RU2570701C2 - Способ получения полиэфирполиолов - Google Patents
Способ получения полиэфирполиолов Download PDFInfo
- Publication number
- RU2570701C2 RU2570701C2 RU2012153907/04A RU2012153907A RU2570701C2 RU 2570701 C2 RU2570701 C2 RU 2570701C2 RU 2012153907/04 A RU2012153907/04 A RU 2012153907/04A RU 2012153907 A RU2012153907 A RU 2012153907A RU 2570701 C2 RU2570701 C2 RU 2570701C2
- Authority
- RU
- Russia
- Prior art keywords
- group
- alkylene oxides
- reactor
- alkyl group
- compounds
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 31
- 229920005906 polyester polyol Polymers 0.000 title claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 50
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 35
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims abstract description 25
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 22
- ADLVDYMTBOSDFE-UHFFFAOYSA-N 5-chloro-6-nitroisoindole-1,3-dione Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC2=C1C(=O)NC2=O ADLVDYMTBOSDFE-UHFFFAOYSA-N 0.000 claims abstract description 12
- 230000003197 catalytic effect Effects 0.000 claims abstract description 10
- 230000001588 bifunctional effect Effects 0.000 claims abstract description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 5
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 5
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims abstract description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 5
- 229920005862 polyol Polymers 0.000 claims description 45
- 150000003077 polyols Chemical class 0.000 claims description 45
- 229920000570 polyether Polymers 0.000 claims description 43
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 42
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- 238000007142 ring opening reaction Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 238000006116 polymerization reaction Methods 0.000 claims description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 4
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000002989 phenols Chemical class 0.000 claims description 4
- 239000000600 sorbitol Substances 0.000 claims description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 3
- 229930006000 Sucrose Natural products 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- 150000002009 diols Chemical class 0.000 claims description 3
- 239000000194 fatty acid Substances 0.000 claims description 3
- 229930195729 fatty acid Natural products 0.000 claims description 3
- 150000004665 fatty acids Chemical class 0.000 claims description 3
- 239000005720 sucrose Substances 0.000 claims description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 2
- 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 claims description 2
- 229930195725 Mannitol Natural products 0.000 claims description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 2
- 239000004359 castor oil Substances 0.000 claims description 2
- 235000019438 castor oil Nutrition 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 2
- 239000008103 glucose Substances 0.000 claims description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000000594 mannitol Substances 0.000 claims description 2
- 235000010355 mannitol Nutrition 0.000 claims description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims description 2
- 229920003987 resole Polymers 0.000 claims description 2
- 229920000877 Melamine resin Polymers 0.000 claims 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 5
- 238000007151 ring opening polymerisation reaction Methods 0.000 abstract description 3
- 238000010517 secondary reaction Methods 0.000 abstract 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 63
- 239000004814 polyurethane Substances 0.000 description 32
- 229920002635 polyurethane Polymers 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 238000004519 manufacturing process Methods 0.000 description 15
- 239000007795 chemical reaction product Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000006555 catalytic reaction Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- LVPDOTLCYRSINR-UHFFFAOYSA-N 1,3-dimethyl-2h-imidazole-2-carboxylic acid Chemical compound CN1C=CN(C)C1C(O)=O LVPDOTLCYRSINR-UHFFFAOYSA-N 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000006260 foam Substances 0.000 description 6
- -1 cyclic siloxanes Chemical class 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- 229920001451 polypropylene glycol Polymers 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 229920001400 block copolymer Polymers 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 150000002596 lactones Chemical class 0.000 description 4
- 238000010791 quenching Methods 0.000 description 4
- 230000000171 quenching effect Effects 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 3
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- GSCLMSFRWBPUSK-UHFFFAOYSA-N beta-Butyrolactone Chemical compound CC1CC(=O)O1 GSCLMSFRWBPUSK-UHFFFAOYSA-N 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical group [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 2
- 239000012038 nucleophile Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229960000380 propiolactone Drugs 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- YZGPSDZIYQHDBF-UHFFFAOYSA-N (5-isocyanato-1,3,3-trimethylcyclohexyl)methyl cyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(COC#N)C1 YZGPSDZIYQHDBF-UHFFFAOYSA-N 0.000 description 1
- UTFSEWQOIIZLRH-UHFFFAOYSA-N 1,7-diisocyanatoheptane Chemical compound O=C=NCCCCCCCN=C=O UTFSEWQOIIZLRH-UHFFFAOYSA-N 0.000 description 1
- HCCUDHUHQPPUFU-UHFFFAOYSA-N 1-butyl-3-methyl-2h-imidazole-2-carboxylic acid Chemical compound CCCCN1C=CN(C)C1C(O)=O HCCUDHUHQPPUFU-UHFFFAOYSA-N 0.000 description 1
- PBZHISVDZCPMPG-UHFFFAOYSA-N 1-ethyl-3-methyl-2h-imidazole-2-carboxylic acid Chemical compound CCN1C=CN(C)C1C(O)=O PBZHISVDZCPMPG-UHFFFAOYSA-N 0.000 description 1
- YSAANLSYLSUVHB-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]ethanol Chemical compound CN(C)CCOCCO YSAANLSYLSUVHB-UHFFFAOYSA-N 0.000 description 1
- WTPYFJNYAMXZJG-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=C(OCCO)C=C1 WTPYFJNYAMXZJG-UHFFFAOYSA-N 0.000 description 1
- LBZZJNPUANNABV-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)phenyl]ethanol Chemical compound OCCC1=CC=C(CCO)C=C1 LBZZJNPUANNABV-UHFFFAOYSA-N 0.000 description 1
- IYBOGQYZTIIPNI-UHFFFAOYSA-N 2-methylhexano-6-lactone Chemical compound CC1CCCCOC1=O IYBOGQYZTIIPNI-UHFFFAOYSA-N 0.000 description 1
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- JEHNLMDRQXUAOQ-UHFFFAOYSA-N 3-benzyloxepan-2-one Chemical compound O=C1OCCCCC1CC1=CC=CC=C1 JEHNLMDRQXUAOQ-UHFFFAOYSA-N 0.000 description 1
- JXHJKUCCXLDGCK-UHFFFAOYSA-N 3-cyclohexyloxepan-2-one Chemical compound O=C1OCCCCC1C1CCCCC1 JXHJKUCCXLDGCK-UHFFFAOYSA-N 0.000 description 1
- XJDBUEGQHFPGOR-UHFFFAOYSA-N 3-ethoxyoxepan-2-one Chemical compound CCOC1CCCCOC1=O XJDBUEGQHFPGOR-UHFFFAOYSA-N 0.000 description 1
- HIWTUNDEYUEBCI-UHFFFAOYSA-N 3-methoxyoxepan-2-one Chemical compound COC1CCCCOC1=O HIWTUNDEYUEBCI-UHFFFAOYSA-N 0.000 description 1
- NYBXFCLDEATPCM-UHFFFAOYSA-N 3-methyloxetan-2-one Chemical compound CC1COC1=O NYBXFCLDEATPCM-UHFFFAOYSA-N 0.000 description 1
- CHRZWHKOEQQAPH-UHFFFAOYSA-N 3-phenyloxepan-2-one Chemical compound O=C1OCCCCC1C1=CC=CC=C1 CHRZWHKOEQQAPH-UHFFFAOYSA-N 0.000 description 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 description 1
- ILXSXFVKKZFOCX-UHFFFAOYSA-N 4,5-ditert-butyl-1H-imidazol-1-ium-2-carboxylate Chemical compound C(C)(C)(C)C1=C(N=C([NH2+]1)C(=O)[O-])C(C)(C)C ILXSXFVKKZFOCX-UHFFFAOYSA-N 0.000 description 1
- 206010067484 Adverse reaction Diseases 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000004605 External Lubricant Substances 0.000 description 1
- 239000004610 Internal Lubricant Substances 0.000 description 1
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
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- 239000012963 UV stabilizer Substances 0.000 description 1
- VDTCDTBSTDUDCT-UHFFFAOYSA-N [3-(cyanatomethyl)cyclohexyl]methyl cyanate Chemical compound N#COCC1CCCC(COC#N)C1 VDTCDTBSTDUDCT-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- ZCXIITBXMHGPKI-UHFFFAOYSA-N [4-(cyanatomethyl)cyclohexyl]methyl cyanate Chemical compound N#COCC1CCC(COC#N)CC1 ZCXIITBXMHGPKI-UHFFFAOYSA-N 0.000 description 1
- BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical group C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
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- 238000009826 distribution Methods 0.000 description 1
- PYBNTRWJKQJDRE-UHFFFAOYSA-L dodecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O PYBNTRWJKQJDRE-UHFFFAOYSA-L 0.000 description 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
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- AQBLLJNPHDIAPN-LNTINUHCSA-K iron(3+);(z)-4-oxopent-2-en-2-olate Chemical compound [Fe+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O AQBLLJNPHDIAPN-LNTINUHCSA-K 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- HLJDOURGTRAFHE-UHFFFAOYSA-N isocyanic acid;3,5,5-trimethylcyclohex-2-en-1-one Chemical compound N=C=O.N=C=O.CC1=CC(=O)CC(C)(C)C1 HLJDOURGTRAFHE-UHFFFAOYSA-N 0.000 description 1
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 1
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- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920000582 polyisocyanurate Polymers 0.000 description 1
- 239000011495 polyisocyanurate Substances 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920003009 polyurethane dispersion Polymers 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 229920006301 statistical copolymer Polymers 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical compound O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 150000004998 toluenediamines Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- C08G65/26—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 and other compounds
- C08G65/2603—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 and other compounds the other compounds containing oxygen
- C08G65/2606—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 and other compounds the other compounds containing oxygen containing hydroxyl groups
-
- 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
- C08G65/26—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 and other compounds
- C08G65/2642—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 and other compounds characterised by the catalyst used
- C08G65/2669—Non-metals or compounds thereof
- C08G65/2672—Nitrogen or compounds thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Polyethers (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10162850 | 2010-05-14 | ||
| EP10162850.1 | 2010-05-14 | ||
| PCT/EP2011/057579 WO2011141492A1 (de) | 2010-05-14 | 2011-05-11 | Verfahren zur herstellung von polyetherolen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2012153907A RU2012153907A (ru) | 2014-06-20 |
| RU2570701C2 true RU2570701C2 (ru) | 2015-12-10 |
Family
ID=44114425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2012153907/04A RU2570701C2 (ru) | 2010-05-14 | 2011-05-11 | Способ получения полиэфирполиолов |
Country Status (11)
| Country | Link |
|---|---|
| EP (2) | EP2569349B1 (enExample) |
| JP (1) | JP5917495B2 (enExample) |
| KR (1) | KR101805227B1 (enExample) |
| CN (1) | CN102892808B (enExample) |
| BR (1) | BR112012028944A2 (enExample) |
| ES (2) | ES2611467T3 (enExample) |
| MX (1) | MX344909B (enExample) |
| PL (1) | PL2569349T3 (enExample) |
| RU (1) | RU2570701C2 (enExample) |
| SG (2) | SG10201502851WA (enExample) |
| WO (1) | WO2011141492A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2644635A1 (de) * | 2012-03-26 | 2013-10-02 | Basf Se | Verfahren zur organokatalytischen ringöffnenden Polymerisation |
| US9156761B2 (en) | 2012-03-26 | 2015-10-13 | Basf Se | Process for preparing polyether polyols |
| EP2644636A1 (de) | 2012-03-26 | 2013-10-02 | Basf Se | Verfahren zur herstellung von polyetherpolyolen |
| US9056945B2 (en) | 2012-03-26 | 2015-06-16 | Basf Se | Process for organocatalytic ring-opening polymerization |
| EP3034537B1 (de) | 2014-12-16 | 2020-02-26 | Basf Se | Verfahren zur organokatalytischen ringöffnenden polymerisation |
| WO2018025970A1 (ja) | 2016-08-04 | 2018-02-08 | 広栄化学工業株式会社 | アミデート化合物、ポリウレタン製造用触媒及びポリウレタン樹脂の製造方法 |
| EP3604287B1 (en) | 2017-03-31 | 2022-08-03 | Koei Chemical Company, Limited | Production method for amidate compound |
| CN116333294B (zh) * | 2023-05-04 | 2023-12-29 | 辽宁奥克药业股份有限公司 | 一种制备嵌段聚醚的催化剂、嵌段聚醚的制备方法 |
| CN116284735B (zh) * | 2023-05-04 | 2023-12-29 | 辽宁奥克药业股份有限公司 | 一种制备嵌段聚醚的催化剂、嵌段聚醚的制备方法 |
Citations (6)
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|---|---|---|---|---|
| US4833176A (en) * | 1987-06-26 | 1989-05-23 | Bayer Aktiengesellschaft | Process for the preparation of cold setting flexible polyurethane molded foams |
| US5001165A (en) * | 1985-09-30 | 1991-03-19 | Sloss Industries Corporation | Polyoxyalkylene solubilizers for polyol blends |
| EP0950679A2 (en) * | 1998-04-16 | 1999-10-20 | Mitsui Chemicals, Inc. | Process for preparing poly(alkylene oxide) |
| RU2177828C2 (ru) * | 1996-04-19 | 2002-01-10 | Арко Кемикал Текноледжи, Л.П. | Высокоактивные двойные металлоцианидные катализаторы |
| US20030036578A1 (en) * | 2001-06-15 | 2003-02-20 | Andreas Arlt | Preparation of highly resilient polyurethane foams |
| EP2110397A1 (de) * | 2008-04-16 | 2009-10-21 | Sika Technology AG | Auf amphiphilen Block-Copolymer basierendes Polyurethan-Polymer und dessen Verwendung als Schlagzähigkeitsmodifikator |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2901774A1 (de) | 1979-01-18 | 1980-07-24 | Elastogran Gmbh | Rieselfaehiges, mikrobenbestaendiges farbstoff- und/oder hilfsmittelkonzentrat auf basis eines polyurethan-elastomeren und verfahren zu seiner herstellung |
| DE3942329A1 (de) * | 1989-12-21 | 1991-06-27 | Basf Ag | Verfahren zur herstellung von polyurethan-weichschaumstoffen mit geringer stauchhaerte und hierfuer verwendbare blockpolyoxypropylen-polyoxyethylen-polyolgemische |
| DE19928156A1 (de) * | 1999-06-19 | 2000-12-28 | Bayer Ag | Aus Polyetherpolyolen hergestellte Polyurethan-Weichschäume |
| EP1338614B1 (de) | 2002-02-23 | 2006-12-20 | Bayer MaterialScience AG | Verfahren zur Herstellung von weichen, gut entformbaren thermoplastischen Polyurethanelastomeren mit geringer Schwindung |
| FR2919296A1 (fr) * | 2007-07-25 | 2009-01-30 | Rhodia Operations Sas | Ouverture de cycles epoxy par des carbenes. |
| CN101665567B (zh) | 2008-09-01 | 2011-11-23 | 南京工业大学 | 卡宾衍生物催化的环状化合物可调控开环聚合方法 |
-
2011
- 2011-05-11 MX MX2012013177A patent/MX344909B/es active IP Right Grant
- 2011-05-11 EP EP11718752.6A patent/EP2569349B1/de not_active Not-in-force
- 2011-05-11 PL PL11718752T patent/PL2569349T3/pl unknown
- 2011-05-11 SG SG10201502851WA patent/SG10201502851WA/en unknown
- 2011-05-11 JP JP2013509557A patent/JP5917495B2/ja active Active
- 2011-05-11 CN CN201180023961.9A patent/CN102892808B/zh not_active Expired - Fee Related
- 2011-05-11 ES ES14166556.2T patent/ES2611467T3/es active Active
- 2011-05-11 RU RU2012153907/04A patent/RU2570701C2/ru not_active IP Right Cessation
- 2011-05-11 WO PCT/EP2011/057579 patent/WO2011141492A1/de not_active Ceased
- 2011-05-11 ES ES11718752.6T patent/ES2492524T3/es active Active
- 2011-05-11 SG SG2012080875A patent/SG185398A1/en unknown
- 2011-05-11 BR BR112012028944A patent/BR112012028944A2/pt not_active IP Right Cessation
- 2011-05-11 KR KR1020127032503A patent/KR101805227B1/ko not_active Expired - Fee Related
- 2011-05-11 EP EP14166556.2A patent/EP2765151B1/de not_active Not-in-force
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5001165A (en) * | 1985-09-30 | 1991-03-19 | Sloss Industries Corporation | Polyoxyalkylene solubilizers for polyol blends |
| US4833176A (en) * | 1987-06-26 | 1989-05-23 | Bayer Aktiengesellschaft | Process for the preparation of cold setting flexible polyurethane molded foams |
| RU2177828C2 (ru) * | 1996-04-19 | 2002-01-10 | Арко Кемикал Текноледжи, Л.П. | Высокоактивные двойные металлоцианидные катализаторы |
| EP0950679A2 (en) * | 1998-04-16 | 1999-10-20 | Mitsui Chemicals, Inc. | Process for preparing poly(alkylene oxide) |
| US20030036578A1 (en) * | 2001-06-15 | 2003-02-20 | Andreas Arlt | Preparation of highly resilient polyurethane foams |
| EP2110397A1 (de) * | 2008-04-16 | 2009-10-21 | Sika Technology AG | Auf amphiphilen Block-Copolymer basierendes Polyurethan-Polymer und dessen Verwendung als Schlagzähigkeitsmodifikator |
Non-Patent Citations (1)
| Title |
|---|
| ANDREW F MASON ET AL "ORGANOCATALYTIC POLYMERIZATION OF ETHYLENE OXIDE AND THE CONTROLLED SYNTHESIS OF PEO-BASED HYDROGEL NETWORKS" POLYMER PREPRINTS, AMERICAN CHEMICAL SOCIETY, US, 47(2), 1999. * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2013526630A (ja) | 2013-06-24 |
| KR101805227B1 (ko) | 2017-12-05 |
| SG185398A1 (en) | 2012-12-28 |
| PL2569349T3 (pl) | 2014-11-28 |
| EP2569349B1 (de) | 2014-06-18 |
| CN102892808A (zh) | 2013-01-23 |
| EP2765151A1 (de) | 2014-08-13 |
| CN102892808B (zh) | 2014-12-31 |
| JP5917495B2 (ja) | 2016-05-18 |
| BR112012028944A2 (pt) | 2016-07-26 |
| WO2011141492A1 (de) | 2011-11-17 |
| KR20130064754A (ko) | 2013-06-18 |
| RU2012153907A (ru) | 2014-06-20 |
| ES2492524T3 (es) | 2014-09-09 |
| ES2611467T3 (es) | 2017-05-09 |
| EP2569349A1 (de) | 2013-03-20 |
| MX2012013177A (es) | 2012-11-29 |
| SG10201502851WA (en) | 2015-05-28 |
| MX344909B (es) | 2017-01-11 |
| EP2765151B1 (de) | 2016-10-19 |
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Legal Events
| Date | Code | Title | Description |
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| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20160512 |