1) D. D. Coffman, E. E. Jenner : JACS, 76, 2685 (1954) 2) A. Weissberger et al.:" Organic Solvent", 390 (1955) 4) L. F. Fieser:" Experiments in Organi

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Transcription:

1) D. D. Coffman, E. E. Jenner : JACS, 76, 2685 (1954) 2) A. Weissberger et al.:" Organic Solvent", 390 (1955) 4) L. F. Fieser:" Experiments in Organic Chemi. stry ", 21 (1955) 5) W. R. Sorenson, T. W. Campbell: Study on Ionic Telomerization I. Synthesis of Glycol of Polystyrene by Ionic Telomerization and Reaction of the Glycol with Diisocyanates By Junji Furukawa*, Shinzo Yamashita* and Tetsuo Sato** Cationic telomerization of styrene was carried out by using both acetic acid and paraformaldehyde. The measurement of IR spectra, molecular weight given in the Rust method, and saponification equivalent of the telomers obtained show clearly that these telomers are mostly diacetate which contains one to five units of styrene. These diacetates were saponified with alcoholic potassium hydroxide to afford glycol. The reaction of these glycols with 2,4-toluene diisocyanate or hexamethylene diisocyanate gave brittle resinous polyurethanes. The intrinsic viscosity of these polyurethanes in toluene was 0.04 to 0.13 at 30 Ž. The result supports the view that these styrene telomers obtained have bifunctional hydroxy groups approximately. *Department of Synthetic Chemistry, Faculty of Engineering **Sakai Chemical Industry Co. (Terada, Suma-ku, Kobe), Kyoto University (Yoshida, Sakyo-ku, Kyoto)

Table 1. Recipe (mol). a) ethylene oxide was used in the place of the aldehyde. b) after reaction for 24 hr, 0.75 mol of paraformaldehyde was added. c) after reaction for 24 hr, 1.66 mol of acetic acid was added. d) after reaction for 24 hr, 3.0 mol of paraformaldohyde was added. e) after reaction for 24 hr and 48 hr, 0.025 mol of BF3 etherate was added respectively.

Table 2. Preparation and characterization of Telomers. a) saponification equivalent, b) molecular weight of diacetate by means of the Rust method, c) hydroxyl equivalent of glycol, d) molecular weight of glycol by means of the Rust method, e) AcOH-Acetic acid, HCHO-formaldehyde.

of poly- Wave number (cm') Fig. 1. IR spectrum of the diacetate isoprene (IA-2). Wave number (cm') \ : Addition of paraformaldehyde ---: No addition Fig. 2. Effect of addition of paraformaldehyde. a) Molecular weight/saponification equivalent, b) Molecular weight (Method of Rust), c) Reacted for 24 hr, not added paraformaldehyde, d) Reacted for 24 hr, added paraformaldehyde Fig. 3. Effect of addition of paraformaldehyde.

(BF3 etherate/isoprene) mol ratio (1), (2), (3) and (4) show sample No. IB, IF, I J and IM-2, respectively. Fig. 6. Effect of the amount of paraformaldehyde added. Wave number (cm-1) Fig. 4. Unsaturated groups of telomer. Wave number (cm-1) Fig. 5. IR spectrum of glycol of polyisoprene (IA'-2). (Paraformaldehyde/Isoprene) mol ratio (1), (2), (3) and (4) show sample No. ID, IA, IN and IK, respectively. Fig. 7. Effect of the amount of BF3 etherate added.

Fig. 9. Effect of the amount of acids added. Fig. 8. Effect of reaction time.

Table 3. Preparation and characterization of polyurethanes. a) melting point of the product: 150 Ž, b) melting point of the product: 80 Ž, c) after reaction the reactant was poured into ethylene diamine., d) in toluene, at 30 Ž, e) in pyridine, at 30 Ž.

a) glycol of polyisoprene: MW (the Rust method) 820, b) polytetramethyleneglycol: MW(the Rust method) 1296, c) diphenylmethanediisocyanate, d) PTMG and DMDI were mixed and reacted during 2 hr at 80 Ž, after that IK' was added and the reaction was continued during 3 hr at 120 Ž, e) in acetone, at 30 Ž, f) Blank polymer, not contained isoprene unit, g) gel portion was seperated. Table 5. Recipe of polyurethane rubber. a) cf. Table 4, b) tetramethylthiuramdisulfide. Table 6. Physical properties of the vulcanizates of polyurethane rubber. Soc., 73, 4348 (1951) 4) A. Weissberger "Organic Solvent", 390 1) D. D. Coffman, E. L. Jenner: J. Am. Chem. Soc., 76, 2685 (1954) 5) A. Weissberger "Organic Solvent", 394 (1955) 3) E. L. Jenner, R. S. Schreiber: J. Am. Chem.

II. Synthesis of Glycol of Polyisoprene by Ionic Telomerization of Isoprene and Reaction of the Glycol with Diisocyanates By Junji Furukawa*, Shinzo Yamashita* and Tetsuo Sato** Cationic telomerization of isoprene was investigated with the catalytic system consisting of paraformaldehyde, acetic acid and BF3 etherate. The telomers obtained possessed 1 to 15 units of isoprene, 0.5 `3.7 units of acetate group and others. Both the number of acetate group per mole and average molecular weight of the telomer were found to be increased by using acetic anhydride. The best condition for the telomerization reaction to obtain the telomer having the structure of diacetate with high molecular weight were studied, and some mechanisms of the telomerization were postulated on the base of the experimental results. Glycol of polyisoprene was able to obtain by saponification of the diacetate and was found to react easily with diisocyanate to give resinous polyurethane. The addition polymer of diisocyanate, polytetramethyleneglycol and glycol of polyisoprene has been found to show good vulcanization properties for conventional sulfur vulcanization. *Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University (Yoshida, Sakyo-ku, Kyoto) **Sakai Chemical Industrial Co. (Terada-cho, Suma-ku, Kobe)

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