DE907599C - Process for the preparation of linear polymeric condensation products containing amide and urethane groups - Google Patents
Process for the preparation of linear polymeric condensation products containing amide and urethane groupsInfo
- Publication number
- DE907599C DE907599C DEB7290D DEB0007290D DE907599C DE 907599 C DE907599 C DE 907599C DE B7290 D DEB7290 D DE B7290D DE B0007290 D DEB0007290 D DE B0007290D DE 907599 C DE907599 C DE 907599C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- condensation products
- products containing
- urethane groups
- preparation
- 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
- 239000007859 condensation product Substances 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 5
- 150000001408 amides Chemical class 0.000 title claims description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title 1
- 239000002253 acid Substances 0.000 claims description 6
- 150000004985 diamines Chemical class 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 4
- 150000002334 glycols Chemical class 0.000 claims description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 3
- 239000012433 hydrogen halide Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- DIORMHZUUKOISG-UHFFFAOYSA-N sulfoformic acid Chemical class OC(=O)S(O)(=O)=O DIORMHZUUKOISG-UHFFFAOYSA-N 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 8
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 4
- 150000004820 halides Chemical group 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- ZEYZKQUPVUMZKV-UHFFFAOYSA-N dichloro carbonate Chemical compound ClOC(=O)OCl ZEYZKQUPVUMZKV-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- -1 ethylene, propylene Chemical group 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- JONTXEXBTWSUKE-UHFFFAOYSA-N 2-(2-aminoethylsulfanyl)ethanamine Chemical compound NCCSCCN JONTXEXBTWSUKE-UHFFFAOYSA-N 0.000 description 1
- YQPCHPBGAALCRT-UHFFFAOYSA-N 2-[1-(carboxymethyl)cyclohexyl]acetic acid Chemical compound OC(=O)CC1(CC(O)=O)CCCCC1 YQPCHPBGAALCRT-UHFFFAOYSA-N 0.000 description 1
- HABHUTWTLGRDDU-UHFFFAOYSA-N 2-oxopimelic acid Chemical compound OC(=O)CCCCC(=O)C(O)=O HABHUTWTLGRDDU-UHFFFAOYSA-N 0.000 description 1
- ZMPRRFPMMJQXPP-UHFFFAOYSA-N 2-sulfobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1S(O)(=O)=O ZMPRRFPMMJQXPP-UHFFFAOYSA-N 0.000 description 1
- FYKCKCYYMXDNHZ-UHFFFAOYSA-N 2-sulfobutanoic acid Chemical compound CCC(C(O)=O)S(O)(=O)=O FYKCKCYYMXDNHZ-UHFFFAOYSA-N 0.000 description 1
- WBGKAOURNYRYBT-UHFFFAOYSA-N 2-sulfopropanoic acid Chemical compound OC(=O)C(C)S(O)(=O)=O WBGKAOURNYRYBT-UHFFFAOYSA-N 0.000 description 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- ZILIDAVDZSTKDH-UHFFFAOYSA-N C(=O)(Cl)Cl.C(CCC)(O)O Chemical compound C(=O)(Cl)Cl.C(CCC)(O)O ZILIDAVDZSTKDH-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical class ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 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
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
Description
Verfahren zur Herstellung linearpolymerer, amid- und urethangruppenhaltiger Kondensationsprodukte Es wurde gefunden, daß man wertvolle Kondensationsprodukte erhält, wenn man Diamine mit Gemischen aus Dihalogenkohlensäureestern von Glykolen und Dihalogeniden zweibasischer, organischer Carbon-, Sulfon- oder Sulfocarbonsäuren unter Mitverwendung Halogenwasserstoff bindender Mittel kondensiert.Process for the production of linear polymeric, amide and urethane groups Condensation products It has been found that valuable condensation products can be obtained obtained when diamines with mixtures of dihalocarbonic acid esters of glycols and dihalides of dibasic, organic carboxylic, sulphonic or sulphocarboxylic acids condensed with the use of hydrogen halide binding agents.
Zweckmäßig benutzt man die Umsetzungsteilnehmer in äquivalenten oder nahezu äquivalenten Mengen derart, daß auf jede Aminogruppe etwa eine Säurehalogenidgruppe kommt, wobei auch die Chlorkohlensäureestergruppe als Säurehalogenidgruppe gilt.The implementation participants are expediently used in equivalent or almost equivalent amounts such that for each amino group there is about one acid halide group comes, whereby the chlorocarbonic acid ester group also counts as an acid halide group.
Als Diamine kommen z. B. in Frage: Äthylendiamin, Butylendiathin, i, 5-Penta-, i, 6-Hexamethylendiamin, ß, ß'-Diaminodiäthylsulfid, p, p'-Diamino-dicyclohexylmethan oder -äthan, oder co, co'-Diaminodipropyläther von Äthylen-, Propylenglykol, i, 4-Butan- oder i, 6-Hexandiol. Als Dihalogenkohlensäureester eignen sich beispielsweise die Dichlorkohlensäureester von i, 4.-Butylenglykol, Thiodiglykol, Diglykol, Triglykol, i, 5-Pentandiol oder i, 6-Hexandiol.As diamines z. B. in question: ethylene diamine, butylene diathine, i, 5-penta-, i, 6-hexamethylenediamine, ß, ß'-diaminodiethyl sulfide, p, p'-diamino-dicyclohexylmethane or -ethane, or co, co'-diaminodipropyl ether of ethylene, propylene glycol, i, 4-butane or i, 6-hexanediol. Suitable dihalocarbonic acid esters are, for example the dichlorocarbonic acid esters of 1,4-butylene glycol, thiodiglycol, diglycol, triglycol, i, 5-pentanediol or i, 6-hexanediol.
Als Halogenide zweibasischer, organischer Säuren kommen z. B. die Chloride der Adipinsäure, Sebacinsäure, Nonan- oder Dekandicarbonsäure, Ketopimelinsäure, Cyclohexandiessigsäure, ferner der Propan-, Butan-, Hexan- oder höherer aliphatischer Sulfonsäuren sowie z. B. p-Benzoldisulfochlorid und Halogenide von Sulfocarbonsäuren, z. B. von Sulfobuttersäure, Sulfopropionsäure und Sulfobenzoesäure, in Betracht.As halides of dibasic organic acids come z. B. the Chlorides of adipic acid, sebacic acid, nonane or decanedicarboxylic acid, ketopimelic acid, Cyclohexanediacetic acid, also propane, butane, hexane or higher aliphatic Sulfonic acids and z. B. p-Benzene disulfochloride and halides of sulfocarboxylic acids, z. B. of sulfobutyric acid, sulfopropionic acid and sulfobenzoic acid into consideration.
Die Umsetzung erfolgt zweckmäßig in Gegenwart von indifferenten Lösungs- oder Verdünnungsmitteln, wie Wasser, Alkoholen oder Kohlenwasserstoffen. Es empfiehlt sich ferner, bei der Umsetzung von vornherein Halogenwasserstoff bindende Mittel, wie Alkali-oder Erdalkalihydroxvde, -carbonate, -bicarbonate, -acetate oder auch indifferente organische Basen, wie Pvridin oder Dimethvlanilin, hinzuzusetzen. Andernfalls müssen die Kondensationsprodukte mit basischen 'Mitteln nachbehandelt werden.The reaction is expediently carried out in the presence of inert solution or diluents such as water, alcohols or hydrocarbons. It recommends furthermore, agents which bind hydrogen halide from the outset during the implementation, like alkali or Alkaline earth hydroxides, carbonates, bicarbonates, acetates or also indifferent organic bases, such as pvridine or dimethvlaniline, to be added. Otherwise the condensation products have to be treated with basic agents will.
Die Umsetzung beginnt im allgemeinen schon bei g ewo öhnlicher Temperatur oder darunter und wird zweckmäßig bei erhöhter Temperatur zu Ende geführt. Vielfach ist es auch vorteilhaft, die in Lösung bzw. in Suspension erhaltenen Kondensationsprodukte durch Erhitzen auf höhere Temperaturen, z. B. i5o bis 300°, nachzukondensieren.The reaction generally begins at a customary temperature or below and is expediently completed at an elevated temperature. Multiple it is also advantageous to use the condensation products obtained in solution or in suspension by heating to higher temperatures, e.g. B. i5o to 300 °, post-condense.
Die erhaltenen Kondensationsprodukte sind wertvolle, z.T. fadenziehende Harze, die in der Lack- und Kunststoffindustrie Verwendung finden können.The condensation products obtained are valuable, some of them stringy Resins that can be used in the paint and plastics industry.
Es ist bekannt, durch Umsetzung von Diaminen mit Dihalogenkohlensäureestern von Glykolen Polyurethane herzustellen. Andererseits hat man bereits durch Unisetzung von Dicarbonsäuredihalogeniden mit Diaminen Polyamide hergestellt. Die nach dem vorliegenden Verfahren erhältlichen gemischten Polyamid-urethane sind von den durch Vermischen von Polvurethanen mit Polyamiden erhältlichen Produkten verschieden. Das vorliegende Verfahren stellt somit eine neue, technisch erwünschte Abwandlungsmöglichkeit in der Herstellung von Polykondensationsprodukten dar, da man hier durch geeignete Wahl der Mengenverhältnisse der einzelnen Komponenten die Eigenschaften der Produkte dem jeweils gewünschten Zweck sehr gut anpassen kann.It is known by reacting diamines with dihalocarbonic acid esters of glycols to produce polyurethanes. On the other hand, one already has by unisposal made of dicarboxylic acid dihalides with diamines polyamides. The after The mixed polyamide-urethanes obtainable by the present processes are from those by Mixing of polyurethanes with polyamides available products different. The present method thus represents a new, technically desirable modification option in the production of polycondensation products, since you can use suitable Choice of the proportions of the individual components the properties of the products can adapt very well to the desired purpose.
Die in den folgenden Beispielen angegebenen Teile sind Glewichtsteile.The parts given in the following examples are parts by weight.
Beispiel i Zu einer Lösung von 268,7 Teilen 1, q-Butandioldichlorkohlensäureester und 228,7 Teilen Adipinsäuredichlorid in 5oo Teilen Benzol läßt man unter Rühren eine Lösung von 29o Teilen Hexamethylendiamin und 57o Teilen 35° oiger Natronlauge in 2ooo Teilen Wasser derart zufließen, daß die Temperatur zwischen o und 5° gehalten wird. Dann wird langsam zum Sieden erhitzt und eine Stunde- bei Siedetemperatur gehalten. Das abgeschiedene Kondensationsprodukt wird abgetrennt, mit Wasser gut gewaschen und getrocknet. Man erhält ein farbloses, pulveriges, klar schmelzendes Kondensationsprodukt, das gut Fäden zieht und in Alkoholen und anderen Lösungsmitteln unlöslich ist.Example i To a solution of 268.7 parts of 1, q-butanediol dichlorocarbonate and 228.7 parts of adipic acid dichloride in 500 parts of benzene are left with stirring a solution of 29o parts of hexamethylenediamine and 57o parts of 35 ° sodium hydroxide solution in 2ooo parts of water so that the temperature is kept between 0 and 5 ° will. Then it is slowly heated to boiling and one hour at boiling temperature held. The deposited condensation product is separated off with water well washed and dried. A colorless, powdery, clear melting one is obtained Condensation product that pulls threads well and in alcohols and other solvents is insoluble.
Beispiel 2 Zu einer Lösung von 288 Teilen i, .1-Butandioldichlorkohlensäureester und 228 Teilen Adipinsäuredichlorid in 5oo Teilen Benzol läßt man unter Rühren bei o bis 5° eine Lösung von 15o Teilen Äthylendiamin und 57o Teilen 35°/oiger -Natronlauge in iooo Teilen Wasser zufließen. Das Reaktionsgemisch wird io bis 12 Stunden bei gewöhnlicher Temperatur nachgerührt. Man trennt dann den entstandenen Niederschlag ab, wäscht ihn mit Wasser und trocknet ihn.Example 2 To a solution of 288 parts of i, .1-Butanediol dichlorocarbonic acid ester and 228 parts of adipic acid dichloride in 500 parts of benzene are added with stirring o to 5 ° a solution of 150 parts of ethylenediamine and 57o parts of 35% sodium hydroxide solution pour in 10000 parts of water. The reaction mixture is 10 to 12 hours at Stirred at ordinary temperature. The precipitate formed is then separated wash it off with water and dry it.
Man erhält ein farbloses Pulver, das in Wasser und 'lethanol unlöslich, in warmem Äthylenglykol dagegen gut löslich ist. Es kann für Lackzwecke Verwendung finden.A colorless powder is obtained which is insoluble in water and ethanol, in contrast, is readily soluble in warm ethylene glycol. It can use for paint purposes Find.
Beispiel 3 Zu einem gekühlten Gemisch aus 2ö8;7 Teilen i, ,l-Butandioldichlorkohlensäureester, 318,7 Teilen Butan-i, 4-disulfochlorid und 3oo Teilen Benzol läßt man unter Rühren eine Lösung von 29o Teilen Hexamethylendiamin und 265 Teilen Natriumcarbonat in 3000 Teilen Wasser derart zutropfen, daß die Temperatur zwischen o und 5' gehalten wird. Nach mehrstündigem Nachrühren bei gewöhnlicher Temperatur wird das entstandene Kondensationsprodukt abgetrennt, mit Wasser gewaschen und getrocknet. EXAMPLE 3 A solution of 29o parts of hexamethylenediamine and 265 parts of sodium carbonate in 3000 parts is added to a cooled mixture of 20.8; 7 parts of i,, l-butanediol dichlorocarbonate, 318.7 parts of 1,4-butane, 4-disulphochloride and 300 parts of benzene Add water dropwise in such a way that the temperature is kept between 0 and 5 '. After several hours of stirring at normal temperature, the condensation product formed is separated off, washed with water and dried.
Man erhält ein farbloses, in Wasser und Methanol unlösliches, in warmem Äthylenglykol dagegen gut lösliches Kondensationsprodukt.One receives a colorless, insoluble in water and methanol, in warm Ethylene glycol, on the other hand, is a readily soluble condensation product.
An Stelle der Dichloride kann man auch die entsprechenden Dibromide bzw. Dij odide verwenden. Beispiel 4. .The corresponding dibromides can also be used in place of the dichlorides or use dijodides. Example 4..
Zu 29o Teilen Hexamethylendiamin wird bei gewöhnlicher Temperatur ein Gemisch aus 268,7 Teilen i, :l-Butandioldichlorkohlensäureester, 228,7 Teilen Adipinsäuredichlorid und --ooo Teilen Benzol langsam zugegeben. Man rührt das Gemisch io bis i2 Stunden bei gewöhnlicher Temperatur nach und läßt dann eine Lösung von 57o Teilen 35°/oiger Natronlauge in 3000 Teilen Wasser unter Kühlung derart einfließen, daß keine nennenswerte Temperatursteigerung eintritt. Das abgeschiedene Kondensationsprodukt wird hierauf abgetrennt, mit Wasser gewaschen und getrocknet.To 290 parts of hexamethylenediamine, a mixture of 268.7 parts of i,: l-butanediol dichlorocarbonate, 228.7 parts of adipic acid dichloride and --ooo parts of benzene is slowly added at ordinary temperature. The mixture is stirred for 10 to 12 hours at normal temperature and a solution of 57o parts of 35% sodium hydroxide solution in 3000 parts of water is then allowed to flow in with cooling in such a way that no appreciable increase in temperature occurs. The deposited condensation product is then separated off, washed with water and dried.
.Man erhält ein farbloses, pulveriges, klar schmelzendes Harz, das in Wasser und Methanol unlöslich, in anderen organischen Lösungsmitteln, z. B. in warmem Äthylenglykol, dagegen gut löslich ist.A colorless, powdery, clear melting resin is obtained, the Insoluble in water and methanol, in other organic solvents, e.g. Am warm ethylene glycol, but it is easily soluble.
Beispiel 5 Man vermischt bei 6o bis 8o° 128 Teile Hexamethylendiamin mit einem Gemisch aus 215 Teilen ButandioldichlorkohlensäUreester und 18 Teilen Adipinsäuredichlorid. Das erhaltene Produkt wird zerkleinert und dann längere Zeit mit einer Lösung von 57o Teilen 35°/oiger Natronlauge in 3ooo Teilen Wasser verrührt. Man erhält ein farbloses Pulver, das in Wasser und Methanol nicht, in warmem Äthylenglykol nur wenig, dagegen ziemlich gut in warmem Phenol löslich ist.Example 5 128 parts of hexamethylenediamine are mixed at 60 to 80 ° with a mixture of 215 parts of butanediol dichlorocarbonate and 18 parts Adipic acid dichloride. The product obtained is crushed and then for a long time stirred with a solution of 57o parts of 35% sodium hydroxide solution in 3ooo parts of water. A colorless powder is obtained that does not work in water and methanol in warm ethylene glycol is only slightly soluble in warm phenol, on the other hand fairly well.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB7290D DE907599C (en) | 1942-05-21 | 1942-05-21 | Process for the preparation of linear polymeric condensation products containing amide and urethane groups |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB7290D DE907599C (en) | 1942-05-21 | 1942-05-21 | Process for the preparation of linear polymeric condensation products containing amide and urethane groups |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE907599C true DE907599C (en) | 1954-03-25 |
Family
ID=6955265
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB7290D Expired DE907599C (en) | 1942-05-21 | 1942-05-21 | Process for the preparation of linear polymeric condensation products containing amide and urethane groups |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE907599C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1006155B (en) * | 1954-06-15 | 1957-04-11 | Bayer Ag | Process for the production of basic condensation products |
| DE1061071B (en) * | 1953-10-26 | 1959-07-09 | Du Pont | Process for the production of curable, rubber-elastic condensation products containing urea and urethane groups |
| DE1125173B (en) * | 1957-05-08 | 1962-03-08 | Du Pont | Process for the production of high-melting mixed polycondensates containing residues of piperazine |
-
1942
- 1942-05-21 DE DEB7290D patent/DE907599C/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1061071B (en) * | 1953-10-26 | 1959-07-09 | Du Pont | Process for the production of curable, rubber-elastic condensation products containing urea and urethane groups |
| DE1006155B (en) * | 1954-06-15 | 1957-04-11 | Bayer Ag | Process for the production of basic condensation products |
| DE1125173B (en) * | 1957-05-08 | 1962-03-08 | Du Pont | Process for the production of high-melting mixed polycondensates containing residues of piperazine |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE831772C (en) | Process for the production of high molecular weight crosslinked plastics | |
| CH642982A5 (en) | POLYAETHER POLYAMIDE. | |
| DE1595092A1 (en) | Process for the production of aromatic polyamide amides | |
| DE1795464B2 (en) | Process for the production of essentially amorphous, transparent polyamides | |
| DE2648774A1 (en) | NEW, TERMINAL AMINO-GROUP POLYAETERS, PROCESSES FOR THEIR MANUFACTURING AND THEIR USE | |
| DE1595354A1 (en) | Process for the production of crystal clear polyamides | |
| DE2855928A1 (en) | NEW COPOLYAMID | |
| DE1643170A1 (en) | Process for the preparation of aromatic diisocyanate dimers | |
| DE907599C (en) | Process for the preparation of linear polymeric condensation products containing amide and urethane groups | |
| DE2125311A1 (en) | Non-thrombogenic polymers | |
| DE1495121A1 (en) | Linear polyester amides and a process for their preparation | |
| DE1301124B (en) | Process for the production of elastic, thermoplastic polyester urethanes | |
| DE2410082A1 (en) | ANTISTATIC FIBER AND METHOD OF MANUFACTURING THEREOF | |
| EP0000492B1 (en) | Transparent polyamides and their use for the manufacture of moulds | |
| DE69024807T2 (en) | IMPACT-RESISTANT HIGH-TEMPERATURE RESIN CONTAINING MATRIX SYSTEM | |
| DE1745400A1 (en) | Hardenable polyamides | |
| DE2737257A1 (en) | TRANSPARENT POLYAMIDE | |
| DE1570249A1 (en) | Process for the recovery of polyol and amine derivatives by the decomposition of polyurethane substances | |
| DE2036903A1 (en) | Process for the preparation of a solution of a polyurethane | |
| AT383138B (en) | Process for preparing cationic imido-functional synthetic resins | |
| DE1001486B (en) | Process for the accelerated curing of thin layers from mixtures of polyisocyanates and polycondensation products containing reactive hydrogen atoms | |
| DE926935C (en) | Process for the production of linear polyester-polyamides | |
| DE1098909B (en) | Process for the production of a leather-like laminate | |
| DE925495C (en) | Process for the production of nitrogen-containing, linear condensation products | |
| DE2045770A1 (en) | New polyamides and methods of making them |