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...

1999-12-30

2003-07-15

Metzmaier, Daniel S. (Department: 1712)

Colloid systems and wetting agents; subcombinations thereof; pro

Continuous liquid or supercritical phase: colloid systems;...

Aqueous continuous liquid phase and discontinuous phase...

C516S058000, C516S064000, C516S075000, C516S907000, C516S909000, C516S913000, C516S919000, C558S024000, C558S026000, C558S070000, C558S114000, C562S008000, C562S020000, C562S022000, C562S036000, C562S583000, C562S512400, C568S619000, C568S679000, C560S149000

Reexamination Certificate

active

06593376

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to amphiphilic compounds with at least, two hydrophilic and at least two hydrophobic groups based on di-, oligo-, or polyenes and also to a process for their preparation, and to their use as dispersants, emulsi-fiers, demulsifiers, as auxiliaries in ore mining, metal working, surface finishing, plastics production or processing, as auxiliaries for the application of crop protectants, as adjuvants in medical applications, as textile auxiliaries, as auxiliaries for the cleaning and washing of textiles, as auxiliaries for the cleaning of hard surfaces, and as auxiliaries for the cleaning and washing of skin and hair.
2. Description of the Related Art
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 moiety.
With the amphiphilic substances there is a need, for ecological reasons, for example regarding the reduction in packaging and transportation expenditure, to achieve an increasingly greater effect per mass of substance employed. Since only little optimization can be achieved by mixing amphiphilic substances, novel amphiphilic substances with greater efficiencies are required. In particular, there is a need for substances having lower critical micelle concentrations and/or lower surface and interfacial tensions in order to significantly reduce the amount of active substance used.
Initial approaches to solving this problem by doubling part of the structure (hydrophilic head group, hydrophobic group) have already been disclosed. 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 with at least two hydrophilic and at least two hydrophobic groups have to date been prepared only 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 regarded as toxicologically objectionable and are rather expensive. Furthermore, epichlorohydrin is used for their preparation, which results in large amounts of residues so that said compounds are no longer in accord with the times both in ecotoxicological and economic aspects.
SUMMARY OF THE INVENTION
Therefore, it was an object of the present invention to prepare amphiphilic compounds which have at least two hydrophilic and at least two, hydrophobic groups, wherein the amphiphilic compounds have very high efficiencies, relative to the feed quantity, and, furthermore, can be prepared from raw materials which are technically readily available without producing large amounts of undesirable by-products.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
According to the present invention, the problem is solved by providing amphiphilic compounds based on di-, oligo-, or polyenes.
The amphiphilic compounds of this invention are compounds which, when alkylene dienes are used, typically correspond to the general formulae I and II. The result is analogous for the reaction of a plurality of double bonds.
Formula I
Formula I
The invention therefore relates to amphiphilic compounds of the general formulae I and II or, on reaction of a plurality of double bonds, analogous structures.
Formula I
Formula II
where
R
1
and R
3
, independently of one another, represent an unbranched or branched, saturated hydrocarbon radical or a partially fluorinated or perfluorinated hydrocarbon radical having 1 to 22, preferably 6 to 18, carbon atoms,
R
2
is a spacer,
and X and Y, independently of one another, are substituents of the formula XV
—(C
2
H
4
O)
&agr;
(C
3
H
6
O)
&bgr;
H  (XV)
 where
&agr;=0 to 50, preferably &agr;=0 to 15,
&bgr;=0 to 60, preferably &bgr;=0 to 10, and
&agr;+&bgr;=1 to 100, preferably &agr;+&bgr;=1 to 20,
 or of the formula XVI
—(C
2
H
4
O)
&ggr;
(C
3
H6O)
&dgr;
—FR  (XVI)
 where
&ggr;=0 to 20, preferably &ggr;=0 to 8,
&dgr;=0 to 20, preferably &dgr;=0 to 12, and
&ggr;+&dgr;=0 to 40, preferably &ggr;+&dgr;=0 to 20, and
FR is a functional radical —CH
2
—COOM, —SO
3
M, —P(O)(OM)
2
, —C
3
H
6
—SO
3
M, or —O—C(O)—C
2
H
3
(SO
3
M)—CO
2
M′ with M, M′ representing alkali, ammonium-, substituted ammonium-, or ½ alkaline earth metal ion,
 and where the alkoxide units are incorporated randomly or blockwise, and the sequence is arbitrary.
Examples of the substituents R
1
and R
3
include 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-henicosyl, n-docosyl, and branched-chain isomers thereof as well as their partially fluorinated or perfluorinated equivalents.
R
2
is a spacer consisting of an unbranched or branched chain with 2 to 30 carbon atoms which comprises 0 to 10 oxygen, 0 to 10 nitrogen, and 0 to 3 sulfur atoms and which has 0 to 10 functional side groups, such as carbonyl, carboxyl, amino and/or acylamino groups.
The spacer R
2
represents in particular
unbranched or branched alkylene chains as a body
—C
a
H
2a
—  (III)
where a=2 to 18, preferably a=2 to 6;
alicyclic compounds ofthe formula IV as a body
—C
f
H
2f
-cycloC
6
H
10
—C
g
H
2g
—  (IV)
where each f and g, independently of one another, is equal to from 1 to 6;
 or of the formula V
-3(4),8(9)-di(methylene)-tricyclo[5.2.1.0
2.6
]decane-  (V)
optionally as a body, substituted aromatics of the formula VI
—C
h
H
2h
—C
6
R
4
—(C
i
H
2i
—C
6
R
4
)
j1
—C
j2
H
2j2
—  (VI)
 or of the formula VII
—C
h
H
2h
—C
10
R
6
—C
j
H
2j
—  (VII)
where each h, j, j
1
, and j
2
, independently of one another, is equal to from 0 to 8, and i is equal to from 0 to 8, and each R in the formulae VI and VII, independently of one another, is equal to H or C
1
— to C
6
-alkyl;
a chain with functional side groups, particularly carbonyl, carboxyl, amino and/or acylamino groups.
The spacer R
2
furthermore comprises in each case from 0 to 10, preferably from 1 to 5, oxygen and/or nitrogen atoms and/or from 0 to 3 sulfur atoms.
Thus, R
2
furthermore represents in particular
a compound of the formula VIII
—C
k
H
2k
—C
x
R
y
—Z—C
x
R
y
—C
1
H
21
—  (VIII)
 where
each k and l, independently of one another, is equal to from 0 to 8, each R, independently of one another, is equal to H or C
1
— to C
6
-alkyl, x is equal to 6 and y is equal to 4, or x is equal to 10 and y is equal to 6, or x is equal to 14 and y is equal to 8, and
Z=O, CO, NH, NR
1
, N—C(O)R
1
, SO
2
 or of the formula IX
—CH
2
—CH(OCH
2
CH(OX)—R
1
)—CH
2
— or an isomer  (IX)
 or 2,2′-methylene-bis-(1,3-dioxolane-5-methylene)-, or acetals, particularly diacetals of dialdehydes and di-, oligo-, or polyols,
wherein R
1
is a hydrocarbon radical having 1 to 22 carbon atoms;
a compound of the formula X
—C
m
H
2m
—(OC
n
H
2n
)
p
—C
q
H
2q
—  (X)
where m=1 to 4, n=2 to 4, p=1 to 20, preferably p=1 to 4, and q=1 to 4, wherein mixed alkoxide units may also be present and if that is the case, the sequence of said alkoxide units is arbitrary;
a compound of the formula XI
—C
r
H
2r
(RNC
s
H
2s
)
t
—C
u
H
2u
—  (XI)
 or of the formula XII
—[C
r
H
2r
[RN—C(O)—NR]
t
—C
u
H
2u
]
w
—  (XII)
 or of the formula XIII
—[C
r
H
2r
[RNC(O)C
v
H
2v
C(O)NR]
t
—C
u
H
2u
]
w
—  (XIII)
 or of the formula XIV
—[C
r
H
2r
[RNC(O)C
x
R
y
C(O)NR]
t
—C
u
H
2u
]

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