CA2491048C - Process for the preparation of block copolymers - Google Patents
Process for the preparation of block copolymers Download PDFInfo
- Publication number
- CA2491048C CA2491048C CA2491048A CA2491048A CA2491048C CA 2491048 C CA2491048 C CA 2491048C CA 2491048 A CA2491048 A CA 2491048A CA 2491048 A CA2491048 A CA 2491048A CA 2491048 C CA2491048 C CA 2491048C
- Authority
- CA
- Canada
- Prior art keywords
- process according
- polymerization
- isoindole
- dihydro
- monomers
- 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 - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 33
- 229920001400 block copolymer Polymers 0.000 title claims abstract description 25
- 230000008569 process Effects 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 239000000178 monomer Substances 0.000 claims abstract description 38
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 32
- 230000000977 initiatory effect Effects 0.000 claims abstract description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 239000003999 initiator Substances 0.000 claims description 10
- 150000003254 radicals Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- -1 alkyl radical Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 5
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- GXQCDKKQWPZUDS-UHFFFAOYSA-N 2-methyl-2-(1,1,3,3-tetraethylisoindol-2-yl)propanenitrile Chemical compound C1=CC=C2C(CC)(CC)N(C(C)(C)C#N)C(CC)(CC)C2=C1 GXQCDKKQWPZUDS-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- NLVPDDMNXQPTDI-UHFFFAOYSA-N 1,1,3,3-tetraethyl-2-(2-phenylethyl)isoindole Chemical compound CCC1(CC)C2=CC=CC=C2C(CC)(CC)N1CCC1=CC=CC=C1 NLVPDDMNXQPTDI-UHFFFAOYSA-N 0.000 claims description 3
- IFWKDEUQTPFDAS-UHFFFAOYSA-N 1,1,3,3-tetramethyl-2-(2-phenylethyl)isoindole Chemical compound CC1(C)C2=CC=CC=C2C(C)(C)N1CCC1=CC=CC=C1 IFWKDEUQTPFDAS-UHFFFAOYSA-N 0.000 claims description 3
- PDBHFHOORUGDOX-UHFFFAOYSA-N 1,1,3,3-tetramethyl-2-(2-phenylpropan-2-yl)isoindole Chemical compound CC1(C)C2=CC=CC=C2C(C)(C)N1C(C)(C)C1=CC=CC=C1 PDBHFHOORUGDOX-UHFFFAOYSA-N 0.000 claims description 3
- NQUVYKGLCGSNQB-UHFFFAOYSA-N 2-methyl-2-(1,1,3,3-tetramethylisoindol-2-yl)propanenitrile Chemical compound C1=CC=C2C(C)(C)N(C(C)(C#N)C)C(C)(C)C2=C1 NQUVYKGLCGSNQB-UHFFFAOYSA-N 0.000 claims description 3
- JNNIDVFHKQRHJF-UHFFFAOYSA-N 1,1,3,3-tetraethyl-2-(2-phenylpropan-2-yl)isoindole Chemical compound CCC1(CC)C2=CC=CC=C2C(CC)(CC)N1C(C)(C)C1=CC=CC=C1 JNNIDVFHKQRHJF-UHFFFAOYSA-N 0.000 claims description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 claims description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 150000002976 peresters Chemical class 0.000 claims description 2
- 150000002978 peroxides Chemical class 0.000 claims description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 20
- 229920000642 polymer Polymers 0.000 description 16
- 239000000047 product Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- IZMUYZWVFCIQJQ-UHFFFAOYSA-N 2-methyl-2-(2,2,6,6-tetramethylpiperidin-1-yl)oxypropanenitrile Chemical compound N#CC(C)(C)ON1C(C)(C)CCCC1(C)C IZMUYZWVFCIQJQ-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- SVHAMPNLOLKSFU-UHFFFAOYSA-N 1,2,2-trichloroethenylbenzene Chemical compound ClC(Cl)=C(Cl)C1=CC=CC=C1 SVHAMPNLOLKSFU-UHFFFAOYSA-N 0.000 description 1
- AUHKVLIZXLBQSR-UHFFFAOYSA-N 1,2-dichloro-3-(1,2,2-trichloroethenyl)benzene Chemical compound ClC(Cl)=C(Cl)C1=CC=CC(Cl)=C1Cl AUHKVLIZXLBQSR-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- XPXMCUKPGZUFGR-UHFFFAOYSA-N 1-chloro-2-(1,2,2-trichloroethenyl)benzene Chemical compound ClC(Cl)=C(Cl)C1=CC=CC=C1Cl XPXMCUKPGZUFGR-UHFFFAOYSA-N 0.000 description 1
- SQQBJYCUVMJZAY-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-(2-phenylethoxy)piperidine Chemical compound CC1(C)CCCC(C)(C)N1OCCC1=CC=CC=C1 SQQBJYCUVMJZAY-UHFFFAOYSA-N 0.000 description 1
- HMVSHELWGDSUJC-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-(2-phenylpropan-2-yloxy)piperidine Chemical compound C=1C=CC=CC=1C(C)(C)ON1C(C)(C)CCCC1(C)C HMVSHELWGDSUJC-UHFFFAOYSA-N 0.000 description 1
- QZTRSTJHBMRGEK-UHFFFAOYSA-N 2-(4-hydroxy-2,2,6,6-tetramethylpiperidin-1-yl)oxy-2-methylpropanenitrile Chemical compound N#CC(C)(C)ON1C(C)(C)CC(O)CC1(C)C QZTRSTJHBMRGEK-UHFFFAOYSA-N 0.000 description 1
- CTHJQRHPNQEPAB-UHFFFAOYSA-N 2-methoxyethenylbenzene Chemical compound COC=CC1=CC=CC=C1 CTHJQRHPNQEPAB-UHFFFAOYSA-N 0.000 description 1
- BTOVVHWKPVSLBI-UHFFFAOYSA-N 2-methylprop-1-enylbenzene Chemical compound CC(C)=CC1=CC=CC=C1 BTOVVHWKPVSLBI-UHFFFAOYSA-N 0.000 description 1
- FMFHUEMLVAIBFI-UHFFFAOYSA-N 2-phenylethenyl acetate Chemical compound CC(=O)OC=CC1=CC=CC=C1 FMFHUEMLVAIBFI-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- OGBVRMYSNSKIEF-UHFFFAOYSA-N Benzylphosphonic acid Chemical class OP(O)(=O)CC1=CC=CC=C1 OGBVRMYSNSKIEF-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- YMOONIIMQBGTDU-VOTSOKGWSA-N [(e)-2-bromoethenyl]benzene Chemical compound Br\C=C\C1=CC=CC=C1 YMOONIIMQBGTDU-VOTSOKGWSA-N 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- YLFIGGHWWPSIEG-UHFFFAOYSA-N aminoxyl Chemical compound [O]N YLFIGGHWWPSIEG-UHFFFAOYSA-N 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- KETWBQOXTBGBBN-UHFFFAOYSA-N hex-1-enylbenzene Chemical compound CCCCC=CC1=CC=CC=C1 KETWBQOXTBGBBN-UHFFFAOYSA-N 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 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
- 229940038597 peroxide anti-acne preparations for topical use Drugs 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Graft Or Block Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerization Catalysts (AREA)
- Polymerisation Methods In General (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI2002A001495 | 2002-07-09 | ||
| IT001495A ITMI20021495A1 (it) | 2002-07-09 | 2002-07-09 | Procedimento per la preparazione di copolimeri a blocchi. |
| PCT/EP2003/006837 WO2004005361A1 (en) | 2002-07-09 | 2003-06-26 | Process for the preparation of block copolymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2491048A1 CA2491048A1 (en) | 2004-01-15 |
| CA2491048C true CA2491048C (en) | 2010-08-31 |
Family
ID=30012500
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2491048A Expired - Fee Related CA2491048C (en) | 2002-07-09 | 2003-06-26 | Process for the preparation of block copolymers |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7388052B2 (https=) |
| EP (1) | EP1519970B1 (https=) |
| JP (1) | JP4477493B2 (https=) |
| CN (1) | CN1308363C (https=) |
| AT (1) | ATE376562T1 (https=) |
| AU (1) | AU2003242772A1 (https=) |
| BR (1) | BR0312348B1 (https=) |
| CA (1) | CA2491048C (https=) |
| DE (1) | DE60317066T2 (https=) |
| ES (1) | ES2295643T3 (https=) |
| IT (1) | ITMI20021495A1 (https=) |
| MX (1) | MXPA04012791A (https=) |
| PL (1) | PL209004B1 (https=) |
| RU (1) | RU2320675C2 (https=) |
| WO (1) | WO2004005361A1 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20040752A1 (it) * | 2004-04-16 | 2004-07-16 | Polimeri Europa Spa | Procedimento per la preparazione di co polimeri vinilaromatici aggraffati su elastometro in modo controllato |
| US8557907B2 (en) * | 2005-08-26 | 2013-10-15 | Macro-M S.A. De C.V. | Reactive block copolymers for the preparation of inorganic tubule-polymer composites |
| US20100311920A1 (en) | 2005-08-26 | 2010-12-09 | Cid Centro De Investigacion Y Desarrollo Tecnologico Sa De Cv | Using Reactive Block Copolymers as Chain Extenders and Surface Modifiers |
| US8357759B2 (en) | 2005-08-26 | 2013-01-22 | CID Centro de Investigación y Desarrollo Tecnológico S.A. de C.V. | Reactive block copolymers |
| US8344058B2 (en) * | 2005-08-26 | 2013-01-01 | CID Centro de Investigación y Desarrollo Technológico S.A. de C.V. | Reactive block copolymers as additives for the preparation of silicate-polymer composites |
| ATE465183T1 (de) * | 2005-08-30 | 2010-05-15 | Basf Se | Aus nitroxylradikalpolymerisation gewonnene polymere |
| US20100311849A1 (en) * | 2006-08-23 | 2010-12-09 | Cid Centro De Investigacion Y Desarrollo Tecnologico Sa De Cv | Using Reactive Block Copolymers as Chain Extenders and Surface Modifiers |
| JP5229167B2 (ja) * | 2009-09-04 | 2013-07-03 | 株式会社リコー | ラジカル重合用組成物及びポリマーの製造方法 |
| ITMI20121973A1 (it) | 2012-11-20 | 2014-05-21 | Versalis Spa | Composizione polimerica autoestinguente |
| FR3008986B1 (fr) * | 2013-07-25 | 2016-12-30 | Arkema France | Procede de controle de la periode caracterisant la morphologie obtenue a partir d'un melange de copolymere a blocs et de (co) polymeres de l'un des blocs |
| JP2017507237A (ja) * | 2014-03-07 | 2017-03-16 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 制御されたラジカル重合 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0876414B1 (de) * | 1996-01-25 | 1999-08-25 | Basf Aktiengesellschaft | Blockcopolymere |
| US6281311B1 (en) * | 1997-03-31 | 2001-08-28 | Pmd Holdings Corp. | Controlled free radical polymerization process |
| US6111025A (en) * | 1997-06-24 | 2000-08-29 | The Lubrizol Corporation | Block copolymer surfactants prepared by stabilized free-radical polymerization |
| FR2781487B1 (fr) * | 1998-07-10 | 2000-12-08 | Atochem Elf Sa | Polymerisation en emulsion en presence d'un radical libre stable |
| US6369162B1 (en) * | 1998-10-26 | 2002-04-09 | The Lubrizol Corporation | Radial polymers prepared by stabilized free radical polymerization |
| US20020010267A1 (en) * | 1999-03-09 | 2002-01-24 | Symyx Technologies, Inc., A Delaware Corporation | Block copolymers |
| US6569162B2 (en) * | 2001-03-29 | 2003-05-27 | Ding Sheng He | Passively self-cooled electrode design for ablation catheters |
| TW572896B (en) * | 2000-05-26 | 2004-01-21 | Ciba Sc Holding Ag | Process for the synthesis of amine ethers from secondary amino oxides |
| TW574236B (en) * | 2000-09-25 | 2004-02-01 | Ciba Sc Holding Ag | Process for controlled radical polymerization in aqueous dispersion |
-
2002
- 2002-07-09 IT IT001495A patent/ITMI20021495A1/it unknown
-
2003
- 2003-06-26 DE DE60317066T patent/DE60317066T2/de not_active Expired - Lifetime
- 2003-06-26 EP EP03762534A patent/EP1519970B1/en not_active Expired - Lifetime
- 2003-06-26 RU RU2004138077/04A patent/RU2320675C2/ru active
- 2003-06-26 MX MXPA04012791A patent/MXPA04012791A/es active IP Right Grant
- 2003-06-26 US US10/518,550 patent/US7388052B2/en not_active Expired - Lifetime
- 2003-06-26 BR BRPI0312348-0A patent/BR0312348B1/pt not_active IP Right Cessation
- 2003-06-26 AU AU2003242772A patent/AU2003242772A1/en not_active Abandoned
- 2003-06-26 CA CA2491048A patent/CA2491048C/en not_active Expired - Fee Related
- 2003-06-26 PL PL373261A patent/PL209004B1/pl unknown
- 2003-06-26 ES ES03762534T patent/ES2295643T3/es not_active Expired - Lifetime
- 2003-06-26 WO PCT/EP2003/006837 patent/WO2004005361A1/en not_active Ceased
- 2003-06-26 JP JP2004518602A patent/JP4477493B2/ja not_active Expired - Fee Related
- 2003-06-26 CN CNB038160951A patent/CN1308363C/zh not_active Expired - Fee Related
- 2003-06-26 AT AT03762534T patent/ATE376562T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BR0312348B1 (pt) | 2012-12-25 |
| ITMI20021495A1 (it) | 2002-10-08 |
| PL209004B1 (pl) | 2011-07-29 |
| US20070219329A1 (en) | 2007-09-20 |
| EP1519970A1 (en) | 2005-04-06 |
| ATE376562T1 (de) | 2007-11-15 |
| RU2004138077A (ru) | 2005-08-20 |
| US7388052B2 (en) | 2008-06-17 |
| JP4477493B2 (ja) | 2010-06-09 |
| PL373261A1 (en) | 2005-08-22 |
| ES2295643T3 (es) | 2008-04-16 |
| DE60317066T2 (de) | 2008-08-07 |
| JP2005532442A (ja) | 2005-10-27 |
| CA2491048A1 (en) | 2004-01-15 |
| CN1665855A (zh) | 2005-09-07 |
| BR0312348A (pt) | 2005-04-05 |
| MXPA04012791A (es) | 2005-02-24 |
| WO2004005361A1 (en) | 2004-01-15 |
| AU2003242772A1 (en) | 2004-01-23 |
| EP1519970B1 (en) | 2007-10-24 |
| DE60317066D1 (de) | 2007-12-06 |
| RU2320675C2 (ru) | 2008-03-27 |
| CN1308363C (zh) | 2007-04-04 |
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| Publication | Publication Date | Title |
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