SA515360567B1 - عملية لتحضير بوليمرات إيبوكسيدية - Google Patents
عملية لتحضير بوليمرات إيبوكسيدية Download PDFInfo
- Publication number
- SA515360567B1 SA515360567B1 SA515360567A SA515360567A SA515360567B1 SA 515360567 B1 SA515360567 B1 SA 515360567B1 SA 515360567 A SA515360567 A SA 515360567A SA 515360567 A SA515360567 A SA 515360567A SA 515360567 B1 SA515360567 B1 SA 515360567B1
- Authority
- SA
- Saudi Arabia
- Prior art keywords
- unsaturated
- polymer
- phase
- hydrogen peroxide
- halobutyl rubber
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims abstract description 101
- 238000000034 method Methods 0.000 title claims abstract description 57
- 230000008569 process Effects 0.000 title claims abstract description 49
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 61
- 125000000542 sulfonic acid group Chemical group 0.000 claims abstract description 14
- 125000000466 oxiranyl group Chemical group 0.000 claims abstract description 6
- -1 unsaturated allylic halide Chemical class 0.000 claims description 43
- 229920001971 elastomer Polymers 0.000 claims description 42
- 238000006243 chemical reaction Methods 0.000 claims description 41
- 239000005060 rubber Substances 0.000 claims description 41
- 229920001577 copolymer Polymers 0.000 claims description 31
- 239000012074 organic phase Substances 0.000 claims description 31
- 125000004968 halobutyl group Chemical group 0.000 claims description 28
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 23
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 22
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 22
- 229920005549 butyl rubber Polymers 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 16
- 239000012071 phase Substances 0.000 claims description 14
- 239000008346 aqueous phase Substances 0.000 claims description 12
- 229920005555 halobutyl Polymers 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 239000003381 stabilizer Substances 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- 239000012670 alkaline solution Substances 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical group FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- IRFSXVIRXMYULF-UHFFFAOYSA-N 1,2-dihydroquinoline Chemical compound C1=CC=C2C=CCNC2=C1 IRFSXVIRXMYULF-UHFFFAOYSA-N 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 238000005345 coagulation Methods 0.000 claims description 2
- 230000015271 coagulation Effects 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 150000002118 epoxides Chemical class 0.000 claims 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N divinylbenzene Substances C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical class CCCCOOCCCC PAOHAQSLJSMLAT-UHFFFAOYSA-N 0.000 claims 1
- 241000511343 Chondrostoma nasus Species 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- SQVRNKJHWKZAKO-PFQGKNLYSA-N N-acetyl-beta-neuraminic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-PFQGKNLYSA-N 0.000 claims 1
- 150000008378 aryl ethers Chemical class 0.000 claims 1
- 238000005119 centrifugation Methods 0.000 claims 1
- 230000001112 coagulating effect Effects 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 150000002978 peroxides Chemical class 0.000 claims 1
- 238000005191 phase separation Methods 0.000 claims 1
- 238000002203 pretreatment Methods 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- 239000000178 monomer Substances 0.000 abstract description 13
- 125000000746 allylic group Chemical group 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 125000005843 halogen group Chemical group 0.000 abstract description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- 150000002924 oxiranes Chemical class 0.000 description 28
- 239000000243 solution Substances 0.000 description 27
- 229920005557 bromobutyl Polymers 0.000 description 22
- 150000001993 dienes Chemical class 0.000 description 14
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 11
- 229920005556 chlorobutyl Polymers 0.000 description 11
- 238000006735 epoxidation reaction Methods 0.000 description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 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
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 230000035699 permeability Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 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
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 229920001429 chelating resin Polymers 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
- 239000007787 solid Substances 0.000 description 5
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
- 239000005062 Polybutadiene Substances 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 230000000737 periodic effect Effects 0.000 description 4
- 229920002857 polybutadiene Polymers 0.000 description 4
- 238000005070 sampling Methods 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 241000917703 Leia Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003518 caustics Substances 0.000 description 3
- 150000001924 cycloalkanes Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 150000004820 halides Chemical group 0.000 description 3
- 229920003049 isoprene rubber Polymers 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 230000002000 scavenging effect Effects 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 2
- CHSRLSSBNJJDSI-UHFFFAOYSA-N 2,3-didehydroquinoline Chemical class C1=CC=CC2=NC#CC=C21 CHSRLSSBNJJDSI-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
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- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 2
- UXKQNCDDHDBAPD-UHFFFAOYSA-N 4-n,4-n-diphenylbenzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 UXKQNCDDHDBAPD-UHFFFAOYSA-N 0.000 description 2
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- 239000004593 Epoxy Substances 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- DPNGUUBTOATYSA-UHFFFAOYSA-N 1-ethenylnaphthalene;styrene Chemical compound C=CC1=CC=CC=C1.C1=CC=C2C(C=C)=CC=CC2=C1 DPNGUUBTOATYSA-UHFFFAOYSA-N 0.000 description 1
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- 230000004888 barrier function Effects 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 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
- VLLYOYVKQDKAHN-UHFFFAOYSA-N buta-1,3-diene;2-methylbuta-1,3-diene Chemical compound C=CC=C.CC(=C)C=C VLLYOYVKQDKAHN-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000002894 chemical waste Substances 0.000 description 1
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229920003211 cis-1,4-polyisoprene Polymers 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- NMGSDTSOSIPXTN-UHFFFAOYSA-N cyclohexa-1,2-diene Chemical compound C1CC=C=CC1 NMGSDTSOSIPXTN-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- WSUTUEIGSOWBJO-UHFFFAOYSA-N dizinc oxygen(2-) Chemical compound [O-2].[O-2].[Zn+2].[Zn+2] WSUTUEIGSOWBJO-UHFFFAOYSA-N 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 238000009837 dry grinding Methods 0.000 description 1
- 239000013013 elastic material Substances 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- PSIQSMXODVNUAM-UHFFFAOYSA-N ethene;2-methylprop-1-ene Chemical class C=C.CC(C)=C PSIQSMXODVNUAM-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000002816 fuel additive Substances 0.000 description 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000012685 gas phase polymerization Methods 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- DPUXQWOMYBMHRN-UHFFFAOYSA-N hexa-2,3-diene Chemical compound CCC=C=CC DPUXQWOMYBMHRN-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N methyl heptene Natural products CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical compound CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 210000005012 myelin Anatomy 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 150000003384 small molecules Chemical class 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
- 238000005496 tempering Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261736656P | 2012-12-13 | 2012-12-13 | |
| PCT/CA2013/001017 WO2014089674A1 (en) | 2012-12-13 | 2013-12-11 | Processes for preparing epoxidized polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SA515360567B1 true SA515360567B1 (ar) | 2018-02-01 |
Family
ID=50933625
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SA515360567A SA515360567B1 (ar) | 2012-12-13 | 2015-06-11 | عملية لتحضير بوليمرات إيبوكسيدية |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9850324B2 (https=) |
| EP (1) | EP2931800B1 (https=) |
| JP (1) | JP6297586B2 (https=) |
| KR (1) | KR20150123786A (https=) |
| CN (1) | CN104854177B (https=) |
| CA (1) | CA2894418A1 (https=) |
| PL (1) | PL2931800T3 (https=) |
| RU (1) | RU2656321C2 (https=) |
| SA (1) | SA515360567B1 (https=) |
| SG (1) | SG11201504453TA (https=) |
| TW (1) | TW201437233A (https=) |
| WO (1) | WO2014089674A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3181598A1 (en) | 2015-12-17 | 2017-06-21 | Lanxess Inc. | Butyl rubber containing allylic alcohol |
| 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 |
| 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 |
| WO2026049469A1 (ko) * | 2024-08-27 | 2026-03-05 | 디엘케미칼 주식회사 | 고순도 히드록실 말단 폴리부타디엔 제조방법 및 이의 용도 |
Family Cites Families (22)
| 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 (https=) * | 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 |
| SU1700008A1 (ru) * | 1989-03-06 | 1991-12-23 | Ярославское научно-производственное объединение "Электронприбор" | Эпоксидированные бутадиен-стирольные олигомеры в качестве пленкообразующих дл покрытий естественной сушки |
| US5789512A (en) * | 1996-12-23 | 1998-08-04 | Sartomer Company | Method for the epoxidation of unsaturated polymers |
| WO2002038626A1 (en) * | 2000-11-13 | 2002-05-16 | Daicel Chemical Industries, Ltd. | Epoxidized thermoplastic polymers and processes for their production |
| CN1260258C (zh) * | 2001-05-14 | 2006-06-21 | 大赛璐化学工业株式会社 | 环氧化二烯烃系聚合物的制造方法 |
| DE10201951A1 (de) * | 2001-12-22 | 2003-07-03 | Degussa | Verfahren zur Herstellung säurefreier, epoxidierter Polyalkenylene |
| BR0318683A (pt) * | 2003-12-24 | 2006-12-12 | Pirelli | processo para a produção de um polìmero elastomérico epoxidado |
| WO2006010479A1 (en) * | 2004-07-28 | 2006-02-02 | Pirelli Tyre S.P.A. | Tyre comprising an epoxidized elastomeric polymer and crosslinkable elastomeric composition |
| 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 |
| 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 |
-
2013
- 2013-12-11 JP JP2015546785A patent/JP6297586B2/ja not_active Expired - Fee Related
- 2013-12-11 US US14/651,379 patent/US9850324B2/en not_active Expired - Fee Related
- 2013-12-11 KR KR1020157018235A patent/KR20150123786A/ko not_active Withdrawn
- 2013-12-11 SG SG11201504453TA patent/SG11201504453TA/en unknown
- 2013-12-11 EP EP13863321.9A patent/EP2931800B1/en active Active
- 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 PL PL13863321T patent/PL2931800T3/pl unknown
- 2013-12-11 CA CA2894418A patent/CA2894418A1/en not_active Abandoned
- 2013-12-11 WO PCT/CA2013/001017 patent/WO2014089674A1/en not_active Ceased
- 2013-12-12 TW TW102145785A patent/TW201437233A/zh unknown
-
2015
- 2015-06-11 SA SA515360567A patent/SA515360567B1/ar unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2931800B1 (en) | 2020-05-13 |
| CN104854177A (zh) | 2015-08-19 |
| EP2931800A1 (en) | 2015-10-21 |
| CA2894418A1 (en) | 2014-06-19 |
| US20150315299A1 (en) | 2015-11-05 |
| KR20150123786A (ko) | 2015-11-04 |
| RU2015127888A (ru) | 2017-01-19 |
| TW201437233A (zh) | 2014-10-01 |
| SG11201504453TA (en) | 2015-07-30 |
| RU2656321C2 (ru) | 2018-06-04 |
| CN104854177B (zh) | 2018-12-04 |
| JP6297586B2 (ja) | 2018-03-20 |
| EP2931800A4 (en) | 2016-08-31 |
| US9850324B2 (en) | 2017-12-26 |
| JP2016504443A (ja) | 2016-02-12 |
| PL2931800T3 (pl) | 2020-10-19 |
| WO2014089674A1 (en) | 2014-06-19 |
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