The Synthesis of New Pseudoceramides using Aldyldetene Dimer and Their Physical Properties

Byeong-Deog Park; Myungjin Lww; Yoon kim; jong Gi Lee

Journal of Industrial and Engineering Chemistry, Vol.5, No.3, 228-234, September, 1999

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The Synthesis of New Pseudoceramides using Aldyldetene Dimer and Their Physical Properties

Byeong-Deog Park^†, Myungjin Lww, Yoon kim, and jong Gi Lee

AKI Central Research Laboratories, Aekyung Industrial Co. LTD., Daejeon 300-200, Korea

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As cosmetic raw materials, novel pseudoceramides have been synthesized and their physical properties have been investigated> The pseudoceramides, PC-4 (N-(2,3-dihydroxyprophl)-2-myristyl/palmityl-3-oxostearamide/arachidamide), and PC-5 (N-(2,3-dihydroxyprophl)-2-myristyl/palmityl-3-oxostearamide/arachidamide), were synthesized according to the reaction between alkylketene dimer (AKD) and alkanolamines. The reduced types of new pseudoceramides, PC-4R (N-(2,3-dihydroxyprophl)-2-myristyl/palmityl-3-hydroxystearamide/arachidamide) and PC-5R (N-(2,3-dihydroxyprophl)-2-myristyl/palmityl-3-hydroxystearamide/arachidamide) were prepared by the reduction of PC-4 and PC-5, respectively. An effective and economical synthetic pathway with high purity and high yield enabled the industrial production of these pseudoceramides. It was confirmed that there were several kinds of hydrogen bonding in them by the FT-IR study. X-ray diffraction (XRD) method and cross-polarized microscopy results make us confirm their intrinsic characteristics of lamellar structure formations. This intrinsic power to form the lamellar structure made it possible to form a pseudo-stratum corneum lipid emulsion, which shows the multi-lamellar structure.

Keywords:pseudoceramide;lamellar;alkylketene dimer;alkanolamine;stratum corneum;emulsion

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[Related Articles]

[1] Wertz P, Downing D, Freinkel R, Trazyk T, J. Invest. Dermatol., 83, 193 (1984)

[2] Elias PM, Arch. Dermatol. Res., 270, 95 (1981)

[3] Yardley HJ, Int. J. Cosmet. Sci., 9, 13 (1987)

[4] Maes D, Marenus K, Smith WP, Cosmet. Toil., 105, 43 (1990)

[5] Kerscher M, Eur. J. Dermatol., 1, 39 (1991)

[6] Imokawa G, Akasaki S, Kawamata A, Yano S, Takaishi T, J. Soc. Cosmet. Chem., 40, 273 (1989)

[7] Rousset G, WO Patent, 92-21321 (1992)

[8] Lambers H, Farin F, Keuning W, Vander Wilden W, 2nd ASCS, 106 (1995)

[9] Casey J, Cheetham P, Harries P, Hyliands D, Michell J, Ralings A, WO Patent, 94-10131 (1994)

[10] Yoshihiro O, Mituo S, Shinji YKawamata A, Okuda M, Imokawa G, U.S. Patent, 5,221,757 (1993)

[11] Peter C, Susan K, Anthony R, Richard SI, WO Patent, 92-06982 (1992)

[12] Farnum D, Johnson J, Hess R, Marshall T, Webster B, J. Am. Chem. Soc., 87, 5191 (1965)

[13] Hurd C, Blancard C, J. Am. Chem. Soc., 72, 1461 (1950)

[14] Rothman E, J. Org. Chem., 32, 1683 (1967)

[15] Hasek RH, Clark RD, Elam EU, Nations RG, J. Org. Chem., 27, 3106 (1962)

[16] Kirk RE, Othmer DF, Encyclopedia of Chemical Technology, Vol. 8, p. 110, The Interscience Encyclopedia, New York (1952)

[17] Iwai H, Fukasawa J, Fukuda M, Sugai I, Uchida H, Suzuki T, J. Jpn. Soc. Cosmet, Chem., 30, 310 (1996)