Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1996-08-15
1998-04-14
Kight, John
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536118, 536120, 536124, 514 25, C07H 1504, C07H 100, A01N 4304, A61K 3170
Patent
active
057393010
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel 1-alkylglycosides functionalized in the alkyl side chain, their preparation and their use as surfactants or emulsifiers in detergents, cleaning compositions or personal hygiene compositions.
Recently, mostly nonionic surface-active substances based on renewable raw materials have come to the fore to an increasing extent from the surfactant and emulsifiers sector. Substances of this type as a rule have good biodegradability, low toxicity and thus good environmental tolerability.
An important group of such nonionic surfactants are alkylglycosides, in which the long-chain hydrophobic alkyl radical is linked directly to the hydrophilic carbohydrate moiety of the molecule in the 1-position by means of an acetal bond. Indeed, such products already largely fulfill the expectations made of them, but in some properties such as foaming and wetting power, interfacial or surface tension or fat dissolving power still prove worthy of improvement.
A process for the preparation of O-(2-hydroxyalkylated) glucose derivatives by reaction of glucose provided with isopropylidene protective groups with alkyl-1,2-epoxides and subsequent removal of the protective groups is known from the reference Chem. Ber. 101, 3721-3723 (1968). This reference states that the position of the alkyl radical introduced into the glucose molecule in this way is unknown. The preparation of these O-alkylated glucose derivatives was of interest, in particular with respect to their interfacial activity and their biodegradability. Nothing is mentioned about possible real applications of these compounds.
It is an object of the present invention to provide nonionic surfactants or emulsifiers based on renewable raw materials, which no longer have the deficiences described above.
We have found that this object is achieved by 1-(2'hydroxy- and 2'-sulfatoalkyl)glycosides of the general formula I ##STR2## where X is a hydroxyl or a sulfato group of the formula OSO.sub.3 M, where substituted by organic radicals, group designated above.
The variable M, in addition to hydrogen, is an alkali metal or unsubstituted or substituted ammonium cation. Suitable sulfuric acid hemiester salts of this type are especially the lithium, potassium and, in particular, sodium salts, in addition also the unsubstituted ammonium salts and also organic amine salts having a tertiary nitrogen atom. Suitable bases on which organic amine salts of this type are based are, in particular, tertiary amines such as trialkylamines having 1 to 4 C atoms in the alkyl, eg. trimethyl- and triethylamine, and trialkanolamines having 2 or 3 C atoms in the alkanol radical, preferably triethanolamine, tri-n-propanolamine or triisopropanolamine.
The long-chain radical R is branched or preferably linear alkyl or alkenyl having, in particular, 8 to 20 C atoms, especially 9 to 16 C atoms. At a chain length of 10 to 14 C atoms for R, an optimum in the application properties is achieved, as obviously the optimum ratio is present here between hydrophobic and hydrophilic entities.
Examples of linear R radicals which may be mentioned are the following alkyl and alkenyl groups:
n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, eicosyl, hexadec-7-enyl, hexadeca-7,10-dienyl and hexadeca-7,10,13-trienyl.
Mixtures of various R radicals can also occur, for example mixtures of n-decyl and n-dodecyl or n-dodecyl and n-tetradecyl.
The monosaccharide radical Gly is built up from customary pentoses or hexoses. Carbohydrates Gly-H of this type are preferably aldopentoses such as ribose, arabinose, xylose and lyxose, aldohexoses such as allose, altrose, glucose, mannose, gulose, idose, galactose and talose, and ketohexoses such as fructose. Of these, mannose, glucose, galactose and fructose are preferred. Glucose is particularly preferred.
Normally the carbohydrates of the D-series occurring in nature are employed, however, representatives of the L-series can also be used.
The linkage of the
REFERENCES:
patent: 4287078 (1981-09-01), Langdon et al.
Klotz Wolfgang
Oetter Gunter
Oftring Alfred
Schmidt Richard
Strecker Beate
BASF - Aktiengesellschaft
Kight John
White Everett
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