JP2004537618A - 重合可能な連鎖移動剤を使用してグラフトコポリマーの分子量を調節する方法 - Google Patents
重合可能な連鎖移動剤を使用してグラフトコポリマーの分子量を調節する方法 Download PDFInfo
- Publication number
- JP2004537618A JP2004537618A JP2003519122A JP2003519122A JP2004537618A JP 2004537618 A JP2004537618 A JP 2004537618A JP 2003519122 A JP2003519122 A JP 2003519122A JP 2003519122 A JP2003519122 A JP 2003519122A JP 2004537618 A JP2004537618 A JP 2004537618A
- Authority
- JP
- Japan
- Prior art keywords
- propylene
- olefin
- ethylene
- weight
- copolymer
- 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.)
- Pending
Links
- 239000012986 chain transfer agent Substances 0.000 title claims abstract description 33
- 229920000578 graft copolymer Polymers 0.000 title claims abstract description 29
- 238000000034 method Methods 0.000 title claims description 14
- 239000000178 monomer Substances 0.000 claims abstract description 47
- 239000002861 polymer material Substances 0.000 claims abstract description 32
- 229920001155 polypropylene Polymers 0.000 claims abstract description 32
- 239000003999 initiator Substances 0.000 claims abstract description 18
- 150000003254 radicals Chemical class 0.000 claims abstract description 15
- 150000004808 allyl alcohols Chemical class 0.000 claims abstract description 6
- 239000007870 radical polymerization initiator Substances 0.000 claims abstract description 5
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 53
- 239000005977 Ethylene Substances 0.000 claims description 53
- 239000004711 α-olefin Substances 0.000 claims description 47
- 125000004432 carbon atom Chemical group C* 0.000 claims description 41
- 229920001577 copolymer Polymers 0.000 claims description 38
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 36
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 36
- -1 Polypropylene Polymers 0.000 claims description 28
- 238000006116 polymerization reaction Methods 0.000 claims description 24
- 150000001336 alkenes Chemical class 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 20
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 17
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 17
- 239000008096 xylene Substances 0.000 claims description 17
- 229920001384 propylene homopolymer Polymers 0.000 claims description 14
- 229920000098 polyolefin Polymers 0.000 claims description 13
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 9
- 150000001993 dienes Chemical class 0.000 claims description 7
- 229920001897 terpolymer Polymers 0.000 claims description 6
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 5
- 229920002397 thermoplastic olefin Polymers 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 229920001198 elastomeric copolymer Polymers 0.000 claims description 3
- 229920001519 homopolymer Polymers 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 229920005606 polypropylene copolymer Polymers 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 6
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims 5
- 125000001033 ether group Chemical group 0.000 claims 2
- 239000004743 Polypropylene Substances 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 abstract description 3
- 229920000642 polymer Polymers 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000007789 gas Substances 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000007619 statistical method Methods 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
- 239000004926 polymethyl methacrylate Substances 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 238000010559 graft polymerization reaction Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- NGFUZFAPKBLICJ-UHFFFAOYSA-N 2-but-1-enylpyridine Chemical compound CCC=CC1=CC=CC=N1 NGFUZFAPKBLICJ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- STEKLRLQGZCGKC-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxyperoxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOOOC(=O)OC1CCC(C(C)(C)C)CC1 STEKLRLQGZCGKC-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
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- LLVWLCAZSOLOTF-UHFFFAOYSA-N 1-methyl-4-[1,4,4-tris(4-methylphenyl)buta-1,3-dienyl]benzene Chemical compound C1=CC(C)=CC=C1C(C=1C=CC(C)=CC=1)=CC=C(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 LLVWLCAZSOLOTF-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
- VCWDAHMQCOZVQD-UHFFFAOYSA-N 2-chloroprop-1-enylbenzene Chemical compound CC(Cl)=CC1=CC=CC=C1 VCWDAHMQCOZVQD-UHFFFAOYSA-N 0.000 description 1
- BSAKKMQHOSYINC-UHFFFAOYSA-N 2-ethyl-2-(4-hydroxy-2-methylpentan-2-yl)peroxyhexanoic acid Chemical compound CCCCC(CC)(C(=O)O)OOC(C)(C)CC(C)O BSAKKMQHOSYINC-UHFFFAOYSA-N 0.000 description 1
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 1
- ZACVGCNKGYYQHA-UHFFFAOYSA-N 2-ethylhexoxycarbonyloxy 2-ethylhexyl carbonate Chemical compound CCCCC(CC)COC(=O)OOC(=O)OCC(CC)CCCC ZACVGCNKGYYQHA-UHFFFAOYSA-N 0.000 description 1
- SMTDFMMXJHYDDE-UHFFFAOYSA-N 2-prop-1-enylpyridine Chemical compound CC=CC1=CC=CC=N1 SMTDFMMXJHYDDE-UHFFFAOYSA-N 0.000 description 1
- BIISIZOQPWZPPS-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-ylbenzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1 BIISIZOQPWZPPS-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- OXGOEZHUKDEEKS-UHFFFAOYSA-N 3-tert-butylperoxy-1,1,5-trimethylcyclohexane Chemical compound CC1CC(OOC(C)(C)C)CC(C)(C)C1 OXGOEZHUKDEEKS-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
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- RMZIOVJHUJAAEY-UHFFFAOYSA-N Allyl butyrate Chemical compound CCCC(=O)OCC=C RMZIOVJHUJAAEY-UHFFFAOYSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 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
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 239000000898 Thymopoietin Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- ATMLPEJAVWINOF-UHFFFAOYSA-N acrylic acid acrylic acid Chemical class OC(=O)C=C.OC(=O)C=C ATMLPEJAVWINOF-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical class CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 229920003244 diene elastomer Polymers 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- XJELOQYISYPGDX-UHFFFAOYSA-N ethenyl 2-chloroacetate Chemical compound ClCC(=O)OC=C XJELOQYISYPGDX-UHFFFAOYSA-N 0.000 description 1
- ANTNQGGUTAZUIC-UHFFFAOYSA-N ethenyl 2-cyanoacetate Chemical compound C=COC(=O)CC#N ANTNQGGUTAZUIC-UHFFFAOYSA-N 0.000 description 1
- GFJVXXWOPWLRNU-UHFFFAOYSA-N ethenyl formate Chemical compound C=COC=O GFJVXXWOPWLRNU-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-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
- 150000004978 peroxycarbonates Chemical class 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920006124 polyolefin elastomer Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000004663 powder metallurgy Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- KOODSCBKXPPKHE-UHFFFAOYSA-N propanethioic s-acid Chemical compound CCC(S)=O KOODSCBKXPPKHE-UHFFFAOYSA-N 0.000 description 1
- YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000011800 void material Substances 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
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- 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
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
- C08F255/02—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Graft Or Block Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/924,253 US6506847B1 (en) | 2001-08-08 | 2001-08-08 | Controlling the molecular weight of graft copolymers using polymerizable chain transfer agents |
| PCT/IB2002/003082 WO2003014175A1 (en) | 2001-08-08 | 2002-08-05 | Controlling the molecular weight of graft copolymers using polymerizable chain transfer agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004537618A true JP2004537618A (ja) | 2004-12-16 |
| JP2004537618A5 JP2004537618A5 (enExample) | 2006-01-05 |
Family
ID=25449955
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003519122A Pending JP2004537618A (ja) | 2001-08-08 | 2002-08-05 | 重合可能な連鎖移動剤を使用してグラフトコポリマーの分子量を調節する方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US6506847B1 (enExample) |
| EP (1) | EP1421124A1 (enExample) |
| JP (1) | JP2004537618A (enExample) |
| CN (1) | CN1249112C (enExample) |
| WO (1) | WO2003014175A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7541402B2 (en) * | 2002-10-15 | 2009-06-02 | Exxonmobil Chemical Patents Inc. | Blend functionalized polyolefin adhesive |
| ES2394304T3 (es) * | 2002-10-15 | 2013-01-30 | Exxonmobil Chemical Patents, Inc. | Sistema de múltiples catalizadores para la polimerización de olefinas y polímeros producidos a partir de éstos |
| US7550528B2 (en) | 2002-10-15 | 2009-06-23 | Exxonmobil Chemical Patents Inc. | Functionalized olefin polymers |
| US7700707B2 (en) | 2002-10-15 | 2010-04-20 | Exxonmobil Chemical Patents Inc. | Polyolefin adhesive compositions and articles made therefrom |
| WO2008020556A1 (en) * | 2006-08-14 | 2008-02-21 | Nippon Shokubai Co., Ltd. | Hydrophilic graft polymer |
| CN102083897B (zh) * | 2008-05-30 | 2013-06-12 | 3M创新有限公司 | 制备配体官能化基底的方法 |
| EP2313183B1 (en) | 2008-05-30 | 2015-11-04 | 3M Innovative Properties Company | Ligand functionalized substrates |
| US20100209693A1 (en) * | 2009-02-18 | 2010-08-19 | 3M Innovative Properties Company | Hydrophilic porous substrates |
| US20100210160A1 (en) * | 2009-02-18 | 2010-08-19 | 3M Innovative Properties Company | Hydrophilic porous substrates |
| JP2012531531A (ja) | 2009-06-23 | 2012-12-10 | スリーエム イノベイティブ プロパティズ カンパニー | 官能化不織布物品 |
| US8377672B2 (en) | 2010-02-18 | 2013-02-19 | 3M Innovative Properties Company | Ligand functionalized polymers |
| EP2889625B1 (en) | 2010-03-03 | 2016-09-14 | 3M Innovative Properties Company | Ligand guanidinyl functionalized polymers |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1166089A (en) | 1966-05-23 | 1969-10-01 | Mitsubishi Rayon Co | Dyeable polypropylene having improved properties and dyeing process for producing dyed articles fast to light |
| GB1217231A (en) * | 1967-01-13 | 1970-12-31 | Asahi Chemical Ind | Modified polymer composition and a process for producing the same |
| GB1244435A (en) * | 1968-06-18 | 1971-09-02 | Lubrizol Corp | Oil-soluble graft polymers derived from degraded ethylene-propylene interpolymers |
| US4000220A (en) | 1971-07-09 | 1976-12-28 | Hitachi, Ltd. | Method for producing thermoplastic resin |
| IT1007901B (it) | 1974-04-12 | 1976-10-30 | Montedison Spa | Procedimento per la produzione di polisterolo resistente all urto |
| US4208490A (en) | 1975-07-31 | 1980-06-17 | Sumitomo Chemical Company, Limited | Process for preparing polymer resins |
| US4012461A (en) * | 1975-08-06 | 1977-03-15 | Exxon Research And Engineering Company | Process for preparing polymer powders |
| DE3002394A1 (de) | 1980-01-24 | 1981-07-30 | Röhm GmbH, 6100 Darmstadt | Verfahren zur herstellung schlagzaeher formmassen |
| DE3023721A1 (de) | 1980-06-25 | 1982-01-21 | Basf Ag, 6700 Ludwigshafen | Verfahren zur kontinuierlichen herstellung von mit kautschuk modifizierten polymerisaten von vinylaromaten |
| US4877834A (en) * | 1987-04-10 | 1989-10-31 | Texaco Inc. | Lubricating oil containing a Mannich base |
| IT1230133B (it) | 1989-04-28 | 1991-10-14 | Himont Inc | Composizioni polipropileniche plasto-elastiche |
| US5140074A (en) | 1990-01-26 | 1992-08-18 | Himont Incorporated | Method of producing olefin polymer graft copolymers |
| DE69018635D1 (de) * | 1990-06-11 | 1995-05-18 | Sumitomo Chemical Co | Thermoplastische harzzusammensetzung. |
| US5212246A (en) | 1990-09-28 | 1993-05-18 | Himont Incorporated | Olefin polymer films |
| JPH0790035A (ja) | 1993-07-27 | 1995-04-04 | Ube Ind Ltd | プロピレンブロック共重合体の製造方法 |
| US5409992A (en) | 1994-02-28 | 1995-04-25 | Himont Incorporated | Calenderable blends containing broad molecular weight distribution propylene polymer material |
| WO1997021745A1 (en) * | 1995-12-08 | 1997-06-19 | Kaneka Corporation | Grafted polyolefin resin and thermoplastic resin composition containing the same |
| DE19607430C1 (de) * | 1996-02-28 | 1997-04-24 | Danubia Petrochem Polymere | Kontinuierliches Verfahren zur Modifizierung von Polyolefinen in der festen Phase |
| DE19629429C2 (de) * | 1996-07-22 | 2001-03-01 | Borealis Gmbh Schwechat Mannsw | Verfahren zur Herstellung von vernetzbaren olefinischen Polymeren |
| US5863994A (en) | 1997-09-29 | 1999-01-26 | Montell North America Inc. | Using nitric oxide to reduce reactor fouling during polypropylene graft copolymerization |
-
2001
- 2001-08-08 US US09/924,253 patent/US6506847B1/en not_active Expired - Fee Related
-
2002
- 2002-08-05 EP EP02765141A patent/EP1421124A1/en not_active Withdrawn
- 2002-08-05 JP JP2003519122A patent/JP2004537618A/ja active Pending
- 2002-08-05 WO PCT/IB2002/003082 patent/WO2003014175A1/en not_active Ceased
- 2002-08-05 CN CN02802697.7A patent/CN1249112C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1466600A (zh) | 2004-01-07 |
| US6506847B1 (en) | 2003-01-14 |
| CN1249112C (zh) | 2006-04-05 |
| WO2003014175A1 (en) | 2003-02-20 |
| EP1421124A1 (en) | 2004-05-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU630539B2 (en) | Mehtod of producing olefin polymer graft copolymers | |
| JP4773658B2 (ja) | フッ素化モノマーで製造されるポリオレフィングラフトコポリマー | |
| AU779017B2 (en) | Making polyolefin graft copolymers with low molecular weight side chains using a polymeric peroxide as an initiator | |
| US5863994A (en) | Using nitric oxide to reduce reactor fouling during polypropylene graft copolymerization | |
| JP2004537618A (ja) | 重合可能な連鎖移動剤を使用してグラフトコポリマーの分子量を調節する方法 | |
| CA2394671C (en) | Irradiation process for making olefin graft copolymers with low molecular weight side chains | |
| KR100588956B1 (ko) | 폴리프로필렌그래프트공중합체의형태제어 | |
| CA2140975C (en) | Process for sequentially grafting olefin polymer materials and grafted polymers therefrom | |
| RU2060999C1 (ru) | Способ получения привитого сополимера полиолефина | |
| JPH06263830A (ja) | グラフト化ビニルポリマーの製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20050805 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20050805 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20080918 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20081006 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20090309 |