CN106604935A - 末端改性共轭二烯聚合物的制造方法、末端改性共轭二烯聚合物、橡胶组合物、以及轮胎 - Google Patents
末端改性共轭二烯聚合物的制造方法、末端改性共轭二烯聚合物、橡胶组合物、以及轮胎 Download PDFInfo
- Publication number
- CN106604935A CN106604935A CN201580044777.0A CN201580044777A CN106604935A CN 106604935 A CN106604935 A CN 106604935A CN 201580044777 A CN201580044777 A CN 201580044777A CN 106604935 A CN106604935 A CN 106604935A
- Authority
- CN
- China
- Prior art keywords
- compound
- stannum
- atom
- terminal
- modified
- 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.)
- Granted
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 82
- 150000001993 dienes Chemical class 0.000 title claims abstract description 70
- 239000000203 mixture Substances 0.000 title claims abstract description 69
- 229920001971 elastomer Polymers 0.000 title claims abstract description 66
- 239000005060 rubber Substances 0.000 title claims abstract description 66
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 41
- 238000000034 method Methods 0.000 title claims abstract description 33
- -1 diene compound Chemical class 0.000 claims abstract description 199
- 150000001875 compounds Chemical class 0.000 claims abstract description 130
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 36
- 239000002685 polymerization catalyst Substances 0.000 claims abstract description 27
- 229910052761 rare earth metal Inorganic materials 0.000 claims abstract description 27
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 20
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical group C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims abstract description 13
- 230000004048 modification Effects 0.000 claims abstract description 7
- 238000012986 modification Methods 0.000 claims abstract description 7
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims abstract description 6
- 125000003454 indenyl group Chemical class C1(C=CC2=CC=CC=C12)* 0.000 claims abstract description 6
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims abstract description 5
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 185
- 229910052782 aluminium Inorganic materials 0.000 claims description 23
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
- 229910052751 metal Inorganic materials 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 230000000737 periodic effect Effects 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
- 125000000524 functional group Chemical group 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 229910052727 yttrium Inorganic materials 0.000 claims description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
- 150000002366 halogen compounds Chemical class 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 229910052718 tin Inorganic materials 0.000 claims description 10
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 9
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 9
- 229910052710 silicon Inorganic materials 0.000 claims description 9
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 229910052732 germanium Inorganic materials 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- 230000008859 change Effects 0.000 claims description 7
- 238000005580 one pot reaction Methods 0.000 claims description 7
- 239000004593 Epoxy Substances 0.000 claims description 6
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 5
- 239000004411 aluminium Substances 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 229910000765 intermetallic Inorganic materials 0.000 claims description 5
- 125000004437 phosphorous atom Chemical group 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 4
- 229910052747 lanthanoid Chemical group 0.000 claims description 4
- 150000002602 lanthanoids Chemical group 0.000 claims description 4
- 150000002902 organometallic compounds Chemical class 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 229910052706 scandium Inorganic materials 0.000 claims description 3
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical group [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 claims description 3
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 3
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical group [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 claims description 3
- KCADUUDDTBWILK-UHFFFAOYSA-N Cumulene Natural products CCCC=C=C=C1OC(=O)C=C1 KCADUUDDTBWILK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004069 aziridinyl group Chemical group 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 238000006884 silylation reaction Methods 0.000 claims 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 51
- 239000002585 base Substances 0.000 description 29
- 150000007513 acids Chemical class 0.000 description 27
- UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 18
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 13
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 12
- 239000003431 cross linking reagent Substances 0.000 description 12
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 150000008040 ionic compounds Chemical class 0.000 description 11
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 10
- 235000011090 malic acid Nutrition 0.000 description 10
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 10
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 9
- CQSWISNVQPOAEM-UHFFFAOYSA-N 6-oxo-6-phenylmethoxyhexanoic acid Chemical class OC(=O)CCCCC(=O)OCC1=CC=CC=C1 CQSWISNVQPOAEM-UHFFFAOYSA-N 0.000 description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 229910052736 halogen Inorganic materials 0.000 description 9
- 150000002367 halogens Chemical class 0.000 description 9
- 239000001630 malic acid Substances 0.000 description 9
- UOBSVARXACCLLH-UHFFFAOYSA-N monomethyl adipate Chemical class COC(=O)CCCCC(O)=O UOBSVARXACCLLH-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 238000005299 abrasion Methods 0.000 description 8
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 8
- 239000004305 biphenyl Substances 0.000 description 8
- 235000010290 biphenyl Nutrition 0.000 description 8
- 238000006555 catalytic reaction Methods 0.000 description 8
- WCRDXYSYPCEIAK-UHFFFAOYSA-N dibutylstannane Chemical compound CCCC[SnH2]CCCC WCRDXYSYPCEIAK-UHFFFAOYSA-N 0.000 description 8
- HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 description 8
- 239000000945 filler Substances 0.000 description 8
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical group C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 7
- SVSRQMUJHHQAAX-UHFFFAOYSA-N dibenzyltin Chemical compound C=1C=CC=CC=1C[Sn]CC1=CC=CC=C1 SVSRQMUJHHQAAX-UHFFFAOYSA-N 0.000 description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000005864 Sulphur Chemical group 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 125000003368 amide group Chemical group 0.000 description 6
- 125000006267 biphenyl group Chemical group 0.000 description 6
- 150000001768 cations Chemical class 0.000 description 6
- 238000005660 chlorination reaction Methods 0.000 description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 230000001976 improved effect Effects 0.000 description 6
- 150000002469 indenes Chemical class 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 6
- 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
- 239000002841 Lewis acid Substances 0.000 description 5
- 239000002879 Lewis base Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 125000001118 alkylidene group Chemical group 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 239000011256 inorganic filler Substances 0.000 description 5
- 229910003475 inorganic filler Inorganic materials 0.000 description 5
- 150000007517 lewis acids Chemical class 0.000 description 5
- 150000007527 lewis bases Chemical class 0.000 description 5
- 150000005309 metal halides Chemical class 0.000 description 5
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 5
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 4
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 4
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 229910052688 Gadolinium Inorganic materials 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000006229 carbon black Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- BRWZYZWZBMGMMG-UHFFFAOYSA-J dodecanoate tin(4+) Chemical compound [Sn+4].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O BRWZYZWZBMGMMG-UHFFFAOYSA-J 0.000 description 4
- 150000002118 epoxides Chemical class 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 4
- 229940049920 malate Drugs 0.000 description 4
- 239000011572 manganese Substances 0.000 description 4
- 229910001507 metal halide Inorganic materials 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 229920002857 polybutadiene Polymers 0.000 description 4
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 4
- 230000005070 ripening Effects 0.000 description 4
- YJGJRYWNNHUESM-UHFFFAOYSA-J triacetyloxystannyl acetate Chemical compound [Sn+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O YJGJRYWNNHUESM-UHFFFAOYSA-J 0.000 description 4
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- 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 3
- OAOABCKPVCUNKO-UHFFFAOYSA-N 8-methyl Nonanoic acid Chemical compound CC(C)CCCCCCC(O)=O OAOABCKPVCUNKO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 244000043261 Hevea brasiliensis Species 0.000 description 3
- 244000147568 Laurus nobilis Species 0.000 description 3
- 235000017858 Laurus nobilis Nutrition 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920000459 Nitrile rubber Polymers 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- 235000005212 Terminalia tomentosa Nutrition 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- REUQOSNMSWLNPD-UHFFFAOYSA-N [2-(diethylamino)phenyl]-phenylmethanone Chemical compound CCN(CC)C1=CC=CC=C1C(=O)C1=CC=CC=C1 REUQOSNMSWLNPD-UHFFFAOYSA-N 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 3
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid ester group Chemical class C(CCCCCCCCCCC)(=O)O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 150000003951 lactams Chemical class 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 229910001629 magnesium chloride Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229920003052 natural elastomer Polymers 0.000 description 3
- 229920001194 natural rubber Polymers 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 241000894007 species Species 0.000 description 3
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 3
- 238000004073 vulcanization Methods 0.000 description 3
- ZFKPJODVPGDYEZ-UHFFFAOYSA-N 1-(aziridin-1-yl)pentan-1-one Chemical compound CCCCC(=O)N1CC1 ZFKPJODVPGDYEZ-UHFFFAOYSA-N 0.000 description 2
- 239000005968 1-Decanol Substances 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- UHOPWFKONJYLCF-UHFFFAOYSA-N 2-(2-sulfanylethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCS)C(=O)C2=C1 UHOPWFKONJYLCF-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 description 2
- BGLQFLIZWKWFBT-UHFFFAOYSA-N 3-benzyl-1h-indene Chemical class C=1CC2=CC=CC=C2C=1CC1=CC=CC=C1 BGLQFLIZWKWFBT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Natural products CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000005046 Chlorosilane Substances 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 229910021380 Manganese Chloride Inorganic materials 0.000 description 2
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 229910000577 Silicon-germanium Inorganic materials 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 2
- 229910001626 barium chloride Inorganic materials 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- LWBPNIJBHRISSS-UHFFFAOYSA-L beryllium dichloride Chemical compound Cl[Be]Cl LWBPNIJBHRISSS-UHFFFAOYSA-L 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- KPWJBEFBFLRCLH-UHFFFAOYSA-L cadmium bromide Chemical compound Br[Cd]Br KPWJBEFBFLRCLH-UHFFFAOYSA-L 0.000 description 2
- OKIIEJOIXGHUKX-UHFFFAOYSA-L cadmium iodide Chemical compound [Cd+2].[I-].[I-] OKIIEJOIXGHUKX-UHFFFAOYSA-L 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 description 2
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000004386 diacrylate group Chemical group 0.000 description 2
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- JJSGABFIILQOEY-UHFFFAOYSA-M diethylalumanylium;bromide Chemical compound CC[Al](Br)CC JJSGABFIILQOEY-UHFFFAOYSA-M 0.000 description 2
- VIGLJKSIDLNMGH-UHFFFAOYSA-N dihexyl oxalate Chemical compound CCCCCCOC(=O)C(=O)OCCCCCC VIGLJKSIDLNMGH-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- KUCPUSUXIGWHFB-UHFFFAOYSA-N diphenyltin Chemical compound C=1C=CC=CC=1[Sn]C1=CC=CC=C1 KUCPUSUXIGWHFB-UHFFFAOYSA-N 0.000 description 2
- JFICPAADTOQAMU-UHFFFAOYSA-L ethylaluminum(2+);dibromide Chemical compound CC[Al](Br)Br JFICPAADTOQAMU-UHFFFAOYSA-L 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 229940116364 hard fat Drugs 0.000 description 2
- 238000010438 heat treatment Methods 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
- 230000002779 inactivation Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 239000011565 manganese chloride Substances 0.000 description 2
- 235000002867 manganese chloride Nutrition 0.000 description 2
- 229940099607 manganese chloride Drugs 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- YDSWCNNOKPMOTP-UHFFFAOYSA-N mellitic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C(C(O)=O)=C1C(O)=O YDSWCNNOKPMOTP-UHFFFAOYSA-N 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 2
- 229920001195 polyisoprene Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003223 protective agent Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000003252 repetitive effect Effects 0.000 description 2
- 229910052702 rhenium Inorganic materials 0.000 description 2
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 238000005987 sulfurization reaction Methods 0.000 description 2
- 150000003571 thiolactams Chemical class 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 2
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- LTOKKZDSYQQAHL-UHFFFAOYSA-N trimethoxy-[4-(oxiran-2-yl)butyl]silane Chemical class CO[Si](OC)(OC)CCCCC1CO1 LTOKKZDSYQQAHL-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- NRWZCOMOLSKCEM-UHFFFAOYSA-M triphenylstannyl dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 NRWZCOMOLSKCEM-UHFFFAOYSA-M 0.000 description 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 2
- OJJVPGJEBAZOIF-UHFFFAOYSA-N (2,3,4,5-tetrafluorophenoxy)boronic acid Chemical compound OB(O)OC1=CC(F)=C(F)C(F)=C1F OJJVPGJEBAZOIF-UHFFFAOYSA-N 0.000 description 1
- JWZGJDATMFMKIO-UHFFFAOYSA-N (2,3,4-trifluorophenoxy)boronic acid Chemical compound OB(O)OC1=CC=C(F)C(F)=C1F JWZGJDATMFMKIO-UHFFFAOYSA-N 0.000 description 1
- LCIOIBLOWNIOOF-UHFFFAOYSA-N (2,3-difluorophenoxy)boronic acid Chemical compound OB(O)OC1=CC=CC(F)=C1F LCIOIBLOWNIOOF-UHFFFAOYSA-N 0.000 description 1
- LKWLQPNRJQQVEB-UHFFFAOYSA-N (2,3-dimethylphenoxy)boronic acid Chemical compound CC1=CC=CC(OB(O)O)=C1C LKWLQPNRJQQVEB-UHFFFAOYSA-N 0.000 description 1
- HTGQCLJTWPSFNL-UHFFFAOYSA-N (2-methylphenoxy)boronic acid Chemical compound CC1=CC=CC=C1OB(O)O HTGQCLJTWPSFNL-UHFFFAOYSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 description 1
- KTTUOEDORYKFIS-UHFFFAOYSA-N 1,6-bis(isocyanatosulfanyl)hexane Chemical class O=C=NSCCCCCCSN=C=O KTTUOEDORYKFIS-UHFFFAOYSA-N 0.000 description 1
- ZCYVBYQBOWLNBU-UHFFFAOYSA-N 1-(aziridin-1-yl)-2-methylpropan-1-one Chemical compound CC(C)C(=O)N1CC1 ZCYVBYQBOWLNBU-UHFFFAOYSA-N 0.000 description 1
- BBORIVJAFPWPPH-UHFFFAOYSA-N 1-(aziridin-1-yl)-3-methylbutan-1-one Chemical compound CC(C)CC(=O)N1CC1 BBORIVJAFPWPPH-UHFFFAOYSA-N 0.000 description 1
- DMYOHQBLOZMDLP-UHFFFAOYSA-N 1-[2-(2-hydroxy-3-piperidin-1-ylpropoxy)phenyl]-3-phenylpropan-1-one Chemical compound C1CCCCN1CC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 DMYOHQBLOZMDLP-UHFFFAOYSA-N 0.000 description 1
- UJPKMTDFFUTLGM-UHFFFAOYSA-N 1-aminoethanol Chemical class CC(N)O UJPKMTDFFUTLGM-UHFFFAOYSA-N 0.000 description 1
- NBHBNYRLTADHQY-UHFFFAOYSA-N 1-benzyl-1h-indene Chemical class C1=CC2=CC=CC=C2C1CC1=CC=CC=C1 NBHBNYRLTADHQY-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- VUQPJRPDRDVQMN-UHFFFAOYSA-N 1-chlorooctadecane Chemical compound CCCCCCCCCCCCCCCCCCCl VUQPJRPDRDVQMN-UHFFFAOYSA-N 0.000 description 1
- IEKPDJDYFASRFB-UHFFFAOYSA-N 1-ethyl-1h-indene Chemical class C1=CC=C2C(CC)C=CC2=C1 IEKPDJDYFASRFB-UHFFFAOYSA-N 0.000 description 1
- LUXJFGUJEPHZGY-UHFFFAOYSA-N 1-ethyl-3-methylimidazol-2-one Chemical class CCN1C=CN(C)C1=O LUXJFGUJEPHZGY-UHFFFAOYSA-N 0.000 description 1
- LRTOHSLOFCWHRF-UHFFFAOYSA-N 1-methyl-1h-indene Chemical class C1=CC=C2C(C)C=CC2=C1 LRTOHSLOFCWHRF-UHFFFAOYSA-N 0.000 description 1
- GGYVTHJIUNGKFZ-UHFFFAOYSA-N 1-methylpiperidin-2-one Chemical class CN1CCCCC1=O GGYVTHJIUNGKFZ-UHFFFAOYSA-N 0.000 description 1
- OPISVEPYALEQJT-UHFFFAOYSA-N 1-phenylazetidin-2-one Chemical compound O=C1CCN1C1=CC=CC=C1 OPISVEPYALEQJT-UHFFFAOYSA-N 0.000 description 1
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 description 1
- NKOGCJIYHZVBDR-UHFFFAOYSA-N 1-phenylpiperidin-2-one Chemical class O=C1CCCCN1C1=CC=CC=C1 NKOGCJIYHZVBDR-UHFFFAOYSA-N 0.000 description 1
- HFZLSTDPRQSZCQ-UHFFFAOYSA-N 1-pyrrolidin-3-ylpyrrolidine Chemical compound C1CCCN1C1CNCC1 HFZLSTDPRQSZCQ-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
- XLXUXTOEGRCZQL-UHFFFAOYSA-N 2,2-bis(2-methylpropyl)hexanedioic acid Chemical compound CC(C)CC(C(O)=O)(CC(C)C)CCCC(O)=O XLXUXTOEGRCZQL-UHFFFAOYSA-N 0.000 description 1
- ZLOUTYIQKOUALY-UHFFFAOYSA-N 2,2-di(propan-2-yl)hexanedioic acid Chemical compound CC(C)C(C(O)=O)(C(C)C)CCCC(O)=O ZLOUTYIQKOUALY-UHFFFAOYSA-N 0.000 description 1
- HRLAUGYEZAMPJU-UHFFFAOYSA-N 2,2-dibenzylhexanedioic acid Chemical compound C=1C=CC=CC=1CC(C(O)=O)(CCCC(=O)O)CC1=CC=CC=C1 HRLAUGYEZAMPJU-UHFFFAOYSA-N 0.000 description 1
- HJXYDPWBEAEQIO-UHFFFAOYSA-N 2,2-dibutylhexanedioic acid Chemical compound CCCCC(CCCC)(C(O)=O)CCCC(O)=O HJXYDPWBEAEQIO-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- FVTNYMPAIVXHHL-UHFFFAOYSA-N 2,2-dioctadecylhexanedioic acid Chemical compound CCCCCCCCCCCCCCCCCCC(C(O)=O)(CCCC(O)=O)CCCCCCCCCCCCCCCCCC FVTNYMPAIVXHHL-UHFFFAOYSA-N 0.000 description 1
- FNSVFYNYEORBIV-UHFFFAOYSA-N 2,2-dioctylhexanedioic acid Chemical compound CCCCCCCCC(C(O)=O)(CCCC(O)=O)CCCCCCCC FNSVFYNYEORBIV-UHFFFAOYSA-N 0.000 description 1
- XOJVKTOUJNDTTO-UHFFFAOYSA-N 2,2-ditert-butylhexanedioic acid Chemical compound CC(C)(C)C(C(C)(C)C)(C(O)=O)CCCC(O)=O XOJVKTOUJNDTTO-UHFFFAOYSA-N 0.000 description 1
- ARTPQCYGVCZFTG-UHFFFAOYSA-N 2,3,3-triphenylprop-2-enoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)=C(C=1C=CC=CC=1)C1=CC=CC=C1 ARTPQCYGVCZFTG-UHFFFAOYSA-N 0.000 description 1
- GVBHCMNXRKOJRH-UHFFFAOYSA-N 2,4,5,6-tetrachloropyrimidine Chemical class ClC1=NC(Cl)=C(Cl)C(Cl)=N1 GVBHCMNXRKOJRH-UHFFFAOYSA-N 0.000 description 1
- JCGGPCDDFXIVQB-UHFFFAOYSA-N 2,4,5-tribromo-1h-imidazole Chemical class BrC1=NC(Br)=C(Br)N1 JCGGPCDDFXIVQB-UHFFFAOYSA-N 0.000 description 1
- DPVIABCMTHHTGB-UHFFFAOYSA-N 2,4,6-trichloropyrimidine Chemical class ClC1=CC(Cl)=NC(Cl)=N1 DPVIABCMTHHTGB-UHFFFAOYSA-N 0.000 description 1
- BTLKROSJMNFSQZ-UHFFFAOYSA-N 2,4-dichloro-6-methylpyrimidine Chemical class CC1=CC(Cl)=NC(Cl)=N1 BTLKROSJMNFSQZ-UHFFFAOYSA-N 0.000 description 1
- BDGCAHYGTNRIOD-UHFFFAOYSA-N 2,5-dibromo-1h-pyrrole Chemical class BrC1=CC=C(Br)N1 BDGCAHYGTNRIOD-UHFFFAOYSA-N 0.000 description 1
- MVMYJQKKCVQHEN-UHFFFAOYSA-N 2,6-bis(2,2-dimethylpropyl)aniline Chemical class CC(C)(C)CC1=CC=CC(CC(C)(C)C)=C1N MVMYJQKKCVQHEN-UHFFFAOYSA-N 0.000 description 1
- WKBALTUBRZPIPZ-UHFFFAOYSA-N 2,6-di(propan-2-yl)aniline Chemical group CC(C)C1=CC=CC(C(C)C)=C1N WKBALTUBRZPIPZ-UHFFFAOYSA-N 0.000 description 1
- LSEAAPGIZCDEEH-UHFFFAOYSA-N 2,6-dichloropyrazine Chemical class ClC1=CN=CC(Cl)=N1 LSEAAPGIZCDEEH-UHFFFAOYSA-N 0.000 description 1
- RZSUJIUTUGMZPG-UHFFFAOYSA-N 2,6-ditert-butylaniline Chemical group CC(C)(C)C1=CC=CC(C(C)(C)C)=C1N RZSUJIUTUGMZPG-UHFFFAOYSA-N 0.000 description 1
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- JTPXVCKCLBROOJ-UHFFFAOYSA-N 2-amino-6-chloropyrazine Chemical class NC1=CN=CC(Cl)=N1 JTPXVCKCLBROOJ-UHFFFAOYSA-N 0.000 description 1
- 150000005798 2-amino-6-chloropyridine Chemical class 0.000 description 1
- JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 description 1
- QAUQHTFRJMMRFK-UHFFFAOYSA-N 2-benzyl-1h-indene Chemical class C=1C2=CC=CC=C2CC=1CC1=CC=CC=C1 QAUQHTFRJMMRFK-UHFFFAOYSA-N 0.000 description 1
- ANIJFZVZXZQFDH-UHFFFAOYSA-N 2-bromo-5-nitro-1,3-thiazole Chemical class [O-][N+](=O)C1=CN=C(Br)S1 ANIJFZVZXZQFDH-UHFFFAOYSA-N 0.000 description 1
- NTYGYRIDBOPKPI-UHFFFAOYSA-N 2-butyl-2-ethyloctanoic acid Chemical compound CCCCCCC(CC)(C(O)=O)CCCC NTYGYRIDBOPKPI-UHFFFAOYSA-N 0.000 description 1
- HTSVYUUXJSMGQC-UHFFFAOYSA-N 2-chloro-1,3,5-triazine Chemical class ClC1=NC=NC=N1 HTSVYUUXJSMGQC-UHFFFAOYSA-N 0.000 description 1
- BSQLQMLFTHJVKS-UHFFFAOYSA-N 2-chloro-1,3-benzothiazole Chemical class C1=CC=C2SC(Cl)=NC2=C1 BSQLQMLFTHJVKS-UHFFFAOYSA-N 0.000 description 1
- BHAKRVSCGILCEW-UHFFFAOYSA-N 2-chloro-4-methylpyrimidine Chemical class CC1=CC=NC(Cl)=N1 BHAKRVSCGILCEW-UHFFFAOYSA-N 0.000 description 1
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical class N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 description 1
- BSHJHVHMLRKHBZ-UHFFFAOYSA-N 2-ethyl-1h-indene Chemical class C1=CC=C2CC(CC)=CC2=C1 BSHJHVHMLRKHBZ-UHFFFAOYSA-N 0.000 description 1
- DJDGWVCBUNYBOO-UHFFFAOYSA-N 2-methylideneoctanoic acid Chemical compound CCCCCCC(=C)C(O)=O DJDGWVCBUNYBOO-UHFFFAOYSA-N 0.000 description 1
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- MBNVSWHUJDDZRH-UHFFFAOYSA-N 2-methylthiirane Chemical compound CC1CS1 MBNVSWHUJDDZRH-UHFFFAOYSA-N 0.000 description 1
- QDISGXQOFWCDLB-UHFFFAOYSA-N 2-phenylhexanedioic acid Chemical compound OC(=O)CCCC(C(O)=O)C1=CC=CC=C1 QDISGXQOFWCDLB-UHFFFAOYSA-N 0.000 description 1
- LZHCVNIARUXHAL-UHFFFAOYSA-N 2-tert-butyl-4-ethylphenol Chemical class CCC1=CC=C(O)C(C(C)(C)C)=C1 LZHCVNIARUXHAL-UHFFFAOYSA-N 0.000 description 1
- CFTYZLBAGNHPIQ-UHFFFAOYSA-N 3,5-dichloro-4-methylpyridazine Chemical class CC1=C(Cl)C=NN=C1Cl CFTYZLBAGNHPIQ-UHFFFAOYSA-N 0.000 description 1
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 1
- YRXLGZMIIFCVJM-UHFFFAOYSA-N 3-ethyl-1h-indene Chemical class C1=CC=C2C(CC)=CCC2=C1 YRXLGZMIIFCVJM-UHFFFAOYSA-N 0.000 description 1
- IUJVWFXPYWSFGL-UHFFFAOYSA-N 3-methyl-1-(2-methylaziridin-1-yl)butan-1-one Chemical class CC(C)CC(=O)N1CC1C IUJVWFXPYWSFGL-UHFFFAOYSA-N 0.000 description 1
- COOKKJGOGWACMY-UHFFFAOYSA-N 3-methyl-1h-indene Chemical class C1=CC=C2C(C)=CCC2=C1 COOKKJGOGWACMY-UHFFFAOYSA-N 0.000 description 1
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 1
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 1
- FCMLONIWOAGZJX-UHFFFAOYSA-N 4,6-dichloro-2-methylsulfanylpyrimidine Chemical class CSC1=NC(Cl)=CC(Cl)=N1 FCMLONIWOAGZJX-UHFFFAOYSA-N 0.000 description 1
- JPZOAVGMSDSWSW-UHFFFAOYSA-N 4,6-dichloropyrimidin-2-amine Chemical class NC1=NC(Cl)=CC(Cl)=N1 JPZOAVGMSDSWSW-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- OBHKONRNYCDRKM-UHFFFAOYSA-N 4-chloro-2-phenylquinazoline Chemical class N=1C2=CC=CC=C2C(Cl)=NC=1C1=CC=CC=C1 OBHKONRNYCDRKM-UHFFFAOYSA-N 0.000 description 1
- LJSMGWBQOFWAPJ-UHFFFAOYSA-N 4-methoxy-3-(naphthalen-1-ylmethyl)-4-oxobutanoic acid Chemical compound C1=CC=C2C(CC(CC(O)=O)C(=O)OC)=CC=CC2=C1 LJSMGWBQOFWAPJ-UHFFFAOYSA-N 0.000 description 1
- BJNZCLXGKOQOEV-UHFFFAOYSA-N 6-chloro-1h-pyrimidine-2-thione Chemical class SC1=NC=CC(Cl)=N1 BJNZCLXGKOQOEV-UHFFFAOYSA-N 0.000 description 1
- UZNLHJCCGYKCIL-UHFFFAOYSA-N 6-ethoxy-6-oxohexanoic acid Chemical compound CCOC(=O)CCCCC(O)=O UZNLHJCCGYKCIL-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical class C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241001614291 Anoplistes Species 0.000 description 1
- NDERRIHSWCOMJJ-UHFFFAOYSA-N C(C(=C)C)(=O)OC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.P(=O)(O)(O)O Chemical compound C(C(=C)C)(=O)OC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.P(=O)(O)(O)O NDERRIHSWCOMJJ-UHFFFAOYSA-N 0.000 description 1
- GEMIKKBXLAEUKA-UHFFFAOYSA-N C(C=C)(=O)OC(C)(C)C.C(C=C)(=O)OC(C)(C)C Chemical compound C(C=C)(=O)OC(C)(C)C.C(C=C)(=O)OC(C)(C)C GEMIKKBXLAEUKA-UHFFFAOYSA-N 0.000 description 1
- MVLIALZGAPLHFS-UHFFFAOYSA-N C(C=C)(=O)OC1=CC=CC=C1.C(C=C)(=O)OC1=CC=CC=C1 Chemical compound C(C=C)(=O)OC1=CC=CC=C1.C(C=C)(=O)OC1=CC=CC=C1 MVLIALZGAPLHFS-UHFFFAOYSA-N 0.000 description 1
- ZLVQJTMXQUSPRT-UHFFFAOYSA-N C(C=C)(=O)OCCCCCC.C(C=C)(=O)OCCCCCC Chemical compound C(C=C)(=O)OCCCCCC.C(C=C)(=O)OCCCCCC ZLVQJTMXQUSPRT-UHFFFAOYSA-N 0.000 description 1
- XGBLLZMCLBLMOH-UHFFFAOYSA-N C=C=S.C=C Chemical compound C=C=S.C=C XGBLLZMCLBLMOH-UHFFFAOYSA-N 0.000 description 1
- DMAWHHOICGGPQF-UHFFFAOYSA-N CCCCCC[SiH2]Cl Chemical class CCCCCC[SiH2]Cl DMAWHHOICGGPQF-UHFFFAOYSA-N 0.000 description 1
- FZGBMUNSAKBIFU-UHFFFAOYSA-N COC(C(O)CC(=O)OC)=O.C1(=CC=CC=C1)[Sn]C1=CC=CC=C1 Chemical compound COC(C(O)CC(=O)OC)=O.C1(=CC=CC=C1)[Sn]C1=CC=CC=C1 FZGBMUNSAKBIFU-UHFFFAOYSA-N 0.000 description 1
- UNMYWSMUMWPJLR-UHFFFAOYSA-L Calcium iodide Chemical compound [Ca+2].[I-].[I-] UNMYWSMUMWPJLR-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 1
- 229920002943 EPDM rubber Polymers 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 229910003803 Gold(III) chloride Inorganic materials 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 1
- HXCANLIEKANFNZ-UHFFFAOYSA-N OP(O)(O)=O.CC(=O)OC=C Chemical compound OP(O)(O)=O.CC(=O)OC=C HXCANLIEKANFNZ-UHFFFAOYSA-N 0.000 description 1
- JKRZOJADNVOXPM-UHFFFAOYSA-N Oxalic acid dibutyl ester Chemical compound CCCCOC(=O)C(=O)OCCCC JKRZOJADNVOXPM-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 229910021612 Silver iodide Inorganic materials 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- FXEDRSGUZBCDMO-PHEQNACWSA-N [(e)-3-phenylprop-2-enoyl] (e)-3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1/C=C/C(=O)OC(=O)\C=C\C1=CC=CC=C1 FXEDRSGUZBCDMO-PHEQNACWSA-N 0.000 description 1
- RVWADWOERKNWRY-UHFFFAOYSA-N [2-(dimethylamino)phenyl]-phenylmethanone Chemical compound CN(C)C1=CC=CC=C1C(=O)C1=CC=CC=C1 RVWADWOERKNWRY-UHFFFAOYSA-N 0.000 description 1
- UVSSPWOKVSKHCU-UHFFFAOYSA-N [2-(trifluoromethyl)phenoxy]boronic acid Chemical compound OB(O)OC1=CC=CC=C1C(F)(F)F UVSSPWOKVSKHCU-UHFFFAOYSA-N 0.000 description 1
- BEUGBYXJXMVRFO-UHFFFAOYSA-N [4-(dimethylamino)phenyl]-phenylmethanone Chemical class C1=CC(N(C)C)=CC=C1C(=O)C1=CC=CC=C1 BEUGBYXJXMVRFO-UHFFFAOYSA-N 0.000 description 1
- ANIJCLSWIOCKPW-UHFFFAOYSA-L [Cl-].[Cl-].[Ge++] Chemical compound [Cl-].[Cl-].[Ge++] ANIJCLSWIOCKPW-UHFFFAOYSA-L 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
- AJTSWTNBFNYRKL-UHFFFAOYSA-J [Re+4].I(=O)(=O)[O-].I(=O)(=O)[O-].I(=O)(=O)[O-].I(=O)(=O)[O-] Chemical compound [Re+4].I(=O)(=O)[O-].I(=O)(=O)[O-].I(=O)(=O)[O-].I(=O)(=O)[O-] AJTSWTNBFNYRKL-UHFFFAOYSA-J 0.000 description 1
- KOOADCGQJDGAGA-UHFFFAOYSA-N [amino(dimethyl)silyl]methane Chemical compound C[Si](C)(C)N KOOADCGQJDGAGA-UHFFFAOYSA-N 0.000 description 1
- FKXJWELJXMKBDI-UHFFFAOYSA-K [butyl-di(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(OC(=O)CCCCCCCCCCC)OC(=O)CCCCCCCCCCC FKXJWELJXMKBDI-UHFFFAOYSA-K 0.000 description 1
- FOZKAQMRLKYHQF-UHFFFAOYSA-K [di(dodecanoyloxy)-hexylstannyl] dodecanoate Chemical class CCCCCC[Sn+3].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O FOZKAQMRLKYHQF-UHFFFAOYSA-K 0.000 description 1
- KRJRCGDNLHOKME-UHFFFAOYSA-K [di(dodecanoyloxy)-octadecylstannyl] dodecanoate Chemical class CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC[Sn+3] KRJRCGDNLHOKME-UHFFFAOYSA-K 0.000 description 1
- AAFQDPRABOKQFY-UHFFFAOYSA-K [diacetyloxy(octadecyl)stannyl] acetate Chemical class CC([O-])=O.CC([O-])=O.CC([O-])=O.CCCCCCCCCCCCCCCCCC[Sn+3] AAFQDPRABOKQFY-UHFFFAOYSA-K 0.000 description 1
- LVIAVDPYLHRLNQ-UHFFFAOYSA-L [dibenzyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound C=1C=CC=CC=1C[Sn](OC(=O)CCCCCCCCCCC)(OC(=O)CCCCCCCCCCC)CC1=CC=CC=C1 LVIAVDPYLHRLNQ-UHFFFAOYSA-L 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- XHGCVHPVWFHMLR-UHFFFAOYSA-L [dodecanoyloxy(dihexyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCC)(CCCCCC)OC(=O)CCCCCCCCCCC XHGCVHPVWFHMLR-UHFFFAOYSA-L 0.000 description 1
- MQNWAKVHGCIHPV-UHFFFAOYSA-L [dodecanoyloxy(dioctadecyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC[Sn++]CCCCCCCCCCCCCCCCCC MQNWAKVHGCIHPV-UHFFFAOYSA-L 0.000 description 1
- XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 description 1
- KJLDTYUGZVCMRD-UHFFFAOYSA-L [dodecanoyloxy(diphenyl)stannyl] dodecanoate Chemical compound C=1C=CC=CC=1[Sn+2]C1=CC=CC=C1.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O KJLDTYUGZVCMRD-UHFFFAOYSA-L 0.000 description 1
- LIQZZAPDGRFJIP-UHFFFAOYSA-L [dodecanoyloxy-bis(2-methylpropyl)stannyl] dodecanoate Chemical compound CC(C)C[Sn+2]CC(C)C.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O LIQZZAPDGRFJIP-UHFFFAOYSA-L 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- LEKJTGQWLAUGQA-UHFFFAOYSA-N acetyl iodide Chemical compound CC(I)=O LEKJTGQWLAUGQA-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000008431 aliphatic amides Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Substances Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 1
- 150000001399 aluminium compounds Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- NKQIMNKPSDEDMO-UHFFFAOYSA-L barium bromide Chemical compound [Br-].[Br-].[Ba+2] NKQIMNKPSDEDMO-UHFFFAOYSA-L 0.000 description 1
- 229910001620 barium bromide Inorganic materials 0.000 description 1
- SGUXGJPBTNFBAD-UHFFFAOYSA-L barium iodide Chemical compound [I-].[I-].[Ba+2] SGUXGJPBTNFBAD-UHFFFAOYSA-L 0.000 description 1
- 229910001638 barium iodide Inorganic materials 0.000 description 1
- 229940075444 barium iodide Drugs 0.000 description 1
- CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 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
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- HPMLGNIUXVXALD-UHFFFAOYSA-N benzoyl fluoride Chemical compound FC(=O)C1=CC=CC=C1 HPMLGNIUXVXALD-UHFFFAOYSA-N 0.000 description 1
- WPCXDBCEDWUSOU-UHFFFAOYSA-N benzoyl iodide Chemical compound IC(=O)C1=CC=CC=C1 WPCXDBCEDWUSOU-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 229910001627 beryllium chloride Inorganic materials 0.000 description 1
- JUCWKFHIHJQTFR-UHFFFAOYSA-L beryllium iodide Chemical compound [Be+2].[I-].[I-] JUCWKFHIHJQTFR-UHFFFAOYSA-L 0.000 description 1
- 229910001639 beryllium iodide Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GJRRTUSXQPXVES-UHFFFAOYSA-N bis(2-methylpropyl) oxalate Chemical compound CC(C)COC(=O)C(=O)OCC(C)C GJRRTUSXQPXVES-UHFFFAOYSA-N 0.000 description 1
- DBDNZCBRIPTLJF-UHFFFAOYSA-N boron(1-) monohydride Chemical compound [BH-] DBDNZCBRIPTLJF-UHFFFAOYSA-N 0.000 description 1
- DKRDVQXZJNVXDP-UHFFFAOYSA-M bromo(dibutyl)alumane Chemical compound [Br-].CCCC[Al+]CCCC DKRDVQXZJNVXDP-UHFFFAOYSA-M 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-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
- ARHOYLIPPGVCTE-UHFFFAOYSA-N butyl prop-2-enoate Chemical compound CCCCOC(=O)C=C.CCCCOC(=O)C=C ARHOYLIPPGVCTE-UHFFFAOYSA-N 0.000 description 1
- BTMVHUNTONAYDX-UHFFFAOYSA-N butyl propionate Chemical compound CCCCOC(=O)CC BTMVHUNTONAYDX-UHFFFAOYSA-N 0.000 description 1
- FQEKAFQSVPLXON-UHFFFAOYSA-N butyl(trichloro)silane Chemical compound CCCC[Si](Cl)(Cl)Cl FQEKAFQSVPLXON-UHFFFAOYSA-N 0.000 description 1
- OCFSGVNHPVWWKD-UHFFFAOYSA-N butylaluminum Chemical compound [Al].[CH2]CCC OCFSGVNHPVWWKD-UHFFFAOYSA-N 0.000 description 1
- QQHRHLXGCZWTDK-UHFFFAOYSA-L butylaluminum(2+);dibromide Chemical compound [Br-].[Br-].CCCC[Al+2] QQHRHLXGCZWTDK-UHFFFAOYSA-L 0.000 description 1
- YMLFYGFCXGNERH-UHFFFAOYSA-K butyltin trichloride Chemical compound CCCC[Sn](Cl)(Cl)Cl YMLFYGFCXGNERH-UHFFFAOYSA-K 0.000 description 1
- 229940075417 cadmium iodide Drugs 0.000 description 1
- 229910001622 calcium bromide Inorganic materials 0.000 description 1
- WGEFECGEFUFIQW-UHFFFAOYSA-L calcium dibromide Chemical compound [Ca+2].[Br-].[Br-] WGEFECGEFUFIQW-UHFFFAOYSA-L 0.000 description 1
- 229910001640 calcium iodide Inorganic materials 0.000 description 1
- 229940046413 calcium iodide Drugs 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical class NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- GTPDFCLBTFKHNH-UHFFFAOYSA-N chloro(phenyl)silicon Chemical compound Cl[Si]C1=CC=CC=C1 GTPDFCLBTFKHNH-UHFFFAOYSA-N 0.000 description 1
- FXEDRSGUZBCDMO-UHFFFAOYSA-N cinnamic acid anhydride Natural products C=1C=CC=CC=1C=CC(=O)OC(=O)C=CC1=CC=CC=C1 FXEDRSGUZBCDMO-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 230000001955 cumulated effect Effects 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical class ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- CHVJITGCYZJHLR-UHFFFAOYSA-N cyclohepta-1,3,5-triene Chemical compound C1C=CC=CC=C1 CHVJITGCYZJHLR-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- PBGGNZZGJIKBMJ-UHFFFAOYSA-N di(propan-2-yl)azanide Chemical compound CC(C)[N-]C(C)C PBGGNZZGJIKBMJ-UHFFFAOYSA-N 0.000 description 1
- LXEMWOPQLGUDCY-UHFFFAOYSA-L di(propan-2-yl)tin(2+);dodecanoate Chemical compound CC(C)[Sn+2]C(C)C.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O LXEMWOPQLGUDCY-UHFFFAOYSA-L 0.000 description 1
- 125000005131 dialkylammonium group Chemical group 0.000 description 1
- ZYZXGWGQYNTGAU-UHFFFAOYSA-N dibenzyl oxalate Chemical compound C=1C=CC=CC=1COC(=O)C(=O)OCC1=CC=CC=C1 ZYZXGWGQYNTGAU-UHFFFAOYSA-N 0.000 description 1
- RJYMRRJVDRJMJW-UHFFFAOYSA-L dibromomanganese Chemical compound Br[Mn]Br RJYMRRJVDRJMJW-UHFFFAOYSA-L 0.000 description 1
- NJKDOKBDBHYMAH-UHFFFAOYSA-N dibutyl(dichloro)silane Chemical compound CCCC[Si](Cl)(Cl)CCCC NJKDOKBDBHYMAH-UHFFFAOYSA-N 0.000 description 1
- VJRUISVXILMZSL-UHFFFAOYSA-M dibutylalumanylium;chloride Chemical compound CCCC[Al](Cl)CCCC VJRUISVXILMZSL-UHFFFAOYSA-M 0.000 description 1
- VTZJFPSWNQFPCQ-UHFFFAOYSA-N dibutylaluminum Chemical compound CCCC[Al]CCCC VTZJFPSWNQFPCQ-UHFFFAOYSA-N 0.000 description 1
- NRAYZPGATNMOSB-UHFFFAOYSA-N dichloro(dihexyl)silane Chemical compound CCCCCC[Si](Cl)(Cl)CCCCCC NRAYZPGATNMOSB-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
- XBPCUCUWBYBCDP-UHFFFAOYSA-O dicyclohexylazanium Chemical compound C1CCCCC1[NH2+]C1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-O 0.000 description 1
- 229920003244 diene elastomer Polymers 0.000 description 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylphenylamine Natural products CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- CPDVHGLWIFENDJ-UHFFFAOYSA-N dihexylalumane Chemical compound C(CCCCC)[AlH]CCCCCC CPDVHGLWIFENDJ-UHFFFAOYSA-N 0.000 description 1
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- JGHYBJVUQGTEEB-UHFFFAOYSA-M dimethylalumanylium;chloride Chemical compound C[Al](C)Cl JGHYBJVUQGTEEB-UHFFFAOYSA-M 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- XMQXMOKIYVQDNL-UHFFFAOYSA-N dioctadecyl oxalate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(=O)OCCCCCCCCCCCCCCCCCC XMQXMOKIYVQDNL-UHFFFAOYSA-N 0.000 description 1
- GNPSMYTXIPVJDU-UHFFFAOYSA-N dioctylalumane Chemical compound C(CCCCCCC)[AlH]CCCCCCCC GNPSMYTXIPVJDU-UHFFFAOYSA-N 0.000 description 1
- KMHJKRGRIJONSV-UHFFFAOYSA-N dioxygen(.1+) Chemical compound [O+]=O KMHJKRGRIJONSV-UHFFFAOYSA-N 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- ULOZDEVJRTYKFE-UHFFFAOYSA-N diphenyl oxalate Chemical compound C=1C=CC=CC=1OC(=O)C(=O)OC1=CC=CC=C1 ULOZDEVJRTYKFE-UHFFFAOYSA-N 0.000 description 1
- HCWOVPZEAFLXPL-UHFFFAOYSA-N diphenyl propanedioate Chemical compound C=1C=CC=CC=1OC(=O)CC(=O)OC1=CC=CC=C1 HCWOVPZEAFLXPL-UHFFFAOYSA-N 0.000 description 1
- OVKPJPPQHUVZFT-UHFFFAOYSA-L diphenyltin(2+);hexanedioate Chemical compound [O-]C(=O)CCCCC([O-])=O.C=1C=CC=CC=1[Sn+2]C1=CC=CC=C1 OVKPJPPQHUVZFT-UHFFFAOYSA-L 0.000 description 1
- NJLLQSBAHIKGKF-UHFFFAOYSA-N dipotassium dioxido(oxo)titanium Chemical compound [K+].[K+].[O-][Ti]([O-])=O NJLLQSBAHIKGKF-UHFFFAOYSA-N 0.000 description 1
- ITHNIFCFNUZYLQ-UHFFFAOYSA-N dipropan-2-yl oxalate Chemical compound CC(C)OC(=O)C(=O)OC(C)C ITHNIFCFNUZYLQ-UHFFFAOYSA-N 0.000 description 1
- VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- CIYGMWIAXRMHQS-UHFFFAOYSA-N ditert-butyl oxalate Chemical compound CC(C)(C)OC(=O)C(=O)OC(C)(C)C CIYGMWIAXRMHQS-UHFFFAOYSA-N 0.000 description 1
- KMLAKVKRWRDDJH-UHFFFAOYSA-L ditert-butyltin(2+);dodecanoate Chemical compound CC(C)(C)[Sn+2]C(C)(C)C.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O KMLAKVKRWRDDJH-UHFFFAOYSA-L 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- UPZLDBJSYQCGBS-UHFFFAOYSA-K dodecanoate phenyltin(3+) Chemical compound [Sn+3]c1ccccc1.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O UPZLDBJSYQCGBS-UHFFFAOYSA-K 0.000 description 1
- PYBNTRWJKQJDRE-UHFFFAOYSA-L dodecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O PYBNTRWJKQJDRE-UHFFFAOYSA-L 0.000 description 1
- AOMUALOCHQKUCD-UHFFFAOYSA-N dodecyl 4-chloro-3-[[3-(4-methoxyphenyl)-3-oxopropanoyl]amino]benzoate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=C(Cl)C(NC(=O)CC(=O)C=2C=CC(OC)=CC=2)=C1 AOMUALOCHQKUCD-UHFFFAOYSA-N 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- CWMKZYCJCZVSHO-UHFFFAOYSA-N ethenethione Chemical compound C=C=S CWMKZYCJCZVSHO-UHFFFAOYSA-N 0.000 description 1
- GCSJLQSCSDMKTP-UHFFFAOYSA-N ethenyl(trimethyl)silane Chemical compound C[Si](C)(C)C=C GCSJLQSCSDMKTP-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- WUOIAOOSKMHJOV-UHFFFAOYSA-N ethyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CC)C1=CC=CC=C1 WUOIAOOSKMHJOV-UHFFFAOYSA-N 0.000 description 1
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 1
- QWUGXIXRFGEYBD-UHFFFAOYSA-M ethylmercuric chloride Chemical compound CC[Hg]Cl QWUGXIXRFGEYBD-UHFFFAOYSA-M 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- WDQNIWFZKXZFAY-UHFFFAOYSA-M fentin acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 WDQNIWFZKXZFAY-UHFFFAOYSA-M 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
- 238000011049 filling Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 238000012685 gas phase polymerization Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
- ATGIETUGWDAYPU-UHFFFAOYSA-M gold monoiodide Chemical compound [Au]I ATGIETUGWDAYPU-UHFFFAOYSA-M 0.000 description 1
- RJHLTVSLYWWTEF-UHFFFAOYSA-K gold trichloride Chemical compound Cl[Au](Cl)Cl RJHLTVSLYWWTEF-UHFFFAOYSA-K 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 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
- BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 description 1
- 229910001641 magnesium iodide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- HMJBVVFSNKQXCS-UHFFFAOYSA-L manganese(2+) diiodate Chemical compound [Mn+2].[O-]I(=O)=O.[O-]I(=O)=O HMJBVVFSNKQXCS-UHFFFAOYSA-L 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229960002523 mercuric chloride Drugs 0.000 description 1
- NGYIMTKLQULBOO-UHFFFAOYSA-L mercury dibromide Chemical compound Br[Hg]Br NGYIMTKLQULBOO-UHFFFAOYSA-L 0.000 description 1
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 1
- 239000005055 methyl trichlorosilane Substances 0.000 description 1
- XBKBZMOLSULOEA-UHFFFAOYSA-L methylaluminum(2+);dibromide Chemical compound C[Al](Br)Br XBKBZMOLSULOEA-UHFFFAOYSA-L 0.000 description 1
- YSTQWZZQKCCBAY-UHFFFAOYSA-L methylaluminum(2+);dichloride Chemical compound C[Al](Cl)Cl YSTQWZZQKCCBAY-UHFFFAOYSA-L 0.000 description 1
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- WXUAQHNMJWJLTG-UHFFFAOYSA-N monomethylpersuccinic acid Natural products OC(=O)C(C)CC(O)=O WXUAQHNMJWJLTG-UHFFFAOYSA-N 0.000 description 1
- CMESPBFFDMPSIY-UHFFFAOYSA-N n,n'-diphenylmethanediimine Chemical compound C1=CC=CC=C1N=C=NC1=CC=CC=C1 CMESPBFFDMPSIY-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 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
- 150000002798 neodymium compounds Chemical class 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 150000002835 noble gases Chemical class 0.000 description 1
- SWASRQFEYPWIPA-UHFFFAOYSA-N octadecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C=C.CCCCCCCCCCCCCCCCCCOC(=O)C=C SWASRQFEYPWIPA-UHFFFAOYSA-N 0.000 description 1
- GJYXGIIWJFZCLN-UHFFFAOYSA-N octane-2,4-dione Chemical compound CCCCC(=O)CC(C)=O GJYXGIIWJFZCLN-UHFFFAOYSA-N 0.000 description 1
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
- NIYCDDDBXZZPFJ-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C.CCCCCCCCOC(=O)C=C NIYCDDDBXZZPFJ-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- PFENPVAFZTUOOM-UHFFFAOYSA-N phenyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC1=CC=CC=C1 PFENPVAFZTUOOM-UHFFFAOYSA-N 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- ODOPKAJVFRHHGM-UHFFFAOYSA-N phenyltin Chemical compound [Sn]C1=CC=CC=C1 ODOPKAJVFRHHGM-UHFFFAOYSA-N 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
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000120 polyethyl acrylate Polymers 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 239000012985 polymerization agent Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920003225 polyurethane elastomer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- KKHRVELQCFDNHS-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound C(C=C)(=O)OC(C)C.C(C=C)(=O)OC(C)C KKHRVELQCFDNHS-UHFFFAOYSA-N 0.000 description 1
- SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical compound ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 description 1
- ZILUASOLDUBEBG-UHFFFAOYSA-N propanenitrile;propan-2-one Chemical compound CCC#N.CC(C)=O ZILUASOLDUBEBG-UHFFFAOYSA-N 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Chemical group O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- IIHQNAXFIODVDU-UHFFFAOYSA-N pyrimidine-2-carbonitrile Chemical class N#CC1=NC=CC=N1 IIHQNAXFIODVDU-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- 229940045105 silver iodide Drugs 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000003746 solid phase reaction Methods 0.000 description 1
- 238000010671 solid-state reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- IEXRMSFAVATTJX-UHFFFAOYSA-N tetrachlorogermane Chemical compound Cl[Ge](Cl)(Cl)Cl IEXRMSFAVATTJX-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 description 1
- 125000001391 thioamide group Chemical group 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- LNANSYMQXPWAEI-UHFFFAOYSA-M tribenzylstannyl acetate Chemical compound C=1C=CC=CC=1C[Sn](CC=1C=CC=CC=1)(OC(=O)C)CC1=CC=CC=C1 LNANSYMQXPWAEI-UHFFFAOYSA-M 0.000 description 1
- RJIFVNWOLLIBJV-UHFFFAOYSA-N tributyl benzene-1,2,4-tricarboxylate Chemical compound CCCCOC(=O)C1=CC=C(C(=O)OCCCC)C(C(=O)OCCCC)=C1 RJIFVNWOLLIBJV-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- JSQJUDVTRRCSRU-UHFFFAOYSA-N tributyl(chloro)silane Chemical compound CCCC[Si](Cl)(CCCC)CCCC JSQJUDVTRRCSRU-UHFFFAOYSA-N 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-O tributylazanium Chemical compound CCCC[NH+](CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-O 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- LFXJGGDONSCPOF-UHFFFAOYSA-N trichloro(hexyl)silane Chemical compound CCCCCC[Si](Cl)(Cl)Cl LFXJGGDONSCPOF-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
- YSCVYRUCAPMZFG-UHFFFAOYSA-K trichlorotin Chemical compound Cl[Sn](Cl)Cl YSCVYRUCAPMZFG-UHFFFAOYSA-K 0.000 description 1
- 125000000169 tricyclic heterocycle group Chemical group 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- UYPYRKYUKCHHIB-UHFFFAOYSA-N trimethylamine N-oxide Chemical compound C[N+](C)(C)[O-] UYPYRKYUKCHHIB-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-O trimethylammonium Chemical compound C[NH+](C)C GETQZCLCWQTVFV-UHFFFAOYSA-O 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- OLFPYUPGPBITMH-UHFFFAOYSA-N tritylium Chemical compound C1=CC=CC=C1[C+](C=1C=CC=CC=1)C1=CC=CC=C1 OLFPYUPGPBITMH-UHFFFAOYSA-N 0.000 description 1
- KPGXUAIFQMJJFB-UHFFFAOYSA-H tungsten hexachloride Chemical compound Cl[W](Cl)(Cl)(Cl)(Cl)Cl KPGXUAIFQMJJFB-UHFFFAOYSA-H 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229940102001 zinc bromide Drugs 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
- C08C19/22—Incorporating nitrogen atoms into the molecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
-
- C—CHEMISTRY; METALLURGY
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/25—Incorporating silicon atoms into the molecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
- C08C19/42—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups
- C08C19/44—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups of polymers containing metal atoms exclusively at one or both ends of the skeleton
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F136/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F136/02—Homopolymers 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
- C08F136/04—Homopolymers 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
- C08F136/06—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
- C08F136/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F136/02—Homopolymers 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
- C08F136/04—Homopolymers 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
- C08F136/08—Isoprene
-
- 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
- C08F4/06—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen
- C08F4/12—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen of boron, aluminium, gallium, indium, thallium or rare earths
-
- 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
- C08F4/54—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 together with other compounds thereof
-
- 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
- C08F4/60—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 together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/602—Component covered by group C08F4/60 with an organo-aluminium compound
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/18—Introducing halogen atoms or halogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/34—Introducing sulfur atoms or sulfur-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/40—Introducing phosphorus atoms or phosphorus-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/04—Carbon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L15/00—Compositions of rubber derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2353/00—Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
- C08J2353/02—Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers of vinyl aromatic monomers and conjugated dienes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerization Catalysts (AREA)
Abstract
本发明的目的是提供:一种末端改性共轭二烯聚合物的制造方法,其能够实现极高的顺式‑1,4键含量而不要求复杂的制造条件;一种使用所述制造方法获得的末端改性共轭二烯聚合物;一种包含所述末端改性共轭二烯聚合物的橡胶组合物;以及一种使用所述橡胶组合物的轮胎。本发明为一种末端改性共轭二烯聚合物的制造方法,其中使用聚合催化剂组合物聚合共轭二烯系化合物,并且使用改性剂将所述聚合中得到的聚合物改性,所述方法的特征在于:所述聚合催化剂组合物包含稀土元素化合物和配位化合物,所述配位化合物具有选自取代或未取代的环戊二烯、取代或未取代的茚、和取代或未取代的芴的环戊二烯骨架;并且所述聚合和改性以一锅方式进行。
Description
技术领域
本公开涉及一种末端改性共轭二烯聚合物的制造方法,特别是在没有复杂制造条件的情况下实现极高的顺式-1,4键含量的末端改性共轭二烯聚合物的制造方法,并且还涉及末端改性共轭二烯聚合物、橡胶组合物和轮胎。
背景技术
近来,基于节约资源和能源的社会需求,对汽车更低的燃油消耗的要求逐渐增长,并且需求耐摩耗性和耐裂纹生长性等优异的轮胎。立构规整地控制配混至轮胎的橡胶组分的微结构已知是改进轮胎耐久性的技术。
另一方面,已知天然橡胶具有其中顺式-1,4键含量为99.7%的微结构,并且认识到由于高立构规整性改进了应变诱导结晶性(strain-induced crystallizability)。关于使用天然橡胶的橡胶组合物,当用于轮胎时,其能够显示高耐久性。此外,已知通过立构规整地控制聚丁二烯的微结构,能够改进耐久性。
PTL1公开了通过使用将共轭二烯单体添加至钕化合物获得的催化剂体系,能够合成具有高顺式-1,4键含量的聚丁二烯。
此外,PTL2公开的是对使用包含镧系稀土金属化合物的催化剂在有机溶剂中聚合共轭二烯系化合物而得到的具有活性有机金属部位的聚合物通过使用特定的改性剂进行改性而制造改性共轭二烯聚合物的技术,该改性共轭二烯聚合物具有特定值以上的改性率且在其共轭二烯部分具有高顺式-1,4含量。
引用列表
专利文献
PTL1:JP2005-530872A
PTL2:WO2006/112450A1
发明内容
发明要解决的问题
然而,根据PTL1和PTL2的技术,为了获得高顺式-1,4键含量,必要的是进行严格的条件管理,例如在低温(室温以下)下聚合。因此,期待开发能在没有复杂条件的情况下有效地获得具有极高的顺式-1,4键含量的末端改性共轭二烯聚合物的技术。
本公开的目的为提供一种在没有复杂制造条件的情况下实现极高的顺式-1,4键含量的末端改性共轭二烯聚合物的制造方法,此外,提供一种使用该制造方法得到的末端改性共轭二烯聚合物而耐久性(耐断裂性、耐摩耗性和耐裂纹生长性)优异的橡胶组合物和轮胎。
用于解决问题的方案
对上述目标进行深入研究后,本发明人发现以下情况且得出本公开:通过使用包含至少一个氮原子的稀土元素化合物和具有特定环戊二烯骨架的配位化合物作为聚合催化剂组合物,这样的配位化合物能够代替常用的助催化剂作为阴离子性配体而改进催化活性,因此即使在高聚合温度下也能够实现极高的顺式-1,4键含量和末端改性率,并且由于一锅(one-pot)聚合和改性能够在没有复杂过程的情况下制造末端改性共轭二烯聚合物。
本公开以这种知识为基础,且其主题如下。
本公开的末端改性共轭二烯聚合物的制造方法为包括如下的末端改性共轭二烯聚合物的制造方法:使用聚合催化剂组合物聚合共轭二烯系化合物,并使用改性剂将经由聚合得到的聚合物改性,
其中所述聚合催化剂组合物包含稀土元素化合物和配位化合物,所述配位化合物具有选自取代或未取代的环戊二烯、取代或未取代的茚、和取代或未取代的芴的环戊二烯骨架,并且
其中所述聚合和改性以一锅法的方式进行。
此处的稀土元素化合物优选为由通式(a-1)表示:
M-(AQ1)(AQ2)(AQ3)…(a-1)
(式中,M为钪、钇或镧系元素;AQ1、AQ2和AQ3为相同或不同的官能团;A为氮、氧或硫;其中具有至少一个M-A键)。这样的化合物能够进一步改进催化活性。
催化剂组合物优选进一步包含由通式(X)表示的化合物。这样的化合物能够进一步改进催化活性。
YR31 aR32 bR33 c…(X)
(式中,Y为选自周期表第1族、第2族、第12族和第13族的金属元素,R31和R32为C1至C10烃基或氢原子,R33为C1至C10烃基,其中R31、R32和R33可彼此相同或不同;此外,当Y为选自周期表第1族的金属元素时,a=1且b、c=0;当Y为选自周期表第2族和第12族的金属元素时,a、b=1且c=0;当Y为选自周期表第13族的金属元素时,a、b、c=1)。
此处的具有环戊二烯骨架的配位化合物优选具有茚基。这样的化合物能够进一步改进催化活性。
另外,聚合催化剂组合物优选进一步包含铝氧烷化合物,和/或包含卤素化合物。这样的化合物能够进一步改进催化活性。
另外,改性剂优选为选自特定化合物(a)至(j)的至少之一。这样的化合物能够改进聚合物的末端改性效果。
(a)为由通式(V)表示的化合物:
(其中X1至X5各自表示氢原子或单价官能团,所述单价官能团包含选自由卤素原子、羰基、硫代羰基、异氰酸酯基、硫代异氰酸酯基、环氧基、硫代环氧基、卤代甲硅烷基、烃氧基甲硅烷基和磺酰氧基组成的组的至少一种并且不包含活性质子或鎓盐;X1至X5可相同或不同,条件是X1至X5中至少之一不为氢原子;R1至R5各自独立地表示单键或二价的C1至C18烃基;且可以通过任意的X1至X5和R1至R5键合多个氮丙啶环);
(b)为由R6 nM'Z4-n、M'Z4、M'Z3、R7 nM'(-R8-COOR9)4-n或R7 nM'(-R8-COR9)4-n表示的卤代有机金属化合物、卤代金属化合物或有机金属化合物,
(其中R6至R8可相同或不同,且各自为C1至C20烃基;R9为C1至C20烃基且任选地在侧链上包含羰基或酯基;M'为锡原子、硅原子、锗原子或磷原子;Z为卤素原子;且n为0至3的整数);
(c)为分子中包含Y=C=Y'键的杂累积双键(heterocumulene)化合物(其中Y为碳原子、氧原子、氮原子或硫原子;且Y'为氧原子、氮原子或硫原子);
(d)为具有由通式(VI)表示的键的杂三元环(heterotricyclic)化合物:
(其中Y'为氧原子或硫原子);
(e)为卤代异氰基化合物;
(f)为由R10-(COOH)m、R11(COZ)m、R12-(COO-R13)、R14-OCOO-R15、R16-(COOCO-R17)m或通式(VII)表示的羧酸、酰卤化物、酯化合物、碳酸酯化合物或酸酐:
(其中R10至R18可相同或不同,且各自为C1至C50烃基;Z为卤素原子;且m为1至5的整数);
(g)为由R19 kM"(OCOR20)4-k、R21 kM"(OCO-R22-COOR23)4-k、或通式(VIII)表示的羧酸金属盐:
(其中R19至R25可相同或不同,且各自为C1至C20烃基;M"为锡原子、硅原子或锗原子;且k为0至3的整数);
(h)为N-取代的氨基酮、N-取代的氨基硫酮、N-取代的氨基醛、N-取代的氨基硫醛、或分子中具有-C-(=M)-N<键的化合物(M表示氧原子或硫原子);
(i)为具有N≡C-键的化合物;和
(j)为具有由通式(I)表示的磷酸残基的化合物:
(通式(I)中,R1和R2各自独立地表示选自直链或支链C1至C20烷基、单价C3至C20脂环族烃基和单价C6至C20芳族烃基的单价烃基,或氢原子)。
本公开的末端改性共轭二烯聚合物由本公开的末端改性共轭二烯聚合物的制造方法制得。
末端改性共轭二烯聚合物的顺式-1,4键含量优选为98%以上,更优选为98.5%以上。
本公开的橡胶组合物包含本公开的末端改性共轭二烯聚合物。
此外,本公开的轮胎使用本公开的橡胶组合物。
发明的效果
根据本公开,能够提供在没有复杂制造条件的情况下能实现极高的顺式-1,4键含量的末端改性共轭二烯聚合物的制造方法,以及由该制造方法制得的末端改性共轭二烯聚合物。
另外,通过使用上述末端改性共轭二烯聚合物,所得到的橡胶组合物和轮胎的耐久性(耐断裂性、耐摩耗性和耐裂纹生长性)优异。
具体实施方式
<末端改性共轭二烯聚合物的制造方法>
以下基于实施方式详细地描述本公开的末端改性共轭二烯聚合物的制造方法。
本公开的末端改性共轭二烯聚合物的制造方法至少包括使用聚合催化剂组合物来聚合共轭二烯系化合物的工序,和使用改性剂将经由聚合得到的聚合物改性的工序,其中聚合和改性以一锅法的方式进行。
(聚合工序)
本公开的聚合工序为使用聚合催化剂组合物来聚合共轭二烯系化合物的工序,该聚合催化剂组合物包含具有至少一个氮原子的稀土元素化合物和具有环戊二烯骨架的配位化合物。
-聚合催化剂组合物-
聚合催化剂组合物包含:
组分(A):稀土元素化合物,和
组分(D):具有选自取代或未取代的环戊二烯、取代或未取代的茚、和取代或未取代的芴的环戊二烯骨架的配位化合物。
此外,聚合催化剂组合物优选包含:
组分(B):选自离子性化合物和卤素化合物中的至少之一,更优选为选自包含非配位性阴离子和阳离子的离子性化合物(B-1)和卤素化合物(B-3)中的至少之一,该卤素化合物(B-3)为选自包含活性卤素的有机化合物、路易斯碱与金属卤化物的配合物、和路易斯酸中的至少之一。另外,如有需要,也可包含铝氧烷(B-2)。
另外,聚合催化剂组合物优选包含:
组分(C):由通式(X)表示的化合物:
YR31 aR32 bR33 c…(X)
(式中,Y为选自周期表第1族、第2族、第12族和第13族的金属元素,R31和R32为C1至C10烃基或氢原子,R33为C1至C10烃基;R31、R32和R33可彼此相同或不同。此外,当Y为选自周期表第1族的金属元素时,a=1且b、c=0;当Y为选自周期表第2族和第12族的金属元素时,a、b=1且c=0;当Y为选自周期表第13族的金属元素时,a、b、c=1)。
另外,当聚合催化剂组合物包含选自上述离子性化合物(B-1)和上述卤素化合物(B-3)中的至少之一时,其必须进一步包含组分(C)。
催化剂组合物的组分(A)为稀土元素化合物,其中含氮的稀土元素化合物包括含有稀土元素和优选的氮原子的化合物、以及该类化合物与路易斯酸的反应产物。
上述稀土元素化合物优选为由通式(a-1)表示的稀土元素化合物:
M-(AQ1)(AQ2)(AQ3)…(a-1)
(式中,M为钪、钇或镧系元素;AQ1、AQ2和AQ3为相同或不同的官能团;A为氮、氧或硫;其中具有至少一个M-A键)。
此外,从改进催化活性和反应控制性的角度看,M优选为钆。
当A为氮时,由AQ1、AQ2和AQ3(即,NQ1、NQ2和NQ3)表示的官能团可为酰胺基等。
酰胺基可为,例如,二甲基酰胺基、二乙基酰胺基、二异丙基酰胺基等脂族酰胺基;苯基酰胺基、2,6-二叔丁基苯基酰胺基、2,6-二异丙基苯基酰胺基、2,6-二新戊基苯基酰胺基、2-叔丁基-6-异丙基苯基酰胺基、2-叔丁基-6-新戊基苯基酰胺基、2-异丙基-6-新戊基苯基酰胺基、2,4,6-叔丁基苯基酰胺基等芳基酰胺基;和双三甲基甲硅烷基酰胺基等双三烷基甲硅烷基酰胺基,并且在这些中,从对脂族烃的溶解性的角度看,优选双三甲基甲硅烷基酰胺基。
这些官能团可单独使用或以两种以上的组合使用。
当A为氧时,由通式(a-1)(即,M-(OQ1)(OQ2)(OQ3))表示的稀土元素化合物没有限制,其可为以下化合物(I)至(II):
由(RO)3M (I)表示的稀土醇盐(rare earth alcoholate),
由(R-CO2)3M (II)表示的稀土羧酸盐(rare earth carboxylate)等。
此处,在各上述化合物(I)或(II)中,R为相同或不同的C1至C10烷基。
另外,组分(A)优选不具有稀土元素与碳的键,因此优选使用上述化合物(I)或化合物(II)。
当A为硫时,由通式(a-1)(即,M-(SQ1)(SQ2)(SQ3))表示的稀土元素化合物没有限制,其可为以下化合物(V)至(VI):
由(RS)3M (V)表示的稀土烷基硫醇盐,
由(R-CS2)3M (VI)表示的化合物等。
此处,在各上述化合物(V)或(VI)中,R为相同或不同的C1至C10烷基。
另外,组分(A)优选不具有稀土元素与碳的键,因此优选使用上述化合物(V)或化合物(VI)。
用作上述聚合催化剂组合物的组分(B)为选自由离子性化合物(B-1)和卤素化合物(B-3)组成的组中的至少一种化合物。此外,如有需要,也可包含铝氧烷(B-2)作为组分(B)。上述聚合催化剂组合物中的组分(B)的总含量优选为组分(A)的摩尔量的0.1至50倍。
上述(B-1)表示的离子性化合物包含非配位性阴离子和阳离子,并且包括通过与对应于上述组分(A)的含氮稀土元素化合物反应可生成阳离子性过渡金属化合物的离子性化合物。此处,非配位性阴离子可为四价的硼阴离子,例如,四苯基硼酸根、四(单氟苯基)硼酸根、四(二氟苯基)硼酸根、四(三氟苯基)硼酸根、四(四氟苯基)硼酸根、四(五氟苯基)硼酸根、四(四氟甲基苯基)硼酸根、四(甲苯基)硼酸根、四(二甲苯基)硼酸根、(三苯基,五氟苯基)硼酸根、[三(五氟苯基)苯基]硼酸根、十三氢化物-7,8-二碳杂十一硼酸根(tridecahydride-7,8-dicarbaundecaborate)等。另一方面,阳离子可为碳鎓阳离子(carbonium cation)、氧鎓阳离子(oxonium cation)、铵阳离子、鏻阳离子、环庚三烯基阳离子、具有过渡金属的二茂铁阳离子等。作为碳鎓阳离子的具体实例,包括三取代的碳鎓阳离子等,例如三苯基碳鎓阳离子、三(取代苯基)碳鎓阳离子等,特别地作为三(取代苯基)羰基阳离子,包括三(甲基苯基)碳鎓阳离子、三(二甲基苯基)碳鎓阳离子等。作为铵阳离子的具体实例,包括三烷基铵阳离子,例如三甲基铵阳离子、三乙基铵阳离子、三丙基铵阳离子、三丁基铵阳离子(例如三(正丁基)铵阳离子)等;N,N-二烷基苯铵阳离子,例如N,N-二甲基苯胺阳离子、N,N-二乙基苯胺阳离子、N,N-2,4,6-五甲基苯胺阳离子等;和二烷基铵阳离子,例如二异丙基铵阳离子、二环己基铵阳离子等。作为鏻阳离子的具体实例,包括三芳基鏻阳离子等,例如三苯基鏻阳离子、三(甲基苯基)鏻阳离子、三(二甲基苯基)鏻阳离子等。因此,离子性化合物优选为具有分别自上述的非配位性阴离子和阳离子选择和组合的离子的化合物,尤其是N,N-二甲基苯胺四(五氟苯基)硼酸盐、三苯基碳鎓四(五氟苯基)硼酸盐等。另外,这些离子性化合物可单独使用或以两种以上的组合使用。此外,上述聚合催化剂组合物中的离子性化合物的含量优选为组分(A)的摩尔量的0.1至10倍,更优选为组分(A)的摩尔量的约1倍。
上述(B-2)表示的铝氧烷为通过使有机铝化合物和缩合剂彼此接触而得到的化合物,例如,具有由通式(-Al(R’)O-)表示的重复单元的链状铝氧烷或环状铝氧烷(式中,R'为C1至C10烃基,其中一部分烃基可被卤素原子和/或烷氧基取代,且重复单元的聚合度优选为5以上,更优选为10以上)。此处,R'具体可为甲基、乙基、丙基、异丁基等,其中优选甲基。另外,用作铝氧烷的原料的有机铝化合物可为例如三甲基铝、三乙基铝、三异丁基铝等三烷基铝,或其混合物,并且特别优选三甲基铝。
例如,可优选使用利用三甲基铝和三丁基铝的混合物作为原料的铝氧烷。此外,上述聚合催化剂组合物中的铝氧烷化合物的含量优选为使铝氧烷中的铝元素Al与组分(A)中含有的稀土元素M的元素比Al/M为约10至1000。
上述(B-3)表示的卤素化合物由选自包含活性卤素的有机化合物、路易斯碱与金属卤化物的配合物、和路易斯酸中的至少之一组成,并且可以,例如,与对应于上述组分(A)的含氮稀土元素化合物反应,并产生阳离子性过渡金属化合物、卤化过渡金属化合物或含有电荷不足(charge-deficient)的过渡金属中心的化合物。特别是,考虑到在空气中的稳定性,优选使用金属卤化物和路易斯碱的配合物,而不是路易斯酸作为(B-3)的卤素化合物。此外,上述聚合催化剂组合物中的卤素化合物的总含量优选为组分(A)的摩尔量的1至5倍。
作为上述路易斯酸,可使用例如B(C6F5)3等含硼卤素化合物、例如Al(C6F5)3等含铝卤素化合物、以及还有包括属于周期表第3族、第4族、第5族、第6族或第8族的元素的卤素化合物。优选地,可使用卤化铝或有机金属卤化物。另外,作为卤素元素,优选氯和溴。作为上述路易斯酸,特别地,可使用甲基二溴化铝、甲基二氯化铝、乙基二溴化铝、乙基二氯化铝、丁基二溴化铝、丁基二氯化铝、二甲基溴化铝、二甲基氯化铝、二乙基溴化铝、二乙基氯化铝、二丁基溴化铝、二丁基氯化铝、倍半甲基溴化铝、倍半甲基氯化铝、倍半乙基溴化铝、倍半乙基氯化铝、二丁基二氯化锡、三溴化铝、三氯化锑、五氯化锑、三氯化磷、五氯化磷、四氯化锡、四氯化钛、六氯化钨等,其中特别优选二乙基氯化铝、倍半乙基氯化铝、乙基二氯化铝、二乙基溴化铝、倍半乙基溴化铝和乙基二溴化铝。当如上述使用卤素化合物时,在一个化合物中包含2个以上的卤素原子的化合物,与仅具有一个卤素原子的化合物相比,具有更好的反应性从而可降低其使用量,因此优选使用。例如,与乙基氯化铝相比,优选使用乙基二氯化铝。
金属卤化物和路易斯碱的配合物中含有的金属卤化物的实例包括氯化铍、溴化铍、碘化铍、氯化镁、溴化镁、碘化镁、氯化钙、溴化钙、碘化钙、氯化钡、溴化钡、碘化钡、氯化锌、溴化锌、碘化锌、氯化镉、溴化镉、碘化镉、氯化汞、溴化汞、碘化汞、氯化锰、溴化锰、碘化锰、氯化铼、溴化铼、碘化铼、氯化铜、碘化铜、氯化银、溴化银、碘化银、氯化金、碘化金和溴化金。其中优选氯化镁、氯化钙、氯化钡、氯化锰、氯化锌和氯化铜,特别优选氯化镁、氯化锰、氯化锌和氯化铜。
与金属卤化物形成配合物的路易斯碱的优选实例包括磷化合物、羰基化合物、氮化合物、醚化合物和醇。这些优选化合物的实例包括磷酸三丁酯、磷酸三-2-乙基己酯、磷酸三苯酯、磷酸三甲苯酯、三乙基膦、三丁基膦、三苯基膦、二乙基膦基乙烷、二苯基膦基乙烷、乙酰丙酮、苯甲酰丙酮、丙腈丙酮、戊酰丙酮、乙基乙酰丙酮、乙酰乙酸甲酯、乙酰乙酸乙酯、乙酰乙酸苯酯、丙二酸二甲酯、丙二酸二乙酯、丙二酸二苯酯、乙酸、辛酸、2-乙基己酸、油酸、硬脂酸、苯甲酸、环烷酸、叔碳酸(Versatic acid)、三乙胺、N,N-二甲基乙酰胺、四氢呋喃、二苯醚、2-乙基己醇、油醇、硬脂醇、苯酚、苯甲醇、1-癸醇和月桂醇。其中,更优选磷酸三(2-乙基己)酯、磷酸三甲苯酯、乙酰丙酮、2-乙基己酸、叔碳酸、2-乙基己醇、1-癸醇和月桂醇。
作为包含上述活性卤素的有机化合物,可使用苄基氯等。
上述聚合催化剂组合物(C)优选为由通式(X)表示的有机金属化合物:
YR31 aR32 bR33 c…(X)
(式中,Y为选自周期表第1族、第2族、第12族和第13族的金属元素,R31和R32为C1至C10烃基或氢原子,R33为C1至C10烃基,其中R31、R32和R33可彼此相同或不同;此外,当Y为选自周期表第1族的金属元素时,a=1且b、c=0;当Y为选自周期表第2族和第12族的金属元素时,a、b=1且c=0;当Y为选自周期表第13族的金属元素时,a、b、c=1),并且优选为由通式(Xa)表示的有机铝化合物:
YR31 aR32 bR33 c…(Xa)
(式中,R31和R32可相同或不同,包括C1至C10烃基或氢原子,R33为C1至C10烃基,且R33可与上述R31或R32相同或不同)。作为通式(X)中的有机铝化合物,可使用三甲基铝、三乙基铝、三正丙基铝、三异丙基铝、三正丁基铝、三异丁基铝、三叔丁基铝、三戊基铝、三己基铝、三环己基铝、三辛基铝;二乙基氢化铝、二正丙基氢化铝、二正丁基氢化铝、二异丁基氢化铝、二己基氢化铝、二异己基氢化铝、二辛基氢化铝、二异辛基氢化铝;乙基二氢化铝、正丙基二氢化铝、异丁基二氢化铝,其中优选三乙基铝、三异丁基铝、二乙基氢化铝、二异丁基氢化铝。此外,用作组分(C)的上述铝化合物可单独使用或以两种以上的组合使用。此外,上述聚合催化剂组合物中的有机铝化合物的含量优选为组合物(A)的摩尔量的1至50倍,更优选为约10倍。
聚合催化剂组合物中含有的组分(D)包含具有选自取代或未取代的环戊二烯、取代或未取代的茚、和取代或未取代的芴的环戊二烯骨架的配位化合物。由于空间位阻的效果,可以以更高的产率得到具有极高顺式-1,4键含量的末端改性共轭二烯聚合物。
而且,在使用能够成为阴离子性配体的常规化合物作为助催化剂的情况下,必需在低温下进行聚合,而在使用本申请的配位化合物的情况下,由于高溶解性和高立体控制性(stereocontrollability),可以在高温下进行聚合。
具有环戊二烯骨架的配位化合物没有限制,只要其具有选自取代或未取代的环戊二烯、取代或未取代的茚、和取代或未取代的芴的环戊二烯骨架即可,但从获得更高催化活性的能力的角度看,优选具有茚基的化合物。这种化合物能够在聚合期间在不使用甲苯作为溶剂的情况下改进活性。
此处,具有茚基的化合物可为茚、1-甲基茚、1-乙基茚、1-苄基茚、2-苯基茚、2-甲基茚、2-乙基茚、2-苄基茚、3-甲基茚、3-乙基茚、3-苄基茚等。
催化剂组合物通过,例如,将组分(A)至(D)溶解在溶剂中来制备。
这些组分的添加顺序不受限制。考虑到高的聚合活性和短的聚合诱导时间,优选将这些组分预先混合,使其反应并熟化。熟化温度典型地为约0至100℃,优选为20至80℃。低于0℃时,熟化可能不足。高于100℃时,催化活性可能降低,分子量分布可能变宽。熟化时间不受限制,并且可以在进给至聚合反应器之前通过在生产线(in the line)上的接触进行。通常,熟化可以实现至少0.5分钟,并且所得的催化剂在数日内是稳定的。
-聚合方法-
聚合方法不受限制,只要将反应物按顺序(以一锅法的方式进行)投入反应体系中即可。作为聚合方法,可使用选自溶液聚合、悬浮聚合、液相本体聚合、乳液聚合、气相聚合法、固相聚合等中的任一种。此外,在聚合反应中使用溶剂的情况下,所使用的溶剂可以是在聚合反应中呈惰性的任何类型。例如,包括正己烷、甲苯、环己烷或其混合物,并且考虑到环境负担和成本,优选使用环己烷、正己烷或混合物。
另外,在聚合工序中,可使用聚合终止剂如甲醇、乙醇、异丙醇等来终止聚合。
在聚合工序中,共轭二烯系化合物的聚合反应优选在惰性气体,优选氮气或氩气的气氛下进行。聚合反应的聚合温度没有限制,但优选选自-100℃至300℃的范围内,也可以设定在室温左右。此外,如果聚合温度升高,聚合反应的顺式-1,4选择性可能降低。另外,为了使足够的共轭二烯系化合物进入聚合反应体系中,聚合反应的压力优选为0.1至10.0MPa。另外,聚合反应的反应时间没有限制,优选为,例如,1秒至10天,也可以根据例如催化剂类型和聚合温度等条件适当选择。
(末端改性工序)
本公开的末端改性工序是使用改性剂将经由聚合工序得到的聚合物改性的工序。该末端改性工序在与聚合工序相同的反应体系中进行(以一锅法的方式进行)。
在末端改性工序中使用的改性剂中,使具有活性有机金属部位的聚合物与具有能够与活性有机金属部位进行取代或加成反应的官能团、且不包含使活性有机金属部位失活的活性质子的化合物进行反应,从而将该官能团并入聚合物中或者分子量通过偶联增加。
代表性的改性剂优选具有选自由如下组成的组中的至少一种官能团:氮杂环丙烷基、酮基、羧基、硫代羧基、碳酸盐、羧酸酐、羧酸金属盐、酰基卤、脲基、硫脲基、酰胺基、硫代酰胺基、异氰酸酯基、硫代异氰酸酯基、卤代异氰基、环氧基、硫代环氧基、亚氨基、和M-Z键(其中M为Sn、Si、Ge、或P,并且Z为卤素原子),并且优选不包含使活性有机金属部位失活的活性质子或鎓盐。
特别地,改性剂优选为选自以下化合物(a)至(j)中的至少之一。
化合物(a)为由通式(V)表示的化合物:
上式中,X1至X5各自为氢原子或单价官能团,所述单价官能团包含选自由卤素原子、羰基、硫代羰基、异氰酸酯基、硫代异氰酸酯基、环氧基、硫代环氧基、卤代甲硅烷基、烃氧基甲硅烷基和磺酰氧基组成的组的至少一种,并且不包含活性质子或鎓盐。X1至X5可相同或不同,条件是它们中至少之一不为氢原子。
R1至R5各自独立地表示单键或二价的C1至C18烃基。二价烃基的实例包括C1至C18亚烷基、C2至C18亚烯基、C6至C18亚芳基、C7至C18亚芳烷基。其中,优选C1至C18亚烷基,特别优选C1至C10亚烷基。亚烷基可以是直链状、支链状或环状的。特别地,优选直链基团。直链状亚烷基的实例包括亚甲基、亚乙基、三亚甲基、四亚甲基、五亚甲基、六亚甲基、八亚甲基和十亚甲基。
或者,可以通过任意的X1至X5和R1至R5键合多个氮丙啶环。
此外,化合物(a)优选不同时满足通式(V)中的X1=氢原子和R1=单键。
由通式(V)表示的改性剂的实例包括但不限于1-乙酰基氮丙啶、1-丙酰基氮丙啶、1-丁酰基氮丙啶、1-异丁酰基氮丙啶、1-戊酰基氮丙啶、1-异戊酰基氮丙啶、1-新戊酰基氮丙啶、1-乙酰基-2-甲基氮丙啶、2-甲基-1-丙酰基氮丙啶、1-丁酰基-2-甲基氮丙啶、2-甲基-1-异丁酰基氮丙啶、2-甲基-1-戊酰基氮丙啶、1-异戊酰基-2-甲基氮丙啶、2-甲基-1-新戊酰基氮丙啶、3-(1-氮丙啶基)丙酸乙酯、3-(1-氮丙啶基)丙酸丙酯、3-(1-氮丙啶基)丙酸丁酯、乙二醇双[3-(1-氮丙啶基)丙酸酯]、三羟甲基丙烷三[3-(1-氮丙啶基)丙酸酯]、3-(2-甲基-1-氮丙啶基)丙酸乙酯、3-(2-甲基-1-氮丙啶基)丙酸丙酯、3-(2-甲基-1-氮丙啶基)丙酸丁酯、乙二醇双[3-(2-甲基-1-氮丙啶基)丙酸酯]、三羟甲基丙烷三[3-(2-甲基-1-氮丙啶基)丙酸酯]、新戊二醇双[3-(1-氮丙啶基)丙酸酯]、新戊二醇双[3-(2-甲基-1-氮丙啶基)丙酸酯]、二(1-氮丙啶基羰基)甲烷、1,2-二(1-氮丙啶基羰基)乙烷、1,3-二(1-氮丙啶基羰基)丙烷、1,4-二(1-氮丙啶基羰基)丁烷、1,5-二(1-氮丙啶基羰基)戊烷、二(2-甲基-1-氮丙啶基羰基)甲烷、1,2-二(2-甲基-1-氮丙啶基羰基)乙烷、1,3-二(2-甲基-1-氮丙啶基羰基)丙烷、和1,4-二(2-甲基-1-氮丙啶基羰基)丁烷。
化合物(b)为由R6 nM'Z4-n或M'Z4、M'Z3表示的卤代有机金属化合物或卤代金属化合物。
(其中R6为相同或不同的C1至C20烃基;M'为锡原子、硅原子、锗原子或磷原子;Z为卤素原子;且n为0至3的整数)。
当上式中的M'为锡原子时,化合物(b)的实例包括三苯基氯化锡、三丁基氯化锡、三异丙基氯化锡、三己基氯化锡、三辛基氯化锡、二苯基二氯化锡、二丁基二氯化锡、二己基二氯化锡、二辛基二氯化锡、苯基三氯化锡、丁基三氯化锡、辛基三氯化锡和四氯化锡。
当上式中的M'为硅原子时,化合物(b)的实例包括三苯基氯硅烷、三己基氯硅烷、三辛基氯硅烷、三丁基氯硅烷、三甲基氯硅烷、二苯基二氯硅烷、二己基二氯硅烷、二辛基二氯硅烷、二丁基二氯硅烷、二甲基二氯硅烷、甲基二氯硅烷、苯基氯硅烷、己基三氯硅烷、辛基三氯硅烷、丁基三氯硅烷、甲基三氯硅烷和四氯化硅。
当上式中的M'为锗原子时,化合物(b)的实例包括三苯基氯化锗、二丁基二氯化锗、二苯基二氯化锗、丁基三氯化锗和四氯化锗。当上式中的M'为磷原子时,化合物(b)的实例包括三氯化磷。
改性剂化合物(b)可为分子中包含由下式表示的酯基或由下式表示的羰基的有机金属化合物:
R7 nM'(-R8-COOR9)4-n
R7 nM'(-R8-COR9)4-n
(其中R7和R8可相同或不同且各自为C1至C20烃基;R9为C1至C20烃基且可在侧链上包含羰基或酯基;M'为锡原子、硅原子、锗原子或磷原子;Z为卤素原子;且n为0至3的整数)。
这些化合物(b)可以以任意的比例组合使用。
化合物(c)为杂累积双键化合物,且为分子中具有Y=C=Y'键的改性剂。
上式中,Y为碳原子、氧原子、氮原子或硫原子,Y'为氧原子、氮原子或硫原子。当Y为碳原子且Y'为氧原子时,化合物(c)为烯酮化合物。当Y为碳原子且Y'为硫原子时,化合物(c)为硫烯酮(thioketene)化合物。当Y为氮原子且Y'为氧原子时,化合物(c)为异氰酸酯化合物。当Y为氮原子且Y'为硫原子时,化合物(c)为硫代异氰酸酯化合物。当Y和Y'均为氮原子时,化合物(c)为碳二亚胺化合物。当Y和Y'均为氧原子时,化合物(c)为二氧化碳。当Y为氧原子且Y'为硫原子时,化合物(c)为硫化羰。当Y和Y'均为硫原子时,化合物(c)为二硫化碳。但是化合物(c)不应局限于这些组合。
烯酮化合物的实例包括乙基烯酮、丁基烯酮、苯基烯酮和甲苯基烯酮。硫烯酮化合物的实例包括亚乙基硫烯酮(ethylene thioketene)、丁基硫烯酮、苯基硫烯酮和甲苯基硫烯酮(tolylthioketene)。异氰酸酯化合物的实例包括异氰酸苯酯、2,4-甲苯二异氰酸酯、2,6-甲苯二异氰酸酯、二苯基甲烷二异氰酸酯、聚合型二苯基甲烷二异氰酸酯、和六亚甲基二异氰酸酯。硫代异氰酸酯化合物的实例包括硫代异氰酸苯酯、2,4-甲苯二硫代异氰酸酯、和六亚甲基二硫代异氰酸酯。碳二亚胺化合物的实例包括N,N'-二苯基碳二亚胺和N,N'-乙基碳二亚胺。
化合物(d)为具有由下式(VI)表示的键的杂三元环化合物:
(其中Y'为氧原子或硫原子)。
当Y'为氧原子时,组分(d)为环氧化合物。当Y'为硫原子时,组分(d)为硫杂丙环化合物。环氧化合物的实例包括环氧乙烷、环氧丙烷、环氧环己烷、氧化苯乙烯、环氧化大豆油、和环氧化天然橡胶。硫杂丙环化合物的实例包括硫杂丙环、甲基硫杂丙环、和苯基硫杂丙环。
化合物(e)为卤代异氰基化合物。
卤代异氰基化合物具有由下式表示的键:
>N=C-X键
(其中X为卤素原子)。
作为化合物(e)的卤代异氰基化合物的实例包括2-氨基-6-氯吡啶、2,5-二溴吡啶、4-氯-2-苯基喹唑啉、2,4,5-三溴咪唑、3,6-二氯-4-甲基哒嗪、3,4,5-三氯哒嗪、4-氨基-6-氯-2-巯基嘧啶、2-氨基-4-氯-6-甲基嘧啶、2-氨基-4,6-二氯嘧啶、6-氯-2,4-二甲氧基嘧啶、2-氯嘧啶、2,4-二氯-6-甲基嘧啶、4,6-二氯-2-(甲硫基)嘧啶、2,4,5,6-四氯嘧啶、2,4,6-三氯嘧啶、2-氨基-6-氯吡嗪、2,6-二氯吡嗪、2,4-双(甲硫基)-6-氯-1,3,5-三嗪、2,4,6-三氯-1,3,5-三嗪、2-溴-5-硝基噻唑、2-氯苯并噻唑、和2-氯苯并噁唑。
化合物(f)包括由R10-(COOH)m、R11(COZ)m、R12-(COO-R13)、R14-OCOO-R15、R16-(COOCO-R17)m或通式(VII)表示的羧酸、酰卤化物、酯化合物、碳酸酯化合物或酸酐。
(其中R10至R18可相同或不同,且各自为C1至C50烃基;Z为卤素原子;且m为1至5的整数)。
化合物(f)的羧酸的实例包括乙酸、硬脂酸、己二酸、马来酸、苯甲酸、丙烯酸、甲基丙烯酸、邻苯二甲酸、间苯二甲酸、对苯二甲酸、偏苯三酸、苯均四酸、苯六甲酸、以及聚甲基丙烯酸酯化合物或聚丙烯酸化合物的完全或部分水解产物。
化合物(f)的酰卤化物的实例包括乙酰氯、丙酰氯、丁酰氯、异丁酰氯、辛酰氯、丙烯酰氯、苯甲酰氯、硬脂酰氯、邻苯二甲酰氯、丙二酰氯、草酰氯、乙酰碘、苯甲酰碘、乙酰氟和苯甲酰氟。
化合物(f)中的酯化合物的实例包括乙酸乙酯、硬脂酸乙酯、己二酸乙酯、马来酸二乙酯、苯甲酸甲酯、丙烯酸乙酯、甲基丙烯酸乙酯、邻苯二甲酸二乙酯、对苯二甲酸二甲酯、偏苯三酸三丁酯、苯均四酸四辛酯、苯六甲酸六乙酯、乙酸苯酯、聚(甲基丙烯酸甲酯)、聚(丙烯酸乙酯)、和聚(丙烯酸异丁酯)。碳酸酯化合物的实例包括碳酸二甲酯、碳酸二乙酯、碳酸二丙酯、碳酸二己酯、和碳酸二苯酯。酸酐的实例包括分子间酸酐,如乙酸酐、丙酸酐、丁酸酐、戊酸酐、庚酸酐、苯甲酸酐和肉桂酸酐;和分子内酸酐,如琥珀酸酐、甲基琥珀酸酐、马来酸酐、戊二酸酐、柠康酸酐、邻苯二甲酸酐、和苯乙烯-马来酸酐共聚物。
在本公开范围内,化合物(f)的化合物可在偶联剂分子中包含非质子极性基团,例如醚基和叔氨基。化合物(f)可以单独使用或以两种以上的组合使用。化合物(f)可包含具有游离的羟基或酚基的化合物作为杂质。化合物(f)可以单独使用或作为两种以上的化合物的混合物使用。
化合物(g)为由R19 kM"(OCOR20)4-k、R21 kM"(OCO-R22-COOR23)4-k、或通式(VIII)表示的羧酸的金属盐:
(其中R19至R25可相同或不同,且各自为C1至C20烃基;M"为锡原子、硅原子或锗原子;且k为0至3的整数)。
化合物(g)中的R19 kM"(OCOR20)4-k包括三苯基月桂酸锡(triphenyltin laurate)、三苯基2-乙基己酸锡、三苯基环烷酸锡、三苯基乙酸锡、三苯基丙烯酸锡、三正丁基月桂酸锡、三正丁基2-乙基己酸锡、三正丁基环烷酸锡、三正丁基乙酸锡、三正丁基丙烯酸锡、三叔丁基月桂酸锡、三叔丁基2-乙基己酸锡、三叔丁基环烷酸锡、三叔丁基乙酸锡、三叔丁基丙烯酸锡、三异丁基月桂酸锡、三异丁基2-乙基己酸锡、三异丁基环烷酸锡、三异丁基乙酸锡、三异丁基丙烯酸锡、三异丙基月桂酸锡、三异丙基2-乙基己酸锡、三异丙基环烷酸锡、三异丙基乙酸锡、三异丙基丙烯酸锡、三己基月桂酸锡、三己基2-乙基己酸锡、三己基乙酸锡、三己基丙烯酸锡、三辛基月桂酸锡、三辛基2-乙基己酸锡、三辛基环烷酸锡、三辛基乙酸锡、三辛基丙烯酸锡、三(2-乙基己基)月桂酸锡、三(2-乙基己基)2-乙基己酸锡、三(2-乙基己基)环烷酸锡、三(2-乙基己基)乙酸锡、三(2-乙基己基)丙烯酸锡、三硬脂基月桂酸锡、三硬脂基2-乙基己酸锡、三硬脂基环烷酸锡、三硬脂基乙酸锡、三硬脂基丙烯酸锡、三苄基月桂酸锡、三苄基2-乙基己酸锡、三苄基环烷酸锡、三苄基乙酸锡、三苄基丙烯酸锡、二苯基二月桂酸锡(diphenyltin dilaurate)、二苯基二-2-乙基己酸锡、二苯基二硬脂酸锡、二苯基二环烷酸锡、二苯基二乙酸锡、二苯基二丙烯酸锡、二正丁基二月桂酸锡、二正丁基二-2-乙基己酸锡、二正丁基二硬脂酸锡、二正丁基二环烷酸锡、二正丁基二乙酸锡、二正丁基二丙烯酸锡、二叔丁基二月桂酸锡、二叔丁基二-2-乙基己酸锡、二叔丁基二硬脂酸锡、二叔丁基二环烷酸锡、二叔丁基二乙酸锡、二叔丁基二丙烯酸锡、二异丁基二月桂酸锡、二异丁基二-2-乙基己酸锡、二异丁基二硬脂酸锡、二异丁基二环烷酸锡、二异丁基二乙酸锡、二异丁基二丙烯酸锡、二异丙基二月桂酸锡、二异丙基二-2-乙基己酸锡、二异丙基二硬脂酸锡、二异丙基二环烷酸锡、二异丙基二乙酸锡、二异丙基二丙烯酸锡、二己基二月桂酸锡、二己基二-2-乙基己酸锡、二己基二硬脂酸锡、二己基二环烷酸锡、二己基二乙酸锡、二己基二丙烯酸锡、二(2-乙基己基)二月桂酸锡、二(2-乙基己基)2-乙基己酸锡、二(2-乙基己基)二硬脂酸锡、二(2-乙基己基)二环烷酸锡、二(2-乙基己基)二乙酸锡、二(2-乙基己基)二丙烯酸锡、二辛基二月桂酸锡、二辛基二-2-乙基己酸锡、二辛基二硬脂酸锡、二辛基二环烷酸锡、二辛基二乙酸锡、二辛基二丙烯酸锡、二硬脂基二月桂酸锡、二硬脂基二-2-乙基己酸锡、二硬脂基二硬脂酸锡、二硬脂基二环烷酸锡、二硬脂基二乙酸锡、二硬脂基二丙烯酸锡、二苄基二月桂酸锡、二苄基二-2-乙基己酸锡、二苄基二硬脂酸锡、二苄基二环烷酸锡、二苄基二乙酸锡、二苄基二丙烯酸锡、苯基三月桂酸锡(phenyltin trilaurate)、苯基三-2-乙基己酸锡、苯基三环烷酸锡、苯基三乙酸锡、苯基三丙烯酸锡、正丁基三月桂酸锡、正丁基三-2-乙基己酸锡、正丁基三环烷酸锡、正丁基三乙酸锡、正丁基三丙烯酸锡、叔丁基三月桂酸锡、叔丁基三-2-乙基己酸锡、叔丁基三环烷酸锡、叔丁基三乙酸锡、叔丁基三丙烯酸锡、异丁基三月桂酸锡、异丁基三-2-乙基己酸锡、异丁基三环烷酸锡、异丁基三乙酸锡、异丁基三丙烯酸锡、异丙基三月桂酸锡、异丙基三-2-乙基己酸锡、异丙基三环烷酸锡、异丙基三乙酸锡、异丙基三丙烯酸锡、己基三月桂酸锡、己基三-2-乙基己酸锡、己基三环烷酸锡、己基三乙酸锡、己基三丙烯酸锡、辛基三月桂酸锡、辛基三-2-乙基己酸锡、辛基三环烷酸锡、辛基三乙酸锡、苄基三丙烯酸锡、2-乙基己基三月桂酸锡、2-乙基己基三-2-乙基己酸锡、2-乙基己基三环烷酸锡、2-乙基己基三乙酸锡、2-乙基己基三丙烯酸锡、硬脂基三月桂酸锡、硬脂基三-2-乙基己酸锡、硬脂基三环烷酸锡、硬脂基三乙酸锡、硬脂基三丙烯酸锡、苄基三月桂酸锡、苄基三-2-乙基己酸锡、苄基三环烷酸锡、苄基三乙酸锡、和苄基三丙烯酸锡。
化合物(g)中的R21 kM"(OCO-R22-COOR23)4-k包括二苯基锡双甲基苹果酸酯(diphenyltin bismethylmalate)、二苯基锡双-2-乙基己酸酯(diphenyltin bis-2-ethylhexanoate)、二苯基锡双辛基苹果酸酯、二苯基锡双辛基苹果酸酯、二苯基锡双苄基苹果酸酯、二正丁基锡双甲基苹果酸酯、二正丁基锡双-2-乙基己酸酯、二正丁基锡双辛基苹果酸酯、二正丁基锡双苄基苹果酸酯、二叔丁基锡双甲基苹果酸酯、二叔丁基锡双-2-乙基己酸酯、二叔丁基锡双辛基苹果酸酯、二叔丁基锡双苄基苹果酸酯、二异丁基锡双甲基苹果酸酯、二异丁基锡双-2-乙基己酸酯、二异丁基锡双辛基苹果酸酯、二异丁基锡双苄基苹果酸酯、二异丙基锡双甲基苹果酸酯、二异丙基锡双-2-乙基己酸酯、二异丙基锡双辛基苹果酸酯、二异丙基锡双苄基苹果酸酯、二己基锡双甲基苹果酸酯、二己基锡双-2-乙基己酸酯、二己基锡双辛基苹果酸酯、二己基锡双苄基苹果酸酯、二-2-乙基己基锡双甲基苹果酸酯、二-2-乙基己基锡双-2-乙基己酸酯、二-2-乙基己基锡双辛基苹果酸酯、二-2-乙基己基锡双苄基苹果酸酯、二辛基锡双甲基苹果酸酯、二辛基锡双-2-乙基己酸酯、二辛基锡双辛基苹果酸酯、二辛基锡双苄基苹果酸酯、二硬脂基锡双甲基苹果酸酯、二硬脂基锡双-2-乙基己酸酯、二硬脂基锡双辛基苹果酸酯、二硬脂基锡双苄基苹果酸酯、二苄基锡双甲基苹果酸酯、二苄基锡双-2-乙基己酸酯、二苄基锡双辛基苹果酸酯、二苄基锡双苄基苹果酸酯、二苯基锡双甲基己二酸酯、二苯基锡双-2-乙基己酸酯、二苯基锡双辛基己二酸酯、二苯基锡双苄基己二酸酯、二正丁基锡双甲基己二酸酯、二正丁基锡双-2-乙基己酸酯、二正丁基锡双辛基己二酸酯、二正丁基锡双苄基己二酸酯、二叔丁基锡双甲基己二酸酯、二叔丁基锡双-2-乙基己酸酯、二叔丁基锡双辛基己二酸酯、二叔丁基锡双苄基己二酸酯、二异丁基锡双甲基己二酸酯、二异丁基锡双-2-乙基己酸酯、二异丁基锡双辛基己二酸酯、二异丁基锡双苄基己二酸酯、二异丙基锡双甲基己二酸酯、二异丙基锡双-2-乙基己酸酯、二异丙基锡双辛基己二酸酯、二异丙基锡双苄基己二酸酯、二己基锡双甲基己二酸酯、二己基锡双-2-乙基己酸酯、二己基锡双甲基己二酸酯、二己基锡双苄基己二酸酯、二-2-乙基己基锡双甲基己二酸酯、二-2-乙基己基锡双-2-乙基己酸酯、二-2-乙基己基锡双辛基己二酸酯、二-2-乙基己基锡双-2-乙基己基锡双苄基己二酸酯(di-2-ethylhexyltin bis-2-ethylhexyltin bisbenzyladipate)、二辛基锡双甲基己二酸酯、二辛基锡双-2-乙基己酸酯、二辛基锡双辛基己二酸酯、二辛基锡双苄基己二酸酯、二硬脂基锡双甲基己二酸酯、二硬脂基锡双-2-乙基己酸酯、二硬脂基锡双辛基己二酸酯、二硬脂基锡双苄基己二酸酯、二苄基锡双甲基己二酸酯、二苄基锡双-2-乙基己酸酯、二苄基锡双辛基己二酸酯、二苄基锡双苄基己二酸酯等。
由式(VIII)表示的化合物的实例包括二苯基苹果酸锡(diphenyltin malate)、二正丁基苹果酸锡、二叔丁基苹果酸锡、二异丁基苹果酸锡、二异丙基苹果酸锡、二己基苹果酸锡、二-2-乙基己基苹果酸锡、二辛基苹果酸锡、二硬脂基苹果酸锡、二苄基苹果酸锡、二苯基己二酸锡(diphenyltin adipate)、二正丁基己二酸锡、二叔丁基己二酸锡、二异丁基己二酸锡、二异丙基己二酸锡、二己基二乙酸锡、二-2-乙基己基己二酸锡、二辛基己二酸锡、二硬脂基己二酸锡、和二苄基己二酸锡。
化合物(h)包括N-取代的氨基酮、N-取代的氨基硫酮、N-取代的氨基醛、N-取代的氨基硫醛、或分子中具有-C-(=M)-N<键(M表示氧原子或硫原子)的化合物。
化合物(h)的实例包括N-取代的氨基酮和相应的N-氨基硫酮,如4-二甲基氨基苯乙酮、4-二乙基氨基苯乙酮、1,3-双(二苯基氨基)-2-丙酮、1,7-双(甲基乙基氨基)-4-庚酮、4-二甲基氨基二苯甲酮、4-二叔丁基氨基二苯甲酮、4-二苯基氨基二苯甲酮、4,4'-双(二甲基氨基)二苯甲酮、4,4'-双(二乙基氨基)二苯甲酮、和4,4'-双(二苯基氨基)二苯甲酮;N-取代的氨基醛和相应的N-取代的氨基硫醛,如4-(二甲基氨基)苯甲醛、4-二苯基氨基苯甲醛、和4-二乙烯基氨基苯甲醛;在其分子中具有-C-(=M)-N<键(M表示氧原子或硫原子)的化合物,如N-取代的内酰胺和相应的N-取代的硫代内酰胺(thiolactams),例如,N-甲基-β-丙内酰胺、N-苯基-β-丙内酰胺、N-甲基-2-吡咯烷酮、N-苯基-2-吡咯烷酮、N-叔丁基-2-吡咯烷酮、N-苯基-5-甲基-2-吡咯烷酮、N-甲基-2-哌啶酮、N-苯基-2-哌啶酮、N-甲基-ε-己内酰胺、N-苯基-ε-己内酰胺、N-甲基-ω-己内酰胺,N-苯基-ω-己内酰胺、N-甲基-ω-十二内酰胺、和N-乙烯基-ω-十二内酰胺;和N-取代的环脲和相应的N-取代的环状硫脲(cyclic thiourea),如1,3-二甲基亚乙基脲、1,3-二乙烯基亚乙基脲、1,3-二乙基-2-咪唑啉酮、1-甲基-3-乙基-2-咪唑啉酮、和1,3-二甲基-2-咪唑啉酮。
化合物(i)为具有N≡C-键的化合物。此处,具有N≡C-键的化合物可为由通式R-CN表示的有机氰基化合物,特别是2-氰基吡啶、3-氰基吡啶、丙烯腈等;以酮、醛、环氧,特别是苯甲醛、二苯甲酮、4-4'-双(二乙基氨基)二苯甲酮、3-缩水甘油基丙基三甲氧基硅烷、芳基缩水甘油醚为代表的亲电子化合物;具有乙烯基的有机化合物,特别是丙烯、1-丁烯、1-己烯、苯乙烯、乙烯基萘、磷酸乙烯酯、乙酸乙烯酯、新戊酸乙烯酯、乙烯基三甲基硅烷、三乙氧基乙烯基硅烷等。
化合物(j)为具有由通式(I)表示的磷酸残基的化合物:
(通式(I)中,R1和R2各自独立地表示选自直链或支链C1至C20烷基、单价C3至C20脂环族烃基和单价C6至C20芳族烃基的单价烃基,或氢原子)。
更具体地,例如,可使用由通式(II)表示的磷酸残基。
这些化合物(a)至(h)可单独使用或以两种以上的组合使用,也可以与化合物(a)至(h)以外的改性剂组合使用。
本公开中的改性反应可以是液相反应或固相反应。优选液相反应(可采用聚合中使用的包含未反应单体的溶液)。任何类型的改性反应均可利用,对其没有限制。例如,可使用间歇反应器、或例如多级连续反应器和串列式(in-line)混合器等连续反应器。聚合反应后的改性反应优选在如溶剂去除、水处理、热处理和聚合物分离等必要工序之前进行。
改性反应的温度可与共轭二烯聚合物的聚合温度相同。优选的温度范围是20至100℃。低于该范围的温度导致聚合物的粘度增加,而高于该范围的温度加速不期望的聚合物活性末端的失活。
用于聚合催化剂组合物的组分(A)的改性剂的量,以摩尔为基准,在优选0.1至100的范围内,更优选为1.0至50,虽然该量取决于所得改性聚合物的末端改性率。这样的改性剂量的范围促进可制备不含甲苯不溶组分(凝胶)并且显示出低发热性和高耐摩耗性的聚合物的改性反应。
该改性反应通常在室温至100℃下搅拌优选0.5分钟至2小时、更优选3分钟至1小时来进行。具有高末端改性率的共轭二烯聚合物可以通过在实现高末端活性率的聚合条件下使用催化剂聚合,然后进行末端改性反应来制造。
<末端改性共轭二烯聚合物>
根据本公开的末端改性共轭二烯聚合物是通过本公开的上述制造方法制造的聚合物。
此处,“末端改性共轭二烯聚合物”是指通过将共轭二烯系化合物(例如1,3-丁二烯,异戊二烯等)作为单体聚合得到的聚合物的末端进行改性而得到的聚合物。
末端改性共轭二烯聚合物的顺式-1,4键含量通常为95%以上,优选为98%以上,更优选为98.5%以上。
通过将顺式-1,4键含量设定为95%以上,聚合物链的取向将会改进,应变诱导结晶性的生成将变得充分;进一步地,通过将其设定为98%以上或98.5%以上,可以生成充分的应变诱导结晶性,从而获得更高的耐久性。
末端改性共轭二烯聚合物的1,2-乙烯基键含量优选为2%以下,更优选为1%以下。
通过将1,2-乙烯基键含量设定为2%以下,应变诱导结晶性将变得不易受干扰。
末端改性共轭二烯聚合物的数均分子量(Mn)优选设定为400,000以上,更优选设定为500,000以上。
<橡胶组合物>
本公开的橡胶组合物至少包含橡胶组分,并且根据目的,可以进一步包含其它组分,例如填料、交联剂等。此外,橡胶组分至少含有通过本公开的制造方法制造的末端改性共轭二烯聚合物。
橡胶组分中的末端改性共轭二烯聚合物的含量没有限制,可以根据目的进行适当选择,其优选为15质量%至100质量%。
通过将橡胶组分中的末端改性共轭二烯聚合物的含量设定为15质量%以上,能够充分地获得末端改性共轭二烯聚合物的特性。
共轭二烯系化合物的种类没有限制,可以根据目的进行适当选择,例如可使用异戊二烯橡胶(BR)、丁苯橡胶(SBR)、丁腈橡胶(NBR)等。
此外,除了共轭二烯系化合物之外,还可将例如氯丁橡胶、乙丙橡胶(EPM)、乙烯-丙烯-非共轭二烯橡胶(EPDM)、聚硫橡胶、硅橡胶、氟橡胶、聚氨酯橡胶、和异戊二烯共聚物等其它橡胶组分混入橡胶组分中。上述橡胶组分可以单独使用或以两种以上的组合使用。
填料没有限制,可以根据目的进行适当选择;例如可使用炭黑、无机填料等,优选使用选自炭黑和无机填料中的至少一种。此处,橡胶组合物更优选包含炭黑。此外,将填料配混至橡胶组合物中以改进加强性能等。
填料的含量没有限制,可以根据目的进行适当选择;相对于100质量份的橡胶组分,优选为10质量份至100质量份,更优选为20质量份至80质量份,甚至更优选为30质量份至60质量份。
通过将填料的含量设定为10质量份以上,观察到添加填料的效果,并且通过将其设定为100质量份以下,可以将填料混合到橡胶组分中,并且可以改进作为橡胶组合物的性能。
另一方面,通过将填料的含量设定在更优选的范围内,或甚至更优选的范围内,将会改进加工性和低损耗性之间的平衡,以及加工性和耐久性之间的平衡。
无机填料没有限制,可以根据目的进行适当选择;例如可使用二氧化硅、氢氧化铝、粘土、氧化铝、滑石、云母、高岭土、玻璃球、玻璃珠、碳酸钙、碳酸镁、氢氧化镁、碳酸钙、氧化镁、氧化钛、钛酸钾、硫酸钡等。上述无机填料可单独使用或以两种以上的组合使用。
此外,当使用无机填料时,也可适当地使用硅烷偶联剂。
交联剂没有限制,可以根据目的进行适当选择;例如可使用硫磺系交联剂、有机过氧化物系交联剂、无机交联剂、多胺交联剂、树脂交联剂、硫化合物系交联剂、肟-亚硝胺系交联剂等,其中,硫磺系交联剂更优选用于轮胎用橡胶组合物。
交联剂的含量没有限制,可以根据目的进行适当选择;相对于100质量份的橡胶组分,优选为0.1质量份至20质量份。
如果交联剂的含量小于0.1质量份,则交联不能充分进行,如果含量大于20质量份,则会存在以下趋势:交联在混炼期间由于部分的交联剂进行,导致交联物质的物性的损失。
本发明的橡胶组合物还可与硫化促进剂一起使用;作为硫化促进剂,可使用胍类、醛胺类、醛氨类、噻唑类、次磺酰胺类、硫脲类、秋兰姆类、二硫代氨基甲酸类、黄原酸类等化合物。
另外,如有需要,可根据目的使用常规手段如软化剂、硫化助剂、着色剂、阻燃剂、润滑剂、发泡剂、增塑剂、加工助剂、抗氧化剂、防老剂、防焦剂、紫外线保护剂(紫外线抑制剂)、抗静电剂、着色保护剂和其它配混剂。
本发明的橡胶组合物可以进行交联并用作交联橡胶组合物。交联橡胶组合物可以是通过交联本发明的橡胶组合物获得的任何类型,对其没有限制,并且可以根据目的进行适当选择。
交联条件没有限制,可以根据目的进行适当选择;优选温度为120℃至200℃和加热时间为1分钟至900分钟。
<轮胎和其它用途>
本公开的轮胎使用本公开的橡胶组合物。
轮胎可以是使用通过交联本发明的橡胶组合物而获得的交联橡胶组合物的任何类型,对其没有限制,并且可以根据目的进行适当选择。
对本公开的橡胶组合物在轮胎上的应用位置没有限制,可以根据目的进行适当选择;例如,可使用如胎面、胎面基部、胎侧、胎侧加强橡胶、和胎圈填料等橡胶构件。
其中,通过将胎面设定为应用位置,对耐久性将是有利的。
可以使用常规方法作为轮胎的制造方法。例如,将包括未硫化橡胶和/或帘线的常用于制造轮胎的构件,例如胎体层、带束层、胎面层等按顺序重叠粘贴于轮胎成型鼓上,然后移去鼓,来得到生胎。接着,根据常规方法通过对生胎进行加热硫化,可制造出期望的轮胎(例如,充气轮胎)。
除了轮胎中的用途之外,本公开的橡胶组合物还可用在防振橡胶、隔震橡胶、带(传送带)、橡胶履带、各种软管等中。
实施例
尽管本发明不限于所公开的实施例,但是以下将根据实施例进一步详细解释本发明。
(实施例1至8)
对充分干燥的1000ml耐压玻璃反应器进行氮置换,并加入含有70g 1,3-丁二烯的己烷溶液400ml。另一方面,在氮气气氛下的手套箱中,将50.4μmol的双(2-苯基茚基)钆双(二甲基甲硅烷基酰胺)[(2-PhC9H6)2GdN(SiHMe2)2]、100μmol的3-苄基茚、750μmol的DIBAL(二异丁基氢化铝)、1ml的TMAO(由Tosoh Corporation制造)、和100μL的DEAC(二乙基氯化铝)以规定的量加入到玻璃容器中,并且溶解于30ml的n-Hex(正己烷),从而得到催化剂溶液。然后,从手套箱中取出催化剂溶液,并将以钆计的40μmol的催化剂溶液加入到单体溶液中,然后在50℃下进行聚合40分钟。聚合后,投入根据表1的改性剂并反应1小时。然后,通过加入具有5质量%的2,2'-亚甲基-双(4-乙基-6-叔丁基苯酚)(NS-5)的异丙醇溶液1mL来终止反应,使用大量的IPA(异丙醇)分离聚合物,并将其在60℃下真空干燥,来获得聚合物的样品。
此处所得到的各聚合物的样品的产量为66g。
(实施例9至16)
除了使用70g的异戊二烯代替70g的1,3-丁二烯作为共轭二烯系化合物以外,在与实施例1至8相同的条件下获得聚合物的样品。所得到的各聚合物的样品的产量为66g。
所使用的改性剂的种类如表2所示。
(实施例17和18)
除了对于实施例17,使用50.4μmol的三(叔丁醇)钆[Gd(OtBu)3]作为聚合催化剂组合物的稀土元素化合物,对于实施例18,使用50.4μmol的三(叔丁醇)钆[Gd(StBu)3]作为聚合催化剂组合物的稀土元素化合物以外,在与实施例1至8相同的条件下获得聚合物的样品。所得到的各聚合物的样品的产量为66g。
所使用的改性剂的种类如表2所示。
<评价>
(1)聚合物的评价
对于所得到的各实施例的聚合物的样品,测定改性率、顺式-1,4键含量、重均分子量(Mw)和分子量分布(MWD)。所得结果如表1和表2所示。
关于分子量分布(Mw/Mn),分别计算通过1H-NMR和13C-NMR[1H-NMR:δ4.6-4.8(3,4-乙烯基单元的=CH2)、5.0-5.2(1,4-单元的-CH=),13C-NMR:[δ23.4(1,4-顺式单元),15.9(1,4-反式单元)和18.6(3,4-单元)]获得的峰的积分比。
使用凝胶渗透色谱[GPC:由Tosoh Corporation制造的HLC-8220GPC,柱:由TosohCorporation制造的GMHXL-2根,检测器:差示折光计(RI)],基于单分散聚苯乙烯,计算聚合物样品的以聚苯乙烯换算的数均分子量(Mn)和分子量分布(MWD:Mw/Mn)。
此外,作为比较例,也示出了聚丁二烯橡胶(由UBE制造的“150L”)和聚异戊二烯橡胶(由JSR制造的“IR2200”)的顺式-1,4键含量、重均分子量和分子量分布。
(2)橡胶组合物的评价
通过使用各实施例中得到的聚合物和比较橡胶,制作通过每100质量份的聚合物组分或橡胶组分配混50质量份炭黑而获得的产物作为橡胶组合物的样品。对于所得的橡胶组合物的样品,进行以下评价。
(a)低损耗性评价
对于所得到的各实施例的橡胶组合物的样品,在160℃的条件下进行硫化20分钟。然后,通过使用Toyo Seiki Co.,Ltd.制造的分光计,在初始负荷:100g、变形:2%、测定频率:50Hz、测定温度:25℃和60℃的条件下测定损耗角正切(tanδ)。
测量值的评价由指数值表示,以比较橡胶的损耗角正切(tanδ)为100,其中值越大显示结果越好。评价结果如表1和表2所示。
(b)低摩耗性
通过使用由实施例1至8、17、18和比较例的聚丁二烯橡胶获得的橡胶组合物的样品作为胎面橡胶,制造样品轮胎。测量安装到车辆上并行驶20,000km后的样品轮胎的剩余槽深度,并且通过以当使用比较橡胶时的剩余槽深度为100的指数表示。指数值越大显示耐摩耗性越优异。
(c)断裂强度
通过使用由实施例9至18和比较例的聚异戊二烯橡胶获得的橡胶组合物的样品作为胎面橡胶,制造样品轮胎。测量橡胶的环形拉伸强度,并通过以比较例的拉伸强度为100的指数表示。指数值越大显示断裂强度越优异。
[表1]
[表2]
※1 4-4'-双(二乙基氨基二苯甲酮)
※2 2-氰基嘧啶
※3 3-缩水甘油基丙基三甲氧基硅烷
从表1和表2的结果可以理解,在各实施例中,可以以高产率合成具有高顺式-1,4键含量(98.5%以上)的聚合物。此外,可理解,聚合可以在高于常规的温度下进行。
此外,可理解,使用各实施例的聚合物的橡胶组合物的低损耗性优异,并且通过使用该橡胶组合物制造的轮胎的耐摩耗性优异。
产业上的可利用性
根据本公开,可以提供能够在没有复杂制造条件的情况下实现极高的顺式-1,4键含量的末端改性共轭二烯聚合物的制造方法,以及通过该制造方法获得的末端改性共轭二烯聚合物。
另外,通过使用上述末端改性共轭二烯聚合物,得到的橡胶组合物和轮胎的耐久性(耐断裂性、耐摩耗性和耐裂纹生长性)优异。
Claims (12)
1.一种末端改性共轭二烯聚合物的制造方法,其特征在于包括:使用聚合催化剂组合物聚合共轭二烯系化合物,并使用改性剂将经由所述聚合得到的聚合物改性,
其中所述聚合催化剂组合物包含稀土元素化合物和配位化合物,所述配位化合物具有选自取代或未取代的环戊二烯、取代或未取代的茚、和取代或未取代的芴的环戊二烯骨架,并且
其中所述聚合和改性以一锅方式进行。
2.根据权利要求1所述的末端改性共轭二烯聚合物的制造方法,其中所述稀土元素化合物由下述通式(a-1)表示:
M-(AQ1)(AQ2)(AQ3)…(a-1)
式中,M为钪、钇或镧系元素;AQ1、AQ2和AQ3为相同或不同的官能团;A为氮、氧或硫;其中具有至少一个M-A键。
3.根据权利要求1或2所述的末端改性共轭二烯聚合物的制造方法,其中所述催化剂组合物进一步包含由下述通式(X)表示的化合物:
YR31 aR32 bR33 c…(X)
式中,Y为选自周期表第1族、第2族、第12族和第13族的金属元素,R31和R32为C1至C10烃基或氢原子,R33为C1至C10烃基,其中R31、R32和R33可彼此相同或不同;此外,当Y为选自周期表第1族的金属元素时,a=1且b、c=0;当Y为选自周期表第2族和第12族的金属元素时,a、b=1且c=0;当Y为选自周期表第13族的金属元素时,a、b、c=1。
4.根据权利要求1至3任一项所述的末端改性共轭二烯聚合物的制造方法,其中具有所述环戊二烯骨架的配位化合物具有茚基。
5.根据权利要求1至4任一项所述的末端改性共轭二烯聚合物的制造方法,其中所述聚合催化剂组合物进一步包含铝氧烷化合物。
6.根据权利要求1至5任一项所述的末端改性共轭二烯聚合物的制造方法,其中所述聚合催化剂组合物进一步包含卤素化合物。
7.根据权利要求1至6任一项所述的末端改性共轭二烯聚合物的制造方法,其中所述改性剂为选自以下化合物(a)至(j)的至少之一:
(a)为由下述通式(V)表示的化合物:
其中X1至X5各自表示氢原子或单价官能团,所述单价官能团包含选自由卤素原子、羰基、硫代羰基、异氰酸酯基、硫代异氰酸酯基、环氧基、硫代环氧基、卤代甲硅烷基、烃氧基甲硅烷基和磺酰氧基组成的组的至少一种,并且不包含活性质子或鎓盐;X1至X5可相同或不同,条件是X1至X5中至少之一不为氢原子;R1至R5各自独立地表示单键或二价的C1至C18烃基;且可以通过任意的X1至X5和R1至R5键合多个氮丙啶环;
(b)为由R6 nM'Z4-n、M'Z4、M'Z3、R7 nM'(-R8-COOR9)4-n或R7 nM'(-R8-COR9)4-n表示的卤代有机金属化合物、卤代金属化合物或有机金属化合物,
其中R6至R8可相同或不同,且各自为C1至C20烃基;R9为C1至C20烃基且任选地在侧链上包含羰基或酯基;M'为锡原子、硅原子、锗原子或磷原子;Z为卤素原子;且n为0至3的整数;
(c)为分子中包含Y=C=Y'键的杂累积双键化合物,其中Y为碳原子、氧原子、氮原子或硫原子;且Y'为氧原子、氮原子或硫原子;
(d)为具有由下述通式(VI)表示的键的杂三元环化合物:
其中Y'为氧原子或硫原子;
(e)为卤代异氰基化合物;
(f)为由R10-(COOH)m、R11(COZ)m、R12-(COO-R13)、R14-OCOO-R15、R16-(COOCO-R17)m或下述通式(VII)表示的羧酸、酰卤化物、酯化合物、碳酸酯化合物或酸酐:
其中R10至R18可相同或不同,且各自为C1至C50烃基;Z为卤素原子;且m为1至5的整数;
(g)为由R19 kM"(OCOR20)4-k、R21 kM"(OCO-R22-COOR23)4-k、或下述通式(VIII)表示的羧酸的金属盐:
其中R19至R25可相同或不同,且各自为C1至C20烃基;M"为锡原子、硅原子或锗原子;且k为0至3的整数;
(h)为N-取代的氨基酮、N-取代的氨基硫酮、N-取代的氨基醛、N-取代的氨基硫醛、或分子中具有-C-(=M)-N<键的化合物,其中M表示氧原子或硫原子;
(i)为具有N≡C-键的化合物;和
(j)为具有由下述通式(I)表示的磷酸残基的化合物:
通式(I)中,R1和R2各自独立地表示选自直链或支链C1至C20烷基、单价C3至C20脂环族烃基和单价C6至C20芳族烃基的单价烃基,或氢原子。
8.一种末端改性共轭二烯聚合物,其是通过根据权利要求1至7任一项所述的末端改性共轭二烯聚合物的制造方法制得的。
9.根据权利要求8所述的末端改性共轭二烯聚合物,其中所述末端改性共轭二烯聚合物的顺式-1,4键含量为98%以上。
10.根据权利要求9所述的末端改性共轭二烯聚合物,其中所述末端改性共轭二烯聚合物的顺式-1,4键含量为98.5%以上。
11.一种橡胶组合物,其包含根据权利要求8至10任一项所述的末端改性共轭二烯聚合物作为橡胶组分。
12.一种轮胎,其使用根据权利要求11所述的橡胶组合物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2014167707 | 2014-08-20 | ||
JP2014-167707 | 2014-08-20 | ||
PCT/JP2015/003347 WO2016027401A1 (ja) | 2014-08-20 | 2015-07-02 | 末端変性共役ジエン重合体の製造方法、末端変性共役ジエン重合体、ゴム組成物及びタイヤ |
Publications (2)
Publication Number | Publication Date |
---|---|
CN106604935A true CN106604935A (zh) | 2017-04-26 |
CN106604935B CN106604935B (zh) | 2019-02-22 |
Family
ID=55350375
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201580044777.0A Active CN106604935B (zh) | 2014-08-20 | 2015-07-02 | 末端改性共轭二烯聚合物的制造方法、末端改性共轭二烯聚合物、橡胶组合物、以及轮胎 |
Country Status (6)
Country | Link |
---|---|
US (1) | US10131722B2 (zh) |
EP (1) | EP3184554B1 (zh) |
JP (1) | JP6645969B2 (zh) |
CN (1) | CN106604935B (zh) |
RU (1) | RU2671351C2 (zh) |
WO (1) | WO2016027401A1 (zh) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110753706A (zh) * | 2017-06-14 | 2020-02-04 | 株式会社普利司通 | 催化剂组合物、改性共轭二烯系聚合物的制造方法、改性共轭二烯系聚合物、橡胶组合物及轮胎 |
CN111051369A (zh) * | 2017-09-04 | 2020-04-21 | 株式会社普利司通 | 共聚物的制造方法、共聚物、橡胶组合物以及轮胎 |
CN111051360A (zh) * | 2017-09-04 | 2020-04-21 | 株式会社普利司通 | 聚合催化剂组合物、聚合物制造方法、聚合物、橡胶组合物和轮胎 |
CN114075307A (zh) * | 2020-08-13 | 2022-02-22 | 中国石油天然气股份有限公司 | 稀土催化剂及其制备方法和应用 |
CN116178594A (zh) * | 2021-11-26 | 2023-05-30 | 中国石油天然气股份有限公司 | 烯烃聚合用原位负载茂金属催化剂及其制备方法和应用 |
CN116178595A (zh) * | 2021-11-26 | 2023-05-30 | 中国石油天然气股份有限公司 | 烯烃聚合用负载茂金属催化剂及其制备方法和应用 |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10246531B2 (en) * | 2014-04-11 | 2019-04-02 | Idemitsu Kosan Co., Ltd. | Production method for olefin-based polymer, olefin polymerization catalyst, and olefin-based polymer |
JP2017203060A (ja) * | 2016-05-09 | 2017-11-16 | 株式会社ブリヂストン | ゴム組成物およびゴム物品 |
EP3456746B1 (en) * | 2016-05-09 | 2023-04-19 | Bridgestone Corporation | Terminal-modified conjugated diene-based polymer, rubber composition, and rubber article |
JPWO2017203830A1 (ja) * | 2016-05-24 | 2019-03-22 | 株式会社ブリヂストン | 末端変性共役ジエン系重合体、ゴム組成物、ゴム製品及び末端変性共役ジエン系重合体の製造方法 |
US11230618B2 (en) | 2016-11-01 | 2022-01-25 | Lg Chem, Ltd. | Modified conjugated diene-based polymer and method of preparing the same |
JPWO2018151300A1 (ja) * | 2017-02-20 | 2019-12-12 | 株式会社ブリヂストン | 変性共役ジエン系重合体の製造方法、変性共役ジエン系重合体、ゴム組成物およびタイヤ |
KR102295642B1 (ko) * | 2017-11-21 | 2021-08-31 | 주식회사 엘지화학 | 고무 조성물 |
EP3732210A4 (en) * | 2017-12-30 | 2021-08-11 | Bridgestone Corporation | COMPOSITION INCLUDING MULTIPLE POLYMERS WITH TERMINAL FUNCTIONALIZATION |
CN113166315B (zh) * | 2018-12-21 | 2023-08-01 | 株式会社Lg化学 | 改性共轭二烯类聚合物的制备方法 |
WO2020208901A1 (ja) | 2019-04-12 | 2020-10-15 | 株式会社ブリヂストン | ポリイソプレン、ゴム組成物及びタイヤ |
JP2023063831A (ja) * | 2021-10-25 | 2023-05-10 | Toyo Tire株式会社 | 末端変性ジエン系ポリマー、及びその製造方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101160328A (zh) * | 2005-04-15 | 2008-04-09 | 株式会社普利司通 | 改性共轭二烯系共聚物、橡胶组合物及轮胎 |
JP4117250B2 (ja) * | 2001-11-27 | 2008-07-16 | 株式会社ブリヂストン | 共役ジエン系重合体、その製法及びそれを用いたゴム組成物 |
CN101889050A (zh) * | 2007-12-07 | 2010-11-17 | 株式会社普利司通 | 轮胎 |
CN102015871A (zh) * | 2008-03-10 | 2011-04-13 | 株式会社普利司通 | 橡胶组合物和使用其的轮胎以及改性共轭二烯类聚合物及其生产方法 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4906706A (en) * | 1986-09-05 | 1990-03-06 | Japan Synthetic Rubber Co., Ltd. | Modified conjugated diene polymer and process for production thereof |
EP0664304B1 (en) * | 1993-12-27 | 1999-08-04 | Mitsui Chemicals, Inc. | Olefin polymerization catalyst and process for olefin polymerization |
WO2003000744A1 (en) * | 2001-06-22 | 2003-01-03 | Borealis Technology Oy | Metallocene catalysts containing an idenyl moiety substituted at the 4-, 5-, 6- or 7-position by a siloxy or germyloxy group |
ES2254934T3 (es) | 2002-05-16 | 2006-06-16 | Societe De Technologie Michelin | Sistema catalitico para preparar polibutadienos y procedimiento de preparacion. |
JP4651921B2 (ja) * | 2003-07-17 | 2011-03-16 | 株式会社ブリヂストン | 空気入りタイヤ |
JP4273887B2 (ja) | 2003-09-10 | 2009-06-03 | 日本ゼオン株式会社 | 変性共役ジエン重合体の製造方法 |
RU2464280C2 (ru) * | 2006-12-27 | 2012-10-20 | ДжейЭсЭр КОРПОРЕЙШН | Способ получения модифицированного сопряженного диенового полимера, модифицированный сопряженный диеновый полимер и резиновая композиция |
US7807763B2 (en) * | 2008-04-07 | 2010-10-05 | Bridgestone Corporation | Method for bulk polymerization |
JP2010163542A (ja) * | 2009-01-16 | 2010-07-29 | Ube Ind Ltd | 共役ジエン重合用触媒の製造方法 |
JP2011111497A (ja) * | 2009-11-25 | 2011-06-09 | Bridgestone Corp | タイヤ |
RU2569673C2 (ru) * | 2010-09-23 | 2015-11-27 | Бриджстоун Корпорейшн | Способ получения полидиенов |
JP5810764B2 (ja) * | 2011-09-02 | 2015-11-11 | 宇部興産株式会社 | ゴム組成物 |
RU2627708C2 (ru) * | 2011-12-27 | 2017-08-10 | Бриджстоун Корпорейшн | Способ полимеризации в массе для получения полидиенов |
WO2013115242A1 (ja) * | 2012-01-31 | 2013-08-08 | 旭化成ケミカルズ株式会社 | 共役ジエン系モノマーの重合触媒組成物 |
JP2013194100A (ja) * | 2012-03-16 | 2013-09-30 | Bridgestone Corp | 重合触媒組成物、及び重合体の製造方法 |
-
2015
- 2015-07-02 CN CN201580044777.0A patent/CN106604935B/zh active Active
- 2015-07-02 EP EP15833853.3A patent/EP3184554B1/en active Active
- 2015-07-02 US US15/503,884 patent/US10131722B2/en not_active Expired - Fee Related
- 2015-07-02 WO PCT/JP2015/003347 patent/WO2016027401A1/ja active Application Filing
- 2015-07-02 RU RU2017108844A patent/RU2671351C2/ru active
- 2015-07-02 JP JP2016543795A patent/JP6645969B2/ja active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4117250B2 (ja) * | 2001-11-27 | 2008-07-16 | 株式会社ブリヂストン | 共役ジエン系重合体、その製法及びそれを用いたゴム組成物 |
CN101160328A (zh) * | 2005-04-15 | 2008-04-09 | 株式会社普利司通 | 改性共轭二烯系共聚物、橡胶组合物及轮胎 |
CN101889050A (zh) * | 2007-12-07 | 2010-11-17 | 株式会社普利司通 | 轮胎 |
US20110112212A1 (en) * | 2007-12-07 | 2011-05-12 | Bridgestone Corporation | Tire |
CN102015871A (zh) * | 2008-03-10 | 2011-04-13 | 株式会社普利司通 | 橡胶组合物和使用其的轮胎以及改性共轭二烯类聚合物及其生产方法 |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110753706A (zh) * | 2017-06-14 | 2020-02-04 | 株式会社普利司通 | 催化剂组合物、改性共轭二烯系聚合物的制造方法、改性共轭二烯系聚合物、橡胶组合物及轮胎 |
CN111051369A (zh) * | 2017-09-04 | 2020-04-21 | 株式会社普利司通 | 共聚物的制造方法、共聚物、橡胶组合物以及轮胎 |
CN111051360A (zh) * | 2017-09-04 | 2020-04-21 | 株式会社普利司通 | 聚合催化剂组合物、聚合物制造方法、聚合物、橡胶组合物和轮胎 |
US11472907B2 (en) | 2017-09-04 | 2022-10-18 | Bridgestone Corporation | Polymerization catalyst composition, polymer manufacturing method, polymer, rubber composition, and tire |
CN111051360B (zh) * | 2017-09-04 | 2022-10-28 | 株式会社普利司通 | 聚合催化剂组合物、聚合物制造方法、聚合物、橡胶组合物和轮胎 |
CN114075307A (zh) * | 2020-08-13 | 2022-02-22 | 中国石油天然气股份有限公司 | 稀土催化剂及其制备方法和应用 |
CN114075307B (zh) * | 2020-08-13 | 2024-03-26 | 中国石油天然气股份有限公司 | 稀土催化剂及其制备方法和应用 |
CN116178594A (zh) * | 2021-11-26 | 2023-05-30 | 中国石油天然气股份有限公司 | 烯烃聚合用原位负载茂金属催化剂及其制备方法和应用 |
CN116178595A (zh) * | 2021-11-26 | 2023-05-30 | 中国石油天然气股份有限公司 | 烯烃聚合用负载茂金属催化剂及其制备方法和应用 |
Also Published As
Publication number | Publication date |
---|---|
JPWO2016027401A1 (ja) | 2017-06-08 |
RU2017108844A3 (zh) | 2018-09-20 |
RU2671351C2 (ru) | 2018-10-30 |
EP3184554A1 (en) | 2017-06-28 |
CN106604935B (zh) | 2019-02-22 |
US10131722B2 (en) | 2018-11-20 |
EP3184554B1 (en) | 2019-09-04 |
RU2017108844A (ru) | 2018-09-20 |
US20170275400A1 (en) | 2017-09-28 |
WO2016027401A1 (ja) | 2016-02-25 |
EP3184554A4 (en) | 2017-08-23 |
JP6645969B2 (ja) | 2020-02-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN106604935B (zh) | 末端改性共轭二烯聚合物的制造方法、末端改性共轭二烯聚合物、橡胶组合物、以及轮胎 | |
CN102639568B (zh) | 官能化聚合物及其制造方法 | |
CN106459311B (zh) | 多元共聚物的制备方法 | |
CN107531853A (zh) | 用于制备基于共轭二烯的聚合物的催化剂组合物和使用其制备的基于共轭二烯的聚合物 | |
CN101225134A (zh) | 生产具有高顺式1,4-键含量和高官能度的官能化顺式1,4-聚二烯的方法 | |
EP3280745A1 (en) | Initiators for the copolymerisation of diene monomers and vinyl aromatic monomers | |
JP5899011B2 (ja) | 重合体、前記重合体を含むゴム組成物、及び、前記ゴム組成物を有するタイヤ | |
JP5941302B2 (ja) | ゴム組成物、及び、前記ゴム組成物を有するタイヤ | |
CN108884271A (zh) | 改性剂和包含由其衍生的官能团的改性共轭二烯类聚合物 | |
CN104159932B (zh) | 聚合物及其制造方法,含有聚合物的橡胶组合物,和具有橡胶组合物的轮胎 | |
CN109153737A (zh) | 末端改性的共轭二烯聚合物、橡胶组合物、橡胶产品和末端改性的共轭二烯聚合物的制造方法 | |
CN104428332B (zh) | 异戊二烯共聚物及其制造方法 | |
CN108884269A (zh) | 改性共轭二烯类聚合物及其制备方法 | |
CN105814087B (zh) | 用含有氰基基团的亚胺化合物官能化的聚合物 | |
CN110325554A (zh) | 改性共轭二烯系聚合物的制造方法、改性共轭二烯系聚合物、橡胶组合物以及轮胎 | |
KR101740773B1 (ko) | 디엔계 중합체의 제조방법 및 이를 이용하여 제조한 디엔계 중합체 | |
WO2017195634A1 (ja) | 末端変性共役ジエン系重合体、ゴム組成物およびゴム物品 | |
WO2020121745A1 (ja) | 共重合体、共重合体の製造方法、ゴム組成物、タイヤ、樹脂組成物及び樹脂製品 | |
WO2019225146A1 (ja) | 重合触媒、及び、共重合体の製造方法 | |
WO2021126003A1 (en) | Branched polydienes, rubber compositions based on thereof | |
JP2016113496A (ja) | ゴム組成物、及び該ゴム組成物を用いたタイヤ | |
KR101726025B1 (ko) | 디엔계 중합체의 제조방법 및 이를 이용하여 제조한 디엔계 중합체 | |
WO2019225145A1 (ja) | 重合触媒、及び、共重合体の製造方法 | |
JP2016003271A (ja) | 分岐イソプレン重合体の製造方法 | |
CN109627359A (zh) | 含硅及磷的改质橡胶及其组合物与制造方法 |
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 | ||
GR01 | Patent grant | ||
GR01 | Patent grant |