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...

1997-07-02

2002-01-29

Kumar, Shailendra (Department: 1621)

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

Organic compounds

Carboxylic acid esters

C252S175000, C252S175000, C252S576000, C510S119000, C510S130000, C510S276000, C510S437000, C558S166000, C562S047000, C564S153000

Reexamination Certificate

active

06342625

ABSTRACT:

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 amides.
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].
Nonionic amides having a gemini structure are described in EP-A-O 258 923. They are employed in specific plasticizer and surfactant compositions and employed together with water-soluble quaternary ammonium compounds and a clay of a certain minimum ion-exchanger capacity.
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.
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- or oligoamides whose basic skeletons can be prepared from di- or oligoamines and fatty acids or fatty acid methyl esters. 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
3
/inert gas (or oleum or chlorosulfonic acid), with polyphosphoric acid, with a haloacetic acid, with a sultone 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
where R
1
, R
2
, R
3
, X, Y and Z in formula I have the meanings described below:
R
1
and R
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
1
and R
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
2
is a spacer consisting of an unbranched or branched chain with 2 to 100 carbon atoms, which in each case contains 0 to 20 oxygen and nitrogen atoms and 0 to 4 sulfur atoms and 0 to 3 phosphorus atoms, and which has 0 to 20 functional side groups such as, for example, hydroxyl, carbonyl, carboxyl, amino and/or acylamino groups.
The spacer R
2
is, in particular,
as basic skeleton, unbranched or branched alkylene chains
—C
a
H
2a
—  (II)
with a=2 to 18, preferably a=3 to 6;
as basic skeleton, unbranched or branched alkenylene chains
 —C
b
H
2b
—CH═CH—C
c
H
2c
—  (III)
with b+c=2 to 16, where b and c are each greater than zero;
as basic skeleton, unbranched or branched alkynylene chains
—C
d
H
2d
—C≡C—C
e
H
2e
—  (IV)
with d+e=2 to 16, where d and e are each greater than zero, and where in the basic skeletons according to formulae II to IV the spacer contains at any desired point in the chain additionally 0 to 4 carbonyl, amino or acylamino groups;
alicycles according to the formula V
—C
f
H
2f
-cyclo C
6
H
10
—C
g
H
2g
—  (V)
with f and g=each 1 to 6
or according to formula VI
-3(4),8(9)-di(methylene)-tricyclo [5.2.1.0
2.6
]decane-  (VI);
unsubstituted or substituted aromatics according to the formula VII
—C
h
H
2h
—C
6
R
4
—(C
i
H
2i
—C
6
R
4
)
j1
—C
j2
H
2j2
—  (VII)
or according to the formula VIII
—C
h
H
2h
—C
10
R
6
—C
j
H
2j
—  (VIII)
with h, j, j
1
and j
2
=each 0 to 8 and i=1 to 8 and with R=independently of one another in each case H or C
1
- to C
4
-alkyl;
a chain with functional side groups, in particular an amino, acylamino, carbonyl or carboxyl functionality.
Furthermore, the spacer R
2
in each case contains 0 to 20, preferably 1 to 12, oxygen and/or nitrogen atoms, 0 to 4 sulfur atoms and 0 to 3 phosphorus atoms, with at least one of the heteroatoms occurring at least once.
R
2
thus furthermore has in particular the meaning
of a compound according to the formula IX
—C
k
H
2k
—C
x
R
y
—Z—C
x
R
y
—C
l
H
2l
—  (IX)
with k and l=each 0 to 8, x=6 and y=4 or x=10 and y=6 or x=14 and y=8, and Z=O, NH, NR
1
, N—C(O)R
1
, SO
2
, where R
1
is a hydrocarbon radical with 1 to 22 carbon atoms and R is, independently of one another, in each case H or C
1
-C
4
-alkyl;
of a compound according to the formula X
—C
m
H
2m
—(OC
n
H
2n
)
p
—C
q
H
2q
—  (X)
with m=1 to 4, n=2 to 4, p=1 to 20, preferably p=1 to 4 and q=1 to 4, where mixed alkoxide units may also occur and then the sequence of the alkoxide units is arbitary;
of a compound according to the formula XI
—C
r
H
2r
(RNC
s
H
2s
)
t
—C
u
H
2u
—  (XI)
or according to the formula XII
—[C
r
H
2r
[RN—C(O)—NR]
t
—C
u
H
2u
]
w
—  (XII)
or according to the formula XIII
—[C
r
H
2r
[RNC(O)C
v
H
2v
C(O)NR]
t
—C
u
H
2u
]
w
—  (XIII)
or according to the formula XIV
—[C
r
H
2r
[RN—C(O)—CH═CH—C(O)—NR]
t
—C
u
H
2u
]
w
—  (XIV)
or according to the formula XV
—[C
r
H
2r
[RNC(O)C
x
R
y
C(O)NR]
t
C
u
H
2u
]
w
—  (XV)
with r=2 to 4, s=2 to 4, t=1 to 20, preferably t=1 to 4, u=2 to 4, v=0 to 12, w=1 to 6, x=6 and y=4 or x=10 and y=6 or x=14 and y=8 with R=independently of one another in each case H or C
1
- to C
4
-alkyl.
X or Y is a substituent of the formula XVI
—(C
2
H
4
O)
&agr;
(C
3
H
6
O)
&bgr;
H  (XVI)
with &agr;=0 to 50, preferably &agr;=10 to 30, &bgr;=0 to 60, preferably &bgr;=20 to 40, and &agr;+&bgr;=1 to 100, preferably &agr;+&bgr;=10 to 50, where R
2
is not C
2
H
4
when &bgr;=0,
and X or Y is a substituent of the formula XVII or X and Y are, independently of one another, subst

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