JPWO2020033357A5 - - Google Patents
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- Publication number
- JPWO2020033357A5 JPWO2020033357A5 JP2021506508A JP2021506508A JPWO2020033357A5 JP WO2020033357 A5 JPWO2020033357 A5 JP WO2020033357A5 JP 2021506508 A JP2021506508 A JP 2021506508A JP 2021506508 A JP2021506508 A JP 2021506508A JP WO2020033357 A5 JPWO2020033357 A5 JP WO2020033357A5
- Authority
- JP
- Japan
- Prior art keywords
- metal oxide
- group
- particles
- polymer
- composite particles
- 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
- 229920000642 polymer Polymers 0.000 claims description 147
- 239000002245 particle Substances 0.000 claims description 134
- 239000011246 composite particle Substances 0.000 claims description 104
- 229910044991 metal oxide Inorganic materials 0.000 claims description 103
- 150000004706 metal oxides Chemical class 0.000 claims description 103
- 239000002184 metal Substances 0.000 claims description 72
- 230000001588 bifunctional effect Effects 0.000 claims description 44
- 239000011159 matrix material Substances 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 35
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- 125000000391 vinyl group Chemical class [H]C([*])=C([H])[H] 0.000 claims description 30
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 22
- 239000006185 dispersion Substances 0.000 claims description 22
- 229920002554 vinyl polymer Polymers 0.000 claims description 22
- -1 methoxy, ethoxy Chemical group 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 239000000203 mixture Chemical class 0.000 claims description 19
- 229920001577 copolymer Polymers 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 239000000843 powder Substances 0.000 claims description 15
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 14
- 239000000178 monomer Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- 238000009826 distribution Methods 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 8
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical class C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 7
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 7
- 150000001336 alkenes Chemical class 0.000 claims description 7
- 229920001567 vinyl ester resin Chemical class 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000012736 aqueous medium Substances 0.000 claims description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 4
- 125000003636 chemical group Chemical group 0.000 claims description 3
- 239000003999 initiator Substances 0.000 claims description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910052734 helium Inorganic materials 0.000 claims description 2
- 239000001307 helium Substances 0.000 claims description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 2
- 229920002239 polyacrylonitrile Chemical class 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 8
- 150000004756 silanes Chemical class 0.000 description 6
- 239000002131 composite material Substances 0.000 description 5
- 239000004971 Cross linker Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- XDQWJFXZTAWJST-UHFFFAOYSA-N 3-triethoxysilylpropyl prop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C=C XDQWJFXZTAWJST-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001343 alkyl silanes Chemical class 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- 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 description 1
- DCEGHEFYVNDALO-UHFFFAOYSA-N 3,3,3-trifluoropropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC(F)(F)F DCEGHEFYVNDALO-UHFFFAOYSA-N 0.000 description 1
- LZMNXXQIQIHFGC-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CO[Si](C)(OC)CCCOC(=O)C(C)=C LZMNXXQIQIHFGC-UHFFFAOYSA-N 0.000 description 1
- JSOZORWBKQSQCJ-UHFFFAOYSA-N 3-[ethoxy(dimethyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CCO[Si](C)(C)CCCOC(=O)C(C)=C JSOZORWBKQSQCJ-UHFFFAOYSA-N 0.000 description 1
- JBDMKOVTOUIKFI-UHFFFAOYSA-N 3-[methoxy(dimethyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CO[Si](C)(C)CCCOC(=O)C(C)=C JBDMKOVTOUIKFI-UHFFFAOYSA-N 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- URDOJQUSEUXVRP-UHFFFAOYSA-N 3-triethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C(C)=C URDOJQUSEUXVRP-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- LUZRKMGMNFOSFZ-UHFFFAOYSA-N but-3-enyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCC=C LUZRKMGMNFOSFZ-UHFFFAOYSA-N 0.000 description 1
- FNNYJATZZFNKNT-UHFFFAOYSA-N but-3-enyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCC=C FNNYJATZZFNKNT-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 description 1
- NHYFIJRXGOQNFS-UHFFFAOYSA-N dimethoxy-bis(2-methylpropyl)silane Chemical compound CC(C)C[Si](OC)(CC(C)C)OC NHYFIJRXGOQNFS-UHFFFAOYSA-N 0.000 description 1
- VHPUZTHRFWIGAW-UHFFFAOYSA-N dimethoxy-di(propan-2-yl)silane Chemical compound CO[Si](OC)(C(C)C)C(C)C VHPUZTHRFWIGAW-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- OCANZHUXNZTABW-UHFFFAOYSA-N triethoxy(pent-4-enyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCC=C OCANZHUXNZTABW-UHFFFAOYSA-N 0.000 description 1
- UZIAQVMNAXPCJQ-UHFFFAOYSA-N triethoxysilylmethyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)COC(=O)C(C)=C UZIAQVMNAXPCJQ-UHFFFAOYSA-N 0.000 description 1
- XYJRNCYWTVGEEG-UHFFFAOYSA-N trimethoxy(2-methylpropyl)silane Chemical compound CO[Si](OC)(OC)CC(C)C XYJRNCYWTVGEEG-UHFFFAOYSA-N 0.000 description 1
- ADQDBBLXGLRLPS-UHFFFAOYSA-N trimethoxy(pent-1-enyl)silane Chemical compound CCCC=C[Si](OC)(OC)OC ADQDBBLXGLRLPS-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
- UOKUUKOEIMCYAI-UHFFFAOYSA-N trimethoxysilylmethyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)COC(=O)C(C)=C UOKUUKOEIMCYAI-UHFFFAOYSA-N 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2023112879A JP2023145500A (ja) | 2018-08-07 | 2023-07-10 | トナー添加剤のための複合粒子 |
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862715556P | 2018-08-07 | 2018-08-07 | |
| US62/715,556 | 2018-08-07 | ||
| US201962858585P | 2019-06-07 | 2019-06-07 | |
| US62/858,585 | 2019-06-07 | ||
| US201962868172P | 2019-06-28 | 2019-06-28 | |
| US62/868,172 | 2019-06-28 | ||
| PCT/US2019/045225 WO2020033357A1 (en) | 2018-08-07 | 2019-08-06 | Composite particles for toner additives |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023112879A Division JP2023145500A (ja) | 2018-08-07 | 2023-07-10 | トナー添加剤のための複合粒子 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2021533239A JP2021533239A (ja) | 2021-12-02 |
| JPWO2020033357A5 true JPWO2020033357A5 (es) | 2024-01-18 |
| JP7455811B2 JP7455811B2 (ja) | 2024-03-26 |
Family
ID=69413328
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021506508A Active JP7455811B2 (ja) | 2018-08-07 | 2019-08-06 | トナー添加剤のための複合粒子 |
| JP2023112879A Pending JP2023145500A (ja) | 2018-08-07 | 2023-07-10 | トナー添加剤のための複合粒子 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023112879A Pending JP2023145500A (ja) | 2018-08-07 | 2023-07-10 | トナー添加剤のための複合粒子 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20210380779A1 (es) |
| EP (1) | EP3834042A4 (es) |
| JP (2) | JP7455811B2 (es) |
| KR (1) | KR20210041024A (es) |
| CN (1) | CN112639625A (es) |
| WO (1) | WO2020033357A1 (es) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112882359B (zh) * | 2021-01-18 | 2022-09-13 | 天津市合成材料工业研究所有限公司 | 一种用于高速复印机的碳粉及其制备方法 |
| CN115322612B (zh) * | 2022-10-18 | 2023-01-10 | 天津大吕电力科技股份有限公司 | 无机填料分散液、超疏水绝缘耐磨涂料及制备方法 |
| EP4372471A1 (en) | 2022-11-17 | 2024-05-22 | Canon Kabushiki Kaisha | External additive for toner and toner |
| EP4372470A1 (en) | 2022-11-17 | 2024-05-22 | Canon Kabushiki Kaisha | External additive for toner and toner |
| WO2024106217A1 (ja) * | 2022-11-17 | 2024-05-23 | キヤノン株式会社 | トナー用外添剤及びトナー |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5424129A (en) * | 1992-11-16 | 1995-06-13 | Xerox Corporation | Composite metal oxide particle processes and toners thereof |
| CA2125427C (en) * | 1994-06-08 | 1999-11-23 | Richard B. Lewis | Composite metal oxide particle processes and toners thereof |
| JP2005221802A (ja) * | 2004-02-06 | 2005-08-18 | Fuji Xerox Co Ltd | 静電潜像現像用トナー及びその製造方法、並びに静電潜像現像剤 |
| US8062820B2 (en) * | 2006-05-12 | 2011-11-22 | Cabot Corporation | Toner composition and method of preparing same |
| US8202502B2 (en) * | 2006-09-15 | 2012-06-19 | Cabot Corporation | Method of preparing hydrophobic silica |
| US20080070146A1 (en) * | 2006-09-15 | 2008-03-20 | Cabot Corporation | Hydrophobic-treated metal oxide |
| US8945804B2 (en) * | 2008-07-09 | 2015-02-03 | Cabot Corporation | Treated metal oxide particles and toner compositions |
| US20110244382A1 (en) * | 2010-04-06 | 2011-10-06 | Christopher Alyson M | Hydrophobic silica particles and method of producing same |
| JP2013092748A (ja) * | 2011-10-26 | 2013-05-16 | Cabot Corp | 複合体粒子を含むトナー添加剤 |
| JP5983661B2 (ja) * | 2014-02-28 | 2016-09-06 | コニカミノルタ株式会社 | 画像形成方法 |
| JP6094525B2 (ja) * | 2014-04-30 | 2017-03-15 | コニカミノルタ株式会社 | 画像形成方法 |
| US9535353B2 (en) * | 2014-12-23 | 2017-01-03 | Lexmark International, Inc. | Formulation for a developer mix having tribocharge uniformity across different temperature and humidity conditions |
| WO2017057068A1 (ja) * | 2015-09-30 | 2017-04-06 | 日本ゼオン株式会社 | 静電荷像現像用トナー |
-
2019
- 2019-08-06 KR KR1020217006439A patent/KR20210041024A/ko not_active Application Discontinuation
- 2019-08-06 EP EP19847447.0A patent/EP3834042A4/en active Pending
- 2019-08-06 JP JP2021506508A patent/JP7455811B2/ja active Active
- 2019-08-06 WO PCT/US2019/045225 patent/WO2020033357A1/en unknown
- 2019-08-06 US US17/265,664 patent/US20210380779A1/en active Pending
- 2019-08-06 CN CN201980053148.2A patent/CN112639625A/zh active Pending
-
2023
- 2023-07-10 JP JP2023112879A patent/JP2023145500A/ja active Pending
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