RU2325402C2 - Способы радикальной полимеризации для получения галогенированных полимеров, галогенированные полимеры и изделия из них - Google Patents
Способы радикальной полимеризации для получения галогенированных полимеров, галогенированные полимеры и изделия из них Download PDFInfo
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- RU2325402C2 RU2325402C2 RU2004136996/04A RU2004136996A RU2325402C2 RU 2325402 C2 RU2325402 C2 RU 2325402C2 RU 2004136996/04 A RU2004136996/04 A RU 2004136996/04A RU 2004136996 A RU2004136996 A RU 2004136996A RU 2325402 C2 RU2325402 C2 RU 2325402C2
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- Prior art keywords
- monomer
- reactor
- monomers
- polymers
- ethylenically unsaturated
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- 229920000642 polymer Polymers 0.000 title claims abstract description 189
- 238000000034 method Methods 0.000 title claims abstract description 62
- 238000010526 radical polymerization reaction Methods 0.000 title claims abstract description 47
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- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 20
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- 238000006116 polymerization reaction Methods 0.000 claims abstract description 14
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- 229920006395 saturated elastomer Polymers 0.000 abstract 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 20
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- 239000002184 metal Substances 0.000 description 19
- 150000002739 metals Chemical class 0.000 description 15
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- 230000003647 oxidation Effects 0.000 description 13
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- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 5
- 229910052747 lanthanoid Inorganic materials 0.000 description 5
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- 229910052723 transition metal Inorganic materials 0.000 description 5
- 150000003624 transition metals Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 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 4
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- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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- 125000005842 heteroatom Chemical group 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
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- 230000008569 process Effects 0.000 description 3
- UOORRWUZONOOLO-OWOJBTEDSA-N (E)-1,3-dichloropropene Chemical compound ClC\C=C\Cl UOORRWUZONOOLO-OWOJBTEDSA-N 0.000 description 2
- JFEVIPGMXQNRRF-UHFFFAOYSA-N 1,1,3-trichloroprop-1-ene Chemical compound ClCC=C(Cl)Cl JFEVIPGMXQNRRF-UHFFFAOYSA-N 0.000 description 2
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- 238000005299 abrasion Methods 0.000 description 2
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- 239000012986 chain transfer agent Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- YTKRILODNOEEPX-NSCUHMNNSA-N crotyl chloride Chemical compound C\C=C\CCl YTKRILODNOEEPX-NSCUHMNNSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
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- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
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- WQJUBZMZVKITBU-UHFFFAOYSA-N (3,4-dimethyl-4-phenylhexan-3-yl)benzene Chemical compound C=1C=CC=CC=1C(C)(CC)C(C)(CC)C1=CC=CC=C1 WQJUBZMZVKITBU-UHFFFAOYSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
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- WGGLDBIZIQMEGH-UHFFFAOYSA-N 1-bromo-4-ethenylbenzene Chemical compound BrC1=CC=C(C=C)C=C1 WGGLDBIZIQMEGH-UHFFFAOYSA-N 0.000 description 1
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- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- VBHXIMACZBQHPX-UHFFFAOYSA-N 2,2,2-trifluoroethyl prop-2-enoate Chemical compound FC(F)(F)COC(=O)C=C VBHXIMACZBQHPX-UHFFFAOYSA-N 0.000 description 1
- FALCMQXTWHPRIH-UHFFFAOYSA-N 2,3-dichloroprop-1-ene Chemical compound ClCC(Cl)=C FALCMQXTWHPRIH-UHFFFAOYSA-N 0.000 description 1
- VFXXTYGQYWRHJP-UHFFFAOYSA-N 4,4'-azobis(4-cyanopentanoic acid) Chemical compound OC(=O)CCC(C)(C#N)N=NC(C)(CCC(O)=O)C#N VFXXTYGQYWRHJP-UHFFFAOYSA-N 0.000 description 1
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- 206010067484 Adverse reaction Diseases 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 240000005428 Pistacia lentiscus Species 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- BJOYVZZDDFVLPI-UHFFFAOYSA-N azanium;tetradecanoate Chemical compound [NH4+].CCCCCCCCCCCCCC([O-])=O BJOYVZZDDFVLPI-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
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- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
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- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
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- 239000011248 coating agent Substances 0.000 description 1
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- 150000004696 coordination complex Chemical class 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229920000359 diblock copolymer Polymers 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
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- 239000003995 emulsifying agent Substances 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- CWINGZLCRSDKCL-UHFFFAOYSA-N ethoxycarbonyloxy ethyl carbonate Chemical compound CCOC(=O)OOC(=O)OCC CWINGZLCRSDKCL-UHFFFAOYSA-N 0.000 description 1
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- 150000004694 iodide salts Chemical class 0.000 description 1
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- DUVTXUGBACWHBP-UHFFFAOYSA-N methyl 2-(1h-benzimidazol-2-ylmethoxy)benzoate Chemical compound COC(=O)C1=CC=CC=C1OCC1=NC2=CC=CC=C2N1 DUVTXUGBACWHBP-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- DWFKOMDBEKIATP-UHFFFAOYSA-N n'-[2-[2-(dimethylamino)ethyl-methylamino]ethyl]-n,n,n'-trimethylethane-1,2-diamine Chemical compound CN(C)CCN(C)CCN(C)CCN(C)C DWFKOMDBEKIATP-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
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- 125000005634 peroxydicarbonate group Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
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- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
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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
- C08F293/005—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 using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
-
- 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
- C08F14/00—Homopolymers and 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 a halogen
-
- 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
- C08F214/00—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 a halogen
- C08F214/18—Monomers containing fluorine
-
- 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
- C08F214/00—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 a halogen
- C08F214/18—Monomers containing fluorine
- C08F214/186—Monomers containing fluorine with non-fluorinated comonomers
-
- 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
-
- 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
- C08F8/18—Introducing halogen atoms or halogen-containing groups
- C08F8/20—Halogenation
- C08F8/22—Halogenation by reaction with free halogens
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
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- 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)
- Graft Or Block Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Polymerization Catalysts (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0206246 | 2002-05-17 | ||
| FR0206246A FR2839724B1 (fr) | 2002-05-17 | 2002-05-17 | Procedes de polymerisation radicalaire pour preparer des polymeres halogenes et polymeres halogenes |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2007144484/04A Division RU2419635C2 (ru) | 2002-05-17 | 2007-11-29 | Способы радикальной полимеризации для получения галогенированных полимеров, галогенированные полимеры и изделия из них |
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| RU2004136996A RU2004136996A (ru) | 2005-07-10 |
| RU2325402C2 true RU2325402C2 (ru) | 2008-05-27 |
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| Application Number | Title | Priority Date | Filing Date |
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| RU2004136996/04A RU2325402C2 (ru) | 2002-05-17 | 2003-05-16 | Способы радикальной полимеризации для получения галогенированных полимеров, галогенированные полимеры и изделия из них |
| RU2007144484/04A RU2419635C2 (ru) | 2002-05-17 | 2007-11-29 | Способы радикальной полимеризации для получения галогенированных полимеров, галогенированные полимеры и изделия из них |
| RU2011102762/04A RU2582616C2 (ru) | 2002-05-17 | 2011-01-25 | Способы радикальной полимеризации для получения галогенированных полимеров, галогенированные полимеры и изделия из них |
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| Application Number | Title | Priority Date | Filing Date |
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| RU2007144484/04A RU2419635C2 (ru) | 2002-05-17 | 2007-11-29 | Способы радикальной полимеризации для получения галогенированных полимеров, галогенированные полимеры и изделия из них |
| RU2011102762/04A RU2582616C2 (ru) | 2002-05-17 | 2011-01-25 | Способы радикальной полимеризации для получения галогенированных полимеров, галогенированные полимеры и изделия из них |
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| Country | Link |
|---|---|
| US (3) | US7078473B2 (https=) |
| EP (3) | EP2045271B1 (https=) |
| JP (3) | JP4357415B2 (https=) |
| CN (3) | CN101597353B (https=) |
| AT (3) | ATE422206T1 (https=) |
| AU (1) | AU2003232808A1 (https=) |
| DE (2) | DE60336359D1 (https=) |
| ES (1) | ES2321926T3 (https=) |
| FR (1) | FR2839724B1 (https=) |
| PT (1) | PT1507807E (https=) |
| RU (3) | RU2325402C2 (https=) |
| WO (1) | WO2003097704A1 (https=) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2839724B1 (fr) | 2002-05-17 | 2005-08-05 | Solvay | Procedes de polymerisation radicalaire pour preparer des polymeres halogenes et polymeres halogenes |
| US7741524B2 (en) * | 2003-04-22 | 2010-06-22 | Solvay (Societe Anonyme) | Iodinated organic substances of low molecular mass and process for preparing them |
| JP5078353B2 (ja) * | 2003-09-23 | 2012-11-21 | ソルヴェイ（ソシエテ アノニム） | ポリマー組成物 |
| 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 |
| KR100899985B1 (ko) * | 2006-06-12 | 2009-05-28 | 주식회사 엘지화학 | 현탁 중합에 의한 염화 비닐계 중합체의 제조 방법 |
| FR2903409A1 (fr) * | 2006-07-04 | 2008-01-11 | Solvay | Procede de polymerisation radicalaire en dispersion aqueuse pour la preparation de polymeres |
| 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 |
| BRPI0808594A2 (pt) * | 2007-04-02 | 2014-08-05 | Akzo Nobel Nv | "solução aceleradora, resina insaturada ou resina de acrilato e uso da solução aceleradora" |
| US20100256299A1 (en) | 2007-06-21 | 2010-10-07 | Tijs Nabuurs | Process for obtaining low free monomer levels in a block copolymer emulsion prepared with (reverse) iodine transfer polymerisation |
| US8366980B2 (en) * | 2007-07-31 | 2013-02-05 | Stella Chemifa Corporation | Method for producing hollow structual body |
| JP2013018953A (ja) * | 2011-06-15 | 2013-01-31 | Canon Inc | 高分子粒子の製造方法 |
| BR112014014967B1 (pt) * | 2011-12-21 | 2020-12-15 | Centre National De La Recherche Scientifique | Processo para a preparação de um polímero de cloreto de vinilideno |
| EP2809698B1 (fr) * | 2012-01-31 | 2016-01-27 | Rhodia Operations | Polymérisation en phase dispersée de monomères vinyliques halogénés en présence de stabilisants réactifs vivants |
| JP2014084411A (ja) * | 2012-10-24 | 2014-05-12 | Canon Inc | 高分子粒子の製造方法 |
| MX2021008506A (es) | 2019-02-11 | 2021-08-19 | Dow Global Technologies Llc | Metodo de polimerizacion por transferencia inversa de yodo y composiciones de este. |
| MX2021008508A (es) | 2019-02-11 | 2021-08-19 | Dow Global Technologies Llc | Metodo de polimerizacion por transferencia de yodo y composiciones a partir del mismo. |
| US11945890B2 (en) | 2022-03-23 | 2024-04-02 | Mexichem Specialty Resins Inc. | Fluorinated PVC copolymer compositions for increased ultraviolet protection |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU365070A1 (ru) * | Способ получения полимеров и сополимеров галоидпроизводных этилена | |||
| SU440378A1 (ru) * | 1972-12-06 | 1974-08-25 | Предприятие П/Я М-5927 | Способ получени блок-сополимеров |
| RU2171262C2 (ru) * | 1995-11-04 | 2001-07-27 | Акцо Нобель Н.В. | Способ радикальной (со)полимеризации |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3251810A (en) * | 1960-12-24 | 1966-05-17 | Dynamit Nobel Ag | Copolymerization of vinyl chloride with a catalyst consisting of aluminum trialkyl, a boric acid ester and a cocatalyst |
| US3467636A (en) * | 1967-02-24 | 1969-09-16 | Du Pont | Redox catalyst system for preparing vinylidene fluoride interpolymers |
| US3467363A (en) * | 1967-08-31 | 1969-09-16 | Richard Alan Reichel | Noise generator for shaking loose packed material |
| DE2000501A1 (de) * | 1970-01-07 | 1971-07-15 | Basf Ag | Verfahren zur Polymerisation von Vinyl- und Vinylidenverbindungen |
| JPS5218787A (en) * | 1975-08-04 | 1977-02-12 | Kanegafuchi Chem Ind Co Ltd | Suspension polymerization process of vinyl chloride |
| JPS5212291A (en) * | 1975-07-18 | 1977-01-29 | Shin Etsu Chem Co Ltd | Process for polymerizing vinyl chloride |
| US4180634A (en) * | 1975-07-18 | 1979-12-25 | Shin-Etsu Chemical Co., Ltd. | Polymerizing vinyl chloride with lowering of scale formation |
| JP2795699B2 (ja) * | 1989-10-06 | 1998-09-10 | 日本メクトロン株式会社 | 含フッ素ブロック共重合体の製造法 |
| JPH0826087B2 (ja) * | 1990-11-29 | 1996-03-13 | ダイキン工業株式会社 | ポリマーの新規な製造方法 |
| JPH075714B2 (ja) * | 1992-09-07 | 1995-01-25 | 工業技術院長 | ポリ（安息香酸）、その製造方法及びそれを用いたポリ（パラフェニレン）の製造方法 |
| US5342910A (en) * | 1992-12-18 | 1994-08-30 | The Dow Chemical Company | Process for preparing vinylidene chloride or vinyl chloride polymer by suspension polymerization |
| EP0974604B1 (en) * | 1993-03-22 | 2003-05-07 | Oxy Vinyls L.P. | Method of synthesising 1-halo-1-iodoethane |
| US5312871A (en) * | 1993-07-27 | 1994-05-17 | Carnegie Mellon University | Free radical polymerization process |
| JPH1144970A (ja) * | 1997-05-28 | 1999-02-16 | Ricoh Co Ltd | 静電荷像現像用乾式現像剤 |
| US6093770A (en) * | 1998-02-02 | 2000-07-25 | Xerox Corporation | Polymers and processes thereof |
| FR2786178A1 (fr) * | 1998-11-25 | 2000-05-26 | Solvay | Monomeres trifluorovinyliques fonctionnels et leur copolymerisation avec des olefines fluorees |
| FR2818580B1 (fr) * | 2000-12-22 | 2003-03-21 | Solvay | Structures a couches polymeriques multiples |
| US6838535B2 (en) * | 2001-03-23 | 2005-01-04 | University Of Pennsylvania | Process for the living radical polymerization of chlorine containing monomers |
| FR2839724B1 (fr) | 2002-05-17 | 2005-08-05 | Solvay | Procedes de polymerisation radicalaire pour preparer des polymeres halogenes et polymeres halogenes |
| US7741524B2 (en) * | 2003-04-22 | 2010-06-22 | Solvay (Societe Anonyme) | Iodinated organic substances of low molecular mass and process for preparing them |
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- 2003-05-16 WO PCT/EP2003/005314 patent/WO2003097704A1/fr not_active Ceased
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU365070A1 (ru) * | Способ получения полимеров и сополимеров галоидпроизводных этилена | |||
| SU440378A1 (ru) * | 1972-12-06 | 1974-08-25 | Предприятие П/Я М-5927 | Способ получени блок-сополимеров |
| RU2171262C2 (ru) * | 1995-11-04 | 2001-07-27 | Акцо Нобель Н.В. | Способ радикальной (со)полимеризации |
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