CN113703296A - Toner and preparation method thereof - Google Patents
Toner and preparation method thereof Download PDFInfo
- Publication number
- CN113703296A CN113703296A CN202110998940.4A CN202110998940A CN113703296A CN 113703296 A CN113703296 A CN 113703296A CN 202110998940 A CN202110998940 A CN 202110998940A CN 113703296 A CN113703296 A CN 113703296A
- Authority
- CN
- China
- Prior art keywords
- acid
- toner
- polyester resin
- dispersing
- toner according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 title abstract description 24
- 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 20
- 125000003118 aryl group Chemical group 0.000 claims abstract description 19
- 150000004662 dithiols Chemical class 0.000 claims abstract description 16
- 239000006185 dispersion Substances 0.000 claims description 59
- 239000002245 particle Substances 0.000 claims description 58
- -1 carboxylic acid compounds Chemical class 0.000 claims description 48
- 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
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 42
- 239000007788 liquid Substances 0.000 claims description 39
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 36
- 238000001816 cooling Methods 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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 25
- 238000003756 stirring Methods 0.000 claims description 24
- 239000000839 emulsion Substances 0.000 claims description 22
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 22
- 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 21
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 21
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 21
- 239000001530 fumaric acid Substances 0.000 claims description 21
- 239000003086 colorant Substances 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
- 238000010438 heat treatment Methods 0.000 claims description 20
- 239000007787 solid Substances 0.000 claims description 20
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 19
- 230000009471 action Effects 0.000 claims description 18
- 238000001035 drying Methods 0.000 claims description 18
- 238000005406 washing Methods 0.000 claims description 18
- JRNVQLOKVMWBFR-UHFFFAOYSA-N 1,2-benzenedithiol Chemical compound SC1=CC=CC=C1S JRNVQLOKVMWBFR-UHFFFAOYSA-N 0.000 claims description 17
- UOQACRNTVQWTFF-UHFFFAOYSA-N decane-1,10-dithiol Chemical compound SCCCCCCCCCCS UOQACRNTVQWTFF-UHFFFAOYSA-N 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 239000003054 catalyst Substances 0.000 claims description 16
- 239000000654 additive Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 150000002009 diols Chemical class 0.000 claims description 11
- 230000003647 oxidation Effects 0.000 claims description 11
- 238000007254 oxidation reaction Methods 0.000 claims description 11
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims description 11
- 125000001931 aliphatic group Chemical group 0.000 claims description 10
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 10
- SRZXCOWFGPICGA-UHFFFAOYSA-N 1,6-Hexanedithiol Chemical compound SCCCCCCS SRZXCOWFGPICGA-UHFFFAOYSA-N 0.000 claims description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 9
- 230000000996 additive effect Effects 0.000 claims description 9
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 8
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 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
- 239000000377 silicon dioxide Substances 0.000 claims description 8
- XSMIOONHPKRREI-UHFFFAOYSA-N undecane-1,11-diol Chemical compound OCCCCCCCCCCCO XSMIOONHPKRREI-UHFFFAOYSA-N 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000003505 polymerization initiator Substances 0.000 claims description 6
- 235000012239 silicon dioxide Nutrition 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 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 5
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-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
- 239000003125 aqueous solvent Substances 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
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-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
- 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
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 claims description 4
- PGTWZHXOSWQKCY-UHFFFAOYSA-N 1,8-Octanedithiol Chemical compound SCCCCCCCCS PGTWZHXOSWQKCY-UHFFFAOYSA-N 0.000 claims description 3
- GJRCLMJHPWCJEI-UHFFFAOYSA-N 1,9-Nonanedithiol Chemical compound SCCCCCCCCCS GJRCLMJHPWCJEI-UHFFFAOYSA-N 0.000 claims description 3
- 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
- RVVRZLSZZKMJCB-UHFFFAOYSA-N heptane-1,7-dithiol Chemical compound SCCCCCCCS RVVRZLSZZKMJCB-UHFFFAOYSA-N 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
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-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
- CCIDWXHLGNEQSL-UHFFFAOYSA-N undecane-1-thiol Chemical compound CCCCCCCCCCCS CCIDWXHLGNEQSL-UHFFFAOYSA-N 0.000 claims description 3
- 239000011159 matrix material Substances 0.000 claims description 2
- 238000003860 storage Methods 0.000 abstract description 11
- 238000004945 emulsification Methods 0.000 abstract description 6
- 238000005886 esterification reaction Methods 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- 235000011087 fumaric acid Nutrition 0.000 description 20
- 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
- 238000006068 polycondensation reaction Methods 0.000 description 12
- 230000001590 oxidative effect Effects 0.000 description 10
- 230000000694 effects Effects 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
- 239000000178 monomer Substances 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- 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
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 229920006125 amorphous polymer Polymers 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- 239000006249 magnetic particle Substances 0.000 description 4
- 239000000203 mixture 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
- 239000000126 substance 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 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
- 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
- 230000009477 glass transition Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
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- DSEKYWAQQVUQTP-XEWMWGOFSA-N (2r,4r,4as,6as,6as,6br,8ar,12ar,14as,14bs)-2-hydroxy-4,4a,6a,6b,8a,11,11,14a-octamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1h-picen-3-one Chemical compound C([C@H]1[C@]2(C)CC[C@@]34C)C(C)(C)CC[C@]1(C)CC[C@]2(C)[C@H]4CC[C@@]1(C)[C@H]3C[C@@H](O)C(=O)[C@@H]1C DSEKYWAQQVUQTP-XEWMWGOFSA-N 0.000 description 2
- 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 2
- 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
- FZXIRTQUJKEDTN-UHFFFAOYSA-N CCCCC(OC(C)(C)OOC(C)(C)C)=O Chemical compound CCCCC(OC(C)(C)OOC(C)(C)C)=O FZXIRTQUJKEDTN-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
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- 229910052772 Samarium Inorganic materials 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
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- 238000009825 accumulation Methods 0.000 description 2
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- 150000004645 aluminates Chemical class 0.000 description 2
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- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
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- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 229910052809 inorganic oxide Inorganic materials 0.000 description 2
- 239000002563 ionic surfactant Substances 0.000 description 2
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- 239000001294 propane Substances 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
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- 229910052706 scandium Inorganic materials 0.000 description 2
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 2
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- LWBHHRRTOZQPDM-UHFFFAOYSA-N undecanedioic acid Chemical compound OC(=O)CCCCCCCCCC(O)=O LWBHHRRTOZQPDM-UHFFFAOYSA-N 0.000 description 2
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- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 2
- 229910052727 yttrium Inorganic materials 0.000 description 2
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- NALFRYPTRXKZPN-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(OOC(C)(C)C)(OOC(C)(C)C)C1 NALFRYPTRXKZPN-UHFFFAOYSA-N 0.000 description 1
- PWVUWMSTEMOYKJ-UHFFFAOYSA-N 1,2-bis(tert-butylperoxy)cyclohexane Chemical compound CC(C)(C)OOC1CCCCC1OOC(C)(C)C PWVUWMSTEMOYKJ-UHFFFAOYSA-N 0.000 description 1
- 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
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- OSNILPMOSNGHLC-UHFFFAOYSA-N 1-[4-methoxy-3-(piperidin-1-ylmethyl)phenyl]ethanone Chemical compound COC1=CC=C(C(C)=O)C=C1CN1CCCCC1 OSNILPMOSNGHLC-UHFFFAOYSA-N 0.000 description 1
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- DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
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- 229910052747 lanthanoid Inorganic materials 0.000 description 1
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- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
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- OHSVLFRHMCKCQY-UHFFFAOYSA-N lutetium atom Chemical compound [Lu] OHSVLFRHMCKCQY-UHFFFAOYSA-N 0.000 description 1
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- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
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- 239000000696 magnetic material Substances 0.000 description 1
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- 229940002712 malachite green oxalate Drugs 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 1
- 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
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- 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
- ABMFBCRYHDZLRD-UHFFFAOYSA-N naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1 ABMFBCRYHDZLRD-UHFFFAOYSA-N 0.000 description 1
- DFFZOPXDTCDZDP-UHFFFAOYSA-N naphthalene-1,5-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1C(O)=O DFFZOPXDTCDZDP-UHFFFAOYSA-N 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
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- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
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- 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
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- 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
- 239000005518 polymer electrolyte Substances 0.000 description 1
- 150000003077 polyols Chemical class 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
- 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
- 239000004172 quinoline yellow Substances 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
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 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
- 229940081623 rose bengal Drugs 0.000 description 1
- 229930187593 rose bengal Natural products 0.000 description 1
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 description 1
- 102220308083 rs1462326368 Human genes 0.000 description 1
- 150000003839 salts Chemical class 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
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- 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
- 235000011044 succinic acid Nutrition 0.000 description 1
- 150000003444 succinic acids Chemical class 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
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 1
- JZFHXRUVMKEOFG-UHFFFAOYSA-N tert-butyl dodecaneperoxoate Chemical compound CCCCCCCCCCCC(=O)OOC(C)(C)C JZFHXRUVMKEOFG-UHFFFAOYSA-N 0.000 description 1
- YOEYNURYLFDCEV-UHFFFAOYSA-N tert-butyl hydroxy carbonate Chemical compound CC(C)(C)OC(=O)OO YOEYNURYLFDCEV-UHFFFAOYSA-N 0.000 description 1
- GSECCTDWEGTEBD-UHFFFAOYSA-N tert-butylperoxycyclohexane Chemical compound CC(C)(C)OOC1CCCCC1 GSECCTDWEGTEBD-UHFFFAOYSA-N 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- FRNOGLGSGLTDKL-UHFFFAOYSA-N thulium atom Chemical compound [Tm] FRNOGLGSGLTDKL-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 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
- 230000007704 transition Effects 0.000 description 1
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 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 aromatic diacid and dithiol are subjected to esterification reaction, a novel polyester resin is prepared by an emulsification method, the toner prepared by using the polyester resin shows excellent developing characteristics, the low-temperature fixing property of the toner is ensured, the toner is not easy to deviate under high-temperature conditions, the charging is uniform at the initial stage of charging and after a period of time, the image quality of a printed image is excellent, the storage property is good, the quality of the printed image is improved, and the pollution to the environment is reduced.
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, demands for higher speed, energy saving, downsizing, and the like of printers and copiers have been increasing, and further improvement of low temperature fixing property of toner has been demanded. Conventionally, a styrene-acrylic resin has been widely used as a binder resin toner, but the styrene-acrylic resin has a large limitation in satisfying energy saving and high gloss image quality in image formation, particularly in low temperature fixing. Therefore, the development of toners using polyester resins as binder resins is rapidly promoted, and the toners tend to be used for printing and copying of the next generation.
With the application of polyester resins as binder resin toners in high-speed printers and copiers, resins having excellent low-temperature fixability and a high-gloss polyester resin structure are mainly used as toners, and although the low-temperature fixability of the toners is ensured by the polyester structure, the resins are easy to generate a shift phenomenon under high-temperature conditions, and the problems of poor image quality, easy blocking during storage and the like caused by a non-uniform phenomenon of a belt point at the initial stage of charging and after a certain period of time are easily caused; the preparation method usually adopts conventional methods such as a phase transition emulsification method and a self-emulsification method, but when the resin particles are dispersed in water, a large amount of organic solvent or a certain amount of surfactant or groups with poor printing effect can be used, and the substances can cause potential adverse effects on the printing quality and the environment.
Disclosure of Invention
The invention provides a toner and a preparation method of the toner, aiming at the problems, the toner which is uniform in particle size, concentrated in dispersion, high in sphericity and good in developing property and storage property is prepared by selecting a dithiol monomer and other various diol monomers to be combined and then carrying out polymerization reaction with an aromatic dicarboxylic acid monomer.
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 obtained 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 of the following compounds in combination: benzene dithiol, 1, 6-hexanedithiol, 1, 7-heptanedithiol, 1, 8-octanedithiol, 1, 9-nonanedithiol, 1, 10-decanedithiol, n-undecanethiol, n-dodecyl mercaptan.
Further, the carboxylic acid compounds comprise one or more of aromatic diacid, aliphatic diacid and trimellitic anhydride; the alcohol compound comprises one or more of bisphenol A ethylene oxide addition product, butanediol and diol with 6-12 carbon atoms.
Further, the aromatic diacid comprises one or more of phthalic acid, isophthalic acid, terephthalic acid, tert-butyl isophthalic acid, 2, 6-naphthalene dicarboxylic acid and 4, 4' -biphenyl dicarboxylic acid;
further, the aliphatic diacid comprises one or more combination of succinic acid, adipic acid, sebacic acid, fumaric acid, maleic acid, and citraconic acid;
further, the diol with 6-12 carbon atoms 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 with 6-12 carbon atoms is 1, 6-hexanediol.
Further, the dithiol accounts for 11.0-16.5 mol% of the alcohol compound, the bisphenol A ethylene oxide adduct accounts for 40-65 mol% of the alcohol compound, and the aromatic diacid accounts for 25-40 mol% of the carboxylic acid compound.
The second aspect of the present invention provides a method for producing a toner, comprising the steps of:
s1: adding a carboxylic acid compound, an alcohol compound and a catalyst into a reaction container, and stirring and reacting for 5-8h at 70-150 ℃ under the protection of nitrogen to obtain polyester resin;
s2: dispersing the prepared polyester resin in a homogenizer for 3-5 min, adding an aqueous solvent, controlling the solid content to be 10-18%, then adding mPEG-SH and/or HS-PEG-SH, reacting by an air oxidation method or a potassium ferricyanide oxidation method, and then stirring at a high speed and dispersing to obtain a 100-200 nm resin emulsion;
s3: adding a coloring agent dispersion liquid and a wax dispersion liquid into the resin emulsion, adjusting the pH to 5.5-7 under the action of a polymerization initiator, slowly heating to 70-85 ℃, keeping for 1-2 hours, then cooling to 50-65 ℃, keeping for 2-3 hours, cooling to room temperature, washing and drying to obtain carbon powder matrix particles, and adding hydrophobized silicon dioxide particles as an external additive to obtain the toner.
Further, the catalyst comprises one or more of titanium tetraethoxide, titanium tetrapropoxide, titanium tetraisopropoxide, titanium tetrabutoxide, dibutyltin dichloride, dibutyltin oxide and diphenyltin oxide, wherein the catalyst accounts for 0.1-0.5 mol% of the total material.
Further, the rotating 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 dispersion degree of 1.10 to 1.32, and a sphericity of 0.96 to 0.98
Has the advantages that:
according to the invention, aromatic diacid and dithiol are subjected to esterification reaction, sulfydryl and sulfur atoms are introduced into polyester resin, the introduction of sulfydryl can effectively replace the addition of a surfactant in the traditional polyester resin preparation process, and the introduction of 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, the burial of the silicon dioxide is reduced, and the storage performance of a toner is improved; the toner prepared by the method has better color density and good storage property, and the toner prepared by the polyester resin has good image quality and keeps higher stability after printing a large number of pages from the perspective of actual printing evaluation effect.
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 illustrative of the present invention and should not be construed as limiting the scope of the present invention. The examples, in which no specific conditions are indicated, were carried out under conventional conditions or conditions recommended by the manufacturer. The reagents or apparatus used are not indicated by the manufacturer, and conventional products are commercially available.
It should be noted that:
in the present invention, all embodiments and preferred methods mentioned herein can be combined with each other to form a new technical solution, if not specifically stated.
In the present invention, unless otherwise specified, the resin range "a-b" represents a shorthand representation of any combination of real numbers between a and b, where a and b are both real numbers, for example, the numerical range "25-40" represents all real numbers between 25-40 that have been fully listed herein, and "25-40" is a shorthand representation of these combinations of numerical values.
In the present invention, unless otherwise specified, each reaction or operation step may be performed in sequence, or may be performed in other sequences, and preferably, the scheme in the present invention is performed in sequence.
Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs, and any methods or materials similar or equivalent to those described herein may be applied to 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 a catalyst into a reaction container, 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 carried out at a temperature of less than or equal to 150 ℃.
The reaction temperature is preferably greater than or equal to 70 ℃ but not greater than 150 ℃; more preferably greater than or equal to 110 ℃ but not more than 140 ℃.
It is preferable to set the reaction temperature to 70 ℃ or higher because this does not cause a decrease in reactivity due to deterioration in solubility of the monomer or activity of the catalyst and does not inhibit an increase in molecular weight. It is also preferable to set the reaction temperature not to exceed 150 ℃ because the production can be carried out with low energy consumption. It is also preferable that no discoloration of the resin occurs or decomposition does not occur on the polyester or the like produced.
< emulsification step >
Dispersing the prepared polyester resin in a homogenizer for 3-5 min, adding an aqueous solvent, controlling the solid content to be 10-18%, then adding mPEG-SH and/or HS-PEG-SH, reacting by an air oxidation method or a potassium ferricyanide oxidation method, and then stirring and dispersing at high speed to obtain 100-200 nm resin emulsion;
among them, examples of the aqueous solvent include: water and alcohols such as distilled water and ion-exchanged water. Particularly preferably, the water-soluble solvent is only water.
Among them, examples of the dispersing equipment used in the emulsification step include a homogenizer, a pressure mixer, an extruder, and a medium disperser, and it is particularly preferable to use a homogenizer in which the rotation speed of the homogenizer is particularly preferably 3000 to 5000 rpm; regarding 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 difficult to aggregate together, and when the average particle diameter exceeds 1 μm, the aggregation potential of the resin particles is enhanced to make the toner particles easier to prepare, but the particle diameter distribution is enlarged.
Wherein mPEG-SH is methoxypolyethyleneglycol thiol, HS-PEG-SH is dimercaptopolyethylene glycol, and the molecular weights of the two substances can be listed as follows: 550, 750, 1000, 2000, 3400, 5000, 10k, 20k, 40k, particularly preferred molecular weight is one or a combination of 1000 and 2000.
< toner combination >
Adding pigment dispersion liquid and wax dispersion liquid into the resin emulsion, adjusting the pH value to 5.5-7 under the action of potassium persulfate or ammonium persulfate, slowly heating to 70-85 ℃, keeping for 1-2 hours, then cooling to 50-65 ℃, keeping for 2-3 hours, cooling to room temperature, washing and drying to obtain carbon powder parent particles, and adding hydrophobized silicon dioxide 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, and when the volume average particle diameter is less than 4 μm, the fluidity of the toner is lowered, which is liable to cause a decrease in the chargeability of each particle on day, background fogging and toner leakage from a developing container due to charge distribution diffusion are liable to occur, and further 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 therefore sufficient image quality may not be obtained, and therefore, it is sometimes difficult to satisfy the recent demand for high image quality.
Alternatively in the present invention, the volume average particle diameter is measured with 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 (aqueous Isoton solution) by ultrasonic treatment for 30 seconds or more, and then used for measurement. The relationship between the measured intensity scale and the range of the divided particle size is plotted, the cumulative distribution of the volume is plotted from the small particle size, and the particle size at which 50% of the volume is accumulated is defined as the volume average particle size.
The average particle size distribution index in the present invention, that is, the particle size dispersion degree of the toner, can be calculated using the values of the particle size up to 16% accumulation defined as the particle size corresponding to the volume D16V and the number D16P and the particle size up to 84% accumulation defined as the particle size corresponding to the volume D84V and the number D84P, and the particle size dispersion degree is preferably 1.10 to 1.32 in the present invention.
In addition, the sphericity of the toner of the present invention is 0.96 to 0.98.
Polyester resin
The polyester resin usable in the present invention can be prepared in an aqueous medium by a direct esterification reaction, a transesterification reaction, etc. using a polycondensation monomer such as aliphatic, alicyclic and aromatic polyfunctional carboxylic acids, alkyl esters and polyhydric alcohols, ester compounds thereof, hydroxycarboxyl groups, etc.
In the present invention, it is preferable to prepare the polyester resin by directly esterifying a carboxylic acid compound and an alcohol compound in the presence of a catalyst.
In the present invention, the polyester resin has a molecular weight of 5,000-1,000,000, more alternatively a weight average molecular weight (Mw) of 7000-500,000, and the number average molecular weight (Mn) of 2,000-10,000, and the high molecular weight distribution Mw/Mn is alternatively 1.5-100, and further alternatively 2-60, based on the molecular weight of the Tetrahydrofuran (THF) soluble substance measured by a Gel Permeation Chromatography (GPC) method, the molecular weight of the resin is calculated by measuring the molecular weight of the THF soluble substance in the THF solution (manufactured by TosoH Corporation) using GPC-HLC-8120 and column-TSK gel super HM-M (15cm), and the molecular weight calibration curve generated from a monodisperse polystyrene standard sample is used. The acid value of the polyester resin (in terms of the amount of KOH necessary for neutralizing 1g of the resin) may be selected from 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 change in temperature or humidity) 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 group at the end of the polyester, i.e., adjusting the mixing ratio of the polycarboxylic acid and the polyol in the raw materials and the reaction rate.
From the viewpoint of the balance between the storage stability and the fixing property of the toner, the glass transition temperature of the amorphous polymer used in the present embodiment is preferably 35 to 100 ℃, and more preferably 50 to 80 ℃. When the glass transition temperature is less than 35 ℃, there is a tendency that the toner easily causes blocking (a phenomenon in which toner particles aggregate to form lumps) 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 amorphous polymer may have a softening point 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 toner and the image stability of the toner after fixing and after storage are drastically deteriorated. When the softening point is higher than 130 ℃, the low-temperature fixability deteriorates. The softening point of the amorphous polymer indicates the softening point of the amorphous polymer in a pre-heated state by a flow tester (trade name CFT-500C; manufactured by Shimadzu Corporation): intermediate temperature between melting start temperature and melting end temperature measured under the condition of 80 ℃,/300 seconds, plunger pressure: 0.980665MPa, die size: temperature rise rate: 3.0 deg.C/min.
Carboxylic acid compound
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 the dicarboxylic acid has two carboxyl groups in one molecule, and the carboxylic acid-based compounds of the present invention include aromatic diacids, aliphatic diacids, and polyfunctional carboxylic acids, and examples thereof include, for example, oxalic acid, glutaric acid, succinic acid, maleic acid, adipic acid, β -methyladipic acid, azelaic acid, sebacic acid, nonanedioic acid, decanedioic acid, 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, tert-butylisophthalic acid, tetrachlorophthalic acid, chlorophthalic acid, nitrophthalic acid, p-carboxyphthalic acid, p-phenylenediacetic acid, m-phenylenediglycolic acid, p-phenylenediglycolic acid, o-phenylenediglycolic acid, diphenylacetic acid, 4' -biphenyldicarboxylic acid, naphthalene-1, 4-dicarboxylic acid, naphthalene-1, 5-dicarboxylic acid, 2, 6-naphthalenedicarboxylic acid, anthracenedicarboxylic acid, cyclohexanedicarboxylic acid, 2, 6-naphthalenedicarboxylic acid, and the like; examples of the polyfunctional carboxylic acid other than the dicarboxylic acid include trimellitic anhydride, pyromellitic acid, naphthalenetricarboxylic acid, naphthalenetetracarboxylic acid, pyrenetricarboxylic acid, pyrenetetracarboxylic acid, and the like.
Preferably, the aromatic diacid comprises one or more combinations of phthalic acid, isophthalic acid, terephthalic acid, t-butyl isophthalic 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 characteristics 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 and succinic acids, and the polyfunctional carboxylic acid is trimellitic anhydride.
Alcohol compounds
The alcohol compound in the present invention includes a polyol compound, i.e., a compound having two or more hydroxyl groups in one molecule, among which diols are compounds 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 the diol include glycerin, pentaerythritol, hexamethylolmelamine, hexahydroxyethylmelamine, tetramethylolbenzoguanamine, and tetrahydroxyethylbenzoguanamine.
In view of the fact that the monomer having a main structure carbon number of 6 or more is easily prepared, and the monomer having a main structure carbon number of 12 or less has a suitable molecular size and the reactivity is not lowered due to the restriction of molecular motion, the alcohol compound preferably contains one or more combinations of 1, 6-hexanediol, 1, 7-heptanediol, 1, 8-octanediol, 1, 9-nonanediol, 1, 10-decanediol, 1, 11-undecanediol, and 1, 12-dodecanediol.
Particularly preferably, the diol having 6 to 12 carbon atoms is 1, 6-hexanediol.
The alcohol compound in the invention also comprises bisphenol A ethylene oxide addition compound; the ethylene oxide addition product can effectively inhibit the delocalization effect generated by resonance stabilization between hydroxyl and aromatic ring in the bisphenol A structure, and can strengthen nucleophilic attack of diol on polycarboxylic acid after the ethylene oxide addition product is added, so that the molecular weight growth and polymerization degree progress can be kept at good level.
The alcohol compound in the present invention includes dithiol, which means a dithiol structure containing two mercapto functional groups in a molecule, and examples thereof include, for example, one or a combination of more of benzenedithiol, 1, 6-hexanedithiol, 1, 7-heptanedithiol, 1, 8-octanedithiol, 1, 9-nonanedithiol, 1, 10-decanedithiol, n-undecanethiol, and n-dodecylthiol.
Preferably, the dithiol comprises one or more of 1, 10-decanedithiol, benzenedithiol, 1, 6-hexanedithiol, and n-dodecyl mercaptan.
The aforementioned dithiol is particularly preferably one or a combination of more of 1, 10-decanedithiol, benzenedithiol, and 1, 6-hexanedithiol, from the viewpoints of good non-crystallization characteristics of the polyester resin and reduction of the odor of the toner itself.
In addition, it has been found that the development property and the storage property can be more effectively improved by including a small amount of butanediol or propylene glycol in the alcohol compound, and particularly preferably, the alcohol compound further includes butanediol.
The amorphous characteristics of the above polyester resin are also referred to as amorphous polyester resin, and "crystallinity" means: distinct endothermic peaks can be distinguished by Differential Scanning Calorimetry (DSC) instead of gradual endothermic changes; more specifically, the half-width of the endothermic peak measured at a heating rate of 10 ℃/minute was in the range of 15 ℃, whereas a resin having the generated endothermic peak with a half-width exceeding 15 ℃ or a resin having no significant endothermic peak indicates that it is amorphous (amorphous).
In the embodiment of the invention, dithiol accounts for 11.0-16.5 mol% of the alcohol compound, preferably dithiol accounts for 13-15.5 mol% of the alcohol compound, and particularly preferably dithiol accounts for 14.5-15.5 mol% of the alcohol compound; the bisphenol A ethylene oxide addition product accounts for 40-65 mol% of the alcohol compound, preferably 44-64 mol% of the alcohol compound, and particularly preferably 44-49 mol% or 60-64 mol% of the alcohol compound; the aromatic diacid accounts for 26 to 38mol percent of the total carboxylic acid compounds, preferably the aromatic diacid accounts for 30 to 38mol percent of the total carboxylic acid compounds, and particularly preferably the aromatic diacid accounts for 35 to 37mol percent of the total carboxylic acid compounds.
Catalyst and process for preparing same
The catalyst of the present invention is an organometallic catalyst, non-limiting examples of which include: such as organotin compounds, organotitanium compounds, organohalogenotin compounds, rare earth metal catalysts, etc.
Specifically, scandium (Sc), yttrium (Y); lanthanoid elements 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). When used as alkyl benzeneThese elements are particularly effective in the structures of acid salts, alkyl sulfates, triflates, and the like. An example of a triflate salt may be represented by the formula X (OSO)2CF3)3Wherein X represents a rare earth metal element, and particularly preferably X is scandium (Sc), yttrium (Y), ytterbium (Yb), samarium (Sm), or the like.
In the embodiment of the invention, one or a combination of an organic tin compound and/or an organic titanium compound is preferred, wherein the organic titanium compound comprises one or a combination of more of titanium tetraethoxide, titanium tetrapropoxide, titanium tetraisopropoxide and titanium tetrabutoxide, and the organic tin compound comprises one or a combination of more of dibutyltin dichloride, dibutyltin oxide and diphenyltin oxide.
Particularly preferably, the catalyst in the embodiment of the invention is dibutyltin oxide, and the feeding amount of the dibutyltin oxide accounts for 0.1-0.5 mol% of the total material amount.
Polymerization initiator
In the present invention, a polymerization initiator is added in the polymerization process, and known polymerization initiators can be used, and specific examples thereof include ammonium persulfate, potassium persulfate, sodium persulfate, 2 ' -azobis (2-methylpropionamido) dihydrochloride, tert-butyl peroxy-2-ethylhexanoate, isopropylphenyl perpivalate, tert-butyl peroxylaurate, benzoyl peroxide, lauroyl peroxide, octanoyl peroxide, di-tert-butyl peroxide, tert-butylcumyl peroxide, dicumyl peroxide, 2 ' -azobisisobutyronitrile, 2 ' -azobis (2-methylbutyronitrile), 2 ' -azobis (2, 4-dimethylvaleronitrile), 2 ' -azobis (4-methoxy-2, 4-dimethylvaleronitrile), 1, 1-bis (t-butylperoxy) -3, 3, 5-trimethylcyclohexane, 1-bis (t-butylperoxy) cyclohexane, 1, 4-bis (t-butylperoxycarbonyl) cyclohexane, 2-bis (t-butylperoxy) octane, n-butyl-4, 4-bis (t-butylperoxyisopropyl) valerate, 2-bis (t-butylperoxy) butane, 1, 3-bis (t-butylperoxyisopropyl) benzene, 2, 5-dimethyl-2, 5-bis (t-butylperoxy) hexane, 2, 5-dimethyl-2, 5-bis (benzoylperoxy) hexane, di-t-butyl-isophthalate, 2-bis (4, 4-di-t-butylperoxycyclohexyl) propane, 2, 1-bis (t-butylperoxy) cyclohexane, 1, 4-t-butylperoxy-isopropyl) propane, n-butyl-4, 4-bis (t-butylperoxy-isopropyl) valerate, 2, 5-dimethyl-2, 5-bis (benzoylperoxy) hexane, 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-butylperoxycarbonate), 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, one or more known additives may be mixed singly or in combination as necessary, and the result of the present invention may not be affected, and for example, a flame retardant aid, a polishing agent, a water repellent agent, a magnetic material, an inorganic filler (surface modifier), an antioxidant, a plasticizer, a surfactant, a dispersant, a lubricant, a filler, a pigment, a binder, a charge control agent, and the like may be added. These additives may be mixed at any time of manufacturing the coating agent.
Colorant dispersion liquid
The colorant dispersion liquid contains a colorant, wherein the colorant dispersion liquid is prepared by dispersing and dissolving the colorant, and preferable examples of an apparatus which is usually used for dispersing the colorant include a medium type dispersing machine such as a rotary shear homogenizer, a ball mill, a sand mill or an attritor, and a high-pressure opposed 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, chroma, brightness, weather resistance, OHP permeability, and dispersibility in the 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 Yellow pigments include hansa Yellow, hansa Yellow 10G, benzidine Yellow GR, Threne 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 Bengal, 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, chalcoi 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 a solid solution state.
Wax dispersion
The toner of the present invention further contains a wax dispersion, wherein examples of the wax dispersion include vegetable waxes such as ester wax, carnauba wax, rice bran wax, candelilla wax, wood wax, jojoba oil, etc.; animal waxes such as beeswax; mineral or petroleum waxes such as montan wax, ozokerite, ceresin, paraffin wax, microcrystalline wax, and Fischer-Tropsch wax; modified products thereof may also be used.
The melting point of the wax is preferably 60 ℃ or higher, more preferably 65 ℃ or higher, and still more preferably 70 ℃ or higher. Since the wax having a melting point in the above range can suppress the fluidity of the toner and filming to the photoreceptor.
The wax is dispersed in water together with an ionic surfactant, a polymer electrolyte such as a polymer acid or a polymer base, and then micronized by using a homogenizer or a pressure-release type disperser capable of applying a strong shearing force while heating to a temperature of the melting point or higher. In this way, a wax dispersion of particles having a particle size of 1 μm or less 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 500 nm. Since the particle diameter of the agglomerated particles can be easily controlled and a good effect as a releasing agent can be obtained by setting the weight average particle diameter of the wax particles within the above range.
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 and charge exchange properties, etc., generally include inorganic oxides such as silica, titania and alumina and are made to adhere to the obtained toner particles. The procedure can be carried out with a V-blender, henschel mixer or LODIGE mixer, and the attachment can be carried out in stages.
Examples of the inorganic particles include particles of silica, alumina, titanium dioxide, barium titanate, magnesium titanate, calcium titanate, strontium titanate, zinc oxide, quartz sand, clay, mica, wollastonite, diatomaceous earth, cerium chloride, red iron oxide, chromium oxide, cerium oxide, antimony trioxide, magnesium oxide, zirconium oxide, silicon carbide, silicon nitride, and the like. Among these, silica particles and/or titania particles are preferable. Particularly, hydrophobized silica particles or titania particles are preferable from the viewpoint of stabilizing the chargeability and developability of the toner.
As a method for surface modification, a known method may be used, specifically including a 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-aminopropyltrimethoxysilane, gamma-chloropropyltrimethoxysilane, gamma-bromopropyltrimethoxysilane, gamma-glycidoxypropyltrimethoxysilane, gamma-mercaptopropyltrimethoxysilane, gamma-ureidopropyltrimethoxysilane, fluoroalkyltrimethoxysilane and hexamethyldisilazane titanate coupling agent aluminate coupling agents.
The amount of the external additive added 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 part by weight, the fluidity of the toner may be deteriorated and further the deterioration of the charging property and the charge exchange property may be observed, and when the amount of the external additive exceeds 5 parts by weight, the toner is in a state of being excessively coated, so that an excessive inorganic oxide is transferred to the contact member, sometimes causing a secondary obstacle.
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 purpose. If the toner for developing an electrostatic image is used alone, a one-component electrostatic image developer is prepared, whereas 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.; 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 having magnetic particles dispersed therein, the carrier comprising the 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 coating 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 with respect to 100 parts by weight of the carrier.
Examples
The present invention is described in detail by referring to examples, but it should be understood that the present invention is not limited thereto, unless otherwise specified in the description.
Preparation of colorant Dispersion
30g of carbon black (Cabot corporation) and 7.5g of sodium lauryl sulfate and 62.5g of water were pre-dispersed at room temperature with stirring, and then this dispersion was added to a high-speed dispersant to carry out dispersion, followed by dispersion for 2 hours, to obtain a colorant dispersion. The particle size of the product is 181nm and the solid content is 30% by a nanometer particle size analyzer.
Preparation of wax Dispersion
30g of carnauba wax (RC-160, manufactured by TOA Kasei Co., Ltd.), 7.5g of sodium lauryl sulfate and 62.5g of water were dissolved with stirring at 90 ℃ and then the mixture was rapidly added to a high-speed dispersant for dispersion for 2 hours to obtain a milky wax dispersion. The particle size was 158nm and the solids content was 30% as measured by a nanometer particle sizer.
Example 1
Preparation of toner-T1
0.01mol (1.66g) of terephthalic acid, 0.01mol (1.16g) of fumaric acid, 0.01mol (1.18g) of succinic acid, 0.02mol (6.32g) of bisphenol A ethylene oxide adduct, 0.004mol (0.472g) of butanediol, 0.005mol (0.590g) of 1, 6-hexanediol, and 0.0979g (0.00032mol) of dibutyltin oxide were charged into a reaction vessel, and the mixture was subjected to polycondensation reaction at 130 ℃ for 7 hours under nitrogen protection with stirring, and then 0.003mol (0.618g) of 1, 10-decanedithiol and 0.002mol (0.284g) 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%, then adding 0.003mol of mPEG-SH-1000(mPEG-SH-1000 represents that mPEG-SH has the molecular weight of 1000), oxidizing by air, stirring at 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, adjusting the pH value to 7 under the action of potassium persulfate, slowly heating to 85 ℃, keeping the temperature for 1h, then cooling to 65 ℃, keeping the temperature 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 (1.328g) of terephthalic acid, 0.013mol (1.508g) of fumaric acid, 0.009mol (1.062g) of succinic acid, 0.018mol (5.688g) of bisphenol A ethylene oxide adduct, 0.005mol (0.59g) of butanediol, 0.006mol (0.709g) of 1, 6-hexanediol, and 0.0979g (0.00032mol) of dibutyltin oxide were charged into a reaction vessel, stirred under nitrogen atmosphere, and polycondensed at 70 ℃ for 8 hours, then 0.003mol (0.618g) of 1, 10-decanedithiol and 0.002mol (0.284g) 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 percent, adding 0.0033mol of mPEG-SH-1000(mPEG-SH-1000 represents that mPEG-SH has the molecular weight of 1000), oxidizing by air, stirring at 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, adjusting the pH value to 5.5 under the action of potassium persulfate, slowly heating to 70 ℃, keeping the temperature for 2h, then cooling to 50 ℃, keeping the temperature for 2h, cooling to room temperature, washing with water, drying, and adding 3.8g of hydrophobically modified silicon dioxide to obtain toner T2.
Example 3
Preparation of toner-T3
0.009mol (1.494g) of terephthalic acid, 0.009mol (1.044g) of fumaric acid, 0.01mol (1.18g) of succinic acid, 0.002mol (0.384g) of trimellitic anhydride, 0.02mol (6.32g) of bisphenol A ethylene oxide adduct, 0.003mol (0.354g) of butanediol, 0.006mol (0.709g) of 1, 6-hexanediol and 0.0979g (0.00032mol) of dibutyltin oxide were charged into a reaction vessel, stirred under nitrogen protection, and polycondensed at 130 ℃ for 7 hours, then 0.0015mol (0.309g) of 1, 10-decanedithiol and 0.0035mol (0.497g) 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%, then adding 0.0028mol of mPEG-SH-1000(mPEG-SH-1000 represents that mPEG-SH has the molecular weight of 1000), oxidizing by air, stirring at 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, adjusting the pH value to 6.5 under the action of potassium persulfate, slowly heating to 85 ℃, keeping the temperature for 1h, then cooling to 65 ℃, keeping the temperature for 2h, cooling to room temperature, washing with water, drying, and adding 3.8g of hydrophobically modified silicon dioxide to obtain toner T3.
Example 4
Preparation of toner-T4
0.0095mol (1.577g) of terephthalic acid, 0.0088mol (1.0208g) of fumaric acid, 0.0107mol (1.2626g) of succinic acid, 0.001mol (0.192g) of trimellitic anhydride, 0.019mol (6.004g) of bisphenol A ethylene oxide adduct, 0.0075mol (0.885g) of butanediol, 0.002mol (0.2363g) of 1, 6-hexanediol and 0.0979g (0.00032mol) of dibutyltin oxide are added into a reaction vessel, stirred under the protection of nitrogen, and subjected to polycondensation reaction at 130 ℃ for 7 hours, then 0.0019mol (0.3914g) of 1, 10-decanedithiol and 0.0026mol (0.3692g) of benzenedithiol are added, and the reaction is continued at 150 ℃ for 7 hours, so as 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%, then adding 0.0027mol of mPEG-SH-1000(mPEG-SH-1000 represents that mPEG-SH has the molecular weight of 1000), oxidizing by air, stirring at 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, adjusting the pH value to 6.5 under the action of potassium persulfate, slowly heating to 85 ℃, keeping the temperature for 1h, then cooling to 65 ℃, keeping the temperature for 2h, cooling to room temperature, washing with water, drying, and adding 3.8g of hydrophobically modified silicon dioxide to obtain toner T4.
Example 5
Preparation of toner-T5
0.0115mol (1.909g) of terephthalic acid, 0.008mol (1.0208g) of fumaric acid, 0.0105mol (1.239g) of succinic acid, 0.0195mol (6.162g) of bisphenol A ethylene oxide adduct, 0.0045mol (0.531g) of butanediol, 0.0048mol (0.5672g) of 1, 6-hexanediol and 0.0979g (0.00032mol) of dibutyltin oxide were charged into a reaction vessel, stirred under the protection of nitrogen, and polycondensed at 130 ℃ for 7 hours, then 0.0025mol (0.515g) of 1, 10-decanedithiol and 0.0017mol (0.2414g) 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 3500rpm of a homogenizer, adding water to adjust the solid content to 15%, then adding 0.0025mol of mPEG-SH-2000(mPEG-SH-2000 represents that the molecular weight of mPEG-SH is 2000), oxidizing by air, stirring at 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, adjusting the pH value to 7 under the action of potassium persulfate, slowly heating to 85 ℃, keeping the temperature for 1h, then cooling to 65 ℃, keeping the temperature 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 (1.4608g) of terephthalic acid, 0.0087mol (1.0092g) of fumaric acid, 0.011mol (1.298g) of succinic acid, 0.0015mol (0.288g) of trimellitic anhydride, 0.0213mol (6.7308g) of bisphenol A ethylene oxide adduct, 0.0054mol (0.6372g) of butanediol, 0.0017mol (0.2009g) of 1, 6-hexanediol and 0.0979g (0.00032mol) of dibutyltin oxide are added into a reaction vessel, stirred under the protection of nitrogen, and polycondensation reaction is carried out at 130 ℃ for 7 hours, then 0.0031mol (0.6386g) of 1, 10-decanedithiol and 0.0022mol (0.3124g) of benzenedithiol are added, and reaction is continued at 150 ℃ for 7 hours, so as to obtain the 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%, then adding 0.0013mol of mPEG-SH-2000 and 0.0015mol of mPEG-SH-1000(mPEG-SH-2000 represents that mPEG-SH molecular weight is 2000, and mPEG-SH-1000 represents that mPEG-SH molecular weight is 1000), oxidizing by air, stirring at 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, adjusting the pH value to 7 under the action of potassium persulfate, slowly heating to 85 ℃, keeping the temperature for 1h, then cooling to 65 ℃, keeping the temperature 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 (1.5272g) of terephthalic acid, 0.011mol (1.0092g) of fumaric acid, 0.0087mol (1.0266g) of succinic acid, 0.0011mol (0.2112g) of trimellitic anhydride, 0.0208mol (6.5728g) of bisphenol A ethylene oxide adduct, 0.0061mol (0.7198g) of butanediol, 0.001mol (0.118g) of 1, 6-hexanediol and 0.0979g (0.00032mol) of dibutyltin oxide are added into a reaction vessel, stirred under the protection of nitrogen, and subjected to polycondensation reaction at 130 ℃ for 7 hours, then 0.0044mol (0.9064g) of 1, 10-decanedithiol and 0.0011mol (0.1562g) of benzenedithiol are added, and the reaction is continued at 150 ℃ for 7 hours, so as to obtain the 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%, then adding 0.0012mol of mPEG-SH-2000 and 0.0011mol of mPEG-SH-1000(mPEG-SH-2000 represents that mPEG-SH molecular weight is 2000, and mPEG-SH-1000 represents that mPEG-SH molecular weight is 1000), oxidizing by air, stirring at 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, adjusting the pH value to 7 under the action of potassium persulfate, slowly heating to 85 ℃, keeping the temperature for 1h, then cooling to 65 ℃, keeping the temperature 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 (1.6434g) of terephthalic acid, 0.0059mol (0.6844g) of fumaric acid, 0.0133mol (1.5694g) of succinic acid, 0.0009mol (0.1728g) of trimellitic anhydride, 0.0188mol (5.9408g) of bisphenol A ethylene oxide adduct, 0.0079mol (0.9322g) of butanediol, 0.002mol (0236g) of 1, 6-hexanediol and 0.0979g (0.00032mol) of dibutyltin oxide are added into a reaction vessel, stirred under the protection of nitrogen, and polycondensation reaction is carried out at 130 ℃ for 7h, then 0.0035mol (0.721g) of 1, 10-decanedithiol and 0.0021mol (0.2982g) of benzenedithiol are added, and reaction is continued at 150 ℃ for 7h, so as 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, then 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 of 2000, and SH-PEG-SH-1000 represents SH-PEG-SH molecular weight of 1000), and after air oxidation, stirring at 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, adjusting the pH value to 7 under the action of potassium persulfate, slowly heating to 85 ℃, keeping the temperature for 1h, then cooling to 65 ℃, keeping the temperature 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 (1.826g) of terephthalic acid, 0.007mol (0.812g) of fumaric acid, 0.0118mol (1.3924g) of succinic acid, 0.0002mol (0.0384g) of trimellitic anhydride, 0.0155mol (4.898g) of bisphenol A ethylene oxide adduct, 0.0088mol (1.0384g) of butanediol, 0.005mol (0.590g) of 1, 6-hexanediol and 0.0979g (0.00032mol) of dibutyltin oxide are added into a reaction vessel, stirred under the protection of nitrogen, and are subjected to polycondensation reaction at 130 ℃ for 7 hours, then 0.0033mol (0.6798g) of 1, 10-decanedithiol, 0.0008mol (0.1136g) of benzenedithiol and 0.0011mol (0.165g) of 1, 6-hexanedithiol are added, and the reaction is continued at 150 ℃ for 7 hours, so as 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 be 14 percent, then 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 of 2000, and SH-PEG-SH-1000 represents SH-PEG-SH molecular weight of 1000), and after air oxidation, stirring at 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, adjusting the pH value to 7 under the action of potassium persulfate, slowly heating to 85 ℃, keeping the temperature for 1h, then cooling to 65 ℃, keeping the temperature 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 (1.66g) of terephthalic acid, 0.0088mol (1.0208g) of fumaric acid, 0.0112mol (1.3216g) of succinic acid, 0.0171mol (5.4036g) of bisphenol A ethylene oxide adduct, 0.0078mol (0.9204g) of butanediol, 0.0045mol (0.532g) of 1, 6-hexanediol, and 0.0979g (0.00032mol) of dibutyltin oxide were charged into a reaction vessel, stirred under the protection of nitrogen, and polycondensed at 130 ℃ for 7 hours, then 0.004mol (0.824g) of 1, 10-decanedithiol, 0.0005mol (0.071g) of benzenedithiol, and 0.0006mol (0.09g) of 1, 6-hexanedithiol 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 be 14 percent, then 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 of 2000, and SH-PEG-SH-1000 represents SH-PEG-SH molecular weight of 1000), and after air oxidation, stirring at 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, adjusting the pH value to 7 under the action of potassium persulfate, slowly heating to 85 ℃, keeping the temperature for 1h, then cooling to 65 ℃, keeping the temperature 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 (1.743g) of terephthalic acid, 0.0105mol (1.218g) of fumaric acid, 0.009mol (1.062g) of succinic acid, 0.0179mol (5.6564g) of bisphenol A ethylene oxide adduct, 0.0088mol (1.0384g) of butanediol, 0.003mol (0.354g) of 1, 6-hexanediol and 0.0979g (0.00032mol) of dibutyltin oxide are added into a reaction vessel, stirred under the protection of nitrogen and polycondensed at 130 ℃ for 7 hours, then 0.0032mol (0.6592g) of 1, 10-decanedithiol, 0.0005mol (0.071g) of benzenedithiol and 0.0001mol (0.015g) of 1, 6-hexanedithiol are added and the reaction is 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, then 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 of 2000, and SH-PEG-SH-1000 represents SH-PEG-SH molecular weight of 1000), and after air oxidation, stirring at 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, adjusting the pH value to 7 under the action of potassium persulfate, slowly heating to 85 ℃, keeping the temperature for 1h, then cooling to 65 ℃, keeping the temperature 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 (1.8426g) of terephthalic acid, 0.0101mol (1.1716g) of fumaric acid, 0.0047mol (0.5546g) of succinic acid, 0.0041mol (0.7872g) of trimellitic anhydride, 0.021mol (6.636g) of bisphenol A ethylene oxide adduct, 0.004mol (0.472g) of butanediol, 0.0033mol (0.389g) of 1, 6-hexanediol and 0.00032mol (0.0979g) of dibutyltin oxide were added into a reaction vessel, stirred under the protection of nitrogen, and polycondensed at 130 ℃ for 7 hours, then 0.004mol (0.824g) of 1, 10-decanedithiol, 0.0005mol (0.071g) of benzenedithiol and 0.0003mol (0.045g) of 1, 6-hexanedithiol were added, and 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, then 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 of 2000, and SH-PEG-SH-1000 represents SH-PEG-SH molecular weight of 1000), and after air oxidation, stirring at 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, adjusting the pH value to 7 under the action of potassium persulfate, slowly heating to 85 ℃, keeping the temperature for 1h, then cooling to 65 ℃, keeping the temperature 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 (1.66g) of terephthalic acid, 0.01mol (1.16g) of fumaric acid, 0.01mol (1.18g) of succinic acid, 0.02mol (6.32g) of bisphenol A ethylene oxide adduct, 0.004mol (0.472g) of butanediol, 0.01mol (1.1817g) of 1, 6-hexanediol, 0.005mol (1.5417g) of dodecyltrimethylammonium bromide and 0.00032mol (0.0979g) of dibutyltin oxide were charged into a reaction vessel, stirred under nitrogen protection 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%, then adding 0.003mol of mPEG-SH-1000(mPEG-SH-1000 represents that mPEG-SH has the molecular weight of 1000), oxidizing by air, stirring at 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, adjusting the pH value to 7 under the action of potassium persulfate, slowly heating to 85 ℃, keeping the temperature for 1h, then cooling to 65 ℃, keeping the temperature 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 (1.66g) of terephthalic acid, 0.01mol (1.16g) of fumaric acid, 0.01mol (1.18g) of succinic acid, 0.02mol (6.32g) of bisphenol A ethylene oxide adduct, 0.004mol (0.472g) of butanediol, 0.006mol (0.709g) of 1, 6-hexanediol, 0.005mol (1.5417g) of dodecyltrimethylammonium bromide and 0.00032mol (0.0979g) of dibutyltin oxide were charged into a reaction vessel, stirred under nitrogen protection, and subjected to polycondensation reaction at 130 ℃ for 7 hours, and then reacted at 150 ℃ for 7 hours to obtain a polyester resin. Obtaining the 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 be 10%, then adding 0.003mol of mPEG-SH-500(mPEG-SH-500 represents that mPEG-SH has the molecular weight of 500), oxidizing by air, stirring at 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, adjusting the pH value to 7 under the action of potassium persulfate, slowly heating to 85 ℃, keeping the temperature for 1h, then cooling to 65 ℃, keeping the temperature 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 (1.66g) of terephthalic acid, 0.01mol (1.16g) of fumaric acid, 0.01mol (1.18g) of succinic acid, 0.02mol (6.32g) of bisphenol A ethylene oxide adduct, 0.004mol (0.472g) of butanediol, 0.005mol (0.590g) of 1, 6-hexanediol, 0.005mol (1.5417g) of dodecyltrimethylammonium bromide and 0.00032mol (0.0979g) of dibutyltin oxide were charged into a reaction vessel, stirred under nitrogen protection, and subjected to polycondensation reaction at 130 ℃ for 7 hours, and then reacted at 150 ℃ for 7 hours to obtain a polyester resin. Obtaining the 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 be 10%, then adding 0.003mol of mPEG-SH-3000(mPEG-SH-3000 represents that mPEG-SH molecular weight is 3000), oxidizing by air, stirring at 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, adjusting the pH value to 7 under the action of potassium persulfate, slowly heating to 85 ℃, keeping the temperature for 1h, then cooling to 65 ℃, keeping the temperature 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 of the above examples and comparative examples was mixed with carrier particles (a magnetic particle for making the toner magnetic for printing and copying) to prepare a finished toner, and the printing effect was tested on a practical machine by: 5000 ten thousand continuous printing tests were performed in a normal temperature and humidity (20 ℃/50% RH) environment, and the test results are shown in table 2 below.
Evaluation of storage Property
10g of the toner was charged into an open-system round container, allowed to stand at 50 ℃ under a 60% humidity environment for 72 hours, and then gently transferred into the container containing the toner, and it was visually observed whether or not the toner was aggregated. No surface aggregation of the toner was observed, which means excellent storability; if the surface of the toner is agglomerated, but the agglomeration can be eliminated without vibration during transfer, and the actual printing effect is not influenced, the effect is represented as good; if the toner surface is aggregated and the vibration is not eliminated during the transfer, the storage stability is poor. The evaluation results are shown in Table 2.
TABLE 2
It should be noted that, according to the explanation and illustration of the above description, the person skilled in the art to which the present invention pertains can make variations and modifications to the above embodiments. Therefore, the present invention is not limited to the specific embodiments disclosed and described above, and some equivalent modifications and variations of the present invention should be covered by the protection scope of the claims of the present invention. Furthermore, although specific terms are employed herein, they are used in a generic and descriptive sense only and not for purposes of limitation.
Claims (10)
1. A toner, characterized by comprising a polyester resin, a colorant, a wax, and an external additive; the polyester resin is obtained by reacting carboxylic acid compounds, alcohol compounds and a catalyst under certain conditions, wherein the alcohol compounds comprise dithiol.
2. The toner according to claim 1, wherein the dithiol comprises one or more combinations of the following compounds: benzene dithiol, 1, 6-hexanedithiol, 1, 7-heptanedithiol, 1, 8-octanedithiol, 1, 9-nonanedithiol, 1, 10-decanedithiol, n-undecanethiol, n-dodecyl mercaptan.
3. The toner according to claim 1, wherein the carboxylic acid-based compound comprises one or more of an aromatic diacid, an aliphatic diacid, and trimellitic anhydride; the alcohol compound comprises one or more of bisphenol A ethylene oxide addition product, butanediol and diol with 6-12 carbon atoms.
4. The toner according to claim 3, wherein the aromatic diacid comprises one or more combinations of phthalic acid, isophthalic acid, terephthalic acid, t-butylisophthalic acid, 2, 6-naphthalenedicarboxylic acid, 4' -biphenyldicarboxylic acid;
the aliphatic diacid comprises one or more combinations of succinic acid, adipic acid, sebacic acid, fumaric acid, maleic acid, citraconic acid;
the diol with 6-12 carbon atoms 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.
5. The toner according to claim 4, 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.
6. The toner according to any one of claims 1 to 4, wherein the dithiol accounts for 11.0 to 16.5 mol% of the alcohol compound, the bisphenol A ethylene oxide adduct accounts for 40 to 65 mol% of the alcohol compound, and the aromatic diacid accounts for 25 to 40 mol% of the carboxylic acid compound.
7. A method for producing a toner, characterized by comprising the steps of:
s1: adding a carboxylic acid compound, an alcohol compound and a catalyst into a reaction container, and stirring and reacting for 5-8h at 70-150 ℃ under the protection of nitrogen to obtain polyester resin;
s2: dispersing the prepared polyester resin in a homogenizer for 3-5 min, adding an aqueous solvent, controlling the solid content to be 10-18%, then adding mPEG-SH and/or HS-PEG-SH, reacting by an air oxidation method or a potassium ferricyanide oxidation method, and then stirring at a high speed and dispersing to obtain a 100-200 nm resin emulsion;
s3: adding a coloring agent dispersion liquid and a wax dispersion liquid into the resin emulsion, adjusting the pH to 5.5-7 under the action of a polymerization initiator, slowly heating to 70-85 ℃, keeping for 1-2 hours, then cooling to 50-65 ℃, keeping for 2-3 hours, cooling to room temperature, washing and drying to obtain carbon powder matrix particles, and adding hydrophobized silicon dioxide particles as an external additive to obtain the toner.
8. The method of preparing the toner according to claim 7, wherein the catalyst comprises one or more of titanium tetraethoxide, titanium tetrapropoxide, titanium tetraisopropoxide, titanium tetrabutoxide, dibutyltin dichloride, dibutyltin oxide and diphenyltin oxide in combination, wherein the catalyst is 0.1 to 0.5 mol% based on the total amount of the materials.
9. The method for producing the toner according to claim 7, wherein a rotation speed of the homogenizer is 3000 to 5000 rpm.
10. The method for producing the toner according to claim 7, wherein the toner has an average particle diameter of 4.5 to 8.5 μm, a dispersion degree of particle diameters of 1.10 to 1.32, and a sphericity of 0.96 to 0.98.
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Citations (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1920677A (en) * | 2005-08-26 | 2007-02-28 | 富士施乐株式会社 | Binder resin for electrostatic image developing toner, binder resin liquid dispersion for electrostatic image developing toner, electrostatic image developing toner, and production processes thereof |
US20070254228A1 (en) * | 2006-04-26 | 2007-11-01 | Xerox Corporation | Toner compositions and processes |
CN101075100A (en) * | 2006-05-17 | 2007-11-21 | 富士施乐株式会社 | Toner for developing electrostatic images, electrostaic image development and imaging method thereof |
CN101089739A (en) * | 2006-02-13 | 2007-12-19 | 株式会社理光 | Toner, developer, toner-containing container, process cartridge, image-forming apparatus and image-forming process |
KR20080051252A (en) * | 2006-12-05 | 2008-06-11 | 에스케이케미칼주식회사 | Polyester resin and toner including the same |
JP2009037255A (en) * | 2008-10-10 | 2009-02-19 | Konica Minolta Business Technologies Inc | Electrostatic latent image developing toner, and manufacturing method of electrostatic latent image developing toner |
CN101655674A (en) * | 2008-08-22 | 2010-02-24 | 富士施乐株式会社 | Electrostatic-image-developing toner, process for producing electrostatic-image-developing toner, electrostatic image developer, image-forming method, and image-forming apparatus |
KR20120056561A (en) * | 2010-11-25 | 2012-06-04 | 주식회사 삼양사 | Polyester resin for toner binder and method for preparing the same, and toner comprising the same |
CN102654736A (en) * | 2012-04-23 | 2012-09-05 | 湖北远东卓越科技股份有限公司 | Low temperature photographic fixing resin used for colour matching agent and preparation method thereof |
CN103123446A (en) * | 2011-11-18 | 2013-05-29 | 花王株式会社 | Toner for electrostatic image development |
US20130216943A1 (en) * | 2012-02-17 | 2013-08-22 | Fuji Xerox Co., Ltd. | Toner, liquid developer, dry developer, developer cartridge, process cartridge, image forming apparatus, and image forming method |
CN103309185A (en) * | 2012-03-15 | 2013-09-18 | 株式会社理光 | Toner, image forming apparatus, image forming method, and process cartridge |
CN103399469A (en) * | 2013-07-15 | 2013-11-20 | 湖北鼎龙化学股份有限公司 | Polyester resin for toner, toner and electrostatic charge image developer |
CN104049478A (en) * | 2013-03-15 | 2014-09-17 | 富士施乐株式会社 | Toner, Liquid Developer, Dry Developer, Developer Cartridge, Process Cartridge, Image Forming Apparatus, And Image Forming Method |
JP2015121580A (en) * | 2013-12-20 | 2015-07-02 | キヤノン株式会社 | Toner |
CN104854514A (en) * | 2012-12-07 | 2015-08-19 | 三菱丽阳株式会社 | Polyester resin for toners, method for producing same, and toner |
JP2016040576A (en) * | 2014-08-12 | 2016-03-24 | 富士ゼロックス株式会社 | Toner, liquid developer, developer, developer cartridge, process cartridge, and image forming apparatus |
CN107908087A (en) * | 2017-11-15 | 2018-04-13 | 湖北鼎龙控股股份有限公司 | A kind of new toner and its preparation process |
-
2021
- 2021-08-28 CN CN202110998940.4A patent/CN113703296B/en active Active
Patent Citations (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1920677A (en) * | 2005-08-26 | 2007-02-28 | 富士施乐株式会社 | Binder resin for electrostatic image developing toner, binder resin liquid dispersion for electrostatic image developing toner, electrostatic image developing toner, and production processes thereof |
CN101089739A (en) * | 2006-02-13 | 2007-12-19 | 株式会社理光 | Toner, developer, toner-containing container, process cartridge, image-forming apparatus and image-forming process |
US20070254228A1 (en) * | 2006-04-26 | 2007-11-01 | Xerox Corporation | Toner compositions and processes |
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KR20080051252A (en) * | 2006-12-05 | 2008-06-11 | 에스케이케미칼주식회사 | Polyester resin and toner including the same |
CN101655674A (en) * | 2008-08-22 | 2010-02-24 | 富士施乐株式会社 | Electrostatic-image-developing toner, process for producing electrostatic-image-developing toner, electrostatic image developer, image-forming method, and image-forming apparatus |
JP2009037255A (en) * | 2008-10-10 | 2009-02-19 | Konica Minolta Business Technologies Inc | Electrostatic latent image developing toner, and manufacturing method of electrostatic latent image developing toner |
KR20120056561A (en) * | 2010-11-25 | 2012-06-04 | 주식회사 삼양사 | Polyester resin for toner binder and method for preparing the same, and toner comprising the same |
CN103123446A (en) * | 2011-11-18 | 2013-05-29 | 花王株式会社 | Toner for electrostatic image development |
US20130216943A1 (en) * | 2012-02-17 | 2013-08-22 | Fuji Xerox Co., Ltd. | Toner, liquid developer, dry developer, developer cartridge, process cartridge, image forming apparatus, and image forming method |
CN103309185A (en) * | 2012-03-15 | 2013-09-18 | 株式会社理光 | Toner, image forming apparatus, image forming method, and process cartridge |
CN102654736A (en) * | 2012-04-23 | 2012-09-05 | 湖北远东卓越科技股份有限公司 | Low temperature photographic fixing resin used for colour matching agent and preparation method thereof |
CN104854514A (en) * | 2012-12-07 | 2015-08-19 | 三菱丽阳株式会社 | Polyester resin for toners, method for producing same, and toner |
CN104049478A (en) * | 2013-03-15 | 2014-09-17 | 富士施乐株式会社 | Toner, Liquid Developer, Dry Developer, Developer Cartridge, Process Cartridge, Image Forming Apparatus, And Image Forming Method |
CN103399469A (en) * | 2013-07-15 | 2013-11-20 | 湖北鼎龙化学股份有限公司 | Polyester resin for toner, toner and electrostatic charge image developer |
JP2015121580A (en) * | 2013-12-20 | 2015-07-02 | キヤノン株式会社 | Toner |
JP2016040576A (en) * | 2014-08-12 | 2016-03-24 | 富士ゼロックス株式会社 | Toner, liquid developer, developer, developer cartridge, process cartridge, and image forming apparatus |
CN107908087A (en) * | 2017-11-15 | 2018-04-13 | 湖北鼎龙控股股份有限公司 | A kind of new toner and its preparation process |
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