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

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

1999-02-18

2001-11-27

Killos, Paul J. (Department: 1623)

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

Organic compounds

Sulfonic acids or salts thereof

C554S094000, C554S096000, C554S097000, C560S149000, C560S151000, C558S030000, C562S102000

Reexamination Certificate

active

06323363

ABSTRACT:

This invention relates to amphiphilic compounds having at least two hydrophilic and at least two hydrophobic groups based on dicarboxylic acid diamides.
A wide variety of anionic, cationic, nonionic, and zwitterionic compounds are known as amphiphilic substances. Most of these substances comprise a hydrophilic head group and at least one hydrophobic moiety.
For ecological reasons, for instance regarding the demand for reduced packaging and transportation expenditure, there is a necessity for increasing the efficiency per mass of amphiphilic substance used. Since only little optimization can be achieved by mixing amphiphilic substances, there exists a need for novel amphiphilic substances having higher efficiencies. In particular, there is a need for substances having lower critical micelle concentrations and/or lower surface and interfacial tension in order to significantly reduce the amount of agent used.
Several routes to solving this problem by doubling part of the structure (hydrophilic head group, hydrophobic group) are known in the art. For example, it is known to prepare cationic surface-active compounds by addition of long-chain alkyl halides to permethylated alkylene diamines [see Zana, R., Benrraou, M., Rueff, R., Langmuir, 7 (1991), p. 1072; Zana, R., Talmon, Y.,
Nature,
362 (1993), p. 228; Alami, E., Beinert, G., Marie, P., Zana, R., Langmuir, 9 (1993), p. 1465].
Anionic surface-active compounds having at least two hydrophilic and at least two hydrophobic groups were prepared on the basis of diglycidyl ethers (cf. U.S. Pat. No. 5,160,450, JP 01 304 033, JP 4 124 165). However, diglycidyl ethers are rated as toxicologically critical and are rather expensive. Furthermore, said compounds are manufactured using epichlorohydrin. This method results in the production of large amounts of residues so that said compounds are obsolete both under ecotoxicological and economic aspects.
A large number of esters of &agr;-sulfocarboxylic acids and polyalkylene oxide glycol ethers, also including amphiphilic compounds, have been described in U.S. Pat. No. 3,246,023. Said compounds are reported to be of nearly universal use, e.g. as emulsifiers for insecticides, pesticides and herbicides, as additives to petroleum products and rubber latices, as foam inhibitors, auxiliaries for road-building materials and for making concrete or paper, as mercerizing assistants, corrosion inhibitors, additives to cosmetic preparations, and, generally, as cleansing agents in hard water.
Therefore, it was an object of the present invention to find amphiphilic compounds having at least two hydrophilic and at least two hydrophobic groups, wherein the amphiphilic compounds are highly efficient, referring to the feed quantity, and, furthermore, can be prepared from technically readily available raw materials without producing large amounts of undesired by-products.
According to the present invention, the problem is solved by providing amphiphilic dicarboxylic acid diamides the basic structures of which can be prepared from dicarboxylic acids or esters thereof and alkyl amines. The corresponding amides can be sulfonated and subsequently neutralized.
The amphiphilic compounds of this invention are compounds having the general formula I
where R
1
, R
2
1
and R
3
in formula I are defined as set forth hereinbelow:
R
1
and R
3
1
independently, represent an unbranched or branched, saturated or unsaturated hydrocarbon residue having 8 to 22 carbon atoms. For instance, the substituents R
1
and R
3
may be the residues 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-henicosyl, n-docosyl, and branched-chain isomers thereof as well as the corresponding mono-, twofold, or threefold unsaturated residues.
The spacer R
2
represents
unbranched or branched alkylene chains of formula II
—C
a
H
2
a—  (II)
 where a is equal to from 2 to 18, preferably 2 to 6;
alicyclic compounds of formula IV
—C
f
H
2f
—cycloC
6
H
10
—C
g
H
2
g—  (IV)
 where each f and g, independently, is equal to from 1 to 6;
optionally, substituted aromatics of formula VI
—C
h
H
2h
—C
6
R
4
—(C
i
H
2i
—C
6
R
4
)
j
—C
j
H
2j
—  (VI)
 or of formula VII
—Ch
h
H
2h
—C
10
R
6
—C
j
H
2j
—  (VII)
 where each h and j, independently, is equal to from 0 to 8 and i is equal to from 0 to 8 and each R, independently, is equal to H or C
1
to C
6
alkyl.
Letter n in formula I represents the number 1.
In addition, R
2
may be derived from a methyl or ethyl ester of a polycarboxylic acid (molecular weight from 500 to 100,000, preferably from 500 to 1,000) the &agr;-carbon atoms of which have a sulfonation degree of from 0 to 100%, preferably 10 to 60%. In this case n is in the range of from 1 to 25,000.
M and M′ represent alkali, ammonium, alkanol ammonium, or ½ alkaline earth ion.
A and B, independently, are —NH—, NR
4
— (where R
4
is equal to methyl, ethyl, propyl, butyl, or methoxyethyl, methoxypropyl, ethoxypropyl), —N(R
5
)—O(C
2
H
4
O) &agr;(C
3
H
6
O)
&bgr;
— (where &agr; is equal to from 0 to 20, preferably 0 to 10, and &bgr; is equal to from 0 to 20, preferably 0 to 10, and &agr; and &bgr; cannot be simultaneously 0, and R
5
is equal to R
4
or to —O(C
2
H
4
O)
&agr;
(C
3
H
6
O)
&bgr;
—H under the conditions set forth hereinabove), or —C(O)N(R
5
)—O(C
2
H
4
O)
&agr;
(C
3
H
6
O)
&bgr;
— under the conditions set forth hereinabove.
The outstanding characteristics of most of the amphiphilic compounds of the present invention are their extremely low critical micelle concentrations (CMC) and very low surface/interfacial tensions, e.g. in contact with paraffin. Said properties are due to the special structures of the compounds, namely at least two hydrophilic and at least two hydrophobic groups.
Furthermore, most of said compounds have rather high hydrophilic suspending power which is rated to be halfway between that of conventional surfactants and pentasodium tripolyphosphate. Some of said compounds have extremely high wetting activities. Salts of sulfonated esters of unsaturated dicarboxylic acids with unsaturated fatty alcohols are described in DE 39 32 492 (unexamined German patent application). However, the structures of said compounds are completely different from those of the compounds of this invention because, according to DE 39 32 492, the SO
3
is exclusively added to double bonds.
The amphiphilic compounds of the present invention are particularly useful as emulsifiers, demulsifiers, detergents, dispersants, and hydrotropes in industrial and domestic applications, e.g. in the fields of metal working, ore mining, surface finishing, washing and cleaning, cosmetics, medicine, foodstuff processing and preparation.
Said compounds may be employed in combination with any customary anionic, nonionic, cationic, and ampholytic surface-active substances. Examples of nonionic surface-active substances suitable for said combinations include fatty acid glycerides, fatty acid polyglycerides, fatty acid esters, ethoxylates of higher alcohols, polyoxyethylene fatty acid glycerides, polyoxyethylene propylene glycol fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene castor oil or hardened castor oil derivatives, polyoxyethylene lanolin derivatives, polyoxyethylene fatty acid amides, polyoxyethylene alkyl amines, alkanol amines, alkylamine oxides, protein hydrolysate derivatives, hydroxy mixed ethers, alkyl polyglycosides, and alkyl glucamides.


REFERENCES:
patent: 2028091 (1936-01-01), Jaeger
patent: 2192906 (1940-03-01), Hanford et al.
patent: 3246023 (1966-04-01), Shen et al.
patent: 5160450 (1992-11-01), Okahara et al.
patent: 3932492 (1991-05-01), None
patent: 1464243 (1966-12-01), None
patent: 1304033 (1989-12-01), None
patent: 4124165 (1992-04-01), None
patent: 07003287 (1995-01-01), None
patent: WO 96/25393 (1996-08-01), None
Chemical Abstracts 98:98705: Kashlinskaya, P.E.; Verezhnikov, V.N.; and Goncharova, N.I.: “Study of the Interaction of

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