Organic compounds -- part of the class 532-570 series – Organic compounds – Sulfonic acids or salts thereof
Patent
1997-06-26
1999-11-02
Geist, Gary
Organic compounds -- part of the class 532-570 series
Organic compounds
Sulfonic acids or salts thereof
562 8, 562 20, 568626, 568672, 568673, 510364, 510418, 510434, C07F 1100
Patent
active
059774045
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
1. Field of the Invention
The invention relates to amphiphilic compounds with at least two hydrophilic and at least two hydrophobic groups based on di-, oligo- or polyol ethers.
2. Description of the Background
A wide variety of anionic, cationic, 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 employed.
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 hydrophobic 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.
SUMMARY OF THE INVENTION
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 di-, oligo- or polyethers whose basic skeletons can be prepared fr di-, oligo- or polyol ethers and .alpha.-epoxides. The corresponding di-, oligo- or polyethers can be alkoxylated and subsequently or directly converted into anionic amphiphilic compounds by, for example, reacting the abovementioned compounds with sulfur trioxide/inert gas, oleum, chlorosulfonic acid or sulfamic acid, with polyphosphoric acid, with a haloacetic acid, with a sultone, with a taurine or with maleic anhydride and sodium bisulfite and subsequently neutralizing in each case.
DETAILED DESCRIPTION OF THE INVENTION
The amphiphilic compounds according to the invention are therefore compounds of the general formula I ##STR1## where R.sup.1, R.sup.2, R.sup.3, X and Y in the formula I have the meanings described below, and where R.sup.1 and R.sup.3 each occur once in the formula I.
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 6 to 18, 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-triadecyl, n-tetradecyl, n-penta-decyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, n-heneicosyl, 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 at
REFERENCES:
patent: 2091956 (1937-09-01), Brenner
patent: 5160450 (1992-11-01), Okahara
CA:111:215073 abs of JP01063538, Mar. 1989.
CA:89:581507 abs of DE2803123, Aug. 1978.
CA:109:169821 abs of "A convenient systhesis of substituted poly ether diols", J Org Chem 53(21), pp. 5179-81, 1988.
"Alkanediyl-.alpha.,.omega.-bis(dimethylalkylammonium bromide) Surfactants. 1. Effect of the Spacer Chain Length on the Critical Micelle Concentration and Micelle Ionization Degreee", R. Zana, et al., Langmuir (1991), vol. 7, pp. 1072-1075.
"Dependence of Aggregate Morphology on Structure of Dimeric Surfactants", Nature, vol. 362, Mar. 18, 1993, R. Zana, et al.
"Alkanediyl-.alpha.,.omega.-bis(dimethylalkylammonium bromide Surfactants. 3. Behavior at the Air-Water Interface" E. Alami, et al., Langmuir 1993, vol. 9, pp. 1465-1467, American Chemistry Society, 1993.
Kwetkat Klaus
Schroder Wolfgang
Geist Gary
Huels Aktiengesellschaft
Vollano Jean F
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