CN113703296B - Toner and preparation method thereof - Google Patents
Toner and preparation method thereof Download PDFInfo
- Publication number
- CN113703296B CN113703296B CN202110998940.4A CN202110998940A CN113703296B CN 113703296 B CN113703296 B CN 113703296B CN 202110998940 A CN202110998940 A CN 202110998940A CN 113703296 B CN113703296 B CN 113703296B
- Authority
- CN
- China
- Prior art keywords
- acid
- toner
- dithiol
- polyester resin
- hours
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 238000002360 preparation method Methods 0.000 title abstract description 23
- 229920001225 polyester resin Polymers 0.000 claims abstract description 82
- 239000004645 polyester resin Substances 0.000 claims abstract description 82
- 238000000034 method Methods 0.000 claims abstract description 22
- 125000003118 aryl group Chemical group 0.000 claims abstract description 19
- 150000004662 dithiols Chemical class 0.000 claims abstract description 19
- 239000002245 particle Substances 0.000 claims description 56
- 239000006185 dispersion Substances 0.000 claims description 53
- -1 carboxylic acid compounds Chemical class 0.000 claims description 51
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 44
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 44
- 239000007788 liquid Substances 0.000 claims description 43
- 238000001816 cooling Methods 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 36
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 34
- 229920005989 resin Polymers 0.000 claims description 28
- 239000011347 resin Substances 0.000 claims description 28
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 26
- WPSWDCBWMRJJED-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol;oxirane Chemical compound C1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 WPSWDCBWMRJJED-UHFFFAOYSA-N 0.000 claims description 25
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 25
- 239000000839 emulsion Substances 0.000 claims description 24
- 230000003647 oxidation Effects 0.000 claims description 23
- 238000007254 oxidation reaction Methods 0.000 claims description 23
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 22
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 22
- 239000001530 fumaric acid Substances 0.000 claims description 22
- 238000010438 heat treatment Methods 0.000 claims description 22
- 239000007787 solid Substances 0.000 claims description 21
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 20
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 claims description 20
- 230000009471 action Effects 0.000 claims description 19
- 239000003086 colorant Substances 0.000 claims description 19
- 238000001035 drying Methods 0.000 claims description 19
- 230000001105 regulatory effect Effects 0.000 claims description 19
- 238000005406 washing Methods 0.000 claims description 19
- JRNVQLOKVMWBFR-UHFFFAOYSA-N 1,2-benzenedithiol Chemical compound SC1=CC=CC=C1S JRNVQLOKVMWBFR-UHFFFAOYSA-N 0.000 claims description 18
- UOQACRNTVQWTFF-UHFFFAOYSA-N decane-1,10-dithiol Chemical compound SCCCCCCCCCCS UOQACRNTVQWTFF-UHFFFAOYSA-N 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 17
- 238000003756 stirring Methods 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000000654 additive Substances 0.000 claims description 12
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 11
- 150000002009 diols Chemical class 0.000 claims description 10
- 230000000996 additive effect Effects 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 claims description 8
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 claims description 8
- 238000009775 high-speed stirring Methods 0.000 claims description 8
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 8
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 8
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 8
- XSMIOONHPKRREI-UHFFFAOYSA-N undecane-1,11-diol Chemical compound OCCCCCCCCCCCO XSMIOONHPKRREI-UHFFFAOYSA-N 0.000 claims description 8
- SRZXCOWFGPICGA-UHFFFAOYSA-N 1,6-Hexanedithiol Chemical compound SCCCCCCS SRZXCOWFGPICGA-UHFFFAOYSA-N 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000003505 polymerization initiator Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims description 6
- 239000003125 aqueous solvent Substances 0.000 claims description 5
- 230000001276 controlling effect Effects 0.000 claims description 5
- PGTWZHXOSWQKCY-UHFFFAOYSA-N 1,8-Octanedithiol Chemical compound SCCCCCCCCS PGTWZHXOSWQKCY-UHFFFAOYSA-N 0.000 claims description 4
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 claims description 4
- GJRCLMJHPWCJEI-UHFFFAOYSA-N 1,9-Nonanedithiol Chemical compound SCCCCCCCCCS GJRCLMJHPWCJEI-UHFFFAOYSA-N 0.000 claims description 4
- QPGBFKDHRXJSIK-UHFFFAOYSA-N 2-tert-butylbenzene-1,3-dicarboxylic acid Chemical compound CC(C)(C)C1=C(C(O)=O)C=CC=C1C(O)=O QPGBFKDHRXJSIK-UHFFFAOYSA-N 0.000 claims description 4
- 239000001361 adipic acid Substances 0.000 claims description 4
- 235000011037 adipic acid Nutrition 0.000 claims description 4
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 claims description 4
- 229940018557 citraconic acid Drugs 0.000 claims description 4
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 claims description 4
- SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 claims description 4
- RVVRZLSZZKMJCB-UHFFFAOYSA-N heptane-1,7-dithiol Chemical compound SCCCCCCCS RVVRZLSZZKMJCB-UHFFFAOYSA-N 0.000 claims description 4
- 230000002209 hydrophobic effect Effects 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- 239000011976 maleic acid Substances 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 claims description 4
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 claims description 3
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 claims description 3
- VPPWQRIBARKZNY-UHFFFAOYSA-N oxo(diphenyl)tin Chemical compound C=1C=CC=CC=1[Sn](=O)C1=CC=CC=C1 VPPWQRIBARKZNY-UHFFFAOYSA-N 0.000 claims description 3
- XTTBFCWRLDKOQU-UHFFFAOYSA-N propan-1-ol;titanium Chemical compound [Ti].CCCO.CCCO.CCCO.CCCO XTTBFCWRLDKOQU-UHFFFAOYSA-N 0.000 claims description 3
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 claims description 3
- 238000004945 emulsification Methods 0.000 abstract description 6
- 238000011161 development Methods 0.000 abstract description 4
- 238000005886 esterification reaction Methods 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- 239000001993 wax Substances 0.000 description 19
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 18
- 239000006229 carbon black Substances 0.000 description 17
- 239000004203 carnauba wax Substances 0.000 description 17
- 235000013869 carnauba wax Nutrition 0.000 description 17
- 239000012299 nitrogen atmosphere Substances 0.000 description 15
- 238000006068 polycondensation reaction Methods 0.000 description 13
- 239000002253 acid Substances 0.000 description 9
- 239000000178 monomer Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 8
- 238000003860 storage Methods 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- 230000001186 cumulative effect Effects 0.000 description 4
- 239000006249 magnetic particle Substances 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 3
- 229920006125 amorphous polymer Polymers 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 3
- XJWSAJYUBXQQDR-UHFFFAOYSA-M dodecyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)C XJWSAJYUBXQQDR-UHFFFAOYSA-M 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
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- 238000012360 testing method Methods 0.000 description 3
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 2
- VEUMANXWQDHAJV-UHFFFAOYSA-N 2-[2-[(2-hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCN=CC1=CC=CC=C1O VEUMANXWQDHAJV-UHFFFAOYSA-N 0.000 description 2
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- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
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- RIPYNJLMMFGZSX-UHFFFAOYSA-N (5-benzoylperoxy-2,5-dimethylhexan-2-yl) benzenecarboperoxoate Chemical compound C=1C=CC=CC=1C(=O)OOC(C)(C)CCC(C)(C)OOC(=O)C1=CC=CC=C1 RIPYNJLMMFGZSX-UHFFFAOYSA-N 0.000 description 1
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- UBRWPVTUQDJKCC-UHFFFAOYSA-N 1,3-bis(2-tert-butylperoxypropan-2-yl)benzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC(C(C)(C)OOC(C)(C)C)=C1 UBRWPVTUQDJKCC-UHFFFAOYSA-N 0.000 description 1
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
- AVWNSSLPOWEOLS-UHFFFAOYSA-N 1,4-bis(tert-butylperoxy)cyclohexane Chemical compound CC(C)(C)OOC1CCC(OOC(C)(C)C)CC1 AVWNSSLPOWEOLS-UHFFFAOYSA-N 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
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- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000004200 microcrystalline wax Substances 0.000 description 1
- 235000019808 microcrystalline wax Nutrition 0.000 description 1
- 239000012184 mineral wax Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000012170 montan wax Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- MZYHMUONCNKCHE-UHFFFAOYSA-N naphthalene-1,2,3,4-tetracarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=C(C(O)=O)C(C(O)=O)=C21 MZYHMUONCNKCHE-UHFFFAOYSA-N 0.000 description 1
- KVQQRFDIKYXJTJ-UHFFFAOYSA-N naphthalene-1,2,3-tricarboxylic acid Chemical compound C1=CC=C2C(C(O)=O)=C(C(O)=O)C(C(=O)O)=CC2=C1 KVQQRFDIKYXJTJ-UHFFFAOYSA-N 0.000 description 1
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- SRSFOMHQIATOFV-UHFFFAOYSA-N octanoyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(=O)CCCCCCC SRSFOMHQIATOFV-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000012736 patent blue V Nutrition 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000012169 petroleum derived wax Substances 0.000 description 1
- 235000019381 petroleum wax Nutrition 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920000867 polyelectrolyte Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- JEVOQXUAWFYIBD-UHFFFAOYSA-N pyrene-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(O)=O)=C2C(C(=O)O)=CC3=CC=CC4=CC=C1C2=C34 JEVOQXUAWFYIBD-UHFFFAOYSA-N 0.000 description 1
- LGZHPCIDRRUTMI-UHFFFAOYSA-N pyrene-1,2,3-tricarboxylic acid Chemical compound C1=CC=C2C=CC3=C(C(O)=O)C(C(=O)O)=C(C(O)=O)C4=CC=C1C2=C43 LGZHPCIDRRUTMI-UHFFFAOYSA-N 0.000 description 1
- 235000012752 quinoline yellow Nutrition 0.000 description 1
- 229940051201 quinoline yellow Drugs 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 239000004172 quinoline yellow Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 239000004170 rice bran wax Substances 0.000 description 1
- 235000019384 rice bran wax Nutrition 0.000 description 1
- 102220308083 rs1462326368 Human genes 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229940116353 sebacic acid Drugs 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- VVNRQZDDMYBBJY-UHFFFAOYSA-M sodium 1-[(1-sulfonaphthalen-2-yl)diazenyl]naphthalen-2-olate Chemical compound [Na+].C1=CC=CC2=C(S([O-])(=O)=O)C(N=NC3=C4C=CC=CC4=CC=C3O)=CC=C21 VVNRQZDDMYBBJY-UHFFFAOYSA-M 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- VEALVRVVWBQVSL-UHFFFAOYSA-N strontium titanate Chemical compound [Sr+2].[O-][Ti]([O-])=O VEALVRVVWBQVSL-UHFFFAOYSA-N 0.000 description 1
- 229920005792 styrene-acrylic resin Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- VEQHTYHLJYNSTG-UHFFFAOYSA-N tert-butyl 9-tert-butylperoxy-9-oxononanoate Chemical compound CC(C)(C)OOC(=O)CCCCCCCC(=O)OC(C)(C)C VEQHTYHLJYNSTG-UHFFFAOYSA-N 0.000 description 1
- DIUUHGMNFWMWFB-UHFFFAOYSA-N tert-butylperoxy hydrogen carbonate Chemical compound CC(C)(C)OOOC(O)=O DIUUHGMNFWMWFB-UHFFFAOYSA-N 0.000 description 1
- GSECCTDWEGTEBD-UHFFFAOYSA-N tert-butylperoxycyclohexane Chemical compound CC(C)(C)OOC1CCCCC1 GSECCTDWEGTEBD-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- FRNOGLGSGLTDKL-UHFFFAOYSA-N thulium atom Chemical compound [Tm] FRNOGLGSGLTDKL-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- 150000008648 triflates Chemical class 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- WCAGGTLUGWSHOV-UHFFFAOYSA-N tris(tert-butylperoxy)-ethenylsilane Chemical compound CC(C)(C)OO[Si](OOC(C)(C)C)(OOC(C)(C)C)C=C WCAGGTLUGWSHOV-UHFFFAOYSA-N 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- UGCDBQWJXSAYIL-UHFFFAOYSA-N vat blue 6 Chemical compound O=C1C2=CC=CC=C2C(=O)C(C=C2Cl)=C1C1=C2NC2=C(C(=O)C=3C(=CC=CC=3)C3=O)C3=CC(Cl)=C2N1 UGCDBQWJXSAYIL-UHFFFAOYSA-N 0.000 description 1
- 239000012178 vegetable wax Substances 0.000 description 1
- JEVGKYBUANQAKG-UHFFFAOYSA-N victoria blue R Chemical compound [Cl-].C12=CC=CC=C2C(=[NH+]CC)C=CC1=C(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 JEVGKYBUANQAKG-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XOSXWYQMOYSSKB-LDKJGXKFSA-L water blue Chemical compound CC1=CC(/C(\C(C=C2)=CC=C2NC(C=C2)=CC=C2S([O-])(=O)=O)=C(\C=C2)/C=C/C\2=N\C(C=C2)=CC=C2S([O-])(=O)=O)=CC(S(O)(=O)=O)=C1N.[Na+].[Na+] XOSXWYQMOYSSKB-LDKJGXKFSA-L 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 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
- G03G9/08742—Binders for toner particles comprising macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- G03G9/08755—Polyesters
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/0802—Preparation methods
- G03G9/0804—Preparation methods whereby the components are brought together in a liquid dispersing medium
- G03G9/0806—Preparation methods whereby the components are brought together in a liquid dispersing medium whereby chemical synthesis of at least one of the toner components takes place
-
- 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
- G03G9/0819—Developers with toner particles characterised by the dimensions of the particles
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/0827—Developers with toner particles characterised by their shape, e.g. degree of sphericity
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Developing Agents For Electrophotography (AREA)
Abstract
The invention discloses a toner and a preparation method thereof, wherein an aromatic diacid and dithiol are subjected to esterification reaction, a novel polyester resin is prepared through an emulsification method, and the toner prepared from the polyester resin has excellent development characteristics, not only ensures the low-temperature fixability of the toner, but also is not easy to deviate under high-temperature conditions, is uniformly charged at the initial stage and after a period of charging, has excellent image quality of printing and good storability, not only improves the printing and copying quality, but also reduces the pollution to the environment.
Description
Technical Field
The invention belongs to the technical field of toners, and particularly relates to a toner and a preparation method thereof.
Background
In recent years, there has been an increasing demand for higher speeds, energy saving, miniaturization, and the like of printers and copiers, and further improvement in low-temperature fixability of toners has been demanded. Styrene-acrylic resins have been widely used as binder resin toners in the past, but they have a great limitation in meeting the energy saving for image formation, high gloss image quality, and especially in low temperature fixing. Thus, the development of a toner using a polyester resin as a binder resin has been accelerated, and the development of a new generation of toners for printing and copying has been promoted.
With the application of polyester resin as adhesive resin toner in high-speed printers and copiers, the resin with excellent low-temperature fixability and high-gloss polyester resin structure is called as the main stream of toner, while the polyester structure can ensure the low-temperature fixability of the toner, offset phenomenon is easy to occur under high-temperature conditions, uneven belt points are easy to occur at the initial stage of charging and after a period of time, and the problems of poor image quality, easy caking during storage and the like are caused; the preparation method generally adopts the conventional methods such as a phase transition emulsification method, a self-emulsification method and the like, but a large amount of organic solvent or a certain amount of surfactant or groups which are not effective for printing are used when the resin particles are dispersed in water, and the substances can have potential adverse effects on the quality and the environment of printing.
Disclosure of Invention
The present invention is directed to the above-mentioned problems, and provides a toner and a method for producing the toner, which are characterized in that a dithiol monomer is selected to be combined with other various glycol monomers and then is polymerized with an aromatic dicarboxylic acid monomer, thereby producing a toner having uniform and concentrated toner particle diameter, high sphericity, and good developing and preserving properties.
The first aspect of the present invention provides a toner comprising a polyester resin, a colorant, a wax, and an external additive;
the polyester resin is prepared by reacting carboxylic acid compounds, alcohol compounds and a catalyst under certain conditions, wherein the alcohol compounds comprise dithiol.
Further, the dithiol comprises one or more combinations of the following compounds: benzene dithiol, 1, 6-hexane dithiol, 1, 7-heptane dithiol, 1, 8-octane dithiol, 1, 9-nonane dithiol, 1, 10-decane dithiol, n-undecyl mercaptan, n-dodecyl mercaptan.
Further, the carboxylic acid compound comprises one or more of aromatic diacid, aliphatic diacid and trimellitic anhydride; the alcohol compound comprises one or more of bisphenol A ethylene oxide adduct, butanediol and diol with 6-12 carbon atoms.
Further, the aromatic diacid comprises one or more combinations of phthalic acid, isophthalic acid, terephthalic acid, tertiary butyl isophthalic acid, 2, 6-naphthalene dicarboxylic acid, 4' -biphenyl dicarboxylic acid;
further, the aliphatic diacid comprises one or more combinations of succinic acid, adipic acid, sebacic acid, fumaric acid, maleic acid, citraconic acid;
Further, the diol with the carbon number of 6-12 comprises one or more of 1, 6-hexanediol, 1, 7-heptanediol, 1, 8-octanediol, 1, 9-nonanediol, 1, 10-decanediol, 1, 11-undecanediol and 1, 12-dodecanediol;
preferably, the aromatic diacid is terephthalic acid, the aliphatic diacid is fumaric acid and/or succinic acid, and the diol having 6 to 12 carbon atoms is 1, 6-hexanediol.
Further, the dithiol accounts for 11.0 to 16.5mol% of the alcohol compound, the bisphenol A ethylene oxide adduct accounts for 40 to 65mol% of the alcohol compound, and the aromatic diacid accounts for 25 to 40mol% of the carboxylic acid compound.
A second aspect of the present invention provides a method for producing a toner, comprising the steps of:
s1: adding carboxylic acid compounds, alcohol compounds and catalysts into a reaction vessel, and stirring and reacting for 5-8 hours at 70-150 ℃ under the protection of nitrogen to obtain polyester resin;
s2: dispersing the prepared polyester resin for 3-5 min under a homogenizer, adding an aqueous solvent, controlling the solid content to be 10-18%, adding mPEG-SH and/or HS-PEG-SH, reacting by an air oxidation method or a potassium ferricyanide oxidation method, and obtaining a resin emulsion of 100-200 nm after high-speed stirring and dispersing;
S3: adding colorant dispersion liquid and wax dispersion liquid into the resin emulsion, regulating the pH to 5.5-7 under the action of a polymerization initiator, slowly heating to 70-85 ℃, keeping the temperature for 1-2 hours, then cooling to 50-65 ℃, keeping the temperature for 2-3 hours, cooling to room temperature, washing and drying to obtain carbon powder parent particles, and adding the hydrophobic silica particles as an external additive to obtain the toner.
Further, the catalyst comprises one or more of titanium tetraethoxide, titanium tetrapropanol, titanium tetraisopropoxide, titanium tetrabutoxide, dibutyl tin dichloride, dibutyl tin oxide and diphenyl tin oxide, wherein the catalyst accounts for 0.1-0.5 mol% of the total material amount.
Further, the rotational speed of the homogenizer is 3000-5000 rpm.
Further, the toner has an average particle diameter of 4.5 to 8.5 μm, a particle diameter dispersity of 1.10 to 1.32, and a sphericity of 0.96 to 0.98
The beneficial effects are that:
according to the invention, the aromatic diacid and dithiol are subjected to esterification reaction, mercapto and sulfur atoms are introduced into the polyester resin, the introduction of the mercapto can effectively replace the addition of a surfactant in the traditional polyester resin preparation process, and the introduction of the sulfur atoms can effectively form hydrogen bonds with silicon dioxide, so that the silicon dioxide is more firmly fixed on the surface of the polyester resin, thereby reducing the burial of the silicon dioxide and improving the storage performance of the toner; the toner prepared by the method shows better color density and good storage characteristic, and from the practical printing evaluation effect, the toner prepared by the polyester resin has good image quality and still keeps higher stability after printing a large number of pages.
Detailed Description
Embodiments of the present invention will be described in detail below with reference to examples, but it will be understood by those skilled in the art that the following examples are only for illustrating the present invention and should not be construed as limiting the scope of the present invention. The specific conditions are not identified in the examples and are carried out under conventional conditions or under conditions recommended by the manufacturer. The reagents or apparatus used are not manufacturer specific and are commercially available as conventional products.
It should be noted that:
in the present invention, all embodiments and preferred methods mentioned herein may be combined with each other to form new technical solutions, unless otherwise specified.
In the present invention, unless otherwise specified, the resin ranges "a-b" represent a shorthand representation of any combination of real numbers between a and b, where a and b are both real numbers, e.g., the numerical ranges "25-40" represent all real numbers between 25-40 that have been fully listed herein, and "25-40" is a shorthand representation of such combinations of values.
In the present invention, each reaction or operation step may be performed sequentially or in other order unless otherwise indicated, and preferably, the present invention is performed sequentially.
Unless otherwise defined, the technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art, and further any methods or materials similar or equivalent to those described may be used in the present invention.
Method for preparing toner
The emulsification method used in the invention comprises the following steps:
< polyester Synthesis >
Adding carboxylic acid compounds, alcohol compounds and catalyst into a reaction vessel, stirring and reacting for 5-8h at 70-150 ℃ under the protection of nitrogen to obtain polyester resin
In the present invention, the polycondensation reaction of the polyester resin is performed at a temperature of 150℃or lower.
The reaction temperature is preferably greater than or equal to 70 ℃, but not greater than 150 ℃; more preferably 110℃or higher, but not more than 140 ℃.
The reaction temperature is preferably set to 70℃or higher, because such a decrease in reactivity due to deterioration in monomer solubility or catalyst activity does not occur and an increase in molecular weight is not suppressed. It is also preferable to set the reaction temperature to not more than 150℃because this allows production with low energy consumption. It is also preferable that no discoloration of the resin or decomposition occur on the produced polyester or the like.
< emulsification step >
Dispersing the prepared polyester resin for 3-5 min under a homogenizer, adding an aqueous solvent, controlling the solid content to be 10-18%, adding mPEG-SH and/or HS-PEG-SH, reacting by an air oxidation method or a potassium ferricyanide oxidation method, and obtaining 100-200 nm resin emulsion after telling, stirring and dispersing;
examples of the aqueous solvent include: water and alcohols such as distilled water and ion-exchanged water. Particularly preferably, the water-soluble solvent is water alone.
Among them, as dispersing equipment used in the emulsification step, there may be mentioned homogenizers, pressure kneaders, extruders and medium dispersers, and it is particularly preferable to use homogenizers, wherein the rotation speed of the homogenizers is particularly preferably 3000 to 5000rpm; for the polyester resin particle size, the average particle diameter (volume average particle diameter) thereof is preferably 1 μm or less, more preferably 50 to 300nm, particularly preferably 100 to 200nm, and when the average particle diameter is less than 50nm, the polyester resin particles become stable particles in the dispersion, and are hard to agglomerate together, and when the average particle diameter exceeds 1 μm, the agglomeration potential of the resin particles is enhanced so that the toner particles are more easily produced, but the particle diameter distribution is enlarged.
Wherein mPEG-SH is methoxy polyethylene glycol mercaptan, HS-PEG-SH is dimercapto polyethylene glycol, and the molecular weight of the two substances can be listed as follows: 550 Particularly preferred molecular weights are one or a combination of 1000 and 2000, 750, 1000, 2000, 3400, 5000, 10k,20k,40 k.
< toner combination >
Adding pigment dispersion liquid and wax dispersion liquid into the resin emulsion, regulating the pH to 5.5-7 under the action of potassium persulfate or ammonium persulfate, slowly heating to 70-85 ℃, keeping the temperature for 1-2 hours, then cooling to 50-65 ℃, keeping the temperature for 2-3 hours, cooling to room temperature, washing and drying to obtain carbon powder parent particles, and adding the hydrophobic silica particles as an external additive to obtain the toner.
The volume average particle diameter of the toner in the present invention is preferably 4 μm or 4 μm to 9 μm or about 9 μm, more preferably 4.5 μm or 4.5 μm to 8.5 μm or about 8.5 μm, particularly preferably 5 μm or 5 μm to 8 μm or about 8 μm, when the volume average particle diameter is less than 4 μm, the fluidity of the toner is lowered, which is liable to be degraded due to the chargeability of each particle per day, background fogging and toner leakage from the developing vessel are liable to occur due to charge distribution diffusion, and furthermore when the volume average particle diameter is less than 4 μm, the cleanability may sometimes be deteriorated, and when the volume average particle diameter exceeds 9 μm, the resolution is lowered, and thus sufficient image quality may not be obtained, and therefore, it is sometimes difficult to satisfy recent demands for high image quality.
Alternatively in the present invention, the volume average particle diameter is measured at a pore diameter of 50 μm using a Coulter Multi-sizer II (trade name, manufactured by Coulter Company), in which case the toner is dispersed in an aqueous electrolyte solution (an aqueous Isoton solution) by ultrasonic treatment for 30 seconds or more, and then used for measurement. The cumulative distribution of volumes is plotted from small particle sizes, with 50% cumulative particle size defined as the volume average particle size, plotted as a function of the measured force division and the partitioned particle size range.
The average particle size distribution index in the present invention, that is, the particle size dispersity of the toner, can be calculated using these values, with the particle size up to 16% cumulative being defined as the particle size corresponding to the volume D16V and the number D16P, and the particle size up to 84% cumulative being defined as the particle size corresponding to the volume D84V and the number D84P, and the particle size dispersity in the present invention is preferably 1.10 to 1.32.
In addition, the sphericity of the toner in the present invention is 0.96 to 0.98.
Polyester resin
The polyester resins useful in the present invention can be prepared in an aqueous medium by direct esterification reaction, transesterification reaction, etc. using polycondensable monomers such as aliphatic, alicyclic and aromatic polyfunctional carboxylic acids, alkyl esters and polyols, ester compounds thereof, hydroxycarboxylic groups, etc.
In the invention, the polyester resin is preferably prepared by directly esterifying carboxylic acid compounds and alcohol compounds under the condition of a catalyst.
In the present invention, the molecular weight of the polyester resin is 5,000-1,000,000, more optionally the weight average molecular weight (Mw) is 7000 to 500,000, the number average molecular weight (Mn) is optionally 2,000 to 10,000, and the high molecular weight distribution Mw/Mn is optionally 1.5 to 100, further optionally 2 to 60, based on the molecular weight of Tetrahydrofuran (THF) soluble matter measured by Gel Permeation Chromatography (GPC), and the molecular weight of the resin is calculated by measuring the molecular weight of THF soluble matter in THF solution using GPC HLC-8120 (manufactured by Tosoh Corporation) and column TSK gel super HM-M (15 cm) (manufactured by Tosohcorcorporation), and using a molecular weight calibration curve generated from a monodisperse polystyrene standard sample. The acid value of the polyester resin (in terms of the amount of KOH required to neutralize 1g of the resin) may be selected to be 1 to 30mg KOH/g, the granulation property of the toner particles is easily maintained in the emulsion dispersion method, and the favorable environmental stability (stability of chargeability upon temperature or humidity change) of the obtained toner is easily maintained, for the reason that the above molecular weight distribution is easily obtained. The acid value of the polyester resin can be adjusted by controlling the carboxyl groups at the end of the polyester, i.e., adjusting the mixing ratio and reaction rate of the polycarboxylic acid and the polyol in the raw material.
In addition, from the viewpoint of balance of storage stability and fixability of the toner, the glass transition temperature of the amorphous polymer usable in this embodiment may be selected to be 35 to 100 ℃, more preferably 50 to 80 ℃. When the glass transition temperature is lower than 35 ℃, there is a tendency that the toner tends to cause clogging (phenomenon in which toner particles aggregate to form agglomerates) during storage or in a developing machine. On the other hand, when the glass transition temperature exceeds 100 ℃, the fixing temperature of the toner becomes high, which is not optional. The softening point of the amorphous polymer may be selected in the range of 80-130 c, more preferably in the range of 90-120 c. When the softening point is less than 80 ℃, the image stability of the toner and the toner after fixing and after storage is drastically deteriorated. When the softening point is higher than 130 ℃, the low-temperature fixability is deteriorated. The softening point of the amorphous polymer is shown by the flow tester (trade name CFT-500C; manufactured by Shimadzu Corporation) after preheating: intermediate temperature between melting onset temperature and melting termination temperature measured at 80 ℃/300 seconds, plunger pressure: 0.980665MPa, die size: heating rate: 3.0 ℃/min.
Carboxylic acid compounds
In the polyester used in the present invention, the polyfunctional carboxylic acid used as the polycondensation monomer includes compounds having two or more carboxyl groups in a single molecule, in which dicarboxylic acid contains two carboxyl groups in one molecule, the carboxylic acid-based compound of the present invention contains an aromatic diacid, an aliphatic diacid, and a polyfunctional carboxylic acid, examples of which include oxalic acid, glutaric acid, succinic acid, maleic acid, adipic acid, β -methyladipic acid, azelaic acid, sebacic acid, nonanedioic acid, decane diacid, undecanedioic acid, dodecanedioic acid, fumaric acid, citraconic acid, diglycolic acid, cyclohexane-3, 5-diene-1, 2-carboxylic acid, malic acid, citric acid, hexahydroterephthalic acid, malonic acid, pimelic acid, tartaric acid, mucic acid, phthalic acid, isophthalic acid, terephthalic acid, t-butylisophthalic acid, tetrachlorophthalic acid, chlorophthalic acid, nitrophthalic acid, terephthaloic acid, m-phenylene diacid, terephthaloyl diglycolic acid, terephthaloyl acid, diphenyldiglycolic acid, 4' -diphenyldicarboxylic acid, 4, 5-naphthalene dicarboxylic acid, 2, 6-naphthalene dicarboxylic acid, 2-naphthalene dicarboxylic acid, and the like; examples of the polyfunctional carboxylic acids other than dicarboxylic acids include trimellitic anhydride, pyromellitic acid, naphthalene tricarboxylic acid, naphthalene tetracarboxylic acid, pyrene tricarboxylic acid, pyrene tetracarboxylic acid, and the like.
Preferably, the aromatic diacid comprises one or more combinations of phthalic acid, isophthalic acid, terephthalic acid, t-butylisophthalic acid, 2, 6-naphthalene dicarboxylic acid, 4' -biphenyl dicarboxylic acid.
Preferably, the aliphatic diacid comprises one or more combinations of succinic acid, adipic acid, sebacic acid, fumaric acid, maleic acid, citraconic acid.
In view of the good non-crystalline nature of the polyester resin, it is particularly preferred that the aromatic diacid is terephthalic acid; the aliphatic diacid comprises one or a combination of fumaric acid and succinic acid, and the multifunctional carboxylic acid is trimellitic anhydride.
Alcohol compound
The alcohol compound in the present invention contains a polyhydric alcohol compound, that is, a compound having two or more hydroxyl groups in one molecule, and among them, a diol is a compound having two hydroxyl groups in one molecule, and examples thereof include, for example, ethylene glycol, propylene glycol, butylene glycol, diethylene glycol, cyclohexanediol, 1, 6-hexanediol, 1, 7-heptanediol, 1, 8-octanediol, 1, 9-nonanediol, 1, 10-decanediol, 1, 11-undecanediol, 1, 12-dodecanediol, and the like. Examples of the polyhydric alcohol other than glycol include glycerin, pentaerythritol, hexamethylol melamine, hexahydroxyethyl melamine, tetramethylol benzoguanamine, and tetraethylol benzoguanamine.
In view of easiness in production of the monomer having a main structural carbon number of 6 or more and suitability in molecular size of the monomer having a main structural carbon number of 12 or less and no decrease in reactivity due to restriction of molecular movement, the above alcohol compound preferably contains one or more of 1, 6-hexanediol, 1, 7-heptanediol, 1, 8-octanediol, 1, 9-nonanediol, 1, 10-decanediol, 1, 11-undecanediol, 1, 12-dodecanediol.
Particularly preferred is 1, 6-hexanediol as the diol having 6 to 12 carbon atoms.
The alcohol compound also comprises bisphenol A ethylene oxide addition product; wherein, the ethylene oxide addition product can effectively inhibit the delocalization effect generated by resonance stabilization between hydroxyl and aromatic rings in the bisphenol A structure, and can strengthen nucleophilic attack of diol to polycarboxylic acid after the ethylene oxide addition product is added, so that the molecular weight increase and the polymerization degree progress are kept at good levels.
In the present invention, the alcohol compound contains dithiol, which means a dithiol structure containing two mercapto functional groups in the molecule, and examples thereof include, for example, one or more of benzene dithiol, 1, 6-hexane dithiol, 1, 7-heptane dithiol, 1, 8-octane dithiol, 1, 9-nonandithiol, 1, 10-decanedithiol, n-undecyl mercaptan, n-dodecyl mercaptan.
Preferably, the dithiol comprises one or more combinations of 1, 10-decanedithiol, benzenedithiol, 1, 6-hexanedithiol, n-dodecyl mercaptan.
In view of the good non-crystalline characteristics of the polyester resin and the reduced odor of the toner itself, it is particularly preferred that the above dithiol is one or a combination of more of 1, 10-decanedithiol, benzenedithiol, 1, 6-hexanedithiol.
In addition, it has been found that the development property and the preservability can be more effectively improved by containing a small amount of butanediol or propylene glycol in the monomer of the alcohol compound, and it is particularly preferable that butanediol is further contained in the alcohol compound.
The above-mentioned amorphous property of the polyester resin is also referred to as amorphous polyester resin, and "crystalline" means: distinct endothermic peaks can be resolved by Differential Scanning Calorimeter (DSC), rather than gradual endothermic changes; more specifically, the half-width of the endothermic peak measured at a heating rate of 10 ℃ per minute was in the range of 15 ℃, whereas a resin having a half-width of the endothermic peak exceeding 15 ℃ or a resin having no significant endothermic peak was produced, indicating that it was amorphous (amorphous).
In the embodiment of the invention, dithiol accounts for 11.0-16.5 mol% of the alcohol compound, and preferable dithiol accounts for 13-15.5 mol% of the alcohol compound, and particularly preferable dithiol accounts for 14.5-15.5 mol% of the alcohol compound; bisphenol A ethylene oxide adduct accounts for 40 to 65mol% of the alcohol compound, preferably bisphenol A ethylene oxide adduct accounts for 44 to 64mol% of the alcohol compound, particularly preferably bisphenol A ethylene oxide adduct accounts for 44 to 49mol% or 60 to 64mol% of the alcohol compound; the aromatic diacid is 26 to 38mol% of the total carboxylic acid compound, preferably 30 to 38mol% of the total carboxylic acid compound, and particularly preferably 35 to 37mol% of the total carboxylic acid compound.
Catalyst
The catalyst in the present invention is an organometallic catalyst, non-limiting examples of which include: such as organotin compounds, organohalotin compounds, rare earth metal catalysts, and the like.
Specifically, scandium (Sc), yttrium (Y) are effective as rare earth metal-containing catalysts; lanthanoids such as lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu). These elements are particularly effective when used as alkylbenzene sulfonate, alkyl sulfate, triflate structures, and the like. Examples of triflates can be represented by structural formula X (OSO 2 CF 3 ) 3 In which X represents a rare earth metal element, and X is particularly preferably scandium (Sc), yttrium (Y), ytterbium (Yb), samarium (Sm), or the like.
Preferred in the embodiments of the present invention are one or a combination of organotin compounds and/or organotin compounds, wherein the organotin compounds comprise one or more combinations of titanium tetraethoxide, titanium tetrapropanol, titanium tetraisopropoxide and titanium tetrabutoxide, and wherein the organotin compounds comprise one or more combinations of dibutyltin dichloride, dibutyltin oxide and diphenyltin oxide.
Particularly preferably, the catalyst in the embodiment of the invention is dibutyl tin oxide, and the feeding amount of the dibutyl tin oxide accounts for 0.1 to 0.5mol percent of the total material amount.
Polymerization initiator
The polymerization initiator is added in the polymerization process of the present invention, and a known polymerization initiator, specifically, examples of the compound include ammonium persulfate, potassium persulfate, sodium persulfate, 2' -azobis (2-methylpropionamide) dihydrochloride, t-butyl peroxy-2-ethylhexanoate, cumyl perpivalate, t-butyl peroxylaurate, benzoyl peroxide, lauroyl peroxide, octanoyl peroxide, di-t-butyl peroxide, t-butylcumyl peroxide, dicumyl peroxide, 2' -azobisisobutyronitrile, 2' -azobis (2-methylbutyronitrile), 2' -azobis (2, 4-dimethylpentanenitrile), and 2,2' -azobis (4-methoxy-2, 4-dimethylvaleronitrile), 1-bis (t-butylperoxy) -3, 5-trimethylcyclohexane, 1-bis (t-butylperoxy) cyclohexane, 1, 4-bis (t-butylperoxy) cyclohexane, 2-bis (t-butylperoxy) octane 4, 4-bis (tert-butylperoxyisopropyl) pentanoic acid (varylate) n-butyl, 2-bis (tert-butylperoxy) butane, 1, 3-bis (tert-butylperoxyisopropyl) benzene, 2, 5-dimethyl-2, 5-bis (tert-butylperoxy) hexane, 2, 5-dimethyl-2, 5-bis (benzoylperoxy) hexane, di-tert-butyl diperoxyphthalate, 2-bis (4, 4-di-tert-butylperoxycyclohexyl) propane, di-tert-butyl peroxy- α -methylsuccinate, di-tert-butyl peroxy-dimethylglutarate, di-tert-butyl peroxy-hexahydroterephthalate, di-tert-butyl peroxy-azelate, 2, 5-dimethyl-2, 5-bis (tert-butylperoxy) hexane, diethylene glycol-bis (tert-butylperoxy carbonate), di-tert-butyl peroxy-trimethyladipate, tris (tert-butylperoxy) triazine, vinyl-tris (tert-butylperoxy) silane, 2' -azobis (2-methylpropionamidine dihydrochloride), 2' -azobis [ N- (2-carboxyethyl) -2-methylpropionamidine ], 4' -azobis (4-cyanovaleric acid), and the like.
Particularly preferably, the polymerization initiator in the present invention comprises one or a combination of potassium persulfate or ammonium persulfate.
In the present invention, known additives alone or in combination of two or more kinds may be mixed as necessary as long as they do not affect the results of the present invention, and for example, flame retardants, flame retardant aids, polishing agents, water repellents, magnetic materials, inorganic fillers (surface modifiers), antioxidants, plasticizers, surfactants, dispersants, lubricants, fillers, pigments, binders, charge control agents, and the like may be added. These additives may be mixed at any time when the coating agent is manufactured.
Colorant dispersion
The colorant dispersion liquid contains a colorant, wherein the colorant dispersion liquid is prepared by dispersing and dissolving a colorant, and preferable examples of a device commonly used for dispersing the colorant include a medium type dispersing machine such as a rotary cutting type homogenizer, a ball mill, a sand mill or an attritor, and a high-pressure counter-collision type dispersing machine.
These colorants can be used to prepare colorant dispersions by dispersing these colorants in an aqueous solution using a homogenizer and an ionic surfactant having polarity.
The colorant may be selected from the viewpoints of hue angle, chromaticity, brightness, weather resistance, OHP permeability, and dispersibility in toner. The amount of the colorant added to the toner of the exemplary embodiment is preferably about 2 parts by mass to about 15 parts by mass with respect to 100 parts by mass of the polyester resin contained in the toner.
The colorant used in the exemplary embodiment may be a known colorant such as a black pigment, a yellow pigment, a red pigment, or a blue pigment.
Examples of the black pigment include carbon black and magnetic powder.
Examples of the Yellow pigment include hansa Yellow, hansa Yellow 10G, benzidine Yellow GR, yellow-Yellow (Yellow), quinoline Yellow, and permanent Yellow NCG.
Examples of red pigments include Bengal (Bengal), lake red, permanent red 4R, lithol red, bright magenta 3B, bright magenta 6B, duPont oil red, pyrazolone red, rhodamine B lake, lake red G, rose red, eosin and alizarin lake.
Examples of blue pigments include berlin blue, cobalt blue, basic lake blue, victoria blue lake, fast sky blue, indanthrene blue BC, aniline blue, ultramarine blue, chalcoio blue, methylene blue chloride, phthalocyanine blue, phthalocyanine green, and malachite green oxalate.
Mixtures of any of these colorants can be used and can be used in the solid solution state.
Wax dispersion
The toner of the present invention further contains a wax dispersion liquid, wherein examples of the wax dispersion liquid include vegetable waxes such as ester wax, carnauba wax, rice bran wax, candelilla wax, wood wax, jojoba oil and the like; animal waxes such as beeswax; mineral or petroleum waxes such as montan wax, ceresin wax, paraffin wax, microcrystalline wax, and Fischer-Tropsch wax; modified products thereof may also be used.
The wax melting point is preferably equal to or higher than 60 ℃, more preferably equal to or higher than 65 ℃, still more preferably equal to or higher than 70 ℃. Since the wax having the melting point in the above range can inhibit fluidity of the toner and filming on the photoreceptor.
The wax is dispersed in water together with an ionic surfactant, a polyelectrolyte such as a polymeric acid and a polymeric base, and then micronized by using a homogenizer or a pressure release type dispersing machine capable of applying a strong shearing force while heating to a temperature of the melting point or above. In this way, a wax dispersion of particles having a particle diameter of less than or equal to 1 μm can be prepared.
The weight average particle diameter of the wax particles in the aqueous medium is preferably 1 μm or less, more preferably 100nm to 700nm, still more preferably 100nm to 500nm. Since setting the weight average particle diameter of the wax particles within the above-described range can easily control the particle diameter of the aggregated particles and can obtain a good effect as a releasing agent.
The amount of the wax added to the toner of the exemplary embodiment is preferably about 2 parts by mass to about 15 parts by mass with respect to 100 parts by mass of the polyester resin contained in the toner.
External additive
External additives that may be added for the purpose of charge adjustment, imparting fluidity, charge exchange property, and the like generally include inorganic oxides such as silica, titania, and alumina and cause them to adhere to the obtained toner particles. The procedure may be performed with a V-blender, henschel mixer, or lodge mixer, and the attachment may be performed in stages.
Examples of the inorganic particles include particles of silica, alumina, titania, barium titanate, magnesium titanate, calcium titanate, strontium titanate, zinc oxide, quartz sand, clay, mica, wollastonite, diatomaceous earth, cerium chloride, red lead, chromium oxide, cerium oxide, antimony trioxide, magnesium oxide, zirconium oxide, silicon carbide, silicon nitride, and the like. Among them, silica particles and/or titania particles are preferable. From the viewpoint of the chargeability and developability of the stable toner, the hydrophobicized silica particles or titania particles are particularly preferable.
As a method for surface modification, a known method may be used, specifically including coupling treatment with silane, titanate or aluminate. Any coupling agent may be used for the coupling treatment without particular limitation. Preferred examples of the coupling agent include: silane coupling agents such as methyltrimethoxysilane, phenyltrimethoxysilane, methylphenyldimethoxysilane, diphenyldimethoxysilane, vinyltrimethoxysilane, gamma-aminopropyl trimethoxysilane, gamma-chloropropyl trimethoxysilane, gamma-bromopropyl trimethoxysilane, gamma-glycidoxypropyl trimethoxysilane, gamma-mercaptopropyl trimethoxysilane, gamma-ureidopropyl trimethoxysilane, fluoroalkyl trimethoxysilane and hexamethyldisilazane titanate coupling agent aluminate coupling agents.
The addition amount of the external additive is 0.1 to 5 parts by weight, more preferably 0.3 to 2 parts by weight, relative to 100 parts by weight of the toner. When the amount of the external additive is less than 0.1 parts by weight, the toner fluidity may deteriorate, and further deterioration of chargeability and charge exchange property may be observed, and when the amount of the external additive exceeds 5 parts by weight, the toner is in an excessively coated state, thereby transferring an excessive amount of inorganic oxide to a contact member, sometimes causing secondary failure.
Electrostatic image developer
The toner for developing an electrostatic image of the present invention can be used for an electrostatic image developer. The toner for developing an electrostatic image is not particularly limited as long as the developer contains the toner for developing an electrostatic image, and the components and composition may be appropriately selected according to the use. If the toner for developing an electrostatic image is used alone, a one-component electrostatic image developer is prepared, and if the toner is combined with a carrier, a two-component electrostatic image developer can be obtained.
The carrier is not particularly limited, and conventionally known carriers such as magnetic particles, e.g., iron powder, ferrite, iron oxide powder, nickel, etc., can be cited; a resin-coated carrier having a resin coating layer, the carrier being formed by coating with a resin such as a styrene resin, a vinyl resin, a rosin resin, a polyester resin, a melamine resin, or with a wax such as stearic acid; and a carrier in which magnetic particles are dispersed, the carrier comprising magnetic particles dispersed in a binder resin. Among them, the resin-coated carrier is preferable because the chargeability of the toner and the electric resistance of the entire carrier can be controlled by the constitution of the resin-coated layer.
In general, the mixing ratio of the toner and the carrier in the two-component electrostatic image developer of the present invention is: the toner is 2 to 10 parts by weight relative to 100 parts by weight of the carrier.
Examples
The invention will be described in detail by reference to examples, but it should be understood that the invention is not limited thereto, unless otherwise specified in the description.
Preparation of colorantsDispersion liquid
30g of carbon black (Cabot corporation) and 7.5g of sodium dodecyl sulfate and 62.5g of water were subjected to stirring at room temperature to be pre-dispersed, and then this dispersion was added to a high-speed dispersant to be dispersed, and a colorant dispersion was obtained by 2 hours of dispersion. The particle diameter is 181nm and the solid content is 30% measured by a nanometer particle size analyzer.
Preparation of wax dispersions
30g of carnauba wax (RC-160, manufactured by TOA Kasei Co., ltd.), 7.5g of sodium dodecyl sulfate and 62.5g of water were dissolved by stirring at 90℃and then the mixture was rapidly added to a high-speed dispersant for 2 hours to disperse, to obtain a milky wax dispersion. The particle diameter is 158nm and the solid content is 30% measured by a nanometer particle size analyzer.
Example 1
Preparation of toner-T1
0.01mol (1.66 g) of terephthalic acid, 0.01mol (1.16 g) of fumaric acid, 0.01mol (1.18 g) of succinic acid, 0.02mol (6.32 g) of bisphenol A ethylene oxide adduct, 0.004mol (0.472 g) of butanediol, 0.005mol (0.590 g) of 1, 6-hexanediol, 0.0979g (0.00032 mol) of dibutyltin oxide were added to the reaction vessel, stirred under nitrogen atmosphere, polycondensed at 130℃for 7 hours, then 0.003mol (0.618 g) of 1, 10-decanedithiol and 0.002mol (0.284 g) of benzenedithiol were added, and the reaction was continued at 150℃for 7 hours to obtain a polyester resin.
Dispersing the prepared polyester resin for 3 minutes under the condition of 3000rpm of a homogenizer, adding water to adjust the solid content to 10%, adding 0.003mol of mPEG-SH-1000 (mPEG-SH-1000 represents mPEG-SH molecular weight of 1000), and obtaining the polyester resin emulsion after high-speed stirring and dispersing after air oxidation.
Adding 0.8g of carbon black dispersion liquid and 0.8g of carnauba wax dispersion liquid, regulating the pH value to 7 under the action of potassium persulfate, slowly heating to 85 ℃, keeping for 1h, cooling to 65 ℃ again, keeping for 2h, cooling to room temperature, washing with water, drying, and adding 3.8g of hydrophobically modified silicon dioxide to obtain the toner T1.
Example 2
Preparation of toner-T2
0.008mol (1.328 g) of terephthalic acid, 0.013mol (1.508 g) of fumaric acid, 0.009mol (1.062 g) of succinic acid, 0.018mol (5.688 g) of bisphenol A ethylene oxide adduct, 0.005mol (0.59 g) of butanediol, 0.006mol (0.709 g) of 1, 6-hexanediol, 0.0979g (0.00032 mol) of dibutyltin oxide were charged into a reaction vessel, stirred under nitrogen atmosphere, polycondensed at 70℃for 8 hours, then 0.003mol (0.618 g) of 1, 10-decanedithiol and 0.002mol (0.284 g) of benzenedithiol were added, and the reaction was continued at 150℃for 7 hours to obtain a polyester resin.
Dispersing the prepared polyester resin for 5 minutes under the condition of 5000rpm of a homogenizer, adding water to adjust the solid content to 18%, adding 0.0033mol of mPEG-SH-1000 (mPEG-SH-1000 represents mPEG-SH molecular weight of 1000), and carrying out air oxidation, and then stirring at a high speed and dispersing to obtain the polyester resin emulsion.
Adding 0.8g of carbon black dispersion liquid and 0.8g of carnauba wax dispersion liquid, regulating the pH value to 5.5 under the action of potassium persulfate, slowly heating to 70 ℃, keeping the temperature for 2 hours, cooling to 50 ℃, keeping the temperature for 2 hours, cooling to room temperature, washing with water, drying, and adding 3.8g of hydrophobically modified silicon dioxide to obtain the toner T2.
Example 3
Preparation of toner-T3
0.009mol (1.494 g) of terephthalic acid, 0.009mol (1.044 g) of fumaric acid, 0.01mol (1.18 g) of succinic acid, 0.002mol (0.384 g) of trimellitic anhydride, 0.02mol (6.32 g) of bisphenol A ethylene oxide adduct, 0.003mol (0.354 g) of butanediol, 0.006mol (0.709 g) of 1, 6-hexanediol, 0.0979g (0.00032 mol) of dibutyltin oxide were added to a reaction vessel, stirred under nitrogen atmosphere, subjected to polycondensation reaction at 130℃for 7 hours, then 0.0015mol (0.309 g) of 1, 10-decanedithiol, and 0.0035mol (0.497 g) of benzenedithiol were added, and the reaction was continued at 140℃for 7 hours to obtain a polyester resin.
Dispersing the prepared polyester resin for 4 minutes under the condition of 4500rpm of a homogenizer, adding water to adjust the solid content to be 14%, adding 0.0028mol of mPEG-SH-1000 (mPEG-SH-1000 represents mPEG-SH molecular weight to be 1000), and obtaining the polyester resin emulsion after high-speed stirring and dispersing after air oxidation.
Adding 0.8g of carbon black dispersion liquid and 0.8g of carnauba wax dispersion liquid, regulating the pH value to 6.5 under the action of potassium persulfate, slowly heating to 85 ℃, keeping for 1h, cooling to 65 ℃ again, keeping for 2h, cooling to room temperature, washing with water, drying, and adding 3.8g of hydrophobically modified silicon dioxide to obtain the toner T3.
Example 4
Preparation of toner-T4
0.0095mol (1.577 g) of terephthalic acid, 0.0088mol (1.0208 g) of fumaric acid, 0.0107mol (1.2626 g) of succinic acid, 0.001mol (0.192 g) of trimellitic anhydride, 0.019mol (6.004 g) of bisphenol A ethylene oxide adduct, 0.0075mol (0.885 g) of butanediol, 0.002mol (0.2363 g) of 1, 6-hexanediol, 0.0979g (0.00032 mol) of dibutyltin oxide were added to a reaction vessel, stirred under nitrogen atmosphere, and subjected to polycondensation reaction at 130℃for 7 hours, followed by addition of 0.0019mol (0.3914 g) of 1, 10-decanedithiol, and 0.0026mol (0.3692 g) of benzenedithiol, followed by further reaction at 150℃for 7 hours to obtain a polyester resin.
Dispersing the prepared polyester resin for 3 minutes under the condition of 3000rpm of a homogenizer, adding water to adjust the solid content to 12%, adding 0.0027mol of mPEG-SH-1000 (mPEG-SH-1000 represents mPEG-SH molecular weight of 1000), and carrying out air oxidation, and then stirring at a high speed and dispersing to obtain the polyester resin emulsion.
Adding 0.8g of carbon black dispersion liquid and 0.8g of carnauba wax dispersion liquid, regulating the pH value to 6.5 under the action of potassium persulfate, slowly heating to 85 ℃, keeping for 1h, cooling to 65 ℃ again, keeping for 2h, cooling to room temperature, washing with water, drying, and adding 3.8g of hydrophobically modified silicon dioxide to obtain the toner T4.
Example 5
Preparation of toner-T5
0.0115mol (1.909 g) of terephthalic acid, 0.008mol (1.0208 g) of fumaric acid, 0.0105mol (1.239 g) of succinic acid, 0.0195mol (6.162 g) of bisphenol A ethylene oxide adduct, 0.0045mol (0.531 g) of butanediol, 0.0048mol (0.5672 g) of 1, 6-hexanediol, 0.0979g (0.00032 g) of dibutyltin oxide were charged into a reaction vessel, stirred under nitrogen atmosphere, polycondensed at 130℃for 7 hours, then 0.0025mol (0.515 g) of 1, 10-decanedithiol, 0.0017mol (0.2414 g) of benzenedithiol were added, and the reaction was continued at 150℃for 7 hours to obtain a polyester resin.
Dispersing the prepared polyester resin for 4 minutes under the condition of 3500rpm of a homogenizer, adding water to adjust the solid content to 15%, adding 0.0025mol of mPEG-SH-2000 (mPEG-SH-2000 represents mPEG-SH molecular weight of 2000), and carrying out air oxidation, and then stirring at a high speed and dispersing to obtain the polyester resin emulsion.
Adding 0.8g of carbon black dispersion liquid and 0.8g of carnauba wax dispersion liquid, regulating the pH value to 7 under the action of potassium persulfate, slowly heating to 85 ℃, keeping for 1h, cooling to 65 ℃ again, keeping for 2h, cooling to room temperature, washing with water, drying, and adding 3.8g of hydrophobically modified silicon dioxide to obtain the toner T5.
Example 6
Preparation of toner-T6
0.0088mol (1.4608 g) of terephthalic acid, 0.0087mol (1.0092 g) of fumaric acid, 0.011mol (1.298 g) of succinic acid, 0.0015mol (0.288 g) of trimellitic anhydride, 0.0213mol (6.7308 g) of bisphenol A ethylene oxide adduct, 0.0054mol (0.6372 g) of butanediol, 0.0017mol (0.2009 g) of 1, 6-hexanediol, 0.0979g (0.00032 mol) of dibutyltin oxide were added to a reaction vessel, stirred under nitrogen atmosphere, and subjected to polycondensation reaction at 130℃for 7 hours, followed by addition of 0.0031mol (0.6386 g) of 1, 10-decanedithiol, and 0.0022mol (0.3124 g) of benzene dithiol, followed by further reaction at 150℃for 7 hours to obtain a polyester resin.
Dispersing the prepared polyester resin for 3 minutes under the condition of 3000rpm of a homogenizer, adding water to adjust the solid content to 10%, adding 0.0013mol of mPEG-SH-2000 and 0.0015mol of mPEG-SH-1000 (mPEG-SH-2000 represents mPEG-SH molecular weight of 2000 and mPEG-SH-1000 represents mPEG-SH molecular weight of 1000), and carrying out air oxidation, stirring at a high speed and dispersing to obtain the polyester resin emulsion.
Adding 0.8g of carbon black dispersion liquid and 0.8g of carnauba wax dispersion liquid, regulating the pH value to 7 under the action of potassium persulfate, slowly heating to 85 ℃, keeping for 1h, cooling to 65 ℃ again, keeping for 2h, cooling to room temperature, washing with water, drying, and adding 3.8g of hydrophobically modified silicon dioxide to obtain the toner T6.
Example 7
Preparation of toner-T7
0.0092mol (1.5272 g) of terephthalic acid, 0.011mol (1.0092 g) of fumaric acid, 0.0087mol (1.0266 g) of succinic acid, 0.0011mol (0.2112 g) of trimellitic anhydride, 0.0208mol (6.5728 g) of bisphenol A ethylene oxide adduct, 0.0061mol (0.7198 g) of butanediol, 0.001mol (0.118 g) of 1, 6-hexanediol, 0.0979g (0.00032 mol) of dibutyltin oxide were added to the reaction vessel, stirred under nitrogen atmosphere, subjected to polycondensation reaction at 130℃for 7 hours, then 0.0044mol (0.9064 g) of 1, 10-decanedithiol, 0.0011mol (0.1562 g) of benzenedithiol were added, and the reaction was continued at 150℃for 7 hours to obtain a polyester resin.
Dispersing the prepared polyester resin for 3 minutes under the condition of 3000rpm of a homogenizer, adding water to adjust the solid content to 10%, adding 0.0012mol of mPEG-SH-2000 and 0.0011mol of mPEG-SH-1000 (mPEG-SH-2000 represents mPEG-SH molecular weight of 2000 and mPEG-SH-1000 represents mPEG-SH molecular weight of 1000), and carrying out air oxidation, stirring at a high speed and dispersing to obtain the polyester resin emulsion.
Adding 0.8g of carbon black dispersion liquid and 0.8g of carnauba wax dispersion liquid, regulating the pH value to 7 under the action of potassium persulfate, slowly heating to 85 ℃, keeping for 1h, cooling to 65 ℃ again, keeping for 2h, cooling to room temperature, washing with water, drying, and adding 3.8g of hydrophobically modified silicon dioxide to obtain the toner T7.
Example 8
Preparation of toner-T8
0.0099mol (1.6434 g) of terephthalic acid, 0.0059mol (0.6844 g) of fumaric acid, 0.0133mol (1.5694 g) of succinic acid, 0.0009mol (0.1728 g) of trimellitic anhydride, 0.0188mol (5.9408 g) of bisphenol A ethylene oxide adduct, 0.0079mol (0.9322 g) of butanediol, 0.002mol (0236 g) of 1, 6-hexanediol, 0.0979g (0.00032 mol) of dibutyltin oxide were charged into a reaction vessel, stirred under nitrogen atmosphere, polycondensed at 130℃for 7 hours, then 0.0035mol (0.721 g) of 1, 10-decanedithiol, 0.0021mol (0.2982 g) of benzenedithiol were charged, and the reaction was continued at 150℃for 7 hours to obtain a polyester resin.
Dispersing the prepared polyester resin for 3 minutes under the condition of 3000rpm of a homogenizer, adding water to adjust the solid content to 10 percent, adding 0.0009mol of SH-PEG-SH-2000 and 0.0023mol of SH-PEG-SH-1000 (SH-PEG-SH-2000 represents SH-PEG-SH molecular weight is 2000 and SH-PEG-SH-1000 represents SH-PEG-SH molecular weight is 1000), and obtaining the polyester resin emulsion after high-speed stirring and dispersing after air oxidation.
Adding 0.8g of carbon black dispersion liquid and 0.8g of carnauba wax dispersion liquid, regulating the pH value to 7 under the action of potassium persulfate, slowly heating to 85 ℃, keeping for 1h, cooling to 65 ℃ again, keeping for 2h, cooling to room temperature, washing with water, drying, and adding 3.8g of hydrophobically modified silicon dioxide to obtain the toner T8.
Example 9
Preparation of toner-T9
0.011mol (1.826 g) of terephthalic acid, 0.007mol (0.812 g) of fumaric acid, 0.0118mol (1.3924 g) of succinic acid, 0.0002mol (0.0384 g) of trimellitic anhydride, 0.0155mol (4.898 g) of bisphenol A ethylene oxide adduct, 0.0088mol (1.0384 g) of butanediol, 0.005mol (0.590 g) of 1, 6-hexanediol, 0.0979g (0.00032 mol) of dibutyltin oxide were added to a reaction vessel, stirred under nitrogen atmosphere, and subjected to polycondensation reaction at 130℃for 7 hours, followed by addition of 0.0033mol (0.6798 g) of 1, 10-decanedithiol, 0.0008mol (0.1136 g) of benzene dithiol, 0.0011mol (0.165 g) of 1, 6-hexanedithiol, and further reaction at 150℃for 7 hours to obtain a polyester resin.
Dispersing the prepared polyester resin for 3 minutes under the condition of 3000rpm of a homogenizer, adding water to adjust the solid content to 14%, adding 0.0008mol of SH-PEG-SH-2000 and 0.002mol of SH-PEG-SH-1000 (SH-PEG-SH-2000 represents SH-PEG-SH molecular weight is 2000 and SH-PEG-SH-1000 represents SH-PEG-SH molecular weight is 1000), and carrying out air oxidation, stirring at a high speed and dispersing to obtain the polyester resin emulsion.
Adding 0.8g of carbon black dispersion liquid and 0.8g of carnauba wax dispersion liquid, regulating the pH value to 7 under the action of potassium persulfate, slowly heating to 85 ℃, keeping for 1h, cooling to 65 ℃ again, keeping for 2h, cooling to room temperature, washing with water, drying, and adding 3.8g of hydrophobically modified silicon dioxide to obtain the toner T9.
Example 10
Preparation of toner-T10
0.01mol (1.66 g) of terephthalic acid, 0.0088mol (1.0208 g) of fumaric acid, 0.0112mol (1.3216 g) of succinic acid, 0.0171mol (5.4036 g) of bisphenol A ethylene oxide adduct, 0.0078mol (0.9204 g) of butanediol, 0.0045mol (0.532 g) of 1, 6-hexanediol, 0.0979g (0.00032 g) of dibutyltin oxide were added to the reaction vessel, stirred under nitrogen atmosphere, and subjected to polycondensation reaction at 130℃for 7 hours, followed by addition of 0.004mol (0.824 g) of 1, 10-decanedithiol, 0.0005mol (0.071 g) of benzenedithiol, and 0.0006mol (0.09 g) of 1, 6-hexanediol, followed by reaction at 150℃for 7 hours to obtain a polyester resin.
Dispersing the prepared polyester resin for 3 minutes under the condition of 3000rpm of a homogenizer, adding water to adjust the solid content to 14%, adding 0.0014mol of SH-PEG-SH-2000 and 0.0018mol of SH-PEG-SH-1000 (SH-PEG-SH-2000 represents SH-PEG-SH molecular weight is 2000 and SH-PEG-SH-1000 represents SH-PEG-SH molecular weight is 1000), and carrying out air oxidation, stirring at a high speed and dispersing to obtain the polyester resin emulsion.
Adding 0.8g of carbon black dispersion liquid and 0.8g of carnauba wax dispersion liquid, regulating the pH value to 7 under the action of potassium persulfate, slowly heating to 85 ℃, keeping for 1h, cooling to 65 ℃ again, keeping for 2h, cooling to room temperature, washing with water, drying, and adding 3.8g of hydrophobically modified silicon dioxide to obtain the toner T10.
Example 11
Preparation of toner-T11
0.0105mol (1.743 g) of terephthalic acid, 0.0105mol (1.218 g) of fumaric acid, 0.009mol (1.062 g) of succinic acid, 0.0179mol (5.6564 g) of bisphenol A ethylene oxide adduct, 0.0088mol (1.0384 g) of butanediol, 0.003mol (0.354 g) of 1, 6-hexanediol, 0.0979g (0.00032 g) of dibutyltin oxide were added to the reaction vessel, stirred under nitrogen atmosphere, and subjected to polycondensation reaction at 130℃for 7 hours, followed by addition of 0.0032mol (0.6592 g) of 1, 10-decanedithiol, 0.0005mol (0.071 g) of benzenedithiol, and 0.0001mol (0.015 g) of 1, 6-hexanediol, followed by further reaction at 150℃for 7 hours to obtain a polyester resin.
Dispersing the prepared polyester resin for 3 minutes under the condition of 3000rpm of a homogenizer, adding water to adjust the solid content to 10%, adding 0.0019mol of SH-PEG-SH-2000 and 0.0013mol of SH-PEG-SH-1000 (SH-PEG-SH-2000 represents SH-PEG-SH molecular weight is 2000 and SH-PEG-SH-1000 represents SH-PEG-SH molecular weight is 1000), and carrying out air oxidation, stirring at a high speed and dispersing to obtain the polyester resin emulsion.
Adding 0.8g of carbon black dispersion liquid and 0.8g of carnauba wax dispersion liquid, regulating the pH value to 7 under the action of potassium persulfate, slowly heating to 85 ℃, keeping for 1h, cooling to 65 ℃ again, keeping for 2h, cooling to room temperature, washing with water, drying, and adding 3.8g of hydrophobically modified silicon dioxide to obtain the toner T11.
Example 12
Preparation of toner-T12
0.0111mol (1.8426 g) of terephthalic acid, 0.0101mol (1.1716 g) of fumaric acid, 0.0047mol (0.5546 g) of succinic acid, 0.0041mol (0.7872 g) of trimellitic anhydride, 0.021mol (6.636 g) of bisphenol A ethylene oxide adduct, 0.004mol (0.472 g) of butanediol, 0.0033mol (0.389 g) of 1, 6-hexanediol, 0.00032mol (0.0979 g) of dibutyltin oxide were added to the reaction vessel, stirred under nitrogen atmosphere, and subjected to polycondensation reaction at 130℃for 7 hours, followed by addition of 0.004mol (0.824 g) of 1, 10-decanedithiol, 0.0005mol (0.071 g) of benzene dithiol, 0.0003mol (0.045 g) of 1, 6-hexanediol, and further reaction at 150℃for 7 hours to give a polyester resin.
Dispersing the prepared polyester resin for 3 minutes under the condition of 3000rpm of a homogenizer, adding water to adjust the solid content to 10%, adding 0.0019mol of SH-PEG-SH-2000 and 0.0018mol of SH-PEG-SH-1000 (SH-PEG-SH-2000 represents SH-PEG-SH molecular weight is 2000 and SH-PEG-SH-1000 represents SH-PEG-SH molecular weight is 1000), and carrying out air oxidation, stirring at a high speed and dispersing to obtain the polyester resin emulsion.
Adding 0.8g of carbon black dispersion liquid and 0.8g of carnauba wax dispersion liquid, regulating the pH value to 7 under the action of potassium persulfate, slowly heating to 85 ℃, keeping for 1h, cooling to 65 ℃ again, keeping for 2h, cooling to room temperature, washing with water, drying, and adding 3.8g of hydrophobically modified silicon dioxide to obtain the toner T12.
Comparative example 1
Preparation of toner-T13
0.01mol (1.66 g) of terephthalic acid, 0.01mol (1.16 g) of fumaric acid, 0.01mol (1.18 g) of succinic acid, 0.02mol (6.32 g) of bisphenol A ethylene oxide adduct, 0.004mol (0.472 g) of butanediol, 0.01mol (1.1817 g) of 1, 6-hexanediol, 0.005mol (1.5417 g) of dodecyltrimethylammonium bromide and 0.00032mol (0.0979 g) of dibutyltin oxide were added to the reaction vessel, stirred under nitrogen atmosphere, and subjected to polycondensation reaction at 130℃for 7 hours to obtain a polyester resin.
Dispersing the prepared polyester resin for 3 minutes under the condition of 3000rpm of a homogenizer, adding water to adjust the solid content to 10%, adding 0.003mol of mPEG-SH-1000 (mPEG-SH-1000 represents mPEG-SH molecular weight of 1000), and obtaining the polyester resin emulsion after high-speed stirring and dispersing after air oxidation.
Adding 0.8g of carbon black dispersion liquid and 0.8g of carnauba wax dispersion liquid, regulating the pH value to 7 under the action of potassium persulfate, slowly heating to 85 ℃, keeping for 1h, cooling to 65 ℃ again, keeping for 2h, cooling to room temperature, washing with water, drying, and adding 3.8g of hydrophobically modified silicon dioxide to obtain the toner T13.
Comparative example 2
Preparation of toner-T14
0.01mol (1.66 g) of terephthalic acid, 0.01mol (1.16 g) of fumaric acid, 0.01mol (1.18 g) of succinic acid, 0.02mol (6.32 g) of bisphenol A ethylene oxide adduct, 0.004mol (0.472 g) of butanediol, 0.006mol (0.709 g) of 1, 6-hexanediol, 0.005mol (1.5417 g) of dodecyltrimethylammonium bromide and 0.00032mol (0.0979 g) of dibutyltin oxide were added to the reaction vessel, stirred under nitrogen atmosphere, and the polycondensation reaction was continued at 130℃for 7 hours and continued at 150℃for 7 hours to obtain a polyester resin. The polyester resin is obtained.
Dispersing the prepared polyester resin for 3 minutes under the condition of 3000rpm of a homogenizer, adding water to adjust the solid content to 10%, adding 0.003mol of mPEG-SH-500 (mPEG-SH-500 represents mPEG-SH molecular weight of 500), and carrying out air oxidation, and then stirring at a high speed and dispersing to obtain the polyester resin emulsion.
Adding 0.8g of carbon black dispersion liquid and 0.8g of carnauba wax dispersion liquid, regulating the pH value to 7 under the action of potassium persulfate, slowly heating to 85 ℃, keeping for 1h, cooling to 65 ℃ again, keeping for 2h, cooling to room temperature, washing with water, drying, and adding 3.8g of hydrophobically modified silicon dioxide to obtain the toner T14.
Comparative example 3
Preparation of toner-T15
0.01mol (1.66 g) of terephthalic acid, 0.01mol (1.16 g) of fumaric acid, 0.01mol (1.18 g) of succinic acid, 0.02mol (6.32 g) of bisphenol A ethylene oxide adduct, 0.004mol (0.472 g) of butanediol, 0.005mol (0.590 g) of 1, 6-hexanediol, 0.005mol (1.5417 g) of dodecyltrimethylammonium bromide and 0.00032mol (0.0979 g) of dibutyltin oxide were added to the reaction vessel, stirred under nitrogen atmosphere, and the polycondensation reaction was continued at 130℃for 7 hours and continued at 150℃for 7 hours to obtain a polyester resin. The polyester resin is obtained.
Dispersing the prepared polyester resin for 3 minutes under the condition of 3000rpm of a homogenizer, adding water to adjust the solid content to 10%, adding 0.003mol of mPEG-SH-3000 (mPEG-SH-3000 represents mPEG-SH molecular weight of 3000), and obtaining the polyester resin emulsion after air oxidation, high-speed stirring and dispersing.
Adding 0.8g of carbon black dispersion liquid and 0.8g of carnauba wax dispersion liquid, regulating the pH value to 7 under the action of potassium persulfate, slowly heating to 85 ℃, keeping for 1h, cooling to 65 ℃ again, keeping for 2h, cooling to room temperature, washing with water, drying, and adding 3.8g of hydrophobically modified silicon dioxide to obtain the toner T15.
The amounts of the main reactants used in examples 1 to 12 and comparative examples 1 to 3 are shown in Table 1.
TABLE 1
The toner finished products formed by externally adding and mixing the toners in the above examples and comparative examples were mixed with carrier particles (a kind of magnetic particles for making the toner magnetic for printing and copying), and were subjected to on-machine test for printing effect, the test procedure was: a 5000-ten-thousand continuous printing test was performed under an ambient temperature and humidity (20 ℃/50% rh) environment, and the test results are shown in table 2 below.
Evaluation of storage Property
10g of toner was placed in a round container of an open system, left to stand at 50℃under 60% humidity for 72 hours, and then gently transferred to the container containing toner, and the presence or absence of aggregation of toner was visually confirmed. No aggregation of the toner surface was observed, representing excellent preservation; if the surface of the toner is coagulated, but vibration is not needed for transferring, the toner can be eliminated, and the actual printing effect is not affected, and the toner is represented as good; if the toner surface is aggregated, vibration during transfer cannot be eliminated, which means poor storage stability. The evaluation results are shown in Table 2.
TABLE 2
It is to be understood that variations and modifications of the above embodiments may be made by those skilled in the art in light of the above description. Therefore, the invention is not limited to the specific embodiments disclosed and described above, but equivalent modifications and variations of the invention should be made within the scope of the claims of the present invention. Furthermore, although specific terms are used herein, such terms are used for convenience in description and are not intended to limit the invention in any way.
Claims (7)
1. A toner, characterized in that the toner is prepared by the steps of:
s1: adding carboxylic acid compounds, alcohol compounds and catalysts into a reaction vessel, and stirring and reacting for 5-8 hours at 70-150 ℃ under the protection of nitrogen to obtain polyester resin;
s2: dispersing the prepared polyester resin for 3-5 min under a homogenizer, adding an aqueous solvent, controlling the solid content to be 10-18%, adding mPEG-SH and/or HS-PEG-SH, reacting by an air oxidation method or a potassium ferricyanide oxidation method, and obtaining a resin emulsion of 100-200 nm after high-speed stirring and dispersing;
s3: adding colorant dispersion liquid and wax dispersion liquid into the resin emulsion, regulating the pH to 5.5-7 under the action of a polymerization initiator, slowly heating to 70-85 ℃, keeping the temperature for 1-2 hours, then cooling to 50-65 ℃, keeping the temperature for 2-3 hours, cooling to room temperature, washing and drying to obtain carbon powder parent particles, and adding hydrophobic silica particles as an external additive to obtain the toner;
the alcohol compound is selected from one or more of dithiol, bisphenol A ethylene oxide addition product, butanediol and diol with 6-12 carbon atoms;
The dithiol is selected from one or more of the following compounds: benzene dithiol, 1, 6-hexane dithiol, 1, 7-heptane dithiol, 1, 8-octane dithiol, 1, 9-nonandithiol, 1, 10-decanedithiol;
the carboxylic acid compound is selected from one or more of aromatic diacid, aliphatic diacid and trimellitic anhydride;
the dithiol accounts for 11.0 to 16.5mol percent of the alcohol compound, the bisphenol A ethylene oxide adduct accounts for 40 to 65mol percent of the alcohol compound, and the aromatic diacid accounts for 25 to 40mol percent of the carboxylic acid compound.
2. The toner according to claim 1, wherein the aromatic diacid is selected from one or more combinations of phthalic acid, isophthalic acid, terephthalic acid, t-butyl isophthalic acid, 2, 6-naphthalene dicarboxylic acid, 4' -biphenyl dicarboxylic acid;
the aliphatic diacid is selected from one or more of succinic acid, adipic acid, sebacic acid, fumaric acid, maleic acid and citraconic acid;
the diol with 6-12 carbon atoms is selected from one or more of 1, 6-hexanediol, 1, 7-heptanediol, 1, 8-octanediol, 1, 9-nonanediol, 1, 10-decanediol, 1, 11-undecanediol and 1, 12-dodecanediol.
3. The toner according to claim 2, wherein the aromatic diacid is terephthalic acid, the aliphatic diacid is fumaric acid and/or succinic acid, and the diol having 6 to 12 carbon atoms is 1, 6-hexanediol.
4. A method for producing a toner, comprising the steps of:
s1: adding carboxylic acid compounds, alcohol compounds and catalysts into a reaction vessel, and stirring and reacting for 5-8 hours at 70-150 ℃ under the protection of nitrogen to obtain polyester resin;
s2: dispersing the prepared polyester resin for 3-5 min under a homogenizer, adding an aqueous solvent, controlling the solid content to be 10-18%, adding mPEG-SH and/or HS-PEG-SH, reacting by an air oxidation method or a potassium ferricyanide oxidation method, and obtaining a resin emulsion of 100-200 nm after high-speed stirring and dispersing;
s3: adding colorant dispersion liquid and wax dispersion liquid into the resin emulsion, regulating the pH to 5.5-7 under the action of a polymerization initiator, slowly heating to 70-85 ℃, keeping the temperature for 1-2 hours, then cooling to 50-65 ℃, keeping the temperature for 2-3 hours, cooling to room temperature, washing and drying to obtain carbon powder parent particles, and adding hydrophobic silica particles as an external additive to obtain the toner;
Wherein the alcohol compound is selected from one or more of dithiol, bisphenol A ethylene oxide addition product, butanediol and diol with 6-12 carbon atoms;
the dithiol is selected from one or more of the following compounds: benzene dithiol, 1, 6-hexane dithiol, 1, 7-heptane dithiol, 1, 8-octane dithiol, 1, 9-nonandithiol, 1, 10-decanedithiol;
the carboxylic acid compound is selected from one or more of aromatic diacid, aliphatic diacid and trimellitic anhydride;
the dithiol accounts for 11.0 to 16.5mol percent of the alcohol compound, the bisphenol A ethylene oxide adduct accounts for 40 to 65mol percent of the alcohol compound, and the aromatic diacid accounts for 25 to 40mol percent of the carboxylic acid compound.
5. The method for producing a toner according to claim 4, wherein the catalyst is one or a combination of more selected from the group consisting of titanium tetraethoxide, titanium tetrapropanol, titanium tetraisopropoxide, titanium tetrabutoxide, dibutyltin dichloride, dibutyltin oxide, and diphenyltin oxide, wherein the catalyst is 0.1 to 0.5mol% based on the total amount of the material.
6. The method of producing a toner according to claim 4, wherein the rotational speed of the homogenizer is 3000 to 5000rpm.
7. The method of producing toner according to claim 4, wherein the toner has an average particle diameter of 4.5 to 8.5 μm, a particle diameter dispersity of 1.10 to 1.32, and a sphericity of 0.96 to 0.98.
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