CH617445A5 - - Google Patents
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- Publication number
- CH617445A5 CH617445A5 CH1596474A CH1596474A CH617445A5 CH 617445 A5 CH617445 A5 CH 617445A5 CH 1596474 A CH1596474 A CH 1596474A CH 1596474 A CH1596474 A CH 1596474A CH 617445 A5 CH617445 A5 CH 617445A5
- Authority
- CH
- Switzerland
- Prior art keywords
- hydroxy
- phenolic
- polymerization
- monomer
- methylstyrene
- Prior art date
Links
- 239000000178 monomer Substances 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 30
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 28
- 229920000642 polymer Polymers 0.000 claims description 26
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 238000007334 copolymerization reaction Methods 0.000 claims description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 11
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 10
- 229920001577 copolymer Polymers 0.000 claims description 10
- 229920002857 polybutadiene Polymers 0.000 claims description 10
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 7
- 239000000839 emulsion Substances 0.000 claims description 7
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims description 7
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 6
- 238000010559 graft polymerization reaction Methods 0.000 claims description 6
- 239000005062 Polybutadiene Substances 0.000 claims description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 238000002329 infrared spectrum Methods 0.000 claims description 4
- 239000004816 latex Substances 0.000 claims description 4
- 229920000126 latex Polymers 0.000 claims description 4
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- OTVDXQWQYPAXTF-UHFFFAOYSA-N 2-tert-butyl-5-ethenylphenol Chemical compound CC(C)(C)C1=CC=C(C=C)C=C1O OTVDXQWQYPAXTF-UHFFFAOYSA-N 0.000 claims description 3
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 3
- JAGRUUPXPPLSRX-UHFFFAOYSA-N 4-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=C(O)C=C1 JAGRUUPXPPLSRX-UHFFFAOYSA-N 0.000 claims description 3
- 230000021736 acetylation Effects 0.000 claims description 3
- 238000006640 acetylation reaction Methods 0.000 claims description 3
- 229940050176 methyl chloride Drugs 0.000 claims description 3
- 239000002683 reaction inhibitor Substances 0.000 claims description 3
- 238000001226 reprecipitation Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 claims description 2
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-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
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 229920000459 Nitrile rubber Polymers 0.000 claims description 2
- 229920001519 homopolymer Polymers 0.000 claims description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 229920003051 synthetic elastomer Polymers 0.000 claims description 2
- 229920001971 elastomer Polymers 0.000 claims 37
- 239000000806 elastomer Substances 0.000 claims 25
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 22
- 239000003505 polymerization initiator Substances 0.000 claims 12
- 239000005060 rubber Substances 0.000 claims 12
- -1 esters peroxides Chemical class 0.000 claims 11
- 239000003054 catalyst Substances 0.000 claims 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- 238000012662 bulk polymerization Methods 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 150000003254 radicals Chemical class 0.000 claims 6
- 125000002091 cationic group Chemical group 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 5
- 150000001993 dienes Chemical class 0.000 claims 5
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 150000002989 phenols Chemical class 0.000 claims 4
- 229920003048 styrene butadiene rubber Polymers 0.000 claims 4
- 238000010557 suspension polymerization reaction Methods 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 3
- 125000000129 anionic group Chemical group 0.000 claims 3
- 238000007720 emulsion polymerization reaction Methods 0.000 claims 3
- 150000002978 peroxides Chemical class 0.000 claims 3
- 150000004965 peroxy acids Chemical class 0.000 claims 3
- 230000009257 reactivity Effects 0.000 claims 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims 2
- CQABDOWDPOBTPG-UHFFFAOYSA-N 2,4-ditert-butyl-5-ethenylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(C=C)C=C1O CQABDOWDPOBTPG-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 2
- YNGIFMKMDRDNBQ-UHFFFAOYSA-N 3-ethenylphenol Chemical compound OC1=CC=CC(C=C)=C1 YNGIFMKMDRDNBQ-UHFFFAOYSA-N 0.000 claims 2
- ULHRXUXEWFGCNC-UHFFFAOYSA-N 5-ethenyl-2,4-di(propan-2-yl)phenol Chemical compound CC(C)C1=CC(C(C)C)=C(C=C)C=C1O ULHRXUXEWFGCNC-UHFFFAOYSA-N 0.000 claims 2
- DRUADBBTQDIPNO-UHFFFAOYSA-N 5-ethenyl-2,4-dimethylphenol Chemical compound CC1=CC(C)=C(C=C)C=C1O DRUADBBTQDIPNO-UHFFFAOYSA-N 0.000 claims 2
- BSNDCRUAZJCYQK-UHFFFAOYSA-N 5-ethenyl-2-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(C=C)C=C1O BSNDCRUAZJCYQK-UHFFFAOYSA-N 0.000 claims 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims 2
- 229920005549 butyl rubber Polymers 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 2
- 238000010538 cationic polymerization reaction Methods 0.000 claims 2
- 101150116749 chuk gene Proteins 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 239000003995 emulsifying agent Substances 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 150000002430 hydrocarbons Chemical class 0.000 claims 2
- 150000002432 hydroperoxides Chemical class 0.000 claims 2
- 239000003999 initiator Substances 0.000 claims 2
- 229910001507 metal halide Inorganic materials 0.000 claims 2
- 150000005309 metal halides Chemical class 0.000 claims 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims 2
- 229920001084 poly(chloroprene) Polymers 0.000 claims 2
- 229920001195 polyisoprene Polymers 0.000 claims 2
- 230000000379 polymerizing effect Effects 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 239000007870 radical polymerization initiator Substances 0.000 claims 2
- 238000010526 radical polymerization reaction Methods 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 229920001567 vinyl ester resin Polymers 0.000 claims 2
- QEDJMOONZLUIMC-UHFFFAOYSA-N 1-tert-butyl-4-ethenylbenzene Chemical compound CC(C)(C)C1=CC=C(C=C)C=C1 QEDJMOONZLUIMC-UHFFFAOYSA-N 0.000 claims 1
- CEBRPXLXYCFYGU-UHFFFAOYSA-N 3-methylbut-1-enylbenzene Chemical compound CC(C)C=CC1=CC=CC=C1 CEBRPXLXYCFYGU-UHFFFAOYSA-N 0.000 claims 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims 1
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 claims 1
- KRMVZBHBXLNLNG-UHFFFAOYSA-N 5-ethenyl-2-methylphenol Chemical compound CC1=CC=C(C=C)C=C1O KRMVZBHBXLNLNG-UHFFFAOYSA-N 0.000 claims 1
- YHYKLQZMEOARHL-UHFFFAOYSA-N 5-ethenyl-2-propan-2-ylphenol Chemical compound CC(C)C1=CC=C(C=C)C=C1O YHYKLQZMEOARHL-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 229910015900 BF3 Inorganic materials 0.000 claims 1
- 239000004342 Benzoyl peroxide Substances 0.000 claims 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 1
- 101150049168 Nisch gene Proteins 0.000 claims 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims 1
- 239000002174 Styrene-butadiene Substances 0.000 claims 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims 1
- 239000000853 adhesive Substances 0.000 claims 1
- 230000001070 adhesive effect Effects 0.000 claims 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 239000002280 amphoteric surfactant Substances 0.000 claims 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 claims 1
- 239000003945 anionic surfactant Substances 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 235000019400 benzoyl peroxide Nutrition 0.000 claims 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims 1
- 239000003093 cationic surfactant Substances 0.000 claims 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 238000012718 coordination polymerization Methods 0.000 claims 1
- 239000008367 deionised water Substances 0.000 claims 1
- 229910021641 deionized water Inorganic materials 0.000 claims 1
- 229920003244 diene elastomer Polymers 0.000 claims 1
- 238000006471 dimerization reaction Methods 0.000 claims 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 239000000835 fiber Substances 0.000 claims 1
- 150000008282 halocarbons Chemical class 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 238000005805 hydroxylation reaction Methods 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 239000002198 insoluble material Substances 0.000 claims 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000005673 monoalkenes Chemical class 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 239000002736 nonionic surfactant Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000003973 paint Substances 0.000 claims 1
- IAOFZFVLKDFCRR-UHFFFAOYSA-N phenol styrene Chemical compound Oc1ccccc1.C=Cc1ccccc1.C=Cc1ccccc1 IAOFZFVLKDFCRR-UHFFFAOYSA-N 0.000 claims 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 claims 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- 229910052703 rhodium Inorganic materials 0.000 claims 1
- 239000010948 rhodium Substances 0.000 claims 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 claims 1
- 239000011115 styrene butadiene Substances 0.000 claims 1
- 239000005061 synthetic rubber Substances 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims 1
- 238000005829 trimerization reaction Methods 0.000 claims 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 238000004073 vulcanization Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 229920006027 ternary co-polymer Polymers 0.000 description 2
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- GSFSVEDCYBDIGW-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-6-chlorophenol Chemical compound OC1=C(Cl)C=CC=C1C1=NC2=CC=CC=C2S1 GSFSVEDCYBDIGW-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- 229940048086 sodium pyrophosphate Drugs 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate 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
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
-
- 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
- C08F279/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
- C08F279/02—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00 on to polymers of conjugated dienes
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)
- Graft Or Block Polymers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP49032766A JPS5853001B2 (ja) | 1974-03-22 | 1974-03-22 | シンキエラストマ− ノ セイゾウホウホウ |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH617445A5 true CH617445A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-05-30 |
Family
ID=12367954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1596474A CH617445A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-03-22 | 1974-12-02 |
Country Status (6)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5160290A (en) * | 1974-11-22 | 1976-05-26 | Sumitomo Chemical Co | Shinkierasutomaano seizohoho |
| US4054676A (en) * | 1974-12-04 | 1977-10-18 | Dynapol | Edible with polymeric hydroquinone antioxidant |
| US4097464A (en) * | 1975-11-03 | 1978-06-27 | The Goodyear Tire & Rubber Company | 2,6-Di-tert-alkyl-4-vinylphenols as polymerizable antioxidants |
| CA1093248A (en) * | 1976-05-20 | 1981-01-06 | Kenneth E. Russell | Phenolic antioxidants with polymer tails |
| JPS57149310A (en) * | 1981-03-13 | 1982-09-14 | Japan Synthetic Rubber Co Ltd | Production of resin |
| US7534837B2 (en) * | 2005-09-26 | 2009-05-19 | E.I. Du Pont De Nemours And Company | Random copolymers of ethylene and 4-vinylphenyl esters and method for preparing the same |
| EP2448985B1 (en) * | 2009-07-01 | 2015-01-14 | Bridgestone Corporation | Method of making hydroxyaryl-functionalized interpolymer by free radical initiated polymerization |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2006517A (en) * | 1932-04-16 | 1935-07-02 | Celanese Corp | Method of preparing vinyl phenols |
| US2490756A (en) * | 1947-11-22 | 1949-12-06 | Eastman Kodak Co | N-alkenyl lactamides |
| US2717248A (en) * | 1948-08-02 | 1955-09-06 | Shell Dev | Polymerization of vinyl chloride with monopermalonate catalyst |
| US2647882A (en) * | 1948-11-24 | 1953-08-04 | British Resin Prod Ltd | Etherification of vinyl phenol polymers and copolymers |
| BE492413A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1948-11-26 | |||
| GB691040A (en) * | 1949-01-13 | 1953-05-06 | British Resin Prod Ltd | Copolymers of vinyl phenols with butadiene compounds |
| CA925242A (en) * | 1968-04-06 | 1973-04-24 | Malamet Georg | Polymeric compounds with polycarbonate side chains |
| CA953442A (en) * | 1970-04-24 | 1974-08-20 | Hugo Vernaleken | Composition comprising polycarbonate |
| JPS4941116A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-09-06 | 1974-04-17 |
-
1974
- 1974-03-22 JP JP49032766A patent/JPS5853001B2/ja not_active Expired
- 1974-12-02 DE DE2456821A patent/DE2456821C3/de not_active Expired
- 1974-12-02 DE DE2462476A patent/DE2462476C3/de not_active Expired
- 1974-12-02 CH CH1596474A patent/CH617445A5/de not_active IP Right Cessation
- 1974-12-02 FR FR7439353A patent/FR2264826B1/fr not_active Expired
- 1974-12-03 CA CA215,139A patent/CA1052944A/en not_active Expired
- 1974-12-05 US US05/529,938 patent/US3993714A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE2456821C3 (de) | 1982-02-25 |
| CA1052944A (en) | 1979-04-17 |
| FR2264826A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-10-17 |
| DE2456821B2 (de) | 1981-03-19 |
| US3993714A (en) | 1976-11-23 |
| DE2462476B2 (de) | 1979-04-05 |
| FR2264826B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-07-13 |
| DE2456821A1 (de) | 1975-10-02 |
| JPS50124981A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-10-01 |
| JPS5853001B2 (ja) | 1983-11-26 |
| DE2462476C3 (de) | 1979-11-22 |
| DE2462476A1 (de) | 1977-03-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |