DK3280745T3 - INITIATORS FOR COPOLYMERIZING DIENMONOMERS AND VINYLAROMATIC MONOMERS - Google Patents
INITIATORS FOR COPOLYMERIZING DIENMONOMERS AND VINYLAROMATIC MONOMERS Download PDFInfo
- Publication number
- DK3280745T3 DK3280745T3 DK16718262.5T DK16718262T DK3280745T3 DK 3280745 T3 DK3280745 T3 DK 3280745T3 DK 16718262 T DK16718262 T DK 16718262T DK 3280745 T3 DK3280745 T3 DK 3280745T3
- Authority
- DK
- Denmark
- Prior art keywords
- copolymer
- groups
- rubber
- carbon atoms
- component
- Prior art date
Links
- 239000000178 monomer Substances 0.000 title claims description 88
- 239000003999 initiator Substances 0.000 title claims description 26
- 229920001577 copolymer Polymers 0.000 claims description 119
- 229920001971 elastomer Polymers 0.000 claims description 78
- 239000005060 rubber Substances 0.000 claims description 68
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
- 229920002554 vinyl polymer Polymers 0.000 claims description 39
- -1 alkali metal salt Chemical class 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 33
- 229910052783 alkali metal Inorganic materials 0.000 claims description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 27
- 239000003795 chemical substances by application Substances 0.000 claims description 27
- 239000007822 coupling agent Substances 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 150000001993 dienes Chemical class 0.000 claims description 25
- 239000000945 filler Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 23
- 238000007334 copolymerization reaction Methods 0.000 claims description 19
- 230000008569 process Effects 0.000 claims description 15
- 150000001340 alkali metals Chemical class 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000000377 silicon dioxide Substances 0.000 claims description 13
- 125000004429 atom Chemical group 0.000 claims description 12
- 230000008878 coupling Effects 0.000 claims description 12
- 238000010168 coupling process Methods 0.000 claims description 12
- 238000005859 coupling reaction Methods 0.000 claims description 12
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 11
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 11
- 229910052744 lithium Inorganic materials 0.000 claims description 11
- 229910052700 potassium Inorganic materials 0.000 claims description 11
- 239000011591 potassium Substances 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 239000010703 silicon Substances 0.000 claims description 9
- 229910052710 silicon Inorganic materials 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 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 claims description 7
- 125000005370 alkoxysilyl group Chemical group 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000129 anionic group Chemical group 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 150000002118 epoxides Chemical class 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
- 239000011630 iodine Substances 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 150000003553 thiiranes Chemical group 0.000 claims description 4
- 239000010936 titanium Substances 0.000 claims description 4
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 claims description 3
- 239000005062 Polybutadiene Substances 0.000 claims description 3
- 230000000977 initiatory effect Effects 0.000 claims description 3
- 229920002857 polybutadiene Polymers 0.000 claims description 3
- 239000005049 silicon tetrachloride Substances 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 2
- 244000043261 Hevea brasiliensis Species 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- VQKBYKIKHWSKDL-UHFFFAOYSA-N difluoro-bis(trifluorosilyl)silane Chemical compound F[Si](F)(F)[Si](F)(F)[Si](F)(F)F VQKBYKIKHWSKDL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052732 germanium Inorganic materials 0.000 claims description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052735 hafnium Inorganic materials 0.000 claims description 2
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 2
- 229920005555 halobutyl Polymers 0.000 claims description 2
- 229920003049 isoprene rubber Polymers 0.000 claims description 2
- 229920003052 natural elastomer Polymers 0.000 claims description 2
- 229920001194 natural rubber Polymers 0.000 claims description 2
- 229920001084 poly(chloroprene) Polymers 0.000 claims description 2
- VSZWPYCFIRKVQL-UHFFFAOYSA-N selanylidenegallium;selenium Chemical compound [Se].[Se]=[Ga].[Se]=[Ga] VSZWPYCFIRKVQL-UHFFFAOYSA-N 0.000 claims description 2
- AIFMYMZGQVTROK-UHFFFAOYSA-N silicon tetrabromide Chemical compound Br[Si](Br)(Br)Br AIFMYMZGQVTROK-UHFFFAOYSA-N 0.000 claims description 2
- ABTOQLMXBSRXSM-UHFFFAOYSA-N silicon tetrafluoride Chemical compound F[Si](F)(F)F ABTOQLMXBSRXSM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- ASWZNPOTXAXUPB-UHFFFAOYSA-N tribromo(tribromosilyl)silane Chemical compound Br[Si](Br)(Br)[Si](Br)(Br)Br ASWZNPOTXAXUPB-UHFFFAOYSA-N 0.000 claims description 2
- LXEXBJXDGVGRAR-UHFFFAOYSA-N trichloro(trichlorosilyl)silane Chemical compound Cl[Si](Cl)(Cl)[Si](Cl)(Cl)Cl LXEXBJXDGVGRAR-UHFFFAOYSA-N 0.000 claims description 2
- QHAHOIWVGZZELU-UHFFFAOYSA-N trichloro(trichlorosilyloxy)silane Chemical compound Cl[Si](Cl)(Cl)O[Si](Cl)(Cl)Cl QHAHOIWVGZZELU-UHFFFAOYSA-N 0.000 claims description 2
- SDNBGJALFMSQER-UHFFFAOYSA-N trifluoro(trifluorosilyl)silane Chemical compound F[Si](F)(F)[Si](F)(F)F SDNBGJALFMSQER-UHFFFAOYSA-N 0.000 claims description 2
- CIEKVFFSPFYSHN-UHFFFAOYSA-N triiodo(triiodosilyl)silane Chemical compound I[Si](I)(I)[Si](I)(I)I CIEKVFFSPFYSHN-UHFFFAOYSA-N 0.000 claims description 2
- QBKQBCIPNZLKNG-UHFFFAOYSA-N 2-benzyl-1-ethenylpyrrolidine Chemical compound C=CN1CCCC1CC1=CC=CC=C1 QBKQBCIPNZLKNG-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000004071 soot Substances 0.000 claims 2
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- IDEKNJPMOJJQNQ-UHFFFAOYSA-N dichloro-methyl-(2-phenylethyl)silane Chemical compound C[Si](Cl)(Cl)CCC1=CC=CC=C1 IDEKNJPMOJJQNQ-UHFFFAOYSA-N 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 239000004711 α-olefin Substances 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 52
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 35
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 28
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 16
- 125000000524 functional group Chemical group 0.000 description 15
- 230000003993 interaction Effects 0.000 description 13
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
- 239000006229 carbon black Substances 0.000 description 8
- 238000007306 functionalization reaction Methods 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 150000002902 organometallic compounds Chemical class 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
- POAVHXRSAJTSTD-UHFFFAOYSA-N 1-[(4-ethenylphenyl)methyl]pyrrolidine Chemical compound C1=CC(C=C)=CC=C1CN1CCCC1 POAVHXRSAJTSTD-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000003505 polymerization initiator Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 5
- 239000000806 elastomer Substances 0.000 description 5
- 239000003607 modifier Substances 0.000 description 5
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 238000005096 rolling process Methods 0.000 description 4
- 150000003388 sodium compounds Chemical class 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 4
- GAODDBNJCKQQDY-UHFFFAOYSA-N 2-methyl-4,6-bis(octylsulfanylmethyl)phenol Chemical compound CCCCCCCCSCC1=CC(C)=C(O)C(CSCCCCCCCC)=C1 GAODDBNJCKQQDY-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 229920006978 SSBR Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 150000003440 styrenes Chemical class 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- RCJMVGJKROQDCB-UHFFFAOYSA-N 2-methylpenta-1,3-diene Chemical compound CC=CC(C)=C RCJMVGJKROQDCB-UHFFFAOYSA-N 0.000 description 2
- XLOUXCBUKZRSQG-UHFFFAOYSA-N 2-oxo-n-(3-trimethoxysilylpropyl)azepane-1-carboxamide Chemical compound CO[Si](OC)(OC)CCCNC(=O)N1CCCCCC1=O XLOUXCBUKZRSQG-UHFFFAOYSA-N 0.000 description 2
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 2
- FDMZCZOHEHPGMW-UHFFFAOYSA-N CCC(C)[K] Chemical compound CCC(C)[K] FDMZCZOHEHPGMW-UHFFFAOYSA-N 0.000 description 2
- QEPCRAGGRXDAIP-UHFFFAOYSA-N CCC(C)[Na] Chemical compound CCC(C)[Na] QEPCRAGGRXDAIP-UHFFFAOYSA-N 0.000 description 2
- KCMZYCFSSYXEQR-UHFFFAOYSA-N CCCC[K] Chemical compound CCCC[K] KCMZYCFSSYXEQR-UHFFFAOYSA-N 0.000 description 2
- IRDQNLLVRXMERV-UHFFFAOYSA-N CCCC[Na] Chemical compound CCCC[Na] IRDQNLLVRXMERV-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 230000003750 conditioning effect Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 150000003112 potassium compounds Chemical class 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000013074 reference sample Substances 0.000 description 2
- 230000002787 reinforcement Effects 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003512 tertiary amines Chemical group 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- MMZPUXVBQAQQDQ-UHFFFAOYSA-N triethoxy(2-pyridin-4-ylethyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC1=CC=NC=C1 MMZPUXVBQAQQDQ-UHFFFAOYSA-N 0.000 description 2
- XVZMLSWFBPLMEA-UHFFFAOYSA-N trimethoxy(2-pyridin-2-ylethyl)silane Chemical compound CO[Si](OC)(OC)CCC1=CC=CC=N1 XVZMLSWFBPLMEA-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 239000004636 vulcanized rubber Substances 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- PCCCQOGUVCNYOI-FNORWQNLSA-N (3e)-2,3-dimethylpenta-1,3-diene Chemical compound C\C=C(/C)C(C)=C PCCCQOGUVCNYOI-FNORWQNLSA-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
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical class C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- CORMBJOFDGICKF-UHFFFAOYSA-N 1,3,5-trimethoxy 2-vinyl benzene Natural products COC1=CC(OC)=C(C=C)C(OC)=C1 CORMBJOFDGICKF-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ODICSUWNOCWVPI-UHFFFAOYSA-N 1-(oxiran-2-ylmethyl)-4-phenylpiperazine Chemical compound C1CN(C=2C=CC=CC=2)CCN1CC1CO1 ODICSUWNOCWVPI-UHFFFAOYSA-N 0.000 description 1
- HNAGOQWONSUAQE-UHFFFAOYSA-N 1-(oxiran-2-ylmethyl)-4-pyridin-2-ylpiperazine Chemical compound C1CN(C=2N=CC=CC=2)CCN1CC1CO1 HNAGOQWONSUAQE-UHFFFAOYSA-N 0.000 description 1
- HSOLVMTWTCTIMI-UHFFFAOYSA-N 1-benzyl-2-ethenylpyrrolidine Chemical group C=CC1CCCN1CC1=CC=CC=C1 HSOLVMTWTCTIMI-UHFFFAOYSA-N 0.000 description 1
- BMBBIQDCHKBYNH-UHFFFAOYSA-N 1-benzyl-4-(oxiran-2-ylmethyl)piperazine Chemical compound C1CN(CC=2C=CC=CC=2)CCN1CC1CO1 BMBBIQDCHKBYNH-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- WJNKJKGZKFOLOJ-UHFFFAOYSA-N 1-dodecyl-4-ethenylbenzene Chemical compound CCCCCCCCCCCCC1=CC=C(C=C)C=C1 WJNKJKGZKFOLOJ-UHFFFAOYSA-N 0.000 description 1
- YHOMZMOAUNOPCN-UHFFFAOYSA-N 1-ethenyl-2,3,4,5-tetraethylbenzene Chemical compound CCC1=CC(C=C)=C(CC)C(CC)=C1CC YHOMZMOAUNOPCN-UHFFFAOYSA-N 0.000 description 1
- HVOKBODBWQEEGI-UHFFFAOYSA-N 1-ethenyl-3,5-diethylbenzene Chemical compound CCC1=CC(CC)=CC(C=C)=C1 HVOKBODBWQEEGI-UHFFFAOYSA-N 0.000 description 1
- XSHXURIGVYRXAD-UHFFFAOYSA-N 1-ethenyl-3,5-diphenylbenzene Chemical compound C=1C(C=C)=CC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 XSHXURIGVYRXAD-UHFFFAOYSA-N 0.000 description 1
- XTUJFEHBYGQMFD-UHFFFAOYSA-N 1-ethenyl-3-hexyl-5-methylbenzene Chemical compound CCCCCCC1=CC(C)=CC(C=C)=C1 XTUJFEHBYGQMFD-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- VVTGQMLRTKFKAM-UHFFFAOYSA-N 1-ethenyl-4-propylbenzene Chemical compound CCCC1=CC=C(C=C)C=C1 VVTGQMLRTKFKAM-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- ZWWNMTKNJXCLRB-UHFFFAOYSA-N 1-methyl-4-(oxiran-2-ylmethyl)-1,4-diazepane Chemical compound C1CN(C)CCCN1CC1OC1 ZWWNMTKNJXCLRB-UHFFFAOYSA-N 0.000 description 1
- HUPJJZNDTARPJL-UHFFFAOYSA-N 1-methyl-4-(oxiran-2-ylmethyl)piperazine Chemical compound C1CN(C)CCN1CC1OC1 HUPJJZNDTARPJL-UHFFFAOYSA-N 0.000 description 1
- XSPASXKSXBJFKB-UHFFFAOYSA-N 11-trimethoxysilylundecan-1-amine Chemical compound CO[Si](OC)(OC)CCCCCCCCCCCN XSPASXKSXBJFKB-UHFFFAOYSA-N 0.000 description 1
- PGZISVXTYZWYPK-UHFFFAOYSA-N 2-(butoxymethyl)oxolane Chemical compound CCCCOCC1CCCO1 PGZISVXTYZWYPK-UHFFFAOYSA-N 0.000 description 1
- VUFKMYLDDDNUJS-UHFFFAOYSA-N 2-(ethoxymethyl)oxolane Chemical compound CCOCC1CCCO1 VUFKMYLDDDNUJS-UHFFFAOYSA-N 0.000 description 1
- YCRFDHHKONBVBR-UHFFFAOYSA-N 2-(hexoxymethyl)oxolane Chemical compound CCCCCCOCC1CCCO1 YCRFDHHKONBVBR-UHFFFAOYSA-N 0.000 description 1
- IEOPZUMPHCZMCS-UHFFFAOYSA-N 2-(methoxymethyl)oxolane Chemical compound COCC1CCCO1 IEOPZUMPHCZMCS-UHFFFAOYSA-N 0.000 description 1
- KOJGQOMKJLGGPI-UHFFFAOYSA-N 2-(propoxymethyl)oxolane Chemical compound CCCOCC1CCCO1 KOJGQOMKJLGGPI-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- PDELBHCVXBSVPJ-UHFFFAOYSA-N 2-ethenyl-1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=C(C=C)C(C)=C1 PDELBHCVXBSVPJ-UHFFFAOYSA-N 0.000 description 1
- CTIFKKWVNGEOBU-UHFFFAOYSA-N 2-hexadecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O CTIFKKWVNGEOBU-UHFFFAOYSA-N 0.000 description 1
- BUWXUSLQPDDDSD-UHFFFAOYSA-N 2-methyl-2-(2-methylbutan-2-yloxy)butane Chemical compound CCC(C)(C)OC(C)(C)CC BUWXUSLQPDDDSD-UHFFFAOYSA-N 0.000 description 1
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
- AQQPJNOXVZFTGE-UHFFFAOYSA-N 2-octadecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O AQQPJNOXVZFTGE-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- HEMGYNNCNNODNX-UHFFFAOYSA-N 3,4-diaminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1N HEMGYNNCNNODNX-UHFFFAOYSA-N 0.000 description 1
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 description 1
- HUPGCAGBHBJUJC-UHFFFAOYSA-N 3-(3-trimethoxysilylpropoxy)aniline Chemical compound CO[Si](OC)(OC)CCCOC1=CC=CC(N)=C1 HUPGCAGBHBJUJC-UHFFFAOYSA-N 0.000 description 1
- WBUSESIMOZDSHU-UHFFFAOYSA-N 3-(4,5-dihydroimidazol-1-yl)propyl-triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN1CCN=C1 WBUSESIMOZDSHU-UHFFFAOYSA-N 0.000 description 1
- GLISOBUNKGBQCL-UHFFFAOYSA-N 3-[ethoxy(dimethyl)silyl]propan-1-amine Chemical compound CCO[Si](C)(C)CCCN GLISOBUNKGBQCL-UHFFFAOYSA-N 0.000 description 1
- FSMHYZUFHYGNHS-UHFFFAOYSA-N 3-[ethoxy-di(propan-2-yl)silyl]propan-1-amine Chemical compound CCO[Si](C(C)C)(C(C)C)CCCN FSMHYZUFHYGNHS-UHFFFAOYSA-N 0.000 description 1
- FHLWSAZOOSCKKZ-UHFFFAOYSA-N 3-dodecylsulfanyl-1-phenylpropan-1-one Chemical compound CCCCCCCCCCCCSCCC(=O)C1=CC=CC=C1 FHLWSAZOOSCKKZ-UHFFFAOYSA-N 0.000 description 1
- UDTHXSLCACXSKA-UHFFFAOYSA-N 3-tetradecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCCCC1=CC=CC(S(O)(=O)=O)=C1 UDTHXSLCACXSKA-UHFFFAOYSA-N 0.000 description 1
- GBQYMXVQHATSCC-UHFFFAOYSA-N 3-triethoxysilylpropanenitrile Chemical compound CCO[Si](OCC)(OCC)CCC#N GBQYMXVQHATSCC-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- OCTVDLUSQOJZEK-UHFFFAOYSA-N 4,5-diethylocta-1,3-diene Chemical compound CCCC(CC)C(CC)=CC=C OCTVDLUSQOJZEK-UHFFFAOYSA-N 0.000 description 1
- QRYFCNPYGUORTK-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-yldisulfanyl)morpholine Chemical compound C1COCCN1SSC1=NC2=CC=CC=C2S1 QRYFCNPYGUORTK-UHFFFAOYSA-N 0.000 description 1
- DXFURPHVJQITAC-UHFFFAOYSA-N 4-benzyl-1-ethenyl-2-ethylbenzene Chemical compound C1=C(C=C)C(CC)=CC(CC=2C=CC=CC=2)=C1 DXFURPHVJQITAC-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- PRKPGWQEKNEVEU-UHFFFAOYSA-N 4-methyl-n-(3-triethoxysilylpropyl)pentan-2-imine Chemical compound CCO[Si](OCC)(OCC)CCCN=C(C)CC(C)C PRKPGWQEKNEVEU-UHFFFAOYSA-N 0.000 description 1
- VZSCYDNKUMPKGV-UHFFFAOYSA-N 4-methyl-n-(3-trimethoxysilylpropyl)pentan-2-imine Chemical compound CO[Si](OC)(OC)CCCN=C(C)CC(C)C VZSCYDNKUMPKGV-UHFFFAOYSA-N 0.000 description 1
- FHQRDEDZJIFJAL-UHFFFAOYSA-N 4-phenylmorpholine Chemical compound C1COCCN1C1=CC=CC=C1 FHQRDEDZJIFJAL-UHFFFAOYSA-N 0.000 description 1
- JBVPVOWGCBEHDA-UHFFFAOYSA-N C(C)(C)(CC(C)(C)C)[K] Chemical compound C(C)(C)(CC(C)(C)C)[K] JBVPVOWGCBEHDA-UHFFFAOYSA-N 0.000 description 1
- LVGCNFOKTRIMSR-UHFFFAOYSA-N C(C)(C)(CC(C)(C)C)[Na] Chemical compound C(C)(C)(CC(C)(C)C)[Na] LVGCNFOKTRIMSR-UHFFFAOYSA-N 0.000 description 1
- OSZXJHYJANINRO-UHFFFAOYSA-N C(CCC)C1=C(C=CC=C1)[K] Chemical compound C(CCC)C1=C(C=CC=C1)[K] OSZXJHYJANINRO-UHFFFAOYSA-N 0.000 description 1
- AABHFFMLFINJOL-UHFFFAOYSA-N C(CCC)C1=C(C=CC=C1)[Na] Chemical compound C(CCC)C1=C(C=CC=C1)[Na] AABHFFMLFINJOL-UHFFFAOYSA-N 0.000 description 1
- KLTQEYRVGGYGKL-UHFFFAOYSA-N C(CCCCCCCCCCC)OCC1CCCO1 Chemical compound C(CCCCCCCCCCC)OCC1CCCO1 KLTQEYRVGGYGKL-UHFFFAOYSA-N 0.000 description 1
- CAQWNKXTMBFBGI-UHFFFAOYSA-N C.[Na] Chemical compound C.[Na] CAQWNKXTMBFBGI-UHFFFAOYSA-N 0.000 description 1
- PUUFXYYECJHNRG-UHFFFAOYSA-N C1(=CC=CC=C1)CCCC[K] Chemical compound C1(=CC=CC=C1)CCCC[K] PUUFXYYECJHNRG-UHFFFAOYSA-N 0.000 description 1
- QDCXMYDCWHSLGX-UHFFFAOYSA-N C1(=CC=CC=C1)CCCC[Na] Chemical compound C1(=CC=CC=C1)CCCC[Na] QDCXMYDCWHSLGX-UHFFFAOYSA-N 0.000 description 1
- UJBRDPRUQIYEHG-UHFFFAOYSA-N C1(CCCC1)[Na] Chemical compound C1(CCCC1)[Na] UJBRDPRUQIYEHG-UHFFFAOYSA-N 0.000 description 1
- LMGAQRHZGBWNDJ-UHFFFAOYSA-N C1=C(C=CC2=CC=CC=C12)[Na] Chemical compound C1=C(C=CC2=CC=CC=C12)[Na] LMGAQRHZGBWNDJ-UHFFFAOYSA-N 0.000 description 1
- ZJQIGHCCYAYDMM-UHFFFAOYSA-N C1=CC=CC2=CC([K])=CC=C21 Chemical compound C1=CC=CC2=CC([K])=CC=C21 ZJQIGHCCYAYDMM-UHFFFAOYSA-N 0.000 description 1
- FWDBZJBJTDRIIY-UHFFFAOYSA-N CC(C)(C)[K] Chemical compound CC(C)(C)[K] FWDBZJBJTDRIIY-UHFFFAOYSA-N 0.000 description 1
- DFGLZFZXSHRQEA-UHFFFAOYSA-N CC(C)[K] Chemical compound CC(C)[K] DFGLZFZXSHRQEA-UHFFFAOYSA-N 0.000 description 1
- HQPSKTOGFFYYKN-UHFFFAOYSA-N CC(C)[Na] Chemical compound CC(C)[Na] HQPSKTOGFFYYKN-UHFFFAOYSA-N 0.000 description 1
- BJPJHOYUNXUIAO-UHFFFAOYSA-N CCCCCCCCCC[K] Chemical compound CCCCCCCCCC[K] BJPJHOYUNXUIAO-UHFFFAOYSA-N 0.000 description 1
- UKZZSQRNPVODAJ-UHFFFAOYSA-N CCCCCCCCCC[Na] Chemical compound CCCCCCCCCC[Na] UKZZSQRNPVODAJ-UHFFFAOYSA-N 0.000 description 1
- ZJGPGQJYWPRTFO-UHFFFAOYSA-N CCC[K] Chemical compound CCC[K] ZJGPGQJYWPRTFO-UHFFFAOYSA-N 0.000 description 1
- AHCDZZIXAMDCBJ-UHFFFAOYSA-N CCC[Na] Chemical compound CCC[Na] AHCDZZIXAMDCBJ-UHFFFAOYSA-N 0.000 description 1
- ZCUFTCUMEDALHC-UHFFFAOYSA-N CC[K] Chemical compound CC[K] ZCUFTCUMEDALHC-UHFFFAOYSA-N 0.000 description 1
- NTZRDKVFLPLTPU-UHFFFAOYSA-N CC[Na] Chemical compound CC[Na] NTZRDKVFLPLTPU-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- PLOSSHSFATUNTF-UHFFFAOYSA-N [K]C1=CC=CC=C1 Chemical compound [K]C1=CC=CC=C1 PLOSSHSFATUNTF-UHFFFAOYSA-N 0.000 description 1
- DXACEQRRNGDQPD-UHFFFAOYSA-N [K]C1CCCC1 Chemical compound [K]C1CCCC1 DXACEQRRNGDQPD-UHFFFAOYSA-N 0.000 description 1
- ZRZMRTYJUQVIAH-UHFFFAOYSA-N [K]C1CCCCC1 Chemical compound [K]C1CCCCC1 ZRZMRTYJUQVIAH-UHFFFAOYSA-N 0.000 description 1
- GZEYBUOHDIOPTH-UHFFFAOYSA-N [Na]C1CCCCC1 Chemical compound [Na]C1CCCCC1 GZEYBUOHDIOPTH-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- IMJGQTCMUZMLRZ-UHFFFAOYSA-N buta-1,3-dien-2-ylbenzene Chemical compound C=CC(=C)C1=CC=CC=C1 IMJGQTCMUZMLRZ-UHFFFAOYSA-N 0.000 description 1
- LYPSJHXEUHLNGO-UHFFFAOYSA-N buta-2,3-dienyl(tributyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)CC=C=C LYPSJHXEUHLNGO-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- DMBOORLKGDADEQ-UHFFFAOYSA-N dichloro-bis[[dichloro(methyl)silyl]methyl]silane Chemical compound C[Si](Cl)(Cl)C[Si](Cl)(Cl)C[Si](C)(Cl)Cl DMBOORLKGDADEQ-UHFFFAOYSA-N 0.000 description 1
- ZRACHDWEPBOVAJ-UHFFFAOYSA-N dichloro-methyl-[2-[2,3,4,5,6-pentakis[2-[dichloro(methyl)silyl]ethyl]phenyl]ethyl]silane Chemical compound C[Si](Cl)(Cl)CCC1=C(CC[Si](C)(Cl)Cl)C(CC[Si](C)(Cl)Cl)=C(CC[Si](C)(Cl)Cl)C(CC[Si](C)(Cl)Cl)=C1CC[Si](C)(Cl)Cl ZRACHDWEPBOVAJ-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001198 elastomeric copolymer Polymers 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- IQEMUADSVZEVNV-UHFFFAOYSA-N lithium;cyclopentane Chemical compound [Li+].C1CC[CH-]C1 IQEMUADSVZEVNV-UHFFFAOYSA-N 0.000 description 1
- SZAVVKVUMPLRRS-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].C[CH-]C SZAVVKVUMPLRRS-UHFFFAOYSA-N 0.000 description 1
- XBEREOHJDYAKDA-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].CC[CH2-] XBEREOHJDYAKDA-UHFFFAOYSA-N 0.000 description 1
- BHGADZKHWXCHKX-UHFFFAOYSA-N methane;potassium Chemical compound C.[K] BHGADZKHWXCHKX-UHFFFAOYSA-N 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- 238000000569 multi-angle light scattering Methods 0.000 description 1
- AQIQPUUNTCVHBS-UHFFFAOYSA-N n,n-dimethyl-3-triethoxysilylpropan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCN(C)C AQIQPUUNTCVHBS-UHFFFAOYSA-N 0.000 description 1
- QIOYHIUHPGORLS-UHFFFAOYSA-N n,n-dimethyl-3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN(C)C QIOYHIUHPGORLS-UHFFFAOYSA-N 0.000 description 1
- IUJLOAKJZQBENM-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-2-methylpropan-2-amine Chemical compound C1=CC=C2SC(SNC(C)(C)C)=NC2=C1 IUJLOAKJZQBENM-UHFFFAOYSA-N 0.000 description 1
- DTPZJXALAREFEY-UHFFFAOYSA-N n-methyl-3-triethoxysilylpropan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCNC DTPZJXALAREFEY-UHFFFAOYSA-N 0.000 description 1
- DVYVMJLSUSGYMH-UHFFFAOYSA-N n-methyl-3-trimethoxysilylpropan-1-amine Chemical compound CNCCC[Si](OC)(OC)OC DVYVMJLSUSGYMH-UHFFFAOYSA-N 0.000 description 1
- UBVMBXTYMSRUDX-UHFFFAOYSA-N n-prop-2-enyl-3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCNCC=C UBVMBXTYMSRUDX-UHFFFAOYSA-N 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- HDBWAWNLGGMZRQ-UHFFFAOYSA-N p-Vinylbiphenyl Chemical compound C1=CC(C=C)=CC=C1C1=CC=CC=C1 HDBWAWNLGGMZRQ-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-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
- 229920001470 polyketone Polymers 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- JHGCXUUFRJCMON-UHFFFAOYSA-J silicon(4+);tetraiodide Chemical compound [Si+4].[I-].[I-].[I-].[I-] JHGCXUUFRJCMON-UHFFFAOYSA-J 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- BBCAQPYJVYMQFB-UHFFFAOYSA-N sodium;2-methylpropane Chemical compound [Na+].C[C-](C)C BBCAQPYJVYMQFB-UHFFFAOYSA-N 0.000 description 1
- KSMWLICLECSXMI-UHFFFAOYSA-N sodium;benzene Chemical compound [Na+].C1=CC=[C-]C=C1 KSMWLICLECSXMI-UHFFFAOYSA-N 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- PZKOFHKJGUNVTM-UHFFFAOYSA-N trichloro-[dichloro(trichlorosilyl)silyl]silane Chemical compound Cl[Si](Cl)(Cl)[Si](Cl)(Cl)[Si](Cl)(Cl)Cl PZKOFHKJGUNVTM-UHFFFAOYSA-N 0.000 description 1
- KMLVDTJUQJXRRH-UHFFFAOYSA-N triethoxy(2-pyridin-2-ylethyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC1=CC=CC=N1 KMLVDTJUQJXRRH-UHFFFAOYSA-N 0.000 description 1
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- JGUUIHSLFPRUSA-UHFFFAOYSA-N trimethoxy-[2-(2-pyridin-2-ylethylsulfanyl)propyl]silane Chemical compound CO[Si](OC)(OC)CC(C)SCCC1=CC=CC=N1 JGUUIHSLFPRUSA-UHFFFAOYSA-N 0.000 description 1
- MQGPKQPSPLQBBD-UHFFFAOYSA-N trimethoxy-[2-(2-pyridin-4-ylethylsulfanyl)propyl]silane Chemical compound CO[Si](OC)(OC)CC(C)SCCC1=CC=NC=C1 MQGPKQPSPLQBBD-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical compound CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical class C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- B60C1/0016—Compositions of the tread
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/22—Incorporating nitrogen atoms into the molecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/25—Incorporating silicon atoms into the molecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
- C08C19/42—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups
- C08C19/44—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups of polymers containing metal atoms exclusively at one or both ends of the skeleton
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/60—Polymerisation by the diene synthesis
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F236/10—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated with vinyl-aromatic monomers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C08F297/02—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F36/14—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated containing elements other than carbon and hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/42—Introducing metal atoms or metal-containing groups
-
- 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
-
- 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
-
- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L15/00—Compositions of rubber derivatives
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2810/00—Chemical modification of a polymer
- C08F2810/20—Chemical modification of a polymer leading to a crosslinking, either explicitly or inherently
-
- 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
- C08K3/06—Sulfur
-
- 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
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
-
- 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
- C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
-
- 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
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
- C08K5/31—Guanidine; Derivatives 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
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/45—Heterocyclic compounds having sulfur in the ring
- C08K5/46—Heterocyclic compounds having sulfur in the ring with oxygen or nitrogen in the ring
- C08K5/47—Thiazoles
-
- 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
- C08K5/54—Silicon-containing compounds
- C08K5/548—Silicon-containing compounds containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2312/00—Crosslinking
- C08L2312/08—Crosslinking by silane
-
- 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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Inorganic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Tires In General (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15461524 | 2015-04-10 | ||
| PCT/EP2016/057757 WO2016162482A1 (en) | 2015-04-10 | 2016-04-08 | Initiators for the copolymerisation of diene monomers and vinyl aromatic monomers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK3280745T3 true DK3280745T3 (en) | 2019-03-25 |
Family
ID=52875658
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK16718262.5T DK3280745T3 (en) | 2015-04-10 | 2016-04-08 | INITIATORS FOR COPOLYMERIZING DIENMONOMERS AND VINYLAROMATIC MONOMERS |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US10584187B2 (enExample) |
| EP (1) | EP3280745B1 (enExample) |
| JP (1) | JP6789236B2 (enExample) |
| KR (2) | KR20240134234A (enExample) |
| CN (1) | CN107743498B (enExample) |
| AU (1) | AU2016244362A1 (enExample) |
| BR (1) | BR112017021222A2 (enExample) |
| CA (1) | CA2981121A1 (enExample) |
| DK (1) | DK3280745T3 (enExample) |
| EA (1) | EA201792253A1 (enExample) |
| ES (1) | ES2714394T3 (enExample) |
| HU (1) | HUE041621T2 (enExample) |
| IL (1) | IL254884A0 (enExample) |
| MX (1) | MX377123B (enExample) |
| PL (1) | PL3280745T3 (enExample) |
| RS (1) | RS58418B1 (enExample) |
| SG (1) | SG11201708115VA (enExample) |
| TN (1) | TN2017000433A1 (enExample) |
| TR (1) | TR201902990T4 (enExample) |
| WO (1) | WO2016162482A1 (enExample) |
| ZA (1) | ZA201707596B (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2692043T3 (es) | 2015-04-10 | 2018-11-29 | Synthos S.A. | Estireno funcionalizado con [bis (trihidrocarbilsilil) aminosililo] y un método para su preparación |
| EA036907B1 (ru) | 2016-10-06 | 2021-01-13 | Синтос Дворы 7 Сполка З Ограничоном Одповедзяльносьцен Сполка Явна | [бис-(тригидрокарбилсилил)аминосилил]-функционализованный стирол и способ его получения |
| CA3011781A1 (en) | 2016-10-06 | 2018-04-12 | Synthos S.A. | Elastomeric copolymers based on [bis(trihydrocarbylsilyl)aminosilyl]-functionalized styrene and their use in the preparation of rubbers |
| KR102102986B1 (ko) * | 2017-09-29 | 2020-04-21 | 주식회사 엘지화학 | 양 말단 변성 공액디엔계 중합체 및 이의 제조방법 |
| WO2019066279A1 (ko) * | 2017-09-29 | 2019-04-04 | 주식회사 엘지화학 | 양 말단 변성 공액디엔계 중합체 및 이의 제조방법 |
| KR102179487B1 (ko) | 2017-12-05 | 2020-11-16 | 주식회사 엘지화학 | 변성 공액디엔계 중합체 및 이를 포함하는 고무 조성물 |
| KR101926619B1 (ko) | 2018-03-29 | 2018-12-11 | 금호석유화학 주식회사 | 기능성 단량체를 포함하는 공중합체 및 그 제조방법 |
| CN111971316B (zh) * | 2018-04-11 | 2023-07-11 | 西索斯公司 | 氨基硅烷基官能化苯乙烯的混合物、它们的制备及它们在弹性体共聚物生产中的使用 |
| EP3911525B1 (en) | 2019-01-24 | 2023-03-08 | Synthos S.A. | Bissilylamino-functionalized conjugated dienes, their preparation and their use in the production of rubbers |
| CN113396165B (zh) * | 2019-09-11 | 2023-05-30 | 株式会社Lg化学 | 改性共轭二烯类聚合物、其制备方法和包含所述改性共轭二烯类聚合物的橡胶组合物 |
| KR102748773B1 (ko) * | 2019-09-11 | 2025-01-02 | 주식회사 엘지화학 | 변성 공액디엔계 중합체, 이의 제조방법 및 이를 포함하는 고무 조성물 |
| KR102889654B1 (ko) | 2020-09-10 | 2025-11-21 | 주식회사 엘지화학 | 변성 공액디엔계 중합체, 이의 제조방법 및 이를 포함하는 고무 조성물 |
| JP7665524B2 (ja) * | 2019-09-11 | 2025-04-21 | エルジー・ケム・リミテッド | 変性共役ジエン系重合体およびそれを含むゴム組成物 |
| WO2021049915A1 (ko) | 2019-09-11 | 2021-03-18 | 주식회사 엘지화학 | 변성 공액디엔계 중합체 및 이를 포함하는 고무 조성물 |
| KR102601721B1 (ko) | 2019-09-11 | 2023-11-15 | 주식회사 엘지화학 | 변성 공액디엔계 중합체 및 이를 포함하는 고무 조성물 |
| SG11202110158PA (en) | 2019-09-11 | 2021-10-28 | Lg Chemical Ltd | Modified conjugated diene-based polymer, method for preparing the same and rubber composition including the same |
| CN111793179A (zh) * | 2020-07-20 | 2020-10-20 | 彤程化学（中国）有限公司 | 一种毛刷状多官能化橡胶聚合物及其制备和应用 |
| JP2024512679A (ja) * | 2021-04-01 | 2024-03-19 | シントス エス．アー． | ２段階でエタノールからの１，３－ブタジエンの生産における触媒システムの使用 |
Family Cites Families (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH415623A (de) | 1960-11-11 | 1966-06-30 | Monsanto Co | Verfahren zur Herstellung von Stickstoff-Silicium-Verbindungen |
| US3109871A (en) | 1960-12-27 | 1963-11-05 | Phillips Petroleum Co | Production and curing of polyfunctional terminally reactive polymers |
| US4196154A (en) | 1977-10-11 | 1980-04-01 | The Dow Chemical Company | Soluble multifunctional lithium containing initiator |
| JPS58154742A (ja) * | 1982-03-09 | 1983-09-14 | Japan Synthetic Rubber Co Ltd | ジエン系ゴム組成物 |
| JPS63118343A (ja) * | 1986-11-07 | 1988-05-23 | Japan Synthetic Rubber Co Ltd | 共役ジエン系ゴム組成物 |
| JPH0778151B2 (ja) | 1987-07-17 | 1995-08-23 | 日本合成ゴム株式会社 | ゴム組成物 |
| DE3729144A1 (de) | 1987-09-01 | 1989-03-09 | Basf Ag | Bifunktionelle alkaliverbindungen, verfahren zu ihrer herstellung und verwendung als polymerisationsinitiatoren |
| US4935471A (en) | 1987-10-15 | 1990-06-19 | The Goodyear Tire & Rubber Company | Capped polydienes |
| US5329005A (en) | 1992-10-02 | 1994-07-12 | Bridgestone Corporation | Soluble anionic polymerization initiators and preparation thereof |
| JP3378313B2 (ja) * | 1993-09-10 | 2003-02-17 | 株式会社ブリヂストン | ゴム組成物 |
| EP0693505B1 (en) * | 1994-07-18 | 1999-05-06 | Bridgestone Corporation | Elastomers and products having reduced hysteresis and process for the preparation thereof |
| US5567815A (en) * | 1994-07-18 | 1996-10-22 | Bridgestone Corporation | Teritary amine containing antonic initiators used in preparing polymers and process for the preparation thereof |
| US5527753A (en) | 1994-12-13 | 1996-06-18 | Fmc Corporation | Functionalized amine initiators for anionic polymerization |
| JP3641868B2 (ja) | 1996-02-23 | 2005-04-27 | Ｊｓｒ株式会社 | ジオレフィン系（共）重合体の製造方法 |
| KR100285229B1 (ko) * | 1999-03-03 | 2001-03-15 | 조충환 | 용액 중합 스티렌-부타디엔 고무 및 부타디엔 고무의 제조방법 |
| US6627721B1 (en) | 2002-09-19 | 2003-09-30 | The Goodyear Tire & Rubber Company | Functionalized elastomers |
| US6627722B2 (en) * | 2000-12-05 | 2003-09-30 | Stephan Rodewald | Functionalized elastomers |
| US6515087B2 (en) | 2000-12-14 | 2003-02-04 | The Goodyear Tire & Rubber Company | Synthesis of elastomers having low hysteresis |
| JP2004059781A (ja) | 2002-07-30 | 2004-02-26 | Jsr Corp | ブロック共重合体及び該共重合体を含有するアスファルト組成物 |
| US6825306B2 (en) | 2002-08-16 | 2004-11-30 | The Goodyear Tire & Rubber Company | Functionalized monomers for synthesis of rubbery polymers |
| US6753447B2 (en) | 2002-08-16 | 2004-06-22 | The Goodyear Tire & Rubber Company | Functionalized monomers for synthesis of rubbery polymers |
| US6693160B1 (en) * | 2002-08-16 | 2004-02-17 | The Goodyear Tire & Rubber Company | Functionalized monomers for synthesis of rubbery polymers |
| US6933358B2 (en) | 2002-08-16 | 2005-08-23 | The Goodyear Tire & Rubber Company | Functionalized monomers for synthesis of rubbery polymers |
| EP1400543B1 (en) * | 2002-09-19 | 2009-11-11 | The Goodyear Tire & Rubber Company | Functionalized elastomers |
| JP4302547B2 (ja) | 2004-02-18 | 2009-07-29 | 株式会社ブリヂストン | 変性天然ゴムラテックス、変性天然ゴム及びそれらの製造方法 |
| DE602005017635D1 (de) | 2004-08-10 | 2009-12-24 | Jsr Corp | Harzzusammensetzung und formteil daraus |
| BRPI0604797A (pt) | 2005-11-30 | 2007-10-09 | Goodyear Tire & Rubber | polìmeros de borracha funcionalizados |
| WO2008072789A1 (ja) | 2006-12-15 | 2008-06-19 | Sumitomo Chemical Company, Limited | エチレン－プロピレン共重合体、およびそれを含有するポリプロピレン樹脂組成物 |
| KR101636090B1 (ko) | 2008-04-30 | 2016-07-04 | 가부시키가이샤 브리지스톤 | 변성 공액 디엔계 공중합체의 제조 방법, 그 방법에 의해 얻어진 변성 공액 디엔계 공중합체, 고무 조성물 및 타이어 |
| CN101724184B (zh) | 2008-10-29 | 2013-05-01 | 住友橡胶工业株式会社 | 橡胶组合物及轮胎 |
| US20100116404A1 (en) | 2008-11-11 | 2010-05-13 | Annette Lechtenboehmer | Tire with component containing polyketone short fiber and functionalized elastomer |
| US20100152364A1 (en) | 2008-12-12 | 2010-06-17 | The Goodyear Tire & Rubber Company | Polymers, rubber compositions, and tires |
| JP5324384B2 (ja) | 2009-10-05 | 2013-10-23 | 住友ゴム工業株式会社 | 重合体、タイヤ用ゴム組成物及び空気入りタイヤ |
| US20110124771A1 (en) | 2009-11-20 | 2011-05-26 | Paul Harry Sandstrom | Pneumatic tire |
| CN102933613B (zh) | 2009-12-21 | 2015-03-11 | 斯泰隆欧洲有限责任公司 | 改性聚合物组合物 |
| JP2011252137A (ja) | 2010-05-06 | 2011-12-15 | Sumitomo Chemical Co Ltd | 共役ジエン系重合体、共役ジエン系重合体組成物、及び、共役ジエン系重合体の製造方法 |
| DE102011109827A1 (de) | 2010-08-11 | 2012-02-16 | Sumitomo Chemical Company, Ltd. | Polymer auf Basis von konjugiertem Dien, Polymerzusammensetzung auf Basis von konjugiertem Dien und Verfahren zur Herstellung von Polymer auf Basis von konjugiertem Dien |
| KR101874071B1 (ko) * | 2010-12-30 | 2018-07-03 | 가부시키가이샤 브리지스톤 | 아미노실란 개시제 및 이로부터 제조된 관능화 중합체 |
| EP2749575B1 (en) | 2011-08-26 | 2015-05-13 | Asahi Kasei Chemicals Corporation | Method for producing modified conjugated diene polymer, modified conjugated diene polymer, modified conjugated diene polymer composition, rubber composition, and tire |
| US9120890B2 (en) | 2011-11-24 | 2015-09-01 | Sumitomo Rubber Industries, Ltd. | Rubber composition and pneumatic tire |
| TR201816162T4 (tr) | 2015-04-10 | 2018-11-21 | Synthos Sa | [Bis(trihidrokarbilsilil)aminosilil] ile fonksiyonelleştirilmiş stiren bazlı elastomerik kopolimerler ve bunların kauçuk hazırlamada kullanımları. |
| ES2692043T3 (es) | 2015-04-10 | 2018-11-29 | Synthos S.A. | Estireno funcionalizado con [bis (trihidrocarbilsilil) aminosililo] y un método para su preparación |
| EA036907B1 (ru) | 2016-10-06 | 2021-01-13 | Синтос Дворы 7 Сполка З Ограничоном Одповедзяльносьцен Сполка Явна | [бис-(тригидрокарбилсилил)аминосилил]-функционализованный стирол и способ его получения |
| CA3011781A1 (en) | 2016-10-06 | 2018-04-12 | Synthos S.A. | Elastomeric copolymers based on [bis(trihydrocarbylsilyl)aminosilyl]-functionalized styrene and their use in the preparation of rubbers |
-
2016
- 2016-04-08 AU AU2016244362A patent/AU2016244362A1/en not_active Abandoned
- 2016-04-08 PL PL16718262T patent/PL3280745T3/pl unknown
- 2016-04-08 KR KR1020247028635A patent/KR20240134234A/ko active Pending
- 2016-04-08 MX MX2017013010A patent/MX377123B/es active IP Right Grant
- 2016-04-08 WO PCT/EP2016/057757 patent/WO2016162482A1/en not_active Ceased
- 2016-04-08 EA EA201792253A patent/EA201792253A1/ru unknown
- 2016-04-08 TR TR2019/02990T patent/TR201902990T4/tr unknown
- 2016-04-08 ES ES16718262T patent/ES2714394T3/es active Active
- 2016-04-08 JP JP2017552919A patent/JP6789236B2/ja active Active
- 2016-04-08 US US15/565,360 patent/US10584187B2/en active Active
- 2016-04-08 RS RS20190312A patent/RS58418B1/sr unknown
- 2016-04-08 SG SG11201708115VA patent/SG11201708115VA/en unknown
- 2016-04-08 BR BR112017021222A patent/BR112017021222A2/pt active Search and Examination
- 2016-04-08 DK DK16718262.5T patent/DK3280745T3/en active
- 2016-04-08 TN TNP/2017/000433A patent/TN2017000433A1/en unknown
- 2016-04-08 CA CA2981121A patent/CA2981121A1/en not_active Abandoned
- 2016-04-08 HU HUE16718262A patent/HUE041621T2/hu unknown
- 2016-04-08 EP EP16718262.5A patent/EP3280745B1/en active Active
- 2016-04-08 CN CN201680034048.1A patent/CN107743498B/zh active Active
- 2016-04-08 KR KR1020177032699A patent/KR102745901B1/ko active Active
-
2017
- 2017-10-03 IL IL254884A patent/IL254884A0/en unknown
- 2017-11-09 ZA ZA2017/07596A patent/ZA201707596B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20240134234A (ko) | 2024-09-06 |
| KR102745901B1 (ko) | 2024-12-23 |
| ZA201707596B (en) | 2018-11-28 |
| RS58418B1 (sr) | 2019-04-30 |
| BR112017021222A2 (pt) | 2018-07-03 |
| IL254884A0 (en) | 2017-12-31 |
| JP2018513896A (ja) | 2018-05-31 |
| CN107743498B (zh) | 2020-04-28 |
| EP3280745A1 (en) | 2018-02-14 |
| MX2017013010A (es) | 2018-04-24 |
| ES2714394T3 (es) | 2019-05-28 |
| EA201792253A1 (ru) | 2018-02-28 |
| AU2016244362A1 (en) | 2017-11-02 |
| KR20180002683A (ko) | 2018-01-08 |
| HUE041621T2 (hu) | 2019-05-28 |
| CA2981121A1 (en) | 2016-10-13 |
| WO2016162482A1 (en) | 2016-10-13 |
| CN107743498A (zh) | 2018-02-27 |
| PL3280745T3 (pl) | 2019-07-31 |
| MX377123B (es) | 2025-03-07 |
| TR201902990T4 (tr) | 2019-03-21 |
| JP6789236B2 (ja) | 2020-11-25 |
| EP3280745B1 (en) | 2018-12-12 |
| US20180072821A1 (en) | 2018-03-15 |
| SG11201708115VA (en) | 2017-11-29 |
| US10584187B2 (en) | 2020-03-10 |
| TN2017000433A1 (en) | 2019-04-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DK3280745T3 (en) | INITIATORS FOR COPOLYMERIZING DIENMONOMERS AND VINYLAROMATIC MONOMERS | |
| KR101972633B1 (ko) | 실란 설파이드 변형된 탄성체 중합체 | |
| JP6258944B2 (ja) | アミノシラン修飾ポリマー | |
| DK3280766T3 (en) | Elastomeric copolymers based on [bis (trihydrocarbylsilyl) aminosilyl] functionalized styrene and their use in the production of rubber | |
| DK3341424T3 (en) | Elastomeric copolymers based on [bis (trihydrocarbylsilyl) aminosilyl] functionalized styrene and their use in the production of rubber | |
| JP2021505712A (ja) | 変性共役ジエン系重合体及びこれを含むゴム組成物 | |
| EP1963110A2 (en) | Silane-sulfide chain end modified elastomeric polymers | |
| CN102066426A (zh) | 改性的弹性体聚合物 | |
| KR20160033105A (ko) | 중합 개시제 | |
| CN108026222B (zh) | 聚合物化合物、使用其制备改性共轭二烯类聚合物的方法以及改性共轭二烯类聚合物 | |
| JP2013528686A (ja) | 低ビニル含量スチレン−ブタジエンポリマーおよびそれを製造する方法 | |
| HK1256871A1 (en) | Elastomeric copolymers based on [bis(trihydrocarbylsilyl)aminosilyl]-functionalized styrene and their use in the preparation of rubbers | |
| KR20190029651A (ko) | 변성 공액 디엔계 중합체 및 그의 고무 조성물, 그리고 타이어 | |
| TW202026323A (zh) | 多官能乙烯基芳香族共聚物及其製造方法、由其獲得的共軛二烯系共聚物、共軛二烯系共聚物組成物、橡膠交聯物和輪胎構件 | |
| US20170369606A1 (en) | Functionalized Elastomeric Polymer Compositions, Their Preparation Methods and Crosslinked Rubber Compositions Thereof |