CN109553720A - 具有有机膦官能的聚二烯和二烯共聚物 - Google Patents
具有有机膦官能的聚二烯和二烯共聚物 Download PDFInfo
- Publication number
- CN109553720A CN109553720A CN201811179193.6A CN201811179193A CN109553720A CN 109553720 A CN109553720 A CN 109553720A CN 201811179193 A CN201811179193 A CN 201811179193A CN 109553720 A CN109553720 A CN 109553720A
- Authority
- CN
- China
- Prior art keywords
- phosphine
- vinyl
- group
- polymer
- organic
- 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.)
- Pending
Links
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 title claims abstract description 349
- 229920001577 copolymer Polymers 0.000 title abstract description 59
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 174
- 239000000178 monomer Substances 0.000 claims abstract description 135
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 109
- 239000003999 initiator Substances 0.000 claims abstract description 79
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 78
- 150000001993 dienes Chemical class 0.000 claims abstract description 56
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims abstract description 36
- 125000000129 anionic group Chemical group 0.000 claims abstract description 32
- 229910052751 metal Inorganic materials 0.000 claims abstract description 26
- 239000002184 metal Substances 0.000 claims abstract description 26
- 229920000642 polymer Polymers 0.000 claims description 201
- 125000000962 organic group Chemical group 0.000 claims description 91
- 238000006116 polymerization reaction Methods 0.000 claims description 60
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 44
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 38
- 229910052744 lithium Inorganic materials 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 230000015572 biosynthetic process Effects 0.000 claims description 14
- 125000004437 phosphorous atom Chemical group 0.000 claims description 14
- 125000001979 organolithium group Chemical group 0.000 claims description 13
- 239000000377 silicon dioxide Substances 0.000 claims description 12
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 8
- 150000002902 organometallic compounds Chemical class 0.000 claims description 8
- 238000004073 vulcanization Methods 0.000 claims description 8
- 239000006229 carbon black Substances 0.000 claims description 7
- 229910052710 silicon Inorganic materials 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 239000010703 silicon Substances 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 178
- 239000002585 base Substances 0.000 description 134
- -1 phosphorous organo-metallic compound Chemical class 0.000 description 127
- 239000003795 chemical substances by application Substances 0.000 description 51
- 150000001875 compounds Chemical class 0.000 description 48
- 239000000463 material Substances 0.000 description 40
- 239000000203 mixture Substances 0.000 description 40
- 229920001971 elastomer Polymers 0.000 description 33
- 239000002904 solvent Substances 0.000 description 33
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 32
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 31
- 239000005060 rubber Substances 0.000 description 30
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 24
- 229910052799 carbon Inorganic materials 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 22
- 125000000524 functional group Chemical group 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 239000003963 antioxidant agent Substances 0.000 description 19
- 230000003078 antioxidant effect Effects 0.000 description 19
- 229930195733 hydrocarbon Natural products 0.000 description 18
- 150000002430 hydrocarbons Chemical class 0.000 description 18
- 239000004215 Carbon black (E152) Substances 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 235000010290 biphenyl Nutrition 0.000 description 17
- 239000004305 biphenyl Substances 0.000 description 17
- AJVBXLXLODZUME-UHFFFAOYSA-N ethenyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=C)C1=CC=CC=C1 AJVBXLXLODZUME-UHFFFAOYSA-N 0.000 description 17
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 17
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 17
- 229920013730 reactive polymer Polymers 0.000 description 17
- 238000002036 drum drying Methods 0.000 description 16
- 229920003048 styrene butadiene rubber Polymers 0.000 description 16
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 15
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 15
- 238000005516 engineering process Methods 0.000 description 15
- 239000004615 ingredient Substances 0.000 description 15
- YWAKXRMUMFPDSH-UHFFFAOYSA-N propyl ethylene Natural products CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- 239000002174 Styrene-butadiene Substances 0.000 description 14
- 239000007858 starting material Substances 0.000 description 14
- 235000021355 Stearic acid Nutrition 0.000 description 13
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 13
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 13
- 239000008117 stearic acid Substances 0.000 description 13
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 12
- 239000001294 propane Substances 0.000 description 12
- 239000005977 Ethylene Substances 0.000 description 11
- 150000002900 organolithium compounds Chemical class 0.000 description 11
- RQPUZGKLFDPSJD-UHFFFAOYSA-N pent-1-enylcyclohexane Chemical group CCCC=CC1CCCCC1 RQPUZGKLFDPSJD-UHFFFAOYSA-N 0.000 description 11
- 229910052698 phosphorus Inorganic materials 0.000 description 11
- 239000011574 phosphorus Substances 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 10
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 125000003342 alkenyl group Chemical group 0.000 description 9
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 9
- 125000006267 biphenyl group Chemical group 0.000 description 9
- 239000007822 coupling agent Substances 0.000 description 9
- 238000000227 grinding Methods 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
- 150000003003 phosphines Chemical class 0.000 description 9
- 229910001220 stainless steel Inorganic materials 0.000 description 9
- 239000010935 stainless steel Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 229910052718 tin Inorganic materials 0.000 description 9
- BSBYTBSLTSLCGJ-UHFFFAOYSA-N 1-cyclohexylpent-1-enylcyclohexane Chemical group C1(CCCCC1)C(=CCCC)C1CCCCC1 BSBYTBSLTSLCGJ-UHFFFAOYSA-N 0.000 description 8
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 8
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 8
- 239000004594 Masterbatch (MB) Substances 0.000 description 8
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 8
- 238000007334 copolymerization reaction Methods 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 230000008859 change Effects 0.000 description 7
- 238000013329 compounding Methods 0.000 description 7
- MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical group C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 description 7
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 238000009991 scouring Methods 0.000 description 7
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 238000007306 functionalization reaction Methods 0.000 description 6
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 150000003233 pyrroles Chemical class 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 239000011135 tin Substances 0.000 description 6
- QXJFOOGXBMTRPJ-UHFFFAOYSA-N 2-cyclohexylethenylphosphane Chemical compound PC=CC1CCCCC1 QXJFOOGXBMTRPJ-UHFFFAOYSA-N 0.000 description 5
- SEAXNMDNBLVDQZ-UHFFFAOYSA-N 2-ethylbut-1-enylphosphane Chemical compound CCC(CC)=CP SEAXNMDNBLVDQZ-UHFFFAOYSA-N 0.000 description 5
- DOGGXPNAGLBDQE-UHFFFAOYSA-N 4-ethylhex-3-en-3-ylphosphane Chemical compound CCC(P)=C(CC)CC DOGGXPNAGLBDQE-UHFFFAOYSA-N 0.000 description 5
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 230000001419 dependent effect Effects 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 229920001002 functional polymer Polymers 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- TZRHLKRLEZJVIJ-UHFFFAOYSA-N parecoxib Chemical compound C1=CC(S(=O)(=O)NC(=O)CC)=CC=C1C1=C(C)ON=C1C1=CC=CC=C1 TZRHLKRLEZJVIJ-UHFFFAOYSA-N 0.000 description 5
- 229960004662 parecoxib Drugs 0.000 description 5
- 239000003505 polymerization initiator Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 230000009257 reactivity Effects 0.000 description 5
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 4
- OLVJQXMRZOUNLO-UHFFFAOYSA-N 1-phenylprop-1-enylbenzene phosphane Chemical compound C1(=CC=CC=C1)C(=CC)C1=CC=CC=C1.P OLVJQXMRZOUNLO-UHFFFAOYSA-N 0.000 description 4
- QNVSZLMXEOSRGN-UHFFFAOYSA-N 2,2-dicyclohexylethenylphosphane Chemical compound C1CCCCC1C(=CP)C1CCCCC1 QNVSZLMXEOSRGN-UHFFFAOYSA-N 0.000 description 4
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N 2,2-dimethylbutane Chemical compound CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 4
- KGXCHACLIFYNOP-UHFFFAOYSA-N 2-phenylethenylphosphane Chemical compound PC=CC1=CC=CC=C1 KGXCHACLIFYNOP-UHFFFAOYSA-N 0.000 description 4
- DXHADBDDSIRVFF-UHFFFAOYSA-N C(C)C(=C)P Chemical compound C(C)C(=C)P DXHADBDDSIRVFF-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 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
- RIXHVLZSVZYHFC-UHFFFAOYSA-N P.C=CC Chemical compound P.C=CC RIXHVLZSVZYHFC-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- 239000005864 Sulphur Substances 0.000 description 4
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- OZFBPQYPJYYLIY-UHFFFAOYSA-N but-1-enylphosphane Chemical compound CCC=CP OZFBPQYPJYYLIY-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 239000002131 composite material Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000011049 filling Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 229910052732 germanium Inorganic materials 0.000 description 4
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 4
- FAEPLNNIANMFJM-UHFFFAOYSA-N hex-3-en-3-ylphosphane Chemical compound CCC=C(P)CC FAEPLNNIANMFJM-UHFFFAOYSA-N 0.000 description 4
- 230000000977 initiatory effect Effects 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 238000010926 purge Methods 0.000 description 4
- 150000003254 radicals Chemical group 0.000 description 4
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 4
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 3
- GEGLBMPXRFOXTK-UHFFFAOYSA-N 1-diphenylphosphanylethenyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(=C)P(C=1C=CC=CC=1)C1=CC=CC=C1 GEGLBMPXRFOXTK-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 239000010692 aromatic oil Substances 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000000994 depressogenic effect Effects 0.000 description 3
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000806 elastomer Substances 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 239000002955 immunomodulating agent Substances 0.000 description 3
- 229940121354 immunomodulator Drugs 0.000 description 3
- 230000002584 immunomodulator Effects 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 150000002642 lithium compounds Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 150000007530 organic bases Chemical group 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229920002857 polybutadiene Polymers 0.000 description 3
- 239000011414 polymer cement Substances 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
- 238000010058 rubber compounding Methods 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 239000001119 stannous chloride Substances 0.000 description 3
- 235000011150 stannous chloride Nutrition 0.000 description 3
- 229920003051 synthetic elastomer Polymers 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 2
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
- UYMQPNRUQXPLCY-UHFFFAOYSA-N 1-(2-piperidin-1-ylethyl)piperidine Chemical compound C1CCCCN1CCN1CCCCC1 UYMQPNRUQXPLCY-UHFFFAOYSA-N 0.000 description 2
- LRKYLKBLUJXTFL-UHFFFAOYSA-N 1-(piperidin-1-ylmethyl)piperidine Chemical compound C1CCCCN1CN1CCCCC1 LRKYLKBLUJXTFL-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
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000005662 Paraffin oil Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 238000009616 inductively coupled plasma Methods 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000005055 methyl trichlorosilane Substances 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
- 229920001194 natural rubber Polymers 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000012766 organic filler Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 150000003053 piperidines Chemical class 0.000 description 2
- 239000003495 polar organic solvent Substances 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 229910000080 stannane Inorganic materials 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 description 1
- BOGRNZQRTNVZCZ-AATRIKPKSA-N (3e)-3-methylpenta-1,3-diene Chemical compound C\C=C(/C)C=C BOGRNZQRTNVZCZ-AATRIKPKSA-N 0.000 description 1
- AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 description 1
- WQJABHBTNKRCBD-UHFFFAOYSA-N 1,1-dicyclohexylpent-1-en-2-yl(diethyl)phosphane Chemical compound C1CCCCC1C(=C(P(CC)CC)CCC)C1CCCCC1 WQJABHBTNKRCBD-UHFFFAOYSA-N 0.000 description 1
- BOGRNZQRTNVZCZ-UHFFFAOYSA-N 1,2-dimethyl-butadiene Natural products CC=C(C)C=C BOGRNZQRTNVZCZ-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- IBVPVTPPYGGAEL-UHFFFAOYSA-N 1,3-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC(C(C)=C)=C1 IBVPVTPPYGGAEL-UHFFFAOYSA-N 0.000 description 1
- OHYWJUVIUOSKLO-UHFFFAOYSA-N 1-cyclohexylethenylcyclohexane Chemical group C1CCCCC1C(=C)C1CCCCC1 OHYWJUVIUOSKLO-UHFFFAOYSA-N 0.000 description 1
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 1
- CBXRMKZFYQISIV-UHFFFAOYSA-N 1-n,1-n,1-n',1-n',2-n,2-n,2-n',2-n'-octamethylethene-1,1,2,2-tetramine Chemical compound CN(C)C(N(C)C)=C(N(C)C)N(C)C CBXRMKZFYQISIV-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- DTZZDUJGZXLUBS-UHFFFAOYSA-N 2,2-dicyclohexylethenyl(diethyl)phosphane Chemical compound C1CCCCC1C(=CP(CC)CC)C1CCCCC1 DTZZDUJGZXLUBS-UHFFFAOYSA-N 0.000 description 1
- MLAQTULNIPRERT-UHFFFAOYSA-N 2,2-dicyclohexylethenyl(diphenyl)phosphane Chemical compound C1CCCCC1C(C1CCCCC1)=CP(C=1C=CC=CC=1)C1=CC=CC=C1 MLAQTULNIPRERT-UHFFFAOYSA-N 0.000 description 1
- BKNHORGMAGRUAE-UHFFFAOYSA-N 2-cyclohexylethenyl(diethyl)phosphane Chemical compound CCP(CC)C=CC1CCCCC1 BKNHORGMAGRUAE-UHFFFAOYSA-N 0.000 description 1
- OJFKEWWXXQNXQF-UHFFFAOYSA-N 2-cyclohexylethenyl(dimethyl)phosphane Chemical compound CP(C)C=CC1CCCCC1 OJFKEWWXXQNXQF-UHFFFAOYSA-N 0.000 description 1
- BZRBWRMBIRNPSO-UHFFFAOYSA-N 2-cyclohexylethenyl(diphenyl)phosphane Chemical compound C1CCC(CC1)C=CP(c1ccccc1)c1ccccc1 BZRBWRMBIRNPSO-UHFFFAOYSA-N 0.000 description 1
- ZMXONZCSTOWHCI-UHFFFAOYSA-N 2-ethylbut-1-enyl(dimethyl)phosphane Chemical compound CCC(CC)=CP(C)C ZMXONZCSTOWHCI-UHFFFAOYSA-N 0.000 description 1
- SBWXAIMYRFOAFI-UHFFFAOYSA-N 2-ethylbut-1-enyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=C(CC)CC)C1=CC=CC=C1 SBWXAIMYRFOAFI-UHFFFAOYSA-N 0.000 description 1
- ROGIWVXWXZRRMZ-UHFFFAOYSA-N 2-methylbuta-1,3-diene;styrene Chemical compound CC(=C)C=C.C=CC1=CC=CC=C1 ROGIWVXWXZRRMZ-UHFFFAOYSA-N 0.000 description 1
- GGIFEFBEDYDOTI-UHFFFAOYSA-N 2-methylbutan-2-ol;potassium Chemical compound [K].CCC(C)(C)O GGIFEFBEDYDOTI-UHFFFAOYSA-N 0.000 description 1
- XMYFZAWUNVHVGI-UHFFFAOYSA-N 3-ethylpent-2-ene Chemical compound CCC(CC)=CC XMYFZAWUNVHVGI-UHFFFAOYSA-N 0.000 description 1
- ZQDPJFUHLCOCRG-UHFFFAOYSA-N 3-hexene Chemical group CCC=CCC ZQDPJFUHLCOCRG-UHFFFAOYSA-N 0.000 description 1
- IGLWCQMNTGCUBB-UHFFFAOYSA-N 3-methylidenepent-1-ene Chemical compound CCC(=C)C=C IGLWCQMNTGCUBB-UHFFFAOYSA-N 0.000 description 1
- DQFMPTUTAAIXAN-UHFFFAOYSA-N 4,4-dimethyl-1h-imidazol-5-one Chemical compound CC1(C)NC=NC1=O DQFMPTUTAAIXAN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- BVPWJMCABCPUQY-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxy-N-[1-(phenylmethyl)-4-piperidinyl]benzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NC1CCN(CC=2C=CC=CC=2)CC1 BVPWJMCABCPUQY-UHFFFAOYSA-N 0.000 description 1
- QFYYCVZQOVVSHL-UHFFFAOYSA-N 4-ethylhex-3-en-3-yl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C(CC)=C(CC)CC)C1=CC=CC=C1 QFYYCVZQOVVSHL-UHFFFAOYSA-N 0.000 description 1
- IBWZAMIZXZMPEB-UHFFFAOYSA-N CC1=CC(C)=C([Na])C(C)=C1 Chemical compound CC1=CC(C)=C([Na])C(C)=C1 IBWZAMIZXZMPEB-UHFFFAOYSA-N 0.000 description 1
- DMAWHHOICGGPQF-UHFFFAOYSA-N CCCCCC[SiH2]Cl Chemical compound CCCCCC[SiH2]Cl DMAWHHOICGGPQF-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 241001441571 Hiodontidae Species 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
- VHOQXEIFYTTXJU-UHFFFAOYSA-N Isobutylene-isoprene copolymer Chemical compound CC(C)=C.CC(=C)C=C VHOQXEIFYTTXJU-UHFFFAOYSA-N 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- 229910021623 Tin(IV) bromide Inorganic materials 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- VRUNJIXLXYZQJZ-UHFFFAOYSA-M [Ge].[Cl-].C(C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [Ge].[Cl-].C(C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 VRUNJIXLXYZQJZ-UHFFFAOYSA-M 0.000 description 1
- OTVSBAVVPOEWSW-UHFFFAOYSA-N [Li]CCC(C)C Chemical compound [Li]CCC(C)C OTVSBAVVPOEWSW-UHFFFAOYSA-N 0.000 description 1
- 229920000800 acrylic rubber Polymers 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005370 alkoxysilyl group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910021502 aluminium hydroxide Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 229910001423 beryllium ion Inorganic materials 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- BJXLRCLSJBPQML-UHFFFAOYSA-N but-1-en-2-yl(dicyclohexyl)phosphane Chemical compound C1CCCCC1P(C(=C)CC)C1CCCCC1 BJXLRCLSJBPQML-UHFFFAOYSA-N 0.000 description 1
- FITRLSVPAUWOMH-UHFFFAOYSA-N but-1-en-2-yl(diethyl)phosphane Chemical compound CCP(CC)C(=C)CC FITRLSVPAUWOMH-UHFFFAOYSA-N 0.000 description 1
- AMJCYAHYICYAMF-UHFFFAOYSA-N but-1-en-2-yl(dimethyl)phosphane Chemical compound CCC(=C)P(C)C AMJCYAHYICYAMF-UHFFFAOYSA-N 0.000 description 1
- AJJSJMQFYVXHOZ-UHFFFAOYSA-N but-1-en-2-yl(ditert-butyl)phosphane Chemical compound CCC(=C)P(C(C)(C)C)C(C)(C)C AJJSJMQFYVXHOZ-UHFFFAOYSA-N 0.000 description 1
- INRPYFUGICVBEW-UHFFFAOYSA-N but-1-enyl(dicyclohexyl)phosphane Chemical compound CCC=CP(C1CCCCC1)C1CCCCC1 INRPYFUGICVBEW-UHFFFAOYSA-N 0.000 description 1
- UVCBBTAHOCQVHW-UHFFFAOYSA-N but-1-enyl(diethyl)phosphane Chemical compound CCC=CP(CC)CC UVCBBTAHOCQVHW-UHFFFAOYSA-N 0.000 description 1
- TYXNKKWXRAERKJ-UHFFFAOYSA-N but-1-enyl(dimethyl)phosphane Chemical compound CCC=CP(C)C TYXNKKWXRAERKJ-UHFFFAOYSA-N 0.000 description 1
- SWMPOWLFUVGWHY-UHFFFAOYSA-N but-1-enyl(ditert-butyl)phosphane Chemical compound CCC=CP(C(C)(C)C)C(C)(C)C SWMPOWLFUVGWHY-UHFFFAOYSA-N 0.000 description 1
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FQEKAFQSVPLXON-UHFFFAOYSA-N butyl(trichloro)silane Chemical compound CCCC[Si](Cl)(Cl)Cl FQEKAFQSVPLXON-UHFFFAOYSA-N 0.000 description 1
- YMLFYGFCXGNERH-UHFFFAOYSA-K butyltin trichloride Chemical compound CCCC[Sn](Cl)(Cl)Cl YMLFYGFCXGNERH-UHFFFAOYSA-K 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229910021386 carbon form Inorganic materials 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- XGRJZXREYAXTGV-UHFFFAOYSA-N chlorodiphenylphosphine Chemical compound C=1C=CC=CC=1P(Cl)C1=CC=CC=C1 XGRJZXREYAXTGV-UHFFFAOYSA-N 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 230000001808 coupling effect Effects 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N deuterated chloroform Substances [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- NJKDOKBDBHYMAH-UHFFFAOYSA-N dibutyl(dichloro)silane Chemical compound CCCC[Si](Cl)(Cl)CCCC NJKDOKBDBHYMAH-UHFFFAOYSA-N 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- CVAGYCLEIYGJQT-UHFFFAOYSA-N dichloro(dioctyl)silane Chemical compound CCCCCCCC[Si](Cl)(Cl)CCCCCCCC CVAGYCLEIYGJQT-UHFFFAOYSA-N 0.000 description 1
- OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 description 1
- GYGJXSOUJMDEPM-UHFFFAOYSA-N dicyclohexyl(1-phenylprop-1-en-2-yl)phosphane Chemical compound CC(=Cc1ccccc1)P(C1CCCCC1)C1CCCCC1 GYGJXSOUJMDEPM-UHFFFAOYSA-N 0.000 description 1
- SQLUTSCIWXQYDF-UHFFFAOYSA-N dicyclohexyl(2,2-dicyclohexylethenyl)phosphane Chemical compound C1CCCCC1P(C1CCCCC1)C=C(C1CCCCC1)C1CCCCC1 SQLUTSCIWXQYDF-UHFFFAOYSA-N 0.000 description 1
- RQUOHGIEYFVPNZ-UHFFFAOYSA-N dicyclohexyl(2-ethylbut-1-enyl)phosphane Chemical compound C1CCCCC1P(C=C(CC)CC)C1CCCCC1 RQUOHGIEYFVPNZ-UHFFFAOYSA-N 0.000 description 1
- DELQIPODFHIAPS-UHFFFAOYSA-N dicyclohexyl(4-ethylhex-3-en-3-yl)phosphane Chemical compound C1CCCCC1P(C(CC)=C(CC)CC)C1CCCCC1 DELQIPODFHIAPS-UHFFFAOYSA-N 0.000 description 1
- GIXIOAJJVHOMKA-UHFFFAOYSA-N dicyclohexyl(hex-3-en-3-yl)phosphane Chemical compound CCC=C(CC)P(C1CCCCC1)C1CCCCC1 GIXIOAJJVHOMKA-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- YJONKGITDIDECI-UHFFFAOYSA-N diethyl(2-ethylbut-1-enyl)phosphane Chemical compound CCP(CC)C=C(CC)CC YJONKGITDIDECI-UHFFFAOYSA-N 0.000 description 1
- KYVURFFDPKTBQE-UHFFFAOYSA-N diethyl(4-ethylhex-3-en-3-yl)phosphane Chemical compound CCP(CC)C(CC)=C(CC)CC KYVURFFDPKTBQE-UHFFFAOYSA-N 0.000 description 1
- JMZPUAASPBRTJC-UHFFFAOYSA-N dimethyl(2-phenylethenyl)phosphane Chemical compound CP(C)C=Cc1ccccc1 JMZPUAASPBRTJC-UHFFFAOYSA-N 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- UMFWLUTUYFDZNQ-UHFFFAOYSA-N diphenyl(2-phenylethenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C=CC1=CC=CC=C1 UMFWLUTUYFDZNQ-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- LVSYKAWWNAMUPC-UHFFFAOYSA-N ditert-butyl(2,2-diphenylethenyl)phosphane Chemical compound C=1C=CC=CC=1C(=CP(C(C)(C)C)C(C)(C)C)C1=CC=CC=C1 LVSYKAWWNAMUPC-UHFFFAOYSA-N 0.000 description 1
- YRXHSSUFVMJWFY-UHFFFAOYSA-N ditert-butyl(2-cyclohexylethenyl)phosphane Chemical compound CC(C)(C)P(C=CC1CCCCC1)C(C)(C)C YRXHSSUFVMJWFY-UHFFFAOYSA-N 0.000 description 1
- HXTHYSXKYKIMNI-UHFFFAOYSA-N ditert-butyl(2-phenylethenyl)phosphane Chemical compound CC(C)(C)P(C=Cc1ccccc1)C(C)(C)C HXTHYSXKYKIMNI-UHFFFAOYSA-N 0.000 description 1
- IGDAICIZVHWKBP-UHFFFAOYSA-N ditert-butyl(4-ethylhex-3-en-3-yl)phosphane Chemical compound CCC(CC)=C(CC)P(C(C)(C)C)C(C)(C)C IGDAICIZVHWKBP-UHFFFAOYSA-N 0.000 description 1
- ULXITRWHFBXFKL-UHFFFAOYSA-N ditert-butyl(ethenyl)phosphane Chemical compound CC(C)(C)P(C=C)C(C)(C)C ULXITRWHFBXFKL-UHFFFAOYSA-N 0.000 description 1
- TVTYKQBUFYESMR-UHFFFAOYSA-N ditert-butyl(hex-3-en-3-yl)phosphane Chemical compound CCC=C(CC)P(C(C)(C)C)C(C)(C)C TVTYKQBUFYESMR-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920005558 epichlorohydrin rubber Polymers 0.000 description 1
- VCKGZOHSRDVCPM-UHFFFAOYSA-N ethenyl(diethyl)phosphane Chemical compound CCP(CC)C=C VCKGZOHSRDVCPM-UHFFFAOYSA-N 0.000 description 1
- LFXOQXVSUFFSHI-UHFFFAOYSA-N ethenyl-bis(1h-pyrrol-2-yl)phosphane Chemical compound C=1C=CNC=1P(C=C)C1=CC=CN1 LFXOQXVSUFFSHI-UHFFFAOYSA-N 0.000 description 1
- SNPFBWKLXBNGNJ-UHFFFAOYSA-N ethenyl-di(piperidin-1-yl)phosphane Chemical compound C1CCCCN1P(C=C)N1CCCCC1 SNPFBWKLXBNGNJ-UHFFFAOYSA-N 0.000 description 1
- SCESWTHQFQXGMV-UHFFFAOYSA-N ethenylphosphane Chemical compound PC=C SCESWTHQFQXGMV-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 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
- NJVOZLGKTAPUTQ-UHFFFAOYSA-M fentin chloride Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 NJVOZLGKTAPUTQ-UHFFFAOYSA-M 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 210000000527 greater trochanter Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- CXPUDADFKNRCJA-UHFFFAOYSA-N hex-3-en-3-yl(dimethyl)phosphane Chemical compound CCC=C(CC)P(C)C CXPUDADFKNRCJA-UHFFFAOYSA-N 0.000 description 1
- HTDJPCNNEPUOOQ-UHFFFAOYSA-N hexamethylcyclotrisiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O1 HTDJPCNNEPUOOQ-UHFFFAOYSA-N 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- ZGEZPSPEVXDOMG-UHFFFAOYSA-N lithium;phosphane Chemical compound [Li].P ZGEZPSPEVXDOMG-UHFFFAOYSA-N 0.000 description 1
- VCPPTNDHEILJHD-UHFFFAOYSA-N lithium;prop-1-ene Chemical class [Li+].[CH2-]C=C VCPPTNDHEILJHD-UHFFFAOYSA-N 0.000 description 1
- SZAVVKVUMPLRRS-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].C[CH-]C SZAVVKVUMPLRRS-UHFFFAOYSA-N 0.000 description 1
- XBEREOHJDYAKDA-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].CC[CH2-] XBEREOHJDYAKDA-UHFFFAOYSA-N 0.000 description 1
- CKVWBMJEETWJTF-UHFFFAOYSA-N lithium;tributyltin Chemical compound CCCC[Sn]([Li])(CCCC)CCCC CKVWBMJEETWJTF-UHFFFAOYSA-N 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- LWLPYZUDBNFNAH-UHFFFAOYSA-M magnesium;butane;bromide Chemical compound [Mg+2].[Br-].CCC[CH2-] LWLPYZUDBNFNAH-UHFFFAOYSA-M 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- UBOGEXSQACVGEC-UHFFFAOYSA-K phenyltin(3+);trichloride Chemical compound Cl[Sn](Cl)(Cl)C1=CC=CC=C1 UBOGEXSQACVGEC-UHFFFAOYSA-K 0.000 description 1
- 239000005054 phenyltrichlorosilane Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 229920003225 polyurethane elastomer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000012673 precipitation polymerization Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- AIFMYMZGQVTROK-UHFFFAOYSA-N silicon tetrabromide Chemical compound Br[Si](Br)(Br)Br AIFMYMZGQVTROK-UHFFFAOYSA-N 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000005486 sulfidation Methods 0.000 description 1
- IDXWRXSYFYGUMJ-UHFFFAOYSA-N sulfocarbamoylsulfamic acid Chemical compound OS(=O)(=O)NC(=O)NS(O)(=O)=O IDXWRXSYFYGUMJ-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920006250 telechelic polymer Polymers 0.000 description 1
- VJHDVMPJLLGYBL-UHFFFAOYSA-N tetrabromogermane Chemical compound Br[Ge](Br)(Br)Br VJHDVMPJLLGYBL-UHFFFAOYSA-N 0.000 description 1
- IEXRMSFAVATTJX-UHFFFAOYSA-N tetrachlorogermane Chemical compound Cl[Ge](Cl)(Cl)Cl IEXRMSFAVATTJX-UHFFFAOYSA-N 0.000 description 1
- FPADWGFFPCNGDD-UHFFFAOYSA-N tetraethoxystannane Chemical compound [Sn+4].CC[O-].CC[O-].CC[O-].CC[O-] FPADWGFFPCNGDD-UHFFFAOYSA-N 0.000 description 1
- LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 description 1
- JSQJUDVTRRCSRU-UHFFFAOYSA-N tributyl(chloro)silane Chemical compound CCCC[Si](Cl)(CCCC)CCCC JSQJUDVTRRCSRU-UHFFFAOYSA-N 0.000 description 1
- RCHUVCPBWWSUMC-UHFFFAOYSA-N trichloro(octyl)silane Chemical compound CCCCCCCC[Si](Cl)(Cl)Cl RCHUVCPBWWSUMC-UHFFFAOYSA-N 0.000 description 1
- INTLMJZQCBRQAT-UHFFFAOYSA-K trichloro(octyl)stannane Chemical compound CCCCCCCC[Sn](Cl)(Cl)Cl INTLMJZQCBRQAT-UHFFFAOYSA-K 0.000 description 1
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 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
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F236/06—Butadiene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F236/14—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated containing elements other than carbon and hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F30/00—Homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F30/02—Homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
-
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/46—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides selected from alkali metals
- C08F4/48—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides selected from alkali metals selected from lithium, rubidium, caesium or francium
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/04—Carbon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261640915P | 2012-05-01 | 2012-05-01 | |
| US61/640,915 | 2012-05-01 | ||
| US201361779399P | 2013-03-13 | 2013-03-13 | |
| US61/779,399 | 2013-03-13 | ||
| CN201380030181.6A CN104364275A (zh) | 2012-05-01 | 2013-05-01 | 具有有机膦官能的聚二烯和二烯共聚物 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201380030181.6A Division CN104364275A (zh) | 2012-05-01 | 2013-05-01 | 具有有机膦官能的聚二烯和二烯共聚物 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109553720A true CN109553720A (zh) | 2019-04-02 |
Family
ID=48464091
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201380030181.6A Pending CN104364275A (zh) | 2012-05-01 | 2013-05-01 | 具有有机膦官能的聚二烯和二烯共聚物 |
| CN201811179193.6A Pending CN109553720A (zh) | 2012-05-01 | 2013-05-01 | 具有有机膦官能的聚二烯和二烯共聚物 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201380030181.6A Pending CN104364275A (zh) | 2012-05-01 | 2013-05-01 | 具有有机膦官能的聚二烯和二烯共聚物 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9868805B2 (enExample) |
| EP (1) | EP2844678B1 (enExample) |
| JP (2) | JP6334514B2 (enExample) |
| KR (1) | KR102051399B1 (enExample) |
| CN (2) | CN104364275A (enExample) |
| BR (1) | BR112014027422B1 (enExample) |
| SG (1) | SG11201407010RA (enExample) |
| WO (1) | WO2013166124A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102051399B1 (ko) * | 2012-05-01 | 2019-12-03 | 가부시키가이샤 브리지스톤 | 유기포스핀 관능기를 갖는 폴리디엔 및 디엔 공중합체 |
| FR3045610B1 (fr) * | 2015-12-21 | 2018-01-05 | Michelin & Cie | Procede de synthese d'un polymere porteur d'au moins un groupe phosphonate, polymere issu de ce procede et composition le contenant |
| EP3366709A1 (en) | 2017-02-24 | 2018-08-29 | ARLANXEO Deutschland GmbH | In-chain phosphine- and phosphonium- containing diene-polymers |
| KR102748379B1 (ko) * | 2019-10-07 | 2024-12-27 | 주식회사 엘지화학 | 블록 공중합체 조성물 |
Citations (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3048638A (en) * | 1958-09-04 | 1962-08-07 | Union Carbide Corp | Vinyl phosphines |
| US3312674A (en) * | 1964-09-10 | 1967-04-04 | Union Carbide Corp | Copolymers of a monovinyl phosphine oxide and a polyvinyl phosphine oxide |
| US3350477A (en) * | 1960-07-07 | 1967-10-31 | Stauffer Chemical Co | Copolymers of vinyl diphenylphosphine oxide |
| US3422079A (en) * | 1963-10-30 | 1969-01-14 | Union Carbide Corp | Coordination complexes of vinylphosphine oxides and metal salts,and polymers thereof |
| US3437719A (en) * | 1963-12-27 | 1969-04-08 | Union Carbide Corp | Dyeable polypropylene compositions |
| US3519607A (en) * | 1962-06-29 | 1970-07-07 | Union Carbide Corp | Polymerization of vinyl phosphoryl compounds |
| US3624057A (en) * | 1969-01-30 | 1971-11-30 | Phillips Petroleum Co | Polymerization with multifunctional iniators prepared from vinylsilanes or vinylphosphines and organomonolithium compounds |
| US3718637A (en) * | 1971-03-25 | 1973-02-27 | A Halasa | Process for the polymerization of conjugated dienes |
| JPH10218908A (ja) * | 1997-01-30 | 1998-08-18 | Enichem Spa | テトラヒドロピラニルメタノールのアルキルエーテルの存在下での共役ジエンとビニルアレーンのアニオン共重合 |
| JP2007091824A (ja) * | 2005-09-27 | 2007-04-12 | National Institute Of Advanced Industrial & Technology | 高分子量ポリジフェニルビニルホスフィンオキシド、その製造方法及び金属抽出剤 |
| US20070167587A1 (en) * | 2004-03-01 | 2007-07-19 | Kuraray Co., Ltd. | Process for producing polymer with functional end |
| JP2008115278A (ja) * | 2006-11-06 | 2008-05-22 | National Institute Of Advanced Industrial & Technology | 光学活性リン含有高分子化合物とその製造方法 |
| JP2009221203A (ja) * | 2008-03-17 | 2009-10-01 | Goodyear Tire & Rubber Co:The | ホウ素含有官能化剤 |
Family Cites Families (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3135716A (en) | 1958-11-06 | 1964-06-02 | Phillips Petroleum Co | Process for preparing terminally reactive polymers |
| US3109871A (en) | 1960-12-27 | 1963-11-05 | Phillips Petroleum Co | Production and curing of polyfunctional terminally reactive polymers |
| DE1300240B (de) | 1964-01-22 | 1969-07-31 | Bayer Ag | Verfahren zur Herstellung von Polymerisaten konjugierter Diolefine |
| US3784637A (en) * | 1969-01-30 | 1974-01-08 | Phillips Petroleum Co | Multifunctional polymerization initiators from vinylsilanes or vinylphosphines and organomonolithium compounds |
| US3652516A (en) | 1969-02-10 | 1972-03-28 | Phillips Petroleum Co | Polymerization of conjugated dienes or monovinyl aromatic monomers with multifunctional initiators from diisopropenylbenzene |
| US3987009A (en) | 1972-06-15 | 1976-10-19 | Union Carbide Corporation | Transition metal catalyst compositions |
| JPS5893709A (ja) | 1981-11-30 | 1983-06-03 | Japan Synthetic Rubber Co Ltd | ウェットスキッド特性及び摩耗特性が改良されたゴム組成物 |
| US4526934A (en) | 1982-03-19 | 1985-07-02 | Bridgestone Tire Company Limited | Branched styrene-butadiene copolymers and pneumatic tires using the same |
| JPS5978214A (ja) | 1982-10-27 | 1984-05-07 | Japan Synthetic Rubber Co Ltd | ブタジエン系ゴム材料 |
| US4429091A (en) | 1983-03-09 | 1984-01-31 | The Firestone Tire & Rubber Company | Oligomeric oxolanyl alkanes as modifiers for polymerization of dienes using lithium-based initiators |
| US4616069A (en) | 1984-10-26 | 1986-10-07 | Nippon Zeon Co., Ltd. | Process for making diene polymer rubbers |
| EP0473206B1 (en) | 1985-10-11 | 1999-06-23 | Asahi Kasei Kogyo Kabushiki Kaisha | Compositions containing a terminal-modified block copolymer |
| JPS6296545A (ja) | 1985-10-23 | 1987-05-06 | Yokohama Rubber Co Ltd:The | タイヤトレツド用ゴム組成物 |
| JP2594809B2 (ja) | 1988-04-02 | 1997-03-26 | 日本ゼオン株式会社 | タイヤトレッド用ゴム組成物 |
| JP2811484B2 (ja) | 1989-12-20 | 1998-10-15 | 日本ゼオン株式会社 | ゴム組成物 |
| US5109907A (en) | 1990-04-09 | 1992-05-05 | Bridgestone/Firestone, Inc. | Diene polymers and copolymers terminated by reaction with N-alkyl and N-aryl imines |
| US5268439A (en) | 1991-01-02 | 1993-12-07 | Bridgestone/Firestone, Inc. | Tin containing elastomers and products having reduced hysteresis properties |
| US5227431A (en) | 1991-04-12 | 1993-07-13 | Bridgestone/Firestone, Inc. | Diene polymers and copolymers jumped by partial crosslinking and terminated with a substituted imine |
| US5717042A (en) * | 1991-05-06 | 1998-02-10 | Bridgestone/Firestone, Inc. | Process for preparing diene oligomers and copolymeric oligomers |
| US5260123A (en) | 1991-06-28 | 1993-11-09 | Bridgestone Corporation | Block copolymers of polysiloxanes and copolymers of conjugated dienes and aromatic vinyl compounds, and multilayer structures containing same |
| US5210145A (en) | 1991-12-20 | 1993-05-11 | Bridgestone/Firestone, Inc. | Diene polymers and copolymers terminated by reaction with fused-ring polynuclear aromatic compounds |
| US5248722A (en) | 1992-06-02 | 1993-09-28 | Bridgestone Corporation | Tire tread composition |
| US5332810A (en) | 1992-10-02 | 1994-07-26 | Bridgestone Corporation | Solubilized anionic polymerization initiator and preparation thereof |
| US5329005A (en) | 1992-10-02 | 1994-07-12 | Bridgestone Corporation | Soluble anionic polymerization initiators and preparation thereof |
| US5552473A (en) | 1992-10-02 | 1996-09-03 | Bridgestone Corporation | Functionalized polymer and rubber compositions produced from solubilized anionic polymerization initiators |
| US5393721A (en) | 1992-10-16 | 1995-02-28 | Bridgestone Corporation | Anionic polymerization initiators and reduced hysteresis products therefom |
| EP0600208B1 (en) | 1992-10-30 | 1997-12-29 | Bridgestone Corporation | Soluble anionic polymerization initiators and products therefrom |
| DE69411984T2 (de) | 1993-04-30 | 1998-12-10 | Bridgestone Corp., Tokio/Tokyo | Anionische Polymerisationsinitiatoren und Produkte mit niedriger Hysteresis |
| US5349024A (en) | 1993-11-03 | 1994-09-20 | Bridgestone/Firestone, Inc. | Elastomers having reduced hysteresis prepared with vinyl polycyclic aromatic hydrocarbon |
| US5491230A (en) | 1993-12-29 | 1996-02-13 | Bridgestone Corporation | Anionic polymerization initiators containing adducts of cyclic secondary amines and conjugated dienes, and products therefrom |
| US5502129A (en) | 1994-05-13 | 1996-03-26 | Bridgestone Corporation | Triorganotin lithium, process to prepare same and anionic polymerization initiated therewith |
| EP0794224B1 (en) | 1994-11-24 | 2000-01-26 | Nippon Zeon Co., Ltd. | Diene rubber, process for producing the same, and rubber composition |
| US5521309A (en) | 1994-12-23 | 1996-05-28 | Bridgestone Corporation | Tertiary-amino allyl-or xylyl-lithium initiators and method of preparing same |
| US5574109A (en) | 1995-02-01 | 1996-11-12 | Bridgestone Corporation | Aminoalkyllithium compounds containing cyclic amines and polymers therefrom |
| US5496940A (en) | 1995-02-01 | 1996-03-05 | Bridgestone Corporation | Alkyllithium compounds containing cyclic amines and their use in polymerization |
| US5736617A (en) | 1996-12-31 | 1998-04-07 | Bridgestone Corporation | Polymers, elastomeric compounds, and products thereof, terminated with novel amine compounds containing side-chain organohalide reactive moieties |
| US5786441A (en) | 1996-12-31 | 1998-07-28 | Bridgestone Corporation | Polymers, elastomeric compounds and products thereof, derived from novel amine compounds containing side-chain organolithium moieties |
| US5877336A (en) | 1996-12-31 | 1999-03-02 | Bridgestone Corporation | Synthesis of tributyltin lithium |
| US5935893A (en) | 1997-08-01 | 1999-08-10 | Bridgestone Corporation | Aliphatic solutions of aminoalkyllithium compounds |
| US6207855B1 (en) | 1998-06-23 | 2001-03-27 | Duke University Medical Center | Stable no-delivering compounds |
| US6596798B1 (en) | 2001-11-05 | 2003-07-22 | Bridgestone Corporation | Preparation of low hysteresis rubber by reacting a lithium polymer with oxazoline compounds |
| WO2004020475A1 (en) | 2002-08-30 | 2004-03-11 | Bridgestone Corporation | Functionalized polymers and improved vulcanizates therefrom |
| US7153919B2 (en) | 2002-10-30 | 2006-12-26 | Bridgestone Corporation | Use of sulfur containing initiators for anionic polymerization of monomers |
| US7598322B1 (en) | 2004-07-26 | 2009-10-06 | Bridgestone Corporation | Functionalized polymers and improved tires therefrom |
| US20060178467A1 (en) | 2005-01-14 | 2006-08-10 | Yasuo Fukushima | Tire treads with reduced hysteresis loss |
| US7335712B2 (en) | 2005-04-21 | 2008-02-26 | Bridgestone Corporation | Process of producing a siloxy-functionalized polymer |
| US7868110B2 (en) | 2005-05-20 | 2011-01-11 | Bridgestone Corporation | Anionic polymerization initiators and polymers therefrom |
| US20060264590A1 (en) | 2005-05-20 | 2006-11-23 | Bridgestone Corporation | Anionic polymerization initiators and polymers therefrom |
| ES2551103T3 (es) | 2007-12-28 | 2015-11-16 | Bridgestone Corporation | Polímeros funcionalizados de hidroxiarilo |
| JP5709094B2 (ja) * | 2009-02-28 | 2015-04-30 | 独立行政法人産業技術総合研究所 | アルケニルリン化合物、アルケニルリン化合物重合体、及びアルケニルリン化合物共重合体 |
| KR102051399B1 (ko) * | 2012-05-01 | 2019-12-03 | 가부시키가이샤 브리지스톤 | 유기포스핀 관능기를 갖는 폴리디엔 및 디엔 공중합체 |
-
2013
- 2013-05-01 KR KR1020147033730A patent/KR102051399B1/ko not_active Expired - Fee Related
- 2013-05-01 CN CN201380030181.6A patent/CN104364275A/zh active Pending
- 2013-05-01 JP JP2015510420A patent/JP6334514B2/ja not_active Expired - Fee Related
- 2013-05-01 CN CN201811179193.6A patent/CN109553720A/zh active Pending
- 2013-05-01 US US14/398,644 patent/US9868805B2/en not_active Expired - Fee Related
- 2013-05-01 WO PCT/US2013/039031 patent/WO2013166124A1/en not_active Ceased
- 2013-05-01 SG SG11201407010RA patent/SG11201407010RA/en unknown
- 2013-05-01 EP EP13723607.1A patent/EP2844678B1/en not_active Not-in-force
- 2013-05-01 BR BR112014027422-3A patent/BR112014027422B1/pt not_active IP Right Cessation
-
2017
- 2017-09-27 JP JP2017187079A patent/JP6604685B2/ja not_active Expired - Fee Related
Patent Citations (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3048638A (en) * | 1958-09-04 | 1962-08-07 | Union Carbide Corp | Vinyl phosphines |
| US3350477A (en) * | 1960-07-07 | 1967-10-31 | Stauffer Chemical Co | Copolymers of vinyl diphenylphosphine oxide |
| US3519607A (en) * | 1962-06-29 | 1970-07-07 | Union Carbide Corp | Polymerization of vinyl phosphoryl compounds |
| US3422079A (en) * | 1963-10-30 | 1969-01-14 | Union Carbide Corp | Coordination complexes of vinylphosphine oxides and metal salts,and polymers thereof |
| US3437719A (en) * | 1963-12-27 | 1969-04-08 | Union Carbide Corp | Dyeable polypropylene compositions |
| US3312674A (en) * | 1964-09-10 | 1967-04-04 | Union Carbide Corp | Copolymers of a monovinyl phosphine oxide and a polyvinyl phosphine oxide |
| US3624057A (en) * | 1969-01-30 | 1971-11-30 | Phillips Petroleum Co | Polymerization with multifunctional iniators prepared from vinylsilanes or vinylphosphines and organomonolithium compounds |
| US3718637A (en) * | 1971-03-25 | 1973-02-27 | A Halasa | Process for the polymerization of conjugated dienes |
| JPH10218908A (ja) * | 1997-01-30 | 1998-08-18 | Enichem Spa | テトラヒドロピラニルメタノールのアルキルエーテルの存在下での共役ジエンとビニルアレーンのアニオン共重合 |
| US20070167587A1 (en) * | 2004-03-01 | 2007-07-19 | Kuraray Co., Ltd. | Process for producing polymer with functional end |
| JP2007091824A (ja) * | 2005-09-27 | 2007-04-12 | National Institute Of Advanced Industrial & Technology | 高分子量ポリジフェニルビニルホスフィンオキシド、その製造方法及び金属抽出剤 |
| JP2008115278A (ja) * | 2006-11-06 | 2008-05-22 | National Institute Of Advanced Industrial & Technology | 光学活性リン含有高分子化合物とその製造方法 |
| JP2009221203A (ja) * | 2008-03-17 | 2009-10-01 | Goodyear Tire & Rubber Co:The | ホウ素含有官能化剤 |
Non-Patent Citations (2)
| Title |
|---|
| DAVID M. PAISLEY,等: "Some polymers and copolymers of vinyldiphenylphosphine", 《JOURNAL OF POLYMER SCIENCE》 * |
| PETERSON, DONALD J.: "3d-Orbital Resonance in Trivalent Organophosphines. II. Additions of Organolithium Compounds to Vinylphosphines1", 《THE JOURNAL OF ORGANIC CHEMISTRY》 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP6604685B2 (ja) | 2019-11-13 |
| JP6334514B2 (ja) | 2018-05-30 |
| JP2017222883A (ja) | 2017-12-21 |
| SG11201407010RA (en) | 2014-11-27 |
| KR102051399B1 (ko) | 2019-12-03 |
| WO2013166124A1 (en) | 2013-11-07 |
| EP2844678B1 (en) | 2017-02-22 |
| CN104364275A (zh) | 2015-02-18 |
| US20150126675A1 (en) | 2015-05-07 |
| BR112014027422A2 (pt) | 2017-06-27 |
| EP2844678A1 (en) | 2015-03-11 |
| KR20150013219A (ko) | 2015-02-04 |
| JP2015516014A (ja) | 2015-06-04 |
| US9868805B2 (en) | 2018-01-16 |
| BR112014027422B1 (pt) | 2020-12-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101527789B1 (ko) | 아민-함유 알콕시실릴-관능화 중합체 | |
| JP6725921B2 (ja) | [ビス(トリヒドロカルビルシリル)アミノシリル]官能化スチレンをベースとするエラストマーコポリマーおよびゴムの製造におけるそれらの使用 | |
| US8962745B2 (en) | Functionalized polymers and vulcanizates with reduced hysteretic loss | |
| TWI585115B (zh) | 經穩定之多價陰離子聚合反應引發劑及其製備方法 | |
| JP2014507405A (ja) | アミノシラン開始剤及びそれを用いた官能化ポリマー | |
| CN107743498A (zh) | 用于二烯单体与乙烯基芳香族单体的共聚合的引发剂 | |
| CN109071708A (zh) | 改性聚合物的制造方法、改性聚合物、橡胶组合物和轮胎 | |
| US20190062483A1 (en) | Elastomeric copolymers based on [bis(trihydrocarbylsilyl)aminosilyl]-functionalized styrene and their use in the preparation of rubbers | |
| JP6604685B2 (ja) | オルガノホスフィン官能基を有するポリジエンおよびジエンコポリマー | |
| JP2025098254A (ja) | 共役ジエン系重合体の製造方法、ならびに、重合体、ゴム、およびそれから製造されるタイヤ | |
| US9127109B2 (en) | Preparation of functional polymers phosphorus-containing organometal initiators | |
| US9163104B2 (en) | Preparation of functional polymers using phosphide initiators | |
| US9499651B2 (en) | Copolymers of conjugated dienes and vinyl organophosphines prepared by anionic polymerization | |
| US10519266B2 (en) | Polydienes and diene copolymers using 1,1-bis(hydrocarbylthio)hydrocarbyl-1-ene compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |