NO332815B1 - Fremgangsmate for fremstilling av monodisperse polymerpartikler - Google Patents
Fremgangsmate for fremstilling av monodisperse polymerpartikler Download PDFInfo
- Publication number
- NO332815B1 NO332815B1 NO20014835A NO20014835A NO332815B1 NO 332815 B1 NO332815 B1 NO 332815B1 NO 20014835 A NO20014835 A NO 20014835A NO 20014835 A NO20014835 A NO 20014835A NO 332815 B1 NO332815 B1 NO 332815B1
- Authority
- NO
- Norway
- Prior art keywords
- particles
- seed particles
- swollen
- water
- monomer
- Prior art date
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- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 239000007970 homogeneous dispersion Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
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- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/16—Making expandable particles
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
-
- 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
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
-
- 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
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/10—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of amides or imides
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/22—After-treatment of expandable particles; Forming foamed products
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/22—After-treatment of expandable particles; Forming foamed products
- C08J9/224—Surface treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2203/00—Foams characterized by the expanding agent
- C08J2203/14—Saturated hydrocarbons, e.g. butane; Unspecified hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2325/00—Characterised by the use of homopolymers or 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; Derivatives of such polymers
- C08J2325/02—Homopolymers or copolymers of hydrocarbons
- C08J2325/04—Homopolymers or copolymers of styrene
- C08J2325/06—Polystyrene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2347/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Derivatives of such polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Paper (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| GBGB9908163.0A GB9908163D0 (en) | 1999-04-09 | 1999-04-09 | Process |
| GBGB0007008.6A GB0007008D0 (en) | 1999-04-09 | 2000-03-22 | Process |
| PCT/GB2000/001334 WO2000061647A1 (en) | 1999-04-09 | 2000-04-10 | Process for the preparation of monodisperse polymer particles |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20014835D0 NO20014835D0 (no) | 2001-10-04 |
| NO20014835L NO20014835L (no) | 2001-12-07 |
| NO332815B1 true NO332815B1 (no) | 2013-01-21 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20014835A NO332815B1 (no) | 1999-04-09 | 2001-10-04 | Fremgangsmate for fremstilling av monodisperse polymerpartikler |
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| Country | Link |
|---|---|
| US (6) | US7217762B1 (zh) |
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| CN (2) | CN1311005C (zh) |
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| CA (1) | CA2369293C (zh) |
| NO (1) | NO332815B1 (zh) |
| TW (1) | TW589330B (zh) |
| WO (1) | WO2000061647A1 (zh) |
Families Citing this family (66)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1177231B1 (en) | 1999-04-09 | 2009-08-19 | Invitrogen Dynal AS | Process for the preparation of monodisperse polymer particles |
| GB0228914D0 (en) | 2002-12-11 | 2003-01-15 | Dynal Biotech Asa | Particles |
| NO20041205L (no) | 2004-03-22 | 2005-09-23 | Polymers Holding As | Lagringsstabile polymer-oligomer partikler og anvendelse av disse i seed polymerisasjon |
| EP2295471B1 (en) * | 2005-09-16 | 2019-10-23 | Rohm and Haas Company | Method for making swellable particles |
| US8444898B2 (en) * | 2006-03-30 | 2013-05-21 | Honeywell International Inc | High molecular weight poly(alpha-olefin) solutions and articles made therefrom |
| WO2007127799A2 (en) * | 2006-04-25 | 2007-11-08 | Research Foundation Of The City University Of New York | Polymer submicron particle preparation by surfactant- mediated precipitation |
| US9738745B2 (en) | 2006-06-29 | 2017-08-22 | Life Technologies As | Particles containing multi-block polymers |
| JP5493248B2 (ja) * | 2007-04-25 | 2014-05-14 | 日油株式会社 | コア−シェル微粒子の製造方法及びその中間体の製造方法 |
| CN101186661B (zh) * | 2007-12-14 | 2012-09-19 | 深圳市纳微科技有限公司 | 一种聚合物颗粒的制备方法 |
| WO2009142231A1 (ja) * | 2008-05-21 | 2009-11-26 | 東レ株式会社 | ポリマー微粒子の製造方法 |
| GB0907372D0 (en) * | 2009-04-29 | 2009-06-10 | Invitrogen Dynal As | Particles |
| US8790916B2 (en) | 2009-05-14 | 2014-07-29 | Genestream, Inc. | Microfluidic method and system for isolating particles from biological fluid |
| JP5483451B2 (ja) * | 2009-12-30 | 2014-05-07 | ローム アンド ハース カンパニー | 均一なポリマービーズを製造する方法 |
| JP5474745B2 (ja) * | 2009-12-30 | 2014-04-16 | ローム アンド ハース カンパニー | 均一なオリゴマー液滴を製造する方法 |
| US9822010B2 (en) | 2010-01-21 | 2017-11-21 | CoLabs International Corporation | Ceramic encapsulation by use of one or more specialized silanes to template oil in an oil in water emulsion |
| US8747084B2 (en) | 2010-07-21 | 2014-06-10 | Aperia Technologies, Inc. | Peristaltic pump |
| US8822663B2 (en) | 2010-08-06 | 2014-09-02 | Moderna Therapeutics, Inc. | Engineered nucleic acids and methods of use thereof |
| AU2011308496A1 (en) | 2010-10-01 | 2013-05-02 | Moderna Therapeutics, Inc. | Engineered nucleic acids and methods of use thereof |
| GB201018380D0 (en) | 2010-10-29 | 2010-12-15 | Conpart As | Process |
| GB201018379D0 (en) | 2010-10-29 | 2010-12-15 | Conpart As | Conductive rf particles |
| EP2663639B1 (en) | 2011-01-14 | 2017-09-13 | Life Technologies Corporation | Methods for isolation, identification, and quantification of mirnas |
| DE12722942T1 (de) | 2011-03-31 | 2021-09-30 | Modernatx, Inc. | Freisetzung und formulierung von manipulierten nukleinsäuren |
| JP2012255135A (ja) * | 2011-05-17 | 2012-12-27 | Rohm & Haas Co | 熱可塑性ポリマーを吸収したラテックス粒子 |
| US9464124B2 (en) | 2011-09-12 | 2016-10-11 | Moderna Therapeutics, Inc. | Engineered nucleic acids and methods of use thereof |
| US20130109596A1 (en) | 2011-09-26 | 2013-05-02 | Life Technologies Corporation | High efficiency, small volume nucleic acid synthesis |
| WO2014153188A2 (en) | 2013-03-14 | 2014-09-25 | Life Technologies Corporation | High efficiency, small volume nucleic acid synthesis |
| WO2013052523A1 (en) | 2011-10-03 | 2013-04-11 | modeRNA Therapeutics | Modified nucleosides, nucleotides, and nucleic acids, and uses thereof |
| CA2859387A1 (en) | 2011-12-16 | 2013-06-20 | Moderna Therapeutics, Inc. | Modified nucleoside, nucleotide, and nucleic acid compositions |
| CN104203964B (zh) | 2012-02-09 | 2017-07-18 | 生命技术公司 | 疏水的二丙烯酰胺化合物 |
| EP2812446B1 (en) | 2012-02-09 | 2017-05-10 | Life Technologies Corporation | Conjugated polymeric particle and method of making same |
| WO2013119936A2 (en) | 2012-02-09 | 2013-08-15 | Life Technologies Corporation | Hydrophilic polymeric particles and methods for making same |
| US9039392B2 (en) | 2012-03-20 | 2015-05-26 | Aperia Technologies, Inc. | Tire inflation system |
| US9572897B2 (en) | 2012-04-02 | 2017-02-21 | Modernatx, Inc. | Modified polynucleotides for the production of cytoplasmic and cytoskeletal proteins |
| US10501512B2 (en) | 2012-04-02 | 2019-12-10 | Modernatx, Inc. | Modified polynucleotides |
| WO2013151669A1 (en) | 2012-04-02 | 2013-10-10 | modeRNA Therapeutics | Modified polynucleotides for the production of cytoplasmic and cytoskeletal proteins |
| US9283287B2 (en) | 2012-04-02 | 2016-03-15 | Moderna Therapeutics, Inc. | Modified polynucleotides for the production of nuclear proteins |
| TWI557160B (zh) * | 2012-04-19 | 2016-11-11 | 國家中山科學研究院 | 高交聯度均一粒徑高分子微球製備方法 |
| GB201212489D0 (en) | 2012-07-13 | 2012-08-29 | Conpart As | Improvements in conductive adhesives |
| US9597380B2 (en) | 2012-11-26 | 2017-03-21 | Modernatx, Inc. | Terminally modified RNA |
| US10144254B2 (en) | 2013-03-12 | 2018-12-04 | Aperia Technologies, Inc. | Tire inflation system |
| US9604157B2 (en) | 2013-03-12 | 2017-03-28 | Aperia Technologies, Inc. | Pump with water management |
| US11453258B2 (en) | 2013-03-12 | 2022-09-27 | Aperia Technologies, Inc. | System for tire inflation |
| US8980864B2 (en) | 2013-03-15 | 2015-03-17 | Moderna Therapeutics, Inc. | Compositions and methods of altering cholesterol levels |
| EP3052521A1 (en) | 2013-10-03 | 2016-08-10 | Moderna Therapeutics, Inc. | Polynucleotides encoding low density lipoprotein receptor |
| CA2926883C (en) * | 2013-12-04 | 2019-04-09 | F. Hoffmann-La Roche Ag | Improved process for producing magnetic monodisperse polymer particles |
| ES2465715B1 (es) | 2014-02-14 | 2015-03-18 | Universitat Autónoma De Barcelona | Péptido, péptido magnético y método para detectar la enfermedad celíaca |
| CN104072663B (zh) * | 2014-06-27 | 2016-02-24 | 西北工业大学 | 一种表面褶皱单分散固定化酶载体的制备方法 |
| EP3557262B1 (en) | 2014-12-09 | 2022-08-10 | Life Technologies Corporation | High efficiency, small volume nucleic acid synthesis |
| CN104788709A (zh) * | 2015-04-17 | 2015-07-22 | 张家港市山牧新材料技术开发有限公司 | 一种超大粒径复合橡胶改性聚苯乙烯树脂的制备方法 |
| CN107922974B (zh) | 2015-07-02 | 2021-11-09 | 生命技术公司 | 羧基官能亲水微珠的偶合 |
| US9868826B2 (en) | 2015-07-02 | 2018-01-16 | Life Technologies Corporation | Polymer substrates formed from carboxy functional acrylamide |
| US10150992B2 (en) | 2015-07-06 | 2018-12-11 | Life Technologies Corporation | Substrates and methods useful in sequencing |
| GB201512725D0 (en) * | 2015-07-20 | 2015-08-26 | Life Technologies As | Polymeric particles |
| CN105131168A (zh) * | 2015-10-23 | 2015-12-09 | 蓝星（成都）新材料有限公司 | 一种大孔甲基丙烯酸羟乙酯树脂及其制备方法 |
| CA3008679C (en) * | 2015-12-21 | 2023-03-21 | Dow Global Technologies Llc | Multistage aqueous emulsion polymer and aqueous coating composition formed therefrom |
| CN109952237B (zh) | 2016-09-06 | 2022-08-26 | 阿佩利亚科技公司 | 用于轮胎充气的系统 |
| CN106589222A (zh) * | 2016-12-05 | 2017-04-26 | 黄晖 | 一种单分散高分子微球及其制备方法 |
| GB201700983D0 (en) | 2017-01-20 | 2017-03-08 | Life Tech As | Polymeric particles |
| BR112019019338A2 (pt) * | 2017-03-27 | 2020-05-05 | Dow Global Technologies Llc | processo. |
| US10406869B2 (en) | 2017-11-10 | 2019-09-10 | Aperia Technologies, Inc. | Inflation system |
| US11851536B2 (en) * | 2018-10-02 | 2023-12-26 | Xerox Corporation | Precipitation process for preparing polystyrene microparticles |
| US11642920B2 (en) | 2018-11-27 | 2023-05-09 | Aperia Technologies, Inc. | Hub-integrated inflation system |
| 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 |
| CN111635551B (zh) * | 2020-06-23 | 2022-04-22 | 哈尔滨工程大学 | 一步法制备聚酰亚胺开孔泡沫的方法及产品 |
| WO2023088864A1 (de) * | 2021-11-18 | 2023-05-25 | Lanxess Deutschland Gmbh | Verfahren zur herstellung von polymerisaten |
| GB2620799A (en) | 2022-07-22 | 2024-01-24 | Life Tech As | Particles |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE483422A (zh) * | 1946-12-13 | |||
| US4382124B1 (en) | 1958-07-18 | 1994-10-04 | Rohm & Haas | Process for preparing macroreticular resins, copolymers and products of said process |
| NL241315A (zh) | 1958-07-18 | |||
| DE1420830A1 (de) * | 1959-07-16 | 1968-10-31 | Wacker Chemie Gmbh | Verfahren zur Kondensation von Organosiloxanen |
| DE1917090C3 (de) | 1968-04-06 | 1980-04-24 | Sekisui Kagaku Kogyo K.K., Osaka (Japan) | Verfahren zur Herstellung von Styrolpolymerteilchen mit einheitlichen Größen |
| FR2238718A1 (en) | 1973-07-27 | 1975-02-21 | Sekisui Chemical Co Ltd | Polystyrene particles of uniform size, esp. for foams - by polymerising in suspension of fine polystyrene particles, contg. catalyst and polymn retarder |
| NO141367C (no) | 1976-11-22 | 1980-02-27 | Sintef | Framgangsmaate for framstilling av findelte emulsjoner av et litt vannloeselig materiale |
| AU530410B2 (en) | 1978-02-21 | 1983-07-14 | Sintef | Preparing aqueous emulsions |
| JPS5829962B2 (ja) * | 1979-08-23 | 1983-06-25 | 東レ株式会社 | 親水性水不溶性微粒子の製造方法 |
| 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 |
| US4564644A (en) | 1982-08-02 | 1986-01-14 | The Dow Chemical Company | Ion exchange resins prepared by sequential monomer addition |
| JPS6126505A (ja) * | 1984-07-17 | 1986-02-05 | Toray Ind Inc | 黒色粒子 |
| EP0326383B1 (en) * | 1988-01-29 | 1994-06-15 | Mita Industrial Co. Ltd. | Process for preparation of monodisperse polymer particles having increased particle size |
| JPH03237105A (ja) | 1989-09-19 | 1991-10-23 | Mita Ind Co Ltd | 単分散重合体粒子の製造方法 |
| JP3135262B2 (ja) | 1991-03-06 | 2001-02-13 | ガーヴァン インスティチュート オブ メディカル リサーチ | ヒトのガラニン、ヒトのガラニンをエンコードするｃＤ ＮＡクローンとヒトのガラニン製造方法 |
| US5130343A (en) * | 1991-03-13 | 1992-07-14 | Cornell Research Foundation, Inc. | Process for producing uniform macroporous polymer beads |
| US5231115A (en) * | 1991-12-19 | 1993-07-27 | The Dow Chemical Company | Seeded porous copolymers and ion-exchange resins prepared therefrom |
| US5306561A (en) | 1992-02-20 | 1994-04-26 | Cornell Research Foundation, Inc. | Preparation of surface-functional polymer particles |
| JP3166296B2 (ja) | 1992-05-20 | 2001-05-14 | 三菱化学株式会社 | 多孔性架橋共重合体粒子表面の付着微粒子の除去方法 |
| US5366782A (en) * | 1992-08-25 | 1994-11-22 | The Procter & Gamble Company | Polymeric web having deformed sections which provide a substantially increased elasticity to the web |
| CA2097630A1 (en) | 1992-12-29 | 1994-06-30 | Ann Louise Mccormack | Stretch-pillowed, bulked laminate |
| JPH06256438A (ja) | 1993-03-09 | 1994-09-13 | Japan Synthetic Rubber Co Ltd | 重合体粒子の製造方法 |
| JPH0727754A (ja) | 1993-07-09 | 1995-01-31 | Mitsubishi Chem Corp | カチオンクロマトグラフィー用充填剤及びその製造方法 |
| NO308414B1 (no) | 1996-04-23 | 2000-09-11 | Polymers Holding As | Fremgangsmate for fremstilling av PVC-partikler, anvendelse av PVC-partiklene, samt PVC-partiklene som sadan |
| JPH101561A (ja) | 1996-06-17 | 1998-01-06 | Dainippon Ink & Chem Inc | 発泡性スチレン系樹脂粒子 |
| CA2262018C (en) | 1996-07-29 | 2007-10-02 | Nanosphere Llc | Nanoparticles having oligonucleotides attached thereto and uses therefor |
| DE19634393A1 (de) | 1996-08-26 | 1998-03-05 | Bayer Ag | Verfahren zur Herstellung vernetzter Polymerisate |
| JP3510089B2 (ja) | 1997-09-22 | 2004-03-22 | ユニ・チャーム株式会社 | 体液吸収性物品の透液性表面シートおよび該シートの製造方法 |
| PL199101B1 (pl) * | 1997-10-10 | 2008-08-29 | Polymer Systems As | Sposoby wytwarzania polimerów w postaci cząstek |
| EP1177231B1 (en) | 1999-04-09 | 2009-08-19 | Invitrogen Dynal AS | Process for the preparation of monodisperse polymer particles |
-
2000
- 2000-04-10 EP EP00919034A patent/EP1177231B1/en not_active Expired - Lifetime
- 2000-04-10 EP EP08162270.6A patent/EP1985639B1/en not_active Expired - Lifetime
- 2000-04-10 US US09/958,431 patent/US7217762B1/en not_active Expired - Lifetime
- 2000-04-10 AU AU39791/00A patent/AU777829B2/en not_active Expired
- 2000-04-10 CN CNB2005100038156A patent/CN1311005C/zh not_active Expired - Lifetime
- 2000-04-10 WO PCT/GB2000/001334 patent/WO2000061647A1/en active IP Right Grant
- 2000-04-10 CN CNB008070474A patent/CN1189495C/zh not_active Expired - Lifetime
- 2000-04-10 CA CA2369293A patent/CA2369293C/en not_active Expired - Lifetime
- 2000-04-20 TW TW089107457A patent/TW589330B/zh not_active IP Right Cessation
-
2001
- 2001-10-04 NO NO20014835A patent/NO332815B1/no not_active IP Right Cessation
-
2004
- 2004-10-18 AU AU2004222716A patent/AU2004222716B2/en not_active Expired
-
2007
- 2007-05-11 US US11/747,860 patent/US20070265390A1/en not_active Abandoned
-
2009
- 2009-12-21 US US12/644,003 patent/US20100099803A1/en not_active Abandoned
-
2012
- 2012-10-10 US US13/649,045 patent/US8658733B2/en not_active Expired - Fee Related
-
2014
- 2014-01-10 US US14/152,793 patent/US9309368B2/en not_active Expired - Fee Related
-
2015
- 2015-09-28 US US14/867,394 patent/US20160075800A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| NO20014835L (no) | 2001-12-07 |
| US20070265390A1 (en) | 2007-11-15 |
| AU2004222716B2 (en) | 2007-07-05 |
| AU777829B2 (en) | 2004-11-04 |
| CA2369293C (en) | 2010-06-08 |
| EP1177231A1 (en) | 2002-02-06 |
| AU2004222716A1 (en) | 2004-11-11 |
| CA2369293A1 (en) | 2000-10-19 |
| US20140256836A1 (en) | 2014-09-11 |
| AU3979100A (en) | 2000-11-14 |
| EP1985639A2 (en) | 2008-10-29 |
| US20100099803A1 (en) | 2010-04-22 |
| CN1189495C (zh) | 2005-02-16 |
| TW589330B (en) | 2004-06-01 |
| WO2000061647A1 (en) | 2000-10-19 |
| EP1985639A3 (en) | 2008-11-12 |
| US7217762B1 (en) | 2007-05-15 |
| NO20014835D0 (no) | 2001-10-04 |
| US20130035418A1 (en) | 2013-02-07 |
| CN1362973A (zh) | 2002-08-07 |
| US9309368B2 (en) | 2016-04-12 |
| EP1177231B1 (en) | 2009-08-19 |
| EP1985639B1 (en) | 2013-08-14 |
| US8658733B2 (en) | 2014-02-25 |
| US20160075800A1 (en) | 2016-03-17 |
| CN1311005C (zh) | 2007-04-18 |
| CN1644606A (zh) | 2005-07-27 |
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| EREP | Power of attorney discontinued | ||
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Representative=s name: ZACCO NORWAY AS, POSTBOKS 2003 VIKA |
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| CHAD | Change of the owner's name or address (par. 44 patent law, par. patentforskriften) |
Owner name: LIFE TECHNOLOGIES AS, NO |
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| MK1K | Patent expired |