DE1645144C3 - Verfahren zur Polymerisation eines Alkenoxyds mit bis zu 20 Kohlenstoffatomen je Molekül - Google Patents
Verfahren zur Polymerisation eines Alkenoxyds mit bis zu 20 Kohlenstoffatomen je MolekülInfo
- Publication number
- DE1645144C3 DE1645144C3 DE1645144A DE1645144A DE1645144C3 DE 1645144 C3 DE1645144 C3 DE 1645144C3 DE 1645144 A DE1645144 A DE 1645144A DE 1645144 A DE1645144 A DE 1645144A DE 1645144 C3 DE1645144 C3 DE 1645144C3
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- compound
- water
- polymerization
- organozinc
- 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
Links
- 150000001336 alkenes Chemical class 0.000 title claims description 30
- 238000006116 polymerization reaction Methods 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 title claims description 8
- 239000003054 catalyst Substances 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- 229920000642 polymer Polymers 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 125000000466 oxiranyl group Chemical group 0.000 claims description 7
- 239000011701 zinc Substances 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 125000000962 organic group Chemical group 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- JQOATXDBTYKMEX-UHFFFAOYSA-N CC[Zn] Chemical compound CC[Zn] JQOATXDBTYKMEX-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000002015 acyclic group Chemical class 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 239000003245 coal Substances 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 claims 1
- 230000007423 decrease Effects 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 239000000049 pigment Substances 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 230000001737 promoting effect Effects 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- 230000035945 sensitivity Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000178 monomer Substances 0.000 description 10
- -1 hydrocarbon radical Chemical class 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000013459 approach Methods 0.000 description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- HEPBQSXQJMTVFI-UHFFFAOYSA-N zinc;butane Chemical compound [Zn+2].CCC[CH2-].CCC[CH2-] HEPBQSXQJMTVFI-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- GXBYFVGCMPJVJX-UHFFFAOYSA-N Epoxybutene Chemical compound C=CC1CO1 GXBYFVGCMPJVJX-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000002370 organoaluminium group Chemical group 0.000 description 2
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- WQAQKERCWPUIMH-UHFFFAOYSA-N 1,5-dimethyl-2-phenylpyrazol-3-one;2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1O.CN1C(C)=CC(=O)N1C1=CC=CC=C1 WQAQKERCWPUIMH-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- CULKVWDDENBOFC-UHFFFAOYSA-N 2,3-diethyl-2,3-bis(prop-1-enyl)oxirane Chemical compound CC=CC1(CC)OC1(CC)C=CC CULKVWDDENBOFC-UHFFFAOYSA-N 0.000 description 1
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
- DJGANOYLPWOJOS-UHFFFAOYSA-N 2-(1-iodoethyl)oxirane Chemical compound CC(I)C1CO1 DJGANOYLPWOJOS-UHFFFAOYSA-N 0.000 description 1
- OITUPSZZKALVRN-UHFFFAOYSA-N 2-(2,3-dimethylphenyl)-3-ethenyloxirane Chemical compound CC1=CC=CC(C2C(O2)C=C)=C1C OITUPSZZKALVRN-UHFFFAOYSA-N 0.000 description 1
- YXIOECOAAMLHPG-UHFFFAOYSA-N 2-(2-methylpropyl)oxirane Chemical compound CC(C)CC1CO1 YXIOECOAAMLHPG-UHFFFAOYSA-N 0.000 description 1
- YVOHHKQKVMEQNV-UHFFFAOYSA-N 2-(cyclopent-3-en-1-ylmethyl)-3-[[3-(cyclopent-3-en-1-ylmethyl)oxiran-2-yl]methoxymethyl]oxirane Chemical compound O1C(CC2CC=CC2)C1COCC1OC1CC1CC=CC1 YVOHHKQKVMEQNV-UHFFFAOYSA-N 0.000 description 1
- OMYHQIQDTINHSB-UHFFFAOYSA-N 2-(ethenoxymethyl)-3-[2-(4-methylphenyl)ethyl]oxirane Chemical compound C1=CC(C)=CC=C1CCC1C(COC=C)O1 OMYHQIQDTINHSB-UHFFFAOYSA-N 0.000 description 1
- LSWYGACWGAICNM-UHFFFAOYSA-N 2-(prop-2-enoxymethyl)oxirane Chemical compound C=CCOCC1CO1 LSWYGACWGAICNM-UHFFFAOYSA-N 0.000 description 1
- WHNBDXQTMPYBAT-UHFFFAOYSA-N 2-butyloxirane Chemical compound CCCCC1CO1 WHNBDXQTMPYBAT-UHFFFAOYSA-N 0.000 description 1
- GULHZPHKRWPYAO-UHFFFAOYSA-N 2-ethenyl-3-[(4-methylcyclohexyl)methyl]oxirane Chemical compound C1CC(C)CCC1CC1C(C=C)O1 GULHZPHKRWPYAO-UHFFFAOYSA-N 0.000 description 1
- SZERAFCDZCHRQS-UHFFFAOYSA-N 2-ethenyl-3-methyloxirane Chemical compound CC1OC1C=C SZERAFCDZCHRQS-UHFFFAOYSA-N 0.000 description 1
- BCJPEZMFAKOJPM-UHFFFAOYSA-N 2-ethyl-3-methyloxirane Chemical compound CCC1OC1C BCJPEZMFAKOJPM-UHFFFAOYSA-N 0.000 description 1
- NHOSOKTUOFENLY-UHFFFAOYSA-N 2-methyl-3-(2-methylpropyl)oxirane Chemical compound CC(C)CC1OC1C NHOSOKTUOFENLY-UHFFFAOYSA-N 0.000 description 1
- DJRFYYLZHVMNKD-UHFFFAOYSA-N 2-methyl-3-[3-[(2-methylpropan-2-yl)oxy]propyl]oxirane Chemical compound CC1OC1CCCOC(C)(C)C DJRFYYLZHVMNKD-UHFFFAOYSA-N 0.000 description 1
- SNAUWGUVQBOHMZ-UHFFFAOYSA-N 2-methyl-3-pentyloxirane Chemical compound CCCCCC1OC1C SNAUWGUVQBOHMZ-UHFFFAOYSA-N 0.000 description 1
- BZCDEFWVFPSNQD-UHFFFAOYSA-N 2-pentadecyl-3-propyloxirane Chemical compound CCCCCCCCCCCCCCCC1OC1CCC BZCDEFWVFPSNQD-UHFFFAOYSA-N 0.000 description 1
- NMOFYYYCFRVWBK-UHFFFAOYSA-N 2-pentyloxirane Chemical compound CCCCCC1CO1 NMOFYYYCFRVWBK-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- SYURNNNQIFDVCA-UHFFFAOYSA-N 2-propyloxirane Chemical compound CCCC1CO1 SYURNNNQIFDVCA-UHFFFAOYSA-N 0.000 description 1
- WUKUJFNYTULCOP-UHFFFAOYSA-N 4-propyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(CCC)CCC2OC21 WUKUJFNYTULCOP-UHFFFAOYSA-N 0.000 description 1
- BRUMNYBXOOTXPK-UHFFFAOYSA-N C(CC)[Zn]CCCCCC Chemical compound C(CC)[Zn]CCCCCC BRUMNYBXOOTXPK-UHFFFAOYSA-N 0.000 description 1
- DOGAATUXUXCHLB-UHFFFAOYSA-M C(CCCC)C(CCCCCC[Zn]Br)CCCCCCC Chemical compound C(CCCC)C(CCCCCC[Zn]Br)CCCCCCC DOGAATUXUXCHLB-UHFFFAOYSA-M 0.000 description 1
- JJMZSJQYQACFHN-UHFFFAOYSA-N C(CCCC)C(CCCCCC[Zn]CCCCCCC(CCCCCCC)CCCCC)CCCCCCC Chemical compound C(CCCC)C(CCCCCC[Zn]CCCCCCC(CCCCCCC)CCCCC)CCCCCCC JJMZSJQYQACFHN-UHFFFAOYSA-N 0.000 description 1
- LOAFPRIBMLTLKC-UHFFFAOYSA-N C(CCCCC)C(C[Zn]CC(CCCCCCCCCCCC)CCCCCC)CCCCCCCCCCCC Chemical compound C(CCCCC)C(C[Zn]CC(CCCCCCCCCCCC)CCCCCC)CCCCCCCCCCCC LOAFPRIBMLTLKC-UHFFFAOYSA-N 0.000 description 1
- DIMLMLFDOBTMGV-UHFFFAOYSA-M C(CCCCC)C(C[Zn]Cl)CCCCCCCCCCCC Chemical compound C(CCCCC)C(C[Zn]Cl)CCCCCCCCCCCC DIMLMLFDOBTMGV-UHFFFAOYSA-M 0.000 description 1
- RUNHUUJGDYOJDA-UHFFFAOYSA-M C(CCCCCCCCCCC)[Zn]F Chemical compound C(CCCCCCCCCCC)[Zn]F RUNHUUJGDYOJDA-UHFFFAOYSA-M 0.000 description 1
- LGXCXCSJTUQXLO-UHFFFAOYSA-N C1(C=CCC=C1)CCC1C(CC(COCC(CC2C(O2)CCC2C=CCC=C2)CC2=CC=CC=C2)CC2=CC=CC=C2)O1 Chemical compound C1(C=CCC=C1)CCC1C(CC(COCC(CC2C(O2)CCC2C=CCC=C2)CC2=CC=CC=C2)CC2=CC=CC=C2)O1 LGXCXCSJTUQXLO-UHFFFAOYSA-N 0.000 description 1
- SBVMBRLXZOVGQH-UHFFFAOYSA-N CC1OC1C(CCC1C=CC=CC1)OC(CCC1C=CC=CC1)C1OC1C Chemical compound CC1OC1C(CCC1C=CC=CC1)OC(CCC1C=CC=CC1)C1OC1C SBVMBRLXZOVGQH-UHFFFAOYSA-N 0.000 description 1
- JIFZSZFDNMGASX-UHFFFAOYSA-N CC=CC(COCC(C1(C2CCCCC2)OC1C1CCCCC1)C=CC)C1(C2CCCCC2)OC1C1CCCCC1 Chemical compound CC=CC(COCC(C1(C2CCCCC2)OC1C1CCCCC1)C=CC)C1(C2CCCCC2)OC1C1CCCCC1 JIFZSZFDNMGASX-UHFFFAOYSA-N 0.000 description 1
- NKKLLBKJYQTMIS-UHFFFAOYSA-N CCC(C(CC=CC=C)OC(CC=CC=C)C(CC)C1(CC)OC1)C1(CC)OC1 Chemical compound CCC(C(CC=CC=C)OC(CC=CC=C)C(CC)C1(CC)OC1)C1(CC)OC1 NKKLLBKJYQTMIS-UHFFFAOYSA-N 0.000 description 1
- VKUHQORMOKRNTP-UHFFFAOYSA-N CCCCC=CC(CCOCCC(CC1OC1)C=CCCCC)CC1OC1 Chemical compound CCCCC=CC(CCOCCC(CC1OC1)C=CCCCC)CC1OC1 VKUHQORMOKRNTP-UHFFFAOYSA-N 0.000 description 1
- JUCGLXJRZMNKAH-UHFFFAOYSA-N CCCCCCCC[Zn]CCCCCCCC Chemical compound CCCCCCCC[Zn]CCCCCCCC JUCGLXJRZMNKAH-UHFFFAOYSA-N 0.000 description 1
- JUOCTSZRGAFSKS-UHFFFAOYSA-N CCCCCC[Zn]CCCCCC Chemical compound CCCCCC[Zn]CCCCCC JUOCTSZRGAFSKS-UHFFFAOYSA-N 0.000 description 1
- FPAYFBDVIZFSFJ-UHFFFAOYSA-N CC[Zn]C Chemical compound CC[Zn]C FPAYFBDVIZFSFJ-UHFFFAOYSA-N 0.000 description 1
- ASAZGNQMIVDKAE-UHFFFAOYSA-N CC[Zn]C(C)C Chemical compound CC[Zn]C(C)C ASAZGNQMIVDKAE-UHFFFAOYSA-N 0.000 description 1
- ASUSLKVOTPUROZ-UHFFFAOYSA-M C[Zn]Cl Chemical compound C[Zn]Cl ASUSLKVOTPUROZ-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- QZDLPGZQNPSDFE-UHFFFAOYSA-M [Cl-].CCC[Zn+] Chemical compound [Cl-].CCC[Zn+] QZDLPGZQNPSDFE-UHFFFAOYSA-M 0.000 description 1
- BKRKJRMBRMDRTH-UHFFFAOYSA-M [I-].CCCCCC[Zn+] Chemical compound [I-].CCCCCC[Zn+] BKRKJRMBRMDRTH-UHFFFAOYSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- OCFSGVNHPVWWKD-UHFFFAOYSA-N butylaluminum Chemical compound [Al].[CH2]CCC OCFSGVNHPVWWKD-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 1
- SGYNQHIAJZFJFU-UHFFFAOYSA-L difluoro(heptyl)alumane Chemical compound C(CCCCCC)[Al](F)F SGYNQHIAJZFJFU-UHFFFAOYSA-L 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- JGHYBJVUQGTEEB-UHFFFAOYSA-M dimethylalumanylium;chloride Chemical compound C[Al](C)Cl JGHYBJVUQGTEEB-UHFFFAOYSA-M 0.000 description 1
- AXAZMDOAUQTMOW-UHFFFAOYSA-N dimethylzinc Chemical compound C[Zn]C AXAZMDOAUQTMOW-UHFFFAOYSA-N 0.000 description 1
- QRQUTSPLBBZERR-UHFFFAOYSA-M dioctylalumanylium;chloride Chemical compound CCCCCCCC[Al](Cl)CCCCCCCC QRQUTSPLBBZERR-UHFFFAOYSA-M 0.000 description 1
- XPSQBNPZMNWIPV-UHFFFAOYSA-N ethenoxyperoxyethene Chemical compound C=COOOC=C XPSQBNPZMNWIPV-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 210000003041 ligament Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- YSTQWZZQKCCBAY-UHFFFAOYSA-L methylaluminum(2+);dichloride Chemical compound C[Al](Cl)Cl YSTQWZZQKCCBAY-UHFFFAOYSA-L 0.000 description 1
- 229910000096 monohydride Inorganic materials 0.000 description 1
- UCAOGXRUJFKQAP-UHFFFAOYSA-N n,n-dimethyl-5-nitropyridin-2-amine Chemical compound CN(C)C1=CC=C([N+]([O-])=O)C=N1 UCAOGXRUJFKQAP-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000002899 organoaluminium compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- USJZIJNMRRNDPO-UHFFFAOYSA-N tris-decylalumane Chemical compound CCCCCCCCCC[Al](CCCCCCCCCC)CCCCCCCCCC USJZIJNMRRNDPO-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- ABIAVOPWHAWUGT-UHFFFAOYSA-N zinc;2-methanidylpropane Chemical compound [Zn+2].CC(C)[CH2-].CC(C)[CH2-] ABIAVOPWHAWUGT-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/08—Saturated oxiranes
- C08G65/10—Saturated oxiranes characterised by the catalysts used
- C08G65/12—Saturated oxiranes characterised by the catalysts used containing organo-metallic compounds or metal hydrides
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polymerization Catalysts (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US462104A US3379660A (en) | 1965-06-07 | 1965-06-07 | Alkene oxide polymerization with a catalyst comprising an organoaluminum compound, an organozinc compound and water |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1645144A1 DE1645144A1 (de) | 1972-04-27 |
| DE1645144B2 DE1645144B2 (de) | 1973-05-30 |
| DE1645144C3 true DE1645144C3 (de) | 1974-01-10 |
Family
ID=23835183
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1645144A Expired DE1645144C3 (de) | 1965-06-07 | 1966-06-07 | Verfahren zur Polymerisation eines Alkenoxyds mit bis zu 20 Kohlenstoffatomen je Molekül |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3379660A (OSRAM) |
| BE (1) | BE682130A (OSRAM) |
| DE (1) | DE1645144C3 (OSRAM) |
| GB (1) | GB1152665A (OSRAM) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3442876A (en) * | 1966-02-16 | 1969-05-06 | Gen Tire & Rubber Co | Novel rubbery polyoxyalkylene copolymers |
| US3459721A (en) * | 1966-10-10 | 1969-08-05 | Exxon Research Engineering Co | Dialkylaluminum acetylacetonate polymerization catalysts |
| FR1542470A (fr) * | 1966-12-02 | 1968-10-18 | Inst Francais Du Petrole | Nouveaux catalyseurs de polymérisation d'oxydes d'alcoylènes |
| US3457197A (en) * | 1968-02-23 | 1969-07-22 | Phillips Petroleum Co | Polymerization of epihalohydrins alone or with oxirane compounds |
| US3697496A (en) * | 1968-07-25 | 1972-10-10 | Sumitomo Chemical Co | Method for the polymerization of a compound containing an oxirane group |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3135705A (en) * | 1959-05-11 | 1964-06-02 | Hercules Powder Co Ltd | Polymeric epoxides |
| BE623510A (OSRAM) * | 1961-10-14 | 1900-01-01 |
-
1965
- 1965-06-07 US US462104A patent/US3379660A/en not_active Expired - Lifetime
-
1966
- 1966-06-06 GB GB25037/66A patent/GB1152665A/en not_active Expired
- 1966-06-06 BE BE682130D patent/BE682130A/xx unknown
- 1966-06-07 DE DE1645144A patent/DE1645144C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1645144A1 (de) | 1972-04-27 |
| BE682130A (OSRAM) | 1966-12-06 |
| US3379660A (en) | 1968-04-23 |
| GB1152665A (en) | 1969-05-21 |
| DE1645144B2 (de) | 1973-05-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |