Synthesis and Physical Properties of Oligo(propylene oxide-block-ethylene oxide) Allyl Methyl Ether

Chang-Sik Kweon; Doo-Won Kim; Hang-Kyu Cho; Si-Tae Noh

Journal of Industrial and Engineering Chemistry, Vol.9, No.2, 146-152, March, 2003

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Synthesis and Physical Properties of Oligo(propylene oxide-block-ethylene oxide) Allyl Methyl Ether

Chang-Sik Kweon, Doo-Won Kim¹, Hang-Kyu Cho, and Si-Tae Noh^†

Department of Chemical Engineering, Hanyang University, Ansan 425-791, Korea
¹Sin-jin Chemical Industry Co., Ltd., Ansan 425-100, Korea

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Oligo(propylene oxide-block-ethylene oxide) allyl methyl ethers (Allyl oligo(PO-b-EO) Me) with varying chain lengths and EO/PO ratios were synthesized using methylation, and addition reaction. Allyl oligo(PO-b-EO) with the reactive allyl end group was prepared by adding PO and EO using allyl alcoholate initiator ionized with KOH. Metallization was applied to the other hydroxy end using t-BuOK. Allyl oligo(PO-b-EO) Me was then synthesized by reacting this metallic anion with MeOTs of a good leaving group using SN2. These mono- and bi-substituted oligomers were identified using FT-IR, 1H-NMR, and GPC. They were then studied for the thermal properties and aqueous solution phase behaviors.

Keywords:ethylene oxide;propylene oxide;allyl ether group;methylation;and phase transition behaviour

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[1] Suzuki T, Tomono T, J. Polym. Sci. A: Polym. Chem., 22, 2829 (1984)

[2] Smith PB, Cutie SS, Henton DE, Powell C, Kosman J, Howell BA, J. Polym. Sci. A: Polym. Chem., 35(4), 799 (1997)

[3] Abuchowski A, VanEs T, Palczuk NC, Davis FF, J. Biol. Chem., 252, 3578 (1977)

[4] Lisli PJ, vanEs T, Abuchowski A, Palczuk NC, Davis FF, J. Appl. Biochem., 4, 19 (1982)

[5] Woghiren C, Sharma B, Stein S, Bioconjugate Chem., 4, 314 (1993)

[6] Zalipsky S, Bioconjugate Chem., 4, 296 (1993)

[7] Lee RJ, Low PS, J. Biol. Chem., 269, 3198 (1994)

[8] Ito K, Yokoyama S, Arakawa F, Yukawa Y, Iwashita T, Yamazaki Y, Polym. Bull., 16, 337 (1986)

[9] Chao D, Itsuno S, Ito K, Polym. J., 23, 1045 (1991)

[10] Cammas S, Nagasaki Y, Kataoka K, Bioconjugate Chem., 6, 226 (1995)

[11] Wagner R, Wu Y, Gzichocki G, Berlepsch HV, Weiland B, Rexin F, Perepelittchenko L, Appl. Organometal. Chem., 13, 611 (1999)

[12] Wagner R, Wu Y, Gzichocki G, Berlepsch HV, Rexin F, Perepelittchenko L, Appl. Organometal. Chem., 13, 201 (1999)

[13] Wagner R, Wu Y, Berlepsch HV, Zastrow H, Weiland B, Perepelittchenko L, Appl. Organometal. Chem., 13, 845 (1999)

[14] Cammas S, Nagasaki Y, Kataoka K, Bioconjugate Chem., 6, 226 (1995)

[15] Yu SH, U.S. Patent, 4,722,978 (1985)

[16] Kang YS, Noh SH, Choi SO, Nam KD, J. Korean Ind. Eng. Chem., 9(5), 749 (1998)

[17] Kang YS, Nam KD, J. Korean Oil Chem. Soc., 14, 23 (1997)

[18] Yoo YC, Rho SH, Ju MJ, Nam KD, J. Korean Ind. Eng. Chem., 7(2), 289 (1996)

[19] Yoo YC, Kim SC, Kim TY, Ju MJ, Nam KD, J. Korean Ind. Eng. Chem., 7(2), 299 (1996)

[20] Saraiva A, Persson O, Fredenslund A, Fluid Phase Equilib., 91, 291 (1993)

[21] Haglund BO, Thermochim. Acta, 114, 97 (1987)

[22] Kim YD, Kim JH, Cho YS, J. Ind. Eng. Chem., 7(1), 1 (2001)