DE1220859B - Process for the preparation of the isocyanuric acid triglycidate - Google Patents
Process for the preparation of the isocyanuric acid triglycidateInfo
- Publication number
- DE1220859B DE1220859B DEF44036A DEF0044036A DE1220859B DE 1220859 B DE1220859 B DE 1220859B DE F44036 A DEF44036 A DE F44036A DE F0044036 A DEF0044036 A DE F0044036A DE 1220859 B DE1220859 B DE 1220859B
- Authority
- DE
- Germany
- Prior art keywords
- cyanuric acid
- epichlorohydrin
- preparation
- isocyanuric acid
- triglycidate
- 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
Links
- 238000000034 method Methods 0.000 title claims description 7
- -1 isocyanuric acid triglycidate Chemical compound 0.000 title description 12
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 17
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 8
- 150000003568 thioethers Chemical class 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 239000004593 Epoxy Substances 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 4
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 229950006389 thiodiglycol Drugs 0.000 description 2
- CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical compound C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 description 1
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 1
- KJWHJDGMOQJLGF-UHFFFAOYSA-N 1-methylsulfanyldodecane Chemical compound CCCCCCCCCCCCSC KJWHJDGMOQJLGF-UHFFFAOYSA-N 0.000 description 1
- LNRIEBFNWGMXKP-UHFFFAOYSA-N 2-ethylsulfanylethanol Chemical compound CCSCCO LNRIEBFNWGMXKP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- BTNRQGYYIMWJRV-UHFFFAOYSA-N butylsulfanylmethylbenzene Chemical compound CCCCSCC1=CC=CC=C1 BTNRQGYYIMWJRV-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000003945 chlorohydrins Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- UJVWNJCGCSRFNP-UHFFFAOYSA-M dibenzyl(methyl)sulfanium;bromide Chemical compound [Br-].C=1C=CC=CC=1C[S+](C)CC1=CC=CC=C1 UJVWNJCGCSRFNP-UHFFFAOYSA-M 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Natural products C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical class [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- XDLNRRRJZOJTRW-UHFFFAOYSA-N thiohypochlorous acid Chemical compound ClS XDLNRRRJZOJTRW-UHFFFAOYSA-N 0.000 description 1
- VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic 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
- C07D405/14—Heterocyclic 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/12—Derivatives of isocyanic acid having isocyanate groups bound to carbon atoms of six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
AUSLEGESCHRIFTEDITORIAL
Int. Cl.:Int. Cl .:
C07dC07d
Deutsche Kl.: 12 ρ -10/05German class: 12 ρ -10/05
Nummer: 1220 859Number: 1220 859
Aktenzeichen: F 44036IV d/12 ρFile number: F 44036IV d / 12 ρ
Anmeldetag: 23. September 1964Filing date: September 23, 1964
Auslegetag: 14. Juli 1966Opening day: July 14, 1966
Es ist bekannt, Epoxydverbindungen durch Umsetzen von Cyanursäure oder funktionellen Derivaten davon aus den entsprechenden Chlorhydrinen herzustellen. Diese lassen sich beispielsweise aus Cyanursäure und Epihalogenhydrinen in Gegenwart von quartären Ammoniumsalzen herstellen. Da bekannterweise quartäre Ammoniumsalze auf Epihalogenhydrine polymerisierend wirken, werden bei diesem Verfahren Epoxydverbindungen mit hohem Chlorgehalt erhalten. Auch nach mehrmaliger Natronlaugebehandlung können nach diesem Verfahren keine chlorfreien monomeren Glycidylverbindungen der Cyanursäure erhalten werden (vgl. USA.-Patentschrift 2 809 942). Demgegenüber werden nach dem Verfahren der Erfindung durch Anwendung der erfindungsgemäß zu verwendenden Katalysatoren in ausgezeichneter Ausbeute 3-Chlor-2-hydroxypropylderivate der Isocyanursäure und teilweise bereits der Isocyanursäuretriglycidester gebildet. In einfacher Weise wird aus dieser Mischung chlorfreier Isocyanursäuretriglycidester mit praktisch theoretischem Epoxidäquivalent erhalten. Derartige Produkte haben für den Einsatz auf dem Elektroisoliergebiet große Bedeutung.It is known to produce epoxy compounds by reacting cyanuric acid or functional derivatives to produce it from the corresponding chlorohydrins. These can be made from cyanuric acid, for example and prepare epihalohydrins in the presence of quaternary ammonium salts. As is well known Quaternary ammonium salts have a polymerizing effect on epihalohydrins in this process Obtained epoxy compounds with high chlorine content. Even after repeated caustic soda treatment you can no chlorine-free monomeric glycidyl compounds of cyanuric acid were obtained by this process (see U.S. Patent 2,809,942). In contrast, according to the method of the invention by using the catalysts to be used according to the invention in excellent yield 3-chloro-2-hydroxypropyl derivatives of isocyanuric acid and in some cases already triglycidic isocyanurate educated. In a simple manner, this mixture becomes chlorine-free isocyanuric acid triglycidate with practically theoretical epoxy equivalent obtained. Such products have for use in the electrical insulation field big meaning.
Es wurde nun ein Verfahren zur Herstellung des Isocyanursäuretriglycidesters durch Umsetzung von Cyanursäure mit überschüssigem Epichlorhydrin in Gegenwart eines Katalysators bei 40 bis 120° C und anschließende, gegebenenfalls mehrfache Behandlung des Reaktionsproduktes mit Alkalien bei 40 bis 85° C gefunden, das dadurch gekennzeichnet ist, daß die Umsetzung der Cyanursäure mit Epichlorhydrin in Gegenwart von Thioäthern und/oder deren SuIf oniumsalzen als Katalysatoren durchgeführt wird.There has now been a process for preparing the isocyanuric acid triglycidate by reacting Cyanuric acid with excess epichlorohydrin in the presence of a catalyst at 40 to 120 ° C and subsequent, if necessary multiple, treatment of the reaction product with alkalis at 40 to 85.degree found, which is characterized in that the reaction of cyanuric acid with epichlorohydrin in The presence of thioethers and / or their sulfonium salts is carried out as catalysts.
Das erfindungsgemäße Verfahren kann beispielsweise so durchgeführt werden, daß man Cyanursäure, das Epichlorhydrin und den Katalysator mischt. Dabei verwendet man einen Überschuß an Epichlorhydrin bis etwa zum Fünffachen der äquivalenten Menge. Der Katalysator, ein Thioäther bzw. dessen" SuIf oniumsalz, wird in Mengen von etwa 0,01 bis 5, vorzugsweise 0,01 bis 0,1 Gewichtsprozent, bezogen auf die Cyanursäure, zugesetzt. Die Mischung wird dann auf Temperaturen zwischen 40 und 120°C, vorzugsweise 50 bis 70° C, erhitzt und bis zur Beendigung der Reaktion auf dieser Temperatur gehalten.The inventive method can be carried out, for example, that cyanuric acid, mixes the epichlorohydrin and the catalyst. An excess of epichlorohydrin is used here up to about five times the equivalent amount. The catalyst, a thioether or its "sulfonium salt, is used in amounts of about 0.01 to 5, preferably 0.01 to 0.1 percent by weight, based on the cyanuric acid, added. The mixture is then to temperatures between 40 and 120 ° C, preferably 50 to 70 ° C. and kept at this temperature until the reaction has ended.
Danach wird bei einer Temperatur zwischen 40 und 85° C innerhalb von 1 bis 10 Stunden, vorzugsweise
2 bis 6 Stunden, festes Kalium- oder Natriumhydroxyd in einer gesamten Menge von 2,7 bis 3,3 Mol pro Mol
eingesetzter Cyanursäure zugegeben. Aus dieser Reaktionslösung werden dann Wasser und überschüssiges
Epichlorhydrin im Vakuum abdestilliert, der Rück-Verf ahren zur Herstellung des
IsocyanursäuretriglycidestersThereafter, solid potassium or sodium hydroxide in a total amount of 2.7 to 3.3 mol per mol of cyanuric acid used is added at a temperature between 40 and 85 ° C. within 1 to 10 hours, preferably 2 to 6 hours. From this reaction solution, water and excess epichlorohydrin are then distilled off in vacuo, the reverse process for the production of the
Triglycidic isocyanurate
Anmelder:Applicant:
Farbenfabriken Bayer Aktiengesellschaft,Paint factories Bayer Aktiengesellschaft,
LeverkusenLeverkusen
Als Erfinder benannt:Named as inventor:
Dr. Robert Schmitz-Josten, Köln-Stammheim;Dr. Robert Schmitz-Josten, Cologne-Stammheim;
Dr. Roland Gipp, Köln-BuchheimDr. Roland Gipp, Cologne-Buchheim
stand mit Wasser und einem nicht mit Wasser mischbaren Lösungsmittel, z. B. Benzol oder Methylen-stood with water and a water-immiscible solvent, e.g. B. benzene or methylene
ao chlorid, aufgenommen und die organische Phase abgetrennt. Diese organische Phase kann dann direkt
destillativ aufgearbeitet werden. Man kann aber auch eine weitere Laugenbehandlung anschließen.
Als Katalysatoren werden niedermolekulare Thioäther und/oder deren Sulfoniumsalze verwendet. Es
können auch Verbindungen eingesetzt werden, welche mit dem Epichlorhydrin in Thioäther oder deren
Sulfoniumverbindungen übergehen können, wie beispielsweise Schwefelwasserstoff, Natriumsulfid oder
Mercaptane.ao chloride, added and the organic phase separated. This organic phase can then be worked up directly by distillation. But you can also follow up with another lye treatment.
Low molecular weight thioethers and / or their sulfonium salts are used as catalysts. It is also possible to use compounds which can be converted into thioethers or their sulfonium compounds with the epichlorohydrin, such as, for example, hydrogen sulfide, sodium sulfide or mercaptans.
Die als Katalysatoren geeigneten Thioäther bzw. Sulfoniumsalze entsprechen den allgemeinen FormelnThe thioethers or sulfonium salts suitable as catalysts correspond to the general formulas
R1-S-R2 bzw.R 1 -SR 2 or
x®x®
worin R1, R2 und R3 gleich oder verschieden sein können undwherein R 1 , R 2 and R 3 can be the same or different and
a) Alkyl-(CrC12)-, Cycloalkyl-, Aralkylreste, z. B.a) alkyl (C r C 12 ), cycloalkyl, aralkyl radicals, e.g. B.
Benzylreste,
b) cü-Hydroxyalkylreste, die durch Heteroatome wie
O, S unterbrochen sein können,
c) cyanäthylierte Oxyalkylreste, z. B.Benzyl residues,
b) cü-hydroxyalkyl radicals, which can be interrupted by heteroatoms such as O, S,
c) cyanoethylated oxyalkyl radicals, e.g. B.
— CH2 — CH2 — O — CH2 — CH2 — CN,- CH 2 - CH 2 - O - CH 2 - CH 2 - CN,
oder
d) Epoxypropylresteor
d) epoxypropyl residues
sowie X- ein einwertiges Anion, vorzugsweise ein Halogenidion bedeutet.and X- is a monovalent anion, preferably one Means halide ion.
609 589/320609 589/320
Als Katalysatoren vorstehender Definition seien beispielsweise genannt: Diäthylsulfid, /S-Hydroxyäthyläthylsulfid, /J-Hydroxypropyl-äthylsulfid, ω-Hydroxytetramethylen-äthylsurfid, Thiodiglykol, Mono-ß-cyanoäthyl-thiodiglykoläther, Dibenzylsulfid, Benzyläthylsulfid, Benzylbutylsulfid, Trimethylsulfoniumjodid, Tris-(^-hydroxyäthyl)-sulfoniumchlorid, Dibenzyl-methylsulfoniumbromid, 2,3-Epoxypropylmethyläthylsulf oniumjodid, Dodecylmethylsulfid, Dithian usw. ίοExamples of catalysts of the above definition are: diethyl sulfide, / S-hydroxyethyl ethyl sulfide, / J-hydroxypropyl ethyl sulfide, ω-hydroxytetramethylene ethyl sulfide, Thiodiglycol, mono-ß-cyanoethyl thiodiglycol ether, dibenzyl sulfide, benzyl ethyl sulfide, Benzyl butyl sulfide, trimethyl sulfonium iodide, tris - (^ - hydroxyethyl) sulfonium chloride, dibenzyl methyl sulfonium bromide, 2,3-epoxypropylmethylethylsulfonium iodide, dodecylmethylsulfide, dithiane etc. ίο
Vorzugsweise werden aliphatische Thioäther mit nicht zu großen Alkylgruppen, besonders mit unverzweigten C1- bis C5-Alkylresten oder auch Oxyalkylresten eingesetzt, um eine sterische Hinderung der katalytischen Wirksamkeit zu vermeiden. Bei Verwendung von SuIfoniumsalzen werden ebenfalls bevorzugt Sulfoniumhalogenide mit aliphatischen Resten eingesetzt. Preference is given to using aliphatic thioethers with not too large alkyl groups, especially with unbranched C 1 - to C 5 -alkyl radicals or else oxyalkyl radicals, in order to avoid steric hindrance of the catalytic activity. When using sulfonium salts, sulfonium halides with aliphatic radicals are also preferably used.
2020th
387 g Cyanursäure (3 Mol), 4164 g Epichlorhydrin (45 Mol) und 15 g 2-Hydroxyäthyl-äthylsulfid werden 64 Stunden bei 60°C gerührt. Nach 24 Stunden ist die Cyanursäure gelöst (bei einer Reaktionstemperatur von 1000C geht die Cyanursäure in einer Stunde in Lösung, und die Reaktion ist nach 16 Stunden beendet). Aus einer von flüchtigen Bestandteilen befreiten aliquoten Probe errechnet sich eine Ausbeute von 1015 g eines Zwischenproduktes mit 4,05 °/0 Chlor und einem Epoxydäquivalent von 239. Der Ansatz wird anschließend bei 50 bis 6O0C portionsweise mit 430 g Natriumhydroxyd (Schuppen) innerhalb von 2,5 Stunden versetzt. Nachdem sich ein pH-Wert von 9 bis 10 eingestellt hat, wird das Reaktionswasser mit Epichlorhydrin zusammen bei 50° C abdestilliert, der Rückstand vom Natriumchlorid abgesaugt und anschließend vom restlichen Epichlorhydrin und höhersiedenden Produkten durch Abdestillieren bis zu einer Sumpftemperatur von 100° C/0,2 Torr befreit. Ausbeute 920 g Rohprodukt mit einem Epoxydäquivalent von 123 (Theorie 99) und einem Chlorgehalt von 1,9 %. Das Rohprodukt ist in heißem Wasser löslich. Durch Lösen in Essigsäureäthylester oder viel Methanol wird das Produkt von harzartigen Bestandteilen befreit und das aus dem Filtrat erhaltene Produkt aus Methanol oder Wasser umkristallisiert. Schmp. des reinen Triglycidyl-isocyanurats 103°C, Epoxydäquivalent 100 (Theorie 99).387 g of cyanuric acid (3 mol), 4164 g of epichlorohydrin (45 mol) and 15 g of 2-hydroxyethyl ethyl sulfide are stirred at 60 ° C. for 64 hours. The cyanuric acid has dissolved after 24 hours (at a reaction temperature of 100 ° C., the cyanuric acid dissolves in one hour and the reaction is complete after 16 hours). From a devolatilized sample aliquot, a yield of 1015 g of an intermediate product calculated with 4.05 ° / 0 chlorine and an epoxy equivalent of 239. The batch is then at 50 to 6O 0 C in portions with 430 g of sodium hydroxide (flakes) within offset by 2.5 hours. After a pH of 9 to 10 has been set, the water of reaction is distilled off together with epichlorohydrin at 50 ° C, the residue is suctioned off from the sodium chloride and then from the remaining epichlorohydrin and higher-boiling products by distilling off up to a bottom temperature of 100 ° C / 0 , 2 torr exempt. Yield 920 g of crude product with an epoxy equivalent of 123 (theory 99) and a chlorine content of 1.9%. The crude product is soluble in hot water. Resin-like constituents are removed from the product by dissolving in ethyl acetate or a large amount of methanol, and the product obtained from the filtrate is recrystallized from methanol or water. Melting point of the pure triglycidyl isocyanurate 103 ° C., epoxy equivalent 100 (theory 99).
Analyse:
Berechnet
gefundenAnalysis:
Calculated
found
C 48,5%, H 5,1%, N 14,1%;
0 48,6%, H 5,3%, N 14,0%.C 48.5%, H 5.1%, N 14.1%;
0 48.6%, H 5.3%, N 14.0%.
Claims (1)
USA.-Patentschrift Nr. 2 809 942.Considered publications:
U.S. Patent No. 2,809,942.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF44036A DE1220859B (en) | 1964-09-23 | 1964-09-23 | Process for the preparation of the isocyanuric acid triglycidate |
| CH1174565A CH473825A (en) | 1964-09-23 | 1965-08-20 | Process for the production of epoxy compounds |
| NL6512075A NL6512075A (en) | 1964-09-23 | 1965-09-16 | |
| FR31878A FR1447036A (en) | 1964-09-23 | 1965-09-18 | Process for preparing epoxy compounds |
| BE669844D BE669844A (en) | 1964-09-23 | 1965-09-20 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF44036A DE1220859B (en) | 1964-09-23 | 1964-09-23 | Process for the preparation of the isocyanuric acid triglycidate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1220859B true DE1220859B (en) | 1966-07-14 |
Family
ID=7099841
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF44036A Pending DE1220859B (en) | 1964-09-23 | 1964-09-23 | Process for the preparation of the isocyanuric acid triglycidate |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE669844A (en) |
| CH (1) | CH473825A (en) |
| DE (1) | DE1220859B (en) |
| NL (1) | NL6512075A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2809942A (en) * | 1955-10-21 | 1957-10-15 | Devoe & Raynolds Co | Process for making polyglycidyl cyanurates |
-
1964
- 1964-09-23 DE DEF44036A patent/DE1220859B/en active Pending
-
1965
- 1965-08-20 CH CH1174565A patent/CH473825A/en not_active IP Right Cessation
- 1965-09-16 NL NL6512075A patent/NL6512075A/xx unknown
- 1965-09-20 BE BE669844D patent/BE669844A/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2809942A (en) * | 1955-10-21 | 1957-10-15 | Devoe & Raynolds Co | Process for making polyglycidyl cyanurates |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6512075A (en) | 1966-03-24 |
| CH473825A (en) | 1969-06-15 |
| BE669844A (en) | 1966-01-17 |
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