DE924538C - Process for the production of nitrogen-containing polycondensation products - Google Patents
Process for the production of nitrogen-containing polycondensation productsInfo
- Publication number
- DE924538C DE924538C DEK7166D DEK0007166D DE924538C DE 924538 C DE924538 C DE 924538C DE K7166 D DEK7166 D DE K7166D DE K0007166 D DEK0007166 D DE K0007166D DE 924538 C DE924538 C DE 924538C
- Authority
- DE
- Germany
- Prior art keywords
- groups
- nitrogen
- amino
- chain
- ester
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims description 3
- 238000006068 polycondensation reaction Methods 0.000 title claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 150000001414 amino alcohols Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- 229910005965 SO 2 Inorganic materials 0.000 claims description 3
- 125000005521 carbonamide group Chemical group 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000000565 sulfonamide group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 238000005809 transesterification reaction Methods 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 125000005586 carbonic acid group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical class SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 claims description 2
- 230000001588 bifunctional effect Effects 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- -1 benzoyl aminobutyl chloride Chemical compound 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical group ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- QUPKOUOXSNGVLB-UHFFFAOYSA-N 1,8-diisocyanatooctane Chemical compound O=C=NCCCCCCCCN=C=O QUPKOUOXSNGVLB-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- RQFUZUMFPRMVDX-UHFFFAOYSA-N 3-Bromo-1-propanol Chemical compound OCCCBr RQFUZUMFPRMVDX-UHFFFAOYSA-N 0.000 description 1
- RIRRYXTXJAZPMP-UHFFFAOYSA-N 4-aminobutane-1-thiol Chemical compound NCCCCS RIRRYXTXJAZPMP-UHFFFAOYSA-N 0.000 description 1
- IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical compound NC1CCC(O)CC1 IMLXLGZJLAOKJN-UHFFFAOYSA-N 0.000 description 1
- LQGKDMHENBFVRC-UHFFFAOYSA-N 5-aminopentan-1-ol Chemical compound NCCCCCO LQGKDMHENBFVRC-UHFFFAOYSA-N 0.000 description 1
- OXBLNJIEAQCZMK-UHFFFAOYSA-N CCCCC(C(Cl)=O)NCC(O)=O Chemical compound CCCCC(C(Cl)=O)NCC(O)=O OXBLNJIEAQCZMK-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- ZIWIWAKGUIFNRP-UHFFFAOYSA-N phenyl n-[6-(phenoxycarbonylamino)hexyl]carbamate Chemical compound C=1C=CC=CC=1OC(=O)NCCCCCCNC(=O)OC1=CC=CC=C1 ZIWIWAKGUIFNRP-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Description
Durch Kondensation von Diisocyanaten mit GIykolen entstehen hochmolekulare Polyurethane, die bei genügend hohem Polymerisationsgrad als Ausgangsmaterial für geformte Gebilde, z. B. Fasern, verwendbar sind. Verspinnbare Produkte dieser Art erhält man z. B. durch Umsetzen von Octamethylendiisocyanat mit i, 4-Butandiol (Patent 728981).By condensation of diisocyanates with glycols high molecular weight polyurethanes are produced, which are used as the starting material with a sufficiently high degree of polymerisation for shaped structures, e.g. B. fibers can be used. Spinnable products of this Type is obtained z. B. by reacting octamethylene diisocyanate with i, 4-butanediol (patent 728981).
Ähnliche Produkte bilden sich nach einem weiteren Vorschlag, wenn man Diurethane, z. B. ' Hexamethylen-bis-carbamidsäurediphenylester mit Glykolen, z. B. Dekamethylenglykol, umsetzt.Similar products are formed according to a further proposal when using diurethanes, e.g. B. ' Diphenyl hexamethylene-bis-carbamate with glycols, e.g. B. decamethylene glycol, implemented.
Man hat auch schon vorgeschlagen, Polyurethanverbindungen herzustellen aus Komponenten, die neben den urethanbildenden Gruppen bereits Arnid-^ gruppen (mit der Carbonylgruppe an C gebundene Carbonamidgruppen, Harnstoffgruppen, Sulfonamidgruppen) in offener Kette oder in heterocyclischen Ringen enthalten.It has also been proposed to use polyurethane compounds produce from components that in addition to the urethane-forming groups already Arnid- ^ groups (with the carbonyl group attached to C carbonamide groups, urea groups, sulfonamide groups) contained in open chain or in heterocyclic rings.
Es wurde nun gefunden, daß man neue wertvolle stickstoffhaltige Polykondensationsprodukte erhält, wenn man Kohlensäureverbindungen von Aminoalkoholen oder Aminomercaptanen mit an gesättigte C-Atome gebundenen Amino- und Hydroxyl- bzw. Sulfhydrylgruppen und mit einer Kette von mindestens vier, gegebenenfalls durch Heteroatome oder -gruppen, wie O, S, SO2, unterbrochenen C-Atomen zwischen endständigem Aminostickstoff und Hydroxyl- bzw. Mercaptogruppe, in welchen der Kohlensäurerest in Form eines N-Carbonsäureester- oder -amidrestes oder einer O-Esterverbindung vorliegt, durch Erhitzen intermolekularIt has now been found that new valuable nitrogen-containing polycondensation products are obtained if carbonic acid compounds of amino alcohols or aminomercaptans with amino and hydroxyl or sulfhydryl groups bonded to saturated carbon atoms and with a chain of at least four, optionally with heteroatoms or groups, such as O, S, SO 2 , interrupted carbon atoms between the terminal amino nitrogen and hydroxyl or mercapto group, in which the carbonic acid residue is present in the form of an N-carboxylic acid ester or amide residue or an O-ester compound, intermolecularly by heating
kondensiert, gegebenenfalls in Gegenwart von Lösungs- oder Verdünnungsmitteln und von Katalysatoren, die die Abspaltung von Ammoniak oder Alkohol begünstigen, insbesondere Stoffen von der Art der Umesterungskatalysatoren, z. B. Kaliumcarbonat, Magnesiumoxyd, Magnesiummethylat, Toluolsulfosäure, Camphersulfosäure, Zinkchlorid. Zu diesen Kondensationen kommen nicht nur Derivate einfacher Aminoalkohole, ζ. Β. Derivate ίο des 4-Aminobutanols, des 5-Aminopentanols, des 4-Aminocyclohexanols, des 4-Aminobutylmercaptans (aus Benzoyl-aminobutylchlorid und Kaliumsulfhydrat mit folgender Hydrolyse) in Betracht, sondern auch komplizierte Aminooxy- bzw. Aminomercaptoverbindungen, deren Kette durch Heteroatome oder Heterogruppen, wie O, S, SO2, unterbrochen sein können, z. B. Derivate des ω-Aminobutyl-co'-oxypropylsulfids (aus Benzoyl-atninobutylmercaptan und 3-Brompropanol). Insbesondere sind auch solche Abkömmlinge von Aminooxy- bzw. Aminomercaptoverbindungen eingeschlossen, deren Kette durch Amidgruppen, z. B. an Kohlenstoff gebundene Carbonamidgruppen, Harnstoffgruppen, Sulfonamidgruppen, unterbrochen ist. Diese Amidgruppen können · sowohl in offener Kette als auch in heterocyclischen, in die Kette eingefügten Kernen oder in beiden zugleich enthalten sein.condensed, optionally in the presence of solvents or diluents and of catalysts that promote the elimination of ammonia or alcohol, in particular substances of the type of transesterification catalysts, eg. B. potassium carbonate, magnesium oxide, magnesium methylate, toluenesulfonic acid, camphor sulfonic acid, zinc chloride. In addition to these condensations, there are not only derivatives of simple amino alcohols, ζ. Β. Derivatives ίο of 4-aminobutanol, of 5-aminopentanol, of 4-aminocyclohexanol, of 4-aminobutyl mercaptan (from benzoyl aminobutyl chloride and potassium sulfhydrate with subsequent hydrolysis) into consideration, but also complicated aminooxy or aminomercapto compounds, their chain through heteroatoms or heteroatoms , such as O, S, SO 2 , can be interrupted, e.g. B. Derivatives of ω-aminobutyl-co'-oxypropyl sulfide (from benzoyl-atninobutyl mercaptan and 3-bromopropanol). In particular, those derivatives of aminooxy or aminomercapto compounds are also included, the chain of which is replaced by amide groups, e.g. B. carbon-bonded carbonamide groups, urea groups, sulfonamide groups, is interrupted. These amide groups can be present both in the open chain and in heterocyclic nuclei inserted into the chain or in both at the same time.
Die nach dem Verfahren der Erfindung erhaltenen Produkte sind je nach ihren Eigenschaften verschiedener und vielseitiger Verwendung fähig. Ausgesprochen hochmolekulare Stoffe können nach den für Polyamide bekannten Methoden aus der Schmelze, aus Lösungen oder thermoplastisch auf orientierte Fasern, Bändchen, Folien oder andere Flächengebilde verarbeitet werden. Sie lassen sich ferner durch Spritzen, Spritzgießen, Pressen auf dreidimensionale Körper verformen. Niedrigerpolymere Stoffe können beispielsweise als Lackrohstoffe Verwendung finden. Weiche Produkte sind als Kunstwächse brauchbar. In organischen Lösungsmitteln relativ leicht lösliche Stoffe hochpolymerer und mittelhochpolymerer Art eignen sich zur Verwendung, als Hilfsmittel in der Textil- und Lederindustrie und verwandten Zweigen der chemischen Technologie, z. B. zu Imprägnierungen oder Fixierung von Pigmenten und Farbstoffen auf Geweben. *The products obtained by the process of the invention are different depending on their properties Capable of various and versatile uses. Extremely high molecular weight substances can by the methods known for polyamides from the melt, from solutions or Processed thermoplastically on oriented fibers, ribbons, foils or other flat structures will. They can also be injected, injection molded or pressed onto three-dimensional bodies deform. Lower polymer materials can be used as paint raw materials, for example. Soft products can be used as artificial waxes. Relatively easily soluble in organic solvents Substances of a high and medium high polymer type are suitable for use as auxiliaries in the textile and leather industry and related branches of chemical technology, e.g. B. for impregnation or fixation of pigments and dyes on fabrics. *
ι. S-Aminopentanolwird mit Chlorameisensäuremethylester in den entsprechenden Carbamidsäuremethylester übergeführt. Man erhitzt dann diesesι. S-aminopentanol is made with methyl chloroformate converted into the corresponding carbamic acid methyl ester. This is then heated
Urethan in Gegenwart von V b b f M UUrethane in the presence of V b b f M U
2Oo h 2O oh
g 2Oo Kalium-g 2O o potassium
carbonat, bezogen auf 1 Mol Urethan, auf 140 bis i8o° bis zum Nachlassen der. Methanolabspaltung und hält die Temperatur schließlich noch 6 Stunden im Vakuum von 0,5 mm auf · i8o°, indem man gleichzeitig einen trockenen, vorgewärmten Stickstoffstrom über die Schmelze hinwegstreichen läßt.carbonate, based on 1 mole of urethane, to 140 to i8o ° until the. Elimination of methanol and finally holds the temperature for a further 6 hours in a vacuum from 0.5 mm to 180 ° by at the same time lets a dry, preheated nitrogen stream sweep over the melt.
Das Reaktionsprodukt kann aus der Schmelze zu orientierbaren Fäden ausgezogen werden.The reaction product can be drawn out of the melt to form orientable threads.
2. N-Carboxymethylaminocapronsäurechlor id, hergestellt aus der Säure mit Thionylchlorid, läßt man in Benzollösung auf eine wäßrige Lösung von i, 4-Aminobutanol in Gegenwart von Alkali unter guter Kühlung einwirken. Das hierbei erhaltene Urethan der Formel2. N-carboxymethylaminocaproic acid chloride, prepared from the acid with thionyl chloride, one leaves in benzene solution on an aqueous solution of i, 4-aminobutanol in the presence of alkali under good cooling effect. The resulting urethane of the formula
CH3- O—CO—NH- (CH2)5—CH 3 - O — CO — NH- (CH 2 ) 5 -
—CO—NH-(CH2)4-OH-CO-NH- (CH 2 ) 4 -OH
kondensiert sich beim Erhitzen auf 140 Ws i8o°, insbesondere in- Gegenwart von Umesterungskatalysatoren, z. B. V200 Mol Natriummethylat, bezogen auf ι Mol Urethan, mit sich selbst unter Abspalrung· von Methanol. Die Reaktion kann mit und ohne Lösungsmittel durchgeführt werden. Ein geeignetes Lösungsmittel ist o-Dichlorbenzol.condenses on heating to 140 Ws i8o °, especially in the presence of transesterification catalysts, e.g. B. V 200 moles of sodium methoxide, based on ι moles of urethane, with itself with elimination · of methanol. The reaction can be carried out with or without a solvent. A suitable solvent is o-dichlorobenzene.
3. Tr.ans-4-Aminocyclohexanol wird in Benzol mit der berechneten Menge Chlorameisensäurephenylester zum Urethan acyliert. Man destilliert dann· das Benzol ab und erhitzt in Gegenwart einer Spur Natriumphenolat in trockenem Phenol so lange auf 170°, bis die Viskosität nicht mehr zunimmt. Das Reaktionsprodukt wird dann mit Aceton als Pulver gefällt. Es kann durch Wiederaufschmelzen und Erhitzen der Schmelze im Hochvakuum noch höherpolymer gemacht werden.3. Tr.ans-4-aminocyclohexanol is acylated in benzene with the calculated amount of phenyl chloroformate to give the urethane. The benzene is then distilled off and heated to 170 ° in the presence of a trace of sodium phenolate in dry phenol until the viscosity no longer increases. The reaction product is then precipitated as a powder with acetone. It can be made even more polymeric by remelting and heating the melt in a high vacuum.
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK7166D DE924538C (en) | 1939-06-13 | 1939-06-13 | Process for the production of nitrogen-containing polycondensation products |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK7166D DE924538C (en) | 1939-06-13 | 1939-06-13 | Process for the production of nitrogen-containing polycondensation products |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE924538C true DE924538C (en) | 1955-03-03 |
Family
ID=7211513
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEK7166D Expired DE924538C (en) | 1939-06-13 | 1939-06-13 | Process for the production of nitrogen-containing polycondensation products |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE924538C (en) |
-
1939
- 1939-06-13 DE DEK7166D patent/DE924538C/en not_active Expired
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