KR102260651B1 - 유화 중합을 통한 양친매성 블록 공중합체의 합성을 포함하는 토너 공정 - Google Patents
유화 중합을 통한 양친매성 블록 공중합체의 합성을 포함하는 토너 공정 Download PDFInfo
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- KR102260651B1 KR102260651B1 KR1020180016794A KR20180016794A KR102260651B1 KR 102260651 B1 KR102260651 B1 KR 102260651B1 KR 1020180016794 A KR1020180016794 A KR 1020180016794A KR 20180016794 A KR20180016794 A KR 20180016794A KR 102260651 B1 KR102260651 B1 KR 102260651B1
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- Prior art keywords
- toner
- block copolymer
- amphiphilic block
- dispersion
- methacrylate
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- 229920000469 amphiphilic block copolymer Polymers 0.000 title claims abstract description 86
- 238000000034 method Methods 0.000 title claims description 95
- 230000008569 process Effects 0.000 title claims description 63
- 238000007720 emulsion polymerization reaction Methods 0.000 title abstract description 12
- 230000002194 synthesizing effect Effects 0.000 title description 2
- 239000002245 particle Substances 0.000 claims abstract description 89
- 229920000126 latex Polymers 0.000 claims abstract description 70
- 239000004816 latex Substances 0.000 claims abstract description 69
- 239000000178 monomer Substances 0.000 claims abstract description 67
- 239000001993 wax Substances 0.000 claims abstract description 59
- 239000006185 dispersion Substances 0.000 claims abstract description 47
- 229920000642 polymer Polymers 0.000 claims abstract description 47
- 239000003086 colorant Substances 0.000 claims abstract description 42
- 239000000203 mixture Substances 0.000 claims abstract description 42
- 239000003999 initiator Substances 0.000 claims abstract description 37
- 238000001246 colloidal dispersion Methods 0.000 claims abstract description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 27
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 26
- 238000010438 heat treatment Methods 0.000 claims abstract description 25
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 23
- 230000009477 glass transition Effects 0.000 claims abstract description 15
- 238000007599 discharging Methods 0.000 claims abstract description 9
- -1 alkyl methacrylate Chemical compound 0.000 claims description 143
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 23
- 229920001400 block copolymer Polymers 0.000 claims description 16
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 12
- 238000001816 cooling Methods 0.000 claims description 12
- 229920000728 polyester Polymers 0.000 claims description 12
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical group [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 10
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 claims description 9
- 229940048053 acrylate Drugs 0.000 claims description 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 8
- FQYPKQOQUNFBDP-QMMMGPOBSA-N (2s)-6-amino-2-(2-methylprop-2-enoylamino)hexanoic acid Chemical compound CC(=C)C(=O)N[C@H](C(O)=O)CCCCN FQYPKQOQUNFBDP-QMMMGPOBSA-N 0.000 claims description 7
- 239000011258 core-shell material Substances 0.000 claims description 7
- 229920001519 homopolymer Polymers 0.000 claims description 7
- RUSMHXACRXXLKQ-UHFFFAOYSA-N n-(2-aminoethyl)-2-methylprop-2-enamide;hydrochloride Chemical compound Cl.CC(=C)C(=O)NCCN RUSMHXACRXXLKQ-UHFFFAOYSA-N 0.000 claims description 7
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 5
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 claims description 5
- CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical group OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 claims description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 5
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- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 5
- XFTALRAZSCGSKN-UHFFFAOYSA-M sodium;4-ethenylbenzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=C(C=C)C=C1 XFTALRAZSCGSKN-UHFFFAOYSA-M 0.000 claims description 5
- SQTUYFKNCCBFRR-UHFFFAOYSA-N (2,4-dimethoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C(OC)=C1 SQTUYFKNCCBFRR-UHFFFAOYSA-N 0.000 claims description 4
- PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 claims description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 4
- PRAMZQXXPOLCIY-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethanesulfonic acid Chemical compound CC(=C)C(=O)OCCS(O)(=O)=O PRAMZQXXPOLCIY-UHFFFAOYSA-N 0.000 claims description 4
- CEXQWAAGPPNOQF-UHFFFAOYSA-N 2-phenoxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC1=CC=CC=C1 CEXQWAAGPPNOQF-UHFFFAOYSA-N 0.000 claims description 4
- IRQWEODKXLDORP-UHFFFAOYSA-N 4-ethenylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=C)C=C1 IRQWEODKXLDORP-UHFFFAOYSA-N 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 4
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 claims description 4
- 239000004815 dispersion polymer Substances 0.000 claims description 4
- OVHHHVAVHBHXAK-UHFFFAOYSA-N n,n-diethylprop-2-enamide Chemical compound CCN(CC)C(=O)C=C OVHHHVAVHBHXAK-UHFFFAOYSA-N 0.000 claims description 4
- 229940047670 sodium acrylate Drugs 0.000 claims description 4
- PNOXUQIZPBURMT-UHFFFAOYSA-M potassium;3-(2-methylprop-2-enoyloxy)propane-1-sulfonate Chemical compound [K+].CC(=C)C(=O)OCCCS([O-])(=O)=O PNOXUQIZPBURMT-UHFFFAOYSA-M 0.000 claims description 3
- 238000013019 agitation Methods 0.000 claims description 2
- QGRSLAYMCFPMHW-UHFFFAOYSA-M sodium;3-(2-methylprop-2-enoyloxy)propane-1-sulfonate Chemical compound [Na+].CC(=C)C(=O)OCCCS([O-])(=O)=O QGRSLAYMCFPMHW-UHFFFAOYSA-M 0.000 claims description 2
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 229920005989 resin Polymers 0.000 description 45
- 239000011347 resin Substances 0.000 description 45
- 239000000049 pigment Substances 0.000 description 41
- 239000000839 emulsion Substances 0.000 description 31
- 239000004094 surface-active agent Substances 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000002270 dispersing agent Substances 0.000 description 16
- 239000000126 substance Substances 0.000 description 14
- 239000000975 dye Substances 0.000 description 12
- 239000000654 additive Substances 0.000 description 11
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
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- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
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- 150000003254 radicals Chemical class 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
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- LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
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- 125000003277 amino group Chemical group 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
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Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F2/12—Polymerisation in non-solvents
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- C08F2/22—Emulsion polymerisation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- G03G9/08702—Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
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- G03G9/08733—Polymers of unsaturated polycarboxylic acids
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- G03G9/08795—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775 characterised by their chemical properties, e.g. acidity, molecular weight, sensitivity to reactants
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- G—PHYSICS
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- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
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Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Developing Agents For Electrophotography (AREA)
- Graft Or Block Polymers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15/444,408 US9958797B1 (en) | 2017-02-28 | 2017-02-28 | Toner process comprising synthesizing amphiphilic block copolymers via emulsion polymerization |
| US15/444,408 | 2017-02-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20180099473A KR20180099473A (ko) | 2018-09-05 |
| KR102260651B1 true KR102260651B1 (ko) | 2021-06-07 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020180016794A Active KR102260651B1 (ko) | 2017-02-28 | 2018-02-12 | 유화 중합을 통한 양친매성 블록 공중합체의 합성을 포함하는 토너 공정 |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US9958797B1 (enExample) |
| JP (1) | JP2018141961A (enExample) |
| KR (1) | KR102260651B1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112384581A (zh) | 2018-06-11 | 2021-02-19 | 宣伟投资管理有限公司 | 包含水分散性丙烯酸类嵌段共聚物的包装涂层 |
| KR101906445B1 (ko) * | 2018-06-29 | 2018-10-10 | (주)이노큐디 | 양자점 필름의 제조방법, 이로써 제조된 양자점 필름, 및 이를 포함하는 파장변환 시트 및 디스플레이 |
| WO2020095127A1 (en) * | 2018-11-05 | 2020-05-14 | Halion Displays Inc. | Optical activation of chemical entities in electrophoretic dispersions for display devices |
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| JP2004163955A (ja) | 2002-11-12 | 2004-06-10 | Samsung Electronics Co Ltd | 両親媒性共重合体を含むドライ電子写真用トナー,その製造方法及びそれを利用した電子写真画像形成方法 |
| JP2005105277A (ja) | 2003-09-30 | 2005-04-21 | Samsung Electronics Co Ltd | ブラック着色剤化合物,その製造方法および使用方法,トナー組成物,インク組成物,および濃縮着色剤組成物 |
| JP2017003861A (ja) | 2015-06-12 | 2017-01-05 | キヤノン株式会社 | トナーの製造方法 |
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| JP2018141961A (ja) | 2018-09-13 |
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