JP6129026B2 - トナー - Google Patents
トナー Download PDFInfo
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- JP6129026B2 JP6129026B2 JP2013177450A JP2013177450A JP6129026B2 JP 6129026 B2 JP6129026 B2 JP 6129026B2 JP 2013177450 A JP2013177450 A JP 2013177450A JP 2013177450 A JP2013177450 A JP 2013177450A JP 6129026 B2 JP6129026 B2 JP 6129026B2
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- Japan
- Prior art keywords
- toner
- resin
- group
- parts
- compound
- 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.)
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- 239000002245 particle Substances 0.000 claims description 130
- 229920005989 resin Polymers 0.000 claims description 99
- 239000011347 resin Substances 0.000 claims description 99
- 150000001875 compounds Chemical class 0.000 claims description 90
- 239000003086 colorant Substances 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 239000011230 binding agent Substances 0.000 claims description 21
- 125000004122 cyclic group Chemical group 0.000 claims description 14
- 125000000524 functional group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 2
- -1 4 Chemical class 0.000 description 93
- 239000006185 dispersion Substances 0.000 description 78
- 238000000034 method Methods 0.000 description 61
- 239000000975 dye Substances 0.000 description 49
- 239000000178 monomer Substances 0.000 description 41
- 238000004519 manufacturing process Methods 0.000 description 36
- 239000001993 wax Substances 0.000 description 30
- 239000000049 pigment Substances 0.000 description 28
- 239000002904 solvent Substances 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 239000000203 mixture Substances 0.000 description 24
- 239000003381 stabilizer Substances 0.000 description 22
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 20
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 19
- 239000004094 surface-active agent Substances 0.000 description 19
- 229920002554 vinyl polymer Polymers 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000012736 aqueous medium Substances 0.000 description 17
- 239000007788 liquid Substances 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
- 229920001225 polyester resin Polymers 0.000 description 14
- 239000004645 polyester resin Substances 0.000 description 14
- 239000000725 suspension Substances 0.000 description 14
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000004458 analytical method Methods 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 12
- 238000004949 mass spectrometry Methods 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 238000009826 distribution Methods 0.000 description 11
- 238000002156 mixing Methods 0.000 description 11
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000009833 condensation Methods 0.000 description 10
- 230000005494 condensation Effects 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 10
- 239000010419 fine particle Substances 0.000 description 10
- 238000010558 suspension polymerization method Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 9
- 239000003945 anionic surfactant Substances 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 238000005469 granulation Methods 0.000 description 9
- 230000003179 granulation Effects 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000004220 aggregation Methods 0.000 description 8
- 230000002776 aggregation Effects 0.000 description 8
- 239000001506 calcium phosphate Substances 0.000 description 8
- 238000011161 development Methods 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 229920001519 homopolymer Polymers 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 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 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000002612 dispersion medium Substances 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000002736 nonionic surfactant Substances 0.000 description 7
- 239000003505 polymerization initiator Substances 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 6
- 229910000389 calcium phosphate Inorganic materials 0.000 description 6
- 235000011010 calcium phosphates Nutrition 0.000 description 6
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 6
- 239000003093 cationic surfactant Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 230000009477 glass transition Effects 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- 239000004372 Polyvinyl alcohol Substances 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 229910000019 calcium carbonate Inorganic materials 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 239000003431 cross linking reagent Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 239000003002 pH adjusting agent Substances 0.000 description 5
- 229920000056 polyoxyethylene ether Polymers 0.000 description 5
- 229940051841 polyoxyethylene ether Drugs 0.000 description 5
- 229920002451 polyvinyl alcohol Polymers 0.000 description 5
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 5
- 238000010298 pulverizing process Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 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
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 4
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 238000002296 dynamic light scattering Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000000696 magnetic material Substances 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229920000609 methyl cellulose Polymers 0.000 description 4
- 239000001923 methylcellulose Substances 0.000 description 4
- 235000010981 methylcellulose Nutrition 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 229920005749 polyurethane resin Polymers 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 229940114930 potassium stearate Drugs 0.000 description 4
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- 239000004576 sand Substances 0.000 description 4
- 238000010008 shearing Methods 0.000 description 4
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 4
- 229940082004 sodium laurate Drugs 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 229920003169 water-soluble polymer Polymers 0.000 description 4
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 3
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 3
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 3
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- 238000004438 BET method Methods 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 150000005215 alkyl ethers Chemical class 0.000 description 3
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000001110 calcium chloride Substances 0.000 description 3
- 229910001628 calcium chloride Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000004386 diacrylate group Chemical group 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 3
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 3
- HBRNMIYLJIXXEE-UHFFFAOYSA-N dodecylazanium;acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN HBRNMIYLJIXXEE-UHFFFAOYSA-N 0.000 description 3
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical compound CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000004927 fusion Effects 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 150000002484 inorganic compounds Chemical class 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 239000002563 ionic surfactant Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 3
- 235000019271 petrolatum Nutrition 0.000 description 3
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 239000011164 primary particle Substances 0.000 description 3
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 3
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 3
- NWZBFJYXRGSRGD-UHFFFAOYSA-M sodium;octadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOS([O-])(=O)=O NWZBFJYXRGSRGD-UHFFFAOYSA-M 0.000 description 3
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- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 1
- 238000000790 scattering method Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 229940067741 sodium octyl sulfate Drugs 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 229960000776 sodium tetradecyl sulfate Drugs 0.000 description 1
- WFRKJMRGXGWHBM-UHFFFAOYSA-M sodium;octyl sulfate Chemical compound [Na+].CCCCCCCCOS([O-])(=O)=O WFRKJMRGXGWHBM-UHFFFAOYSA-M 0.000 description 1
- SMECTXYFLVLAJE-UHFFFAOYSA-M sodium;pentadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCOS([O-])(=O)=O SMECTXYFLVLAJE-UHFFFAOYSA-M 0.000 description 1
- UPUIQOIQVMNQAP-UHFFFAOYSA-M sodium;tetradecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCOS([O-])(=O)=O UPUIQOIQVMNQAP-UHFFFAOYSA-M 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 229940083466 soybean lecithin Drugs 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000002130 sulfonic acid ester group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- XLKZJJVNBQCVIX-UHFFFAOYSA-N tetradecane-1,14-diol Chemical compound OCCCCCCCCCCCCCCO XLKZJJVNBQCVIX-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 229940096522 trimethylolpropane triacrylate Drugs 0.000 description 1
- KQBSGRWMSNFIPG-UHFFFAOYSA-N trioxane Chemical compound C1COOOC1 KQBSGRWMSNFIPG-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- ZRQNRTRXAVFCMB-UHFFFAOYSA-N tris(2,4,5-trioxa-1-stanna-3-borabicyclo[1.1.1]pentan-1-yl) borate Chemical compound [Sn+4].[Sn+4].[Sn+4].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-] ZRQNRTRXAVFCMB-UHFFFAOYSA-N 0.000 description 1
- GRPURDFRFHUDSP-UHFFFAOYSA-N tris(prop-2-enyl) benzene-1,2,4-tricarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C(C(=O)OCC=C)=C1 GRPURDFRFHUDSP-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
Images
Classifications
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- 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
- G03G9/0906—Organic dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
-
- 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
- G03G9/0802—Preparation methods
- G03G9/0804—Preparation methods whereby the components are brought together in a liquid dispersing medium
-
- 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
- G03G9/0802—Preparation methods
- G03G9/0804—Preparation methods whereby the components are brought together in a liquid dispersing medium
- G03G9/0806—Preparation methods whereby the components are brought together in a liquid dispersing medium whereby chemical synthesis of at least one of the toner components takes place
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- 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
- G03G9/0802—Preparation methods
- G03G9/0808—Preparation methods by dry mixing the toner components in solid or softened state
-
- 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
- G03G9/0906—Organic dyes
- G03G9/0924—Dyes characterised by specific substituents
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Developing Agents For Electrophotography (AREA)
Description
R1、R2及びR6は、それぞれ独立して、アルキル基を表し、
R3乃至R5は、それぞれ独立して、アルキル基を表す、或いは、以下のi)及びii)のいずれかを満たす、
i)R3とR4とが結合しており、R3とR4とが同時に結合している炭素原子とR3とR4とが含まれる環式有機官能基が形成され、R5は、アルキル基である、
ii)R3乃至R5が結合しており、R3乃至R5が同時に結合している炭素原子とR3とR4とR5とが含まれる環式有機官能基が形成される、
R7及びR8は、それぞれ独立して、アルキル基又はアシル基を表す、或いは、R7とR8とが結合しており、R7とR8とが同時に結合している窒素原子とR7とR8とが含まれる環式有機官能基が形成される。]
R1、R2及びR6は、それぞれ独立して、アルキル基を表し、
R3乃至R5は、それぞれ独立して、アルキル基を表す、或いは、以下のi)及びii)のいずれかを満たす、
i)R3とR4とが結合しており、R3とR4とが同時に結合している炭素原子とR3とR4とが含まれる環式有機官能基が形成され、R5は、アルキル基である、
ii)R3乃至R5が結合しており、R3乃至R5が同時に結合している炭素原子とR3とR4とR5とが含まれる環式有機官能基が形成される、
R7及びR8は、それぞれ独立して、アルキル基又はアシル基を表す、或いは、R7とR8とが結合しており、R7とR8とが同時に結合している窒素原子とR7とR8とが含まれる環式有機官能基が形成される。]
本発明に用いる結着樹脂としては、特に限定されるものではないが、例えば、熱可塑性樹脂などを挙げることができる。
ワックス成分とは、トナー定着時のオフセットを防止する目的で使用される材料を意味する。
本発明のトナー母粒子を構成する着色剤としては、一般式(1)で表される色素化合物を用いるが、必要に応じて他の着色剤を併用することできる。
本発明のトナーにおいては、必要に応じて荷電制御剤をトナー母粒子と混合して用いることも可能である。これにより、現像システムに応じた最適の摩擦帯電量のコントロールが可能となる。
本発明のトナーは、トナー母粒子に、流動化剤として無機微粉体が外部添加されていてもよい。すなわち、この流動化剤としての無機微粉体は、外添剤として機能する。無機微粉体としては、シリカ、酸化チタン、アルミナまたはそれらの複酸化物や、これらを表面処理したもの等の微粉体が使用できる。
次に、本発明のトナーに用いられる色素分散体について説明する。本発明で言う分散媒体とは、水、有機溶剤又はそれらの混合物のことを指す。
懸濁重合法によるトナー母粒子の製造について説明する。
懸濁造粒法によるトナー母粒子の製造について説明する。懸濁造粒法の製造工程では加熱工程を有さないため、低融点ワックスを用いた場合に起こる樹脂とワックス成分の相溶化を抑制し、相溶化に起因するトナーのガラス転移温度の低下を防止することができる。また、懸濁造粒法は、結着樹脂となるトナー材料の選択肢が広く、一般的に定着性に有利とされるポリエステル樹脂を主成分にすることが容易である。そのため、懸濁重合法を適用できない樹脂組成のトナーを製造する場合に有利な製造方法である。
粉砕によってトナー母粒子を製造する場合には、必要に応じて磁性体やワックス、荷電制御剤、その他の添加剤等が用いられる。
次に、乳化凝集法によるトナー母粒子の製造方法について説明する。
本発明に用いられるワックス分散液は、ワックスを水系媒体に分散させてなる。ワックス分散液は公知の方法で調製される。
本発明に用いる樹脂粒子分散液は、樹脂粒子を水系媒体に分散させてなる。
着色剤粒子分散液は、一般式(1)で表される色素化合物等の着色剤を界面活性剤と共に水系媒体に分散させてなる。
凝集体粒子を形成させる方法としては、特に限定されるものではないが、pH調整剤、凝集剤、安定剤等を上記混合液中に添加・混合し、温度、機械的動力(撹拌)等を適宜加える方法が好適に例示できる。
融合工程では、上記凝集体粒子を加熱して融合することでトナー母粒子を形成する。
融合工程後に得られた粒子を、適切な条件で洗浄、濾過、乾燥等することにより、トナー母粒子を得る。この場合、トナーとして十分な帯電特性、信頼性を確保するために、上記トナー母粒子を十分に洗浄することが好ましい。
乾燥は、通常の振動型流動乾燥法、スプレードライ法、凍結乾燥法、フラッシュジェット法など、公知の方法を利用することができる。トナー粒子の乾燥後の含水分率は、1.5質量%以下であることが好ましく、より好ましくは1.0質量%以下である。
以下、液体現像剤の製造方法について説明する。
一般式(1)で表される色素化合物は、公知の方法によって合成することが可能である。
ピリドン化合物(1)10mmolのトルエン20mL懸濁液に、p−トルエンスルホン酸100mgを加え、70℃に昇温し、アルデヒド化合物(1)10mmolのトルエン20mL溶液を滴下した。更に、共沸脱水を行いながら、160℃で6時間加熱還流させた。反応終了後、室温に冷却し、イソプロパノールで希釈した。減圧下濃縮後、残さをカラムクロマトグラフィーによる精製(展開溶媒:酢酸エチル/ヘプタン)して4.6g(収率78%)の化合物(1)を得た。図1に、化合物(1)のCDCl3中、室温、400MHzにおける1H−NMRスペクトルを示す。
[1]1H−NMR(400MHz、CDCl3、室温):δ(ppm)=0.97(3H、t、J=7.33Hz)、1.03(3H、t、J=7.33Hz)、1.36(2H、dd、J=7.33、14.7Hz)、1.43−1.58(11H、m)、1.66−1.78(4H、m)、2.48(3H、s)、2.56(3H、s)、3.50(2H、t、J=7.56Hz)、3.80(2H、t、J=7.33Hz)、7.34(2H、t、J=7.56Hz)、7.45(1H、t、J=6.87Hz)、7.68(2H、d、J=8.24Hz)、8.24(1H、s)
[2]質量分析(ESI−TOF):m/z=590.2989(M+H)+
アルデヒド化合物(2)10mmol及びピリドン化合物(4)10mmolのメタノール50mL溶液を室温で3日間撹拌した。反応終了後、イソプロパノールで希釈し、ろ過して5.4g(収率82%)の化合物(3)を得た。
[1]1H−NMR(400MHz、CDCl3、室温):δ(ppm)=0.93(12H、q、J=6.87Hz)、1.14(6H、s)、1.30−1.39(17H、m)、1.39−1.60(11H、m)、1.84−1.92(2H、m)、2.54(3H、s)、3.16(2H、s)、3.37−3.48(3H、m)、3.58−3.92(2H、dm)、8.31(1H、s)
[2]質量分析(ESI−TOF):m/z=654.4611(M+H)+
アルデヒド化合物(2)10mmol及びピリドン化合物(7)10mmolのエタノール50mL溶液を室温で3日間撹拌した。反応終了後、イソプロパノールで希釈し、ろ過して5.1g(収率87%)の化合物(6)を得た。
[1]1H−NMR(400MHz、CDCl3、室温):δ(ppm)=0.92(12H、q、J=7.02Hz)、1.22−1.41(16H、m)、1.54(9H、s)、1.85−1.90(2H、m)、2.50(3H、s)、3.00(6H、s)、3.37(2H、d、J=5.50Hz)、3.73(2H、dq、J=4.27、17.2Hz)、8.28(1H、s)
[2]質量分析(ESI−TOF):m/z=584.4211(M+H)+
製造例2において、ピリドン化合物(4)を用いる代わりにピリドン化合物(9)に変更した以外は、製造例2と同様の方法を行うことで、4.8g(収率77%)の化合物(10)を得た。
[1]1H−NMR(400MHz、CDCl3、室温):δ(ppm)=0.92(12H、dt、J=7.90、23.1Hz)、1.20−1.34(18H、m)、1.53(3H、s)、1.73(4H、q、J=5.65Hz)、1.86−1.93(2H、m)、2.49(3H、s)、3.22(2H、dd、J=4.58、10.1Hz)、3.37−3.41(4H、m)、3.71−3.75(2H、m)、8.24(1H、s)
[2]質量分析(ESI−TOF):m/z=624.4531(M+H)+
製造例2において、アルデヒド化合物(2)及びピリドン化合物(4)を対応するアルデヒド化合物及びピリドン化合物に変更した以外は、製造例2と同様の方法を行うことで、対応する化合物(4)、(12)、(13)、(15)、(18)、(20)、(21)、(22)を得た。
[1]1H−NMR(400MHz、CDCl3、室温):δ(ppm)=0.90−1.01(15H、m)、1.14(7H、s)、1.24−1.39(16H、m)、1.52−1.66(13H、m)、1.82−1.92(2H、m)、2.84−2.89(2H、m)、3.16(2H、s)、3.37−3.42(3H、m)、3.61−3.94(2H、m)、8.29(1H、d、J=9.62Hz)
[2]質量分析(ESI−TOF):m/z=696.4972(M+H)+
[1]1H−NMR(400MHz、CDCl3、室温):δ(ppm)=0.98(6H、q、J=7.33Hz)、1.14(7H、s)、1.33−1.44(6H、m)、1.56(9H、t、J=14.2Hz)、1.64−1.75(4H、m)、2.54(3H、d、J=13.3Hz)、3.17(2H、s)、3.48(3H、t、J=8.01Hz)、3.80(2H、t、J=7.33Hz)、8.31(1H、s)
[2]質量分析(ESI−TOF):m/z=542.3279(M+H)+
[1]1H−NMR(400MHz、CDCl3、室温):δ(ppm)=0.94(12H、tt、J=5.88、18.3Hz)、1.27−1.46(16H、m)、1.55(9H、s)、1.87−1.95(2H、m)、2.43(3H、s)、3.29−3.44(5H、m)、3.60−3.92(2H、m)、7.21−7.33(3H、m)、7.44−7.49(2H、m)、8.17(1H、s)
[2]質量分析(ESI−TOF):m/z=674.4189(M+H)+
[1]1H−NMR(400MHz、CDCl3、室温):δ(ppm)=0.89−0.96(15H、m)、1.22−1.42(18H、m)、1.57(8H、t、J=16.5Hz)、1.88−1.91(9H、m)、2.01−2.13(4H、m)、2.57(3H、s)、3.12(3H、s)、3.38−3.57(2H、d、J=13.3Hz)、3.73−3.96(2H、m)、8.33(1H、s)
[2]質量分析(ESI−TOF):m/z=732.4933(M+H)+
[1]1H−NMR(400MHz、CDCl3、室温):δ(ppm)=0.87−0.95(12H、m)、1.11−1.24(8H、m)、1.30−1.38(18H、m)、1.53−1.60(12H、t、J=13.5Hz)、1.84−1.92(1H、m)、2.54(3H、d、J=11.5Hz)、3.37−3.41(2H、m)、3.54−3.91(4H、m)、8.31(1H、d、J=11.9Hz)
[2]質量分析(ESI−TOF):m/z=668.4662(M+H)+
[1]1H−NMR(400MHz、CDCl3、室温):δ(ppm)=0.89−1.01(15H、m)、1.25−1.42(16H、m)、1.56(11H、t、J=10.5Hz)、1.60−1.75(2H、m)、1.82−1.95(5H、m)、2.86−2.91(2H、m)、3.19(3H、m)、3.35−3.42(2H、m)、3.73−3.79(2H、m)、8.32(1H、s)
[2]質量分析(ESI−TOF):m/z=654.4399(M+H)+
[1]1H−NMR(400MHz、CDCl3、室温):δ(ppm)=0.88−1.01(17H、m)、1.24−1.46(18H、m)、1.51(9H、s)、1.87−1.96(2H、m)、2.70−2.74(2H、m)、3.33(3H、s)、3.40−3.50(2H、m)、3.61−3.86(2H、m)、7.22(2H、t、J=7.56Hz)、7.46(3H、t、J=8.70Hz)、8.15(1H、s)
[2]質量分析(ESI−TOF):m/z=716.4511(M+H)+
[1]1H−NMR(400MHz、CDCl3、室温):δ(ppm)=0.81(2H、t、J=6.18Hz)、0.89−0.95(12H、m)、1.03(8H、t、J=3.66Hz)、1.14(7H、d、J=1.83Hz)、1.26−1.39(17H、m)、1.55(12H、t、J=5.95Hz)、1.84−1.91(3H、m)、2.69−2.81(1H、m)、2.98−3.08(1H、m)、3.18(2H、J=1.83Hz)、3.45−3.48(3H,m)、3.56−3.89(2H、m)、8.32(1H、t、J=6.87Hz)
[2]質量分析(ESI−TOF):m/z=738.5329(M+H)+
以下に記載する方法で本発明のトナー及び比較トナーを製造した。
色素化合物である上記化合物(1)12部、スチレン単量体120部の混合物をアトライター(三井鉱山社製)により3時間分散させて色素分散体(1)を得た。
・色素分散体(1) 133.2部
・スチレン単量体 46.0部
・n−ブチルアクリレート単量体 34.0部
・サリチル酸アルミニウム化合物 2.0部
(オリエント化学工業株式会社製 ボントロンE−88)
・極性樹脂 10.0部
(プロピレンオキサイド変性ビスフェノールAとイソフタル酸との重縮合物、Tg=65℃、Mw=10000、Mn=6000)
・エステルワックス 25.0部
(DSC測定における最大吸熱ピークのピーク温度=70℃、Mn=704)
・ジビニルベンゼン単量体 0.10部
上記処方を60℃に加温し、T.K.ホモミキサーを用いて5000rpmにて均一に溶解・分散した。これに重合開始剤である2,2’−アゾビス(2,4−ジメチルバレロニトリル)10部を溶解し、重合性単量体組成物を調製した。
実施例1において、化合物(1)を表1に示す化合物に各々変更した以外は実施例1と同様にして本発明のトナー(2)乃至(8)を得た。
実施例1において、化合物(1)12部を用いる代わりに、化合物(1)6部とC.I.Pigment Red 122(クラリアント社製、商品名「Toner Magenta E」)を6部の2種類を用いることに変更した以外は実施例1と同様にして本発明のトナー(9)を得た。
実施例9において、化合物(1)を化合物(22)に変更した以外は実施例9と同様にして本発明のトナー(10)を得た。
実施例1において、化合物(1)を用いる代わりに、下記の比較用色素(1)乃至(3)を用いる以外は実施例1と同様にして比較用トナー(比1)、(比2)、(比3)を得た。
スチレン82.6部、アクリル酸n−ブチル9.2部、アクリル酸1.3部、ヘキサンジオールジアクリレート0.4部、n−ラウリルメルカプタン3.2部を混合し溶解させた。この溶液にネオゲンRK(第一工業製薬社製)1.5部のイオン交換水150部の水溶液を添加して、分散させた。さらに10分間ゆっくりと撹拌しながら、過硫酸カリウム0.15部のイオン交換水10部の水溶液を添加した。窒素置換をした後、70℃で6時間乳化重合を行った。重合終了後、反応液を室温まで冷却し、イオン交換水を添加することで固形分濃度が12.5質量%、体積基準のメジアン径が0.2μmの樹脂粒子分散液を得た。
着色剤粒子の体積基準のメジアン径は、0.15μmであった。
実施例11において、化合物(1)を用いる代わりに表1に示す化合物に各々変更した以外は実施例11と同様の操作で本発明のトナー(12)乃至(17)を得た。
C.I.Pigment Red 122(クラリアント社製、商品名「Toner Magenta E」)100部、アニオン性界面活性剤(ネオゲンRK、第一工業製薬(株)製)15部をイオン交換水885部に混合させ、湿式ジェットミル JN100((株)常光製)を用いて約1時間分散して顔料分散液(1)を得た。
実施例18において、化合物(1)を用いる代わりに化合物(20)を用いて、同様の操作で分散液(20)を得た。次に、実施例18において、分散液(1)を分散液(20)に変更した以外は、実施例18と同様の操作でトナー(19)を得た。
実施例11において、化合物(1)を用いる代わりに、比較用色素(1)乃至(3)に変更した以外は実施例11と同様にして比較用トナー(比4)乃至(比6)を得た。
結着樹脂(ポリエステル樹脂):100部(Tg55℃、酸価20mgKOH/g、水酸基価16mgKOH/g、分子量:Mp(ピークトップ分子量)4500、Mn2300、Mw38000)、化合物(1):6部、1,4−ジ−t−ブチルサリチル酸アルミニウム化合物:0.5部、パラフィンワックス(最大吸熱ピーク温度78℃):5部を、ヘンシェルミキサー(FM−75J型、三井鉱山(株)製)でよく混合した後、温度130℃に設定した2軸混練機(PCM−45型、池貝鉄鋼(株)製)にて60kg/hrのFeed量で混練(吐出時の混練物温度は約150℃)した。得られた混練物を冷却し、ハンマーミルで粗砕した後、機械式粉砕機(T−250:ターボ工業(株)製)にて20kg/hrのFeed量で微粉砕した。
実施例20において、化合物(1)を用いる代わりに表1に示す化合物に変更した以外は、実施例20と同様な方法で本発明のトナー(21)乃至(28)を得た。なお、実施例27においては、化合物(1)とC.I.Pigment Red 122(クラリアント社製、商品名「Toner Magenta E」)の質量比は2:1、また実施例8においては、化合物(4)とC.I.Pigment Red 122の質量比は3:2の割合で使用した。
実施例20において、化合物(1)を用いる代わりに、比較用色素(1)乃至(3)に変更した以外は実施例20と同様にして比較用トナー(比7)乃至(比9)を得た。
上記トナーの個数平均粒径(D1)及び重量平均粒径(D4)はコールター法による粒度分布解析にて測定した。測定装置として、コールターカウンターTA−IIあるいはコールターマルチサイザーII(ベックマン・コールター株式会社製)を用い、該装置の操作マニュアルに従い測定した。電解液は、1級塩化ナトリウムを用いて、約1%塩化ナトリウム水溶液を調製した。例えば、ISOTON−II(コールターサイエンティフィックジャパン株式会社製)が使用できる。具体的な測定方法としては、前記電解水溶液100乃至150mL中に分散剤として、界面活性剤(好ましくはアルキルベンゼンスルホン酸塩)を、0.1乃至5mL加え、更に測定試料(トナー粒子)を2乃至20mg加える。試料を懸濁した電解液は、超音波分散器で約1乃至3分間分散処理を行う。得られた分散処理液を、アパーチャーとして100μmアパーチャーを装着した前記測定装置により、2.00μm以上のトナーの体積、個数を測定してトナーの体積分布と個数分布とを算出する。それから、トナーの個数分布から求めた個数平均粒径(D1)と、トナーの体積分布から求めたトナーの重量平均粒径(D4)(各チャンネルの中央値をチャンネル毎の代表値とする)及びD4/D1を求めた。
A:D4/D1が1.30以下(粒度分布が非常に良い)
B:D4/D1が1.30より大きく1.35以下(粒度分布が良い)
C:D4/D1が1.35より大きい(粒度分布が悪い)
2cm2のガラス基板上に0.5gのトナーを均一に敷き詰め、BIG HEATER(井元製作所製)で160℃、1kgの条件で熱プレスを行い、耐光性評価用サンプルを作製した。
A:ΔE<6(耐光性が非常に優れる)
B:6≦ΔE<10(耐光性に優れる)
C:10≦ΔE(耐光性が悪い)
Claims (4)
- 結着樹脂、ワックス及び着色剤を含有するトナー母粒子を有するトナーであって、着色剤として、一般式(1)で表される色素化合物を含有することを特徴とするトナー。
R1、R2及びR6は、それぞれ独立して、アルキル基を表し、
R3乃至R5は、それぞれ独立して、アルキル基を表す、或いは、以下のi)及びii)のいずれかを満たす、
i)R3とR4とが結合しており、R3とR4とが同時に結合している炭素原子とR3とR4とが含まれる環式有機官能基が形成され、R5は、アルキル基である、
ii)R3乃至R5が結合しており、R3乃至R5が同時に結合している炭素原子とR3とR4とR5とが含まれる環式有機官能基が形成される、
R7及びR8は、それぞれ独立して、アルキル基又はアシル基を表す、或いは、R7とR8とが結合しており、R7とR8とが同時に結合している窒素原子とR7とR8とが含まれる環式有機官能基が形成される。] - 前記一般式(1)中のR7、R8のどちらか一方が、アルキル基であることを特徴とする請求項1に記載のトナー。
- 前記一般式(1)中のR3乃至R5がいずれも、メチル基であることを特徴とする請求項1又は2に記載のトナー。
- 前記トナー母粒子の表面に外添剤を有することを特徴とする請求項1乃至3のいずれか1項に記載のトナー。
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