RU2459844C2 - Эластомерные полимеры, модифицированные сульфидом - Google Patents
Эластомерные полимеры, модифицированные сульфидом Download PDFInfo
- Publication number
- RU2459844C2 RU2459844C2 RU2009127763/05A RU2009127763A RU2459844C2 RU 2459844 C2 RU2459844 C2 RU 2459844C2 RU 2009127763/05 A RU2009127763/05 A RU 2009127763/05A RU 2009127763 A RU2009127763 A RU 2009127763A RU 2459844 C2 RU2459844 C2 RU 2459844C2
- Authority
- RU
- Russia
- Prior art keywords
- alkyl
- aralkyl
- aryl
- polymer
- independently selected
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims abstract description 311
- 125000003118 aryl group Chemical group 0.000 claims abstract description 177
- 239000000203 mixture Substances 0.000 claims abstract description 174
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 163
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 160
- 239000003607 modifier Substances 0.000 claims abstract description 120
- 239000001257 hydrogen Substances 0.000 claims abstract description 72
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 72
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 63
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 61
- 239000010703 silicon Substances 0.000 claims abstract description 61
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 55
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 39
- 150000001412 amines Chemical class 0.000 claims abstract description 39
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims abstract description 38
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 38
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 37
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 37
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 36
- 150000001983 dialkylethers Chemical class 0.000 claims abstract description 36
- 150000002825 nitriles Chemical class 0.000 claims abstract description 36
- 125000004001 thioalkyl group Chemical group 0.000 claims abstract description 36
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims abstract description 33
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims abstract description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 28
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000001301 oxygen Substances 0.000 claims abstract description 25
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 25
- 150000001336 alkenes Chemical class 0.000 claims abstract description 19
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000000126 substance Substances 0.000 claims abstract description 12
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims abstract 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 85
- -1 tin halide Chemical class 0.000 claims description 71
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 59
- 239000003795 chemical substances by application Substances 0.000 claims description 57
- 239000000945 filler Substances 0.000 claims description 54
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 47
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 45
- 229920001577 copolymer Polymers 0.000 claims description 45
- 239000000377 silicon dioxide Substances 0.000 claims description 45
- 238000005859 coupling reaction Methods 0.000 claims description 40
- 229910052717 sulfur Inorganic materials 0.000 claims description 39
- 239000011593 sulfur Substances 0.000 claims description 38
- 239000006229 carbon black Substances 0.000 claims description 36
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 36
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 34
- 239000003921 oil Substances 0.000 claims description 27
- 239000000047 product Substances 0.000 claims description 23
- 235000012239 silicon dioxide Nutrition 0.000 claims description 22
- 229920001897 terpolymer Polymers 0.000 claims description 15
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 claims description 8
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 7
- 229920001519 homopolymer Polymers 0.000 claims description 6
- 239000004793 Polystyrene Substances 0.000 claims description 5
- 229920002223 polystyrene Polymers 0.000 claims description 5
- 229920002943 EPDM rubber Polymers 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 claims description 2
- 239000012634 fragment Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 6
- 239000005864 Sulphur Substances 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 description 53
- 150000001875 compounds Chemical class 0.000 description 46
- 238000006243 chemical reaction Methods 0.000 description 41
- 239000000178 monomer Substances 0.000 description 38
- 238000000034 method Methods 0.000 description 33
- 150000001993 dienes Chemical class 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 229920001971 elastomer Polymers 0.000 description 27
- 239000005060 rubber Substances 0.000 description 26
- 239000000243 solution Substances 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 229920002554 vinyl polymer Polymers 0.000 description 21
- 238000004073 vulcanization Methods 0.000 description 21
- 239000003999 initiator Substances 0.000 description 19
- 239000002904 solvent Substances 0.000 description 19
- 230000000875 corresponding effect Effects 0.000 description 18
- 229920006395 saturated elastomer Polymers 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 17
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 16
- 150000004662 dithiols Chemical class 0.000 description 16
- 238000004519 manufacturing process Methods 0.000 description 16
- 230000004048 modification Effects 0.000 description 16
- 238000012986 modification Methods 0.000 description 16
- 229920002857 polybutadiene Polymers 0.000 description 16
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
- 238000011049 filling Methods 0.000 description 12
- 125000001931 aliphatic group Chemical group 0.000 description 11
- 238000005096 rolling process Methods 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- 239000005062 Polybutadiene Substances 0.000 description 10
- 238000005299 abrasion Methods 0.000 description 10
- 238000009826 distribution Methods 0.000 description 10
- 150000002978 peroxides Chemical class 0.000 description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 238000006011 modification reaction Methods 0.000 description 9
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- 238000010094 polymer processing Methods 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- 229920003048 styrene butadiene rubber Polymers 0.000 description 9
- 239000002879 Lewis base Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 150000007527 lewis bases Chemical class 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 150000003573 thiols Chemical class 0.000 description 8
- 239000004711 α-olefin Substances 0.000 description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 7
- 125000000129 anionic group Chemical group 0.000 description 7
- 238000007334 copolymerization reaction Methods 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 229910052744 lithium Inorganic materials 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 230000002051 biphasic effect Effects 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 5
- 238000007306 functionalization reaction Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 230000003993 interaction Effects 0.000 description 5
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 229920001194 natural rubber Polymers 0.000 description 5
- 150000002900 organolithium compounds Chemical class 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 5
- 125000004665 trialkylsilyl group Chemical group 0.000 description 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 4
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 244000043261 Hevea brasiliensis Species 0.000 description 4
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 4
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 4
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 4
- 239000012967 coordination catalyst Substances 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- 238000001879 gelation Methods 0.000 description 4
- 229920005669 high impact polystyrene Polymers 0.000 description 4
- 239000004797 high-impact polystyrene Substances 0.000 description 4
- 239000004816 latex Substances 0.000 description 4
- 229920000126 latex Polymers 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 229920003052 natural elastomer Polymers 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 229920002959 polymer blend Polymers 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 4
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- 238000004566 IR spectroscopy Methods 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 229910052779 Neodymium Inorganic materials 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 229920006037 cross link polymer Polymers 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 150000002902 organometallic compounds Chemical class 0.000 description 3
- 229920001195 polyisoprene Polymers 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical class [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003377 silicon compounds Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000004071 soot Substances 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- 150000003440 styrenes Chemical class 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- 229910052720 vanadium Inorganic materials 0.000 description 3
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- 235000014692 zinc oxide Nutrition 0.000 description 3
- APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 description 2
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 2
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 2
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 2
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 2
- BBDKZWKEPDTENS-UHFFFAOYSA-N 4-Vinylcyclohexene Chemical compound C=CC1CCC=CC1 BBDKZWKEPDTENS-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- CJSBUWDGPXGFGA-UHFFFAOYSA-N 4-methylpenta-1,3-diene Chemical compound CC(C)=CC=C CJSBUWDGPXGFGA-UHFFFAOYSA-N 0.000 description 2
- ZZMVLMVFYMGSMY-UHFFFAOYSA-N 4-n-(4-methylpentan-2-yl)-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)CC(C)C)=CC=C1NC1=CC=CC=C1 ZZMVLMVFYMGSMY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 241001441571 Hiodontidae Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910003902 SiCl 4 Inorganic materials 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
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- YUOWTJMRMWQJDA-UHFFFAOYSA-J tin(iv) fluoride Chemical compound [F-].[F-].[F-].[F-].[Sn+4] YUOWTJMRMWQJDA-UHFFFAOYSA-J 0.000 description 1
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- FBBATURSCRIBHN-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyldisulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSCCC[Si](OCC)(OCC)OCC FBBATURSCRIBHN-UHFFFAOYSA-N 0.000 description 1
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- C08C19/00—Chemical modification of rubber
- C08C19/20—Incorporating sulfur atoms into the molecule
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- 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
- C08K5/37—Thiols
- C08K5/372—Sulfides, e.g. R-(S)x-R'
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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
- B60C1/0016—Compositions of the tread
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
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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
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
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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
- 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
- C08K5/57—Organo-tin compounds
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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
Landscapes
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- Health & Medical Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2599641C2 (ru) * | 2013-10-25 | 2016-10-10 | Чайна Петролеум Энд Кемикал Корпорейшн | Функциональный полидиен, способ его получения и каучуковая композиция, содержащая его |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DE102007044175A1 (de) * | 2007-09-15 | 2009-03-19 | Lanxess Deutschland Gmbh | Funktionalisierte Hochvinyl-Dienkautschuke |
| KR101707693B1 (ko) | 2008-11-11 | 2017-02-16 | 트린세오 유럽 게엠베하 | 개질된 중합체의 제조시 실란올을 제거하는 방법 |
| US9074073B2 (en) * | 2009-12-07 | 2015-07-07 | The Goodyear Tire & Rubber Company | Rubber composition containing silica reinforcement and functionalized crosslinks and products with component thereof |
| WO2012041804A2 (en) | 2010-09-30 | 2012-04-05 | Styron Europe Gmbh | Polymer compositions |
| CN103370377B (zh) * | 2010-12-14 | 2019-01-15 | 卡博特公司 | 控制填料-聚合物组合物中的电阻率的方法以及与其相关的产品 |
| TWI432470B (zh) * | 2011-12-30 | 2014-04-01 | Chi Mei Corp | 改質的高順式共軛二烯聚合物及其製造方法 |
| US8993669B2 (en) | 2012-03-28 | 2015-03-31 | The Goodyear Tire & Rubber Company | Functionalized polymer, rubber composition and pneumatic tire |
| US9186933B2 (en) | 2012-10-12 | 2015-11-17 | The Goodyear Tire & Rubber Company | Functionalized polymer, rubber composition and pneumatic tire |
| TWI458768B (zh) * | 2012-12-28 | 2014-11-01 | Chi Mei Corp | 橡膠組成及其製造方法 |
| WO2014165151A1 (en) | 2013-03-13 | 2014-10-09 | Cabot Corporation | Coatings having filler-polymer compositions with combined low dielectric constant, high resistivity, and optical density properties and controlled electrical resistivity, devices made therewith, and methods for making same |
| ITRM20130706A1 (it) * | 2013-12-20 | 2015-06-21 | Bridgestone Corp | Mescola in gomma per la preparazione di pneumatici |
| DE102016207744A1 (de) * | 2016-05-04 | 2017-11-09 | Continental Reifen Deutschland Gmbh | Kautschukmischung, Vulkanisat der Kautschukmischung und Fahrzeugreifen |
| EP3241853A1 (de) | 2016-05-04 | 2017-11-08 | Trinseo Europe GmbH | Elastomere polymere mit thioether-modifiziertem rückgrat |
| CN116444953B (zh) * | 2023-04-07 | 2024-11-15 | 江苏麒祥高新材料有限公司 | 一种聚酯组合物的制备方法及其在橡胶中的应用 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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2007
- 2007-12-14 KR KR1020097014940A patent/KR101501296B1/ko not_active Expired - Fee Related
- 2007-12-14 JP JP2009543101A patent/JP5587608B2/ja not_active Expired - Fee Related
- 2007-12-14 CN CN2007800514713A patent/CN101610917B/zh not_active Expired - Fee Related
- 2007-12-14 US US12/519,587 patent/US8053512B2/en not_active Expired - Fee Related
- 2007-12-14 RU RU2009127763/05A patent/RU2459844C2/ru not_active IP Right Cessation
- 2007-12-14 MX MX2009006746A patent/MX2009006746A/es active IP Right Grant
- 2007-12-14 BR BRPI0719461-7A patent/BRPI0719461A2/pt not_active Application Discontinuation
- 2007-12-14 WO PCT/US2007/087564 patent/WO2008076875A1/en not_active Ceased
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| RU2119498C1 (ru) * | 1991-12-13 | 1998-09-27 | Эксон Кемикэл Пейтентс Инк. | Способ модификации термопластичного полимера, способ получения улучшенного многофункционального модификатора вязкости и способ получения функционализированного термопластичного полимера |
| RU2190641C2 (ru) * | 1995-09-14 | 2002-10-10 | ЭНИКЕМ С.п.А. | Эластомерная композиция для протекторов шин |
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| RU2266929C2 (ru) * | 1999-12-30 | 2005-12-27 | Сосьете Де Текноложи Мишлен | Резиновая композиция для пневматических шин и их полупродуктов, содержащая связующий агент (белая сажа/эластомер) со сложноэфирной функцией, и способ ее получения |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2599641C2 (ru) * | 2013-10-25 | 2016-10-10 | Чайна Петролеум Энд Кемикал Корпорейшн | Функциональный полидиен, способ его получения и каучуковая композиция, содержащая его |
Also Published As
| Publication number | Publication date |
|---|---|
| JP5587608B2 (ja) | 2014-09-10 |
| RU2009127763A (ru) | 2011-01-27 |
| WO2008076875A1 (en) | 2008-06-26 |
| CN101610917B (zh) | 2012-10-10 |
| US20100069568A1 (en) | 2010-03-18 |
| KR20090100414A (ko) | 2009-09-23 |
| KR101501296B1 (ko) | 2015-03-10 |
| JP2010513697A (ja) | 2010-04-30 |
| BRPI0719461A2 (pt) | 2014-02-04 |
| EP2121350A1 (en) | 2009-11-25 |
| US8053512B2 (en) | 2011-11-08 |
| CN101610917A (zh) | 2009-12-23 |
| MX2009006746A (es) | 2009-08-28 |
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