DE1110406B - Verfahren zur Herstellung von Schaumstoffen auf Isocyanatbasis - Google Patents
Verfahren zur Herstellung von Schaumstoffen auf IsocyanatbasisInfo
- Publication number
- DE1110406B DE1110406B DEF27499A DEF0027499A DE1110406B DE 1110406 B DE1110406 B DE 1110406B DE F27499 A DEF27499 A DE F27499A DE F0027499 A DEF0027499 A DE F0027499A DE 1110406 B DE1110406 B DE 1110406B
- Authority
- DE
- Germany
- Prior art keywords
- tin
- weight
- parts
- compounds
- alcoholates
- 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.)
- Pending
Links
- 239000006260 foam Substances 0.000 title claims description 28
- 239000012948 isocyanate Substances 0.000 title claims description 10
- 150000002513 isocyanates Chemical class 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 230000008569 process Effects 0.000 title claims description 6
- 229910052718 tin Inorganic materials 0.000 claims description 25
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- XITYWQKWNJFZEG-UHFFFAOYSA-J tetraphenoxystannane Chemical class [Sn+4].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 XITYWQKWNJFZEG-UHFFFAOYSA-J 0.000 claims description 10
- 238000005187 foaming Methods 0.000 claims description 9
- 229920001228 polyisocyanate Polymers 0.000 claims description 9
- 239000005056 polyisocyanate Substances 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 229920001296 polysiloxane Polymers 0.000 claims description 7
- 150000001298 alcohols Chemical class 0.000 claims description 6
- 150000002989 phenols Chemical class 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 5
- FJEKUEUBQQWPBY-UHFFFAOYSA-N 1$l^{2}-stanninane Chemical group C1CC[Sn]CC1 FJEKUEUBQQWPBY-UHFFFAOYSA-N 0.000 claims description 2
- 238000003889 chemical engineering Methods 0.000 claims 1
- 229920001521 polyalkylene glycol ether Polymers 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 10
- -1 oxide Chemical compound 0.000 description 10
- 150000003606 tin compounds Chemical class 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 8
- 229920001451 polypropylene glycol Polymers 0.000 description 8
- 238000005809 transesterification reaction Methods 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- 238000007792 addition Methods 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 150000001414 amino alcohols Chemical class 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- 229920001515 polyalkylene glycol Polymers 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000004707 phenolate Chemical class 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- 230000000630 rising effect Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 2
- ZXDVQYBUEVYUCG-UHFFFAOYSA-N dibutyltin(2+);methanolate Chemical compound CCCC[Sn](OC)(OC)CCCC ZXDVQYBUEVYUCG-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002736 metal compounds Chemical group 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920006324 polyoxymethylene Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
- HKQJSGYKMWHHHT-UHFFFAOYSA-N 1,4-diisocyanatobutane prop-1-ene Chemical compound C(CCCN=C=O)N=C=O.C=CC HKQJSGYKMWHHHT-UHFFFAOYSA-N 0.000 description 1
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
- AEEZXQFUVDKVFT-UHFFFAOYSA-N 2-(benzylamino)phenol Chemical class OC1=CC=CC=C1NCC1=CC=CC=C1 AEEZXQFUVDKVFT-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- HNNLFNCNYGQNQW-UHFFFAOYSA-N 3-methyloxiran-2-amine Chemical compound CC1OC1N HNNLFNCNYGQNQW-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-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
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229910009053 Sn—O—Sn Inorganic materials 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical class NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005521 carbonamide group Chemical group 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- MKANCOHERYHKAT-UHFFFAOYSA-L dibenzyltin(2+);dichloride Chemical compound C=1C=CC=CC=1C[Sn](Cl)(Cl)CC1=CC=CC=C1 MKANCOHERYHKAT-UHFFFAOYSA-L 0.000 description 1
- UROKUKHYYXBCQE-UHFFFAOYSA-L dibutyl(diphenoxy)stannane Chemical compound C=1C=CC=CC=1O[Sn](CCCC)(CCCC)OC1=CC=CC=C1 UROKUKHYYXBCQE-UHFFFAOYSA-L 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- MACVNMKPAKPZQG-UHFFFAOYSA-N dioctyltin(2+);methanolate Chemical compound CCCCCCCC[Sn](OC)(OC)CCCCCCCC MACVNMKPAKPZQG-UHFFFAOYSA-N 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- JVSOUDUOUOBHKA-UHFFFAOYSA-N ethyl(methoxy)tin Chemical compound C(C)[Sn]OC JVSOUDUOUOBHKA-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000004872 foam stabilizing agent Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical class CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- UISUQHKSYTZXSF-UHFFFAOYSA-N methanolate;tin(2+) Chemical compound [Sn+2].[O-]C.[O-]C UISUQHKSYTZXSF-UHFFFAOYSA-N 0.000 description 1
- QQKLEWWGQDVDND-UHFFFAOYSA-N methoxytin Chemical compound CO[Sn] QQKLEWWGQDVDND-UHFFFAOYSA-N 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QAZHYRJYZIMJJI-UHFFFAOYSA-N n-ethylpiperazin-1-amine Chemical class CCNN1CCNCC1 QAZHYRJYZIMJJI-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003527 tetrahydropyrans Chemical class 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical group C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- 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
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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
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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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- 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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- 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
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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
- C08G2110/0041—Foam properties having specified density
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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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
Priority Applications (15)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE587687D BE587687A (en, 2012) | 1959-01-17 | ||
NL247436D NL247436A (en, 2012) | 1959-01-17 | ||
BE586595D BE586595A (en, 2012) | 1959-01-17 | ||
DEF27498A DE1109878B (de) | 1959-01-17 | 1959-01-17 | Verfahren zur Herstellung von Schaumstoffen auf Isocyanatbasis |
DEF27499A DE1110406B (de) | 1959-01-17 | 1959-01-17 | Verfahren zur Herstellung von Schaumstoffen auf Isocyanatbasis |
DEF27728A DE1111377B (de) | 1959-01-17 | 1959-02-18 | Verfahren zur Herstellung von Schaumstoffen auf Isocyanatbasis |
DEF27732A DE1112285B (de) | 1959-01-17 | 1959-02-18 | Verfahren zur Herstellung von Urethangruppen aufweisenden Schaumstoffen |
CH6160A CH419597A (de) | 1959-01-17 | 1960-01-06 | Verfahren zur Herstellung von Schaumstoffen auf Isocyanatbasis |
US1878A US3047540A (en) | 1959-01-17 | 1960-01-12 | Polyurethane plastics |
US1870A US3164557A (en) | 1959-01-17 | 1960-01-12 | Polyurethane production catalyzed by an organo-tin compound, which compound containstertiary nitrogen |
GB1603/60A GB936395A (en) | 1959-01-17 | 1960-01-15 | A process for the production of foamed polyurethanes |
FR815711A FR1253978A (fr) | 1959-01-17 | 1960-01-15 | Procédé de préparation de matières en mousse à base d'isocyanates |
SE038160A SE218461C1 (en, 2012) | 1959-01-17 | 1960-01-15 | |
FR827059A FR1259632A (fr) | 1959-01-17 | 1960-05-13 | Procédé de préparation de matières alvéolaires à base d'isocyanates |
GB18550/60A GB908337A (en) | 1959-01-17 | 1960-05-25 | A process for the production of foam materials |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF27499A DE1110406B (de) | 1959-01-17 | 1959-01-17 | Verfahren zur Herstellung von Schaumstoffen auf Isocyanatbasis |
DEF27498A DE1109878B (de) | 1959-01-17 | 1959-01-17 | Verfahren zur Herstellung von Schaumstoffen auf Isocyanatbasis |
DEF27728A DE1111377B (de) | 1959-01-17 | 1959-02-18 | Verfahren zur Herstellung von Schaumstoffen auf Isocyanatbasis |
CH545160A CH416077A (de) | 1960-05-12 | 1960-05-12 | Verfahren zur Herstellung von Schaumstoffen |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1110406B true DE1110406B (de) | 1961-07-06 |
Family
ID=27428892
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEF27499A Pending DE1110406B (de) | 1959-01-17 | 1959-01-17 | Verfahren zur Herstellung von Schaumstoffen auf Isocyanatbasis |
DEF27498A Pending DE1109878B (de) | 1959-01-17 | 1959-01-17 | Verfahren zur Herstellung von Schaumstoffen auf Isocyanatbasis |
DEF27728A Pending DE1111377B (de) | 1959-01-17 | 1959-02-18 | Verfahren zur Herstellung von Schaumstoffen auf Isocyanatbasis |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEF27498A Pending DE1109878B (de) | 1959-01-17 | 1959-01-17 | Verfahren zur Herstellung von Schaumstoffen auf Isocyanatbasis |
DEF27728A Pending DE1111377B (de) | 1959-01-17 | 1959-02-18 | Verfahren zur Herstellung von Schaumstoffen auf Isocyanatbasis |
Country Status (6)
Country | Link |
---|---|
US (2) | US3047540A (en, 2012) |
BE (2) | BE587687A (en, 2012) |
CH (1) | CH419597A (en, 2012) |
DE (3) | DE1110406B (en, 2012) |
GB (2) | GB936395A (en, 2012) |
NL (1) | NL247436A (en, 2012) |
Families Citing this family (56)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3355435A (en) * | 1960-12-29 | 1967-11-28 | Goodyear Tire & Rubber | Polyurethane casting compositions crosslinked by bis (aminoarylene) sulfones |
BE617305A (en, 2012) * | 1961-05-06 | |||
BE620026A (en, 2012) * | 1961-07-12 | |||
DE1153900B (de) * | 1961-10-31 | 1963-09-05 | Bayer Ag | Verfahren zur Herstellung von kautschukartigen thermoplastischen Polyurethanen |
US3251916A (en) * | 1961-12-27 | 1966-05-17 | Best available copy | |
US3248349A (en) * | 1962-05-03 | 1966-04-26 | Mobay Chemical Corp | Cellular polyurethane plastics prepared from a tall oil ester |
NL293505A (en, 2012) * | 1962-05-31 | |||
GB1044629A (en) * | 1962-06-28 | 1966-10-05 | Ici Ltd | Improvements in or relating to the use of polysiloxanes in the manufacture of cellular polyurethanes |
NL121970C (en, 2012) * | 1964-06-09 | |||
US3388101A (en) * | 1964-10-23 | 1968-06-11 | Pittsburgh Plate Glass Co | Silicon-containing polyurethanes |
US3931065A (en) * | 1966-02-18 | 1976-01-06 | Nisshin Boseki Kabushiki Kaisha | Polyurethane-modified polyisocyanurate foam and a method for the preparation thereof |
US4405725A (en) * | 1967-03-24 | 1983-09-20 | Mobay Chemical Corporation | Foamed polyisocyanurates |
US3625872A (en) * | 1967-06-15 | 1971-12-07 | Nisshin Spinning | Flame-resistive polyurethane foam composition |
US3981828A (en) * | 1972-06-19 | 1976-09-21 | Basf Wyandotte Corporation | Flexible cellular polyurethane foam compositions having increased flame retardance |
LU68552A1 (en, 2012) * | 1973-10-03 | 1975-06-16 | ||
JPS5432479B2 (en, 2012) * | 1973-11-28 | 1979-10-15 | ||
US4029610A (en) * | 1974-05-23 | 1977-06-14 | Basf Wyandotte Corporation | Carbodiimide-isocyanurate foams containing urethane linkages |
US3989651A (en) * | 1974-07-09 | 1976-11-02 | The Upjohn Company | Catalyst for sprayable polyisocyanurate foam composition |
US3954684A (en) * | 1974-07-09 | 1976-05-04 | The Upjohn Company | Foam process using tertiary amine/quaternary ammonium salt catalyst |
US4107069A (en) * | 1975-07-02 | 1978-08-15 | M&T Chemicals Inc. | Storage-stable precursors for rigid polyurethane foams |
CH601370A5 (en, 2012) * | 1975-09-16 | 1978-07-14 | M & T Chemicals Inc | |
US4085072A (en) * | 1975-12-18 | 1978-04-18 | M&T Chemicals Inc. | Process for preparing oxidatively stable polyurethane foam |
US4039487A (en) * | 1976-01-19 | 1977-08-02 | The Upjohn Company | Cellular isocyanurate polymer |
GB1543458A (en) * | 1976-06-01 | 1979-04-04 | Bayer Ag | Process for the production of polyurethanes |
US4101470A (en) * | 1976-11-11 | 1978-07-18 | Texaco Development Corp. | Urethane catalysts |
US4115634A (en) * | 1976-12-01 | 1978-09-19 | Air Products & Chemicals, Inc. | Amine salts of amino acids as delayed action catalysts |
US4129693A (en) * | 1976-12-20 | 1978-12-12 | Basf Wyandotte Corporation | Urethane-modified isocyanurate foams having enhanced physical properties |
DE2854384A1 (de) | 1978-12-16 | 1980-07-03 | Bayer Ag | Verfahren zur herstellung von polyurethan-kunststoffen |
US4212952A (en) * | 1978-12-21 | 1980-07-15 | Union Carbide Corporation | N,N,N',N'-Tetramethyl-αω-polymethlenediamines as catalysts for the preparation of urethane foams |
US4251636A (en) * | 1979-04-30 | 1981-02-17 | Texaco Development Corporation | Stannous halide complexes and their use in preparing polyurethane foams |
DE3039883A1 (de) | 1980-10-22 | 1982-05-19 | Bayer Ag, 5090 Leverkusen | Einbaufaehige reaktiv-treibmittel enthaltende polyol-gemische und ihre verwendung zur herstellung geschaeumter polyurethane |
US4360670A (en) * | 1981-02-02 | 1982-11-23 | Air Products And Chemicals, Inc. | Amino and amido dialkyl tin carboxylates |
US4464490A (en) * | 1981-02-02 | 1984-08-07 | Air Products And Chemicals, Inc. | Amino and amido dialkyl tin carboxylates and their use in preparing polyurethane products |
US4430456A (en) | 1981-02-02 | 1984-02-07 | Air Products And Chemicals, Inc. | Polyurethane-forming process using amino and amido dialkyl tin carboxylates |
US4632785A (en) * | 1983-08-11 | 1986-12-30 | The Dow Chemical Company | Thermally activable trimerization catalyst |
US4540781A (en) * | 1983-08-11 | 1985-09-10 | The Upjohn Company | Product and process trimerization of organic isocyanates |
US4478959A (en) * | 1983-09-29 | 1984-10-23 | Air Products And Chemicals, Inc. | Amino and amido divalent metal carboxylates useful as catalysts for polyurethane formulations |
US4644027A (en) * | 1985-07-15 | 1987-02-17 | Stepan Company | Self-compatibilizing phthalate-based polyester polyols |
US4675422A (en) * | 1985-10-23 | 1987-06-23 | Stepan Company | Organometallic compounds |
GB8712988D0 (en) * | 1987-06-03 | 1987-07-08 | Ici Plc | Polyurethane foams |
US4900776A (en) * | 1988-12-01 | 1990-02-13 | Georgia-Pacific Resins, Inc. | Potassium catalyst system for preparing polyurethane based plywood-patch compositions |
US5011902A (en) * | 1989-11-01 | 1991-04-30 | Georgia-Pacific Resins, Inc. | Co-catalyst system for preparing polyurethane based plywood-patch compositions |
DE59308932D1 (de) * | 1992-01-31 | 1998-10-01 | Henkel Kgaa | Verfahren zur herstellung von kunststoffen mit amid-gruppen |
US5591781A (en) * | 1993-10-27 | 1997-01-07 | Tosoh Corporation | Process for producing polyurethane foam with high curing rate |
US20060175575A1 (en) * | 2001-06-15 | 2006-08-10 | Kaplan Warren A | Method for preparing phthalate polyester polyol-based dimensionally stable spray polyurethane foam |
US20050194713A1 (en) * | 2003-12-29 | 2005-09-08 | John Erickson | Method of making a molded article |
US20060035994A1 (en) * | 2004-05-17 | 2006-02-16 | Kaplan Warren A | Method for preparing phthalate polyester polyol-based dimensionally stable spray polyurethane foam |
DE102008021980A1 (de) | 2008-05-02 | 2009-11-05 | Bayer Materialscience Ag | Neue Katalysatoren und deren Einsatz bei der Herstellung von Polyurethanen |
US9834638B2 (en) * | 2008-06-04 | 2017-12-05 | Covestro Llc | Process for preparing rigid polyisocyanurate foams using natural-oil polyols |
DE102009033710A1 (de) * | 2009-07-18 | 2011-01-20 | Evonik Goldschmidt Gmbh | Verwendung von Metallsalzen einer Carbonsäure bei der Herstellung von Polyurethansystemen |
DE102009051445A1 (de) | 2009-10-30 | 2011-05-05 | Bayer Materialscience Ag | Verwendung spezieller Katalysatoren für die Herstellung von Polyurethanbeschichtungen |
US20150252138A1 (en) | 2012-09-25 | 2015-09-10 | Bayer Materialscience, Ag | Polyisocyanate-polyaddition products |
CN104640896B (zh) | 2012-09-25 | 2019-03-15 | 科思创德国股份有限公司 | 多异氰酸酯加聚产物 |
WO2015164408A1 (en) | 2014-04-21 | 2015-10-29 | Gaco Western, LLC | Foam compositions |
CN109422896B (zh) * | 2017-08-24 | 2021-04-13 | 山东理工大学 | 包含伯胺盐和丙醇胺盐的发泡剂及用于聚氨酯冰箱冰柜泡沫体材料的用途 |
CN114341225A (zh) * | 2019-08-20 | 2022-04-12 | 巴斯夫欧洲公司 | 具有改进加工性能的含可选择的发泡剂的阻燃聚氨酯泡沫 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB760782A (en) * | 1953-08-19 | 1956-11-07 | Bayer Ag | Process for the production of foamed products based on polyisocyanates |
US2933462A (en) * | 1957-07-03 | 1960-04-19 | Aerojet General Co | Method for the preparation of foamed polyurethanes |
NL106889C (en, 2012) * | 1957-09-25 | 1900-01-01 |
-
0
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- BE BE587687D patent/BE587687A/xx unknown
- NL NL247436D patent/NL247436A/xx unknown
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1959
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- 1960-01-15 GB GB1603/60A patent/GB936395A/en not_active Expired
- 1960-05-25 GB GB18550/60A patent/GB908337A/en not_active Expired
Non-Patent Citations (1)
Title |
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None * |
Also Published As
Publication number | Publication date |
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GB936395A (en) | 1963-09-11 |
GB908337A (en) | 1962-10-17 |
BE586595A (en, 2012) | |
DE1109878B (de) | 1961-06-29 |
US3047540A (en) | 1962-07-31 |
US3164557A (en) | 1965-01-05 |
NL247436A (en, 2012) | |
DE1111377B (de) | 1961-07-20 |
CH419597A (de) | 1966-08-31 |
BE587687A (en, 2012) |
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