Abstract

We report on both polar and nonpolar light-induced orientation of a polyimide of high glass transition temperature (<i>T</i><sub>g</sub>≈210 °C) with nonlinear optical azo dye molecules in the side chain. This photoinduced orientation is shown to occur at room temperature, i.e., at least 190 °C below the <i>T</i><sub>g</sub> value of the polymer, which indicates that the photoisomerization-induced movement of the nonlinear optical chromophores induces, in turn, a movement of the polyimide main chain. This allows for an efficient orientation of the dye molecules in spite of the stiffness of the polyimide main chain. A nonpolar orientation is induced by polarized light irradiation alone, whereas polar orientation is achieved by application of a dc field during the photoisomerization process. Further light irradiation in the absence of a dc field destroys the previously induced stable polar order. A detailed theoretical study of this light-induced depoling process is also presented.

© 1996 Optical Society of America

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1995

Z. Sekkat, C.-S. Kang, E. F. Aust, G. Wegner, and W. Knoll, “Room-temperature photoinduced poling and thermal pol-ing of a rigid main chain polymer with polar azo dyes in the side chain,” Chem. Mater. 7, 142(1995).

T. Verbiest, D. M. Burland, M. C. Jurich, V. Y. Lee, R. D. Miller, and W. Volksen, “Exceptionally thermally stable polyimides for second-order nonlinear optical applications,” Science 268, 1604(1995).

Z. Sekkat and W. Knoll, “Creation of second-order nonlinear optical effects by photoisomerization of polar azo dyes in polymeric films: theoretical study of steady-state and transient properties,” J. Opt. Soc. Am. B 12, 1855(1995).

1994

Z. Sekkat and W. Knoll, “Stationary state and dynamics of birefringence and nonlinear optical properties induced by electric field poling in polymeric films,” Ber. Bunsenges. Phys. Chem. 98, 1231(1994).

C.-S. Kang, H.-J. Winkelhahn, M. Schultze, D. Neher, and G. Wegner, “Synthesis and properties of aromatic main chain polyesters having disperse-red-1 nonlinear optical chromophores in the side chain,” Chem. Mater. 6, 2159(1994).

D. M. Burland, R. D. Miller, C. A. Walsh, “Second-order nonlinearity in poled-polymer systems,” Chem. Rev. 94, 31 (1994).

Z. Sekkat, M. Büchel, H. Orendi, H. Menzel, and W. Knoll, “Photoinduced alignment of azobenzene moities in the side chains of polyglutamate films,” Chem. Phys. Lett. 220, 497(1994).

1993

Z. Sekkat and M. Dumont, “Photoinduced orientation of azo dyes in polymeric films. Characterization of molecular angular mobility,” Synth. Met. 54, 373(1993).

T. Seki, M. Skuragi, Y. Kawanishi, Y. Suzuki, T. Tamaki, R. Fukuda, and K. Ichimura, “Command surfaces of Langmuir–Blodgett films. Photoregulation of liquid crystal alignment by molecularly tailored surface azobenzene layers,” Langmuir 9, 211(1993).

F. Charra, F. Kajzar, J. M. Nunzi, P. Raimond, and E. Idiart, “Light-induced second harmonic generation in azo dye polymers,” Opt. Lett. 12, 941(1993).

1992

K. W. Beeson, P. M. Ferm, K. A. Horn, M. J. McFarland, A. Nahata, J. Shan, C. Wu, and J. T. Yardley, “Loss measurements in electro-optic polymer waveguides,” Proc. SPIE 1775, 133(1992).

P. A. Chollet, G. Gadret, F. Kajzar, and P. Raimond, “Electro-optic organic thin films in waveguided devices,” Proc. SPIE 1775, 121(1992).

1991

S. Barry and D. Soane, “Poling of polymeric thin films at ambient temperatures for second-harmonic generation,” Appl. Phys. Lett. 58, 1134(1991).

Y. Shi, W. H. Steier, L. Yu, M. Shen, and L. R. Dalton, “Large photoinduced birefringence in an optically nonlinear polyester polymer,” Appl. Phys. Lett. 59, 2935(1991).

1989

1984

1979

S. J. Lalama and A. F. Garito, “Origin of the nonlinear second-order optical susceptibilities of organic systems,” Phys. Rev. A 20, 1179(1979).

Aust, E. F.

Z. Sekkat, C.-S. Kang, E. F. Aust, G. Wegner, and W. Knoll, “Room-temperature photoinduced poling and thermal pol-ing of a rigid main chain polymer with polar azo dyes in the side chain,” Chem. Mater. 7, 142(1995).

Barry, S.

S. Barry and D. Soane, “Poling of polymeric thin films at ambient temperatures for second-harmonic generation,” Appl. Phys. Lett. 58, 1134(1991).

Beeson, K. W.

K. W. Beeson, P. M. Ferm, K. A. Horn, M. J. McFarland, A. Nahata, J. Shan, C. Wu, and J. T. Yardley, “Loss measurements in electro-optic polymer waveguides,” Proc. SPIE 1775, 133(1992).

Büchel, M.

Z. Sekkat, M. Büchel, H. Orendi, H. Menzel, and W. Knoll, “Photoinduced alignment of azobenzene moities in the side chains of polyglutamate films,” Chem. Phys. Lett. 220, 497(1994).

Burland, D. M.

T. Verbiest, D. M. Burland, M. C. Jurich, V. Y. Lee, R. D. Miller, and W. Volksen, “Exceptionally thermally stable polyimides for second-order nonlinear optical applications,” Science 268, 1604(1995).

D. M. Burland, R. D. Miller, C. A. Walsh, “Second-order nonlinearity in poled-polymer systems,” Chem. Rev. 94, 31 (1994).

Charra, F.

Chollet, P. A.

P. A. Chollet, G. Gadret, F. Kajzar, and P. Raimond, “Electro-optic organic thin films in waveguided devices,” Proc. SPIE 1775, 121(1992).

Dalton, L. R.

Y. Shi, W. H. Steier, L. Yu, M. Shen, and L. R. Dalton, “Large photoinduced birefringence in an optically nonlinear polyester polymer,” Appl. Phys. Lett. 59, 2935(1991).

Dumont, M.

Z. Sekkat and M. Dumont, “Photoinduced orientation of azo dyes in polymeric films. Characterization of molecular angular mobility,” Synth. Met. 54, 373(1993).

Ferm, P. M.

K. W. Beeson, P. M. Ferm, K. A. Horn, M. J. McFarland, A. Nahata, J. Shan, C. Wu, and J. T. Yardley, “Loss measurements in electro-optic polymer waveguides,” Proc. SPIE 1775, 133(1992).

Fukuda, R.

T. Seki, M. Skuragi, Y. Kawanishi, Y. Suzuki, T. Tamaki, R. Fukuda, and K. Ichimura, “Command surfaces of Langmuir–Blodgett films. Photoregulation of liquid crystal alignment by molecularly tailored surface azobenzene layers,” Langmuir 9, 211(1993).

Gadret, G.

P. A. Chollet, G. Gadret, F. Kajzar, and P. Raimond, “Electro-optic organic thin films in waveguided devices,” Proc. SPIE 1775, 121(1992).

Garito, A. F.

S. J. Lalama and A. F. Garito, “Origin of the nonlinear second-order optical susceptibilities of organic systems,” Phys. Rev. A 20, 1179(1979).

Horn, K. A.

K. W. Beeson, P. M. Ferm, K. A. Horn, M. J. McFarland, A. Nahata, J. Shan, C. Wu, and J. T. Yardley, “Loss measurements in electro-optic polymer waveguides,” Proc. SPIE 1775, 133(1992).

Ichimura, K.

T. Seki, M. Skuragi, Y. Kawanishi, Y. Suzuki, T. Tamaki, R. Fukuda, and K. Ichimura, “Command surfaces of Langmuir–Blodgett films. Photoregulation of liquid crystal alignment by molecularly tailored surface azobenzene layers,” Langmuir 9, 211(1993).

Idiart, E.

Jurich, M. C.

T. Verbiest, D. M. Burland, M. C. Jurich, V. Y. Lee, R. D. Miller, and W. Volksen, “Exceptionally thermally stable polyimides for second-order nonlinear optical applications,” Science 268, 1604(1995).

Kajzar, F.

F. Charra, F. Kajzar, J. M. Nunzi, P. Raimond, and E. Idiart, “Light-induced second harmonic generation in azo dye polymers,” Opt. Lett. 12, 941(1993).

P. A. Chollet, G. Gadret, F. Kajzar, and P. Raimond, “Electro-optic organic thin films in waveguided devices,” Proc. SPIE 1775, 121(1992).

Kang, C.-S.

Z. Sekkat, C.-S. Kang, E. F. Aust, G. Wegner, and W. Knoll, “Room-temperature photoinduced poling and thermal pol-ing of a rigid main chain polymer with polar azo dyes in the side chain,” Chem. Mater. 7, 142(1995).

C.-S. Kang, H.-J. Winkelhahn, M. Schultze, D. Neher, and G. Wegner, “Synthesis and properties of aromatic main chain polyesters having disperse-red-1 nonlinear optical chromophores in the side chain,” Chem. Mater. 6, 2159(1994).

Kawanishi, Y.

T. Seki, M. Skuragi, Y. Kawanishi, Y. Suzuki, T. Tamaki, R. Fukuda, and K. Ichimura, “Command surfaces of Langmuir–Blodgett films. Photoregulation of liquid crystal alignment by molecularly tailored surface azobenzene layers,” Langmuir 9, 211(1993).

King, L. A.

Knoll, W.

Z. Sekkat and W. Knoll, “Creation of second-order nonlinear optical effects by photoisomerization of polar azo dyes in polymeric films: theoretical study of steady-state and transient properties,” J. Opt. Soc. Am. B 12, 1855(1995).

Z. Sekkat, C.-S. Kang, E. F. Aust, G. Wegner, and W. Knoll, “Room-temperature photoinduced poling and thermal pol-ing of a rigid main chain polymer with polar azo dyes in the side chain,” Chem. Mater. 7, 142(1995).

Z. Sekkat, M. Büchel, H. Orendi, H. Menzel, and W. Knoll, “Photoinduced alignment of azobenzene moities in the side chains of polyglutamate films,” Chem. Phys. Lett. 220, 497(1994).

Z. Sekkat and W. Knoll, “Stationary state and dynamics of birefringence and nonlinear optical properties induced by electric field poling in polymeric films,” Ber. Bunsenges. Phys. Chem. 98, 1231(1994).

Kuzyk, M. G.

Lalama, S. J.

S. J. Lalama and A. F. Garito, “Origin of the nonlinear second-order optical susceptibilities of organic systems,” Phys. Rev. A 20, 1179(1979).

Lee, V. Y.

T. Verbiest, D. M. Burland, M. C. Jurich, V. Y. Lee, R. D. Miller, and W. Volksen, “Exceptionally thermally stable polyimides for second-order nonlinear optical applications,” Science 268, 1604(1995).

McFarland, M. J.

K. W. Beeson, P. M. Ferm, K. A. Horn, M. J. McFarland, A. Nahata, J. Shan, C. Wu, and J. T. Yardley, “Loss measurements in electro-optic polymer waveguides,” Proc. SPIE 1775, 133(1992).

Menzel, H.

Z. Sekkat, M. Büchel, H. Orendi, H. Menzel, and W. Knoll, “Photoinduced alignment of azobenzene moities in the side chains of polyglutamate films,” Chem. Phys. Lett. 220, 497(1994).

Miller, R. D.

T. Verbiest, D. M. Burland, M. C. Jurich, V. Y. Lee, R. D. Miller, and W. Volksen, “Exceptionally thermally stable polyimides for second-order nonlinear optical applications,” Science 268, 1604(1995).

D. M. Burland, R. D. Miller, C. A. Walsh, “Second-order nonlinearity in poled-polymer systems,” Chem. Rev. 94, 31 (1994).

Nahata, A.

K. W. Beeson, P. M. Ferm, K. A. Horn, M. J. McFarland, A. Nahata, J. Shan, C. Wu, and J. T. Yardley, “Loss measurements in electro-optic polymer waveguides,” Proc. SPIE 1775, 133(1992).

Neher, D.

C.-S. Kang, H.-J. Winkelhahn, M. Schultze, D. Neher, and G. Wegner, “Synthesis and properties of aromatic main chain polyesters having disperse-red-1 nonlinear optical chromophores in the side chain,” Chem. Mater. 6, 2159(1994).

Nikolova, L.

Nunzi, J. M.

Orendi, H.

Z. Sekkat, M. Büchel, H. Orendi, H. Menzel, and W. Knoll, “Photoinduced alignment of azobenzene moities in the side chains of polyglutamate films,” Chem. Phys. Lett. 220, 497(1994).

Raimond, P.

F. Charra, F. Kajzar, J. M. Nunzi, P. Raimond, and E. Idiart, “Light-induced second harmonic generation in azo dye polymers,” Opt. Lett. 12, 941(1993).

P. A. Chollet, G. Gadret, F. Kajzar, and P. Raimond, “Electro-optic organic thin films in waveguided devices,” Proc. SPIE 1775, 121(1992).

Schultze, M.

C.-S. Kang, H.-J. Winkelhahn, M. Schultze, D. Neher, and G. Wegner, “Synthesis and properties of aromatic main chain polyesters having disperse-red-1 nonlinear optical chromophores in the side chain,” Chem. Mater. 6, 2159(1994).

Seki, T.

T. Seki, M. Skuragi, Y. Kawanishi, Y. Suzuki, T. Tamaki, R. Fukuda, and K. Ichimura, “Command surfaces of Langmuir–Blodgett films. Photoregulation of liquid crystal alignment by molecularly tailored surface azobenzene layers,” Langmuir 9, 211(1993).

Sekkat, Z.

Z. Sekkat, C.-S. Kang, E. F. Aust, G. Wegner, and W. Knoll, “Room-temperature photoinduced poling and thermal pol-ing of a rigid main chain polymer with polar azo dyes in the side chain,” Chem. Mater. 7, 142(1995).

Z. Sekkat and W. Knoll, “Creation of second-order nonlinear optical effects by photoisomerization of polar azo dyes in polymeric films: theoretical study of steady-state and transient properties,” J. Opt. Soc. Am. B 12, 1855(1995).

Z. Sekkat and W. Knoll, “Stationary state and dynamics of birefringence and nonlinear optical properties induced by electric field poling in polymeric films,” Ber. Bunsenges. Phys. Chem. 98, 1231(1994).

Z. Sekkat, M. Büchel, H. Orendi, H. Menzel, and W. Knoll, “Photoinduced alignment of azobenzene moities in the side chains of polyglutamate films,” Chem. Phys. Lett. 220, 497(1994).

Z. Sekkat and M. Dumont, “Photoinduced orientation of azo dyes in polymeric films. Characterization of molecular angular mobility,” Synth. Met. 54, 373(1993).

Shan, J.

K. W. Beeson, P. M. Ferm, K. A. Horn, M. J. McFarland, A. Nahata, J. Shan, C. Wu, and J. T. Yardley, “Loss measurements in electro-optic polymer waveguides,” Proc. SPIE 1775, 133(1992).

Shen, M.

Y. Shi, W. H. Steier, L. Yu, M. Shen, and L. R. Dalton, “Large photoinduced birefringence in an optically nonlinear polyester polymer,” Appl. Phys. Lett. 59, 2935(1991).

Shi, Y.

Y. Shi, W. H. Steier, L. Yu, M. Shen, and L. R. Dalton, “Large photoinduced birefringence in an optically nonlinear polyester polymer,” Appl. Phys. Lett. 59, 2935(1991).

Singer, K. D.

Skuragi, M.

T. Seki, M. Skuragi, Y. Kawanishi, Y. Suzuki, T. Tamaki, R. Fukuda, and K. Ichimura, “Command surfaces of Langmuir–Blodgett films. Photoregulation of liquid crystal alignment by molecularly tailored surface azobenzene layers,” Langmuir 9, 211(1993).

Soane, D.

S. Barry and D. Soane, “Poling of polymeric thin films at ambient temperatures for second-harmonic generation,” Appl. Phys. Lett. 58, 1134(1991).

Steier, W. H.

Y. Shi, W. H. Steier, L. Yu, M. Shen, and L. R. Dalton, “Large photoinduced birefringence in an optically nonlinear polyester polymer,” Appl. Phys. Lett. 59, 2935(1991).

Suzuki, Y.

T. Seki, M. Skuragi, Y. Kawanishi, Y. Suzuki, T. Tamaki, R. Fukuda, and K. Ichimura, “Command surfaces of Langmuir–Blodgett films. Photoregulation of liquid crystal alignment by molecularly tailored surface azobenzene layers,” Langmuir 9, 211(1993).

Tamaki, T.

T. Seki, M. Skuragi, Y. Kawanishi, Y. Suzuki, T. Tamaki, R. Fukuda, and K. Ichimura, “Command surfaces of Langmuir–Blodgett films. Photoregulation of liquid crystal alignment by molecularly tailored surface azobenzene layers,” Langmuir 9, 211(1993).

Todorov, T.

Tomova, N.

Verbiest, T.

T. Verbiest, D. M. Burland, M. C. Jurich, V. Y. Lee, R. D. Miller, and W. Volksen, “Exceptionally thermally stable polyimides for second-order nonlinear optical applications,” Science 268, 1604(1995).

Volksen, W.

T. Verbiest, D. M. Burland, M. C. Jurich, V. Y. Lee, R. D. Miller, and W. Volksen, “Exceptionally thermally stable polyimides for second-order nonlinear optical applications,” Science 268, 1604(1995).

Walsh, C. A.

D. M. Burland, R. D. Miller, C. A. Walsh, “Second-order nonlinearity in poled-polymer systems,” Chem. Rev. 94, 31 (1994).

Wegner, G.

Z. Sekkat, C.-S. Kang, E. F. Aust, G. Wegner, and W. Knoll, “Room-temperature photoinduced poling and thermal pol-ing of a rigid main chain polymer with polar azo dyes in the side chain,” Chem. Mater. 7, 142(1995).

C.-S. Kang, H.-J. Winkelhahn, M. Schultze, D. Neher, and G. Wegner, “Synthesis and properties of aromatic main chain polyesters having disperse-red-1 nonlinear optical chromophores in the side chain,” Chem. Mater. 6, 2159(1994).

Winkelhahn, H.-J.

C.-S. Kang, H.-J. Winkelhahn, M. Schultze, D. Neher, and G. Wegner, “Synthesis and properties of aromatic main chain polyesters having disperse-red-1 nonlinear optical chromophores in the side chain,” Chem. Mater. 6, 2159(1994).

Wu, C.

K. W. Beeson, P. M. Ferm, K. A. Horn, M. J. McFarland, A. Nahata, J. Shan, C. Wu, and J. T. Yardley, “Loss measurements in electro-optic polymer waveguides,” Proc. SPIE 1775, 133(1992).

Yardley, J. T.

K. W. Beeson, P. M. Ferm, K. A. Horn, M. J. McFarland, A. Nahata, J. Shan, C. Wu, and J. T. Yardley, “Loss measurements in electro-optic polymer waveguides,” Proc. SPIE 1775, 133(1992).

Yu, L.

Y. Shi, W. H. Steier, L. Yu, M. Shen, and L. R. Dalton, “Large photoinduced birefringence in an optically nonlinear polyester polymer,” Appl. Phys. Lett. 59, 2935(1991).

Zahn, H. E.

Appl. Opt.

Appl. Phys. Lett.

Y. Shi, W. H. Steier, L. Yu, M. Shen, and L. R. Dalton, “Large photoinduced birefringence in an optically nonlinear polyester polymer,” Appl. Phys. Lett. 59, 2935(1991).

S. Barry and D. Soane, “Poling of polymeric thin films at ambient temperatures for second-harmonic generation,” Appl. Phys. Lett. 58, 1134(1991).

Ber. Bunsenges. Phys. Chem.

Z. Sekkat and W. Knoll, “Stationary state and dynamics of birefringence and nonlinear optical properties induced by electric field poling in polymeric films,” Ber. Bunsenges. Phys. Chem. 98, 1231(1994).

Chem. Mater.

Z. Sekkat, C.-S. Kang, E. F. Aust, G. Wegner, and W. Knoll, “Room-temperature photoinduced poling and thermal pol-ing of a rigid main chain polymer with polar azo dyes in the side chain,” Chem. Mater. 7, 142(1995).

C.-S. Kang, H.-J. Winkelhahn, M. Schultze, D. Neher, and G. Wegner, “Synthesis and properties of aromatic main chain polyesters having disperse-red-1 nonlinear optical chromophores in the side chain,” Chem. Mater. 6, 2159(1994).

Chem. Phys. Lett.

Z. Sekkat, M. Büchel, H. Orendi, H. Menzel, and W. Knoll, “Photoinduced alignment of azobenzene moities in the side chains of polyglutamate films,” Chem. Phys. Lett. 220, 497(1994).

Chem. Rev.

D. M. Burland, R. D. Miller, C. A. Walsh, “Second-order nonlinearity in poled-polymer systems,” Chem. Rev. 94, 31 (1994).

J. Opt. Soc. Am. B

Langmuir

T. Seki, M. Skuragi, Y. Kawanishi, Y. Suzuki, T. Tamaki, R. Fukuda, and K. Ichimura, “Command surfaces of Langmuir–Blodgett films. Photoregulation of liquid crystal alignment by molecularly tailored surface azobenzene layers,” Langmuir 9, 211(1993).

Opt. Lett.

Phys. Rev. A

S. J. Lalama and A. F. Garito, “Origin of the nonlinear second-order optical susceptibilities of organic systems,” Phys. Rev. A 20, 1179(1979).

Proc. SPIE

K. W. Beeson, P. M. Ferm, K. A. Horn, M. J. McFarland, A. Nahata, J. Shan, C. Wu, and J. T. Yardley, “Loss measurements in electro-optic polymer waveguides,” Proc. SPIE 1775, 133(1992).

P. A. Chollet, G. Gadret, F. Kajzar, and P. Raimond, “Electro-optic organic thin films in waveguided devices,” Proc. SPIE 1775, 121(1992).

Science

T. Verbiest, D. M. Burland, M. C. Jurich, V. Y. Lee, R. D. Miller, and W. Volksen, “Exceptionally thermally stable polyimides for second-order nonlinear optical applications,” Science 268, 1604(1995).

Synth. Met.

Z. Sekkat and M. Dumont, “Photoinduced orientation of azo dyes in polymeric films. Characterization of molecular angular mobility,” Synth. Met. 54, 373(1993).

Other

M. Sawodny, A. Schmidt, M. Stamm, W. Knoll, C. Urban, and H. Ringsdorf, “Photoreactive Langmuir–Blodgett–Kuhn multilayer assemblies from functionalized liquid crystalline side chain polymers. I. Homopolymers containing azobenzene chromophores,” Polym. Adv. Technol. 2, 127 (1991).

Z. Sekkat, “Création d’anisotropie et d’effets non linéaires du second ordre par photoisomérisation de dérivés de l’azobenzène dans des films de polymères,” Ph.D. dissertation (Paris-Sud University, Paris, 1992).

Z. Sekkat and M. Dumont, “Photoassisted poling of azo dye doped polymeric films at room temperature,” Appl. Phys. B 54, 486(1992); “Poling of polymer films by photoisomerization of azo dye chromophores,” Mol. Cryst. Liq. Cryst. Sci. Tech. B 2, 359 (1992).

R. D. Miller, D. M. Burland, M. C. Jurich, V. Y. Lee, C. R. Moylan, R. J. Tweig, J. Thackara, T. Verbiest, W. Volksen, and C. A. Walsh, “High temperature nonlinear polyimides for χ(2) applications,” in Polymers for Second-Order Nonlinear Optics, G. Lindsay and K. D. Singer, eds., ACS Symposium Series 601 (American Chemical Society, Washington, D. C., 1995), Chap. 10, pp. 130–146.

Z. Sekkat, E. F. Aust, and W. Knoll, “Photoinduced poling of polar azo dyes in polymeric films. Toward second-order applications,” in Polymers for Second-Order Nonlinear Optics, G. Lindsay and K. D. Singer, eds., ACS Symposium Series 601 (American Chemical Society, Washington, D. C., 1995), Chap. 19, pp. 255–274.

H. Rau, “Photoisomerization of azobenzenes,” in Photochemistry and Photophysics, F. J. Rabeck, ed. (CRC, Boca Raton, Fla., 1990), Vol. 2, Chap. 4, pp. 119–141. This paper contains a large bibliography on photoisomerization.

R. Loucif-Saibi, K. Nakatani, J. A. Delaire, M. Dumont, and Z. Sekkat, “Photoisomerization and second-harmonic generation in disperse red one-doped and-functionalized poly(methyl methacrylate) films,” Chem. Mater. 5, 229 (1993).

R. E. Robertson, “Effect of free volume fluctuations on polymer relaxation in the glassy state,” J. Polym. Sci. Polym. Symp. 1, 173 (1978).

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