RU2656321C2 - Способы получения эпоксидированных полимеров - Google Patents
Способы получения эпоксидированных полимеров Download PDFInfo
- Publication number
- RU2656321C2 RU2656321C2 RU2015127888A RU2015127888A RU2656321C2 RU 2656321 C2 RU2656321 C2 RU 2656321C2 RU 2015127888 A RU2015127888 A RU 2015127888A RU 2015127888 A RU2015127888 A RU 2015127888A RU 2656321 C2 RU2656321 C2 RU 2656321C2
- Authority
- RU
- Russia
- Prior art keywords
- polymer
- epoxidized
- rubber
- organic phase
- unsaturated
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims abstract description 100
- 238000000034 method Methods 0.000 title claims abstract description 45
- 230000008569 process Effects 0.000 title abstract description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 42
- 229920001971 elastomer Polymers 0.000 claims abstract description 27
- 239000005060 rubber Substances 0.000 claims abstract description 26
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000012074 organic phase Substances 0.000 claims abstract description 23
- 229920005549 butyl rubber Polymers 0.000 claims abstract description 21
- 125000004968 halobutyl group Chemical group 0.000 claims abstract description 16
- 229920005555 halobutyl Polymers 0.000 claims abstract description 15
- 239000000126 substance Substances 0.000 claims abstract description 11
- 239000008346 aqueous phase Substances 0.000 claims abstract description 10
- -1 alicyclic hydrocarbon Chemical class 0.000 claims description 37
- 229920001577 copolymer Polymers 0.000 claims description 24
- 229920005557 bromobutyl Polymers 0.000 claims description 21
- 150000001993 dienes Chemical class 0.000 claims description 19
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 14
- 229920005556 chlorobutyl Polymers 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000003381 stabilizer Substances 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 239000000178 monomer Substances 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 6
- 239000012670 alkaline solution Substances 0.000 claims description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 239000012071 phase Substances 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000000466 oxiranyl group Chemical group 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 230000004888 barrier function Effects 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 230000003993 interaction Effects 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 238000005119 centrifugation Methods 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 238000002203 pretreatment Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 57
- 239000000243 solution Substances 0.000 description 27
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 23
- 238000006735 epoxidation reaction Methods 0.000 description 21
- 239000000203 mixture Substances 0.000 description 19
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 18
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 15
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical class CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 11
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 229920000307 polymer substrate Polymers 0.000 description 7
- 238000012545 processing Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 6
- 239000005977 Ethylene Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 235000019253 formic acid Nutrition 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 230000035699 permeability Effects 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 239000003518 caustics Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 229920002313 fluoropolymer Polymers 0.000 description 3
- 150000004820 halides Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229920002857 polybutadiene Polymers 0.000 description 3
- 238000004073 vulcanization Methods 0.000 description 3
- IRFSXVIRXMYULF-UHFFFAOYSA-N 1,2-dihydroquinoline Chemical class C1=CC=C2C=CCNC2=C1 IRFSXVIRXMYULF-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- VETPHHXZEJAYOB-UHFFFAOYSA-N 1-n,4-n-dinaphthalen-2-ylbenzene-1,4-diamine Chemical compound C1=CC=CC2=CC(NC=3C=CC(NC=4C=C5C=CC=CC5=CC=4)=CC=3)=CC=C21 VETPHHXZEJAYOB-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- RCJMVGJKROQDCB-UHFFFAOYSA-N 2-methylpenta-1,3-diene Chemical compound CC=CC(C)=C RCJMVGJKROQDCB-UHFFFAOYSA-N 0.000 description 2
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- 229920002943 EPDM rubber Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
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- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001924 cycloalkanes Chemical class 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- DECIPOUIJURFOJ-UHFFFAOYSA-N ethoxyquin Chemical compound N1C(C)(C)C=C(C)C2=CC(OCC)=CC=C21 DECIPOUIJURFOJ-UHFFFAOYSA-N 0.000 description 2
- 235000019285 ethoxyquin Nutrition 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
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- 125000000524 functional group Chemical group 0.000 description 2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
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- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
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- 230000035515 penetration Effects 0.000 description 2
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- 238000000746 purification Methods 0.000 description 2
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- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000006720 (C1-C6) alkyl (C6-C10) aryl group Chemical group 0.000 description 1
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- 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 description 1
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- WJNKJKGZKFOLOJ-UHFFFAOYSA-N 1-dodecyl-4-ethenylbenzene Chemical compound CCCCCCCCCCCCC1=CC=C(C=C)C=C1 WJNKJKGZKFOLOJ-UHFFFAOYSA-N 0.000 description 1
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- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 1
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- MHRQEWIVJIGIMI-UHFFFAOYSA-N 2,3-dimethylpenta-1,3-diene;hexa-1,3-diene Chemical compound CCC=CC=C.CC=C(C)C(C)=C MHRQEWIVJIGIMI-UHFFFAOYSA-N 0.000 description 1
- XUGNJOCQALIQFG-UHFFFAOYSA-N 2-ethenylquinoline Chemical compound C1=CC=CC2=NC(C=C)=CC=C21 XUGNJOCQALIQFG-UHFFFAOYSA-N 0.000 description 1
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- RVXLBLSGEPQBIO-UHFFFAOYSA-N 6-chloro-1h-indole-2,3-dione Chemical compound ClC1=CC=C2C(=O)C(=O)NC2=C1 RVXLBLSGEPQBIO-UHFFFAOYSA-N 0.000 description 1
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- 244000043261 Hevea brasiliensis Species 0.000 description 1
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- 101100388055 Mus musculus Polm gene Proteins 0.000 description 1
- UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 description 1
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- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 1
- OUBMGJOQLXMSNT-UHFFFAOYSA-N N-isopropyl-N'-phenyl-p-phenylenediamine Chemical compound C1=CC(NC(C)C)=CC=C1NC1=CC=CC=C1 OUBMGJOQLXMSNT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 1
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- IMJGQTCMUZMLRZ-UHFFFAOYSA-N buta-1,3-dien-2-ylbenzene Chemical compound C=CC(=C)C1=CC=CC=C1 IMJGQTCMUZMLRZ-UHFFFAOYSA-N 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002894 chemical waste Substances 0.000 description 1
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- 238000005345 coagulation Methods 0.000 description 1
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- UVJHQYIOXKWHFD-UHFFFAOYSA-N cyclohexa-1,4-diene Chemical compound C1C=CCC=C1 UVJHQYIOXKWHFD-UHFFFAOYSA-N 0.000 description 1
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- 238000004821 distillation Methods 0.000 description 1
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- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000002816 fuel additive Substances 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
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- 238000012685 gas phase polymerization Methods 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- OLERVPDKBAOPBW-UHFFFAOYSA-K methyl(trioctyl)azanium;phosphate Chemical compound [O-]P([O-])([O-])=O.CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC.CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC.CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC OLERVPDKBAOPBW-UHFFFAOYSA-K 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-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
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
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- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/04—Oxidation
- C08C19/06—Epoxidation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/08—Epoxidation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/134—Phenols containing ester groups
-
- 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
- C08F2810/00—Chemical modification of a polymer
- C08F2810/50—Chemical modification of a polymer wherein the polymer is a copolymer and the modification is taking place only on one or more of the monomers present in minority
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Epoxy Resins (AREA)
Applications Claiming Priority (3)
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| US201261736656P | 2012-12-13 | 2012-12-13 | |
| US61/736,656 | 2012-12-13 | ||
| PCT/CA2013/001017 WO2014089674A1 (en) | 2012-12-13 | 2013-12-11 | Processes for preparing epoxidized polymers |
Publications (2)
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| RU2015127888A RU2015127888A (ru) | 2017-01-19 |
| RU2656321C2 true RU2656321C2 (ru) | 2018-06-04 |
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| RU2015127888A RU2656321C2 (ru) | 2012-12-13 | 2013-12-11 | Способы получения эпоксидированных полимеров |
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| US (1) | US9850324B2 (enExample) |
| EP (1) | EP2931800B1 (enExample) |
| JP (1) | JP6297586B2 (enExample) |
| KR (1) | KR20150123786A (enExample) |
| CN (1) | CN104854177B (enExample) |
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| SG (1) | SG11201504453TA (enExample) |
| TW (1) | TW201437233A (enExample) |
| WO (1) | WO2014089674A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3181595A1 (en) | 2015-12-17 | 2017-06-21 | Lanxess Inc. | Treatment of epoxidized unsaturated isoolefin copolymers |
| EP3181596A1 (en) * | 2015-12-17 | 2017-06-21 | Lanxess Inc. | Process for epoxidation of unsaturated polymer |
| EP3181598A1 (en) * | 2015-12-17 | 2017-06-21 | Lanxess Inc. | Butyl rubber containing allylic alcohol |
| WO2018101916A1 (en) | 2016-11-29 | 2018-06-07 | Compagnie General Des Etablissements Michelin | Rubber compositions reinforced with iron oxide |
| WO2018125200A1 (en) | 2016-12-30 | 2018-07-05 | Compagnie Generale Des Etablissements Michelin | Anisotropic rubber composition |
Citations (6)
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|---|---|---|---|---|
| SU1700008A1 (ru) * | 1989-03-06 | 1991-12-23 | Ярославское научно-производственное объединение "Электронприбор" | Эпоксидированные бутадиен-стирольные олигомеры в качестве пленкообразующих дл покрытий естественной сушки |
| EP0946600B1 (en) * | 1996-12-23 | 2002-08-14 | Sartomer Company, Inc. | Method for the epoxidation of unsaturated polymers |
| DE10201951A1 (de) * | 2001-12-22 | 2003-07-03 | Degussa | Verfahren zur Herstellung säurefreier, epoxidierter Polyalkenylene |
| WO2005063821A1 (en) * | 2003-12-24 | 2005-07-14 | Pirelli Pneumatici S.P.A. | Process for producing an epoxidized elastomeric polymer |
| EP1771309B1 (en) * | 2004-07-28 | 2009-05-06 | PIRELLI TYRE S.p.A. | Tyre comprising an epoxidized elastomeric polymer and crosslinkable elastomeric composition |
| RU2465285C1 (ru) * | 2011-04-20 | 2012-10-27 | Государственное образовательное учреждение высшего профессионального образования "Башкирский государственный университет" ГОУ ВПО БашГУ | Способ получения эпоксидированных 1,2-полибутадиенов |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3410761A (en) * | 1966-04-28 | 1968-11-12 | Fmc Corp | Recovery of epoxy polybutadiene by plural stage flash distillation |
| US3852253A (en) * | 1972-12-22 | 1974-12-03 | Exxon Research Engineering Co | Heterogeneous process for preparing conjugated diene butyl |
| JPS5144037B2 (enExample) * | 1974-01-30 | 1976-11-26 | ||
| US3970608A (en) | 1974-04-05 | 1976-07-20 | Bridgestone Tire Company Limited | Epoxidized acetylene-conjugated diene random copolymer and the curable composition comprising the same |
| JPS5299776A (en) * | 1976-02-18 | 1977-08-22 | Hitachi Ltd | Radiation sensitive high polymeric material |
| PL103054B1 (pl) * | 1976-09-12 | 1979-05-31 | Instytut Ciezkiejsyntezy Organic | Sposob przerobki odpadow z procesu wytwarzania dwufenylolopropanu |
| US4341672A (en) * | 1977-12-19 | 1982-07-27 | Phillips Petroleum Company | Sulfur or peroxy cured epoxidized diene rubbers |
| US6903164B2 (en) * | 2000-11-13 | 2005-06-07 | Daicel Chemical Industries, Ltd. | Epoxidized thermoplastic polymers and processes for their production |
| WO2002092636A1 (en) * | 2001-05-14 | 2002-11-21 | Daicel Chemical Industries, Ltd. | Process for producing epoxidized diene polymer |
| DE102005041789A1 (de) | 2005-09-02 | 2007-03-08 | Basf Ag | Epoxidierung von Isobutenpolymeren |
| CA2575652A1 (en) | 2006-02-15 | 2007-08-15 | Lanxess Inc. | Method of halogenating butyl rubber without acid neutralization agents |
| JP2009280728A (ja) * | 2008-05-23 | 2009-12-03 | Mitsui Chemicals Inc | エポキシ基含有重合体およびその誘導体の製造方法 |
| JP5475336B2 (ja) * | 2009-06-16 | 2014-04-16 | 株式会社ブリヂストン | フィラー含有エラストマー組成物の製造方法、ゴム組成物の製造方法及びタイヤの製造方法 |
| CN101654488A (zh) * | 2009-09-10 | 2010-02-24 | 中国热带农业科学院农产品加工研究所 | 一种环氧化天然橡胶制备技术 |
| JP2011137092A (ja) * | 2009-12-28 | 2011-07-14 | Nippon Soda Co Ltd | 硬化性組成物 |
| CN101942043A (zh) * | 2010-09-25 | 2011-01-12 | 中国热带农业科学院农产品加工研究所 | 一种环氧化天然橡胶的制备方法 |
-
2013
- 2013-12-11 SG SG11201504453TA patent/SG11201504453TA/en unknown
- 2013-12-11 CA CA2894418A patent/CA2894418A1/en not_active Abandoned
- 2013-12-11 KR KR1020157018235A patent/KR20150123786A/ko not_active Withdrawn
- 2013-12-11 WO PCT/CA2013/001017 patent/WO2014089674A1/en not_active Ceased
- 2013-12-11 PL PL13863321T patent/PL2931800T3/pl unknown
- 2013-12-11 EP EP13863321.9A patent/EP2931800B1/en active Active
- 2013-12-11 JP JP2015546785A patent/JP6297586B2/ja not_active Expired - Fee Related
- 2013-12-11 RU RU2015127888A patent/RU2656321C2/ru not_active IP Right Cessation
- 2013-12-11 CN CN201380065681.3A patent/CN104854177B/zh not_active Expired - Fee Related
- 2013-12-11 US US14/651,379 patent/US9850324B2/en active Active
- 2013-12-12 TW TW102145785A patent/TW201437233A/zh unknown
-
2015
- 2015-06-11 SA SA515360567A patent/SA515360567B1/ar unknown
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1700008A1 (ru) * | 1989-03-06 | 1991-12-23 | Ярославское научно-производственное объединение "Электронприбор" | Эпоксидированные бутадиен-стирольные олигомеры в качестве пленкообразующих дл покрытий естественной сушки |
| EP0946600B1 (en) * | 1996-12-23 | 2002-08-14 | Sartomer Company, Inc. | Method for the epoxidation of unsaturated polymers |
| DE10201951A1 (de) * | 2001-12-22 | 2003-07-03 | Degussa | Verfahren zur Herstellung säurefreier, epoxidierter Polyalkenylene |
| WO2005063821A1 (en) * | 2003-12-24 | 2005-07-14 | Pirelli Pneumatici S.P.A. | Process for producing an epoxidized elastomeric polymer |
| EP1771309B1 (en) * | 2004-07-28 | 2009-05-06 | PIRELLI TYRE S.p.A. | Tyre comprising an epoxidized elastomeric polymer and crosslinkable elastomeric composition |
| RU2465285C1 (ru) * | 2011-04-20 | 2012-10-27 | Государственное образовательное учреждение высшего профессионального образования "Башкирский государственный университет" ГОУ ВПО БашГУ | Способ получения эпоксидированных 1,2-полибутадиенов |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20150123786A (ko) | 2015-11-04 |
| SA515360567B1 (ar) | 2018-02-01 |
| PL2931800T3 (pl) | 2020-10-19 |
| CA2894418A1 (en) | 2014-06-19 |
| US20150315299A1 (en) | 2015-11-05 |
| TW201437233A (zh) | 2014-10-01 |
| EP2931800B1 (en) | 2020-05-13 |
| CN104854177B (zh) | 2018-12-04 |
| WO2014089674A1 (en) | 2014-06-19 |
| CN104854177A (zh) | 2015-08-19 |
| EP2931800A4 (en) | 2016-08-31 |
| SG11201504453TA (en) | 2015-07-30 |
| JP6297586B2 (ja) | 2018-03-20 |
| EP2931800A1 (en) | 2015-10-21 |
| RU2015127888A (ru) | 2017-01-19 |
| US9850324B2 (en) | 2017-12-26 |
| JP2016504443A (ja) | 2016-02-12 |
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