DK2315784T3 - Process for the synthesis of functionalized poly (1,3-alkadienes) and their use in the production of impact-resistant vinyl aromatic polymers - Google Patents
Process for the synthesis of functionalized poly (1,3-alkadienes) and their use in the production of impact-resistant vinyl aromatic polymers Download PDFInfo
- Publication number
- DK2315784T3 DK2315784T3 DK09777874.0T DK09777874T DK2315784T3 DK 2315784 T3 DK2315784 T3 DK 2315784T3 DK 09777874 T DK09777874 T DK 09777874T DK 2315784 T3 DK2315784 T3 DK 2315784T3
- Authority
- DK
- Denmark
- Prior art keywords
- vinyl aromatic
- polymerization
- mixture
- solvent
- elastomer
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims description 49
- 238000000034 method Methods 0.000 title claims description 36
- 229920002554 vinyl polymer Polymers 0.000 title claims description 34
- 230000008569 process Effects 0.000 title claims description 23
- 230000015572 biosynthetic process Effects 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 238000003786 synthesis reaction Methods 0.000 title claims description 6
- 229920001971 elastomer Polymers 0.000 claims description 54
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 42
- 239000000806 elastomer Substances 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 34
- -1 bromine alkanes Chemical class 0.000 claims description 32
- 239000002904 solvent Substances 0.000 claims description 31
- 239000000178 monomer Substances 0.000 claims description 30
- 238000006116 polymerization reaction Methods 0.000 claims description 30
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 29
- 229920001577 copolymer Polymers 0.000 claims description 23
- 239000012071 phase Substances 0.000 claims description 18
- 229910052744 lithium Inorganic materials 0.000 claims description 15
- 239000003999 initiator Substances 0.000 claims description 12
- 239000002245 particle Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 239000011159 matrix material Substances 0.000 claims description 8
- 239000012454 non-polar solvent Substances 0.000 claims description 7
- 239000011258 core-shell material Substances 0.000 claims description 5
- 239000007791 liquid phase Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 4
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical group CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 238000004064 recycling Methods 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 28
- 229920002857 polybutadiene Polymers 0.000 description 26
- 239000005062 Polybutadiene Substances 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 19
- 150000003254 radicals Chemical class 0.000 description 16
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
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- 238000002360 preparation method Methods 0.000 description 13
- 238000004458 analytical method Methods 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000009826 distribution Methods 0.000 description 9
- 238000005227 gel permeation chromatography Methods 0.000 description 9
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- 239000003963 antioxidant agent Substances 0.000 description 8
- 238000000569 multi-angle light scattering Methods 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical group C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 7
- 229920002223 polystyrene Polymers 0.000 description 7
- 229920003048 styrene butadiene rubber Polymers 0.000 description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 6
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- 239000003153 chemical reaction reagent Substances 0.000 description 5
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- 229920005669 high impact polystyrene Polymers 0.000 description 5
- 239000004797 high-impact polystyrene Substances 0.000 description 5
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- 239000011541 reaction mixture Substances 0.000 description 5
- 238000010561 standard procedure Methods 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 241001237745 Salamis Species 0.000 description 4
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- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- 239000002174 Styrene-butadiene Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
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- 229930195733 hydrocarbon Natural products 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 239000005051 trimethylchlorosilane Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
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- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000013626 chemical specie Substances 0.000 description 2
- 230000002596 correlated effect Effects 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
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- 150000002170 ethers Chemical class 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
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- 230000003287 optical effect Effects 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
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- 239000003505 polymerization initiator Substances 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
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- 241000894007 species Species 0.000 description 2
- 238000001370 static light scattering Methods 0.000 description 2
- 239000011115 styrene butadiene Substances 0.000 description 2
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 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
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- NALFRYPTRXKZPN-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(OOC(C)(C)C)(OOC(C)(C)C)C1 NALFRYPTRXKZPN-UHFFFAOYSA-N 0.000 description 1
- HSLFISVKRDQEBY-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)cyclohexane Chemical compound CC(C)(C)OOC1(OOC(C)(C)C)CCCCC1 HSLFISVKRDQEBY-UHFFFAOYSA-N 0.000 description 1
- SVHAMPNLOLKSFU-UHFFFAOYSA-N 1,2,2-trichloroethenylbenzene Chemical compound ClC(Cl)=C(Cl)C1=CC=CC=C1 SVHAMPNLOLKSFU-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- AUHKVLIZXLBQSR-UHFFFAOYSA-N 1,2-dichloro-3-(1,2,2-trichloroethenyl)benzene Chemical compound ClC(Cl)=C(Cl)C1=CC=CC(Cl)=C1Cl AUHKVLIZXLBQSR-UHFFFAOYSA-N 0.000 description 1
- XPXMCUKPGZUFGR-UHFFFAOYSA-N 1-chloro-2-(1,2,2-trichloroethenyl)benzene Chemical compound ClC(Cl)=C(Cl)C1=CC=CC=C1Cl XPXMCUKPGZUFGR-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
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- BTOVVHWKPVSLBI-UHFFFAOYSA-N 2-methylprop-1-enylbenzene Chemical compound CC(C)=CC1=CC=CC=C1 BTOVVHWKPVSLBI-UHFFFAOYSA-N 0.000 description 1
- FMFHUEMLVAIBFI-UHFFFAOYSA-N 2-phenylethenyl acetate Chemical compound CC(=O)OC=CC1=CC=CC=C1 FMFHUEMLVAIBFI-UHFFFAOYSA-N 0.000 description 1
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- 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
- XRUKRHLZDVJJSX-UHFFFAOYSA-N 4-cyanopentanoic acid Chemical compound N#CC(C)CCC(O)=O XRUKRHLZDVJJSX-UHFFFAOYSA-N 0.000 description 1
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- 239000012963 UV stabilizer Substances 0.000 description 1
- 241000405217 Viola <butterfly> Species 0.000 description 1
- YMOONIIMQBGTDU-VOTSOKGWSA-N [(e)-2-bromoethenyl]benzene Chemical compound Br\C=C\C1=CC=CC=C1 YMOONIIMQBGTDU-VOTSOKGWSA-N 0.000 description 1
- LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
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- GSECCTDWEGTEBD-UHFFFAOYSA-N tert-butylperoxycyclohexane Chemical compound CC(C)(C)OOC1CCCCC1 GSECCTDWEGTEBD-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 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
- C08C19/30—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
- C08F2/00—Processes of polymerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
-
- 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
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/12—Monomers containing a branched unsaturated aliphatic radical or a ring substituted by an alkyl radical
-
- 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
- C08F279/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
- C08F279/02—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00 on to polymers of conjugated dienes
-
- 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
- C08F291/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
-
- 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
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
- C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
-
- 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
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/04—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to rubbers
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)
- Graft Or Block Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI2008A001524A IT1391109B1 (it) | 2008-08-20 | 2008-08-20 | Procedimento per la sintesi di poli(1,3-alcadieni) funzionalizzati e loro impiego nella preparazione di polimeri vinilaromatici ad alta resistenza all'urto |
| PCT/EP2009/005893 WO2010020374A1 (en) | 2008-08-20 | 2009-08-07 | Process for the synthesis of functionalized poly(1,3-alkadienes) and use thereof in the preparation of high impact vinyl aromatic polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2315784T3 true DK2315784T3 (en) | 2017-02-27 |
Family
ID=40802003
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK09777874.0T DK2315784T3 (en) | 2008-08-20 | 2009-08-07 | Process for the synthesis of functionalized poly (1,3-alkadienes) and their use in the production of impact-resistant vinyl aromatic polymers |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US9029479B2 (enExample) |
| EP (1) | EP2315784B1 (enExample) |
| JP (1) | JP5642677B2 (enExample) |
| CN (1) | CN102164968B (enExample) |
| BR (1) | BRPI0917857B1 (enExample) |
| DK (1) | DK2315784T3 (enExample) |
| ES (1) | ES2616517T3 (enExample) |
| HU (1) | HUE033188T2 (enExample) |
| IT (1) | IT1391109B1 (enExample) |
| PL (1) | PL2315784T3 (enExample) |
| PT (1) | PT2315784T (enExample) |
| RU (1) | RU2493174C2 (enExample) |
| WO (1) | WO2010020374A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20121018A1 (it) * | 2012-06-12 | 2013-12-13 | Versalis Spa | Procedimento per la preparazione di copolimeri elastomerici funzionalizzati e ramificati e loro impiego in composizioni elastomeriche vulcanizzabili |
| TWI674295B (zh) * | 2015-08-20 | 2019-10-11 | 日商日本瑞翁股份有限公司 | 含腈基之共聚橡膠、交聯性橡膠組合物及橡膠交聯物 |
| WO2017186511A1 (en) * | 2016-04-29 | 2017-11-02 | Sabic Global Technologies B.V. | Process for the production of copolymers |
| RU2666724C1 (ru) * | 2018-05-15 | 2018-09-12 | Публичное Акционерное Общество "Нижнекамскнефтехим" | Способ получения полимеров бутадиена или сополимеров бутадиена со стиролом с низким содержанием 1,2-звеньев в бутадиеновой части |
| TW202330677A (zh) | 2021-12-10 | 2023-08-01 | 義大利商佛沙里斯股份有限公司 | 橡膠強化的乙烯芳香族(共)聚合物及其製備方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2730241B1 (fr) * | 1995-02-07 | 1997-02-28 | Atofina | Procede de fabrication d'une composition comprenant un polymere vinylaromatique et un caoutchouc par polymerisation en presence d'un radical libre stable |
| IT1274361B (it) * | 1995-02-16 | 1997-07-17 | Enichem Spa | Procedimento per la preparazione di copolimeri vinilaromatici rinforzati con gomma |
| BR9708300A (pt) * | 1996-03-29 | 1999-08-03 | Dow Chemical Co | Processo de polimerização em massa por radical livre |
| FR2768739B1 (fr) * | 1997-09-19 | 2004-08-06 | Atochem Elf Sa | Polymere vinylaromatique choc obtenu a partir d'un caoutchouc porteur d'un groupement generateur d'un radical libre stable |
| IT1318479B1 (it) * | 2000-04-20 | 2003-08-25 | Enichem Spa | Procedimento per la preparazione di gomme sbr con miglioratalavorabilita' e minore resistenza al rotolamento. |
| ITMI20031420A1 (it) * | 2003-07-11 | 2005-01-12 | Polimeri Europa Spa | Polimeri vinilaromatici rinforzati con gomma |
| ITMI20040752A1 (it) * | 2004-04-16 | 2004-07-16 | Polimeri Europa Spa | Procedimento per la preparazione di co polimeri vinilaromatici aggraffati su elastometro in modo controllato |
| US7125934B1 (en) * | 2005-06-28 | 2006-10-24 | The Goodyear Tire & Rubber Company | Functionalization of living rubbery polymers with nitrones |
| JP4286300B2 (ja) * | 2007-04-16 | 2009-06-24 | 横浜ゴム株式会社 | 変性ポリマー |
| EP2139946A1 (en) * | 2007-04-18 | 2010-01-06 | Dow Global Technologies Inc. | Improved monovinylidene aromatic polymers comprising sulfanylsilane functionalized elastomeric polymers |
-
2008
- 2008-08-20 IT ITMI2008A001524A patent/IT1391109B1/it active
-
2009
- 2009-08-07 PT PT97778740T patent/PT2315784T/pt unknown
- 2009-08-07 WO PCT/EP2009/005893 patent/WO2010020374A1/en not_active Ceased
- 2009-08-07 PL PL09777874T patent/PL2315784T3/pl unknown
- 2009-08-07 ES ES09777874.0T patent/ES2616517T3/es active Active
- 2009-08-07 CN CN2009801371400A patent/CN102164968B/zh active Active
- 2009-08-07 JP JP2011523337A patent/JP5642677B2/ja active Active
- 2009-08-07 DK DK09777874.0T patent/DK2315784T3/en active
- 2009-08-07 EP EP09777874.0A patent/EP2315784B1/en active Active
- 2009-08-07 US US13/059,533 patent/US9029479B2/en active Active
- 2009-08-07 HU HUE09777874A patent/HUE033188T2/hu unknown
- 2009-08-07 BR BRPI0917857A patent/BRPI0917857B1/pt active IP Right Grant
- 2009-08-07 RU RU2011107115/04A patent/RU2493174C2/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| WO2010020374A1 (en) | 2010-02-25 |
| PL2315784T3 (pl) | 2017-06-30 |
| RU2011107115A (ru) | 2012-09-27 |
| BRPI0917857B1 (pt) | 2019-01-02 |
| EP2315784B1 (en) | 2016-11-23 |
| US9029479B2 (en) | 2015-05-12 |
| RU2493174C2 (ru) | 2013-09-20 |
| BRPI0917857A2 (pt) | 2015-11-24 |
| US20110207884A1 (en) | 2011-08-25 |
| PT2315784T (pt) | 2017-02-28 |
| ITMI20081524A1 (it) | 2010-02-21 |
| CN102164968A (zh) | 2011-08-24 |
| CN102164968B (zh) | 2013-04-17 |
| JP5642677B2 (ja) | 2014-12-17 |
| HUE033188T2 (hu) | 2017-11-28 |
| JP2012500310A (ja) | 2012-01-05 |
| EP2315784A1 (en) | 2011-05-04 |
| IT1391109B1 (it) | 2011-11-18 |
| ES2616517T3 (es) | 2017-06-13 |
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