ES2325697T3 - Injerto de monomeros etilenicamente insaturados sobre polimeros. - Google Patents
Injerto de monomeros etilenicamente insaturados sobre polimeros. Download PDFInfo
- Publication number
- ES2325697T3 ES2325697T3 ES99944478T ES99944478T ES2325697T3 ES 2325697 T3 ES2325697 T3 ES 2325697T3 ES 99944478 T ES99944478 T ES 99944478T ES 99944478 T ES99944478 T ES 99944478T ES 2325697 T3 ES2325697 T3 ES 2325697T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- baselineskip
- cycloalkyl
- substituted
- radical
- 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.)
- Expired - Lifetime
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- 229920000642 polymer Polymers 0.000 claims abstract description 86
- 238000000034 method Methods 0.000 claims abstract description 46
- 239000000178 monomer Substances 0.000 claims abstract description 42
- 229920000578 graft copolymer Polymers 0.000 claims abstract description 25
- YLFIGGHWWPSIEG-UHFFFAOYSA-N aminoxyl Chemical compound [O]N YLFIGGHWWPSIEG-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 21
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 19
- 238000002360 preparation method Methods 0.000 claims abstract description 14
- 239000003999 initiator Substances 0.000 claims abstract description 12
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- 238000001816 cooling Methods 0.000 claims abstract description 3
- -1 bis-azo compound Chemical class 0.000 claims description 189
- 125000000217 alkyl group Chemical group 0.000 claims description 136
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 77
- 239000001257 hydrogen Substances 0.000 claims description 70
- 229910052739 hydrogen Inorganic materials 0.000 claims description 70
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 69
- 150000003254 radicals Chemical class 0.000 claims description 60
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 59
- 150000002431 hydrogen Chemical class 0.000 claims description 49
- 229920001577 copolymer Polymers 0.000 claims description 47
- 239000002253 acid Substances 0.000 claims description 43
- 229910052736 halogen Inorganic materials 0.000 claims description 39
- 150000002367 halogens Chemical class 0.000 claims description 39
- 229910052799 carbon Inorganic materials 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 34
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 34
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 34
- 125000004429 atom Chemical group 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
- 125000002947 alkylene group Chemical group 0.000 claims description 27
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 25
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 24
- 125000003342 alkenyl group Chemical group 0.000 claims description 22
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000001931 aliphatic group Chemical group 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 239000004743 Polypropylene Substances 0.000 claims description 18
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000001624 naphthyl group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 13
- 239000005977 Ethylene Substances 0.000 claims description 13
- 229910004013 NO 2 Inorganic materials 0.000 claims description 13
- 150000001993 dienes Chemical class 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 229920002857 polybutadiene Polymers 0.000 claims description 13
- 229920001155 polypropylene Polymers 0.000 claims description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 12
- 239000005062 Polybutadiene Substances 0.000 claims description 12
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 12
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 12
- 239000004698 Polyethylene Substances 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000001589 carboacyl group Chemical group 0.000 claims description 11
- 229920000573 polyethylene Polymers 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 10
- 150000001721 carbon Chemical group 0.000 claims description 10
- 229920001971 elastomer Polymers 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 9
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
- 150000002978 peroxides Chemical class 0.000 claims description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 claims description 7
- OLRJXMHANKMLTD-UHFFFAOYSA-N silyl Chemical compound [SiH3] OLRJXMHANKMLTD-UHFFFAOYSA-N 0.000 claims description 7
- 229920001897 terpolymer Polymers 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
- 239000004793 Polystyrene Substances 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- 239000000853 adhesive Substances 0.000 claims description 6
- 230000001070 adhesive effect Effects 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 239000011574 phosphorus Substances 0.000 claims description 6
- 229920002959 polymer blend Polymers 0.000 claims description 6
- 239000005060 rubber Substances 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229920002223 polystyrene Polymers 0.000 claims description 5
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 4
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical compound CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 claims description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 4
- 125000003031 C5-C7 cycloalkylene group Chemical group 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 4
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 4
- 229910021386 carbon form Inorganic materials 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 claims description 4
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 4
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 4
- 229920001195 polyisoprene Polymers 0.000 claims description 4
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical class CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000006839 xylylene group Chemical group 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 238000010494 dissociation reaction Methods 0.000 claims description 3
- 230000005593 dissociations Effects 0.000 claims description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 3
- 239000012744 reinforcing agent Substances 0.000 claims description 3
- 230000003252 repetitive effect Effects 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 229920006132 styrene block copolymer Polymers 0.000 claims description 3
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 3
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 claims description 3
- WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 claims description 2
- KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 claims description 2
- OXYKVVLTXXXVRT-UHFFFAOYSA-N (4-chlorobenzoyl) 4-chlorobenzenecarboperoxoate Chemical compound C1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1 OXYKVVLTXXXVRT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 2
- NALFRYPTRXKZPN-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(OOC(C)(C)C)(OOC(C)(C)C)C1 NALFRYPTRXKZPN-UHFFFAOYSA-N 0.000 claims description 2
- HSLFISVKRDQEBY-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)cyclohexane Chemical compound CC(C)(C)OOC1(OOC(C)(C)C)CCCCC1 HSLFISVKRDQEBY-UHFFFAOYSA-N 0.000 claims description 2
- CCNDOQHYOIISTA-UHFFFAOYSA-N 1,2-bis(2-tert-butylperoxypropan-2-yl)benzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1C(C)(C)OOC(C)(C)C CCNDOQHYOIISTA-UHFFFAOYSA-N 0.000 claims description 2
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 claims description 2
- HQOVXPHOJANJBR-UHFFFAOYSA-N 2,2-bis(tert-butylperoxy)butane Chemical compound CC(C)(C)OOC(C)(CC)OOC(C)(C)C HQOVXPHOJANJBR-UHFFFAOYSA-N 0.000 claims description 2
- CCTFAOUOYLVUFG-UHFFFAOYSA-N 2-(1-amino-1-imino-2-methylpropan-2-yl)azo-2-methylpropanimidamide Chemical compound NC(=N)C(C)(C)N=NC(C)(C)C(N)=N CCTFAOUOYLVUFG-UHFFFAOYSA-N 0.000 claims description 2
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- QSFTWOJPCWPORR-UHFFFAOYSA-N 2-(2-tert-butylperoxypropan-2-ylperoxy)-2-methylpropane Chemical compound CC(C)(C)OOC(C)(C)OOC(C)(C)C QSFTWOJPCWPORR-UHFFFAOYSA-N 0.000 claims description 2
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 claims description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 2
- LDQYWNUWKVADJV-UHFFFAOYSA-N 2-[(1-amino-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanamide;dihydrate Chemical compound O.O.NC(=O)C(C)(C)N=NC(C)(C)C(N)=O LDQYWNUWKVADJV-UHFFFAOYSA-N 0.000 claims description 2
- PFHOSZAOXCYAGJ-UHFFFAOYSA-N 2-[(2-cyano-4-methoxy-4-methylpentan-2-yl)diazenyl]-4-methoxy-2,4-dimethylpentanenitrile Chemical compound COC(C)(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)(C)OC PFHOSZAOXCYAGJ-UHFFFAOYSA-N 0.000 claims description 2
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 claims description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 2
- JJRDRFZYKKFYMO-UHFFFAOYSA-N 2-methyl-2-(2-methylbutan-2-ylperoxy)butane Chemical compound CCC(C)(C)OOC(C)(C)CC JJRDRFZYKKFYMO-UHFFFAOYSA-N 0.000 claims description 2
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 claims description 2
- QRIQYQXNFSXNGR-UHFFFAOYSA-N 3,3,6,6,9,9-hexamethyl-1,2,4,5-tetraoxonane Chemical compound CC1(C)CCC(C)(C)OOC(C)(C)OO1 QRIQYQXNFSXNGR-UHFFFAOYSA-N 0.000 claims description 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 2
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 2
- JJHHIGCUQPTUHO-UHFFFAOYSA-N 3-tert-butylperoxy-3-phenyl-2-benzofuran-1-one Chemical compound O1C(=O)C2=CC=CC=C2C1(OOC(C)(C)C)C1=CC=CC=C1 JJHHIGCUQPTUHO-UHFFFAOYSA-N 0.000 claims description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 2
- XKXGWYAQJRXDPI-UHFFFAOYSA-N 7-methyloctanoyl 7-methyloctaneperoxoate Chemical compound CC(C)CCCCCC(=O)OOC(=O)CCCCCC(C)C XKXGWYAQJRXDPI-UHFFFAOYSA-N 0.000 claims description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- 101100348503 Caenorhabditis elegans nhr-106 gene Proteins 0.000 claims description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 2
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000003926 acrylamides Chemical class 0.000 claims description 2
- 229920006397 acrylic thermoplastic Polymers 0.000 claims description 2
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 2
- WPKWPKDNOPEODE-UHFFFAOYSA-N bis(2,4,4-trimethylpentan-2-yl)diazene Chemical compound CC(C)(C)CC(C)(C)N=NC(C)(C)CC(C)(C)C WPKWPKDNOPEODE-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- BSVQJWUUZCXSOL-UHFFFAOYSA-N cyclohexylsulfonyl ethaneperoxoate Chemical compound CC(=O)OOS(=O)(=O)C1CCCCC1 BSVQJWUUZCXSOL-UHFFFAOYSA-N 0.000 claims description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 2
- GKCPCPKXFGQXGS-UHFFFAOYSA-N ditert-butyldiazene Chemical compound CC(C)(C)N=NC(C)(C)C GKCPCPKXFGQXGS-UHFFFAOYSA-N 0.000 claims description 2
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 claims description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 2
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
-
- 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
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
-
- 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
-
- 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
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F291/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
- C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/003—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L53/02—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- C09D151/003—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D153/00—Coating compositions based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J151/003—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J153/00—Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymerisation Methods In General (AREA)
- Graft Or Block Polymers (AREA)
- Polymerization Catalysts (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98810878 | 1998-09-03 | ||
| EP98810878 | 1998-09-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2325697T3 true ES2325697T3 (es) | 2009-09-14 |
Family
ID=8236299
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES99944478T Expired - Lifetime ES2325697T3 (es) | 1998-09-03 | 1999-08-23 | Injerto de monomeros etilenicamente insaturados sobre polimeros. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6525151B1 (enExample) |
| EP (1) | EP1115765B1 (enExample) |
| JP (1) | JP4516212B2 (enExample) |
| KR (1) | KR100575170B1 (enExample) |
| CN (1) | CN1298755C (enExample) |
| AT (1) | ATE434635T1 (enExample) |
| AU (1) | AU759408B2 (enExample) |
| BR (1) | BR9913419A (enExample) |
| CA (1) | CA2341372A1 (enExample) |
| DE (1) | DE69941028D1 (enExample) |
| ES (1) | ES2325697T3 (enExample) |
| WO (1) | WO2000014134A1 (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG82601A1 (en) * | 1998-03-09 | 2001-08-21 | Ciba Sc Holding Ag | 1-alkoxy-polyalkyl-piperidine derivatives and their use as polymerization regulators |
| AU760128B2 (en) * | 1998-09-03 | 2003-05-08 | Ciba Specialty Chemicals Holding Inc. | Grafting of ethylenically unsaturated monomers onto polymers |
| KR20020030822A (ko) * | 1999-09-15 | 2002-04-25 | 에프. 아. 프라저, 에른스트 알테르 (에. 알테르), 한스 페터 비틀린 (하. 페. 비틀린), 피. 랍 보프, 브이. 스펜글러, 페. 아에글러 | 펄프에 대한 친화성이 높은 중합성 안정화제 |
| US6414048B1 (en) * | 1999-12-07 | 2002-07-02 | Sumitomo Electric Fine Polymer, Inc. | Chemical grafting onto a substrate and coating composition |
| TW541303B (en) | 2000-03-22 | 2003-07-11 | Ciba Sc Holding Ag | 2,2,6,6 diethyl-dimethyl-1-alkoxy-piperidine compounds and their corresponding 1-oxides |
| CA2444971C (en) | 2001-05-15 | 2011-02-22 | Ciba Specialty Chemicals Holding Inc. | Method of grafting ethylenically unsaturated carboxylic acid derivatives onto thermoplastic polymers using hydroxylamine esters |
| MXPA04012671A (es) * | 2002-06-20 | 2005-03-23 | Ciba Sc Holding Ag | INJERTO DE OLIGOMEROS O POLIMEROS TERMINADOS EN NITROXILO SOBRE POLIMEROS TERMOPLáSTICOS. |
| AU2003297182A1 (en) * | 2002-12-18 | 2004-07-22 | Crompton Corporation | Styrenic polymer composites |
| WO2004069887A2 (en) * | 2003-02-10 | 2004-08-19 | Ciba Specialty Chemicals Holding Inc. | Comb copolymers with defined side chains and process for their manufacture |
| US20040220345A1 (en) * | 2003-05-01 | 2004-11-04 | Firestone Polymers, Llc | Stable free radical polymers |
| US6967228B2 (en) * | 2003-05-01 | 2005-11-22 | Firestone Polymers, Llc | Stable free radical polymers |
| US20070106029A1 (en) * | 2003-06-26 | 2007-05-10 | Mitsubishi Rayon Co., Ltd. | Modified polyolefin resin and composition |
| US7279527B2 (en) * | 2005-04-22 | 2007-10-09 | Bridgestone Corporation | Method of converting anionic living end to protected free radical living end and applications thereof |
| KR100666818B1 (ko) * | 2006-02-20 | 2007-01-09 | 주식회사 엘지화학 | 우수한 저온색상안정성을 갖는 열가소성 성형재 |
| JP2008044996A (ja) * | 2006-08-11 | 2008-02-28 | Mitsui Chemicals Inc | オレフィン系重合体 |
| JP4819616B2 (ja) * | 2006-08-11 | 2011-11-24 | 三井化学株式会社 | オレフィン系重合体 |
| US8030410B2 (en) * | 2006-12-29 | 2011-10-04 | Bridgestone Corporation | Method for generating free radical capable polymers using carbonyl-containing compounds |
| US7737218B2 (en) | 2006-12-29 | 2010-06-15 | Bridgestone Corporation | Method for generating free radical capable polymers using tin or silicon halide compounds |
| US7396887B1 (en) * | 2006-12-29 | 2008-07-08 | Bridgestone Corporation | Insitu removal of chelator from anionic polymerization reactions |
| US7560509B2 (en) * | 2006-12-29 | 2009-07-14 | Bridgestone Corporation | Method of directing grafting by controlling the location of high vinyl segments in a polymer |
| US20080157641A1 (en) * | 2006-12-31 | 2008-07-03 | Rachael Wren Grout | Multi-use Free Standing Seating and Storage Unit |
| CN102167784B (zh) * | 2010-12-30 | 2013-02-20 | 长春工业大学 | 一种水性化三元乙丙橡胶的制备方法 |
| CN102139229B (zh) * | 2011-01-19 | 2012-10-10 | 华东师范大学 | 一种负载型金催化剂的制备方法及其应用 |
| CN104140484B (zh) * | 2013-05-08 | 2016-08-17 | 中国石油化工股份有限公司 | 一种支化稀土异戊橡胶及其制备方法和橡胶组合物 |
| US10538611B2 (en) | 2014-04-18 | 2020-01-21 | Nippon A&L Inc. | Graft copolymer and thermoplastic resin composition |
| CN104650766A (zh) * | 2014-12-17 | 2015-05-27 | 浙江科达利实业有限公司 | 反应粘合剂胶料及其制造工艺 |
| CN105419440A (zh) * | 2015-12-18 | 2016-03-23 | 蚌埠市鑫晟新材料科技有限公司 | 一种可减少污染的内墙涂料添加剂的制备方法 |
| CN108017744B (zh) * | 2016-11-03 | 2021-07-30 | 中国石油化工股份有限公司 | 一种粉末羧基丁苯橡胶及其制备方法和应用 |
| CN109485795B (zh) * | 2018-11-08 | 2021-06-25 | 万华化学集团股份有限公司 | 一种共聚物相容剂及其制备方法和应用 |
| CN112876614A (zh) * | 2021-02-06 | 2021-06-01 | 中交第四公路工程局有限公司 | 一种杜仲胶与马来酸酐的熔融接枝方法 |
| TW202330677A (zh) | 2021-12-10 | 2023-08-01 | 義大利商佛沙里斯股份有限公司 | 橡膠強化的乙烯芳香族(共)聚合物及其製備方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6089452A (ja) * | 1983-07-11 | 1985-05-20 | コモンウエルス サイエンテイフイツク アンド インダストリアル リサ−チ オ−ガニゼ−シヨン | 遊離基重合開始用化合物 |
| DE3486145T2 (de) * | 1983-07-11 | 1993-09-23 | Commw Scient Ind Res Org | Verfahren zur polymerisation und nach diesem verfahren hergestellte polymere. |
| US5322912A (en) * | 1992-11-16 | 1994-06-21 | Xerox Corporation | Polymerization processes and toner compositions therefrom |
| FR2730240A1 (fr) * | 1995-02-07 | 1996-08-09 | Atochem Elf Sa | Stabilisation d'un polymere par un radical libre stable |
| WO1997036944A1 (en) * | 1996-03-29 | 1997-10-09 | The Dow Chemical Company | In situ block copolymer formation during polymerization of a vinyl aromatic monomer |
| US5723511A (en) | 1996-06-17 | 1998-03-03 | Xerox Corporation | Processes for preparing telechelic, branched and star thermoplastic resin polymers |
| US5910549A (en) * | 1996-08-22 | 1999-06-08 | Carnegie-Mellon University | Method for preparation of alkoxyamines from nitroxyl radicals |
| FR2754535A1 (fr) | 1996-10-16 | 1998-04-17 | Atochem Elf Sa | Polymeres greffes a viscosite controlee |
| US6281311B1 (en) * | 1997-03-31 | 2001-08-28 | Pmd Holdings Corp. | Controlled free radical polymerization process |
| FR2768739B1 (fr) * | 1997-09-19 | 2004-08-06 | Atochem Elf Sa | Polymere vinylaromatique choc obtenu a partir d'un caoutchouc porteur d'un groupement generateur d'un radical libre stable |
| DE19752394A1 (de) | 1997-11-19 | 1999-05-20 | Basf Ag | Verfahren zur Herstellung von Pfropfpolymerisaten |
| AU760128B2 (en) * | 1998-09-03 | 2003-05-08 | Ciba Specialty Chemicals Holding Inc. | Grafting of ethylenically unsaturated monomers onto polymers |
-
1999
- 1999-08-23 WO PCT/EP1999/006171 patent/WO2000014134A1/en not_active Ceased
- 1999-08-23 CN CNB998104655A patent/CN1298755C/zh not_active Expired - Fee Related
- 1999-08-23 KR KR1020017002032A patent/KR100575170B1/ko not_active Expired - Fee Related
- 1999-08-23 CA CA002341372A patent/CA2341372A1/en not_active Abandoned
- 1999-08-23 DE DE69941028T patent/DE69941028D1/de not_active Expired - Lifetime
- 1999-08-23 ES ES99944478T patent/ES2325697T3/es not_active Expired - Lifetime
- 1999-08-23 EP EP99944478A patent/EP1115765B1/en not_active Expired - Lifetime
- 1999-08-23 AU AU57387/99A patent/AU759408B2/en not_active Ceased
- 1999-08-23 AT AT99944478T patent/ATE434635T1/de not_active IP Right Cessation
- 1999-08-23 BR BR9913419-5A patent/BR9913419A/pt not_active Application Discontinuation
- 1999-08-23 US US09/786,186 patent/US6525151B1/en not_active Expired - Fee Related
- 1999-08-23 JP JP2000568889A patent/JP4516212B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR20010072721A (ko) | 2001-07-31 |
| CN1315971A (zh) | 2001-10-03 |
| EP1115765A1 (en) | 2001-07-18 |
| AU759408B2 (en) | 2003-04-17 |
| BR9913419A (pt) | 2001-05-22 |
| ATE434635T1 (de) | 2009-07-15 |
| DE69941028D1 (de) | 2009-08-06 |
| AU5738799A (en) | 2000-03-27 |
| WO2000014134A1 (en) | 2000-03-16 |
| JP2002524589A (ja) | 2002-08-06 |
| JP4516212B2 (ja) | 2010-08-04 |
| KR100575170B1 (ko) | 2006-04-28 |
| CN1298755C (zh) | 2007-02-07 |
| CA2341372A1 (en) | 2000-03-16 |
| EP1115765B1 (en) | 2009-06-24 |
| US6525151B1 (en) | 2003-02-25 |
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