JPH0264652A - Production of toner for developing electrostatic charge image - Google Patents
Production of toner for developing electrostatic charge imageInfo
- Publication number
- JPH0264652A JPH0264652A JP63217712A JP21771288A JPH0264652A JP H0264652 A JPH0264652 A JP H0264652A JP 63217712 A JP63217712 A JP 63217712A JP 21771288 A JP21771288 A JP 21771288A JP H0264652 A JPH0264652 A JP H0264652A
- Authority
- JP
- Japan
- Prior art keywords
- toner
- polymer particles
- water
- weight
- acid
- 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 13
- 239000002245 particle Substances 0.000 claims abstract description 57
- 229920000642 polymer Polymers 0.000 claims abstract description 36
- 239000000843 powder Substances 0.000 claims abstract description 29
- 239000006185 dispersion Substances 0.000 claims abstract description 22
- 239000003381 stabilizer Substances 0.000 claims abstract description 22
- 239000007788 liquid Substances 0.000 claims abstract description 10
- 239000000725 suspension Substances 0.000 claims abstract description 5
- 239000000178 monomer Substances 0.000 claims description 45
- 229910017053 inorganic salt Inorganic materials 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 19
- 239000003960 organic solvent Substances 0.000 claims description 14
- 239000003086 colorant Substances 0.000 claims description 12
- 238000005406 washing Methods 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 239000002612 dispersion medium Substances 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 16
- 229910001868 water Inorganic materials 0.000 abstract description 16
- 239000003513 alkali Substances 0.000 abstract description 14
- 238000004140 cleaning Methods 0.000 abstract description 13
- 238000000034 method Methods 0.000 abstract description 9
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 150000003839 salts Chemical class 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 37
- 239000007864 aqueous solution Substances 0.000 description 15
- 238000006116 polymerization reaction Methods 0.000 description 11
- -1 vinyl aromatic hydrocarbons Chemical class 0.000 description 10
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 239000000049 pigment Substances 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 238000010298 pulverizing process Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 229920003169 water-soluble polymer 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
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 238000010557 suspension polymerization reaction Methods 0.000 description 3
- 229920001567 vinyl ester resin Polymers 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-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
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-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
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 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
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000006229 carbon black Substances 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
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- 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 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-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
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 239000000696 magnetic material Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000005673 monoalkenes Chemical class 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 108091008695 photoreceptors Proteins 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000001054 red pigment Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000010558 suspension polymerization method Methods 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- 235000014692 zinc oxide Nutrition 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OSNILPMOSNGHLC-UHFFFAOYSA-N 1-[4-methoxy-3-(piperidin-1-ylmethyl)phenyl]ethanone Chemical compound COC1=CC=C(C(C)=O)C=C1CN1CCCCC1 OSNILPMOSNGHLC-UHFFFAOYSA-N 0.000 description 1
- PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical compound CCCCOOCCCC PAOHAQSLJSMLAT-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
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-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
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-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
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- FWLHAQYOFMQTHQ-UHFFFAOYSA-N 2-N-[8-[[8-(4-aminoanilino)-10-phenylphenazin-10-ium-2-yl]amino]-10-phenylphenazin-10-ium-2-yl]-8-N,10-diphenylphenazin-10-ium-2,8-diamine hydroxy-oxido-dioxochromium Chemical compound O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.Nc1ccc(Nc2ccc3nc4ccc(Nc5ccc6nc7ccc(Nc8ccc9nc%10ccc(Nc%11ccccc%11)cc%10[n+](-c%10ccccc%10)c9c8)cc7[n+](-c7ccccc7)c6c5)cc4[n+](-c4ccccc4)c3c2)cc1 FWLHAQYOFMQTHQ-UHFFFAOYSA-N 0.000 description 1
- JFMYRCRXYIIGBB-UHFFFAOYSA-N 2-[(2,4-dichlorophenyl)diazenyl]-n-[4-[4-[[2-[(2,4-dichlorophenyl)diazenyl]-3-oxobutanoyl]amino]-3-methylphenyl]-2-methylphenyl]-3-oxobutanamide Chemical compound C=1C=C(C=2C=C(C)C(NC(=O)C(N=NC=3C(=CC(Cl)=CC=3)Cl)C(C)=O)=CC=2)C=C(C)C=1NC(=O)C(C(=O)C)N=NC1=CC=C(Cl)C=C1Cl JFMYRCRXYIIGBB-UHFFFAOYSA-N 0.000 description 1
- MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 1
- LBNDGEZENJUBCO-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethyl]butanedioic acid Chemical compound CC(=C)C(=O)OCCC(C(O)=O)CC(O)=O LBNDGEZENJUBCO-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
- MLMGJTAJUDSUKA-UHFFFAOYSA-N 2-ethenyl-1h-imidazole Chemical compound C=CC1=NC=CN1 MLMGJTAJUDSUKA-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-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
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- DWDURZSYQTXVIN-UHFFFAOYSA-N 4-[(4-aminophenyl)-(4-methyliminocyclohexa-2,5-dien-1-ylidene)methyl]aniline Chemical compound C1=CC(=NC)C=CC1=C(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 DWDURZSYQTXVIN-UHFFFAOYSA-N 0.000 description 1
- LVOJOIBIVGEQBP-UHFFFAOYSA-N 4-[[2-chloro-4-[3-chloro-4-[(5-hydroxy-3-methyl-1-phenylpyrazol-4-yl)diazenyl]phenyl]phenyl]diazenyl]-5-methyl-2-phenylpyrazol-3-ol Chemical compound CC1=NN(C(O)=C1N=NC1=CC=C(C=C1Cl)C1=CC(Cl)=C(C=C1)N=NC1=C(O)N(N=C1C)C1=CC=CC=C1)C1=CC=CC=C1 LVOJOIBIVGEQBP-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
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 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
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- REEFSLKDEDEWAO-UHFFFAOYSA-N Chloraniformethan Chemical compound ClC1=CC=C(NC(NC=O)C(Cl)(Cl)Cl)C=C1Cl REEFSLKDEDEWAO-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
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- AOADSHDCARXSGL-ZMIIQOOPSA-M alkali blue 4B Chemical compound CC1=CC(/C(\C(C=C2)=CC=C2NC2=CC=CC=C2S([O-])(=O)=O)=C(\C=C2)/C=C/C\2=N\C2=CC=CC=C2)=CC=C1N.[Na+] AOADSHDCARXSGL-ZMIIQOOPSA-M 0.000 description 1
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- 239000000987 azo dye Substances 0.000 description 1
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- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
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- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
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- 159000000007 calcium salts Chemical class 0.000 description 1
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- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
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- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
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- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
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- 238000010894 electron beam technology Methods 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
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- 150000002170 ethers Chemical class 0.000 description 1
- PLYDMIIYRWUYBP-UHFFFAOYSA-N ethyl 4-[[2-chloro-4-[3-chloro-4-[(3-ethoxycarbonyl-5-oxo-1-phenyl-4h-pyrazol-4-yl)diazenyl]phenyl]phenyl]diazenyl]-5-oxo-1-phenyl-4h-pyrazole-3-carboxylate Chemical compound CCOC(=O)C1=NN(C=2C=CC=CC=2)C(=O)C1N=NC(C(=C1)Cl)=CC=C1C(C=C1Cl)=CC=C1N=NC(C(=N1)C(=O)OCC)C(=O)N1C1=CC=CC=C1 PLYDMIIYRWUYBP-UHFFFAOYSA-N 0.000 description 1
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- HTENFZMEHKCNMD-UHFFFAOYSA-N helio brilliant orange rk Chemical compound C1=CC=C2C(=O)C(C=C3Br)=C4C5=C2C1=C(Br)C=C5C(=O)C1=CC=CC3=C14 HTENFZMEHKCNMD-UHFFFAOYSA-N 0.000 description 1
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- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 1
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- CUSDLVIPMHDAFT-UHFFFAOYSA-N iron(3+);manganese(2+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Mn+2].[Fe+3].[Fe+3] CUSDLVIPMHDAFT-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- YOBAEOGBNPPUQV-UHFFFAOYSA-N iron;trihydrate Chemical compound O.O.O.[Fe].[Fe] YOBAEOGBNPPUQV-UHFFFAOYSA-N 0.000 description 1
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- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- ZTERWYZERRBKHF-UHFFFAOYSA-N magnesium iron(2+) oxygen(2-) Chemical compound [Mg+2].[O-2].[Fe+2].[O-2] ZTERWYZERRBKHF-UHFFFAOYSA-N 0.000 description 1
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- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229940107698 malachite green Drugs 0.000 description 1
- FDZZZRQASAIRJF-UHFFFAOYSA-M malachite green Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 FDZZZRQASAIRJF-UHFFFAOYSA-M 0.000 description 1
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- 239000011572 manganese Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- 229910052759 nickel Inorganic materials 0.000 description 1
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- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000001053 orange pigment Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001057 purple pigment Substances 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 235000012752 quinoline yellow Nutrition 0.000 description 1
- 239000004172 quinoline yellow Substances 0.000 description 1
- 229940051201 quinoline yellow Drugs 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- VEALVRVVWBQVSL-UHFFFAOYSA-N strontium titanate Chemical compound [Sr+2].[O-][Ti]([O-])=O VEALVRVVWBQVSL-UHFFFAOYSA-N 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- RBKBGHZMNFTKRE-UHFFFAOYSA-K trisodium 2-[(2-oxido-3-sulfo-6-sulfonatonaphthalen-1-yl)diazenyl]benzoate Chemical compound C1=CC=C(C(=C1)C(=O)[O-])N=NC2=C3C=CC(=CC3=CC(=C2[O-])S(=O)(=O)O)S(=O)(=O)[O-].[Na+].[Na+].[Na+] RBKBGHZMNFTKRE-UHFFFAOYSA-K 0.000 description 1
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
- JEVGKYBUANQAKG-UHFFFAOYSA-N victoria blue R Chemical compound [Cl-].C12=CC=CC=C2C(=[NH+]CC)C=CC1=C(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 JEVGKYBUANQAKG-UHFFFAOYSA-N 0.000 description 1
- 239000012463 white pigment Substances 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
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
Landscapes
- Physics & Mathematics (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)
本発明は電子写真法や静電印刷法に使用される静電荷像
現像用トナーを′?A濁重合によって直接的に製造する
方法に関し、より詳細には重合後の重合体粒子表面の分
散安定剤が有効に除去できる静電荷像現像用トナーの製
造方法に関する。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to toner for developing electrostatic images used in electrophotography and electrostatic printing. A: This invention relates to a direct production method by turbid polymerization, and more particularly relates to a method for producing a toner for developing electrostatic images, which can effectively remove a dispersion stabilizer from the surface of polymer particles after polymerization.
(従来技術)
電子写真法、静電印刷法の分野では、像担持体上に形成
された静電潜像を可視像化する目的でトナーを使用して
いる。このトナーは、樹脂媒質中に着色剤等の添加剤が
分散された着色樹脂粒子であり、一般に5乃至30μm
の粒度範囲を有するものである。樹脂媒質としては所望
の検電性と結着性を備えた樹脂、例えばスチレン系樹脂
、ポリエステル系樹脂等の各種樹脂が使用され、着色剤
としてはカーボンブラックや他の有機系または無機系の
着色顔料が使用される。(Prior Art) In the fields of electrophotography and electrostatic printing, toner is used for the purpose of visualizing an electrostatic latent image formed on an image carrier. This toner is colored resin particles in which additives such as colorants are dispersed in a resin medium, and generally has a particle size of 5 to 30 μm.
It has a particle size range of . As the resin medium, various resins with desired electrodetection properties and binding properties are used, such as styrene resins and polyester resins, and as the coloring agent, carbon black or other organic or inorganic coloring agents are used. pigments are used.
従来より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、所謂粉砕法よって製造してきた。しかしながら、
この粉砕法による混練及び粉砕工程には多大なエネルギ
ーを必要とし、また微粉や粗大粒子を多く発生するため
に生産効率が低く、コスト高になる欠点が従来より指摘
されてきた。また、粉砕法により得られるトナーは粒子
の形状が不定形であるために、トナーの流動性が概して
低く、ブロッキングを発生したり、耐久性に乏しく、ま
た粒子個々の帯電電荷の蓄積性が異なるため、低帯電量
トナーを発生し易いという特性上の欠点も指摘されてき
た。Conventionally, the most typical manufacturing method for this toner consists of the steps of melt-kneading the aforementioned resin medium and colorant, cooling and pulverizing this kneaded material, and classifying the pulverized material to align the particle size within a certain range. It has been manufactured by the crushing method. however,
It has been pointed out that the kneading and pulverizing steps by this pulverization method require a large amount of energy and generate a large amount of fine powder and coarse particles, resulting in low production efficiency and high costs. In addition, since the toner obtained by the pulverization method has irregular particle shapes, the toner generally has low fluidity, may cause blocking, has poor durability, and the accumulation of electrical charges differs between individual particles. Therefore, it has been pointed out that the toner tends to generate a low charge amount toner, which is a characteristic disadvantage.
そこで、粉砕法によるトナー及び製造上の欠点を解消し
、ブロッキングを発生することなく、流動性、電荷蓄積
性及び耐久性が良好な球形のトナーを効率よく製造する
ために懸濁重合によるトナーの製造方法が提案された。Therefore, in order to eliminate the toner and manufacturing defects caused by the pulverization method and efficiently produce spherical toner with good fluidity, charge accumulation property, and durability without causing blocking, toner production by suspension polymerization was developed. A manufacturing method was proposed.
懸濁重合法においては重合性単量体に着色剤等のトナー
特性付与剤を添加混合した単量体組成物を分散安定剤が
存在する水中に懸濁分散して該組成物からなる油滴粒子
生成し、その後に重合して適正粒径のトナーを直接的に
得るものである。In the suspension polymerization method, a monomer composition prepared by adding and mixing a toner characteristic imparting agent such as a colorant to a polymerizable monomer is suspended and dispersed in water containing a dispersion stabilizer to form oil droplets made of the composition. Particles are generated and then polymerized to directly obtain a toner having an appropriate particle size.
−船釣に分散安定剤としては水溶性高分子、界面活性剤
、難水溶性無機塩微粉末等が使用される。-Water-soluble polymers, surfactants, poorly water-soluble inorganic salt fine powders, etc. are used as dispersion stabilizers for boat fishing.
例えば特開昭59−152447号公報、// 59−
152448号公報等においてしめされるように、難水
溶性無機塩微粉末が水中での帯電することを利用して電
気的に油滴粒子を安定化でき、均一粒径の粒子に油滴粒
子を安定化できるという利点から無機塩微粉末が好まし
く使用される。そして重合後は重合体粒子(トナー)表
面に付着する無機塩微粉末が吸湿性を示してトナーの環
境安定性を阻害するために、酸またはアルカリによる洗
浄によって無機塩微粉末の除去を行っている。For example, JP-A-59-152447, //59-
As shown in Publication No. 152448, etc., it is possible to electrically stabilize oil droplet particles by utilizing the fact that poorly water-soluble inorganic salt fine powder is charged in water, and it is possible to stabilize oil droplet particles into particles of uniform particle size. Inorganic salt fine powder is preferably used because of its ability to be stabilized. After polymerization, the fine inorganic salt powder adhering to the surface of the polymer particles (toner) exhibits hygroscopic properties and inhibits the environmental stability of the toner, so the fine inorganic salt powder is removed by washing with acid or alkali. There is.
(発明が解決しようとする問題点)
上記酸またはアルカリによる洗浄は、酸またはアルカリ
が溶解した水溶液に重合物を投入して、重合体粒子表面
の無機塩微粉末を酸またはアルカリと反応させて、粒子
表面より引き離し水溶液中に溶解させることよりなされ
ている。しかしながら、洗浄初期は粒子表面の無機塩微
粉末のために重合体粒子が酸またはアルカリ水溶液中に
分散した状態で粒子個々に酸またはアルカリが反応して
除去反応が行われるが、洗浄の進行にともなって無機塩
微粉末が粒子表面からある程度除去されると重合体粒子
が水溶液中で凝集しはじめ、個々の重合体粒子に酸また
はアルカリがまんべんなく接触しなくなって除去反応が
進行しな(なり、完全な無機塩微粉末の除去がなされな
いことが分かった。また、同様に水溶性高分子や界面活
性剤を使用した際においても、重合後の熱水や水による
洗浄中に粒子同士の凝集によって完全に分散安定剤が除
去できないことがわかった。(Problems to be Solved by the Invention) The above-mentioned acid or alkali cleaning is performed by adding a polymer to an aqueous solution in which an acid or alkali is dissolved, and causing the inorganic salt fine powder on the surface of the polymer particles to react with the acid or alkali. This is done by separating the particles from the surface and dissolving them in an aqueous solution. However, at the initial stage of cleaning, the polymer particles are dispersed in an acid or alkali aqueous solution due to the inorganic salt fine powder on the particle surface, and the acid or alkali reacts with each particle to perform a removal reaction, but as the cleaning progresses, When the inorganic salt fine powder is removed to some extent from the particle surface, the polymer particles begin to aggregate in the aqueous solution, and the acid or alkali does not evenly contact the individual polymer particles, preventing the removal reaction from proceeding. It was found that the inorganic salt fine powder was not completely removed.Also, even when water-soluble polymers and surfactants were used, particles agglomerated during washing with hot water or water after polymerization. It was found that the dispersion stabilizer could not be completely removed by this method.
本発明は上述する点に鑑Aされたものであり、その目的
は重合体粒子表面に残留付着する無機塩微粉末等の分散
安定剤をを有効に除去する方法を提供することにある。The present invention has been made in consideration of the above points, and its object is to provide a method for effectively removing dispersion stabilizers such as inorganic salt fine powder remaining on the surface of polymer particles.
本発明の他の目的は、トナーの環境安定性を良好にし、
優れた現像性の得られるトナーを提供することにある。Another object of the present invention is to improve the environmental stability of the toner;
The purpose of the present invention is to provide a toner with excellent developability.
更に、本発明の他の目的は、短時間で効率よく行える分
散安定剤の洗浄方法を提供することにある。Furthermore, another object of the present invention is to provide a method of cleaning a dispersion stabilizer that can be carried out efficiently in a short time.
(問題点を解決するための手段)
本発明によれば、重合性単量体及び着色剤等の添加剤の
混合物からなる単量体組成物を、分散安定剤が分散され
た分散媒中で懸濁重合して重合体粒子を得た後、該重合
体粒子表面に付着する分散安定剤を水系液体で洗浄して
除去する工程からなる静電荷像現像用トナーの製造方法
において、前記水系液体中に水溶性有機溶剤を添加して
除去操作を行うことにより、本発明の目的が達成される
。(Means for Solving the Problems) According to the present invention, a monomer composition consisting of a mixture of a polymerizable monomer and an additive such as a colorant is prepared in a dispersion medium in which a dispersion stabilizer is dispersed. A method for producing a toner for developing an electrostatic image, which comprises a step of obtaining polymer particles by suspension polymerization, and then removing the dispersion stabilizer adhering to the surface of the polymer particles by washing with an aqueous liquid. The object of the present invention can be achieved by adding a water-soluble organic solvent therein and performing a removal operation.
(作用)
本発明は懸濁重合後の水系液体による重合体粒子の洗浄
工程において、水系液体中に適量の水溶性の有機溶剤を
添加することを特徴とする。(Function) The present invention is characterized by adding an appropriate amount of a water-soluble organic solvent to the aqueous liquid in the step of washing the polymer particles with the aqueous liquid after suspension polymerization.
以下、分散安定剤として難水溶性無機塩微粉末を使用す
る場合について説明すると、水溶液中の酸またはアルカ
リとの反応によって無機塩微粉末がある程度除去された
重合体粒子は、水溶液との濡れ性が低下して粒子同志が
凝集性をしめす。ここで、水溶性の有機溶剤が適量溶解
した水溶液を用いると、無機塩微粉末の存在量によらず
とも重合体粒子と水溶液との濡れ性が確保され、常に粒
子価々が独立に分散した状態で酸またはアルカリと無機
塩微粉末との反応(除去反応)が均−且つ速やかに進行
し、重合体粒子表面から完全或いはほぼ完全に無機塩微
粉末が除去することができる。Below, we will explain the case of using poorly water-soluble inorganic salt fine powder as a dispersion stabilizer. Polymer particles from which a certain amount of inorganic salt fine powder has been removed by reaction with an acid or alkali in an aqueous solution have a high wettability with an aqueous solution. decreases and the particles show cohesion. Here, when an aqueous solution containing an appropriate amount of a water-soluble organic solvent is used, the wettability of the polymer particles with the aqueous solution is ensured regardless of the amount of inorganic salt fine powder present, and the particles are always dispersed independently. In this state, the reaction (removal reaction) between the acid or alkali and the inorganic salt fine powder proceeds evenly and rapidly, and the inorganic salt fine powder can be completely or almost completely removed from the surface of the polymer particles.
以下に、本発明を更に詳細に説明する。The present invention will be explained in more detail below.
本発明におけるトナーを構成する重合性の単量体として
は、従来公知の懸濁重合法によりトナーを製造する場合
に使用される重合性単量体が使用され、生成される重合
体が定着性及び帯電性とを有する熱可塑性樹脂を形成し
得るものであり、ビニル芳香族単量体、アクリル単量体
、ビニルエステル単量体、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
。As the polymerizable monomer constituting the toner in the present invention, the polymerizable monomer used when producing toner by a conventionally known suspension polymerization method is used, and the resulting polymer has fixing properties. It is capable of forming thermoplastic resins having chargeability and electrostatic properties, including vinyl aromatic monomers, acrylic monomers, vinyl ester monomers, vinyl ether monomers, diolefin monomers, and monoolefins. system monomers, etc.
ビニル芳香族単量体としては 式、
式中、R,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、ニトロ基、或いはビニル基である
、
の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、0−
1m−1p−クロロスチレン、p−エチルスチレン、ジ
ビニルベンゼンの単独または2種以上の組み合わせを挙
げるとかでき、更に前述した他の単量体としては以下の
ものを挙げることができる。The vinyl aromatic monomer has the following formula: In the formula, R 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, a nitro group, or a vinyl group. certain vinyl aromatic hydrocarbons, such as styrene, α-methylstyrene, vinyltoluene, α-chlorostyrene, 0-
Examples include 1m-1p-chlorostyrene, p-ethylstyrene, and divinylbenzene alone or in combination of two or more, and other monomers mentioned above include the following.
式、
式中、R1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、ヒドロキシルアルキル
基、或いはビニルエステル基である、
のアクリル系単量体、例えばアクリル酸メチル、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、メタクリル酸メチル、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、T−ヒドロキシアクリル酸プロピル、σ
−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、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。Acrylic monomers, such as methyl acrylate, of the formula, where R1 is a hydrogen atom or a lower alkyl group R4 is a hydrogen atom, a hydrocarbon group having up to 12 carbon atoms, a hydroxyalkyl group, or a vinyl ester group; Ethyl acrylate, butyl acrylate, 2-ethylhexyl acrylate, cyclohexyl acrylate, phenyl acrylate, methyl methacrylate, methyl methacrylate, 2-ethylhexyl methacrylate, ethyl β-hydroxyacrylate, T-hydroxyacrylic acid Propyl, σ
-Butyl hydroxyacrylate, β-hydroxyethyl methacrylate, ethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, etc.
式、
式、
式中、R4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−n−ブチルエーテ
ル、ビニルフェニルエーテル、ビニルシクロへキサシル
エーテル等。Vinyl ethers of the formula, formula, where R4 is a monovalent hydrocarbon group having up to 12 carbon atoms, such as vinyl-n-butyl ether, vinyl phenyl ether, vinyl cyclohexacyl ether, etc.
式、
式中、Rs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 the formula, wherein Rs is a hydrogen atom or a lower alkyl group, such as vinyl formate, vinyl acetate, vinyl propionate, etc.
式中、R7、R11,R,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、クロロブレン類。Diolefins, particularly butadiene, isoprene, and chloroprenes, wherein each of R7, R11, and R is a hydrogen atom, a lower alkyl group, or a halogen atom.
式、
式中、Rl 0% RI 1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
ブチレン、ブテン−1、ペンテン−1,4−メチルペン
テン−1等。Monoolefins of the formula, in which each of Rl 0% RI 1 is a hydrogen atom or a lower alkyl group, particularly ethylene, propylene, isobutylene, butene-1, pentene-1,4-methylpentene-1, etc.
上記単量体のうち好適な単量体としては、スチレン系単
量体、アクリル系単量体等である。Suitable monomers among the above monomers include styrene monomers and acrylic monomers.
そして、上記単量体とともに着色剤をはじめとする他の
トナー特性付与剤を添加混合して重合性単量体と共に着
色剤をはじめとする他のトナー特性付与剤を添加混合し
て単量体組成物とする。Then, other toner characteristic imparting agents such as colorants are added and mixed together with the above monomers, and other toner characteristic imparting agents including colorants are added and mixed together with the polymerizable monomers to form monomers. A composition.
着色剤としては以下に記す従来公知のトナー用の種々の
顔料や染料(以下単に着色顔料と呼ぶ)使用できる。As the coloring agent, various conventionally known pigments and dyes for toners (hereinafter simply referred to as coloring pigments) described below can be used.
黒色顔料
カーボンブラック、アセチレンブラック、ランプブラッ
ク、アニリンブラック。Black pigments carbon black, acetylene black, lamp black, aniline black.
黄色顔料
黄鉛、亜鉛黄、カドミウムイエロー、黄色酸化鉄、ミネ
ラルファーストイエロー、ニッケルチタンイエロー、ネ
ーブルスイエロー、ナフトールイエローS1ハンザイエ
ロー10G1ベンジジンイエローG、 キノリンイエロ
ーレーキ、パーマネンエローNCG、タートラジンレー
キ。Yellow pigments yellow lead, zinc yellow, cadmium yellow, yellow iron oxide, mineral first yellow, nickel titanium yellow, nabels yellow, naphthol yellow S1 Hansa yellow 10G1 benzidine yellow G, quinoline yellow lake, permanent yellow NCG, tartrazine lake.
橙色顔料
赤口黄鉛、モリブテンオレンジ、パーマネントオレンジ
GTR,ピラゾロンオレンジ、パルカンオレンジ、イン
ダンスレンブリリアントオレンジRK、ベンジジンオレ
ンジG1インダンスレンブリリアントオレンジGK。Orange pigment red yellow lead, molybdenum orange, permanent orange GTR, pyrazolone orange, palkan orange, indanthrene brilliant orange RK, benzidine orange G1 indanthrene brilliant orange GK.
赤色顔料
ベンガラ、カドミュウムレッド、鉛丹、硫化水銀カドミ
ウム、パーマネントオレンジ4R、リソールレッド、ピ
ラゾロンレッド、ウオッチングレッドカルシウム塩、レ
ーキレッドD、ブリリアンドカーミン6B、エオシンレ
ーキ、ローダミンレーキB1アリザリンレーキ、ブリリ
アントカーミン3B。Red pigment red pigment Red Garla, Cadmium Red, Red Lead, Mercury Cadmium Sulfide, Permanent Orange 4R, Lysol Red, Pyrazolone Red, Watching Red Calcium Salt, Lake Red D, Brilliant Carmine 6B, Eosin Lake, Rhodamine Lake B1 Alizarin Lake, Brilliant Carmine 3B.
紫色顔料
マンガン紫、ファストバイオレットB1メチルバイオレ
ットレーキ。Purple pigment Manganese Purple, Fast Violet B1 Methyl Violet Lake.
青色顔料
紺青、コバルトフルー、アルカリブルーレーキ、ビクト
リアブルーレーキ、フタロヒアニンブルー無金属フタロ
シアニンブルー、フタロシアニンブル一部分塩素化物、
ファーストスカイブルー、インダンスエンブルーBC。Blue pigments navy blue, cobalt flu, alkali blue lake, Victoria blue lake, phthalophyanine blue metal-free phthalocyanine blue, phthalocyanine blue partially chlorinated,
First Sky Blue, Indance Blue BC.
緑色顔料
クロムグリーン、酸化クロム、ピグメントグリーンB1
マラカイトグリーンレーキ、ファナルイエローグリーン
G0
白色顔料
亜鉛華、酸化チタン、アンチモン白、硫化亜鉛。Green pigment chrome green, chromium oxide, pigment green B1
Malachite Green Lake, Final Yellow Green G0 White pigment zinc white, titanium oxide, antimony white, zinc sulfide.
体質顔料
パライト粉、炭酸バリウム、クレー、シリカ、ホワイト
カーボン、タルク、アルミホワイト。Extender pigments Palite powder, barium carbonate, clay, silica, white carbon, talc, aluminum white.
磁性材料顔料としては、例えば四三酸化鉄(FezO4
) 、三二酸化鉄(T −PezOa) 、酸化鉄亜鉛
(ZnFezOn) 、酸化鉄イツトリウム(YJes
O+z)、酸化カドミウム(GdtFesO+z) 、
酸化鉄銅(CuFezOa)、酸化鉄錯(PbFel□
08.) 酸化鉄ネオジウム(NdFeOt)、酸化
鉄バリウム(BaFe+zO+、)、酸化鉄マグネシウ
ム(MgFet04) 、酸化鉄マンガン(MnFez
Oa) 、酸化鉄ランタン(LaFeOt)、鉄粉(F
e)、コバルト粉 (Go)、ニッケル粉(Ni)等が
知られているが、本発明においてもこれら公知の磁性材
料の微粉末の任意のものを用いることができる。As the magnetic material pigment, for example, triiron tetroxide (FezO4
), iron sesquioxide (T-PezOa), zinc iron oxide (ZnFezOn), iron yttrium oxide (YJes
O+z), cadmium oxide (GdtFesO+z),
Iron copper oxide (CuFezOa), iron oxide complex (PbFel□
08. ) Neodymium iron oxide (NdFeOt), barium iron oxide (BaFe+zO+, ), magnesium iron oxide (MgFet04), manganese iron oxide (MnFez)
Oa), lanthanum iron oxide (LaFeOt), iron powder (F
e), cobalt powder (Go), nickel powder (Ni), etc., and any of these known fine powders of magnetic materials can be used in the present invention.
これら着色剤は使用する単量体によっても異なるが、−
船釣に言って重合性単量体100重量部当たり0.1乃
至50重量部、特に1乃至20重量部が好ましく使用で
きる。These colorants vary depending on the monomers used, but -
For boat fishing, it is preferably used in an amount of 0.1 to 50 parts by weight, particularly 1 to 20 parts by weight, per 100 parts by weight of the polymerizable monomer.
また、トナー粒子の電荷を制御するために、トナー粒子
中に電荷制御剤、例えば、ニグロシン染料、オイルブラ
ック、スビロンブラック等の油溶性の染料や、ナフテン
酸、サリチル酸、オクチル酸、高級脂肪酸、樹脂酸のマ
ンガン、鉄、コバルト、鉛、亜鉛、セリウム、カルシウ
ム、ニッケル等の金属塩である金属石鹸等或いは含金属
アゾ染料、ピリミジン化合物、アルキルサリチル酸の金
属キレート等を、重合性単量体樹脂100重量部当たり
0.01乃至10重量部、好ましくは0゜1乃至5重量
部含有させることができる。In addition, in order to control the charge of the toner particles, charge control agents such as oil-soluble dyes such as nigrosine dye, oil black, and soubiron black, naphthenic acid, salicylic acid, octylic acid, higher fatty acids, etc. are added to the toner particles. Metal soaps, etc., which are metal salts of resin acids such as manganese, iron, cobalt, lead, zinc, cerium, calcium, and nickel, or metal-containing azo dyes, pyrimidine compounds, metal chelates of alkyl salicylic acids, etc., are used as polymerizable monomer resins. It can be contained in an amount of 0.01 to 10 parts by weight, preferably 0.1 to 5 parts by weight per 100 parts by weight.
また、定着性の向上と、オフセット現像の防止のために
上記単量体中にオフセット防止剤として、例えば低分子
量ポリプロピレン、低分子量ポリエチレン、パラフィン
ワックス等の各種ワックス、炭素数4以上のオレフィン
系単量体の低分子量オレフィン重合体、脂肪酸アミド、
シリコーンオイル等を、重合性単量体100重量部当た
り0. 1乃至10重量部、特に1.5乃至3重量部を
使用することがきる。In addition, in order to improve fixing properties and prevent offset development, offset inhibitors may be added to the above monomers, such as various waxes such as low molecular weight polypropylene, low molecular weight polyethylene, paraffin wax, and olefin monomers having 4 or more carbon atoms. low molecular weight olefin polymer, fatty acid amide,
Silicone oil etc. is added at 0.00% per 100 parts by weight of the polymerizable monomer. 1 to 10 parts by weight can be used, especially 1.5 to 3 parts by weight.
そして、上記方法により得られた球形のトナー粒子は平
均粒形が5乃至20μm、特に6乃至15μmが好まし
く使用できる。The spherical toner particles obtained by the above method preferably have an average particle size of 5 to 20 μm, particularly 6 to 15 μm.
また、電荷制御性及びワックスの単量体中での分散安定
性等の目的で極性基を有する重合体を添加することもで
きる。Furthermore, a polymer having a polar group may be added for the purpose of charge control and dispersion stability in the wax monomer.
例えば、以下に記す極性単量体の単独重合体か或いは前
述した重合性単量体と極性単量体との共重合体であって
もよい。For example, it may be a homopolymer of polar monomers described below or a copolymer of the above-mentioned polymerizable monomer and polar monomer.
ヱ三7F7血爪量婆
本発明に使用されるアニオン性単量体としては、アクリ
ル酸、メタクリル酸の不飽和カルボン酸、マレイン酸、
フマル酸等の不飽和二塩基酸、無水マレイン酸、無水イ
タコン酸等の不飽和二塩基酸の無水物、スチレンスルホ
ン酸、2−アクリルアミド−2−2メチルプロパンスル
ホン酸、モノ(2−メタクリロイルオキシエチル)アシ
ドホスフェート、2−メタクリロイルオキシエチルコハ
ク酸等を挙げることができる。The anionic monomers used in the present invention include unsaturated carboxylic acids such as acrylic acid and methacrylic acid, maleic acid,
Unsaturated dibasic acids such as fumaric acid, anhydrides of unsaturated dibasic acids such as maleic anhydride and itaconic anhydride, styrenesulfonic acid, 2-acrylamido-2-2methylpropanesulfonic acid, mono(2-methacryloyloxy) (ethyl) acid phosphate, 2-methacryloyloxyethylsuccinic acid, and the like.
左土土ヱ血垂1体
ジメチルアミノ(メタ)アクリレート、ジエチルアミノ
エチル(メタ)アクリレート、ジエチルアミノプロピル
(メタ)アクリレート、N−アミノエチルアミノプロピ
ル(メタ)アクリレート、ビニルピリジン、2−ビニル
イミダゾール、2ヒドロキシ−3−アクリルオキシプロ
ピルメチルアンモニウムクロライド等の含む窒素単量体
等を使用することができる。1 body dimethylamino(meth)acrylate, diethylaminoethyl(meth)acrylate, diethylaminopropyl(meth)acrylate, N-aminoethylaminopropyl(meth)acrylate, vinylpyridine, 2-vinylimidazole, 2hydroxy Nitrogen monomers such as -3-acryloxypropylmethylammonium chloride can be used.
上記極性単量体等からなる極性基含有重合体は、前述し
た定着樹脂を形成しうる重合体単量体との溶解性及び生
成されたトナーの帯電性等を香料して適宜決定されるが
、−iに重合性単量体100重量部当り0.1乃至10
重量部使用される。The polar group-containing polymer made of the above-mentioned polar monomers etc. is appropriately determined by considering the solubility with the polymer monomer that can form the fixing resin mentioned above and the chargeability of the produced toner. , -i is 0.1 to 10 per 100 parts by weight of the polymerizable monomer.
Parts by weight are used.
前記重合性単量体及び上記着色剤をはじめとする単量体
組成物を無機塩微粉末、水溶性高分子及び界面活性剤を
分散安定剤として溶解乃至分散した水系の分散媒中に懸
濁分散して油滴粒子を生成する。無機塩微粉末としては
、単量体組成物の極性等によって適宜選択されるが、硫
酸カルシウム、リン酸カルシウム、炭酸マグネシウム、
炭酸バリウム、炭酸カルシウム、水酸化アルミニウム等
の難水溶性無機塩微粉末が使用される。また、水溶性高
分子としてはポリビニルアルコール、メチルセルロース
等や界面活性剤としては界面活性剤この分野で使用され
るノニオン系或いはイオン系の界面活性剤が使用される
。A monomer composition including the polymerizable monomer and the colorant is suspended in an aqueous dispersion medium in which a fine inorganic salt powder, a water-soluble polymer, and a surfactant are dissolved or dispersed as a dispersion stabilizer. Disperses to produce oil droplet particles. The inorganic salt fine powder is appropriately selected depending on the polarity of the monomer composition, and calcium sulfate, calcium phosphate, magnesium carbonate,
Fine powder of poorly water-soluble inorganic salts such as barium carbonate, calcium carbonate, aluminum hydroxide, etc. is used. Further, as the water-soluble polymer, polyvinyl alcohol, methyl cellulose, etc. are used, and as the surfactant, nonionic or ionic surfactants used in this field are used.
上記分散安定剤は水当り1乃至50重量%、特に10乃
至25重量%の量で加えるとよい。懸濁油滴の粒子サイ
ズは5乃至30μm、特に8乃至12μmに調整するの
が適当である。The above-mentioned dispersion stabilizer is preferably added in an amount of 1 to 50% by weight, particularly 10 to 25% by weight, based on water. The particle size of the suspended oil droplets is suitably adjusted to 5 to 30 μm, particularly 8 to 12 μm.
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、ジクミルペルオキシド、ジーも一
ブチルペルオキシド、過酸化ベンゾイル、過酸化ラウロ
イル等の過酸化物等の油溶性の開始剤が使用される。Examples of polymerization initiators include azo compounds such as azobisisobutyronitrile, and peroxides such as cumene hydroperoxide, t-butyl hydroperoxide, dicumyl peroxide, di-butyl peroxide, benzoyl peroxide, and lauroyl peroxide. Oil-soluble initiators such as
この他にT−線、加速電子線のようなイオン化放射線や
各種増感剤との組み合わせも使用される。In addition, combinations with ionizing radiation such as T-rays and accelerated electron beams and various sensitizers are also used.
アゾ化合物、過酸化物等の重合開始剤の配合量は、所謂
触媒量でよく、一般に仕込み単量体当たり0. 1乃至
10重量%の量で用いるのがよい。The amount of the polymerization initiator, such as an azo compound or peroxide, may be a so-called catalytic amount, and is generally 0.00% per monomer charged. It is preferable to use it in an amount of 1 to 10% by weight.
重厚温度及び時間は、公知のそれでよく、一般に40乃
至100″Cの温度で1時間乃至50時間の重合で充分
である。そして、粒径1乃至30μm、特に5乃至20
μmの重合体粒子を生成する。The polymerization temperature and time may be those known in the art, and generally polymerization for 1 to 50 hours at a temperature of 40 to 100''C is sufficient.
Produces micrometer polymer particles.
、′ による2゛
上記生成された表面に分散安定剤が付着した重合体粒子
を、重合反応液から濾過して取り出す。, ' 2゛The above-produced polymer particles with the dispersion stabilizer attached to their surfaces are filtered and removed from the polymerization reaction solution.
そして、難水溶性無機塩微粉末を使用する際は酸または
アルカリ及び適量の水溶性のf機溶剤が溶解した水溶液
によって洗浄操作を数回繰り返す。When a poorly water-soluble inorganic salt fine powder is used, the cleaning operation is repeated several times with an aqueous solution containing an acid or alkali and an appropriate amount of a water-soluble organic solvent.
また、水溶性高分子を使用する際は熱水に適量の水溶性
の有機溶剤を添加し、界面活性剤の場合は水に適量の水
溶性の有機溶剤を添加して洗浄操作を繰り返す。また、
濾過後のスラリー状の重合体粒子に水溶性の有機溶剤を
少量添加混合した後に、各種水系液体によって洗浄操作
を行ってもよく、これらは併用しても差し支えない。Further, when using a water-soluble polymer, add an appropriate amount of a water-soluble organic solvent to hot water, and when using a surfactant, add an appropriate amount of a water-soluble organic solvent to water and repeat the washing operation. Also,
After adding and mixing a small amount of a water-soluble organic solvent to the slurry-like polymer particles after filtration, a washing operation may be performed with various aqueous liquids, and these may be used in combination.
上記水溶性の有機溶剤としては、メタノール、エタノー
ル、プロパツール、ブタノール、イソブタノール、te
r t−ブタノール、ヘキサノール、オクタツール等の
アルコール類、ジオキサン、ジメチルエーテル、ジエチ
ルエーテル、テトラヒドロフラン、エチレングリコール
モノメチルエーテル、エチレングリコールモノエチルエ
ーテル、エチレングリコールジメチルエーテル、エチレ
ングリコールジエチルエーテル等のエーテル類、アセト
ン、メチルエチルケトン、シクロヘキサノン等のケトン
類、アセトニトリル、ホルムアミド、ジメチルホルムア
ミド等の種々の水溶性の有機溶媒が例示できる。このう
ち重合体粒子の表面性を安定に保つことからメタノール
等のアルコール類が好ましい。そして上記有機溶剤は1
種または2種以上が混合して用いられる。Examples of the water-soluble organic solvents include methanol, ethanol, propatool, butanol, isobutanol, te
r Alcohols such as t-butanol, hexanol, octatool, etc., ethers such as dioxane, dimethyl ether, diethyl ether, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, acetone, methyl ethyl ketone , ketones such as cyclohexanone, and various water-soluble organic solvents such as acetonitrile, formamide, and dimethylformamide. Among these, alcohols such as methanol are preferred because they keep the surface properties of the polymer particles stable. And the above organic solvent is 1
A species or a mixture of two or more species may be used.
これら有機溶剤は水溶液全体当たり1乃至1゜0%、特
に5乃至90%になるように添加することが好ましい。These organic solvents are preferably added in an amount of 1 to 1.0%, particularly 5 to 90%, based on the entire aqueous solution.
添加量が少なすぎると本発明の効果が付与されず、水溶
液中での重合体粒子の分散性が悪(なり分散安定剤の除
去作用が不完全になる。また、直接濾過後のスラリー状
の重合体粒子に上記水溶性の有機溶剤を添加混合しても
よい。If the amount added is too small, the effect of the present invention will not be imparted, and the dispersibility of the polymer particles in the aqueous solution will be poor (and the removal effect of the dispersion stabilizer will be incomplete. The above-mentioned water-soluble organic solvent may be added and mixed with the polymer particles.
無機塩微粉末と反応する酸、アルカリとしては従来より
用いられていものでよく、酸としては塩酸、硫酸、硝酸
、酢酸等があげられ、またアルカリとしては、水酸化カ
リウム、水酸化ナトリウム、水酸化カルシウム、水酸化
テトラメチルアンモニウム、炭酸アンモニウム、炭酸カ
リウム、炭酸ナナトリウム等があげられる。The acid or alkali that reacts with the inorganic salt fine powder may be any conventionally used acid or alkali. Examples of the acid include hydrochloric acid, sulfuric acid, nitric acid, acetic acid, etc., and examples of the alkali include potassium hydroxide, sodium hydroxide, water, etc. Examples include calcium oxide, tetramethylammonium hydroxide, ammonium carbonate, potassium carbonate, and sodium carbonate.
洗浄操作は水溶液中に重合体粒子を投入して、緩やかな
攪拌を施すことによって行われる。そして、洗浄後は濾
過後、乾燥してトナーとする。The washing operation is performed by introducing the polymer particles into an aqueous solution and gently stirring the solution. After washing, the toner is filtered and dried to form a toner.
生成されたトナーには、必要により流動性及び感光体の
清浄性を高めるために有機又は無機の微粒子を外部添加
してトナー組成物とすることができる。例えば、シリカ
、アルミナ、二酸化チタン、三酸化アンチモン、チタン
酸バリウム、チタン酸ストロンチウム、酸化マグネシウ
ム、ケイ酸カルシウム、酸化亜鉛等が挙げられ、特にコ
ロイド状シリカ、表面処理した疎水性シリカが好ましい
。If necessary, organic or inorganic fine particles can be externally added to the produced toner to improve fluidity and cleanliness of the photoreceptor to form a toner composition. Examples include silica, alumina, titanium dioxide, antimony trioxide, barium titanate, strontium titanate, magnesium oxide, calcium silicate, zinc oxide, etc., and colloidal silica and surface-treated hydrophobic silica are particularly preferred.
これら粒子の粒径は0.001乃至5μmのものが好ま
しく使用される。また、そのうち粒径が0.1乃至1μ
mのものは特に感光体の清掃性、クリニング性を向上さ
せる点で好ましい。These particles preferably have a particle size of 0.001 to 5 μm. In addition, the particle size is 0.1 to 1 μm.
Particularly preferred is m, since it improves the cleaning properties and cleaning properties of the photoreceptor.
(発明の効果)
本発明によれば重合反応後に得られる重合体粒子の表面
に付着する無機塩微粉等の分散安定剤を有効に除去する
ことができ、得られるトナーは環境安定性に優れ、また
帯電特性もより良好なものに改善される。更に、従来に
比べて洗浄時間の短縮も図ることができる。(Effects of the Invention) According to the present invention, dispersion stabilizers such as inorganic salt fine powder adhering to the surface of polymer particles obtained after a polymerization reaction can be effectively removed, and the obtained toner has excellent environmental stability. Furthermore, the charging characteristics are also improved. Furthermore, the cleaning time can be shortened compared to the conventional method.
以下、実施例によって本発明を更に詳細に説明する。Hereinafter, the present invention will be explained in more detail with reference to Examples.
(実施例1)
スチレン 80重量部メタクリ
ル酸−2−エチルへキシル
20重量部
グラフト化カーボンブラック 5重量部電荷制御
剤
ボントロンS−34(オリエント化学社製)1重量部
ジビニルベンゼン 0.5重量部A[BN
2重量部上記混合物を単
量体組成物とし、分散安定剤としての第三リン酸カルシ
ウム0.086%を含む水480重量部中に投入し、T
Kホモミキサー(特殊機化工業社製)を用いて懸濁分散
し、窒素雰囲気下80°Cで通常の攪拌を行い、10時
間重合させて重合体粒子を含む懸濁液を得た。懸濁液を
濾過し、得られたスラリーに20%のメタノール水溶液
400重量部及び12Nの塩酸20重量部を加えて攪拌
後濾過した。この操作を2回繰り返した。更に20%の
メタノール水溶液400重量部にて洗浄、濾過を3回繰
り返した後減圧乾燥してトナーを得た。(Example 1) Styrene 80 parts by weight 2-ethylhexyl methacrylate 20 parts by weight Grafted carbon black 5 parts by weight Charge control agent Bontron S-34 (manufactured by Orient Chemical Co., Ltd.) 1 part by weight Divinylbenzene 0.5 parts by weight A[BN
2 parts by weight The above mixture was made into a monomer composition, and added to 480 parts by weight of water containing 0.086% of tribasic calcium phosphate as a dispersion stabilizer.
The mixture was suspended and dispersed using a K-homo mixer (manufactured by Tokushu Kika Kogyo Co., Ltd.), stirred normally at 80°C under a nitrogen atmosphere, and polymerized for 10 hours to obtain a suspension containing polymer particles. The suspension was filtered, and 400 parts by weight of a 20% aqueous methanol solution and 20 parts by weight of 12N hydrochloric acid were added to the resulting slurry, stirred, and then filtered. This operation was repeated twice. Further, washing with 400 parts by weight of a 20% aqueous methanol solution and filtration were repeated three times, followed by drying under reduced pressure to obtain a toner.
得られたトナーを用いて電子写真複写機DC−111C
によって画像形成を行ったところ常温・常温(20°C
160%)と高温・高温(35°C185%)において
もカブリのない鮮明画像が得られた。また、トナー帯電
量も殆ど変動しなかった。Using the obtained toner, electrophotographic copying machine DC-111C
When image formation was performed using
160%) and high temperatures (35°C, 185%), clear images without fog were obtained. Further, the amount of toner charge hardly changed.
(実施例2)
上記実施例1と同様にして重合物を得、濾過して得られ
たスラリーにメタノール80重量部を加えて充分に分散
させた後、水320重量部、12N塩酸の20重量部を
加えて攪拌、濾過を2回繰り返した。この後得られたス
ラリーにメタノール80重量部を加えて充分に分散させ
、水320重量部を加えて攪拌、濾過を3回繰り返し、
減圧乾燥してトナーを得た。(Example 2) A polymer was obtained in the same manner as in Example 1, and 80 parts by weight of methanol was added to the slurry obtained by filtration and thoroughly dispersed, followed by 320 parts by weight of water and 20 parts by weight of 12N hydrochloric acid. of the mixture, stirring and filtration were repeated twice. After that, 80 parts by weight of methanol was added to the resulting slurry to fully disperse it, 320 parts by weight of water was added, stirring and filtration were repeated three times.
A toner was obtained by drying under reduced pressure.
得られたトナーを用いて電子写真複写機DC−11Cに
よって画像形成を行ったところ、常温・常温或いは高温
・高温においてもカブリのない鮮明画像が得られた。When an image was formed using the obtained toner using an electrophotographic copying machine DC-11C, a clear image without fogging was obtained even at normal temperature or high temperature.
(比較例1)
スラリー〇洗浄にメタノールを添加せず、他は実施例1
と同様の操作を行ってトナーを得た。そして得られたト
ナーを用いて画像形成を行ったところ、高温・高湿下に
おいてカブリの発生と画像濃度の低下が認められた。(Comparative Example 1) Slurry 〇 No methanol was added to the cleaning, except for Example 1
A toner was obtained by performing the same operation as above. When an image was formed using the obtained toner, fogging and a decrease in image density were observed under high temperature and high humidity conditions.
(比較例2)
実施例1で得られた重合物の洗浄に、メタノールを用い
ずに水400重量部、12N塩酸20重量部にて濾過、
洗浄を5回繰り返した後、水40.0重量部にて10回
洗浄した。更に、同様にして得られたトナーを用いて画
像形成を行ったところ、高温・高湿下においてカブリの
発生と画像濃度の低下が認められた。(Comparative Example 2) The polymer obtained in Example 1 was washed by filtration with 400 parts by weight of water and 20 parts by weight of 12N hydrochloric acid without using methanol.
After repeating the washing 5 times, it was washed 10 times with 40.0 parts by weight of water. Furthermore, when images were formed using toners obtained in the same manner, fogging and a decrease in image density were observed under high temperature and high humidity conditions.
(実施例3)
上記実施例1と同様の単量体組成物を、2%のポリビニ
ルアルコール(ケン化度88%、重合度500)水溶液
400重量部中に投入し、TKホモミキサーにて550
0rpmで10分間攪拌した後、80″Cにて10時間
で重合反応を完結させた。濾過した後、200%のメタ
ノール水溶液400重量部中にて60°Cの温度で攪拌
、洗浄を5回繰り返し減圧乾燥した。(Example 3) The same monomer composition as in Example 1 was added to 400 parts by weight of a 2% aqueous solution of polyvinyl alcohol (degree of saponification 88%, degree of polymerization 500), and
After stirring at 0 rpm for 10 minutes, the polymerization reaction was completed at 80"C for 10 hours. After filtration, the mixture was stirred and washed 5 times in 400 parts by weight of a 200% methanol aqueous solution at a temperature of 60°C. It was repeatedly dried under reduced pressure.
得られたトナーを用いて画像形成を行ったところ、常温
・常温或いは高温・高温においてもカブリのない鮮明画
像が得られた。When an image was formed using the obtained toner, a clear image without fogging was obtained even at normal temperature or high temperature.
(比較例3)
実施例3において洗浄にメタノールを使用しない以外は
同様にしてトナーを得た。(Comparative Example 3) A toner was obtained in the same manner as in Example 3 except that methanol was not used for cleaning.
得られたトナーを用いて画像形成を行ったところ、高温
・高温下においてカブリの発生と画像濃度の低下が認め
られた。When an image was formed using the obtained toner, fogging and a decrease in image density were observed at high temperatures.
(実施例4)
実施例1と同様の重合性組成物を0.05%のドデシル
ベンゼンスルホン酸ナトリウム水溶液400重量部に投
入し、TKホモミキサーによって6500rpmで10
分間攪拌した後、80°Cで10時間重合を行い完結さ
せた。この重合物を濾過した後、20%のメタノール溶
液400重量部にて洗浄、攪拌を5回繰り返した。そし
て減圧乾燥してトナーを得た。(Example 4) The same polymerizable composition as in Example 1 was added to 400 parts by weight of a 0.05% aqueous solution of sodium dodecylbenzenesulfonate, and the mixture was mixed with a TK homomixer at 6500 rpm for 10 min.
After stirring for a minute, polymerization was completed at 80°C for 10 hours. After filtering this polymer, washing with 400 parts by weight of a 20% methanol solution and stirring were repeated five times. Then, it was dried under reduced pressure to obtain a toner.
得られたトナーを用いて画像形成を行ったところ、常温
・常温或いは高温・高温においてもカブリのない鮮明画
像が得られた。When an image was formed using the obtained toner, a clear image without fogging was obtained even at normal temperature or high temperature.
(比較例4)
実施例4において洗浄にメタノールを使用しない以外は
同様にしてトナーを得た。得られたトナーを用いて画像
形成を行ったところ、高温・高湿下においてカブリと画
像濃度の低下が認められた。(Comparative Example 4) A toner was obtained in the same manner as in Example 4 except that methanol was not used for cleaning. When an image was formed using the obtained toner, fogging and a decrease in image density were observed under high temperature and high humidity conditions.
Claims (3)
なる単量体組成物を、分散安定剤が分散された分散媒中
で懸濁重合して重合体粒子を得た後、該重合体粒子表面
に付着する分散安定剤を水系液体で洗浄して除去する工
程からなる静電荷像現像用トナーの製造方法において、 前記水系液体中に水溶性有機溶剤を添加することを特徴
とする静電荷像現像用トナーの製造方法。(1) After obtaining polymer particles by suspension polymerizing a monomer composition consisting of a mixture of a polymerizable monomer and an additive such as a colorant in a dispersion medium in which a dispersion stabilizer is dispersed, A method for producing an electrostatic image developing toner comprising the step of removing the dispersion stabilizer adhering to the surface of the polymer particles by washing with an aqueous liquid, characterized in that a water-soluble organic solvent is added to the aqueous liquid. A method for producing a toner for developing an electrostatic image.
を特徴とする特許請求の範囲第1項に記載の静電荷像現
像用トナーの製造方法。(2) The method for producing a toner for developing an electrostatic image according to claim 1, wherein the dispersion stabilizer is a poorly water-soluble inorganic salt fine powder.
特徴とする特許請求の範囲第1及び2項に記載の静電荷
像現像用トナーの製造方法。(3) The method for producing a toner for developing an electrostatic image according to claims 1 and 2, wherein the water-soluble organic solvent is a lower alcohol.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP63217712A JP2501880B2 (en) | 1988-08-31 | 1988-08-31 | Method for manufacturing toner for developing electrostatic image |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP63217712A JP2501880B2 (en) | 1988-08-31 | 1988-08-31 | Method for manufacturing toner for developing electrostatic image |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH0264652A true JPH0264652A (en) | 1990-03-05 |
JP2501880B2 JP2501880B2 (en) | 1996-05-29 |
Family
ID=16708556
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP63217712A Expired - Lifetime JP2501880B2 (en) | 1988-08-31 | 1988-08-31 | Method for manufacturing toner for developing electrostatic image |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP2501880B2 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0588409A (en) * | 1991-03-22 | 1993-04-09 | Canon Inc | Developer for electrostatic charge image development, image forming method, and heating fixing method |
WO2001057599A1 (en) * | 2000-02-02 | 2001-08-09 | Zeon Corporation | Electrophotographic developer, process for producing the same, and method of forming image |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5753756A (en) * | 1980-09-16 | 1982-03-30 | Konishiroku Photo Ind Co Ltd | Manufacture of toner for developing electrostatic charge image |
JPS6057854A (en) * | 1983-09-09 | 1985-04-03 | Canon Inc | Production of toner for developing electrostatic charge image |
JPS61258260A (en) * | 1985-05-10 | 1986-11-15 | Kanegafuchi Chem Ind Co Ltd | Production of dry process one-component type electrophotographic developer with less deposit on surface |
JPH01302271A (en) * | 1988-05-30 | 1989-12-06 | Bando Chem Ind Ltd | Production of toner for developing electrostatic latent image |
JPH01306864A (en) * | 1988-06-03 | 1989-12-11 | Bando Chem Ind Ltd | Production of toner for development of electrostatic latent image |
-
1988
- 1988-08-31 JP JP63217712A patent/JP2501880B2/en not_active Expired - Lifetime
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5753756A (en) * | 1980-09-16 | 1982-03-30 | Konishiroku Photo Ind Co Ltd | Manufacture of toner for developing electrostatic charge image |
JPS6057854A (en) * | 1983-09-09 | 1985-04-03 | Canon Inc | Production of toner for developing electrostatic charge image |
JPS61258260A (en) * | 1985-05-10 | 1986-11-15 | Kanegafuchi Chem Ind Co Ltd | Production of dry process one-component type electrophotographic developer with less deposit on surface |
JPH01302271A (en) * | 1988-05-30 | 1989-12-06 | Bando Chem Ind Ltd | Production of toner for developing electrostatic latent image |
JPH01306864A (en) * | 1988-06-03 | 1989-12-11 | Bando Chem Ind Ltd | Production of toner for development of electrostatic latent image |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0588409A (en) * | 1991-03-22 | 1993-04-09 | Canon Inc | Developer for electrostatic charge image development, image forming method, and heating fixing method |
WO2001057599A1 (en) * | 2000-02-02 | 2001-08-09 | Zeon Corporation | Electrophotographic developer, process for producing the same, and method of forming image |
US6818371B2 (en) | 2000-02-02 | 2004-11-16 | Zeon Corporation | Electrophotographic developer, process for producing the same, and method of forming image |
US7008747B2 (en) | 2000-02-02 | 2006-03-07 | Zeon Corporation | Electrophotographic developer, production process thereof and image forming process |
Also Published As
Publication number | Publication date |
---|---|
JP2501880B2 (en) | 1996-05-29 |
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