CN101845157B - 可固化的聚合物组合物 - Google Patents
可固化的聚合物组合物 Download PDFInfo
- Publication number
- CN101845157B CN101845157B CN200910261327.3A CN200910261327A CN101845157B CN 101845157 B CN101845157 B CN 101845157B CN 200910261327 A CN200910261327 A CN 200910261327A CN 101845157 B CN101845157 B CN 101845157B
- Authority
- CN
- China
- Prior art keywords
- polymer
- monomer
- ethylenically unsaturated
- weight
- dicarboxylic acid
- 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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- 229920000642 polymer Polymers 0.000 title claims abstract description 308
- 239000000203 mixture Substances 0.000 title claims abstract description 101
- -1 alkali metal salt Chemical class 0.000 claims abstract description 94
- 229920000768 polyamine Polymers 0.000 claims abstract description 54
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 38
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 27
- 239000000178 monomer Substances 0.000 claims description 292
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 claims description 113
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 claims description 88
- 229910052799 carbon Inorganic materials 0.000 claims description 59
- 239000002585 base Substances 0.000 claims description 58
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 57
- OEBXWWBYZJNKRK-UHFFFAOYSA-N 1-methyl-2,3,4,6,7,8-hexahydropyrimido[1,2-a]pyrimidine Chemical compound C1CCN=C2N(C)CCCN21 OEBXWWBYZJNKRK-UHFFFAOYSA-N 0.000 claims description 52
- 150000002825 nitriles Chemical class 0.000 claims description 47
- 150000001993 dienes Chemical class 0.000 claims description 38
- 239000004971 Cross linker Substances 0.000 claims description 28
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 23
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 23
- FVKFHMNJTHKMRX-UHFFFAOYSA-N 3,4,6,7,8,9-hexahydro-2H-pyrimido[1,2-a]pyrimidine Chemical compound C1CCN2CCCNC2=N1 FVKFHMNJTHKMRX-UHFFFAOYSA-N 0.000 claims description 22
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 claims description 21
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 20
- 239000000945 filler Substances 0.000 claims description 20
- 239000003963 antioxidant agent Substances 0.000 claims description 19
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 18
- 150000002148 esters Chemical class 0.000 claims description 18
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 17
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical class OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 claims description 15
- 230000003078 antioxidant effect Effects 0.000 claims description 13
- 229940018557 citraconic acid Drugs 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 11
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 10
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 9
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 8
- 229910052808 lithium carbonate Inorganic materials 0.000 claims description 8
- 150000008065 acid anhydrides Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- XLYMOEINVGRTEX-UHFFFAOYSA-N fumaric acid monoethyl ester Natural products CCOC(=O)C=CC(O)=O XLYMOEINVGRTEX-UHFFFAOYSA-N 0.000 claims description 7
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- XLYMOEINVGRTEX-ARJAWSKDSA-N Ethyl hydrogen fumarate Chemical compound CCOC(=O)\C=C/C(O)=O XLYMOEINVGRTEX-ARJAWSKDSA-N 0.000 claims description 5
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 239000012973 diazabicyclooctane Substances 0.000 claims description 5
- 239000001530 fumaric acid Substances 0.000 claims description 5
- 239000011976 maleic acid Substances 0.000 claims description 5
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- ZMQWRASVUXJXGM-VOTSOKGWSA-N (e)-4-cyclohexyloxy-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C\C(=O)OC1CCCCC1 ZMQWRASVUXJXGM-VOTSOKGWSA-N 0.000 claims description 4
- QKUGKZFASYQCGO-VOTSOKGWSA-N (e)-4-oxo-4-phenylmethoxybut-2-enoic acid Chemical compound OC(=O)\C=C\C(=O)OCC1=CC=CC=C1 QKUGKZFASYQCGO-VOTSOKGWSA-N 0.000 claims description 4
- QKUGKZFASYQCGO-SREVYHEPSA-N (z)-4-oxo-4-phenylmethoxybut-2-enoic acid Chemical compound OC(=O)\C=C/C(=O)OCC1=CC=CC=C1 QKUGKZFASYQCGO-SREVYHEPSA-N 0.000 claims description 4
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 claims description 4
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 4
- QUEPLWQMCBQXGI-UHFFFAOYSA-N 3-phenylmethoxycarbonylbut-3-enoic acid Chemical compound OC(=O)CC(=C)C(=O)OCC1=CC=CC=C1 QUEPLWQMCBQXGI-UHFFFAOYSA-N 0.000 claims description 4
- NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 claims description 4
- UTOVMEACOLCUCK-SNAWJCMRSA-N (e)-4-butoxy-4-oxobut-2-enoic acid Chemical compound CCCCOC(=O)\C=C\C(O)=O UTOVMEACOLCUCK-SNAWJCMRSA-N 0.000 claims description 3
- ZMQWRASVUXJXGM-SREVYHEPSA-N (z)-4-cyclohexyloxy-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C/C(=O)OC1CCCCC1 ZMQWRASVUXJXGM-SREVYHEPSA-N 0.000 claims description 3
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- UTOVMEACOLCUCK-PLNGDYQASA-N butyl maleate Chemical compound CCCCOC(=O)\C=C/C(O)=O UTOVMEACOLCUCK-PLNGDYQASA-N 0.000 claims description 3
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 claims description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 claims description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims description 2
- ZJYCLOLEIIBKBW-SREVYHEPSA-N (Z)-4-(1-ethylcyclohexyl)oxy-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C/C(=O)OC1(CC)CCCCC1 ZJYCLOLEIIBKBW-SREVYHEPSA-N 0.000 claims description 2
- YXVCXHNQDCQCPE-PLNGDYQASA-N (Z)-4-(1-methylcyclopentyl)oxy-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C/C(=O)OC1(C)CCCC1 YXVCXHNQDCQCPE-PLNGDYQASA-N 0.000 claims description 2
- ZJYCLOLEIIBKBW-VOTSOKGWSA-N (e)-4-(1-ethylcyclohexyl)oxy-4-oxobut-2-enoic acid Chemical compound OC(=O)/C=C/C(=O)OC1(CC)CCCCC1 ZJYCLOLEIIBKBW-VOTSOKGWSA-N 0.000 claims description 2
- YXVCXHNQDCQCPE-SNAWJCMRSA-N (e)-4-(1-methylcyclopentyl)oxy-4-oxobut-2-enoic acid Chemical compound OC(=O)/C=C/C(=O)OC1(C)CCCC1 YXVCXHNQDCQCPE-SNAWJCMRSA-N 0.000 claims description 2
- QCAHYQPONLPBNQ-AATRIKPKSA-N (e)-4-cyclopentyloxy-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C\C(=O)OC1CCCC1 QCAHYQPONLPBNQ-AATRIKPKSA-N 0.000 claims description 2
- XLYMOEINVGRTEX-ONEGZZNKSA-N (e)-4-ethoxy-4-oxobut-2-enoic acid Chemical compound CCOC(=O)\C=C\C(O)=O XLYMOEINVGRTEX-ONEGZZNKSA-N 0.000 claims description 2
- GPTNZCCQHNGXMS-VOTSOKGWSA-N (e)-4-oxo-4-phenoxybut-2-enoic acid Chemical compound OC(=O)\C=C\C(=O)OC1=CC=CC=C1 GPTNZCCQHNGXMS-VOTSOKGWSA-N 0.000 claims description 2
- AYAUWVRAUCDBFR-ONEGZZNKSA-N (e)-4-oxo-4-propoxybut-2-enoic acid Chemical compound CCCOC(=O)\C=C\C(O)=O AYAUWVRAUCDBFR-ONEGZZNKSA-N 0.000 claims description 2
- QCAHYQPONLPBNQ-WAYWQWQTSA-N (z)-4-cyclopentyloxy-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C/C(=O)OC1CCCC1 QCAHYQPONLPBNQ-WAYWQWQTSA-N 0.000 claims description 2
- GPTNZCCQHNGXMS-SREVYHEPSA-N (z)-4-oxo-4-phenoxybut-2-enoic acid Chemical compound OC(=O)\C=C/C(=O)OC1=CC=CC=C1 GPTNZCCQHNGXMS-SREVYHEPSA-N 0.000 claims description 2
- AYAUWVRAUCDBFR-ARJAWSKDSA-N (z)-4-oxo-4-propoxybut-2-enoic acid Chemical compound CCCOC(=O)\C=C/C(O)=O AYAUWVRAUCDBFR-ARJAWSKDSA-N 0.000 claims description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 2
- CMPIGRYBIGUGTH-UHFFFAOYSA-N 2-bromoprop-2-enenitrile Chemical compound BrC(=C)C#N CMPIGRYBIGUGTH-UHFFFAOYSA-N 0.000 claims description 2
- OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 claims description 2
- PGZYFKWYHCLTIX-UHFFFAOYSA-N 3-phenoxycarbonylbut-3-enoic acid Chemical compound OC(=O)CC(=C)C(=O)OC1=CC=CC=C1 PGZYFKWYHCLTIX-UHFFFAOYSA-N 0.000 claims description 2
- IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 claims description 2
- KMKWGXGSGPYISJ-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 KMKWGXGSGPYISJ-UHFFFAOYSA-N 0.000 claims description 2
- IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- UTTHLMXOSUFZCQ-UHFFFAOYSA-N benzene-1,3-dicarbohydrazide Chemical compound NNC(=O)C1=CC=CC(C(=O)NN)=C1 UTTHLMXOSUFZCQ-UHFFFAOYSA-N 0.000 claims description 2
- 229940117916 cinnamic aldehyde Drugs 0.000 claims description 2
- ZWLIYXJBOIDXLL-UHFFFAOYSA-N decanedihydrazide Chemical compound NNC(=O)CCCCCCCCC(=O)NN ZWLIYXJBOIDXLL-UHFFFAOYSA-N 0.000 claims description 2
- 229940018564 m-phenylenediamine Drugs 0.000 claims description 2
- NKHAVTQWNUWKEO-IHWYPQMZSA-N methyl hydrogen fumarate Chemical compound COC(=O)\C=C/C(O)=O NKHAVTQWNUWKEO-IHWYPQMZSA-N 0.000 claims description 2
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 claims description 2
- 229940074369 monoethyl fumarate Drugs 0.000 claims description 2
- NKHAVTQWNUWKEO-NSCUHMNNSA-N monomethyl fumarate Chemical compound COC(=O)\C=C\C(O)=O NKHAVTQWNUWKEO-NSCUHMNNSA-N 0.000 claims description 2
- 229940005650 monomethyl fumarate Drugs 0.000 claims description 2
- QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 claims description 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims description 2
- DIBHLCJAJIKHGB-UHFFFAOYSA-N dec-5-ene Chemical compound [CH2]CCCC=CCCCC DIBHLCJAJIKHGB-UHFFFAOYSA-N 0.000 claims 4
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 claims 4
- 229940018560 citraconate Drugs 0.000 claims 3
- 125000004185 ester group Chemical group 0.000 claims 3
- NQHWGQCRGNOLOD-UHFFFAOYSA-N 3-cyclohexyloxycarbonylbut-3-enoic acid Chemical compound OC(=O)CC(=C)C(=O)OC1CCCCC1 NQHWGQCRGNOLOD-UHFFFAOYSA-N 0.000 claims 2
- 150000002688 maleic acid derivatives Chemical class 0.000 claims 2
- HWQBUJSWKVPMFY-SNAWJCMRSA-N (e)-4-ethoxy-3-methyl-4-oxobut-2-enoic acid Chemical compound CCOC(=O)C(\C)=C\C(O)=O HWQBUJSWKVPMFY-SNAWJCMRSA-N 0.000 claims 1
- YZUIBMVKWXNSHB-WAYWQWQTSA-N (z)-3-methyl-4-oxo-4-propoxybut-2-enoic acid Chemical compound CCCOC(=O)C(\C)=C/C(O)=O YZUIBMVKWXNSHB-WAYWQWQTSA-N 0.000 claims 1
- UFZCRECDCVOYAU-SREVYHEPSA-N (z)-4-butoxy-3-methyl-4-oxobut-2-enoic acid Chemical compound CCCCOC(=O)C(\C)=C/C(O)=O UFZCRECDCVOYAU-SREVYHEPSA-N 0.000 claims 1
- BVCYGKIVZPIAMH-FPLPWBNLSA-N (z)-4-cycloheptyloxy-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C/C(=O)OC1CCCCCC1 BVCYGKIVZPIAMH-FPLPWBNLSA-N 0.000 claims 1
- HWQBUJSWKVPMFY-PLNGDYQASA-N (z)-4-ethoxy-3-methyl-4-oxobut-2-enoic acid Chemical compound CCOC(=O)C(\C)=C/C(O)=O HWQBUJSWKVPMFY-PLNGDYQASA-N 0.000 claims 1
- BGMFJTUTJOZHHZ-ARJAWSKDSA-N (z)-4-methoxy-3-methyl-4-oxobut-2-enoic acid Chemical compound COC(=O)C(\C)=C/C(O)=O BGMFJTUTJOZHHZ-ARJAWSKDSA-N 0.000 claims 1
- WCNAIVFTIXQMMZ-UHFFFAOYSA-N 2-hydroxy-2-(2-oxo-2-phenylmethoxyethyl)butanedioic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(=O)OCC1=CC=CC=C1 WCNAIVFTIXQMMZ-UHFFFAOYSA-N 0.000 claims 1
- TVONJMOVBKMLOM-UHFFFAOYSA-N 2-methylidenebutanenitrile Chemical compound CCC(=C)C#N TVONJMOVBKMLOM-UHFFFAOYSA-N 0.000 claims 1
- LYJULXSXXSDOJA-UHFFFAOYSA-N 3-(1-ethylcyclohexyl)oxycarbonylbut-3-enoic acid Chemical compound OC(=O)CC(=C)C(=O)OC1(CC)CCCCC1 LYJULXSXXSDOJA-UHFFFAOYSA-N 0.000 claims 1
- NGDAEKXSRNRFQY-UHFFFAOYSA-N 3-(1-methylcyclopentyl)oxycarbonylbut-3-enoic acid Chemical compound OC(=O)CC(=C)C(=O)OC1(C)CCCC1 NGDAEKXSRNRFQY-UHFFFAOYSA-N 0.000 claims 1
- SSXZBUGTRRPNGB-UHFFFAOYSA-N 3-cyclopentyloxycarbonylbut-3-enoic acid Chemical compound OC(=O)CC(=C)C(=O)OC1CCCC1 SSXZBUGTRRPNGB-UHFFFAOYSA-N 0.000 claims 1
- NEAHVGRDHLQWPP-UHFFFAOYSA-N 3-propoxycarbonylbut-3-enoic acid Chemical compound CCCOC(=O)C(=C)CC(O)=O NEAHVGRDHLQWPP-UHFFFAOYSA-N 0.000 claims 1
- VVAAYFMMXYRORI-UHFFFAOYSA-N 4-butoxy-2-methylidene-4-oxobutanoic acid Chemical compound CCCCOC(=O)CC(=C)C(O)=O VVAAYFMMXYRORI-UHFFFAOYSA-N 0.000 claims 1
- RTTAGBVNSDJDTE-UHFFFAOYSA-N 4-ethoxy-2-methylidene-4-oxobutanoic acid Chemical compound CCOC(=O)CC(=C)C(O)=O RTTAGBVNSDJDTE-UHFFFAOYSA-N 0.000 claims 1
- OIYTYGOUZOARSH-UHFFFAOYSA-N 4-methoxy-2-methylidene-4-oxobutanoic acid Chemical compound COC(=O)CC(=C)C(O)=O OIYTYGOUZOARSH-UHFFFAOYSA-N 0.000 claims 1
- BVCZEBOGSOYJJT-UHFFFAOYSA-N ammonium carbamate Chemical compound [NH4+].NC([O-])=O BVCZEBOGSOYJJT-UHFFFAOYSA-N 0.000 claims 1
- YRBZGRNHVLUISF-UHFFFAOYSA-N benzoic acid;hexane-1,6-diamine Chemical compound NCCCCCCN.OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 YRBZGRNHVLUISF-UHFFFAOYSA-N 0.000 claims 1
- 229910003002 lithium salt Inorganic materials 0.000 claims 1
- 159000000002 lithium salts Chemical class 0.000 claims 1
- 238000004132 cross linking Methods 0.000 abstract description 19
- 238000000465 moulding Methods 0.000 abstract 1
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- 238000001723 curing Methods 0.000 description 17
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- 239000003795 chemical substances by application Substances 0.000 description 16
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- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 8
- 238000005984 hydrogenation reaction Methods 0.000 description 8
- 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 7
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
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- 229920001568 phenolic resin Polymers 0.000 description 6
- 239000005011 phenolic resin Substances 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- 230000007774 longterm Effects 0.000 description 5
- 230000001590 oxidative effect Effects 0.000 description 5
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000012190 activator Substances 0.000 description 4
- 230000003679 aging effect Effects 0.000 description 4
- 230000003712 anti-aging effect Effects 0.000 description 4
- 229920005549 butyl rubber Polymers 0.000 description 4
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- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- GFSJJVJWCAMZEV-UHFFFAOYSA-N n-(4-anilinophenyl)-2-methylprop-2-enamide Chemical compound C1=CC(NC(=O)C(=C)C)=CC=C1NC1=CC=CC=C1 GFSJJVJWCAMZEV-UHFFFAOYSA-N 0.000 description 1
- HKLPOBRVSAUJSG-UHFFFAOYSA-N n-(4-anilinophenyl)prop-2-enamide Chemical compound C1=CC(NC(=O)C=C)=CC=C1NC1=CC=CC=C1 HKLPOBRVSAUJSG-UHFFFAOYSA-N 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
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 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
- 150000002978 peroxides Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920005596 polymer binder Polymers 0.000 description 1
- 239000002491 polymer binding agent Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 239000011995 wilkinson's catalyst Substances 0.000 description 1
- UTODFRQBVUVYOB-UHFFFAOYSA-P wilkinson's catalyst Chemical compound [Cl-].C1=CC=CC=C1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)[Rh+](P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 UTODFRQBVUVYOB-UHFFFAOYSA-P 0.000 description 1
- 239000011787 zinc oxide 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/18—Homopolymers or copolymers of nitriles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/24—Acids; Salts thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/24—Acids; Salts thereof
- C08K3/26—Carbonates; Bicarbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3445—Five-membered rings
- C08K5/3447—Five-membered rings condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3472—Five-membered rings
- C08K5/3475—Five-membered rings condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
- C08L25/02—Homopolymers or copolymers of hydrocarbons
- C08L25/04—Homopolymers or copolymers of styrene
- C08L25/08—Copolymers of styrene
- C08L25/12—Copolymers of styrene with unsaturated nitriles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/06—Unsaturated polyesters
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Polyamides (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08022135 | 2008-12-19 | ||
| EP08022135.1 | 2008-12-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101845157A CN101845157A (zh) | 2010-09-29 |
| CN101845157B true CN101845157B (zh) | 2014-07-09 |
Family
ID=42060659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200910261327.3A Expired - Fee Related CN101845157B (zh) | 2008-12-19 | 2009-12-18 | 可固化的聚合物组合物 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20100179277A1 (enExample) |
| EP (1) | EP2199326B1 (enExample) |
| JP (1) | JP5634706B2 (enExample) |
| KR (1) | KR101636079B1 (enExample) |
| CN (1) | CN101845157B (enExample) |
| BR (1) | BRPI0905154A2 (enExample) |
| CA (1) | CA2688735C (enExample) |
| MX (1) | MX2009013898A (enExample) |
| TW (1) | TWI475063B (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5429097B2 (ja) * | 2010-07-30 | 2014-02-26 | 日本ゼオン株式会社 | ニトリル基含有高飽和共重合体ゴム |
| TWI509007B (zh) | 2010-10-06 | 2015-11-21 | Vanderbilt Chemicals Llc | 彈性體產品及其製造方法 |
| EP2471851A1 (de) * | 2010-12-29 | 2012-07-04 | LANXESS Deutschland GmbH | Vulkanisierbare Zusammensetzungen auf Basis Epoxygruppen-haltiger Nitrilkautschuke |
| EP2471852A1 (de) | 2010-12-29 | 2012-07-04 | Lanxess Deutschland GmbH | Vulkanisierbare Zusammensetzungen auf Basis Epoxygruppen-haltiger Nitrilkautschuke |
| US8765876B2 (en) | 2011-03-31 | 2014-07-01 | E I Du Pont De Nemours And Company | Curable fluoroelastomer composition |
| EP2581409A1 (de) | 2011-10-11 | 2013-04-17 | Lanxess Deutschland GmbH | Vulkanisierbare Zusammensetzungen auf Basis Epoxygruppen-haltiger Nitrilkautschuke |
| CN102558578B (zh) * | 2011-12-26 | 2013-11-13 | 北京化工大学 | 一种衣康酸酯/异戊二烯共聚物型生物工程橡胶及其制备方法 |
| EP2902437B1 (en) * | 2012-09-26 | 2017-01-25 | Zeon Corporation | Crosslinkable rubber composition and crosslinked rubber |
| JP2014074112A (ja) * | 2012-10-03 | 2014-04-24 | Midori Anzen Co Ltd | 酸化亜鉛を含まない又は酸化亜鉛含有量を低減したエラストマー成形物及びエラストマー製品 |
| WO2014111292A1 (en) | 2013-01-18 | 2014-07-24 | Basf Se | Acrylic dispersion-based coating compositions |
| JP6701734B2 (ja) * | 2014-01-30 | 2020-05-27 | 日本ゼオン株式会社 | 架橋性ニトリルゴム組成物およびゴム架橋物 |
| JPWO2015194539A1 (ja) * | 2014-06-19 | 2017-04-20 | 日本ゼオン株式会社 | ゴム架橋物 |
| WO2015194538A1 (ja) * | 2014-06-19 | 2015-12-23 | 日本ゼオン株式会社 | ゴム架橋物 |
| US20170240712A1 (en) * | 2014-10-17 | 2017-08-24 | Zeon Corporation | Cross-linkable nitrile rubber composition and cross-linked rubber |
| MX2019010745A (es) | 2017-03-17 | 2019-12-05 | Zeon Corp | Caucho de copolimero que contiene grupo nitrilo. |
| KR20230158047A (ko) * | 2021-03-16 | 2023-11-17 | 보레알리스 아게 | 반도전성 중합체 조성물 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0943657A2 (en) * | 1998-03-19 | 1999-09-22 | Nippon Mektron, Limited | Acrylic elastomer composition |
| US6214922B1 (en) * | 1998-03-06 | 2001-04-10 | Bayer Inc. | Nitrile polymer vulcanizate and process for the production thereof |
| CN1860171A (zh) * | 2003-09-30 | 2006-11-08 | 日本瑞翁株式会社 | 交联性橡胶组合物及交联物 |
| CN101031415A (zh) * | 2004-09-29 | 2007-09-05 | 日本瑞翁株式会社 | 橡胶积层体 |
| EP1964882A1 (en) * | 2005-12-21 | 2008-09-03 | Zeon Corporation | Crosslinkable rubber composition and rubber crosslinked product |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE565690A (enExample) * | 1953-01-02 | |||
| US3700637A (en) * | 1970-05-08 | 1972-10-24 | Shell Oil Co | Diene-nitrile rubbers |
| CA1203047A (en) * | 1982-12-08 | 1986-04-08 | Hormoz Azizian | Polymer hydrogenation process |
| 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 |
| DE3529252A1 (de) * | 1985-08-16 | 1987-02-19 | Bayer Ag | Verfahren zur selektiven hydrierung ungesaettigter verbindungen |
| DE3540918A1 (de) * | 1985-11-19 | 1987-05-21 | Bayer Ag | Verfahren zur selektiven hydrierung ungesaettigter verbindungen |
| US4812528A (en) * | 1987-07-06 | 1989-03-14 | University Of Waterloo | Polymer hydrogenation process |
| JP4062828B2 (ja) * | 1999-08-20 | 2008-03-19 | 日本ゼオン株式会社 | 架橋性ゴム組成物および架橋物 |
| AU2002213847A1 (en) * | 2000-08-16 | 2002-02-25 | Bayer Aktiengesellschaft | Antioxidant agent based on phenolic salts |
| JP2006206659A (ja) | 2005-01-26 | 2006-08-10 | Nippon Zeon Co Ltd | ホースおよびその製造方法 |
| JP5176267B2 (ja) * | 2005-08-31 | 2013-04-03 | 日本ゼオン株式会社 | ニトリルゴム組成物および架橋物 |
| WO2007049651A1 (ja) * | 2005-10-25 | 2007-05-03 | Zeon Corporation | ニトリルゴム、ニトリルゴム組成物および架橋物 |
| JP5061641B2 (ja) * | 2006-03-03 | 2012-10-31 | ダイソー株式会社 | ゴム組成物及び加硫ゴム成形体 |
| US8034881B2 (en) * | 2008-01-31 | 2011-10-11 | Zeon Corporation | Cross-linkable nitrile rubber composition and cross-linked rubber |
| EP2145920A1 (en) * | 2008-07-15 | 2010-01-20 | Lanxess Deutschland GmbH | Vulcanizable polymer compositions |
-
2009
- 2009-12-09 EP EP09178459.5A patent/EP2199326B1/en not_active Revoked
- 2009-12-16 CA CA2688735A patent/CA2688735C/en active Active
- 2009-12-17 MX MX2009013898A patent/MX2009013898A/es active IP Right Grant
- 2009-12-17 US US12/640,108 patent/US20100179277A1/en not_active Abandoned
- 2009-12-17 BR BRPI0905154-6A patent/BRPI0905154A2/pt not_active IP Right Cessation
- 2009-12-18 CN CN200910261327.3A patent/CN101845157B/zh not_active Expired - Fee Related
- 2009-12-18 KR KR1020090126862A patent/KR101636079B1/ko not_active Expired - Fee Related
- 2009-12-18 TW TW098143502A patent/TWI475063B/zh not_active IP Right Cessation
- 2009-12-18 JP JP2009288213A patent/JP5634706B2/ja not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6214922B1 (en) * | 1998-03-06 | 2001-04-10 | Bayer Inc. | Nitrile polymer vulcanizate and process for the production thereof |
| EP0943657A2 (en) * | 1998-03-19 | 1999-09-22 | Nippon Mektron, Limited | Acrylic elastomer composition |
| CN1860171A (zh) * | 2003-09-30 | 2006-11-08 | 日本瑞翁株式会社 | 交联性橡胶组合物及交联物 |
| CN101031415A (zh) * | 2004-09-29 | 2007-09-05 | 日本瑞翁株式会社 | 橡胶积层体 |
| EP1964882A1 (en) * | 2005-12-21 | 2008-09-03 | Zeon Corporation | Crosslinkable rubber composition and rubber crosslinked product |
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0905154A2 (pt) | 2011-03-22 |
| KR20100071930A (ko) | 2010-06-29 |
| JP5634706B2 (ja) | 2014-12-03 |
| US20100179277A1 (en) | 2010-07-15 |
| MX2009013898A (es) | 2010-06-22 |
| TWI475063B (zh) | 2015-03-01 |
| CA2688735C (en) | 2018-01-02 |
| KR101636079B1 (ko) | 2016-07-04 |
| JP2010144176A (ja) | 2010-07-01 |
| CN101845157A (zh) | 2010-09-29 |
| EP2199326B1 (en) | 2014-10-29 |
| TW201035203A (en) | 2010-10-01 |
| CA2688735A1 (en) | 2010-06-19 |
| EP2199326A1 (en) | 2010-06-23 |
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