Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1993-02-18
1997-11-18
Naff, David M.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 185, C07G 300, C07G 1100
Patent
active
056889291
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to galacturonic acid-derivatives, methods for preparing them and their various applications, especially as nonionic or anionic surface-active agents.
The grafting of alkyl groups on carbohydrates leads to surface-active agents whose surface-active properties are very valuable and whose biodegradability is generally good (R. D. SWISHER, "Surfactant biodegradation", Marcel Dekker, Inc. New York, 1987).
The most widely used raw materials are sucrose and glucose and the reactions performed on these unprotected substrates lead to complex mixtures of nonionic surfactants, this being due to random grafting (mono-,di- and triaddition) and to inter- and/or intramolecular oligomerization phenomena (see EP 0249013, DE 3842541, DE 3723826, H. LUDERS and P. HOFFMANN "Synthesis, Chemical Structure and Properties of Alkylpolyglucosides", Cesio, 2nd International Congress on Surfactants, 24-27 May 1988, PARIS, and D. BALZET "Alkylpolyglucosides, their physicochemical properties and their uses", Tenside Surf. Det. 28, 1991, 6). The reaction temperatures used in these preparations are generally high (above 100.degree. C.), which leads to partial degradation of the substrates and causes coloration of the products.
In the case of carbohydrate-based anionic surfactants, the rare compounds described in the literature are obtained by bioconversion (lipid-containing sophoroses, rhamnolipids and the like: see DE 3526417; G. Georgiu, S. C. Lin and M. M. Sharma, "Surface active compounds from microorganisms", Bio./Biotechnology, Vol. 10, January 1992, 60-65; D. F. Gerson and J. E. Zajic "microbial biosurfactants", Process Biochemistry, July 1979, 20-29; D. G. Cooper "Biosurfactants", Microbiological Sciences, Vol. 3, No. 5, 1986, 145-149) or by oxidation of the primary hydroxyl of D-octylglucopyranoside, .alpha.-D-dodecylglucopyranoside, .alpha.-D-tetradecylglucopyranoside, .beta.-D-decyimaltoside and .alpha.-D-tetradecylmaltoside (see EP 0326673; Bocker J. Thiem J., Tenside, Surf, Det., 26, 318, (1989); Van Bekkum H. in "Carbohydrates as organic raw materials" Lichtenthaler F. W. (Ed), V. C. H. Weinheim 289 (1991) and references cited; GOEDE A. T. J. W., de Wit P., Vinki P., Van Rantwijk F. and Van Bekkum H., presentation at the 6th European Congress on the chemistry of carbohydrates, Edinburgh, 1991), either catalytically, Anderson C. E. and Kent P. W., Biochem. J., 181, 387, (1979)! to give the corresponding carboxylated or sulphated compounds respectively. These documents do not describe galactose derivatives nor their properties, of course, in spite of dangerous generalizations. Furthermore, the substrates required for these syntheses are difficult to obtain and the only procedures leading to compounds with well-defined structures always require prior protection, use organic solvents and expensive reagents (silver carbonate); such is the case in particular for octyl glucoside and its homologues (see Rosayear P., van Aken T., Baxter J., Fergusson-Miller S., Biochemistry 19, 4108, 1980; Shimamoto T., Saito S., Tsuchiya T., J. Biochem., 97, 1807, 1985; Schmidt R. R., Angews Chem. Intern. Ed. Engl., 25, 212, 1986; Straathof A. J. T., Romein F., van Rantwijk F., Kieboom A. P. G. and van Bekkum H., Starch, 39 (10), 362, 1987).
These techniques do not meet the current demand for nonionic surfactants (especially forming a two-phase system), or anionic surfactants, which can be prepared at low cost and with greater efficacy than those used up until now.
Recent attempts (D. Plusquellec and colleagues, Anal. Bioch. 179, 145 (1989); EP 334498; EP 427210, F. Bjorkling and colleagues, J. Chem. Soc., Chem. Commun. 934 (1989); K. Adelhorst and colleagues, Synthesis, 112-115 (1989); M. P. de NiJs and colleagues, Recl. Tray. Chim., The Netherlands, 109, 429-433 (1990), enable nonionic surface-active agents of well-defined structure to be obtained, and without protection of the hydrophilic substrate. However, they require a chemical glycosilation step and an enzymatic step which enables the grafting of a second alkyl
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de Baynast Regis
Favre Serge
Petit Serge
Ralainirina Robert
Agro Industrie Recherches et Developpements (A.R.D.)
Lankford L. Blaine
Naff David M.
Zschimmer & Schwarz GmbH & Co. Chemische Fabriken
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