CA2304501A1 - Process for hydrogenating carboxylated nitrile rubber, the hydrogenated rubber and its uses - Google Patents
Process for hydrogenating carboxylated nitrile rubber, the hydrogenated rubber and its uses Download PDFInfo
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- CA2304501A1 CA2304501A1 CA002304501A CA2304501A CA2304501A1 CA 2304501 A1 CA2304501 A1 CA 2304501A1 CA 002304501 A CA002304501 A CA 002304501A CA 2304501 A CA2304501 A CA 2304501A CA 2304501 A1 CA2304501 A1 CA 2304501A1
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- Prior art keywords
- polymer
- process according
- catalyst
- hydrogenated
- weight
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 42
- 230000008569 process Effects 0.000 title claims description 32
- 229920000459 Nitrile rubber Polymers 0.000 title claims description 13
- 229920001971 elastomer Polymers 0.000 title description 33
- 239000005060 rubber Substances 0.000 title description 32
- 229920000642 polymer Polymers 0.000 claims abstract description 104
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 239000003054 catalyst Substances 0.000 claims abstract description 21
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 19
- 239000010948 rhodium Substances 0.000 claims abstract description 17
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 15
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000001993 dienes Chemical class 0.000 claims abstract description 10
- 150000002825 nitriles Chemical class 0.000 claims abstract description 10
- 125000002560 nitrile group Chemical group 0.000 claims abstract description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 7
- 238000005984 hydrogenation reaction Methods 0.000 claims description 60
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 48
- 239000003426 co-catalyst Substances 0.000 claims description 30
- 239000003446 ligand Substances 0.000 claims description 15
- 229920000126 latex Polymers 0.000 claims description 14
- 239000004816 latex Substances 0.000 claims description 10
- -1 sulphonyl group Chemical group 0.000 claims description 8
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 239000005864 Sulphur Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- 239000004952 Polyamide Substances 0.000 claims description 4
- 239000000835 fiber Substances 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- 229920002647 polyamide Polymers 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 2
- 229910021604 Rhodium(III) chloride Inorganic materials 0.000 claims description 2
- LYEZAEXHLSEXON-UHFFFAOYSA-N [RhH3].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [RhH3].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 LYEZAEXHLSEXON-UHFFFAOYSA-N 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 229910052785 arsenic Inorganic materials 0.000 claims description 2
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims description 2
- FCQRKDSALKMOGU-UHFFFAOYSA-K rhodium(3+);triphenylphosphane;trichloride Chemical compound Cl[Rh](Cl)Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 FCQRKDSALKMOGU-UHFFFAOYSA-K 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 claims 1
- 238000005299 abrasion Methods 0.000 abstract description 18
- 230000001070 adhesive effect Effects 0.000 abstract description 4
- 238000012360 testing method Methods 0.000 description 26
- 239000002253 acid Substances 0.000 description 22
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 20
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite group Chemical group N(=O)[O-] IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 16
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 12
- 239000004677 Nylon Substances 0.000 description 11
- 229920001778 nylon Polymers 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 9
- 150000002826 nitrites Chemical class 0.000 description 9
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 230000009467 reduction Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000004744 fabric Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 229920013647 Krynac Polymers 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 150000002978 peroxides Chemical class 0.000 description 6
- 229920001897 terpolymer Polymers 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000012190 activator Substances 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000006229 carbon black Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 238000004566 IR spectroscopy Methods 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 241001441571 Hiodontidae Species 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000003568 Sodium, potassium and calcium salts of fatty acids Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229920006170 Therban® Polymers 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 238000004378 air conditioning Methods 0.000 description 2
- 150000007824 aliphatic compounds Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 239000004760 aramid Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- IETKMTGYQIVLRF-UHFFFAOYSA-N carbon monoxide;rhodium;triphenylphosphane Chemical compound [Rh].[O+]#[C-].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 IETKMTGYQIVLRF-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- RIPYNJLMMFGZSX-UHFFFAOYSA-N (5-benzoylperoxy-2,5-dimethylhexan-2-yl) benzenecarboperoxoate Chemical compound C=1C=CC=CC=1C(=O)OOC(C)(C)CCC(C)(C)OOC(=O)C1=CC=CC=C1 RIPYNJLMMFGZSX-UHFFFAOYSA-N 0.000 description 1
- 238000011925 1,2-addition Methods 0.000 description 1
- IUNJCFABHJZSKB-UHFFFAOYSA-N 2,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1 IUNJCFABHJZSKB-UHFFFAOYSA-N 0.000 description 1
- ODBCKCWTWALFKM-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhex-3-yne Chemical compound CC(C)(C)OOC(C)(C)C#CC(C)(C)OOC(C)(C)C ODBCKCWTWALFKM-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-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
- QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 description 1
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 1
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- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
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- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
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- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- DLINORNFHVEIFE-UHFFFAOYSA-N hydrogen peroxide;zinc Chemical compound [Zn].OO DLINORNFHVEIFE-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000005555 metalworking Methods 0.000 description 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 1
- 229940117841 methacrylic acid copolymer Drugs 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003129 oil well Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical class CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 235000013966 potassium salts of fatty acid Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 230000001012 protector Effects 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000013875 sodium salts of fatty acid Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical group C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229940105296 zinc peroxide Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/02—Hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L13/00—Compositions of rubbers containing carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L15/00—Compositions of rubber derivatives
- C08L15/005—Hydrogenated nitrile rubber
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Laminated Bodies (AREA)
- Sealing Material Composition (AREA)
Priority Applications (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002304501A CA2304501A1 (en) | 2000-04-10 | 2000-04-10 | Process for hydrogenating carboxylated nitrile rubber, the hydrogenated rubber and its uses |
| SK1448-2002A SK14482002A3 (sk) | 2000-04-10 | 2001-04-09 | Spôsob hydrogenácie karboxylovaného nitrilového kaučuku, hydrogenovaný kaučuk a jeho použitie |
| PCT/CA2001/000485 WO2001077185A1 (en) | 2000-04-10 | 2001-04-09 | Process for hydrogenating carboxylated nitrile rubber, the hydrogenated rubber and its uses |
| JP2001575655A JP4694082B2 (ja) | 2000-04-10 | 2001-04-09 | カルボキシル化ニトリルゴムの水素化方法 |
| KR1020027013519A KR20030007512A (ko) | 2000-04-10 | 2001-04-09 | 카르복실화된 니트릴 고무의 수소화 방법, 수소화된 고무및 그의 용도 |
| EP01925236A EP1276773B1 (en) | 2000-04-10 | 2001-04-09 | Process for hydrogenating carboxylated nitrile rubber, the hydrogenated rubber and its uses |
| HU0300336A HUP0300336A3 (en) | 2000-04-10 | 2001-04-09 | Process for hydrogenating carboxylated nitrile rubber, the hydrogenated rubber and its uses |
| PL01358059A PL358059A1 (en) | 2000-04-10 | 2001-04-09 | Process for hydrogenating carboxylated nitrile rubber, the hydrogenated rubber and its uses |
| US10/258,245 US7265185B2 (en) | 2000-04-10 | 2001-04-09 | Process for hydrogenating carboxylated nitrile rubber, the hydrogenated rubber and its uses |
| RU2002129931/04A RU2002129931A (ru) | 2000-04-10 | 2001-04-09 | Способ гидрирования карбоксилированного нитрильного каучука, гидрированный каучук и его использование |
| CNB018078958A CN100523013C (zh) | 2000-04-10 | 2001-04-09 | 羧基化丁腈橡胶的加氢方法、氢化橡胶及其应用 |
| AT01925236T ATE454406T1 (de) | 2000-04-10 | 2001-04-09 | Verfahren zur hydrierung von carboxyliertem nitrilkautschuk und dessen verwendung |
| DE60141007T DE60141007D1 (de) | 2000-04-10 | 2001-04-09 | Verfahren zur hydrierung von carboxyliertem nitrilkautschuk und dessen verwendung |
| MXPA02009754A MXPA02009754A (es) | 2000-04-10 | 2001-04-09 | Proceso para hidrogenar caucho nitrilo carboxilado, el caucho hidrogenado y sus usos. |
| AU2001252059A AU2001252059A1 (en) | 2000-04-10 | 2001-04-09 | Process for hydrogenating carboxylated nitrile rubber, the hydrogenated rubber and its uses |
| CA2404295A CA2404295C (en) | 2000-04-10 | 2001-04-09 | Process for hydrogenating carboxylated nitrile rubber, the hydrogenated rubber and its uses |
| HK03106862.9A HK1054558B (en) | 2000-04-10 | 2001-04-09 | Process for hydrogenating carboxylated nitrile rubber, the hydrogenated rubber and its uses |
| BRPI0109933-7A BR0109933B1 (pt) | 2000-04-10 | 2001-04-09 | "processo para hidrogenar um polìmero de um dieno conjugado, uma nitrila não saturada e um ácido carboxìlico não saturado". |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002304501A CA2304501A1 (en) | 2000-04-10 | 2000-04-10 | Process for hydrogenating carboxylated nitrile rubber, the hydrogenated rubber and its uses |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2304501A1 true CA2304501A1 (en) | 2001-10-10 |
Family
ID=4165825
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002304501A Withdrawn CA2304501A1 (en) | 2000-04-10 | 2000-04-10 | Process for hydrogenating carboxylated nitrile rubber, the hydrogenated rubber and its uses |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7265185B2 (enExample) |
| EP (1) | EP1276773B1 (enExample) |
| JP (1) | JP4694082B2 (enExample) |
| KR (1) | KR20030007512A (enExample) |
| CN (1) | CN100523013C (enExample) |
| AT (1) | ATE454406T1 (enExample) |
| AU (1) | AU2001252059A1 (enExample) |
| BR (1) | BR0109933B1 (enExample) |
| CA (1) | CA2304501A1 (enExample) |
| DE (1) | DE60141007D1 (enExample) |
| HU (1) | HUP0300336A3 (enExample) |
| MX (1) | MXPA02009754A (enExample) |
| PL (1) | PL358059A1 (enExample) |
| RU (1) | RU2002129931A (enExample) |
| SK (1) | SK14482002A3 (enExample) |
| WO (1) | WO2001077185A1 (enExample) |
Cited By (6)
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| WO2005056665A1 (en) * | 2003-12-12 | 2005-06-23 | Lanxess Inc. | Rubber composition for tire treads |
| WO2005056664A1 (en) * | 2003-12-12 | 2005-06-23 | Lanxess Inc. | Butyl rubber composition for tire treads |
| US7037982B2 (en) | 2001-01-17 | 2006-05-02 | Bayer Aktiengesellschaft | Rubber mixtures for roll coverings |
| EP1669395A1 (en) | 2004-12-10 | 2006-06-14 | Lanxess Inc. | Multistage process for the manufacture of peroxide cured hxnbr-polyamide thermoplastic vulcanizates |
| EP2918612A1 (de) | 2014-03-10 | 2015-09-16 | LANXESS Deutschland GmbH | Aminomethylgruppenhaltiger hydrierter Nitrilkautschuk, Verfahren zu dessen Herstellung, vulkanisierbare Zusammensetzungen enthaltend aminomethylgruppenhaltigen hydrierten Nitrilkautschuk, Verfahren zu deren Vulkanisation und dadurch erhältliche Vulkanisate |
| EP2692788B1 (en) | 2011-03-31 | 2015-12-30 | Zeon Corporation | Highly saturated nitrile rubber composition and crosslinked rubber |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CA2355578A1 (en) | 2001-07-31 | 2003-01-31 | Bayer Inc. | Covulcanisation of polymers |
| US6905319B2 (en) * | 2002-01-29 | 2005-06-14 | Halliburton Energy Services, Inc. | Stator for down hole drilling motor |
| CA2413636A1 (en) * | 2002-12-05 | 2004-06-05 | Bayer Inc. | Adhesive compositions |
| CA2413607A1 (en) * | 2002-12-05 | 2004-06-05 | Bayer Inc. | Process for the preparation of low molecular weight hydrogenated nitrile rubber |
| US20040132886A1 (en) * | 2003-01-06 | 2004-07-08 | Jian Tao | Accelerator free nitrile gloves |
| CA2428222A1 (en) * | 2003-05-08 | 2004-11-08 | Bayer Inc. | Rubber compound comprising nitrile rubbers |
| DE10321875A1 (de) * | 2003-05-15 | 2004-12-02 | Bayer Ag | HXNBR-Kautschuk als Vernetzungsmittel |
| DE10327452A1 (de) * | 2003-06-18 | 2005-01-05 | Bayer Materialscience Ag | Klebstoffe |
| CA2437406A1 (en) * | 2003-08-14 | 2005-02-14 | Bayer Inc. | Butyl compositions comprising nitrile polymers |
| CA2438111A1 (en) * | 2003-08-25 | 2005-02-25 | Bayer Inc. | Nitrile polymer compounds for magntic seal applications |
| CA2478431A1 (en) * | 2004-06-23 | 2005-12-23 | Richard Pazur | Elastomeric compositions having improved mechanical properties and scorch resistance |
| US20060110559A1 (en) * | 2004-10-05 | 2006-05-25 | Victor Nasreddine | Crosslinking of carboxylated nitrile polymers with organo functional silanes: a curable plasticizer composition |
| CA2487744A1 (en) | 2004-11-18 | 2006-05-18 | Lanxess Inc. | Peroxide curable rubber composition comprising hnbr |
| JP4791725B2 (ja) * | 2004-11-19 | 2011-10-12 | 日本板硝子株式会社 | 歯付ベルトを補強するための補強用シートならびに歯付ベルトおよびその製造方法 |
| CA2501203A1 (en) * | 2005-03-18 | 2006-09-18 | Lanxess Inc. | Hydrogenation of diene-based polymer latex |
| CA2501199A1 (en) * | 2005-03-18 | 2006-09-18 | Lanxess Inc. | Organic solvent-free hydrogenation of diene-based polymers |
| CN100376611C (zh) * | 2005-05-20 | 2008-03-26 | 中国石油天然气股份有限公司 | 一种丁腈橡胶的加氢方法 |
| DE102005042265A1 (de) | 2005-09-06 | 2007-03-08 | Lanxess Deutschland Gmbh | Vernetzbare Zusammensetzungen, daraus erhältliche thermoplastische Elastomere und deren Verwendung |
| DE102005047115A1 (de) | 2005-09-30 | 2007-04-05 | Lanxess Deutschland Gmbh | Vernetzbare Zusammensetzungen, Verfahren zu deren Herstellung und deren Verwendung |
| US7741392B2 (en) * | 2006-02-23 | 2010-06-22 | Lanxess Inc. | Rubber compositions having improved physical and low temperature properties |
| US7666950B2 (en) * | 2006-06-01 | 2010-02-23 | Lanxess Deutschland Gmbh | Process for preparing hydrogenated nitrile rubbers |
| JP4669443B2 (ja) * | 2006-06-12 | 2011-04-13 | 三菱電線工業株式会社 | シール材用ゴム組成物およびそれを用いたシール材 |
| US7765720B2 (en) | 2007-01-12 | 2010-08-03 | Nike, Inc, | Outsole for an article of footwear |
| FR2919613B1 (fr) | 2007-07-30 | 2009-10-09 | Inergy Automotive Systems Res | Objet a base d'une composition contenant un melange reticule d'elastomeres |
| US7858540B2 (en) * | 2007-12-21 | 2010-12-28 | Honeywell International Inc. | Environmentally resistant ballistic composite based on a nitrile rubber binder |
| JP4792053B2 (ja) * | 2008-03-19 | 2011-10-12 | 日本板硝子株式会社 | 補強用繊維に塗布される水性処理剤 |
| BRPI0806233A2 (pt) | 2008-06-23 | 2011-09-06 | Lanxess Deutschland Gmbh | composição vulcanizável, processo de preparação da composição vulcanizável, método de preparação de polìmero vulcanizado e polìmero vulcanizado |
| PL2368916T3 (pl) * | 2010-03-25 | 2013-03-29 | Lanxess Int Sa | Sposób wytwarzania kauczuków nitrylowych wolnych od wody i rozpuszczalników |
| CN101870744A (zh) * | 2010-06-11 | 2010-10-27 | 北京化工大学 | 一种丁腈酯橡胶的加氢方法 |
| US8091855B1 (en) * | 2010-06-30 | 2012-01-10 | Hydril Usa Manufacturing Llc | Fluorinated elastomeric blowout preventer packers and method |
| CN101987874A (zh) * | 2010-09-15 | 2011-03-23 | 郴州高鑫铂业有限公司 | 一种纳米Pd/C催化剂合成氢化丁腈橡胶的方法 |
| US9484123B2 (en) | 2011-09-16 | 2016-11-01 | Prc-Desoto International, Inc. | Conductive sealant compositions |
| CN102875861A (zh) * | 2012-10-17 | 2013-01-16 | 浙江固特气动机械有限公司 | 用于火电除灰阀门密封圈的改性氢化丁腈材料及其制造工艺 |
| EP2868676A1 (de) | 2013-10-30 | 2015-05-06 | LANXESS Deutschland GmbH | Funktionalisierter nitrilgruppenhaltiger Copolymerkautschuk |
| EP3196239A1 (de) | 2016-01-25 | 2017-07-26 | ARLANXEO Deutschland GmbH | Vulkanisierbare zusammensetzungen auf basis von hydriertem nitrilkautschuk, verfahren zu deren herstellung und deren verwendung |
| EP3248989B1 (en) * | 2016-05-23 | 2020-12-02 | University Of Waterloo | Hydrogenation of nitrile groups in hydrogenated nitrile butadiene rubber and tandem hydrogenation of nitrile groups and olefinic groups in nitrile butadiene rubber using a ruthenium or rhodium complex and a basic reagent |
| EP3248988B1 (en) * | 2016-05-23 | 2020-12-02 | University Of Waterloo | Hydrogenation of nitrile groups in hydrogenated nitrile butadiene rubber and tandem hydrogenation of nitrile groups and olefinic groups in nitrile butadiene rubber using an unsupported rhodium containing catalyst |
| EP3255088B1 (de) | 2016-06-07 | 2020-04-29 | ARLANXEO Deutschland GmbH | Verwendung von vulkanisierbaren zusammensetzungen und vulkanisaten in kontakt mit kühlmittel enthaltend silan-beschichteten wollastonit |
| EP3668922B1 (de) | 2017-08-16 | 2022-03-16 | ARLANXEO Deutschland GmbH | Vulkanisierbare zusammensetzungen enthaltend hydrierten nitrilkautschuk, daraus hergestellte vulkanisate und deren verwendung |
| JP7252212B2 (ja) | 2017-09-20 | 2023-04-04 | アランセオ・ドイチュランド・ゲーエムベーハー | 高い熱伝導性を有する加硫可能なｈｎｂｒ組成物 |
| US11370849B2 (en) * | 2018-01-26 | 2022-06-28 | Zeon Corporation | Method for producing carboxy group-containing hydrogenated nitrile rubber |
| EP3770309B1 (en) * | 2018-03-19 | 2023-08-09 | Nippon Sheet Glass Company, Limited | Cord for rubber reinforcement, method for producing same, and rubber product |
| CN108993608B (zh) * | 2018-07-27 | 2020-11-06 | 北京化工大学 | 一种多功能催化剂及产氢加氢合成氢化丁腈橡胶的方法 |
| CN112940185B (zh) * | 2021-03-29 | 2022-04-22 | 黄河三角洲京博化工研究院有限公司 | 一种共聚物胶乳的选择性加氢方法 |
| WO2025219242A1 (en) | 2024-04-18 | 2025-10-23 | ARLANXEO High Performance Elastomers (Changzhou) Co., Ltd. | Binder composition for an electrochemical energy storage device and method of preparing the same |
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| DE2539132C2 (de) * | 1975-09-03 | 1987-04-09 | Bayer Ag, 5090 Leverkusen | Verwendung hydrierter Dien-Copolymere als temperaturbeständige Materialien auf dem Dichtungssektor |
| CA1220300A (en) * | 1982-12-08 | 1987-04-07 | Polysar Limited | Polymer hydrogenation process |
| DE3329974A1 (de) | 1983-08-19 | 1985-02-28 | Bayer Ag, 5090 Leverkusen | Herstellung von hydrierten nitrilkautschuken |
| DE3433392A1 (de) | 1984-09-12 | 1986-03-20 | Bayer Ag, 5090 Leverkusen | Hydrierung nitrilgruppenhaltiger ungesaettigter polymerer |
| DE3618907A1 (de) * | 1986-06-05 | 1987-12-10 | Bayer Ag | Verbundwerkstoffe aus vorbehandeltem fasermaterial und vulkanisaten aus hnbr |
| JPH0796629B2 (ja) | 1987-06-29 | 1995-10-18 | 日本ゼオン株式会社 | ゴム組成物 |
| US4843114A (en) * | 1988-01-29 | 1989-06-27 | The United States Of America As Represented By The Secretary Of The Army | Rubber compound for tracked vehicle track pads |
| US4914160A (en) * | 1988-06-23 | 1990-04-03 | Hormoz Azizian | Deuteration of unsaturated polymers and copolymers |
| JPH03220206A (ja) * | 1989-10-26 | 1991-09-27 | Asahi Chem Ind Co Ltd | テレケリック液状水素化ニトリルゴムおよびその製造方法 |
| CN1058218C (zh) * | 1993-06-09 | 2000-11-08 | 机械工厂股份有限公司 | 用注塑法制造的部分结晶合成树脂预塑坯料的加热方法和装置 |
| US5852093A (en) * | 1994-11-30 | 1998-12-22 | Nippon Zeon Co., Ltd. | Vulcanizable rubber composition, seal used in dynamic state, and sealing material |
| US5561197A (en) * | 1995-06-27 | 1996-10-01 | University Of Waterloo | Hydrogenation of diene copolymers |
| CN1058725C (zh) * | 1997-05-08 | 2000-11-22 | 南帝化学工业股份有限公司 | 一种不饱和共聚物加氢的方法及其所用的含双金属的催化剂体系 |
| DE19753302A1 (de) * | 1997-12-01 | 1999-06-02 | Basf Ag | Verfahren zur selektiven Hydrierung von ethylenisch ungesättigten Doppelbindungen in Polymerisaten |
-
2000
- 2000-04-10 CA CA002304501A patent/CA2304501A1/en not_active Withdrawn
-
2001
- 2001-04-09 PL PL01358059A patent/PL358059A1/xx not_active Application Discontinuation
- 2001-04-09 AU AU2001252059A patent/AU2001252059A1/en not_active Abandoned
- 2001-04-09 MX MXPA02009754A patent/MXPA02009754A/es active IP Right Grant
- 2001-04-09 WO PCT/CA2001/000485 patent/WO2001077185A1/en not_active Ceased
- 2001-04-09 US US10/258,245 patent/US7265185B2/en not_active Expired - Lifetime
- 2001-04-09 BR BRPI0109933-7A patent/BR0109933B1/pt not_active IP Right Cessation
- 2001-04-09 DE DE60141007T patent/DE60141007D1/de not_active Expired - Lifetime
- 2001-04-09 SK SK1448-2002A patent/SK14482002A3/sk not_active Application Discontinuation
- 2001-04-09 EP EP01925236A patent/EP1276773B1/en not_active Expired - Lifetime
- 2001-04-09 KR KR1020027013519A patent/KR20030007512A/ko not_active Abandoned
- 2001-04-09 CN CNB018078958A patent/CN100523013C/zh not_active Expired - Lifetime
- 2001-04-09 JP JP2001575655A patent/JP4694082B2/ja not_active Expired - Lifetime
- 2001-04-09 HU HU0300336A patent/HUP0300336A3/hu unknown
- 2001-04-09 RU RU2002129931/04A patent/RU2002129931A/ru not_active Application Discontinuation
- 2001-04-09 AT AT01925236T patent/ATE454406T1/de not_active IP Right Cessation
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7037982B2 (en) | 2001-01-17 | 2006-05-02 | Bayer Aktiengesellschaft | Rubber mixtures for roll coverings |
| WO2005056665A1 (en) * | 2003-12-12 | 2005-06-23 | Lanxess Inc. | Rubber composition for tire treads |
| WO2005056664A1 (en) * | 2003-12-12 | 2005-06-23 | Lanxess Inc. | Butyl rubber composition for tire treads |
| EP1669395A1 (en) | 2004-12-10 | 2006-06-14 | Lanxess Inc. | Multistage process for the manufacture of peroxide cured hxnbr-polyamide thermoplastic vulcanizates |
| EP2692788B1 (en) | 2011-03-31 | 2015-12-30 | Zeon Corporation | Highly saturated nitrile rubber composition and crosslinked rubber |
| US10280298B2 (en) | 2011-03-31 | 2019-05-07 | Zeon Corporation | Highly saturated nitrile rubber composition and cross-linked rubber |
| EP2918612A1 (de) | 2014-03-10 | 2015-09-16 | LANXESS Deutschland GmbH | Aminomethylgruppenhaltiger hydrierter Nitrilkautschuk, Verfahren zu dessen Herstellung, vulkanisierbare Zusammensetzungen enthaltend aminomethylgruppenhaltigen hydrierten Nitrilkautschuk, Verfahren zu deren Vulkanisation und dadurch erhältliche Vulkanisate |
Also Published As
| Publication number | Publication date |
|---|---|
| BR0109933A (pt) | 2003-05-27 |
| JP4694082B2 (ja) | 2011-06-01 |
| HUP0300336A2 (hu) | 2003-06-28 |
| SK14482002A3 (sk) | 2003-04-01 |
| US7265185B2 (en) | 2007-09-04 |
| DE60141007D1 (de) | 2010-02-25 |
| MXPA02009754A (es) | 2003-03-27 |
| AU2001252059A1 (en) | 2001-10-23 |
| WO2001077185A1 (en) | 2001-10-18 |
| HK1054558A1 (zh) | 2003-12-05 |
| BR0109933B1 (pt) | 2011-05-03 |
| HUP0300336A3 (en) | 2005-06-28 |
| EP1276773B1 (en) | 2010-01-06 |
| RU2002129931A (ru) | 2004-03-27 |
| KR20030007512A (ko) | 2003-01-23 |
| ATE454406T1 (de) | 2010-01-15 |
| US20030171500A1 (en) | 2003-09-11 |
| CN100523013C (zh) | 2009-08-05 |
| CN1422284A (zh) | 2003-06-04 |
| PL358059A1 (en) | 2004-08-09 |
| EP1276773A1 (en) | 2003-01-22 |
| JP2003530467A (ja) | 2003-10-14 |
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| Date | Code | Title | Description |
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| EEER | Examination request | ||
| AZWI | Withdrawn application |