Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1998-01-29
1999-10-05
Geist, Gary
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
560151, 562556, 562564, 252341, 252344, C07C22922, C07C31506, B01D 1704
Patent
active
059627263
DESCRIPTION:
BRIEF SUMMARY
The invention relates to amphiphilic compounds with a plurality of hydrophilic and hydrophobic groups based on amines and/or amides and di-, oligo- or polycarboxylic acids.
A wide variety of anionic, cationic, nonionic and zwitterionic compounds are known as amphiphilic substances. By far the majority of these substances consist of a hydrophilic head group and at least one hydrophobic moiety.
With the amphiphilic substances there is a need, for ecological reasons, for example concerning the reduction in the cost of packaging and transport, to achieve an increasingly great effect per mass of substance employed. Since optimization by mixing amphiphilic substances produces only very limited advances, novel amphiphilic substances with greater efficiency are required. It is therefore necessary in particular to find substances with lower critical micelle concentrations and/or lower surface and interfacial tensions in order to be able to reduce markedly the amounts of active substance used. In addition, they must be easily obtainable, most favourably from readily available starting substances.
Initial approaches to a solution in this direction by doubling one part of the structure (hydrophilic head group, hydrophobic group) have already been disclosed. Thus, cationic surface-active compounds can be obtained by Zana, M. Benrraou, R. Rueff, Langmuir, 7 (1991) 1072; R. Zana, Y. Talmon, Nature, 362 (1993) 228; E. Alami, G. Beinert, P. Marie, R. Zana, Langmuir, 9 (1993) 1465!.
Anionic surface-active compounds with at least two hydrophilic and at least two hydrophobic groups have to date been prepared on the basis of diglycidyl ethers (U.S. Pat. No. 5,160,450, JP 01 304 033, JP 4 124 165). However, diglycidyl ethers are regarded as toxicologically objectionable and are rather costly. Furthermore, epichlorohydrin is used for their preparation, which leads to large amounts of residues, so that these compounds are no longer in accord with the times from the ecotoxicological and economic viewpoints.
The object therefore was to find amphiphilic compounds which have at least two hydrophilic and at least two hydrophobic groups, the amphiphilic compounds having a very high efficiency relative to the amount used, and which furthermore can be prepared from raw materials which are readily available industrially and without large amounts of unwanted byproducts being formed.
The object is achieved according to the invention by amphiphilic di- or oligoesters whose basic skeletons can be prepared from di-, oligo- or polycarboxylic acids and alkoxylated fatty amines or fatty acid amides. The corresponding di- or oligoesters are nonionic surfactants which, however, can be reacted further to give anionic amphiphilic compounds, for which sulphation, carboxymethylation or conversion, for example, into isethionates, taurates or sulphosuccinates are suitable.
The invention therefore relates to amphiphilic compounds of the general formula I: ##STR2## in which R.sup.1 and R.sup.2 are, independently of one another, an unbranched or branched, saturated or unsaturated hydrocarbon radical with 1 to 22, preferably 6 to 18, carbon atoms or an unbranched or branched, saturated or unsaturated acyl radical with 2 to 23, preferably 7 to 19, carbon atoms, A is a spacer and Y and Z are hydrogen or functional groups, and n and m are each, independently of one another, at least 1.
Specific substituents R.sup.1 and R.sup.2 which may be mentioned are the radicals methyl,;..ethyl, n-propyl, n-butyl, n-pentyl, 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, n-nonadecyl, n-eicosyl, n-uneicosyl, n-docosyl and their branched-chain isomers, and the corresponding singly, doubly or triply unsaturated radicals and the corresponding acyl compounds.
A is a straight-chain or branched, saturated or unsaturated, acyclic or cyclic, aliphatic or aromatic di-, oligo- or polycarboxylic acid.
a, b, c, d, e, f, g and h are, independently of one another, numbers from 0 to 15, wher
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American Chemical Society, vol. 7, No. 6, (1991), pp. 1072-1075, "Alkanediyl-.alpha.,.omega. bis(dimethylalkylammonium bromide) Surfactants. 1. Effect of the Spacer Chain Length on the Critical Micelle Concentration and Micelle Ionization Degree", R. Zana, et al.
American Chemical Society, vol. 9, (1993), pp. 1465-1467, "Alkanediyl-.alpha.,.omega.-bis (dimethylalkylammonium bromide) Surfactants. 3. Behavior at the Air-Water Interface", E. Alami, et al.
Nature, vol. 362, Mar. 18, (1993), pp. 228-230, "Dependence of aggregate morphology on structure of dimeric surfactants", R. Zana, et al.
Koch Herbert
Kwetkat Klaus
Ruback Wulf
Davis Brian J.
Geist Gary
Huls Aktiengesellschaft
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