DE1125905B - Process for the production of nonionic, surface-active polyoxyureas - Google Patents

Process for the production of nonionic, surface-active polyoxyureas

Info

Publication number
DE1125905B
DE1125905B DED33644A DED0033644A DE1125905B DE 1125905 B DE1125905 B DE 1125905B DE D33644 A DED33644 A DE D33644A DE D0033644 A DED0033644 A DE D0033644A DE 1125905 B DE1125905 B DE 1125905B
Authority
DE
Germany
Prior art keywords
active
polyoxyureas
nonionic
production
water
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
Application number
DED33644A
Other languages
German (de)
Inventor
Dr Ernst Ulsperger
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.)
Akademie der Wissenschaften der DDR
Original Assignee
Akademie der Wissenschaften der DDR
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Akademie der Wissenschaften der DDR filed Critical Akademie der Wissenschaften der DDR
Priority to DED33644A priority Critical patent/DE1125905B/en
Publication of DE1125905B publication Critical patent/DE1125905B/en
Pending legal-status Critical Current

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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4833—Polyethers containing oxyethylene units
    • 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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
    • 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/73—Polyisocyanates or polyisothiocyanates acyclic

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

Description

Verfahren zur Herstellung nichtionogener, grenzflächenaktiver Polyoxyharnstoffe Es wurde gefunden, daß Mono- und Diisocyanate, z. B. n-Octylisocyanat oder Octamethylen-diisocyanat mit mehr als 5 C-Atomen in der Kette mit Polyoxyaminen wie beispielsweise Glucamin, N-Methylglucamin, N-Methyl-maltosamin und N-N"-Digluconyl-diäthylen-triamin in Wasser bei Temperaturen von 20 bis 100= C oder Alkoholen, wie beispielsweise Methylalkohol, zu nichtionogenen, grenzflächenaktiven Polyhydroxyharnstoffen umgesetzt werden können, ohne daß in einer gleichzeitigen Nebenreaktion die entsprechenden N-N'-disubstituierten Harnstoffe oder Urethane in nennenswerter Menge gebildet werden. Für eine gute Verteilung des mit Wasser nicht mischbaren Isocyanats im Reaktionsgemisch ist durch mechanisches Rühren oder Schütteln Sorge zu tragen.Process for the preparation of nonionic, surface-active polyoxyureas It has been found that mono- and diisocyanates, e.g. B. n-octyl isocyanate or octamethylene diisocyanate with more than 5 carbon atoms in the chain with polyoxyamines such as glucamine, N-methylglucamine, N-methyl-maltosamine and N-N "-digluconyl-diethylenetriamine in water at temperatures from 20 to 100 = C or alcohols, such as methyl alcohol, can be converted to nonionic, surface-active polyhydroxyureas, without the corresponding N-N'-disubstituted in a simultaneous side reaction Urea or urethanes are formed in appreciable quantities. For a good distribution of the water-immiscible isocyanate in the reaction mixture is mechanical Take care of stirring or shaking.

Die nach dem Verfahren der Erfindung herstellbaren Verbindungen werden als Textilhilfsmittel, Waschmittel, Körperreinigungsmittel, Netzmittel und als Emulgatoren verwendet. Beispiel 1 N-Methyl-N-(2,3,4,5,6-penta-hydroxy-n-hexyl)-N'-n-octyl-harnstoff CH2-N-(CH3)-CO-NH-CH,-CH2-CH,-CH2-CI2-CH,-CH2-CHg H C O H 1 g N-Methylglucamin werden bei 20° C in 5 ccm Wasser gelöst. Die wäßrige Lösung wird mit 0,8 g HOCH n-Octylisocyanat versetzt und kräftig geschüttelt. Sie erstarrt nach kurzer Zeit zu einer homogenen Masse. C H O H 3o Dem Reaktionsprodukt wird das Wasser entzogen und das Rohprodukt aus einem Methylalkohol-Äther- Gemisch (10 ccm Methanol und 10 ccm Äther) um- C H O H kristallisiert. Weiße Substanz vom Schmelzpunkt 105 bis 108° C. (i HJ-) H 17,8 g D-Gluconsäure-8-lacton werden unter Rückfluß und Feuchtigkeitsausschluß in 450 ccm abs. Methanol gelöst, 5,15 g Diäthylentriamin hinzugefügt und die Lösung 1 Stunde lang zum Sieden erhitzt. Nach dem Abkühlen gibt man 7,75 g n-Octyl isocyanat hinzu, wonach sich in kurzer Zeit das Reaktionsprodukt abscheidet. Es wird aus Wasser, dann aus Wasser-Aceton umkristallisiert und schmilzt bei 176 bis 177° C. Die Ausbeute ist nahezu quantitativ. 1,95 g N-Methylglucamin werden bei 20° C in 10 ccm Wasser gelöst, mit 0,84 g Hexamethylendiisocyanat versetzt und kräftig geschüttelt. Nach Ablauf der Reaktion wird von ungelösten Anteilen getrennt und die wäßrige Lösung unter Vakuum und über P20" bis zur vollständigen Trockne eingedampft. Das Rohprodukt wird durch Umfällen aus Methanol-Äther gereinigt. Weiße Substanz vom Schmelzpunkt 132 bis 134° C.The compounds which can be prepared by the process of the invention are used as textile auxiliaries, detergents, personal cleansing agents, wetting agents and as emulsifiers. example 1 N-methyl-N- (2,3,4,5,6-penta-hydroxy-n-hexyl) -N'-n-octyl urea CH2-N- (CH3) -CO-NH-CH, -CH2-CH, -CH2-CI2-CH, -CH2-CHg HCOH 1 g of N-methylglucamine are at 20 ° C in 5 ccm Dissolved in water. The aqueous solution is 0.8 g HOCH n-octyl isocyanate added and shaken vigorously. she solidifies after a short time to a homogeneous mass. CHOH 3o The water is removed from the reaction product and the crude product from a methyl alcohol ether Mixture (10 ccm methanol and 10 ccm ether) CHOH crystallizes. White matter with a melting point of 105 up to 108 ° C. (i HJ-) H 17.8 g of D-gluconic acid-8-lactone are under reflux and with exclusion of moisture in 450 ccm abs. Dissolved methanol, added 5.15 g of diethylenetriamine and heated the solution to boiling for 1 hour. After cooling, 7.75 g of n-octyl isocyanate are added, after which the reaction product separates out in a short time. It is recrystallized from water and then from water-acetone and melts at 176 to 177 ° C. The yield is almost quantitative. 1.95 g of N-methylglucamine are dissolved in 10 cc of water at 20 ° C., 0.84 g of hexamethylene diisocyanate are added and the mixture is shaken vigorously. After the end of the reaction, undissolved constituents are separated and the aqueous solution is evaporated to complete dryness under vacuum and over P20 ". The crude product is purified by reprecipitation from methanol-ether. White substance with a melting point of 132 to 134 ° C.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung nichtionogener, grenzflächenaktiver Polyoxyhamstoffe, dadurch gekennzeichnet, daß Mono- oder Diisocyanate mit mehr als 5 C-Atomen in der Kette mit Polyoxyaminen in Wasser und heterogener Phase bei 20 bis 100° C unter mechanischem Rühren oder Schütteln oder in Methanol als Lösungsmittel umgesetzt werden.PATENT CLAIM: Process for the production of non-ionic, surface-active Polyoxyureas, characterized in that mono- or diisocyanates with more than 5 carbon atoms in the chain with polyoxyamines in water and heterogeneous phase at 20 up to 100 ° C with mechanical stirring or shaking or in methanol as solvent implemented.
DED33644A 1957-08-05 1957-08-05 Process for the production of nonionic, surface-active polyoxyureas Pending DE1125905B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DED33644A DE1125905B (en) 1957-08-05 1957-08-05 Process for the production of nonionic, surface-active polyoxyureas

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DED33644A DE1125905B (en) 1957-08-05 1957-08-05 Process for the production of nonionic, surface-active polyoxyureas

Publications (1)

Publication Number Publication Date
DE1125905B true DE1125905B (en) 1962-03-22

Family

ID=7041832

Family Applications (1)

Application Number Title Priority Date Filing Date
DED33644A Pending DE1125905B (en) 1957-08-05 1957-08-05 Process for the production of nonionic, surface-active polyoxyureas

Country Status (1)

Country Link
DE (1) DE1125905B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0383023A2 (en) * 1989-02-13 1990-08-22 Südzucker Aktiengesellschaft Mannheim/Ochsenfurt Polymerisable N'-polyhydroxy-N'-alkyl urea derivatives, process for their preparation, their use and their homo- or copolymers
EP0383024A2 (en) * 1989-02-13 1990-08-22 Südzucker Aktiengesellschaft Mannheim/Ochsenfurt N-polyhydroxy-N'-alkyl urea derivatives, process for their preparation and their use

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0383023A2 (en) * 1989-02-13 1990-08-22 Südzucker Aktiengesellschaft Mannheim/Ochsenfurt Polymerisable N'-polyhydroxy-N'-alkyl urea derivatives, process for their preparation, their use and their homo- or copolymers
EP0383024A2 (en) * 1989-02-13 1990-08-22 Südzucker Aktiengesellschaft Mannheim/Ochsenfurt N-polyhydroxy-N'-alkyl urea derivatives, process for their preparation and their use
EP0383023A3 (en) * 1989-02-13 1991-03-20 Südzucker Aktiengesellschaft Mannheim/Ochsenfurt Polymerisable N'-polyhydroxy-N'-alkyl urea derivatives, process for their preparation, their use and their homo- or copolymers
EP0383024A3 (en) * 1989-02-13 1991-03-27 Südzucker Aktiengesellschaft Mannheim/Ochsenfurt N-polyhydroxy-n'-alkyl urea derivatives, process for their preparation and their use

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