JP6289905B2 - 水および溶媒を含まないニトリルゴムの製造方法 - Google Patents
水および溶媒を含まないニトリルゴムの製造方法 Download PDFInfo
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- JP6289905B2 JP6289905B2 JP2013500453A JP2013500453A JP6289905B2 JP 6289905 B2 JP6289905 B2 JP 6289905B2 JP 2013500453 A JP2013500453 A JP 2013500453A JP 2013500453 A JP2013500453 A JP 2013500453A JP 6289905 B2 JP6289905 B2 JP 6289905B2
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- JP
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- Prior art keywords
- nitrile rubber
- extruder
- fluid
- unsaturated
- degassing
- 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
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- 229920000459 Nitrile rubber Polymers 0.000 title claims description 112
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 34
- 239000002904 solvent Substances 0.000 title description 17
- 238000004519 manufacturing process Methods 0.000 title description 5
- -1 hydroxyimino, carbamoyl Chemical group 0.000 claims description 151
- 239000012530 fluid Substances 0.000 claims description 113
- 238000007872 degassing Methods 0.000 claims description 68
- 238000000034 method Methods 0.000 claims description 66
- 150000001875 compounds Chemical class 0.000 claims description 56
- 229920006395 saturated elastomer Polymers 0.000 claims description 35
- 229920000642 polymer Polymers 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 239000000178 monomer Substances 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 26
- 238000009825 accumulation Methods 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
- 150000001993 dienes Chemical class 0.000 claims description 19
- 230000008569 process Effects 0.000 claims description 19
- 239000004593 Epoxy Substances 0.000 claims description 18
- 150000002825 nitriles Chemical class 0.000 claims description 18
- 125000004043 oxo group Chemical group O=* 0.000 claims description 18
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 18
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 17
- 238000003303 reheating Methods 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000004104 aryloxy group Chemical group 0.000 claims description 14
- 239000012855 volatile organic compound Substances 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 238000004891 communication Methods 0.000 claims description 11
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000005110 aryl thio group Chemical group 0.000 claims description 10
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- 150000002513 isocyanates Chemical class 0.000 claims description 9
- NONOKGVFTBWRLD-UHFFFAOYSA-N isocyanatosulfanylimino(oxo)methane Chemical compound O=C=NSN=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 claims description 9
- CYFLXLSBHQBMFT-UHFFFAOYSA-N sulfamoxole Chemical group O1C(C)=C(C)N=C1NS(=O)(=O)C1=CC=C(N)C=C1 CYFLXLSBHQBMFT-UHFFFAOYSA-N 0.000 claims description 9
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 9
- NNBZRMINUVCKKA-UHFFFAOYSA-N S(=O)(O)OSS(=O)(=O)O Chemical compound S(=O)(O)OSS(=O)(=O)O NNBZRMINUVCKKA-UHFFFAOYSA-N 0.000 claims description 8
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 8
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 8
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 7
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 7
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 7
- 150000001345 alkine derivatives Chemical class 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
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- 229920000728 polyester Polymers 0.000 claims description 6
- 229920001296 polysiloxane Polymers 0.000 claims description 6
- 238000003860 storage Methods 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
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- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 5
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 4
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 3
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 4
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims 4
- 125000005300 thiocarboxy group Chemical group C(=S)(O)* 0.000 claims 4
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 2
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 24
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- 239000003999 initiator Substances 0.000 description 20
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- 230000000087 stabilizing effect Effects 0.000 description 17
- 230000032258 transport Effects 0.000 description 17
- 150000005840 aryl radicals Chemical class 0.000 description 16
- 238000006116 polymerization reaction Methods 0.000 description 16
- 239000005060 rubber Substances 0.000 description 16
- 150000003839 salts Chemical class 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 15
- 125000004452 carbocyclyl group Chemical group 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 12
- 239000003431 cross linking reagent Substances 0.000 description 12
- 125000005842 heteroatom Chemical group 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 12
- 125000004429 atom Chemical group 0.000 description 11
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 11
- 239000007789 gas Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 239000011593 sulfur Substances 0.000 description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- 238000004898 kneading Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000007792 addition Methods 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 150000002978 peroxides Chemical class 0.000 description 9
- 238000010526 radical polymerization reaction Methods 0.000 description 9
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
- 238000011144 upstream manufacturing Methods 0.000 description 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 8
- 125000005907 alkyl ester group Chemical group 0.000 description 8
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 8
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 8
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 8
- 230000000977 initiatory effect Effects 0.000 description 8
- 150000002763 monocarboxylic acids Chemical class 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 8
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- 125000004183 alkoxy alkyl group Chemical group 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 239000000945 filler Substances 0.000 description 7
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 7
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- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
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- OPNUROKCUBTKLF-UHFFFAOYSA-N 1,2-bis(2-methylphenyl)guanidine Chemical compound CC1=CC=CC=C1N\C(N)=N\C1=CC=CC=C1C OPNUROKCUBTKLF-UHFFFAOYSA-N 0.000 description 5
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 5
- 239000004606 Fillers/Extenders Substances 0.000 description 5
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C2/00—Treatment of rubber solutions
- C08C2/02—Purification
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C1/00—Treatment of rubber latex
- C08C1/02—Chemical or physical treatment of rubber latex before or during concentration
- C08C1/075—Concentrating
- C08C1/12—Concentrating by evaporation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C2/00—Treatment of rubber solutions
-
- 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
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- 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
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
-
- 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
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F236/12—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated with nitriles
-
- 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
- C08F6/00—Post-polymerisation treatments
- C08F6/06—Treatment of polymer solutions
- C08F6/10—Removal of volatile materials, e.g. solvents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
- C08L9/02—Copolymers with acrylonitrile
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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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10157844A EP2368916B1 (en) | 2010-03-25 | 2010-03-25 | Process for the production of water and solvent-free nitrile rubbers |
| EP10157844.1 | 2010-03-25 | ||
| PCT/EP2011/054257 WO2011117194A1 (en) | 2010-03-25 | 2011-03-21 | Process for the production of water and solvent-free nitrile rubbers |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015213145A Division JP6257570B2 (ja) | 2010-03-25 | 2015-10-29 | 水および溶媒を含まないニトリルゴムの製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013523901A JP2013523901A (ja) | 2013-06-17 |
| JP2013523901A5 JP2013523901A5 (enExample) | 2014-04-03 |
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| JP2015213145A Expired - Fee Related JP6257570B2 (ja) | 2010-03-25 | 2015-10-29 | 水および溶媒を含まないニトリルゴムの製造方法 |
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| WO (1) | WO2011117194A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2368916B1 (en) * | 2010-03-25 | 2012-08-22 | LANXESS International SA | Process for the production of water and solvent-free nitrile rubbers |
| EP2610296A1 (de) | 2011-12-29 | 2013-07-03 | Lanxess Deutschland GmbH | Verfahren zur Herstellung von gereinigten Nitrilkautschuken |
| US20150044559A1 (en) | 2012-03-26 | 2015-02-12 | Zeon Corporation | Composite particles for negative electrodes of secondary batteries, use of same, method for producing same, and binder composition |
| EP2810956A1 (de) * | 2013-06-03 | 2014-12-10 | LANXESS Deutschland GmbH | Über Bisdihydropyrazol-Gruppen gekuppelte Nitrilkautschuke, deren Herstellung und Verwendung |
| EP2860196A1 (de) * | 2013-10-14 | 2015-04-15 | LANXESS Deutschland GmbH | Nitrilkautschuke mit niedrigen Emissionswerten |
| WO2016013218A1 (ja) | 2014-07-25 | 2016-01-28 | 日本ゼオン株式会社 | 架橋性ゴム組成物およびゴム架橋物 |
| EP3081689A1 (de) * | 2015-04-13 | 2016-10-19 | ARLANXEO Deutschland GmbH | Textile bodenbeläge mit niedrigen emissionswerten |
| EP3283538B1 (de) | 2015-04-13 | 2019-06-19 | ARLANXEO Deutschland GmbH | Emissionsarme, nitrilkautschuke enthaltende pulverförmige mischungen |
| JP6752053B2 (ja) * | 2016-05-24 | 2020-09-09 | 旭化成株式会社 | 共役ジエン重合体の製造方法及びゴムベールの製造方法 |
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| US4198265A (en) * | 1977-11-30 | 1980-04-15 | The Firestone Tire & Rubber Company | Method of removing volatiles from an elastomer |
| JPS5653104A (en) * | 1979-10-09 | 1981-05-12 | Mitsui Petrochem Ind Ltd | Separation of polymer from polymer solution |
| DE3118200A1 (de) * | 1981-05-08 | 1982-11-25 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung hochnitrilhaltiger kautschuklatices |
| NL8203281A (nl) | 1982-08-21 | 1984-03-16 | Stamicarbon | Inrichting en werkwijze voor het winnen van polymeer uit een oplossing. |
| DE3618907A1 (de) | 1986-06-05 | 1987-12-10 | Bayer Ag | Verbundwerkstoffe aus vorbehandeltem fasermaterial und vulkanisaten aus hnbr |
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| EP2009050B1 (en) * | 2006-04-17 | 2011-08-31 | Zeon Corporation | Crosslinkable nitrile rubber composition and crosslinked rubber product |
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| EP2368916B1 (en) * | 2010-03-25 | 2012-08-22 | LANXESS International SA | Process for the production of water and solvent-free nitrile rubbers |
| JP5751407B2 (ja) | 2011-01-19 | 2015-07-22 | セイコーエプソン株式会社 | 液体噴射ヘッド、液体噴射装置、圧電素子、超音波センサー及び赤外線センサー |
-
2010
- 2010-03-25 EP EP10157844A patent/EP2368916B1/en not_active Revoked
- 2010-03-25 PL PL10157844T patent/PL2368916T3/pl unknown
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2011
- 2011-03-21 CN CN201180015957.8A patent/CN102822205B/zh not_active Expired - Fee Related
- 2011-03-21 EP EP11709940A patent/EP2550301A1/en not_active Withdrawn
- 2011-03-21 US US13/635,810 patent/US9469697B2/en not_active Expired - Fee Related
- 2011-03-21 CA CA2792840A patent/CA2792840C/en not_active Expired - Fee Related
- 2011-03-21 WO PCT/EP2011/054257 patent/WO2011117194A1/en not_active Ceased
- 2011-03-21 KR KR1020127027740A patent/KR101456351B1/ko not_active Expired - Fee Related
- 2011-03-21 JP JP2013500453A patent/JP6289905B2/ja not_active Expired - Fee Related
- 2011-03-21 BR BR112012024354A patent/BR112012024354B1/pt active IP Right Grant
- 2011-03-24 TW TW100110105A patent/TWI511981B/zh not_active IP Right Cessation
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Also Published As
| Publication number | Publication date |
|---|---|
| TW201211064A (en) | 2012-03-16 |
| JP6257570B2 (ja) | 2018-01-10 |
| JP2013523901A (ja) | 2013-06-17 |
| CA2792840C (en) | 2018-05-15 |
| US10858455B2 (en) | 2020-12-08 |
| US9469697B2 (en) | 2016-10-18 |
| JP2016026262A (ja) | 2016-02-12 |
| WO2011117194A1 (en) | 2011-09-29 |
| KR101456351B1 (ko) | 2014-11-03 |
| EP2550301A1 (en) | 2013-01-30 |
| US20130211031A1 (en) | 2013-08-15 |
| CN102822205B (zh) | 2014-09-24 |
| TWI511981B (zh) | 2015-12-11 |
| BR112012024354B1 (pt) | 2020-01-14 |
| KR20130027488A (ko) | 2013-03-15 |
| CN102822205A (zh) | 2012-12-12 |
| EP2368916B1 (en) | 2012-08-22 |
| EP2368916A1 (en) | 2011-09-28 |
| BR112012024354A2 (pt) | 2016-05-24 |
| BR112012024354A8 (pt) | 2016-08-02 |
| PL2368916T3 (pl) | 2013-03-29 |
| CA2792840A1 (en) | 2011-09-29 |
| US20160369014A1 (en) | 2016-12-22 |
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