Drug – bio-affecting and body treating compositions – Live hair or scalp treating compositions – Cationic surfactant containing
Reexamination Certificate
1999-10-25
2003-01-21
Page, Thurman K. (Department: 1615)
Drug, bio-affecting and body treating compositions
Live hair or scalp treating compositions
Cationic surfactant containing
C424S070100, C424S070280, C424S401000
Reexamination Certificate
active
06509012
ABSTRACT:
The present invention relates to aqueous cationic surfactant formulations, to a process for their preparation and to their use.
Cationic surfactants are sought-after compounds which are used for numerous applications and are described in a large number of publications and patents. For example, DE-A 34 17 646 and DE-A 27 10 468 describe quaternary ammonium compounds as the most important representatives of the cationic surfactants, such as cetyltrimethylammonium chloride or stearyltrimethylammonium chloride, for use in hair after treatment compositions. A disadvantage when using these cationic surfactants is that they have a strong corrosive effect.
EP-B-0 098 802 describes the preparation of quaternary ammonium compounds, for example cetyldimethyl-2-hydroxyethylammonium dihydrogen phosphate with ethylene oxide in the presence of acids, preferably phosphoric acid, and the use of these cationic surfactants in hair cosmetics. Like the abovementioned compounds, these surfactants are easily frozen out of the solutions. Consequently, they have to be dissolved and homogenized before use. Alternatively, they have to be stored in special storage tanks such that they are unable to freeze out. Both measures entail additional costs.
DE-A 31 16 087 describes a process for preparing quaternary ammonium compounds from a tertiary amine and epoxides in the presence of quaternary ammonium compounds as catalyst. This method can be used to prepare cationic surfactants such as 2-hydroxyhexadecyl-2-hydroxyethyldimethylammonium chloride. These compounds too are easily frozen out and have a corrosive effect.
Cationic surfactants are required to have a range of advantageous properties. Examples of important requirements made of such surfactants are
1. good solubilization,
2. good compatibility with anionic surfactants,
3. good foam stabilization,
4. little or no corrosive effect,
5. good biocidal action,
6. good stability on storage,
7. no freezing out from the surfactant solution,
8. absence of halogen,
9. good conditioning effect,
10. good wetting, emulsifying and dispersing capacity, and
11. ease of preparation.
It is an object of the present invention to develop a cationic surfactant which provides as many as possible of these advantageous properties without having the disadvantages of the cationic surfactants known to date. We have found that this object is achieved by the aqueous cationic surfactant formulations of the invention, comprising in solution
a) from 10 to 50% by weight of a quaternary ammonium compound of the formula I:
where:
R
1
, R
2
, R
3
and R
4
independently are substituted or unsubstituted, branched or unbranched C
1
-C
4
- or substituted or unsubstituted, branched or unbranched, saturated or unsaturated C
8
-C
16
-alkyl, at least one and not more than two of R
1
, R
2
, R
3
and R
4
being substituted or unsubstituted, branched or unbranched, saturated or unsaturated C
8
-C
16
-alkyl, and a water-soluble anion of the Formula (II) is R
5
—O—SO
3
—, where R
5
is C
1
-C
4
-alkyl,
b) from 0.01 to 15% by weight of an amine of the Formula III:
where R
1
, R
2
and R
3
are as defined above and not more than two of R
1
, R
2
and R
3
are substituted or unsubstituted, branched or unbranched, saturated or unsaturated C
8
-C
16
-alkyl, and
c) from 0.1 to 5.0% by weight of a buffer which maintains a pH in a range from 4 to 9.
In the formulae I and III R
1
, R
2
, R
3
and R
4
ind ependently are substituted or unsubstituted, branched or unbranched C
1
-C
4
-alkyl or substituted or unsubstituted, branched or unbranched, saturated or unsaturated C
8
-C
16
-alkyl, it being possible for at least one and not more than two, of R
1
, R
2
, R
3
and R
4
to be substituted or unsubstituted, branched or unbranched, saturated or unsaturated C
8
-C
16
-alkyl and advantageous definitions being as follows:
C
1
-C
4
-alkyl branched or unbranched C
1
-C
4
-alkyl chains such as methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl, preferably methyl or ethyl;
C
8
-C
16
-alkyl: branched or unbranched, saturated C
8
-C
16
-alkyl chains such as n-octyl, 2-methylheptyl, 3-methylheptyl, 4-methylheptyl, 2,2-dimethylhexyl, 2,3-dimethylhexyl, 2,4-dimethylhexyl, 2,5-dimethylhexyl, 3,3-dimethylhexyl, 2,2,3-trimethylpentyl, 2,2,4-trimethylpentyl, 3,3,2-trimethylpentyl, 3,3,4-trimethylpentyl, 4,4,2-trimethylpentyl, 4,4,3-trimethylpentyl, 2,3,4-trimethylpentyl, 2-ethylhexyl, 3-ethylhexyl, n-nonyl, 3-ethyl-2-methylhexyl, 2-methyloctyl, 4-methyloctyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, 3-ethyl-5-isopropyl-4-methyloctyl, n-pentadecyl, n-hexadecyl, or branched or unbranched unsaturated C
8
-C
16
-alkyl chains, for example branched or unbranched C
8
-C
16
-alkenyl chains such as 1-octenyl, 2-octenyl, 3-octenyl, 4-octenyl, 5-octenyl, 6-octnyl or 7-octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, n-pentadecenyl, or n-hexadecenyl; preference is given to saturated and unsaturated alkyls or alkenyls which can be derived from amines of fatty alcohols such as caproyl alcohol, enanthyl alcohol, caprylyl alcohol, pelargonyl alcohol, capryl alcohol, lauryl alcohol, myristyl alcohol, pentadecanol, or cetyl alcohol, or amines of linear Ziegler alcohols (amination of the alcohols to the amine); particular preference is given to saturated C
12
-
16
-alkyl chains and very particular preference to saturated C
12
-C
14
-alkyl chains which can be prepared on the basis, for example, of coconut oil or palm kernel oil. Advantageous branched alkyls can be prepared, for example, on the basis of alcohols from the Guerbet reaction or the oxo reaction.
Examples of substituents of R
1
, R
2
, R
3
and R
4
are alkyl, hydroxylalkyl or hydroxylalkyl ether radicals.
R
5
in the formula II is, advantageously, substituted or unsubstituted, branched or unbranched C
1
-C
4
-alkyl such as methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, or 1,1-dimethylethyl, preferably methyl or ethyl. Suitable substituents of R
5
are alkyl, hydroxyalkyl or hydroxyalkyl ether radicals.
The content of quaternary ammonium compounds (a) of the formula I is in a range from 10 to 50% by weight, preferably from 15 to 40% by weight and, with particular preference, from 20 to 35% by weight, based on the overall weight of the surfactant formulation. Particularly preferred cationic surfactants in the surfactant formulation of the invention are surfactants having only one C
8
-C
16
-alkyl chain, preferably a C
12
-C
16
-alkyl chain and, with particular preference, with a C
12
-C
14
-alkyl chain, as in N,N,N-trimethyl-C
12
/C
14
-ammonium methyl sulfate.
The content of amines (b) of the Formula II is in a range from 0,01 to 15 % by weight, preferably from 0,1 to 10 % by weight and, with particular preference, from 0.5 to 5 % by weight, based on the overall weight of the surfactant formulation. Particularly preferred amines in the surfactant formulation of the invention are those having a long C
8
-C
16
-alkyl chain, preferably with a C
12
-C
16
-alkyl chain and, with particular preference, with a C
12
-C
14
-alkyl chain and two short C
1
-C
4
-alkyl chains, such as N,N-dimethyl-C
12
/C
14
-amine.
It has been found that by adding the buffer to the surfactant solution it is possible to bring about a marked improvement in the stability of the surfactant solution on storage without affecting the surfactant activity. Furthermore, it has likewise been possible to bring about a marked improvement in the solubilizer effect of the surfactant solution by adding the buffer.
The surfactant formulations of the invention comprise advantageously from 0.1 to 5.0% by weight, preferably from 0.5 to 4% by weight, and, with particular preference, from 1.0 to 3.5% by weight of buffer (c) based on the overall weight of the surfactant formulation.
Suitable buffers for the aqueous cationic surfactant formulations of the invention are in principle all those known buffers which maintain a pH in a range from 4 to 9, preferably from 5 to 8 and, with particular preference, f
Hössel Peter
Kasel Wolfgang
Oppenländer Knut
Schunter Walter
Wirsing Friedrich
BASF - Aktiengesellschaft
Channavajjala Lakshmi
Page Thurman K.
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