Drug – bio-affecting and body treating compositions – Preparations characterized by special physical form – Cosmetic – antiperspirant – dentifrice
Reexamination Certificate
1998-03-11
2001-07-24
Kulkosky, Peter F. (Department: 1615)
Drug, bio-affecting and body treating compositions
Preparations characterized by special physical form
Cosmetic, antiperspirant, dentifrice
C252S391000, C252S391000
Reexamination Certificate
active
06264961
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to new o/w emulsifiers containing selected surfactants in combination with certain polymers and to their use for the production of cosmetic or pharmaceutical formulations.
2. Discussion of Related Art
Polyglycerol polyricinoleates have long been known as emulsifiers and may be used for the formulation of low-viscosity emulsions [cf. EP-A1 0559013 (Th. Goldschmidt), EP-A1 0440203 (Lotte Co.) and WO 85/04346 (Meiji Milk Prods.)]. However, it has been found that commercially available polyglycerol polyricinoleates do not form emulsions with all the oils typically used in cosmetics, but only with those within a certain polarity range. In addition, these emulsions show limited stability in storage. A major disadvantage is, above all, that the commercially available products are not capable of sufficiently stabilizing emulsions containing highly polar oils, for example vegetable oils. In view of the particular ecotoxicological compatibility of such emulsions, however, this is very much a market requirement.
European patent EP-B1 0 553 241 (SEPPIC) also describes self-emulsifying mixtures containing alkyl polyglucosides and fatty alcohols of corresponding chain length. However, where emulsifiers such as these are used, unwanted changes in viscosity over the storage time are observed in many cases.
Now, the problem addressed by the present invention was to provide new ethylene-oxide-free o/w emulsifiers which would form storable emulsions with a broad range of oils.
DESCRIPTION OF THE INVENTION
The present invention relates to o/w emulsifiers containing
a1) alkyl and/or alkenyl oligoglycosides,
a2) fatty acid N-alkyl polyhydroxyalkylamides and/or
a3) acyl glutamates and
b) polyol polyhydroxystearates,
with the proviso that the ratio by weight of a) to b) is in the range from 90:10 to 10:90, preferably in the range from 70:30 to 30:70 and more preferably in the range from 60:40 to 40:60.
It has surprisingly been found that, where mixtures of the above-mentioned surfactants, preferably C
12/14
alkyl oligoglucosides, with polyol polyhydroxystearates, preferably polyglycerol poly-12-hydroxystearates, are used as o/w emulsifiers, the emulsions obtained are stable in storage, even in the event of temperature variations, irrespective of the polarity of the oil used. The invention includes the observation that the mixtures are liquid and readily pumpable, particularly when at least one polyol, preferably glycerol, is used as an additional component.
Alkyl and/or Alkenyl Oligoglycosides
Alkyl and alkenyl oligoglycosides are known nonionic surfactants which correspond to formula (I):
R
1
O—[G]
p
(I)
where R
1
is an alkyl and/or alkenyl radical containing 4 to 22 carbon atoms, G is a sugar unit containing 5 or 6 carbon atoms and p is a number of 1 to 10. They may be obtained by the relevant methods of preparative organic chemistry. EP-A1-0 301 298 and WO 90/03977 are cited as representative of the extensive literature available on this subject.
The alkyl and/or alkenyl oligoglycosides may be derived from aldoses or ketoses containing 5 or 6 carbon atoms, preferably glucose. Accordingly, the preferred alkyl and/or alkenyl oligoglycosides are alkyl and/or alkenyl oligoglucosides.
The index p in general formula (I) indicates the degree of oligomerization (DP degree), i.e. the distribution of mono- and oligoglycosides, and is a number of 1 to 10. Whereas p in a given compound must always be an integer and, above all, may assume a value of 1 to 6, the value p for a certain alkyl oligoglycoside is an analytically determined calculated quantity which is generally a broken number. Alkyl and/or alkenyl oligoglycosides having an average degree of oligomerization p of 1.1 to 3.0 are preferably used. Alkyl and/or alkenyl oligoglycosides having a degree of oligomerization of less than 1.7 and, more particularly, between 1.2 and 1.4 are preferred from the applicational point of view.
The alkyl or alkenyl radical R
1
may be derived from primary alcohols containing 4 to 11 and preferably 8 to 10 carbon atoms. Typical examples are butanol, caproic alcohol, caprylic alcohol, capric alcohol and undecyl alcohol and the technical mixtures thereof obtained, for example, in the hydrogenation of technical fatty acid methyl esters or in the hydrogenation of aldehydes from Roelen's oxosynthesis. Alkyl oligoglucosides having a chain length of C
8
to C
10
(DP=1to 3), which are obtained as first runnings in the separation of technical C
8-18
coconut oil fatty alcohol by distillation and which may contain less than 6% by weight of C
12
alcohol as an impurity, and also alkyl oligoglucosides based on technical C
9/11
oxoalcohols (DP=1 to 3) are preferred.
In addition, the alkyl or alkenyl radical R
1
may also be derived from primary alcohols containing 12 to 22 and preferably 12 to 14 carbon atoms. Typical examples are lauryl alcohol, myristyl alcohol, cetyl alcohol, palmitoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, brassidyl alcohol and technical mixtures thereof which may be obtained as described above. Alkyl oligoglucosides based on hydrogenated C
12/14
coconut oil fatty alcohol having a DP of 1 to 3 are preferred.
Fatty Acid N-alkyl Polyhydroxyalkylamides
Fatty acid N-alkyl polyhydroxyalkylamides are nonionic surfactants which correspond to formula (II):
where R
2
CO is an aliphatic acyl radical containing 6 to 22 carbon atoms, R
3
is hydrogen, an alkyl or hydroxyalkyl radical containing 1 to 4 carbon atoms and [Z] is a linear or branched polyhydroxyalkyl radical containing 3 to 12 carbon atoms and 3 to 10 hydroxyl groups.
The fatty acid N-alkyl polyhydroxyalkylamides are known compounds which may normally be obtained by reductive amination of a reducing sugar with ammonia, an alkylamine or an alkanolamine and subsequent acylation with a fatty acid, a fatty acid alkyl ester or a fatty acid chloride. Processes for their production are described in U.S. Pat. Nos. 1,985,424, 2,016,962 and 2,703,798 and in International patent application WO 92/06984. An overview of this subject by H. Kelkenberg can be found in Tens. Surf. Det. 25, 8 (1988). The fatty acid N-alkyl polyhydroxyalkylamides are preferably derived from reducing sugars containing 5 or 6 carbon atoms, more particularly from glucose. Accordingly, the preferred fatty acid N-alkyl polyhydroxyalkylamides are fatty acid N-alkyl glucamides which correspond to formula (III):
Preferred fatty acid N-alkyl polyhydroxyalkylamides are glucamides corresponding to formula (III) in which R
3
is hydrogen or an alkyl group and R
2
CO represents the acyl component of caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselic acid, linoleic acid, linolenic acid, arachic acid, gadoleic acid, behenic acid or erucic acid or technical mixtures thereof. Fatty acid N-alkyl glucamides (III) obtained by reductive amination of glucose with methylamine and subsequent acylation with lauric acid or C
12/14
coconut oil fatty acid or a corresponding derivative are particularly preferred. In addition, the polyhydroxyalkylamides may also be derived from maltose and palatinose.
The use of fatty acid N-alkyl polyhydroxyalkylamides is also the subject of a number of publications. For example, their use as thickeners is known from European patent application EP-A1 0 285 768 (Hüls). FR-A 1 580 491 (Henkel) describes water-containing detergent mixtures based on sulfates and/or sulfonates, nonionic surfactants and optionally soaps which contain fatty acid N-alkyl glucamides as foam regulators. Mixtures of short-chain and relatively long-chain glucamides are described in DE-C1 44 00 632 (Henkel). In addition, DE-A1 42 36 958 and DE-A1 43 09 567 (Henkel) report on the use of glucamides with relatively long alkyl chains as
Ansmann Achim
Gondek Helga
Kawa Rolf
Koester Josef
Kreisig Annette
Drach John E.
Grandmaison Real J.
Henkel Kommanditgesellschaft auf Aktien
Kulkosky Peter F.
Trzaska Steven J.
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