TWI565758B - 橡膠組成物及輪胎 - Google Patents
橡膠組成物及輪胎 Download PDFInfo
- Publication number
- TWI565758B TWI565758B TW102106117A TW102106117A TWI565758B TW I565758 B TWI565758 B TW I565758B TW 102106117 A TW102106117 A TW 102106117A TW 102106117 A TW102106117 A TW 102106117A TW I565758 B TWI565758 B TW I565758B
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- TW
- Taiwan
- Prior art keywords
- rubber
- rubber composition
- polymer
- mass
- polymerization
- Prior art date
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- 229920001971 elastomer Polymers 0.000 title claims description 140
- 239000005060 rubber Substances 0.000 title claims description 140
- 239000000203 mixture Substances 0.000 title claims description 112
- 229920000642 polymer Polymers 0.000 claims description 73
- 239000010455 vermiculite Substances 0.000 claims description 36
- 229910052902 vermiculite Inorganic materials 0.000 claims description 36
- 235000019354 vermiculite Nutrition 0.000 claims description 36
- 239000006229 carbon black Substances 0.000 claims description 34
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 31
- 239000002245 particle Substances 0.000 claims description 22
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 20
- 229920002857 polybutadiene Polymers 0.000 claims description 19
- 239000005062 Polybutadiene Substances 0.000 claims description 18
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 17
- 229920002554 vinyl polymer Polymers 0.000 claims description 17
- 229920003049 isoprene rubber Polymers 0.000 claims description 15
- 244000043261 Hevea brasiliensis Species 0.000 claims description 13
- 229920003052 natural elastomer Polymers 0.000 claims description 13
- 229920001194 natural rubber Polymers 0.000 claims description 13
- 239000000155 melt Substances 0.000 claims description 6
- 238000009826 distribution Methods 0.000 claims description 5
- JSNRRGGBADWTMC-UHFFFAOYSA-N (6E)-7,11-dimethyl-3-methylene-1,6,10-dodecatriene Chemical compound CC(C)=CCCC(C)=CCCC(=C)C=C JSNRRGGBADWTMC-UHFFFAOYSA-N 0.000 claims 2
- CXENHBSYCFFKJS-UHFFFAOYSA-N (3E,6E)-3,7,11-Trimethyl-1,3,6,10-dodecatetraene Natural products CC(C)=CCCC(C)=CCC=C(C)C=C CXENHBSYCFFKJS-UHFFFAOYSA-N 0.000 claims 1
- 229930009668 farnesene Natural products 0.000 claims 1
- 229920001519 homopolymer Polymers 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- 239000004575 stone Substances 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 description 71
- -1 amine compound Chemical class 0.000 description 51
- 238000005096 rolling process Methods 0.000 description 41
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 230000000052 comparative effect Effects 0.000 description 39
- 238000000034 method Methods 0.000 description 34
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 32
- 238000004519 manufacturing process Methods 0.000 description 29
- 238000002156 mixing Methods 0.000 description 28
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 22
- 239000002174 Styrene-butadiene Substances 0.000 description 20
- 238000004073 vulcanization Methods 0.000 description 19
- 239000012295 chemical reaction liquid Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 238000001035 drying Methods 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 15
- 239000007822 coupling agent Substances 0.000 description 15
- 229920001195 polyisoprene Polymers 0.000 description 15
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 14
- 150000001336 alkenes Chemical class 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- 229910052783 alkali metal Inorganic materials 0.000 description 12
- 150000001339 alkali metal compounds Chemical class 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 11
- 230000003712 anti-aging effect Effects 0.000 description 11
- 230000000704 physical effect Effects 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 150000001340 alkali metals Chemical class 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 9
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 9
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 9
- 238000006467 substitution reaction Methods 0.000 description 9
- 235000021355 Stearic acid Nutrition 0.000 description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- 239000003607 modifier Substances 0.000 description 8
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 239000008117 stearic acid Substances 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- 239000011593 sulfur Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000011787 zinc oxide Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000005299 abrasion Methods 0.000 description 6
- 229910052788 barium Inorganic materials 0.000 description 6
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 6
- 238000010556 emulsion polymerization method Methods 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 230000009477 glass transition Effects 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 239000007870 radical polymerization initiator Substances 0.000 description 6
- 229910052761 rare earth metal Inorganic materials 0.000 description 6
- 150000002910 rare earth metals Chemical class 0.000 description 6
- 229920000459 Nitrile rubber Polymers 0.000 description 5
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 238000007711 solidification Methods 0.000 description 5
- 230000008023 solidification Effects 0.000 description 5
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 5
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000012986 chain transfer agent Substances 0.000 description 4
- 239000003431 cross linking reagent Substances 0.000 description 4
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 238000007720 emulsion polymerization reaction Methods 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
- 229910052746 lanthanum Inorganic materials 0.000 description 4
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 4
- 239000004816 latex Substances 0.000 description 4
- 229920000126 latex Polymers 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 4
- 150000002900 organolithium compounds Chemical class 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 229910052712 strontium Inorganic materials 0.000 description 4
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 4
- 229920003051 synthetic elastomer Polymers 0.000 description 4
- 239000005061 synthetic rubber Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- 241001515965 unidentified phage Species 0.000 description 4
- YKFLAYDHMOASIY-UHFFFAOYSA-N γ-terpinene Chemical compound CC(C)C1=CCC(C)=CC1 YKFLAYDHMOASIY-UHFFFAOYSA-N 0.000 description 4
- FRGJFERYCDBOQD-UHFFFAOYSA-N 1,1,1,2-tetrachlorodecane Chemical compound CCCCCCCCC(Cl)C(Cl)(Cl)Cl FRGJFERYCDBOQD-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 229920002943 EPDM rubber Polymers 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 3
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 3
- 229920005549 butyl rubber Polymers 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000006232 furnace black Substances 0.000 description 3
- 229920005555 halobutyl Polymers 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 150000001451 organic peroxides Chemical class 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 150000003464 sulfur compounds Chemical class 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- WJMXTYZCTXTFJM-UHFFFAOYSA-N 1,1,1,2-tetraethoxydecane Chemical compound C(C)OC(C(OCC)(OCC)OCC)CCCCCCCC WJMXTYZCTXTFJM-UHFFFAOYSA-N 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 2
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- SXPGQGNWEWPWQZ-UHFFFAOYSA-N 4-(triethoxymethyl)dodecan-1-amine Chemical compound NCCCC(C(OCC)(OCC)OCC)CCCCCCCC SXPGQGNWEWPWQZ-UHFFFAOYSA-N 0.000 description 2
- DFYGYTNMHPUJBY-UHFFFAOYSA-N 4-(trimethoxymethyl)dodecane-1-thiol Chemical compound SCCCC(C(OC)(OC)OC)CCCCCCCC DFYGYTNMHPUJBY-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- IVMHSZOMAQNCML-UHFFFAOYSA-N C(C)OC(CCCCCCCCCCCCSSSSCCCCCCCCCCCCC(OCC)(OCC)OCC)(OCC)OCC Chemical compound C(C)OC(CCCCCCCCCCCCSSSSCCCCCCCCCCCCC(OCC)(OCC)OCC)(OCC)OCC IVMHSZOMAQNCML-UHFFFAOYSA-N 0.000 description 2
- ZGNIGDDEGYHHCL-UHFFFAOYSA-N C.[Li].[Li] Chemical compound C.[Li].[Li] ZGNIGDDEGYHHCL-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 2
- 229920001174 Diethylhydroxylamine Polymers 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- 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 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
- 239000005639 Lauric acid Substances 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- YLPJWBQVQIERHM-UHFFFAOYSA-M [Co].C(C)[Al](CC)Cl Chemical compound [Co].C(C)[Al](CC)Cl YLPJWBQVQIERHM-UHFFFAOYSA-M 0.000 description 2
- 239000006230 acetylene black Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
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Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F136/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F136/22—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having three or more carbon-to-carbon double bonds
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- 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
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
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- 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
- C08K3/02—Elements
- C08K3/04—Carbon
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- 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
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L47/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Compositions of derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L7/00—Compositions of natural rubber
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- 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
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- 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
- C08L9/06—Copolymers with styrene
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- 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
- C08K2201/00—Specific properties of additives
- C08K2201/002—Physical properties
- C08K2201/003—Additives being defined by their diameter
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- 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
- C08K2201/00—Specific properties of additives
- C08K2201/002—Physical properties
- C08K2201/005—Additives being defined by their particle size in general
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02T—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
- Y02T10/00—Road transport of goods or passengers
- Y02T10/80—Technologies aiming to reduce greenhouse gasses emissions common to all road transportation technologies
- Y02T10/86—Optimisation of rolling resistance, e.g. weight reduction
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Tires In General (AREA)
Applications Claiming Priority (2)
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| WO2013047348A1 (ja) * | 2011-09-30 | 2013-04-04 | 株式会社クラレ | ゴム組成物及びタイヤ |
| JP6021734B2 (ja) * | 2013-05-10 | 2016-11-09 | 住友ゴム工業株式会社 | ゴム組成物及び空気入りタイヤ |
| CN104072825A (zh) | 2013-03-27 | 2014-10-01 | 住友橡胶工业株式会社 | 冬季用无钉轮胎 |
| JP6159574B2 (ja) * | 2013-05-16 | 2017-07-05 | 住友ゴム工業株式会社 | 分枝共役ジエン共重合体および水添分枝共役ジエン共重合体、ゴム組成物、並びに空気入りタイヤ |
| JP6164927B2 (ja) * | 2013-05-16 | 2017-07-19 | 住友ゴム工業株式会社 | 空気入りタイヤ |
| KR102180162B1 (ko) * | 2013-08-23 | 2020-11-19 | 주식회사 쿠라레 | 고무 조성물 및 타이어 |
| JP6084911B2 (ja) | 2013-09-10 | 2017-02-22 | 住友ゴム工業株式会社 | 空気入りタイヤ |
| TWI617589B (zh) * | 2013-09-30 | 2018-03-11 | 可樂麗股份有限公司 | 樹脂組成物、使其硬化而成之硬化物及含有該樹脂組成物之光學用黏著劑 |
| JP6199682B2 (ja) * | 2013-09-30 | 2017-09-20 | 株式会社クラレ | 樹脂組成物、これを硬化させた硬化物及びこの樹脂組成物を含む光学用粘着剤 |
| JP2015074699A (ja) * | 2013-10-08 | 2015-04-20 | 株式会社クラレ | ゴム組成物及びタイヤ |
| JP6539947B2 (ja) * | 2014-05-16 | 2019-07-10 | 横浜ゴム株式会社 | タイヤトレッド用ゴム組成物 |
| JP6352691B2 (ja) * | 2014-06-16 | 2018-07-04 | 住友ゴム工業株式会社 | トラック・バスタイヤ |
| JP6348348B2 (ja) * | 2014-06-16 | 2018-06-27 | 住友ゴム工業株式会社 | 夏用タイヤ |
| JP6375174B2 (ja) * | 2014-08-11 | 2018-08-15 | 株式会社クラレ | 変性ファルネセン重合体、及びその製造方法、ゴム組成物、並びにタイヤ |
| JP6562603B2 (ja) * | 2014-08-11 | 2019-08-21 | 株式会社クラレ | 変性ファルネセン重合体を含むゴム組成物及びタイヤ、並びに変性ファルネセン重合体の製造方法 |
| JP6530173B2 (ja) | 2014-10-27 | 2019-06-12 | 株式会社ブリヂストン | タイヤ |
| CN107109187B (zh) * | 2014-10-28 | 2020-03-06 | 株式会社可乐丽 | 密封材料组合物 |
| JP2016089051A (ja) * | 2014-11-05 | 2016-05-23 | 株式会社クラレ | ゴム組成物及びタイヤ |
| US9334394B1 (en) * | 2015-06-03 | 2016-05-10 | Fina Technology, Inc. | Farnesene resins, rubber compositions, and tire compositions |
| JP6430901B2 (ja) * | 2015-06-30 | 2018-11-28 | 株式会社クラレ | ゴム組成物、及びタイヤ |
| JP6423322B2 (ja) * | 2015-06-30 | 2018-11-14 | 株式会社クラレ | ゴム組成物、及びタイヤ |
| WO2017038724A1 (ja) * | 2015-08-31 | 2017-03-09 | 株式会社クラレ | 被覆重合体粒子、樹脂改質剤、ゴム組成物及びタイヤ |
| WO2017038725A1 (ja) * | 2015-08-31 | 2017-03-09 | 株式会社クラレ | 被覆重合体粒子、樹脂改質剤、ゴム組成物及びタイヤ |
| JP6360107B2 (ja) * | 2016-07-05 | 2018-07-18 | 住友ゴム工業株式会社 | ゴム組成物及び空気入りタイヤ |
| ZA201900664B (en) | 2016-08-17 | 2021-09-29 | Paul Ehrlich Strasse 15 Tuebingen 72076 Germany | T cell receptors and immune therapy using the same |
| RU2742878C1 (ru) * | 2017-03-01 | 2021-02-11 | Сумитомо Раббер Индастриз, Лтд. | Нешипованная шина |
| TWI672217B (zh) | 2017-06-14 | 2019-09-21 | 台灣奈米碳素股份有限公司 | 胎面膠以及用於生產胎面膠的配方 |
| TWI614311B (zh) | 2017-06-14 | 2018-02-11 | 台灣奈米碳素股份有限公司 | 用於製造彈性複合材料的配方、以及彈性複合材料之製造方法 |
| PT3677636T (pt) * | 2017-09-01 | 2022-04-04 | Kuraray Co | Composições de borracha para pneu de pesados e pneu |
| PT3677634T (pt) * | 2017-09-01 | 2022-04-04 | Kuraray Co | Composição de borracha para pneu de alta aderência |
| WO2019044893A1 (ja) | 2017-09-01 | 2019-03-07 | 株式会社クラレ | 重荷重タイヤ用ゴム組成物およびタイヤ |
| JP7225620B2 (ja) * | 2017-09-29 | 2023-02-21 | 住友ゴム工業株式会社 | タイヤ |
| JP2018048349A (ja) * | 2017-12-14 | 2018-03-29 | 株式会社クラレ | ゴム組成物及びタイヤ |
| JP6992477B2 (ja) * | 2017-12-14 | 2022-01-13 | 住友ゴム工業株式会社 | タイヤ用ゴム組成物及び空気入りタイヤ |
| KR102017320B1 (ko) * | 2018-02-05 | 2019-09-02 | 한국타이어앤테크놀로지 주식회사 | 타이어 트레드용 고무 조성물 및 이를 이용하여 제조한 윈터 타이어 |
| KR102044886B1 (ko) * | 2018-02-05 | 2019-11-14 | 한국타이어앤테크놀로지 주식회사 | 타이어 트레드용 고무 조성물 및 이를 이용하여 제조한 윈터 타이어 |
| KR102017321B1 (ko) * | 2018-02-05 | 2019-09-02 | 한국타이어앤테크놀로지 주식회사 | 타이어 트레드용 고무 조성물 및 이를 이용하여 제조한 타이어 |
| FR3091653B1 (fr) | 2019-01-10 | 2023-01-13 | Total Marketing Services | Composition epaississante biosourcee |
| EP3769973A1 (en) | 2019-07-25 | 2021-01-27 | The Goodyear Tire & Rubber Company | A rubber composition and a tire comprising a tread |
| US20230391996A1 (en) * | 2020-10-28 | 2023-12-07 | Kuraray Co., Ltd. | Curable composition and sealant |
| WO2023000097A1 (en) * | 2021-07-21 | 2023-01-26 | ARLANXEO Canada Inc. | Branched poly(isobutylene-co-paramethylstyrene) polymers |
| JP2023115896A (ja) * | 2022-02-08 | 2023-08-21 | 住友ゴム工業株式会社 | ゴム組成物およびタイヤ |
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| CN102164974A (zh) * | 2008-09-04 | 2011-08-24 | 阿迈瑞斯生物技术公司 | 法呢烯互聚物 |
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| JP3497925B2 (ja) * | 1994-07-06 | 2004-02-16 | 三井化学株式会社 | 不飽和性エチレン系共重合体およびその製造方法 |
| US5901766A (en) | 1997-08-26 | 1999-05-11 | The Goodyear Tire & Rubber Company | Pneumatic tire having a tread compound containing high levels of low Tg polymer and resin |
| WO2004000931A1 (ja) * | 2002-06-19 | 2003-12-31 | Bridgestone Corporation | タイヤ用ゴム組成物及びこれを用いたタイヤ |
| JP4316920B2 (ja) * | 2003-04-24 | 2009-08-19 | 住友ゴム工業株式会社 | ゴム組成物およびそれを用いたタイヤ |
| JP5030367B2 (ja) * | 2003-07-23 | 2012-09-19 | 株式会社ブリヂストン | タイヤ |
| JP2005047968A (ja) * | 2003-07-30 | 2005-02-24 | Yokohama Rubber Co Ltd:The | シリカ配合ゴム組成物 |
| US20070037908A1 (en) | 2005-08-09 | 2007-02-15 | Wolfgang Pille-Wolf | Rubber compositions containing improved tackifiers |
| DE602006004826D1 (de) * | 2005-11-29 | 2009-03-05 | Sumitomo Rubber Ind | Kautschukzusammensetzung und Luftreifen, der diese verwendet |
| JP2009120819A (ja) | 2007-10-22 | 2009-06-04 | Sumitomo Rubber Ind Ltd | ゴム組成物およびそれを用いた空気入りタイヤ |
| FR2928647B1 (fr) * | 2008-03-13 | 2011-11-25 | Michelin Soc Tech | Composition de caoutchouc pour bande de roulement de pneumatique hiver |
| KR101620991B1 (ko) * | 2008-09-04 | 2016-05-13 | 아미리스 인코퍼레이티드 | 폴리파네센을 포함하는 접착제 조성물 |
| JP5402112B2 (ja) | 2009-03-11 | 2014-01-29 | Ｊｓｒ株式会社 | ゴム組成物及び空気入りタイヤ |
| US20120237632A1 (en) | 2009-09-10 | 2012-09-20 | David Phillips | Chewing gums having improved removability based on extensional flow properties |
| CA2773870C (en) * | 2009-09-10 | 2015-07-14 | Wm. Wrigley Jr. Company | Chewing gum compositions |
| US20120269924A1 (en) | 2009-09-10 | 2012-10-25 | David Phillips | Chewing gums having improved removability based on linear viscoelastic shear rheology |
| JP2011132298A (ja) | 2009-12-22 | 2011-07-07 | Sumitomo Rubber Ind Ltd | 変性共重合体、それを用いたゴム組成物および空気入りタイヤ |
| JP2013529896A (ja) * | 2010-04-30 | 2013-07-25 | エフ．ホフマン−ラ ロシュ アーゲー | アクイフェックス・エオリカス由来の無機ピロホスファターゼの精製および使用のためのシステムおよび方法 |
| WO2013047348A1 (ja) * | 2011-09-30 | 2013-04-04 | 株式会社クラレ | ゴム組成物及びタイヤ |
| BR112014007431B1 (pt) | 2011-09-30 | 2020-10-13 | Kuraray Co., Ltd. | composição e pneu de borracha |
| JP6173923B2 (ja) * | 2012-02-01 | 2017-08-02 | 住友ゴム工業株式会社 | 分枝共役ジエン共重合体、ゴム組成物および空気入りタイヤ |
| US9434804B2 (en) * | 2012-02-02 | 2016-09-06 | Sumitomo Rubber Industries, Ltd. | Branched conjugated diene copolymer, rubber composition and pneumatic tire |
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- 2013-02-18 CN CN201610743525.3A patent/CN106317520A/zh active Pending
- 2013-02-18 CA CA3073378A patent/CA3073378C/en active Active
- 2013-02-18 PT PT137517181T patent/PT2818507T/pt unknown
- 2013-02-18 TR TR2018/02865T patent/TR201802865T4/tr unknown
- 2013-02-18 JP JP2013529896A patent/JP5617040B2/ja active Active
- 2013-02-18 KR KR1020197007520A patent/KR20190031591A/ko not_active Ceased
- 2013-02-18 CN CN201380010563.2A patent/CN104245818B/zh active Active
- 2013-02-18 RU RU2014138498A patent/RU2617481C2/ru active
- 2013-02-18 ES ES13751718.1T patent/ES2614822T3/es active Active
- 2013-02-18 EP EP16002494.9A patent/EP3156445B1/en active Active
- 2013-02-18 KR KR1020147023404A patent/KR101961513B1/ko active Active
- 2013-02-18 US US14/380,534 patent/US9228077B2/en active Active
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- 2013-02-18 EP EP13751718.1A patent/EP2818507B1/en active Active
- 2013-02-22 TW TW102106117A patent/TWI565758B/zh active
- 2013-07-09 JP JP2013144020A patent/JP2013241609A/ja active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102164974A (zh) * | 2008-09-04 | 2011-08-24 | 阿迈瑞斯生物技术公司 | 法呢烯互聚物 |
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| BR112014020827B1 (pt) | 2020-10-13 |
| CA3059169A1 (en) | 2013-08-29 |
| EP2818507A1 (en) | 2014-12-31 |
| PT3156445T (pt) | 2018-03-20 |
| JP5617040B2 (ja) | 2014-10-29 |
| EP3156445B1 (en) | 2018-01-17 |
| KR20140129044A (ko) | 2014-11-06 |
| JP2013241609A (ja) | 2013-12-05 |
| EP2818507B1 (en) | 2017-01-11 |
| PT2818507T (pt) | 2017-03-08 |
| WO2013125496A1 (ja) | 2013-08-29 |
| HUE038502T2 (hu) | 2018-10-29 |
| EP2818507A4 (en) | 2015-11-04 |
| US9228077B2 (en) | 2016-01-05 |
| TR201802865T4 (tr) | 2018-03-21 |
| RU2014138498A (ru) | 2016-04-10 |
| TW201343795A (zh) | 2013-11-01 |
| CN104245818A (zh) | 2014-12-24 |
| KR101961513B1 (ko) | 2019-03-22 |
| JPWO2013125496A1 (ja) | 2015-07-30 |
| CN106317520A (zh) | 2017-01-11 |
| KR20190031591A (ko) | 2019-03-26 |
| US20150051332A1 (en) | 2015-02-19 |
| ES2614822T3 (es) | 2017-06-02 |
| RU2617481C2 (ru) | 2017-04-25 |
| CA3073378A1 (en) | 2013-08-29 |
| EP3156445A1 (en) | 2017-04-19 |
| CA2865378A1 (en) | 2013-08-29 |
| CA3073378C (en) | 2022-01-04 |
| CA2865378C (en) | 2021-05-11 |
| CN104245818B (zh) | 2016-10-19 |
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