JPS63210849A - Electrostatic charge image developing toner and its manufacture - Google Patents
Electrostatic charge image developing toner and its manufactureInfo
- Publication number
- JPS63210849A JPS63210849A JP62043069A JP4306987A JPS63210849A JP S63210849 A JPS63210849 A JP S63210849A JP 62043069 A JP62043069 A JP 62043069A JP 4306987 A JP4306987 A JP 4306987A JP S63210849 A JPS63210849 A JP S63210849A
- Authority
- JP
- Japan
- Prior art keywords
- carbon black
- toner
- coupling agent
- aluminum coupling
- resin
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000006229 carbon black Substances 0.000 claims abstract description 66
- 239000002245 particle Substances 0.000 claims abstract description 41
- 239000007822 coupling agent Substances 0.000 claims abstract description 34
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 29
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000000178 monomer Substances 0.000 claims abstract description 25
- 239000000203 mixture Substances 0.000 claims abstract description 11
- 239000012736 aqueous medium Substances 0.000 claims abstract description 5
- 229920005989 resin Polymers 0.000 claims description 27
- 239000011347 resin Substances 0.000 claims description 27
- 239000012798 spherical particle Substances 0.000 claims description 7
- 239000003999 initiator Substances 0.000 claims description 3
- 229920005992 thermoplastic resin Polymers 0.000 claims description 2
- 238000004040 coloring Methods 0.000 abstract description 4
- 230000000903 blocking effect Effects 0.000 abstract description 3
- 239000007870 radical polymerization initiator Substances 0.000 abstract description 2
- 238000010526 radical polymerization reaction Methods 0.000 abstract 1
- 235000019241 carbon black Nutrition 0.000 description 57
- 238000006116 polymerization reaction Methods 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 13
- 238000000034 method Methods 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 239000002270 dispersing agent Substances 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 8
- 239000002609 medium Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 241000872198 Serjania polyphylla Species 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- -1 vinyl- Chemical group 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229920001567 vinyl ester resin Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000000889 atomisation Methods 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000006082 mold release agent Substances 0.000 description 2
- 150000005673 monoalkenes Chemical class 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 229920003169 water-soluble polymer Polymers 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-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
- XHAFIUUYXQFJEW-UHFFFAOYSA-N 1-chloroethenylbenzene Chemical compound ClC(=C)C1=CC=CC=C1 XHAFIUUYXQFJEW-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
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 1
- OTKLRHWBZHQJOP-UHFFFAOYSA-N 3-aminopropyl prop-2-enoate Chemical compound NCCCOC(=O)C=C OTKLRHWBZHQJOP-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 101100438426 Drosophila melanogaster Art4 gene Proteins 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- KFKPWTFHOVSSSI-UHFFFAOYSA-N butyl 2-hydroxyprop-2-enoate Chemical compound CCCCOC(=O)C(O)=C KFKPWTFHOVSSSI-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000002079 cooperative effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- NHOGGUYTANYCGQ-UHFFFAOYSA-N ethenoxybenzene Chemical compound C=COC1=CC=CC=C1 NHOGGUYTANYCGQ-UHFFFAOYSA-N 0.000 description 1
- VGIYPVFBQRUBDD-UHFFFAOYSA-N ethenoxycyclohexane Chemical compound C=COC1CCCCC1 VGIYPVFBQRUBDD-UHFFFAOYSA-N 0.000 description 1
- GFJVXXWOPWLRNU-UHFFFAOYSA-N ethenyl formate Chemical compound C=COC=O GFJVXXWOPWLRNU-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- UPWSFLJBKRQKBD-UHFFFAOYSA-N ethyl 3-hydroxy-2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=CO UPWSFLJBKRQKBD-UHFFFAOYSA-N 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 1
- 239000004137 magnesium phosphate Substances 0.000 description 1
- 229960002261 magnesium phosphate Drugs 0.000 description 1
- 229910000157 magnesium phosphate Inorganic materials 0.000 description 1
- 235000010994 magnesium phosphates Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- AYOOGWWGECJQPI-NSHDSACASA-N n-[(1s)-1-(5-fluoropyrimidin-2-yl)ethyl]-3-(3-propan-2-yloxy-1h-pyrazol-5-yl)imidazo[4,5-b]pyridin-5-amine Chemical compound N1C(OC(C)C)=CC(N2C3=NC(N[C@@H](C)C=4N=CC(F)=CN=4)=CC=C3N=C2)=N1 AYOOGWWGECJQPI-NSHDSACASA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 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
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- OGOBWYZAVILZEC-UHFFFAOYSA-N propyl 2-hydroxyprop-2-enoate Chemical compound CCCOC(=O)C(O)=C OGOBWYZAVILZEC-UHFFFAOYSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 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
- G03G9/097—Plasticisers; Charge controlling agents
- G03G9/09783—Organo-metallic compounds
-
- 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
- G03G9/0827—Developers with toner particles characterised by their shape, e.g. degree of sphericity
-
- 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
- G03G9/09—Colouring agents for toner particles
- G03G9/0902—Inorganic compounds
- G03G9/0904—Carbon black
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は静電荷像現像用トナー及びその製造方法に関す
るもので、より詳細には、流動性、黒色度、着色力に優
れたトナー及び該トナーを定着用樹脂の重合工程中で収
率よく製造する方法に関する。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a toner for developing electrostatic images and a method for producing the same. The present invention relates to a method for producing toner with good yield during a fixing resin polymerization step.
（従来の技術）
電子写真法等で静電荷像を可視像化（現像）するための
トナーとしては、スチレン系樹脂等の定着用樹脂媒質と
、この樹脂媒質中に分散させたカーボンブラック等の着
色剤との組成物を粒状化したものが広く使用されている
。(Prior art) A toner for visualizing (developing) an electrostatic charge image using electrophotography or the like uses a fixing resin medium such as styrene resin, and carbon black etc. dispersed in this resin medium. A granulated composition containing a coloring agent is widely used.
このトナーの最も代表的な製法は、前述した樹脂媒質と
着色剤とを溶融混練し、この混練組成物を冷却粉砕し、
粉砕物を分級して一定の粒度範囲に揃える工程から成る
。しかしながら、カーボンブラックは樹脂中でもチェン
構造をとりやすく、樹脂中に一様に微粒化分散すること
が困難である。The most typical manufacturing method for this toner is to melt and knead the aforementioned resin medium and colorant, cool and pulverize this kneaded composition, and
It consists of the process of classifying the pulverized material and aligning it within a certain particle size range. However, carbon black tends to form a chain structure even in the resin, making it difficult to uniformly atomize and disperse it in the resin.
この欠点を解消するものとして、特開昭６０−９３４５
２号公報には、アルミニウム系カップリング剤によって
処理されたカーボンブラックを、溶融混練、によってバ
インダー樹脂中に均一に分散させ、次いで粉砕、分級に
よってトナーを製造することが記載されている。As a solution to this drawback, Japanese Patent Application Laid-Open No. 60-9345
No. 2 describes that carbon black treated with an aluminum-based coupling agent is uniformly dispersed in a binder resin by melt-kneading, and then pulverized and classified to produce a toner.
（発明が解決しようとする問題点）
しかしながら、この粉砕・分級により得られるトナーの
収率は低く、またこれらの操作のために多大な設備を必
要とし、そのためにトナーの製造コストを極めて高いも
のとしている。また、得られる粒子の形状が不規則であ
るため、トナーの流動性が概して低く、ブロッキングを
発生し易いという欠点も認められる。(Problems to be Solved by the Invention) However, the yield of toner obtained by this pulverization and classification is low, and a large amount of equipment is required for these operations, which makes toner manufacturing cost extremely high. It is said that Further, since the shape of the obtained particles is irregular, the fluidity of the toner is generally low, and there is also a drawback that blocking is likely to occur.
更に、定着用樹脂との溶融混練によっては、カーボンブ
ラックの表面処理を行っても、完全な微粒化分散は未だ
困難である。Further, even if carbon black is surface-treated by melt-kneading with a fixing resin, complete atomization and dispersion is still difficult.
定着用樹脂媒質中でのカーボンブラックの分散が不均一
であると、黒色度、着色力が劣り、画像濃度の低下をも
たらす。また、カップリング剤によるカーボンブラック
の処理の効果は、単にカップリング剤の種類や処理量に
依存するだけではなく、カーボンブラックそのものの表
面の化学的及び物理的特性にも大きく依存すると共に、
定着用樹脂との混合操作によっても影響されることから
、従来の手段では十分満足し得る成果を挙げるに至フて
いない。If the carbon black is not uniformly dispersed in the fixing resin medium, the degree of blackness and coloring power will be poor, leading to a decrease in image density. Furthermore, the effect of treating carbon black with a coupling agent does not simply depend on the type of coupling agent and the amount of treatment, but also greatly depends on the chemical and physical properties of the surface of the carbon black itself.
Since it is also affected by the mixing operation with the fixing resin, conventional means have not been able to achieve sufficiently satisfactory results.
（問題点を解決するための手段）
本発明者等は、トナー用のカーボンブラックとして比較
的比表面が小さく、かつｐＨ値が７．０以下のカーボン
ブラックを選択すること；この特定のカーボンブラック
とラジカル重合性単量体とを含む重合性組成物を水性媒
体中に懸濁させて球状粒子への重合を行うこと；及びこ
の重合性組成物中にアルミニウムカップリング剤を添加
することが、定着用樹脂媒質中にカーボンブラックを一
様に分散された球状トナー粒子を得る上で重要であるこ
とを見出した。(Means for Solving the Problems) The present inventors selected carbon black with a relatively small specific surface and a pH value of 7.0 or less as carbon black for toner; and a radically polymerizable monomer and suspended in an aqueous medium to polymerize into spherical particles; and adding an aluminum coupling agent to this polymerizable composition, It has been found that this is important in obtaining spherical toner particles in which carbon black is uniformly dispersed in a fixing resin medium.
本発明によれば、ラジカル重合型熱可塑性樹脂から成る
定着用樹脂とこの定着用樹脂中に分散したカーボンブラ
ックとの組成物から成る静電荷像現像用トナーにおいて
、該トナーは下記式式中、ｒｌ はトナー粒子の長径
を表わし、ｒｓはトナー粒子の短径を表わす、
で定義される真円度が０．９０以上の球状粒子から成り
、カーボンブラックは比表面積が３００ｒｎ’／ｇ以下
かつｐＨ値が７．０以下のカーボンブラックであり、且
つ該トナー中にはアルミニウムカップリング剤が存在す
ることを特徴とするトナーが提供される。According to the present invention, there is provided a toner for developing an electrostatic image comprising a composition of a fixing resin made of a radically polymerizable thermoplastic resin and carbon black dispersed in the fixing resin, in which the toner has the following formula: rl represents the long axis of the toner particle, and rs represents the short axis of the toner particle. Carbon black consists of spherical particles with a circularity of 0.90 or more defined as Provided is a toner characterized in that it is carbon black having a value of 7.0 or less, and an aluminum coupling agent is present in the toner.
本発明によればまた、ラジカル重合性単量体、比表面積
が３００ｒｎ″／ｇ以下かつ、ｐｉ（値が７．０以下の
カーボンブラック及びアルミニウムカップリング剤を含
有する組成物を水性媒体中に懸濁させ、この懸濁粒子を
ラジカル開始剤の存在下に重合させ、定着用樹脂と該樹
脂中に分散したカーボンブラックとから成る球状粒子を
取得することから成る静電荷像現像用トナーの製造方法
が提供される。According to the present invention, a composition containing a radically polymerizable monomer, a carbon black having a specific surface area of 300 rn''/g or less, a pi value of 7.0 or less, and an aluminum coupling agent is added to an aqueous medium. Production of a toner for developing electrostatic images, which comprises suspending the particles and polymerizing the suspended particles in the presence of a radical initiator to obtain spherical particles consisting of a fixing resin and carbon black dispersed in the resin. A method is provided.
（作 用）
本発明において、トナー用のカーボンブラックとして比
較的比表面積の小さい、即ち比表面積（ＢＥＴ）が３０
０ｍ″／ｇ以下でｐＨ値が７．０以下のものを用いるの
が第一の特徴である。カーボンブラックのｐＨ値とは、
カーボンブラックの水性懸濁液のｐＨのことであり、ｐ
Ｈ値の低いカーボンブラックはその製法、処理法に由来
して、炭素、水素と相当量の酸素（一般に２乃至１２重
量％）とを含有することが特徴である。この酸素はカー
ボンブラック粒子表面に極性基として存在するものと認
められるが、これらの極性基の存在がアルミニウムカッ
プリング剤との協働作用により、カーボンブラック粒子
を定着樹脂用単量体中に一様に微粒−化分散させるもの
と誌められる。(Function) In the present invention, carbon black for toner has a relatively small specific surface area, that is, a specific surface area (BET) of 30
The first characteristic is to use carbon black with a pH value of 7.0 or less at a temperature of 0 m''/g or less.The pH value of carbon black is
The pH of an aqueous suspension of carbon black, p
Carbon black with a low H value is characterized by containing carbon, hydrogen, and a considerable amount of oxygen (generally 2 to 12% by weight) due to its manufacturing and processing methods. It is recognized that this oxygen exists as a polar group on the surface of the carbon black particles, but the existence of these polar groups causes the carbon black particles to be integrated into the fixing resin monomer due to the cooperative action with the aluminum coupling agent. It is said to be a method of atomization and dispersion.
このカーボンブラックは３００ｍ’／ｇ以下の比表面積
を有することも重要であり、比表面積がこの範囲を超え
て大きくなると、アルミニウムカップリング剤と組合せ
て用いたとしても、定着樹脂用単量体中に一様に微粒化
分散させることが困難となり、更に単量体の重合体への
転化率や重合速度も低下する傾向が表われる。これは比
表面積が大きい程、表面活性が犬となり粒子相互の凝集
傾向が大となること、及びアルミニウムカップリング剤
の効果が十分に及ばなくなることと関連していると思わ
れる。It is also important that this carbon black has a specific surface area of 300 m'/g or less, and if the specific surface area exceeds this range, even if it is used in combination with an aluminum coupling agent, It becomes difficult to uniformly atomize and disperse the monomer, and the conversion rate of monomer to polymer and polymerization rate also tend to decrease. This seems to be related to the fact that the larger the specific surface area, the greater the surface activity and the greater the tendency for particles to aggregate with each other, and the less effective the aluminum coupling agent is.
本発明の目的に適したチャンネル型カーボンブラックは
、スペシャル・ブラック４、スペシャル・ブラック５、
ＭＡ−１００等として入手し得るが、勿論これらに限定
されない。Channel type carbon blacks suitable for the purpose of the present invention include Special Black 4, Special Black 5,
It is available as MA-100, but is of course not limited to these.
本発明においては、上記チャンネル型カーボンブラック
、定着用樹脂単量体及びアルミニウムカップリング剤を
含む組成物を水性媒体中に懸濁させ、この懸濁粒子をラ
ジカル開始剤の存在下に重合させることが第二の特徴で
ある。In the present invention, a composition containing the channel carbon black, a fixing resin monomer, and an aluminum coupling agent is suspended in an aqueous medium, and the suspended particles are polymerized in the presence of a radical initiator. is the second characteristic.
即ち、この手段を採用することにより、定着用樹脂の重
合工程でトナーに適した粒度の樹脂−カーボンブラック
組成物の球状粒子が一挙に製造されるという利点が得ら
れるばかりではなく、カーボンブラック粒子の樹脂中へ
の分散が、極めて微細になるという利点がある。また、
本発明によれば、アルミニウムカップリング剤は、個々
のカーボンブラック粒子を表面処理するという操作は不
要であり、単にアルミニウムカップリング剤を単量体中
に添加するという簡便な操作で、均一な微粒化分散が可
能となるものである。That is, by adopting this method, not only can spherical particles of the resin-carbon black composition with a particle size suitable for the toner be produced all at once in the polymerization process of the fixing resin, but also carbon black particles can be produced at once. It has the advantage that the dispersion in the resin becomes extremely fine. Also,
According to the present invention, the aluminum coupling agent does not require surface treatment of individual carbon black particles, and can be made into uniform fine particles by simply adding the aluminum coupling agent into the monomer. This makes it possible to perform chemical dispersion.
一般に定着用樹脂単量体中にカーボンブラックを添加す
ると、その重合速度は小さくなり、また重合体への転化
率も小さくなる傾向が認められる。これはカーボンブラ
ック表面にキノイド状酸素があり、これが重合禁止作用
を示すためと考えられる。本発明によれば、カーボンブ
ラックとして比表面積の比較的小さいカーボンブラック
を使用し、しかも重合組成物中にアルミニウムカップリ
ング剤を含有させることにより、重合速度及び重合体へ
の転化率をも高いレベルに維持することが可能となるも
のである。Generally, when carbon black is added to a fixing resin monomer, its polymerization rate tends to decrease, and the conversion rate to a polymer also tends to decrease. This is thought to be due to the presence of quinoidal oxygen on the surface of carbon black, which exhibits a polymerization inhibiting effect. According to the present invention, by using carbon black with a relatively small specific surface area as the carbon black and also containing an aluminum coupling agent in the polymerization composition, the polymerization rate and conversion rate to a polymer can be increased to a high level. This makes it possible to maintain the
カップリング剤としては、アルミニウム系以外のものと
して、シラン系及びチタン系のカップリング剤が多数知
られており、また各方面にも広く使用されている。しか
しながら、本発明者等の研究によると、シラン系カップ
リング剤やチタン系カップリング剤をこの目的に使用し
たのでは殆んど効果が得られず、前述した種々の作用は
アルミニウム系カップリング剤に特有のものである。ア
ルミニウム系カップリング剤の適当な例は、これに限定
されないが、アセトアルコキシアルミニウムジイソプロ
ピレートである。As coupling agents, many silane-based and titanium-based coupling agents other than aluminum-based coupling agents are known, and are also widely used in various fields. However, according to the research conducted by the present inventors, the use of silane coupling agents and titanium coupling agents for this purpose has little effect, and that the various effects described above are caused by the use of aluminum coupling agents. It is unique to A suitable example of an aluminum-based coupling agent is, but is not limited to, acetalkoxyaluminum diisopropylate.
本発明において、チャンネル型カーボンブラックは、単
量体当り１乃至２０重量％、特に２乃至１０ｆｉ量％の
量で用いることが望ましく、一方アルミニウムカップリ
ング剤は、カーボンブラック当り０．１乃至３０重量％
、特に１０乃至３０重量％の量で用いるのがよい。In the present invention, the channel type carbon black is preferably used in an amount of 1 to 20% by weight, particularly 2 to 10% by weight, based on the monomer, while the aluminum coupling agent is used in an amount of 0.1 to 30% by weight, based on the carbon black.
, especially in an amount of 10 to 30% by weight.
本発明において、使用する単量体はラジカル重合性のも
のであり、しかも生成重合体がトナーに要求される定着
性と検電性を有するものであり、エチレン系不飽和を有
する単量体の１種又は２種以上の組合せが前述した制限
のもとに使用される。このような単量体の適当な例は、
モノビニル芳香族単量体、アクリル系単量体、ビニルエ
ステル系単量体、ビニルエーテル系単量体、ジオレフィ
ン系単量体、モノオレフィン系単量体等である。In the present invention, the monomers used are radically polymerizable, and the resulting polymer has the fixing properties and electrodetection properties required for toners. One type or a combination of two or more types may be used subject to the above-mentioned limitations. Suitable examples of such monomers are:
These include monovinyl aromatic monomers, acrylic monomers, vinyl ester monomers, vinyl ether monomers, diolefin monomers, monoolefin monomers, and the like.
モノビニル芳香族車量体としては、
式
式中、Ｒ１は水素原子、低級アルキル基又はハロゲン原
子であり、Ｒ２は水素原子、低級アルキル基、ハロゲン
原子、アルコキシ基、アミノ基、ニトロ基、ビニル基或
いはカルボキシル基である、
のモノビニル芳香族炭化水素、例えばスチレン、α−メ
チルスチレン、ビニルトルエン、α−クロロスチレン、
ｏ ＋、ｍ ＋、ｐ−クロロスチレン、ｐ−エチルスチ
レン、スチレンスルホン酸ナトリウム、ジビニルベンゼ
ンの単独又は２ｆｆｆ１以上の組合せを挙げることがで
き、更に前述した他の単量体としては以下のものが夫々
挙げられる。As a monovinyl aromatic carmer, R1 is a hydrogen atom, a lower alkyl group, or a halogen atom, and R2 is a hydrogen atom, a lower alkyl group, a halogen atom, an alkoxy group, an amino group, a nitro group, or a vinyl group. or a monovinyl aromatic hydrocarbon which is a carboxyl group, such as styrene, α-methylstyrene, vinyltoluene, α-chlorostyrene,
o +, m +, p-chlorostyrene, p-ethylstyrene, sodium styrene sulfonate, divinylbenzene alone or in combination of 2fff1 or more, and furthermore, the other monomers mentioned above include the following: Each can be mentioned.
式
％式％（２）
式中、Ｒ３は水素原子又は低級アルキル基、Ｒ４は水素
原子、炭素数１２迄の炭化水素基、ヒドロキシアルキル
基、ビニルエステル基又はアミノアルキル基である、の
アクリル系単量体、例えばアクリル酸、メタクリル酸、
アクリル酸メチル、アクリル酸エチル、アクリル酸ブチ
ル、アクリル酸−２−エチルヘキシル、アクリル酸シク
ロヘキシル、アクリル酸フェニル、メタクリル酸メチル
、メタクリル酸ヘキシル、メタクリル酸−２−エチルヘ
キシル、β−ヒドロキシアクリル酸エチル、γ−ヒドロ
キシアクリル酸プロピル、δ−ヒドロキシアクリル酸ブ
チル、β−ヒドロキシメタクリル酸エチル、γ−アミノ
アクリル酸プロピル、γ−Ｎ−Ｎ−ジエチルアミノアク
リル酸プロピル、エチレングリコールジメタクリル酸エ
ステル、テトラエチレングリコールジメタクリル酸エス
テル等。Formula % Formula % (2) In the formula, R3 is a hydrogen atom or a lower alkyl group, and R4 is a hydrogen atom, a hydrocarbon group having up to 12 carbon atoms, a hydroxyalkyl group, a vinyl ester group, or an aminoalkyl group. Monomers such as acrylic acid, methacrylic acid,
Methyl acrylate, ethyl acrylate, butyl acrylate, 2-ethylhexyl acrylate, cyclohexyl acrylate, phenyl acrylate, methyl methacrylate, hexyl methacrylate, 2-ethylhexyl methacrylate, β-hydroxyethyl acrylate, γ -Propyl hydroxyacrylate, δ-butyl hydroxyacrylate, β-ethyl hydroxymethacrylate, γ-aminopropyl acrylate, γ-N-N-diethylaminopropyl acrylate, ethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate acid esters, etc.
式
％式％
式中、Ｒ６は水素原子又は低級アルキル基である、
のビニルエステル、例えばギ酸ビニル、酢酸ビニル、プ
ロピオン酸ビニル等。Vinyl esters of formula % formula % where R6 is a hydrogen atom or a lower alkyl group, such as vinyl formate, vinyl acetate, vinyl propionate, etc.
式
％式％
式中、Ｒ６は炭素数１２迄の１価炭化水素基である、
のビニルエーテル、例えばビニルメチルエーテル、ビニ
ルエチルエーテル、ビニル−〇−ブチルエーテル、ビニ
ルフェニルエーテル、ビニルシクロヘキシルエーテル等
。Vinyl ethers such as vinyl methyl ether, vinyl ethyl ether, vinyl-〇-butyl ether, vinyl phenyl ether, vinyl cyclohexyl ether, etc., where R6 is a monovalent hydrocarbon group having up to 12 carbon atoms.
式、
式中、Ｒ７％ Ｒｅ ｓ Ｒ９の各々は水素原子、低級
アルキル基又はハロゲン原子である、
のジオレフィン類、特にブタジェン、イソプレン、クロ
ロブレン等。Diolefins of the formula, in which each of R7%ResR9 is a hydrogen atom, a lower alkyl group, or a halogen atom, particularly butadiene, isoprene, chlorobrene, and the like.
式、
ＩＧ
ＣＨ２＝Ｃ−Ｒ１１・・・・・・・・・・・・（６）式
中、Ｒ３゜、Ｒ１１の各々は水素原子又は低級アルキル
基である、
のモノオレフィン類、特にエチレン、プロピレン、イソ
フチレン、フテンー１、ペンテン−１，４−メチルペン
テン−１等。Monoolefins of the formula, IG CH2=C-R11 (6), in which each of R3゜ and R11 is a hydrogen atom or a lower alkyl group, especially ethylene, Propylene, isophthylene, phthene-1, pentene-1,4-methylpentene-1, etc.
本発明においては、上述した必須成分以外にトナーに含
有させることが望ましい添加剤成分を、重合に先立って
重合系中に配合しておくことができる。In the present invention, in addition to the above-mentioned essential components, additive components that are desirable to be included in the toner can be blended into the polymerization system prior to polymerization.
例えば、二成分系顔料としての用途には、それ自体公知
の荷電制御剤、例えばニグロシンベース（Ｃ１５０４５
）、オイルブラック（ＣＩ２６１５０） 、スピロンブ
ラック等の油溶性染料や、ナフテン酸金属塩、脂肪金属
石鹸、樹脂酸石鹸等を配合することができ、また、トナ
ーにオフセット防止効果を付加するために、低分子量ポ
リエチレン、低分子量ポリプロピレン、各種ワックス、
シリコーン油等の離型剤を含有させることができる。For example, for use as a two-component pigment, charge control agents known per se, such as nigrosine base (C15045
), Oil Black (CI26150), Spiron Black, and other oil-soluble dyes, naphthenic acid metal salts, fatty metal soaps, resin acid soaps, etc. can be blended. , low molecular weight polyethylene, low molecular weight polypropylene, various waxes,
A mold release agent such as silicone oil can be included.
本発明方法では、前述した原料を水中に懸濁させる。水
中での懸濁状態を安定化させるため、有機又は無機の分
散剤を一般に使用する。In the method of the present invention, the above-mentioned raw materials are suspended in water. Organic or inorganic dispersants are generally used to stabilize the suspension in water.
有機分散剤としては、ゼラチン、澱粉、水溶性澱粉話導
体、カルボキシメチルセルロースやエトセル等の水溶性
セルロース話導体、ポリビニルアルコール、水溶性アク
リル樹脂、ビニルエーテル・マレイン酸共重合体等の水
溶性高分子や、アニオン系、ノニオン系、カチオン系或
いは両性系の界面活性剤が挙げられる。Examples of organic dispersants include gelatin, starch, water-soluble starch conductors, water-soluble cellulose conductors such as carboxymethylcellulose and etocel, water-soluble polymers such as polyvinyl alcohol, water-soluble acrylic resins, vinyl ether-maleic acid copolymers, etc. , anionic, nonionic, cationic or amphoteric surfactants.
無機系分散剤としては、難溶性の無機微粒子、例えば炭
酸カルシウム、炭酸マグネシウム、リン酸マグネシウム
、硫酸バリウム、シリカ、アルミナ、タルク、ベントナ
イト等の各種クレイ、ケイソウ上等を挙げることができ
る。Examples of the inorganic dispersant include poorly soluble inorganic fine particles such as various clays such as calcium carbonate, magnesium carbonate, magnesium phosphate, barium sulfate, silica, alumina, talc, and bentonite, diatomaceous clay, and the like.
これらの無機或いは有機の分散剤は単独でも或いは２種
以上の組合せでも用いることができる。These inorganic or organic dispersants can be used alone or in combination of two or more.
本発明の場合、一般に必要でないが、所望によっては、
媒体比重、表面張力、粘度等の調整の目的で、上記分散
剤以外に、ＮａＣ１、にＣ１，Ｎａ２ＳＯ４等の水溶性
塩類を用いることもできる。In the case of the present invention, if desired, although generally not necessary,
In addition to the above-mentioned dispersant, water-soluble salts such as NaCl, C1, Na2SO4, etc. can also be used for the purpose of adjusting the specific gravity, surface tension, viscosity, etc. of the medium.
重合開始剤としては、アゾビスイソブチロニトリル等の
アゾ化合物や、クメンヒドロペルオキシド、ｔ−ブチル
ヒドロペルオキシド、過酸化ベンゾイル、過酸化ラウロ
イル等の過酸化物など車量体に可溶なものが使用される
。As the polymerization initiator, azo compounds such as azobisisobutyronitrile, and peroxides such as cumene hydroperoxide, t-butyl hydroperoxide, benzoyl peroxide, and lauroyl peroxide, which are soluble in the polymer, are used. used.
単量体と水との比は、かなり大幅に変化させ得るが、一
般に１＝９９乃至５０ ： ５０、特に５：９５乃至３
０ ： ７０の重量比で用いるのがよい。分散剤の使用
量は種類によでも相違するが、水溶性高分子分散剤は、
本当り０．１乃至１０重量％、特に０．５乃至５１量％
で用いるのがよく、また無機分散剤は単量体当り０．０
１乃至１０重量％、特に０．１乃至５重量％の量で用い
るのがよい。界面活性剤を使用する場合には、懸濁粒子
がエマルジョンサイズになるような量で使用してはなら
ない。ラジカル重合開始剤は単量体当り０．１乃至 。The ratio of monomer to water can vary quite widely, but is generally from 1=99 to 50:50, especially from 5:95 to 3.
It is preferable to use a weight ratio of 0:70. The amount of dispersant used varies depending on the type, but for water-soluble polymer dispersants,
0.1 to 10% by weight, especially 0.5 to 51% by weight
It is best to use an inorganic dispersant at a concentration of 0.0 per monomer.
It is preferred to use amounts of 1 to 10% by weight, especially 0.1 to 5% by weight. If surfactants are used, they should not be used in amounts such that the suspended particles become emulsion sized. The amount of the radical polymerization initiator is 0.1 to 0.1 per monomer.
１０重量％、特に０，５乃至５重量％の量で用いるのが
よい。It is preferred to use an amount of 10% by weight, especially 0.5 to 5% by weight.
重合温度は一般に４０乃至１００℃、特に５０乃至９０
℃の範囲が適当であり、重合時間は単量体の種類によっ
ても相違するが、２乃至２０時間の範囲から重合が完結
する時間を選ぶのがよい。The polymerization temperature is generally 40 to 100°C, particularly 50 to 90°C.
The temperature range is suitable, and although the polymerization time varies depending on the type of monomer, it is preferable to select a time for completing the polymerization from a range of 2 to 20 hours.
本発明によれば、かくして前記式で定義される真円度（
Ｄ）が０．９以上、特に０．９５以上の範囲内にある真
球状の粒子が得られる。また、本発明によれば、上記条
件下に重合を行うことにより、生成重合体粒子、即ちト
ナー粒子の粒径を１乃至３０μｍ１特に５乃至２０μｍ
の範囲に制御することが容易であり、しかもその粒度分
布は極めてシャープであり、その標準偏差は一般に３以
内である。生成粒子は反応媒質から分離し、必要により
洗浄等の精製操作を行い、乾燥してトナー製品とする。According to the invention, the roundness (
True spherical particles having D) in a range of 0.9 or more, particularly 0.95 or more are obtained. Further, according to the present invention, by carrying out polymerization under the above conditions, the particle size of the produced polymer particles, that is, toner particles, can be adjusted to 1 to 30 μm, particularly 5 to 20 μm.
It is easy to control the particle size within this range, and its particle size distribution is extremely sharp, and its standard deviation is generally within 3. The generated particles are separated from the reaction medium, subjected to purification operations such as washing if necessary, and dried to produce a toner product.
このトナー用着色粒子には、必要により、カーボンブラ
ック、疎水性シリカ等をまぶして、最終トナーとする。The colored particles for toner are sprinkled with carbon black, hydrophobic silica, etc., if necessary, to form a final toner.
（発明の効果）
本発明によれば、カーボンブラックを定着用樹脂媒質中
に完全に一様に微粒化分散させることにより、トナーの
黒色度及び着色度を高め、高濃度の画像形成を行うこと
ができる。また、このトナーは真球状で且つトナー中に
残存子ツマ−が含有されていないことから、流動性に優
れており、現像に際してブロッキング傾向も殆んどない
。(Effects of the Invention) According to the present invention, by completely and uniformly atomizing and dispersing carbon black in a fixing resin medium, it is possible to increase the degree of blackness and coloring of a toner and form a high-density image. Can be done. Furthermore, since this toner is perfectly spherical and contains no residual particles, it has excellent fluidity and has almost no blocking tendency during development.
また、定着用樹脂の重合工程で一挙に所定粒度の球状ト
ナー粒子が得られ、収率が高く、生産性も高いという利
点を有する。Further, it has the advantage that spherical toner particles of a predetermined particle size can be obtained all at once in the polymerization process of the fixing resin, resulting in a high yield and high productivity.
本発明の実施例を下記に示すが、これにより本発明が限
定されるものでない。Examples of the present invention are shown below, but the present invention is not limited thereto.
実施例−１
カーボンブラック：ＭＡ−Ｚｏｏ（比表面積１３４ｒｒ
？／ｇ、 ｐＨ値３．０）（三菱化成工業■製）５重量
部を、アルミニウムカップリング剤ＡＬ−Ｍ（アセトア
ルコキシジイソプロピレート）（味の素■製〕１重量部
を溶解させたトルエン２０重量部にて浸漬し、減圧乾燥
させた後アルミニウムカップリング剤処理カーボンブラ
ックを得た。そして、このＡＬ−Ｍ処理カーボンブラッ
ク５重量部に、スチレン７０重量部、ｎ−ブチルメタク
リレート３０重量部を加え、ＴＫホモミキサー〔特殊機
化工業■製〕を用いて、３０００ ｒｐｍにて５分間攪
拌することにより、カーボンブラック分散液を得た。こ
の得られたカーボンブラック分散液を光学顕微ｔ（ｘｓ
ｏｏ）にて観察したところ、カーボンブラックの凝集物
は認められず、分散性は良好であった。Example-1 Carbon black: MA-Zoo (specific surface area 134rr
? 20 weight parts of toluene in which 5 parts by weight of the aluminum coupling agent AL-M (acetalkoxydiisopropylate) (manufactured by Ajinomoto ■) was dissolved in 5 parts by weight of the aluminum coupling agent AL-M (acetalkoxydiisopropylate) (manufactured by Ajinomoto ■) After drying under reduced pressure, carbon black treated with an aluminum coupling agent was obtained.70 parts by weight of styrene and 30 parts by weight of n-butyl methacrylate were added to 5 parts by weight of this AL-M treated carbon black. A carbon black dispersion was obtained by stirring for 5 minutes at 3000 rpm using a TK homomixer (manufactured by Tokushu Kika Kogyo).The obtained carbon black dispersion was examined under an optical microscope t(xs
When observed at oo), no carbon black aggregates were observed, and the dispersibility was good.
このカーボンブラック分散液に、荷電制御剤ボントロン
Ｓ−３４（オリエント化学■製）２ｉｉ量部、離型剤ビ
スコール５５０Ｐ（三洋化成■製〕２重量部、重合開始
剤２．２′−アゾビス−（２−４ジメチルバレロニトリ
ル）５重量部を加えて、充分に分散させた。次に、２重
量％のポリビニルアルコール水溶液中に上記分散物を添
加し、ＴＫホモミキサーを用い６０００ ｒｐｍにて１
０分間攪拌し、油滴を得た。この油滴は非常に安定で、
光学顕微鏡で観察した結果、油滴中には、カーボンブラ
ック等の特性付与剤が均一に分散していた。その後、通
常攪拌機で６０ ｒｐｍの攪拌速度で、窒素気流下７０
℃で５時間にて重合反応を完結させた。To this carbon black dispersion, 2 parts by weight of charge control agent Bontron S-34 (manufactured by Orient Kagaku ■), 2 parts by weight of mold release agent Viscol 550P (manufactured by Sanyo Chemical ■), and 2 parts by weight of polymerization initiator 2'-azobis-( 2-4 dimethylvaleronitrile) was added and thoroughly dispersed.Next, the above dispersion was added to a 2% by weight polyvinyl alcohol aqueous solution, and mixed at 6000 rpm using a TK homomixer.
After stirring for 0 minutes, oil droplets were obtained. These oil droplets are very stable;
As a result of observation with an optical microscope, the property imparting agent such as carbon black was uniformly dispersed in the oil droplets. Thereafter, the stirrer was stirred at a stirring speed of 60 rpm for 70 min under a nitrogen stream.
The polymerization reaction was completed at ℃ for 5 hours.
重合反応終了後、脱水、洗浄を繰り返し乾燥させ、平均
粒径１２μｍの本発明のトナーを得た。After the polymerization reaction was completed, dehydration and washing were repeated and dried to obtain a toner of the present invention having an average particle size of 12 μm.
上記の如くして得られたトナーを用いて、電子写真複写
機ＤＣ−１００１（三田工業■製）にて、画像形成させ
たところ、カブリが少なく、高い黒化度を有する画像が
得られた。またこれを反射濃度計で測定したところ、カ
ブリ濃度０．００３、黒ベタ部の画像濃度１．４と良好
な結果が得られた。When an image was formed using the toner obtained as described above in an electrophotographic copying machine DC-1001 (manufactured by Sanda Kogyo ■), an image with little fog and a high degree of blackening was obtained. . Further, when this was measured with a reflection densitometer, good results were obtained, with a fog density of 0.003 and an image density of a solid black area of 1.4.
実施例−２
カーボンブラック：スペシャルブラック５（比表面積１
３４ｒｒ？／ｇ、ｐＨ値２．７ ） （デグサ社製）
５部を、実施例−１と同一の方法でアルミニウムカップ
リング剤ＡＬ−Ｍにて処理し、油滴形成を行フた結果、
油滴中のカーボンブラックの分散性は良好であった。こ
の得られた油滴を実施例１と同一の手法にてトナー合成
し、平均粒径１２μｍの本発明のトナーを得た。このト
ナーを用いてＤＣ−１００１にて画像形成させたところ
、カブリ濃度０．００３ 、画像濃度１．４を有する良
好な画像が得られた。Example-2 Carbon black: Special black 5 (specific surface area 1
34rr? /g, pH value 2.7) (manufactured by Degussa)
5 parts were treated with aluminum coupling agent AL-M in the same manner as in Example-1 to form oil droplets. As a result,
The dispersibility of carbon black in the oil droplets was good. A toner was synthesized from the obtained oil droplets in the same manner as in Example 1 to obtain a toner of the present invention having an average particle size of 12 μm. When this toner was used to form an image using DC-1001, a good image having a fog density of 0.003 and an image density of 1.4 was obtained.
比較例−１
カーボンブラックＦＷ２００ （比表面積４６０ｍ２／
ｇ、ｐ）ｌ値２．５ ） （デグサ社製〕を５部用い
て、実施例−１と同一の方法で、アルミニウムカップリ
ング剤ＡＬ−Ｍにて処理し、油滴形成を行った結果、油
滴中には１〜２μｍ程のカーボンブラックの凝集物が見
られた。この懸濁液を実施例−１と同一の手法によりト
ナー合成し、平均粒径１２μｍの本発明のトナーを得た
。このトナーを用いてＤＣ−１００１にて画像形成した
ところ、カブリ濃度０．００７ 、画像濃度１．１とカ
ブリが発生し、画像濃度の低いものが得られた。Comparative example-1 Carbon black FW200 (specific surface area 460 m2/
g, p) l value 2.5) (manufactured by Degussa) was treated with aluminum coupling agent AL-M in the same manner as in Example-1 to form oil droplets. , carbon black aggregates of approximately 1 to 2 μm in size were observed in the oil droplets. This suspension was synthesized into a toner using the same method as in Example 1 to obtain the toner of the present invention with an average particle size of 12 μm. When an image was formed with DC-1001 using this toner, fogging occurred with a fogging density of 0.007 and an image density of 1.1, and an image with a low density was obtained.
比較例−２
カーボンブラックニブリンテックスしく比表面積１５０
ゴ／ｇ、ｐＨ値１３．５ ） （デグサ社製〕を５部
用いて、実施例−１と同一の方法でアルミニウムカップ
リング剤ＡＬ−Ｍにて処理し、油滴形成を行った結果油
滴中には、２〜３μｍ程のカーボンブラックの凝集物が
見られた。この懸濁液を実施例−１と同一の手法により
トナー合成し、平均粒径１２μｍのトナーを得た。この
トナーを用いてＤＣ−１００１にて画像形成したところ
、カブリ濃度Ｇ、Ｑ１２ 、画像濃度０．９と十分な画
像濃度は得られなかった。Comparative example-2 Carbon black Niblintex specific surface area 150
(manufactured by Degussa) was treated with aluminum coupling agent AL-M in the same manner as in Example 1 to form oil droplets. Carbon black aggregates of about 2 to 3 μm in size were observed in the droplets. This suspension was synthesized into a toner using the same method as in Example 1 to obtain a toner with an average particle size of 12 μm. When an image was formed using DC-1001, fog density G, Q12, image density 0.9, and sufficient image density could not be obtained.
比較例−３
アルミニウムカップリング剤で処理を行っていない、カ
ーボンブラック：ＭＡ−１００（比表面積１３４ｄ／ｇ
、 ｐ）Ｉ値３．０）（三菱化成工業■製）を５部用い
て、実施例−１と同一の方法で油滴形成を行った結果、
油滴中には５〜１０μｍ程のカーボンブラックの凝集物
がみられた。この懸濁液を実施例−１と同一の手法にて
トナー合成し、平均粒径１３μｍのトナーを得た。この
トナーを用いてＤＣ−１００１にて画像形成したところ
、カブリ濃度０．０２画像濃度０．７５であった。Comparative Example-3 Carbon black: MA-100 (specific surface area 134 d/g) not treated with an aluminum coupling agent
, p) I value 3.0) (manufactured by Mitsubishi Chemical Industries, Ltd.) was used to form oil droplets in the same manner as in Example-1. As a result,
Carbon black aggregates of about 5 to 10 μm were observed in the oil droplets. A toner was synthesized from this suspension in the same manner as in Example 1 to obtain a toner having an average particle size of 13 μm. When an image was formed with DC-1001 using this toner, the fog density was 0.02 and the image density was 0.75.
比較例−４
アルミニウムカップリング剤で処理を行フていない、カ
ーボンブラック：スペシャルブラック５（比表面積１３
４ｍ’／ｇ、 ｐｕ値２．７ ） （デグサ社製〕を
５部用いて、実施例−１と同一の方法で油滴形成を行っ
た結果、油滴中には、５〜１０μｍ程のカーボンブラッ
クの凝集物がみられた。この懸濁液を実施例−１と同一
の手法にてトナー合成し、平均粒径１４μｍのトナーを
得た。このトナーを用いてＤＣ−１００１にて画像形成
したところ、カブリ濃度０．０２、画像濃度０．７８で
あった。Comparative Example-4 Carbon black not treated with aluminum coupling agent: Special Black 5 (specific surface area 13
4 m'/g, pu value 2.7) (manufactured by Degussa) to form oil droplets in the same manner as in Example-1. Aggregates of carbon black were observed.This suspension was synthesized into a toner using the same method as in Example 1 to obtain a toner with an average particle size of 14 μm.Using this toner, an image was produced using DC-1001. When formed, the fog density was 0.02 and the image density was 0.78.
比較例−５
アルミニウムカップリング剤で処理を行っていない。カ
ーボンブラック：ＦＷ２００（比表面積４６０ｒｎ”／
ｇ、ｐＨ値２．５ ） （デグサ社製）を５部用いて
、実施例−１と同一の方法で油滴形成を行った結果、油
滴中には、２〜１０μｍ程のカーボンブラックの凝集物
がみられた。この懸濁液を実施例−１と同一の手法にて
トナー合成し、平均粒径１４μｍのトナーを得た。この
トナーを用いてＤＣ−１００１にて画像形成したところ
、カブリ濃度０．０２、画像濃度０．６９であフた。Comparative Example-5 No treatment with aluminum coupling agent. Carbon black: FW200 (specific surface area 460rn”/
(g, pH value 2.5) (manufactured by Degussa) to form oil droplets in the same manner as in Example 1. As a result, carbon black of about 2 to 10 μm was found in the oil droplets. Aggregates were observed. A toner was synthesized from this suspension in the same manner as in Example 1 to obtain a toner having an average particle size of 14 μm. When an image was formed using this toner using DC-1001, the fog density was 0.02 and the image density was 0.69.
比較例−６
アルミニウムカップリング剤で処理を行っていないカー
ボンブラック：プリンテックスしく比表面積１５ ｏｒ
ｎ”／ｇ、 ｐＨ値８．５ ） （デグサ社製）を５
部用いて、実施例−１と同一の方法で油滴形成を行った
結果、油滴中には、５〜１０μ程のカーボンブラックの
凝集物がみられた。この懸濁液を実施例−１と同一の手
法にてトナー合成し、ＤＣ−１００１にて画像形成した
とこ′ろ、カブリ濃度０．０３、画像濃度０．７２であ
った。Comparative Example-6 Carbon black not treated with aluminum coupling agent: Printex has a specific surface area of 15 or
n”/g, pH value 8.5) (manufactured by Degussa) at 5
As a result of forming oil droplets in the same manner as in Example 1, carbon black aggregates of about 5 to 10 μm in size were observed in the oil droplets. A toner was synthesized from this suspension in the same manner as in Example 1, and an image was formed using DC-1001, resulting in a fog density of 0.03 and an image density of 0.72.
上記、実施例１．２、比較例１〜６の結果をまとめ表１
に示した。Table 1 summarizes the results of Example 1.2 and Comparative Examples 1 to 6 above.
It was shown to.
尚、前述した各実施例においては、分級されたトナー粒
子を所定の大ぎさの正方開口のメツシュを用いて篩にか
け、部落とされたトナーを更にもう一度同じ正方開口の
篩にかける。これを数回繰り返すことによって真円度の
高いトナーを得た。In each of the above-described embodiments, the classified toner particles are sieved using a mesh with square openings of a predetermined size, and the separated toner particles are passed through a sieve with the same square openings again. By repeating this several times, a toner with high roundness was obtained.
また比較例のトナーは、通常の分級後のトナーをそのま
ま用いた。Further, as the toner of the comparative example, the toner after normal classification was used as it was.
以下に真円度（Ｄ）の値を示す。The values of roundness (D) are shown below.
トナー −スヱ１以り
実施例１ ０．９３
実施例２ ０．９２
比較例ｔ ｏ、ａ ａ
比較例２ ０．８７
比較例３ ０．８８
比較例４ ０．８６
比較例５ ０．８７
比較例６ ０．８６
真円度の測定は、トナー粒子を電子顕＠鏡観察し、その
長径と短径を計測し、直径法によって算出した。Toner - Sue 1 Example 1 0.93 Example 2 0.92 Comparative example to,a a Comparative example 2 0.87 Comparative example 3 0.88 Comparative example 4 0.86 Comparative example 5 0.87 Comparison Example 6 0.86 The roundness was measured by observing the toner particles under an electron microscope, measuring the major axis and minor axis, and calculating by the diameter method.
Claims (2)
とこの定着用樹脂中に分散したカーボンブラックとの組
成物から成る静電荷像現像用トナーにおいて、 該トナーは下記式 Ｄ＝√（ｒ＿ｌ・ｒ＿ｓ）／ｒ＿ｌ 式中、ｒ＿ｌはトナー粒子の長径を表わし、ｒ＿ｓはト
ナー粒子の短径を表わす、 で定義される真円度が０．９０以上の球状粒子から成り
、 カーボンブラックは比表面積が３００ｍ＾２／ｇ以下で
ｐＨ値が７．０以下のカーボンブラックであり、且つ該
トナー中にはアルミニウムカップリング剤が存在するこ
とを特徴とするトナー。(1) In an electrostatic image developing toner comprising a composition of a fixing resin made of a radically polymerizable thermoplastic resin and carbon black dispersed in the fixing resin, the toner has the following formula D=√(r_l・r_s)/r_l In the formula, r_l represents the major axis of the toner particle, and r_s represents the minor axis of the toner particle. Carbon black consists of spherical particles with a circularity of 0.90 or more, defined as A toner comprising carbon black having a carbon black of 300 m^2/g or less and a pH value of 7.0 or less, and in which an aluminum coupling agent is present.
／ｇ以下かつ、ｐＨ値７．０以下のカーボンブラック及
びアルミニウムカップリング剤を含有する組成物と水性
媒体中に懸濁させ、 この懸濁粒子をラジカル開始剤の存在下に重合させ、 定着用樹脂と該樹脂中に分散したカーボンブラックとか
ら成る球状粒子を取得することから成る静電荷像現像用
トナーの製造方法。(2) Radical polymerizable monomer, specific surface area is 300m^2
/g or less and a composition containing carbon black and an aluminum coupling agent with a pH value of 7.0 or less in an aqueous medium, and the suspended particles are polymerized in the presence of a radical initiator for fixing. A method for producing a toner for developing electrostatic images, which comprises obtaining spherical particles consisting of a resin and carbon black dispersed in the resin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62043069A JP2588886B2 (en) | 1987-02-27 | 1987-02-27 | Method for producing toner for developing electrostatic images |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62043069A JP2588886B2 (en) | 1987-02-27 | 1987-02-27 | Method for producing toner for developing electrostatic images |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63210849A true JPS63210849A (en) | 1988-09-01 |
| JP2588886B2 JP2588886B2 (en) | 1997-03-12 |
Family
ID=12653565
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62043069A Expired - Lifetime JP2588886B2 (en) | 1987-02-27 | 1987-02-27 | Method for producing toner for developing electrostatic images |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2588886B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0430706A2 (en) * | 1989-11-30 | 1991-06-05 | Mita Industrial Co., Ltd. | Toner for developing electrostatic images and a method of manufacturing the same |
| US6030737A (en) * | 1996-11-11 | 2000-02-29 | Canon Kabushiki Kaisha | Non-magnetic toner for developing electrostatic image, process for producing non-magnetic toner particles, and image forming method |
| US6316157B1 (en) | 1999-07-05 | 2001-11-13 | Canon Kabushiki Kaisha | Toner and image forming method |
| JP2006195277A (en) * | 2005-01-14 | 2006-07-27 | Kyocera Chemical Corp | Toner and method for manufacturing toner |
Citations (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5333151A (en) * | 1976-09-08 | 1978-03-28 | Mitsubishi Chem Ind | Toner composition |
| JPS57181553A (en) * | 1981-04-30 | 1982-11-09 | Konishiroku Photo Ind Co Ltd | Toner for developing electrostatic charge image and its manufacture |
| JPS5950452A (en) * | 1982-09-17 | 1984-03-23 | Ricoh Co Ltd | Electrostatic image developing toner and its manufacture |
| JPS5964854A (en) * | 1982-10-05 | 1984-04-12 | Konishiroku Photo Ind Co Ltd | Developer |
| JPS59211050A (en) * | 1983-05-17 | 1984-11-29 | Hitachi Metals Ltd | Reversal development method |
| JPS6045260A (en) * | 1983-08-23 | 1985-03-11 | Canon Inc | Toner |
| JPS60117254A (en) * | 1983-11-30 | 1985-06-24 | Canon Inc | Electrostatic charge image developing toner |
| JPS60117252A (en) * | 1983-11-30 | 1985-06-24 | Canon Inc | Electrostatic charge image developing toner |
| JPS60117255A (en) * | 1983-11-30 | 1985-06-24 | Canon Inc | Electrostatic charge image developing toner |
| JPS60117253A (en) * | 1983-11-30 | 1985-06-24 | Canon Inc | Electrostatic charge image developing toner |
| JPS60138563A (en) * | 1983-12-27 | 1985-07-23 | Minolta Camera Co Ltd | Toner for developing electrostatic latent image |
| JPS6122353A (en) * | 1984-07-11 | 1986-01-30 | Showa Denko Kk | Production of toner for developing electrostatic charge image |
-
1987
- 1987-02-27 JP JP62043069A patent/JP2588886B2/en not_active Expired - Lifetime
Patent Citations (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5333151A (en) * | 1976-09-08 | 1978-03-28 | Mitsubishi Chem Ind | Toner composition |
| JPS57181553A (en) * | 1981-04-30 | 1982-11-09 | Konishiroku Photo Ind Co Ltd | Toner for developing electrostatic charge image and its manufacture |
| JPS5950452A (en) * | 1982-09-17 | 1984-03-23 | Ricoh Co Ltd | Electrostatic image developing toner and its manufacture |
| JPS5964854A (en) * | 1982-10-05 | 1984-04-12 | Konishiroku Photo Ind Co Ltd | Developer |
| JPS59211050A (en) * | 1983-05-17 | 1984-11-29 | Hitachi Metals Ltd | Reversal development method |
| JPS6045260A (en) * | 1983-08-23 | 1985-03-11 | Canon Inc | Toner |
| JPS60117254A (en) * | 1983-11-30 | 1985-06-24 | Canon Inc | Electrostatic charge image developing toner |
| JPS60117252A (en) * | 1983-11-30 | 1985-06-24 | Canon Inc | Electrostatic charge image developing toner |
| JPS60117255A (en) * | 1983-11-30 | 1985-06-24 | Canon Inc | Electrostatic charge image developing toner |
| JPS60117253A (en) * | 1983-11-30 | 1985-06-24 | Canon Inc | Electrostatic charge image developing toner |
| JPS60138563A (en) * | 1983-12-27 | 1985-07-23 | Minolta Camera Co Ltd | Toner for developing electrostatic latent image |
| JPS6122353A (en) * | 1984-07-11 | 1986-01-30 | Showa Denko Kk | Production of toner for developing electrostatic charge image |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0430706A2 (en) * | 1989-11-30 | 1991-06-05 | Mita Industrial Co., Ltd. | Toner for developing electrostatic images and a method of manufacturing the same |
| JPH03171144A (en) * | 1989-11-30 | 1991-07-24 | Mita Ind Co Ltd | Electrostatic charge image developing toner and manufacture of same |
| US6030737A (en) * | 1996-11-11 | 2000-02-29 | Canon Kabushiki Kaisha | Non-magnetic toner for developing electrostatic image, process for producing non-magnetic toner particles, and image forming method |
| US6316157B1 (en) | 1999-07-05 | 2001-11-13 | Canon Kabushiki Kaisha | Toner and image forming method |
| JP2006195277A (en) * | 2005-01-14 | 2006-07-27 | Kyocera Chemical Corp | Toner and method for manufacturing toner |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2588886B2 (en) | 1997-03-12 |
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