DE2032186A1 - Verfahren zur Herstellung von Urethangruppen enthaltenden Schaumstoffen mit Hilfe von modifizierten Silamorpholinen - Google Patents
Verfahren zur Herstellung von Urethangruppen enthaltenden Schaumstoffen mit Hilfe von modifizierten SilamorpholinenInfo
- Publication number
- DE2032186A1 DE2032186A1 DE19702032186 DE2032186A DE2032186A1 DE 2032186 A1 DE2032186 A1 DE 2032186A1 DE 19702032186 DE19702032186 DE 19702032186 DE 2032186 A DE2032186 A DE 2032186A DE 2032186 A1 DE2032186 A1 DE 2032186A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- silicon compound
- production
- compounds
- containing urethane
- 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 20
- 238000000034 method Methods 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims description 4
- 229920000570 polyether Polymers 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 150000003377 silicon compounds Chemical class 0.000 claims description 11
- 229920000728 polyester Polymers 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 6
- 239000005056 polyisocyanate Substances 0.000 claims description 5
- 229920001228 polyisocyanate Polymers 0.000 claims description 5
- 239000004604 Blowing Agent Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 16
- 239000003054 catalyst Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 7
- 230000035699 permeability Effects 0.000 description 7
- GGPLWEZGITVTJX-UHFFFAOYSA-N 2,2,4-trimethyl-1,4,2-oxazasilinane Chemical compound CN1CCO[Si](C)(C)C1 GGPLWEZGITVTJX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229920005830 Polyurethane Foam Polymers 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000011496 polyurethane foam Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 2
- OYWRDHBGMCXGFY-UHFFFAOYSA-N 1,2,3-triazinane Chemical class C1CNNNC1 OYWRDHBGMCXGFY-UHFFFAOYSA-N 0.000 description 1
- DEBOQSQEMSJOST-UHFFFAOYSA-N 3,3,4-trimethyl-1,4,2-oxazasilinane Chemical compound CC1(N(CCO[SiH2]1)C)C DEBOQSQEMSJOST-UHFFFAOYSA-N 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- CNTRZROSTQPQPP-UHFFFAOYSA-N bromomethyl-ethoxy-dimethylsilane Chemical compound CCO[Si](C)(C)CBr CNTRZROSTQPQPP-UHFFFAOYSA-N 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 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
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 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 1
- 238000010438 heat treatment Methods 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- -1 siloxanes Chemical class 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/20—Heterocyclic amines; Salts thereof
- C08G18/209—Heterocyclic amines; Salts thereof having heteroatoms other than oxygen and nitrogen in the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702032186 DE2032186A1 (de) | 1970-06-30 | 1970-06-30 | Verfahren zur Herstellung von Urethangruppen enthaltenden Schaumstoffen mit Hilfe von modifizierten Silamorpholinen |
| GB3012271A GB1351627A (en) | 1970-06-30 | 1971-06-23 | Process for the production of foam resins which contain urethane groups using silamorpholines |
| US00157684A US3723492A (en) | 1970-06-30 | 1971-06-28 | Process for preparing cellular polyurethanes |
| GB2734173A GB1351628A (en) | 1970-06-30 | 1971-06-28 | Catalysts for the production of foam resins |
| NL7108980A NL7108980A (enExample) | 1970-06-30 | 1971-06-29 | |
| FR7124001A FR2096619A1 (enExample) | 1970-06-30 | 1971-06-30 | |
| BE769344A BE769344A (fr) | 1970-06-30 | 1971-06-30 | Procede de preparation de mousses contenant des groupes urethannes a l'aide de silamorpholines modifiees |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702032186 DE2032186A1 (de) | 1970-06-30 | 1970-06-30 | Verfahren zur Herstellung von Urethangruppen enthaltenden Schaumstoffen mit Hilfe von modifizierten Silamorpholinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2032186A1 true DE2032186A1 (de) | 1972-01-13 |
Family
ID=5775306
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702032186 Pending DE2032186A1 (de) | 1970-06-30 | 1970-06-30 | Verfahren zur Herstellung von Urethangruppen enthaltenden Schaumstoffen mit Hilfe von modifizierten Silamorpholinen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3723492A (enExample) |
| BE (1) | BE769344A (enExample) |
| DE (1) | DE2032186A1 (enExample) |
| FR (1) | FR2096619A1 (enExample) |
| GB (2) | GB1351627A (enExample) |
| NL (1) | NL7108980A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2042534A1 (de) * | 2007-09-28 | 2009-04-01 | Evonik Goldschmidt GmbH | Aminkatalysatoren geeignet zur Herstellung emissionsarmer, rekatalysestabiler Polyurethanweichschaumstoffe |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4794192A (en) * | 1987-07-06 | 1988-12-27 | General Electric Company | Cyclic aminoalkylsilanes and their use as adhesion promoters in room temperature vulcanizable polydiorganosiloxane compositions |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1545800C3 (de) * | 1965-04-03 | 1973-12-13 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von 4 Alkyl 2,2 dimethyl 2 silamorpholinen |
| US3479383A (en) * | 1968-01-02 | 1969-11-18 | Gen Electric | Cyclic silyl amides |
-
1970
- 1970-06-30 DE DE19702032186 patent/DE2032186A1/de active Pending
-
1971
- 1971-06-23 GB GB3012271A patent/GB1351627A/en not_active Expired
- 1971-06-28 GB GB2734173A patent/GB1351628A/en not_active Expired
- 1971-06-28 US US00157684A patent/US3723492A/en not_active Expired - Lifetime
- 1971-06-29 NL NL7108980A patent/NL7108980A/xx unknown
- 1971-06-30 FR FR7124001A patent/FR2096619A1/fr not_active Withdrawn
- 1971-06-30 BE BE769344A patent/BE769344A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2042534A1 (de) * | 2007-09-28 | 2009-04-01 | Evonik Goldschmidt GmbH | Aminkatalysatoren geeignet zur Herstellung emissionsarmer, rekatalysestabiler Polyurethanweichschaumstoffe |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2096619A1 (enExample) | 1972-02-18 |
| US3723492A (en) | 1973-03-27 |
| GB1351628A (en) | 1974-05-01 |
| BE769344A (fr) | 1971-11-03 |
| GB1351627A (en) | 1974-05-01 |
| NL7108980A (enExample) | 1972-01-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2631733C2 (enExample) | ||
| DE2523633C2 (de) | Verfahren zur Herstellung von Polyurethanschaumstoffen und Katalysatoren zur Durchführung des Verfahrens | |
| EP0624611B1 (de) | Verfahren zur Herstellung von Polyurethan-Schaumstoffen | |
| DE2624527A1 (de) | Verfahren zur herstellung von polyurethanen | |
| DE1966261A1 (de) | Verfahren zur Herstellung von hochtemperaturbestaendigen,zelligen Polymeren | |
| DE3621039A1 (de) | Verfahren zur herstellung von hydroxylgruppen aufweisenden oligoestern und deren verwendung | |
| EP0001800B1 (de) | Polyätherpolyole, Verfahren zu ihrer Herstellung und Verfahren zur Herstellung von Polyurethanschaumstoffen | |
| DE3310124C2 (enExample) | ||
| EP0368031B1 (de) | Reaktivsysteme und ein Verfahren zur Herstellung von Polyurethankunststoffen | |
| DE69403824T2 (de) | Polyol-Zusammensetzungen und Polyisocynate sowie ihre Verwendung zur Herstellung von Polyurethanen | |
| EP0152861A2 (de) | Verfahren zur Herstellung von urethanmodifizierten Polyisocyanat-Zubereitungen und ihre Verwendung bei der Herstellung von Polyurethankunststoffen oder von Polyisocyanatkunststoffen | |
| EP0471260A2 (de) | Verfahren zur Herstellung von offenzelligen Polyurethan-Weichschaumstoffen und deren Verwendung als Polstermaterial | |
| DE3910100C1 (enExample) | ||
| DE2648594A1 (de) | Verfahren zur herstellung eines kunststoff-schaums und eine zur katalysierung dieses verfahrens geeignete verbindung | |
| DE1243865B (de) | Polyisocyanatmischungen zur Herstellung von Kunststoffen | |
| EP0761727A1 (de) | Verfahren zur Herstellung von Polyurethan-Hart- oder -Halbhartschaumstoffen und derartige Polyurethan-Schaumstoffe enthaltende Verbundelemente | |
| DE2029293C3 (de) | Verfahren zur Herstellung von Polyurethanschaumstoffen Bayer AG, 5090 Leverkusen | |
| DE2139317C3 (de) | Verfahren zur Herstellung von gegebenenfalls verschäumten Polyurethanen | |
| EP0220485B1 (de) | Sulfonsäureestergruppen aufweisenden Polyhydroxylverbindungen und ihre Verwendung als Polyolkomponente in Giessharzen | |
| DE1222666B (de) | Verfahren zur Herstellung von Polyurethanschaumstoffen | |
| EP0082397A1 (de) | Verfahren zur Herstellung von Polyurethan-polyisocyanurat-schaumstoffen | |
| EP0360087B1 (de) | Neue Estergruppen gebunden enthaltende Dihydroxyverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| EP0625997B1 (de) | Aminocarbonat-verbindungen und deren anwendung als katalysatoren | |
| DE3232752A1 (de) | N-substituierte perhydrodioxazepine, verfahren zu ihrer herstellung und ihre anwendung zur herstellung von polyurethanen | |
| DE2342432A1 (de) | Neue hydroxyalkyl-verbindungen und das verfahren zu ihrer herstellung |