Aqueous compositions and their use

Details Aqueous compositions and their use Aqueous compositions and their use

1999-06-23

2001-02-20

Cain, Edward J. (Department: 1714)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Processes of preparing a desired or intentional composition...

C424S047000, C424S070150

Reexamination Certificate

active

06191188

ABSTRACT:

The present invention relates to aqueous preparations and to their use in cosmetic formulations.
Lang et al. in WO 94/08554 describe compositions for setting the hair, comprising at least one polymer and also ethoxylated C
12
-C
20
-fatty alcohols and at least one water-soluble, halogen-free organic solvent. These solvents have the undesirable effect of drying out the hair and thus leading to its embrittlement. They may also be a cause of skin irritation.
EP-B 155 400 describes compositions for setting the hairstyle and caring for the hair, comprising—in addition to a quaternized copolymer of vinylpyrrolidone and dimethylaminoethyl methacrylate—tetraoxyethylene lauryl ether.
EP-B 331 930 likewise describes compositions for setting the hairstyle and caring for the hair, with a copolymer of vinylpyrrolidone and vinylimidazole methochloride and with tetraoxyethylene lauryl ether.
A disadvantage of the composition described above, however, is that it can lead, especially in conditions of high atmospheric humidity, to unnatural stickiness of the hair. Moreover, these compositions also show weaknesses in the setting of hair. Another disadvantage of the copolymers specified in EP-B 155 400 is the comparatively poor dry-combability of the treated hair.
EP-A 715 843 describes aerosol foams with copolymers based on vinylcaprolactam, vinylpyrrolidone and vinylimidazole, an emulsifier such as cetyldimethyl-2-hydroxyethylammonium dihydrogen phosphate or Ceteareth-25® (=polyoxyethlene [sic] cetyl ether) and customary cosmetic auxiliaries, with or without a propellant. The setting effect on hair that is achieved using these aerosol foams, however, is inadequate.
Cosmetic preparations, especially preparations for hair, are intended to have a range of advantageous properties. Examples of major requirements based on such cosmetic compositions are
1. skin compatibility (no irritant or toxic effects on the skin),
2. good feeling on and adhesion to the skin or hair,
3. water resistance,
4. good compatibility with other cosmetic substances,
5. flexible setting of the hair (no stickiness of the hair even with high atmospheric humidity),
6. prevention of electrostatic charging of the hair,
7. provision of a good feel to the hair (good holding, good hair volume and little tackiness),
8. good wet-combability,
9. good flexural strength,
10. enhancement of luster, and
11. good solubility in cosmetic solutions and preparations.
It is an object of the present invention to provide a preparation which meets as many as possible of the advantageous properties and which does not have the disadvantages of the compositions known to date. We have found that this object is achieved by the novel aqueous preparation comprising
a) from 0.1 to 10% by weight of a copolymer based on N-vinylcaprolactam, N-vinylpyrrolidone and N-vinylimidazole and
b) from 0.1 to 10% by weight of at least one polyoxyethylene C
6
-C
15
-monoalkyl ether.
Advantageous copolymers (a) are all those which include N-vinylcaprolactam, N-vinylpyrrolidone and N-vinylimidazole. Suitable polymers are preferably those obtainable by free-radically initiated copolymerization of monomer mixtures comprising
(a
1
) from 20 to 80% by weight, preferably from 40 to 60% by weight, of N-vinylcaprolactam,
(b
1
) from 10 to 60% by weight, preferably from 20 to 50% by weight, of N-vinylpyrrolidone,
(c
1
) from 5 to 50% by weight, preferably from 7 to 20% by weight, of an N-vinylimidazole or quaternized N-vinylimidazole, and
(d
1
) from 0 to 30% by weight, preferably from 0 to 50% by weight, of a further free-radically copolymerizable monomer whose homopolymer has a glass transition temperature of more than 20° C.
and, where the monomer (c
1
) employed is a nonquaternized N-vinylimidazole, advantageously by subsequent quaternization of the polymer.
Suitable N-vinylimidazoles (monomers (c
1
) are 1-vinylimidazole derivatives of the general formula I,
where R
1
is hydrogen, C
1
-C
4
-alkyl or phenyl and R
2
and R
3
are identical or different and are hydrogen or C
1
-C
4
-alkyl.
The vinylimidazoles can be employed as free bases or in quaternized form, the copolymerization of quaternized vinylimidazoles being preferred. If the vinylimidazoles are employed in the copolymerization in the form of the free bases, then it is advantageous to conduct quaternization after the polymerization.
Examples of compounds suitable for quaternizing the vinylimidazole are C
1
-C
22
-alkyl halides, for example methyl chloride, bromide and iodide, ethyl chloride and bromide, propyl, hexyl, dodecyl and lauryl chlorides and benzyl halides, especially the chloride and the bromide. Further suitable quaternizing agents are dialkyl sulfates, especially dimethyl or diethyl sulfate. The vinylimidazoles can also be quaternized with alkylene oxides, such as ethylene or propylene oxide, in the presence of acids. Preferred quaternizing agents are methyl chloride, dimethyl sulfate and diethyl sulfate. Further particularly preferred monomers of group (c
1
) are 3-methyl-1-vinylimidazolium chloride and 3-methyl-1-vinylimidazolium methyl sulfate. The quaternization of the monomers or of a polymer with one of the abovementioned quaternizing agents can be performed by methods which are general knowledge.
Examples of suitable monomers (d
1
) are C
1
-C
12
-alkyl acrylates or methacrylates, such as tert-butyl acrylate, isobutyl methacrylate, n-butyl methacrylate, methyl methacrylate, ethyl methacrylate, t-butyl methacrylate, isobornyl acrylate or isobornyl methacrylate, or acrylamides, such as N-tert-butylacrylamide or N-tert-octylarylamide [sic]. Also suitable are monomers whose solubility in water at 25° C. is more than 5% by weight, examples being acrylic, methacrylic and crotonic acid, N-methylolmethacrylamide, N-vinyl-N-methylacetamide, N-vinylformamide, acrylamide, N,N-dimethylacrylamide, methacrylamide, N-vinyloxazolidone, N-vinyltriazole, hydroxyalkyl(meth)acrylates or alkylethylene glycol(meth)acrylates having 1-50 ethylene glycol units in the molecule.
Very particularly preferred copolymers are those of
(a) from 5 to 30% by weight of 3-methyl-1-vinylimidazolium methyl sulfate,
(b) from 40 to 60% by weight of N-vinylcaprolactam, and
(c) from 30 to 50% by weight of N-vinylpyrrolidone.
The polymers can be prepared by the conventional techniques of free-radically initiated polymerization. They are preferably prepared by solution polymerization in solvents such as water, methanol, ethanol, isopropanol or a mixture thereof. The amounts of monomers and solvents are judiciously chosen so as to give solutions with concentrations of from 15 to 60% by weight. Polymerization is normally conducted at from 60° C. to 130° C. under atmospheric or the autogenous pressure.
Initiators that can be employed for the free-radical polymerization are the customary peroxo and/or azo compounds, examples being dibenzoyl peroxide, tert-butyl perpivalate, tert-butyl 2-ethylhexanoate, di-tert-butyl peroxide, tert-butyl hydroperoxide, azobisisobutyronitrile, azobis(2-amidinopropane)dihydrochloride or 2,2′-azobis(2-methylbutyronitrile). Also suitable are initiator mixtures or customary redox initiators. The initiators can be employed in the usual amounts, for example from 0.05 to 5% by weight based on the amount of monomers to be polymerized.
The molecular weight can be adjusted if desired by adding regulators, for example compounds containing sulfur in bonded form.
The K values of the polymers should be from 10 to 350, preferably from 50 to 300. The particular K value desired can be established in a conventional manner by choosing the polymerization conditions, for example the period of polymerization and the concentrations of initiator and regulator. The K values are measured by the method of Fikentscher, Cellulosechemie, 13, (1932) 58-64 at 25° C. in a 0.1% strength by weight aqueous solution.
In the aqueous cosmetic composition the copolymers are used in an amount of from 0.1 to 10% by weight, preferably from 0.1 to 5% by weight and, with very particular preference, from 0.5 to 2.5% by weight

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