Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1994-05-09
1995-08-15
Robinson, Douglas W.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 185, 536118, 536120, 536122, 536124, C08B 3700
Patent
active
054420466
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to alkyl and/or alkenyl oligoglycoside isethionates obtainable by reaction of alkyl and/or alkenyl oligoglycosides with vinyl sulfonates in the presence of basic compounds, to a process for their production and to their use in surface-active preparations.
2. Statement of Related Art
Isethionates are anionic surfactants containing an --O--CH.sub.2 CH.sub.2 --SO.sub.3.sup.-- group which, by virtue of their favorable dermatological compatibility, may be used with advantage in cosmetic preparations (Parr. Kosm., 42, 203 (1961)). They are usually produced from fatty acids or fatty acid esters by condensation with sodium isethionate, propane or butanesultone (Bull. Chem. Soc. Jap., 43, 2236 (1970)).
Unfortunately, the disadvantage of isethionic acid salts and sultones is that their handling involves strict safety requirements and that the products may contain small quantities of these substances as impurities which is undesirable from the toxicological point of view. In addition, known isethionates are not alkali-stable and can contain fatty acids as hydrolysis products which has an adverse effect on their performance properties.
Accordingly, the problem addressed by the present invention was to develop new isethionates which would be free from the disadvantages mentioned above.
DESCRIPTION OF THE INVENTION
This invention relates to alkyl and/or alkenyl oligoglycoside isethionates which are obtained by reaction of alkyl and/or alkenyl oligoglycosides corresponding to formula (I): 6 to 22 carbon atoms and 0, 1, 2 or 3 double bonds, of basic compounds.
It has surprisingly been found that alkyl and/or alkenyl oligoglycosides can be reacted with vinyl sulfonates in the presence of basic catalysts to form compounds having an isethionate structure. The products show unexpectedly good dermatological compatibility, excellent detergent properties, high alkali stability and are readily biodegradable.
Alkyl oligoglycoside isethionates having particularly favorable performance properties are obtained when alkyl oligoglycosides corresponding to formula (I), in which R.sup.1 is a C.sub.12-18 alkyl radical, G is a glucose unit and/or p is a number of 1.1 to 3.0, are used as the starting material.
The present invention also relates to a process for the production of alkyl and/or alkenyl oligoglycoside isethionates which is characterized in that alkyl and/or alkenyl oligoglycosides corresponding to formula (I): 6 to 22 carbon atoms and 0, 1, 2 or 3 double bonds, to 10, the presence of basic compounds.
Alkyl and/or alkenyl glycosides are known compounds which may be obtained by the relevant methods of preparative organic chemistry. They may be produced from monosugars or polysugars, such as for example glucose or starch, which are acetalized with fatty alcohols in the presence of acidic catalysts either directly or via the intermediate stage of lower alkyl and/or alkenyl glycosides. European patent applications EP 0 301 298 A1 and EP 0 362 671 A1 are cited as representative of the extensive literature available on this subject.
Alkyl and/or alkenyl glycosides (I) in which the glycose unit (G) is derived from aldoses or ketoses are used as starting materials for the production of the alkyl and/or alkenyl glycoside isethionates according to the invention. The reducing saccharides, the aldoses, are preferably used by virtue of their better reactivity. Among the aldoses, glucose is particularly suitable because it is easy to obtain and commercially available. Accordingly, the alkyl and/or alkenyl glycosides particularly preferred as starting materials are the alkyl and/or alkenyl glucosides.
The index p in general formula (I) indicates the degree of oligomerization, i.e. the distribution of monoglycosides and oligoglycosides, and stands for a number of 1 to 10. Whereas p in a given compound must always be an integer and, above all, may assume a value of 1 to 6, the value p for a certain alkyl glycoside is an analytically determined calculated quantity wh
REFERENCES:
patent: 2580352 (1951-12-01), Grassie
patent: 4990609 (1991-02-01), Herzog
chemical Abstracts, vol. 116, No. 23, Jun. 8, 1992, Columbus, Ohio, Abstract No. 236083u (Document Unavailable--see Japan 03/291295 above).
Parf. Kosm., 42, 203 (1961).
Bull. Chem. Soc. Jap.,43, 2236 (1970).
Drach John E.
Fonda Kathleen Kahler
Henkel Kommanditgesellschaft auf Aktien
Jaeschke Wayne C.
Millson Jr. Henry E.
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