계면중합에 의한 Poly(enaminonitrile)의 합성과 그들의 열적성질

김상태; 이진오; 김영식; 공명선

Polymer(Korea), Vol.15, No.1, 95-101, February, 1991

Export Citation

계면중합에 의한 Poly(enaminonitrile)의 합성과 그들의 열적성질

Synthesis of Poly(enaminonitrile) by Interfacial Polymerization and Their Thermal Properties

김상태, 이진오, 김영식, 공명선

초록

2관능성 dicyanovinyl 화합물인 p-bis(α-chloro-β, β-dicyanovinyl) benzene을 합성하고 이를 1, 2-diaminoethane, 1,4-diaminobutane, 1,6-diaminohexane, 1,8-diaminooctane, piperazine과 같은 alkylene-diamine과 계면 중합 방법에 의하여 poly(enaminonitrile)을 합성하였다. 합성된 중합체는 N-methyl pyrrolidinone, N,N-dimethylformamide, N,N- dimethylacetamide, dimethylsulfoxide 등에는 매우 잘 녹았으며 그 외의 일반 유기 용매에는 녹지 않았다. 시차 열분석으로부터 합성된 중합체들은 320∼400℃사이에서 이성화 및 가교화를 나타내는 큰 열방출 피크를 보여주고 있다. 또한 열중량 분석에 의하여 5%의 중량 감소가 380℃ 부근에서 관찰되었으며, 500℃에서의 잔류 중량은 72% 이상이었다.

Poly(enaminonitriles) were synthesized by reacting p-bis(α-chloro-β, β-dicyanovinyl) benzene as an difunctional dicyanovinyl compound with alkylene diamine such as 1, 2-diaminoethane, 1,4-diaminobutane, 1,6-diaminohexane, 1,8-diaminooctane, piperazine by interfacial polymerization techniques. Poly(enaminonitriles) were soluble in N-methyl pyrrolidinone, N, N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, but not soluble in common organic solvents. A large exothermic peak due to isomerization and cross-linking is observed in differential scanning calorimetry(DSC) thermogram around 320∼400℃ region. And thermal gravimetric analysis(TGA) curves of these polymers show 5% of weight loss around 380℃. Residual weight at 500℃ was above 72% in most of the polymers.

[References]

Rapport Z, Adv. Phys. Org. Chem., 7, 1823 (1969)
Josey AD, Dickinson CL, J. Org. Chem., 32, 1941 (1969)
Stamatoff J, Proc. SPIE, 682, 85 (1986)
Hall HK, J. Macromol. Sci.-Chem., A25(5-7), 792 (1988)
Moore JA, Kochanowski JE, Macromolecules, 8, 121 (1975)
Mehta PG, Moore JA, Polym. Mater. Sci. Eng., 63 (1990)
Moore JA, Mitchell TD, J. Polym. Sci. A: Polym. Chem., 18, 3029 (1980)
Rappoport Z, Adv. Phys. Org. Chem., 7, 1823 (1969)
Katz HH, Singer KD, Mater. Res. Soc. Symp. Proc., 109, 127 (1988)
Moore JA, Robello DR, Macromolecules, 22, 1084 (1989)
Hall HK, Padias AB, Deutschman A, Westerman IJ, J. Org. Chem., 44, 2038 (1979)
Nakamura T, Soma M, Onishi T, Tamaru K, Macromol. Chem., 135, 241 (1970)
Modena G, Accounts Chem. Res., 4, 73 (1971)

[Referenced By]

[1] Rapport Z, Adv. Phys. Org. Chem., 7, 1823 (1969)

[2] Josey AD, Dickinson CL, J. Org. Chem., 32, 1941 (1969)

[3] Stamatoff J, Proc. SPIE, 682, 85 (1986)

[4] Hall HK, J. Macromol. Sci.-Chem., A25(5-7), 792 (1988)

[5] Moore JA, Kochanowski JE, Macromolecules, 8, 121 (1975)

[6] Mehta PG, Moore JA, Polym. Mater. Sci. Eng., 63 (1990)

[7] Moore JA, Mitchell TD, J. Polym. Sci. A: Polym. Chem., 18, 3029 (1980)

[8] Rappoport Z, Adv. Phys. Org. Chem., 7, 1823 (1969)

[9] Katz HH, Singer KD, Mater. Res. Soc. Symp. Proc., 109, 127 (1988)

[10] Moore JA, Robello DR, Macromolecules, 22, 1084 (1989)

[11] Hall HK, Padias AB, Deutschman A, Westerman IJ, J. Org. Chem., 44, 2038 (1979)

[12] Nakamura T, Soma M, Onishi T, Tamaru K, Macromol. Chem., 135, 241 (1970)

[13] Modena G, Accounts Chem. Res., 4, 73 (1971)