Synthesis of Aliphatic and Aromatic Aldoximes and Used as Modificators in Epoxide Resins

Yıl 2006, Cilt: 6 Sayı: 2, 13 - 21, 01.12.2006

Gülderen Uysal Akkuş Sultan Kurbanlı Mehmet Sezgin

Öz

Anahtar Kelimeler

-

ALİFATİK VE AROMATİK ALDOKSİMLERİN SENTEZİ VE EPOKSİT REÇİNELERİNE MODİFİKATÖR (KATKI MADDESİ) OLARAK KULLANILMASI

Öz

Bu çalışmada, çıkış maddesi olarak doymuş ve doymamış alifatik ve aromatik aldehitler (3Hidroksibütanal, 2-Bütenal, 3-Fenil-3-Hidroksipropanal, 3-Fenil-2-Propenal) kullanıldı. Bunlar benzen veya dikloretan beraberinde hidroksilaminhidroklorür ile 75 - 80 °C’da üç saat süreyle karıştırılarak uygun oksimlerine dönüştürüldü. Elde edilen oksimlerin yapıları aydınlatıldıktan sonra sanayide oldukça yaygın olarak kullanılan epoksit reçinelerine değişik oranlarda katkı maddesi olarak ilave edilerek reçineler sertleştirildi. Böylece elde edilen çeşitli polimer numunelerinin fiziki mekanik özellikleri tayin edildi. Daha sonra amacımıza uygun olarak modifîye edilmiş polimer kompozisyonunun kimyasal maddelere karşı dayanıklılığı ve adezyon kabiliyeti araştırıldı. Analiz sonucunda, epoksit reçinesi zincirine oksim grubunun katılmasıyla adezyon kabiliyetinin % 95 - 100 oranında arttığı görüldü

Anahtar Kelimeler

Alifatik ve aromatik oksialdehit, epoksit reçinesi ( ED-20 ), Oksim, Spektroskopik Yapı Tayini

Kaynakça

• Abboud, K.A., Jircitano, A.J., Westcott, B.L., Sommerer, S.O., 1995, The synthesis and structure of two novel metal-di-2-pyridyl ketone oxime dimers, Inorg. Chim. Acta, 238, 1-2, 149-153.
• Aglietto, M., Ruggeri, G., Tarquini, B., Ciardelli, F., Gianni, P., 1980, Synthesis and catalytic activity of optically active polymers containing oxime groups, Polymer, 21,5, 541- 544. and characterization of epoxy resins containing transition metals, Polymer, 34, 13, 2860-2864. Dehydration of Alkyl- and Arylaldoximes as a New Cytochrome P450-Catalyzed Reaction: Mechanism and Stereochemical Characteristics, Biochemistry, 33, 25, 7811- 7818.
• Brown, D., Gallagher, P. T., Lightfoot, A. P., Moody, C.J., Slawin, A.M.Z., Swann, E., 1995, Chiral oximes in asymmetric synthesis. Addition of organometallic reagents to o-(1- phenylethyl) aldoximes, Tetrahedron, 51, 42, 11473-11488.
• Deagostino, A.,Prandi, C., Venturello, P., 1996, Reaction of α,β-unsaturated and α-phenyl acetals with epoxides, promoted by lithium. Potassium mixed base LICKOR: Synthesis of homoallyl alcohols, Tetrahedron, 52, 4, 1433- 1442.
• DeMaster, E.G., Shirota, F.N., Nagasawa, H.T., 1992, A Beckmann-type dehydration of n- butyraldoxime catalyzed by cytochrome P- 450, J. Org. Chem., 57, 19, 5074-5075.
• Güler, E., Şen, N., Kurbanov, S., Mirzaoğlu, R., 1998, Investigation of the alkylation of aromatic and hydroaromatic aldoximes with halohydrins, Org. Prep. and proced., 30, 2, 195-202.
• Hasebe, M., Tsuchiya, T., 1986, Phtochemical generation of aliphatic radicals from benzophenone oxime esters: simple synthesis of alkylbenzenes and alkylpyridines, Tetrahedron Letters, 27, 28, 3239-3242.
• Hedrick, J.L., Yilgor, I., Jurek,M., Hedrick, J.C., Wilkes,G.L., McGrath, J.E., 1991, Chemical modification of matrix resin networks with engineering thermoplastics: 1. Synthesis, morphology, physical behaviour and toughening mechanisms of poly(arylene ether sulphone) modified epoxy networks, Polymer, 32, 11, 2020-2032.
• Kameyama, A., Nishikubo, T.,1996, A Novel Synthesis of Reactive Polyethers with Pendant Chloromethyl Group by Polyaddition of Bis(epoxide)s with Aromatic Dichlorides, React. and Funct. Polym.,, 30, 1-3, 235-239.
• Karlos, D.D.,., David, A., 1972, Oximes as Accelators for The Amino Curing of Epoxi Resins Amer. Pat. N. 3703497
• Kurbanlı, S., Şen, N., Güler, E., Koçak, A., 2004, The Investigation of the Alkylation Reactions of Hydroxy and En-Oximes with Some Halohydrins and Epoxides, Preparative Organic Chemistry, 34, 9, 1663-1675. ,
• Lawrance, F.K., 1976, Catalytic Processes, Amer. Pat.N.3965777
• Leclerc, G, Andre, M., 1977, Synthesis and ß- Adrenerjik Bloking Activity of A Novel Class Aromatic Oxime Ethers, J. Med. Chem. N. 12 1657 -1662
• Lin, M-S., Yang, T., Huang, K-Y., 1994, Kinetic studies of compatible simultaneous interpenetrating polymer networks based on poly(poly(ethylene glycol) maleate) and epoxy resin, 35, 3, 594-599.
• Nakama, K., Seki, S., Kanemasa, S., 2001, A new synthetic access to N-alkylated nitrones through Lewis acid-catalyzed conjugate additions of aldoximes, Tetrahedron Letters, 42,38, 6719-6722.
• Ösapay, G., Profit, A., Taylor, J. W., 1990, Synthesis of tyrocidine a: Use of oxime resin for peptide chain assembly and cyclization, 31, 43, 6121-6124.
• Palacios, F., Aparicio, D., Santos, J.M., Rodríguez, E., 1996, An improved and general method for the synthesis of α,β- unsaturated oximes from phosphine oxide allenes, Tetrahedron Letters,37, 8,19, 1289- 1292.
• Qipeng, G., 1993, Phase behaviour in epoxy resin containing phenolphthalein poly (ether ether sulphone), Polymer, 34, 1, 70-76.
• Rickborn,B.,1991,Acid-catalyzed Rearrangements of Epoxides, Comp. Org. Synt., 3,733-775.
• Tillyer, R.D., Boudreau, C., Tschaen, Dolling, U. H.,D., Reider, P. J.,1995, Asymmetric reduction of keto oxime ethers using oxazaborolidine reagents. The enantioselective synthesis of cyclic amino alcohols, Tetrahedron Letters, 36, 25, 4337- 4340.
• Tkachev, A.V., Chibiryaev, A.M., Denisov, A.Y., Gatilov, Y.V., 1995, Reaction of certain α,β-unsaturated terpenic oximes with sodium nitrite in acetic acid: A facile synthesis of allylic nitro compounds, Tetrahedron, 51, 6, 1789-1808.
• Udagawa, A., Sasuga, T., 1991, Molecular motion of several epoxy resins and influence of electron irradiation, Polymer, 32, 3, 402- 408.