Abstract
A series of noncyclic acetal-linked cleavable surfactants were simply prepared by condensation of aldehydes with poly(ethylene glycol) monomethyl ethers. All of the products were characterized by1H nuclear magnetic resonance. Their hydrophile-lipophile balance, surface tension, cloud point, critical micelle concentration, and foam height were determined. Hydrolysis kinetic studies, followed by gas chromatography, showed that they had higher hydrolytic reactivity in acidic solution than cyclic acetal-linked cleavable surfactants.
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References
Jaeger, D.A., J. Mohebalian, and P.L. Rose, Acid-Catalyzed Hydrolysis and Monolayer Properties of Ketal-Based Cleavable Surfactants,Langmuir 6:547–554 (1990).
Jaeger, D.A., J. Jamrozik, T.G. Golich, M.W. Clennan, and J. Mohebalian, Preparation and Characterization of Glycerol-Based Cleavable Surfactants and Derived Vesicles,J. Am. Chem. Soc. 111:3001–3006 (1989).
Jaeger, D.A., P.K. Chou, D. Bolikal, D. Ok, K.Y. Kim, J.B. Huff, E. Yi, and N.A. Porter, Kinetics of Amphiphilic Ketone Epimerizations in Cleavable Surfactant Hosts.,110:5123–5129 (1988).
Jaeger, D.A., and T.G. Golich, Preparation and Characterization of Double-Chain Destructible Surfactants and Derived Vesicles,J. Am. Oil Chem. Soc. 64:1550–1551 (1987).
Jaeger, D.A., C.A. Martin, and T.G. Golich, Destructible Surfactants Based on a Ketal Group,J. Org. Chem. 49:4545–4547 (1984).
Jaeger, D.A., and M.R. Frey, Preparation and Characterization of Destructible Surfactants,47:311–315 (1982).
Yamamura, S., M. Nakamura, K. Kasai, H. Sato, and T. Takeda, Synthesis and Properties of Destructible Anionic Surfactants with a 1,3-Dioxolane Ring and Their Use as Emulsifier for Emulsion Polymerization,J. Jpn. Oil Chem. Soc. 40:1002–1006 (1991).
Yamamura, S., M. Nakamura, K. Tanaka, and T. Takeda, Synthesis and Properties of Acetal-Containing Surface-Active Alkanolamides and Aminopolyether,40:104–108 (1991).
Yamamura, S., K. Shimaki, T. Nakajima, T. Takeda, I. Iketa, and M. Okahara, Synthesis and Properties of Destructible Cationic Surfactants with a 1,3-Dioxolane Ring from Acetonyl Alkyl Ether of Aldehyde,40: 16–19 (1991).
Yamamura, S., M. Nakamura, and T. Takeda, Synthesis and Properties of Destructible Anionic and Cationic Surfactants with a 1,3-Dioxolane Ring,J. Am. Oil Chem. Soc. 66:1165–1170 (1989).
Jaeger, D.A., Y.M. Sayed, and A.K. Dutta, Second-Generation Single-Chain Cleavable Surfactants,Tetrahedron Lett. 31:449–450 (1990).
Ono, D., A. Masuyama, and M. Okahara, Preparation of New Acetal Type Cleavable Surfactants from Epichlorohydrin,J. Org. Chem. 55:4461–4464 (1990).
Jaeger, D.A., C.T. Fionley, M.R. Walter, and C.A. Martin, Preparation and Characterization of Base-Sensitive Destructible Surfactants.51:3956–3959 (1986).
Jaeger, D.A., M.D. Ward, and A.K. Dutta, Preparation and Characterization of Cleavable Surfactants Based on a Silicon-Oxygen Bond,53:1577–1580 (1988).
Hayashi, Y., F. Shirai, T. Shimizu, Y. Nagano, and K. Teramura, Synthesis and Properties of 2-Alkoxy-N,N-DimethylethylamineN-Oxides,J. Am. Chem. Soc. 62:555–557 (1985).
Epstein, W.W., D.S. Jones, E. Brunenger, and H.C. Rilling, The Synthesis of a Photolabile Detergent and Its Use in the Isolation and Characterization of Protein,Anal. Biochem. 119:304–312 (1982).
Sokolowski, A., A. Piasecki, and B. Burczyk, Synthesis and Surface Properties of Chemodegradable Anionic Surfactants: Sodium Salts of Sulfated 2-n-Alkyl-5-Hydroxymethyl-5-Methyl-1,3-Dioxanes.J. Am. Oil Chem. Soc. 69:633–638 (1992).
Burczyk, B., M. Banaszczyk, A. Sokolowski, and A. Piasecki, Synthesis and Surface Properties of Oxyethylenated 2-Alkyl-5-Hydroxymethyl-5-Ethyl-1,3-Dioxanes,65:1204–1210 (1988).
Kida, T., A. Masuyama, and M. Okahara, Preparation of Trihydroxy-Carboxylates Bearing a Long-Chain Alkyl Acetal Group From Glucono-1,5-Lactone,Tetrahedron Lett. 31:5939–5942 (1990).
Burczyk, B., and A. Sokolowski, Relation Between Chemical Structure and Surface Activity I: Synthesis and Properties of Aqueous Solutions of Acetals Formed from Aliphatic Aldehydes and Monoalkyl Ethers of Ethylene Glycols,Tenside Det. 15:68–71 (1978).
Myers, D.,Surfactant Science and Technology, 2nd edn, VCH Publishers, Inc., New York, 1992, pp. 66–67.
ASTM Methods, Standard Test Method for Cloud Point of Nonionic Surfactants, American Society for Testing and Materials, Philadelphia, 1986, D2024.
Griffin, W., Calculations of HLB Values of Nonionic Surfactants,J. Soc. Cos. Chem. 5:249–256 (1954).
Kita, T., N. Morishima, A. Masuyama, and Y. Nakatsuji, New Cleavable Surfactants Derived from Glucono-1,5-Lactone,J. Am. Oil Chem. Soc. 71:705–710 (1994).
Rosen, M.J.,Surfactants and Interfacial Phenomena, 1st edn., John Wiley & Sons, Inc., New York, 1978, pp. 165–166.
Miesiac, I., and J. Szymanowski, Influence of Hydroxyl Group Substitution on Micellar Properties of Polyoxyethylene Alcohols,Progr. Colloid Polym. Sci. 76:96–100 (1988).
Sela, Y., N. Garti, and S. Magdassi, Surface Activity and Emulsification Properties of New Polyethylene Glycol Based Nonionic Surfactants,J. Dispersion Sci. Tech. 14:237–247 (1993).
Schott, H. Hydrophile-Lipophile Balance and Cloud Points of Nonionic Surfactants.J. Pharm. Sci. 58:1443–1449 (1969).
Ono, D., T. Tanaka, and M. Okahara, Cleavable Surfactants of the Acetal Type,Tenside Surf. Det. 29:412–417 (1992).
Wilk, K.A., A. Bieniecki, B. Burczyk, and A. Sokolowski, Synthesis and Hydrolysis of Chemodegradable Cationic Surfactants Containing the 1,3-Dioxolane Moiety,J. Am. Oil Chem. Soc. 71:81–85 (1994).
Cordes, E.H., and H.G. Bull, Mechanism and Catalysis for Hydrolysis of Acetals, Ketals and Ortho Esters,Chem. Rev. 74:581–603 (1974).
Jensen, J.L., and R. Siegel, Effect of Conjugation on the Rates of the Acid-Catalyzed Hydrolyses of Acetals,J. Org. Chem. 53:6105–6106 (1988).
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Yue, C., Harris, J.M., Hellberg, PE. et al. Synthesis and characterization of cleavable surfactants derived from poly(ethylene glycol) monomethyl ether. J Am Oil Chem Soc 73, 841–845 (1996). https://doi.org/10.1007/BF02517984
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DOI: https://doi.org/10.1007/BF02517984