Amphiphilic compounds with a plurality of hydrophilic and hydrop

Details Amphiphilic compounds with a plurality of hydrophilic and hydrop Amphiphilic compounds with a plurality of hydrophilic and hydrop

1998-06-22

2000-05-23

Ambrose, Michael G.

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

Organic compounds

Carbonate esters

252 881, 252351, 508552, 510119, 510130, 510235, 510332, 510499, C07C 6996

Patent

active

060667559

DESCRIPTION:

BRIEF SUMMARY
The invention relates to amphiphilic compounds containing a plurality of hydrophilic and hydrophobic groups, based on carbonic acid derivatives.
Known amphiphilic substances encompass a wide variety of anionic, cationic, nonionic and zwitterionic compounds. By far the majority of these substances consist of a hydrophilic head group and at least one hydrophobic part.
With amphiphilic substances there is a need, for ecological reasons, for example reduction packaging and transportation, to achieve an increasingly greater effect per unit mass of substance employed. Since optimization by mixing amphiphilic substances produces only very limited advances, novel amphiphilic substances with greater effectiveness are required. It is therefore necessary in particular to find substances with lower critical micelle concentrations and/or lower surface tensions in order to be able to reduce markedly the amounts of active substance employed. Initial approaches to a solution in the direction of higher-performance amphiphilic substances by doubling one part of the structure (hydrophilic head group, hydrophobic group) are already known. 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 containing at least two hydrophilic groups 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 up to date from ecotoxicological and economic viewpoints.
The object was therefore to find amphiphilic compounds which have at least two hydrophilic groups and at least two hydrophobic groups, are very effective relative to the amount used, and furthermore can be prepared from raw materials which are readily available industrially and without large amounts of unwanted by-products being formed. In addition, the compounds should be easy to cleave again.
The object is achieved according to the invention by amphiphilic di-, oligo- or polycarbonates whose basic skeleton can be prepared from di-, oligo- or polycarbonic acid derivatives and alkoxylated fatty amines and fatty acid amides. The corresponding di-, oligo- or polycarbonates are nonionic surfactants which, nevertheless, can be further reacted to give anionic amphiphilic compounds. In this context, suitable reactions are sulfonation, carboxymethylation and conversion to, for example, isethionates, taurates and sulfosuccinates.
The amphiphilic compounds according to the invention are thus compounds of the general formula I: ##STR3## in which R.sup.1 and R.sup.2, independently of one another, are an unbranched or branched, saturated or unsaturated hydrocarbon radical having from 1 to 22, preferably from 6 to 18, carbon atoms and an unbranched or branched, saturated or unsaturated acyl radical having from 2 to 23, preferably from 7 to 19, carbon atoms, n and m, independently of one another, are at least 1 and the sum of n and m is a number from 2 to 200, preferably from 2 to 100 and particularly preferably from 2 to 10.
a, b, c, d, e, f, g and h are, independently of one another, numbers from 0 to 15, and the sum of a and b, c and d, e and f and g and h must in each case be at least 1. The alkoxide units are incorporated randomly or blockwise, and the sequence is arbitrary. Y and Z. independently of one another, are hydrogen or functional groups. Functional groups which may be mentioned are --CH.sub.2 COOM, --SO.sub.3 M, --C.sub.2 H.sub.4 SO.sub.3 M, --C(O)C.sub.2 H.sub.3 (SO.sub.3 M)COOM', --P(O)(OM).sub.2, where M and M' are alkali metal, ammonium, alkanolammonium or 1/2 alkaline earth metal

REFERENCES:
patent: 5160450 (1992-11-01), Okahara et al.
patent: 5723590 (1998-03-01), Koch et al.
Derwent Abstract No. 92-189237, Derwent Information Ltd.; JP 04-124165, Sep. 12, 1990, abstract.
Chemical Abstract, vol. 101, No. 12, Sep. 17, (1984), p. 89 abstract No. 92741; Takemoto Oil and Fat Co., Ltd, "Lubricant finishes for synthetic fibers".
R. Zana, M. Benrraou, R. Rueff, Langmuir, 7 (1991) 1072-1075.
R. Zana, Y. Talmon, Nature, 362 (1993) 228.
E. Alami, G. Beinert, P. Marie, R. Zana, Langmuir, 9 (1993) 1465-1467.

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