Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1995-11-14
1997-10-28
Kight, John
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 186, 25217417, C07H 1504, C11D 322
Patent
active
056819498
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to a new alkyl glycoside presenting an advantageous combination of good cleaning power and low foaming, which renders it particularly suitable for cleaning hard surfaces.
In recent years, attention has focused on alkyl glycosides, since these have proved to be more easily biodegradable than other non-ionic surfactants, such as ethylene oxide adducts of fatty alcohols. U.S. Pat. No. 3,839,318 thus describes the production of alkyl glucosides and alkyl oligosaccharides, such as n-octyl glucoside, n-hexyl glucoside, n-decyl glucoside, n-dodecyl glucoside, isodecyl glucoside, isoundecyl glucoside, isotridecyl glucoside and the corresponding oligosaccharides. The U.S. Stationary Invention Registration H171 states that alkyl glycosides of formulae R(OG) and R(O).sub.x are excellent surfactants. In these formulae, R is an alkyl or alkenyl group which is branched at the second carbon atom or at a higher carbon atom, the branch being selected from the group methyl, ethyl, isopropyl, n-propyl, butyl, pentyl, hexyl and mixtures thereof, provided that R contains from about 7 to about 30 carbon atoms; G is a saccharide group selected from the group glucose, fructose, mannose, galaclose, talose, allose, altrose, idose, arabinose, xylose, lyxose, ribose and mixtures thereof; and x is 2 or more. Example 1 contains a description of the production of two product mixtures substantially made up of 2-ethylhexyl glycoside and isooctyl glycoside, respectively.
DE 20 36 472, EP 306 650, EP 306 651 and EP 306 652, inter alia, also describe alkyl glucosides.
Even though alkyl glycosides generally are easily biodegradable, they are only used to a limited extent in many ranges of application, such as the cleaning of hard surfaces, since they are too high-foaming and/or have a poor cleaning power. Also, alkyl glycoside products containing branched alkyl groups often have a disagreeable smell. It is therefore a desideratum to provide non-ionic surfactants which are about as easily biodegradable, but which have a better cleaning power and/or are more low-foaming than known alkyl glycosides.
According to the invention, it has now surprisingly been found that an alkyl glycosides of the general formula ##STR2## wherein R.sup.1 is an alkyl group having 2-5 carbon atoms, preferably 2-4 carbon atoms; R.sup.2 is an alkyl group having 4-7 carbon atoms, preferably 5 or 6 carbon atoms, the sum of the carbon atoms in R.sup.1 and R.sup.2 being 7-11, preferably 7-9, G is a monosaccharide residue, and x is 1-4, preferably 1 or 2, has good cleaning and wetting properties and is low-foaming compared with other alkyl glycosides of approximately the same chain length. Compounds of formula (I) in which R.sup.1 is an alkyl group having 3 carbon atoms, R.sup.2 is an alkyl group having 5 carbon atoms, and G is a glucose residue, are especially preferred. The glycosides according to the invention do not have any disagreeable smell. In addition, they have been found to be easily degradable and have low biotoxicity. Tests have not shown any skin irritations caused by the alkyl glycosides.
The inventive compounds can be produced in conventional manner by reacting an alcohol of formula ##STR3## wherein R.sup.1 and R.sup.2 are as indicated above, with a monosaccharide, the molar ratio of the alcohol to the monosaccharide being 2:1-80:1, in the presence of an acid catalyst. The catalyst may be an inorganic or organic acid. The reaction is carried out under vacuum at 90.degree.-120.degree. C. for about 1-4 h. Conveniently, the resulting reaction mixture is first filtered and then neutralised with an organic and/or an inorganic base. Finally, excess alcohol is carefully removed, e.g. by distillation, if so desired.
The alcohols of formula (II) can be obtained by a Guerbet reaction starting from n-pentanol, n-hexanol or mixtures of n-pentanol and n-hexanol, n-pentanol and n-butanol, n-hexanol and n-butanol, and n-hexanol and n-pentanol, or by an aldol condensation of the corresponding aldehydes. Preferably, the alkanol of formula (II) is
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Dahlgren Lennart
Johansson Ingegard
Akzo Nobel nv
Kight John
Lee Howard C.
Mancini Ralph J.
Morris Louis A.
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