Drug – bio-affecting and body treating compositions – Preparations characterized by special physical form – Cosmetic – antiperspirant – dentifrice
Reexamination Certificate
1999-06-21
2002-11-19
Page, Thurman K. (Department: 1615)
Drug, bio-affecting and body treating compositions
Preparations characterized by special physical form
Cosmetic, antiperspirant, dentifrice
C514S937000, C514S938000, C510S417000, C252S062200
Reexamination Certificate
active
06482418
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to cosmetic and/or pharmaceutical formulations which contain selected dialkyl carbonates as oils and, in addition, emulsifiers, preferably alkyl oligoglucosides, and to the use of the dialkyl carbonates as substitutes for silicone oils.
2. Discussion of the Related Art
Silicones are used in skin and hair cosmetics as additives for influencing feel and shine. Unfortunately, a disadvantage of silicones in this regard is the so-called build-up effect. The build-up effect occurs when silicone-containing products are repeatedly applied to skin or hair where they build up a layer of polymers which is difficult to remove simply by washing. In the case of hair in particular, other treatments, for example waving or coloring, can be affected and possibly impaired by the build-up effect. Another disadvantage of many silicone types is their poor biological degradability. The use of silicones in cosmetics has been reviewed, for example, by K. Schnurrbusch in Seifen-Fette-Öle-Wasche 100, 173 (1974).
The use of Guerbet carbonates based on alcohols containing at least 6 carbon atoms as oils for cosmetic formulations is known from DE-A1 40 40 154 (Henkel). DE-A1 43 17 683 (Henkel) relates to carbonates based on ethoxylated fatty alcohols and to their use for cleaning hard surfaces.
Accordingly, the problem addressed by the present invention was to find substitutes for silicones which would not accumulate in use, but which would nevertheless show comparable performance properties in regard to feel and shine.
DESCRIPTION OF THE INVENTION
The present invention relates to cosmetic and/or pharmaceutical formulations containing:
(a) dialkyl carbonates corresponding to formula (I);
in which R
1
is a linear alkyl and/or alkenyl group containing 6 to 22 carbon atoms, a 2-ethylhexyl, isotridecyl or isostearyl group or a group derived from a polyol containing 2 to 15 carbon atoms and at least two hydroxyl groups, R
2
has the same meaning as R
1
or is an alkyl group containing 1 to 5 carbon atoms and n and m independently of one another stand for 0 or numbers of 1 to 100, and
(b) emulsifiers.
It has surprisingly been found that, in sensorial terms, formulations containing the selected dialkyl carbonates perform at least as well as silicone oils in regard to feel and shine without undesirably accumulating on the skin and hair. The present invention also includes the observation that the dialkyl carbonates corresponding to formula (I) are capable of covering a broad spectrum of different sensorial properties.
Dialkyl Carbonates
Dialkyl carbonates are basically known compounds even through some of the claimed compounds are being described for the first time in the present specification. Basically, they may be prepared by transesterification of dimethyl or diethyl carbonate with the hydroxy compounds mentioned using known methods. A review of these methods can be found, for example, in Chem. Rev. 96, 951 (1996). Dialkyl carbonates corresponding to formula (I) which are particularly suitable for solving the stated problem satisfy one of the following requirements:
(a) R
1
is a linear alkyl group containing 8 to 18 carbon atoms or a 2-ethylhexyl group and R
2
has the same meaning as R
1
or represents methyl;
(b) R
1
is a linear alkyl group containing 12 to 18 carbon atoms, R
2
has the same meaning as R
1
or represents methyl and n and m stand for numbers of 1 to 10;
(c) R
1
is a residue of a polyol selected from the group consisting of glycerol, alkylene glycols, technical oligoglycerol mixtures, methylol compounds, lower alkyl glucosides, sugar alcohols, sugars and aminosugars and R
2
has the same meaning as R
1
or represents a linear or branched alkyl group containing 8 to 12 carbon atoms or methyl.
Typical examples of dialkyl carbonates belonging to the two groups (a) and (b) are complete or partial transesterification products of dimethyl and/or diethyl carbonate with caproic alcohol, caprylic alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmitoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolyl alcohol, linolenyl alcohol, elaeostearyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol and brassidyl alcohol and the technical mixtures thereof formed, for example, in the high-pressure hydrogenation of technical methyl esters based on fats and oils or aldehydes from Roelen's oxosynthesis and as monomer fraction in the dimerization of unsaturated fatty alcohols. The transesterification products of the lower carbonates with the alcohols mentioned in the form of their adducts with 1 to 100, preferably 2 to 50 and more preferably 5 to 20 moles of ethylene oxide are also suitable.
The carbonates of group (c) are being described for the first time in the present specification. They are compounds which are obtained by complete or partial transesterification of dimethyl and/or diethyl carbonate with polyols. Polyols suitable for the purposes of the invention preferably contain 2 to 15 carbon atoms and at least two hydroxyl groups. Typical examples are
glycerol;
alkylene glycols such as, for example, ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol and also polyethylene glycols with an average molecular weight of 100 to 1,000 dalton;
technical oligoglycerol mixtures with a degree of self-condensation of 1.5 to 10, for example technical diglycerol mixtures with a diglycerol content of 40 to 50% by weight;
methylol compounds such as, in particular, trimethylol ethane, trimethylol propane, trimethylol butane, pentaerythritol and dipentaerythritol;
lower alkyl glucosides, more particularly those containing 1 to 8 carbon atoms in the alkyl group, for example methyl and butyl glucoside;
sugar alcohols containing 5 to 12 carbon atoms such as, for example, sorbitol or mannitol;
sugars containing 5 to 12 carbon atoms such as, for example, glucose or sucrose and
aminosugars such as, for example, glucamine.
This reaction can of course not only result in replacement of a methyl or ethyl group by a polyol residue, it also gives a mixture in which several hydroxy groups or even all the hydroxyl groups of the polyol are attached to carbonate groups so that an oligomeric or polymeric net structure may even be obtained. In the context of the invention, compounds of this type are also meant to fall within the scope of general formula (I).
Emulsifiers
Suitable emulsifiers are, for example, nonionic surfactants from at least one of the following groups:
(1) products of the addition of 2 to 30 moles of ethylene oxide and/or 0 to 5 moles of propylene oxide to linear fatty alcohols containing 8 to 22 carbon atoms, to fatty acids containing 12 to 22 carbon atoms and to alkylphenols containing 8 to 15 carbon atoms in the alkyl group;
(2) C
12/18
fatty acid monoesters and diesters of products of the addition of 1 to 30 moles of ethylene oxide to glycerol;
(3) glycerol monoesters and diesters and sorbitan monoesters and diesters of saturated and unsaturated fatty acids containing 6 to 22 carbon atoms and ethylene oxide adducts thereof;
(4) alkyl mono- and oligoglycosides containing 8 to 22 carbon atoms in the alkyl group and ethoxylated analogs thereof;
(5) adducts of 15 to 60 moles of ethylene oxide with castor oil and/or hydrogenated castor oil;
(6) polyol esters and, in particular, polyglycerol esters such as, for example, polyglycerol polyricinoleate or polyglycerol poly-12-hydroxystearate. Mixtures of compounds from several of these classes are also suitable;
(7) products of the addition of 2 to 15 moles of ethylene oxide to castor oil and/or hydrogenated castor oil;
(8) partial esters based on linear, branched, unsaturated or saturated C
6/22
fatty acids, ricinoleic acid and 12-hydroxystearic acid and glycerol, polyglycerol, pentaerythritol, dipentaerythritol, sugar alcohols (for example sorbitol), alkyl glucosides (for example methyl glucoside, butyl
Ansmann Achim
Gassenmeier Thomas
Hensen Hermann
Kahre Joerg
Loehl Thorsten
Channavajjala Lakshmi
Drach John E.
Ettelman Aaron R.
Henkel Kommanditgesellschaft auf Aktien
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