Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...
Patent
1992-01-14
1993-08-17
Dees, Jose G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Fatty compounds having an acid moiety which contains the...
554149, C07C 5900
Patent
active
052370801
DESCRIPTION:
BRIEF SUMMARY
This invention relates to alkoxylation products of OH-functional C.sub.10-22 carboxylic acid derivatives and/or OH-functional C.sub.10-22 carboxylic acids and to a process for the production of these alkoxylation products.
Ethoxylated and/or propoxylated castor oils are used, for example, in cosmetic preparations, detergents and lubricating oils and as antistatic agents for nylon carpets (Kirk-Othmer: "Encyclopedia of Chemical Technology", Vol. 5, page 9, John Wiley, New York (1979)). Where ethoxylated and/or propoxylated castor oils are used, however, it has to be accepted that the quantities of castor oil and hence ethoxylated and/or propoxylated castor oils available on the market are subject to considerable fluctuations. Poor harvests in the main growing areas of Brazil and India lead to a shortage of the starting material, castor oil, at more or less long intervals. Accordingly, there is a need for an equivalent substitute for alkoxylated castor oils. Above all, the substitute product should be accessible from a broader and less crisis-prone raw material base and should be both ecologically and toxicologically safe.
It has now been found that certain OH-functional carboxylic acids and/or OH-functional carboxylic acid derivatives alkoxylated with alkylene oxides can be used as a substitute for alkoxylated castor oils.
Accordingly, the present invention relates to alkoxylation products obtainable by reaction of ethylene oxide, propylene oxide and/or butylene oxide with C.sub.10-22 carboxylic acid derivatives and/or C.sub.10-22 carboxylic acids containing carboxylic acid functions which, in the 9,10 and/or 13,14 position, contain structural units corresponding to the following general formula ##STR3## in which R is a hydrogen atom, an OH group or an OR.sup.1 group, ##STR4## group or, where the corresponding mono-, di- and/or triglycerides are used as the C.sub.10-22 carboxylic acid derivatives, R.sup.1 is a C.sub.9-18 alkyl group, a C.sub.9-18 alkenyl group or a ##STR5## group and R.sup.2 is a hydrogen atom a C.sub.1-21 alkyl group or a C.sub.2-21 alkenyl group.
The present invention also relates to a process for the production of alkoxylation products, characterized in that C.sub.10-22, carboxylic acid derivatives and/or C.sub.10-22 carboxylic acids containing carboxylic acid functions which, in the 9,10 and/or 13,14 position, contain structural units corresponding to the following general formula ##STR6## in which R is a hydrogen atom, an OH group or an OR.sup.1 group, ##STR7## group or, where the corresponding mono-, di- and/or triglycerides are used as the C.sub.10-22 carboxylic acid derivatives, R.sup.1 is a C.sub.9-18 alkyl group, a C.sub.9-18 alkenyl group or a ##STR8## group and R.sup.2 is a hydrogen atom, a C.sub.1-21 alkyl group or a C.sub.2-21 alkenyl group, temperatures of 110 to 200.degree. C. and under pressures of 10.sup.5 to 2.multidot.10.sup.6 Pa.
The alkoxylation products according to the invention may be prepared by standard organic synthesis methods. Suitable starting materials for alkoxylated OH-functional C.sub.10-22 carboxylic acids are any OH-free, unsaturated C.sub.10-22 carboxylic acids of natural and/or synthetic origin containing at least one or two double bonds in the 9 and/or 13 position, for example 9c-dodecenoic acid, 9c-tetradecenoic acid, 9c-hexadecenoic acid, 9c-octadecenoic acid, 9t-octadecenoic acid, 9c,12c-octadecadienoic acid, 9c,12c,15c-octadecatrienoic acid, 9c-eicosenoic acid and/or 13c-docosenoic acid, and/or mixtures having at least a high content of such unsaturated carboxylic acids. Preferred educts are carboxylic acids containing 16 to 22 carbon atoms and at least one or two double bonds in the 9 and/or 13 position or carboxylic acid mixtures having at least a high content of carboxylic acids containing 16 to 22 carbon atoms and at least one or two double bonds in the 9 and/or 13 position.
Suitable educts for alkoxylated OH-functional C.sub.10-22 carboxylic acid derivatives are any OH-free, unsaturated, naturally occurring and/or synthetically obtainable C.s
REFERENCES:
patent: 4615837 (1986-10-01), Abel et al.
patent: 4699998 (1987-10-01), Green
patent: 4897225 (1990-01-01), Biehm et al.
patent: 5055230 (1991-10-01), Clubley et al.
Daute Peter
Stoll Gerhard
Carr D. D.
Dees Jos,e G.
Henkel Kommanditgesellschaft auf Aktien
Jaeschke Wayne C.
Millson Jr. Henry E.
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