ES2719589T3 - Polioles híbridos de poliéster y poliéter - Google Patents
Polioles híbridos de poliéster y poliéter Download PDFInfo
- Publication number
- ES2719589T3 ES2719589T3 ES11717149T ES11717149T ES2719589T3 ES 2719589 T3 ES2719589 T3 ES 2719589T3 ES 11717149 T ES11717149 T ES 11717149T ES 11717149 T ES11717149 T ES 11717149T ES 2719589 T3 ES2719589 T3 ES 2719589T3
- Authority
- ES
- Spain
- Prior art keywords
- reactor
- polyether
- catalyst
- polyester
- weight
- 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.)
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- 229920005862 polyol Polymers 0.000 title claims abstract description 142
- 150000003077 polyols Chemical class 0.000 title claims abstract description 135
- 229920000570 polyether Polymers 0.000 title claims abstract description 121
- 239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 119
- 229920000728 polyester Polymers 0.000 title claims abstract description 80
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 218
- 239000003054 catalyst Substances 0.000 claims abstract description 153
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims abstract description 76
- 239000003930 superacid Substances 0.000 claims abstract description 73
- 239000002253 acid Substances 0.000 claims abstract description 71
- 229910052751 metal Inorganic materials 0.000 claims abstract description 57
- 239000002184 metal Substances 0.000 claims abstract description 57
- 238000006243 chemical reaction Methods 0.000 claims abstract description 38
- 150000003839 salts Chemical class 0.000 claims abstract description 36
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 35
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 239000012970 tertiary amine catalyst Substances 0.000 claims abstract description 19
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims abstract description 14
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229920005906 polyester polyol Polymers 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 238000003918 potentiometric titration Methods 0.000 claims abstract description 6
- 150000002924 oxiranes Chemical class 0.000 claims abstract 5
- 238000000034 method Methods 0.000 claims description 46
- 230000008569 process Effects 0.000 claims description 30
- -1 epoxide compound Chemical class 0.000 claims description 29
- 238000005227 gel permeation chromatography Methods 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 21
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical group OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 21
- 229920002635 polyurethane Polymers 0.000 claims description 14
- 239000004814 polyurethane Substances 0.000 claims description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 10
- 150000008065 acid anhydrides Chemical class 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 8
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims description 8
- NJWSNNWLBMSXQR-UHFFFAOYSA-N 2-hexyloxirane Chemical compound CCCCCCC1CO1 NJWSNNWLBMSXQR-UHFFFAOYSA-N 0.000 claims description 7
- 150000001735 carboxylic acids Chemical class 0.000 claims description 7
- 238000009472 formulation Methods 0.000 claims description 6
- 125000001302 tertiary amino group Chemical group 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000004593 Epoxy Substances 0.000 abstract description 14
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 abstract 2
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 78
- 238000003756 stirring Methods 0.000 description 69
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 39
- 239000007788 liquid Substances 0.000 description 37
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 35
- 230000029087 digestion Effects 0.000 description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- 239000011541 reaction mixture Substances 0.000 description 34
- 229910001220 stainless steel Inorganic materials 0.000 description 31
- 239000010935 stainless steel Substances 0.000 description 31
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 30
- 150000002118 epoxides Chemical class 0.000 description 29
- 235000011187 glycerol Nutrition 0.000 description 24
- 239000000126 substance Substances 0.000 description 24
- 229910052757 nitrogen Inorganic materials 0.000 description 23
- 230000002829 reductive effect Effects 0.000 description 23
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 22
- 239000006260 foam Substances 0.000 description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 229910052748 manganese Inorganic materials 0.000 description 19
- 239000007787 solid Substances 0.000 description 19
- 230000004913 activation Effects 0.000 description 18
- 230000007423 decrease Effects 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000003039 volatile agent Substances 0.000 description 15
- 229920013701 VORANOL™ Polymers 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 12
- 150000008064 anhydrides Chemical class 0.000 description 11
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 11
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 10
- 239000008139 complexing agent Substances 0.000 description 10
- 239000003999 initiator Substances 0.000 description 10
- 239000006185 dispersion Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 150000003512 tertiary amines Chemical class 0.000 description 9
- 125000002947 alkylene group Chemical group 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 8
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 150000002825 nitriles Chemical class 0.000 description 8
- 229920005830 Polyurethane Foam Polymers 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 239000011496 polyurethane foam Substances 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 229910052725 zinc Inorganic materials 0.000 description 7
- 239000011701 zinc Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 5
- 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 description 5
- 230000008901 benefit Effects 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 230000000670 limiting effect Effects 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 4
- 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 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 229910017052 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- 238000007906 compression Methods 0.000 description 4
- 230000006835 compression Effects 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- 239000000600 sorbitol Substances 0.000 description 4
- 235000010356 sorbitol Nutrition 0.000 description 4
- 150000008648 triflates Chemical class 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 229910002651 NO3 Inorganic materials 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229920000604 Polyethylene Glycol 200 Polymers 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 3
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 3
- IQEIPKSTLDOYQR-UHFFFAOYSA-N [Zn+3] Chemical compound [Zn+3] IQEIPKSTLDOYQR-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 150000001450 anions Chemical group 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- SZAVHWMCBDFDCM-KTTJZPQESA-N cobalt-60(3+);hexacyanide Chemical compound [60Co+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] SZAVHWMCBDFDCM-KTTJZPQESA-N 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 3
- UETZVSHORCDDTH-UHFFFAOYSA-N iron(2+);hexacyanide Chemical compound [Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] UETZVSHORCDDTH-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229920001515 polyalkylene glycol Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 2
- SUBFZYQWYBUTGO-UHFFFAOYSA-N 2-ethyl-n,n-di(propan-2-yl)butan-1-amine Chemical compound CCC(CC)CN(C(C)C)C(C)C SUBFZYQWYBUTGO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- 239000004604 Blowing Agent Substances 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-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
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229960004543 anhydrous citric acid Drugs 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- FKOASGGZYSYPBI-UHFFFAOYSA-K bis(trifluoromethylsulfonyloxy)alumanyl trifluoromethanesulfonate Chemical compound [Al+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F FKOASGGZYSYPBI-UHFFFAOYSA-K 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- RKBAPHPQTADBIK-UHFFFAOYSA-N cobalt;hexacyanide Chemical compound [Co].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] RKBAPHPQTADBIK-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000012973 diazabicyclooctane Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Natural products CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000004088 foaming agent Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000012774 insulation material Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
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- YOIAWAIKYVEKMF-UHFFFAOYSA-N trifluoromethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)F.OS(=O)(=O)C(F)(F)F YOIAWAIKYVEKMF-UHFFFAOYSA-N 0.000 description 1
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- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4866—Polyethers having a low unsaturation value
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- 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
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- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/672—Dicarboxylic acids and dihydroxy compounds
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- 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
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- 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
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- C08G65/2663—Metal cyanide catalysts, i.e. DMC's
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G65/2669—Non-metals or compounds thereof
- C08G65/2672—Nitrogen or compounds thereof
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- 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
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- 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
- C08G65/2678—Sulfur or compounds thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
- C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
- C08J9/141—Hydrocarbons
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- 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
- C08G2110/00—Foam properties
- C08G2110/0025—Foam properties rigid
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
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Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Toxicology (AREA)
- Polyurethanes Or Polyureas (AREA)
- Polyethers (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32921910P | 2010-04-29 | 2010-04-29 | |
| US201161453152P | 2011-03-16 | 2011-03-16 | |
| PCT/US2011/033346 WO2011137011A1 (en) | 2010-04-29 | 2011-04-21 | Hybrid polyester-polyether polyols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2719589T3 true ES2719589T3 (es) | 2019-07-11 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES11717149T Active ES2719589T3 (es) | 2010-04-29 | 2011-04-21 | Polioles híbridos de poliéster y poliéter |
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| Country | Link |
|---|---|
| US (1) | US8680211B2 (enExample) |
| EP (1) | EP2563834B1 (enExample) |
| JP (1) | JP5986070B2 (enExample) |
| CN (1) | CN102869696B (enExample) |
| ES (1) | ES2719589T3 (enExample) |
| MX (1) | MX2012012617A (enExample) |
| PL (1) | PL2563834T3 (enExample) |
| WO (1) | WO2011137011A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102009031584A1 (de) * | 2009-07-03 | 2011-01-05 | Bayer Materialscience Ag | Verfahren zur Herstellung von Polyetherpolyolen mit primären Hydroxyl-Endgruppen |
| JP5731651B2 (ja) * | 2010-08-20 | 2015-06-10 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | ポリエーテルエステルポリオールの製造方法 |
| JP6060092B2 (ja) | 2010-12-27 | 2017-01-11 | ダウ グローバル テクノロジーズ エルエルシー | 複合金属シアン化物触媒錯体およびマグネシウム、第３族〜第１５族金属またはランタニド系列金属化合物を用いるアルキレンオキシド重合 |
| EP2678370B1 (en) | 2011-02-23 | 2016-03-30 | Council of Scientific & Industrial Research | Process for preparing hyperbranched polyesters |
| EP2744839B1 (de) * | 2011-08-16 | 2016-02-24 | Covestro Deutschland AG | Verfahren zur herstellung eines polyurethan-polyisocyanurat-hartschaums |
| BR112014008018A2 (pt) * | 2011-10-14 | 2017-04-11 | Dow Global Technologies Llc | poliol poliéster-poliéter, mistura de poliol, sistema de reação para produção de uma espuma rígida e processo para preparar uma espuma de poliuretano rígida |
| KR102008546B1 (ko) * | 2011-12-18 | 2019-08-07 | 다우 글로벌 테크놀로지스 엘엘씨 | 하이브리드 폴리에스테르-폴리에테르 폴리올의 제조 방법 |
| CN104619736B (zh) | 2012-07-31 | 2017-08-18 | 科思创德国股份有限公司 | 使用乳化发泡剂制备聚氨酯泡沫的方法 |
| CN103193953B (zh) * | 2013-03-18 | 2014-10-29 | 江苏利田科技股份有限公司 | 一种12 官能度聚氨酯丙烯酸酯及其制备方法和应用 |
| WO2014166898A1 (de) * | 2013-04-11 | 2014-10-16 | Bayer Materialscience Ag | Polyesterpolyole mit langkettigen polyetherpolyol-bausteinen und deren verwendung in pur-/pir-hartschaumstoffen |
| CN103242507B (zh) * | 2013-04-23 | 2015-02-11 | 江苏利田科技股份有限公司 | 一种8官能度聚氨酯丙烯酸酯及其制备方法和应用 |
| CN103242508B (zh) * | 2013-04-23 | 2015-10-28 | 江苏利田科技股份有限公司 | 一种4官能度聚氨酯丙烯酸酯及其制备方法和应用 |
| EP2978601B1 (en) * | 2013-05-30 | 2018-07-25 | Dow Global Technologies LLC | Lamination method |
| WO2014193623A1 (en) | 2013-05-30 | 2014-12-04 | Dow Global Technologies Llc | Hybrid polyols |
| WO2015042300A1 (en) | 2013-09-19 | 2015-03-26 | Dow Global Technologies Llc | Vacuum assisted process to make closed cell rigid polyurethane foams using mixed blowing agents |
| EP3161046B1 (de) * | 2014-06-26 | 2026-03-25 | Covestro Deutschland AG | Verbundbauteile auf basis von hydrophoben polyolen |
| EP3209706B1 (en) * | 2014-10-22 | 2018-09-05 | Dow Global Technologies LLC | Dual catalyst system for high primary hydroxyl polyols |
| DK3133097T3 (da) * | 2015-08-17 | 2022-12-19 | Evonik Operations Gmbh | Fremstilling af blødt polyurethanskum med forbedret hårdhed |
| CN108026247B (zh) | 2015-09-29 | 2022-03-25 | 陶氏环球技术有限责任公司 | 基于甲苯二异氰酸酯缩二脲的聚氨酯泡沫预聚物 |
| WO2017089417A1 (de) * | 2015-11-26 | 2017-06-01 | Covestro Deutschland Ag | Pur-/pir-hartschäume aus polyadditions-oligoestern |
| PL3426708T3 (pl) * | 2016-03-11 | 2020-07-13 | Invista Textiles (U.K.) Limited | Pianki poliuretanowe i poliizocyjanuranowe oraz sposoby ich wytwarzania |
| CN109642046B (zh) | 2016-06-28 | 2022-01-25 | Ptt全球化学公众有限公司 | 基于天然油多元醇的杂化多元醇 |
| CN107189049B (zh) * | 2017-06-14 | 2019-03-01 | 江南大学 | 一种杂化型聚酯及其制备方法 |
| EA202091138A1 (ru) * | 2017-11-14 | 2020-10-06 | Дау Глоубл Текнолоджиз Ллк | Состав и синтез обладающих высокой молекулярной массой ароматических сложных полиэфирполиолов |
| WO2020057933A1 (en) * | 2018-09-18 | 2020-03-26 | Byk-Chemie Gmbh | An amine functional compound having a urethane group |
| CN109212005B (zh) * | 2018-09-28 | 2020-07-24 | 山东一诺威新材料有限公司 | 利用电位滴定测定聚醚多元醇中伯羟基含量的方法 |
| CN109438690A (zh) * | 2018-11-13 | 2019-03-08 | 耿佃勇 | 新型不饱和聚醚多元醇 |
| CN111307888B (zh) * | 2018-12-11 | 2022-04-12 | 辽宁奥克化学股份有限公司 | 一种嵌段聚醚多元醇中伯羟基含量的检测方法 |
| CN113891903A (zh) | 2019-05-24 | 2022-01-04 | 陶氏环球技术有限责任公司 | 用于制备阻燃硬质聚氨酯泡沫的储存稳定的含hfo或hcfo的多元醇组合物 |
| WO2021011226A1 (en) * | 2019-07-12 | 2021-01-21 | Dow Global Technologies Llc | Metal polyols for use in a polyurethane polymer |
| TWI887244B (zh) * | 2019-07-12 | 2025-06-21 | 美商陶氏全球科技有限責任公司 | 基於溶劑之組合物 |
| MX2022002308A (es) | 2019-09-02 | 2022-07-19 | Dow Global Technologies Llc | Espuma de poliuretano rigida fabricada con un agente soplante de hidrocarburo y 1,1,1,4,4,4-hexafluorobut-2-eno. |
| EP4025420A1 (en) | 2019-09-02 | 2022-07-13 | Dow Global Technologies LLC | Apparatus and method for applying a foaming reaction mixture onto a laminator |
| EP3875510A1 (de) * | 2020-03-03 | 2021-09-08 | Covestro Deutschland AG | Verfahren zur herstellung eines etheresterols |
| CN111518251A (zh) * | 2020-04-08 | 2020-08-11 | 上海抚佳精细化工有限公司 | 一种聚氨酯硬质泡沫及其制备方法 |
| US20250115711A1 (en) * | 2021-10-25 | 2025-04-10 | Dow Global Technologies Llc | Polyether polymerization process |
| MX2024007189A (es) | 2021-12-20 | 2024-06-26 | Dow Global Technologies Llc | Aparato y metodo para aplicar una mezcla de reaccion espumante sobre un laminador usando una tobera divergente. |
| CN118382653A (zh) | 2021-12-30 | 2024-07-23 | 美国圣戈班性能塑料公司 | 聚氨酯泡沫及其形成方法 |
| JP2025529073A (ja) | 2022-08-31 | 2025-09-04 | ダウ グローバル テクノロジーズ エルエルシー | 成形ポリマー発泡体を作製するための方法 |
| EP4608890A1 (en) * | 2022-10-28 | 2025-09-03 | Shell Internationale Research Maatschappij B.V. | Batch process for preparing a polyether polyol using a double metal cyanide catalyst |
| JP2026512357A (ja) | 2023-04-12 | 2026-04-15 | ステパン カンパニー | 低残留モノマーグリコール芳香族ポリエステルポリオール |
| CN116199855B (zh) * | 2023-05-06 | 2023-07-18 | 成都瑞吉龙科技有限责任公司 | 一种聚醚-聚酯混合型聚氨酯及其制备方法 |
| CN121152715A (zh) | 2023-06-08 | 2025-12-16 | 陶氏环球技术有限责任公司 | 用于使用再循环材料生产波纹形层压板的方法 |
| CN121464027A (zh) | 2023-06-09 | 2026-02-03 | 陶氏环球技术有限责任公司 | 用于生产波纹形层压板的方法 |
| WO2025007334A1 (en) * | 2023-07-06 | 2025-01-09 | Dow Global Technologies Llc | Composites formed using lewis-acid polymerized polyols and methods of preparing same |
| KR20260033052A (ko) * | 2023-07-06 | 2026-03-10 | 다우 글로벌 테크놀로지스 엘엘씨 | 루이스-산 중합된 폴리올을 사용하여 형성된 복합재 및 이의 제조 방법 |
| WO2026096846A1 (en) | 2024-10-31 | 2026-05-07 | Dow Global Technologies Llc | Alkoxylations using polyhedral borate catalysts |
| CN119571514A (zh) * | 2025-02-08 | 2025-03-07 | 江苏多来运纺织有限公司 | 一种吸湿透汗雪尼尔纱线及其生产工艺 |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3427256A (en) | 1963-02-14 | 1969-02-11 | Gen Tire & Rubber Co | Double metal cyanide complex compounds |
| US3427334A (en) | 1963-02-14 | 1969-02-11 | Gen Tire & Rubber Co | Double metal cyanides complexed with an alcohol aldehyde or ketone to increase catalytic activity |
| US3278459A (en) | 1963-02-14 | 1966-10-11 | Gen Tire & Rubber Co | Method of making a polyether using a double metal cyanide complex compound |
| US3459733A (en) * | 1964-10-15 | 1969-08-05 | Mobil Oil Corp | Monomeric polyesters of polyhydroxy compounds and process for preparing same |
| US3941849A (en) | 1972-07-07 | 1976-03-02 | The General Tire & Rubber Company | Polyethers and method for making the same |
| AU538363B2 (en) * | 1980-06-13 | 1984-08-09 | Ici Australia Limited | Alkoxylation of organic compounds |
| AU551979B2 (en) | 1982-03-31 | 1986-05-15 | Shell Internationale Research Maatschappij B.V. | Epoxy polymerisation catalysts |
| FR2536069A1 (fr) | 1982-11-17 | 1984-05-18 | Bp Chimie Sa | Procede de preparation de produits d'addition d'epoxydes et de composes hydroxyles |
| DE3315381A1 (de) * | 1983-04-28 | 1984-10-31 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von polyester- oder polyether-polyester-polyolen |
| US4701477A (en) * | 1983-07-13 | 1987-10-20 | Chardonol, Division Of Freeman Corporation | Low viscosity aromatic polyols and methods for their preparation |
| US4707535A (en) * | 1983-10-27 | 1987-11-17 | Union Carbide Corporation | Low viscosity adducts of a poly(active hydrogen) organic compound and polyepoxide |
| DE3613875A1 (de) * | 1986-04-24 | 1987-10-29 | Basf Ag | Verfahren zur herstellung von polyester-polyolen |
| JP3097854B2 (ja) * | 1989-05-12 | 2000-10-10 | 旭硝子株式会社 | ポリウレタン類の製造方法 |
| NZ234512A (en) * | 1989-07-19 | 1992-05-26 | Mitsui Toatsu Chemicals | Polyols prepared by adding alkylene oxide onto a compound containing at least one ester and/or amide linkage; polyurethane resins and foams prepared therefrom |
| JPH03285906A (ja) * | 1989-07-19 | 1991-12-17 | Mitsui Toatsu Chem Inc | ポリオール、ポリウレタン樹脂とその利用 |
| CA2082564A1 (en) * | 1991-11-12 | 1993-05-13 | John N. Argyropoulos | Substituted 1,5-pentanediols and processes for the preparation thereof |
| US5158922A (en) | 1992-02-04 | 1992-10-27 | Arco Chemical Technology, L.P. | Process for preparing metal cyanide complex catalyst |
| US5304688A (en) | 1993-04-13 | 1994-04-19 | The Dow Chemical Company | Process for the preparation of bishydroxy aromatic compounds |
| US5470813A (en) | 1993-11-23 | 1995-11-28 | Arco Chemical Technology, L.P. | Double metal cyanide complex catalysts |
| US5482908A (en) | 1994-09-08 | 1996-01-09 | Arco Chemical Technology, L.P. | Highly active double metal cyanide catalysts |
| JP3308411B2 (ja) * | 1994-12-20 | 2002-07-29 | 三井化学株式会社 | エステルポリオールの製造方法 |
| DE19702787A1 (de) * | 1997-01-27 | 1998-07-30 | Bayer Ag | Verfahren zur Herstellung von Polyetherpolyolen |
| US6376645B1 (en) * | 1999-07-09 | 2002-04-23 | The Dow Chemical Company | Complexing agent-modified hexacyanometallate hexanitrometallate catalysts |
| DE19949091A1 (de) * | 1999-10-12 | 2001-04-26 | Basf Ag | Polyester-Polyetherblockcopolymere |
| US6989432B2 (en) | 2002-01-10 | 2006-01-24 | Invista North America S.A.R.L. | Copolymers of tetrahydrofuran, ethylene oxide and an additional cyclic ether |
| DE10243362A1 (de) | 2002-09-18 | 2004-04-01 | Basf Ag | Herstellung von Alkanolalkoxylaten bei optimierten Reaktionstemperaturen |
| EP1687385B1 (en) * | 2003-11-17 | 2013-04-03 | Bayer MaterialScience LLC | Ultraviolet-curable polyols and polyurethane compositions made therefrom |
| US20050107486A1 (en) * | 2003-11-17 | 2005-05-19 | Bi Le-Khac | UV-curable polyols |
| JP4239814B2 (ja) * | 2003-12-22 | 2009-03-18 | 旭硝子株式会社 | ポリエーテル類の製造法 |
| CN101516954B (zh) * | 2006-09-27 | 2011-07-20 | 旭硝子株式会社 | 软质聚氨酯泡沫塑料的制造方法 |
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2011
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- 2011-04-21 EP EP11717149.6A patent/EP2563834B1/en active Active
- 2011-04-21 US US13/640,429 patent/US8680211B2/en not_active Expired - Fee Related
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- 2011-04-21 CN CN201180021395.8A patent/CN102869696B/zh not_active Expired - Fee Related
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| JP5986070B2 (ja) | 2016-09-06 |
| JP2013525573A (ja) | 2013-06-20 |
| PL2563834T3 (pl) | 2019-07-31 |
| WO2011137011A1 (en) | 2011-11-03 |
| EP2563834B1 (en) | 2019-02-27 |
| CN102869696B (zh) | 2015-02-04 |
| US8680211B2 (en) | 2014-03-25 |
| EP2563834A1 (en) | 2013-03-06 |
| CN102869696A (zh) | 2013-01-09 |
| US20130035467A1 (en) | 2013-02-07 |
| MX2012012617A (es) | 2012-12-17 |
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