DE69832334T2 - Durch radikalische polymerisation hergestellte copolymere von polyolefinen mit hohem vinylidenegehalt und vinyl- oder vinyliden-monomeren - Google Patents
Durch radikalische polymerisation hergestellte copolymere von polyolefinen mit hohem vinylidenegehalt und vinyl- oder vinyliden-monomeren Download PDFInfo
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- DE69832334T2 DE69832334T2 DE69832334T DE69832334T DE69832334T2 DE 69832334 T2 DE69832334 T2 DE 69832334T2 DE 69832334 T DE69832334 T DE 69832334T DE 69832334 T DE69832334 T DE 69832334T DE 69832334 T2 DE69832334 T2 DE 69832334T2
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- copolymer
- alkyl
- highly reactive
- copolymers
- molecular weight
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- 229920001577 copolymer Polymers 0.000 title claims description 121
- 239000000178 monomer Substances 0.000 title claims description 82
- 229920002554 vinyl polymer Polymers 0.000 title claims description 53
- 238000010526 radical polymerization reaction Methods 0.000 title claims description 11
- -1 VINYLIDEN Chemical class 0.000 title description 56
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical class C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 title description 5
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical class C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 title 1
- 229920000642 polymer Polymers 0.000 claims description 89
- 229920000098 polyolefin Polymers 0.000 claims description 86
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 claims description 66
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 50
- 239000001257 hydrogen Substances 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- 239000003999 initiator Substances 0.000 claims description 34
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 28
- 238000002360 preparation method Methods 0.000 claims description 28
- 238000006116 polymerization reaction Methods 0.000 claims description 25
- 150000001336 alkenes Chemical class 0.000 claims description 24
- 150000003254 radicals Chemical class 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 238000000576 coating method Methods 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 13
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 12
- 229920002367 Polyisobutene Polymers 0.000 claims description 12
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 12
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 10
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 10
- 239000011248 coating agent Substances 0.000 claims description 10
- 229920000578 graft copolymer Polymers 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
- 239000000203 mixture Substances 0.000 description 56
- 229920001083 polybutene Polymers 0.000 description 56
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 49
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 38
- 238000006243 chemical reaction Methods 0.000 description 37
- 239000000243 solution Substances 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 32
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 27
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 27
- 125000004432 carbon atom Chemical group C* 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 23
- 239000002904 solvent Substances 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 239000000839 emulsion Substances 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 22
- 239000002244 precipitate Substances 0.000 description 21
- 229910052782 aluminium Inorganic materials 0.000 description 20
- 238000012360 testing method Methods 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000003973 paint Substances 0.000 description 18
- 239000000376 reactant Substances 0.000 description 17
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 16
- 239000004711 α-olefin Substances 0.000 description 16
- 239000007788 liquid Substances 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 14
- AQZWEFBJYQSQEH-UHFFFAOYSA-N 2-methyloxaluminane Chemical compound C[Al]1CCCCO1 AQZWEFBJYQSQEH-UHFFFAOYSA-N 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 14
- 239000010408 film Substances 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 229910007926 ZrCl Inorganic materials 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- 239000004743 Polypropylene Substances 0.000 description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 11
- 239000008367 deionised water Substances 0.000 description 11
- 229910021641 deionized water Inorganic materials 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000002861 polymer material Substances 0.000 description 11
- 229920001155 polypropylene Polymers 0.000 description 11
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 11
- 239000004753 textile Substances 0.000 description 11
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 10
- 239000000853 adhesive Substances 0.000 description 10
- 230000001070 adhesive effect Effects 0.000 description 10
- 238000005227 gel permeation chromatography Methods 0.000 description 10
- 238000010626 work up procedure Methods 0.000 description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 9
- 239000004793 Polystyrene Substances 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 229920002223 polystyrene Polymers 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 8
- 239000005977 Ethylene Substances 0.000 description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 8
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 8
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 8
- 239000011230 binding agent Substances 0.000 description 8
- 239000004568 cement Substances 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 239000002131 composite material Substances 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 8
- 150000002430 hydrocarbons Chemical class 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 238000011084 recovery Methods 0.000 description 8
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical class CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 7
- 150000002367 halogens Chemical group 0.000 description 7
- 238000002955 isolation Methods 0.000 description 7
- 239000004800 polyvinyl chloride Substances 0.000 description 7
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 6
- 125000006659 (C1-C20) hydrocarbyl group Chemical group 0.000 description 6
- 239000004342 Benzoyl peroxide Substances 0.000 description 6
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 6
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 235000019400 benzoyl peroxide Nutrition 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 238000007334 copolymerization reaction Methods 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 238000004806 packaging method and process Methods 0.000 description 6
- 239000000123 paper Substances 0.000 description 6
- 229920002239 polyacrylonitrile Polymers 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 6
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 6
- 239000013557 residual solvent Substances 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- 229920001567 vinyl ester resin Polymers 0.000 description 6
- 239000011345 viscous material Substances 0.000 description 6
- 239000012855 volatile organic compound Substances 0.000 description 6
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000008199 coating composition Substances 0.000 description 5
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 125000005395 methacrylic acid group Chemical class 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
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- 239000007858 starting material Substances 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
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- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 3
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- 239000012044 organic layer Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 239000011087 paperboard Substances 0.000 description 1
- GYDSPAVLTMAXHT-UHFFFAOYSA-N pentyl 2-methylprop-2-enoate Chemical compound CCCCCOC(=O)C(C)=C GYDSPAVLTMAXHT-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- ULDDEWDFUNBUCM-UHFFFAOYSA-N pentyl prop-2-enoate Chemical compound CCCCCOC(=O)C=C ULDDEWDFUNBUCM-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000006069 physical mixture Substances 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005629 polypropylene homopolymer Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000007781 pre-processing Methods 0.000 description 1
- 238000012673 precipitation polymerization Methods 0.000 description 1
- 239000001294 propane Substances 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 238000009419 refurbishment Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000009436 residential construction Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000003763 resistance to breakage Effects 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000010454 slate Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000011145 styrene acrylonitrile resin Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical group CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical class C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 229920000428 triblock copolymer Polymers 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical group C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 125000002348 vinylic group Chemical group 0.000 description 1
- 229920001959 vinylidene polymer Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 150000003738 xylenes Chemical class 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
- 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
- C08F290/042—Polymers of hydrocarbons as defined in group C08F10/00
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Graft Or Block Polymers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Paints Or Removers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4204397P | 1997-02-25 | 1997-02-25 | |
| US3912397P | 1997-02-25 | 1997-02-25 | |
| US39123P | 1997-02-25 | ||
| US42043P | 1997-02-25 | ||
| US4203697P | 1997-03-28 | 1997-03-28 | |
| US4211497P | 1997-03-28 | 1997-03-28 | |
| US42114P | 1997-03-28 | ||
| US42036P | 1997-03-28 | ||
| PCT/US1998/002990 WO1998037112A1 (en) | 1997-02-25 | 1998-02-17 | Copolymers of high vinylidene polyolefins with vinyl or vinylidene monomers produced by free radical polymerization |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69832334D1 DE69832334D1 (de) | 2005-12-22 |
| DE69832334T2 true DE69832334T2 (de) | 2006-09-14 |
Family
ID=27488582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69832334T Expired - Fee Related DE69832334T2 (de) | 1997-02-25 | 1998-02-17 | Durch radikalische polymerisation hergestellte copolymere von polyolefinen mit hohem vinylidenegehalt und vinyl- oder vinyliden-monomeren |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6583228B2 (enExample) |
| EP (1) | EP0894102B8 (enExample) |
| JP (1) | JP2001524996A (enExample) |
| CN (1) | CN100366653C (enExample) |
| AR (1) | AR011165A1 (enExample) |
| AT (1) | ATE310032T1 (enExample) |
| BR (1) | BR9805903A (enExample) |
| CA (1) | CA2252525C (enExample) |
| DE (1) | DE69832334T2 (enExample) |
| TW (1) | TWI251597B (enExample) |
| WO (1) | WO1998037112A1 (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040071980A1 (en) * | 2000-07-12 | 2004-04-15 | Mcbain Douglas S. | Method for in-mold coating a polyolefin article |
| US7589150B2 (en) | 2000-12-12 | 2009-09-15 | Baker Hughes Incorporated | Low molecular weight isotactic polypropylene polymers, copolymers and derivatives and materials prepared therewith |
| US6642298B2 (en) * | 2001-03-16 | 2003-11-04 | National Starch And Chemical Investment Holding Corporation | Rubber-acrylic adhesive formulation |
| TW593614B (en) | 2001-03-16 | 2004-06-21 | Nat Starch Chem Invest | Rubber-acrylic adhesive formulation |
| DE10297685T5 (de) * | 2002-03-25 | 2005-03-03 | National Starch And Chemical Investment Holding Corporation, New Castle | Kautschuk-Acryl-Kleber-Formulierung |
| US7781552B2 (en) * | 2003-11-06 | 2010-08-24 | Asahi Kasei Chemicals Corporation | Styrene copolymer and process for producing the same |
| US7763687B2 (en) * | 2004-02-20 | 2010-07-27 | Cornell Research Foundation, Inc. | Polymers containing quaternized nitrogen |
| US7709055B2 (en) * | 2004-02-20 | 2010-05-04 | Cornell Research Foundation, Inc. | Polymers with ether containing side chains and compositions thereof |
| US7887790B2 (en) * | 2004-02-20 | 2011-02-15 | Cornell Research Foundation, Inc. | Polymers and polymer coatings |
| US20070044493A1 (en) * | 2005-08-23 | 2007-03-01 | International Business Machines Corporation | Systems and methods for cooling electronics components employing vapor compression refrigeration with selected portions of expansion structures coated with polytetrafluorethylene |
| US20070048249A1 (en) | 2005-08-24 | 2007-03-01 | Purdue Research Foundation | Hydrophilized bactericidal polymers |
| EP1971216B2 (en) * | 2005-12-29 | 2019-04-10 | Wm. Wrigley Jr. Company | Chewing gum containing styrene-diene block copolymers |
| US20080044666A1 (en) * | 2006-08-17 | 2008-02-21 | Anderson Jerrel C | Amine-neutralized ethylene acid copolymers, shaped articles and laminates produced therefrom |
| US8889200B2 (en) * | 2007-03-12 | 2014-11-18 | Wm. Wrigley Jr. Company | Chewing gum and gum bases containing polyolefin thermoplastic elastomer |
| TWI512103B (zh) | 2012-11-12 | 2015-12-11 | Ind Tech Res Inst | 細胞培養系統、以及無血清細胞培養方法 |
| WO2018222622A1 (en) | 2017-05-27 | 2018-12-06 | Poly Group LLC | Dispersible antimicrobial complex and coatings therefrom |
| PL3638740T3 (pl) | 2017-06-16 | 2024-10-14 | Poly Group LLC | Polimerowy przeciwdrobnoustrojowy środek powierzchniowo czynny |
| WO2019157002A1 (en) * | 2018-02-06 | 2019-08-15 | Northwestern University | Highly branched, low molecular weight polyolefins and methods for their production |
| EP3902867A4 (en) * | 2018-12-28 | 2022-09-14 | Dow Global Technologies LLC | CURABLE COMPOSITIONS CONTAINING UNSATURATED POLYOLEFINS |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4524188A (en) * | 1983-05-02 | 1985-06-18 | University Of Akron | Synthesis and copolymerization of asymmetric polymers |
| TW211019B (enExample) * | 1991-12-20 | 1993-08-11 | Shell Internat Res Schappej B V | |
| DE4330971A1 (de) * | 1993-09-13 | 1995-03-16 | Basf Ag | Copolymerisate sowie deren Reaktionsprodukte mit Aminen als Kraftstoff- und Schmierstoffadditiv |
| JP3363904B2 (ja) * | 1993-10-26 | 2003-01-08 | 出光興産株式会社 | 分岐状エチレン系マクロモノマー及びそれを用いた重合体 |
| DE19528369A1 (de) * | 1994-08-08 | 1996-02-15 | Basf Ag | Polypropylenhaftkleber |
| US5733993A (en) * | 1996-11-14 | 1998-03-31 | Ethyl Corporation | Polymeric dispersants via novel terpolymers |
| US6100224A (en) * | 1997-10-01 | 2000-08-08 | Exxon Chemical Patents Inc | Copolymers of ethylene α-olefin macromers and dicarboxylic monomers and derivatives thereof, useful as additives in lubricating oils and in fuels |
-
1998
- 1998-02-17 BR BR9805903A patent/BR9805903A/pt not_active IP Right Cessation
- 1998-02-17 US US09/171,574 patent/US6583228B2/en not_active Expired - Fee Related
- 1998-02-17 EP EP98905105A patent/EP0894102B8/en not_active Expired - Lifetime
- 1998-02-17 WO PCT/US1998/002990 patent/WO1998037112A1/en not_active Ceased
- 1998-02-17 CN CNB988001799A patent/CN100366653C/zh not_active Expired - Fee Related
- 1998-02-17 DE DE69832334T patent/DE69832334T2/de not_active Expired - Fee Related
- 1998-02-17 CA CA002252525A patent/CA2252525C/en not_active Expired - Fee Related
- 1998-02-17 AT AT98905105T patent/ATE310032T1/de not_active IP Right Cessation
- 1998-02-17 JP JP53677198A patent/JP2001524996A/ja not_active Ceased
- 1998-02-20 TW TW087102389A patent/TWI251597B/zh not_active IP Right Cessation
- 1998-02-24 AR ARP980100816A patent/AR011165A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20020161156A1 (en) | 2002-10-31 |
| US6583228B2 (en) | 2003-06-24 |
| WO1998037112A1 (en) | 1998-08-27 |
| TWI251597B (en) | 2006-03-21 |
| AR011165A1 (es) | 2000-08-02 |
| JP2001524996A (ja) | 2001-12-04 |
| BR9805903A (pt) | 1999-08-24 |
| CA2252525A1 (en) | 1998-08-27 |
| EP0894102B1 (en) | 2005-11-16 |
| DE69832334D1 (de) | 2005-12-22 |
| CA2252525C (en) | 2006-08-15 |
| EP0894102A1 (en) | 1999-02-03 |
| CN1217728A (zh) | 1999-05-26 |
| CN100366653C (zh) | 2008-02-06 |
| ATE310032T1 (de) | 2005-12-15 |
| EP0894102B8 (en) | 2006-01-18 |
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Legal Events
| Date | Code | Title | Description |
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| 8327 | Change in the person/name/address of the patent owner |
Owner name: O&D USA LLC, CHICAGO, ILL., US |
|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: INNOVENE USA LLC, CHICAGO, ILL., US |
|
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: INEOS USA LLC, WILMINGTON, DEL., US |
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| 8339 | Ceased/non-payment of the annual fee |