ES2353165T3 - Poliestireno isotáctico con grupos reactivos. - Google Patents
Poliestireno isotáctico con grupos reactivos. Download PDFInfo
- Publication number
- ES2353165T3 ES2353165T3 ES08750145T ES08750145T ES2353165T3 ES 2353165 T3 ES2353165 T3 ES 2353165T3 ES 08750145 T ES08750145 T ES 08750145T ES 08750145 T ES08750145 T ES 08750145T ES 2353165 T3 ES2353165 T3 ES 2353165T3
- Authority
- ES
- Spain
- Prior art keywords
- isotactic polystyrene
- alkyl
- functionalized
- polystyrene
- methyl
- 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.)
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- 239000004793 Polystyrene Substances 0.000 title claims abstract description 107
- 229920002223 polystyrene Polymers 0.000 title claims abstract description 107
- 238000000034 method Methods 0.000 claims abstract description 63
- 230000008569 process Effects 0.000 claims abstract description 50
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 34
- 238000005649 metathesis reaction Methods 0.000 claims abstract description 29
- 150000001336 alkenes Chemical class 0.000 claims abstract description 28
- 238000004519 manufacturing process Methods 0.000 claims abstract description 21
- 238000005859 coupling reaction Methods 0.000 claims abstract description 19
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 claims abstract description 19
- 229920002725 thermoplastic elastomer Polymers 0.000 claims abstract description 16
- 230000008878 coupling Effects 0.000 claims abstract description 11
- 238000010168 coupling process Methods 0.000 claims abstract description 11
- 238000007334 copolymerization reaction Methods 0.000 claims abstract description 10
- 150000001925 cycloalkenes Chemical class 0.000 claims abstract description 10
- 238000010526 radical polymerization reaction Methods 0.000 claims abstract description 6
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims description 65
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 54
- 238000006243 chemical reaction Methods 0.000 claims description 33
- -1 preferable H Chemical group 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 20
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 11
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 11
- 150000001993 dienes Chemical class 0.000 claims description 11
- 238000006735 epoxidation reaction Methods 0.000 claims description 9
- 239000002667 nucleating agent Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 230000003197 catalytic effect Effects 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 230000026030 halogenation Effects 0.000 claims description 7
- 238000005658 halogenation reaction Methods 0.000 claims description 7
- 229920010524 Syndiotactic polystyrene Polymers 0.000 claims description 6
- 125000002524 organometallic group Chemical group 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 238000009826 distribution Methods 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 229910052735 hafnium Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 19
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
- 229920001400 block copolymer Polymers 0.000 description 13
- 239000000178 monomer Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 238000007306 functionalization reaction Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 6
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 6
- 239000004913 cyclooctene Substances 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 6
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 6
- 229920000428 triblock copolymer Polymers 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 5
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 4
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- 239000004205 dimethyl polysiloxane Substances 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- VJHGSLHHMIELQD-UHFFFAOYSA-N nona-1,8-diene Chemical compound C=CCCCCCC=C VJHGSLHHMIELQD-UHFFFAOYSA-N 0.000 description 4
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 230000031709 bromination Effects 0.000 description 3
- 238000005893 bromination reaction Methods 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- NLDGJRWPPOSWLC-UHFFFAOYSA-N deca-1,9-diene Chemical compound C=CCCCCCCC=C NLDGJRWPPOSWLC-UHFFFAOYSA-N 0.000 description 3
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 229920000578 graft copolymer Polymers 0.000 description 3
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 3
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- VOSLXTGMYNYCPW-UHFFFAOYSA-N 1,10-Undecadiene Chemical compound C=CCCCCCCCC=C VOSLXTGMYNYCPW-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- QGFSQVPRCWJZQK-UHFFFAOYSA-N 9-Decen-1-ol Chemical compound OCCCCCCCCC=C QGFSQVPRCWJZQK-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 2
- XUKFPAQLGOOCNJ-UHFFFAOYSA-N dimethyl(trimethylsilyloxy)silicon Chemical compound C[Si](C)O[Si](C)(C)C XUKFPAQLGOOCNJ-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- IYPLTVKTLDQUGG-UHFFFAOYSA-N dodeca-1,11-diene Chemical compound C=CCCCCCCCCC=C IYPLTVKTLDQUGG-UHFFFAOYSA-N 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 238000006459 hydrosilylation reaction Methods 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000012038 nucleophile Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- JVVPJOMYWVYPOF-UHFFFAOYSA-N 10-bromodec-1-ene Chemical compound BrCCCCCCCCC=C JVVPJOMYWVYPOF-UHFFFAOYSA-N 0.000 description 1
- GIEMHYCMBGELGY-UHFFFAOYSA-N 10-undecen-1-ol Chemical compound OCCCCCCCCCC=C GIEMHYCMBGELGY-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000005922 Phosphane Substances 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- KOMDZQSPRDYARS-UHFFFAOYSA-N cyclopenta-1,3-diene titanium Chemical compound [Ti].C1C=CC=C1.C1C=CC=C1 KOMDZQSPRDYARS-UHFFFAOYSA-N 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 229910000064 phosphane Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920000576 tactic polymer Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000004260 weight control Methods 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
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/20—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 unconjugated
-
- 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
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- 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
- C08F12/00—Homopolymers and 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
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F12/06—Hydrocarbons
- C08F12/08—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
- C08F257/00—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00
- C08F257/02—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00 on to polymers of styrene or alkyl-substituted styrenes
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/04—Polymers provided for in subclasses C08C or C08F
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
-
- 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
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/08—Epoxidation
-
- 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
- C08F8/20—Halogenation
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- C—CHEMISTRY; METALLURGY
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
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- C08F8/00—Chemical modification by after-treatment
- C08F8/42—Introducing metal atoms or metal-containing groups
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
- C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
- C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
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- 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
- C08L51/003—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 macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L53/02—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes
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- 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
- C08F2438/00—Living radical polymerisation
- C08F2438/01—Atom Transfer Radical Polymerization [ATRP] or reverse ATRP
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- 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
- C08F2810/00—Chemical modification of a polymer
- C08F2810/40—Chemical modification of a polymer taking place solely at one end or both ends of the polymer backbone, i.e. not in the side or lateral chains
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- 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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Polymerization Catalysts (AREA)
- Graft Or Block Polymers (AREA)
- Laminated Bodies (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07108764 | 2007-05-23 | ||
| EP07108764 | 2007-05-23 |
Publications (1)
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|---|---|
| ES2353165T3 true ES2353165T3 (es) | 2011-02-25 |
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Family Applications (1)
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| ES08750145T Active ES2353165T3 (es) | 2007-05-23 | 2008-05-07 | Poliestireno isotáctico con grupos reactivos. |
Country Status (8)
| Country | Link |
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| US (1) | US20100152387A1 (enExample) |
| EP (1) | EP2152770B1 (enExample) |
| JP (1) | JP5666902B2 (enExample) |
| AT (1) | ATE484530T1 (enExample) |
| DE (1) | DE502008001538D1 (enExample) |
| DK (1) | DK2152770T3 (enExample) |
| ES (1) | ES2353165T3 (enExample) |
| WO (1) | WO2008141941A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2009007358A1 (en) * | 2007-07-10 | 2009-01-15 | Basf Se | Flame retardant thermoplastic molding compositions |
| JP5653754B2 (ja) * | 2007-09-14 | 2015-01-14 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | スチレン−ブタジエンブロック共重合体混合物に基づく透明で強靭で剛性のある成形組成物 |
| US8802797B2 (en) | 2008-06-20 | 2014-08-12 | Exxonmobil Chemical Patents Inc. | Vinyl-terminated macromonomer oligomerization |
| US8399725B2 (en) | 2008-06-20 | 2013-03-19 | Exxonmobil Chemical Patents Inc. | Functionalized high vinyl terminated propylene based oligomers |
| US8283428B2 (en) | 2008-06-20 | 2012-10-09 | Exxonmobil Chemical Patents Inc. | Polymacromonomer and process for production thereof |
| US8283419B2 (en) | 2008-06-20 | 2012-10-09 | Exxonmobil Chemical Patents Inc. | Olefin functionalization by metathesis reaction |
| US8372930B2 (en) | 2008-06-20 | 2013-02-12 | Exxonmobil Chemical Patents Inc. | High vinyl terminated propylene based oligomers |
| MX2010013464A (es) | 2008-06-27 | 2010-12-21 | Basf Se | Mezclas de copolimero de bloque de estireno butadieno para peliculas de envoltura de encogimiento. |
| JP4608584B1 (ja) * | 2009-06-29 | 2011-01-12 | 株式会社資生堂 | 皮膚外用剤 |
| US8426659B2 (en) | 2011-03-25 | 2013-04-23 | Exxonmobil Chemical Patents Inc. | Vinyl terminated higher olefin polymers and methods to produce thereof |
| US8455597B2 (en) | 2011-03-25 | 2013-06-04 | Exxonmobil Chemical Patents Inc. | Catalysts and methods of use thereof to produce vinyl terminated polymers |
| CN103443199B (zh) * | 2011-03-25 | 2016-04-06 | 埃克森美孚化学专利公司 | 通过开环易位聚合得到的烯烃三嵌段聚合物 |
| US8940839B2 (en) | 2011-03-25 | 2015-01-27 | Exxonmobil Chemical Patents Inc. | Diblock copolymers prepared by cross metathesis |
| US8835563B2 (en) | 2011-03-25 | 2014-09-16 | Exxonmobil Chemical Patents Inc. | Block copolymers from silylated vinyl terminated macromers |
| EP2688921B1 (en) * | 2011-03-25 | 2019-04-24 | ExxonMobil Chemical Patents Inc. | Diblock copolymers prepared by cross metathesis |
| US8841397B2 (en) | 2011-03-25 | 2014-09-23 | Exxonmobil Chemical Patents Inc. | Vinyl terminated higher olefin polymers and methods to produce thereof |
| US8623974B2 (en) | 2011-03-25 | 2014-01-07 | Exxonmobil Chemical Patents Inc. | Branched vinyl terminated polymers and methods for production thereof |
| US8399724B2 (en) | 2011-03-25 | 2013-03-19 | Exxonmobil Chemical Patents Inc. | Vinyl terminated higher olefin copolymers and methods to produce thereof |
| US8604148B2 (en) | 2011-11-29 | 2013-12-10 | Exxonmobil Chemical Patents Inc. | Functionalization of vinyl terminated polymers by ring opening cross metathesis |
| EP2785763A4 (en) * | 2011-11-29 | 2015-06-03 | Exxonmobil Chem Patents Inc | FUNCTIONALIZATION OF POLYMERS WITH VINYL TERMINATION BY METATHESIS CROSSED BY CYCLE OPENING |
| US8796376B2 (en) | 2012-03-26 | 2014-08-05 | Exxonmobil Chemical Patents Inc. | Functionalized polymers and oligomers |
| EP3286018B1 (en) | 2015-04-24 | 2021-03-10 | Pirelli Tyre S.p.A. | High-performance tyre |
| MX387287B (es) * | 2015-04-24 | 2025-03-18 | Pirelli | Neumatico de alto desempeño. |
| EP4161786B1 (en) * | 2020-06-09 | 2024-05-01 | Pirelli Tyre S.P.A. | High performance tyre |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US3459832A (en) * | 1965-09-24 | 1969-08-05 | Monsanto Co | Crystalline polystyrene having activity as a polymerization catalyst |
| US3639517A (en) * | 1969-09-22 | 1972-02-01 | Phillips Petroleum Co | Resinous branched block copolymers |
| GB1482921A (en) * | 1973-07-31 | 1977-08-17 | Glaxo Lab Ltd | Polymers |
| JPS5575441A (en) * | 1978-12-04 | 1980-06-06 | Asahi Chem Ind Co Ltd | Styrene resin composition having excellent impact resistance |
| DE4011162A1 (de) * | 1990-04-06 | 1991-10-10 | Basf Ag | Thermoplastische formmasse |
| DE4420952A1 (de) * | 1994-06-17 | 1995-12-21 | Basf Ag | Thermoplastisches Elastomer |
| JPH10237139A (ja) * | 1997-02-21 | 1998-09-08 | Idemitsu Petrochem Co Ltd | グラフト共重合体及びその製造方法 |
| JPH10251336A (ja) * | 1997-03-14 | 1998-09-22 | Mitsui Chem Inc | スチレン類の重合方法 |
| DE19810141A1 (de) * | 1998-03-10 | 1999-09-16 | Basf Ag | Polymermischungen aus Styrolpolymeren |
| DE19858141A1 (de) * | 1998-12-16 | 2000-06-21 | Basf Ag | Thermoplasische Formmassen |
| US6593430B1 (en) * | 1999-03-27 | 2003-07-15 | Basf Aktiengesellschaft | Transparent, impact-resistant polystyrene on a styrene-butadiene block copolymer basis |
| DE19914075A1 (de) * | 1999-03-27 | 2000-09-28 | Basf Ag | Glasklares, schlagzähes Polystyrol auf Basis von Styrol-Butadien-Blockcopolymeren |
| JP2000319319A (ja) * | 1999-05-10 | 2000-11-21 | Agency Of Ind Science & Technol | 末端変性シンジオタクチックスチレン系重合体およびその製造方法 |
| DE10037280A1 (de) * | 2000-07-28 | 2002-02-07 | Basf Ag | Verfahren zur Agglomeration dispergierter Kautschuke |
| JP2004509202A (ja) * | 2000-09-15 | 2004-03-25 | ダウ グローバル テクノロジーズ インコーポレイティド | 清澄度の改善されたスチレンポリマー組成物 |
| JP2002348336A (ja) * | 2001-05-28 | 2002-12-04 | Idemitsu Petrochem Co Ltd | オレフィン系重合体、その製造方法及び該重合体を含む熱可塑性樹脂組成物 |
| DE102005001637A1 (de) * | 2005-01-12 | 2006-07-20 | Basf Ag | Styrol-Butadien-Blockcopolymermischungen für Schrumpffolien |
| KR101322076B1 (ko) * | 2006-06-27 | 2013-10-30 | 바스프 에스이 | 고투명성 및 인성-강성 스티렌-부타디엔 블록 공중합체 혼합물 |
| WO2009007358A1 (en) * | 2007-07-10 | 2009-01-15 | Basf Se | Flame retardant thermoplastic molding compositions |
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2008
- 2008-05-07 DE DE502008001538T patent/DE502008001538D1/de active Active
- 2008-05-07 US US12/601,147 patent/US20100152387A1/en not_active Abandoned
- 2008-05-07 WO PCT/EP2008/055625 patent/WO2008141941A1/de not_active Ceased
- 2008-05-07 ES ES08750145T patent/ES2353165T3/es active Active
- 2008-05-07 EP EP08750145A patent/EP2152770B1/de not_active Not-in-force
- 2008-05-07 JP JP2010508788A patent/JP5666902B2/ja not_active Expired - Fee Related
- 2008-05-07 AT AT08750145T patent/ATE484530T1/de active
- 2008-05-07 DK DK08750145.8T patent/DK2152770T3/da active
Also Published As
| Publication number | Publication date |
|---|---|
| US20100152387A1 (en) | 2010-06-17 |
| EP2152770B1 (de) | 2010-10-13 |
| DE502008001538D1 (de) | 2010-11-25 |
| DK2152770T3 (da) | 2011-02-07 |
| EP2152770A1 (de) | 2010-02-17 |
| JP2010528137A (ja) | 2010-08-19 |
| ATE484530T1 (de) | 2010-10-15 |
| JP5666902B2 (ja) | 2015-02-12 |
| WO2008141941A1 (de) | 2008-11-27 |
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