JP5634706B2 - 加硫可能なポリマー組成物 - Google Patents
加硫可能なポリマー組成物 Download PDFInfo
- Publication number
- JP5634706B2 JP5634706B2 JP2009288213A JP2009288213A JP5634706B2 JP 5634706 B2 JP5634706 B2 JP 5634706B2 JP 2009288213 A JP2009288213 A JP 2009288213A JP 2009288213 A JP2009288213 A JP 2009288213A JP 5634706 B2 JP5634706 B2 JP 5634706B2
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- monomer
- weight
- ethylenically unsaturated
- 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
Links
- 229920000642 polymer Polymers 0.000 title claims description 218
- 239000000203 mixture Substances 0.000 title claims description 79
- 239000000178 monomer Substances 0.000 claims description 207
- -1 unsaturated dicarboxylic acid diester Chemical class 0.000 claims description 89
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 claims description 75
- 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 68
- 229920000768 polyamine Polymers 0.000 claims description 38
- 150000002825 nitriles Chemical class 0.000 claims description 34
- 239000003431 cross linking reagent Substances 0.000 claims description 32
- 125000002619 bicyclic group Chemical group 0.000 claims description 31
- 238000004132 cross linking Methods 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 29
- 150000001993 dienes Chemical class 0.000 claims description 27
- 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 26
- 239000003963 antioxidant agent Substances 0.000 claims description 21
- 239000000945 filler Substances 0.000 claims description 19
- 238000004073 vulcanization Methods 0.000 claims description 18
- 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 16
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 claims description 15
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 15
- 230000003078 antioxidant effect Effects 0.000 claims description 14
- UURSXESKOOOTOV-UHFFFAOYSA-N dec-5-ene Chemical compound CCCCC=CCCCC UURSXESKOOOTOV-UHFFFAOYSA-N 0.000 claims description 9
- 159000000000 sodium salts Chemical class 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 5
- 239000004971 Cross linker Substances 0.000 claims description 4
- QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 claims 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- 229920000459 Nitrile rubber Polymers 0.000 description 38
- 239000002585 base Substances 0.000 description 31
- 229910052799 carbon Inorganic materials 0.000 description 23
- 229920001971 elastomer Polymers 0.000 description 23
- 230000032683 aging Effects 0.000 description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 21
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
- 229910052783 alkali metal Inorganic materials 0.000 description 19
- 150000002148 esters Chemical class 0.000 description 16
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 15
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 13
- 229920001577 copolymer Polymers 0.000 description 13
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 13
- 239000005060 rubber Substances 0.000 description 13
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 229940018557 citraconic acid Drugs 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 238000007906 compression Methods 0.000 description 10
- 230000006835 compression Effects 0.000 description 10
- 239000000806 elastomer Substances 0.000 description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 9
- 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 8
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 8
- 229920001897 terpolymer Polymers 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 7
- 229910052808 lithium carbonate Inorganic materials 0.000 description 7
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000011976 maleic acid Substances 0.000 description 6
- 229920001568 phenolic resin Polymers 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 5
- 239000001530 fumaric acid Substances 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 230000007774 longterm Effects 0.000 description 5
- 230000001590 oxidative effect Effects 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 239000012190 activator Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- XLYMOEINVGRTEX-UHFFFAOYSA-N fumaric acid monoethyl ester Natural products CCOC(=O)C=CC(O)=O XLYMOEINVGRTEX-UHFFFAOYSA-N 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 4
- 229960002447 thiram Drugs 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- XSQHUYDRSDBCHN-UHFFFAOYSA-N 2,3-dimethyl-2-propan-2-ylbutanenitrile Chemical compound CC(C)C(C)(C#N)C(C)C XSQHUYDRSDBCHN-UHFFFAOYSA-N 0.000 description 3
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XLYMOEINVGRTEX-ARJAWSKDSA-N Ethyl hydrogen fumarate Chemical compound CCOC(=O)\C=C/C(O)=O XLYMOEINVGRTEX-ARJAWSKDSA-N 0.000 description 3
- 244000043261 Hevea brasiliensis Species 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229920005549 butyl rubber Polymers 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 239000011243 crosslinked material Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229920006168 hydrated nitrile rubber Polymers 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229920003052 natural elastomer Polymers 0.000 description 3
- 229920001194 natural rubber Polymers 0.000 description 3
- 125000000962 organic group Chemical group 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- 239000004711 α-olefin Substances 0.000 description 3
- UTOVMEACOLCUCK-SNAWJCMRSA-N (e)-4-butoxy-4-oxobut-2-enoic acid Chemical group CCCCOC(=O)\C=C\C(O)=O UTOVMEACOLCUCK-SNAWJCMRSA-N 0.000 description 2
- 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 description 2
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 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
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- UJAWGGOCYUPCPS-UHFFFAOYSA-N 4-(2-phenylpropan-2-yl)-n-[4-(2-phenylpropan-2-yl)phenyl]aniline Chemical compound C=1C=C(NC=2C=CC(=CC=2)C(C)(C)C=2C=CC=CC=2)C=CC=1C(C)(C)C1=CC=CC=C1 UJAWGGOCYUPCPS-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 229920002943 EPDM rubber Polymers 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 101001024605 Homo sapiens Next to BRCA1 gene 1 protein Proteins 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- 102100037001 Next to BRCA1 gene 1 protein Human genes 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000005396 acrylic acid ester group Chemical group 0.000 description 2
- 230000003679 aging effect Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- UTOVMEACOLCUCK-PLNGDYQASA-N butyl maleate Chemical group CCCCOC(=O)\C=C/C(O)=O UTOVMEACOLCUCK-PLNGDYQASA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
- 238000010556 emulsion polymerization method Methods 0.000 description 2
- 229920005558 epichlorohydrin rubber Polymers 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 description 2
- NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 231100001231 less toxic Toxicity 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 2
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 125000002560 nitrile group Chemical group 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920005596 polymer binder Polymers 0.000 description 2
- 239000002491 polymer binding agent Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000011417 postcuring Methods 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 230000035882 stress Effects 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- VMEZXMFPKOMWHR-UHFFFAOYSA-N (dimethylamino)methyl prop-2-enoate Chemical compound CN(C)COC(=O)C=C VMEZXMFPKOMWHR-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- BVCYGKIVZPIAMH-BQYQJAHWSA-N (e)-4-cycloheptyloxy-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C\C(=O)OC1CCCCCC1 BVCYGKIVZPIAMH-BQYQJAHWSA-N 0.000 description 1
- 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 description 1
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- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 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 description 1
- 150000003336 secondary aromatic amines Chemical class 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
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000007858 starting material 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
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- 230000008961 swelling Effects 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
- 239000004408 titanium dioxide Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- APEJMQOBVMLION-VOTSOKGWSA-N trans-cinnamamide Chemical compound NC(=O)\C=C\C1=CC=CC=C1 APEJMQOBVMLION-VOTSOKGWSA-N 0.000 description 1
- 239000011995 wilkinson's catalyst Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 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 (3)
| Publication Number | Publication Date |
|---|---|
| JP2010144176A JP2010144176A (ja) | 2010-07-01 |
| JP2010144176A5 JP2010144176A5 (enExample) | 2012-11-29 |
| JP5634706B2 true JP5634706B2 (ja) | 2014-12-03 |
Family
ID=42060659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009288213A Expired - Fee Related JP5634706B2 (ja) | 2008-12-19 | 2009-12-18 | 加硫可能なポリマー組成物 |
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 |
Family Cites Families (22)
| 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 |
| CA2231300A1 (en) * | 1998-03-06 | 1999-09-06 | Bayer Inc. | Improved nitrile polymer vulcanizate and process for the production thereof |
| JP3717302B2 (ja) * | 1998-03-19 | 2005-11-16 | ユニマテック株式会社 | アクリル系エラストマー組成物 |
| 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 |
| US20070037930A1 (en) * | 2003-09-30 | 2007-02-15 | Yoshiyuki Odagawa | Cross-linkable rubber composition and cross-linked product |
| CN101031415A (zh) * | 2004-09-29 | 2007-09-05 | 日本瑞翁株式会社 | 橡胶积层体 |
| 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 |
| CN101331183B (zh) * | 2005-12-21 | 2011-11-02 | 日本瑞翁株式会社 | 交联性橡胶组合物以及橡胶交联物 |
| 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
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0905154A2 (pt) | 2011-03-22 |
| KR20100071930A (ko) | 2010-06-29 |
| 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 |
| CN101845157B (zh) | 2014-07-09 |
| CA2688735A1 (en) | 2010-06-19 |
| EP2199326A1 (en) | 2010-06-23 |
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