CH362078A - Process for the preparation of ethyleneimine derivatives - Google Patents
Process for the preparation of ethyleneimine derivativesInfo
- Publication number
- CH362078A CH362078A CH362078DA CH362078A CH 362078 A CH362078 A CH 362078A CH 362078D A CH362078D A CH 362078DA CH 362078 A CH362078 A CH 362078A
- Authority
- CH
- Switzerland
- Prior art keywords
- dependent
- starting material
- bromo
- ethyl ester
- acid ethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical class C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 15
- 239000007858 starting material Substances 0.000 claims description 9
- -1 cyano, carboxyl Chemical group 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000004202 carbamide Chemical group 0.000 claims description 2
- 235000013877 carbamide Nutrition 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229960001330 hydroxycarbamide Drugs 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 8
- 239000002253 acid Substances 0.000 claims 1
- BOIWYTYYWPXGAT-UHFFFAOYSA-N ethyl 2-phenylprop-2-enoate Chemical compound CCOC(=O)C(=C)C1=CC=CC=C1 BOIWYTYYWPXGAT-UHFFFAOYSA-N 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 5
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- MGPDSKXOTDLPJE-UHFFFAOYSA-N ethyl aziridine-1-carboxylate Chemical compound CCOC(=O)N1CC1 MGPDSKXOTDLPJE-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- 101100125371 Caenorhabditis elegans cil-1 gene Proteins 0.000 description 1
- DYDCUQKUCUHJBH-UHFFFAOYSA-N DL-Cycloserine Chemical compound NC1CONC1=O DYDCUQKUCUHJBH-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 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
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- QRHKUWPDXPZWDX-UHFFFAOYSA-N propan-2-yl aziridine-1-carboxylate Chemical compound CC(C)OC(=O)N1CC1 QRHKUWPDXPZWDX-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Äthylenimin-Derivaten
Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von Athylenimin-Derivaten der Formel
EMI1.1
worin R, Wasserstoff, eine Alkyl-, Cycloalkyl-, Aryl-oder Aralkylgruppe und R2 eine Cyan-, Carboxyl-, Carbamid-, N-Hydroxycarbamid-oder Carbalkoxygruppe darstellt, welches dadurch gekennzeichnet ist, dass man Verbindungen der Formel
EMI1.2
mit flüssigem Ammoniak umsetzt.
Zur Verhinderung der Polymerisation werden dem Reaktionsgemisch vorzugsweise Polymerisationsinhibitoren zugesetzt, wie z. B. Hydrochinon, p-Phenylen-diamin, Diphenylamin, Phenylb naphthyl- amin. Wenn in der Formel II das Symbol R2 eine Carbomethoxygruppe darstellt, dann erhält man zur Hauptsache das Säureamid. Bei den höher homologen Estern, wie z. B. dem Athyl-, Propyl-oder Butylester, bleibt die Estergruppe zum grössten Teil erhalten. Als Ausgangsverbindungen der Formel II werden vorzugsweise solche verwendet, in denen Ri Wasserstoff, Methyl, ¯thyl, Heptyl, Octyl, Cyclohexyl, Phenyl, p-Nitro-phenyl oder Benzyl bedeutet.
Man kann auch von den leicht zugänglichen a"t :-Di-brom-verbindungen der Formel
EMI1.3
ausgehen, die bei der Umsetzung mit flüssigem Ammoniak zuerst in die entsprechenden Verbindungen der Formel II übergeführt werden und dann bei Fortsetzung der Reaktion zu den Verbindungen der Formel I führen.
Die erfindungsgemäss erhältlichen Verbindungen sollen als Zwischenprodukte für die Herstellung von Arzneimitteln, insbesondere für die Herstellung von AminosÏuren, 4-Amino-isoxazolidon und dessen Substitutionsprodukten in 5-Stellung verwendet werden.
Beispiel 1
28 g a-Brom-acrylsäureäthylester werden in 500 cm3 flüssiges Ammoniak eingetropft und wÏhrend 4 Stunden gerührt. Darauf wird zur Trockne eingedampft und der Rückstand mit 500 cm3 Acetonitril ausgezogen, wobei das gebildete Ammoniumbromid zurückbleibt. Das Filtrat wird eingedampft und mit 400 cm3 absolutem Ather extrahiert, wobei eine kleine Menge eines harzigen Rückstandes zu rückbleibt. Das eingedampfte Filtrat besteht aus einem roten 01, welches den farblosen Athylenimincarbonsäureäthylester mit einem Siedepunkt von 53 bis 54¯C/11 mm Hg enthält ;
n2D5 = 1, 4372, d20 = 1, 0592
Beispiel 2
78 g a, ?-Di-brom-propionsäureäthylester werden in 200-300 cm3 flüssiges Ammoniak eingetropft und 2 Stunden gerührt. Darauf wird wie in Beispiel 1 aufgearbeitet, wobei der reine Athylenimincarbonsäureäthylester gefasst wird.
Beispiel 3
26 g a"B-Di-brom-propionsäureäthylester werden in 200 cm3 flüssigem Ammoniak gelöst und während 3 Stunden gerührt. Nach der Entfernung des Ammoniaks wird der Rückstand direkt im Hochvakuum destilliert. Das Destillat, bestehend aus Athylenimin- carbonsäure-äthylester, wird in einer Kühlfalle (Aceton-Trockeneis) kondensiert.
Beispiel 4
78 g a"S-Di-brom-propionsäureäthylester werden in einem Liter flüssigem Ammoniak gelöst und wÏhrend 40 Minuten gerührt. Darauf wird eingedampft und mit 50 cm3 Wasser versetzt, um den Rückstand vollständig zu lösen. Man sättigt mit Kochsalz und extrahiert viermal mit 400 cm3 Äther, trocknet das Extrakt mit Natriumsulfat und dampft das Filtrat bei 20¯C/12 mm Hg ein. Man erhält einen ¯ligen Rückstand, welcher nach Destillation den Äthylenimincarbonsäureäthylester liefert.
Beispiel 5
74 g α¯-Di-brom-propionsÏuremethylester werden in 1, 2 l flüssiges Ammoniak eingedampft. Der Rückstand wird mit 600 cm3 Acetonitril ausgezogen.
Zurück bleiben 64 g eines zur Hauptsache aus Ammoniumbromid bestehenden Rückstandes. Das Filtrat wird eingedampft, wieder mit Methylenchlorid ausgezogen, das Filtrat wieder eingedampft und mit Äther extrahiert. Nach dem Eindlampfen der ätheri- schen Lösung bleibt ein helles, d nnfl ssiges Íl zur ck, welches nach der dritten Destillation bei 50 bis 65 C/11 mm Hg den Äthylenimincarbonsäure- methylester liefert. n D 24¯ = l, 4390, d20 = 1, 1181.
Aus dem Rückstand der Ätherextraktion konnte auch Athylenimincarbonsäureamid isoliert werden.
Aus Athanol-Ather umkristallisiert, zeigt dieses einen Schmelzpunkt von 116-118 C.
Beispiel 6
40 g a, -Di-brom-propionsÏure-n-butylester werden in 500 cm3 flüssigem Ammoniak während 4 Stunden gerührt. Der Eindampfrückstand wird mit Acetonitril ausgezogen, wobei ein Ammoniumbro midrückstand von 22 g abgetrennt werden kann. Das eingedampfte Filtrat wird mit Äther ausgezogen. Die ätherische Lösung wird eingedampft und das zurückbleibende 01 im Vakuum bei 83-84 C/13 mm Hg destilliert, wobei der Äthylenimincarbonsäurebutyl- ester erhalten wird. n D 25 = 1, 4400.
Beispiel 7
82, 2 g a, ss-Di-brom-buttersäureäthylester werden in 900 cm3 flüssigem Ammoniak eine halbe Stunde gerührt. Der Eindampfrückstand wird mit 700 cm3 Acetonitril ausgezogen. Zurück bleiben 50 g Ammoniumbromid. Das Filtrat wird eingedampft und der Rückstand mit 500 cm3 Äther extrahiert. Man filtriert, dampft die ätherische Lösung ein, und es bleibt ein 01 zurück. Dieses liefert nach Destillation bei 70-75 C/12 mm Hg das 2-Methyl-3carbÏthoxy-Ïthylenimin. nid = 1, 4404.
Beispiel 8
Man lässt 82 g α¯-Di-brom-propionsÏureiso- propylester während 11/w Stunden in 1, 2 1 flüssiges Ammoniak, welches 0, 8 g N-Phenyl-, B-naphthyl-amin als Stabilisator enthält, tropfenweise einfliessen. Das Gemisch wird noch 3 Stunden weitergerührt und das Ammoniak darauf im Vakuum abgedampft. Den festen Rückstand nimmt man in 500 cm3 Äther und 200 cm3 gesättigter Kochsalzlösung auf. Die wd6rige Lösung zieht man noch zweimal mit je 500 cm3 Äther aus. Die vereinigten Atherextrakte trocknet man mit Natriumsulfat und dampft die filtrierte Lö sung im Vakuum ein.
Durch Destillation des öligen Rückstandes erhält man Athylenimincarbonsäure- isopropylester ; Siedepunkt 52-53 Cil 1 mm Hg ; n2D = 1, 4350.
Process for the preparation of ethyleneimine derivatives
The present invention relates to a process for the preparation of ethyleneimine derivatives of the formula
EMI1.1
in which R, hydrogen, an alkyl, cycloalkyl, aryl or aralkyl group and R 2 is a cyano, carboxyl, carbamide, N-hydroxycarbamide or carbalkoxy group, which is characterized in that compounds of the formula
EMI1.2
Reacts with liquid ammonia.
To prevent the polymerization, polymerization inhibitors are preferably added to the reaction mixture, such as. B. hydroquinone, p-phenylenediamine, diphenylamine, phenylb naphthylamine. If the symbol R2 in formula II represents a carbomethoxy group, then the main thing is the acid amide. In the higher homologous esters, such as. B. the ethyl, propyl or butyl ester, the ester group remains for the most part. The starting compounds of the formula II are preferably those in which Ri is hydrogen, methyl, ¯thyl, heptyl, octyl, cyclohexyl, phenyl, p-nitro-phenyl or benzyl.
One can also use the easily accessible a "t: -di-bromine compounds of the formula
EMI1.3
go out, which are first converted into the corresponding compounds of formula II in the reaction with liquid ammonia and then lead to the compounds of formula I when the reaction is continued.
The compounds obtainable according to the invention are intended to be used as intermediates for the production of medicaments, in particular for the production of amino acids, 4-amino-isoxazolidone and its substitution products in the 5-position.
example 1
28 g of a-bromo-acrylic acid ethyl ester are added dropwise to 500 cm3 of liquid ammonia and the mixture is stirred for 4 hours. It is then evaporated to dryness and the residue is extracted with 500 cm3 of acetonitrile, the ammonium bromide formed remaining behind. The filtrate is evaporated and extracted with 400 cm3 of absolute ether, leaving a small amount of a resinous residue. The evaporated filtrate consists of a red oil containing the colorless ethylenimine carboxylic acid ethyl ester with a boiling point of 53 to 54¯C / 11 mm Hg;
n2D5 = 1, 4372, d20 = 1, 0592
Example 2
78 g of a,? -Di-bromopropionic acid ethyl ester are added dropwise to 200-300 cm3 of liquid ammonia and stirred for 2 hours. It is then worked up as in Example 1, the pure ethylenimine carboxylic acid ethyl ester being collected.
Example 3
26 ga "of ethyl B-di-bromopropionate are dissolved in 200 cm3 of liquid ammonia and stirred for 3 hours. After the ammonia has been removed, the residue is distilled directly in a high vacuum. The distillate, consisting of ethyl ethyleneimine carboxylate, is in a Cold trap (acetone dry ice) condenses.
Example 4
78 g of S-di-bromopropionic acid ethyl ester are dissolved in one liter of liquid ammonia and stirred for 40 minutes. It is then evaporated and 50 cm3 of water are added to completely dissolve the residue. It is saturated with sodium chloride and extracted four times with 400 cm3 Ether, the extract is dried with sodium sulfate and the filtrate is evaporated at 20 ° C / 12 mm Hg. An oily residue is obtained which, after distillation, gives the ethylenimine carboxylic acid ethyl ester.
Example 5
74 g of methyl α ¯-di-bromopropionate are evaporated in 1.2 l of liquid ammonia. The residue is extracted with 600 cm3 of acetonitrile.
What remains are 64 g of a residue consisting mainly of ammonium bromide. The filtrate is evaporated, extracted again with methylene chloride, the filtrate evaporated again and extracted with ether. After evaporation of the ethereal solution, a light, thin liquid oil remains, which after the third distillation at 50 to 65 C / 11 mm Hg yields the methyl ethylene imine carboxylate. n D 24¯ = 1,4390, d20 = 1,181.
Athylenimincarboxamide could also be isolated from the residue of the ether extraction.
Recrystallized from ethanol ether, this shows a melting point of 116-118 C.
Example 6
40 g of a, -di-bromopropionic acid-n-butyl ester are stirred in 500 cm3 of liquid ammonia for 4 hours. The evaporation residue is extracted with acetonitrile, whereby an ammonium bromide residue of 22 g can be separated off. The evaporated filtrate is extracted with ether. The ethereal solution is evaporated and the remaining oil is distilled in vacuo at 83-84 ° C./13 mm Hg, the butyl ethyleneimine carboxylate being obtained. n D 25 = 1,4400.
Example 7
82.2 g of a, ss-di-bromobutyric acid ethyl ester are stirred in 900 cm3 of liquid ammonia for half an hour. The evaporation residue is extracted with 700 cm3 of acetonitrile. 50 g of ammonium bromide remain. The filtrate is evaporated and the residue extracted with 500 cm3 ether. It is filtered, the ethereal solution is evaporated, and an 01 remains. After distillation at 70-75 C / 12 mm Hg, this gives 2-methyl-3carbÏthoxy-ethyleneimine. nid = 1,4404.
Example 8
82 g of α-di-bromopropionic acid isopropyl ester are allowed to flow dropwise into 1.2 liters of liquid ammonia which contains 0.8 g of N-phenyl-, B-naphthyl-amine as stabilizer for 11 / w hours. The mixture is stirred for a further 3 hours and the ammonia is then evaporated off in vacuo. The solid residue is taken up in 500 cm3 of ether and 200 cm3 of saturated sodium chloride solution. The aqueous solution is extracted twice more with 500 cm3 of ether each time. The combined ether extracts are dried with sodium sulfate and the filtered solution is evaporated in vacuo.
Ethyleniminecarboxylic acid isopropyl ester is obtained by distilling the oily residue; Boiling point 52-53 cil 1 mm Hg; n2D = 1,4350.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH362078T | 1957-10-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH362078A true CH362078A (en) | 1962-05-31 |
Family
ID=4513162
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH362078D CH362078A (en) | 1957-10-25 | 1957-10-25 | Process for the preparation of ethyleneimine derivatives |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH362078A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0171787A1 (en) * | 1984-08-13 | 1986-02-19 | Research Association For Utilization Of Light Oil | Process for production of aziridine-2-carboxylic acid amide |
| CN119462757A (en) * | 2024-11-25 | 2025-02-18 | 湖北固润科技股份有限公司 | Cationic photopolymerizable phosphorus-containing bifunctional oxetane monomer, preparation method and application thereof |
-
1957
- 1957-10-25 CH CH362078D patent/CH362078A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0171787A1 (en) * | 1984-08-13 | 1986-02-19 | Research Association For Utilization Of Light Oil | Process for production of aziridine-2-carboxylic acid amide |
| CN119462757A (en) * | 2024-11-25 | 2025-02-18 | 湖北固润科技股份有限公司 | Cationic photopolymerizable phosphorus-containing bifunctional oxetane monomer, preparation method and application thereof |
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