Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof
Patent
1998-08-31
2000-03-07
Geist, Gary
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acids and salts thereof
562564, 562555, 254356, C07C22922, C07C22924, C07C22926, C07C27102
Patent
active
060342714
DESCRIPTION:
BRIEF SUMMARY
The invention relates to amphoteric surfactants with at least two hydrophilic and at least two hydrophobic groups (betaine gemini surfactants), which are structured in such a way that complete surfactant units are linked together in each instance.
A large number of anionic, cationic, non-ionic, and hybrid ionic compounds are known as amphiphilic substances. By far most of these substances are composed of a hydrophilic head group and at least one hydrophobic part. For ecological reasons, for example in order to reduce packaging and transport costs, as well as for the purpose of saving natural resources, it is necessary to constantly achieve a greater effect per mass of substance used. Since optimization by means of mixing amphiphilic substances leads only to limited additional results, new amphiphilic substances with a greater degree of effect are necessary. Therefore substances with lower critical micelle formation concentrations and lower surface tensions, in particular, must be found, in order to be able to clearly reduce the amounts of active substance used. In addition, they must be easily obtainable, if possible from easily accessible starting substances.
Preliminary attempts at finding a solution, in the direction of more powerful amphiphilic substances, by doubling part of the structure (hydrophilic head group, hydrophobic group) are already known. For example, cationic surfactant compounds can be obtained by the addition of long-chain alkyl halogenides to permethylated alkylene diamines [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]. Obviously it is possible to improve the performance of surfactant compounds by a suitable linkage of several surfactant units (composed of a hydrophilic head group and a hydrophobic chain) [R. Zana, H. Levy, D. Papoutsi, G. Beinert, Langmuir, 11 (1995) 3694].
Since amphoteric compounds are known to be particularly mild for the skin, it was therefore a particular task to produce amphoteric surfactant compounds which have at least two hydrophilic and two hydrophobic groups, where the amphiphilic compounds have a very high degree of effectiveness, with reference to the amount used, and which furthermore can be produced from raw materials which are easily available on a technical scale, without undesirable by-products. Amphoteric surfactants which can contain two or more hydrophilic groups are described in Offenlegungsschrift DE 43 09 900, but the way in which the structural units are linked there does not result in an increase in performance in comparison with monomer amphoteric surfactants.
The task of increasing performance is achieved, according to the invention, by amphoteric compounds with at least two hydrophilic and at least two hydrophobic groups, which are structured in such a way that complete surfactant units are linked with each other in each instance. Compounds according to Formula (I) are therefore the object of the invention: ##STR2##
Here, R.sup.1 stands for a saturated or unsaturated, branched or unbranched, cyclic or acyclic hydrocarbon radical with 6 to 22 carbon atoms, R.sup.2 stands for a spacer with 2 to 200 atoms, R.sup.3 stands for a hydrogen atom or an alkyl radical with 1 to 4 carbon atoms, R.sup.4, independent of the other substituents, stands for a saturated or unsaturated, branched or unbranched, cyclic or acyclic hydrocarbon radical with 6 to 22 carbon atoms, and R.sup.5 stands for a hydrogen atom or an alkyl radical with 1 to 4 carbon atoms. n can have values from 1 to 100,000, preferably from 1 to 1,000, especially preferably from 1 to 100, and very especially preferably from 1 to 10, where mixtures of different homologues can also occur. Therefore n can also have fractional values, on average.
The compounds according to the invention, according to Formula (I), can occur in mixtures with derivatives which deviate from Formula (I) with regard to the degree of alkylation or protonation.
The spacer R.sup.2 is part of a commer
REFERENCES:
Langmuir 1991, vol. 7, "Alkanediyl-a,w-bis(Dimethylalkylammonium Bromide) Surfactants. 1. Effect of the Spacer Chain Length on the Critical Micelle Concentration and Micelle Ionization Degree", R. Zana, et al. p. 1072-1075.
Nature, vol. 362, Mar. 1993, "Letters to Nature", R. Zana, et al. "Dependence of Aggregate Morphology on Structure of Dimeric Surfactants" p. 228-230.
Langmuir 1993, vol. 9, E.Alami, et al. "Alkanediyl-a, w-bis (Dimethylalkylammonium Bromide) Surfactants. 3. Behavior at the Air-Water Interface", 1465-1467.
Langmuir 1995, vol. 11, R.Zana, et al. "Micellization of Two Triquaternary Ammonium Surfactants in Aqueous Solution" p. 3694-3698.
Davis Brian J.
Geist Gary
Huels Aktiengesellschaft
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