CA1163399A - Homo-and co-polymers of 1,3-dienes bearing reactive silyl groups - Google Patents
Homo-and co-polymers of 1,3-dienes bearing reactive silyl groupsInfo
- Publication number
- CA1163399A CA1163399A CA000380111A CA380111A CA1163399A CA 1163399 A CA1163399 A CA 1163399A CA 000380111 A CA000380111 A CA 000380111A CA 380111 A CA380111 A CA 380111A CA 1163399 A CA1163399 A CA 1163399A
- Authority
- CA
- Canada
- Prior art keywords
- homo
- polymer
- radical
- carbon atoms
- polymers
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229920001577 copolymer Polymers 0.000 title claims abstract description 36
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 title claims abstract description 23
- 229920000642 polymer Polymers 0.000 claims abstract description 22
- 239000000203 mixture Substances 0.000 claims abstract description 15
- 239000007767 bonding agent Substances 0.000 claims abstract description 12
- 239000012764 mineral filler Substances 0.000 claims abstract description 9
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 9
- 239000010703 silicon Substances 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 15
- -1 alkyl radical Chemical class 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000005062 Polybutadiene Substances 0.000 claims description 11
- 229920002857 polybutadiene Polymers 0.000 claims description 11
- 150000003377 silicon compounds Chemical class 0.000 claims description 11
- 229920001971 elastomer Polymers 0.000 claims description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 claims description 8
- 239000005050 vinyl trichlorosilane Substances 0.000 claims description 8
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 claims description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 4
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 claims description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 4
- XSDCTSITJJJDPY-UHFFFAOYSA-N chloro-ethenyl-dimethylsilane Chemical compound C[Si](C)(Cl)C=C XSDCTSITJJJDPY-UHFFFAOYSA-N 0.000 claims description 3
- YLJJAVFOBDSYAN-UHFFFAOYSA-N dichloro-ethenyl-methylsilane Chemical compound C[Si](Cl)(Cl)C=C YLJJAVFOBDSYAN-UHFFFAOYSA-N 0.000 claims description 3
- ZLNAFSPCNATQPQ-UHFFFAOYSA-N ethenyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C=C ZLNAFSPCNATQPQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 3
- 229920003052 natural elastomer Polymers 0.000 claims description 3
- 229920001194 natural rubber Polymers 0.000 claims description 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims description 2
- 239000005047 Allyltrichlorosilane Substances 0.000 claims description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 2
- 230000021615 conjugation Effects 0.000 claims description 2
- JMESBNITMFZEGN-UHFFFAOYSA-N dibutoxy(prop-2-enyl)silane Chemical compound CCCCO[SiH](CC=C)OCCCC JMESBNITMFZEGN-UHFFFAOYSA-N 0.000 claims description 2
- 238000009826 distribution Methods 0.000 claims description 2
- MBGQQKKTDDNCSG-UHFFFAOYSA-N ethenyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(C=C)OCC MBGQQKKTDDNCSG-UHFFFAOYSA-N 0.000 claims description 2
- 229920001519 homopolymer Polymers 0.000 claims description 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims description 2
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims description 2
- 229920003051 synthetic elastomer Polymers 0.000 claims description 2
- 229920001169 thermoplastic Polymers 0.000 claims description 2
- HKFSBKQQYCMCKO-UHFFFAOYSA-N trichloro(prop-2-enyl)silane Chemical compound Cl[Si](Cl)(Cl)CC=C HKFSBKQQYCMCKO-UHFFFAOYSA-N 0.000 claims description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 150000003254 radicals Chemical class 0.000 claims 2
- KGBRVYGSZOKOEN-UHFFFAOYSA-N 3-methoxypropoxy(prop-2-enyl)silane Chemical compound C(=C)C[SiH2]OCCCOC KGBRVYGSZOKOEN-UHFFFAOYSA-N 0.000 claims 1
- JUELBUGNCRAGDE-UHFFFAOYSA-N chloro-ethyl-prop-2-enylsilane Chemical compound C(=C)C[SiH](Cl)CC JUELBUGNCRAGDE-UHFFFAOYSA-N 0.000 claims 1
- WDBBXBNCJUQSRZ-UHFFFAOYSA-N diethoxy(prop-2-enoxy)silane Chemical compound C(=C)CO[SiH](OCC)OCC WDBBXBNCJUQSRZ-UHFFFAOYSA-N 0.000 claims 1
- 239000000806 elastomer Substances 0.000 claims 1
- 239000005061 synthetic rubber Substances 0.000 claims 1
- 150000004756 silanes Chemical class 0.000 abstract description 8
- LLVWLCAZSOLOTF-UHFFFAOYSA-N 1-methyl-4-[1,4,4-tris(4-methylphenyl)buta-1,3-dienyl]benzene Chemical compound C1=CC(C)=CC=C1C(C=1C=CC(C)=CC=1)=CC=C(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 LLVWLCAZSOLOTF-UHFFFAOYSA-N 0.000 abstract description 4
- 150000001993 dienes Chemical group 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 31
- 238000004132 cross linking Methods 0.000 description 11
- 238000012360 testing method Methods 0.000 description 10
- 239000003921 oil Substances 0.000 description 9
- 239000005060 rubber Substances 0.000 description 9
- 229910000077 silane Inorganic materials 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 235000012239 silicon dioxide Nutrition 0.000 description 6
- 229920003048 styrene butadiene rubber Polymers 0.000 description 6
- 229920002943 EPDM rubber Polymers 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 239000005864 Sulphur Substances 0.000 description 5
- 239000006229 carbon black Substances 0.000 description 5
- 235000019241 carbon black Nutrition 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000006459 hydrosilylation reaction Methods 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000000306 component Substances 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 239000002174 Styrene-butadiene Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 230000006835 compression Effects 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000007788 liquid Substances 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
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000008117 stearic acid Substances 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
- 229960001296 zinc oxide Drugs 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 229940024545 aluminum hydroxide Drugs 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229910052681 coesite Inorganic materials 0.000 description 2
- 229910052906 cristobalite Inorganic materials 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 229940042472 mineral oil Drugs 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920000136 polysorbate Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000003014 reinforcing effect Effects 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 229960004029 silicic acid Drugs 0.000 description 2
- 125000005624 silicic acid group Chemical group 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910052682 stishovite Inorganic materials 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical class S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 2
- 229910052905 tridymite Inorganic materials 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- BJEMXPVDXFSROA-UHFFFAOYSA-N 3-butylbenzene-1,2-diol Chemical compound CCCCC1=CC=CC(O)=C1O BJEMXPVDXFSROA-UHFFFAOYSA-N 0.000 description 1
- OJOWICOBYCXEKR-UHFFFAOYSA-N 5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical class C1C2C(=CC)CC1C=C2 OJOWICOBYCXEKR-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229920000181 Ethylene propylene rubber Polymers 0.000 description 1
- 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 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 208000037062 Polyps Diseases 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000011398 Portland cement Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000005157 alkyl carboxy group Chemical group 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940024548 aluminum oxide Drugs 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229940116441 divinylbenzene Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- XQSGMDOZMWXUJB-UHFFFAOYSA-N ethenyl-diethoxy-methoxysilane Chemical compound CCO[Si](OC)(C=C)OCC XQSGMDOZMWXUJB-UHFFFAOYSA-N 0.000 description 1
- CKKQRAPQQVMKCH-UHFFFAOYSA-N ethenyl-methoxy-methyl-propoxysilane Chemical compound CCCO[Si](C)(OC)C=C CKKQRAPQQVMKCH-UHFFFAOYSA-N 0.000 description 1
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000004872 foam stabilizing agent Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 229960000443 hydrochloric acid Drugs 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000006263 metalation reaction Methods 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical class O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 238000010060 peroxide vulcanization Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920003245 polyoctenamer Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
- C08C19/28—Reaction with compounds containing carbon-to-carbon unsaturated bonds
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Graft Or Block Polymers (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3022898.9 | 1980-06-19 | ||
| DE3022898 | 1980-06-19 | ||
| DEP3028839.2 | 1980-07-30 | ||
| DE3028839A DE3028839C2 (de) | 1980-07-30 | 1980-07-30 | Verfahren zur Herstellung von reaktive Silylgruppen tragenden Homo- und Copolymeren von 1,3-Dienen sowie deren Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1163399A true CA1163399A (en) | 1984-03-06 |
Family
ID=25786083
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000380111A Expired CA1163399A (en) | 1980-06-19 | 1981-06-18 | Homo-and co-polymers of 1,3-dienes bearing reactive silyl groups |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4396751A (https=) |
| EP (1) | EP0042481B1 (https=) |
| JP (2) | JPS5730707A (https=) |
| CA (1) | CA1163399A (https=) |
| DE (1) | DE3167793D1 (https=) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3129082A1 (de) * | 1981-07-23 | 1983-02-10 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung von reaktive silylgruppen tragenden homo- oder copolymeren von 1,3-dienen |
| NO158806C (no) * | 1982-07-28 | 1988-11-02 | Goldschmidt Ag Th | Organosilisiummodifiserte polydiener, fremgangsmaate til deres fremstilling og deres anvendelse som demulgatorer forjordolje. |
| JPS6250346A (ja) * | 1985-08-30 | 1987-03-05 | Bridgestone Corp | タイヤ用ゴム組成物 |
| JPS62225514A (ja) * | 1986-03-26 | 1987-10-03 | Shin Etsu Chem Co Ltd | ブロツク・グラフト共重合体及びその製造法 |
| US4739021A (en) * | 1986-05-12 | 1988-04-19 | E. I. Du Pont De Nemours And Company | Unsaturated silylated vinyl alcohol polymers |
| US4759992A (en) * | 1986-09-10 | 1988-07-26 | Uniroyal Chemical Company, Inc. | Process for coating moisture-curable low molecular weight polymers and composites thereof |
| GB8927003D0 (en) * | 1989-11-29 | 1990-01-17 | Swift Adhesives Ltd | Chemical compounds |
| DK0497730T3 (da) * | 1991-01-28 | 1994-09-26 | Hydrostress Ag | Føringsskinne med støttebuk til væg- og gulvfræsemaskiner |
| TWI405781B (zh) * | 2009-07-08 | 2013-08-21 | Tsrc Corp | 偶合共聚物及其製造方法 |
| CN102782005B (zh) * | 2010-01-14 | 2015-03-11 | 日本瑞翁株式会社 | 环戊烯开环聚合物及其制造方法 |
| JP5316459B2 (ja) * | 2010-03-30 | 2013-10-16 | 住友化学株式会社 | 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 |
| KR101824752B1 (ko) | 2010-07-23 | 2018-02-01 | 스미토모 고무 고교 가부시키가이샤 | 고무 조성물 및 공기 타이어 |
| US8334339B2 (en) * | 2010-08-11 | 2012-12-18 | Sumitomo Chemical Co., Ltd. | Conjugated diene-based polymer, conjugated diene-based polymer composition, and process for producing conjugated diene-based polymer |
| DE102011109823B4 (de) * | 2010-08-11 | 2023-10-12 | Sumitomo Chemical Company, Limited | Polymer auf Basis von konjugiertem Dien, Polymerzusammensetzung auf Basis von konjugiertem Dien und Verfahren zur Herstellung von Polymer auf Basis von konjugiertem Dien |
| EP2463310B1 (en) * | 2010-12-13 | 2014-02-19 | Sumitomo Rubber Industries, Ltd. | Rubber composition and pneumatic tire |
| JP5249404B2 (ja) | 2010-12-13 | 2013-07-31 | 住友ゴム工業株式会社 | ゴム組成物及び空気入りタイヤ |
| TWI413648B (zh) * | 2010-12-31 | 2013-11-01 | Chi Mei Corp | 共軛二烯－乙烯基芳香烴共聚物及其製備方法 |
| TWI428357B (zh) * | 2010-12-31 | 2014-03-01 | Chi Mei Corp | 共軛二烯－乙烯基芳香烴共聚物及其製備方法 |
| BR112013024592A2 (pt) | 2011-03-25 | 2016-12-27 | Sumitomo Rubber Ind | composição de borracha e pneu |
| EP2674457B1 (en) | 2011-04-22 | 2016-09-14 | Sumitomo Rubber Industries, Ltd. | Rubber composition and pneumatic tire |
| CN103502345B (zh) | 2011-04-28 | 2016-01-20 | 住友橡胶工业株式会社 | 橡胶组合物及充气轮胎 |
| CN103562297A (zh) * | 2011-06-01 | 2014-02-05 | 竹本油脂株式会社 | 无机填充材料用分散剂及其制备方法 |
| WO2013183743A1 (ja) | 2012-06-08 | 2013-12-12 | 住友ゴム工業株式会社 | トレッド用ゴム組成物及び空気入りタイヤ |
| US20140121316A1 (en) | 2012-11-01 | 2014-05-01 | Cray Valley Usa, Llc | Silane functionalized oligomer and rubber compound comprising the same |
| JP6181529B2 (ja) | 2013-11-25 | 2017-08-16 | 住友ゴム工業株式会社 | 空気入りタイヤ |
| JP6424868B2 (ja) * | 2016-09-07 | 2018-11-21 | 信越化学工業株式会社 | シラン変性共重合体、その製造方法および密着向上剤 |
| US10457752B2 (en) | 2017-06-07 | 2019-10-29 | Fina Technology, Inc. | Silane functionalized poly (farnesene) and rubber compound comprising the same |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2475122A (en) * | 1948-08-19 | 1949-07-05 | Dow Chemical Co | Hydrochlorosilyl addition product with rubber |
| US2557778A (en) * | 1949-04-21 | 1951-06-19 | Dow Corning | Bonding rubber to glass |
| US2952576A (en) * | 1955-11-02 | 1960-09-13 | Phillips Petroleum Co | Glass fiber treated with the reaction product of a liquid polymer of a conjugated diene and silicon halide |
| DE1720527U (de) | 1956-02-10 | 1956-04-19 | Holstein & Kappert Maschf | Waermeaustausch-plattenapparat mit zwei erhitzungsabteilungen. |
| US3244664A (en) * | 1960-10-24 | 1966-04-05 | Phillips Petroleum Co | Silicon-containing polymers |
| NL127712C (https=) * | 1964-12-21 | |||
| GB1090328A (https=) * | 1965-10-23 | |||
| US3655633A (en) * | 1970-08-25 | 1972-04-11 | Dow Corning | Method of silylating organic vinylic polymers |
| US3772353A (en) * | 1970-10-21 | 1973-11-13 | Union Carbide Corp | Silyl acyl peroxides and acyl peroxy polysiloxanes |
| US3719650A (en) * | 1970-10-21 | 1973-03-06 | Union Carbide Corp | Hydrolyzable functional sylyl alkyl alkyl peroxides |
| US3746611A (en) * | 1970-10-21 | 1973-07-17 | Union Carbide Corp | Silyl acyl peroxide and acyl peroxy polysiloxane binders |
| US3772349A (en) * | 1970-10-21 | 1973-11-13 | Union Carbide Corp | Alkyl peroxides |
| US3776977A (en) * | 1971-06-18 | 1973-12-04 | Stauffer Chemical Co | Method of curing organic siloxane polymers and copolymers |
| US3726943A (en) * | 1971-08-12 | 1973-04-10 | Union Carbide Corp | Ethylenically unsaturated monomer polymerization with silyl acyl peroxides and acyl peroxy polysiloxanes |
| US3759869A (en) * | 1971-09-14 | 1973-09-18 | Skeist Labor Inc | Silane substituted polydienes |
| DE2157405C3 (de) * | 1971-11-19 | 1975-10-16 | Chemische Werke Huels Ag, 4370 Marl | Verfahren zur Herstellung von polymeren Kohlenwasserstoffen mit reaktiven SiIyIe ndgruppen |
| US3929850A (en) * | 1971-11-19 | 1975-12-30 | Huels Chemische Werke Ag | Process for the production of polymeric hydrocarbons having reactive silyl end groups |
| US3920715A (en) * | 1971-11-19 | 1975-11-18 | Huels Chemische Werke Ag | Process for the production of polymeric hydrocarbons having reactive silyl end groups |
| US3881536A (en) * | 1972-08-31 | 1975-05-06 | Ppg Industries Inc | Rubber vulcanizates |
| DE2314543C3 (de) * | 1973-03-23 | 1980-09-11 | Chemische Werke Huels Ag, 4370 Marl | Verfahren zur Herstellung von polymeren Kohlenwasserstoffen mit reaktiven Silylseitengruppen |
| US3920714A (en) * | 1972-11-16 | 1975-11-18 | Weber Heinrich | Process for the production of polymeric hydrocarbons with reactive silyl side groups |
| DE2333567A1 (de) | 1973-07-02 | 1975-01-23 | Henkel & Cie Gmbh | Verfahren zur herstellung von alkoxysilangruppen enthaltenden polymeren |
| DE2333566A1 (de) | 1973-07-02 | 1975-01-30 | Henkel & Cie Gmbh | Verfahren zur herstellung von alkoxysilangruppen enthaltenden verbindungen |
| DE2344734A1 (de) * | 1973-09-05 | 1975-03-13 | Bayer Ag | Verfahren zur herstellung von siliziummodifizierten polymeren |
| DE2635601C3 (de) * | 1976-08-07 | 1985-06-05 | Chemische Werke Hüls AG, 4370 Marl | Polymere Haftvermittler für vulkanisierbare Mischungen aus Kautschuken und mineralischen Füllstoffen |
-
1981
- 1981-04-29 DE DE8181103223T patent/DE3167793D1/de not_active Expired
- 1981-04-29 EP EP81103223A patent/EP0042481B1/de not_active Expired
- 1981-06-15 US US06/273,289 patent/US4396751A/en not_active Expired - Fee Related
- 1981-06-18 JP JP9312481A patent/JPS5730707A/ja active Granted
- 1981-06-18 CA CA000380111A patent/CA1163399A/en not_active Expired
-
1989
- 1989-07-10 JP JP1175750A patent/JPH0249006A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE3167793D1 (en) | 1985-01-31 |
| EP0042481B1 (de) | 1984-12-19 |
| JPH0249006A (ja) | 1990-02-19 |
| US4396751A (en) | 1983-08-02 |
| EP0042481A1 (de) | 1981-12-30 |
| JPH0160490B2 (https=) | 1989-12-22 |
| JPS5730707A (en) | 1982-02-19 |
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Legal Events
| Date | Code | Title | Description |
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| MKEX | Expiry |