Cleaning compositions for solid surfaces – auxiliary compositions – Cleaning compositions or processes of preparing – For cleaning a specific substrate or removing a specific...
Patent
1994-10-03
1996-08-13
Rollins, John W.
Cleaning compositions for solid surfaces, auxiliary compositions
Cleaning compositions or processes of preparing
For cleaning a specific substrate or removing a specific...
536116, 536120, 536124, 536115, 424 701, 510276, 510130, 510151, 510235, 510470, C07H 1100, C07H 1504
Patent
active
055457312
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to alkyl and/or alkenyl oligoglycoside carbonates, to a process for their production and to their use for the production of surfactants.
2. Statement of Related Art
For some years now, there has been an increasing trend to produce speciality chemicals for detergents from renewable raw materials, such as for example sugar or starch. One example of this are the alkyl oligoglycosides which, for example, may form an alternative to conventional nonionic surfactants based on fatty alcohol and ethylene oxide. However, the properties of alkyl oligoglycosides are not entirely satisfactory for certain cosmetic applications. Accordingly, esters of alkyl oligoglycosides with carboxylic acids of varying chain length are preferably used instead of alkyl oligoglycosides (Seifen- Ole-Fette-Wachse, 117, 124 (1991).
However, the production of these alkyl oligoglycoside esters is attended by two problems, namely:
1. the thermal instability of the glycoside base under the esterification conditions with the danger of caramelization and
2. the inadequate solubility of alkyl oligoglycosides in standard solvents.
There has been no shortage of attempts in the past to provide technical solutions to these problems:
For example, Gibbons and Swanson report in J. Am. Oil Chem. Soc., 36, 553 (1959) on their efforts to prepare mono- and diesters from methyl glucoside and fatty acids in the presence of sodium hydroxide, lead oxide and tin soap in xylene as solvent. However, any process for the production of cosmetic products which involves the use of xylene and lead compounds is extremely critical in toxicological terms.
The attempts made by Albano-Garcia and Lorica to repeat the esterification in the presence of acidic and basic catalysts in DMF proved unsatisfactory. The reaction products were inhomogeneous and caramelized. The esterification of coconut oil with methyl glucosides using metallic sodium and potassium soap as catalysts also produced dark-colored products which had to be purified with ethyl acetate and water (J. Coconut. Stud., 5(1), 51 (1980)). A process as complicated as this is also totally unsuitable for working on an industrial scale.
Finally, Zedlinski reports on the direct esterification of fatty acid chlorides with methyl glucoside in Bull. Acad. Polon, Sci. 9, 103 (1961). However, the use of fatty acid chlorides imposes stringent works safety requirements and is undesirable for this reason alone.
Accordingly, the problem addressed by the present invention was to provide new alkyl and/or alkenyl oligoglucoside esters of which the production would not be attended by the disadvantages described above.
DESCRIPTION OF THE INVENTION
The present invention relates to alkyl and/or alkenyl oligoglycoside carbonates obtainable by condensation of alkyl and/or alkenyl oligoglycosides corresponding to formula (I) radicals,
Accordingly, the new alkyl and/or alkenyl oligoglycoside esters are carbonic acid esters of alkyl and/or alkenyl oligoglycosides. It has surprisingly been found that the condensation of alkyl and/or alkenyl oligoglycosides with dialkyl carbonates takes place substantially completely without any discoloration of the reaction products, irrespective of the chain length of the starting materials. In addition, the problem of inadequate solubility can be overcome by using the dialkyl carbonates in excess and, hence, both as transesterification component and as solvent.
The present invention also relates to a process for the production of alkyl and/or alkenyl oligoglycoside carbonates in which alkyl and/or alkenyl oligoglycosides corresponding to formula (I) radicals,
Alkyl and/or alkenyl oligoglycosides, which may be used as starting materials for the production of the alkyl and/or alkenyl oligoglycoside carbonates according to the invention, are known compounds which may be obtained by the relevant methods of preparative organic chemistry. One process for their production is based, for example, on the acid-catalyzed acetalization of gl
REFERENCES:
patent: 5068321 (1991-11-01), Buysch et al.
Seifen- ole-Fette-Wachse, 117, 124 (1991).
J. Am. Oil Chem. Soc., 36, 553 (1959).
J. Coconut. Stud., 5(1), 51 (1980).
Bull. Acad. Polon, Sci. 9, 103 (1961).
Chim. L'Industr., 18 (1990).
Drach John E.
Henkel Kommanditgesellschaft auf Aktien
Jaeschke Wayne C.
Millson Jr. Henry E.
Rollins John W.
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