JPH0425535B2 - - Google Patents
Info
- Publication number
- JPH0425535B2 JPH0425535B2 JP57056961A JP5696182A JPH0425535B2 JP H0425535 B2 JPH0425535 B2 JP H0425535B2 JP 57056961 A JP57056961 A JP 57056961A JP 5696182 A JP5696182 A JP 5696182A JP H0425535 B2 JPH0425535 B2 JP H0425535B2
- Authority
- JP
- Japan
- Prior art keywords
- toner
- polymer
- weight
- fixing
- parts
- 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.)
- Expired - Lifetime
Links
- 150000001412 amines Chemical class 0.000 claims description 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- 229920002554 vinyl polymer Polymers 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 description 51
- 238000000034 method Methods 0.000 description 39
- 239000011572 manganese Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 229920001577 copolymer Polymers 0.000 description 17
- 229920005989 resin Polymers 0.000 description 16
- 239000011347 resin Substances 0.000 description 16
- 238000004132 cross linking Methods 0.000 description 13
- 239000000178 monomer Substances 0.000 description 13
- -1 ethylene, propylene, Ethylene olefins Chemical class 0.000 description 12
- 239000000654 additive Substances 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 9
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 8
- 230000005291 magnetic effect Effects 0.000 description 8
- 239000000155 melt Substances 0.000 description 8
- 238000011161 development Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 6
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 108091008695 photoreceptors Proteins 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 229920006037 cross link polymer Polymers 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 4
- 238000004898 kneading Methods 0.000 description 4
- 239000000434 metal complex dye Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-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
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- 238000011088 calibration curve Methods 0.000 description 2
- 238000012668 chain scission Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000008119 colloidal silica Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 230000005294 ferromagnetic effect Effects 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000006247 magnetic powder Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229920013730 reactive polymer Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000010008 shearing Methods 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- 229920002379 silicone rubber Polymers 0.000 description 2
- 239000004945 silicone rubber Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical compound C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 2
- QLLUAUADIMPKIH-UHFFFAOYSA-N 1,2-bis(ethenyl)naphthalene Chemical compound C1=CC=CC2=C(C=C)C(C=C)=CC=C21 QLLUAUADIMPKIH-UHFFFAOYSA-N 0.000 description 1
- VDYWHVQKENANGY-UHFFFAOYSA-N 1,3-Butyleneglycol dimethacrylate Chemical compound CC(=C)C(=O)OC(C)CCOC(=O)C(C)=C VDYWHVQKENANGY-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
- JKRCFFQHGMPORJ-UHFFFAOYSA-N 1-chloro-1h-indene Chemical compound C1=CC=C2C(Cl)C=CC2=C1 JKRCFFQHGMPORJ-UHFFFAOYSA-N 0.000 description 1
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
- UIBFMDRTPXEPOA-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene;1-ethenylnaphthalene Chemical compound ClC1=CC=C(C=C)C=C1.C1=CC=C2C(C=C)=CC=CC2=C1 UIBFMDRTPXEPOA-UHFFFAOYSA-N 0.000 description 1
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
- IEXQFYPEUSYMHN-UHFFFAOYSA-N 2-[2-[2-(2-hydroxyethoxy)ethyl-octadecylamino]ethoxy]ethanol Chemical compound CCCCCCCCCCCCCCCCCCN(CCOCCO)CCOCCO IEXQFYPEUSYMHN-UHFFFAOYSA-N 0.000 description 1
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-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
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 229920006358 Fluon Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- IRERQBUNZFJFGC-UHFFFAOYSA-L azure blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[S-]S[S-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] IRERQBUNZFJFGC-UHFFFAOYSA-L 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- DFYKHEXCUQCPEB-UHFFFAOYSA-N butyl 2-methylprop-2-enoate;styrene Chemical compound C=CC1=CC=CC=C1.CCCCOC(=O)C(C)=C DFYKHEXCUQCPEB-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- HIZDLVPIKOYIOY-UHFFFAOYSA-N butyl prop-2-enoate;2-methylprop-2-enoic acid;styrene Chemical compound CC(=C)C(O)=O.C=CC1=CC=CC=C1.CCCCOC(=O)C=C HIZDLVPIKOYIOY-UHFFFAOYSA-N 0.000 description 1
- IYCOKCJDXXJIIM-UHFFFAOYSA-N butyl prop-2-enoate;prop-2-enoic acid;styrene Chemical compound OC(=O)C=C.C=CC1=CC=CC=C1.CCCCOC(=O)C=C IYCOKCJDXXJIIM-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 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 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 229920006244 ethylene-ethyl acrylate Polymers 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007849 furan resin Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052595 hematite Inorganic materials 0.000 description 1
- 239000011019 hematite Substances 0.000 description 1
- PBZROIMXDZTJDF-UHFFFAOYSA-N hepta-1,6-dien-4-one Chemical compound C=CCC(=O)CC=C PBZROIMXDZTJDF-UHFFFAOYSA-N 0.000 description 1
- UCNNJGDEJXIUCC-UHFFFAOYSA-L hydroxy(oxo)iron;iron Chemical compound [Fe].O[Fe]=O.O[Fe]=O UCNNJGDEJXIUCC-UHFFFAOYSA-L 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- LIKBJVNGSGBSGK-UHFFFAOYSA-N iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Fe+3].[Fe+3] LIKBJVNGSGBSGK-UHFFFAOYSA-N 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 230000005389 magnetism Effects 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
- 238000005259 measurement Methods 0.000 description 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 1
- 229940117841 methacrylic acid copolymer Drugs 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 229920003146 methacrylic ester copolymer Polymers 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- ZARXZEARBRXKMO-UHFFFAOYSA-N n,n-bis(ethenyl)aniline Chemical compound C=CN(C=C)C1=CC=CC=C1 ZARXZEARBRXKMO-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- HILCQVNWWOARMT-UHFFFAOYSA-N non-1-en-3-one Chemical compound CCCCCCC(=O)C=C HILCQVNWWOARMT-UHFFFAOYSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000003960 organic solvent Substances 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pentâ4âenâ2âone Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 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
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920002102 polyvinyl toluene Polymers 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 1
- 229920006249 styrenic copolymer Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 235000013799 ultramarine blue Nutrition 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
- 229960000834 vinyl ether Drugs 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/087—Binders for toner particles
- G03G9/08702—Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- G03G9/08726—Polymers of unsaturated acids or derivatives thereof
- G03G9/08731—Polymers of nitriles
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/087—Binders for toner particles
- G03G9/08784—Macromolecular material not specially provided for in a single one of groups G03G9/08702Â -Â G03G9/08775
- G03G9/08793—Crosslinked polymers
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Developing Agents For Electrophotography (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
ãçºæã®è©³çŽ°ãªèª¬æã
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ç¹ã«ç±ããŒã©ãŒå®çã«é©ãããããŒã«é¢ãããDETAILED DESCRIPTION OF THE INVENTION The present invention relates to a toner for developing electrostatic images in electrophotography, electrostatic recording, electrostatic printing, etc.
In particular, it relates to a toner suitable for heat roller fixing.
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å®çãè€åç©ãåŸããã®ã§ããã Conventionally, as an electrophotographic method, U.S. Patent No. 2297691
Specification of No. 42-23910 and Special Publication No. 1973
Many methods are known, as described in Japanese Patent No. 24748, etc., but in general, a photoconductive substance is used to form an electrical latent image on a photoreceptor by various means, and then the A latent image is developed using toner, and after the toner image is transferred to a transfer material such as paper as necessary, it is fixed by heat, pressure, solvent vapor, etc. to obtain a copy.
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ã©ãŒã«ããå§çå ç±æ¹åŒã§ããã Various methods and devices have been developed for the above-mentioned final step, which is the step of fixing the toner image on a sheet such as paper. The most common method at present is the compression heating method using a heated roller.
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é æ¡ä»¶ã®ïŒã€ãšãããŠããã The pressure heating method using a heated roller performs fixing by passing the toner image surface of the sheet to be fixed under pressure while contacting the surface of a heated roller whose surface is made of a material that has releasability for toner. . In this method, the surface of the heat roller and the toner image on the sheet to be fixed come into contact with each other under pressure, so the thermal efficiency when fusing the toner image onto the sheet to be fixed is extremely good, and the fixing can be carried out quickly. It is very effective in high-speed electrophotographic copying machines. However, in the above method, since the surface of the heat roller and the toner image contact each other under pressure in a molten state, a portion of the toner image adheres to and transfers to the surface of the fixing roller, and this is transferred again to the next sheet to be fixed. A so-called offset phenomenon may occur, and the sheet to be fixed may be stained. One of the essential conditions for the heat roller fixing method is to prevent toner from adhering to the surface of the heat fixing roller.
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ãŒã®éçºãæãŸããŠããã®ãçŸç¶ã§ããã Conventionally, in order to prevent toner from adhering to the fixing roller surface, for example, the roller surface is made of a material that has excellent releasability for toner, such as silicone rubber or fluorine-based resin, and the surface is also coated with anti-offset and roller surface coatings. In order to prevent fatigue, the surface of the roller is coated with a thin film of a liquid with good mold releasability, such as silicone oil. However, although this method is extremely effective in preventing toner offset, it requires a device to supply a liquid for preventing offset, resulting in problems such as a complicated fixing device. .
Therefore, it is not preferable to prevent offset by supplying an offset-preventing liquid, but rather the development of a toner with high offset resistance over a wide fixing temperature range is currently desired.
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é¡ãå€ãã As described in Japanese Patent Publication No. 51-23354, such an offset phenomenon tends to occur when a low molecular weight resin is used. Therefore, as described in the same publication, it may be possible to prevent the offset phenomenon by using a crosslinked resin, but the present inventors have investigated and found that simply creating a crosslinked resin does not necessarily prevent the offset phenomenon. I found out that it wasn't good. In particular, when the degree of crosslinking is increased, the fixing temperature increases, and in the case of magnetic toner, the fixing temperature increases and the offset resistance deteriorates, causing many problems.
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ããŠãããããŒãæãŸããŠããã Of course, in addition to fixing properties, toners also need to be excellent in anti-blocking properties, development properties, transferability, cleaning properties, etc., but conventional toners must have the following defects: I had one or more. That is, many toners that are easily melted at relatively low temperatures by heating tend to cake or aggregate during storage or in a copying machine. Many toners have poor triboelectric and rheological properties due to environmental humidity changes. In addition, with many toners, the density of the resulting image decreases due to mutual deterioration of the toner, carrier particles, and photosensitive plate due to collisions between toner particles and carrier particles due to repeated development due to continuous use and contact between them and the photosensitive plate surface. or increase the background density, reducing the quality of the copy. Furthermore, with many toners, when an attempt is made to increase the density of a copied image by increasing the amount of toner adhering to the surface of a photosensitive plate having a latent image, the background density usually increases, resulting in a so-called fog phenomenon. Therefore, there is a need for a toner that has excellent various toner properties and is suitable for hot roller fixing.
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ããããŒãæäŸããããšã«ããã Therefore, it is an object of the present invention to provide a toner having excellent physical and chemical properties that overcomes the above-mentioned toner deficiencies.
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ããã®ã§ããã SUMMARY OF THE INVENTION An object of the present invention is to provide a toner for hot roller fixing which has good fixing properties and particularly good offset resistance.
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ãŒãæäŸãããã®ã§ããã A further object of the present invention is to provide a toner for hot roller fixing that has good chargeability and always exhibits stable chargeability during use, and provides clear and fog-free images.
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çšã®ãããŒãæäŸãããã®ã§ããã A further object of the present invention is to provide a toner for hot roller fixing that has excellent fluidity, does not cause aggregation, and has excellent impact resistance.
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ã®ãããŒãæäŸãããã®ã§ããã A further object of the present invention is to provide a toner for hot roller fixing that has less deposits on the surface of a toner holding member or photoreceptor.
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ãå¯èœãªç£æ§ãããŒãæäŸãããã®ã§ããã A further object of the present invention is to provide a magnetic toner which, when used as a magnetic developer, exhibits good and uniform magnetism and can be fixed by a hot roller.
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è·åçŸåçšãããŒã«ããã Its feature is the ratio of weight average molecular weight (Mw) to number average molecular weight (Mn) (Mw/
Mn) is greater than 4, Mw is greater than 100000,
A toner for developing electrostatic images contains a vinyl polymer having a carboxyl group crosslinked with an amine represented by the following formula.
åŒäžãïœãšïœã¯ããããïŒãïŒã®æŽæ°ãïœãšïœ
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ã¢ã«ãã«åºãå«ãïŒã§ããã In the formula, a and b are integers of 2 to 4, respectively, x and y
are each an integer from 1 to 50, and R is an alkyl group consisting of 8 to 30 carbon atoms (including branched and cycloalkyl groups).
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åäžããããšãå¯èœã«ãªãã The toner for thermal roller fixing according to the present invention has excellent physical and chemical properties, and by using this toner, no offset occurs even when no offset prevention liquid is applied to the surface of the fixing roller. Since it can perform good heat roller fixing, the fixing device can be simplified and lightened.Furthermore, it has stable and excellent developing characteristics, so it significantly improves the stability and reliability of copying machines. becomes possible.
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äœæãããšããšã»ãŒåçã®å®ç枩床ã瀺ãã That is, in the toner of the present invention, although the detailed reaction mechanism is unknown, the binder resin reacts with the amine and undergoes a type of crosslinking, resulting in improved mechanical properties at room temperature and improved impact resistance. It has excellent toughness and toughness, and also has improved charging characteristics, resulting in improved development characteristics as a toner. Furthermore, when the toner of the present invention is fixed with a hot roller fixer, offset resistance at high temperatures is significantly improved. However, the fixing temperature is approximately the same as when the toner is prepared with the corresponding unreacted polymer.
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ååãåãæ³ã§æž¬å®ãè¡ãªã€ãã The above fixing characteristics are obtained when the melt index of the toner is in the range of 0.01 to 10 g/10 min (particularly preferably 0.1 to 6 g/10 min) (test conditions are temperature 125°C, load 10 kg, filling amount 5 ~8g),
Shows especially excellent fixing properties. The melt index here was measured by a manual cutting method using an apparatus described in JIS K7210, a flow test method for thermoplastic plastics according to the Japanese Industrial Standards.
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ãã®ã§ããã In the present invention, particularly preferable results can be obtained when a vinyl polymer having a carboxyl group with a weight average molecular weight/number average molecular weight (Mw/Mn) value of greater than 4.0 (particularly preferably greater than 10) is used. Furthermore, by using a polymer with such a molecular weight distribution, it is possible to easily produce a polymer having a desired melt viscosity through a mild reaction by reaction with an amine, thereby achieving desired fixing characteristics. Therefore, it is possible to stably produce toner having the following properties.
ããã«ãã«ã«ããã·ã«åºãæããéåäœã®ã¡ã«
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ã®æ¡ä»¶äžã§0.01ã10ïœïŒminã奜ãŸãããããã«
0.1ãïŒïœïŒminã«ãããšç¹ã«å¥œãŸããã Furthermore, the melt index value of a polymer having a carboxyl group is 125â, a charge of 2 kg
0.01 to 10 g/min is preferable under the conditions of
Particularly preferred is 0.1 to 5 g/min.
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ç»åãåŸãããšãå°é£ã«ãªãã In addition to the above-mentioned fixing properties and mechanical properties, an important electrophotographic property that a toner should have is triboelectric charging properties.To improve the charging properties, a charge control agent is added to the toner. is commonly added. Therefore, if additives such as charge control agents are not uniformly dispersed in the toner,
The triboelectric charging properties of the toner are significantly impaired, making it difficult to obtain clear images.
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ããã Therefore, when manufacturing toner, in order to uniformly disperse additives such as charge control agents and colorants in the polymer, raw materials are melt-kneaded at a temperature near the softening point of the polymer, at which the polymer exhibits a high melt viscosity state. It is commonly done. When melt-kneaded in the high melt viscosity region,
Additives such as charge control agents and colorants are uniformly dispersed in the toner by shearing force caused by internal friction of the polymer, and a toner with desired coloring and charging properties is obtained.
ããããMwïŒMnïŒïŒã®ãããªéåäœãè»å
ç¹ååŸã®é«æº¶èç²åºŠé åã§æº¶èæ··ç·Žãããšãéå
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éšæ©æŠãéåžžã«å€§ãããããæåã匷ã
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äžãæãããªãã»ããæ§ã«æªåœ±é¿ãäžãããäŸã
ã°ãã¡ã«ãã€ã³ããã¯ã¹ãçŽïŒïœïŒ10minçšåºŠã®
åèšéåäœãããŒã«ãã«ãçšããŠãããŒã«ã¢ã³ã
ãªã³ã°æ³ã§æž¬å®ããéåäœã®è»åç¹ïŒçŽ135âïŒ
ããè¥å¹²äœã枩床ïŒ120âãããïŒã§æº¶èæ··ç·Žã
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枩床ïŒ180âïŒã§æº¶èæ··ç·Žããå Žåãããéåžžã«
çããªãã However, when a polymer with Mw/Mn > 4 is melt-kneaded in the high melt viscosity region around the softening point, the internal friction in the polymer becomes extremely large and the shearing force becomes too strong, causing molecular chain scission. , which leads to a decrease in melt viscosity and adversely affects offset properties. For example, the softening point (about 135°C) of the polymer whose melt index is about 5 g/10 min was measured by the ball and ring method using a roll mill.
When melt-kneaded at a slightly lower temperature (approximately 120°C), the melt index increases significantly, almost doubling the value, and the fixing temperature range in which the offset phenomenon does not occur is considerably higher than the softening point of the polymer. It becomes much narrower than when melting and kneading at (180â).
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æ§ãšã®åé¡ã解決ããã«ã¯ãåèšéåäœã溶èæ··
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ããã The present inventors believe that in order to solve the problem of offset resistance and additive dispersibility, it is possible to apply some crosslinking when melt-kneading the polymer to cancel out the decrease in viscosity caused by molecular chain scission. I found something good.
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ç²åºŠé åã§æº¶èæ··ç·Žã§ããã®ã§ãæ·»å å€ãéåžžã«
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ãã According to the above-mentioned method, it is possible to melt and knead the polymer in a high viscosity region near its softening point, so it is possible to obtain a toner in which the additives are dispersed very uniformly, the charging characteristics are stabilized, and the non-offset temperature range is wide. It will be done.
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å®çç¹æ§ãæãããããŒãåŸãããã«ã¯ãMwïŒ
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çç£ããããšãã§ããªãã As will be specifically shown later, when a polymer with Mw/Mn<4 is used, in order to obtain a toner having desired fixing characteristics through reaction with an amine, it is necessary to increase Mw/Mn<4.
Compared to when using a polymer with Mn of 4.0 or more, it is necessary to set the amount of diamine and reaction conditions so that the above reaction occurs more actively. It is very difficult to stop the reaction with just the right amount and not enough, making it impossible to stably produce toner with desired fixing characteristics with good reproducibility.
äžæ¹ãMwïŒMnïŒïŒã®éåäœãçšãããšãè
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ãæãããããšãå¯èœã«ãªãã On the other hand, when using a polymer with Mw/Mn > 4, in order to impart offset resistance to the toner, the polymer only needs to be slightly reacted with an amine and crosslinked.
The reaction can be carried out under mild conditions, the reaction can be easily controlled, and toner with excellent fixing properties can be stably produced. Furthermore, when a polymer with Mw/Mn>4, more preferably Mw>100000 is lightly crosslinked,
As the molecular weight distribution becomes wider, it becomes possible to provide the toner with offset resistance while keeping the minimum fixing temperature low.
MwïŒMnã®å€ã4.0ããã倧ããã奜ãŸããã¯
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éæãããã The value of Mw/Mn is greater than 4.0, preferably
Polymers with Mw greater than 100,000 can be synthesized using well-known polymerization methods such as solution polymerization, suspension polymerization, emulsion polymerization, and bulk polymerization. Methods for adjusting Mw/Mn include methods of melting or mixing several types of resins with different molecular weights in a molten state, changing the reaction temperature during the polymerization reaction, and using initiators, chain transfer agents, etc. There are methods of manufacturing by blending and methods of increasing Mw/Mn and Mw by applying a certain degree of crosslinking when forming a polymer from monomers, among these manufacturing methods, The method most suitable for the present invention is to control the degree of crosslinking within a low range and adjust Mw/Mn, and this is, for example, by adding a trace amount of a polyfunctional monomer to the polymerization reaction system, preferably 0.01 to 10% by weight. achieved by.
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倧ããªéåäœãåŸãå Žåã«ã¯éååå¿ã®å¶åŸ¡ãé
åžžã«é£ããã On the other hand, as a process for synthesizing the above polymer, a solution polymerization method is preferred. This is because in emulsion polymerization and suspension polymerization, monomers are emulsified or dispersed using additives such as surfactants and dispersion stabilizers in water, which is a continuous phase, and then polymerized by adding salts, etc. The resulting polymer contains the hydrophilic additives mentioned above. When such hydrophilic additives are present in the toner,
Under high humidity conditions, the toner often absorbs moisture, which adversely affects the electrical properties of the toner, such as a decrease in specific resistance. Furthermore, since the polymer used in the present invention has a hydrophilic carboxyl group, it is difficult to obtain a stable reaction. Furthermore, in the bulk polymerization method, problems such as a gel effect occur when the degree of polymerization increases, and it is extremely difficult to control the polymerization reaction when obtaining a polymer with a large Mw/Mn.
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ççšãããŒã«é©çšããããšãå¯èœã«ãªãã On the other hand, in the solution polymerization method, the polymerization reaction is generally carried out in a hydrophobic organic solvent, so a hydrophilic additive is not required, and the presence of a solvent makes it relatively easy to control the polymerization reaction. However, the solution polymerization method has a problem in that when the degree of crosslinking is increased, a gel is formed that is insoluble in the solvent, making it difficult to control the polymerization reaction and to recover the polymer after polymerization. Therefore, a polymer having a degree of crosslinking within a range that does not cause the above-mentioned problems is synthesized by solution polymerization, and further, according to the present invention, a polymer having a degree of crosslinking created by the solution polymerization method is synthesized by solution polymerization. It is produced by a solution polymerization method that has the above-mentioned excellent properties by reacting a polymer and an amine during the toner manufacturing process and increasing the degree of crosslinking to the extent that it provides a melt viscosity suitable for the fixing characteristics of the toner. It becomes possible to more easily apply the polymer to a toner for hot roller fixing.
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åšãçšããã In the present invention, the value of Mw/Mn was calculated from the value measured by gel permeation chromatography. The measurement conditions are as follows: Tetrahydrofuran is flowed as a solvent at a flow rate of 1 ml per minute at a temperature of 25° C., and 0.5 ml of a sample solution of tetrahydrofuran with a sample concentration of 8 mg/ml is injected. In addition, in order to accurately measure the molecular weight range of 10 3 to 2 à 10 6 as a column, it is recommended to combine multiple commercially available polystyrene gel columns, such as ÎŒ-styragel 500, 10 manufactured by Waters. A combination of 3 , 10 4 , 10 5 or shodex A-802, 803, 804, 805 made by Showa Denko is good. When measuring the molecular weight of a sample,
The molecular weight distribution of the sample was calculated from the relationship between the logarithm value and the count number of a calibration curve prepared using several types of monodisperse polystyrene standard samples. For example, standard polystyrene samples for creating a calibration curve include:
Manufactured by Pressure Chemical Co. or Toryo Soda Kogyo Co., Ltd., with a molecular weight of 6Ã10 2 , 2.1Ã10 3 , 4Ã10 3 ,
1.75Ã10 4 , 5.1Ã10 4 , 1.1Ã10 5 , 3.9Ã10 5 , 8.6Ã
It is appropriate to use at least 10 standard polystyrene samples of 10 5 , 2Ã10 6 , and 4.48Ã10 6 . In addition, an RI (refractive index) detector is used as a detector.
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ããŠçšããããšãã§ããã Examples of monomers copolymerizable with the above carboxyl group-containing monomers include styrene, α-methylstyrene, p-chlorostyrene vinylnaphthalene, methyl acrylate, ethyl acrylate, butyl acrylate, dodecyl acrylate, and acrylic. octyl acid, phenyl acrylate,
Substituted monocarboxylic acids with double bonds such as methyl methacrylate, ethyl methacrylate, butyl methacrylate, octyl methacrylate, acrylonitrile, methacrylonitrile, acrylamide, etc.; for example, dibutyl maleate, dimethyl maleate, etc. diester derivatives of dicarboxylic acids having double bonds such as; vinyl esters such as vinyl chloride, vinyl acetate, vinyl benzoate; such as ethylene, propylene,
Ethylene olefins such as butylene;
Vinyl ketones such as vinyl methyl ketone, vinyl hexyl ketone, etc.; vinyl datals such as vinyl methyl ether, vinyl ethyl ether, vinyl isobutyl ether, etc.; aromatic divinyl compounds such as vinylbenzene, divinylnaphthalene, etc.; For example, carboxylic acid esters having two double bonds such as ethylene glycol diacrylate, ethylene glycol dimethacrylate, 1,3-butanediol dimethacrylate, divinylaniline,
Divinyl compounds such as divinyl ether, divinyl sulfide, and divinyl sulfone and compounds having three or more vinyl groups can be used alone or as a mixture.
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ã®ç¯å²ã«ãããšãç¹ã«å¥œãŸããçµæãåŸãããã The proportion of carboxyl group-containing monomers contained in the carboxyl group-containing polymer is 0.1
~30 wt% gives good results, 0.5-20 wt%
Particularly preferable results can be obtained within the range of .
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ã§ããã Next, in the present invention, the amine for crosslinking the carboxyl group-containing polymer has the following general formula.
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æåããåã³ã·ã¯ãã¢ã«ãã«åºãå«ãïŒã§ããã In the formula, a and b represent integers of 2 to 4 and may be the same or different, x and y represent integers of 1 to 50 and may be the same or different, and R
is an alkyl group consisting of 8 to 30 carbon atoms (however,
(including branched and cycloalkyl groups).
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ããã Among the alkoxylated amines having the above general formula, those which are wax-like solid substances under normal pressure and room temperature conditions are excellent. Low-molecular-weight liquid alkoxylated amines crosslink polymers with carboxyl groups in the same way as solid alkoxylated amines, but there are problems such as unreacted liquid alkoxylated amines bleeding out of the toner. Preferred are alkoxylated amines.
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ãããšãç¹ã«åªããçµæãåŸãããã In the present invention, the reaction between the polymer and the amine is
Since not all of the amine used will react,
The amount of reactive alkoxylated amine is required in excess, and although it varies depending on the type of amine, it is generally from 0.01 to 100 parts by weight of the polymer, including unreacted amine. Preferably, it is contained in an amount of 20 parts by weight, and particularly good results are obtained when 0.1 to 10 parts by weight are used.
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ããŠãè¯ãã The reaction between the vinyl polymer and the reactive amine in the present invention can be carried out by a method in which the above-mentioned amine is reacted with the reactive polymer in a roll mill,
There is a method of adding an amine to a hot xylene solution of a reactive polymer and causing a reaction. Taking into account post-treatment steps after the reaction, the reaction by melt-kneading method is most suitable for the present invention. A polymer reactant may be first produced through the reaction to form a binder, and then a toner may be produced together with other toner materials.
The above reaction itself may be carried out during heating and kneading of the toner material during the toner manufacturing process, and then finely pulverized to form a toner.
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ãŠ50æéæœåºããã On the other hand, in the toner of the present invention, if the gel content of the polymer after reacting with the amine is 50% or more, the crosslinking of the polymer will proceed too much, and the temperature at which the polymer becomes soft will rise significantly, resulting in the formation of a toner. In this case, the fixing temperature becomes high, which is undesirable. Therefore, the gel content of the crosslinked polymer should be less than 50%;
In particular, if it is 35% or less, the fixing temperature is almost the same as that of an uncrosslinked polymer, and particularly good results can be obtained.
The gel content in the present invention refers to the proportion of the polymer portion that has been crosslinked and is insoluble in a solvent, and can be used as a kind of index representing the degree of crosslinking of a highly crosslinked polymer. Here, gel content is defined as a value measured as follows. That is, a certain weight (W 1 g) of the polymer after reacting with the diamine was weighed, and the soluble components in the polymer were removed with a solvent using a Soxhlet extractor using a G-3 glass filter. , and the sample that remained unextracted was dried and weighed (W 2 g). Gel content is W 2 /W 1 Ã 100 (%)
It is calculated as As such a solvent, a nonpolar solvent is preferable, and in this case, extraction was performed using benzene for 50 hours.
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ãã€ãŠæž¬å®ã§ããã Furthermore, among binder polymers crosslinked by reaction with amines, the glass transition temperature is 50%.
â or above is excellent because it does not cause problems such as toner aggregation in the developing device or adhesion to the photoreceptor surface, etc., and in particular, one with a glass transition temperature of 50â to 80â is more preferable. . Thus, in order for the glass transition point of the crosslinked polymer to be 50°C or higher, it is preferable that the glass transition point of the polymer having a carboxyl group before crosslinking is 40°C or higher. Note that the glass transition temperature of the polymer can be measured using a differential scanning calorimeter.
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ã³ãã³æš¹èãç³æ²¹ç³»æš¹èããªã©ã䜿çšã§ããã The toner of the present invention has a binder polymer crosslinked by the method described above as a main resin component, but other polymers and resins can be mixed and used as necessary. Other resins that can be used in combination include, for example, polystyrene,
Monopolymers of styrene and its substituted products such as poly-p-chlorostyrene and polyvinyltoluene; styrene-p-chlorostyrene copolymers, styrene-
Vinyltoluene copolymer, styrene-vinylnaphthalene copolymer, styrene-acrylic ester copolymer, styrene-methacrylic ester copolymer, styrene-α-methyl chloromethacrylate copolymer, styrene-acrylonitrile copolymer , styrene-vinyl methyl ether copolymer,
Styrene-vinyl ethyl ether copolymer, styrene-vinyl methyl ketone copolymer, styrene-
Styrenic copolymers such as butadiene copolymer, styrene-isoprene copolymer, styrene-acrylonitrile-indene copolymer; polyethylene, polypropylene, polyvinyl chloride, phenolic resin, natural resin-modified phenolic resin, acrylic ester resin, Methacrylic acid ester resin, polyvinyl acetate, silicone resin, polyurethane, furan resin, epoxy resin, xylene resin,
Polyvinyl butyral, terpene resin, chloroindene resin, petroleum resin, etc. can be used.
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ããã In particular, by adding 0.1 to 10% by weight (more preferably 0.2 to 5% by weight) of an ethylene olefin monopolymer or ethylene olefin copolymer having a melt viscosity of 10 to 10 6 cps at 140°C to the toner. The dispersibility and compatibility of the pigment and magnetic fine particles with the toner are improved, and the adverse effects on the photoreceptor surface, cleaning member, etc. are reduced. Examples of the ethylene-based olefin monopolymer or ethylene-based olefin copolymer include polyethylene, polypropylene, and ethylene-olefin copolymer.
Propylene copolymer, ethylene-vinyl acetate copolymer, ethylene-ethyl acrylate copolymer,
The above copolymers preferably contain 50 mol% to 100 mol% (more preferably 60 mol% to 100 mol%) of olefin monomers.
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åä»ãããã®ãçšããã The Brookfield method was used to measure the melt viscosity, and here a B-type viscometer equipped with a small sample adapter was used.
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ã®æé¡æãããã Any suitable pigment or dye can be used as a colorant in the toner of the present invention. For example, there are known dyes and pigments such as carbon black, iron black, phthalocyanine blue, ultramarine blue, quinacridone, and benzidine yellow.
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ç¥ãããŠãããã®ã䜿ããã Furthermore, when the toner of the present invention is a magnetic toner, it contains magnetic powder, which may also serve as a coloring agent. Magnetic powders include ferromagnetic elements, alloys containing these, compounds such as magnetite, hematite, and ferrite, alloys and compounds of iron such as cobalt, nickel, and manganese, and other ferromagnetic alloys. You can use what is provided.
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ãŠãè¯ãã As other additives, carbon black, nigrosine, metal complex salts, colloidal silica powder, fluororesin powder, metal salts of higher fatty acids, etc. may be added for purposes such as charge control and prevention of agglomeration.
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ããã The toner of the present invention can be applied to various developing methods.
For example, magnetic brush development method, cascade development method, method using conductive magnetic toner described in U.S. Pat. No. 3,909,258, and JP-A-53-31136
A method using a high-resistance magnetic toner described in Japanese Patent Publication No. 54-42141, a method described in Japanese Patent Application Laid-Open No. 55-18656, etc., a fur brush development method,
There are powder cloud method, impression method, etc.
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ã®ã䜿çšã§ããã The toner image formed on a fixing sheet such as paper using the toner according to the present invention does not cause the toner offset phenomenon even when a fixing roller that does not supply offset prevention liquid to the surface of the toner image is used. Fixing can be done with a heated roller. The fixing roller has a smooth surface made of a fluorine-based resin such as Teflon (manufactured by DuPont), Fluon (manufactured by ICI), and Keru F (manufactured by 3M), silicone rubber, or silicone resin. In some cases, those having a metal surface can be used.
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26ã§ãMwã¯243000ã§ãã€ãã[Example 1] 90 parts by weight of xylene was placed in a separable flask, 75 parts by weight of styrene, 20 parts by weight of butyl methacrylate, 5 parts by weight of maleic acid, and 0.5 parts by weight of divinylbenzene were added, and the gas phase was purged with nitrogen gas. After purging, the temperature was maintained at 80°C, and a solution of 0.8 parts by weight of benzoyl peroxide dissolved in 10 parts by weight of xylene was added dropwise over 30 minutes using a dropping funnel purged with nitrogen gas.
The mixture was further stirred at 80°C for 10 hours. Next, 5 parts by weight of a toluene solution containing 0.3 parts by weight of benzoyl peroxide was added dropwise, and the temperature was further raised to 90°C and maintained at that temperature for 5 hours to complete polymerization. After cooling, precipitate the polymer in a large amount of methanol, separate the precipitate, and heat at 60°C.
It was dried and collected. Mw/Mn of this polymer is
26, Mw was 243,000.
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åïŒã¶ãã³ãã¢ãŒã¹ããã©ãã¯ïŒ¢ïŒC.I.Acid
Black63ïŒBASF瀟補ïŒïŒéééšãããŒã«ãã«äž
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ã«ãã€ã³ããã¯ã¹ã¯125âã»10Kgã®æ¡ä»¶äžã§ã
1.36ïœïŒ10minã§ãã€ãããã®ãããŒ100éééš
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âãã210âãŸã§èªããããªãã€ãã 100 parts by weight of the above polymer, Naimeen S-202 (a condensation product of ethylene oxide of a primary aliphatic amine having an alkyl group having 13 to 17 carbon atoms, commercially available from NOF Corporation, x+y=2) 0.3 parts by weight, 60 parts by weight of magnetite, metal complex dye (product name: Zapon First Black B, CIAcid
4 parts by weight of Black 63 (manufactured by BASF) were melt-kneaded at 150°C for 30 minutes on a roll mill. After cooling, it is finely pulverized using an air jet type pulverizer, and then classified by air to
Particles of 20ÎŒ were selected and used as toner. The toner melt index is under the conditions of 125â and 10Kg.
It was 1.36g/10min. 0.5 parts by weight of hydrophobic colloidal silica was externally added to 100 parts by weight of this toner to form a developer, and evaluated using a commercially available copying machine (trade name, NP-400RE manufactured by Canon Inc.). The minimum fixing temperature of the above developer is 150â, and the offset phenomenon is 150â.
It was not observed from â to 210â.
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é¡ã¯çºçããªãã€ãã Furthermore, we set the temperature of the fixing roller to 170°C and conducted a continuous durability test of 50,000 sheets, but the image reflection density remained stable from the initial stage to after 50,000 sheets, staying around 1.0. Maintained. Even after 50,000 sheets were printed, there was no offset phenomenon to the fixing roller, and no problems such as adhesion to the surface of the photoreceptor drum or agglomeration within the developing device occurred.
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ãšããã[Comparative Example 1] A toner was prepared and used as a developer in the same manner as in Example 1 except that Nymeen S-202 was not added.
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ãã16.86ïœïŒ10minïŒã§ãã€ãã Melt index of this toner (125â, 10
Kg) was approximately equal to the value of the copolymer for toner material, which was 16.86 g/10 min).
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ããšç»åã®è·¡ãèªãããããŸã§ã«ãªã€ãã The minimum fixing temperature was 150°C, which was the same as the toner of Example 1, but as the temperature increased, the offset became more severe, and at 180°C, permanent image marks were observed on the surface of the fixing roller. .
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ãã¹ããäžæ¢ããã A continuous durability test was conducted in the same manner as in Example 1, but after about 500 copies, traces of the offset material retransferred from the fixing roller appeared on the image, which became even more severe after 1000 copies, so the durability test was discontinued.
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ãã[Example 2] Styrene-butyl acrylate-acrylic acid copolymer (monomer ratio: 80:18:2, Mw/Mn=19,
Mw=188000) 100 parts by weight, Naimeen T 2 â260
(polyoxyethylene tallow alkylamine commercially available from NOF Corporation, x+y=60) 0.5 parts by weight, 60 parts by weight of magnetite, 4 parts by weight of the metal complex dye of Example 1, polyethylene wax (with a melt viscosity of 2 parts by weight (120 centipoise at 140° C.) was prepared into a toner in the same manner as in Example 1 and evaluated. A toner with excellent offset resistance and stable developability was obtained.
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æããŠããã[Example 3] Styrene-butyl acrylate-methacrylic acid copolymer (monomer ratio: 75:15:10, Mw=
310000, Mw/Mn=28) 100 parts by weight, polyoxyethylene octadecylamine (x+y=10) 0.2
A toner prepared in substantially the same manner as in Example 1 using 60 parts by weight of magnetite and 4 parts by weight of the metal complex dye of Example 1 had good fixing properties and stable durability.
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ããã[Example 4] Styrene-butyl methacrylate-monobutyl maleate copolymer (monomer ratio: 70:15:15,
Mw=115000, Mw/Mn=8) 100 parts by weight, Naimeen S-220 (ethylene oxide derivative of octadecylamine manufactured by NOF Corporation, x+y=20) 1
Parts by weight, 8 parts by weight of carbon black, and 4 parts by weight of the metal complex dye of Example 1 were melt-kneaded in a small pressure kneader. After cooling, finely pulverize to approximately 5-20Ό
The particles were selected and used as toner. 10 parts by weight of this toner and carrier iron powder (product name: EFV250/400,
(manufactured by Nippon Tetsuko Co., Ltd.) was mixed with 90 parts by weight to prepare a developer. This developer is applied to a commercially available copying machine (product name: NP-
5000, manufactured by Canon Inc.), it was fixed at 150°C and no offset was observed at temperatures above 200°C. It also had excellent durability.
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MwïŒçŽ230000ïŒã調補ããã[Comparative Example 2] Styrene-butyl methacrylate having no carboxyl group was produced in the same manner as in Example 1 except that 80 parts by weight of styrene, 20 parts by weight of butyl methacrylate and 0.5 parts by weight of divinylbenzene were used. Divinylbenzene copolymer (Mw/Mn=approx. 22,
Mw=about 230000) was prepared.
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ããŒãšåæ§ã§ãã€ããã枩床180âã§ãªãã»ãã
çŸè±¡ãæçœã«çºçŸããã A toner (melt index: approximately 18 g/10 min under the conditions of 125° C. and 10 kg) was prepared in the same manner as in Example 1, except that the prepared styrene-butyl methacrylate-divinylbenzene copolymer was used. A fixing test was conducted in the same manner as in Example 1. The minimum fixing temperature was 150°C, which was the same as the toner of Example 1, but the offset phenomenon clearly appeared at a temperature of 180°C.
Claims (1)
ïŒMnïŒã®æ¯ïŒMwïŒMnïŒãïŒãã倧ãããMw
ã100000ãã倧ããã«ã«ããã·ã«åºãæãããã
ã«ç³»éåäœã次åŒã§ç€ºãããã¢ãã³ã§æ¶æ©ããé
åäœãå«æããéé»è·åçŸåçšãããŒã ãåŒäžãïœãšïœã¯ããããïŒãïŒã®æŽæ°ãïœãš
ïœã¯ããããïŒã50ã®æŽæ°ãã¯ïŒã30ã®ççŽ å
åããæãã¢ã«ãã«åºïŒäœããæåããåã³ã·ã¯
ãã¢ã«ãã«åºãå«ãïŒã瀺ããã ïŒ è©²ããã«ç³»éåäœã®MwïŒMnãïŒä»¥äžã§ã
ãç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé ã®éé»è·åçŸåçšãã
ãŒã ïŒ è©²ããã«ç³»éåäœããæ¶æ©ãããããã«ç³»é
åäœã§ããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé ãŸãã¯ç¬¬ïŒé ã®
éé»è·åçŸåçšãããŒã[Claims] 1. The ratio of weight average molecular weight (Mw) to number average molecular weight (Mn) (Mw/Mn) is greater than 4, and Mw
A toner for developing electrostatic images containing a vinyl polymer having a carboxyl group having a carboxyl group of greater than 100,000 and crosslinked with an amine represented by the following formula. [In the formula, a and b are each an integer of 2 to 4, x and y are each an integer of 1 to 50, and R is an alkyl group (including branched and cycloalkyl groups) consisting of 8 to 30 carbon atoms. show. 2. The toner for developing electrostatic images according to claim 1, wherein the vinyl polymer has a Mw/Mn of 8 or more. 3. The toner for developing an electrostatic image according to claim 1 or 2, wherein the vinyl polymer is a crosslinked vinyl polymer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57056961A JPS58173756A (en) | 1982-04-06 | 1982-04-06 | Toner |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57056961A JPS58173756A (en) | 1982-04-06 | 1982-04-06 | Toner |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58173756A JPS58173756A (en) | 1983-10-12 |
| JPH0425535B2 true JPH0425535B2 (en) | 1992-05-01 |
Family
ID=13042125
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57056961A Granted JPS58173756A (en) | 1982-04-06 | 1982-04-06 | Toner |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58173756A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0428186B1 (en) * | 1985-03-29 | 1995-01-18 | Komatsu Zenoah Co. | Portable engine unit |
| US5389484A (en) * | 1991-04-16 | 1995-02-14 | Canon Kabushiki Kaisha | Toner for developing electrostatic images, image forming apparatus, apparatus unit and facsimile apparatus |
-
1982
- 1982-04-06 JP JP57056961A patent/JPS58173756A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58173756A (en) | 1983-10-12 |
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