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DE935025C - Process for the preparation of super polymeric condensation products - Google Patents

Process for the preparation of super polymeric condensation products

Info

Publication number
DE935025C
DE935025C DED4105D DED0004105D DE935025C DE 935025 C DE935025 C DE 935025C DE D4105 D DED4105 D DE D4105D DE D0004105 D DED0004105 D DE D0004105D DE 935025 C DE935025 C DE 935025C
Authority
DE
Germany
Prior art keywords
super
condensation products
preparation
polymeric condensation
carbon atoms
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
DED4105D
Other languages
German (de)
Inventor
Winfried Dr Hentrich
Alfred Dr Kirstahler
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.)
DEHYDAG GmbH
Dehydag Deutsche Hydrierwerke GmbH
Original Assignee
DEHYDAG GmbH
Dehydag Deutsche Hydrierwerke GmbH
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 DEHYDAG GmbH, Dehydag Deutsche Hydrierwerke GmbH filed Critical DEHYDAG GmbH
Priority to DED4105D priority Critical patent/DE935025C/en
Application granted granted Critical
Publication of DE935025C publication Critical patent/DE935025C/en
Expired 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
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
    • C08G18/3863—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing groups having sulfur atoms between two carbon atoms, the sulfur atoms being directly linked to carbon atoms or other sulfur atoms
    • C08G18/3865—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing groups having sulfur atoms between two carbon atoms, the sulfur atoms being directly linked to carbon atoms or other sulfur atoms containing groups having one sulfur atom between two carbon atoms
    • 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
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/775—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur sulfur
    • 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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
    • C08G63/6884—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/6886—Dicarboxylic acids and dihydroxy 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyesters Or Polycarbonates (AREA)

Description

(WiGBl. S. 175)(WiGBl. P. 175)

AUSGEGEBEN AM 10. NOVEMBER 1955ISSUED NOVEMBER 10, 1955

D D. 4105 IVc4105 IVc

(Ges. v. 15. 7. 19-5Ij (Ges. V. July 15, 19-5Ij

Es wurde gefunden, daß man wertvolle superpolymere Kondensationsprodukte erhält, wenn man Glykole mit mindestens 4 Kohlenstoffatomen, welche die Hydroxylgruppen möglichst endständig, jedenfalls an 2 verschiedene, nicht benachbarte aliphatisch^ Kohlenstoffatom; gebunden enthalten und in der Kohleiistoffolge ein oder mehrmals durch S, S O oder insbesondere S O., unterbrochen sind, mit Dicarbonsäuren bzw. deren funktionellen Derivaten oder auch Diisocyanaten bzw. Diisothiocyanaten, die in der Kohlenstoffolge ein oder mehrmals durch eine Snlfoiigruppe unterbrochen sind, bis zur Bildung superpolymerer Erzeugnisse auf Temperaturen zwischen 150 und 300- erhitzt.It has been found that valuable superpolymeric condensation products are obtained if glycols with at least 4 carbon atoms, which the hydroxyl groups as terminally as possible, at least on 2 different, non-adjacent aliphatic carbon atoms; contain bound and are interrupted one or more times in the carbon sequence by S, SO or in particular S O. heated to temperatures between 150 and 300- to form super polymeric products.

Solche Stoffe sind beispielsweise Äthylen-bissulfonessigsäure, Diäthyl - snlfon -2, 2 - dicarbonsäure, Diäthyl-sulfon-2, 2'-diisocyanat, Di-n-hexylsulfon-6. ö'-diisocyanat. Hierbei können auch Ausgangsstoffe verwendet werden, die die Kohlenstoffatome in cyclischer Anordnung enthalten. Schließ-Hch lassen sich auch (^-Aminocarbonsäuren oder andere bifunktionelle Stoffe bei der Kondensation mitverwenden. Die so erhaltenen superpolymeren Kondensationsprodukte sind vornehmlich durch eine gewisse Hydrophil ie ausgezeichnet.Such materials are for example ethylene bissulfonessigsäure, diethyl - snlfon -2, 2 - dicarboxylic acid, diethyl sulfone-2, 2'-diisocyanate, di-n-hexylsulfon-sixth ö'-diisocyanate. It is also possible here to use starting materials which contain the carbon atoms in a cyclic arrangement. In addition, (^ -aminocarboxylic acids or other bifunctional substances can also be used in the condensation. The superpolymeric condensation products obtained in this way are primarily distinguished by a certain hydrophilicity.

Beispielexample

Erhitzt man äquimolekulare Mengen von 2, 2'-Dioxydiäthyl-sulfon und Di-n-hexyl-sulfon-6,6'-diisocyanat in Gegenwart eines geeigneten Lösungs- oder Verteilungsmittels während 1 bis 2 Stunden am RückflulJkühler sowie 2 weitere StundenEquimolecular amounts of 2,2'-dioxydiethyl-sulfone and di-n-hexyl-sulfone-6,6'-diisocyanate are heated in the presence of a suitable solvent or distribution agent for 1 to 2 hours on the reflux condenser and for 2 more hours

nach dem Abdestillieren der zugesetzten Hilfsflüssigkeit im Vakuum von etwa 2 mm auf 220 bis 2400, so erhält man ein helles superpolymeres Produkt, das sich aus dem Schmelzfluß zu Fäden verspinnen läßt.after the added auxiliary liquid has been distilled off in vacuo from about 2 mm to 220 to 240 ° , a light-colored superpolymeric product is obtained which can be spun into threads from the melt flow.

Claims (1)

PATENTANSPRUCH:PATENT CLAIM: Verfahren zur Herstellung superpolymerer Kondensationsprodukte aus Glykolen mit mindestens 4 Kohlenstoffatomen, welche die Hydroxylgruppen möglichst endständig, jedenfalls an 2 verschiedene, nicht benachbarte aliphatische Kohlenstoffatome gebunden enthalten und in der Kohlenstoffolge ein- oder mehrmals durch S, SO oder insbesondere durch SO3 unterbrochen sind, und Dicarbonsäuren bzw. ihren funktioneilen Derivaten oder Diisocyanaten, dadurch gekennzeichnet, daß man die beschriebenen Glykole mit solchen Dicarbonsäuren oder deren funktionellen Derivaten oder Diisocyanaten bzw. Diisothiocyanaten, die in der Kohlenstoffolge ein oder mehrmals durch die Sulfongruppe unterbrochen sind, bis zur Bildung superpolymerer Erzeugnisse auf Temperaturen zwischen 150 und 3000 erhitzt.Process for the production of super polymeric condensation products from glycols with at least 4 carbon atoms, which contain the hydroxyl groups as terminally as possible, in any case bound to 2 different, non-adjacent aliphatic carbon atoms and are interrupted one or more times in the carbon sequence by S, SO or in particular by SO 3, and Dicarboxylic acids or their functional derivatives or diisocyanates, characterized in that the glycols described with such dicarboxylic acids or their functional derivatives or diisocyanates or diisothiocyanates, which are interrupted one or more times in the carbon sequence by the sulfone group, up to the formation of superpolymer products at temperatures heated between 150 and 300 0. Angezogene Druckschriften:Referred publications: Französische Patentschrift Nr. 845917; deutsche Patentschrift Nr. 728981;
USA.-Patentschriften Nr. 2191556, 2071 251.French Patent No. 845917; German Patent No. 728981;
U.S. Patent Nos. 2191556, 2071 251. © 509571 11.55© 509571 11.55
DED4105D 1942-04-23 1942-05-30 Process for the preparation of super polymeric condensation products Expired DE935025C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DED4105D DE935025C (en) 1942-04-23 1942-05-30 Process for the preparation of super polymeric condensation products

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE894134X 1942-04-23
DED4105D DE935025C (en) 1942-04-23 1942-05-30 Process for the preparation of super polymeric condensation products

Publications (1)

Publication Number Publication Date
DE935025C true DE935025C (en) 1955-11-10

Family

ID=25955816

Family Applications (1)

Application Number Title Priority Date Filing Date
DED4105D Expired DE935025C (en) 1942-04-23 1942-05-30 Process for the preparation of super polymeric condensation products

Country Status (1)

Country Link
DE (1) DE935025C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1149519B (en) * 1961-02-27 1963-05-30 Bayer Ag Process for the production of non-thermoplastic, non-meltable plastics based on polyhydroxyl compounds and polyisocyanates containing sulfone groups

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2071251A (en) * 1931-07-03 1937-02-16 Du Pont Fiber and method of producing it
FR845917A (en) * 1937-11-12 1939-09-05 Ig Farbenindustrie Ag Process for the production of polymerization products and products obtained by this process
US2191556A (en) * 1936-07-01 1940-02-27 Du Pont Polyamides
DE728981C (en) * 1937-11-13 1942-12-07 Ig Farbenindustrie Ag Process for the production of polyurethanes or polyureas

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2071251A (en) * 1931-07-03 1937-02-16 Du Pont Fiber and method of producing it
US2191556A (en) * 1936-07-01 1940-02-27 Du Pont Polyamides
FR845917A (en) * 1937-11-12 1939-09-05 Ig Farbenindustrie Ag Process for the production of polymerization products and products obtained by this process
DE728981C (en) * 1937-11-13 1942-12-07 Ig Farbenindustrie Ag Process for the production of polyurethanes or polyureas

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1149519B (en) * 1961-02-27 1963-05-30 Bayer Ag Process for the production of non-thermoplastic, non-meltable plastics based on polyhydroxyl compounds and polyisocyanates containing sulfone groups

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