insulating toner i was added as a core material and spray-dried. The above components were coated on the surface of the insulating toner by spray drying according to the method to obtain a toner (23) having an average particle size of I4 μm.
トナー（２４）の調製（比較）
スチレン−アクリル共重合樹脂＝１００重量部（軟化点
（Ｔｍ）；１３５℃、ガラス転移点（Ｔｇ）；５８℃）
銅フタロシアニンブルー
（大日本インキ化学工業社製）： ５重量部ビスコー
ル５５０Ｐ
（工注化成工業社製） ： ５重量部ニグロ
シン系染料ボントロンＮ−０１
（オリエント化学工業社製） ： ３重量部上記の
材料を絶縁性トナーｉと同様の製造方法にて平均粒径１
３μｍのトナー（２４）を得た。Preparation of toner (24) (comparison) Styrene-acrylic copolymer resin = 100 parts by weight (softening point (Tm): 135°C, glass transition point (Tg): 58°C)
Copper phthalocyanine blue (manufactured by Dainippon Ink & Chemicals): 5 parts by weight Viscoel 550P (manufactured by Kochu Kasei Kogyo): 5 parts by weight Nigrosine dye Bontron N-01 (manufactured by Orient Chemical Industries): 3 parts by weight The average particle size of the material is 1 using the same manufacturing method as insulating toner i.
A 3 μm toner (24) was obtained.
トナー（２５〜３１）の調整
スチレン−アクリル共重合樹脂
（軟化点（Ｔｍ）：１３５℃、ガラス転移点（Ｔｇ）：
５８℃）：１００重量部
スチレン−アミノアクリル樹脂
（参考例４） ＝ ２重量部銅フタ
ロシアニン顔料
（大日精化工業社製） ； ６重量部ビスコ
ール５５０Ｐ
（工注化成工業社製） ： ５重量部上記の
材料をボールミルで十分に混合した後、１３０℃に熱し
た３本ロール上で混練した。混練物を放置冷却後、フェ
ザ−ミルで粗粉砕した後、ジェット気流を用いた微粉砕
機で粉砕し、さらに風力分級して平均粒径１３μｍのト
ナーｉｖを得た。Preparation of toner (25-31) Styrene-acrylic copolymer resin (softening point (Tm): 135°C, glass transition point (Tg):
58°C): 100 parts by weight Styrene-aminoacrylic resin (Reference Example 4) = 2 parts by weight Copper phthalocyanine pigment (manufactured by Dainichiseika Kogyo Co., Ltd.); 6 parts by weight Viscoel 550P (manufactured by Kochu Kasei Kogyo Co., Ltd.): 5 parts by weight The above materials were thoroughly mixed in a ball mill and then kneaded on three rolls heated to 130°C. The kneaded material was allowed to cool and then coarsely pulverized with a feather mill, pulverized with a pulverizer using a jet stream, and further classified with air to obtain a toner iv having an average particle size of 13 μm.
上記のトナ−１ｖ１００重量部とニグロシン（ボントロ
ンＮ−０１：オリエント化学工業社製）０．４重盪部を
ＩＯＱヘンシェルミキサーに入れ１５００ ｒｐ＋ｅの
回転数で２分間撹拌し、トナーの表面にニグロシンを付
着させた。次に１２０℃に加熱した気流内に粒子を分散
して、約１〜３秒間瞬間加熱してトナーの表層部を局部
的に熱溶融し、ニグロシンをトナー表面に固着させトナ
ー２５を得た。100 parts by weight of the above toner 1v and 0.4 parts by weight of Nigrosine (Bontron N-01, manufactured by Orient Chemical Industry Co., Ltd.) were placed in an IOQ Henschel mixer and stirred for 2 minutes at a rotation speed of 1500 RP+E to coat the surface of the toner with Nigrosine. Attached. Next, the particles were dispersed in an air stream heated to 120° C., and instantaneously heated for about 1 to 3 seconds to locally melt the surface layer of the toner, thereby fixing nigrosine to the toner surface to obtain toner 25.
同様の方法でトナー１ｖの表面にボントロンＮ−０１を
表５に示した重量部添加してトナー２５〜３１を得た。In the same manner, Bontron N-01 was added in the weight parts shown in Table 5 to the surface of toner 1v to obtain toners 25 to 31.
表５
トナー（３２）の調製
スチレン−アクリル共重合樹脂：１００重量部（軟化点
（Ｔｍ）：１３５℃、ガラス転移点（Ｔｇ）：５ｇ℃）
第４級アンモニウム塩 Ｐ−５１
（オリエント化学工業社製） ： ２重量部レーキ
レッドＣ（大日精化工業社製）
： ４重量部
カーボンブラックＭＡ＃８
（三菱化成工業社製） ： １重量部ビスコ
ール５５０Ｐ
（三菱化成工業社製） ： ５重量部をトナ
ーｉｖの製造方法と同様の方法にて平均粒径１４μｍの
トナーＶを得た。このトナー１００重量部に対しニグロ
シンベースＥＸ（オリエント化学工業社製）を０．５重
量部を１０ｉ２ヘンシエルミキサーに入れ正荷電性トナ
ー２５と同様の方法によりニグロシンをトナー表面に固
着させトナー３２を得た。Table 5 Preparation of toner (32) Styrene-acrylic copolymer resin: 100 parts by weight (softening point (Tm): 135°C, glass transition point (Tg): 5g°C)
Quaternary ammonium salt P-51 (manufactured by Orient Chemical Industries, Ltd.): 2 parts by weight Lake Red C (manufactured by Dainichiseika Industries, Ltd.): 4 parts by weight Carbon black MA#8 (manufactured by Mitsubishi Chemical Industries, Ltd.): 1 part by weight Viscol 550P (manufactured by Mitsubishi Chemical Industries, Ltd.): Toner V having an average particle size of 14 μm was obtained using 5 parts by weight in the same manner as the method for producing toner iv. To 100 parts by weight of this toner, 0.5 parts by weight of Nigrosine Base EX (manufactured by Orient Kagaku Kogyo Co., Ltd.) was placed in a 10i2 Henschel mixer, and Nigrosine was fixed on the toner surface in the same manner as positively charged toner 25 to form toner 32. Obtained.
トナー（３３）の調製
スチレン−アクリル共重合樹脂：１００重景景気軟化点
（Ｔｍ）：１３５℃、ガラス転移点（Ｔｇ）＋５８℃）
スチレン−アクリル樹脂（参考例２ ）： ２ ？Ｉｉ
１部第４級アンモニウム塩 Ｐ−５１
（オリエント化学工業社製） ： １重量部Ｓ ｙ
ｉｕｌｅｒ Ｆ ａｓｋ Ｙ ｅｌｌｏｗ ５Ｇ Ｆ
： ８重１部を、トナーｉｖの製造方法と同様の方
法にて平均粒径１３μ１ｌＩＱトナーｖｉを得た。この
トナー１００重量部に対し、ニグロシンベースＥ Ｘ
（ｔ ’）エンド化学工業社製）０．４重量部を１０Ｃ
ヘンシエルミキサーに入れ、トナー２５と同様の方法に
よりニグロシンをトナー表面に固着させ、正荷電性トナ
ー３３を得た。Preparation of toner (33) Styrene-acrylic copolymer resin: 100 economic softening point (Tm): 135°C, glass transition point (Tg) + 58°C)
Styrene-acrylic resin (Reference example 2): 2? Ii
1 part quaternary ammonium salt P-51 (manufactured by Orient Chemical Industry Co., Ltd.): 1 part by weight S y
iuler F ask Y yellow 5G F
: 1 part of 8x was used to obtain an IQ toner vi with an average particle size of 13 μl by the same method as the manufacturing method of toner iv. For 100 parts by weight of this toner, Nigrosine base EX
(t') manufactured by Endo Kagaku Kogyo Co., Ltd.) 0.4 parts by weight at 10C
The toner was placed in a Henschel mixer, and nigrosine was fixed on the surface of the toner in the same manner as toner 25 to obtain positively charged toner 33.
トナー（ｖｉｉ）の調製
スチレン−アミノアクリル樹脂（参考例４）を３０重量
部とする以外は正荷電性トナーｉｖと同じ組成、製法に
より、平均粒径１３μｍの正荷電性トナーｖｉｉを得た
。Preparation of Toner (vii) A positively charged toner vii having an average particle size of 13 μm was obtained using the same composition and manufacturing method as the positively charged toner iv except that 30 parts by weight of the styrene-aminoacrylic resin (Reference Example 4) was used.
トナー（ｖｉ）の調製
第４級アンモニウム塩Ｐ−５１（オリエント化学工業社
製）を１０重量部とする以外は、トナーＶと同じ組成、
製法により平均粒径１３μｍの正荷電性トナーｖｉを得
た。Preparation of toner (vi) Same composition as toner V except that quaternary ammonium salt P-51 (manufactured by Orient Chemical Industry Co., Ltd.) was used in an amount of 10 parts by weight.
A positively charged toner vi having an average particle size of 13 μm was obtained by the manufacturing method.
トナー（ｉｘ）の調製
スチレン−アミノアクリル共重合樹脂（参考例２）２０
重量部、第４級アンモニウム塩Ｐ−５１（オリエント化
学工業社製）５重量部とする以外は、トナーｖｉと同じ
組成、製法により平均粒径１３μｍの正荷電性トナーｉ
ｘを得た。Preparation of toner (ix) Styrene-aminoacrylic copolymer resin (Reference Example 2) 20
Positively charged toner i with an average particle size of 13 μm was prepared using the same composition and manufacturing method as toner vi, except that the weight part was 5 parts by weight of quaternary ammonium salt P-51 (manufactured by Orient Chemical Industry Co., Ltd.).
I got x.
トナー（３４〜３７）の調製
トナーｉｘ １００重量部に対し、ニグロシンベースＥ
Ｘ（オリエント化学社製）の下記表６に示した重量部を
１０＋２ヘンシエルミキサーに入れ、トナー２５と同様
に方法によりトナーｉｘの表面にニグロシン粒子を固着
させた。Preparation of toners (34 to 37) Toner ix 100 parts by weight, Nigrosine base E
The weight parts of X (manufactured by Orient Kagaku Co., Ltd.) shown in Table 6 below were placed in a 10+2 Henschel mixer, and nigrosine particles were fixed on the surface of toner ix in the same manner as toner 25.
表６
トナー（３８）の調製
ニグロシン（ボントロンＮ−０１：オリエント化学工業
社製）を０．５重量部添加する以外はトナーｉｖと同じ
組成、製法により、平均粒径１３μｍの正荷電性トナー
３８を得た。Table 6 Preparation of toner (38) Positively charged toner 38 with an average particle size of 13 μm was prepared using the same composition and manufacturing method as toner iv except that 0.5 parts by weight of nigrosine (Bontron N-01: manufactured by Orient Chemical Industry Co., Ltd.) was added. I got it.
トナー（３９）の調製
第４級アンモニウム塩Ｐ−５１の代わりにフェノチアジ
ン化合物（住良化学工業社製）を２重量部用いた以外は
トナー３２と同じ組成、製法により平均粒径１３μｍの
正荷電性トナー３９を得た。Preparation of Toner (39) A positively charged toner with an average particle size of 13 μm was prepared using the same composition and manufacturing method as Toner 32, except that 2 parts by weight of a phenothiazine compound (manufactured by Sumira Chemical Industries, Ltd.) was used in place of the quaternary ammonium salt P-51. A sex toner 39 was obtained.
トナー（４０）の調製
スチレン ：６０重量部ｎ−ブチ
ルメタクリレート ：３０重量部２．２，３．３
−テトラフルオロ
プロピルアクリレート ： ５重量部２．２−
アゾビス（２，４−ジメ
チルバレロニトリル） ： ０．５ｆ［Ｉ１
１１分子量酸化型ポリプロピレン
「ビスコールＴＳ−２００Ｊ
（工注化成工業社製） ＝ ３重量部レーキ
レッドＣ（大日精化工業社製）
； ５重量部
上記組成物をサンドスターラーにより充分混合して重合
性組成物を調製した。この重合性組成物を濃度３重量％
のアラビアゴム水溶液中に撹拌機ｒＴ−にオートホモミ
クサー」（特殊機化工業社製）により回転数２５０ Ｏ
ｒｐｍで撹拌しながら添加し、その後通常の撹拌機によ
り回転数８ Ｏｒｐｍで撹拌しながら温度６０℃で６時
間重合反応させ、さらに温度を８０℃に上昇し、重合反
応させた。重合反応終了後、反応系を冷却して５回水洗
後、ろ過し乾燥して得られた平均粒径１３．３μｍの球
状粒子をトナーＸとする。この球状粒子の軟化点（Ｔｍ
）、１４１℃ガラス転移点（Ｔｇ）６１”Ｃであった。Preparation of toner (40) Styrene: 60 parts by weight n-butyl methacrylate: 30 parts by weight 2.2, 3.3
-Tetrafluoropropyl acrylate: 5 parts by weight 2.2-
Azobis(2,4-dimethylvaleronitrile): 0.5f[I1
11 molecular weight oxidized polypropylene "Viscol TS-200J (manufactured by Kochu Kasei Kogyo Co., Ltd.) = 3 parts by weight Lake Red C (manufactured by Dainichiseika Kogyo Co., Ltd.); 5 parts by weight The above composition was thoroughly mixed with a sand stirrer to achieve polymerizability. A composition was prepared.The concentration of this polymerizable composition was 3% by weight.
Aqueous solution of gum arabic was mixed with a stirrer rT- using an auto homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.) at a rotation speed of 250 O.
The mixture was added while stirring at 80 rpm, and then a polymerization reaction was carried out at a temperature of 60° C. for 6 hours while stirring at a rotational speed of 8 Orpm using a conventional stirrer, and the temperature was further raised to 80° C. to carry out a polymerization reaction. After the polymerization reaction is completed, the reaction system is cooled, washed with water five times, filtered, and dried to obtain spherical particles with an average particle diameter of 13.3 μm, which is referred to as Toner X. The softening point (Tm
), and the glass transition point (Tg) was 61"C at 141°C.
上記トナーＸ粒子１００重量部と荷電付与剤ニグロシン
系染料ボントロンＮ−０１（オリエント化学工業社製）
０．１重量部を用いトナー２５と同じ方法で製造した。100 parts by weight of the above Toner
It was manufactured in the same manner as Toner 25 using 0.1 part by weight.
ここで得られた正荷電性トナーをトナー４０とする。The positively charged toner obtained here is referred to as toner 40.
スチレン−アクリル共重合樹脂：１００重量部（軟化点
（Ｔ ａｎ） ；１３５℃、ガラス転移点（Ｔｇ）；５
８℃）スチレン／ブチルアクリレート／
２．２．２−トリフルオロエチル
アクリレート＝７０／１５／１５ ： １０重量
部銅フタロシアニン顔料
（大日精化工業社製） ： ６重量部ビスコ
ール５５０Ｐ
（工注化成工業社製） ： ５重量部上記の
材料をボールミルで十分に混合した後、１３０℃に熱し
た３本ロール上で混練した。混線物を放置冷却後、フェ
ザ−ミルで粗粉砕した後、ジェット気流を用いた微粉砕
機で粉砕し、さらに風力分級して平均粒径１３μｍのト
ナーｘｉを得た。Styrene-acrylic copolymer resin: 100 parts by weight (softening point (Tan): 135°C, glass transition point (Tg): 5
8°C) Styrene/butyl acrylate/2.2.2-trifluoroethyl acrylate = 70/15/15: 10 parts by weight Copper phthalocyanine pigment (manufactured by Dainichiseika Kogyo Co., Ltd.): 6 parts by weight Viscoel 550P (Kochu Kasei Kogyo Co., Ltd.) ): 5 parts by weight The above materials were thoroughly mixed in a ball mill, and then kneaded on three rolls heated to 130°C. After cooling the mixture, it was roughly pulverized with a feather mill, then pulverized with a pulverizer using a jet stream, and further classified with air to obtain a toner xi having an average particle size of 13 μm.
上記のトナーｘｉ １００重量部とクロム錯塩型染料ス
ピロンブラックＴＲＨ（保土谷化学工業社製）０．５重
量部を１０１２ヘンシエルミキサーに入れ１５００ ｒ
ｐｍの回転数で２分間撹拌し、トナーｘｉの表面にスビ
ロンブラックＴＲＨを付着させた。次に２００℃に加熱
した気流内に粒子を分散して、約１〜３秒間瞬間加熱し
てトナーの表層部を局部的に熱溶融し、クロム錯塩型染
料をトナー表面に固着させ負荷電性トナー４１を得た。100 parts by weight of the above toner xi and 0.5 parts by weight of chromium complex dye Spiron Black TRH (manufactured by Hodogaya Chemical Industry Co., Ltd.) were placed in a 1012 Henschel mixer and heated at 1500 r.
The mixture was stirred for 2 minutes at a rotational speed of pm to adhere Subiron Black TRH to the surface of the toner xi. Next, the particles are dispersed in an air stream heated to 200°C and instantaneously heated for about 1 to 3 seconds to locally melt the surface layer of the toner, fixing the chromium complex dye to the toner surface and creating a negative charge. Toner 41 was obtained.
同様に、トナーｘｉの表面にスピロンブラックＴＲＨを
下記表７に示した重量部固着させ負荷電性トナー４２〜
４４を調製した。Similarly, Spiron black TRH was adhered to the surface of toner xi in the weight parts shown in Table 7 below to form negatively charged toners 42 to 42.
44 was prepared.
スチレン−アクリル共重合樹脂：１００重量部（軟化点
（Ｔｍ）＋１３５℃、ガラス転移点（Ｔｇ）：５ｇ℃）
スチレン／ブチルアクリレート／
２．２．２−）リフルオロエチル
アクリレート＝７０／１５／１５ ： ｌ Ｏ重量
部スチレン／ブチルアクリレート／
２，２，３．３−テトラフルオロプロピルアクリレート
−７５／２５１５ ： ５重虫部Ｓｙｍｕｌｅｒ
Ｆａｓｔ Ｙｅｌｌｏｗ ５ＧＦ： ８重嘔部ビス
コール５５０Ｐ
（工注化成工業社製） ＝ ５重量部を、トナ
ーｘｉの製造方法と同様の方法にて平均粒径１４μｍの
負荷電性トナーｘｉｉを得た。このトナーｘｉｉ１００
重量部に対し、Ｓ−３４（オリエント化学工業社製）０
．５重量部をｌＯｅヘンシェルミキサーに入れ、トナー
４１と同様の方法によりクロム錯塩型染料をトナー表面
に固着さけ、負荷電性トナー４５を得た。Styrene-acrylic copolymer resin: 100 parts by weight (softening point (Tm) +135°C, glass transition point (Tg): 5g°C)
Styrene/butyl acrylate/2.2.2-)lifluoroethyl acrylate = 70/15/15: 1 O parts by weight Styrene/butyl acrylate/2,2,3.3-tetrafluoropropyl acrylate -75/2515: 5 Symuler
Fast Yellow 5GF: A negatively charged toner xii having an average particle size of 14 μm was obtained using 5 parts by weight of 8-part Viscoel 550P (manufactured by Kochu Kasei Kogyo Co., Ltd.) in the same manner as the method for producing toner xi. This toner xii100
Based on parts by weight, S-34 (manufactured by Orient Chemical Industry Co., Ltd.) 0
．． 5 parts by weight were placed in a 1Oe Henschel mixer, and the chromium complex dye was prevented from sticking to the toner surface in the same manner as toner 41, to obtain negatively charged toner 45.
トナー（４６）の調製
スチレン ＝６０重量部ｎ−ブチル
メタクリレート ：２５重量部２．２．２−トリフ
ルオロ
エチルアクリレート ：１５５重量部 ２．２
−アゾビス（２，４−ジメ
チルバレロニトリル） 二〇、５重量部低分
子量ポリプロピレン 「ビスコール５５Ｐ」（工注化成
工業社製） ・ ３重Ｂ部赤色顔料レーキレッ
ドＣ
（大日精化工業社製） ： ５重量部上記材料
をサンドスターラーにより充分混合して、重合性組成物
を調製した。この重合性組成物を濃度３重量％のアラビ
アゴム水溶液中に撹拌機ｒＴ−にオートホモミクサー」
（特殊機化工業社製）により回転数３００Ｏｒｐｍで撹
拌しながら、温度６０℃で６時間重合反応させ、さらに
温度を８０℃に上昇し、重合反応させた。重合反応終了
後、反応系を冷却して５回水洗後、ろ過し乾燥して球状
粒子を得た。Preparation of toner (46) Styrene = 60 parts by weight n-butyl methacrylate: 25 parts by weight 2.2.2-Trifluoroethyl acrylate: 155 parts by weight 2.2
-Azobis(2,4-dimethylvaleronitrile) 20.5 parts by weight Low molecular weight polypropylene "Viscol 55P" (manufactured by Kochu Kasei Kogyo Co., Ltd.) - Triple B part red pigment Lake Red C (manufactured by Dainichiseika Kogyo Co., Ltd.) : 5 parts by weight The above materials were thoroughly mixed using a sand stirrer to prepare a polymerizable composition. This polymerizable composition was added to an aqueous gum arabic solution with a concentration of 3% by weight using an autohomogen mixer.
(manufactured by Tokushu Kika Kogyo Co., Ltd.) while stirring at a rotational speed of 300 rpm, a polymerization reaction was carried out at a temperature of 60°C for 6 hours, and the temperature was further raised to 80°C to carry out a polymerization reaction. After the polymerization reaction was completed, the reaction system was cooled, washed with water five times, filtered and dried to obtain spherical particles.
得られた球状粒子の平均粒径１１，６μｍ、軟化点（Ｔ
ａｇ）は１４４℃、ガラス転移点（Ｔｇ）は６４℃であ
った。The average particle diameter of the obtained spherical particles was 11.6 μm, the softening point (T
ag) was 144°C, and the glass transition point (Tg) was 64°C.
この粒子をトナーｘ ｉｉｉとする。These particles are referred to as toner x iii.
トナーｘ ｉｉｉを１００重量部とクロム錯塩型染料ス
ピロンブラックＴＲＨ（保土谷化学工業社製）０．５重
量部とする以外はトナーの製造例２２と同様の方法によ
りトナー４６を得た。Toner 46 was obtained in the same manner as Toner Production Example 22, except that 100 parts by weight of toner x iii and 0.5 parts by weight of chromium complex dye Spilon Black TRH (manufactured by Hodogaya Chemical Industries, Ltd.) were used.
マイクロキャリアの調製
実施例に用いられる現像剤を構成するキャリアはバイン
ダー型キャリアで以下のようにして製造される。Preparation of Microcarrier The carrier constituting the developer used in the Examples is a binder type carrier and is manufactured as follows.
マグネタイト
（ＢＬ−８Ｐ：チタン工業社製）：５００重量部スチレ
ン−アクリル共重合樹脂
（ブライオライドＡＣＬ：グッドイヤーケミカル社製）
：Ｉ００重量部シリカ＃２
００
（日本アエロジル社製） ： ２重量部以上の
成分をスーパーミキサーで十分混合して二軸押出混練機
で混練後、冷却粗粉砕し、ハンマーミルで平均粒径５０
μｍに粉砕し風力分級機で粗粉・微粉を分級し、平均４
０μｍのマイクロキャリアを得た。比重を測定すると３
．３であった。Magnetite (BL-8P: manufactured by Titan Kogyo Co., Ltd.): 500 parts by weight Styrene-acrylic copolymer resin (Bryolide ACL: manufactured by Goodyear Chemical Company)
: I00 parts by weight Silica #2
00 (manufactured by Nippon Aerosil Co., Ltd.): 2 parts by weight or more of the ingredients were thoroughly mixed in a super mixer, kneaded in a twin-screw extrusion kneader, cooled and coarsely pulverized, and then reduced to an average particle size of 50 in a hammer mill.
Grind to μm and classify coarse powder and fine powder using a wind classifier, with an average of 4
Microcarriers of 0 μm were obtained. When you measure the specific gravity, it is 3.
．． It was 3.
現像剤の調製および帯電量・飛散量測定前述のトナー１
〜４６、ｉ ＝ ｘ ｉｉｉをそれぞれ１００重量部に
対してコロイダルシリカＲ−９７２（日本アエロジル社
製）：０．１重量部で表面処理を行った（このコロイダ
ルシリカはトナー表面に固着されてはいない。）。表面
処理されたトナー５９とマイクロキャリア２７９とを５
０ｃｃのポリ瓶に入れ、回転架台にのせて１２０ ｒｐ
ｎ＋で回転させたときのトナーの帯電量の立ち上がりを
調べるために、３分、１０分、３０分間撹拌後の帯電量
を測定し、またその時の飛散量を調べた。Preparation of developer and measurement of charge amount and scattering amount Toner 1 mentioned above
~46, i = x iii was surface treated with 0.1 part by weight of colloidal silica R-972 (manufactured by Nippon Aerosil Co., Ltd.) for 100 parts by weight of each (this colloidal silica did not adhere to the toner surface. not present.). The surface-treated toner 59 and the microcarrier 279 are
Put it in a 0cc plastic bottle, put it on a rotating stand and spin it at 120 rp.
In order to investigate the rise in the charge amount of the toner when rotated at n+, the charge amount after stirring for 3 minutes, 10 minutes, and 30 minutes was measured, and the amount of scattering at that time was also investigated.
、飛散量測定は、デジタル粉塵計Ｐ５Ｈ２型（柴田化学
社製）で測定した。前記粉塵計とマグネットロールとを
１０ｃｍ離れたところに設置し、このマグネットロール
の上に現像剤２ｇをセットした後、マグネットを２００
０ ｒｐｍで回転させたときに発塵するトナーの粒子を
前記粉塵計が粉塵として読み取って、１分間のカウント
数ｃｐＩＩ＋で表示する。The amount of scattering was measured using a digital dust meter model P5H2 (manufactured by Shibata Chemical Co., Ltd.). The dust meter and the magnet roll were installed at a distance of 10 cm, and after setting 2 g of developer on the magnet roll, the magnet was placed at a distance of 20 cm.
The dust meter reads the toner particles generated when the toner is rotated at 0 rpm as dust, and displays the number of counts per minute cpII+.
なお、飛散量の実用レベルとしては５００ ｃｐｍ以下
を目標とした。The practical level of scattering amount was set at 500 cpm or less.
カラー画像上の荷電付与剤による色の濁り測定路トナー
により得られたカラー画像を色彩色差計ＣＲ−１００（
ミノルタカメラ社製）を用い彩度を測定し、ニグロシン
系染料なしのトナーによる彩度との差を求めることによ
り色の濁りに対する優劣を評価した。なお、◎、○、×
は次のことを意味する。Color turbidity caused by the charge imparting agent on the color image Measurement path The color image obtained with the toner was measured using a color difference meter CR-100 (
The saturation was measured using a toner (manufactured by Minolta Camera Co., Ltd.), and the difference between the saturation and the saturation of a toner without nigrosine dye was evaluated to evaluate whether the color was cloudy or not. In addition, ◎, ○, ×
means the following:
◎： 色の濁りがほとんどないもの
○： 色の濁りが実用上気にならないもの×： 色の濁
りが極めてひどいもの
吸光光度法によるニグロシンベースＥＸの」■ ニグロ
シンベースＥＸを和光純薬工業社製特級エタノールを溶
媒として分光光度計を用いた吸光光度法によりλｍａｘ
＝ ５６７ ｎｍに対する吸光度を求めることにより検
量線を求める。この時得られた検量線を第１図に示す。◎: Almost no color turbidity ○: Color turbidity is not a practical concern ×: Extremely severe color turbidity Nigrosine Base EX measured by spectrophotometry ■ Nigrosine Base EX manufactured by Wako Pure Chemical Industries, Ltd. λmax was determined by absorption photometry using a spectrophotometer using special grade ethanol as a solvent.
A calibration curve is determined by determining the absorbance at = 567 nm. The calibration curve obtained at this time is shown in FIG.
■ 試料となるトナーを約５０１精秤し、これを２５＋
ｙ１２エタノール中に浸漬させ、その後適当時間シェー
キングを行ってトナー表面のニグロシンベースＥｘを溶
出させる。エタノール溶液は樹脂や他成分に対しては難
溶性を示す為、本測定に対し有効に利用できる。■ Accurately weigh approximately 501 pieces of toner as a sample, and weigh this to 25+
The toner is immersed in y12 ethanol and then shaken for an appropriate period of time to elute the nigrosine base Ex on the toner surface. Ethanol solutions are poorly soluble in resins and other components, so they can be effectively used for this measurement.
■ この溶出液をＮｏ、２ろ紙を用いろ別し、残留トナ
ーと溶出ろ液とに分離を行う。(2) This eluate is filtered using No. 2 filter paper to separate the residual toner and the eluate filtrate.
■ 分離した溶出液を分光光度計により■と同様λｍａ
ｘ＝ ５６７ ｎｍにおける吸光度を求める事により検
量線と■で精秤したトナーサンプル量より単位トナー重
量当りのニグロシンベースＥＸの定量を行う。■ The separated eluate was measured using a spectrophotometer to measure λma as in ■.
By determining the absorbance at x=567 nm, nigrosine base EX per unit weight of toner is determined from the calibration curve and the amount of toner sample accurately weighed in (■).
荷電付与剤として使用したスビロンブラックＴＲＨを定
量する場合も上記方法と同様の方法が適用できる。A method similar to the above method can also be applied when quantifying Subiron Black TRH used as a charge imparting agent.
なお、スピロンブラックＴｒｔＨは、λｍａｘ＝ ５７
７ｎ１１における吸光度を求める事により定量を行った
。In addition, Spiron black TrtH has λmax=57
Quantification was performed by determining the absorbance at 7n11.
スビロンブラックＴＲＨに対する検量線を第２図に示す
。A calibration curve for Subiron Black TRH is shown in FIG.
以上の帯電量、飛散量、カラー画像の濁り度、表面固着
量の測定結果を表８および表９に示す。Tables 8 and 9 show the measurement results of the amount of charge, amount of scattering, turbidity of color images, and amount of surface adhesion.
なお、表８には、本発明の目的を満足するトナーについ
ての評価結果をまとめ、表９には、本発明の目的を十分
に満足しないトナーについての結果をまとめた。Note that Table 8 summarizes the evaluation results for toners that satisfy the objectives of the present invention, and Table 9 summarizes the results for toners that do not fully satisfy the objectives of the present invention.
帯電量分布測定
帯電量分布の測定には、１９８６年１１月２８日に開催
された電子写真学会主催の第５８回研究討論会で、ミノ
ルタカメラ（株）の青板らによって発表された装置を用
いた。原理についての詳細は、同研究討論会で配布され
た資料に記載されており、ここでは簡単に説明する。第
３図にその構成を示す。Charge amount distribution measurement To measure the charge amount distribution, we used a device announced by Seita et al. of Minolta Camera Co., Ltd. at the 58th Research Conference sponsored by the Electrophotography Society held on November 28, 1986. Using. The details of the principle are described in the materials distributed at the same research discussion group, and will be briefly explained here. Figure 3 shows its configuration.
、測定方法を以下に説明する。, the measurement method will be explained below.
マグネットロール（３）の回転数は１００ ｒｐｍにセ
ットし、現像剤としては３０分撹拌後のものを用いた。The rotation speed of the magnet roll (3) was set to 100 rpm, and the developer used was one after stirring for 30 minutes.
この現像剤３９を精密天秤で計量し、導電性スリーブ（
２）表面全体に均一になるように乗せる。次にバイアス
電源（４）よりバイアス電圧を０〜ｌ０ＫＶ逐字印加し
、５秒間スリーブ（２）を回転させ、スリーブ（２）停
止時の電位Ｖ＋＋＋を読み取る。そのとき円筒電極（１
）に付着した分離トナー（７）の重量Ｍｉを精密天秤で
計量し、平均トナー帯電量を求める。この様にして求め
たトナーの質量の重量％を縦軸に、また帯電量Ｑ／Ｍを
対数として横軸にグラフ化したものを第４図に例示した
。第４図は、トナーｌについて測定したものである。This developer 39 is weighed with a precision balance, and the conductive sleeve (
2) Place it evenly over the entire surface. Next, a bias voltage of 0 to 10 KV is applied sequentially from the bias power supply (4), the sleeve (2) is rotated for 5 seconds, and the potential V+++ when the sleeve (2) is stopped is read. At that time, the cylindrical electrode (1
) The weight Mi of the separated toner (7) attached to the toner (7) is measured using a precision balance, and the average toner charge amount is determined. FIG. 4 shows a graph in which the weight % of the mass of the toner thus determined is plotted on the vertical axis, and the charge amount Q/M is plotted as a logarithm on the horizontal axis. FIG. 4 shows measurements made for toner l.
また、第４図において、横軸（Ｑ／Ｍ）の１０゜〜１０
！の範囲を２０等分した１目盛りを１チヤンネルとし、
このＱ／Ｍ１チャンネルにおける重量％が多いものから
順に３チヤンネルの累積重量％を求め表１Ｏおよび表１
１に示した。In addition, in Fig. 4, the horizontal axis (Q/M) is 10° to 10°.
! One channel is one scale that divides the range into 20 equal parts,
The cumulative weight % of the 3 channels was calculated in descending order of weight % in this Q/M1 channel and Table 1O and Table 1
Shown in 1.
表１０
表 １０ （続き）
表 １０ （続き）
耐印性テスト
前記ギヤ９フ１００重！部に対して下記のトナーを１０
重量部の割合で混合し２成分系現像剤を調製した。Table 10 Table 10 (Continued) Table 10 (Continued) Stamp resistance test Gear 9 gear 100 weight! 10 parts of the following toner
A two-component developer was prepared by mixing parts by weight.
上記の現像剤をＥＰ−４７０Ｚ又はＥＰ−５７０（ミノ
ルタカメラ社製）で耐刷テストを行い、初期および耐刷
時における帯電量及びカブリを測定しその結果を表２に
示した。 。The above developer was subjected to a printing durability test using EP-470Z or EP-570 (manufactured by Minolta Camera Co., Ltd.), and the amount of charge and fog at the initial stage and during printing were measured. The results are shown in Table 2. .
カブリについては、画像の評価よりランク付けを行った
。Regarding fog, ranking was performed based on image evaluation.
◎：地肌カブリがほとんどない乙の
Ｏ：地肌カブリが実用的に気にならないもの△：地肌カ
ブリが目立つもの
Ｘ：地肌カブリが極めてひどいもの
Ｉ 、Ｄ、の評価は、サクラ反射濃度計を用いて測定を
行った。なお、カラー画像に対しては、それぞれ適当な
カラーフィルターを通しての測定で評価を行った。◎: There is almost no background fogging O: The background fogging is not a practical concern △: The background fogging is noticeable X: The background fogging is extremely severe I and D were evaluated using a Sakura reflection densitometer. The measurements were carried out. Note that color images were evaluated by measurement through appropriate color filters.
なお、比較例１１を除いては、耐刷テスト途中画像のカ
ブリがひどくなったため、耐刷テストを中止した。Note that, except for Comparative Example 11, the printing durability test was discontinued because fogging of the image became severe during the printing durability test.
発明の効果
本発明のトナーは、帯電量の分布が狭く、かつ帯電量が
安定しているため、カブリおよびトナーの飛散が生じな
い。Effects of the Invention Since the toner of the present invention has a narrow charge amount distribution and a stable charge amount, fogging and toner scattering do not occur.
また、本発明においては、有色の荷電付与剤でもトナー
表面に必要量使用することにより、画像上かぶりもなく
さらに、カラー画像として鮮明で色の濁りもなかった。Further, in the present invention, by using the colored charge imparting agent in the required amount on the toner surface, there was no fogging on the image, and furthermore, the color image was clear and there was no color turbidity.
第１図および第２図は、吸光光度法で使用する検量線を
示す図である。
第３図は、本発明に係る帯電量分布測定装置の概略構成
を示す図である。
第４図は、帯電量分布の測定結果を例示する図である。
Ｉ・・・円筒電極 ２・・・導電性スリーブ３
・・・磁石ロール ４・・・バイアス電源５・・
・基準コンデンサー ６・・・現像剤７・・・分離トナ
ー
第３図FIGS. 1 and 2 are diagrams showing calibration curves used in the spectrophotometric method. FIG. 3 is a diagram showing a schematic configuration of a charge amount distribution measuring device according to the present invention. FIG. 4 is a diagram illustrating the measurement results of the charge amount distribution. I... Cylindrical electrode 2... Conductive sleeve 3
...Magnet roll 4...Bias power supply 5...
・Reference condenser 6...Developer 7...Separated toner Figure 3
Claims (1)
よりなる静電潜像現像用カラートナーにおいて、少なく
とも熱可塑性樹脂と着色剤よりなるトナー芯材と、該芯
材表面に固着した０．０３〜１ｗｔ％の荷電付与剤より
なることを特徴とする静電潜像現像用カラートナー。 ２、少なくとも熱可塑性樹脂、着色剤および荷電付与剤
よりなる静電潜像現像用カラートナーにおいて、少なく
とも含窒素極性官能基あるいは含弗素極性官能基を有す
る単量体成分を含有する樹脂および着色剤よりなるトナ
ー芯材と、該芯材表面に固着した０．００５〜１ｗｔ％
の荷電付与剤とからなることを特徴とする静電潜像現像
用カラートナー。[Scope of Claims] 1. A color toner for developing an electrostatic latent image comprising at least a thermoplastic resin, a coloring agent, and a charge imparting agent, a toner core comprising at least a thermoplastic resin and a coloring agent, and a toner core material comprising at least a thermoplastic resin and a coloring agent; A color toner for developing electrostatic latent images, characterized by comprising 0.03 to 1 wt% of a fixed charge imparting agent. 2. A color toner for developing electrostatic latent images comprising at least a thermoplastic resin, a colorant, and a charge imparting agent, a resin and a colorant containing a monomer component having at least a nitrogen-containing polar functional group or a fluorine-containing polar functional group. A toner core material consisting of 0.005 to 1 wt% fixed to the surface of the core material.
A color toner for developing an electrostatic latent image, comprising a charge imparting agent.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63005341A JPS64573A (en) | 1987-02-17 | 1988-01-12 | Electrostatic latent image developing color toner |
| US07/566,890 US5149611A (en) | 1987-02-17 | 1990-08-13 | Color toner for developing electrostatic latent image |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62-35189 | 1987-02-17 | ||
| JP62035189 | 1987-02-17 | ||
| JP63005341A JPS64573A (en) | 1987-02-17 | 1988-01-12 | Electrostatic latent image developing color toner |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01573A true JPH01573A (en) | 1989-01-05 |
| JPS64573A JPS64573A (en) | 1989-01-05 |
Family
ID=26339259
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63005341A Pending JPS64573A (en) | 1987-02-17 | 1988-01-12 | Electrostatic latent image developing color toner |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US5149611A (en) |
| JP (1) | JPS64573A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2623886B2 (en) * | 1990-01-26 | 1997-06-25 | 富士ゼロックス株式会社 | Electrophotographic toner and method for producing the same |
| DE69400108T2 (en) * | 1993-06-09 | 1996-10-02 | Agfa Gevaert Nv | POSITIVELY CHARGED TONER FOR ELECTROSTATOGRAPHY |
| JPH09319134A (en) * | 1996-05-29 | 1997-12-12 | Konica Corp | Static-charge-image development toner and multicolor image forming method |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3196032A (en) * | 1962-02-20 | 1965-07-20 | Burroughs Corp | Process for producing electrostatic ink powder |
| BE674776A (en) * | 1965-01-08 | 1966-05-03 | ||
| US3590000A (en) * | 1967-06-05 | 1971-06-29 | Xerox Corp | Solid developer for latent electrostatic images |
| GB1343698A (en) * | 1971-05-21 | 1974-01-16 | Agfa Gevaert | Development of electrostatic images |
| US4137188A (en) * | 1975-11-07 | 1979-01-30 | Shigeru Uetake | Magnetic toner for electrophotography |
| JPS5933908B2 (en) * | 1978-01-26 | 1984-08-18 | キヤノン株式会社 | Developer for electrostatic images |
| JPS5754953A (en) * | 1980-08-11 | 1982-04-01 | Xerox Corp | Method of producing toner composition |
| JPS5764250A (en) * | 1980-10-07 | 1982-04-19 | Hitachi Metals Ltd | Charge type magnetic toner |
| JPS5764249A (en) * | 1980-10-07 | 1982-04-19 | Hitachi Metals Ltd | Charge type magnetic toner |
| JPS57125943A (en) * | 1981-01-30 | 1982-08-05 | Canon Inc | Method for developing electrostatic latent image |
| JPS59174857A (en) * | 1983-03-24 | 1984-10-03 | Pilot Pen Co Ltd:The | Manufacture of pressure-fixable magnetic toner |
| JPS628169A (en) * | 1985-07-05 | 1987-01-16 | Fuji Photo Film Co Ltd | Production of toner for electrophotography |
| JPS62129866A (en) * | 1985-12-02 | 1987-06-12 | Konishiroku Photo Ind Co Ltd | Positively electrifiable developer for developing electrostatic image |
| JPS62159155A (en) * | 1985-12-30 | 1987-07-15 | Canon Inc | Developer for developing electrostatic charge image |
| JPS62212852A (en) * | 1986-03-14 | 1987-09-18 | Fujitsu Ltd | Storage protecting system |
| JPS63104064A (en) * | 1986-10-22 | 1988-05-09 | Sharp Corp | Toner for electrophotography |
| US4839255A (en) * | 1987-03-31 | 1989-06-13 | Canon Kabushiki Kaisha | Process for producing toner for developing electrostatic images |
-
1988
- 1988-01-12 JP JP63005341A patent/JPS64573A/en active Pending
-
1990
- 1990-08-13 US US07/566,890 patent/US5149611A/en not_active Expired - Lifetime
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