CA2378498A1 - Block copolymer based on conjugated diolefins and polar monomers - Google Patents
Block copolymer based on conjugated diolefins and polar monomers Download PDFInfo
- Publication number
- CA2378498A1 CA2378498A1 CA002378498A CA2378498A CA2378498A1 CA 2378498 A1 CA2378498 A1 CA 2378498A1 CA 002378498 A CA002378498 A CA 002378498A CA 2378498 A CA2378498 A CA 2378498A CA 2378498 A1 CA2378498 A1 CA 2378498A1
- Authority
- CA
- Canada
- Prior art keywords
- polymerized
- iii
- polar monomers
- conjugated
- dimes
- 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.)
- Abandoned
Links
- 239000000178 monomer Substances 0.000 title claims abstract description 55
- 229920001400 block copolymer Polymers 0.000 title claims abstract description 53
- 150000001993 dienes Chemical class 0.000 title claims abstract description 42
- 229910052761 rare earth metal Inorganic materials 0.000 claims abstract description 33
- 150000002910 rare earth metals Chemical class 0.000 claims abstract description 33
- 239000003054 catalyst Substances 0.000 claims abstract description 26
- 239000000203 mixture Substances 0.000 claims abstract description 26
- 239000000945 filler Substances 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 4
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 4
- 230000004048 modification Effects 0.000 claims abstract description 3
- 238000012986 modification Methods 0.000 claims abstract description 3
- 229920002725 thermoplastic elastomer Polymers 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 28
- 238000006116 polymerization reaction Methods 0.000 claims description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 25
- -1 cyclic sulfides Chemical class 0.000 claims description 23
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 18
- 229910052779 Neodymium Inorganic materials 0.000 claims description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 150000002596 lactones Chemical class 0.000 claims description 7
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 claims description 6
- RCJMVGJKROQDCB-UHFFFAOYSA-N 2-methylpenta-1,3-diene Chemical compound CC=CC(C)=C RCJMVGJKROQDCB-UHFFFAOYSA-N 0.000 claims description 6
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 6
- 150000005676 cyclic carbonates Chemical class 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 4
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 claims description 4
- 239000002841 Lewis acid Substances 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 150000007942 carboxylates Chemical class 0.000 claims description 4
- 125000005594 diketone group Chemical group 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 150000007517 lewis acids Chemical class 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 235000021317 phosphate Nutrition 0.000 claims description 4
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 claims description 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 3
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 claims description 3
- 150000003951 lactams Chemical class 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims description 3
- 239000012815 thermoplastic material Substances 0.000 claims description 3
- 150000003571 thiolactams Chemical class 0.000 claims description 3
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- ARWCRSVRKCNEDI-UHFFFAOYSA-K neodymium(3+);octanoate Chemical compound [Nd+3].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O ARWCRSVRKCNEDI-UHFFFAOYSA-K 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 2
- 239000003849 aromatic solvent Substances 0.000 claims 2
- GSCLMSFRWBPUSK-UHFFFAOYSA-N beta-Butyrolactone Chemical compound CC1CC(=O)O1 GSCLMSFRWBPUSK-UHFFFAOYSA-N 0.000 claims 2
- 150000002118 epoxides Chemical class 0.000 claims 2
- 230000000379 polymerizing effect Effects 0.000 claims 2
- 239000001273 butane Substances 0.000 claims 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 25
- 239000003795 chemical substances by application Substances 0.000 abstract description 7
- 229920006112 polar polymer Polymers 0.000 abstract description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- 229920001971 elastomer Polymers 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 239000005060 rubber Substances 0.000 description 12
- ATINCSYRHURBSP-UHFFFAOYSA-K neodymium(iii) chloride Chemical compound Cl[Nd](Cl)Cl ATINCSYRHURBSP-UHFFFAOYSA-K 0.000 description 11
- 239000005062 Polybutadiene Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 9
- 238000012661 block copolymerization Methods 0.000 description 8
- ICAKDTKJOYSXGC-UHFFFAOYSA-K lanthanum(iii) chloride Chemical compound Cl[La](Cl)Cl ICAKDTKJOYSXGC-UHFFFAOYSA-K 0.000 description 8
- LHBNLZDGIPPZLL-UHFFFAOYSA-K praseodymium(iii) chloride Chemical compound Cl[Pr](Cl)Cl LHBNLZDGIPPZLL-UHFFFAOYSA-K 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 239000011521 glass Substances 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- 229910014323 Lanthanum(III) bromide Inorganic materials 0.000 description 6
- 229960004592 isopropanol Drugs 0.000 description 6
- 229910052746 lanthanum Inorganic materials 0.000 description 6
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 6
- XKUYOJZZLGFZTC-UHFFFAOYSA-K lanthanum(iii) bromide Chemical compound Br[La](Br)Br XKUYOJZZLGFZTC-UHFFFAOYSA-K 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- LBWLQVSRPJHLEY-UHFFFAOYSA-K neodymium(3+);tribromide Chemical compound Br[Nd](Br)Br LBWLQVSRPJHLEY-UHFFFAOYSA-K 0.000 description 6
- 229920002857 polybutadiene Polymers 0.000 description 6
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229920002521 macromolecule Polymers 0.000 description 5
- 239000011159 matrix material Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- PLKCYEBERAEWDR-UHFFFAOYSA-K praseodymium(3+);tribromide Chemical compound Br[Pr](Br)Br PLKCYEBERAEWDR-UHFFFAOYSA-K 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 4
- 238000001291 vacuum drying Methods 0.000 description 4
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 3
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229910052777 Praseodymium Inorganic materials 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 150000005840 aryl radicals Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- MGDOJPNDRJNJBK-UHFFFAOYSA-N ethylaluminum Chemical compound [Al].C[CH2] MGDOJPNDRJNJBK-UHFFFAOYSA-N 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- CZMAIROVPAYCMU-UHFFFAOYSA-N lanthanum(3+) Chemical compound [La+3] CZMAIROVPAYCMU-UHFFFAOYSA-N 0.000 description 3
- 229940049964 oleate Drugs 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 3
- WCWKKSOQLQEJTE-UHFFFAOYSA-N praseodymium(3+) Chemical compound [Pr+3] WCWKKSOQLQEJTE-UHFFFAOYSA-N 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 238000004627 transmission electron microscopy Methods 0.000 description 3
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 2
- NMXLXQGHBSPIDR-UHFFFAOYSA-N 2-(2-methylpropyl)oxaluminane Chemical compound CC(C)C[Al]1CCCCO1 NMXLXQGHBSPIDR-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- XZMKUVNUDMQGLO-UHFFFAOYSA-N 2-ethylhexan-1-olate;neodymium(3+) Chemical compound [Nd+3].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-] XZMKUVNUDMQGLO-UHFFFAOYSA-N 0.000 description 2
- AQZWEFBJYQSQEH-UHFFFAOYSA-N 2-methyloxaluminane Chemical compound C[Al]1CCCCO1 AQZWEFBJYQSQEH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 101100378709 Arabidopsis thaliana AIR3 gene Proteins 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- OHVSOKQNNQBGQB-UHFFFAOYSA-N C(CCCCCCC)OP(OCCCCCCCC)=O.[Nd+3] Chemical compound C(CCCCCCC)OP(OCCCCCCCC)=O.[Nd+3] OHVSOKQNNQBGQB-UHFFFAOYSA-N 0.000 description 2
- YBTXYRSEXVNDOQ-UHFFFAOYSA-N C(CCCCCCCCC)[O-].[Nd+3].C(CCCCCCCCC)[O-].C(CCCCCCCCC)[O-] Chemical compound C(CCCCCCCCC)[O-].[Nd+3].C(CCCCCCCCC)[O-].C(CCCCCCCCC)[O-] YBTXYRSEXVNDOQ-UHFFFAOYSA-N 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 229910052772 Samarium Inorganic materials 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000006193 alkinyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- YPEWLXGESTWIDH-UHFFFAOYSA-N butan-1-olate;neodymium(3+) Chemical compound [Nd+3].CCCC[O-].CCCC[O-].CCCC[O-] YPEWLXGESTWIDH-UHFFFAOYSA-N 0.000 description 2
- DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 229920003193 cis-1,4-polybutadiene polymer Polymers 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- VTZJFPSWNQFPCQ-UHFFFAOYSA-N dibutylaluminum Chemical compound CCCC[Al]CCCC VTZJFPSWNQFPCQ-UHFFFAOYSA-N 0.000 description 2
- BYLOHCRAPOSXLY-UHFFFAOYSA-N dichloro(diethyl)silane Chemical compound CC[Si](Cl)(Cl)CC BYLOHCRAPOSXLY-UHFFFAOYSA-N 0.000 description 2
- JJSGABFIILQOEY-UHFFFAOYSA-M diethylalumanylium;bromide Chemical compound CC[Al](Br)CC JJSGABFIILQOEY-UHFFFAOYSA-M 0.000 description 2
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-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
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 2
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- AKNMPWVTPUHKCG-UHFFFAOYSA-N 2-cyclohexyl-6-[(3-cyclohexyl-2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound OC=1C(C2CCCCC2)=CC(C)=CC=1CC(C=1O)=CC(C)=CC=1C1CCCCC1 AKNMPWVTPUHKCG-UHFFFAOYSA-N 0.000 description 1
- KMGAHAHNJQKKTP-UHFFFAOYSA-K 2-ethylbutanoate;lanthanum(3+) Chemical compound [La+3].CCC(CC)C([O-])=O.CCC(CC)C([O-])=O.CCC(CC)C([O-])=O KMGAHAHNJQKKTP-UHFFFAOYSA-K 0.000 description 1
- PQXQGYCQXZLXPU-UHFFFAOYSA-K 2-ethylbutanoate;neodymium(3+) Chemical compound [Nd+3].CCC(CC)C([O-])=O.CCC(CC)C([O-])=O.CCC(CC)C([O-])=O PQXQGYCQXZLXPU-UHFFFAOYSA-K 0.000 description 1
- PPNFILUQDVDXDA-UHFFFAOYSA-K 2-ethylhexanoate;lanthanum(3+) Chemical compound [La+3].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O PPNFILUQDVDXDA-UHFFFAOYSA-K 0.000 description 1
- QBKTXRLYEHZACW-UHFFFAOYSA-K 2-ethylhexanoate;neodymium(3+) Chemical compound [Nd+3].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O QBKTXRLYEHZACW-UHFFFAOYSA-K 0.000 description 1
- LJLKMNSTMFZSEO-UHFFFAOYSA-K 2-ethylhexanoate;praseodymium(3+) Chemical compound [Pr+3].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O LJLKMNSTMFZSEO-UHFFFAOYSA-K 0.000 description 1
- YVSMQHYREUQGRX-UHFFFAOYSA-N 2-ethyloxaluminane Chemical compound CC[Al]1CCCCO1 YVSMQHYREUQGRX-UHFFFAOYSA-N 0.000 description 1
- MBNVSWHUJDDZRH-UHFFFAOYSA-N 2-methylthiirane Chemical compound CC1CS1 MBNVSWHUJDDZRH-UHFFFAOYSA-N 0.000 description 1
- OQOIYECUXDNABI-UHFFFAOYSA-N 2-phenylthiirane Chemical compound C1SC1C1=CC=CC=C1 OQOIYECUXDNABI-UHFFFAOYSA-N 0.000 description 1
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 1
- LLQHSBBZNDXTIV-UHFFFAOYSA-N 6-[5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-4,5-dihydro-1,2-oxazol-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC1CC(=NO1)C1=CC2=C(NC(O2)=O)C=C1 LLQHSBBZNDXTIV-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- SMJBXUGRWBYCPM-UHFFFAOYSA-K C(C)C(C(=O)[O-])CC.[Pr+3].C(C)C(C(=O)[O-])CC.C(C)C(C(=O)[O-])CC Chemical compound C(C)C(C(=O)[O-])CC.[Pr+3].C(C)C(C(=O)[O-])CC.C(C)C(C(=O)[O-])CC SMJBXUGRWBYCPM-UHFFFAOYSA-K 0.000 description 1
- XRBLOPCCLRDKJO-UHFFFAOYSA-N C(C)C(C[O-])CCCC.[La+3].C(C)C(C[O-])CCCC.C(C)C(C[O-])CCCC Chemical compound C(C)C(C[O-])CCCC.[La+3].C(C)C(C[O-])CCCC.C(C)C(C[O-])CCCC XRBLOPCCLRDKJO-UHFFFAOYSA-N 0.000 description 1
- HFCMDKFFOOECKP-UHFFFAOYSA-N C(C)C(C[O-])CCCC.[Pr+3].C(C)C(C[O-])CCCC.C(C)C(C[O-])CCCC Chemical compound C(C)C(C[O-])CCCC.[Pr+3].C(C)C(C[O-])CCCC.C(C)C(C[O-])CCCC HFCMDKFFOOECKP-UHFFFAOYSA-N 0.000 description 1
- QDLPVTOUHYVOFX-UHFFFAOYSA-N C(CCC)OP(OCCCC)=O.[Nd+3] Chemical compound C(CCC)OP(OCCCC)=O.[Nd+3] QDLPVTOUHYVOFX-UHFFFAOYSA-N 0.000 description 1
- BOISDYXPANFGAY-UHFFFAOYSA-N C(CCCC)OP(OCCCCC)=O.[Nd+3] Chemical compound C(CCCC)OP(OCCCCC)=O.[Nd+3] BOISDYXPANFGAY-UHFFFAOYSA-N 0.000 description 1
- SCGGGQZVUDQGHO-UHFFFAOYSA-N C(CCCCC)OP(OCCCCCC)=O.[Nd+3] Chemical compound C(CCCCC)OP(OCCCCCC)=O.[Nd+3] SCGGGQZVUDQGHO-UHFFFAOYSA-N 0.000 description 1
- VSJQTWWWJMTGQQ-UHFFFAOYSA-N C(CCCCCC)OP(OCCCCCCC)=O.[Nd+3] Chemical compound C(CCCCCC)OP(OCCCCCCC)=O.[Nd+3] VSJQTWWWJMTGQQ-UHFFFAOYSA-N 0.000 description 1
- PLNKJSMTLNRWBB-UHFFFAOYSA-N C(CCCCCCCC)OP(OCCCCCCCCC)=O.[Nd+3] Chemical compound C(CCCCCCCC)OP(OCCCCCCCCC)=O.[Nd+3] PLNKJSMTLNRWBB-UHFFFAOYSA-N 0.000 description 1
- AVOOJGZNRAQOEO-UHFFFAOYSA-N C(CCCCCCCCC)[O-].[La+3].C(CCCCCCCCC)[O-].C(CCCCCCCCC)[O-] Chemical compound C(CCCCCCCCC)[O-].[La+3].C(CCCCCCCCC)[O-].C(CCCCCCCCC)[O-] AVOOJGZNRAQOEO-UHFFFAOYSA-N 0.000 description 1
- ACUOWFBJMGDGQW-UHFFFAOYSA-N C(CCCCCCCCC)[O-].[Pr+3].C(CCCCCCCCC)[O-].C(CCCCCCCCC)[O-] Chemical compound C(CCCCCCCCC)[O-].[Pr+3].C(CCCCCCCCC)[O-].C(CCCCCCCCC)[O-] ACUOWFBJMGDGQW-UHFFFAOYSA-N 0.000 description 1
- FZJOSBGGSLZARI-UHFFFAOYSA-N C(CCCCCCCCCCC)OP(OCCCCCCCCCCCC)=O.[Nd+3] Chemical compound C(CCCCCCCCCCC)OP(OCCCCCCCCCCCC)=O.[Nd+3] FZJOSBGGSLZARI-UHFFFAOYSA-N 0.000 description 1
- MLGMKBHDVSSSCC-UHFFFAOYSA-K C1(CCCCC1)C(=O)[O-].[La+3].C1(CCCCC1)C(=O)[O-].C1(CCCCC1)C(=O)[O-] Chemical compound C1(CCCCC1)C(=O)[O-].[La+3].C1(CCCCC1)C(=O)[O-].C1(CCCCC1)C(=O)[O-] MLGMKBHDVSSSCC-UHFFFAOYSA-K 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 238000004639 Schlenk technique Methods 0.000 description 1
- SZKKRCSOSQAJDE-UHFFFAOYSA-N Schradan Chemical group CN(C)P(=O)(N(C)C)OP(=O)(N(C)C)N(C)C SZKKRCSOSQAJDE-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- PTISNQVXRPCWIC-UHFFFAOYSA-K [Pr+3].CCC([O-])=O.CCC([O-])=O.CCC([O-])=O Chemical compound [Pr+3].CCC([O-])=O.CCC([O-])=O.CCC([O-])=O PTISNQVXRPCWIC-UHFFFAOYSA-K 0.000 description 1
- 238000004847 absorption spectroscopy Methods 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 1
- 239000011952 anionic catalyst Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000003712 anti-aging effect Effects 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
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- APLHDUWNMGJBFD-UHFFFAOYSA-N azepane-2-thione Chemical compound S=C1CCCCCN1 APLHDUWNMGJBFD-UHFFFAOYSA-N 0.000 description 1
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- NZIXICKPQWIFAU-UHFFFAOYSA-K bromo(dimethyl)alumane;dibromo(methyl)alumane Chemical compound C[Al](C)Br.C[Al](Br)Br NZIXICKPQWIFAU-UHFFFAOYSA-K 0.000 description 1
- ACBSZXDTALWBAM-UHFFFAOYSA-N butan-1-olate praseodymium(3+) Chemical compound [Pr+3].CCCC[O-].CCCC[O-].CCCC[O-] ACBSZXDTALWBAM-UHFFFAOYSA-N 0.000 description 1
- NYPANIKZEAZXAE-UHFFFAOYSA-N butan-1-olate;lanthanum(3+) Chemical compound [La+3].CCCC[O-].CCCC[O-].CCCC[O-] NYPANIKZEAZXAE-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
- SHOVVTSKTTYFGP-UHFFFAOYSA-L butylaluminum(2+);dichloride Chemical compound CCCC[Al](Cl)Cl SHOVVTSKTTYFGP-UHFFFAOYSA-L 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000006364 carbonyl oxy methylene group Chemical group [H]C([H])([*:2])OC([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- HYZXMVILOKSUKA-UHFFFAOYSA-K chloro(dimethyl)alumane;dichloro(methyl)alumane Chemical compound C[Al](C)Cl.C[Al](Cl)Cl HYZXMVILOKSUKA-UHFFFAOYSA-K 0.000 description 1
- NNKJLYMBVRDUEI-UHFFFAOYSA-N chloro-tris(ethenyl)silane Chemical compound C=C[Si](Cl)(C=C)C=C NNKJLYMBVRDUEI-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000012967 coordination catalyst Substances 0.000 description 1
- ACIIURKHTPQCPL-UHFFFAOYSA-K cyclohexanecarboxylate;neodymium(3+) Chemical compound [Nd+3].[O-]C(=O)C1CCCCC1.[O-]C(=O)C1CCCCC1.[O-]C(=O)C1CCCCC1 ACIIURKHTPQCPL-UHFFFAOYSA-K 0.000 description 1
- CHNDFUGIWKLFGN-UHFFFAOYSA-K cyclohexanecarboxylate;praseodymium(3+) Chemical compound [Pr+3].[O-]C(=O)C1CCCCC1.[O-]C(=O)C1CCCCC1.[O-]C(=O)C1CCCCC1 CHNDFUGIWKLFGN-UHFFFAOYSA-K 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- NNPWWKQUTCVLAD-UHFFFAOYSA-N di(nonyl)phosphinic acid Chemical compound CCCCCCCCCP(O)(=O)CCCCCCCCC NNPWWKQUTCVLAD-UHFFFAOYSA-N 0.000 description 1
- VJRUISVXILMZSL-UHFFFAOYSA-M dibutylalumanylium;chloride Chemical compound CCCC[Al](Cl)CCCC VJRUISVXILMZSL-UHFFFAOYSA-M 0.000 description 1
- XYBPXKSKJGTKJB-UHFFFAOYSA-K dibutylphosphinate;neodymium(3+) Chemical compound [Nd+3].CCCCP([O-])(=O)CCCC.CCCCP([O-])(=O)CCCC.CCCCP([O-])(=O)CCCC XYBPXKSKJGTKJB-UHFFFAOYSA-K 0.000 description 1
- MAYIDWCWWMOISO-UHFFFAOYSA-N dichloro-bis(ethenyl)silane Chemical compound C=C[Si](Cl)(Cl)C=C MAYIDWCWWMOISO-UHFFFAOYSA-N 0.000 description 1
- BRJZEGHWEPTWAX-UHFFFAOYSA-K didodecylphosphinate;neodymium(3+) Chemical compound [Nd+3].CCCCCCCCCCCCP([O-])(=O)CCCCCCCCCCCC.CCCCCCCCCCCCP([O-])(=O)CCCCCCCCCCCC.CCCCCCCCCCCCP([O-])(=O)CCCCCCCCCCCC BRJZEGHWEPTWAX-UHFFFAOYSA-K 0.000 description 1
- HJXBDPDUCXORKZ-UHFFFAOYSA-N diethylalumane Chemical compound CC[AlH]CC HJXBDPDUCXORKZ-UHFFFAOYSA-N 0.000 description 1
- JTGUKNQMNXAFIS-UHFFFAOYSA-K diheptylphosphinate;neodymium(3+) Chemical compound [Nd+3].CCCCCCCP([O-])(=O)CCCCCCC.CCCCCCCP([O-])(=O)CCCCCCC.CCCCCCCP([O-])(=O)CCCCCCC JTGUKNQMNXAFIS-UHFFFAOYSA-K 0.000 description 1
- XHFZHPQZVCWVBA-UHFFFAOYSA-K dihexylphosphinate;neodymium(3+) Chemical compound [Nd+3].CCCCCCP([O-])(=O)CCCCCC.CCCCCCP([O-])(=O)CCCCCC.CCCCCCP([O-])(=O)CCCCCC XHFZHPQZVCWVBA-UHFFFAOYSA-K 0.000 description 1
- ZGMHEOLLTWPGQX-UHFFFAOYSA-M dimethylalumanylium;bromide Chemical compound C[Al](C)Br ZGMHEOLLTWPGQX-UHFFFAOYSA-M 0.000 description 1
- JGHYBJVUQGTEEB-UHFFFAOYSA-M dimethylalumanylium;chloride Chemical compound C[Al](C)Cl JGHYBJVUQGTEEB-UHFFFAOYSA-M 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- UZSAHKACJKVKEK-UHFFFAOYSA-K dioctylphosphinate;neodymium(3+) Chemical compound [Nd+3].CCCCCCCCP([O-])(=O)CCCCCCCC.CCCCCCCCP([O-])(=O)CCCCCCCC.CCCCCCCCP([O-])(=O)CCCCCCCC UZSAHKACJKVKEK-UHFFFAOYSA-K 0.000 description 1
- YTMRJBAHYSIRMZ-UHFFFAOYSA-N dioctylphosphinic acid Chemical compound CCCCCCCCP(O)(=O)CCCCCCCC YTMRJBAHYSIRMZ-UHFFFAOYSA-N 0.000 description 1
- CMISOYBKHBNISI-UHFFFAOYSA-K dipentylphosphinate;neodymium(3+) Chemical compound [Nd+3].CCCCCP([O-])(=O)CCCCC.CCCCCP([O-])(=O)CCCCC.CCCCCP([O-])(=O)CCCCC CMISOYBKHBNISI-UHFFFAOYSA-K 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 239000002044 hexane fraction Substances 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000011078 in-house production Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002655 kraft paper Substances 0.000 description 1
- ILPVRBLJWLAMPB-UHFFFAOYSA-N lanthanum(3+) propan-1-olate Chemical compound [La+3].CCC[O-].CCC[O-].CCC[O-] ILPVRBLJWLAMPB-UHFFFAOYSA-N 0.000 description 1
- HDIBUQNJDKISLA-MUCWUPSWSA-K lanthanum(3+);(e)-4-oxopent-2-en-2-olate Chemical compound [La+3].C\C([O-])=C/C(C)=O.C\C([O-])=C/C(C)=O.C\C([O-])=C/C(C)=O HDIBUQNJDKISLA-MUCWUPSWSA-K 0.000 description 1
- NCRUJFPNHKQCJG-UHFFFAOYSA-K lanthanum(3+);propanoate Chemical compound [La+3].CCC([O-])=O.CCC([O-])=O.CCC([O-])=O NCRUJFPNHKQCJG-UHFFFAOYSA-K 0.000 description 1
- ILRDAEXCKRFJPK-UHFFFAOYSA-K lanthanum(3+);tribenzoate Chemical compound [La+3].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 ILRDAEXCKRFJPK-UHFFFAOYSA-K 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 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
- 239000002808 molecular sieve Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 150000002798 neodymium compounds Chemical class 0.000 description 1
- SIINVGJQWZKNSJ-UHFFFAOYSA-K neodymium(3+);octadecanoate Chemical compound [Nd+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O SIINVGJQWZKNSJ-UHFFFAOYSA-K 0.000 description 1
- IRGLOWNFSUBRSR-UHFFFAOYSA-N neodymium(3+);propan-1-olate Chemical compound [Nd+3].CCC[O-].CCC[O-].CCC[O-] IRGLOWNFSUBRSR-UHFFFAOYSA-N 0.000 description 1
- RILQQYPQBCNTQF-UHFFFAOYSA-K neodymium(3+);propanoate Chemical compound [Nd+3].CCC([O-])=O.CCC([O-])=O.CCC([O-])=O RILQQYPQBCNTQF-UHFFFAOYSA-K 0.000 description 1
- HPCGPGSYNUPEKZ-UHFFFAOYSA-K neodymium(3+);tribenzoate Chemical compound [Nd+3].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 HPCGPGSYNUPEKZ-UHFFFAOYSA-K 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- HKITTYDLDOKDRC-UHFFFAOYSA-K octadecanoate;praseodymium(3+) Chemical compound [Pr+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HKITTYDLDOKDRC-UHFFFAOYSA-K 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920001291 polyvinyl halide Polymers 0.000 description 1
- RETHCFDWOPJAIU-UHFFFAOYSA-N praseodymium(3+);propan-1-olate Chemical compound [Pr+3].CCC[O-].CCC[O-].CCC[O-] RETHCFDWOPJAIU-UHFFFAOYSA-N 0.000 description 1
- UMIVUKFKISBKQB-UHFFFAOYSA-N praseodymium(3+);propan-2-olate Chemical compound [Pr+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] UMIVUKFKISBKQB-UHFFFAOYSA-N 0.000 description 1
- XDFGURDROXHOOM-UHFFFAOYSA-K praseodymium(3+);tribenzoate Chemical compound [Pr+3].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 XDFGURDROXHOOM-UHFFFAOYSA-K 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- IMWUREPEYPRYOR-UHFFFAOYSA-N pyrrolidine-2-thione Chemical compound S=C1CCCN1 IMWUREPEYPRYOR-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- RSNQKPMXXVDJFG-UHFFFAOYSA-N tetrasiloxane Chemical compound [SiH3]O[SiH2]O[SiH2]O[SiH3] RSNQKPMXXVDJFG-UHFFFAOYSA-N 0.000 description 1
- VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical compound CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 0.000 description 1
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- JOJQVUCWSDRWJE-UHFFFAOYSA-N tripentylalumane Chemical compound CCCCC[Al](CCCCC)CCCCC JOJQVUCWSDRWJE-UHFFFAOYSA-N 0.000 description 1
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C08F297/06—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the coordination type
Landscapes
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Polymerization Catalysts (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10115106A DE10115106A1 (de) | 2001-03-27 | 2001-03-27 | Blockcopolymerisat auf Basis von konjugierten Diolefinen und polaren Monomeren |
| DE10115106.3 | 2001-03-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2378498A1 true CA2378498A1 (en) | 2002-09-27 |
Family
ID=7679267
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002378498A Abandoned CA2378498A1 (en) | 2001-03-27 | 2002-03-22 | Block copolymer based on conjugated diolefins and polar monomers |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US6734257B2 (enExample) |
| EP (1) | EP1245600B1 (enExample) |
| JP (1) | JP3997313B2 (enExample) |
| CA (1) | CA2378498A1 (enExample) |
| DE (2) | DE10115106A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2266457T3 (es) * | 2001-02-28 | 2007-03-01 | Bridgestone Corporation | Procedimiento continuo para la produccion de polimeros de dieno conjugados que tienen distribucion de peso molecular estrecha y productos de los mismos. |
| FR2824834B1 (fr) * | 2001-05-18 | 2005-05-13 | Rhodia Elect & Catalysis | Procede de preparation de copolymeres blocs, copolymeres blocs ainsi obtenus et utilisation comme agents compatibilisants |
| US7671095B2 (en) | 2006-05-31 | 2010-03-02 | The Trustees Of The Boston University | Films and particles |
| US7662883B2 (en) * | 2006-12-28 | 2010-02-16 | The Goodyear Tire & Rubber Company | Rubbery block polymers containing polylactone and rubber compounds including the same |
| DE102007038442A1 (de) | 2007-08-16 | 2009-02-19 | Lanxess Deutschland Gmbh | Modifizierte Polymere auf Basis von konjugierten Dienen oder von konjugierten Dienen und vinylaromatischen Verbindungen, ein Verfahren zu deren Herstellung sowie deren Verwendung |
| DE102007038439A1 (de) | 2007-08-16 | 2009-02-19 | Lanxess Deutschland Gmbh | Nanostrukturierte Polymere auf Basis von konjugierten Dienen |
| DE102007038441A1 (de) | 2007-08-16 | 2009-02-19 | Lanxess Deutschland Gmbh | Gekoppelte und Heteroatome enthaltende modifizierte Polymere auf Basis von konjugierten Dienen |
| US8795707B2 (en) * | 2008-05-13 | 2014-08-05 | Trustees Of Boston University | Compliant composites for application of drug-eluting coatings to tissue surfaces |
| KR101696238B1 (ko) * | 2013-08-30 | 2017-01-16 | 요코하마 고무 가부시키가이샤 | 타이어용 고무 조성물 및 이것을 이용하는 공기입 타이어 |
| EP3053934A1 (en) | 2015-02-06 | 2016-08-10 | LANXESS Deutschland GmbH | Heteroatom containing modified diene polymers |
| JP6630138B2 (ja) * | 2015-12-01 | 2020-01-15 | 株式会社ブリヂストン | 共重合体の製造方法、共重合体、ゴム組成物、及びゴム製品 |
| CN109880008B (zh) * | 2019-01-29 | 2021-07-02 | 大连理工大学 | 间戊二烯-异戊二烯共聚橡胶及其制备方法 |
| WO2024148045A1 (en) * | 2023-01-03 | 2024-07-11 | Bridgestone Corporation | Polydienes and polydiene copolymers with poly(alkylene oxide) grafts and the use of the same in the manufacture of tire components |
| CN117487102B (zh) * | 2023-12-29 | 2024-03-19 | 新疆独山子石油化工有限公司 | 一种sbs改性剂及其制备方法和应用 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL216657A (enExample) * | 1956-04-25 | |||
| IT1085663B (it) | 1977-08-01 | 1985-05-28 | Snam Progetti | Procedimento per la polimerizzazione e copolimerizzazione di diolefine e mezzi adatti allo scopo |
| DE2830080A1 (de) | 1978-07-08 | 1980-01-17 | Bayer Ag | Katalysator, dessen herstellung und verwendung zur loesungspolymerisation von butadien |
| DE2848964A1 (de) | 1978-11-11 | 1980-05-22 | Bayer Ag | Katalysator, dessen herstellung und verwendung zur loesungspolymerisation von butadien |
| IT1140452B (it) | 1981-09-25 | 1986-09-24 | Anic Spa | Procedimento per la polimerizzazione di diolefine coniugate e mezzi adatti allo scopo |
| US4436864A (en) * | 1981-12-11 | 1984-03-13 | Owens-Corning Fiberglas Corporation | Aqueous emulsions of acrylamide and rubber modified asphalts |
| IT1151542B (it) | 1982-04-15 | 1986-12-24 | Anic Spa | Procedimento per la polimerizzazione di diolefine coniugate e mezzi adatti allo scopo |
| IT1151543B (it) | 1982-04-15 | 1986-12-24 | Anic Spa | Procedimento per la polimerizzazione di diolefine coniugate e mezzi adatti allo scopo |
| IT1186747B (it) | 1985-07-01 | 1987-12-16 | Enichem Elastomers | Procedimento migliorato per la polimerizzazione o copolimerizzazione del butadiene |
| US4906706A (en) * | 1986-09-05 | 1990-03-06 | Japan Synthetic Rubber Co., Ltd. | Modified conjugated diene polymer and process for production thereof |
| AU608016B2 (en) * | 1987-07-06 | 1991-03-21 | Dow Chemical Company, The | Block polymers of methacrylates and derivatives thereof |
| US5002676A (en) * | 1989-12-06 | 1991-03-26 | Shell Oil Company | Block copolymers |
| GB9119234D0 (en) * | 1991-09-09 | 1991-10-23 | Enichem Elastomers Ltd | Conjugated diene polymerisation |
| IT1265049B1 (it) | 1993-08-06 | 1996-10-28 | Eniricerche Spa | Complessi alogenati dei lantanidi e loro uso nella polimerizzazione di monomeri insaturi |
| IT1273753B (it) | 1994-02-11 | 1997-07-10 | Eniriceche Spa | Sistema catalitico e processo per la produzione di polidiolefine |
| US5807944A (en) * | 1996-06-27 | 1998-09-15 | Ciba Vision Corporation | Amphiphilic, segmented copolymer of controlled morphology and ophthalmic devices including contact lenses made therefrom |
-
2001
- 2001-03-27 DE DE10115106A patent/DE10115106A1/de not_active Withdrawn
-
2002
- 2002-03-14 EP EP02005335A patent/EP1245600B1/de not_active Expired - Lifetime
- 2002-03-14 DE DE50208674T patent/DE50208674D1/de not_active Expired - Lifetime
- 2002-03-21 US US10/102,761 patent/US6734257B2/en not_active Expired - Lifetime
- 2002-03-22 CA CA002378498A patent/CA2378498A1/en not_active Abandoned
- 2002-03-27 JP JP2002088696A patent/JP3997313B2/ja not_active Expired - Fee Related
-
2004
- 2004-02-03 US US10/772,005 patent/US20040167276A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| DE50208674D1 (de) | 2006-12-28 |
| US20040167276A1 (en) | 2004-08-26 |
| EP1245600A1 (de) | 2002-10-02 |
| JP3997313B2 (ja) | 2007-10-24 |
| DE10115106A1 (de) | 2002-10-10 |
| EP1245600B1 (de) | 2006-11-15 |
| US6734257B2 (en) | 2004-05-11 |
| US20020183467A1 (en) | 2002-12-05 |
| JP2002356557A (ja) | 2002-12-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0743325B1 (en) | Novel polymer containing a modified cyclic monomer unit | |
| CA1223396A (en) | Process for producing conjugated diene polymer | |
| US3716495A (en) | Polymerization initiator composition and use thereof | |
| US6734257B2 (en) | Block copolymer based on conjugated diolefins and polar monomers | |
| KR101681043B1 (ko) | 공액 디엔의 입체특이적 중합을 위한 희토류 착물로 제조된 촉매 시스템 | |
| CA2142229C (en) | Catalytic system and process for the production of polydiolefins | |
| EP2599800B1 (en) | Copolymer and manufacturing method for same | |
| US9315590B2 (en) | Catalytic system for conjugated diene polymerisation, polymerisation method and functional polymer obtained | |
| US6706830B2 (en) | Copolymerization of conjugated dienes with non-conjugated olefins by means of rare earth catalysts | |
| KR101781699B1 (ko) | 공액 디엔의 중합용 촉매 조성물 | |
| KR20010071951A (ko) | 비닐방향족 용매 존재하 희토류 촉매를 사용한 공액디올레핀 (디엔)의 중합 방법 | |
| JPS60228511A (ja) | 溶液重合によるゴム状共重合体 | |
| KR20190103363A (ko) | 폴리부타디엔, 그의 생산 및 용도 | |
| WO2015186667A1 (ja) | 共役ジエン系重合体、その製造方法及びそれを含む組成物 | |
| US3470144A (en) | Process for producing copolymer | |
| US20070260009A1 (en) | Block copolymer preparation method, block copolymers thus obtained and use thereof as compatibilizers | |
| US6566465B1 (en) | Method for polymerizing conjugated diolefins (dienes) with catalysts based on vanadium compounds in the presence of vinylaromatic solvents | |
| KR20010070979A (ko) | 비닐방향족 용매 존재하 코발트 화합물 기재 촉매를사용한 공액 디올레핀(디엔)의 중합 방법 | |
| KR100780478B1 (ko) | 스티렌-부타디엔 고분자와 고 1,4-시스 폴리부타디엔의공중합체 및 이의 제조방법 | |
| KR102794125B1 (ko) | 변형 폴리다이엔(변형체)의 생산 방법 | |
| KR20010113961A (ko) | 고무 용액을 사용한 열가소성 성형물의 제조 방법 | |
| EP0336874A1 (en) | Inverse phase polymerization | |
| KR20020081485A (ko) | 비닐 방향족 용매의 존재하에 희토류 촉매로 공액디올레핀 (디엔)을 중합시키는 방법 | |
| KR20100112359A (ko) | 분자량 조절이 가능한 고 1,4-트랜스 폴리부타디엔 제조용 촉매 | |
| JPS5811446B2 (ja) | トウメイセイブロツクキヨウジユウゴウタイジユシノ セイゾウホウホウ |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |