Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1995-10-18
1997-07-01
Kight, John
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 185, 536 186, 536120, 510245, 510470, C07G 300, C07H 1504, C11D 100
Patent
active
056440413
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/SE94/00198.
This invention relates to an alkyl glycoside in which the alkyl group is methyl-branched, as well as the use of the alkyl glycoside as a surfactant in the cleaning of hard surfaces. The invention also concerns a cleaning composition in which the alkyl glycoside is combined with a solubiliser and preferably also with a complexing agent.
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 glycosides and alkyl oligosaccharides, such as n-octyl glycoside, n-hexyl glycoside, n-decyl glycoside, n-dodecyl glycoside, isodecyl glycoside, isoundecyl glycoside, isotridecyl glucoside and the corresponding oligosaccharides. The United States Stationary Invention Registration H171 states that alkyl glycosides of formulae R(OG) and R(OG).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, galactose, 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 glycosides.
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 too poor a cleaning power. It is therefore a desideratum to provide non-ionic surfactants which are about as easily biodegradable, but which have a better cleaning effect on hard surfaces and/or are more low-foaming than known alkyl glycosides.
According to the present invention, it has now surprisingly been found that an alkyl glycosides of formula
RCH.sub.2 O(G).sub.x H (I) containing 2-4 groups of formula --CH(CH.sub.3)-- in its carbon chain, G is a monosaccharide residue, and x is 1-4, is advantageously used as a surfactant in compositions for cleaning hard surfaces. The alkyl glycosides of formula I shows good cleaning and wetting properties, as well as low foaming compared with other alcohols of approximately the same chain length. In addition, the alkyl glycosides has proved to be easily degradable and have low biotoxicity. Tests have not shown any skin irritations caused by the alkyl glycosides. Preferably, there are 2 or 3 methyl groups. Compounds in which R contains 9 or 10 carbon atoms and x is 1 or 2 are especially preferred, having a good cleaning power and being comparatively easy to produce.
The compounds according to the invention can be produced in conventional manner by reacting an alcohol of formula
RCH.sub.2 OH (II) an acid catalyst, the molar ratio of the alcohol to the monosaccharide being 2:1-80:1. The catalyst may be an inorganic or organic acid. The reaction is performed 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, whereupon excess alcohol is carefully removed e.g. by distillation, if so desired.
The alcohols of formula (I) can be produced in conventional manner by condensing propene, butene or mixtures thereof, whereupon the di-, tri- or tetramers obtained are prolonged with a carbon atom by the oxoprocess. The resulting aldehydes may then easily be converted to the corresponding alcohols. The alcohols obtained form a complex mixture of methyl-branched structures, although some ethyl
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U.S. Statutory Invention Registration, Reg. No. H171, Published Dec. 2, 1986.
U.S. Statutory Invention Registration, Reg. No. H468, Published May 3, 1988.
Justus Leibig's Annalen Der Chemie (1985), (8) , pp. 1513-1536 Paulsen et al.
Akzo Nobel nv
Kight John
Mancini Ralph J.
Morris Louis A.
White Everett
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