DE60225203T2 - Verfahren zur Herstellung von Polymerpartikeln mit enger Teilchengrössen-Verteilung - Google Patents
Verfahren zur Herstellung von Polymerpartikeln mit enger Teilchengrössen-Verteilung Download PDFInfo
- Publication number
- DE60225203T2 DE60225203T2 DE2002625203 DE60225203T DE60225203T2 DE 60225203 T2 DE60225203 T2 DE 60225203T2 DE 2002625203 DE2002625203 DE 2002625203 DE 60225203 T DE60225203 T DE 60225203T DE 60225203 T2 DE60225203 T2 DE 60225203T2
- Authority
- DE
- Germany
- Prior art keywords
- cyclodextrin
- polymer particles
- polymerization
- monomer
- monodisperse
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 238000006116 polymerization reaction Methods 0.000 claims description 35
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 25
- 229960004853 betadex Drugs 0.000 claims description 21
- 230000002209 hydrophobic effect Effects 0.000 claims description 21
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- MKRBAPNEJMFMHU-UHFFFAOYSA-N 1-benzylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1=CC=CC=C1 MKRBAPNEJMFMHU-UHFFFAOYSA-N 0.000 claims description 3
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 claims description 3
- QTKPMCIBUROOGY-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)F QTKPMCIBUROOGY-UHFFFAOYSA-N 0.000 claims description 3
- VBHXIMACZBQHPX-UHFFFAOYSA-N 2,2,2-trifluoroethyl prop-2-enoate Chemical compound FC(F)(F)COC(=O)C=C VBHXIMACZBQHPX-UHFFFAOYSA-N 0.000 claims description 3
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- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 3
- CEBFLGHPYLIZSC-UHFFFAOYSA-N n-benzyl-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCC1=CC=CC=C1 CEBFLGHPYLIZSC-UHFFFAOYSA-N 0.000 claims description 3
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- 150000003923 2,5-pyrrolediones Chemical class 0.000 claims description 2
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- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 2
- 150000003926 acrylamides Chemical class 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 2
- 150000001993 dienes Chemical class 0.000 claims 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 33
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- 238000004519 manufacturing process Methods 0.000 description 25
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- 238000006243 chemical reaction Methods 0.000 description 20
- -1 poly(methyl methacrylate) Polymers 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000004094 surface-active agent Substances 0.000 description 18
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- 229940080345 gamma-cyclodextrin Drugs 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 description 9
- 229940043377 alpha-cyclodextrin Drugs 0.000 description 9
- 239000011324 bead Substances 0.000 description 8
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- 229920002521 macromolecule Polymers 0.000 description 8
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 8
- 239000004926 polymethyl methacrylate Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 7
- 239000003945 anionic surfactant Substances 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 239000012736 aqueous medium Substances 0.000 description 6
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- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 5
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 description 5
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- QUKRIOLKOHUUBM-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl prop-2-enoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCOC(=O)C=C QUKRIOLKOHUUBM-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000003491 array Methods 0.000 description 4
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 4
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- 125000005395 methacrylic acid group Chemical group 0.000 description 4
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
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- 150000002148 esters Chemical class 0.000 description 3
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 description 3
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- 238000001338 self-assembly Methods 0.000 description 3
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- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- VPKQPPJQTZJZDB-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl prop-2-enoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCOC(=O)C=C VPKQPPJQTZJZDB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
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- FDENMIUNZYEPDD-UHFFFAOYSA-L disodium [2-[4-(10-methylundecyl)-2-sulfonatooxyphenoxy]phenyl] sulfate Chemical compound [Na+].[Na+].CC(C)CCCCCCCCCc1ccc(Oc2ccccc2OS([O-])(=O)=O)c(OS([O-])(=O)=O)c1 FDENMIUNZYEPDD-UHFFFAOYSA-L 0.000 description 2
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- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
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- 159000000000 sodium salts Chemical class 0.000 description 1
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- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
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- 238000000108 ultra-filtration Methods 0.000 description 1
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Landscapes
- Polymerisation Methods In General (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01000099 | 2001-03-29 | ||
| EP01000099 | 2001-03-29 |
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| Publication Number | Publication Date |
|---|---|
| DE60225203D1 DE60225203D1 (de) | 2008-04-10 |
| DE60225203T2 true DE60225203T2 (de) | 2009-02-19 |
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ID=8176032
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2002625203 Expired - Lifetime DE60225203T2 (de) | 2001-03-29 | 2002-02-20 | Verfahren zur Herstellung von Polymerpartikeln mit enger Teilchengrössen-Verteilung |
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|---|---|
| JP (1) | JP2002332302A (enExample) |
| DE (1) | DE60225203T2 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015101621A1 (en) | 2013-12-30 | 2015-07-09 | Averis As | Process for the preparation of solid particulate vinyl aromatic polymer compositions |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060094844A1 (en) * | 2004-10-29 | 2006-05-04 | Council Of Scientific And Industrial Research | Inclusion complexes of unsaturated monomers, their polymers and process for preparation thereof |
| JP5486147B2 (ja) * | 2006-11-08 | 2014-05-07 | 富士フイルム株式会社 | 顔料分散組成物、それを含有する着色感光性樹脂組成物及び感光性樹脂転写材料、並びにそれらを用いたカラーフィルタ及び液晶表示装置 |
| WO2010131628A1 (ja) * | 2009-05-11 | 2010-11-18 | Ａｇｃセイミケミカル株式会社 | 単分散性クロロメチルスチレン重合体およびその製造方法 |
| JP2012236797A (ja) * | 2011-05-12 | 2012-12-06 | Adeka Corp | 複合体及びその製造方法 |
| KR101942966B1 (ko) * | 2011-08-18 | 2019-01-29 | 삼성전자주식회사 | 단분산 입자의 제조 방법, 이에 따라 제조된 단분산 입자 및 가변 광결정 소자 |
| TW201718663A (zh) * | 2015-08-28 | 2017-06-01 | Nippon Catalytic Chem Ind | 有機聚合物微粒子 |
| CN110950989B (zh) * | 2019-11-05 | 2023-01-10 | N科研中心私人投资有限公司 | 用于制备单分散颗粒的方法 |
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2002
- 2002-02-20 DE DE2002625203 patent/DE60225203T2/de not_active Expired - Lifetime
- 2002-03-20 JP JP2002078073A patent/JP2002332302A/ja active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015101621A1 (en) | 2013-12-30 | 2015-07-09 | Averis As | Process for the preparation of solid particulate vinyl aromatic polymer compositions |
| US9976006B2 (en) | 2013-12-30 | 2018-05-22 | Averis As | Process for the preparation of solid particulate vinyl aromatic polymer compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| DE60225203D1 (de) | 2008-04-10 |
| JP2002332302A (ja) | 2002-11-22 |
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