JP2003528179A - 機能性重合体粒子の製造方法 - Google Patents
機能性重合体粒子の製造方法Info
- Publication number
- JP2003528179A JP2003528179A JP2001569025A JP2001569025A JP2003528179A JP 2003528179 A JP2003528179 A JP 2003528179A JP 2001569025 A JP2001569025 A JP 2001569025A JP 2001569025 A JP2001569025 A JP 2001569025A JP 2003528179 A JP2003528179 A JP 2003528179A
- Authority
- JP
- Japan
- Prior art keywords
- monomer
- seed material
- polymerization
- particles
- seed
- 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.)
- Pending
Links
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- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
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- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
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- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
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- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
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- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
-
- 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
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by heteroatoms or groups containing heteroatoms
- C08F212/26—Nitrogen
- C08F212/28—Amines
-
- 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
- C08F257/00—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00
- C08F257/02—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00 on to polymers of styrene or alkyl-substituted styrenes
-
- 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
- C08F285/00—Macromolecular compounds obtained by polymerising monomers on to preformed graft polymers
-
- 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
- C08F291/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
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| GB0007005.2 | 2000-03-22 | ||
| GB0007005A GB0007005D0 (en) | 2000-03-22 | 2000-03-22 | Process |
| GB0023070.6 | 2000-09-20 | ||
| GB0023070A GB0023070D0 (en) | 2000-09-20 | 2000-09-20 | Process |
| GB0023673.7 | 2000-09-27 | ||
| GB0023673A GB0023673D0 (en) | 2000-09-27 | 2000-09-27 | Process |
| PCT/GB2001/001278 WO2001070825A1 (en) | 2000-03-22 | 2001-03-22 | Process for the preparation of functionalised polymer particles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003528179A true JP2003528179A (ja) | 2003-09-24 |
| JP2003528179A5 JP2003528179A5 (enExample) | 2008-05-22 |
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Family Applications (1)
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|---|---|---|---|
| JP2001569025A Pending JP2003528179A (ja) | 2000-03-22 | 2001-03-22 | 機能性重合体粒子の製造方法 |
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| US (3) | US6984702B2 (enExample) |
| EP (1) | EP1268563B1 (enExample) |
| JP (1) | JP2003528179A (enExample) |
| AT (1) | ATE346098T1 (enExample) |
| AU (1) | AU2001239422A1 (enExample) |
| DE (1) | DE60124686T2 (enExample) |
| NO (1) | NO20024517L (enExample) |
| WO (1) | WO2001070825A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5942429B2 (ja) * | 2010-06-10 | 2016-06-29 | 三菱レイヨン株式会社 | アクリル系重合体の製造方法、及びプラスチゾル組成物の製造方法 |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6984702B2 (en) | 2000-03-22 | 2006-01-10 | Dynal Biotech Asa | Process for the preparation of functionalized polymer particles |
| CN100439406C (zh) | 2003-04-14 | 2008-12-03 | 阿克佐诺贝尔股份有限公司 | 向苯乙烯聚合的悬浮方法中计量加料过氧化物 |
| AU2004264038B2 (en) | 2003-07-17 | 2010-09-23 | Life Technologies As | Process for preparing coated magnetic particles |
| NO20041205L (no) * | 2004-03-22 | 2005-09-23 | Polymers Holding As | Lagringsstabile polymer-oligomer partikler og anvendelse av disse i seed polymerisasjon |
| JP5443682B2 (ja) * | 2007-11-05 | 2014-03-19 | 日東電工株式会社 | ヒドロキシ基又は第１級アミノ基を有する多孔質樹脂粒子とその製造方法 |
| US8366692B2 (en) * | 2008-01-08 | 2013-02-05 | Richard Scott Weston | Sustained variable negative pressure wound treatment and method of controlling same |
| EP2364329B1 (en) | 2008-12-12 | 2018-09-26 | Jackon GmbH | Process for the preparation of an expandable polymer composition in the form of beads |
| DK2356173T3 (en) | 2008-12-12 | 2018-08-27 | Jackon Gmbh | PROCEDURE FOR THE PREPARATION OF AN EXPANDABLE POLYMER COMPOSITION IN THE FORM OF BALLS |
| US8790916B2 (en) | 2009-05-14 | 2014-07-29 | Genestream, Inc. | Microfluidic method and system for isolating particles from biological fluid |
| US8747084B2 (en) | 2010-07-21 | 2014-06-10 | Aperia Technologies, Inc. | Peristaltic pump |
| CN103781811B (zh) * | 2011-09-15 | 2016-03-23 | 拜耳知识产权有限责任公司 | 连续生产水可分散乙烯基聚合物的方法 |
| PL2828103T3 (pl) | 2012-03-20 | 2017-09-29 | Aperia Technologies | System pompowania opon |
| US9604157B2 (en) | 2013-03-12 | 2017-03-28 | Aperia Technologies, Inc. | Pump with water management |
| US10144254B2 (en) | 2013-03-12 | 2018-12-04 | Aperia Technologies, Inc. | Tire inflation system |
| US11453258B2 (en) | 2013-03-12 | 2022-09-27 | Aperia Technologies, Inc. | System for tire inflation |
| WO2018048885A1 (en) | 2016-09-06 | 2018-03-15 | Aperia Technologies, Inc. | System for tire inflation |
| US10406869B2 (en) | 2017-11-10 | 2019-09-10 | Aperia Technologies, Inc. | Inflation system |
| US11642920B2 (en) | 2018-11-27 | 2023-05-09 | Aperia Technologies, Inc. | Hub-integrated inflation system |
| US12442364B2 (en) | 2023-12-11 | 2025-10-14 | Aperia Technologies, Inc. | Two-stage pump and method of operation |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61215604A (ja) * | 1985-03-22 | 1986-09-25 | Japan Synthetic Rubber Co Ltd | ポリマ−粒子の製造方法 |
| JPS62181301A (ja) * | 1986-02-06 | 1987-08-08 | Fuji Xerox Co Ltd | 重合体粒子の製造方法 |
| JPH02140212A (ja) * | 1988-11-21 | 1990-05-29 | Mitsui Petrochem Ind Ltd | 変性ポリオレフィン粒子の製造法 |
| JPH05214042A (ja) * | 1990-09-24 | 1993-08-24 | Rohm & Haas Co | コアー−シェル重合体を含有する組成物 |
| JPH08134115A (ja) * | 1994-11-15 | 1996-05-28 | Sekisui Chem Co Ltd | 高単分散微粒子の製造方法 |
| JPH11116610A (ja) * | 1997-10-10 | 1999-04-27 | Dyno Ind Asa | 重合種子として実質的に単分散のポリマー粒子の使用、ポリマー粒子の製造方法および実質的に単分散な微粒子状ポリマー材料 |
| JP2002542319A (ja) * | 1999-04-09 | 2002-12-10 | ポリマー システムズ エイエス | ポリマー粒子の製造法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU530410B2 (en) | 1978-02-21 | 1983-07-14 | Sintef | Preparing aqueous emulsions |
| NO149108C (no) | 1981-10-21 | 1984-02-15 | Sintef | Fremgangsmaate for fremstilling av vandige dispersjoner av organisk materiale og eventuelt videre omdannelse til en polymerdispersjon naar det organiske materiale er en polymeriserbar monomer |
| ES2236939T3 (es) | 1997-10-10 | 2005-07-16 | Microbeads As | Metodo de produccion de polimeros en forma de particulas. |
| US6984702B2 (en) | 2000-03-22 | 2006-01-10 | Dynal Biotech Asa | Process for the preparation of functionalized polymer particles |
-
2001
- 2001-03-01 US US10/239,492 patent/US6984702B2/en not_active Expired - Lifetime
- 2001-03-22 DE DE60124686T patent/DE60124686T2/de not_active Expired - Lifetime
- 2001-03-22 AT AT01914034T patent/ATE346098T1/de not_active IP Right Cessation
- 2001-03-22 WO PCT/GB2001/001278 patent/WO2001070825A1/en not_active Ceased
- 2001-03-22 EP EP01914034A patent/EP1268563B1/en not_active Expired - Lifetime
- 2001-03-22 AU AU2001239422A patent/AU2001239422A1/en not_active Abandoned
- 2001-03-22 JP JP2001569025A patent/JP2003528179A/ja active Pending
-
2002
- 2002-09-20 NO NO20024517A patent/NO20024517L/no unknown
-
2005
- 2005-11-14 US US11/273,438 patent/US20060069217A1/en not_active Abandoned
-
2007
- 2007-08-21 US US11/842,836 patent/US7763689B2/en not_active Expired - Lifetime
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61215604A (ja) * | 1985-03-22 | 1986-09-25 | Japan Synthetic Rubber Co Ltd | ポリマ−粒子の製造方法 |
| JPS62181301A (ja) * | 1986-02-06 | 1987-08-08 | Fuji Xerox Co Ltd | 重合体粒子の製造方法 |
| JPH02140212A (ja) * | 1988-11-21 | 1990-05-29 | Mitsui Petrochem Ind Ltd | 変性ポリオレフィン粒子の製造法 |
| JPH05214042A (ja) * | 1990-09-24 | 1993-08-24 | Rohm & Haas Co | コアー−シェル重合体を含有する組成物 |
| JPH08134115A (ja) * | 1994-11-15 | 1996-05-28 | Sekisui Chem Co Ltd | 高単分散微粒子の製造方法 |
| JPH11116610A (ja) * | 1997-10-10 | 1999-04-27 | Dyno Ind Asa | 重合種子として実質的に単分散のポリマー粒子の使用、ポリマー粒子の製造方法および実質的に単分散な微粒子状ポリマー材料 |
| JP2002542319A (ja) * | 1999-04-09 | 2002-12-10 | ポリマー システムズ エイエス | ポリマー粒子の製造法 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5942429B2 (ja) * | 2010-06-10 | 2016-06-29 | 三菱レイヨン株式会社 | アクリル系重合体の製造方法、及びプラスチゾル組成物の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| NO20024517D0 (no) | 2002-09-20 |
| US20080039578A1 (en) | 2008-02-14 |
| NO20024517L (no) | 2002-11-22 |
| US20030109657A1 (en) | 2003-06-12 |
| WO2001070825A1 (en) | 2001-09-27 |
| US7763689B2 (en) | 2010-07-27 |
| DE60124686D1 (de) | 2007-01-04 |
| AU2001239422A1 (en) | 2001-10-03 |
| EP1268563A1 (en) | 2003-01-02 |
| EP1268563B1 (en) | 2006-11-22 |
| US20060069217A1 (en) | 2006-03-30 |
| US6984702B2 (en) | 2006-01-10 |
| ATE346098T1 (de) | 2006-12-15 |
| DE60124686T2 (de) | 2007-09-13 |
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