JP2012246377A - 顔料分散体、イエロートナー - Google Patents
顔料分散体、イエロートナー Download PDFInfo
- Publication number
- JP2012246377A JP2012246377A JP2011118270A JP2011118270A JP2012246377A JP 2012246377 A JP2012246377 A JP 2012246377A JP 2011118270 A JP2011118270 A JP 2011118270A JP 2011118270 A JP2011118270 A JP 2011118270A JP 2012246377 A JP2012246377 A JP 2012246377A
- Authority
- JP
- Japan
- Prior art keywords
- group
- pigment
- yellow
- toner
- general formula
- 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
- 239000000049 pigment Substances 0.000 title claims abstract description 137
- 239000006185 dispersion Substances 0.000 title claims abstract description 119
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- 239000002612 dispersion medium Substances 0.000 claims abstract description 26
- 239000001052 yellow pigment Substances 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 4
- 239000002245 particle Substances 0.000 claims description 58
- 229920005989 resin Polymers 0.000 claims description 35
- 239000011347 resin Substances 0.000 claims description 35
- 239000011230 binding agent Substances 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims description 3
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000003086 colorant Substances 0.000 abstract description 31
- 238000004040 coloring Methods 0.000 abstract description 13
- 230000003247 decreasing effect Effects 0.000 abstract description 2
- 239000000178 monomer Substances 0.000 description 41
- -1 methylcyclohexyl group Chemical group 0.000 description 33
- 238000000034 method Methods 0.000 description 29
- 238000004519 manufacturing process Methods 0.000 description 26
- 239000000203 mixture Substances 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- 239000003381 stabilizer Substances 0.000 description 19
- 239000007788 liquid Substances 0.000 description 15
- 239000001993 wax Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- 239000012736 aqueous medium Substances 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 238000005469 granulation Methods 0.000 description 8
- 230000003179 granulation Effects 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000010419 fine particle Substances 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 229920001225 polyester resin Polymers 0.000 description 7
- 239000004645 polyester resin Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000003505 polymerization initiator Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 238000010558 suspension polymerization method Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000001506 calcium phosphate Substances 0.000 description 5
- 229910000389 calcium phosphate Inorganic materials 0.000 description 5
- 235000011010 calcium phosphates Nutrition 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 229940051841 polyoxyethylene ether Drugs 0.000 description 5
- 229920000056 polyoxyethylene ether Polymers 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 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 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003431 cross linking reagent Substances 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-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
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 239000003093 cationic surfactant Substances 0.000 description 3
- 229920001577 copolymer Polymers 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
- 238000011161 development Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 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
- 238000009775 high-speed stirring Methods 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000002736 nonionic surfactant Substances 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
- 239000003973 paint Substances 0.000 description 3
- 239000011164 primary particle Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- QHVBLSNVXDSMEB-UHFFFAOYSA-N 2-(diethylamino)ethyl prop-2-enoate Chemical compound CCN(CC)CCOC(=O)C=C QHVBLSNVXDSMEB-UHFFFAOYSA-N 0.000 description 2
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 2
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-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
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 2
- CMVNWVONJDMTSH-UHFFFAOYSA-N 7-bromo-2-methyl-1h-quinazolin-4-one Chemical compound C1=CC(Br)=CC2=NC(C)=NC(O)=C21 CMVNWVONJDMTSH-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-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
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-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
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 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
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 125000004386 diacrylate group Chemical group 0.000 description 2
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 description 2
- KHAYCTOSKLIHEP-UHFFFAOYSA-N docosyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCOC(=O)C=C KHAYCTOSKLIHEP-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
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Landscapes
- Developing Agents For Electrophotography (AREA)
Abstract
【解決手段】分散媒体中に、一般式(1)で表される化合物とC.I.Pigment Yellow 180で例示されるイエロー顔料を含有する顔料分散体。
【選択図】なし
Description
本発明の顔料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事を指す。
次に本発明のトナーについて説明する。
本発明の顔料分散体は、結着樹脂、イエロー顔料、ワックス成分等を含有するトナー粒子を作製する際に、着色剤として用いることができる。本発明の顔料分散体を着色剤として用いることにより、分散媒中で分散粘度の増加を抑制できるため、トナー製造工程上のハンドリングが容易になるとともに、着色剤の分散性が良好に保たれる。その結果、高着色力を有するイエロートナーを得ることができる。
以下に、懸濁重合法によりトナー粒子を製造する方法について説明する。まず、本発明にかかる顔料分散体を含む着色剤、重合性単量体、ワックス成分および重合開始剤等を混合して重合性単量体組成物を調製する。次に、該重合性単量体組成物を水系媒体中に分散して重合性単量体組成物の粒子を造粒する。そして、水系媒体中にて重合性単量体組成物の粒子中の重合性単量体を重合させてトナー粒子を得る。
本発明の顔料分散体は、液体現像法に用いられる現像剤(以下液体現像剤と呼ぶ)に用いる事が出来る。以下、液体現像剤の製造方法について説明する。
着色剤は単独、または2種以上を組み合わせて用いることもできる。
樹脂及びワックスは、前記と同様のものが用いられる。
一般式(1)で表される化合物として、化合物(1)、(4)、(5)、(7)を、下記の様にして得た。なお、本実施例における化合物(1)、(4)、(5)、(7)は、前述した一般式(1)で表される化合物の具体例における化合物(1)、(4)、(5)、(7)と対応している。
化合物(1)として、商品名「リカクリア PC1」(新日本理化株式会社製)を入手し、これを用いた。
クレゾール13.0g(120mmol)、1,2,3−プロパントリカルボン酸7.0g(40mmol)、三酸化二ホウ素1.0g(14.4mmol)のキシレン150mL溶液にn−ドデシルアミン44.5g(240mmol)を添加し、6時間加熱還流させ脱水させた。反応終了後、減圧下濃縮した後、アセトニトリル150mLで、50℃で1時間攪拌させ懸濁洗浄を行った。固体をろ過し、化合物(4)10.0g(収率37%)を得た。
[1]1H NMR(400MHz、DMSO−d6、室温):δ[ppm]=0.85(t、9H、J=6.64Hz)、1.17(m、60H)、2.50(t、11H、J=1.83Hz)、7.64(s、1H)、8.03(s、1H)、10.8(s、1H)
[2]質量分析(ESI−TOF):m/z=676.6414(M−H)−
製造例1における化合物(1)のn−ドデシルアミンを、2−エチルヘキシルアミンに変更したこと以外は、製造例1と同様に製造し、化合物(5)7.3g(収率36%)を得た。
[1]1H NMR(400MHz、DMSO−d6、室温):δ[ppm]=0.80(td、9H、J=7.44、3.51Hz)、0.86(t、9H、J=6.87Hz)、1.2(t、24H、8.47Hz)、1.32(dd、3H、J=11.7、5.72Hz)、2.10(dd、2H、J=14.7、6.87Hz)、2.32(dd、2H、J=14.9、8.01Hz)、2.50(t、1H、J=1.83Hz)、2.96(dtd、6H、J=39.1、13.1、6.41Hz)、7.60(t、1H、6.00Hz)、7.68(t、2H、6.00Hz)
[2]質量分析(ESI−TOF):m/z=508.4524(M−H)−
製造例1における化合物(1)のn−ドデシルアミンを、3−ブトキシプロピルアミンに変更したこと以外は、製造例1と同様に製造し、化合物(7)4.8g(収率23%)を得た。
[1]1H NMR(400MHz、DMSO−d6、室温):δ[ppm]=0.92−0.82(m、9H)、1.3(td、6H、J=14.9、7.48Hz)、1.46(dt、6H、J=15.7、5.95Hz)、1.57(td、6H、J=13.3、6.4Hz)、2.07(dd、2H、J=14.7、6.41Hz)、2.28(dd、2H、J=14.7、7.79Hz)、2.5(t、1H、J=1.60Hz)、2.99(tt、7H、J=22.4、7.56Hz)、3.36−3.30(m、12H)、7.72(dt、3H、J=29.5、5.61Hz)
[2]質量分析(ESI−TOF):m/z=514.3906(M−H)−
[顔料分散体の製造]
<実施例1>
C.I.Pigment Yellow 180(クラリアント社製、商品名「TONER YELLOW HG」)12部と化合物(1)0.12部の混合物にポリエステル樹脂(モノマー組成(モル比)/ポリオキシプロピレン(2.2)−2,2−ビス(4−ヒドロキシフェニル)プロパン:ポリオキシエチレン(2.0)−2,2−ビス(4−ヒドロキシフェニル)プロパン:テレフタル酸:フマル酸:トリメリット酸=30:20:26:20:4、酸価が11mgKOH/g、重量平均分子量(Mw)が11,000、分子量500以上2,000未満の成分が8.5%、Tgが56℃)48部と酢酸エチル120部を混合し、アトライター(三井鉱山社製)により3時間分散させて顔料分散体(1)を得た。
実施例1において、酢酸エチルをトルエン、エチルメチルケトンに変更した以外は実施例1と同様の操作で、顔料分散体(2)、(3)を得た。
実施例1において、ポリエステル樹脂を添加しない事と、酢酸エチルをスチレンに、または酢酸エチル/トルエン混合物(60部/60部)にそれぞれ変更したこと以外は、実施例1と同様の操作で、顔料分散体(4)、(5)を得た。
実施例1において、ポリエステル樹脂を添加しない事と、化合物(1)を用いる代わりに化合物(7)を用い、酢酸エチルをスチレン/キシレン混合物(70部/50部)に変更した以外は実施例1と同様の操作で、顔料分散体(6)を得た。
C.I.Pigment Yellow 180 6部、化合物(1)0.06部、ドデシル硫酸ナトリウム1.2部の混合物に水60部を混合し、アトライター(三井鉱山社製)により3時間分散させて、顔料分散体(7)を得た。
実施例1〜7において、化合物(1)または化合物(7)を入れないこと以外は、実施例1〜7と同様の操作で、顔料分散体(8)〜(14)を得た。
顔料分散体の分散性の評価を以下のように行った。粒度測定器(グラインドメーター)(テスター産業株式会社)を用い、顔料の組織粒の大きさを測定する事によって決定した。
A:顔料の組織粒の大きさが2.5μm未満である。(分散性が非常に良い)
B:顔料の組織粒の大きさが2.5μm以上4.5μm未満である。(分散性が良い)
C:顔料の組織粒の大きさが4.5μm以上である。(分散性が悪い)
また、前記顔料分散体をアルミ基板上に展開し、溶媒を自然乾燥によって除去したサンプルを走査電子顕微鏡 S−4800(日立製作所社製)によって100,000倍に拡大観察して分散性を確認した。
(表1において、PY180は、C.I.Pigment Yellow 180を表す。)
C.I.Pigment Yellow 180 12部と化合物(1)0.12部の混合物にスチレン120部を混合し、アトライター(三井鉱山社製)により3時間分散させて、顔料分散体(15)を得た。
実施例8において、用いる化合物(1)の質量部を、0.06部、0.36部にそれぞれ変更したこと以外は、実施例8と同様の操作で、顔料分散体(16)、(17)を得た。
実施例8において、C.I.Pigment Yellow 180を用いる代わりに、C.I.Pigment Yellow 74に変更したこと以外は、実施例8と同様の操作で、顔料分散体(18)を得た。
実施例8において、化合物(1)を、化合物(4)、化合物(5)、化合物(7)に変更したこと以外は、実施例8と同様の操作で、顔料分散体(19)〜(21)を得た。
実施例8において、C.I.Pigment Yellow 180を、C.I.Pigment Yellow 74に変更し、化合物(1)を、化合物(5)に変更し、それ以外は実施例8と同様の操作で、顔料分散体(22)を得た。
実施例8において、化合物(1)を入れないこと以外は、実施例8と同様の操作で、比較用である顔料分散体(23)を得た。
実施例11において、化合物(1)を入れないこと以外は、実施例11と同様の操作で、比較用である顔料分散体(24)を得た。
顔料分散体の粘度は、レオメータPHYSICA MCR 300(Pear Physica社)により測定した。そして、顔料分散体(15)〜(17)、(19)〜(21)は、顔料分散体(23)に対して、顔料分散体(18)、(22)は、顔料分散体(24)に対しての粘度低下率をそれぞれ求めた。
コーンプレート型測定治具:75mm径、1°
せん断速度:10s−1
A:比較用の顔料分散体に対する粘度低下率が、15%以上である。
B:比較用の顔料分散体に対する粘度低下率が、5%以上15%未満である。
C:比較用の顔料分散体に対する粘度低下率が、5%未満である。
顔料分散体の光沢性の評価を以下のように行った。顔料分散体をスポイトですくい取り、アート紙(王子製紙(株)製、商品名「SA金藤+、秤量209.3g/m2」)上部に直線状に載せ、ワイヤーバー(#10)を用いて均一にアート紙上に塗工した。乾燥させた後、アート紙上の線の光沢度(反射角:60°)を光沢計VG7000(日本電色工業株式会社)により測定した。そして、顔料分散体(15)〜(17)、(19)〜(21)は、顔料分散体(23)に対して、顔料分散体(18)、(22)は、顔料分散体(24)に対しての光沢度の倍率をそれぞれ求めた。
A:比較用の顔料分散体に対する光沢度の倍率が、2倍以上である。
B:比較用の顔料分散体に対する光沢度の倍率が、1.5倍以上2倍未満である。
C:比較用の顔料分散体に対する光沢度の倍率が、1.5倍未満である。
(表2において、PY180はC.I.Pigment Yellow 180を表す。また、PY74は、C.I.Pigment Yellow 74を表す。)
<実施例16>
高速撹拌装置T.K.ホモミキサー(プライミクス株式会社製)を備えた2L用四つ口フラスコ中にイオン交換水710部と0.1mol/l−リン酸三ナトリウム水溶液450部を添加し、回転数を12000rpmに調製し、60℃に加温した。ここに1.0mol/l−塩化カルシウム水溶液68部を徐々に添加し、微小な難水溶性分散安定剤リン酸カルシウムを含む水系分散媒体を調製した。
・顔料分散体(15):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
実施例16において、サリチル酸アルミニウム化合物を添加しないこと以外は、実施例16と同様にしてイエロートナー(2)を得た。
実施例16において、顔料分散体(15)を、顔料分散体(21)に変更したこと以外は、実施例16と同様にしてイエロートナー(3)を得た。
実施例16において、顔料分散体(15)を、顔料分散体(23)に変更したこと以外は、実施例16と同様にしてイエロートナー(4)を得た。
実施例17において、顔料分散体(15)を、顔料分散体(23)に変更したこと以外は、実施例17と同様にしてイエロートナー(5)を得た。
上記イエロートナー(1)〜(5)の評価を以下のように行った。
上記トナーの個数平均粒径(D1)及び重量平均粒径(D4)を、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を行った。電解液としては、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)を用いた。具体的な測定方法としては、前記電解水溶液100ml中に、分散剤として界面活性剤(アルキルベンゼンスルホン酸塩)を、0.1ml程度加え、更に測定試料(トナー粒子)を2mg程度加えた。試料を懸濁した電解液に対して、超音波分散器で約1〜3分間分散処理を行った。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した。トナー粒子の個数分布から求めた個数平均粒径(D1)と、トナー粒子の体積分布から求めたトナー粒子の重量平均粒径(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。
フロー式粒子像測定装置「FPIA−2100型」(シスメックス株式会社製)を用いて測定を行い、下式を用いて円形度を求め、平均円形度を算出した。
通常環境(温度25℃/湿度60%RH)下において、最大トナー乗り量を0.45mg/cm2に調整した16階調画像サンプルをカラー複写機CLC−1100改造機(キヤノン(株)製、定着オイル塗布機構を省いた)を用いて、画像サンプルを出力した。画像サンプルの基紙としては、CLCカラーコピー用紙(キヤノン(株)製)を用いた。SpectroLino(Gretag Machbeth社製)を用いて、得られた画像サンプルのイエロー色の濃度OD(Y)を測定した。
A:OD(Y)が1.6以上である。(着色性が非常に良い)
B:OD(Y)が1.5以上、1.6未満である。(着色性が良い)
C:OD(Y)が1.5未満である。(着色性が悪い)
Claims (6)
- 分散媒体中に、一般式(1)で表される化合物と一般式(2)で表されるイエロー顔料を含有する顔料分散体。
[一般式(1)において、R1〜R3、及びR’1〜R’3は各々独立して水素原子、アルキル基、アリール基又はアラルキル基を表す。]
[一般式(2)中、R4〜R8は各々独立して水素原子、アルコキシル基、フェニル基、カルボン酸基、カルボン酸エステル基、カルバモイル基、ニトロ基、トリフルオロメチル基、ハロゲン原子を表し、R9〜R13は各々独立して水素原子、アルキル基、アルコキシル基、アシルアミノ基、ハロゲン原子を表し、R10とR11は互いに結合して環を形成しても良い。] - 前記一般式(1)において、R1、R2及びR3が同一であり、R’1、R’2及びR’3が同一である請求項1に記載の顔料分散体。
- 前記一般式(1)において、R1〜R3がアルキル基、R’1〜R’3が水素原子である請求項1又は2に記載の顔料分散体。
- 前記一般式(2)で表されるイエロー顔料が、C.I.Pigment Yellow 74、C.I.Pigment Yellow 180からなる群より選ばれる1種以上のイエロー顔料である請求項1〜3のいずれか1項に記載の顔料分散体。
- 前記一般式(2)で表されるイエロー顔料が、C.I.Pigment Yellow 180である請求項1〜3のいずれか1項に記載の顔料分散体。
- 結着樹脂、イエロー顔料及びワックス成分を含有するイエロートナー粒子を有するトナーであって、請求項1〜5のいずれか1項に記載の顔料分散体を用いて作製されたことを特徴とするイエロートナー。
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