JPH04170557A - Developer - Google Patents
DeveloperInfo
- Publication number
- JPH04170557A JPH04170557A JP2295418A JP29541890A JPH04170557A JP H04170557 A JPH04170557 A JP H04170557A JP 2295418 A JP2295418 A JP 2295418A JP 29541890 A JP29541890 A JP 29541890A JP H04170557 A JPH04170557 A JP H04170557A
- Authority
- JP
- Japan
- Prior art keywords
- developer
- toner
- group
- monoazo dye
- weight
- 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.)
- Granted
Links
- 229920005989 resin Polymers 0.000 claims abstract description 67
- 239000011347 resin Substances 0.000 claims abstract description 67
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 claims abstract description 61
- 239000002253 acid Substances 0.000 claims abstract description 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 27
- 150000004696 coordination complex Chemical class 0.000 claims abstract description 25
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 20
- 239000003086 colorant Substances 0.000 claims abstract description 10
- 239000011230 binding agent Substances 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 230000005291 magnetic effect Effects 0.000 claims description 5
- 239000000696 magnetic material Substances 0.000 claims description 5
- 239000003446 ligand Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical group NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- 230000007613 environmental effect Effects 0.000 abstract description 18
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract description 3
- 150000004700 cobalt complex Chemical class 0.000 abstract description 3
- 150000004698 iron complex Chemical class 0.000 abstract description 3
- 230000002542 deteriorative effect Effects 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 57
- 239000000843 powder Substances 0.000 description 47
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 42
- 238000000034 method Methods 0.000 description 30
- -1 acrylic ester Chemical class 0.000 description 27
- 229910052751 metal Inorganic materials 0.000 description 21
- 239000002184 metal Substances 0.000 description 21
- 239000000203 mixture Substances 0.000 description 21
- 239000000377 silicon dioxide Substances 0.000 description 21
- 150000008064 anhydrides Chemical class 0.000 description 17
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 16
- 239000000987 azo dye Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- 239000002245 particle Substances 0.000 description 15
- 230000007423 decrease Effects 0.000 description 11
- 239000000178 monomer Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 229920006163 vinyl copolymer Polymers 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 8
- 125000004386 diacrylate group Chemical group 0.000 description 8
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 8
- VEALVRVVWBQVSL-UHFFFAOYSA-N strontium titanate Chemical compound [Sr+2].[O-][Ti]([O-])=O VEALVRVVWBQVSL-UHFFFAOYSA-N 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 229920002554 vinyl polymer Polymers 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 238000012662 bulk polymerization Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 238000010557 suspension polymerization reaction Methods 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 3
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229920002545 silicone oil Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229910000859 α-Fe Inorganic materials 0.000 description 3
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-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
- 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
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000010556 emulsion polymerization method Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- 235000013980 iron oxide Nutrition 0.000 description 2
- 230000005415 magnetization Effects 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 239000000434 metal complex dye Substances 0.000 description 2
- 229920003146 methacrylic ester copolymer Polymers 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000006902 nitrogenation reaction Methods 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 238000010558 suspension polymerization method Methods 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- CGBYBGVMDAPUIH-ONEGZZNKSA-N (e)-2,3-dimethylbut-2-enedioic acid Chemical compound OC(=O)C(/C)=C(\C)C(O)=O CGBYBGVMDAPUIH-ONEGZZNKSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 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
- BJQFWAQRPATHTR-UHFFFAOYSA-N 1,2-dichloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1Cl BJQFWAQRPATHTR-UHFFFAOYSA-N 0.000 description 1
- YQJPWWLJDNCSCN-UHFFFAOYSA-N 1,3-diphenyltetramethyldisiloxane Chemical compound C=1C=CC=CC=1[Si](C)(C)O[Si](C)(C)C1=CC=CC=C1 YQJPWWLJDNCSCN-UHFFFAOYSA-N 0.000 description 1
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QOVCUELHTLHMEN-UHFFFAOYSA-N 1-butyl-4-ethenylbenzene Chemical compound CCCCC1=CC=C(C=C)C=C1 QOVCUELHTLHMEN-UHFFFAOYSA-N 0.000 description 1
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-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
- WJNKJKGZKFOLOJ-UHFFFAOYSA-N 1-dodecyl-4-ethenylbenzene Chemical compound CCCCCCCCCCCCC1=CC=C(C=C)C=C1 WJNKJKGZKFOLOJ-UHFFFAOYSA-N 0.000 description 1
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
- OEVVKKAVYQFQNV-UHFFFAOYSA-N 1-ethenyl-2,4-dimethylbenzene Chemical compound CC1=CC=C(C=C)C(C)=C1 OEVVKKAVYQFQNV-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- WHFHDVDXYKOSKI-UHFFFAOYSA-N 1-ethenyl-4-ethylbenzene Chemical compound CCC1=CC=C(C=C)C=C1 WHFHDVDXYKOSKI-UHFFFAOYSA-N 0.000 description 1
- LCNAQVGAHQVWIN-UHFFFAOYSA-N 1-ethenyl-4-hexylbenzene Chemical compound CCCCCCC1=CC=C(C=C)C=C1 LCNAQVGAHQVWIN-UHFFFAOYSA-N 0.000 description 1
- LUWBJDCKJAZYKZ-UHFFFAOYSA-N 1-ethenyl-4-nonylbenzene Chemical compound CCCCCCCCCC1=CC=C(C=C)C=C1 LUWBJDCKJAZYKZ-UHFFFAOYSA-N 0.000 description 1
- HLRQDIVVLOCZPH-UHFFFAOYSA-N 1-ethenyl-4-octylbenzene Chemical compound CCCCCCCCC1=CC=C(C=C)C=C1 HLRQDIVVLOCZPH-UHFFFAOYSA-N 0.000 description 1
- RCSKFKICHQAKEZ-UHFFFAOYSA-N 1-ethenylindole Chemical compound C1=CC=C2N(C=C)C=CC2=C1 RCSKFKICHQAKEZ-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical class C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- SXAMGRAIZSSWIH-UHFFFAOYSA-N 2-[3-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,2,4-oxadiazol-5-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NOC(=N1)CC(=O)N1CC2=C(CC1)NN=N2 SXAMGRAIZSSWIH-UHFFFAOYSA-N 0.000 description 1
- WHBAYNMEIXUTJV-UHFFFAOYSA-N 2-chloroethyl prop-2-enoate Chemical compound ClCCOC(=O)C=C WHBAYNMEIXUTJV-UHFFFAOYSA-N 0.000 description 1
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- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 1
- FQMIAEWUVYWVNB-UHFFFAOYSA-N 3-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OC(C)CCOC(=O)C=C FQMIAEWUVYWVNB-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
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- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- MPVDXIMFBOLMNW-ISLYRVAYSA-N 7-hydroxy-8-[(E)-phenyldiazenyl]naphthalene-1,3-disulfonic acid Chemical compound OC1=CC=C2C=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C1\N=N\C1=CC=CC=C1 MPVDXIMFBOLMNW-ISLYRVAYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
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- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
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- 239000003208 petroleum Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 229930187593 rose bengal Natural products 0.000 description 1
- 229940081623 rose bengal Drugs 0.000 description 1
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 description 1
- VDNLFJGJEQUWRB-UHFFFAOYSA-N rose bengal free acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C(O)=C(I)C=C21 VDNLFJGJEQUWRB-UHFFFAOYSA-N 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- CAPIMQICDAJXSB-UHFFFAOYSA-N trichloro(1-chloroethyl)silane Chemical compound CC(Cl)[Si](Cl)(Cl)Cl CAPIMQICDAJXSB-UHFFFAOYSA-N 0.000 description 1
- FLPXNJHYVOVLSD-UHFFFAOYSA-N trichloro(2-chloroethyl)silane Chemical compound ClCC[Si](Cl)(Cl)Cl FLPXNJHYVOVLSD-UHFFFAOYSA-N 0.000 description 1
- KHOQXNHADJBILQ-UHFFFAOYSA-N trimethyl(sulfanyl)silane Chemical compound C[Si](C)(C)S KHOQXNHADJBILQ-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- GRPURDFRFHUDSP-UHFFFAOYSA-N tris(prop-2-enyl) benzene-1,2,4-tricarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C(C(=O)OCC=C)=C1 GRPURDFRFHUDSP-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XOSXWYQMOYSSKB-LDKJGXKFSA-L water blue Chemical compound CC1=CC(/C(\C(C=C2)=CC=C2NC(C=C2)=CC=C2S([O-])(=O)=O)=C(\C=C2)/C=C/C\2=N\C(C=C2)=CC=C2S([O-])(=O)=O)=CC(S(O)(=O)=O)=C1N.[Na+].[Na+] XOSXWYQMOYSSKB-LDKJGXKFSA-L 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Developing Agents For Electrophotography (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、電子写真法、静電記録法、静電印刷法に用い
られる静電荷像現像用トナーに関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a toner for developing electrostatic images used in electrophotography, electrostatic recording, and electrostatic printing.
［従来の技術］
従来、電子写真法としては米国特許第
２．２９７，６９１号明細書、特公昭４２−２３９１０
号公報及び特公昭４３−２４７４８号公報等に記載され
ている如く多数の方法が知られているが、一般には光導
電性物質を利用し、種々の手段により感光体上に電気的
潜像を形成し、次いで該潜像をトナーを用いて現像し、
必要に応じて紙等の転写材にトナー画像を転写した後、
加熱、圧力或いは溶剤蒸気などにより定着し複写物を得
るものである。[Prior Art] Conventionally, as an electrophotographic method, US Pat.
A number of methods are known, such as those described in Japanese Patent Publication No. 43-24748, etc., but in general, a photoconductive substance is used to form an electrical latent image on a photoreceptor by various means. forming a latent image, and then developing the latent image using toner;
After transferring the toner image to a transfer material such as paper as necessary,
Copies are obtained by fixing by heat, pressure, solvent vapor, etc.
上述の最終工程であるトナー像を紙などのシートに定着
する工程に関して種々の方法や装置が開発されているが
、現在量も一般的な方法は熱ローラーによる圧着加熱方
式である。Various methods and apparatuses have been developed for the above-mentioned final step of fixing the toner image on a sheet such as paper, but the most common method at present is a compression heating method using a heated roller.
加熱ローラーによる圧着加熱方式はトナーに対し離型性
を有する表面を形成した熱ローラーの表面に被定着シー
トのトナー像面を加圧下で接触しながら通過せしめるこ
とにより定着を行なうものである。この方法は加熱ロー
ラー表面と被定着シートのトナー像とが加圧下で接触す
るため、トナー像を被定着シート上に融着する際の熱効
率が極めて良好であり、迅速に定着を行なうことができ
、高速度電子写真複写機において非常に有効である。In the press-heating method using a heated roller, fixing is carried out by passing the toner image surface of the fixing sheet while contacting it under pressure with the surface of a heated roller, which has a surface that has releasability for the toner. In this method, the surface of the heating roller and the toner image on the sheet to be fixed come into contact under pressure, so the thermal efficiency when fusing the toner image onto the sheet to be fixed is extremely good, and the fixing can be carried out quickly. , which is very effective in high-speed electrophotographic copying machines.
このような定着方法において、定着性を向上させるため
に酸成分を含有する結着樹脂の使用が特開昭５５−１３
４８６１号公報で提案されている。しかしながら、この
様な結着樹脂を用いたトナーは、高湿下での帯電不足、
低湿下での帯電過剰を生じ易いなど環境変動の影響を受
は易い。In such a fixing method, the use of a binder resin containing an acid component in order to improve fixing properties was disclosed in Japanese Patent Application Laid-open No. 55-13.
This is proposed in Publication No. 4861. However, toners using such binder resins suffer from insufficient charging under high humidity.
It is easily affected by environmental changes, such as excessive charging in low humidity environments.
又、カブリ、画像濃度など十分な現像性が得られないこ
ともある。Further, sufficient developability such as fog and image density may not be obtained.
このように定着性、耐オフセット性を向上させるために
、トナー結着樹脂中に酸成分或いは酸無水物成分を樹脂
構成成分として含有せしめることが行われている。しか
し、そのような結着樹脂を用いた場合には、高湿下にお
ける吸着水分量が増加するために帯電量低下を引き起こ
し、濃度低下を引き起こし、更に低湿下においては、負
帯電性が過剰になり過ぎるために、カブリや濃度低下を
生じることがある。このように、トナーの定着性能、耐
オフセツト性能を満足するとともに、トナーの帯電性能
においても十分な性能を与えることが求められている。In order to improve the fixing properties and anti-offset properties as described above, an acid component or an acid anhydride component is incorporated into the toner binder resin as a resin component. However, when such a binder resin is used, the amount of adsorbed water increases under high humidity, causing a decrease in the amount of charge and concentration, and furthermore, under low humidity, the negative chargeability becomes excessive. This may cause fogging or a decrease in density. As described above, it is required to satisfy toner fixing performance and offset resistance performance, and to provide sufficient toner charging performance.
帯電特性を制御するために、トナー中に電荷制御剤を主
にＩＦ電付与を目的として添加することが広く行われて
いる。電荷制御剤を添加されたトナーにおける帯電特性
は、結着樹脂の種類と電荷制御剤の種類の組み合わせに
より異なる。このような電荷制御剤の中で、モノアゾ染
料の金属錯体を用いることが知られている。In order to control charging characteristics, it is widely practiced to add a charge control agent to a toner mainly for the purpose of imparting IF charge. The charging characteristics of a toner to which a charge control agent has been added differ depending on the combination of the type of binder resin and the type of charge control agent. Among such charge control agents, it is known to use metal complexes of monoazo dyes.
このようなモノアゾ染料の金属錯体を含有せしめたトナ
ーは優れた帯電特性を有するが、スリーブ等のトナー担
持体に付着し易く、複写を続けるとトナー担持体を汚染
し、画像濃度の低下を引き起こすという大きな難点を持
っている。又、そのままではトナーの流動性が低く、画
質の低下を招く。Toners containing such metal complexes of monoazo dyes have excellent charging properties, but they tend to adhere to toner carriers such as sleeves, and if they continue to be copied, they contaminate the toner carriers and cause a decrease in image density. It has a big drawback. Further, if left as is, the fluidity of the toner will be low, leading to deterioration in image quality.
これらを改善、解消し、優れた現像剤とするにはシリカ
、アルミナ、酸化チタン等の流動性向上剤を添加しなけ
ればならない。しかし、流動性向上剤はそれ自身が帯電
性を有するとともに、現像剤中に含有せしめた場合に、
現像剤の摩擦帯電特性を大きく変化させる作用がある。In order to improve or eliminate these problems and make an excellent developer, fluidity improvers such as silica, alumina, and titanium oxide must be added. However, the fluidity improver itself has charging properties, and when included in the developer,
It has the effect of greatly changing the triboelectric charging characteristics of the developer.
これらの流動性向上剤のうち、あるものは低温低湿下で
の摩擦帯電量を過剰にする傾向を有し、又あるものは高
温高湿下での摩擦帯電量を低下し過ぎる傾向を有する。Among these fluidity improvers, some tend to excessively increase the amount of triboelectric charge under low temperature and low humidity conditions, while others tend to reduce the amount of triboelectric charge too much under high temperature and high humidity conditions.
又、摩擦帯電量の環境依存性が比較的小さいものは流動
性付与、トナーへの付着性の面で劣ることが少なくない
。Furthermore, those whose triboelectric charge amount has relatively low environmental dependence are often inferior in terms of fluidity imparting and adhesion to toner.
又、トナーの帯電量と流動性向上剤などの添加剤を加え
た後の現像剤の帯電量は、多くの場合同一ではなく、又
ある条件下で同じであっても環境条件、構成比等で変わ
ってしまう。そのため現像剤を使用中にトナーと流動性
向上剤が剥離し、その構成比が変化するとｆｉｔ量変化
、画像濃度変化が生じてしまう。そこで流動性向上剤に
はトナーから剥離しにくいこと、構成比が変化しないこ
とが望まれている。Furthermore, the amount of charge on the toner and the amount of charge on the developer after adding additives such as fluidity improvers are often not the same, and even if they are the same under certain conditions, environmental conditions, composition ratios, etc. It will change. Therefore, when the toner and the fluidity improver are separated during use of the developer and their composition ratio changes, a change in fit amount and a change in image density occur. Therefore, it is desired that the fluidity improver is difficult to peel off from the toner and that the composition ratio does not change.
このように現在のところ、現像剤の湿度依存性を少なく
し、且つ高い流動性を付与し、構成比の安定な優れた流
動性向上剤、或いはそれを実現する手段、方法が求めら
れている。As such, there is currently a need for an excellent fluidity improver that reduces the humidity dependence of the developer, provides high fluidity, and has a stable composition ratio, or a means or method to achieve this. .
［発明が解決しようとする課題］
本発明の目的は、上述の如き問題点を解決した静電荷像
現像用現像剤を提供するものである。[Problems to be Solved by the Invention] An object of the present invention is to provide a developer for developing electrostatic images that solves the above-mentioned problems.
即ち、本発明の目的は、定着性を損なうことなくカブリ
がなく高濃度の画像が得られる静電荷像現像用現像剤を
提供するものである。That is, an object of the present invention is to provide a developer for developing electrostatic images, which can provide fog-free and high-density images without impairing fixing properties.
更に本発明の他の目的は、環境変動に影響されることも
なく、低湿下及び高湿下においても良好な画像を与える
静電荷像現像用現像剤を提供するものである。Still another object of the present invention is to provide a developer for developing electrostatic images that is not affected by environmental changes and provides good images even under low humidity and high humidity conditions.
更に発明−明の他の目的は、高速機においても安定して
良好な画像を与え、適用機種を選ばない静電荷像現像用
現像剤を提供するものである。Another object of the invention is to provide a developer for developing electrostatic images that can stably produce good images even in high-speed machines and can be applied to any type of machine.
［課題を解決するための手段及び作用コ本発明は、少な
くとも、結着樹脂、着色剤、電荷制御剤、流動性向上剤
を含有する静電荷像現像用現像剤において、
結着樹脂の酸価が１００ｍｇＫＯＨ／ｇ以下であり、少
なくともモノアゾ染料の金属錯体を含有し、かつ、ヒド
ロキシ基を２基以上有するモノアゾ染料を含有すること
を特徴とする現像剤に関する。[Means and Effects for Solving the Problems] The present invention provides a developer for developing electrostatic images containing at least a binder resin, a colorant, a charge control agent, and a fluidity improver. 100 mgKOH/g or less, contains at least a metal complex of a monoazo dye, and contains a monoazo dye having two or more hydroxy groups.
更に本発明に関して詳しく説明する。Further, the present invention will be explained in detail.
本発明の現像剤においては、定着性、耐オフセット性、
ブロッキング性を向上するために、結着樹脂中に酸成分
を含有している。従来はこのように結着樹脂中に酸成分
を含有せしめると帯電量の環境依存性が悪化し、低湿下
での帯電量過剰、高湿下での帯電量不足を引き起こす傾
向があった。そこで本発明者らは、十分な定着性能を保
持しつつ帯電量の環境依存性を安定化し、鮮明な画像を
得るために鋭意検討した結果、少なくともトナー中にモ
ノアゾ染料の金属錯体を含有し、かつ、現像剤中にヒド
ロキシ基を２基以上有するモノアゾ染料を含有せしめる
ことによって帯電量の環境依存性が良好化し、低湿下で
の帯電量過剰、高湿下での帯電量不足を抑制するととも
に、良好な画像が安定して得られることを見いだした。The developer of the present invention has fixing properties, offset resistance,
An acid component is contained in the binder resin to improve blocking properties. Conventionally, when an acid component is included in a binder resin in this manner, the environmental dependence of the charge amount tends to deteriorate, resulting in an excessive charge amount under low humidity and an insufficient charge amount under high humidity. The inventors of the present invention have conducted intensive studies to stabilize the environmental dependence of the charge amount while maintaining sufficient fixing performance and to obtain clear images. In addition, by containing a monoazo dye having two or more hydroxyl groups in the developer, the environmental dependence of the charge amount is improved, suppressing excessive charge amount under low humidity and insufficient charge amount under high humidity. It has been found that good images can be stably obtained.
本発明における結着樹脂中の酸成分或いは酸無水物成分
に由来する酸価は、高温高湿下における吸水性を抑え、
現像剤の流動性を得、トナーの良好な帯電特性を得るた
め１００ｍｇＫＯＨ／ｇ以下である。酸価が１００ｍｇ
ＫＯＨ／ｇを越えると、高温高湿下において現像剤の流
動性が低下し、得られる複写画像はがさついたものにな
る。The acid value derived from the acid component or acid anhydride component in the binder resin in the present invention suppresses water absorption under high temperature and high humidity,
The amount is 100 mgKOH/g or less in order to obtain fluidity of the developer and good charging characteristics of the toner. Acid value is 100mg
When KOH/g is exceeded, the fluidity of the developer decreases under high temperature and high humidity conditions, and the resulting copied image becomes rough.
又帯電量の環境依存性が大きくなり、低湿下での帯電量
過剰による画像濃度の低下現象が発生する。Furthermore, the dependence of the amount of charge on the environment increases, and a phenomenon in which the image density decreases due to the excessive amount of charge occurs under low humidity conditions.
本発明における結着樹脂としては、少なくともビニル系
重合体を含有する結着樹脂が好ましい。As the binder resin in the present invention, a binder resin containing at least a vinyl polymer is preferable.
特にスチレン、アクリルエステル類を構成成分として含
有する樹脂がより好ましい。In particular, resins containing styrene and acrylic esters as constituent components are more preferred.
結着樹脂成分がスチレン或いはアクリルエステルを主構
成成分としている樹脂においては、結着樹脂中の酸成分
或いは酸無水物成分に由来する全＃！価は、２ ｍ ｇ
Ｋ ＯＨ／ ｇ以上、７０ｍｇＫＯＨ／ｇ以下が好ま
しい、１１価が２ｍｇＫＯＨ／ｇ未満の場合には結着樹
脂の臨界表面張力が低下し、定着ローラーとの親和性が
増加するためにトナーと定着ローラーとが離型し難くな
り、オフセットを発生し易くなる。又、７０ｍｇＫＯＨ
／ｇを越える場合には、高温高湿下で耐久性能がやや劣
り、画像濃度の低下を引き起こすことがある。In a resin in which the binder resin component is mainly composed of styrene or acrylic ester, all #! The value is 2 mg
KOH/g or more and 70mgKOH/g or less are preferable. If the 11 value is less than 2mgKOH/g, the critical surface tension of the binder resin decreases and the affinity with the fixing roller increases, so that the toner and the fixing roller It becomes difficult to release from the mold, and offset tends to occur. Also, 70mgKOH
If it exceeds /g, the durability performance under high temperature and high humidity may be slightly inferior, leading to a decrease in image density.
本発明に招ける必須の構成要素として、モノアゾ染料の
金属錯体を含有することが挙げられる。An essential component of the present invention is the inclusion of a metal complex of a monoazo dye.
酸価を有する樹脂を用いたトナーと鉄などの金属或いは
酸化鉄などの金属酸化物との摩擦帯電では、酸価を有す
る樹脂を用いたトナーは高い帯電量を有するとともに、
環境依存性も激しく、更に帯電量の立ち上がりが遅く飽
和摩擦帯電量に達するまでの時間が長い、しかし、酸価
を有する樹脂を用いたトナー中にモノアゾ染料の金属錯
体を含有せしめた場合には、これらを含有しない場合よ
り摩擦帯電量が低くなるとともに、トナー帯電量の環境
依存性も良好化し、ｆ電量の立ち上がりも早くなり、す
ぐに飽和摩擦帯電量に達する。又、負摩擦帯電量が低く
なることから、電荷制御剤として正：ｌＩＦ′ＷＬ性の
高いものを選べば、定着性能が優れた正ｆ電性トナーが
得られる。In frictional charging between a toner using a resin having an acid value and a metal such as iron or a metal oxide such as iron oxide, the toner using a resin having an acid value has a high charge amount, and
It is also highly dependent on the environment, and furthermore, the charge build-up is slow and it takes a long time to reach the saturated triboelectric charge.However, when a metal complex of a monoazo dye is contained in a toner using a resin with an acid value, , the amount of triboelectric charge is lower than when these are not contained, the environmental dependence of the toner charge amount is also improved, and the amount of f charge increases quickly, reaching the saturation triboelectricity amount quickly. In addition, since the amount of negative triboelectric charge is low, if a charge control agent with high positive:lIF'WL property is selected, a positive f-electrification toner with excellent fixing performance can be obtained.
本発明のモノアゾ染料の金属錯体は、下記一般式（Ｉ）
に示す構造の錯体がトナー中への分散性を考慮すると好
ましい。The metal complex of the monoazo dye of the present invention has the following general formula (I).
A complex having the structure shown below is preferable in consideration of dispersibility in the toner.
現像剤中におけるこのようなモノアゾ染料のクロム錯体
、鉄錯体或いはコバルト錯体の含有量は、結着樹脂の構
成成分、酸価、分子量等によって決定されるもので一義
的に限定されないが、結着樹脂１００重量部に対して０
．０１〜６重量部である。０．０１重量部未満であると
本発明の効果をほとんど示さず、６重量部を越えると錯
体の分散性が悪（、得られる画像にカブリを生じる。The content of the chromium complex, iron complex, or cobalt complex of the monoazo dye in the developer is determined by the constituent components, acid value, molecular weight, etc. of the binder resin, and is not specifically limited; 0 per 100 parts by weight of resin
．． 01 to 6 parts by weight. If it is less than 0.01 part by weight, the effect of the present invention will hardly be exhibited, and if it exceeds 6 parts by weight, the dispersibility of the complex will be poor (and the resulting image will be foggy).
より好ましくは、４重量部以下である。４重量部を越え
るとトナー担持体への付着量が多くなり、多量の複写を
行った場合に画像濃度の低下を引き起こす。More preferably, it is 4 parts by weight or less. If the amount exceeds 4 parts by weight, the amount of toner adhering to the toner carrier increases, causing a decrease in image density when a large amount of copying is performed.
本発明必須の構成要素は、ヒドロキシ基を２基以上有す
るモノアゾ染料を含有することである。An essential component of the present invention is that it contains a monoazo dye having two or more hydroxy groups.
アゾ染料を着色剤として、二成分現像剤におけるトナー
中に含有せしめることは、良く知られている。しかし、
着色剤として用いられるアゾ染料は、金属塩化されてい
るものが多く、それらは吸水性も高く、本発明のアゾ染
料とは、目的、効果、構成を全く異にする。又、特開昭
６３−７３２７０号公報には、電荷付与を目的としてア
ゾ染料をトナー組成物として含有せしめることが提案さ
れている。しかしそこに示されたアゾ染料の構造は本発
明のものとは異なり、本発明に示される効果を示さず、
本発明とは別個のものである。It is well known that an azo dye is contained as a colorant in a toner in a two-component developer. but,
Azo dyes used as coloring agents are often metal chlorinated, have high water absorption, and are completely different in purpose, effect, and structure from the azo dyes of the present invention. Furthermore, Japanese Patent Application Laid-Open No. 63-73270 proposes that a toner composition contain an azo dye for the purpose of imparting electric charge. However, the structure of the azo dye shown therein is different from that of the present invention, and does not exhibit the effects shown in the present invention.
It is separate from the present invention.
本発明者らは、複写における画像濃度の安定性を得るこ
とを目的として、トナーと流動性向上剤（７） 組成比
（７） −走化について鋭意検討したところによると、
アゾ染料がカルボン酸金属塩基或いはスルホン酸金属塩
基を有する場合には、染料の吸水性が高く、得られる現
像剤の摩擦帯電量及び複写画像濃度の環境依存性が大き
いため、実用上問題がある。そこで、アゾ染料における
極性基をほとんどなくすと、トナーと流動性向上剤が遊
離し、それらの組成比が一定化せず、目的を達成しない
。しかし、アゾ染料が二基以上のヒドロキシ基を有する
場合には、摩擦？電量及び画像濃度の環境依存性は少な
く、又トナーと流動性向上剤の組成比が安定化する。又
少なくとも二つのヒドロキシ基は、アゾ染料における二
つの芳香環上に少なくとも一つずつあるほうが流動性向
上剤との親和性の面から好ましい。The present inventors have conducted intensive studies on toner and fluidity improver (7) composition ratio (7) - chemotaxis for the purpose of obtaining stability of image density in copying.
When the azo dye has a metal carboxylate base or a metal sulfonate base, there is a practical problem because the dye has high water absorption and the triboelectric charge amount of the resulting developer and the density of the copied image are highly dependent on the environment. . Therefore, if most of the polar groups in the azo dye are eliminated, the toner and fluidity improver will be liberated, their composition ratio will not be constant, and the objective will not be achieved. However, if the azo dye has two or more hydroxy groups, friction? The amount of electricity and image density are less dependent on the environment, and the composition ratio of the toner and fluidity improver is stabilized. Further, it is preferable that at least two hydroxy groups exist on each of the two aromatic rings in the azo dye from the viewpoint of affinity with the fluidity improver.
さらに、本発明のヒドロキシ基を２基以上有するモノア
ゾ染料は、画像濃度の安定性を考慮すると下記一般式（
ＩＩ）で表される化合物であることがより好ましい。Furthermore, the monoazo dye having two or more hydroxy groups of the present invention has the following general formula (
A compound represented by II) is more preferred.
このモノアゾ染料を現像剤中に含有せしめることで、モ
ノアゾ染料の金属錯体だけをトナー中に含有せしめた場
合より、現像剤の帯電量の環境依存性が安定化するとと
もに、トナーと流動性向上剤の構成比が変化しにくくな
ったために、複写中における現像剤の帯電量が安定し、
高温低湿にかかわらず、高い濃度の画像が安定に得られ
る。これはヒドロキシ基を２基以上有するモノアゾ染料
のために、流動性向上剤がトナー表面から剥離しにくく
なったためである。By incorporating this monoazo dye into the developer, the environmental dependence of the amount of charge on the developer becomes more stable than when only the metal complex of the monoazo dye is included in the toner, and the toner and fluidity improver Because the composition ratio of the developer is less likely to change, the amount of charge of the developer becomes stable during copying,
High density images can be stably obtained regardless of high temperature and low humidity. This is because the fluidity improver becomes difficult to peel off from the toner surface due to the monoazo dye having two or more hydroxy groups.
又、本発明のモノアゾ染料は、トナー中にモノアゾ染料
の金属錯体を含有しない場合にはその効果を発揮しない
。Further, the monoazo dye of the present invention does not exhibit its effect if the toner does not contain a metal complex of the monoazo dye.
本発明のヒドロキシ基を２基以上有するモノアゾ染料は
、モノアゾ染料の金属錯体における配位子と同一の化合
物がより好ましい。異なると低温低湿下においてカブリ
を生じ易くなる。The monoazo dye having two or more hydroxy groups of the present invention is more preferably the same compound as the ligand in the metal complex of the monoazo dye. If they are different, fogging is likely to occur at low temperatures and low humidity.
本発明における現像剤中のヒドロキシ基を２基以上有す
るモノアゾ染料の含有量は、トナー中にアゾ染料を添加
する方法、結着樹脂の構成成分、酸価、分子量、モノア
ゾ染料の金属錯体の含有量、含有される電荷制御剤の種
類と含有量等により決定されるもので、一義的には限定
することはできないが、結着樹脂１００重量部に対し、
ｏ、ｏｏｔ重量部以上５重量部以下が好ましい。The content of the monoazo dye having two or more hydroxyl groups in the developer in the present invention is determined by the method of adding the azo dye into the toner, the constituent components of the binder resin, the acid value, the molecular weight, and the content of the metal complex of the monoazo dye. It is determined by the amount, type and content of the charge control agent contained, etc., and cannot be uniquely limited, but for 100 parts by weight of the binder resin,
o, oot is preferably from 5 parts by weight to 5 parts by weight.
０．００１重量部未満であると本発明の効果が現れにく
い。又５重量部を越えると、現像剤の吸水性が増加し、
高湿下で画像濃度の低下を引き起こすとともに、モノア
ゾ染料がトナー中の他の材料の均一分散を阻害し、画像
上にカブリを生じる。If the amount is less than 0.001 part by weight, the effects of the present invention will be difficult to achieve. Moreover, if it exceeds 5 parts by weight, the water absorption of the developer increases,
In addition to causing a decrease in image density under high humidity conditions, the monoazo dye inhibits uniform dispersion of other materials in the toner, causing fog on the image.
より好ましくは、０．００５重量部以上、３重量部以下
である。ｏ、ｏｏｓ重量部未満であると均一分散が難し
くカブリを生じ易い、３重量部を越えると多量に複写し
た場合に、モノアゾ染料の一部が現像剤の担持体に付着
し、画像濃度の低下を引き起こし易い。More preferably, it is 0.005 parts by weight or more and 3 parts by weight or less. If the amount is less than o, oos parts by weight, uniform dispersion will be difficult and fog will easily occur; if it exceeds 3 parts by weight, when a large amount is copied, a portion of the monoazo dye will adhere to the developer carrier, resulting in a decrease in image density. easy to cause.
本発明においては、ヒドロキシ基を２基以上有するモノ
アゾ染料が、トナー中における存在量にかかわらず、複
写機内現像容器中のトナーにおいてトナー表面上に存在
することが実買上重要である。つまり、複写機内にある
程度放置されたトナーにおいて、トナー表面上に存在す
るモノアゾ染料の金属錯体を基準（１００重量％）した
時、トナー表面上のヒドロキシ基を２基以上有するアゾ
染料が、０．１重量％以上存在することが好ましく、５
重量％以上がより好ましい、また、他に本発明における
錯体の中心金属と同じ金属を有する錯体又は塩等を電荷
制御剤として含有している場合には、それらとモノアゾ
染料の金属錯体のトナー表面上に存在する重量の０．１
重量％以上存在することが好ましく、５重量％以上存在
することがより好ましい。ヒドロキシ基を２基以上有す
るモノアゾ染料が５重量％未満であると、複写機の現像
器内で長い間現像剤が消費されない状況でトナー担持体
との摺擦を繰り返した場合、表面上のアゾ染料が除かれ
、本発明の効果を現さなくなることがある。より好まし
くは、１０重量％以上である０本発明のモノアゾ染料が
１０重量％未満だと、多量に複写中、トナーと流動性向
上剤との構成比がやや変化する傾向がある。In the present invention, it is important for actual purchase that the monoazo dye having two or more hydroxy groups exists on the surface of the toner in the developer container in the copying machine, regardless of the amount present in the toner. In other words, in a toner that has been left in a copying machine for some time, when based on the metal complex of the monoazo dye present on the toner surface (100% by weight), the azo dye having two or more hydroxyl groups on the toner surface is 0. Preferably, the content is 1% by weight or more, and 5% by weight or more.
It is more preferable that the amount is % by weight or more, and when the charge control agent contains a complex or salt having the same metal as the central metal of the complex in the present invention, the toner surface of the metal complex of the monoazo dye with them is more preferable. 0.1 of the weight present on
It is preferably present in an amount of 5% by weight or more, more preferably 5% by weight or more. If the monoazo dye having two or more hydroxyl groups is less than 5% by weight, the azo dye on the surface may be repeatedly rubbed against the toner carrier in a situation where the developer is not consumed for a long time in the developing device of a copying machine. The dye may be removed and the effect of the present invention may no longer be exhibited. More preferably, it is 10% by weight or more. If the monoazo dye of the present invention is less than 10% by weight, the composition ratio of the toner and the fluidity improver tends to change slightly during copying in large quantities.
ここで百う「複写機内にある程度放置されたトナーにお
いて、トナー表面上に存在するモノアゾ染料の金属錯体
を基準にしたとき、ヒドロキシ基を２基以上有するモノ
アゾ染料が５重量％以上存在するノ状態とは、次のよう
な実験を行ったときの分析値、実験値とする。Here, ``in a toner that has been left in a copying machine for some time, a state in which 5% by weight or more of a monoazo dye having two or more hydroxyl groups is present, based on the metal complex of the monoazo dye present on the toner surface.'' is the analytical value or experimental value obtained when the following experiment is conducted.
１リツトルのポリプロピレン製カップに現像剤１００ｇ
を入れ、温度５０℃で１週間放置する。100g of developer in a 1 liter polypropylene cup
and leave it for one week at a temperature of 50°C.
その後、この現像剤１０ｇに対し、エタノール１０ｇを
加え、３０秒秒間上うした後、濾過し、濾液に金属錯体
、アゾ染料を収集する。表面上の金属錯体、アゾ染料の
存在比は、このとき収集された重量比とする。収集され
た化合物を好ましくはカラムクロマトにより樹脂成分と
分離し、更に液体クロマトグラフィーで分離、分析して
両者の比率を求める。定量は、検量線法によるのが好ま
しい。この分析値を換算した結果、モノアゾ染料の金属
錯体を基準にしたとき、ヒドロキシ基を２基以上有する
モノアゾ染料が５重量％以上であることである。Thereafter, 10 g of ethanol is added to 10 g of this developer, and the mixture is stirred for 30 seconds and then filtered to collect the metal complex and azo dye in the filtrate. The abundance ratio of the metal complex and azo dye on the surface is the weight ratio collected at this time. The collected compound is preferably separated from the resin component by column chromatography, and further separated and analyzed by liquid chromatography to determine the ratio of the two. Preferably, the quantitative determination is by a calibration curve method. As a result of converting this analytical value, the monoazo dye having two or more hydroxy groups accounts for 5% by weight or more, based on the metal complex of the monoazo dye.
本発明を実現する方法としては、例えば、結着樹脂とし
て酸価が１００ｍｇＫＯＨ／ｇ以下の樹脂を用い、モノ
アゾ染料の金属錯体を含有し、モノアゾ染料を含まない
もしくは含もトナーに、モノアゾ染料と流動性向上剤を
外添する方法、酸価が１００ｍｇＫＯＨ／ｇ以下の結着
樹脂中に、少なくともスチレン或いはアクリルエステル
を主構成成分とする樹脂を１０重量％以上含有し、モノ
アゾ染料の金属錯体を含有し、且つヒドロキシ基を２基
以上有するモノアゾ染料を好ましくはモノアゾ染料の金
属錯体の５重量％以上内添せしめトナーを製造し、更に
流動性向上剤を外添する方法、又は、酸価が１００ｍｇ
ＫＯＨ／ｇ以下の結着樹脂中に、少なくともスチレン或
いはアクリルエステルを主構成成分とする樹脂を１０重
量％以上含有し、モノアゾ染料の金属錯体を含有し、且
つ、反応して本発明のアゾ染料を生成する化合物類をト
ナー中に含有せしめ、トナー製造後に流動性向上剤を外
添する方法等が挙げられる。As a method for realizing the present invention, for example, a resin having an acid value of 100 mgKOH/g or less is used as a binder resin, a metal complex of a monoazo dye is contained, and a toner containing or not containing a monoazo dye is mixed with a monoazo dye. A method of externally adding a fluidity improver, a method in which a binder resin with an acid value of 100 mgKOH/g or less contains 10% by weight or more of a resin whose main constituent is at least styrene or acrylic ester, and a metal complex of a monoazo dye is added. A method in which a monoazo dye having two or more hydroxyl groups is internally added, preferably 5% or more by weight of a metal complex of a monoazo dye, and a fluidity improver is further externally added, or 100mg
A binder resin of KOH/g or less contains at least 10% by weight or more of a resin mainly composed of styrene or acrylic ester, contains a metal complex of a monoazo dye, and reacts to form the azo dye of the present invention. Examples include a method in which compounds that produce the following are contained in the toner, and a fluidity improver is externally added after the toner is manufactured.
以下に本発明に用いるモノアゾ染料の金属錯体、及びヒ
ドロキシ基を２基以上有するモノアゾ染料の具体例を示
すが、これは合成法の容易さ等も考慮した代表例であり
、本発明の化合物を何ら限定するものではない。Specific examples of metal complexes of monoazo dyes and monoazo dyes having two or more hydroxy groups used in the present invention are shown below, but these are representative examples taking into consideration the ease of the synthesis method, etc. It is not limited in any way.
以下にモノアゾ染料の金属錯体例を示す。Examples of metal complexes of monoazo dyes are shown below.
（以下余白）
以下にヒドロキシ基を２基以上有するモノアゾ染料の具
体例を示す。(The following is a blank space) Specific examples of monoazo dyes having two or more hydroxy groups are shown below.
例Ｂ−１
例Ｂ−１０
例Ｂ−１１
本発明の特徴とする結着樹脂を得るためには、ビニル系
重合体のモノマーとして以下のものを用いることができ
る。Example B-1 Example B-10 Example B-11 In order to obtain the binder resin that characterizes the present invention, the following monomers can be used as vinyl polymer monomers.
例えばマレイン酸、シトラコン酸、ジメチルマレイン酸
、イタコン酸、アルケニルコハク酸、及びこれらの無水
物；フマル酸、メタコン酸、ジメチルフマル酸；などの
不飽和二塩基酸、無水物子ツマー０更に上記不飽和二塩
基酸のモノエステル、また、アクリル酸、メタクリル酸
、クロトン酸、ケイヒ酸及びこれらの無水物：上記α、
β−不飽和酸間の無水物及び低級脂肪酸との無水物：な
どのα、β−不飽和酸、これらの無水物モノマー。アル
ケニルマロン酸、アルケニルグルタル酸、アルケニルア
ジピン酸及びこれらの無水物、モノエステル。For example, unsaturated dibasic acids such as maleic acid, citraconic acid, dimethylmaleic acid, itaconic acid, alkenylsuccinic acid, and their anhydrides; fumaric acid, methaconic acid, dimethyl fumaric acid; Monoesters of saturated dibasic acids, as well as acrylic acid, methacrylic acid, crotonic acid, cinnamic acid and their anhydrides: the above α,
Anhydrides between β-unsaturated acids and anhydrides with lower fatty acids: α, β-unsaturated acids, anhydrides thereof, monomers, etc. Alkenyl malonic acid, alkenyl glutaric acid, alkenyl adipic acid and their anhydrides and monoesters.
これらの中でも、マレイン酸、フマル酸、コハク酸の如
ぎ構造をもつα、β−不飽和二塩基酸のモノエステル類
が本発明の結着樹脂を得る千ツマ−として特に好ましく
用いられる。Among these, monoesters of α,β-unsaturated dibasic acids having structures such as maleic acid, fumaric acid, and succinic acid are particularly preferably used as the binder for obtaining the binder resin of the present invention.
更にビニル重合体のコモノマーとしては、次のようなも
のが挙げられる。Furthermore, examples of comonomers for vinyl polymers include the following.
例えばスチレン、０−メチルスチレン、ｍ−メチルスチ
レン、ｐ−メチルスチレン、ｐ−メトキシスチレン、ｐ
−フェニルスチレン、ｐ−クロルスチレン、３．４−ジ
クロルスチレン、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、ｐ ｊ ｅ
ｒ 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、
等のスチレン及びその説導体：エチレン、プロピレン、
ブチレン、イソブチレンなどのエチレン不飽和モノオレ
フィン類；ブタジェン等の不飽和ポリエン類：塩化ビニ
ル、塩化ビニリデン、臭化ビニル、沸化ビニルなどのハ
ロゲン化ビニル類；酢酸ビニル、プロピオン酸ビニル、
ヘンゾエ酸ビニルなどのビニルエステル類；メタクリル
酸メチル、メタクリル酸エチル、メタクリル酸プロピル
、メタクリル酸ｎ−ブチル、メタクリル酸イソブチル、
メタクリル酸ｎ−オクチル、メタクリル酸ドデシル、メ
タクリル酸−２−エチルヘキシル、メタクリル酸ステア
リル、メタクリル酸フェニル、メタクリル酸ジメチルア
ミノエチル、メタクリル酸ジエチルアミノエチルなどの
α−メチレン脂肪族モノカルボン酸エステル類；アクリ
ル酸メチル、アクリル酸エチル、アクリル酸ｎ−ブチル
、アクリル酸イソブチル、アクリル酸プロピル、アクリ
ル酸ｎ−オクチル、アクリル酸ドデシル、アクリル酸２
−エチルヘキシル、アクリル酸ステアリル、アクリル酸
２−クロルエチル、アクリル酸フェニルなどのアクリル
酸エステル類；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などのビニルエーテ
ル類：ビニルメチルケトン、ビニルへキシルケトン、メ
チルイソプロペニルケトンなどのビニルケトン類；Ｎ−
ビニルビロール、Ｎ−ビニルカルバゾール、Ｎ−ビニル
インドール、Ｎ−ビニルピロリドンなどのＮ−ビニル化
合物；ビニルナフタリン類；アクリロニトリル、メタク
リロニトリル、アクリルアミドなどのアクリル酸もしく
はメタクリル酸誘導体；前述のα、β−不飽和酸のエス
テル、二塩基酸のジエステル類；のビニル系モノマーが
単独もしくは２つ以上で用いられる。For example, styrene, 0-methylstyrene, m-methylstyrene, p-methylstyrene, p-methoxystyrene, p
-Phenylstyrene, p-chlorostyrene, 3,4-dichlorostyrene, p-ethylstyrene, 2,4-dimethylstyrene, p-n-butylstyrene, p j e
r t-butylstyrene, p-n-hexylstyrene,
p-n-octylstyrene, p-n-nonylstyrene,
p-n-decylstyrene, p-n-dodecylstyrene,
Styrene and its conductors such as: ethylene, propylene,
Ethylenically unsaturated monoolefins such as butylene and isobutylene; unsaturated polyenes such as butadiene; vinyl halides such as vinyl chloride, vinylidene chloride, vinyl bromide, and vinyl fluoride; vinyl acetate, vinyl propionate,
Vinyl esters such as vinyl henzoate; methyl methacrylate, ethyl methacrylate, propyl methacrylate, n-butyl methacrylate, isobutyl methacrylate,
α-Methylene aliphatic monocarboxylic acid esters such as n-octyl methacrylate, dodecyl methacrylate, 2-ethylhexyl methacrylate, stearyl methacrylate, phenyl methacrylate, dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate; acrylic acid Methyl, ethyl acrylate, n-butyl acrylate, isobutyl acrylate, propyl acrylate, n-octyl acrylate, dodecyl acrylate, acrylic acid 2
- Acrylic acid esters such as ethylhexyl, stearyl acrylate, 2-chloroethyl acrylate, and phenyl acrylate; Vinyl ethers such as vinyl methyl ether, vinyl ethyl ether, and vinyl isobutyl ether: vinyl methyl ketone, vinyl hexyl ketone, and methyl isopropenyl Vinyl ketones such as ketones; N-
N-vinyl compounds such as vinylpyrrole, N-vinylcarbazole, N-vinylindole, and N-vinylpyrrolidone; vinylnaphthalenes; acrylic acid or methacrylic acid derivatives such as acrylonitrile, methacrylonitrile, and acrylamide; Vinyl monomers such as esters of saturated acids and diesters of dibasic acids may be used alone or in combination of two or more.
これらの中でもスチレン系共重合体、スチレンアクリル
系共重合体となるような千ツマ−の組み合わせが好まし
い。Among these, combinations of styrene-based copolymers and styrene-acrylic copolymers are preferred.
又架橋性千ツマ−としては主として２個以上の重合可能
な二重結合を有するモノマーが用いられる。Furthermore, as the crosslinkable polymer, monomers having two or more polymerizable double bonds are mainly used.
本発明に用いられる結着樹脂は、必要に応じて以下に例
示する様な架橋性モノマーで架橋された重合体であって
もよい。The binder resin used in the present invention may be a polymer crosslinked with a crosslinkable monomer as exemplified below, if necessary.
芳香族ジビニル化合物、例えば、ジビニルベンゼン、ジ
ビニルナフタレン等；アルキル鎖で結ばれたジアクリレ
ート化合物類、例えば、エチレングリコールジアクリレ
ート、１．３−ブチレングリコールジアクリレート、１
．４−ブタンジオールジアクリレート、１，５−ベンタ
ンジオ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、ネオベンチルグリコールジアクリレー
ト、及び以上の化合物のアクリレートをメタアクリレー
トに代えたもの；エーテル結合を含むアルキル鎖で結ば
れたジアクリレート化合物類、例えば、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＃４００ジアクリレート、ポリ
エチレングリコール＃６００ジアクリレート、ジプロピ
レングリコールジアクリレート、及び以上の化合物のア
クリレートをメタアクリレートに代えたもの；芳香族基
及びエーテル結合を含む鎖で結ばれたジアクリレート化
合物類、例えば、ポリオキシエチレン（２）−２，２−
ビス（４−ヒドロキシフェニル）プロパンジアクリレー
ト、ポリオキシエチレン（４）−２，２−ビス（４−ヒ
ドロキシフェニル）プロパンジアクリレート、及び、以
上の化合物のアクリレートをメタアクリレートに代えた
もの；更には、ポリエステル型ジアクリレート化合物類
、例えば、商品名ＭＡＮＤＡ （日本化薬）が掲げられ
る。多官能の架橋剤としては、ペンタエリスリトールト
リアクリレート、トリメチロールエタントリアクリレー
ト、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、オリゴエステル
アクリレート、及び以上の化合物のアクリレートをメタ
アクリレートに代えたものニトリアリルシアヌレート、
トリアリルトリメリテート；等が挙げられる。Aromatic divinyl compounds, such as divinylbenzene, divinylnaphthalene, etc.; diacrylate compounds linked with an alkyl chain, such as ethylene glycol diacrylate, 1,3-butylene glycol diacrylate, 1
．． 4-butanediol diacrylate, 1,5-bentanediol diacrylate, 1,6-hexanediol diacrylate, neobentyl glycol diacrylate, and the above compounds in which the acrylate is replaced with methacrylate; containing an ether bond Diacrylate compounds linked with alkyl chains, such as diethylene glycol diacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate,
Polyethylene glycol #400 diacrylate, polyethylene glycol #600 diacrylate, dipropylene glycol diacrylate, and the above compounds in which the acrylate is replaced with methacrylate; diacrylate compounds connected by a chain containing an aromatic group and an ether linkage such as polyoxyethylene (2)-2,2-
Bis(4-hydroxyphenyl)propane diacrylate, polyoxyethylene (4)-2,2-bis(4-hydroxyphenyl)propane diacrylate, and the above compounds in which the acrylate is replaced with methacrylate; , polyester type diacrylate compounds, for example, the trade name MANDA (Nippon Kayaku). Examples of polyfunctional crosslinking agents include pentaerythritol triacrylate, trimethylolethane triacrylate, trimethylolpropane triacrylate, tetramethylolmethanetetraacrylate, oligoester acrylate, and nitriarylic compounds obtained by replacing the acrylate of the above compounds with methacrylate. Lucianurate,
and triallyl trimellitate.
これらの架橋剤は、他の千ツマー成分１００重量％に対
して、０．０１〜５重量％程度（更に好ましくは０．０
３〜３重量％程度）用いることができる。These crosslinking agents should be used in an amount of approximately 0.01 to 5% by weight (more preferably 0.0% by weight) based on 100% by weight of other 100% components.
3 to 3% by weight).
これらの架橋性子ツマ−のうち、トナー用樹脂に、定着
性、耐オフセット性の点から好適に用いられるものとし
て、芳香族ジビニル化合物（特にジビニルベンゼン）、
芳香族基及びエーテル結合を含む鎖で結ばれたジアクリ
レート化合物類が挙げられる。Among these crosslinking compounds, aromatic divinyl compounds (particularly divinylbenzene),
Mention may be made of chain diacrylate compounds containing aromatic groups and ether linkages.
本発明に関わる結着樹脂は、前述のビニル系千ツマ−の
単重合体、共重合体、ポリエステル、ポリウレタン、エ
ポキシ樹脂、ポリビニルブチラール、ロジン、変性ロジ
ン、テルペン樹脂、フェノール樹脂、脂肪族又は脂環族
炭化水素樹脂、芳香族系石油樹脂、へロバラフイン、パ
ラフィンワックス等と必要に応じて混合して用いること
ができる。Binder resins related to the present invention include the above-mentioned vinyl-based monopolymers, copolymers, polyesters, polyurethanes, epoxy resins, polyvinyl butyral, rosins, modified rosins, terpene resins, phenolic resins, aliphatic or fatty resins. It can be used by mixing with a cyclic hydrocarbon resin, an aromatic petroleum resin, a helobaraffin, a paraffin wax, etc., if necessary.
更に本発明の結着樹脂中の酸価はＪＩＳ Ｋ００７０
による。Furthermore, the acid value in the binder resin of the present invention is JIS K0070.
by.
本発明に係る結着樹脂を合成する方法としては、塊状重
合法、溶液重合法、懸濁重合法、乳化重合法などが利用
できる。カルボン酸千ツマー１無水物干ツマ−を用いる
場合には千ツマ−の性質上塊状重合法、溶液重合法を利
用することが好ましい。As a method for synthesizing the binder resin according to the present invention, a bulk polymerization method, a solution polymerization method, a suspension polymerization method, an emulsion polymerization method, etc. can be used. When using anhydrous carboxylic acid, it is preferable to use a bulk polymerization method or a solution polymerization method due to the nature of the carboxylic acid.
又ビニル系重合体を得るためには一例として次のような
方法が挙げられる。ジカルボン酸、ジカルボン酸無水物
、ジカルボン酸モノエステル等の千ツマ−を用い、塊状
重合法、溶液重合法によりビニル系共重合体を得ること
ができる。また、溶液重合法においては、溶媒留去時に
ジカルボン酸、ジカルボン酸モノエステル単位を留去条
件を工夫することにより一部無水化することができる。Further, in order to obtain a vinyl polymer, the following method may be mentioned as an example. Vinyl copolymers can be obtained by bulk polymerization or solution polymerization using dicarboxylic acids, dicarboxylic anhydrides, dicarboxylic acid monoesters, and the like. In addition, in the solution polymerization method, it is possible to partially anhydride the dicarboxylic acid and dicarboxylic acid monoester units by adjusting the distillation conditions during solvent distillation.
更に、塊状重合法、溶液重合法によって得られたビニル
系共重合体を加熱処理することで更に無水化を行うこと
ができる。又無水物をアルコール等により一部エステル
化することもできる。Furthermore, the vinyl copolymer obtained by bulk polymerization method or solution polymerization method can be further rendered anhydrous by heat treatment. Further, the anhydride can also be partially esterified with alcohol or the like.
逆に、この様にして得られたビニル系共重合体を加水分
解処理で無水物を開環させ、一部ジカルボン酸とするこ
とができる。Conversely, the vinyl copolymer obtained in this manner can be hydrolyzed to open the anhydride to form a portion of the dicarboxylic acid.
一方、ジカルボン酸千ノエステルモノマーを用い、懸濁
重合法、乳化重合法で得られたビニル系共重合体を加熱
処理、加水分解処理により無水化及び開環により無水物
、ジカルボン酸を得ることができる。又塊状重合法、溶
液重合法で得られたビニル系共重合体を、千ツマー中に
溶解させ、懸濁重合法、乳化重合法により、ビニル系重
合体を得る方法を用いれば、無水物の一部は開環してジ
カルボン酸を得ることができる。この際、モノマー中に
他の樹脂を混合してもよく、得られた樹脂を加熱処理、
弱アルカリ水処理、アルコール処理により、無水化、開
環、エステル化を行なうことができる。On the other hand, using a dicarboxylic acid monoester monomer, a vinyl copolymer obtained by a suspension polymerization method or an emulsion polymerization method is heated and hydrolyzed to anhydride and ring-opened to obtain an anhydride and a dicarboxylic acid. I can do it. In addition, if a vinyl copolymer obtained by bulk polymerization or solution polymerization is dissolved in 100% water, and then a vinyl copolymer is obtained by suspension polymerization or emulsion polymerization, an anhydride can be obtained. A portion can be ring-opened to obtain a dicarboxylic acid. At this time, other resins may be mixed into the monomer, and the resulting resin is heated and
Anhydration, ring opening, and esterification can be carried out by treatment with weak alkaline water and alcohol.
ところで、ジカルボン酸、ジカルボン酸無水物モノマー
は交互重合性が強いので、無水物、ジカルボン酸などの
官能基をランダムに分散させたビニル系共重合体を得る
ためには以下の方法が好ましい方法の一つである。ジカ
ルボン酸千ノエステルモノマーを用い溶液重合法によっ
てビニル系共重合体を得、このビニル系共重合体をモノ
マー中に溶解させ、懸濁重合法によって結着樹脂を得る
方法である。この方法では、溶液重合後の溶媒留去時に
処理条件によりジカルボン酸モノエステル部を脱アルコ
ール閉環無水化させることができ酸無水物を得ることが
できる。又、懸濁重合時には酸無水物が加水分解開環し
、ジカルボン酸が得られる。By the way, since dicarboxylic acid and dicarboxylic anhydride monomers have strong alternating polymerizability, the following method is the preferred method for obtaining a vinyl copolymer in which functional groups such as anhydride and dicarboxylic acid are randomly dispersed. There is one. In this method, a vinyl copolymer is obtained by solution polymerization using a dicarboxylic acid ester monomer, this vinyl copolymer is dissolved in the monomer, and a binder resin is obtained by suspension polymerization. In this method, when the solvent is distilled off after solution polymerization, the dicarboxylic acid monoester moiety can be dealcoholized and ring-closing anhydride depending on the processing conditions, and an acid anhydride can be obtained. Further, during suspension polymerization, the acid anhydride undergoes hydrolytic ring opening to obtain a dicarboxylic acid.
本発明の現像剤は必要に応じ電荷制御剤を加えることも
できる。トナーを負荷電性に制御するものとして本発明
のモノアゾ金属錯体をそのまま用いることができるが、
更に従来公知の負の電荷制御剤を使用することもできる
。A charge control agent may be added to the developer of the present invention if necessary. Although the monoazo metal complex of the present invention can be used as it is to control the negative chargeability of the toner,
Furthermore, conventionally known negative charge control agents can also be used.
例えば有機金属錯体、キレート化合物が有効で前述した
様なモノアゾ金属錯体、アセチルアセトン金属錯体、芳
香族ハイドロキシカルボン酸、芳香族ダイカルボン酸系
の金属錯体がある。他には、芳香族ハイドロキシカルボ
ン酸、芳香族モノ及びポリカルボン酸及びその金属塩、
無水物、エステル類、ビスフェノール等のフェノール誘
導体類がある。For example, organometallic complexes and chelate compounds are effective, including the aforementioned monoazo metal complexes, acetylacetone metal complexes, aromatic hydroxycarboxylic acids, and aromatic dicarboxylic acid-based metal complexes. Others include aromatic hydroxycarboxylic acids, aromatic mono- and polycarboxylic acids and their metal salts,
There are phenol derivatives such as anhydrides, esters, and bisphenols.
トナーを正荷電性に制御するものとして下記物質がある
。The following substances are used to control the toner to be positively charged.
ニグロシン及び脂肪酸金属塩等による変成物。Modified products with nigrosine and fatty acid metal salts.
トリブチルベンジルアンモニウム−１−ヒドロキシ−４
−ナフトスルフォン酸塩、テトラブチルアンモニウムテ
トラフルオロボレートなどの四級アンモニウム塩、及び
これらの類似体であるホスホニウム塩等のオニウム塩及
びこれらのレーキ顔料。トリフェニルメタン染料及びこ
れらのレーキ顔料。（レーキ化剤としては、りんタング
ステン酸、りんモリブデン酸、りんタングステンそりブ
デン酸、タンニン酸、ラウリン酸、没食子酸、フェリシ
アン化物、フェロシアン化物など）高級脂肪酸の金属塩
、アセチルアセトン金属錯体。ジブチルスズオキサイド
。ジオクチルスズオキサイド、ジシクロへキシルスズオ
キサイドなどのジオルガノスズオキサイド；ジブチルス
ズボレート、ジオクチルスズボレート、ジシクロヘキシ
ルスズボレートなどのジオルガノスズボレート。これら
を単独で或いは２種類以上組合せて用いることができる
。これらの中でも、ニグロシン系、四級アンモニウム塩
の如き電荷制御剤が特に好ましく用いられる。Tributylbenzylammonium-1-hydroxy-4
- Onium salts such as naphthosulfonates, quaternary ammonium salts such as tetrabutylammonium tetrafluoroborate, and phosphonium salts that are analogs thereof, and lake pigments thereof. Triphenylmethane dyes and their lake pigments. (Lake-forming agents include phosphotungstic acid, phosphomolybdic acid, phosphotungsten tribdic acid, tannic acid, lauric acid, gallic acid, ferricyanide, ferrocyanide, etc.) Metal salts of higher fatty acids, acetylacetone metal complexes. Dibutyltin oxide. Diorganotin oxides such as dioctyltin oxide and dicyclohexyltin oxide; diorganotin borates such as dibutyltin borate, dioctyltin borate, and dicyclohexyltin borate. These can be used alone or in combination of two or more. Among these, charge control agents such as nigrosine and quaternary ammonium salts are particularly preferably used.
本発明の現像剤としては、流動性付与、現像性向上、耐
久性向上等を目的として、流動性向上剤の添加が必要で
ある。The developer of the present invention requires the addition of a fluidity improver for the purpose of imparting fluidity, improving developability, improving durability, and the like.
流動性向上剤としては、シリカ微粉末、酸化アルミ微粉
末、酸化チタン微粉末等が挙げられる。Examples of the fluidity improver include fine silica powder, fine aluminum oxide powder, and fine titanium oxide powder.
更にこれらを疎水化したものが好ましい。また、テフロ
ン、ステアリン酸亜鉛、ステアリン酸アルミ等の脂肪酸
金属塩、ポリフッ化ビニリデン、酸化セリウム、炭化珪
素、窒化珪素、カーボンブラック、酸化亜鉛、酸化アン
チモン、酸化錫、酸化はう素、更には有機微粒子なども
現像性の向上を計るとともに流動性向上剤として用いる
ことができる。Furthermore, those made hydrophobic are preferable. In addition, fatty acid metal salts such as Teflon, zinc stearate, aluminum stearate, polyvinylidene fluoride, cerium oxide, silicon carbide, silicon nitride, carbon black, zinc oxide, antimony oxide, tin oxide, boron oxide, and even organic Fine particles can also be used to improve developability and as a fluidity improver.
これらの内でも、シリカ微粉末を添加することが好まし
い。Among these, it is preferable to add silica fine powder.
本発明に用いられるシリカ微粉末は、ＢＥＴ法で測定し
た窒素吸着による比表面積が３０ｍ２／ｇ以上（特に５
０〜４００ｍ２／ｇ）の範囲内のものが良好な結果を与
える。トナー１００重量部に対してシリカ微粉体０．０
１〜８重量部、好ましくは０．１〜５重量部使用するの
が良い。The silica fine powder used in the present invention has a specific surface area of 30 m2/g or more (especially 5
0 to 400 m2/g) gives good results. Silica fine powder 0.0 per 100 parts by weight of toner
It is good to use 1 to 8 parts by weight, preferably 0.1 to 5 parts by weight.
又、本発明に用いられるシリカ微粉末は、必要に応じ、
疎水化、帯電性コントロール、などの目的でシリコーン
オイル、各種変性シリコーンワニス、シリコーンオイル
、各種変性シリコーンオイル、シランカップリング剤、
官能基を有するシランカップリング剤、その他の有機ケ
イ素化合物等の処理剤で、或いは種々の処理剤で併用し
て処理されていることも好ましい。In addition, the fine silica powder used in the present invention may include, if necessary,
Silicone oil, various modified silicone varnishes, silicone oil, various modified silicone oils, silane coupling agents, etc. for the purpose of hydrophobicization, charge control, etc.
It is also preferable that the material be treated with a treatment agent such as a silane coupling agent having a functional group or another organosilicon compound, or with a combination of various treatment agents.
又、処理方法も公知の方法が用いられ、シリカ微粉体と
反応或いは物理吸着する上記処理剤で処理される。処理
剤の具体例としては、例えば、ヘキサメチルジシラザン
、トリメチルシラン、トリメチルクロルシラン、トリメ
チルエトキシシラン、ジメチルジクロルシラン、メチル
トリクロルシラン、アリルジメチルクロルシラン、アリ
ルフエニルジクロルシラン、ベンジルジメチルクロルシ
ラン、ブロムメチルジメチルクロルシラン、α−クロル
エチルトリクロルシラン、β−クロルエチルトリクロル
シラン、クロルメチルジメチルクロルシラン、トリオル
ガノシリルメルカプタン、トリメチルシリルメルカプタ
ン、トリオルガノシリルアクリレート、ビニルジメチル
アセトキシシラン、ジメチルエトキシシラン、ジメチル
ジメトキシシラン、ジフェニルジェトキシシラン、ヘキ
サメチルジシロキサン、１，３−ジビニルテトラメチル
ジシロキサン、１．３−ジフェニルテトラメチルジシロ
キサン、及び１分子当り２から１２個のシロキサン単位
を有し末端に位置する単位にそれぞれ１個宛の３１に結
合した水酸基を含有するジメチルポリシロキサン等が挙
げられる。Also, a known treatment method is used, and the treatment is performed with the above-mentioned treatment agent that reacts with or physically adsorbs to the silica fine powder. Specific examples of the treatment agent include hexamethyldisilazane, trimethylsilane, trimethylchlorosilane, trimethylethoxysilane, dimethyldichlorosilane, methyltrichlorosilane, allyldimethylchlorosilane, allyl phenyldichlorosilane, and benzyldimethylchlorosilane. Silane, bromomethyldimethylchlorosilane, α-chloroethyltrichlorosilane, β-chloroethyltrichlorosilane, chloromethyldimethylchlorosilane, triorganosilylmercaptan, trimethylsilylmercaptan, triorganosilylacrylate, vinyldimethylacetoxysilane, dimethylethoxysilane, Dimethyldimethoxysilane, diphenyljethoxysilane, hexamethyldisiloxane, 1,3-divinyltetramethyldisiloxane, 1,3-diphenyltetramethyldisiloxane, and terminal-terminated siloxane units having 2 to 12 siloxane units per molecule. Examples include dimethylpolysiloxane containing one 31-bonded hydroxyl group in each located unit.
これらは２種以上の混合物で用いることもできる。These can also be used in a mixture of two or more.
更に本発明においては流動性向上剤と併用してチタン酸
ストロンチウムを添加することがより好ましい。チタン
酸ストロンチウムを加えることによって、適度な流動性
、現像特性が、湿度依存性少なく、現像剤に与えられる
。チタン酸ストロンチウムの添加量としてはトナー１０
０重量部に対して０．０１〜１０重量部が好ましい。０
．０１重量部未満だと効果があられれず、１０重量部を
越えると保存中、トナーと遊離してしまう。現像特性を
考えると０．５〜６重量部がより好ましい。又本発明の
モノアゾ染料を含有する現像剤においては流動性向上剤
であるシリカとチタン酸ストロンチウムの両方を含有す
ることが好ましい。Furthermore, in the present invention, it is more preferable to add strontium titanate in combination with a fluidity improver. By adding strontium titanate, appropriate fluidity and development characteristics are imparted to the developer with less humidity dependence. The amount of strontium titanate added is 10 toner.
It is preferably 0.01 to 10 parts by weight relative to 0 parts by weight. 0
．． If it is less than 0.01 parts by weight, the effect will not be achieved, and if it exceeds 10 parts by weight, it will be separated from the toner during storage. Considering development characteristics, 0.5 to 6 parts by weight is more preferable. The developer containing the monoazo dye of the present invention preferably contains both silica and strontium titanate, which are fluidity improvers.
シリカ量をＸ、チタン酸ストロンチウム量をｙとすると
本発明の現像剤においては
０．５≦二≦２０
の範囲内にあるのが現像の特性上から好ましい。When the amount of silica is X and the amount of strontium titanate is y, in the developer of the present invention, it is preferable that they fall within the range of 0.5≦2≦20 from the viewpoint of development characteristics.
又本発明においては着色剤が必要に応じて加えられる。Further, in the present invention, a coloring agent may be added as necessary.
着色剤としては、カーボンブラック、ランプブラック、
鉄黒、群青、ニグロシン染料、アニリンブルー、フタロ
シアニンブルー、フタロシアニングリーン、ハンザイエ
ロー０１ ローダミン６Ｇ。Colorants include carbon black, lamp black,
Iron black, ultramarine blue, nigrosine dye, aniline blue, phthalocyanine blue, phthalocyanine green, Hansa Yellow 01 Rhodamine 6G.
レーキ、カルコオイルブルー、クロムイエロー、キナク
リドン、ベンジジンイエロー、ローズベンガル、トリア
リールメタン系染料、モノアゾ系、ジスアゾ系染顔料等
、従来公知の染顔料を隼独或いは混合して使用し得る。Conventionally known dyes and pigments such as lake, calco oil blue, chrome yellow, quinacridone, benzidine yellow, rose bengal, triarylmethane dyes, monoazo dyes, and disazo dyes and pigments can be used alone or in combination.
着色剤は結着樹脂１００重量部に対して０．１〜１０重
量部使用するのが好ましい。The colorant is preferably used in an amount of 0.1 to 10 parts by weight per 100 parts by weight of the binder resin.
又、熱ロール定着時の離型性を良くする目的で低分子量
ポリエチレン、低分子量ポリプロピレン、マイクロクリ
スタリンワックス、カルナバワックス、サゾールワック
ス、パラフィンフックス等のワックス状物質をバインダ
ー樹脂１００重量部に対し０．５〜１０重量％程度をト
ナーに加えることも本発明の好ましい形態の１つである
。In addition, in order to improve mold releasability during hot roll fixing, 0% of waxy substances such as low molecular weight polyethylene, low molecular weight polypropylene, microcrystalline wax, carnauba wax, Sasol wax, paraffin fuchs, etc. are added to 100 parts by weight of the binder resin. It is also one of the preferred embodiments of the present invention to add about .5 to 10% by weight to the toner.
更に本発明の現像剤は磁性材料を含有させ磁性現像剤と
しても使用しうる。この場合、磁性材料は着色剤の役割
を兼ねている。本発明の磁性トナー中に含まれる磁性材
料としては、マグネタイト、ヘマタイト、フェライト等
の酸化鉄；鉄、コバルト、ニッケルのような金属或いは
これらの金属のアルミニウム、コバルト、銅、鉛、マグ
ネシウム、スズ、亜鉛、アンチモン、ベリリウム、ビス
マス、カドミウム、カルシウム、マンガン、セレン、チ
タン、タングステン、バナジウムのような金属の合金及
びその混合物等が挙げられる。Furthermore, the developer of the present invention can be used as a magnetic developer by containing a magnetic material. In this case, the magnetic material also serves as a coloring agent. The magnetic materials contained in the magnetic toner of the present invention include iron oxides such as magnetite, hematite, and ferrite; metals such as iron, cobalt, and nickel; and aluminum, cobalt, copper, lead, magnesium, tin, and other metals such as iron, cobalt, and nickel. Examples include alloys of metals such as zinc, antimony, beryllium, bismuth, cadmium, calcium, manganese, selenium, titanium, tungsten, and vanadium, and mixtures thereof.
これらの強磁性体は平均粒子が０．１〜２μｍ１好まし
くは０．１〜０．５μｍ程度のものが好ましく、トナー
中に含有させる量としては樹脂成分１００重量部に対し
約２０〜２００重量部、特に好ましくは樹脂成分１００
重量部に対し４０〜１５０重量部が良い。The average particle size of these ferromagnetic materials is preferably about 0.1 to 2 μm, preferably about 0.1 to 0.5 μm, and the amount contained in the toner is about 20 to 200 parts by weight per 100 parts by weight of the resin component. , particularly preferably resin component 100
It is preferably 40 to 150 parts by weight.
又、１０６Ｋｅ印加での磁気特性が抗磁力２０〜１５０
０ｅ飽和磁化５０〜２００ ｅ ｍ ｕ ／ ｇ、残留
磁化２〜２０ ｅ ｍ ｕ ／ ｇのものが望ましい。In addition, the magnetic properties when 106Ke is applied are coercive force 20 to 150.
0e saturation magnetization of 50 to 200 emu/g and residual magnetization of 2 to 20 emu/g are desirable.
更に本発明のトナーは、キャリアと混合して二成分トナ
ーとして用いることもできる。本発明に使用し得るキャ
リアとしては、公知のものが使用可能であり、例えば鉄
粉、フェライト粉、ニッケル粉の様な磁性を有する粉体
、ガラスピーズ等、及びこれらの表面を樹脂等で処理し
たものが掲げられる。又、キャリア表面を被覆する樹脂
としては、スチレン−アクリル酸エステル共重合体、ス
チレン−メタクリル酸エステル共重合体、アクリル酸エ
ステル共重合体、メタクリル酸エステル共重合体、シリ
コーン樹脂、フッ素含有樹脂、ポリアミド樹脂、アイオ
ノマー樹脂、ポリフェニレンサルファイド樹脂など或い
は、これらの混合物を用いることができる。Furthermore, the toner of the present invention can be mixed with a carrier and used as a two-component toner. As the carrier that can be used in the present invention, known carriers can be used, such as iron powder, ferrite powder, magnetic powder such as nickel powder, glass beads, etc., and carriers whose surfaces are treated with resin etc. Those who have done so will be listed. Further, as the resin for coating the carrier surface, styrene-acrylic ester copolymer, styrene-methacrylic ester copolymer, acrylic ester copolymer, methacrylic ester copolymer, silicone resin, fluorine-containing resin, Polyamide resin, ionomer resin, polyphenylene sulfide resin, etc. or a mixture thereof can be used.
本発明に係る静電荷像現像用トナーを作製するには結着
樹脂、着色剤としての顔料、又は染料、磁性体、必要に
応して荷電制御剤、その他の添加剤等を、ヘンシェルミ
キサー、ボールミル等の混合機により充分混合してから
加熱ロール、ニーダ−、エクストルーダーの如き熱混練
機を用いて溶融、捏和及び練肉して樹脂類を互いに相溶
せしめた中に金属化合物、顔料、染料、磁性体を分散又
は溶解せしめ、冷却固化後粉砕及び分級を行って本発明
に係るところのトナーを得ることかできる。To prepare the toner for developing an electrostatic image according to the present invention, a binder resin, a pigment or dye as a coloring agent, a magnetic material, a charge control agent if necessary, other additives, etc. are mixed in a Henschel mixer, After thoroughly mixing with a mixer such as a ball mill, the resins are melted, kneaded, and kneaded using a heat kneader such as a heated roll, kneader, or extruder, and the metal compounds and pigments are mixed in the mixture. The toner according to the present invention can be obtained by dispersing or dissolving dyes and magnetic substances, cooling and solidifying, and then crushing and classifying.
更に必要に応じ所望の添加剤をヘンシェルミキサー等の
混合機により充分混合し、本発明に係る静電荷像現像用
現像剤を得ることができる。Further, if necessary, desired additives are thoroughly mixed using a mixer such as a Henschel mixer to obtain the developer for developing electrostatic images according to the present invention.
［実施例コ
以下、本発明を実施例により更に具体的に説明する。尚
、以下の配合における「部」は全て重量部である。又、
画像濃度はマクベス反射濃度計により測定した値である
。[Example] Hereinafter, the present invention will be explained in more detail with reference to Examples. In addition, all "parts" in the following formulations are parts by weight. or,
The image density is a value measured using a Macbeth reflection densitometer.
合成例１
上記化合物を、還流温度まで加熱したキシレン２００部
中に４時間かけて滴下した。更にキシレン還流下（１３
８〜１４４℃）で重合を完了し、減圧下で２００℃まで
昇温させながらキシレンを除去した。このようにして得
られた樹脂を樹脂Ａとする。Synthesis Example 1 The above compound was added dropwise over 4 hours to 200 parts of xylene heated to reflux temperature. Further under reflux of xylene (13
Polymerization was completed at a temperature of 8 to 144°C), and xylene was removed while raising the temperature to 200°C under reduced pressure. The resin thus obtained is referred to as resin A.
合成例２
上記化合物を用いて合成例１と同様にして樹脂Ｂを得た
。Synthesis Example 2 Resin B was obtained in the same manner as in Synthesis Example 1 using the above compound.
上記化合物を用いて合成例１と同様にして樹脂Ｃを得た
。Resin C was obtained in the same manner as in Synthesis Example 1 using the above compound.
合成例４
上記混合液にポリビニルアルコール部分ケン化物０．１
２重量部を溶解した水１７０重量部を加え、激しく攪拌
し、懸濁分散液とした。水５０重量部を入れ窒素置換し
た反応器に上記懸濁分散液を添加し、反応温度８０℃で
８時間懸濁重合反応させた。反応終了後、水洗し、脱水
、乾燥して樹脂りを得た。Synthesis Example 4 Add 0.1% of partially saponified polyvinyl alcohol to the above mixture.
170 parts by weight of water in which 2 parts by weight was dissolved was added and vigorously stirred to form a suspension dispersion. The above suspension dispersion was added to a reactor containing 50 parts by weight of water and purged with nitrogen, and suspension polymerization reaction was carried out at a reaction temperature of 80° C. for 8 hours. After the reaction was completed, the resin was washed with water, dehydrated, and dried to obtain a resin.
合成例５
上記混合液を用いて合成例４と同様にして反応せしめ、
反応終了後、ｐＨ−１０のアルカリ水により洗浄し、更
に弱酸水、水で洗浄し、脱水、乾燥して樹脂Ｅを得た。Synthesis Example 5 Using the above mixture, react in the same manner as in Synthesis Example 4,
After the reaction was completed, the resin was washed with alkaline water of pH-10, further washed with weak acid water and water, dehydrated and dried to obtain Resin E.
上記混合液を用いて合成例４と同様にして樹Ｈ旨Ｆを得
た。Tree Hji F was obtained in the same manner as in Synthesis Example 4 using the above mixed solution.
合成例７
１スチレン ７５．２部上記化合
物を、還流温度まで加熱したキシレン２００重量部中に
４時間かけて滴下した。更に、キシレン還流下（１３８
〜１４４℃）で重合を完了し、減圧下で２００℃に加熱
し、キシレンを除去した。このようにして得られた樹脂
を樹脂Ｇとする。Synthesis Example 7 1 75.2 parts of styrene The above compound was added dropwise over 4 hours to 200 parts by weight of xylene heated to reflux temperature. Furthermore, under xylene reflux (138
Polymerization was completed at ˜144° C.) and heated to 200° C. under reduced pressure to remove xylene. The resin thus obtained is referred to as resin G.
上記混合液にポリビニルアルコール部分ケン化物０．１
２重量部を溶解した水１７０重量部を加え、激しく攪拌
し、懸濁分散液とした。水５０重量部を入れ窒素置換し
た反応器に上記懸濁分散液を添加し、反応温度８０℃で
８時間懸濁重合反応させた。反応終了後、水洗し、脱水
、乾燥して樹脂Ｈを得た。Add 0.1% of partially saponified polyvinyl alcohol to the above mixture.
170 parts by weight of water in which 2 parts by weight was dissolved was added and vigorously stirred to form a suspension dispersion. The above suspension dispersion was added to a reactor containing 50 parts by weight of water and purged with nitrogen, and suspension polymerization reaction was carried out at a reaction temperature of 80° C. for 8 hours. After the reaction was completed, Resin H was obtained by washing with water, dehydrating, and drying.
上記材料をヘンシェルミキサーでよく前混合した後、１
４０℃に設定した２軸混練押出機にて溶融混練した。得
られた混練物を冷却し、カッターミルにて粗粉砕した後
、ジェット気流を用いた微粉砕機を用いて微粉砕し、更
に得られた微粉砕粉を風力分級機で分級した。体積平均
粒径９．５μｍの微粉体（トナー）を得た。After pre-mixing the above ingredients thoroughly with a Henschel mixer, 1
The mixture was melt-kneaded using a twin-screw kneading extruder set at 40°C. The obtained kneaded product was cooled and coarsely pulverized using a cutter mill, then finely pulverized using a pulverizer using a jet stream, and the obtained pulverized powder was further classified using an air classifier. A fine powder (toner) having a volume average particle diameter of 9.5 μm was obtained.
得られた微粉体１００部にヘキサメチルジシラザンによ
り疎水化処理したシリカ微粉末（ＢＥＴ比表面積３００
ｍ” ７ｇ）Ｑ、６部及びチタン酸ストロンチウム２．
５部を加え、ヘンシェルミキサーで混合して現像剤とし
た。100 parts of the obtained fine powder was added with silica fine powder (BET specific surface area: 300
m” 7g) Q, 6 parts and strontium titanate 2.
5 parts were added and mixed in a Henschel mixer to prepare a developer.
このトナーを市販の複写機（商品名ＮＰ−６６５０、キ
ャノン（株）製）に適用して２３℃／６０％の環境条件
下、複写試験をしたところ、１００枚複写後の画像濃度
は１．３６でカブリやがさつきがなく、鮮明な画像が得
られた。更に、１万枚複写して耐久性能を調べたところ
、画像濃度１．３８でカブリやがさつきが無く、初期の
画像と比較して遜色のない良好な画像が得られた。When this toner was applied to a commercially available copying machine (product name NP-6650, manufactured by Canon Inc.) and subjected to a copying test under environmental conditions of 23°C/60%, the image density after copying 100 sheets was 1. 36, clear images were obtained without fogging or roughness. Furthermore, when 10,000 copies were made and the durability was examined, it was found that the image density was 1.38, there was no fogging or roughness, and a good image comparable to the initial image was obtained.
又、現像スリーブ上のトナーの摩擦帯電量を測定したと
ころ、初期においては−１１，５μＣ／ｇ、１万枚複写
後は、−１１，０ＡＩｃ／ｇとほとんどスリーブ汚染は
認められなかった。Furthermore, when the amount of triboelectric charge of the toner on the developing sleeve was measured, it was -11.5 .mu.C/g at the initial stage and -11.0 AIc/g after 10,000 copies, showing that almost no sleeve contamination was observed.
又、得られた画像上にはオフセット、裏汚れは見られず
、定着ローラー上にも汚れは見られなかった。Further, no offset or back stain was observed on the obtained image, and no stain was observed on the fixing roller.
次いで、１５℃／１０％の環境条件下、複写試験をした
ところ、同様に高濃度で良好な画質の画像が得られれた
。１万枚の複写試験においても同様に良好な成績であっ
た。更に、文字画像濃度０．５％の画像サンプルを連続
して５００枚複写時の前後の画像濃度を比較したところ
、大きな濃度低下は見られなかった。この環境条件下で
の結果を表２にまとめた。Then, when a copying test was carried out under an environmental condition of 15° C./10%, similarly high density and good quality images were obtained. Similarly, good results were obtained in a 10,000 copy test. Furthermore, when the image density before and after 500 consecutive copies of an image sample with a character image density of 0.5% was compared, no significant decrease in density was observed. The results under these environmental conditions are summarized in Table 2.
３５℃／８５％の環境条件下、同し複写試験、１万枚複
写試験を行なったところ、良好な結果であフた。この環
境条件下での結果を表３にまとめた。The same copying test and 10,000-sheet copying test were conducted under environmental conditions of 35° C./85%, and good results were obtained. The results under these environmental conditions are summarized in Table 3.
又、１リツトルのポリプロピレン製カップにこの現像剤
１００ｇ入れ、温度５０℃で１週間放置後、よく振とう
した後に容器に付着したモノアゾ染料の金属錯体とモノ
アゾ染料を分析しモノアゾ染料の金属錯体を基準とした
時のモノアゾ染料の重量比を求めた。この結果を表４に
まとめた。In addition, 100 g of this developer was placed in a 1 liter polypropylene cup, left at a temperature of 50°C for one week, and after shaking well, the metal complex of the monoazo dye and the metal complex of the monoazo dye attached to the container were analyzed. The weight ratio of the monoazo dye when used as a standard was determined. The results are summarized in Table 4.
上記材料を用いて実施例１と同様にして、体積平均粒径
９，５μｍの微粉体（トナー）を得た。A fine powder (toner) having a volume average particle diameter of 9.5 μm was obtained in the same manner as in Example 1 using the above materials.
得らねた微粉体１００部に化合物Ｂ−１００１部を加え
、ヘンシェルミキサーで混合した後、更にヘキサメチル
ジシラザンにより疎水化処理したシリカ微粉末（ＢＥＴ
比表面積３００ｍ２／ｇ）０６部及びチタン酸ストロン
チウム３．０部を加え、ヘンシェルミキサーで混合して
現像剤とした。100 parts of Compound B-1 was added to 100 parts of the obtained fine powder, and after mixing in a Henschel mixer, fine silica powder (BET) was further hydrophobized with hexamethyldisilazane.
06 parts (specific surface area: 300 m2/g) and 3.0 parts of strontium titanate were added and mixed in a Henschel mixer to prepare a developer.
この現像剤を実施例１と同様に評価した。This developer was evaluated in the same manner as in Example 1.
上記材料を用いて実施例１と同様にして、体積平均粒径
９．５μｍの微粉体（トナー）を得た。A fine powder (toner) having a volume average particle diameter of 9.5 μm was obtained in the same manner as in Example 1 using the above materials.
得られた微粉体１００部に化合物Ｂ−１０、，０１部を
加え、ヘンシェルミキサーで混合した後、更にヘキサメ
チルジシラザンにより疎水化処理したシリカ微粉末（Ｂ
ＥＴ比表面積３００ｍ２／ｇ）０．６部を加え、ヘンシ
ェルミキサーで混合して現像剤とした。After adding 1 part of compound B-10,01 to 100 parts of the obtained fine powder and mixing with a Henschel mixer, fine silica powder (B
ET specific surface area 300 m2/g) was added and mixed in a Henschel mixer to prepare a developer.
この現像剤を実施例１と同様に評価した。This developer was evaluated in the same manner as in Example 1.
上記材料を用いて実施例１と同様にして、体積平均粒径
９．５μｍの微粉体（トナー）を得た。A fine powder (toner) having a volume average particle diameter of 9.5 μm was obtained in the same manner as in Example 1 using the above materials.
得られた微粉体１００部にヘキサメチルジシラザンによ
り疎水化処理したシリカ微粉末（ＢＥＴ比表面積３００
ｍ’／ｇ）ｏ、６部を加え、ヘンシェルミキサーで混合
して現像剤とした。100 parts of the obtained fine powder was added with silica fine powder (BET specific surface area: 300
6 parts of m'/g)o were added and mixed in a Henschel mixer to prepare a developer.
この現像剤を実施例１と同様に評価した。This developer was evaluated in the same manner as in Example 1.
上記材料を用いて実施例１と同様にして、体積平均粒径
９．５μｍの微粉体（トナー）を得た。A fine powder (toner) having a volume average particle diameter of 9.5 μm was obtained in the same manner as in Example 1 using the above materials.
得られた微粉体１００部にヘキサメチルジシラザンによ
り疎水化処理したシリカ微粉末（ＢＥＴ比表面積３００
ｍ２／ｇ）ｏ、６部を加え、ヘンシェルミキサーで混合
して現像剤とした。100 parts of the obtained fine powder was added with silica fine powder (BET specific surface area: 300
6 parts of m2/g)o were added and mixed in a Henschel mixer to prepare a developer.
この現像剤を実施例１と同様に評価した。This developer was evaluated in the same manner as in Example 1.
上記材料を用いて実施例１と同様にして、体積平均粒径
９．５μｍの微粉体（トナー）を得た。A fine powder (toner) having a volume average particle diameter of 9.5 μm was obtained in the same manner as in Example 1 using the above materials.
得られた微粉体１００部に、ヘキサメチルジシラザンに
より疎水化処理したシリカ微粉末（ＢＥＴ比表面積３０
０ｍ２７ｇ）０．６部を加え、ヘンシェルミキサーで混
合して現像剤とした。To 100 parts of the obtained fine powder, silica fine powder (BET specific surface area 30
0.6 parts of 0m27g) were added and mixed in a Henschel mixer to prepare a developer.
この現像剤を実施例１と同様に評価した。This developer was evaluated in the same manner as in Example 1.
上記材料を用いて実施例１と同様にして、体積平均粒径
９．５μｍの微粉体（トナー）を得た。A fine powder (toner) having a volume average particle diameter of 9.5 μm was obtained in the same manner as in Example 1 using the above materials.
得られた微粉体１００部にヘキサメチルジシラザンによ
り疎水化処理したシリカ微粉末（ＢＥＴ比表面積３００
ｍ’ ７ｇ）０．６部を加え、ヘンシェルミキサーで混
合して現像剤とした。100 parts of the obtained fine powder was added with silica fine powder (BET specific surface area: 300
m' 7g) was added and mixed in a Henschel mixer to prepare a developer.
この現像剤を実施例１と同様に評価した。This developer was evaluated in the same manner as in Example 1.
上記材料を用いて実施例１と同様にして、体積平均粒径
９．５μｍの微粉体（トナー）を得た。A fine powder (toner) having a volume average particle diameter of 9.5 μm was obtained in the same manner as in Example 1 using the above materials.
得られた微粉体１００部にヘキサメチルジシラザンによ
り疎水化処理したシリカ微粉末（ＢＥＴ比表面積３００
ｍ２／ｇ）０．６部を加え、ヘンシェルミキサーで混合
して現像剤とした。100 parts of the obtained fine powder was added with silica fine powder (BET specific surface area: 300
m2/g) was added and mixed using a Henschel mixer to prepare a developer.
この現像剤を実施例１と同様に評価した。This developer was evaluated in the same manner as in Example 1.
上記材料を用いて実施例１と同様にして、体積平均粒径
８．９μｍの微粉体を得、この微粉体１００部にジメチ
ルジクロロシランで疎水化処理されたシリカ微粉末（Ｂ
ＥＴ比表面積２００ｍ２／ｇ）０．６部を加え、ヘンシ
ェルミキサーで混合してトナーとした。A fine powder with a volume average particle diameter of 8.9 μm was obtained using the above materials in the same manner as in Example 1, and 100 parts of this fine powder was added to silica fine powder (B
0.6 part of ET specific surface area 200 m2/g) was added and mixed in a Henschel mixer to prepare a toner.
次いで平均粒径６５μｍのアクリルコートフェライトキ
ャリア１００部に対して得られたトナー６部を混合して
現像剤とした。Next, 6 parts of the obtained toner were mixed with 100 parts of an acrylic coated ferrite carrier having an average particle size of 65 μm to prepare a developer.
この現像剤を市販の複写機（商品名ＮＰ−６６５０、キ
ャノン（株）製）に通用して、実施例１と同様な評価を
行った。This developer was used in a commercially available copying machine (trade name NP-6650, manufactured by Canon Inc.) and evaluated in the same manner as in Example 1.
比較例１
上記材料を用いて実施例１と同様にして、体積平均粒径
９．５μｍの微粉体（トナー）を得た。Comparative Example 1 A fine powder (toner) having a volume average particle diameter of 9.5 μm was obtained in the same manner as in Example 1 using the above materials.
得られた微粉体１００部にヘキサメチルジシラザンによ
り疎水化処理したシリカ微粉末（ＢＥＴ比表面積３００
ｍ２／ｇ）ｏ、６部及びチタン酸ストロンチウム２．５
部を加え、ヘンシェルミキサーで混合して現像剤とした
。100 parts of the obtained fine powder was added with silica fine powder (BET specific surface area: 300
m2/g) o, 6 parts and strontium titanate 2.5
and mixed with a Henschel mixer to prepare a developer.
この現像剤を実施例１と同様に評価したところ、初期画
像及び１万枚複写後、十分な濃度の画像が得られたが、
オフセット、裏汚れが生した。When this developer was evaluated in the same manner as in Example 1, images with sufficient density were obtained in the initial image and after copying 10,000 copies.
Offset and back stains occurred.
比較例２
上記材料を用いて実施例１と同様にして、体積平均粒径
９．５μｍの微粉体（トナー）を得た。Comparative Example 2 A fine powder (toner) having a volume average particle diameter of 9.5 μm was obtained in the same manner as in Example 1 using the above materials.
得られた微粉体１００部にヘキサメチルジシラザンによ
り疎水化処理したシリカ微粉末（ＢＥＴ比表面積３００
ｍ２／ｇ）０．６部を加え、ヘンシェルミキサーで混合
して現像剤とした。100 parts of the obtained fine powder was added with silica fine powder (BET specific surface area: 300
m2/g) was added and mixed using a Henschel mixer to prepare a developer.
この現像剤を実施例１と同様に評価したところ、３５℃
／８５％の環境条件下、複写試験中、画像濃度が著しく
低下した。When this developer was evaluated in the same manner as in Example 1, it was found that
/85%, the image density decreased significantly during the copying test.
比較例３
１樹脂Ｇ １００部上記材
料を用いて実施例１と同様にして、体積平均粒径９．５
μｍの微粉体（トナー）を得た。Comparative Example 3 1 Resin G 100 parts In the same manner as in Example 1 using the above materials, the volume average particle size was 9.5.
A fine powder (toner) of μm size was obtained.
得られた微粉体１００部にヘキサメチルジシラザンによ
り疎水化処理したシリカ微粉末（ＢＥＴ比表面積３００
ｍ２／ｇ）０．６部を加え、ヘンシェルミキサーで混合
して現像剤とした。100 parts of the obtained fine powder was added with silica fine powder (BET specific surface area: 300
m2/g) was added and mixed using a Henschel mixer to prepare a developer.
この現像剤を実施例１と同様に評価したところ、１５℃
／１０％の環境条件下での５００枚の連続複写試験にお
いて、画像濃度が著しく低下した。When this developer was evaluated in the same manner as in Example 1, it was found that
In a continuous copying test of 500 sheets under environmental conditions of /10%, the image density was significantly reduced.
比較例４
上記材料を用いて実施例１と同様にして、体積平均粒径
９，５μｍの微粉体（トナー）を得た。Comparative Example 4 A fine powder (toner) having a volume average particle diameter of 9.5 μm was obtained in the same manner as in Example 1 using the above materials.
得られた微粉体１００部にアゾ染料オレンジＧ（Ｃ，１
，１６２３０）０．０１部を加え、ヘンシェルミキサー
で混合した後、更にヘキサメチルジシラザンにより疎水
化処理したシリカ微粉末（ＢＥＴ比表面積３００ｍ２７
ｇ）０．６部を加え、ヘンシェルミキサーで混合して現
像剤とした。Azo dye Orange G (C,1
, 16230) was added, mixed in a Henschel mixer, and then hydrophobized with hexamethyldisilazane (BET specific surface area: 300 m27).
g) 0.6 part was added and mixed in a Henschel mixer to prepare a developer.
この現像剤を実施例１と同様に評価したところ、３５℃
／８５％の環境条件下、複写試験中、画像濃度が著しく
低下するとともにカブリが生じた。When this developer was evaluated in the same manner as in Example 1, it was found that
/85%, during the copying test, the image density was significantly reduced and fogging occurred.
表１ 結着樹脂の酸価
表２ １５℃／１０％
◎優 ○良 △可 ×不可
表３ ３２．５℃／８０％
◎優 ○良 △可 ×不可
表４
［発明の効果］
上述したように、本発明のトナー結着樹脂の酸価が１０
０ｍｇＫＯＨ／ｇ以下であり、少なくともモノアゾ染料
のクロム錯体、鉄錯体或はコバルト錯体を含有し、ヒド
ロキシ基を２基以上有するモノアゾ染料を含有し、流動
性向上剤を含有することを特徴とする現像剤か、定着性
、耐オフセット性を向上するとともに、ｆ電量の環境依
存性か良好化する。Table 1 Acid value of binder resin Table 2 15°C/10% ◎ Excellent ○ Good △ Acceptable × Not possible Table 3 32.5°C/80% ◎ Excellent ○ Good △ Acceptable × Not possible Table 4 [Effects of the invention] As mentioned above The acid value of the toner binder resin of the present invention is 10.
0 mgKOH/g or less, contains at least a chromium complex, iron complex, or cobalt complex of a monoazo dye, contains a monoazo dye having two or more hydroxy groups, and contains a fluidity improver. In addition to improving fixing properties and anti-offset properties, it also improves the environmental dependence of the amount of electric current.
低湿下におけるｆ電量過剰、高湿下での！電量不足を抑
制するために、広範囲な環境条件下で、十分な濃度の画
像を提供する。更に、不均一１！：電を防ぐために、カ
ブリの無く良好な品質の画像を与える。又トナーと流動
性向上剤の組成比か一定化し、トナー担持体の汚染が減
少したために、大量に複写した後も、十分な濃度で優れ
た品質の画像が得られる。Excessive f charge under low humidity, under high humidity! Provide images with sufficient density under a wide range of environmental conditions to suppress power shortages. Furthermore, unevenness 1! : Provides a good quality image without fogging to prevent electromagnetic interference. Furthermore, since the composition ratio of the toner and the fluidity improver is kept constant and contamination of the toner carrier is reduced, images with sufficient density and excellent quality can be obtained even after copying in large quantities.
Claims (5)
性向上剤を含有する現像剤において、 酸価が１００ｍｇＫＯＨ／ｇ以下の結着樹脂、 モノアゾ染料の金属錯体、 ヒドロキシ基を２基以上有するモノアゾ染料を少なくと
も含有することを特徴とする現像剤。(1) In a developer containing at least a binder resin, a colorant, a charge control agent, and a fluidity improver, a binder resin with an acid value of 100 mgKOH/g or less, a metal complex of a monoazo dye, and two or more hydroxy groups A developer characterized in that it contains at least a monoazo dye.
表される化合物であり、ヒドロキシ基を２基以上有する
モノアゾ染料が下記一般式（II）で表される化合物であ
ることを特徴とする請求項（１）記載の現像剤。 ▲数式、化学式、表等があります▼（ I ） 〔式中、ＭはＣｒ＾III、、Ｆｅ＾III、Ｃｏ＾III、Ｃ
ｕ＾ I またはＣｕ＾II、Ｚｎ＾IIを、Ａ＾■はＨ＾■
アルカリ金属、炭素数８以下の４級アンモニウムを、Ｒ
＿１とＲ＿２は水素、ハロゲン原子、ニトロ基、アルキ
ル基を、Ｒ＿３は水素、ハロゲン原子、ニトロ基、カル
ボキシル基、ヒドロキシル基、アルキル基、或いは、ハ
ロゲン、ニトロ基を有しても良いベンズアミド基もしく
はベンズスルホアミド基を示す。〕 ▲数式、化学式、表等があります▼（II） 式中、Ｒ＿４、Ｒ＿５は水素、ハロゲン、ニトロ基、ア
ルキル基を、Ｒ＿６は水素、ハロゲン原子、ニトロ基、
カルボキシル基、ヒドロキシル基、アルキル基、或いは
、ハロゲン、ニトロ基を有しても良いベンズアミド基も
しくはベンズスルホアミド基を示す。(2) The metal complex of the monoazo dye is a compound represented by the following general formula (I), and the monoazo dye having two or more hydroxy groups is a compound represented by the following general formula (II). The developer according to claim (1). ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, M is Cr^III, , Fe^III, Co^III, C
u^I or Cu^II, Zn^II, A^■ is H^■
Alkali metal, quaternary ammonium having 8 or less carbon atoms, R
_1 and R_2 are hydrogen, a halogen atom, a nitro group, an alkyl group, and R_3 is a hydrogen, a halogen atom, a nitro group, a carboxyl group, a hydroxyl group, an alkyl group, or a benzamide group that may have a halogen or a nitro group, or Indicates a benzsulfamide group. ] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (II) In the formula, R_4 and R_5 are hydrogen, halogen, nitro group, alkyl group, and R_6 is hydrogen, halogen atom, nitro group,
Indicates a carboxyl group, hydroxyl group, alkyl group, or a benzamide group or benzsulfoamide group which may have a halogen or nitro group.
ロキシ基を２基以上有するモノアゾ染料と同一の化合物
であることを特徴とする請求項（１）、（２）記載の現
像剤。(3) The developer according to claims (1) and (2), wherein the ligand in the metal complex of the monoazo dye is the same compound as the monoazo dye having two or more hydroxy groups.
ナー表面に、モノアゾ染料の金属錯体の重量の少なくと
も０．１重量％以上存在することを特徴とする請求項（
１）〜（３）記載の現像剤。(4) A claim characterized in that the monoazo dye having two or more hydroxy groups is present on the toner surface in an amount of at least 0.1% by weight based on the weight of the metal complex of the monoazo dye (
Developers described in 1) to (3).
ることを特徴とする請求項（１）〜（４）記載の現像剤
。(5) The developer according to any one of claims (1) to (4), wherein the developer contains a magnetic material and is a one-component magnetic developer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2295418A JP2737026B2 (en) | 1990-11-02 | 1990-11-02 | Developer for developing electrostatic images |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2295418A JP2737026B2 (en) | 1990-11-02 | 1990-11-02 | Developer for developing electrostatic images |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04170557A true JPH04170557A (en) | 1992-06-18 |
| JP2737026B2 JP2737026B2 (en) | 1998-04-08 |
Family
ID=17820351
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2295418A Expired - Fee Related JP2737026B2 (en) | 1990-11-02 | 1990-11-02 | Developer for developing electrostatic images |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2737026B2 (en) |
-
1990
- 1990-11-02 JP JP2295418A patent/JP2737026B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2737026B2 (en) | 1998-04-08 |
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