CH396022A - Process for the preparation of new water-soluble compounds containing epoxy groups - Google Patents

Process for the preparation of new water-soluble compounds containing epoxy groups

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Publication number
CH396022A
CH396022A CH1166464A CH1166464A CH396022A CH 396022 A CH396022 A CH 396022A CH 1166464 A CH1166464 A CH 1166464A CH 1166464 A CH1166464 A CH 1166464A CH 396022 A CH396022 A CH 396022A
Authority
CH
Switzerland
Prior art keywords
radical
soluble compounds
epoxy groups
preparation
formula
Prior art date
Application number
CH1166464A
Other languages
German (de)
Inventor
Batzer Hans Dr Prof
Willy Dr Fisch
Daniel Dr Porret
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Priority to CH1166464A priority Critical patent/CH396022A/en
Priority claimed from CH7833359A external-priority patent/CH395114A/en
Publication of CH396022A publication Critical patent/CH396022A/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00Polycondensates 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
    • C08G59/18Macromolecules 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
    • C08G59/20Macromolecules 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 epoxy compounds used
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00Polycondensates 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
    • C08G59/18Macromolecules 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
    • C08G59/20Macromolecules 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 epoxy compounds used
    • C08G59/22Di-epoxy compounds
    • C08G59/26Di-epoxy compounds heterocyclic
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00Polycondensates 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
    • C08G59/18Macromolecules 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
    • C08G59/20Macromolecules 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 epoxy compounds used
    • C08G59/32Epoxy compounds containing three or more epoxy groups
    • C08G59/3236Heterocylic compounds
    • C08G59/3245Heterocylic compounds containing only nitrogen as a heteroatom
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423Amino-aldehyde resins
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/55Epoxy resins

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Epoxy Resins (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

  

  Verfahren zur Herstellung von neuen epoxydgruppenhaltigen wasserlöslichen Verbindungen    Gegenstand des vorliegenden Patentes ist ein       Verfahren    zur Herstellung von neuen, mindestens  zwei Epoxydgruppen enthaltenden, wasserlöslichen  Verbindungen der Formel  
EMI0001.0001     
    worin Z einen mindestens eine Epoxydgruppe ent  haltenden Alkylrest bedeutet und worin Y für einen  Rest -CH=CH2 oder einen Rest -CH2-CH2-O-Z  steht.  



  Die neuen Epoxyde werden erfindungsgemäss er  halten, indem man Derivate des     Triacrylylperhydro-          triazins    der Formel  .,  
EMI0001.0004     
    worin Z' einen     mindestens    eine Halogenwasserstoff  gruppierung enthaltenden Alkylrest bedeutet und  worin Y' für einen Rest -CH=CH2 oder einen Rest  -CH2CH2-O-Z' steht, mit halogenwasserstoffabspal    tenden Mitteln behandelt.  



  Die beim erfindungsgemässen Verfahren als Aus  gangsstoffe verwendeten ungesättigten Verbindungen    der Formel (II) sind beispielsweise zugänglich, indem  man in einer ersten Stufe mindestens 2 Mol eines  Alkohols der Formel Z'-OH an 1 Mal     Triacrylyl-          perhydrotriazin    anlagert.  



  Der Alkohol Z'-OH enthält eine epoxydierbare  Gruppe. Genannt seien das     Glycerin-ss-monochlor-          hydrin,    GLycerin-a-bromhydrin und insbesondere  Glycerin-a-monochlorhydrin sowie Mischungen sol  cher Monochlorhydrine, wie z. B. das technische Ge  misch von Glycerin-ss-monochlorhydrin und     Glycerin-          a-monochlorhydrin.     



  Die Anlagerung des Alkohols Z'-OH an die  C=C-Doppelbindung der a,B-ungesättigten Verbin  dungen erfolgt zweckmässig in an sich bekannter  Weise in     Gegenwart    von basischen Katalysatoren,  wie Natriumhydroxyd oder insbesondere von sauren  Katalysatoren bzw. Lewis-Säuren, wie z. B. Schwe  felsäure oder Bortrifluorid.  



  Die     erfindungsgemässe        Behandlung        umfasst    die       Einwirkung    von Halogenwasserstoff abspaltenden  Mitteln, wie Kaliumhydroxyd oder Natriumhydroxyd  auf die Halogenhydringruppen, z. B. die     Glycerin-          monochlorhydringruppe,    unter Bildung der entspre  chenden 1,2-Epoxydgruppe bzw. einer     Glycidyl-          gruppe.     



  Bei der Epoxydierung können neben den     Di-          bzw.    Polyepoxyden infolge Nebenreaktionen gleich  zeitig auch ganz oder nur teilweise hydrolysierte  Epoxyde entstehen, das heisst Verbindungen, bei  denen die Epoxydgruppe des Polyepoxyds der For  mel (I)     ganz    oder teilweise zu     Hydraxylgruppen     verseift worden sind.  



  Es wurde festgestellt, dass die     Anwesenheit    sol  cher Nebenprodukte die     technischen    Eigenschaften  der gehärteten     Polyepoxyde    in der Regel     günstig        be-          einflussen.    Daher empfiehlt es sich im     allgemeinen,         auf eine Isolierung der reinen Polyepoxyde aus dem  Reaktionsgemisch zu verzichten.  



  Die Verbindungen der Formel (1) reagieren mit  den üblichen Härtern für Epoxydverbindungen. Sie  lassen sich daher durch Zusatz solcher Härter analog  wie andere polyfunktionelle Epoxydverbindungen  bzw. Epoxyharze vernetzen bzw. aushärten. Sie  eignen sich besonders gut zum     Veredeln,    speziell  zum Knitterechtmachen, insbesondere von     hydroxy-          lierten    Faserstoffen, wie Cellulose. Das Textilmaterial  wird zu diesem Zweck mit einer wässrigen Flotte,  welche eine Verbindung (I) und ferner einen in der  Wärme Säure abspaltenden Katalysator gelöst ent  hält, imprägniert und nach dem Trocknen bei er  höhter     Temperatur    gehärtet.  



  Als in der Wärme Säure abspaltende Härtungs  katalysatoren kommen z. B. in Frage: Ammonium  salze starker Säuren, wie Ammoniumchlorid, Ammo  niumsulfat, Ammoniumsilikofluorid oder Metallsalze,  wie Magnesiumchlorid, Zinknitrat, vorzugsweise je  doch Friedel-Crafts-Katalysatoren, wie Aluminium  chlorid, Borfluorid und dessen Komplexverbindun  gen, insbesondere Zinkfluorborat.  



  Die Imprägnierung kann unter den üblichen Be  dingungen und in den üblichen Apparaturen erfolgen,  wie sie für die Knitterfreiausrüstung bekannt sind.  Die Härtung     erfolgt    vorzugsweise zwischen 120 bis  160 . Werden sogenannte Düsentrockner verwendet,  so kann die Trocknung und Härtung in einem Ar  beitsgang     erfolgen.     



  Wird ein solches Veredlungsverfahren zur Fixie  rung von mechanisch erzeugten Effekten herangezo  gen, so können die bei diesen     Verfahren    üblichen  Zusätze, wie Weichmacher, Polyvinylalkohol usw.  gemacht werden.    Anstatt eine Verbindung der Formel (I) allein       anzuwenden,    können sie auch in Mischung mit  Aminoplasten, z. B. Melamin-, Harnstoff-, Äthylen-.  harnstoff-Formaldehydkondensationsprodukten, ver  wendet werden, wobei vorteilhaft solche Aminoplaste  benützt werden, die ein geringes Chlorrückhalte  vermögen aufweisen.  



  Als hydroxylierte Faserstoffe, die mit den Ver  bindungen (I) veredelt werden können, kommen  solche aus Polyvinylalkohol und insbesondere Cellu  lose enthaltende Materialien in Betracht. Hierbei  können solche aus regenerierter Cellulose, wie  Viskosegewebe oder solche aus natürlicher Cellu  lose, z. B. Baumwollgewebe oder Leinenstoffe, be  handelt werden.  



  Im nachfolgenden Beispiel bedeuten Teile Ge  wichtsteile, Prozente Gewichtsprozente; das Ver  hältnis der Gewichtsteile zu den Volumteilen ist  dasselbe wie beim Kilogramm zum Liter; die Tempe  raturen sind in Celsiusgraden angegeben.  



  <I>Beispiel</I>  Eine Mischung von 50 Teilen     Triacrylylperhydro-          triazin,    67 Teilen Glycerin-monochlorhydrin und  100 Volumteilen Benzol wird unter Schütteln mit 27  Teilen gepulverter NaOH (97%ig) versetzt. Es tritt  eine exotherme Reaktion auf, die 45 Minuten dauert,  wobei die Temperatur auf 35-40' gehalten wird.  Nach einer Stunde lässt man abkühlen, filtriert vom  gebildeten     Kochsalz    ab und engt im Vakuum ein.  Man erhält 85 Teile eines zähflüssigen, vollständig  wasserlöslichen Harzes mit einem Epoxydgehalt  von 5,45     Epoxydäquivalenten    pro kg.  



  Es besteht in der Hauptsache aus dem     Triepoxyd     der Formel  
EMI0002.0013     
    und kann beispielsweise für die Textilappretur verwendet werden.



  Process for the preparation of new water-soluble compounds containing epoxy groups The subject of the present patent is a process for the preparation of new water-soluble compounds of the formula containing at least two epoxy groups
EMI0001.0001
    where Z is an alkyl radical containing at least one epoxy group and where Y is a radical -CH =CH2 or a radical -CH2-CH2-O-Z.



  According to the invention, the new epoxides are kept by using derivatives of triacrylyl perhydrotriazines of the formula.
EMI0001.0004
    where Z 'denotes an alkyl radical containing at least one hydrogen halide group and where Y' denotes a radical -CH = CH2 or a radical -CH2CH2-O-Z ', treated with agents which split off hydrogen halide.



  The unsaturated compounds of the formula (II) used as starting materials in the process according to the invention can be obtained, for example, by adding at least 2 mol of an alcohol of the formula Z'-OH to triacrylyl perhydrotriazine once in a first stage.



  The alcohol Z'-OH contains an epoxidizable group. The glycerol-ss-monochlorohydrin, GLycerol-a-bromohydrin and in particular glycerol-a-monochlorohydrin and mixtures of such monochlorohydrins, such as. B. the technical Ge mixture of glycerol-ss-monochlorohydrin and glycerol-a-monochlorohydrin.



  The addition of the alcohol Z'-OH to the C = C double bond of the a, B-unsaturated connec tions is expediently carried out in a manner known per se in the presence of basic catalysts, such as sodium hydroxide or, in particular, of acidic catalysts or Lewis acids, such as z. B. sulfuric acid or boron trifluoride.



  The treatment according to the invention comprises the action of agents that split off hydrogen halide, such as potassium hydroxide or sodium hydroxide, on the halohydrin groups, e.g. B. the glycerol monochlorohydrin group, with the formation of the corresponding 1,2-epoxy group or a glycidyl group.



  During epoxidation, in addition to di- or polyepoxides as a result of side reactions, completely or only partially hydrolyzed epoxides can be formed at the same time, i.e. compounds in which the epoxy group of the polyepoxide of the formula (I) has been wholly or partially saponified to hydraxyl groups.



  It was found that the presence of such by-products generally favorably influence the technical properties of the cured polyepoxides. It is therefore generally advisable not to isolate the pure polyepoxides from the reaction mixture.



  The compounds of formula (1) react with the usual hardeners for epoxy compounds. By adding such hardeners, they can therefore be crosslinked or cured in the same way as other polyfunctional epoxy compounds or epoxy resins. They are particularly suitable for finishing, especially for making crease-proof, especially hydroxylated fiber materials such as cellulose. For this purpose, the textile material is impregnated with an aqueous liquor which contains a compound (I) and also a catalyst which splits off acid when heated, and, after drying, hardened at an elevated temperature.



  As the heat-releasing acid curing catalysts come z. B. in question: ammonium salts of strong acids, such as ammonium chloride, ammonium sulfate, ammonium fluorosilicate or metal salts such as magnesium chloride, zinc nitrate, but preferably Friedel-Crafts catalysts such as aluminum chloride, boron fluoride and its complex compounds, especially zinc fluoroborate.



  The impregnation can take place under the usual conditions and in the usual equipment, as they are known for the anti-crease finish. The hardening takes place preferably between 120 and 160. If so-called nozzle dryers are used, drying and curing can be carried out in one work step.



  If such a finishing process is used to fix mechanically produced effects, the additives customary in these processes, such as plasticizers, polyvinyl alcohol, etc., can be made. Instead of using a compound of formula (I) alone, they can also be mixed with aminoplasts, e.g. B. melamine, urea, ethylene. urea-formaldehyde condensation products, ver used, such aminoplasts are advantageously used, which have a low chlorine retention capacity.



  As hydroxylated fibrous materials which can be refined with the compounds (I), those made of polyvinyl alcohol and especially cellulose-containing materials come into consideration. Here, those made of regenerated cellulose, such as viscose fabric or those made of natural cellulose, z. B. cotton fabrics or linen fabrics, be treated.



  In the following example, parts are parts by weight, percentages are percentages by weight; the ratio of parts by weight to parts by volume is the same as that of the kilogram to the liter; the temperatures are given in degrees Celsius.



  <I> Example </I> A mixture of 50 parts of triacrylyl perhydrotriazine, 67 parts of glycerol monochlorohydrin and 100 parts by volume of benzene is mixed with 27 parts of powdered NaOH (97%) while shaking. An exothermic reaction occurs which lasts 45 minutes with the temperature being held at 35-40 '. After one hour the mixture is allowed to cool, the sodium chloride formed is filtered off and concentrated in vacuo. 85 parts of a viscous, completely water-soluble resin with an epoxy content of 5.45 epoxy equivalents per kg are obtained.



  It consists mainly of the triepoxide of the formula
EMI0002.0013
    and can be used, for example, for textile finishing.

 

Claims (1)

PATENTANSPRUCH I Verfahren zur Herstellung von neuen, mindesten zwei Epoxydgruppen enthaltenden, wasserlöslichen Verbindungen der Formel EMI0002.0016 worin Z einen mindestens eine Epoxydgruppe ent haltenden Alkylrest bedeutet und worin Y für einen Rest -CH=CH2 oder einen Rest -CH2-CH2-O-Z steht, dadurch gekennzeichnet, dass man Derivate des Triacrylylperhydrotriazins der Formel EMI0003.0000 <B>-CH</B> worin Z' einen mindestens eine Halogenhydrin- gruppierung enthaltenden Alkylrest bedeutet und worin Y' für einen Rest -CH=CH2 oder einen Rest -CH2CH2-O-Z' steht, mit halogenwasserstoffabspal tenden Mitteln behandelt. PATENT CLAIM I Process for the preparation of new, water-soluble compounds of the formula containing at least two epoxy groups EMI0002.0016 in which Z is an alkyl radical containing at least one epoxy group and in which Y is a radical -CH = CH2 or a radical -CH2-CH2-O-Z, characterized in that derivatives of triacrylyl perhydrotriazine of the formula EMI0003.0000 -CH where Z 'denotes an alkyl radical containing at least one halohydrin grouping and where Y' denotes a radical -CH = CH2 or a radical -CH2CH2-O-Z ', treated with agents which split off hydrogen halides. UNTERANSPRUCH Verfahren gemäss Patentanspruch I, dadurch ge kennzeichnet, dass man von solchen Derivaten des Triacrylylperhydrotriazins ausgeht, in denen der Rest Z' einen Rest der Formel EMI0003.0005 bedeutet. PATENTANSPRUCH II Verwendung der nach dem Verfahren gemäss Patentanspruch I erhaltenen, mindestens 2 Epoxyd- gruppen enthaltenden wasserlöslichen Verbindungen in härtbaren Dompositionen, die Härtungsmittel für Epoxyharze enthalten. SUBSTANTIAL CLAIM Process according to patent claim I, characterized in that one starts from those derivatives of triacrylyl perhydrotriazine in which the radical Z 'is a radical of the formula EMI0003.0005 means. PATENT CLAIM II Use of the water-soluble compounds containing at least 2 epoxy groups obtained by the process according to Patent Claim I in curable compositions which contain curing agents for epoxy resins.
CH1166464A 1959-09-17 1959-09-17 Process for the preparation of new water-soluble compounds containing epoxy groups CH396022A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CH1166464A CH396022A (en) 1959-09-17 1959-09-17 Process for the preparation of new water-soluble compounds containing epoxy groups

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH7833359A CH395114A (en) 1959-09-17 1959-09-17 Process for the preparation of new water-soluble compounds containing epoxy groups
CH1166464A CH396022A (en) 1959-09-17 1959-09-17 Process for the preparation of new water-soluble compounds containing epoxy groups

Publications (1)

Publication Number Publication Date
CH396022A true CH396022A (en) 1965-07-31

Family

ID=25708719

Family Applications (1)

Application Number Title Priority Date Filing Date
CH1166464A CH396022A (en) 1959-09-17 1959-09-17 Process for the preparation of new water-soluble compounds containing epoxy groups

Country Status (1)

Country Link
CH (1) CH396022A (en)

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