DE3314790A1 - Mehrstufenverfahren zur herstellung von 3-isocyanatomethyl-3,5,5-trimethyl-cyclohexylisocyanat - Google Patents
Mehrstufenverfahren zur herstellung von 3-isocyanatomethyl-3,5,5-trimethyl-cyclohexylisocyanatInfo
- Publication number
- DE3314790A1 DE3314790A1 DE19833314790 DE3314790A DE3314790A1 DE 3314790 A1 DE3314790 A1 DE 3314790A1 DE 19833314790 DE19833314790 DE 19833314790 DE 3314790 A DE3314790 A DE 3314790A DE 3314790 A1 DE3314790 A1 DE 3314790A1
- Authority
- DE
- Germany
- Prior art keywords
- trimethyl
- stage
- alcohol
- isocyanatomethyl
- cyclohexyl isocyanate
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 24
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 title description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 42
- 238000006243 chemical reaction Methods 0.000 claims description 36
- -1 alkyl carbamates Chemical class 0.000 claims description 21
- 238000003776 cleavage reaction Methods 0.000 claims description 19
- 230000007017 scission Effects 0.000 claims description 19
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 18
- 238000009833 condensation Methods 0.000 claims description 16
- 230000005494 condensation Effects 0.000 claims description 16
- 239000011541 reaction mixture Substances 0.000 claims description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
- 239000004814 polyurethane Substances 0.000 claims description 14
- 229920002635 polyurethane Polymers 0.000 claims description 14
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- 238000004821 distillation Methods 0.000 claims description 8
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- 239000004202 carbamide Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 5
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 230000004992 fission Effects 0.000 claims description 5
- 239000010409 thin film Substances 0.000 claims description 5
- 239000010936 titanium Substances 0.000 claims description 5
- 229910052719 titanium Inorganic materials 0.000 claims description 5
- 229910001369 Brass Inorganic materials 0.000 claims description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 239000010951 brass Substances 0.000 claims description 4
- 229910052804 chromium Inorganic materials 0.000 claims description 4
- 239000011651 chromium Substances 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 239000011261 inert gas Substances 0.000 claims description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 4
- 229910000831 Steel Inorganic materials 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 239000010959 steel Substances 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000010453 quartz Substances 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 8
- LAPNHXJSISCJHH-UHFFFAOYSA-N (1-isocyanato-3,3,5-trimethylcyclohexyl)methyl cyanate Chemical compound CC1CC(C)(C)CC(COC#N)(N=C=O)C1 LAPNHXJSISCJHH-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 22
- 239000000203 mixture Substances 0.000 description 11
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 7
- 235000013877 carbamide Nutrition 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 239000005056 polyisocyanate Substances 0.000 description 4
- 229920001228 polyisocyanate Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 3
- QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- 239000011733 molybdenum Substances 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 229910052797 bismuth Inorganic materials 0.000 description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
- SKKTUOZKZKCGTB-UHFFFAOYSA-N butyl carbamate Chemical compound CCCCOC(N)=O SKKTUOZKZKCGTB-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 2
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- PKQYSCBUFZOAPE-UHFFFAOYSA-N 1,2-dibenzyl-3-methylbenzene Chemical compound C=1C=CC=CC=1CC=1C(C)=CC=CC=1CC1=CC=CC=C1 PKQYSCBUFZOAPE-UHFFFAOYSA-N 0.000 description 1
- ZQVHTTABFLHMPA-UHFFFAOYSA-N 2-(4-chlorophenoxy)-5-nitropyridine Chemical compound N1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1 ZQVHTTABFLHMPA-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910021556 Chromium(III) chloride Inorganic materials 0.000 description 1
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910021576 Iron(III) bromide Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910021380 Manganese Chloride Inorganic materials 0.000 description 1
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 1
- 241001077660 Molo Species 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 244000078856 Prunus padus Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- COQLPRJCUIATTQ-UHFFFAOYSA-N Uranyl acetate Chemical compound O.O.O=[U]=O.CC(O)=O.CC(O)=O COQLPRJCUIATTQ-UHFFFAOYSA-N 0.000 description 1
- 229910021551 Vanadium(III) chloride Inorganic materials 0.000 description 1
- RVYQMGHGNQWXHF-UHFFFAOYSA-I [V+5].CC(=O)CCC([O-])=O.CC(=O)CCC([O-])=O.CC(=O)CCC([O-])=O.CC(=O)CCC([O-])=O.CC(=O)CCC([O-])=O Chemical compound [V+5].CC(=O)CCC([O-])=O.CC(=O)CCC([O-])=O.CC(=O)CCC([O-])=O.CC(=O)CCC([O-])=O.CC(=O)CCC([O-])=O RVYQMGHGNQWXHF-UHFFFAOYSA-I 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 125000005910 alkyl carbonate group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- OVHDZBAFUMEXCX-UHFFFAOYSA-N benzyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1=CC=CC=C1 OVHDZBAFUMEXCX-UHFFFAOYSA-N 0.000 description 1
- HUTDDBSSHVOYJR-UHFFFAOYSA-H bis[(2-oxo-1,3,2$l^{5},4$l^{2}-dioxaphosphaplumbetan-2-yl)oxy]lead Chemical compound [Pb+2].[Pb+2].[Pb+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O HUTDDBSSHVOYJR-UHFFFAOYSA-H 0.000 description 1
- JHXKRIRFYBPWGE-UHFFFAOYSA-K bismuth chloride Chemical compound Cl[Bi](Cl)Cl JHXKRIRFYBPWGE-UHFFFAOYSA-K 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- ZZHGIUCYKGFIPV-UHFFFAOYSA-N butylcarbamic acid Chemical compound CCCCNC(O)=O ZZHGIUCYKGFIPV-UHFFFAOYSA-N 0.000 description 1
- AMJQWGIYCROUQF-UHFFFAOYSA-N calcium;methanolate Chemical compound [Ca+2].[O-]C.[O-]C AMJQWGIYCROUQF-UHFFFAOYSA-N 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 1
- 239000011636 chromium(III) chloride Substances 0.000 description 1
- 235000007831 chromium(III) chloride Nutrition 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- 229940044175 cobalt sulfate Drugs 0.000 description 1
- 229910000361 cobalt sulfate Inorganic materials 0.000 description 1
- KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Substances Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- IKUPISAYGBGQDT-UHFFFAOYSA-N copper;dioxido(dioxo)molybdenum Chemical compound [Cu+2].[O-][Mo]([O-])(=O)=O IKUPISAYGBGQDT-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- ISXUHJXWYNONDI-UHFFFAOYSA-L dichloro(diphenyl)stannane Chemical compound C=1C=CC=CC=1[Sn](Cl)(Cl)C1=CC=CC=C1 ISXUHJXWYNONDI-UHFFFAOYSA-L 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- OTCKNHQTLOBDDD-UHFFFAOYSA-K gold(3+);triacetate Chemical compound [Au+3].CC([O-])=O.CC([O-])=O.CC([O-])=O OTCKNHQTLOBDDD-UHFFFAOYSA-K 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910000398 iron phosphate Inorganic materials 0.000 description 1
- WBJZTOZJJYAKHQ-UHFFFAOYSA-K iron(3+) phosphate Chemical compound [Fe+3].[O-]P([O-])([O-])=O WBJZTOZJJYAKHQ-UHFFFAOYSA-K 0.000 description 1
- PVFSDGKDKFSOTB-UHFFFAOYSA-K iron(3+);triacetate Chemical compound [Fe+3].CC([O-])=O.CC([O-])=O.CC([O-])=O PVFSDGKDKFSOTB-UHFFFAOYSA-K 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229940046892 lead acetate Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 1
- LTRVAZKHJRYLRJ-UHFFFAOYSA-N lithium;butan-1-olate Chemical compound [Li+].CCCC[O-] LTRVAZKHJRYLRJ-UHFFFAOYSA-N 0.000 description 1
- AZVCGYPLLBEUNV-UHFFFAOYSA-N lithium;ethanolate Chemical compound [Li+].CC[O-] AZVCGYPLLBEUNV-UHFFFAOYSA-N 0.000 description 1
- MXIRPJHGXWFUAE-UHFFFAOYSA-N lithium;propan-1-olate Chemical compound [Li+].CCC[O-] MXIRPJHGXWFUAE-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 1
- 239000011565 manganese chloride Substances 0.000 description 1
- 235000002867 manganese chloride Nutrition 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- AHSBSUVHXDIAEY-UHFFFAOYSA-K manganese(iii) acetate Chemical compound [Mn+3].CC([O-])=O.CC([O-])=O.CC([O-])=O AHSBSUVHXDIAEY-UHFFFAOYSA-K 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- UIEKYBOPAVTZKW-UHFFFAOYSA-L naphthalene-2-carboxylate;nickel(2+) Chemical compound [Ni+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 UIEKYBOPAVTZKW-UHFFFAOYSA-L 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 150000002835 noble gases Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000011049 pearl Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- 229940071536 silver acetate Drugs 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011885 synergistic combination Substances 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- DPNUIZVZBWBCPB-UHFFFAOYSA-J titanium(4+);tetraphenoxide Chemical compound [Ti+4].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 DPNUIZVZBWBCPB-UHFFFAOYSA-J 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 description 1
- DAOVYDBYKGXFOB-UHFFFAOYSA-N tris(2-methylpropoxy)alumane Chemical compound [Al+3].CC(C)C[O-].CC(C)C[O-].CC(C)C[O-] DAOVYDBYKGXFOB-UHFFFAOYSA-N 0.000 description 1
- ZNOKGRXACCSDPY-UHFFFAOYSA-N tungsten(VI) oxide Inorganic materials O=[W](=O)=O ZNOKGRXACCSDPY-UHFFFAOYSA-N 0.000 description 1
- GAAKLDANOSASAM-UHFFFAOYSA-N undec-10-enoic acid;zinc Chemical compound [Zn].OC(=O)CCCCCCCCC=C GAAKLDANOSASAM-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229940118257 zinc undecylenate Drugs 0.000 description 1
- NXCSCNJIBXRQNK-UHFFFAOYSA-L zinc;4-oxopentanoate Chemical compound [Zn+2].CC(=O)CCC([O-])=O.CC(=O)CCC([O-])=O NXCSCNJIBXRQNK-UHFFFAOYSA-L 0.000 description 1
- JDLYKQWJXAQNNS-UHFFFAOYSA-L zinc;dibenzoate Chemical compound [Zn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 JDLYKQWJXAQNNS-UHFFFAOYSA-L 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- ZPEJZWGMHAKWNL-UHFFFAOYSA-L zinc;oxalate Chemical compound [Zn+2].[O-]C(=O)C([O-])=O ZPEJZWGMHAKWNL-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/10—Derivatives of isocyanic acid having isocyanate groups bound to carbon atoms of rings other than six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833314790 DE3314790A1 (de) | 1983-04-23 | 1983-04-23 | Mehrstufenverfahren zur herstellung von 3-isocyanatomethyl-3,5,5-trimethyl-cyclohexylisocyanat |
| US06/599,821 US4596679A (en) | 1983-04-23 | 1984-04-13 | Multiple-step process for the preparation of 3-isocyanatomethyl-3,5,5-trimethylcyclohexylisocyanate |
| DE8484104353T DE3462887D1 (en) | 1983-04-23 | 1984-04-17 | Multi-step process for the production of 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanates |
| EP84104353A EP0126300B1 (de) | 1983-04-23 | 1984-04-17 | Mehrstufenverfahren zur Herstellung von 3-Isocyanatomethyl-3,5,5-trimethyl-cyclohexylisocyanat |
| CA000452345A CA1225997A (en) | 1983-04-23 | 1984-04-18 | Multiple-step process for the preparation of 3- isocyanatomethyl-3,5,5-trimethylcyclohexylisocyanate |
| JP59078815A JPS59205353A (ja) | 1983-04-23 | 1984-04-20 | ３−イソシアネ−トメチル−３，５，５−トリメチル−シクロヘキシルイソシアネ−トの多工程式製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833314790 DE3314790A1 (de) | 1983-04-23 | 1983-04-23 | Mehrstufenverfahren zur herstellung von 3-isocyanatomethyl-3,5,5-trimethyl-cyclohexylisocyanat |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3314790A1 true DE3314790A1 (de) | 1984-10-25 |
Family
ID=6197202
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19833314790 Withdrawn DE3314790A1 (de) | 1983-04-23 | 1983-04-23 | Mehrstufenverfahren zur herstellung von 3-isocyanatomethyl-3,5,5-trimethyl-cyclohexylisocyanat |
| DE8484104353T Expired DE3462887D1 (en) | 1983-04-23 | 1984-04-17 | Multi-step process for the production of 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanates |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8484104353T Expired DE3462887D1 (en) | 1983-04-23 | 1984-04-17 | Multi-step process for the production of 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanates |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4596679A (OSRAM) |
| EP (1) | EP0126300B1 (OSRAM) |
| JP (1) | JPS59205353A (OSRAM) |
| CA (1) | CA1225997A (OSRAM) |
| DE (2) | DE3314790A1 (OSRAM) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5087739A (en) * | 1988-08-18 | 1992-02-11 | Huels Aktiengesellschaft | Circulation process for the production of aliphatic and cycloaliphatic diisocyanates |
| EP0566925A3 (en) * | 1992-04-21 | 1993-12-08 | Basf Ag | Multi-step method for the continuous preparation of organic polyisocyanates |
| EP0568782A3 (de) * | 1992-05-05 | 1993-12-08 | Hüls Aktiengesellschaft | Kontinuierliches mehrstufiges Verfahren zur Herstellung von (cyclo)-aliphatischen Diisocyanaten |
| DE19754748B4 (de) * | 1997-12-10 | 2004-04-29 | Gras, Rainer, Dipl.-Chem. Dr. | Verfahren zur Herstellung eines blockierten Lackpolyisocyanats und dessen Verwendung für PUR-Lacke |
Families Citing this family (105)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2538222B2 (ja) * | 1986-12-26 | 1996-09-25 | ダイセル化学工業株式会社 | イソホロンジイソシアネ−トの製造方法 |
| US4883908A (en) * | 1989-02-02 | 1989-11-28 | Arco Chemical Technology, Inc. | Process for the preparation of aromatic isocyanates from dialkyl ureas using an organic sulfonic acid promoter |
| US4978779A (en) * | 1989-03-09 | 1990-12-18 | Arco Chemical Technology, Inc. | Preparation of methylene diphenylene diisocyanates and polymethylene polyphenylene poly (isocyanates) using an organic sulfonic acid promoter |
| US5179223A (en) * | 1990-12-13 | 1993-01-12 | Union Carbide Chemicals & Plastics Technology Corporation | Process for producing carbamates from oximes |
| DE4342426A1 (de) * | 1993-12-13 | 1995-06-14 | Bayer Ag | Verfahren zur Herstellung von Diurethanen und ihre Verwendung zur Herstellung von Diisocyanaten |
| DE19523386A1 (de) * | 1995-06-23 | 1997-01-09 | Bayer Ag | Verfahren zur Entfernung von Nebenprodukten aus Diurethanen |
| ES2166922T3 (es) * | 1996-03-15 | 2002-05-01 | Bayer Ag | Uso de disolventes o mezclas de disolventes de alto punto de ebullicion como medio intercambiador de calor para la disociacion termica de esteres de acidos carbamicos. |
| DE19758050A1 (de) * | 1997-12-29 | 1999-07-01 | Huels Chemische Werke Ag | Verfahren zur Herstellung eines farbreduzierten isocyanatgruppenhaltigen Polyisocyanats auf Basis von 1-Isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexan (IPDI) |
| DE19944373A1 (de) | 1999-09-16 | 2001-03-22 | Degussa | Katalysator und Verfahren zur Herstellung von farbreduzierten isocyanuratgruppenhaltigen Polyisocyananten |
| DE10033099A1 (de) | 2000-07-07 | 2002-01-17 | Degussa | Verfahren zur Herstellung von geruchsarmen und lagerstabilen monomerhaltigen Polyisocyanuraten aus Isophorondiisocyanat |
| DE10065176A1 (de) | 2000-12-23 | 2002-06-27 | Degussa | Katalysator und Verfahren zur Herstellung von niedrigviskosen und farbreduzierten isocyanuratgruppenhaltigen Polyisocyanaten |
| JP5320653B2 (ja) * | 2001-03-26 | 2013-10-23 | Ｊｓｒ株式会社 | 膜形成用組成物および絶縁膜形成用材料 |
| DE10131525A1 (de) * | 2001-07-02 | 2003-01-16 | Degussa | Verfahren zur Herstellung von geruchsarmen und lagerstabilen monomerhaltigen Polyisocyanuraten aus Isophorondiisocyanat |
| DE10338509A1 (de) * | 2003-08-22 | 2005-03-17 | Degussa Ag | Mehrstufiges Verfahren zur kontinuierlichen Herstellung von cycloaliphatischen Diisocyanaten |
| DE10338511A1 (de) * | 2003-08-22 | 2005-03-17 | Degussa Ag | Mehrstufiges Verfahren zur kontinuierlichen Herstellung von cycloaliphatischen Diisocyanaten |
| DE10338508A1 (de) | 2003-08-22 | 2005-03-17 | Degussa Ag | Mehrstufiges Verfahren zur kontinuierlichen Herstellung von cycloaliphatischen Diisocyanaten |
| DE102004022626A1 (de) | 2004-05-07 | 2005-12-15 | Degussa Ag | Mehrstufiges Verfahren zur kontinuierlichen Herstellung von cycloaliphatischen Diisocyanaten |
| DE102004026451A1 (de) * | 2004-05-29 | 2005-12-15 | Degussa Ag | Mehrstufiges Verfahren zur kontinuierlichen Herstellung von cycloaliphatischen Diisocyanaten |
| DE102004036499A1 (de) * | 2004-07-28 | 2006-03-23 | Degussa Ag | Mehrstufiges Verfahren zur kontinuierlichen Herstellung von cycloaliphatischen Diisocyanaten |
| DE102005057683A1 (de) | 2005-12-01 | 2007-06-06 | Basf Ag | Strahlungshärtbare wasserelmulgierbare Polyisocyanate |
| JP4859255B2 (ja) * | 2006-11-17 | 2012-01-25 | 旭化成ケミカルズ株式会社 | イソシアネートの製造方法 |
| EP2099838B1 (de) * | 2006-12-04 | 2017-06-14 | Basf Se | Verfahren zur herstellung von polyisocyanaten |
| TW200844080A (en) | 2007-01-11 | 2008-11-16 | Asahi Kasei Chemicals Corp | Process for producing isocyanate |
| EP2139935B1 (de) * | 2007-03-26 | 2010-12-01 | Basf Se | Wasseremulgierbare polyisocyanate |
| EP2132244B1 (de) | 2007-03-27 | 2018-08-22 | Basf Se | Verfahren zur herstellung von farblosen isocyanuraten von diisocyanaten |
| EP2147909B1 (en) | 2007-03-30 | 2016-12-14 | Asahi Kasei Kabushiki Kaisha | Method for production of isocyanate using composition comprising carbamic acid ester and aromatic hydroxy compound, and composition for transport or storage of carbamic acid ester |
| DE102007026196A1 (de) | 2007-06-04 | 2008-12-11 | Basf Se | Verfahren zur Herstellung wasseremulgierbarer Polyurethanacrylate |
| DE102008002008A1 (de) | 2007-06-04 | 2008-12-11 | Basf Se | Verfahren zur Herstellung wasseremulgierbarer Polyurethanacrylate |
| US8193279B2 (en) * | 2007-06-21 | 2012-06-05 | Basf Se | Flexible, radiation-curable coating compositions |
| EP2205655B1 (de) * | 2007-10-22 | 2013-06-26 | Basf Se | Urethangruppenhaltige polyisocyanate |
| DE102008043202A1 (de) | 2007-10-29 | 2009-04-30 | Basf Se | Verfahren zur Kantenleimung von Textilien |
| CN101888994B (zh) * | 2007-12-06 | 2015-01-07 | 巴斯夫欧洲公司 | 含有脲基甲酸酯基团的多异氰酸酯 |
| DE102008054974A1 (de) | 2008-01-14 | 2009-07-16 | Basf Se | Zweikomponentige Polyurethanbeschichtungsmassen |
| DE102008054981A1 (de) | 2008-01-14 | 2009-07-16 | Basf Se | Strahlungshärtbare Polyurethanbeschichtungsmassen |
| EP2275405B1 (en) * | 2008-05-15 | 2019-04-24 | Asahi Kasei Kabushiki Kaisha | Process for producing isocyanate using diaryl carbonate |
| WO2009139062A1 (ja) | 2008-05-15 | 2009-11-19 | 旭化成ケミカルズ株式会社 | イソシアネートの製造方法 |
| CN102257026B (zh) | 2008-10-22 | 2014-04-30 | 巴斯夫欧洲公司 | 制备无色多异氰酸酯的方法 |
| JP5752045B2 (ja) | 2008-12-17 | 2015-07-22 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 速乾性の被覆材料 |
| WO2010076114A1 (de) | 2008-12-17 | 2010-07-08 | Basf Se | Schnelltrocknende beschichtungsmassen |
| DE102010001956A1 (de) | 2009-02-17 | 2010-08-19 | Basf Se | Verfahren zur Herstellung wasseremulgierbarer Polyurethanacrylate |
| DE102010003308A1 (de) | 2009-03-31 | 2011-01-13 | Basf Se | Strahlungshärtbare wasseremulgierbare Polyurethan(meth)acrylate |
| EP2421905B1 (de) | 2009-04-22 | 2013-03-13 | Basf Se | Strahlungshärtbare beschichtungsmassen |
| US9212252B2 (en) | 2009-08-06 | 2015-12-15 | Basf Se | Radiation-curable, water-dispersible polyurethanes and polyurethane dispersions |
| EP2289963B1 (de) | 2009-08-27 | 2013-05-29 | Basf Se | Beschichtungsmassen mit allophanatgruppenhaltigen Polyisocyanaten |
| CN102712734B (zh) | 2009-11-23 | 2014-10-01 | 巴斯夫欧洲公司 | 聚氨酯涂料化合物的催化剂 |
| DE102009054749A1 (de) | 2009-12-16 | 2011-06-22 | Evonik Degussa GmbH, 45128 | Zusammensetzung aus (cyclo)aliphatischen Diisocyanaten und aromatischen Säurehalogeniden |
| US8492472B2 (en) | 2009-12-18 | 2013-07-23 | Basf Se | Polymer dispersions for corrosion control |
| ES2375824T3 (es) | 2009-12-18 | 2012-03-06 | Basf Se | Dispersiones de pol�?meros. |
| WO2011124710A1 (de) | 2010-04-09 | 2011-10-13 | Basf Se | Durch energieeintrag reparable beschichtungen |
| US8586697B2 (en) | 2010-04-09 | 2013-11-19 | Basf Se | Coatings repairable by introduction of energy |
| US9550857B2 (en) | 2010-07-13 | 2017-01-24 | Basf Se | High-functionality polyisocyanates containing urethane groups |
| EP2593490B1 (de) | 2010-07-13 | 2015-09-09 | Basf Se | Hochfunktionelle urethangruppen aufweisende polyisocyanate |
| EP2598549A1 (de) | 2010-07-30 | 2013-06-05 | Basf Se | Hochfunktionelle urethangruppen aufweisende polyisocyanate |
| US8580887B2 (en) | 2010-07-30 | 2013-11-12 | Basf Se | High-functionality polyisocyanates containing urethane groups |
| CN103403052B (zh) | 2011-02-22 | 2015-06-17 | 巴斯夫欧洲公司 | 用于可辐射固化的涂料材料的流变剂 |
| US9090736B2 (en) | 2011-02-22 | 2015-07-28 | Basf Se | Rheological agent for radiation-curable coating compositions |
| US8609887B2 (en) | 2011-03-03 | 2013-12-17 | Basf Se | Process for preparing polyisocyanates comprising biuret groups |
| WO2012117099A1 (de) | 2011-03-03 | 2012-09-07 | Basf Se | Verfahren zur herstellung von biuretgruppenhaltigen polyisocyanaten |
| US9617402B2 (en) | 2011-10-28 | 2017-04-11 | Basf Se | Process for preparing polyisocyanates which are flocculation-stable in solvents from (cyclo)aliphatic diisocyanates |
| EP2773612B1 (de) | 2011-10-28 | 2018-12-12 | Basf Se | Verfahren zur herstellung von in lösungsmitteln flockulationsstabilen polyisocyanaten von (cyclo)aliphatischen diisocyanaten |
| WO2013060614A1 (de) | 2011-10-28 | 2013-05-02 | Basf Se | Farbstabile härterzusammensetzungen enthaltend polyisocyanate (cyclo)aliphatischer diisocyanate |
| US8728455B2 (en) | 2012-01-27 | 2014-05-20 | Basf Se | Radiation-curable antimicrobial coatings |
| WO2013110504A1 (en) | 2012-01-27 | 2013-08-01 | Basf Se | Radiation-curable antimicrobial coatings |
| EP2828348B1 (en) | 2012-03-19 | 2016-04-20 | Basf Se | Radiation-curable coating compositions |
| CN104204021B (zh) | 2012-03-19 | 2018-04-20 | 巴斯夫欧洲公司 | 可辐射固化的含水分散体 |
| US9193888B2 (en) | 2012-03-19 | 2015-11-24 | Basf Se | Radiation-curable aqueous dispersions |
| CN104812793B (zh) | 2012-09-28 | 2017-11-14 | 巴斯夫欧洲公司 | 水分散性多异氰酸酯 |
| WO2014048776A2 (de) | 2012-09-28 | 2014-04-03 | Basf Se | Wasseremulgierbare isocyanate mit verbessertem glanz |
| DE102012219324A1 (de) | 2012-10-23 | 2014-04-24 | Evonik Industries Ag | Zusammensetzungen umfassend alkoxysilanhaltige Isocyanateund saure Stabilisatoren |
| CA2885130A1 (en) | 2012-10-24 | 2014-05-01 | Basf Se | Radiation-curing, water-dispersible polyurethane (meth)acrylates |
| EP2941446B1 (de) | 2013-01-07 | 2018-10-10 | Basf Se | Katalysatoren für polyurethanbeschichtungsmassen |
| US9902871B2 (en) | 2013-05-02 | 2018-02-27 | Basf Se | Water-emulsifiable isocyanates for coatings having an improved gloss |
| WO2014191503A1 (de) | 2013-05-28 | 2014-12-04 | Basf Se | Antimikrobielle polyurethanbeschichtungen |
| KR20160051814A (ko) | 2013-08-26 | 2016-05-11 | 바스프 에스이 | 방사선 경화성의 수분산성 폴리우레탄 (메트)아크릴레이트 |
| US10227504B2 (en) | 2013-09-25 | 2019-03-12 | Basf Se | Crosslinkers for coating compounds |
| RU2656392C2 (ru) | 2013-10-16 | 2018-06-06 | Басф Се | Способ получения водоэмульгируемых полиуретанакрилатов |
| JP6649893B2 (ja) | 2014-03-12 | 2020-02-19 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 速乾性で、硬弾性で、耐引掻性で、かつ安定なコーティング材料 |
| EP2808354A1 (de) | 2014-08-08 | 2014-12-03 | Basf Se | Schnelltrocknende, hart-elastische, kratzfeste und beständige Beschichtungsmassen |
| WO2016087240A1 (de) | 2014-12-03 | 2016-06-09 | Basf Se | Bindemittelsystem für hochglänzende anstriche |
| WO2016150780A1 (de) | 2015-03-26 | 2016-09-29 | Basf Se | Zweikomponenten beschichtungszusammensetzung enthaltend ein in gegenwart von lignin-sulfonat hergestelltes polymerisat |
| US10358576B2 (en) | 2015-04-20 | 2019-07-23 | Basf Se | Two-component coating compounds |
| US10696776B2 (en) | 2015-09-07 | 2020-06-30 | Basf Se | Water-emulsifiable isocyanates with improved properties |
| KR102586277B1 (ko) | 2015-09-23 | 2023-10-11 | 바스프 에스이 | 2성분 코팅 화합물 |
| ES2769001T3 (es) | 2015-12-09 | 2020-06-24 | Basf Se | Poliisocianatos dispersables en agua |
| EP3305824A1 (de) | 2016-10-07 | 2018-04-11 | Basf Se | Farbstabile härterzusammensetzungen enthaltend polyisocyanate (cyclo)aliphatischer diisocyanate |
| EP3305863A1 (de) | 2016-10-07 | 2018-04-11 | Basf Se | Verfahren zur herstellung von in lösungsmitteln flockulationsstabilen polyisocyanaten von (cyclo)aliphatischen diisocyanaten |
| EP3555164B1 (de) | 2016-12-14 | 2021-06-02 | Basf Se | Wasseremulgierbare isocyanate mit verbesserten eigenschaften |
| EP3401344B1 (de) | 2017-05-09 | 2020-04-08 | Evonik Operations GmbH | Verfahren zur herstellung von trimeren und/oder oligomeren von diisocyanaten |
| EP3431521A1 (de) | 2017-07-20 | 2019-01-23 | Basf Se | Farbstabile härterzusammensetzungen enthaltend polyisocyanate (cyclo)aliphatischer diisocyanate |
| EP3336117A1 (de) | 2017-09-20 | 2018-06-20 | Basf Se | Verfahren zur herstellung von in lösungsmitteln flockulationsstabilen polyisocyanaten von (cyclo)aliphatischen diisocyanaten |
| EP3336118A1 (de) | 2017-09-20 | 2018-06-20 | Basf Se | Farbstabile härterzusammensetzungen enthaltend polyisocyanate (cyclo)aliphatischer diisocyanate |
| WO2019068529A1 (en) | 2017-10-06 | 2019-04-11 | Basf Se | DISPERSIBLE POLYISOCYANATES IN WATER |
| DK3820927T3 (da) | 2018-07-13 | 2024-10-07 | Miwon Austria Forschung Und Entw Gmbh | Vanddispergible polyurethan (meth)akrylater til aktiniske strålingshærdende belægninger |
| CN114502668B (zh) | 2019-10-08 | 2023-09-19 | 巴斯夫欧洲公司 | 可热固化的双组分涂料复配物 |
| US20220403207A1 (en) | 2019-10-24 | 2022-12-22 | Basf Se | Removal of monomeric aliphatic diisocyanate in an aliphatic polyisocyanate using scavengers |
| EP4097157A1 (en) | 2020-01-30 | 2022-12-07 | Basf Se | Color-stable curing agent compositions comprising water-dispersible polyisocyanates |
| EP4251657B1 (en) | 2020-11-26 | 2025-01-08 | Basf Se | Waterbased binder for two-component coating composition |
| JP2023553750A (ja) | 2020-12-18 | 2023-12-25 | ベーアーエスエフ・エスエー | （シクロ）脂肪族ジイソシアネートのポリイソシアネートを含む色安定性硬化剤組成物 |
| WO2023280648A1 (en) | 2021-07-08 | 2023-01-12 | Basf Se | Polyisocyanate-containing formulations |
| CN118401583A (zh) | 2021-12-15 | 2024-07-26 | 巴斯夫欧洲公司 | 具有改进性能的可水乳化的异氰酸酯 |
| WO2023117883A1 (en) | 2021-12-21 | 2023-06-29 | Basf Se | Chemical product passport |
| CN117326982B (zh) * | 2022-09-30 | 2024-08-23 | 四川元理材料科技有限公司 | 采用尿素法合成异佛尔酮二氨基甲酸正丁酯的工业化工艺 |
| CN117402084B (zh) * | 2022-09-30 | 2025-08-29 | 四川元理材料科技有限公司 | 可工业化的ipdi合成工艺 |
| WO2025093348A1 (en) | 2023-10-30 | 2025-05-08 | Basf Se | Water-emulsifiable isocyanates with improved properties |
| WO2025093409A1 (en) | 2023-10-30 | 2025-05-08 | Basf Se | Two-component coating composition |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5748546B2 (OSRAM) * | 1974-03-04 | 1982-10-16 | ||
| DE2917490A1 (de) * | 1979-04-30 | 1980-11-13 | Basf Ag | Verfahren zur herstellung von aliphatischen und cycloaliphatischen di- und polyurethanen |
| DE2942503A1 (de) * | 1979-10-20 | 1981-05-07 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von aromatischen di- und/oder polyisocyanaten |
| DE2943480A1 (de) * | 1979-10-27 | 1981-05-07 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von n,o-disubstituierten urethanen, sowie ihre verwendung als ausgangsmaterial zur herstellung von isocyanaten |
| DE3108990A1 (de) * | 1981-03-10 | 1982-09-23 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von polyisocyanaten |
-
1983
- 1983-04-23 DE DE19833314790 patent/DE3314790A1/de not_active Withdrawn
-
1984
- 1984-04-13 US US06/599,821 patent/US4596679A/en not_active Expired - Lifetime
- 1984-04-17 DE DE8484104353T patent/DE3462887D1/de not_active Expired
- 1984-04-17 EP EP84104353A patent/EP0126300B1/de not_active Expired
- 1984-04-18 CA CA000452345A patent/CA1225997A/en not_active Expired
- 1984-04-20 JP JP59078815A patent/JPS59205353A/ja active Granted
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5087739A (en) * | 1988-08-18 | 1992-02-11 | Huels Aktiengesellschaft | Circulation process for the production of aliphatic and cycloaliphatic diisocyanates |
| EP0566925A3 (en) * | 1992-04-21 | 1993-12-08 | Basf Ag | Multi-step method for the continuous preparation of organic polyisocyanates |
| EP0568782A3 (de) * | 1992-05-05 | 1993-12-08 | Hüls Aktiengesellschaft | Kontinuierliches mehrstufiges Verfahren zur Herstellung von (cyclo)-aliphatischen Diisocyanaten |
| US5360931A (en) * | 1992-05-05 | 1994-11-01 | Huels Aktiengesellschaft | Continuous multi-stage process for the preparation of (cyclo) aliphatic diisocyanates |
| DE19754748B4 (de) * | 1997-12-10 | 2004-04-29 | Gras, Rainer, Dipl.-Chem. Dr. | Verfahren zur Herstellung eines blockierten Lackpolyisocyanats und dessen Verwendung für PUR-Lacke |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0126300B1 (de) | 1987-04-01 |
| US4596679A (en) | 1986-06-24 |
| CA1225997A (en) | 1987-08-25 |
| JPS59205353A (ja) | 1984-11-20 |
| EP0126300A1 (de) | 1984-11-28 |
| JPH0573737B2 (OSRAM) | 1993-10-15 |
| DE3462887D1 (en) | 1987-05-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3314790A1 (de) | Mehrstufenverfahren zur herstellung von 3-isocyanatomethyl-3,5,5-trimethyl-cyclohexylisocyanat | |
| EP0126299B1 (de) | Mehrstufenverfahren zur Herstellung von Hexamethylen-diisocyanat-1,6 und/oder isomeren aliphatischen Diisocyanaten mit 6 Kohlenstoffatomen im Alkylenrest | |
| EP0566925B1 (de) | Mehrstufiges Verfahren zur kontinuierlichen Herstellung von organischen Polyisocyanaten | |
| EP2091911B1 (de) | Verfahren zur kontinuierlichen herstellung von (cyclo)aliphatischen diisocyanaten | |
| EP0582930B1 (de) | Verfahren zur Herstellung von Diarylcarbonaten | |
| EP1420012B1 (de) | Verfahren zur Herstellung von aliphatischen Isocyanaten aus aromatischen Isocyanaten | |
| DE4231417A1 (de) | Kontinuierliches mehrstufiges Verfahren zur Herstellung von (cyclo)aliphatischen Diisocyanaten | |
| DE3828033A1 (de) | Kreislaufverfahren zur herstellung von (cyclo)aliphatischen diisocyanaten | |
| EP1593669B1 (de) | Mehrstufiges Verfahren zur kontinuierlichen Herstellung von cycloaliphatischen Diisocyanaten | |
| EP1512682B1 (de) | Mehrstufiges Verfahren zur kontinuierlichen Herstellung von cycloaliphatischen Diisocyanaten | |
| EP0572870B1 (de) | Verfahren zur Herstellung von organischen Carbonaten mit mindestens einer aromatischen Estergruppe | |
| EP1512680B1 (de) | Mehrstufiges Verfahren zur kontinuierlichen Herstellung von cycloaliphatischen Diisocyanaten | |
| EP1512681B1 (de) | Mehrstufiges Verfahren zur kontinuierlichen Herstellung von cycloaliphatischen Diisocyanaten | |
| EP1634868A2 (de) | Mehrstufiges Verfahren zur kontinuierlichen Herstellung von cycloaliphatischen Diisocyanaten | |
| EP1602643B1 (de) | Mehrstufiges Verfahren zur kontinuierlichen Herstellung von cycloaliphatischen Diisocyanaten | |
| EP0261604B1 (de) | Neue 2-(Alkoximethyl)-pentan-1,5-diisocyanate, - diurethane und dicarbamidsäurechloride, Verfahren zu ihrer Herstellung und deren Verwendung | |
| DE19627552A1 (de) | Verfahren zur Herstellung von organischen Polyisocyanaten | |
| EP0449110B1 (de) | Neue 2,2-Dialkylpentan-1,5-diisocyanate, -diurethane und -dicarbamidsäure-chloride, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| EP0068283A1 (de) | Verfahren zur Herstellung von alkylsubstituierten Anilinen | |
| DE4413580A1 (de) | Verfahren zur Herstellung von 1,4-Diisocyanatobutan (BDI) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |