WO2013068395A1 - Polymers based on grafted polyolefins - Google Patents
Polymers based on grafted polyolefins Download PDFInfo
- Publication number
- WO2013068395A1 WO2013068395A1 PCT/EP2012/072025 EP2012072025W WO2013068395A1 WO 2013068395 A1 WO2013068395 A1 WO 2013068395A1 EP 2012072025 W EP2012072025 W EP 2012072025W WO 2013068395 A1 WO2013068395 A1 WO 2013068395A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polymer
- component
- composition
- polyolefin
- compound
- Prior art date
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 126
- 229920001112 grafted polyolefin Polymers 0.000 title description 7
- 229920000098 polyolefin Polymers 0.000 claims abstract description 81
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims description 71
- 239000000178 monomer Substances 0.000 claims description 39
- 239000004743 Polypropylene Substances 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 31
- -1 polypropylene Polymers 0.000 claims description 25
- 229920001155 polypropylene Polymers 0.000 claims description 23
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 19
- 239000004698 Polyethylene Substances 0.000 claims description 16
- 229920000573 polyethylene Polymers 0.000 claims description 16
- 238000006116 polymerization reaction Methods 0.000 claims description 14
- 238000013329 compounding Methods 0.000 claims description 12
- 238000001125 extrusion Methods 0.000 claims description 11
- 229920001684 low density polyethylene Polymers 0.000 claims description 11
- 239000004702 low-density polyethylene Substances 0.000 claims description 11
- 239000004700 high-density polyethylene Substances 0.000 claims description 10
- 229920001577 copolymer Polymers 0.000 claims description 9
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 8
- 229920001903 high density polyethylene Polymers 0.000 claims description 7
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
- 229920010126 Linear Low Density Polyethylene (LLDPE) Polymers 0.000 claims description 5
- 239000000155 melt Substances 0.000 claims description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 150000008065 acid anhydrides Chemical class 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 3
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 claims description 3
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 claims description 3
- VJDDQSBNUHLBTD-GGWOSOGESA-N [(e)-but-2-enoyl] (e)-but-2-enoate Chemical compound C\C=C\C(=O)OC(=O)\C=C\C VJDDQSBNUHLBTD-GGWOSOGESA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 claims description 3
- 229940018557 citraconic acid Drugs 0.000 claims description 3
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 3
- 239000001530 fumaric acid Substances 0.000 claims description 3
- 229920004889 linear high-density polyethylene Polymers 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- 239000011976 maleic acid Substances 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 3
- 239000012744 reinforcing agent Substances 0.000 claims description 3
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 3
- VJDDQSBNUHLBTD-UHFFFAOYSA-N trans-crotonic acid-anhydride Natural products CC=CC(=O)OC(=O)C=CC VJDDQSBNUHLBTD-UHFFFAOYSA-N 0.000 claims description 3
- 239000006096 absorbing agent Substances 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 239000002216 antistatic agent Substances 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 150000002443 hydroxylamines Chemical class 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 claims description 2
- 239000006078 metal deactivator Substances 0.000 claims description 2
- 239000002667 nucleating agent Substances 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 2
- 239000000049 pigment Substances 0.000 claims description 2
- 239000004014 plasticizer Substances 0.000 claims description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 14
- 150000003254 radicals Chemical class 0.000 description 10
- 239000000523 sample Substances 0.000 description 9
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 8
- 239000004970 Chain extender Substances 0.000 description 7
- 239000004593 Epoxy Substances 0.000 description 7
- 150000002978 peroxides Chemical class 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 5
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- 229920005692 JONCRYL® Polymers 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 3
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 3
- 150000002924 oxiranes Chemical class 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229920002725 thermoplastic elastomer Polymers 0.000 description 3
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-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-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 229940119545 isobornyl methacrylate Drugs 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- LBHPSYROQDMVBS-UHFFFAOYSA-N (1-methylcyclohexyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1(C)CCCCC1 LBHPSYROQDMVBS-UHFFFAOYSA-N 0.000 description 1
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-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
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- ISRGONDNXBCDBM-UHFFFAOYSA-N 2-chlorostyrene Chemical compound ClC1=CC=CC=C1C=C ISRGONDNXBCDBM-UHFFFAOYSA-N 0.000 description 1
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- BBDKZWKEPDTENS-UHFFFAOYSA-N 4-Vinylcyclohexene Chemical compound C=CC1CCC=CC1 BBDKZWKEPDTENS-UHFFFAOYSA-N 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-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
- 239000004952 Polyamide Substances 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 238000010101 extrusion blow moulding Methods 0.000 description 1
- 238000010096 film blowing Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000012764 mineral filler Substances 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003336 secondary aromatic amines Chemical class 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- C08F8/00—Chemical modification by after-treatment
-
- 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
- C08F8/14—Esterification
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/04—Homopolymers or copolymers of ethene
- C08L23/08—Copolymers of ethene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/10—Homopolymers or copolymers of propene
-
- 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
- C08L51/06—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 homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond
Definitions
- the present invention relates to a polymer (P1 ) obtainable by reaction of at least one grafted polyolefin with a compound containing at least two epoxy groups.
- the present invention relates further to a composition containing said polymer (P1 ) and at least one further polymer (P2).
- said composition is processed.
- the present invention also relates to a process for producing the polymer (P1 ) and to a process for producing the composition containing the polymer (P1 ) and the polymer (P2).
- the present invention relates to the use of said polymer (P1 ) to reduce the melt flow rate (MFR), in particular in recycled polyolefins.
- Polyolefins in particular polypropylene (PP), are a well-known class of polymers which can be employed in many different fields.
- An advantage of polyolefins is that products made out of polyolefins can be recycled.
- the loss of molecular weight of polyolefins, in particular of recycled polyolefins, during processing of the polyolefins is a well-known problem.
- the loss of (molecular) weight leads to a reduced melt strength (by consequence, an increased melt flow rate is measured) within the items made from polyolefin during processing, in particular by extrusion applications.
- the processing problem of polyolefins with an increased melt flow rate has already been addressed in literature.
- WO 00/26286 relates to a process for modifying the molecular weight of polyolefins and to a composition comprising a polyolefin and multifunctional epoxides.
- the molecular weight of the polyolefins is modified by adding at least one compound (A), which contains at least one epoxy group and at least one alkenyl group.
- a radical former such as a peroxide, and/or perchlorates are added in addition to compound (A).
- Disadvantages of said method are uncontrolled side reactions due to chain breaking and/or gel formation due to crosslinking, which effects are mainly caused by employing peroxides and/or perchlorates.
- WO 97/301 12 relates to a process for stabilizing polyolefin recyclates, to a stabilizer mixture and to a recycled polyolefin obtainable by said process.
- the polyolefin recyclate is stabilized against oxidative, thermal or light-induced degradation by adding at least one secondary aromatic amine and at least one polyfunctional epoxide to the polyolefin recyclate.
- US-B 6,884,851 relates to a process for producing polyolefins having special rheological and compatibilization properties, as well as to the resulting polyolefins and to their use.
- the polyolefins obtained by said process are grafted polyolefins, which show different melt strength properties compared to polyolefins, which are not grafted.
- the polyolefins to be grafted may be homo- or copolymers based on linear olefins containing from 2 to 8 carbon atoms, such as ethylene, propylene or 1-octene.
- the grafting is carried out with graftable monomers bearing at least one functional group chosen from a carbonyl and an acid anhydride and having a vinyl-unsaturated group.
- the grafted polymers according to US-B 6,884,851 are not reacted further after the grafting.
- EP-A 0 269 275 relates to a thermoplastic elastomer composition having an excellent heat bondability to various resins and metals and having a high rubbery elasticity and a good moldability.
- Said thermoplastic elastomer composition comprises a) a peroxide- crosslinking olefin copolymer rubber, b) an olefinic plastic and c) less than 10 % compared to the amount of components a) and b) of an unsaturated epoxy monomer or an unsaturated hydroxyl monomer.
- Said thermoplastic elastomer composition is partially crosslinked.
- the rubber component a) does not contain any grafted olefin.
- the unsaturated epoxy monomer may be, for example, glycidyl esters of unsaturated monocarboxylic acids such as glycidyl acrylate or glycidyl methacrylate.
- the composition is produced by blending said components and dynamically heat-treating the blend in the presence of an organic peroxide to obtain partial crosslinking.
- US-A 2004/0138381 relates to chain extenders made from epoxy-functional monomers, polymeric compositions and articles made therefrom.
- the chain extender comprises a polymerization product of a) at least one epoxy-functional (meth)acrylic monomer and b) at least one styrenic and/or (meth)acrylic monomer.
- Said chain extender has to fulfill further parameters, such as an epoxy equivalent weight of from about 180 to about 2800.
- Said chain extender can be employed in a chain extended polymeric composition comprising (besides said chain extender) at least one condensation polymer. Within said composition at least a portion of said chain extender has reacted with a portion of said condensation polymer to produce a chain-extended condensation polymer.
- Condensation polymers to be employed are selected from, for example, polyesters, polyamides or polyurethanes.
- the object is achieved by a polymer (P1 ) obtainable by reaction of at least one component a) with at least one component b), wherein a) is at least one polyolefin (A), which is grafted with at least one compound (G), and b) is at least one compound (B) containing at least two epoxy groups.
- a big advantage of the present invention can be found by employing a grafted polyolefin as component a) to obtain the polymer (P1 ). Due to the grafting and the maintained functionality, chain extension can be obtained via a straight forward reaction way resulting in stable bondings of compound (B) to the polyolefin of component a). Since compound (B) contains at least two epoxy groups, at least two (individual) grafted polyolefins according to component a) can be linked together. By consequence, a new and stable polymer (P1 ) is obtained having a significant increase in molecular weight compared to an ordinary polyolefin, which is not grafted.
- the torque of the new polymer (P1 ) is increased compared to a conventional polymer according to component a).
- An additional advantage of the polymer (P1 ) compared to (recycled) polyolefins as described in, for example, WO 00/26286 is that no free radical initiators are employed when preparing the polymer (P1 ) by reacting at least one component a) with at least one component b).
- the method according to WO 00/26286 requires the employment of free radical initiators (radical formers such as peroxides), otherwise the multifunctional epoxides cannot be connected to the polyolefins.
- the polymers (P1 ) according to the present invention can be successfully employed together with different polymers, especially with polyolefins, in particular with recycled polyolefins. Due to the stable bonding and, by consequence, the controlled built up of high molecular weight polyolefin according to polymer (P1 ) of the present invention, the molecular weight decrease of polyolefins, especially recycled polyolefins obtained by processing, can be compensated. This means that the quality/the properties of recycled polyolefins can be significantly increased by adding at least some amount of the novel polymer (P1 ) having an increased molecular weight compared to ordinary polyolefin, which is not grafted and/or not chain-extended.
- the polymer (P1 ) obtainable by reaction of the components a) and b) is defined in more detail.
- a composition containing at least one polymer (P1 ) and at least one further polymer (P2) as well as methods for preparing said polymer (P1 ) or said compositions containing said polymers (P1 ) and (P2) are defined afterwards in the text below.
- the component a), which is used for obtaining a polymer (P1 ), comprises at least one polyolefin (A), which is grafted with at least one compound (G).
- the polyolefin (A) as such may be any polyolefin known to a person skilled in the art, which is not grafted. Suitable polyolefins to be employed as polyolefin (A) are described, for example, in WO 00/26286.
- the polyolefins can be prepared, for example, by radical polymerization or catalytic polymerization.
- the polyolefin may be a homopolymer or a copolymer based on at least two different olefins.
- the polyolefin (A) is a polymer based on (at least one) linear olefins containing from 2 to 8 carbon atoms, such as ethylene, propylene, 1 -butene, 1 -pentene, 1 -hexene and 1 - octene.
- the comonomers are additionally (to the above linear olefins) chosen from 4- vinylcyclohexene, dicyclopentadiene, methylene and ethylidene norbornene, 1 ,3- butadiene, isoprene and 1 ,3-pentadiene.
- the polyolefin (A) is selected from polypropylene (PP), PP- copolymers, polyethylene (PE), or metallocene based polyolefins.
- Polyethylene is preferably low density polyethylene (LDPE), linear low density polyethylene (LLDPE), or high density polyethylene (HDPE).
- LDPE low density polyethylene
- LLDPE linear low density polyethylene
- HDPE high density polyethylene
- the PP copolymer and the metallocene based polyolefins are based on the same monomers as described in the previous paragraph, last two sentences.
- the polyolefin (A) of component a) is polypropylene (PP) or polyethylene (PE).
- the compound (G), which is grafted onto at least one polyolefin (A), may be any compound known to a person skilled in the art known to be useful for being grafted on polyolefins.
- Said compound (G) has at least one functional group, which is still present after being grafted onto at least one polyolefin (A).
- said functional group is able to react with an epoxy group of compound (B) as described below.
- compound (G) may be a graftable monomer bearing at least one functional group chosen from a carbonyl and an acid anhydride.
- graftable monomers examples include unsaturated monocarboxylic or dicarboxylic acids and derivatives thereof and unsaturated monocarboxylic or dicarboxylic acid anhydrides and derivatives thereof.
- the graftable monomer according to compound (G) preferably contains from 3 to 20 carbon atoms.
- further graftable monomers may be employed as a mixture together with at least one compound (G).
- Said further graftable monomers bear a vinyl unsaturated group and, optionally, one or more aromatic rings.
- the compound (G) of component a) is one compound selected from acrylic acid, methyacrylic acid, maleic acid, fumaric acid, itaconic acid, crotonic acid, citraconic acid, maleic anhydride, itaconic anhydride, crotonic anhydride or citraconic anhydride. Most preferably, the compound (G) of component a) is maleic anhydride.
- the component a) according to the present invention is most preferably a polypropylene or polyethylene, which is grafted with maleic anhydride.
- the component b), which is used for obtaining the polymer (P1 ), is at least one compound (B) containing at least two epoxy groups.
- Such compounds are known to a person skilled in the art and are described, for example, in US-A 2004/0138381 or WO 00/26286.
- Component b) / compound (B) may be considered as having the function of a chain extender in respect of component (a).
- the compound (B) according to the present invention may be a polymer or oligomer itself under the provision that - after the compound (B) is produced, for example, by polymerization - said compound (B) still contains at least two epoxy groups.
- the compound (B) of component b) is a polymerization product of b1 ) at least one epoxy-functional (meth)acrylic monomer and b2) at least one styrenic and/or (meth)acrylic monomer.
- Examples of such polymerization products containing at least two epoxy groups to be employed as component b) are styrene (meth)acrylic copolymers having at least two epoxy groups produced from monomers (according to component b1 ) and b2)) of at least one epoxy-functional (meth)acrylic monomer and at least one non-functional styrenic and/or (meth)acrylic monomer.
- (meth)acrylic monomer includes both acrylic and methacrylic monomers and relates to the corresponding esters (acrylate and methacrylate) of acrylic or methacrylic acid such as methyl acrylate and methyl methacrylate.
- Suitable acrylic and methacrylic monomers for use in the context in this invention include, but are not limited to, methyl acrylate, ethyl acrylate, n-propyl acrylate, n-butyl acrylate, n-hexyl acrylate, n-octyl acrylate, cyclohexyl acrylate, isobornyl acrylate, methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, n-butyl methacrylate iso-butyl methacrylate, methylcyclohexyl methacrylate and isobornyl methacrylate.
- epoxy-functional (meth)acrylic monomers for use in the present invention as component b1 ), therefore, include, but are not limited to, those containing 1 ,2-epoxy groups such as glycidyl acrylate and glycidyl methacrylate.
- suitable epoxy- functional monomers include allyl glycidyl ether, glycidyl ethacrylate, and glycidyl itoconate.
- Styrenic monomers for use in the present invention as component b2) include, but are not limited to, styrene, alpha-methyl styrene, vinyl toluene, p-methyl styrene, t-butyl styrene, o-chlorostyrene, vinyl pyridine, and mixtures of these species.
- the styrenic monomers for use in the present invention are styrene and alpha-methyl styrene.
- Preferred monomers according to component b2) are styrene, alpha-methyl styrene and non-functional acrylate or non-functional methacrylate monomers selected from methyl acrylate, n-butyl acrylate, n-hexyl acrylate, cyclohexyl acrylate, isobornyl acrylate methyl methacrylate, n-butyl methacrylate, iso-butyl methacrylate, cyclohexyl methacrylate, and isobornyl methacrylate and combinations thereof.
- the compound (B) according to the above definition has an epoxy equivalent weight (EEW-value) of from about 180 to about 2800 [g/mol], an Efn value of less than about 30, an Efw value of up to about 140, an M w value of less than 25000 [g/mol], and an M n value of less than 6000 [g/mol].
- Efn means the number average epoxy functionality (per polymer chain)
- Efw means the weight average epoxy functionality (per polymer chain)
- M w means weight average molecular weight
- M n means the number average molecular weight.
- the compound (B) containing at least two epoxy groups according to component b) of the present invention is a polymerization product of at least one monomer selected from glycidyl acrylate and glycidyl methacrylate and at least one monomer selected from styrene, methyl acrylate, n-butyl acrylate, n-hexyl acrylate, and methyl methacrylate.
- the polymer (P1 ) is obtainable by a reaction of the component a) and b), wherein component a) reacts via a functional group selected form acid anhydride (-CO-0-CO-), -COOH, -OH or a salt thereof with an epoxy group of compound (B) to obtain the polymer (P1 ).
- component a) reacts via a functional group selected form acid anhydride (-CO-0-CO-), -COOH, -OH or a salt thereof with an epoxy group of compound (B) to obtain the polymer (P1 ).
- the term "salt thereof” only relates to the functional groups -COOH and -OH.
- a suitable salt is, for example, the corresponding Na-salt such as -COO " Na + Since compound (B) contains at least two epoxy groups, it is preferred that at least two of those epoxy groups are reacted with component a), preferably with two individual polymers falling under the definition of compound a).
- said reaction is carried out in absence of any radical formers (free radical initiators), such as peroxides and/or any perchlorates.
- the polymer (P2) may be any polymer known to a person skilled in the art, which does not fall under the above definitions of polymer (P1 ).
- the polymer (P2) is a polyolefin (C).
- the polyolefin (C) may have the same or a different definition compared to the polyolefin (A) according to component a) of polymer (P1 ). This means that the polyolefin (C) is preferably not grafted. More preferably, the polyolefin (C) has the same definition as polyolefin (A) according to component a) of polymer (P1 ).
- the polyolefin (C) is selected from polypropylene (PP), PP- copolymers, polyethylene (PE), or metallocene based polyolefins.
- Polyethylene is preferably low density polyethylene (LDPE), linear low density polyethylene (LLDPE), or high density polyethylene (HDPE).
- LDPE low density polyethylene
- LLDPE linear low density polyethylene
- HDPE high density polyethylene
- the PP copolymer and the metallocene based polyolefins are based on the same monomers as described above in connection with polyolefin (A).
- the polyolefin (C) of component a) is polypropylene (PP) or polyethylene (PE).
- the composition according to the present invention may contain at least one polymer (P1 ) and at least one further polymer (P2) in any suitable ratio known to a person skilled in the art.
- the composition contains 0,2 to 10 wt.-%, more preferably 1 to 5 wt.-%, of polymer (P1 ) related to the amount of polymer (P2).
- the composition according to the present invention may contain besides at least one polymer (P1 ) and at least one further polymer (P2) further components, which are known to a person skilled in the art.
- said components are preferably selected from stabilizers, antioxidants, UV-absorbers, metal deactivators, metal quenchers, phosphites, hydroxylamines, nucleating agents, fillers, reinforcing agents, plasticizers, lubricants, emulsifiers, pigments, catalysts, flow promotors, optical brighteners or antistatic agents, wherein the amount of said further components is 0.1 to 50 wt.-% related to the sum of polymers (P1 ) and (P2).
- a preferred filler is a mineral filler, more preferably talcum.
- a preferred reinforcing agent are glass fibers.
- the composition according to the present invention is a processed composition, preferably the processed composition is a composition, which is compounded and afterwards optionally converted.
- the processing of the composition, in particular the compounding, is preferably carried out, by extrusion. The processing steps such as compounding or conversion are described in more detail below in connection with the process for producing polymer (P1 ) or the composition containing at least one polymer (P1 ) and at least one further polymer (P2).
- the composition contains at least one polymer (P1 ) obtainable by reaction of at least one polyolefin (A) selected from polypropylene (PP), PP- copolymers, low density polyethylene (LDPE), linear low density polyethylene (LLDPE), high density polyethylene (HDPE) or metallocene based polyolefins, which polyolefin (A) is grafted with at least one compound (G) selected from acrylic acid, methyacrylic acid, maleic acid, fumaric acid, itaconic acid, crotonic acid, citraconic acid, maleic anhydride, itaconic anhydride, crotonic anhydride or citraconic anhydride, with at least one compound (B) containing at least two epoxy groups, wherein the compound (B) is a polymerization product of b1 ) at least one epoxy-functional (meth)acrylic monomer and at least one styrenic and/or (meth)acrylic monomer
- said composition is a processed composition, preferably the processed composition is a composition, which is compounded and afterwards optionally converted.
- the processing of the composition, in particular the compounding, is preferably carried out by extrusion.
- Said composition may optionally contain further components, preferably talcum.
- Another subject of the present invention is a process for producing a polymer (P1 ) according to the above definitions and a process for producing a composition according to the above definitions containing at least one polymer (P1 ) and at least one further polymer (P2).
- the polymer (P1 ) may be obtained in the presence or absence of any further polymers, such as polymer (P2).
- component a) according to the above definitions is reacted with component b) according to the above definitions by methods known to a person skilled in the art.
- said reaction is carried out in absence of any radical formers (free radical initiators), such as peroxides and/or any perchlorates.
- the obtained polymer (P1 ) may be processed, preferably compounded and afterwards optionally converted in the presence or absence of any further polymers, such as polymer (P2).
- a composition according to the present invention which composition contains at least one polymer (P1 ) and at least one further polymer (P2). It is preferred to carry out the reaction for producing polymer (P1 ) in the presence of at least one further polymer (P2) in order to obtain said composition.
- a composition according to the present invention by preparing at least one polymer (P1 ) and at least one further polymer (P2) separately and mixing said polymers after the respective production or polymerization process.
- the production of said composition is carried out in absence of any radical formers (free radical initiators), such as peroxides and/or any perchlorates.
- compositions according to the present invention are preferably produced according to a process, wherein component a) and/or component b) according to the above definitions is dispersed in polymer (P2) prior to the production of polymer (P1 ).
- composition according to the present invention is processed, preferably compounded and afterwards optionally converted. Most preferably, the processing of the composition and the production of polymer (P1 ) is carried out simultaneously, in particular during the compounding step.
- Processing of a composition is a technique, which is known to a person skilled in the art. Processing usually comprises the steps of compounding and afterwards optionally converting the compounded polymers. It is quite common that the polymers are obtained as resins and/or powder after carrying out the polymerization step. Processing means that granulates (due to the compounding step) or even specific products (items) such as a blown film or a plastic part (due to the optional conversion step afterwards) are made out of said resins or powders. The step of adding some additional compounds such as stabilizers or additives to the resin or powder is usually carried out together within the compounding step. According to the present invention, the compounding (step) is preferably carried out by extrusion.
- the extrusion within the compounding step may be carried out with any extruder known to be useful by a person skilled in the art.
- the preferred type of extruder is a twin screw extruder, however, a single screw extruder with barrier elements is also possible.
- the extruded composition is preferably obtained as granulates.
- a conversion step may be carried out with the compositions according to the present invention, which composition is preferably provided in the shape of (individual) granulates prior to the conversion step.
- Said conversion (step) can be carried out by any method known to a person skilled in the art in order to obtain specific products (items) such as a blown film or a plastic part.
- the conversion is preferably carried out by extrusion or injection moulding.
- the extrusion techniques within said step comprise film blowing, casting, extrusion blow moulding profile extrusion, sheet thermoforming, and sheet foaming.
- the composition is produced by a process, wherein a mixture of polymer (P2) and component a) is processed, preferably compounded by extrusion and component b) is added during said processing of the mixture of polymer (P2) and component a) in order to produce polymer (P1 ), wherein components a) and b) have the above definitions.
- Another subject of the present invention is the use of a polymer (P1 ) according to the above definitions to reduce the melt flow rate (MFR) in polymers, in particular in recycled polyolefins.
- Example 1 a polymer (P1 ) according to the present invention is prepared in the presence of one further polymer (P2).
- CO-PP relates to said polymer (P2)
- PRIEX25050 and PRIEX25090 relate to component a)
- JoncrylADR4370-S relates to component b) according to the above definition.
- PRIEX25095 and JoncrylADR4370-S are reacted to obtain polymer (P1 ).
- Said polymers or components are all commercially available and are specified as follows: CO-PP: random PP (R520Y) from SK corporation
- PRI EX25095 and PRIEX25050 polypropylene grafted with maleic anhydride (PP-g- MAH) from Addcomp Holland B.V. in The Netherlands.
- the two PRIEX polymers differ in respect of the amount of grafted maleic anhydride (PRI EX25095: 0,465%; PRI EX25050: 0, 1 %)
- JoncrylADR4370S (BASF SE, Ludwigshafen, Germany): polymerization product of at least one epoxy-functional (meth)acrylic monomer and at least one styrenic monomer, which polymerization product contains at least two epoxy groups.
- JoncrylADR4370S has an EEW-value of 285 [g/mol] and a M w -value of 6800 [g/mol].
- the mentioned temperatures are the temperature settings of the successive heating zones of the extruder, starting at the die (end of the extruder, where the composition leaves the extruder) to the zone immediately after feeder (this is the head of the extruder). The first zone, where the raw materials are dropped into the extruder, was not heated
- Sample 5 CO-PP +0.50 %PRIEX25050 +0.05 %JoncrylADR4370S
- Sample 6 CO-PP +0.25 %PRIEX25050 +0.0125 %JoncrylADR4370S
- compositions containing a polymer (P1 ) according to the present invention show reduced MFR values compared to the control sample.
- the torque is measured as a function of time for two samples on a 15 cm 3 DSM Conical Twin-Screw Micro Compounder.
- the experimental conditions are as follows: screw speed: 80 rpm, processing temperature: 220 °C, and total residence time in the extruder: 2 minutes.
- the samples are used without predrying.
- the samples are: 1. PRIEX 15005 (reference: component a) only), and 2. PRIEX 15005 plus 0.6 % of Joncryl ADR4368-CS (polymer (P1 )).
- Priex 15005 is a LDPE from Addcomp Holland B.V., on which 0.45 % of maleic anhydride has been grafted.
- Joncryl® ADR 4368-CS (BASF SE, Ludwigshafen, Germany) is a polymerization product of at least one epoxy-fu notional (meth)acrylic monomer and at least one styrenic monomer, which polymerization product contains at least two epoxy groups.
- JoncrylADR4368-CS has an EEW-value of 285 [g/mol] and a Mw-value of 6800 [g/mol].
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)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Graft Or Block Polymers (AREA)
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2014540434A JP2014534998A (ja) | 2011-11-09 | 2012-11-07 | グラフトされたポリオレフィンを基礎とするポリマー |
EP12787416.2A EP2776474A1 (en) | 2011-11-09 | 2012-11-07 | Polymers based on grafted polyolefins |
IN3176CHN2014 IN2014CN03176A (enrdf_load_stackoverflow) | 2011-11-09 | 2012-11-07 | |
CN201280054061.5A CN103917566A (zh) | 2011-11-09 | 2012-11-07 | 基于接枝聚烯烃的聚合物 |
KR1020147011945A KR20140088872A (ko) | 2011-11-09 | 2012-11-07 | 그래프트된 폴리올레핀 기반 중합체 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP11188421.9 | 2011-11-09 | ||
EP11188421 | 2011-11-09 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2013068395A1 true WO2013068395A1 (en) | 2013-05-16 |
Family
ID=47189915
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2012/072025 WO2013068395A1 (en) | 2011-11-09 | 2012-11-07 | Polymers based on grafted polyolefins |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP2776474A1 (enrdf_load_stackoverflow) |
JP (1) | JP2014534998A (enrdf_load_stackoverflow) |
KR (1) | KR20140088872A (enrdf_load_stackoverflow) |
CN (1) | CN103917566A (enrdf_load_stackoverflow) |
IN (1) | IN2014CN03176A (enrdf_load_stackoverflow) |
WO (1) | WO2013068395A1 (enrdf_load_stackoverflow) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20140147421A (ko) * | 2013-06-19 | 2014-12-30 | 주식회사 엘지화학 | 수지 혼합물 |
CN104419101A (zh) * | 2013-08-23 | 2015-03-18 | 上海杰事杰新材料(集团)股份有限公司 | 一种聚丙烯极性接枝物微孔发泡材料及其制备方法 |
EP3739597A1 (en) * | 2019-05-16 | 2020-11-18 | Borealis AG | Composition |
RU2818291C2 (ru) * | 2019-05-16 | 2024-05-02 | Бореалис Аг | Композиции, содержащие пэнп и функционализированные полиолефины |
US12187878B2 (en) | 2019-05-16 | 2025-01-07 | Borealis Ag | Polymer composition for cable insulation |
US12391824B2 (en) | 2019-05-16 | 2025-08-19 | Borealis Ag | Polymer compositions comprising mixtures of polyolefins |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112424278A (zh) * | 2018-05-23 | 2021-02-26 | 博里利斯股份公司 | 一种包含第一烯烃聚合物和第二烯烃聚合物的可交联的聚烯烃组合物 |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4528329A (en) * | 1982-05-17 | 1985-07-09 | Toa Nenryo Kogyo Kabushiki Kaisha | Production of polyolefin copolymer |
EP0269275A2 (en) | 1986-10-29 | 1988-06-01 | Mitsui Petrochemical Industries, Ltd. | Thermoplastic elastomer composition |
EP0443346A2 (en) * | 1990-01-30 | 1991-08-28 | Sumitomo Chemical Company, Limited | Thermoplastic resin composition |
WO1997030112A1 (en) | 1996-02-15 | 1997-08-21 | Ciba Specialty Chemicals Holding Inc. | Stabilisation of polyolefin-recyclates |
WO2000026286A1 (en) | 1998-11-03 | 2000-05-11 | Ciba Specialty Chemicals Holding Inc. | Multifunctional epoxides for modifying the molecular weight of polyolefins |
US20040138381A1 (en) | 2002-02-01 | 2004-07-15 | Blasius William George | Oligomeric chain extenders for processing, post-processing and recycling of condensation polymers, synthesis, compositions and applications |
US6884851B2 (en) | 1999-04-29 | 2005-04-26 | Solvay (Societe Anonyme) | Polyolefins and process for manufacturing them |
US20050261422A1 (en) * | 2004-05-21 | 2005-11-24 | National Research Council Of Canada | Primer composition and uses thereof |
-
2012
- 2012-11-07 JP JP2014540434A patent/JP2014534998A/ja active Pending
- 2012-11-07 WO PCT/EP2012/072025 patent/WO2013068395A1/en active Application Filing
- 2012-11-07 IN IN3176CHN2014 patent/IN2014CN03176A/en unknown
- 2012-11-07 KR KR1020147011945A patent/KR20140088872A/ko not_active Withdrawn
- 2012-11-07 EP EP12787416.2A patent/EP2776474A1/en not_active Withdrawn
- 2012-11-07 CN CN201280054061.5A patent/CN103917566A/zh active Pending
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4528329A (en) * | 1982-05-17 | 1985-07-09 | Toa Nenryo Kogyo Kabushiki Kaisha | Production of polyolefin copolymer |
EP0269275A2 (en) | 1986-10-29 | 1988-06-01 | Mitsui Petrochemical Industries, Ltd. | Thermoplastic elastomer composition |
EP0443346A2 (en) * | 1990-01-30 | 1991-08-28 | Sumitomo Chemical Company, Limited | Thermoplastic resin composition |
WO1997030112A1 (en) | 1996-02-15 | 1997-08-21 | Ciba Specialty Chemicals Holding Inc. | Stabilisation of polyolefin-recyclates |
WO2000026286A1 (en) | 1998-11-03 | 2000-05-11 | Ciba Specialty Chemicals Holding Inc. | Multifunctional epoxides for modifying the molecular weight of polyolefins |
US6884851B2 (en) | 1999-04-29 | 2005-04-26 | Solvay (Societe Anonyme) | Polyolefins and process for manufacturing them |
US20040138381A1 (en) | 2002-02-01 | 2004-07-15 | Blasius William George | Oligomeric chain extenders for processing, post-processing and recycling of condensation polymers, synthesis, compositions and applications |
US20050261422A1 (en) * | 2004-05-21 | 2005-11-24 | National Research Council Of Canada | Primer composition and uses thereof |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20140147421A (ko) * | 2013-06-19 | 2014-12-30 | 주식회사 엘지화학 | 수지 혼합물 |
KR101677791B1 (ko) * | 2013-06-19 | 2016-11-18 | 주식회사 엘지화학 | 수지 혼합물 |
CN104419101A (zh) * | 2013-08-23 | 2015-03-18 | 上海杰事杰新材料(集团)股份有限公司 | 一种聚丙烯极性接枝物微孔发泡材料及其制备方法 |
EP3739597A1 (en) * | 2019-05-16 | 2020-11-18 | Borealis AG | Composition |
WO2020229659A1 (en) * | 2019-05-16 | 2020-11-19 | Borealis Ag | Compositions comprising ldpe and functionalised polyolefins |
US20220235211A1 (en) * | 2019-05-16 | 2022-07-28 | Borealis Ag | Compositions comprising ldpe and functionalised polyolefins |
RU2818291C2 (ru) * | 2019-05-16 | 2024-05-02 | Бореалис Аг | Композиции, содержащие пэнп и функционализированные полиолефины |
US12187878B2 (en) | 2019-05-16 | 2025-01-07 | Borealis Ag | Polymer composition for cable insulation |
US12391824B2 (en) | 2019-05-16 | 2025-08-19 | Borealis Ag | Polymer compositions comprising mixtures of polyolefins |
Also Published As
Publication number | Publication date |
---|---|
EP2776474A1 (en) | 2014-09-17 |
KR20140088872A (ko) | 2014-07-11 |
CN103917566A (zh) | 2014-07-09 |
JP2014534998A (ja) | 2014-12-25 |
IN2014CN03176A (enrdf_load_stackoverflow) | 2015-07-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP0335649B2 (en) | Graft copolymers and blends thereof with polyolefins | |
US5229456A (en) | Graft copolymers and blends thereof with polyolefins | |
US5705565A (en) | Graft-modified substantially linear ethylene polymers and methods for their use | |
EP2776474A1 (en) | Polymers based on grafted polyolefins | |
US20130267636A1 (en) | Process for preparing high melt strength propylene polymers | |
US20060293416A1 (en) | Polyester masterbatch composition | |
US8987368B2 (en) | Polymers based on grafted polyolefins | |
US5128410A (en) | Graft copolymers and blends thereof with polyolefins | |
CN112876799A (zh) | 一种低光泽高韧性耐刮擦聚丙烯复合材料及其制备方法 | |
EP0431733B1 (en) | Polyolefin compositions with improved impact strength | |
TWI406876B (zh) | 兩性共聚物及其製造方法及包含其之高分子組合物 | |
WO2022268662A1 (en) | Vitrimer polymers derived from functionalized polyolefins | |
US5147932A (en) | Polyolefin compositions with improved impact strength | |
EP1373406A1 (en) | Chain branching agent and polyamide composition containing the same | |
JP2001523745A (ja) | ポリオレフィン樹脂およびポリアミド樹脂に基づくポリマーブレンド | |
US6921792B2 (en) | Chemically modified polyolefin elastomer composition and method for preparing the same | |
JP2009114402A (ja) | 射出成形用ポリエステル樹脂組成物及びその成形品 | |
TW200523282A (en) | Process for enhancing the melt strength of polypropylene | |
WO1995017466A1 (en) | Polyolefin-condensation polymer blend | |
JP7397717B2 (ja) | 形態改質された異相プロピレン共重合体およびその製品 | |
CA1340066C (en) | Graft copolymers and blends thereof with polyolefins | |
EP0867476B1 (fr) | Mélange de polymères thermoplastiques présentant des propriétés mécaniques améliorées | |
AU625059B2 (en) | Graft copolymers and blends thereof with polyolefins | |
EP3292171B1 (en) | Compositions for automotive interior parts | |
US20230103854A1 (en) | Polyolefin/ polyester resin |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 12787416 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 20147011945 Country of ref document: KR Kind code of ref document: A |
|
ENP | Entry into the national phase |
Ref document number: 2014540434 Country of ref document: JP Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2012787416 Country of ref document: EP |