DE731030C - Process for the production of soluble nitrogen-containing condensation products that can be converted into insoluble, hard products by self-condensation - Google Patents
Process for the production of soluble nitrogen-containing condensation products that can be converted into insoluble, hard products by self-condensationInfo
- Publication number
- DE731030C DE731030C DEI63676D DEI0063676D DE731030C DE 731030 C DE731030 C DE 731030C DE I63676 D DEI63676 D DE I63676D DE I0063676 D DEI0063676 D DE I0063676D DE 731030 C DE731030 C DE 731030C
- Authority
- DE
- Germany
- Prior art keywords
- condensation
- products
- insoluble
- self
- hard
- 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
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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/10—Polycondensates containing more than one epoxy group per molecule of polyamines with epihalohydrins or precursors thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/5006—Amines aliphatic
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Description
Verfahren zur Herstellung von löslichen, durch Selbstkondensation in unlösliche, harte Produkte überführbaren stickstoffhaltigen Kondensationsprodukten Es ist bekannt, Äthylendiamin mit Epichlorhydrin umzusetzen. Hierbei wurde auf i 1\2o1 des Amins i Mol Epichlorhydrin verwendet, und es wurde ein sirup.öses Rveaktionsprodukt erhalten, das sich beim Stehen oder Erwärmen :nicht 'merklich verändert.Process for the preparation of soluble, by self-condensation nitrogen-containing condensation products that can be converted into insoluble, hard products It is known to implement ethylenediamine with epichlorohydrin. Here, i 1 \ 2o1 of the amine in 1 mole of epichlorohydrin was used, and it was a syrupy reaction product that does not change noticeably when standing or warming up.
Es würde nun gefunden, daß sich überraschenderweise aus Diaminen. oder Polyaminen mit mindestens zwei primären Amino=-gruppen und einem Epihalogenhydrin, threndioxyd oder Diglycidäther stickstilthaltige Kondensationsprodukte herstellen lassen. welche einer Selbstkondensation unter Bildung harter ' und unlöslicher Produkte fähig sind, wenn man die Basenmengc geringer hält, als es dem molaren Verhältnis der Komponenten entspricht. -Das neue Verfahren kann so durchgeführt werden, daß man die eine oder mehrere Äthylenoxydbrücken enthaltende Verbindung irr überschuß auf das Amin einwirken läßt. Die Kondensation verläuft, exotherm. Durch geeignete Wahl der Reaktionsbedingungen lassen sich Produkte isolieren, die in Wasser bzw. in organischen Lösungsmitteln noch löslich sind. und: die spontan oder beim Ei"värmen in harte, unlösliche Stoffe übergehen können. Um derartige lösliche Zwischenstufen zu fassen, sind bei der Kondensation zu starke Temperatursteigerungen zu vermeiden. Es empfiehlt sich auch häufig, die Kondensationsprodukte in Lösung zu belassen und sie, gcgebcnenfalls nach Konzentrierung und Mntfernung nicht umgesetzter Anteile, in dieser Form direkt praktisch zu verwenden, da die Kondensationsprodukte in lösungsmittelfneiem Zustand oft schon ein so großes Seibstkondensationsbcstreben haben, daß sie sofort in unlösliche und harte Produkte übergehen,. In manchen Fällen lassen sich die löslichen Zwischenstufen aber auch durch Fällung oder durch Verdampfen des Lösungsmittels abscheiden. Oft kann auch so gearbeitet werden, daß man zunächst molare Mengen der I'@eaktionsteilnehmer zur Umsetzung bringt und anschließend durch Zusatz weiterer Mengen der Äthylenoxydverbindung die gewünschte Kondensation herbeiführt.It has now been found, surprisingly, to consist of diamines. or polyamines with at least two primary amino groups and one epihalohydrin, Threndioxyd or diglycidether produce nitrogenous condensation products permit. which result in self-condensation with the formation of hard and insoluble products are capable, if the base amount is kept lower than the molar ratio of the components. -The new procedure can be carried out so that the compound containing one or more ethylene oxide bridges is in excess lets act on the amine. The condensation is exothermic. Through suitable By choosing the reaction conditions, products can be isolated which are dissolved in water or are still soluble in organic solvents. and: they warm up spontaneously or by the egg can change into hard, insoluble substances. Such soluble intermediates To grasp, excessive temperature increases are to be avoided during the condensation. It is also often advisable to leave the condensation products in solution and they, possibly after concentration and removal of unreacted portions, in this Form directly practical to use, as the condensation products in the solvent-free state there is often such a great tendency towards self-condensation have that they immediately turn into insoluble and hard products. In some cases however, the soluble intermediate stages can also be obtained by precipitation or evaporation to separate the solvent. Often one can also work in such a way that one first brings molar amounts of I '@ eaktion participants to the implementation and then through Addition of further amounts of the ethylene oxide compound brings about the desired condensation.
Die nach dem Verfahren erhältlichen neuen Produkte bieten infolge ihrer Fähigkeit, spontan oder durch Erwärmen zu erhärten und unlöslich zu werden, besonderes Interesse für die Industrie, z. B. auf dem Gebiet der Kunststoffe und Textilhilfsmittel.The new products available by the process offer as a result their ability to harden and become insoluble, either spontaneously or by heating, special interest in industry, e.g. B. in the field of plastics and Textile auxiliaries.
Beispiel 1 Eine Lösung von 92 Gewichtsteilen Epichlorhydrin in 25 Gewichtsteilen Methanol wird auf 4o bis 42' angewärmt und unter Rühren allmählich mit 4o Gewichtsteilen,einer 72,9o/oigen wäßrigen Äthylendiaminlösung versetzt. Man läßt die Temperatur auf 6o' ansteigen und rührt noch eine Zeitlang nach. Man erhält eine klare, gelbliche, viscose Lö: sung, die das Kondensationsprodukt enthält. Sie läßt sich durch Erwärmen auf 5o bis 70` im Vakuum konzentrieren. Dampft man z. B. auf einen Rückstand von 125 bis 13o Gewichtsteilen ein, so erhält man ein sehr zähes. gelbliches Harz, das sich beim Aufbewahren langsam, viel schneller beim Erhitzen in ein hartes, festes, in allen Lösungsmitteln unlösliches Produkt verwandelt. In frisch hergestelltem Zustand ist es jedoch z. B. in Wasser, Alkoholen und io%iger Natronlauge löslich. Die Lösungen hinterlassen beim Eindampfen oder Eindunsten einen ebenfalls. leicht härtbaren Rückstand.Example 1 A solution of 92 parts by weight of epichlorohydrin in 25 Parts by weight of methanol are warmed to 40 to 42 'and gradually increased with stirring with 40 parts by weight of a 72.9% aqueous ethylenediamine solution. Man lets the temperature rise to 60 'and stirs for a while. You get a clear, yellowish, viscous solution that contains the condensation product. she can be concentrated by heating to 5o to 70` in a vacuum. If you vape z. B. to a residue of 125 to 130 parts by weight, a very tough one is obtained. yellowish resin that dissolves slowly when stored, much faster when heated transformed into a hard, solid product, insoluble in all solvents. In However, in the freshly prepared state it is z. B. in water, alcohols and io% Sodium hydroxide soluble. The solutions leave a residue when they evaporate or evaporate Likewise. easily hardenable residue.
Ähnliche Kondensationsprodukte erhält man aus Epichlorhydrin und 1 # 4-Tetramethylelldiamin, 1 # 6-Hexamethylendiamin, 1 # Zo-Dekamethylendiamin oder Triäthylentetramin.Similar condensation products are obtained from epichlorohydrin and 1 # 4-tetramethylelliamine, 1 # 6-hexamethylenediamine, 1 # zo-decamethylenediamine or Triethylenetetramine.
Beispiel z 93 Gewichtsteile Epichlorhydrin würden in 175 Gewichtsteilen Wasser suspendiert und allmählich mit 38 Gewichtsteilen-,einer 7Sojoigen wäßrigen Lösung von Äthylendiamin versetzt, so daß die Temperatur 6o bis 65' nicht übersteigt. Man erhält eine klare viscose Lösung, aus der durch Zusatz von Natronlauge ein leicht härtendes Kondensationsprodukt abgeschieden -wird.Example z 93 parts by weight of epichlorohydrin would be suspended in 175 parts by weight of water and gradually admixed with 38 parts by weight of a 7Sojoigen aqueous solution of ethylenediamine so that the temperature does not exceed 60 to 65 '. A clear viscous solution is obtained from which a slightly hardening condensation product is deposited by adding sodium hydroxide solution.
Beispiel 3 Zu einer Lösung von 17,2 Gewichtsteilen F ry threndioxyd in 6o Gewichtsteilen Methanol werden allmählich unter Rühren 13 Gewichtsteile 1 # 6-Hexamefhylendiamin in 38 Gewichtsteilen Methanol gegeben. Die sich erwärmende Mischung -wird durch Kühlung zwischen 55 und 6o' gehalten und nach beendetem Zusatz noch kurze Zeit nachgerührt. Man erhält eine viscose Lösung des Kondensationsproduktes, die nach einiger Zeit koaguliert, jedoch durch Verdünnung mit Methanol oder Wasser stabilisiert werden kann.Example 3 To a solution of 17.2 parts by weight of methylene dioxide 13 parts by weight of 1 # 6-hexamethylene diamine in 38 parts by weight of methanol are gradually added to 60 parts by weight of methanol with stirring. The warming mixture is kept between 55 and 6o 'by cooling and is stirred for a short time after the addition has ended. A viscous solution of the condensation product is obtained which coagulates after some time, but can be stabilized by dilution with methanol or water.
Es ist auch möglich, zunächst das Amin mit der molaren Menge (14 Gewichtsteile) Crythrendioxy d umzusetzen und das erhaltene Produkt mit etwa 5 Gewichtsteilen Erythrendioxyd nachzubehandeln. Auch hierbei wird ein Produkt erhalten, welches unter Selbstkondensation in ein hartes und unlösliches Harz übergeht.It is also possible to first add the amine with the molar amount (14 parts by weight) Crythrendioxy d to implement and the product obtained with about 5 parts by weight of erythrendioxyd post-treatment. Here, too, a product is obtained which undergoes self-condensation turns into a hard and insoluble resin.
Statt des Erythrendioxyds im ersten Absatz dieses Beispiels kann auch eine äquivalente Menge Diglycidäther verwendet werden.Instead of the erythrene dioxide in the first paragraph of this example, an equivalent amount of diglycidyl ether can also be used be used.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEI63676D DE731030C (en) | 1939-02-02 | 1939-02-02 | Process for the production of soluble nitrogen-containing condensation products that can be converted into insoluble, hard products by self-condensation |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEI63676D DE731030C (en) | 1939-02-02 | 1939-02-02 | Process for the production of soluble nitrogen-containing condensation products that can be converted into insoluble, hard products by self-condensation |
Publications (1)
Publication Number | Publication Date |
---|---|
DE731030C true DE731030C (en) | 1943-02-02 |
Family
ID=7195960
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEI63676D Expired DE731030C (en) | 1939-02-02 | 1939-02-02 | Process for the production of soluble nitrogen-containing condensation products that can be converted into insoluble, hard products by self-condensation |
Country Status (1)
Country | Link |
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DE (1) | DE731030C (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE915329C (en) * | 1950-10-12 | 1957-07-11 | Bayer Ag | Process for the production of pigment prints or pads |
US2849411A (en) * | 1952-11-19 | 1958-08-26 | Bayer Ag | Stabilization of basic condensation products of epichlorohydrin |
DE1211922B (en) * | 1961-08-09 | 1966-03-03 | Bayer Ag | Aid for filler retention in papermaking |
DE1213226B (en) * | 1952-12-02 | 1966-03-24 | Bayer Ag | Process for increasing the wet strength of paper |
DE1253390B (en) * | 1961-12-02 | 1967-11-02 | Universal Oil Prod Co | Stabilizer for hydrocarbon distillates |
-
1939
- 1939-02-02 DE DEI63676D patent/DE731030C/en not_active Expired
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE915329C (en) * | 1950-10-12 | 1957-07-11 | Bayer Ag | Process for the production of pigment prints or pads |
US2849411A (en) * | 1952-11-19 | 1958-08-26 | Bayer Ag | Stabilization of basic condensation products of epichlorohydrin |
DE1213226B (en) * | 1952-12-02 | 1966-03-24 | Bayer Ag | Process for increasing the wet strength of paper |
DE1211922B (en) * | 1961-08-09 | 1966-03-03 | Bayer Ag | Aid for filler retention in papermaking |
DE1211922C2 (en) * | 1961-08-09 | 1973-05-10 | Bayer Ag | Aid for filler retention in papermaking |
DE1253390B (en) * | 1961-12-02 | 1967-11-02 | Universal Oil Prod Co | Stabilizer for hydrocarbon distillates |
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