1,6-Diphenyl-4,7-dioxaspiro[2.4]heptane의 합성 및 개환 중합

이주연; 조성옥; 조의환

Polymer(Korea), Vol.15, No.4, 453-458, August, 1991

Export Citation

1,6-Diphenyl-4,7-dioxaspiro[2.4]heptane의 합성 및 개환 중합

Synthesis and Ring-Opening Polymerization of 1,6-Diphenyl-4,'7-dioxaspiro[2.4] heptane

이주연, 조성옥, 조의환

초록

t-BuO^-K⁺ 존재하에서 (2,2-dichlorocyclopropyl)benzene과 (±)-1-phenyl-1,2-ethanediol을 반응시켜서 1,6-diphenyl-4,7-dioxaspiro(2.4)heptane (1)을 합성하쳤다. 단량체 1을 BF₃와 같은 양이온 개시제로 중합시킨 결과 페닐기를 가지는 폴리에스테르 2를 얻었다. 양이온 중합은 이중고리열림 메카니즘으로 진행되었다. 폴리에스테르 2는 상용 용매에 잘 녹았으며 고유점도는 0.10-0.12dL/g을 보였다. 용액으로 부터 만들어진 중합체 필름은 투명하고 취약성을 보였으며 유리전이 온도는 58℃였다.

1,6-Diphenyl-4,7-dioxaspiro[2.4]heptane (1) was prepared from (2,2-dichlorocyclopropal)benzene and (±)-1-phenyl-1,2-ethanedio1 in the presence of potassium tert-butoxide. Compound 1 was Polymerized by cationic initiators such as boron trifluoride etherate to obtain Polyester (2) containing phenyl group. The cationic polymerization proceeded via double ring-opening mechanism. Polyester 2 was soluble in common solvents and the inherent viscosities were In the range of 0.10-0.12 dL/g. Solution-cast film was clear and brittle, showing T_g value of 58℃.

[References]

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Rasoul HAA, McKinney MA, Aiani KE, Polym. Prepr. Am. Chem. Soc. Div. Polym. Chem., 31, 26 (1990)

[1] Takahashi T, Yamashita I, J. Polym. Sci. C: Polym. Lett., 3, 251 (1965)

[2] Takahashi T, Yamashita I, Miyakawa T, Bull. Chem. Soc. Jpn., 37, 131 (1964)

[3] Takahashi T, J. Polym. Sci. A: Polym. Chem., 6, 403 (1968)

[4] Cho I, Ahn KD, J. Polym. Sci. C: Polym. Lett., 15, 751 (1977)

[5] Cho I, Ahn KD, J. Polym. Sci. A: Polym. Chem., 17, 3169 (1979)

[6] Cho I, Ahn KD, J. Polym. Sci. A: Polym. Chem., 17, 3183 (1979)

[7] Cho I, Kim JB, J. Polym. Sci. A: Polym. Chem., 18, 3053 (1980)

[8] Cho I, Lee JY, Makromol. Chem. Rapid Commun., 5, 263 (1984)

[9] Borchert AE, Overberger CG, J. Polym. Sci., 44, 483 (1960)

[10] Overberger CG, Borchert AE, Katchman A, J. Polym. Sci., 44, 492 (1960)

[11] Cho I, Song SS, J. Polym. Sci. A: Polym. Chem., 27, 3151 (1989)

[12] Cho I, Kim WT, J. Polym. Sci. C: Polym. Lett., 24, 109 (1986)

[13] Bailey WJ, Polym. J., 17, 85 (1985)

[14] Bailey WJ, Wu SR, Ni Z, J. Macromol. Sci.-Chem., 18, 973 (1982)

[15] Bailey WJ, Gapud B, ACS Symp. Ser., 280, 423 (1985)

[16] Bailey WJ, Ni Z, Wu SR, Macromolecules, 15, 711 (1982)

[17] Bailey WJ, Ni Z, Wu SR, J. Polym. Sci. A: Polym. Chem., 20, 3021 (1982)

[18] Cho I, Gong MS, J. Polym. Sci. C: Polym. Lett., 20, 361 (1982)

[19] Cho I, Kim SK, J. Polym. Sci. C: Polym. Lett., 28, 417 (1990)

[20] Yokozawa T, Hayashi R, Endo T, J. Polym. Sci. A: Polym. Chem., 28, 3739 (1990)

[21] Rasoul HAA, McKinney MA, Aiani KE, Polym. Prepr. Am. Chem. Soc. Div. Polym. Chem., 31, 26 (1990)