HUE029872T2 - Modified elastomeric polymers - Google Patents
Modified elastomeric polymers Download PDFInfo
- Publication number
- HUE029872T2 HUE029872T2 HUE09759093A HUE09759093A HUE029872T2 HU E029872 T2 HUE029872 T2 HU E029872T2 HU E09759093 A HUE09759093 A HU E09759093A HU E09759093 A HUE09759093 A HU E09759093A HU E029872 T2 HUE029872 T2 HU E029872T2
- Authority
- HU
- Hungary
- Prior art keywords
- alkyl
- polymer
- vagy vagy
- formula
- aryl
- Prior art date
Links
- 229920000642 polymer Polymers 0.000 title claims description 473
- 125000000217 alkyl group Chemical group 0.000 claims description 250
- 150000001875 compounds Chemical class 0.000 claims description 227
- 239000000203 mixture Substances 0.000 claims description 198
- 125000003118 aryl group Chemical group 0.000 claims description 174
- 239000003607 modifier Substances 0.000 claims description 155
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 144
- 239000003795 chemical substances by application Substances 0.000 claims description 92
- 239000000945 filler Substances 0.000 claims description 55
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 47
- -1 polypropylene Polymers 0.000 claims description 47
- 229910000077 silane Inorganic materials 0.000 claims description 47
- 150000001412 amines Chemical class 0.000 claims description 42
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- 229910052717 sulfur Inorganic materials 0.000 claims description 36
- 239000011593 sulfur Substances 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 238000002360 preparation method Methods 0.000 claims description 24
- 125000000129 anionic group Chemical group 0.000 claims description 22
- 229920001971 elastomer Polymers 0.000 claims description 19
- 125000001931 aliphatic group Chemical group 0.000 claims description 17
- 239000007795 chemical reaction product Substances 0.000 claims description 12
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 9
- 229910052744 lithium Inorganic materials 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 4
- 239000000806 elastomer Substances 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 229920001296 polysiloxane Polymers 0.000 claims description 2
- 210000004556 brain Anatomy 0.000 claims 4
- 229910019567 Re Re Inorganic materials 0.000 claims 3
- 102100025840 Coiled-coil domain-containing protein 86 Human genes 0.000 claims 1
- 101000932708 Homo sapiens Coiled-coil domain-containing protein 86 Proteins 0.000 claims 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims 1
- 108091034117 Oligonucleotide Proteins 0.000 claims 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims 1
- 239000004743 Polypropylene Substances 0.000 claims 1
- 241000219492 Quercus Species 0.000 claims 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 235000008429 bread Nutrition 0.000 claims 1
- 238000002485 combustion reaction Methods 0.000 claims 1
- 238000004049 embossing Methods 0.000 claims 1
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 1
- 235000012054 meals Nutrition 0.000 claims 1
- 229920001155 polypropylene Polymers 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 239000011435 rock Substances 0.000 claims 1
- 230000011664 signaling Effects 0.000 claims 1
- 239000004575 stone Substances 0.000 claims 1
- 239000006228 supernatant Substances 0.000 claims 1
- 235000012976 tarts Nutrition 0.000 claims 1
- 238000012986 modification Methods 0.000 description 85
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 83
- 238000006116 polymerization reaction Methods 0.000 description 73
- 239000007822 coupling agent Substances 0.000 description 69
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 68
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 51
- 230000004048 modification Effects 0.000 description 50
- 239000000377 silicon dioxide Substances 0.000 description 48
- 229920001577 copolymer Polymers 0.000 description 40
- 229920006395 saturated elastomer Polymers 0.000 description 40
- 125000004001 thioalkyl group Chemical group 0.000 description 40
- 125000003545 alkoxy group Chemical group 0.000 description 38
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 37
- 150000001983 dialkylethers Chemical class 0.000 description 37
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 36
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 34
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 34
- 239000000178 monomer Substances 0.000 description 34
- 239000003921 oil Substances 0.000 description 34
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 34
- 125000001183 hydrocarbyl group Chemical group 0.000 description 33
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 32
- 229910052757 nitrogen Inorganic materials 0.000 description 32
- 239000001301 oxygen Substances 0.000 description 32
- 229910052760 oxygen Inorganic materials 0.000 description 32
- 229910052710 silicon Inorganic materials 0.000 description 32
- 239000010703 silicon Substances 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 31
- 229920002857 polybutadiene Polymers 0.000 description 29
- 238000004073 vulcanization Methods 0.000 description 29
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 28
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 28
- 239000000243 solution Substances 0.000 description 28
- 239000006229 carbon black Substances 0.000 description 25
- 125000004122 cyclic group Chemical group 0.000 description 23
- 150000001993 dienes Chemical class 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- 229920003048 styrene butadiene rubber Polymers 0.000 description 21
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 20
- 239000005062 Polybutadiene Substances 0.000 description 20
- 229920002554 vinyl polymer Polymers 0.000 description 20
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 18
- 229920002521 macromolecule Polymers 0.000 description 17
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
- 239000003999 initiator Substances 0.000 description 16
- 238000005859 coupling reaction Methods 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- 229920001897 terpolymer Polymers 0.000 description 15
- 239000005060 rubber Substances 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 125000002947 alkylene group Chemical group 0.000 description 13
- 229920001195 polyisoprene Polymers 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000006011 modification reaction Methods 0.000 description 12
- 238000005259 measurement Methods 0.000 description 11
- 239000004606 Fillers/Extenders Substances 0.000 description 10
- 238000005299 abrasion Methods 0.000 description 10
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 10
- 239000000470 constituent Substances 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
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000009826 distribution Methods 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- 238000005096 rolling process Methods 0.000 description 9
- 125000004665 trialkylsilyl group Chemical group 0.000 description 9
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 8
- 239000002879 Lewis base Substances 0.000 description 8
- 230000008878 coupling Effects 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- 238000005227 gel permeation chromatography Methods 0.000 description 8
- 150000007527 lewis bases Chemical class 0.000 description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- 229920002959 polymer blend Polymers 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- UEKQGZQLUMSLNW-UHFFFAOYSA-N Propyl isome Chemical compound C1=C2C(C(=O)OCCC)C(C(=O)OCCC)C(C)CC2=CC2=C1OCO2 UEKQGZQLUMSLNW-UHFFFAOYSA-N 0.000 description 7
- 150000001336 alkenes Chemical class 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- ZPFKRQXYKULZKP-UHFFFAOYSA-N butylidene Chemical group [CH2+]CC[CH-] ZPFKRQXYKULZKP-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 229920005669 high impact polystyrene Polymers 0.000 description 7
- 239000004797 high-impact polystyrene Substances 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 6
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000007334 copolymerization reaction Methods 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 230000003993 interaction Effects 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229920001194 natural rubber Polymers 0.000 description 6
- 239000010959 steel Substances 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
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 244000043261 Hevea brasiliensis Species 0.000 description 5
- 239000006087 Silane Coupling Agent Substances 0.000 description 5
- 239000002174 Styrene-butadiene Substances 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 125000002877 alkyl aryl group Chemical group 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000012512 characterization method Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 5
- 230000006870 function Effects 0.000 description 5
- VETJSQFHYYLGFF-UHFFFAOYSA-N heptadecyl-[heptadecyl(dimethyl)silyl]sulfanyl-dimethylsilane Chemical compound CCCCCCCCCCCCCCCCC[Si](C)(C)S[Si](C)(C)CCCCCCCCCCCCCCCCC VETJSQFHYYLGFF-UHFFFAOYSA-N 0.000 description 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 5
- 229920003052 natural elastomer Polymers 0.000 description 5
- 230000037361 pathway Effects 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 239000011591 potassium Substances 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical class S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 238000004846 x-ray emission Methods 0.000 description 5
- 125000006732 (C1-C15) 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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-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
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 4
- OVXZVDMCQPLHIY-QXGOIDDHSA-L calcium;4-[[(2r)-2,4-dihydroxy-3,3-dimethylbutanoyl]amino]butanoate Chemical compound [Ca+2].OCC(C)(C)[C@@H](O)C(=O)NCCCC([O-])=O.OCC(C)(C)[C@@H](O)C(=O)NCCCC([O-])=O OVXZVDMCQPLHIY-QXGOIDDHSA-L 0.000 description 4
- 239000000460 chlorine Chemical group 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
- 229960004132 diethyl ether Drugs 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 150000002900 organolithium compounds Chemical class 0.000 description 4
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 4
- 150000003573 thiols Chemical class 0.000 description 4
- 239000005051 trimethylchlorosilane Substances 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910052779 Neodymium Inorganic materials 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001339 alkali metal compounds Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003153 chemical reaction reagent Substances 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
- 230000001010 compromised effect Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- ORTRWBYBJVGVQC-UHFFFAOYSA-N hexadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCS ORTRWBYBJVGVQC-UHFFFAOYSA-N 0.000 description 3
- 229920006158 high molecular weight polymer Polymers 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 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
- 159000000001 potassium salts Chemical class 0.000 description 3
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical class [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 125000000101 thioether group Chemical group 0.000 description 3
- 125000003396 thiol group Chemical class [H]S* 0.000 description 3
- 125000005106 triarylsilyl group Chemical group 0.000 description 3
- 239000003039 volatile agent Substances 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
- 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
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- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
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- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 150000002641 lithium Chemical group 0.000 description 1
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- 238000010551 living anionic polymerization reaction Methods 0.000 description 1
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- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- DZRKBPWATCKLKY-UHFFFAOYSA-N n-benzyl-n-methylprop-2-en-1-amine Chemical compound C=CCN(C)CC1=CC=CC=C1 DZRKBPWATCKLKY-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
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- LDIPVKABLDWRGC-UHFFFAOYSA-N phenylmethoxymethylbenzene;potassium Chemical compound [K].C=1C=CC=CC=1COCC1=CC=CC=C1 LDIPVKABLDWRGC-UHFFFAOYSA-N 0.000 description 1
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- WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 description 1
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- 230000003449 preventive effect Effects 0.000 description 1
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- JPPLPDOXWBVPCW-UHFFFAOYSA-N s-(3-triethoxysilylpropyl) octanethioate Chemical compound CCCCCCCC(=O)SCCC[Si](OCC)(OCC)OCC JPPLPDOXWBVPCW-UHFFFAOYSA-N 0.000 description 1
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- 239000011780 sodium chloride Substances 0.000 description 1
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- 241000894007 species Species 0.000 description 1
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- 239000008117 stearic acid Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
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- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- LZOZLBFZGFLFBV-UHFFFAOYSA-N sulfene Chemical compound C=S(=O)=O LZOZLBFZGFLFBV-UHFFFAOYSA-N 0.000 description 1
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Classifications
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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
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
-
- 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
- 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
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/46—Reaction with unsaturated dicarboxylic acids or anhydrides thereof, e.g. maleinisation
-
- 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
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02T—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
- Y02T10/00—Road transport of goods or passengers
- Y02T10/80—Technologies aiming to reduce greenhouse gasses emissions common to all road transportation technologies
- Y02T10/86—Optimisation of rolling resistance, e.g. weight reduction
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5927808P | 2008-06-06 | 2008-06-06 |
Publications (1)
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|---|---|
| HUE029872T2 true HUE029872T2 (en) | 2017-04-28 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HUE09759093A HUE029872T2 (en) | 2008-06-06 | 2009-05-29 | Modified elastomeric polymers |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US8729167B2 (enExample) |
| EP (1) | EP2283046B1 (enExample) |
| JP (1) | JP5379225B2 (enExample) |
| KR (1) | KR101604503B1 (enExample) |
| CN (1) | CN102066426B (enExample) |
| BR (1) | BRPI0909545A2 (enExample) |
| ES (1) | ES2599309T3 (enExample) |
| HU (1) | HUE029872T2 (enExample) |
| MX (1) | MX2010013397A (enExample) |
| PL (1) | PL2283046T3 (enExample) |
| RU (1) | RU2504555C2 (enExample) |
| TW (1) | TWI498338B (enExample) |
| WO (1) | WO2009148932A1 (enExample) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUE029872T2 (en) | 2008-06-06 | 2017-04-28 | Trinseo Europe Gmbh | Modified elastomeric polymers |
| KR101707693B1 (ko) | 2008-11-11 | 2017-02-16 | 트린세오 유럽 게엠베하 | 개질된 중합체의 제조시 실란올을 제거하는 방법 |
| TW201134837A (en) | 2009-12-21 | 2011-10-16 | Styron Europe Gmbh | Modified polymer compositions |
| US8895684B2 (en) | 2009-12-21 | 2014-11-25 | Styron Europe Gmbh | Modified polymer compositions |
| WO2012041804A2 (en) | 2010-09-30 | 2012-04-05 | Styron Europe Gmbh | Polymer compositions |
| JP2012240927A (ja) * | 2011-05-16 | 2012-12-10 | Shin-Etsu Chemical Co Ltd | 有機ケイ素化合物及びその製造方法、ゴム用配合剤、ゴム組成物並びにタイヤ |
| KR101265254B1 (ko) * | 2011-10-07 | 2013-05-16 | 금호석유화학 주식회사 | 실리카 보강재에 대한 상용성이 우수한 말단변성 디엔계 공중합체 및 이의 제조방법 |
| JP2013119529A (ja) * | 2011-12-07 | 2013-06-17 | Shin-Etsu Chemical Co Ltd | 有機ケイ素化合物及びその製造方法、ゴム用配合剤並びにゴム組成物 |
| CA2865902C (en) | 2012-03-02 | 2016-06-07 | Cabot Corporation | Elastomeric composites containing modified fillers and functionalized elastomers |
| EP2828301B1 (en) * | 2012-03-20 | 2016-10-05 | Trinseo Europe GmbH | Modified polymer compositions |
| US8993669B2 (en) | 2012-03-28 | 2015-03-31 | The Goodyear Tire & Rubber Company | Functionalized polymer, rubber composition and pneumatic tire |
| ES2642163T3 (es) | 2012-09-14 | 2017-11-15 | Trinseo Europe Gmbh | Polímeros modificados por amino silano |
| BR112015005407A2 (pt) * | 2012-09-14 | 2017-07-04 | Trinseo Europe Gmbh | modificador de sulfeto de silano, método para fabricar um modificador de sulfeto de silano, composto macromolecular elastomérico modificado de sulfeto de silano, método para fabricar um composto macromolecular elastomérico modificado de sulfeto de silano, composição de polímero, composição de polímero vulcanizado, método para fazer uma composição de polímero vulcanizado e artigo |
| US10005869B2 (en) * | 2013-07-22 | 2018-06-26 | Trinseo Europe Gmbh | Polymerisation initiators |
| JP6313850B2 (ja) * | 2013-09-27 | 2018-04-18 | トリンゼオ ヨーロッパ ゲゼルシャフト ミット ベシュレンクテル ハフツング | 低ビニル結合の変性エラストマー性コポリマー |
| JP6461940B2 (ja) | 2013-10-18 | 2019-01-30 | トリンゼオ ヨーロッパ ゲゼルシャフト ミット ベシュレンクテル ハフツング | 機能性をもたせたエラストマー重合体における使用のためのビニルシラン |
| EP3080205A1 (en) | 2013-12-09 | 2016-10-19 | Trinseo Europe GmbH | Silane modified elastomeric polymers |
| WO2016008507A1 (en) | 2014-07-14 | 2016-01-21 | Trinseo Europe Gmbh | Aminosilyl-substituted diarylethene compounds for anionic polymerisation |
| EP3045495B1 (en) | 2015-01-14 | 2017-07-26 | Trinseo Europe GmbH | Functionalized elastomeric polymer compositions, their preparation methods and crosslinked rubber compositions thereof |
| EP3059256B1 (en) * | 2015-02-18 | 2017-11-15 | Trinseo Europe GmbH | A functionalized polymer blend for a tire |
| PL3059099T3 (pl) | 2015-02-18 | 2018-07-31 | Trinseo Europe Gmbh | Mieszanina polimerów do wytwarzania opon |
| HUE051407T2 (hu) | 2015-02-18 | 2021-03-01 | Trinseo Europe Gmbh | Funkcionalizált elasztomer polimerekhez elágazó ágensként alkalmazott multivinil-amino-szilánok |
| FR3038313B1 (fr) | 2015-07-02 | 2017-07-21 | Michelin & Cie | Elastomere dienique modifie a ip reduit et composition de caoutchouc le contenant |
| EP3133093A1 (en) | 2015-08-20 | 2017-02-22 | Trinseo Europe GmbH | Elastomeric polymer |
| EP3159346B1 (en) | 2015-10-21 | 2018-07-04 | Trinseo Europe GmbH | Aminosilane-functionalized dienes for use in functionalization of elastomeric polymers |
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-
2009
- 2009-05-29 HU HUE09759093A patent/HUE029872T2/en unknown
- 2009-05-29 CN CN2009801206687A patent/CN102066426B/zh active Active
- 2009-05-29 EP EP09759093.9A patent/EP2283046B1/en active Active
- 2009-05-29 JP JP2011512536A patent/JP5379225B2/ja active Active
- 2009-05-29 KR KR1020117000257A patent/KR101604503B1/ko active Active
- 2009-05-29 MX MX2010013397A patent/MX2010013397A/es active IP Right Grant
- 2009-05-29 ES ES09759093.9T patent/ES2599309T3/es active Active
- 2009-05-29 PL PL09759093T patent/PL2283046T3/pl unknown
- 2009-05-29 WO PCT/US2009/045553 patent/WO2009148932A1/en not_active Ceased
- 2009-05-29 RU RU2010153583/05A patent/RU2504555C2/ru active
- 2009-05-29 BR BRPI0909545-4A patent/BRPI0909545A2/pt not_active Application Discontinuation
- 2009-05-29 US US12/996,200 patent/US8729167B2/en active Active
- 2009-06-05 TW TW098118752A patent/TWI498338B/zh active
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| KR20110058767A (ko) | 2011-06-01 |
| CN102066426A (zh) | 2011-05-18 |
| RU2504555C2 (ru) | 2014-01-20 |
| TW201002738A (en) | 2010-01-16 |
| PL2283046T3 (pl) | 2017-02-28 |
| RU2010153583A (ru) | 2012-07-20 |
| TWI498338B (zh) | 2015-09-01 |
| MX2010013397A (es) | 2011-05-10 |
| JP5379225B2 (ja) | 2013-12-25 |
| JP2011522928A (ja) | 2011-08-04 |
| WO2009148932A1 (en) | 2009-12-10 |
| BRPI0909545A2 (pt) | 2020-06-23 |
| EP2283046B1 (en) | 2016-10-19 |
| US20110082253A1 (en) | 2011-04-07 |
| ES2599309T3 (es) | 2017-02-01 |
| EP2283046A1 (en) | 2011-02-16 |
| CN102066426B (zh) | 2012-10-17 |
| US8729167B2 (en) | 2014-05-20 |
| KR101604503B1 (ko) | 2016-03-25 |
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