Amphiphilic compounds with at least two hydrophilic and at least

Details Amphiphilic compounds with at least two hydrophilic and at least Amphiphilic compounds with at least two hydrophilic and at least

1997-08-18

2000-09-19

Kumar, Shailendra

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

25217421, 25217422, 252550, 510119, 510130, 510276, 510437, 558 30, 558166, 562 47, 564153, C07C22900, B01D 1704

Patent

active

061214825

DESCRIPTION:

BRIEF SUMMARY
The invention relates to amphiphilic compounds with at least two hydrophilic and at least two hydrophobic groups based on diamides.
A wide variety of anionic, cationic or nonionic and zwitterionic compounds are known as amphiphilic substances. By far the most of these substances consist of a hydrophilic head group and at least one hydrophobic part.
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 greater 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.
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 adding long-chain alkyl halides onto permethylated alkylenediamines [R. 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 only 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 easily available industrially and without large amounts of unwanted by-products being formed.
The object is achieved according to the invention by amphiphilic diamides whose basic skeleton can be prepared from dicarboxylic acids or their esters and amines. The corresponding di- or oligoamides can be alkoxylated. These nonionic amphiphilic compounds can be converted into anionic amphiphilic compounds by, for example, reacting the abovementioned compounds with SO.sub.3 /inert gas (or oleum chlorosulfonic acid or sulfamic acid), with polyphosphoric acid, with a haloacetic acid, with a sultone, with maleic anhydride and sodium bisulfite or with a taurine and, in each case, subsequently neutralizing.
The amphiphilic compounds according to the invention are therefore compounds of the general formula I ##STR2## where R.sup.1, R.sup.2, R.sup.3, X and Y in formula I have the meanings described below:
R.sup.1 and R.sup.3 are, independently of one another, an unbranched or branched, saturated or unsaturated hydrocarbon radical with 1 to 22, preferably 7 to 17, carbon atoms.
Specific substituents R.sup.1 and R.sup.3 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.
R.sup.2 is a spacer consisting of an unbranched or branched chain with 2 to 100 carbon atoms, which contains 0 to 20 oxygen and/or 0 to 20 nitrogen atoms and/or 0 to 4 sulfur atoms and/or 0 to 3 phosphorus atoms, and which has 0 to 20 functional side groups.
The spacer R.sup.2 is, in particular, skeleton n the compounds according to formulae II to IV the

REFERENCES:
patent: 5160450 (1992-11-01), Okahara et al.
Chemical Abstracts, AN 92 189237, JP 04 124165, Apr. 24, 1992.
R. Zana, et al., Langmuir, American Chemical Society, vol. 7, No. 6, pp. 1072-1075, "Alkanediyl-A,W-Bis(Dimethylalkylammonium Bromide) Surfactants. 1. Effects of the Spacer Chain Length on the Critical Micelle Concentration and Micelle Ionization Degree", 1991.
R. Zana, et al., Nature, vol. 362, pp. 228-230, "Dependence of Aggregate Morphology on Structure of Dimeric Surfactants", Mar. 18, 1993.
E. Alami, et al., Langmuir, American Chemical Society, vol. 9, No. 6, pp. 1465-1467, "Alkanediyl-A,W-Bis(Dimethylalkylammonium Bromide) Surfactants. 3. Behavior at the Air-Water Interface", 1993.
A. Behler, et al., Chemieprodukte, vol. 116, No. 2, pp. 60-67, New Thickening Agents for Surfactants, Feb. 7, 1990.
A. Khatory, et al., Langmuir, American Chemical Society, vol. 9, No. 6, pp. 1456-1464, "Linear and Nonlinear Viscoelasticity of Semidilute Solutions of Wormlike Micelles at High Salt Content", 1993.
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Dieter Balzer, Langmuir, American Chemical Society, vol. 9, No. 12, pp. 3375-3384, "Cloud Point Phenomena in the Phase Behavior of Alkyl Polyglucosides in Water", 1993.
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