JPS63169664A - Toner for electrostatic charge image development - Google Patents
Toner for electrostatic charge image developmentInfo
- Publication number
- JPS63169664A JPS63169664A JP62001182A JP118287A JPS63169664A JP S63169664 A JPS63169664 A JP S63169664A JP 62001182 A JP62001182 A JP 62001182A JP 118287 A JP118287 A JP 118287A JP S63169664 A JPS63169664 A JP S63169664A
- Authority
- JP
- Japan
- Prior art keywords
- toner
- group
- weight
- methacrylate
- acrylate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000178 monomer Substances 0.000 claims abstract description 42
- 229920005989 resin Polymers 0.000 claims abstract description 34
- 239000011347 resin Substances 0.000 claims abstract description 34
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 32
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 26
- 229920000642 polymer Polymers 0.000 claims abstract description 17
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 10
- 239000011230 binding agent Substances 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000000470 constituent Substances 0.000 claims description 2
- 125000005462 imide group Chemical group 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 2
- 229910006069 SO3H Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
- 239000000843 powder Substances 0.000 description 16
- -1 Methacrylic nitrile Chemical class 0.000 description 13
- 239000000377 silicon dioxide Substances 0.000 description 13
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 239000003086 colorant Substances 0.000 description 11
- 239000002245 particle Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 230000002209 hydrophobic effect Effects 0.000 description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 229910017052 cobalt Inorganic materials 0.000 description 8
- 239000010941 cobalt Substances 0.000 description 8
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 239000006247 magnetic powder Substances 0.000 description 6
- 229910052724 xenon Inorganic materials 0.000 description 6
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 238000004140 cleaning Methods 0.000 description 5
- 229920001577 copolymer Polymers 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
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 230000007547 defect Effects 0.000 description 4
- 125000004386 diacrylate group Chemical group 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000011133 lead Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 3
- 108091008695 photoreceptors Proteins 0.000 description 3
- 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 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- OSNILPMOSNGHLC-UHFFFAOYSA-N 1-[4-methoxy-3-(piperidin-1-ylmethyl)phenyl]ethanone Chemical compound COC1=CC=C(C(C)=O)C=C1CN1CCCCC1 OSNILPMOSNGHLC-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- 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
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
- PLXMOAALOJOTIY-FPTXNFDTSA-N Aesculin Natural products OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)[C@H]1Oc2cc3C=CC(=O)Oc3cc2O PLXMOAALOJOTIY-FPTXNFDTSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 108091005944 Cerulean Proteins 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- KWORKYDIARWARF-UHFFFAOYSA-N N-(4-chloro-2-methylphenyl)-4-[(4-chloro-2-methylphenyl)diazenyl]-3-hydroxynaphthalene-2-carboxamide Chemical compound Cc1cc(Cl)ccc1NC(=O)c1cc2ccccc2c(N=Nc2ccc(Cl)cc2C)c1O KWORKYDIARWARF-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- MRQIXHXHHPWVIL-ISLYRVAYSA-N Sudan I Chemical compound OC1=CC=C2C=CC=CC2=C1\N=N\C1=CC=CC=C1 MRQIXHXHHPWVIL-ISLYRVAYSA-N 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- ZWPUSIPAMUKNJR-UHFFFAOYSA-N [Br].[Cu] Chemical compound [Br].[Cu] ZWPUSIPAMUKNJR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 229910052793 cadmium Inorganic materials 0.000 description 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- HBHZKFOUIUMKHV-UHFFFAOYSA-N chembl1982121 Chemical compound OC1=CC=C2C=CC=CC2=C1N=NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HBHZKFOUIUMKHV-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- CVAGYCLEIYGJQT-UHFFFAOYSA-N dichloro(dioctyl)silane Chemical compound CCCCCCCC[Si](Cl)(Cl)CCCCCCCC CVAGYCLEIYGJQT-UHFFFAOYSA-N 0.000 description 2
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 description 2
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- PLYDMIIYRWUYBP-UHFFFAOYSA-N ethyl 4-[[2-chloro-4-[3-chloro-4-[(3-ethoxycarbonyl-5-oxo-1-phenyl-4h-pyrazol-4-yl)diazenyl]phenyl]phenyl]diazenyl]-5-oxo-1-phenyl-4h-pyrazole-3-carboxylate Chemical compound CCOC(=O)C1=NN(C=2C=CC=CC=2)C(=O)C1N=NC(C(=C1)Cl)=CC=C1C(C=C1Cl)=CC=C1N=NC(C(=N1)C(=O)OCC)C(=O)N1C1=CC=CC=C1 PLYDMIIYRWUYBP-UHFFFAOYSA-N 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- UCNNJGDEJXIUCC-UHFFFAOYSA-L hydroxy(oxo)iron;iron Chemical compound [Fe].O[Fe]=O.O[Fe]=O UCNNJGDEJXIUCC-UHFFFAOYSA-L 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
- CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical compound OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- MBDIPBHBEVOYQB-UHFFFAOYSA-N nigerone Chemical compound O1C(C)=CC(=O)C2=C1C(C1=C3C(C(C=C(C)O3)=O)=C(O)C3=C(OC)C=C(C=C31)OC)=C1C=C(OC)C=C(OC)C1=C2O MBDIPBHBEVOYQB-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 150000003440 styrenes Chemical class 0.000 description 2
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 2
- SMYMJHWAQXWPDB-UHFFFAOYSA-N (2,4,5-trichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl SMYMJHWAQXWPDB-UHFFFAOYSA-N 0.000 description 1
- HFXVXHPSVLHXCC-UHFFFAOYSA-N (2-hydroxy-3-phenoxypropyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)COC1=CC=CC=C1 HFXVXHPSVLHXCC-UHFFFAOYSA-N 0.000 description 1
- HHQAGBQXOWLTLL-UHFFFAOYSA-N (2-hydroxy-3-phenoxypropyl) prop-2-enoate Chemical compound C=CC(=O)OCC(O)COC1=CC=CC=C1 HHQAGBQXOWLTLL-UHFFFAOYSA-N 0.000 description 1
- SZCWBURCISJFEZ-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl) 3-hydroxy-2,2-dimethylpropanoate Chemical compound OCC(C)(C)COC(=O)C(C)(C)CO SZCWBURCISJFEZ-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- VTWGIDKXXZRLGH-CMDGGOBGSA-N (e)-4-octoxy-4-oxobut-2-enoic acid Chemical compound CCCCCCCCOC(=O)\C=C\C(O)=O VTWGIDKXXZRLGH-CMDGGOBGSA-N 0.000 description 1
- NALFRYPTRXKZPN-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(OOC(C)(C)C)(OOC(C)(C)C)C1 NALFRYPTRXKZPN-UHFFFAOYSA-N 0.000 description 1
- HSLFISVKRDQEBY-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)cyclohexane Chemical compound CC(C)(C)OOC1(OOC(C)(C)C)CCCCC1 HSLFISVKRDQEBY-UHFFFAOYSA-N 0.000 description 1
- QMMJWQMCMRUYTG-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl QMMJWQMCMRUYTG-UHFFFAOYSA-N 0.000 description 1
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- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- KRLHYNPADOCLAJ-UHFFFAOYSA-N undecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCOC(=O)C(C)=C KRLHYNPADOCLAJ-UHFFFAOYSA-N 0.000 description 1
- RRLMGCBZYFFRED-UHFFFAOYSA-N undecyl prop-2-enoate Chemical compound CCCCCCCCCCCOC(=O)C=C RRLMGCBZYFFRED-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 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
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- ODNJVAVDJKOYFK-GRVYQHKQSA-L zinc;(9z,12z)-octadeca-9,12-dienoate Chemical compound [Zn+2].CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O.CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O ODNJVAVDJKOYFK-GRVYQHKQSA-L 0.000 description 1
- LPEBYPDZMWMCLZ-CVBJKYQLSA-L zinc;(z)-octadec-9-enoate Chemical compound [Zn+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O LPEBYPDZMWMCLZ-CVBJKYQLSA-L 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/087—Binders for toner particles
- G03G9/08702—Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- G03G9/0874—Polymers comprising hetero rings in the side chains
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- 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、静電記録等の分野で使用される静電
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 fields such as electrophotography and electrostatic recording.
電子写真、静電記録等では、感光体上に種々の手法によ
り静電荷像を形成させた後、該静電荷像をトナー粒子で
現像し1次いで像を形成したトナーを紙、マイラーフィ
ルム等の他の転写材に転移させ、加熱ロール、加圧ロー
ル、熱圧ロール或いはキセノンランプ等のフラッシュ光
等で定着を行うことによって印写物を得る。In electrophotography, electrostatic recording, etc., an electrostatic charge image is formed on a photoreceptor by various methods, and then the electrostatic charge image is developed with toner particles. A printed matter is obtained by transferring it to another transfer material and fixing it with a heating roll, pressure roll, hot pressure roll, or flash light from a xenon lamp.
印写物は汚れや損傷を防ぎ、長期間使用あるいは保管す
る目的で、軟質塩ビ重合体シートからなる用紙入れに挟
んでおかれることが多い。Prints are often placed in paper containers made of soft PVC polymer sheets to prevent stains and damage and to allow long-term use or storage.
電子写真、静電記録の分野に使用される静電荷像現像用
トナーとしては、ポリスチレン樹脂を用いたトナー(特
公昭44−16118号公報)やスチレン−メタクリル
酸ブチル共重合樹脂を用いたトナー(特公昭56−11
143号公報)等のビニル系樹脂を用いて1〜ナー、ビ
スフェノールとエピクロルヒドリンを反応させて得られ
るビスフェノール型エポキシ樹脂を用いたトナー(特開
昭57−96354号公報)、ビスフェノール骨格を有
するグリコールと多塩基酸とを反応させて得られるポリ
エステル樹脂を用いたトナー(特公昭52−25420
号公報)等が知られているが、ビニル系樹脂は他の樹脂
に比べて分子量、ガラス転移点、溶融粘度等の樹脂物性
を広範囲に操作でき、トナーの設計上、極めて有利であ
ることからトナーの大半はこのビニル系樹脂を用いたト
ナーで占められている。Toners for developing electrostatic images used in the fields of electrophotography and electrostatic recording include toners using polystyrene resin (Japanese Patent Publication No. 44-16118) and toners using styrene-butyl methacrylate copolymer resin ( Special Public Service 1986-11
Toner using a bisphenol-type epoxy resin obtained by reacting bisphenol with epichlorohydrin (Japanese Patent Application Laid-open No. 1982-96354), glycol having a bisphenol skeleton, etc. Toner using polyester resin obtained by reacting with polybasic acid (Japanese Patent Publication No. 52-25420)
However, compared to other resins, vinyl resins are extremely advantageous in terms of toner design, as their physical properties such as molecular weight, glass transition point, and melt viscosity can be controlled over a wide range. The majority of toners are toners using this vinyl resin.
ところで、印写物は汚れや損傷を防ぎ、長時間使用ある
いは保管する目的で、軟質塩ビ重合体シートからなる用
紙入れに挟んでおかれることが多い。しかし、従来のビ
ニル系樹脂を用いたトナーは、該トナーを用いた印写物
を軟質塩ビ重合体シートに挟むと、印写した文字や図形
が該シートに付着して印字欠損を生じ、判読不能になる
という重大な欠点を有していた。By the way, in order to prevent stains and damage and to use or store the printed matter for a long time, the printed matter is often placed in a paper case made of a soft vinyl chloride polymer sheet. However, with conventional toners using vinyl resin, when printed matter made with the toner is sandwiched between soft PVC polymer sheets, the printed characters and figures adhere to the sheets, causing print defects and making them difficult to read. It had the serious drawback of becoming incapacitated.
本発明は前記の問題点を解決し、トナーとして必要な画
像濃度耐カブリ性及び、耐ブロッキング性を有すると共
に軟質塩ビ重合体シートに付着しないトナーを提供する
ことを目的とする。SUMMARY OF THE INVENTION An object of the present invention is to solve the above-mentioned problems and provide a toner that has the image density fog resistance and blocking resistance necessary for a toner and does not adhere to a soft vinyl chloride polymer sheet.
本発明は、下記、一般式(Iンで表されるビニルモノマ
ーを構成成分として有する重合体を結着剤〔但し、一般
式(り中、R1は水素又はメチル基、Rzは炭素数1〜
6のアルキレン基又は脂環若しであり、Ra、 Ran
Ran R7t Ra及びR9は水素、炭素数1〜3
のアルキル基、ハロゲン、でもよい。The present invention uses a polymer having as a constituent component a vinyl monomer represented by the following general formula (I) as a binder [wherein R1 is hydrogen or a methyl group, and Rz has 1 to 1 carbon atoms]
6 alkylene group or alicyclic group, Ra, Ran
Ran R7t Ra and R9 are hydrogen, carbon number 1-3
may be an alkyl group or a halogen.
謁
なお、上記式中のR2のt環又は芳香環を有する二価の
有機基を具体的に例示すると、次のものがある。Specific examples of the divalent organic group having a t ring or an aromatic ring for R2 in the above formula include the following.
但し、R′は、炭素数1〜6のアルキレン基、←炭素数
1〜6のアルキレン基→〇−1又は−(炭素数1〜6の
アルキレン基→O←炭素数1〜6のアルキレン基→であ
る。However, R' is an alkylene group having 1 to 6 carbon atoms, ←alkylene group having 1 to 6 carbon atoms→〇-1 or -(alkylene group having 1 to 6 carbon atoms→O←alkylene group having 1 to 6 carbon atoms) → is.
本発明に係る静電荷像現像用トナーの結着剤樹脂は、上
記一般式(I)で表されるビニルモノマー(以下、「本
発明の特定上ツマ−」という)を必須成分として含むも
のであるが、そのためには、結着剤として次のものが使
用される。The binder resin of the toner for developing electrostatic images according to the present invention contains a vinyl monomer represented by the above general formula (I) (hereinafter referred to as "the specific monomer of the present invention") as an essential component. , for which the following are used as binders:
(A)本発明の特定モノマーのうち1種の重合体若しく
は2種以上の共重合体又はそれらの混合物を成分とする
樹脂。(A) A resin containing one kind of polymer, two or more kinds of copolymers, or a mixture thereof among the specific monomers of the present invention.
(B)本発明の特定モノマーのうち1種以上及び他の付
加重合性モノマーの1種以上の共重合体又はそれらの混
合物を成分とする樹脂。(B) A resin containing as a component a copolymer of one or more of the specific monomers of the present invention and one or more other addition-polymerizable monomers, or a mixture thereof.
(C)上記(A)の樹脂と上記(B)の樹脂の混合物。(C) A mixture of the resin of (A) above and the resin of (B) above.
(D)上記(A)の樹脂及び/又は上記(B)の樹脂と
他の樹脂との混合物。(D) A mixture of the resin of (A) above and/or the resin of (B) above and another resin.
本発明の特定モノマーは、そのうちの少なくとも1種が
結着剤中に、成分として好ましくは5〜90重量%、さ
らに好ましくは20〜70重量%、特に好ましくは25
〜60重量%含まれるように配合される。本発明の特定
モノマーの配合量が少なすぎるとトナーの塩ビ重合体に
対する耐付着性が不充分となり、多すぎるとトナーとし
ての性能が不充分になる傾向がある。At least one of the specific monomers of the present invention is contained in the binder as a component, preferably 5 to 90% by weight, more preferably 20 to 70% by weight, particularly preferably 25% by weight.
It is blended to contain up to 60% by weight. If the amount of the specific monomer of the present invention is too small, the adhesion resistance of the toner to the vinyl chloride polymer tends to be insufficient, and if it is too large, the performance as a toner tends to be insufficient.
本発明の特定モノマーは、例えば、対応する脂環式構造
を有する酸無水物と炭素数1〜5のアルキレン基又は脂
環若しくは芳香環を有するアミノアルコールをイミド化
反応させた後、アクリル酸若しくはメタクリル酸又はこ
れらの低級アルキルエステルを加え、エステル化反応又
はエステル交換反応させることにより製造することがで
き、代表的なものとしては、次のモノマーが挙げられる
。The specific monomer of the present invention can be produced by, for example, imidizing an acid anhydride having a corresponding alicyclic structure with an alkylene group having 1 to 5 carbon atoms or an amino alcohol having an alicyclic ring or an aromatic ring, and then producing acrylic acid or an aromatic ring. It can be produced by adding methacrylic acid or a lower alkyl ester thereof and carrying out an esterification reaction or transesterification reaction, and typical monomers include the following monomers.
(ビニルモノマーA)
(ビニルモノマーD)
(ビニルモノマーB)
上記特定モノマーと共重合させることができる他の付加
重合性モノマーは必要に応じて使用されるが、共重合成
分である全ビニルモノマーに対して10〜95重景%配
重量れるのが好ましい、他の付加重合性モノマーの具体
例を以下に示す。(Vinyl monomer A) (Vinyl monomer D) (Vinyl monomer B) Other addition-polymerizable monomers that can be copolymerized with the above specific monomers are used as necessary, but the total vinyl monomer that is the copolymerization component Specific examples of other addition-polymerizable monomers, which preferably have a distribution weight of 10 to 95% relative to the total weight, are shown below.
スチレン、メトキシスチレン、ブトキシスチレン、α−
メチルスチレン、p−メチルスチレン。Styrene, methoxystyrene, butoxystyrene, α-
Methylstyrene, p-methylstyrene.
p−t−ブチルスチレン、p−クロルスチレン等のスチ
レン誘導体、メタクリル酸、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
ブチル、メタクリル酸ペンチル、メタクリル酸ヘキシル
、メタクリル酸ヘプチル、メタクリル酸デシル、メタク
リル酸ウンデシル、メタクリル酸ドデシル、メタクリル
酸グリシジル、メタクリル酸メトキシエチル、メタクリ
ル酸プロポキシエチル、メタクリル酸ブトキシエチル、
メタクリル酸メトキシジエチレングリコール。Styrene derivatives such as pt-butylstyrene and p-chlorostyrene, methacrylic acid, methyl methacrylate, ethyl methacrylate, propyl methacrylate, butyl methacrylate, pentyl methacrylate, hexyl methacrylate, heptyl methacrylate, decyl methacrylate , undecyl methacrylate, dodecyl methacrylate, glycidyl methacrylate, methoxyethyl methacrylate, propoxyethyl methacrylate, butoxyethyl methacrylate,
Methoxydiethylene glycol methacrylate.
メタクリル酸エトキシジエチレングリコール、メタクリ
ル酸メトキシエチレングリコール、メタクリル酸ブトキ
シトリエチレングリコール、メタクリル酸メトキシジプ
ロピレングリコール、メタクリル酸フェノキシエチル、
メタクリル酸フェノキシジエチレングリコール、メタク
リル酸フェノキシテトラエチレングリコール、メタクリ
ル酸ベンジル、メタクリル酸シクロヘキシル、メタクリ
ル酸テトラヒドロフルフリル、メタクリル酸ジシクロペ
ンテニル、メタクリル酸ジシクロペンテニルオキシエチ
ル、メタクリル酸N−ビニル−2−ピロリドン、メタク
リ口ニトリル、メタクリルアミド、N−メチロールメタ
クリルアミド、メタクリル酸エチルモルホリン、メタク
リル酸2−ヒドロキシエチル、メタクリル酸ヒドロキシ
プロピル。Ethoxydiethylene glycol methacrylate, methoxyethylene glycol methacrylate, butoxytriethylene glycol methacrylate, methoxydipropylene glycol methacrylate, phenoxyethyl methacrylate,
Phenoxydiethylene glycol methacrylate, phenoxytetraethylene glycol methacrylate, benzyl methacrylate, cyclohexyl methacrylate, tetrahydrofurfuryl methacrylate, dicyclopentenyl methacrylate, dicyclopentenyloxyethyl methacrylate, N-vinyl-2-pyrrolidone methacrylate, Methacrylic nitrile, methacrylamide, N-methylolmethacrylamide, ethylmorpholine methacrylate, 2-hydroxyethyl methacrylate, hydroxypropyl methacrylate.
メタクリル酸ヒドロキシブチル、メタクリル酸2−ヒド
ロキシ−3−フェニルオキシプロピル、ジアセトンメタ
クリルアミド、アクリル酸、アクリル酸メチル、アクリ
ル酸エチル、アクリル酸プロピル、アクリル酸ブチル、
アクリル酸ペンチル。Hydroxybutyl methacrylate, 2-hydroxy-3-phenyloxypropyl methacrylate, diacetone methacrylamide, acrylic acid, methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate,
Pentyl acrylate.
アクリル酸ヘキシル、アクリル酸ヘプチル、アクリル酸
オクチル、アクリル酸ノニル、アクリル酸デシル、アク
リル酸ウンデシル、アクリル酸ドデシル、アクリル酸グ
リシジル、アクリル酸メトキシエチル、アクリル酸プロ
ポキシエチル、アクリル酸ブトキシエチル、アクリル酸
メトキシジエチレングリコール、アクリル酸エトキシジ
エチレングリコール、アクリル酸メトキシエチレングリ
コール、アクリル酸ブトキシトリエチレングリコール、
アクリル酸メトキシジプロピレングリコール。Hexyl acrylate, heptyl acrylate, octyl acrylate, nonyl acrylate, decyl acrylate, undecyl acrylate, dodecyl acrylate, glycidyl acrylate, methoxyethyl acrylate, propoxyethyl acrylate, butoxyethyl acrylate, methoxy acrylate Diethylene glycol, ethoxydiethylene glycol acrylate, methoxyethylene glycol acrylate, butoxytriethylene glycol acrylate,
Methoxydipropylene glycol acrylate.
アクリル酸フェノキシエチル、アクリル酸フェノキシジ
エチレングリコール、アクリル酸フェノキシテトラエチ
レングリコール、アクリル酸ベンジル、アクリル酸シク
ロヘキシル、アクリル酸テトラヒドロフルフリル、アク
リル酸ジシクロペンテニル、アクリル酸ジシクロペンテ
ニルオキシエチル、アクリル酸N−ビニル−2−ピロリ
ドン、アクリル酸ヒドロキシエチル、アクリル酸ヒドロ
キシプロピル、アクリル酸ヒドロキシブチル、アクリル
酸2−ヒドロキシ−3−フェニルオキシプロピル、アク
リル酸グリシジル、アクリロニトリル。Phenoxyethyl acrylate, phenoxydiethylene glycol acrylate, phenoxytetraethylene glycol acrylate, benzyl acrylate, cyclohexyl acrylate, tetrahydrofurfuryl acrylate, dicyclopentenyl acrylate, dicyclopentenyloxyethyl acrylate, N-vinyl acrylate -2-pyrrolidone, hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxybutyl acrylate, 2-hydroxy-3-phenyloxypropyl acrylate, glycidyl acrylate, acrylonitrile.
アクリルアミド、N−メチロールアクリルアミド。Acrylamide, N-methylolacrylamide.
ジアセトンアクリルアミド、メタクリル酸ジエチルアミ
ノエチル、メタクリル酸ジメチルアミノエチル、アクリ
ル酸エチルモルホリン、ビニルピリジンマレイン酸ジエ
チル、マレイン酸ジブチル。Diacetone acrylamide, diethylaminoethyl methacrylate, dimethylaminoethyl methacrylate, ethylmorpholine acrylate, vinylpyridine diethyl maleate, dibutyl maleate.
フマル酸ジエチル、フマル酸ジブチル、フマル酸オクチ
ル等の1分子中に1個のビニル基を有するビニルモノマ
ーや、ジビニルベンゼン、グリコールとメタクリル酸あ
るいはアクリル酸との反応生成物、例えばエチレングリ
コールジメタクリレート、1.3−ブチレンゲリコール
ジメタクリレート、1,4−ブタンジオールジメタクリ
レート。Vinyl monomers having one vinyl group in each molecule such as diethyl fumarate, dibutyl fumarate, and octyl fumarate, divinylbenzene, reaction products of glycol and methacrylic acid or acrylic acid, such as ethylene glycol dimethacrylate, 1.3-butylene gelicol dimethacrylate, 1,4-butanediol dimethacrylate.
1.5−ベンタンジオールジメタクリレート、1゜6−
ヘキサンジオールジアクリレート、ネオペンチルグリコ
ールジメタクリレート、ジエチレングリコールジメタク
リレート、トリエチレングリコールジメタクリレート、
ポリエチレングリコールジメタクリレート、トリプロピ
レングリコールジメタクリレート、ヒドロキシピバリン
酸ネオペンチルグリコールエステルジメタクリレート、
トリメチロールエタントリメタクリレート、トリメチロ
ールプロパントリメタクリレート、ペンタエリトリット
トリメタクリレート、ペンタエリトリットテトラメタク
リレート、トリスメタクリロキシエチルホスフェート、
ビス(メタクリロイルオキシエチル)ヒドロキシエチル
イソシアヌレート。1.5-bentanediol dimethacrylate, 1゜6-
Hexanediol diacrylate, neopentyl glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate,
Polyethylene glycol dimethacrylate, tripropylene glycol dimethacrylate, hydroxypivalic acid neopentyl glycol ester dimethacrylate,
Trimethylolethane trimethacrylate, trimethylolpropane trimethacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, trismethacryloxyethyl phosphate,
Bis(methacryloyloxyethyl)hydroxyethyl isocyanurate.
トリス(メタクリロイルオキシエチル)イソシアヌレー
ト、エチレングリコールジアクリレート。Tris (methacryloyloxyethyl) isocyanurate, ethylene glycol diacrylate.
1.3−ブチレンゲ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、ネオペンチルグリコールジアクリレート、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、ポリエチレングリコールジアク
リレート。1.3-Butylene gelicol diacrylate, 1゜4-
Butanediol diacrylate, 1,5-bentanediol diacrylate, 1,6-hexanediol diacrylate, neopentyl glycol diacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, polyethylene glycol diacrylate.
トリプロピレンジアクリレート、ヒドロキシピバリン酸
ネ建ペンチルグリコールジアクリレート。Tripropylene diacrylate, hydroxypivalic acid pentyl glycol diacrylate.
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、ペンタエリトリットトリ
アクリレート、ペンタエリトリットテトラアクリレート
、トリスアクリロキシエチルホスフェート、ビス(メタ
クリロイルオキシエチル)ヒドロキシエチルイソシアヌ
レート、トリス(メタクリロイルオキシエチル)イソシ
アヌレート、メタクリル酸グリシジルとメタクリル酸あ
るいはアクリル酸のハーフェステル化物、ビスフェノー
ル型エポキシ樹脂とメタクリル酸あるいはアクリル酸の
ハーフェステル化物、アクリル酸グリシジルとメタクリ
ル酸あるいはアクリル酸のハーフェステル化物等の1分
子中に2個以上のビニル基を有するビニルモノマーを挙
げることができる。Trimethylolethane triacrylate, trimethylolpropane triacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, trisacryloxyethyl phosphate, bis(methacryloyloxyethyl)hydroxyethyl isocyanurate, tris(methacryloyloxyethyl)isocyanurate, Two or more vinyls in one molecule, such as a halfester compound of glycidyl methacrylate and methacrylic acid or acrylic acid, a halfester compound of bisphenol-type epoxy resin and methacrylic acid or acrylic acid, and a halfester compound of glycidyl acrylate and methacrylic acid or acrylic acid. Mention may be made of vinyl monomers having groups.
これらのビニルモノマーのうち特に好ましいのは、1分
子中41個のビニル基を有するビニルモノマーでは、ス
チレン、スチレン誘導体、メタクリル酸エステル、アク
リル酸エステル等があり、特にアルキル基に1〜5個の
炭素原子を有するメタクリル酸あるいはアクリル酸のア
ルキルエステルが好ましい、1分子中に2個以上のビニ
ル基を有するビニルモノマーでは、ジビニルベンゼン。Among these vinyl monomers, particularly preferred vinyl monomers having 41 vinyl groups in one molecule include styrene, styrene derivatives, methacrylic esters, acrylic esters, and especially those having 1 to 5 vinyl groups in the alkyl group. Among the vinyl monomers having two or more vinyl groups in one molecule, preferred are alkyl esters of methacrylic acid or acrylic acid having carbon atoms, such as divinylbenzene.
炭素原子数2〜6個のメチレングリコールのジメタクリ
レート及びジアクリレート等が好ましく。Dimethacrylates and diacrylates of methylene glycol having 2 to 6 carbon atoms are preferred.
これらは全ビニルモノマー中、0〜20重量%使用され
る。これら1分子中に1個のビニル基を有するビニルモ
ノマー及び1分子中に2個のビニル基を有するビニルモ
ノマーは単独で又は2種以上を組み合わせて使用するこ
とができる。These are used in an amount of 0 to 20% by weight based on the total vinyl monomers. These vinyl monomers having one vinyl group in one molecule and vinyl monomers having two vinyl groups in one molecule can be used alone or in combination of two or more.
上記ビニルモノマーは、溶液重合、塊状重合。The above vinyl monomer can be polymerized in solution or in bulk.
乳化重合、懸濁重合等任意の方法で重合させることがで
きる。Polymerization can be carried out by any method such as emulsion polymerization or suspension polymerization.
これらのモノマーの重合に際し、使用される重合開始剤
としては2,2′−アゾビスイソブチロニトリル、2.
2’−アゾビス−(2,4−ジメチルバレロニトリル)
、2.2’−アゾビス(4−メトキシ−2,4−ジメチ
ルバレロニトリル等のアゾ系化合物、t−ブチルパーオ
キシ(2−エチルヘキサノエート)11−ブチルパーオ
キシイソブチレート等のパーオキシエステル、1.1−
ビス(t−ブチルパーオキシ)3,3.5−トリメチル
シクロヘキサン、1,1−ビス(t−ブチルパーオキシ
)シクロヘキサン等のパーオキシケタール、ジクミルパ
ーオキサイド、2,5−ジメチル−2,5−ジ(t−ブ
チルパーオキシ)ヘキサン等のジアルキルパーオキサイ
ド、ベンゾイルパーオキサイド、アセチルパーオキサイ
ド等のジアシルパーオキサイドがある。これらは全ビ丘
ルモノマーに対して0.1〜15重量%使用されるのが
好ましい。In the polymerization of these monomers, the polymerization initiators used include 2,2'-azobisisobutyronitrile, 2.
2'-azobis-(2,4-dimethylvaleronitrile)
, azo compounds such as 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), peroxy compounds such as t-butylperoxy(2-ethylhexanoate) 11-butylperoxyisobutyrate ester, 1.1-
Peroxyketals such as bis(t-butylperoxy)3,3.5-trimethylcyclohexane and 1,1-bis(t-butylperoxy)cyclohexane, dicumyl peroxide, 2,5-dimethyl-2,5 There are dialkyl peroxides such as -di(t-butylperoxy)hexane, diacyl peroxides such as benzoyl peroxide, and acetyl peroxide. Preferably, these are used in an amount of 0.1 to 15% by weight based on the total molecular monomers.
また、これらのモノマーの重合に際し、公知の連鎖移動
剤を使用することができる。連鎖移動剤は全モノマーに
対して、0〜5重量%使用されるのが好ましい。Furthermore, known chain transfer agents can be used during polymerization of these monomers. The chain transfer agent is preferably used in an amount of 0 to 5% by weight based on the total monomers.
本発明になる結着剤樹脂は、ガラス転移温度が40〜1
00℃に調整されるのが好ましく、特に50〜90”C
が好ましい、40℃未満ではトナーの耐ブロッキング性
が劣る傾向があり、100℃を越えるとトナーの粉砕性
が低下する傾向がある。The binder resin of the present invention has a glass transition temperature of 40 to 1
It is preferable to adjust the temperature to 00"C, especially 50 to 90"C.
If the temperature is less than 40°C, the blocking resistance of the toner tends to be poor, and if it exceeds 100°C, the crushability of the toner tends to decrease.
本発明になるトナーは、さらに着色剤及び/又は磁性粉
を含有してなる。The toner of the present invention further contains a colorant and/or magnetic powder.
着色剤としては、カーボンブラック、アセチレンブラッ
ク、ランプブラック、黒鉛、鉄黒、アニリンブラック、
シアニンブラック等の黒色着色剤。Colorants include carbon black, acetylene black, lamp black, graphite, iron black, aniline black,
Black colorants such as cyanine black.
黄鉛、カドミウムイエロー、黄色酸化鉄、チタン黄、ナ
フトールイエロー、ハンザイエロー、ピグメントイエロ
ー、ベンジジンイエロー、パーマネントイエロー、キノ
リンイエローレーキ、アンスラピリミジンイエロー等の
黄色着色剤、パーマネントオレンジ、パルカンファスト
オレンジ、ベンジジンオレンジ、インダンスレンブリリ
アントオレンジ等の橙色着色剤、酸化鉄、アンバー、パ
ーマネントブラウン等の褐色着色剤、ベンガラ、アンチ
モン朱、パーマネントレッド、ファイヤーレッド、ブリ
リアントカーミン、ライトファスレッドトーナー、パー
マネントカーミン、ピラゾロンレッド、ボルドー、ヘリ
オボルドー、ローダミンレーキ、チオインジゴレッド、
チオインジゴレッドン等の赤色着色剤、コバルト紫、フ
ァストバイオレット、ジオキサジンバイオレット等の紫
色着色剤、コバルトブルー、セルリアンブルー、無金属
フタロシアニンブルー、フタロシアニンブルー。Yellow coloring agents such as yellow lead, cadmium yellow, yellow iron oxide, titanium yellow, naphthol yellow, Hansa yellow, pigment yellow, benzidine yellow, permanent yellow, quinoline yellow lake, anthrapyrimidine yellow, permanent orange, palkan fast orange, benzidine Orange, orange colorants such as indanthrene brilliant orange, iron oxide, amber, brown colorants such as permanent brown, red iron oxide, antimony vermilion, permanent red, fire red, brilliant carmine, light fast red toner, permanent carmine, pyrazolone red , Bordeaux, Heliobordeaux, Rhodamine Lake, Thioindigo Red,
Red colorants such as thioindigo reddon, purple colorants such as cobalt violet, fast violet, dioxazine violet, cobalt blue, cerulean blue, metal-free phthalocyanine blue, phthalocyanine blue.
インダンスレンブル−、インジゴ等の青色着色剤。Blue coloring agents such as indanthremble and indigo.
クロムグリーン、コバルトグリーン、グリーンゴールド
、フタロシアニングリーン、ポリクロムブロム銅フタロ
シアニン等の緑色着色剤等があり、耐熱分解性を必要と
する場合にはカーボンブラック、鉄黒、シアニンブラッ
ク、黄色酸化鉄、チタン黄、ハンザイエロー、ベンジジ
ンイエロー、パーマネントオレンジ、パルカンファスト
オレンジ。There are green coloring agents such as chrome green, cobalt green, green gold, phthalocyanine green, polychrome bromine copper phthalocyanine, etc., and when heat decomposition resistance is required, carbon black, iron black, cyanine black, yellow iron oxide, and titanium are used. Yellow, Hansa Yellow, Benzidine Yellow, Permanent Orange, Palkan Fast Orange.
酸化鉄、ベンガラ、ファイヤーレッド、ライトファスレ
ッドトーナー、パーマネントカーミン、ピラゾロンレッ
ド、ボルドー、チオインジゴマルーン、コバルト紫、コ
バルトブルー、セルリアンブルー、フタロシアニンブル
ー、コバルトグリーン。Iron oxide, Red Garla, Fire Red, Light Fast Red Toner, Permanent Carmine, Pyrazolone Red, Bordeaux, Thioindigo Maroon, Cobalt Purple, Cobalt Blue, Cerulean Blue, Phthalocyanine Blue, Cobalt Green.
フタロシアニングリーン、ポリクロムブロム銅フタロシ
アニン等が特に好ましい。これら着色剤は全トナー成分
中に1〜60重量%配合されるのが好ましい。1重量%
未満では着色が不充分であり、60重量%を越えるとト
ナーの定着強度が低下する傾向がある。Particularly preferred are phthalocyanine green, polychrome bromine copper phthalocyanine, and the like. These colorants are preferably blended in an amount of 1 to 60% by weight in the total toner components. 1% by weight
If it is less than 60% by weight, the coloring is insufficient, and if it exceeds 60% by weight, the fixing strength of the toner tends to decrease.
なお、本発明になるトナーをキセノン閃光照射法による
定着法に適用する場合は、トナー中にキャノン光の最大
強度である800〜11000nの光を吸収しうるキャ
ノン光吸収剤が含有されるが、これらの中には、カーボ
ンブラック、トリアゾ化合物フタロシアニン化合物、ナ
フトロシアニン化合物等の自ら着色能力をも備えるもの
があるので、そのようなキャノン光吸収剤を使用する時
には、新たに他の着色剤を加えなくてもよい場合もある
。キセノン光吸収剤はその他、ポリメチン化合物、アズ
レニウム塩+ Cr F z g Cu CQ z +
FeCQs 、 Fe5Oa・7Hz○、MoCQ
s。Note that when the toner of the present invention is applied to a fixing method using a xenon flash irradiation method, the toner contains a Cannon light absorber that can absorb light of 800 to 11000 nm, which is the maximum intensity of Cannon light. Some of these compounds, such as carbon black, triazo compounds, phthalocyanine compounds, and naphthrocyanine compounds, have the ability to color themselves, so when using such Canon light absorbers, it is necessary to add another colorant. In some cases, it may not be necessary to add it. Other xenon light absorbers include polymethine compounds, azulenium salts + Cr F z g Cu CQ z +
FeCQs, Fe5Oa・7Hz○, MoCQ
s.
N1CQz、VCQa、VC+l14.VFa、VSO
a・7HxO等があり、これらは、全トナー成分中に1
〜20重量%配合されるのが好ましく、特に3〜15重
景%重量ましい、1重量%未満ではキセノン光の吸収が
不足し定着強度が低下する傾向があり、20重量%を越
えても、より高い効果は期待できない上、帯電性の低下
等の弊害発生の頻度が高まる傾向がある。N1CQz, VCQa, VC+l14. VFa, VSO
a・7HxO, etc., and these contain 1% of the total toner components.
It is preferable that the amount of xenon is 20% by weight, especially 3-15% by weight.If it is less than 1% by weight, the absorption of xenon light will be insufficient and the fixing strength will tend to decrease, but if it exceeds 20% by weight, , higher effects cannot be expected, and the frequency of occurrence of adverse effects such as a decrease in chargeability tends to increase.
磁性粉は、使用形態が一成分トナーの場合に配合される
。磁性粉としては、鉄、マンガン、ニッケル、コバルト
等の金属粉末、アルミニウム、コバルト、鋼鉄、鉛、マ
グネシウム、ニッケル、錫。Magnetic powder is blended when the toner is used as a one-component toner. Magnetic powders include metal powders such as iron, manganese, nickel, and cobalt, aluminum, cobalt, steel, lead, magnesium, nickel, and tin.
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。Zinc, antimony, beryllium, bismuth, cadmium, calcium, manganese, selenium, titanium.
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、酸化アルミニウム、酸化鉄、酸化銅、酸化ニッ
ケル、酸化亜鉛、酸化チタン、酸化マグネシウム、酸化
クロムのような金属酸化物を含む金属化合物、又は熱処
理を施すと強磁性を示す合金、例えばマンガン−銅−ア
ルミニウム、マンガン−銅−錫等のボイスカー合金等を
使用することができる。磁性粉の粒径は10μm以下が
好ましく、特に1μm以下が好ましい、これら磁性粉は
トナー中に30〜70重量%の量で含有させる。磁性粉
を用いる場合、上記着色剤をさらに添加してもよく、そ
の量はトナー中に10重量%以下が好ましい。Metal alloys and mixtures thereof such as tungsten, vanadium, metal compounds including metal oxides such as aluminum oxide, iron oxide, copper oxide, nickel oxide, zinc oxide, titanium oxide, magnesium oxide, chromium oxide, or heat treatment. Alloys that exhibit ferromagnetism when applied, such as Boyceker alloys such as manganese-copper-aluminum and manganese-copper-tin, can be used. The particle size of the magnetic powder is preferably 10 μm or less, particularly preferably 1 μm or less. These magnetic powders are contained in the toner in an amount of 30 to 70% by weight. When using magnetic powder, the above colorant may be further added, and the amount thereof is preferably 10% by weight or less in the toner.
また5本発明になるトナーには、必要に応じて他の樹脂
や、帯電制御剤、流動性向上剤、クリーニング性向上剤
、オフセット防止剤等の添加剤を使用することができる
。Further, the toner of the present invention may contain other resins and additives such as a charge control agent, a fluidity improver, a cleanability improver, and an anti-offset agent, if necessary.
他の樹脂としては、スチレン樹脂、スチレンアグリル樹
脂、シリコン樹脂、ポリエステルカーボネート樹脂、キ
シレン樹脂、エポキシ樹脂、フェノール樹脂、ジエン系
樹脂、クマロン樹脂、アミド樹脂、アミノ樹脂、ウレタ
ン樹脂等があり、これらは全トナー成分中に好ましくは
0〜30重量%範囲で配合される。Other resins include styrene resin, styrene agril resin, silicone resin, polyester carbonate resin, xylene resin, epoxy resin, phenol resin, diene resin, coumaron resin, amide resin, amino resin, urethane resin, etc. is preferably blended in the total toner components in an amount of 0 to 30% by weight.
帯電制御剤としてはニゲロン染料、脂肪配変性ニグロシ
ン染料、テトラアルキルアンモニウムハライド、トリア
ルキルアンモニウムハライド。As the charge control agent, nigerone dye, adipose-modified nigrosine dye, tetraalkylammonium halide, and trialkylammonium halide are used.
(式中X′はハロゲンを表し、Rは炭素原子数1〜3個
のアルキレン基、nは0又は1を表す)、構造単位を有
するポリアミン化合物。(In the formula, X' represents a halogen, R represents an alkylene group having 1 to 3 carbon atoms, and n represents 0 or 1), a polyamine compound having a structural unit.
R1’
鵞
−CHz −C(CH) −
(式中R1’ は水素又は炭素原子数1〜3個のアル
キル基を表す)の構造単位を有するニトリル化(式中R
Cはアルコキシ基又はフェノキシ基を表し、R8’
は水素、アルコキシ基又はフェノキシ基を表す)の化合
物、モノアルキル錫オキシド。Nitrilation (in the formula, R
C represents an alkoxy group or a phenoxy group, R8'
represents hydrogen, an alkoxy group or a phenoxy group), monoalkyltin oxide.
ジアルキル錫オキシド、モノアリール錫オキシド。Dialkyltin oxide, monoaryltin oxide.
式:
(式中Rν、Rs’ 、R,’及びR7’は水素、炭素
原子数1〜9個のアルキル基又は芳香環若しくはシクロ
ヘキセン環を有する置換基を表すが、2個以上の基が同
時に水素を表さず、MeはCr。Formula: (In the formula, Rν, Rs', R,' and R7' represent hydrogen, an alkyl group having 1 to 9 carbon atoms, or a substituent having an aromatic ring or a cyclohexene ring, but two or more groups simultaneously It does not represent hydrogen, and Me is Cr.
CO又はFeを表し、Mは水素、カリウム、ナトリウム
又は脂肪酸アンモニウムを表す)の化合物。CO or Fe, M represents hydrogen, potassium, sodium or fatty acid ammonium).
式:
(式中Rs ’及びRg/は炭素原子数1〜9個のアル
キレン基、芳香環又はシクロヘキセン環を表し、Me及
びMは前記のものを表す)の化合物、式:(式中T、Y
及びZは水素、ハロゲン、カルボキシル基、ヒドロキシ
ル基、ニトロ基、スルホン基又はスルホンアミド基を表
し1M及びMeは前記のものを表す)、テトラチアフル
バレン、アルミナ微粉末等を使用でき、トナー中に通常
O〜20重景%重量で添加される。A compound of the formula: (wherein Rs' and Rg/ represent an alkylene group, an aromatic ring, or a cyclohexene ring having 1 to 9 carbon atoms, and Me and M represent the above), a compound of the formula: (wherein T, Y
and Z represent hydrogen, halogen, carboxyl group, hydroxyl group, nitro group, sulfone group or sulfonamide group; 1M and Me represent the above), tetrathiafulvalene, alumina fine powder, etc. can be used, and in the toner. It is usually added in an amount of 0 to 20% by weight.
但し本発明の特定モノマーのうち1分子中にIO
0ゲン、−〇−51−Rlz、 −NOx又は−5Oa
H1x
を有する特定モノマーは重合体に、それぞれ正帯電性及
び負帯電性を与えるためこれらのモノマーを成分として
有する重合体を用いる場合は正帯電性トナーあるいは負
帯電性トナーを製造する際に。However, among the specific monomers of the present invention, one molecule contains IO0gen, -〇-51-Rlz, -NOx or -5Oa.
The specific monomer having H1x imparts positive chargeability and negative chargeability to the polymer, respectively, so when a polymer containing these monomers is used as a component, it is necessary to produce a positively chargeable toner or a negatively chargeable toner.
ニグロシン染料、アゾ化合物及びサリチル酸金属錯体等
の帯電制御剤を加えることは必ずしも必要としない。It is not necessary to add charge control agents such as nigrosine dyes, azo compounds and metal salicylate complexes.
流動性向上剤は、トナーに高い流動性を付与し、トナー
の連続供給を容易にして良好な画質の可視画像を形成す
る役目をなす、流動性向上剤としては、疎水性化したシ
リカ粉末が最適である。このような疎水性シリカ粉末は
1表面珪素原子がシラノール基になっている二酸化珪素
の微粉末を、例えばオクチルトリクロルシラン、デシル
トリクロルシラン、ノニルトリクロルシラン、4−イソ
プロピルフェニルトリクロルシラン、4−tart−ブ
チルフェニルトリクロルシラン、ジメチルジクロルシラ
ン、ジペンチルジクロルシラン、ジヘキシルジク口ルシ
ラン、ジオクチルジクロルシラン。The fluidity improver imparts high fluidity to the toner, facilitates continuous toner supply, and forms visible images of good quality.As the fluidity improver, hydrophobicized silica powder is used as a fluidity improver. Optimal. Such hydrophobic silica powder is a fine powder of silicon dioxide in which one surface silicon atom is a silanol group, such as octyltrichlorosilane, decyltrichlorosilane, nonyltrichlorosilane, 4-isopropylphenyltrichlorosilane, 4-tart- Butylphenyltrichlorosilane, dimethyldichlorosilane, dipentyldichlorosilane, dihexyldichlorosilane, dioctyldichlorosilane.
ジドデシルジクロルシラン、4−tart−ブチルフェ
ニルオクチルジクロルシラン、ジオクチルジクロルシラ
ン、ジデセニルジク口ルシラン、ジノネニルジク口ルシ
ラン、ジー2−エチルへキシルジクロルシラン、ジー3
,3−ジメチルペンチルジクロルシラン、トリメチルク
ロルシラン、トリへキシルクロルシラン、トリオクチル
クロルシラン。Didodecyl dichlorosilane, 4-tart-butylphenyl octyl dichlorosilane, dioctyl dichlorosilane, didecenyl dichlorosilane, dinonenyl dichlorosilane, di-2-ethylhexyl dichlorosilane, di-3
, 3-dimethylpentyldichlorosilane, trimethylchlorosilane, trihexylchlorosilane, trioctylchlorosilane.
トリデシルクロルシラン、ジオクチルクロルシラン、オ
クチルジメチルクロルシラン、4−インプロピルフェニ
ルジエチルクロルシラン等の化合物と反応させることに
より、二酸化珪素粒子の表面珪素原子に酸素原子を介し
て疎水性基を結合させたものである。By reacting with a compound such as tridecylchlorosilane, dioctylchlorosilane, octyldimethylchlorosilane, or 4-impropylphenyldiethylchlorosilane, a hydrophobic group is bonded to the surface silicon atoms of silicon dioxide particles via oxygen atoms. It is something that
これらの疎水性シリカ粉末は、その平均粒径が1vμm
〜1100uの範囲内にあるのが好ましく。These hydrophobic silica powders have an average particle size of 1vμm.
It is preferably within the range of ~1100u.
特に2’p m〜50 μmにあるのが好ましい、 1
mμm未満であると、粉末が飛散しやすく、取り扱いが
困廻であり、100μmを越えると、感光体に損傷を与
えやすい。In particular, it is preferably between 2'p m and 50 μm, 1
If it is less than mμm, the powder tends to scatter and is difficult to handle, and if it exceeds 100μm, the photoreceptor is likely to be damaged.
このような疎水性シリカ粉末は、アエロジルR972,
シリカD−17,R812,RA200H。Such hydrophobic silica powders include Aerosil R972,
Silica D-17, R812, RA200H.
RX−C(以上1日本アエロジル(株)Iり並びにタラ
ノックス500 (Tulco社製)等の商品名で市販
されている。It is commercially available under trade names such as RX-C (manufactured by Nippon Aerosil Co., Ltd.) and Tallanox 500 (manufactured by Tulco).
前記のような疎水性シリカ粉末を他のトナー材料と一緒
に配合してトナーを製造してもよいが、トナーを製造し
、その後に疎水性シリカ粉末を添加するのが好ましい。Although a toner may be manufactured by blending the hydrophobic silica powder as described above with other toner materials, it is preferable to manufacture the toner and then add the hydrophobic silica powder.
疎水性シリカ粉末を添加する場合疎水性シリカ粉末は、
疎水性シリカ粉末を含まないトナー粉末に対して0.0
1〜15重量%の量で加えるのが好ましく、特に、0.
1〜10重量%の添加量が好ましい。この添加量が0.
01 重量%未満であると、流動性向上の効果が現れに
くく、15重量%を越えて添加しても、それだけ効果が
増すものではない。When adding hydrophobic silica powder, hydrophobic silica powder is
0.0 for toner powder without hydrophobic silica powder
It is preferably added in an amount of 1 to 15% by weight, especially 0.
The amount added is preferably 1 to 10% by weight. This addition amount is 0.
If the amount is less than 01% by weight, the effect of improving fluidity is difficult to appear, and even if it is added in excess of 15% by weight, the effect will not increase that much.
クリーニング性向上剤は、トナー成分の一部が感光体あ
るいはキャリア表面に付着する、いわゆるフィルミング
現象を防止し、長期間の連続使用においても常にカプリ
のない鮮明な可視画像を形成する役目をなす。The cleaning performance improver prevents the so-called filming phenomenon, in which a portion of the toner components adheres to the photoreceptor or carrier surface, and plays the role of always forming clear visible images without capri, even after long-term continuous use. .
クリーニング性向上剤としては、飽和又は不飽和脂肪酸
の金属塩9例えば、マレイン酸、ステアリン酸、オレイ
ン酸、バルミチン酸、カプロン酸。Cleanability improvers include metal salts of saturated or unsaturated fatty acids, such as maleic acid, stearic acid, oleic acid, valmitic acid, and caproic acid.
リノール酸、リシノール酸又はリシルイン酸と亜鉛、マ
グネシウム、カルシウム、カドミウム。Linoleic acid, ricinoleic acid or ricylic acid with zinc, magnesium, calcium, cadmium.
鉛、鉄、ニッケル、コバルト、鋼若しくはアルミニウム
との塩又は前述した他の樹脂の微粒子が挙げられ、特に
ステアリン酸亜鉛、ステアリン酸カルシウム、ステアリ
ン酸マグネシウム又は1〜10μmの樹脂粒子が好まし
い。Fine particles of salts with lead, iron, nickel, cobalt, steel or aluminum or other resins mentioned above may be mentioned, and zinc stearate, calcium stearate, magnesium stearate or resin particles of 1 to 10 μm are particularly preferred.
クリーニング性向上剤を使用する場合クリーニング性向
上剤は、前記の疎水性シリカ粉末と同様にして添加する
のが、特に好ましい、これらは該添加剤を含まないトナ
ー粉末に対して0.01〜25重量%、特に0.1〜1
0重量%加えるのが好ましい、0.01 重量%未満で
は、クリーニング性向上の効果が現れにくい、しかし、
25重量%を越えて添加しても、効果が増すものではな
い。When a cleaning performance improver is used, it is particularly preferable to add the cleaning performance improvement agent in the same manner as the hydrophobic silica powder described above. % by weight, especially 0.1-1
It is preferable to add 0% by weight. If it is less than 0.01% by weight, the effect of improving cleaning performance is difficult to appear. However,
Addition of more than 25% by weight does not increase the effect.
トナー像の像支持体への定着は、一般に加熱定着方式に
よるのが主流であり、この加熱定着方式にはオーブン定
着等の非接触加熱定着方式と、熱ロール定着等の接触加
熱方式とがあるが、接触加熱定着方式は熱効率が高く、
機器を小形化でき。Generally, toner images are fixed on image supports by heat fixing methods, and these heat fixing methods include non-contact heat fixing methods such as oven fixing, and contact heating methods such as heated roll fixing. However, the contact heat fixing method has high thermal efficiency;
Equipment can be made smaller.
消費電力が少なくてすむ等の利点がある。しかしながら
、接触加熱定着方式においては、トナー像を担持した像
支持体が熱ロール通過時にトナー像の一部が熱ロールに
転移し、熱ロールが1回転した後に、転移したトナー像
が像支持体に再転移して汚染するという所謂オフセット
が発生しやすい。It has advantages such as low power consumption. However, in the contact heat fixing method, when the image support carrying the toner image passes through the heat roll, part of the toner image is transferred to the heat roll, and after the heat roll has made one revolution, the transferred toner image is transferred to the image support. The so-called offset, in which the particles are re-transferred and contaminated, is likely to occur.
オフセット防止剤は、熱ロール定着方式においてもオフ
セットを起こさず、良質の画像を形成させる役目をなす
。The anti-offset agent does not cause offset even in the hot roll fixing method and plays a role in forming high-quality images.
オフセット防止剤としては、エチレン、プロピレン、ブ
テン、ペンテン、ヘキセン、ヘプテン。Anti-offset agents include ethylene, propylene, butene, pentene, hexene, and heptene.
オクテン、ノネン、デセン、3−メチル−1−ブテン、
3−メチル−2−ペンテン、3−プロピル−5−メチル
−2−ヘキセン等のオレフィンモノマーの重合体あるい
は前記のようなオレフィンモノマーとアクリル酸、メタ
クリル酸、酢酸ビニル等との共重合体、ステアリン酸ブ
チル、ステアリン酸プロピル等の脂肪酸の低級アルコー
ルエステル、カスタ・ワックス(伊藤製油(株)製)、
ダイヤモンドワックス(新日本理化(株)製)等の脂肪
酸の多価アルコールエステル、パームアセチ(日本油脂
(株)製)、ヘキストワックスE、ヘキストワックスー
OP(ヘキストアクチェンゲゼルシャフト社製)、カル
ナウバワックス等の脂肪酸の高級アルコールエステル、
ビスアマイドプラストフロー(日東化学工業(株)製)
、アマイド6L、7S及び6H(用研ファインケミカル
(株)製)、ヘキストワックスC(ヘキスト・アクチェ
ンゲゼルシャフト社11)等のアルキレンビス脂肪酸ア
ミド化合物、ステアリン酸亜鉛、ステアリン酸カルシウ
ム、ステアリン酸マグネシウム、ステアリン酸バリウム
、ステアリン酸銅、ステアリン酸アルミニウム、オレイ
ン酸亜鉛、オレイン酸マグネシウム、カプリル酸亜鉛、
カプリル酸マグネシウム、リノール酸亜鉛、リノール酸
カルシウム等の脂肪酸金属塩、ニラポールNBR,20
57S。octene, nonene, decene, 3-methyl-1-butene,
Polymers of olefin monomers such as 3-methyl-2-pentene and 3-propyl-5-methyl-2-hexene, or copolymers of the above-mentioned olefin monomers with acrylic acid, methacrylic acid, vinyl acetate, etc., stearin Lower alcohol esters of fatty acids such as butyl stearate and propyl stearate, casta wax (manufactured by Ito Oil Co., Ltd.),
Polyhydric alcohol esters of fatty acids such as diamond wax (manufactured by Shin Nihon Rika Co., Ltd.), palm acetic acid (manufactured by Nippon Oil & Fats Co., Ltd.), Hoechst wax E, Hoechst wax-OP (manufactured by Hoechst Akchengesellschaft), carnauba wax Higher alcohol esters of fatty acids such as
Bisamide Plast Flow (manufactured by Nitto Chemical Industry Co., Ltd.)
, Amide 6L, 7S and 6H (manufactured by Yoken Fine Chemical Co., Ltd.), alkylene bis fatty acid amide compounds such as Hoechst Wax C (Hoechst Akchengesellschaft 11), zinc stearate, calcium stearate, magnesium stearate, stearic acid. Barium, copper stearate, aluminum stearate, zinc oleate, magnesium oleate, zinc caprylate,
Fatty acid metal salts such as magnesium caprylate, zinc linoleate, calcium linoleate, etc., Nirapol NBR, 20
57S.
2007J、BR1220等の重量平均分子量が5万以
上のジエン系樹脂、ヒドロキシル基含有ビニル系樹脂、
カルボキシル基含有ビニル系樹脂等がある。オフセット
防止剤は、トナー中に0.1〜50重量%、特に1〜3
0重量%の量で加えるのが好ましい。0.1重量%未満
では、オフセット防止の効果が現れにくく、50重量%
を越えて添加すると定着性が低下するようになる。Diene resins with a weight average molecular weight of 50,000 or more, such as 2007J and BR1220, hydroxyl group-containing vinyl resins,
Examples include carboxyl group-containing vinyl resins. The offset inhibitor is contained in the toner in an amount of 0.1 to 50% by weight, especially 1 to 3% by weight.
Preferably it is added in an amount of 0% by weight. If it is less than 0.1% by weight, the effect of preventing offset is difficult to appear, and if it is less than 50% by weight.
If it is added in excess of this amount, the fixing properties will deteriorate.
本発明において、前記の他の樹脂及び各種添加剤は、単
独で添加してもよく、また併用してもよい。In the present invention, the other resins and various additives mentioned above may be added alone or in combination.
前記の材料を、例えば次の方法で混合し、静電荷像現像
用トナーを製造することができる。The above-mentioned materials can be mixed, for example, by the following method to produce a toner for developing electrostatic images.
秤量した材料を、Wコーン、■ブレンダー、ヘンシェル
ミキサー等で予備混合した後、加圧ニーダ−、バンバリ
ーミキサ−1熱ロール、エクストルーダー等を用いて樹
脂が溶融する温度下で混練する。冷却後、フェザ−ミル
、ピンミル、プルベライザー、ハンマーミル等で粗粉砕
する0次いで、アキュカット、アルピネ分級機で篩分し
て、好ましくは5〜30μmの粒径に調整する。The weighed materials are premixed using a W cone, (1) blender, Henschel mixer, etc., and then kneaded using a pressure kneader, Banbury mixer 1 hot roll, extruder, etc. at a temperature at which the resin melts. After cooling, the mixture is coarsely pulverized using a feather mill, pin mill, pulverizer, hammer mill, etc., and then sieved using an Accucut or Alpine classifier to adjust the particle size to preferably 5 to 30 μm.
本発明になるトナーの使用形態が、2成分である場合に
は、上記トナーとキャリアが組み合わされて現像剤が作
製される。When the toner of the present invention is used in a two-component manner, the toner and carrier are combined to prepare a developer.
キャリアとしては、偏平状、スポンジ状、コイン状、疑
球状若しくは球状の鉄粉、該鉄粉表面とテフロン、シリ
コン、ビニル系等の熱可塑若しくは熱硬化型の樹脂で被
覆したもの、又は本発明になる一成分トナーが好ましい
、更にキャリアは使用目的に応じて粒径、電気抵抗値、
比表面積等が調整される。Examples of carriers include flat, sponge-shaped, coin-shaped, pseudospherical, or spherical iron powder, the surface of the iron powder coated with thermoplastic or thermosetting resin such as Teflon, silicone, vinyl, or the like, or the present invention. It is preferable to use a one-component toner with a particle size, electrical resistance value,
Specific surface area etc. are adjusted.
2成分現像剤のトナー濃度は、一般にキャリアの比表面
積に依存し、使用するキャリアが不定形又は細粒径であ
るときは3〜10重量%に1球形又は粗粒径であるとき
は1〜5重量%にされるのが好ましい。The toner concentration of a two-component developer generally depends on the specific surface area of the carrier, and when the carrier used is amorphous or has a fine particle size, it is 1 to 3 to 10% by weight when the carrier is spherical or has a coarse particle size. Preferably it is 5% by weight.
本発明になるトナーは、種々の公知現像法に適用するこ
とができる。The toner of the present invention can be applied to various known developing methods.
また1本発明になるトナーは、種々の定着法。Further, the toner according to the present invention can be used in various fixing methods.
例えば所謂オイルレス及びオイル塗布熱ロール法キセノ
ン閃光照射法、オーブン法及び圧力定着法等に用いるこ
とができる。For example, it can be used in so-called oil-less and oil-coated heated roll methods, xenon flash irradiation methods, oven methods, pressure fixing methods, and the like.
更に、本発明になるトナーは、種々のクリーニング方法
1例えば所謂ファーブラシ法、ブレード法等に用いるこ
とができる。Further, the toner of the present invention can be used in various cleaning methods such as the so-called fur brush method and blade method.
本発明になる静電荷像現像用トナーは、結着剤樹脂に含
有される一般式(りで表されるイミド基含有モノマーに
よって、軟質塩化ビニル重合体への優れた耐付着性を示
す、また、トナーに必要な印字濃度、耐カブリ性及び耐
ブロッキング性を充分に満足している。The electrostatic image developing toner of the present invention exhibits excellent adhesion resistance to soft vinyl chloride polymers due to the imide group-containing monomer represented by the general formula (R) contained in the binder resin. , fully satisfies the print density, fog resistance and blocking resistance required for toner.
次に本発明の実施例を示す。 Next, examples of the present invention will be shown.
(I)共重合体A−1〜A−6及びB−1〜B−2の製
造
部分ケン化ポリビニルアルコール(デンカポバールW
−24、電気化学工業(株)製)3重量部を溶解した水
分散媒体2000重量部を収容した反応容器に表1に示
す組成のビニルモノマーを1000重量部及び表1に示
す重合開始剤を表1に示す量で加え、窒素気流下、80
〜90℃で10時間反応させた。冷却後、濾過熱風乾燥
して共重合体を得た。(I) Production of copolymers A-1 to A-6 and B-1 to B-2 Partially saponified polyvinyl alcohol (Denka Poval W
-24, manufactured by Denki Kagaku Kogyo Co., Ltd., in a reaction vessel containing 2000 parts by weight of an aqueous dispersion medium in which 3 parts by weight of the vinyl monomer having the composition shown in Table 1 and the polymerization initiator shown in Table 1 were added. Add in the amount shown in Table 1, under nitrogen stream, 80
The reaction was carried out at ~90°C for 10 hours. After cooling, the mixture was filtered and dried with hot air to obtain a copolymer.
(2)実施例1〜6及び比較例1〜2のトナーの製造
表2に示す組成の各成分を一括して乾式混合した後、2
軸ニーダ−を用いて160℃で溶融混練した。冷却した
後、ジェットエアーで微粉砕して粒径範[5〜25μm
のトナーを得た。(2) Production of toners of Examples 1 to 6 and Comparative Examples 1 to 2 After dry-mixing each component of the composition shown in Table 2,
The mixture was melt-kneaded at 160°C using a shaft kneader. After cooling, finely pulverize with jet air to obtain particles in the particle size range [5-25μm].
I got the toner.
(3)評価
トナー3重量%と、見掛密度が4〜4.5 g/d、電
気抵抗値が10δ〜108Ωで44〜177μmの粒径
の含有量が90重量%以上である酸化鉄粉キャリア97
重景%とを混合した現像剤を作製し、該現像剤を用いて
、周速約30am/秒で回転するセレンドラムをコロナ
電圧+4kVで一様に正帯電後、He −N eレーザ
ーで情報を書き込み、磁気ブラシ方式により反転現像し
た。次いで、記録紙に担持されたトナー像を1表面温度
170±5℃のテフロンロールで定着させた。(3) Evaluation toner of 3% by weight, iron oxide powder having an apparent density of 4 to 4.5 g/d, an electrical resistance value of 10δ to 108Ω, and a particle size content of 44 to 177 μm of 90% by weight or more. career 97
Using this developer, a selenium drum rotating at a circumferential speed of about 30 am/sec is uniformly positively charged with a corona voltage of +4 kV, and then information is generated using a He-Ne laser. was written and reversely developed using a magnetic brush method. Next, the toner image carried on the recording paper was fixed with a Teflon roll having a surface temperature of 170±5°C.
続いて、トナーの評価試験を行い表2にまとめた。Subsequently, an evaluation test was conducted on the toner and the results are summarized in Table 2.
試験方法を以下に示す。The test method is shown below.
(i)印字濃度及びカブリ濃度
東京重色(株)!1の反射濃度計TC−6DS型を用い
て測定した。(i) Print density and fog density Tokyo Juishiki Co., Ltd.! The measurement was performed using a reflection densitometer TC-6DS model No. 1.
(it)軟質塩化ビニル重合体への耐付着性印刷物をジ
オクチルフタレートが30重量%含まれる軟質塩化ビニ
ル重合体に温度40℃、圧力5 g f /ad、時間
200時間接着させた後、印刷物をはく離して印字欠損
の程度を次の基準で判定した。(it) Adhesion resistance to soft vinyl chloride polymer After adhering the printed matter to a soft vinyl chloride polymer containing 30% by weight of dioctyl phthalate at a temperature of 40°C and a pressure of 5 gf/ad for 200 hours, the printed matter was After peeling off, the degree of print loss was judged based on the following criteria.
3:印字欠損は全くない
2:印字欠損は部分的に認められるが、印字の判読は可
能
1:印字欠損が多大で、印字の判読は回置(Lit)耐
ブロッキング性
トナーを50℃、60%RH下に18時間静置した後・
塊状物0有無を調4た・ 以Tr白〔発明の効果
〕
以上の結果から明らかなように、本発明になる静電荷像
現像用トナーは、軟質塩化ビニル重合体への優れた耐付
着性を示し、実用性のあるトナーとして必要な良好な画
像濃度、耐カブリ性及び耐ブロッキング性を有する。3: No printing defects at all 2: Printing defects are partially observed, but the printing is legible 1: There is a large amount of printing defects, and the printing is legible. After standing under %RH for 18 hours.
[Effects of the Invention] As is clear from the above results, the toner for developing electrostatic images of the present invention has excellent adhesion resistance to soft vinyl chloride polymers. It has good image density, fog resistance, and blocking resistance necessary for a practical toner.
一一゛( 代理人 弁理士 若林邦彦 ・) (、デパ 一こp)111゛( Agent Patent Attorney Kunihiko Wakabayashi ・) (, department store 1 p) 1
Claims (1)
ルモノマーを構成成分として有する重合体を結着剤樹脂
として含有してなる静電荷像現像用トナー。 一般式( I ) ▲数式、化学式、表等があります▼ 〔但し、一般式( I )中、R_1は水素又はメチル基
、R_2は炭素数1〜6のアルキレン基又は脂環若しく
は芳香環を有する二価の有機基及びR_3は▲数式、化
学式、表等があります▼、▲数式、化学式、表等があり
ます▼又は▲数式、化学式、表等があります▼ であり、R_4、R_5、R_6、R_7、R_8及び
R_9は水素、炭素数1〜3のアルキル基、ハロゲン、
▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、−NO_2、−SO_3H又は−N
_3であり、これらは同一でも異なつていてもよく、R
_1_0、R_1_1及びR_1_2は、水素又は炭素
数1〜5のアルキル基であり、これらは同一でも異なっ
ていてもよい。[Scope of Claims] 1. A toner for developing electrostatic images comprising, as a binder resin, a polymer having as a constituent component an imide group-containing vinyl monomer represented by the following general formula (I). General formula (I) ▲There are numerical formulas, chemical formulas, tables, etc.▼ [However, in general formula (I), R_1 is hydrogen or a methyl group, and R_2 is an alkylene group having 1 to 6 carbon atoms or an alicyclic or aromatic ring. The divalent organic group and R_3 are ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, and R_4, R_5, R_6, R_7 , R_8 and R_9 are hydrogen, an alkyl group having 1 to 3 carbon atoms, halogen,
▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, -NO_2, -SO_3H or -N
_3, which may be the same or different, and R
_1_0, R_1_1 and R_1_2 are hydrogen or an alkyl group having 1 to 5 carbon atoms, and may be the same or different.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP62001182A JPS63169664A (en) | 1987-01-07 | 1987-01-07 | Toner for electrostatic charge image development |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP62001182A JPS63169664A (en) | 1987-01-07 | 1987-01-07 | Toner for electrostatic charge image development |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS63169664A true JPS63169664A (en) | 1988-07-13 |
Family
ID=11494309
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP62001182A Pending JPS63169664A (en) | 1987-01-07 | 1987-01-07 | Toner for electrostatic charge image development |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS63169664A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008088154A (en) * | 2006-09-07 | 2008-04-17 | Arakawa Chem Ind Co Ltd | New alicyclic compound, method for producing the same and polymer composition |
-
1987
- 1987-01-07 JP JP62001182A patent/JPS63169664A/en active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008088154A (en) * | 2006-09-07 | 2008-04-17 | Arakawa Chem Ind Co Ltd | New alicyclic compound, method for producing the same and polymer composition |
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