CH653693A5 - Amorphe chloralkylen-alkohole, verfahren und katalysatorsystem zu ihrer herstellung und ihre verwendung. - Google Patents
Amorphe chloralkylen-alkohole, verfahren und katalysatorsystem zu ihrer herstellung und ihre verwendung. Download PDFInfo
- Publication number
- CH653693A5 CH653693A5 CH4558/79A CH455879A CH653693A5 CH 653693 A5 CH653693 A5 CH 653693A5 CH 4558/79 A CH4558/79 A CH 4558/79A CH 455879 A CH455879 A CH 455879A CH 653693 A5 CH653693 A5 CH 653693A5
- Authority
- CH
- Switzerland
- Prior art keywords
- atoms
- formula
- catalyst system
- hydroxyl
- alcohols
- Prior art date
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- 239000003054 catalyst Substances 0.000 title claims description 39
- 238000000034 method Methods 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 150000001298 alcohols Chemical class 0.000 title claims 8
- 229920005862 polyol Polymers 0.000 claims description 47
- 150000003077 polyols Chemical class 0.000 claims description 46
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 43
- 239000000463 material Substances 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
- -1 C 1 -C 7 -alkyl Chemical group 0.000 claims description 19
- 150000003606 tin compounds Chemical class 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000004814 polyurethane Substances 0.000 claims description 8
- 229920002635 polyurethane Polymers 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- 229910052796 boron Inorganic materials 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 229910052787 antimony Chemical group 0.000 claims description 4
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 4
- 229910052785 arsenic Inorganic materials 0.000 claims description 4
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000011574 phosphorus Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- MYIAPBDBTMDUDP-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)methylsulfonyl-trifluoromethane Chemical compound FC(F)(F)S(=O)(=O)C(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F MYIAPBDBTMDUDP-UHFFFAOYSA-N 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229920001228 polyisocyanate Polymers 0.000 claims description 2
- 239000005056 polyisocyanate Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 2
- 230000003197 catalytic effect Effects 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 229920000642 polymer Polymers 0.000 claims 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims 1
- 229920005830 Polyurethane Foam Polymers 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 230000002411 adverse Effects 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 238000010538 cationic polymerization reaction Methods 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 150000002222 fluorine compounds Chemical class 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- 239000011496 polyurethane foam Substances 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 24
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 239000011368 organic material Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- MBAKFIZHTUAVJN-UHFFFAOYSA-I hexafluoroantimony(1-);hydron Chemical compound F.F[Sb](F)(F)(F)F MBAKFIZHTUAVJN-UHFFFAOYSA-I 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- DTYWIPLKZHQUMW-UHFFFAOYSA-N dibutyl(diphenyl)stannane Chemical compound C=1C=CC=CC=1[Sn](CCCC)(CCCC)C1=CC=CC=C1 DTYWIPLKZHQUMW-UHFFFAOYSA-N 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- MXLMTQWGSQIYOW-UHFFFAOYSA-N 3-methyl-2-butanol Chemical compound CC(C)C(C)O MXLMTQWGSQIYOW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229910004039 HBF4 Inorganic materials 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000008570 general process Effects 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 150000004072 triols Chemical class 0.000 description 2
- 150000003673 urethanes Chemical class 0.000 description 2
- XONFSEOHZGSMJG-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4-nonafluoro-4-(1,1,2,2,3,3,4,4,4-nonafluorobutylsulfonylmethylsulfonyl)butane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)CS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F XONFSEOHZGSMJG-UHFFFAOYSA-N 0.000 description 1
- NHKMCDLYQRNJNI-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoro-4-(2,2,3,3,4,4,4-heptafluorobutylsulfonylmethylsulfonyl)butane Chemical compound FC(F)(F)C(F)(F)C(F)(F)CS(=O)(=O)CS(=O)(=O)CC(F)(F)C(F)(F)C(F)(F)F NHKMCDLYQRNJNI-UHFFFAOYSA-N 0.000 description 1
- BFFOGQAVMGLUJF-UHFFFAOYSA-N 1,1,3,3-tetrakis(trifluoromethylsulfonyl)propane Chemical compound FC(F)(F)S(=O)(=O)C(S(=O)(=O)C(F)(F)F)CC(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F BFFOGQAVMGLUJF-UHFFFAOYSA-N 0.000 description 1
- WRSVERXVRBGMSE-UHFFFAOYSA-N 1,1-bis(trifluoromethylsulfonyl)octadecane Chemical compound CCCCCCCCCCCCCCCCCC(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F WRSVERXVRBGMSE-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- DFLWCPKNTKCYHU-UHFFFAOYSA-N 1-[bis(trifluoromethylsulfonyl)methyl]-4-bromobenzene Chemical compound FC(F)(F)S(=O)(=O)C(S(=O)(=O)C(F)(F)F)C1=CC=C(Br)C=C1 DFLWCPKNTKCYHU-UHFFFAOYSA-N 0.000 description 1
- BZQAOASUJNTSGD-UHFFFAOYSA-N 1-[bis(trifluoromethylsulfonyl)methyl]naphthalene Chemical compound C1=CC=C2C(C(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F)=CC=CC2=C1 BZQAOASUJNTSGD-UHFFFAOYSA-N 0.000 description 1
- VUSYFNXNYLAECV-UHFFFAOYSA-N 2,3-bis(chloromethyl)oxirane Chemical compound ClCC1OC1CCl VUSYFNXNYLAECV-UHFFFAOYSA-N 0.000 description 1
- UENUNSBHNNOPBF-UHFFFAOYSA-N 2,3-bis(dichloromethyl)oxirane Chemical compound ClC(Cl)C1OC1C(Cl)Cl UENUNSBHNNOPBF-UHFFFAOYSA-N 0.000 description 1
- ZXCYIJGIGSDJQQ-UHFFFAOYSA-N 2,3-dichloropropan-1-ol Chemical compound OCC(Cl)CCl ZXCYIJGIGSDJQQ-UHFFFAOYSA-N 0.000 description 1
- YHWDZWQQFQKTRM-UHFFFAOYSA-N 2-(1,1,2,2,2-pentachloroethyl)oxirane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)C1CO1 YHWDZWQQFQKTRM-UHFFFAOYSA-N 0.000 description 1
- CJTAOJBBFSUSNB-UHFFFAOYSA-N 2-(1,1,2,2-tetrachloroethyl)oxirane Chemical compound ClC(Cl)C(Cl)(Cl)C1CO1 CJTAOJBBFSUSNB-UHFFFAOYSA-N 0.000 description 1
- CWZYYACZLHIHAN-UHFFFAOYSA-N 2-(1,2,2,2-tetrachloroethyl)oxirane Chemical compound ClC(Cl)(Cl)C(Cl)C1CO1 CWZYYACZLHIHAN-UHFFFAOYSA-N 0.000 description 1
- VRZNYSQBNMDONE-UHFFFAOYSA-N 2-(2,2-dichloroethyl)oxirane Chemical compound ClC(Cl)CC1CO1 VRZNYSQBNMDONE-UHFFFAOYSA-N 0.000 description 1
- VVHFXJOCUKBZFS-UHFFFAOYSA-N 2-(chloromethyl)-2-methyloxirane Chemical compound ClCC1(C)CO1 VVHFXJOCUKBZFS-UHFFFAOYSA-N 0.000 description 1
- CSGMQHXVHFJWST-UHFFFAOYSA-N 2-(dichloromethyl)-2-methyloxirane Chemical compound ClC(Cl)C1(C)CO1 CSGMQHXVHFJWST-UHFFFAOYSA-N 0.000 description 1
- FQYGHYRJXOSDIN-UHFFFAOYSA-N 2-(dichloromethyl)-3-(trichloromethyl)oxirane Chemical compound ClC(Cl)C1OC1C(Cl)(Cl)Cl FQYGHYRJXOSDIN-UHFFFAOYSA-N 0.000 description 1
- DIYZRTRTCGAIKG-UHFFFAOYSA-N 2-(dichloromethyl)oxirane Chemical compound ClC(Cl)C1CO1 DIYZRTRTCGAIKG-UHFFFAOYSA-N 0.000 description 1
- SHEHNAAPSUJGHG-UHFFFAOYSA-N 2-[bis(trifluoromethylsulfonyl)methyl]thiophene Chemical compound FC(F)(F)S(=O)(=O)C(S(=O)(=O)C(F)(F)F)C1=CC=CS1 SHEHNAAPSUJGHG-UHFFFAOYSA-N 0.000 description 1
- DRBNEGNJVLGPIU-UHFFFAOYSA-N 2-[bromo(dichloro)methyl]oxirane Chemical compound ClC(Cl)(Br)C1CO1 DRBNEGNJVLGPIU-UHFFFAOYSA-N 0.000 description 1
- MDUHTZMPRUWKFF-UHFFFAOYSA-N 2-[chloro(difluoro)methyl]oxirane Chemical compound FC(F)(Cl)C1CO1 MDUHTZMPRUWKFF-UHFFFAOYSA-N 0.000 description 1
- VEVSUNRHFFVJGJ-UHFFFAOYSA-N 2-[dichloro(fluoro)methyl]oxirane Chemical compound FC(Cl)(Cl)C1CO1 VEVSUNRHFFVJGJ-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- LAMUXTNQCICZQX-UHFFFAOYSA-N 3-chloropropan-1-ol Chemical compound OCCCCl LAMUXTNQCICZQX-UHFFFAOYSA-N 0.000 description 1
- NBUAJOLSZMKRIT-UHFFFAOYSA-N 5-methyloctan-3-ol Chemical compound CCCC(C)CC(O)CC NBUAJOLSZMKRIT-UHFFFAOYSA-N 0.000 description 1
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
- 229910017049 AsF5 Inorganic materials 0.000 description 1
- 241000209761 Avena Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- MZSSNBZQBIYWHE-UHFFFAOYSA-N FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)C(F)(F)S(=O)(=O)C(F)(F)F Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)C(F)(F)S(=O)(=O)C(F)(F)F MZSSNBZQBIYWHE-UHFFFAOYSA-N 0.000 description 1
- 229910004713 HPF6 Inorganic materials 0.000 description 1
- JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 description 1
- 229910021174 PF5 Inorganic materials 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 1
- APQHKWPGGHMYKJ-UHFFFAOYSA-N Tributyltin oxide Chemical compound CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC APQHKWPGGHMYKJ-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
- YBGKQGSCGDNZIB-UHFFFAOYSA-N arsenic pentafluoride Chemical compound F[As](F)(F)(F)F YBGKQGSCGDNZIB-UHFFFAOYSA-N 0.000 description 1
- ZMWKYYJODBYKHO-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)methylbenzene Chemical compound FC(F)(F)S(=O)(=O)C(S(=O)(=O)C(F)(F)F)C1=CC=CC=C1 ZMWKYYJODBYKHO-UHFFFAOYSA-N 0.000 description 1
- PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 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
- UQZGDPBXFWNERN-UHFFFAOYSA-N chloro-[[chloro(difluoro)methyl]sulfonylmethylsulfonyl]-difluoromethane Chemical compound FC(F)(Cl)S(=O)(=O)CS(=O)(=O)C(F)(F)Cl UQZGDPBXFWNERN-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- FFKSUTHTFIDTNU-UHFFFAOYSA-N dibutyl-bis(ethenyl)stannane Chemical compound CCCC[Sn](C=C)(C=C)CCCC FFKSUTHTFIDTNU-UHFFFAOYSA-N 0.000 description 1
- LCGVYMRFNOWPGQ-UHFFFAOYSA-N dibutyl-bis(prop-2-enyl)stannane Chemical compound CCCC[Sn](CC=C)(CC=C)CCCC LCGVYMRFNOWPGQ-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- AAMBSBLPYBJZMV-UHFFFAOYSA-N ethyl 4-bromo-6,6-bis(trifluoromethylsulfonyl)hexanoate Chemical compound CCOC(=O)CCC(Br)CC(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F AAMBSBLPYBJZMV-UHFFFAOYSA-N 0.000 description 1
- WDQNIWFZKXZFAY-UHFFFAOYSA-M fentin acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 WDQNIWFZKXZFAY-UHFFFAOYSA-M 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- OBCUTHMOOONNBS-UHFFFAOYSA-N phosphorus pentafluoride Chemical compound FP(F)(F)(F)F OBCUTHMOOONNBS-UHFFFAOYSA-N 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- DFNPRTKVCGZMMC-UHFFFAOYSA-M tributyl(fluoro)stannane Chemical compound CCCC[Sn](F)(CCCC)CCCC DFNPRTKVCGZMMC-UHFFFAOYSA-M 0.000 description 1
- QBOFWVRRMVGXIG-UHFFFAOYSA-N trifluoro(trifluoromethylsulfonylmethylsulfonyl)methane Chemical compound FC(F)(F)S(=O)(=O)CS(=O)(=O)C(F)(F)F QBOFWVRRMVGXIG-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5003—Polyethers having heteroatoms other than oxygen having halogens
- C08G18/5006—Polyethers having heteroatoms other than oxygen having halogens having chlorine and/or bromine atoms
- C08G18/5009—Polyethers having heteroatoms other than oxygen having halogens having chlorine and/or bromine atoms having chlorine atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
- C08G65/223—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens
-
- 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
- C08G65/2645—Metals or compounds thereof, e.g. salts
-
- 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
- C08G65/2645—Metals or compounds thereof, e.g. salts
- C08G65/266—Metallic elements not covered by group C08G65/2648 - C08G65/2645, or compounds thereof
-
- 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
- C08G65/2684—Halogens or compounds thereof
-
- 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
- C08G65/269—Mixed catalyst systems, i.e. containing more than one reactive component or catalysts formed in-situ
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyurethanes Or Polyureas (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US90674478A | 1978-05-17 | 1978-05-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH653693A5 true CH653693A5 (de) | 1986-01-15 |
Family
ID=25422907
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH4558/79A CH653693A5 (de) | 1978-05-17 | 1979-05-16 | Amorphe chloralkylen-alkohole, verfahren und katalysatorsystem zu ihrer herstellung und ihre verwendung. |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS54150497A (ja) |
| AU (1) | AU534485B2 (ja) |
| BR (1) | BR7903018A (ja) |
| CA (1) | CA1187107A (ja) |
| CH (1) | CH653693A5 (ja) |
| DE (1) | DE2919834A1 (ja) |
| FR (1) | FR2426060A1 (ja) |
| GB (2) | GB2021606B (ja) |
| IT (1) | IT1116819B (ja) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4405497A (en) * | 1979-09-18 | 1983-09-20 | Minnesota Mining And Manufacturing Company | Catalyst system containing a fluorinated acid and a polyvalent tin compound |
| DE3035138A1 (de) * | 1979-09-18 | 1981-04-02 | Minnesota Mining and Manufacturing Co., 55101 Saint Paul, Minn. | Amorphe poly-(halogenalkylenaether) mit hydroxyl-endgruppen und zweikomponentenkatalysatorsystem |
| US4431845A (en) * | 1980-12-04 | 1984-02-14 | Minnesota Mining And Manufacturing Company | Method for the preparation of hydroxyl-terminated poly(haloalkylene ethers) |
| US4393199A (en) | 1981-05-12 | 1983-07-12 | S R I International | Cationic polymerization |
| CA1197832A (en) * | 1982-06-01 | 1985-12-10 | Kang Yang | Catalysts for alkoxylation reactions |
| US4483941A (en) * | 1982-09-02 | 1984-11-20 | Conoco Inc. | Catalysts for alkoxylation reactions |
| US4485211A (en) * | 1982-09-15 | 1984-11-27 | The B. F. Goodrich Company | Poly(glycidyl ether)block copolymers and process for their preparation |
| US4451618A (en) * | 1982-09-29 | 1984-05-29 | The B. F. Goodrich Company | Block copolymers and process for their preparation |
| US4540742A (en) * | 1982-11-12 | 1985-09-10 | The B. F. Goodrich Company | Graft copolymers and process for their preparation |
| US4879419A (en) * | 1985-07-01 | 1989-11-07 | Minnesota Mining And Manufacturing Company | Hydroxyl-terminated polyepichlorohydrin polymers |
| CA1339576C (en) * | 1985-08-30 | 1997-12-09 | Minnesota Mining And Manufacturing Company | Hydroxyl-termitated polyepichlorohydrin and derivatives |
| US5117010A (en) * | 1991-08-15 | 1992-05-26 | Ciba-Geigy Corporation | Process for the preparation of addition products of epoxides and alcohols |
| TW224108B (ja) * | 1992-05-06 | 1994-05-21 | Ciba Geigy | |
| CN103497322B (zh) * | 2013-09-09 | 2015-05-27 | 江苏雅克科技股份有限公司 | 一种反应型含卤阻燃聚醚多元醇的制备方法和用途 |
| JP7387987B2 (ja) * | 2019-01-21 | 2023-11-29 | 東ソー株式会社 | 熱可塑性ポリウレタン樹脂及び熱可塑性ポリウレタン樹脂組成物 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2327053A (en) * | 1939-11-18 | 1943-08-17 | Shell Dev | Production of hydroxy ethers |
| DE1281420B (de) * | 1963-09-23 | 1968-10-31 | Olin Mathieson | Verfahren zur Herstellung von linearen oder verzweigten Polyalkylenglykolaethern |
| US3305565A (en) * | 1964-07-08 | 1967-02-21 | Shell Oil Co | Polyepihalohydrin preparation using fluoboric acid catalyst |
| DE1793581C3 (de) * | 1965-04-23 | 1974-02-28 | L'oreal, Paris | Polychloräther und Verfahren zu ihrer Herstellung. Ausscheidung aus: 1593217 |
| FR94928E (fr) * | 1965-04-23 | 1970-01-23 | Oreal | Nouveaux agents tensio-actifs non ioniques et leur procédé de préparation. |
| GB1047557A (en) * | 1965-05-04 | 1966-11-09 | Shell Int Research | Polymers of epoxy-halo-substituted alkanes |
| CH568343A5 (ja) * | 1972-05-15 | 1975-10-31 | Solvay | |
| US3850856A (en) * | 1973-08-20 | 1974-11-26 | Goodrich Co B F | Hydroxyl-ended epihalohydrin polymers by cationic polymerization |
| DE2639083C2 (de) * | 1976-08-31 | 1983-02-10 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Polyätherpolyolen und ihre Verwendung als Ausgangsmaterialien für Polyurethankunststoffe |
-
1979
- 1979-04-23 CA CA000326143A patent/CA1187107A/en not_active Expired
- 1979-05-16 BR BR7903018A patent/BR7903018A/pt unknown
- 1979-05-16 CH CH4558/79A patent/CH653693A5/de not_active IP Right Cessation
- 1979-05-16 AU AU47100/79A patent/AU534485B2/en not_active Ceased
- 1979-05-16 FR FR7912393A patent/FR2426060A1/fr active Granted
- 1979-05-16 GB GB7917067A patent/GB2021606B/en not_active Expired
- 1979-05-16 IT IT49061/79A patent/IT1116819B/it active
- 1979-05-16 DE DE19792919834 patent/DE2919834A1/de active Granted
- 1979-05-16 JP JP6024779A patent/JPS54150497A/ja active Granted
-
1981
- 1981-11-09 GB GB08133787A patent/GB2104403B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BR7903018A (pt) | 1979-12-04 |
| AU4710079A (en) | 1979-11-22 |
| FR2426060A1 (fr) | 1979-12-14 |
| GB2021606B (en) | 1982-12-01 |
| JPS6332813B2 (ja) | 1988-07-01 |
| JPS54150497A (en) | 1979-11-26 |
| FR2426060B1 (ja) | 1983-05-20 |
| GB2021606A (en) | 1979-12-05 |
| DE2919834C2 (ja) | 1991-02-28 |
| DE2919834A1 (de) | 1979-11-22 |
| CA1187107A (en) | 1985-05-14 |
| GB2104403B (en) | 1983-07-13 |
| IT1116819B (it) | 1986-02-10 |
| GB2104403A (en) | 1983-03-09 |
| AU534485B2 (en) | 1984-02-02 |
| IT7949061A0 (it) | 1979-05-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |