Oligomerization of Substituted Phenyl Glycidyl Ethers with Tertiary Amine |
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Authors: | Yoshio Tanaka Masao Tomio Hiroshi Kakiuchi |
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Institution: | 1. DEPARTMENT OF APPLIED CHEMISTRY, FACULTY OF ENGINEERING , YOKOHAMA NATIONAL UNIVERSITY , MINAMI-KU, YOKOHAMA, JAPAN;2. DEPARTMENT OF APPLIED CHEMISTRY, FACULTY OF ENGINEERING , YOKOHAMA NATIONAL UNIVERSITY , MINAMI-KU, YOKOHAMA, JAPAN;3. Showa Electro-Chemical Industry Co., Ltd. , Chidorimachi 5, Kawasaki, Japan |
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Abstract: | The oligomerization of substituted phenyl glycidyl ethers was studied kinetically in the presence of dimethylbenzylamine using toluene or dioxane as a solvent. The infrared spectra of the resultant oligomers suggest that the reaction products have the internal carbon-carbon double-bond un-saturation, which is confirmed by the catalytic hydrogenation. The molecular weights of the oligomers also suggest that γ-phenoxy allyl alcohol produced by the initial reaction step, in which the γ-proton of phenyl glycidyl ether is attracted by a base, amine, reacts with other phenyl glycidyl ether and thus proceeds further, yielding the oligomer. The value of the reaction constant ρ is obtained positive for this reaction, which indicates that electron-withdrawing substituents of phenyl gylcidyl ethers increase the rate of oligomerization. A kinetic analysis shows that the proposed reaction sequence accounts for all the characteristics of the polymerization including sigmoidal shapes of monomer consumption curves, reaction rates, and induction periods. |
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