Effect of Reaction Conditions on Production of Catechinone Hair Dyestuff in Water/Alcohol Mixed Solution
Affiliation(s)
Department of Mechanical Engineering, College of Industrial Technology, Amagasaki, Japan. Department of Biobased Materials Science, Kyoto Institute of Technology, Kyoto, Japan.
Department of Mechanical Engineering, College of Industrial Technology, Amagasaki, Japan. Department of Biobased Materials Science, Kyoto Institute of Technology, Kyoto, Japan.
ABSTRACT
Catechinone hair dyestuff was produced chemically from (+)-catechin by the oxidation with O2 in basic water/alcohol mixed solution. The effects of reaction conditions such as basicity, sorts of added base, temperature, alcohol molar fraction of solvent and sorts of added alcohols on the catechinone formation were studied in order to increase the efficiency of the dyestuff production. The amount of obtained catechinone increases with increasing basicity of the reaction solution. The dyestuff is obtained by adding monoethanol amine, diethanol amine, triethanol amine, l-arginine, Na2CO3, K2CO3, Na3PO4 or NaOH into the solution as a base and the most preferable base is monoethanol amine. The optimum temperature for the production in water/ethanol solution is 30°C. It was found that water-soluble alcohols such as methanol, ethanol, 2-propanol, 1-propanol and tert-butyl alcohol are available for preparing the dyestuff. The optimum alcohol molar fraction of the mixed solvent used for the dye formation is 0.45 for methanol, 0.25 for ethanol and 0.20 for 2-propanol, 0.15 for 1-propanol and 0.10 for tert-butyl alcohol. The amount of the obtained dyestuff reaches a maximum at 1) 0.35 and 0.59, 2) 0.35 or 3) 0.35 mol·kg¨1 of the concentration of (+)-catechin for the 1) water/methanol, 2) water/ethanol or 3) water/1-propanol system, respectively.
Catechinone hair dyestuff was produced chemically from (+)-catechin by the oxidation with O2 in basic water/alcohol mixed solution. The effects of reaction conditions such as basicity, sorts of added base, temperature, alcohol molar fraction of solvent and sorts of added alcohols on the catechinone formation were studied in order to increase the efficiency of the dyestuff production. The amount of obtained catechinone increases with increasing basicity of the reaction solution. The dyestuff is obtained by adding monoethanol amine, diethanol amine, triethanol amine, l-arginine, Na2CO3, K2CO3, Na3PO4 or NaOH into the solution as a base and the most preferable base is monoethanol amine. The optimum temperature for the production in water/ethanol solution is 30°C. It was found that water-soluble alcohols such as methanol, ethanol, 2-propanol, 1-propanol and tert-butyl alcohol are available for preparing the dyestuff. The optimum alcohol molar fraction of the mixed solvent used for the dye formation is 0.45 for methanol, 0.25 for ethanol and 0.20 for 2-propanol, 0.15 for 1-propanol and 0.10 for tert-butyl alcohol. The amount of the obtained dyestuff reaches a maximum at 1) 0.35 and 0.59, 2) 0.35 or 3) 0.35 mol·kg¨1 of the concentration of (+)-catechin for the 1) water/methanol, 2) water/ethanol or 3) water/1-propanol system, respectively.
KEYWORDS
Catechinone, Hair Dyestuff, (+)-Catechin, Chemical Preparation, Water/Alcohol Mixed Solution
Catechinone, Hair Dyestuff, (+)-Catechin, Chemical Preparation, Water/Alcohol Mixed Solution
Cite this paper
Matsubara, T. , Wataoka, I. , Urakawa, H. and Yasunaga, H. (2014) Effect of Reaction Conditions on Production of Catechinone Hair Dyestuff in Water/Alcohol Mixed Solution. Advances in Chemical Engineering and Science, 4, 292-299. doi: 10.4236/aces.2014.43032.
Matsubara, T. , Wataoka, I. , Urakawa, H. and Yasunaga, H. (2014) Effect of Reaction Conditions on Production of Catechinone Hair Dyestuff in Water/Alcohol Mixed Solution. Advances in Chemical Engineering and Science, 4, 292-299. doi: 10.4236/aces.2014.43032.
References
[1] Corbett, J.F. (1971) Hair Dyes. In: Venkataraman, K., Ed., The Chemistry of Synthetic Dyes Vol. V, Academic Press, Inc., New York, 475-495. http://dx.doi.org/10.1016/B978-0-12-717005-3.50014-0 [2] Robbins, C.R. (2012) Chemical and Physical Behavior of Human Hair. 5th Edition, Springer-Verlag, Berlin Heidelberg, 447-464. http://dx.doi.org/10.1007/978-3-642-25611-0 [3] Sosted, H., Agner, T., Andersen, K.E. and Menne, T. (2002) 55 Cases of Allergic Reactions to Hair Dye: A Descriptive, Consumer Complaint-Based Study. Contact Dermatitis, 47, 299-303.
http://dx.doi.org/10.1034/j.1600-0536.2002.470508.x [4] Ishida, W., Makino, T. and Shimizu, T. (2011) Severe Hair Loss of the Scalp Due to a Hair Dye Containing Para Phenylenediamine. ISRN Dermatology, 2011, Article ID: 947284.
http://dx.doi.org/10.5402/2011/947284 [5] Yasunaga, H., Takahashi, A., Ito, K., Ueda, M. and Urakawa, H. (2012) Hair Dyeing by Using Catechinone Obtained from (+)-Catechin. Journal of Cosmetics, Dermatological Sciences and Applications, 2, 158-163. http://dx.doi.org/10.4236/jcdsa.2012.23031 [6] Matsubara, T., Wataoka, I., Urakawa, H. and Yasunaga, H. (2013) Effect of Reaction pH and CuSO4 Addition on the Formation of Catechinone Due to Oxidation of (+)-Catechin. International Journal of Cosmetic Science, 35, 362-367. http://dx.doi.org/10.1111/ics.12051 [7] Matsubara, T., Wataoka, I., Urakawa, H. and Yasunaga, H. (2014) High-Efficient Chemical Preparation of Catechi-none Hair Dyestuff by Oxidation of (+)-Catechin in Water/Ethanol Mixed Solution. Sen’i Gakkaishi, 70, 19-22. http://dx.doi.org/10.2115/fiber.70.19 [8] Perrin, D.D. and Dempsey, B. (1974) Buffers for pH and Metal Ion Control. Chapman & Hall Ltd., London, 161-162. [9] Mochizuki, M., Yamazaki, S., Kano, K. and Ikeda, T. (2002) Kinetic Analysis and Mechanistic Aspects of Autoxidation of Catechins. Biochim. Biophys. Acta—General Subjects, 1569, 35-44.
http://dx.doi.org/10.1016/S0304-4165(01)00230-6
[1] Corbett, J.F. (1971) Hair Dyes. In: Venkataraman, K., Ed., The Chemistry of Synthetic Dyes Vol. V, Academic Press, Inc., New York, 475-495. http://dx.doi.org/10.1016/B978-0-12-717005-3.50014-0 [2] Robbins, C.R. (2012) Chemical and Physical Behavior of Human Hair. 5th Edition, Springer-Verlag, Berlin Heidelberg, 447-464. http://dx.doi.org/10.1007/978-3-642-25611-0 [3] Sosted, H., Agner, T., Andersen, K.E. and Menne, T. (2002) 55 Cases of Allergic Reactions to Hair Dye: A Descriptive, Consumer Complaint-Based Study. Contact Dermatitis, 47, 299-303.
http://dx.doi.org/10.1034/j.1600-0536.2002.470508.x [4] Ishida, W., Makino, T. and Shimizu, T. (2011) Severe Hair Loss of the Scalp Due to a Hair Dye Containing Para Phenylenediamine. ISRN Dermatology, 2011, Article ID: 947284.
http://dx.doi.org/10.5402/2011/947284 [5] Yasunaga, H., Takahashi, A., Ito, K., Ueda, M. and Urakawa, H. (2012) Hair Dyeing by Using Catechinone Obtained from (+)-Catechin. Journal of Cosmetics, Dermatological Sciences and Applications, 2, 158-163. http://dx.doi.org/10.4236/jcdsa.2012.23031 [6] Matsubara, T., Wataoka, I., Urakawa, H. and Yasunaga, H. (2013) Effect of Reaction pH and CuSO4 Addition on the Formation of Catechinone Due to Oxidation of (+)-Catechin. International Journal of Cosmetic Science, 35, 362-367. http://dx.doi.org/10.1111/ics.12051 [7] Matsubara, T., Wataoka, I., Urakawa, H. and Yasunaga, H. (2014) High-Efficient Chemical Preparation of Catechi-none Hair Dyestuff by Oxidation of (+)-Catechin in Water/Ethanol Mixed Solution. Sen’i Gakkaishi, 70, 19-22. http://dx.doi.org/10.2115/fiber.70.19 [8] Perrin, D.D. and Dempsey, B. (1974) Buffers for pH and Metal Ion Control. Chapman & Hall Ltd., London, 161-162. [9] Mochizuki, M., Yamazaki, S., Kano, K. and Ikeda, T. (2002) Kinetic Analysis and Mechanistic Aspects of Autoxidation of Catechins. Biochim. Biophys. Acta—General Subjects, 1569, 35-44.
http://dx.doi.org/10.1016/S0304-4165(01)00230-6