DE448738C - Process for the preparation of water-soluble condensation products from amino compounds or acid amides and acetaldehyde disulfonic acids - Google Patents

Process for the preparation of water-soluble condensation products from amino compounds or acid amides and acetaldehyde disulfonic acids

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Publication number
DE448738C
DE448738C DEA44669D DEA0044669D DE448738C DE 448738 C DE448738 C DE 448738C DE A44669 D DEA44669 D DE A44669D DE A0044669 D DEA0044669 D DE A0044669D DE 448738 C DE448738 C DE 448738C
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DE
Germany
Prior art keywords
water
condensation products
amino compounds
acid amides
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
Application number
DEA44669D
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German (de)
Inventor
Kr Bitterfeld
Dr Wilhelm Buttenschoen
Dr Theodor Mariam
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
IG Farbenindustrie AG
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IG Farbenindustrie AG
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Filing date
Publication date
Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to DEA44669D priority Critical patent/DE448738C/en
Application granted granted Critical
Publication of DE448738C publication Critical patent/DE448738C/en
Expired legal-status Critical Current

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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
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
    • C08G12/24—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with sulfonic acid amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/13—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
    • C07C309/14—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton containing amino groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
    • C07C309/46—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton having the sulfo groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • 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
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
    • C08G12/06—Amines

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung von wasserlöslichen Kondensationsprodukten aus Aminoverbindungen oder Säureamiden und Acetaldehyddisulfosäure. Durch die Arbeiten von B u c h e r e r und Schwalbe, Ber. d. d. chem. Ges. 39 [rgo6], Sexte a796, sind Kondensationsprodukte von primären und sekundären Aminen mit Aldehydbisulfiten bekannt geworden, die als w-Sulfosäuren bezeichnet werden. Es sind wasserlösliche Verbindungen, die sich durch leichte hydrolytische Spaltbarkeit auszeichnen.Process for the preparation of water-soluble condensation products from amino compounds or acid amides and acetaldehyde disulfonic acid. By working by B u c h e r e r and Schwalbe, Ber. d. d. chem. Ges. 39 [rgo6], Sexte a796, are Condensation products of primary and secondary amines with aldehyde bisulfites are known which are known as w-sulfonic acids. They are water-soluble compounds which are characterized by easy hydrolytic cleavage.

Es hat sich nun gezeigt, daß man zu Kondensationsprodukten mit ähnlichen Eigenschaften gelangt, wenn man an Stelle von Aldehvdbisulfiten Acetaldehyddisulfosäure auf Aminov erbindungen einwirken läßt. Während die nach B u c h e r e r erhaltenen Kondensationsprodukte die allgemeine Formel X-N -R-CH-R'-S03H (X - Alkyl oder Aryl; R und R' - Alky1, Aryl oder H) besitzen, lassen sich die nach vorliegendem Verfahren erhältlichen Körper von der allgemeinen Formel R-N : CH-CH (SO;H), (R - Alkyl, Aryl oder Säurerest) ableiten. Es sind also Verbindungen nach Art der Schiffschen Basen, die in der Seitenkette zwei Sulfogruppen enthalten. Die neuen Kondensationsprodukte bieten in noch höherem Maße als die Aldehydbisulfid-Kondensationsprodukte die Möglichkeit, schwer lösliche Aminoverbindungen ohne Zuhilfenahme von Säure leicht wasserlöslich zu machen, weshalb sie weitergehende Verwendung finden als jene. Sie sind nämlich selbst dann noch wasserlöslich, wenn sie sich von höher molekularen Aminoverbindungen herleiten, deren Aldehydbisulfitverbindungen bereits schwer löslich sind.It has now been shown that condensation products with similar Properties obtained when acetaldehyde disulfonic acid is used instead of aldehyde bisulfites affects Aminov connections. While the after B u c h e r e r received Condensation products have the general formula X-N -R-CH-R'-SO3H (X - alkyl or aryl; R and R '- alkyl, aryl or H) can be used according to the present process available body of the general formula R-N: CH-CH (SO; H), (R - alkyl, aryl or acid residue). So there are connections in the manner of Schiff's bases, which contain two sulfo groups in the side chain. The new condensation products offer the possibility to an even greater extent than the aldehyde bisulfide condensation products poorly soluble amino compounds easily soluble in water without the aid of acid to make, which is why they are used more widely than those. Because you are even then still water-soluble if they are made up of higher molecular weight amino compounds derive whose aldehyde bisulfite compounds are already sparingly soluble.

Hierauf und auf ihrer leichten hydrolytischen Spaltbarkeit beruht unter anderm ihre Verwendung als Zwischenprodukte zur Herstellung von Azofarbstoffen. Kondensationsprodukte von Acetaldehyddisulfosäure mit Farbbasen, die freie Aminogruppen enthalten, können unmittelbar als Farbstoffe verwendet werden.This is based on this and on their easy hydrolytic cleavage among other things their use as intermediate products for the production of azo dyes. Condensation products of acetaldehyde disulfonic acid with color bases containing free amino groups can be used directly as dyes.

Beispiel r. 3oo Teile acetaldehyddisulfosaures Kalium werden in der Wärme in z 6oo Teilen Wasser gelöst und mit 68 Teilen Methylaminchlorhydrat behandelt. In der Kälte scheiden sich :28o Teile des farblosen Kondensationsproduktes aus.Example r. 300 parts of potassium acetaldehyde disulfonate are used in the Heat dissolved in 600 parts of water and treated with 68 parts of methylamine chlorohydrate. In the cold: 28o parts of the colorless condensation product separate out.

B e i s p i e 1 a. Eine heiße Lösung von 3.1o Teilen acetaldehyddisulfosaurem Barium in der fünffachen Wassermenge wird mit 6o Teilen Harnstoff versetzt. Beim Erkalten scheidet sich das aus i Mol. Harnstoff und i Mol. acetaldehyddisulfosaurem Barium entstandene Reaktionsprodukt in Form schneeweißer Kristalle aus.Example 1 a. A hot solution of 3.1o parts acetaldehyddisulfosaurem Sixty parts of urea are added to barium in five times the amount of water. At the Cool down it separates from 1 mol. urea and 1 mol. acetaldehyddisulfosaurem Barium formed reaction product in the form of snow-white crystals.

Beispiel 3. 248 Teile acetaldehyddisulfosaures Natrium werden in der sechsfachen Menge Wasser gelöst und io9 Teile m-Aminophenol zugesetzt. Aus der so erhaltenen Lösung läßt sich das m-oxyanilidoacetaldehvddisulfosaure Natrium mit einer Ausbeute von 98 Prozent mit Kochsalz aussalzen.Example 3. 248 parts of sodium acetaldehyde disulphonate are used in the Dissolved six times the amount of water and added 10 9 parts of m-aminophenol. From the so The solution obtained can be mixed with sodium m-oxyanilidoacetaldehydisulfosaure Salt out with table salt for a yield of 98 percent.

Beispiel q.. In eine heiße Lösung von 3oo Teilen acetaldehyddisulfosaurem Kalium in der achtfachen Menge Wasser werden 1z3 Teile o-Dianisidinbase eingetragen. Nach dem Aussalzen mit 3oo Teilen Chlorkalium erhält man 92 Prozent der Theorie an o-dianisi@dindiacetaldehvddisulfosaurem Kalium. B e i s p i e 1 5. 75 Teile acetaldehyddisulfosaures Natrium, gelöst in 5oo Teilen Wasser, werden mit 25 Teilen Chrysoidinbase in der Wärme digeriert. Die erhaltene Lösung wird mit r25 Teilen Kochsalz ausgesalzen und das Kondensationsprodukt bei niedriger Temperatur getrocknet. Man erhält 103 g eines noch kochsalzhaltigen dunkelbraunroten Pulvers, welches Acetatseide aus neutralem Bade in sattem rotem Gelb anfärbt.Example q .. 1t3 parts of o-dianisidine base are introduced into a hot solution of 300 parts of potassium acetaldehyde disulfonate in eight times the amount of water. After salting out with 300 parts of potassium chloride, 92 percent of the theory of potassium o-dianisi @ dindiacetaldehvddisulfosaurem is obtained. Example 1 5. 75 parts of sodium acetaldehyde disulfonate, dissolved in 500 parts of water, are digested with 25 parts of chrysoidin base in the heat. The solution obtained is salted out with 25 parts of common salt and the condensation product is dried at low temperature. 103 g of a dark brown-red powder which still contains saline and which dyes acetate silk from a neutral bath in a deep red yellow are obtained.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von wasserlöslichen Kondensationsprodukten aus Aminoverbindung.en oder Säureamiden und Acetald.ehydd'isulfosüure, dadurch gekennzeichnet, daß man Acetaldehyddisulfosäure oder ihre Salze auf aliphatische oder aromatische Aminoverbindungen bzw. auf Siäureamxde einwirken gärt.PATENT CLAIM: Process for the production of water-soluble condensation products from Aminoverbindungen.en or acid amides and Acetald.ehydd'isulfosüure, characterized in that that one acetaldehyde disulfonic acid or its salts to aliphatic or aromatic Amino compounds and / or on Siäureamxde ferment.
DEA44669D 1925-04-08 1925-04-08 Process for the preparation of water-soluble condensation products from amino compounds or acid amides and acetaldehyde disulfonic acids Expired DE448738C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEA44669D DE448738C (en) 1925-04-08 1925-04-08 Process for the preparation of water-soluble condensation products from amino compounds or acid amides and acetaldehyde disulfonic acids

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEA44669D DE448738C (en) 1925-04-08 1925-04-08 Process for the preparation of water-soluble condensation products from amino compounds or acid amides and acetaldehyde disulfonic acids

Publications (1)

Publication Number Publication Date
DE448738C true DE448738C (en) 1927-08-26

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