WO2000033795A1

WO2000033795A1 - Cosmetic preparations containing organic pigments from the class of pyrrolo-[3,4-c]-pyrroles

Info

Publication number: WO2000033795A1
Application number: PCT/EP1999/009243
Authority: WO
Inventors: Philippe Bugnon
Original assignee: Ciba Specialty Chemicals Holding Inc.
Priority date: 1998-12-08
Filing date: 1999-11-29
Publication date: 2000-06-15
Also published as: AR021561A1; AU2094100A; EP1137390A1

Abstract

The invention relates to cosmetic preparations or formulations for applying to the lips or skin as make-up and for colouring hair or nails, containing organic pigments from the class of pyrrolo-[3,4-c]-pyrroles.

Description

COSMETIC PREPARATIONS CONTAINING ORGANIC PIGMENTS FROM THE CLASS PYRROLO- [3,4-C] -PYRR0LE

The present invention relates to new cosmetic preparations or preparations for applying make-up to the lips or the skin and for coloring the hair or the nails, containing organic pigments with excellent fastness properties. For example, lipsticks, cheek make-up, make-up basics, nail polishes and hair shampoos.

Numerous cosmetic preparations, such as lipsticks and nail polishes with pigments, are already commercially available. In many cases, these pigments are calcium, barium, zirconium or aluminum salts of acidic dyes. In EP-A-0408498 organic effect pigments, which are in the form of platelets of precisely defined size, and their use u. a. described in cosmetic preparations.

Nevertheless, there is still a need for further preparations with changed color shades, which, in addition to being well tolerated, should have excellent fastness properties in as many areas as possible.

It has now been found that the preparations according to the invention meet these conditions.

Thanks to the pigments used according to the invention in the new preparations, it is possible to achieve hues that were previously difficult or impossible to achieve. In addition, there is no change in the color of the preparations over time and this color is almost identical to the colorations of the skin and nails that can be achieved with the new preparations. This makes it very easy to achieve the exact shade you want. Above all, the new preparations are characterized by the fact that they do not show any "bleeding" of the pigments into the skin and nails. that is, they give you sharp contours on the skin and that the nails themselves are not stained.

The invention thus relates to cosmetic preparations or preparations containing, based on the total weight, a) 0.0001-20% of a red pigment from the class of the pyrrolo- [3,4-c] pyrroles, which is not in the form of the EP-A-0 408 498 is present, and b) 80-99.9999% of a cosmetically suitable carrier material. Preferred red pigments are those of the formula (I) or (II)

in question, in which A and B independently of one another each a group of the formula

mean where

Ri and R ₂ are each independently hydrogen, halogen, d-Csalkyl, -O-Cι-C ₅ alkyl,

-S-Cι-C ₅ alkyl, -N (R ₃ ) -dC ₅ alkyl, -CF ₃ , -CN or a group of the formula

fl

R _{3 is} hydrogen or dC ₅ alkyl and R ₄ and R ₅ are each independently hydrogen, halogen, d-Csalkyl, -OdC ₅ alkyl, -SC C ₅ alkyl or -CN.

The dC ₅ alkyl groups can be linear or branched. It is e.g. B. is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl or 2,2-dimethylpropyl.

Halogen primarily means bromine or especially chlorine.

Compounds of the formula (I) which are preferably used are those in which the two substituents A are identical and a group of the formula

mean in which R ^ is hydrogen, chlorine, bromine, cyan, methyl, ethyl, tert-butyl or phenyl and R is hydrogen, chlorine, methyl or cyan.

Preferred among these are 3,6-diphenyl-, 3,6-di (4-chlorophenyl) -, 3,6-di (4-tert-butylphenyl) -, 3,6-di (3-cyan -phenyl) -, 3,6-di (4-cyanophenyl) -, 3,6-di (biphenyl-1 -yl) -, 3,6-

Di (4-methylphenyl) - and 3,6-di (3,4-dichlorophenyl) -1, 4-diketo-2,5-dihydro-pyrrolo- [3,4-c] - pyrrole all 3,6-di (4-chlorophenyl) - or 3,6-di (biphenyl-1-yl) - 1,4-diketo-2,5-dihydropyrrolo [3,4-c] pyrrole .

The pigments contained in the cosmetic preparations and preparations according to the invention are known, for. B. from the European patent application EP-A-0 094 911, or can be represented in a manner known per se.

These pigments can be used individually or as mixtures containing two or more pigments of the formula (1). It is also possible to use one or more pigments of the formula (1) together with other pigments and / or dyes, such as those used in cosmetic preparations.

If desired, the pigments can also be used in the form of surface-modified pigments, e.g. B. modified by perfluoroalkyl phosphate, methylpolysiloxanes, methyl-hydrogen polysiloxanes or chitosan. Suitable modified pigments are, for example, those of B. G. Hays in Am. Inkmaker, (June, 1984) 28, (Oct., 1986) 13 and (Nov., 1990) 28.

In addition, solid solutions of pyrrolo- [3,4-c] pyrroles can also be used, e.g. B. solid solutions consisting of two different such compounds as described in US Pat. No. 4,783,540, or solid solutions of pyrrolo [3,4-c] pyrroles and quinacridones as described in US Pat. No. 4,810,304 are, or solid solutions consisting of two different pyrrolo- [3,4-c] pyrroles and quinacridones as described in US Pat. No. 5,529,623.

These optionally modified pigments are advantageously used as pigment preparations in which the pigment is already in dispersed form. Suitable preparations are e.g. B. in W. Herbst, K. Hunger: Industrielle organic pigments, VCH Verlagsgesellschaft 1995, pages 92 ff. The cosmetic preparations and preparations according to the invention preferably contain the pigment in an amount between 0.005 and 20% by weight, based on the total weight of the preparation.

The usual materials used in such agents are suitable as carrier materials for the cosmetic preparations and preparations according to the invention.

The cosmetic preparations and preparations according to the invention can, for. B. in the form of sticks, ointments, creams, emulsions, suspensions, dispersions, powders or solutions. For example, lipsticks, mascara preparations, face cheeks, eye shadows, make-up basics, eyeliners, powder or nail polishes.

If the preparations in the form of pens, e.g. B. lipsticks, eye shadows, face painting or make-up basics are present, these preparations consist to a large extent of fat bodies, which can consist of one or more waxes, for example ozokerite, lanolin, lanolin alcohol, hydrogenated lanolin, acetylated lanolin, lanolin wax, beeswax , candelilla wax, microcrystalline wax, carnauba wax, cetyl alcohol, stearyl alcohol, cocoa butter, lanolin fatty acids, petrolatum, petroleum jelly, solid at 25 ° C mono-, di- or triglycerides or -Fettester, silicone waxes such as Methyloctadecan-oxypolysiloxan and poly (dimethylsiloxy) stearoxysiloxan, Stearinsäuremonoethanolamin , Colophane and derivatives thereof, such as glycolabietates and glycerinabietates, hydrogenated oils solid at 25 ° C., sugar glycerides and oleates, myristates, lanolates, stearates and dihydroxystearates of calcium, magnesium, zirconium and aluminum.

The fat body can also consist of a mixture of at least one wax and at least one oil, in which case, for. B. the following oils are suitable: paraffin oil, purcellin oil, perhydrosqualene, sweet almond oil, avocado oil, callophyllum oil, castor oil, sesame oil, jojoba oil, mineral oils with a boiling point between approx. 310 and 410 ° C., silicone oils, such as dimethylpolysiloxane, linoleic alcohol, linoleic alcohol, olefin alcohol Cereal germ oils such as wheat germ oil, isopropyl alcoholate, isopropyl palmitate, isopropyl myristate, butyl myristate, cetyl myristate, hexadecyl stearate, butyl stearate, decyl oleate, acetylglycerides, octanoates and decanoates of alcohols and polyalcohols, e.g. B. of glycol and glycerin, Ricinoleates of alcohols and polyalcohols, e.g. B. of cetyl alcohol, isostearyl alcohol, isocetyl alcoholate, isopropyl adipate, hexyl laurate and octyldodecanol.

The fat bodies in these preparations in the form of sticks can generally make up to 99.91% by weight of the total weight of the preparation.

The cosmetic preparations and preparations according to the invention can additionally contain further constituents, such as, for. B. glycols, polyethylene glycols, polypropylene glycols, monoalkanolamides, undyed polymeric, inorganic or organic fillers, preservatives, UV filters or other auxiliaries and additives customary in cosmetics,

It is, for example, a natural or a synthetic or a partially synthetic di- or triglyceride, a mineral oil, a silicone oil, a wax, a fatty alcohol, a Guerbet alcohol or its ester, a lipophilic functional cosmetic ingredient including a sunscreen filter or a mixture of these substances .

An iipophilic functional cosmetic active ingredient which is suitable for skin cosmetics, an active ingredient composition or an active ingredient extract is an ingredient or a mixture of ingredients which is approved for dermal or topical administration. Examples include:

Active ingredients that have a cleansing effect on the skin surface and hair. This includes all substances that serve to clean the skin, such as oils, soaps, syndets and solid substances;

Active ingredients with deodorant and antiperspirant properties: these include antiperspirants based on aluminum or zinc salts, deodorants containing bactericidal or bacteriostatic deodorizing substances such as triclosan, hexachlorophene, alcohols and cationic substances, such as quaternary ammonium salts and odor absorbers, for example ^® Grillocin (combination of zinc ricinoleate and various additives) or triethyicrate, optionally in combination with an antioxidant such as butylated hydroxytoluene) or ion exchange resins;

Active ingredients that offer protection against sunlight (UV filters): Suitable active ingredients are filter substances ("sunscreens") that can absorb UV radiation from sunlight and convert it into heat. Depending on the effect you want the following light stabilizers are preferred: light stabilizers which selectively absorb high-energy UV radiation which produces sunburn in the range from approx. 280-315 nm (UV-B absorber) and transmit the longer-wave range from approx. 315-400 nm (UV-A range) , as well as light stabilizers, which only absorb the longer-wave radiation in the UV-A range of 315-400 nm (UV-A absorber).

Suitable light stabilizers are e.g. organic UV absorbers from the class of p-aminobenzoic acid derivatives, salicylic acid derivatives, benzophenone derivatives, dibenzoyl methane derivatives, diphenylacrylate derivatives, benzofuran derivatives, polymeric UV absorbers containing one or more organosilicon radicals, cinnamic acid derivatives, camphor derivatives, trianilimino acid derivatives, trianiliminoazole derivative, trianiliminoazole derivatives their salts, menthyl anthranilates, benzotriazole derivatives, and / or an inorganic micropigment selected from TiO 2, zinc oxide or mica coated with aluminum oxide or silicon dioxide.

Active substances against insects ("repellents): Repellents are agents which are intended to prevent insects from touching the skin and becoming active there. They drive the animals away and evaporate slowly. The most frequently used repellent is diethyl tolulamide (DEET). Other common repellents are in" W. Raab and U. Kindl, "Pfiegekosmetik", Gustav-Fischer- Stuttgart / New York, 1991, p.161.

Active substances to protect against chemical and mechanical effects: this includes all substances that form a barrier between the skin and the outer noxa, e.g. Paraffin oils, silicone oils, vegetable oils, PCL products and lanolin for protection against aqueous solutions, film formers such as sodium alginate, triethanolamine alginate, polyacrylates, polyvinyl alcohol or cellulose ethers against the action of organic solvents, or substances based on mineral oils, vegetable oils or silicone oils as "lubricants" against strong mechanical stress on the skin;

Humectants: as moisturizer regulators ("moisturizers") find e.g. following substances use: sodium lactate, urea, alcohols, sorbitol, glycerin, propylene glycol, collagen, elastin or hyaluronic acid;

Active substances with keratoplastic effect: benzoyl peroxide, retinoic acid, colloidal sulfur and resorcinol;

Antimicrobial agents such as triclosan or quaternary ammonium compounds; Dermally applicable oily or oil-soluble vitamins or vitamin derivatives: eg vitamin A (getinol in the form of the free acid or its derivatives), panthenol, pantothenic acid, folic acid, and combinations thereof, vitamin E (tocopherol), F; essential fatty acids; or niacinamide (nicotinamide);

Vitamin-based placenta extracts: active ingredient compositions primarily with vitamins A, C, E, B ₂₁ B ₁₂ , folic acid and biotin, amino acids and ferments as well as compounds of the trace elements magnesium, silicon, phosphorus, calcium, manganese, iron or copper.

Skin repair complexes: available from inactivated and disintegrated cultures of bacteria from the bifidus group;

Plants and plant extracts: such as Arnica, aloe, beard lichen, ivy, nettle, ginseng, henna, chamomile, marigold, rosemary, sage, horsetail or thyme;

Animal extracts: such as Royal jelly, propolis, proteins or thymus extracts; dermally applicable cosmetic oils: neutral oils of the Miglyol 812 type, apricot kernel oil, avocado oil, babassu oil, cottonseed oil, borage oil, safflower oil, peanut oil, gamma-oryzanol, rosehip seed oil, hemp oil, hazelnut oil, currant seed oil, linseed oil, corn oil, corn oil, corn oil, corn oil, cherry oil, jojoba oil, corn oil, corn oil, corn oil, corn oil, corn oil , Evening primrose oil, mink oil, olive oil, pecan oil, peach seed oil, pistachio seed oil, rapeseed oil, rice germ oil, castor oil, safflower oil, sesame oil, soybean oil, sunflower oil, tea tree oil, grape seed oil or wheat germ oil.

The preparations in the form of sticks are preferably anhydrous, but in certain cases they can contain a certain amount of water which, however, generally does not exceed 40% by weight, based on the total weight of the cosmetic preparation.

If the cosmetic preparations and preparations according to the invention are in the form of semi-solid products, ie as ointments or creams, they can also be anhydrous or aqueous. These are, for example, mascaras, eyeliner, make-up basics, cheek make-up, eye shadows or agents for the treatment of dark circles. If, on the other hand, these ointments or creams are aqueous, they are in particular emulsions of the water-in-oil type or of the oil-in-water type which, apart from the pigment, contain 1 to 98.8% by weight of the fat phase, 1 contain up to 98.8% by weight of the aqueous phase and 0.2 to 30% by weight of an emulsifier.

These ointments and creams can also contain other conventional additives, such as. B. fragrances, antioxidants, preservatives, gelling agents, UV filters, dyes, pigments, pearlescent agents, undyed polymers and inorganic or organic fillers.

If the preparations are in the form of a powder, they consist essentially of a mineral or inorganic or organic filler, such as. B. talc, kaolin, starch, polyethylene powder or polyamide powder, and auxiliaries such as binders, dyes, etc.

Such preparations can also contain various cosmetic auxiliaries, such as fragrances, antioxidants, preservatives, etc.

If the cosmetic preparations and preparations according to the invention are nail varnishes, they essentially consist of nitrocellulose and a natural or synthetic polymer in the form of a solution in a solvent system, this solution optionally containing other auxiliaries, such as, for. B. pearlescent contains.

In this embodiment, the colored polymer is present in a proportion between approximately 0.1 and 5% by weight.

The cosmetic preparations and preparations according to the invention can also be used for dyeing hair, in which case they are used in the form of shampoos, creams or gels, which are composed of the basic materials customary in the cosmetics industry, and a red pigment of the formula given above (I) or (II) contains. The cosmetic preparations and preparations according to the invention are produced in a customary manner, for example by mixing or stirring the components, if appropriate with heating, so that the mixtures melt.

The following examples serve to illustrate the invention without restricting it thereto. Parts mean parts by weight and percentages by weight. The temperatures are given in degrees Celsius.

Example 1: A lipstick base of the following composition is used:

Number substance quantity [%]

1 Cera alba 11, 4

2 candelilla waxes 8.1

3 carnauba wax 3.8

4 Lunacera M 6.0

5 castor oil 38.8

6 Controx KS 0.1

7 aromatic oil 1, 0

8 Amerlate P 2.5

9 OH Ian 1, 6

10 isopropyl palmitate 10.1

11 Dow Corning 556 2.8

12 Dow Corning 1401 3.3

13 TiO ₂ pigment 2.3

14 red pigment 8.2

100.0

The red pigment is 3,6-di (4-chlorophenyl) -1,4-diketo-2,5-dihydro-pyrrolo [3,4-c] pyrrole.

Substances 8-10 are mixed and substances 13 and 14 are dispersed in this mixture. The paste obtained is then passed several times over a three-roller. In the meantime, substances 1 - 6 are melted, mixed homogeneously with one another and then substances 7, 11 and 12 are stirred in.

Then the two mixtures are mixed hot until a homogeneous distribution is achieved. Then the hot mass is poured into a lipstick mold and allowed to cool.

You get lipsticks with an intense bright red color, excellent lightfastness and very good shine, which show no bleeding.

Example 2: A make-up base of the following composition is used:

Number substance quantity [%]

1 Cutina KD 16 0.80

2 Cutina FS 45 1, 40

3 Lanette 16 1, 00

4 Arlacel 60 0.20

5 paraffin oil pearl. 8.00

6 isopropyl stearate 6.00

7 Myritol 318 4.00

8 Softisan 100 2.00

9 Abil 100 0.20

10 Controx KS 0.05

11 Uniphen P 23 1, 00

12 Talcum Pharma G 5.00

13 titanium white 6.00

14 red pigment 1, 50

15 demineralized H ₂ O 56.10

16 propylene carbonate 0.10

17 Veegum ultra 0.80

18 glycerol 87% 5.00

19 Natrosol 250 HHR 0.3

20 TEA C, pure 0.55 100.00

The red pigment has the same formula as in Example 1.

The substances 1-11 are melted together and the substance 12 is dispersed in this mixture. The mixture is then heated to 75-80.degree.

Independently of this, substances 15 and 16 are mixed and substances 17 are dispersed homogeneously in this mixture. Then you distribute the substance 19 homogeneously in this mixture, wait until the swelling no longer increases, stir in the substance 18 and heat the entire mixture to 75-80 ° C.

The second mixture is then added to the first mixture with vigorous stirring, substance 20 is then stirred in homogeneously and the resulting emulsion is stirred until it has cooled to room temperature. The substances 13 and 14 are then dispersed in using a dissolver and the make-up obtained is then passed over a three-roller.

You get a red make-up with perfect usage properties and with an intense bright red color of excellent lightfastness.

Example 3: The following substances are used for a nail polish:

Number substance quantity [%

1 sodium selenite 0.01

2 ethyl acetate 20.00

3 isobutyl acetate 26.99

4 isopropyl alcohol 2.00

5 toluene 20.00

6 nitrocellulose 17.00

7 sucrose acetate isobutyrate 8.00

8 dibutyl phthalate 3.80

9 1,3-butylene glycol 0.20

10 pigment from Example 1 1, 00 11 stearylalkonium hectorite 1, 00

100.0 You get a red nail polish with very good fastness properties and excellent shine. After applying the nail polish, waiting for three days and removing the nail polish, it shows that the nail has remained completely undyed.

Example 4: The following substances are used for a mascara formulation:

Number substance quantity [%]

1 stearic acid 3.50

2 glycerol stearate 6.00

3 beeswax 7.00

4 propylparaben 0.10

5 demineralized water 38.25

6 methyl paraben 0.10

7 polyvinyl pyrrolidone 6.00

8 propylene glycol 3.00

9 Na carboxymethyl cellulose 0.15

10 pigment from Example 1 10.40

11 kaolin 3.50

12 ethyl acrylates / methyl acrylate (8/2) 22.00

100.0 A mixture of substances 1 to 4 and 5 to 9 is heated separately from one another until homogeneous mixtures are formed, then combined and stirred well until a homogeneous phase is obtained. Then components 10 and 11 are dispersed in part of this phase and the dispersion is then added to the rest. Then component 12 is added with stirring.

This gives a mascara formulation with flawless usage properties. Example 5: A mascara formulation for hair is made from the following components:

Component Composition Quantity [%]

A mascara base (mixture of beeswax, camauba wax,

Stearic acid, cceteareth 25, PEG-2 stearate, mineral oil, hydrogenated

Coconut oil and cetyl alcohol) 15.00

Dimethicone 1, 50

B preservative 0.50

C demineralized water 42.10

D Triethanolamine 85% 0.45

E Thickener mixture (xanthan gum, hectorite, cellulose gum) 0.45

F pigment from Example 1 10.00

G Acrylate copolymer 30.00

100.0

Components A are heated in a steel tank with slow stirring to about 75 ° C. In a separate kettle, component B is dissolved in C and E is added so that a gel which is homogeneous at room temperature is obtained. Then add D and heat to approx. 75 ° C. With moderate stirring, add the mixture of components B, C, D and E to components A and stir until the product is homogeneous. In a part of this product, component F is dispersed using a three-roller mill, component G is added with stirring, the dispersion is then added to the rest of the product and mixed well.

A mascara formulation for hair with good usage properties is obtained.

Example 6: The following substances are used for a water-based nail polish:

Number substance quantity [%]

1 demineralized water 58.85

2 titanium dioxide 5.60 3 pigment from Example 1 2.16

4 talc 5.72

5 potassium cetyl phosphate 1, 50

6 propylene glycol 8.00

7 mg Al silicate 1.00

8 cellulose gum (highly viscous) 0.14

9 esters of sucrose and coconut fatty acid 0.20

10 methyl paraben 0.20

11 EDTA 0.05

12 propylene glycol dicaprylate / dicaprate 10.00

13 isostearyl stearyl stearate 2.00

14 sorbitan monolaurate 3.0

15 cetyl alcohol 0.5

16 propylparaben 0.10

17 DMDM hydantoin 0.18

Example 7: A water-in-oil lipstick emulsion of the following composition is prepared analogously to Example 1:

Ingredients (% by weight)

Mineral oil 20.00

Glycerin bis (2-heptylundecanoate) 20.00

Red pigment according to Example 1 9.20

Polyethylene wax 7.00

Candelilla wax 7.00

Ceresin wax 4.00

Water 3.00

Glycerin 2.00 Camauba wax 1.00

Castor oil 1.00

Magnesium aluminum silicate 0.15

Benzyldimethylstearylammonium chloride 0.05

Hydrogenated lecithin 0.05

Example 8: An oil-in-water lipstick emulsion of the following composition is prepared analogously to Example 1:

Ingredients (% by weight)

Glycerol tri-2-ethylhexanoate 31.80

Jojobaöll 20.00

Ceresin wax 10.00

Castor oil 10.00

Red pigment according to Example 1 10.00

Lanolin oil 5.00

Water 5.00

Microcrystalline wax 3.00

Canauba wax 2.00 Surfactants based on alkyl ether 2.00

Glycerin 1.00

Polyvinyl alcohol 0.20

Example 9: Analogously to Example 1, a non-greasy lipstick of the following composition is produced:

Ingredients (% by weight)

White beeswax 20.0

Ozekerite 10.0

Red pigment according to Example 1 9.0

Anhydrous lanolin 5.0 Propylene glycol recinoate 4.0

Liquid paraffin 3.0

Isopropyl myristate 3.0

Carnauba wax 2.5

Cetyl alcohol 2.0

Cl Pigment Blue 15 1.0

Castor Oil to 100

Example 10: Analogously to Example 1, a transfer-resistant lipstick of the following composition is produced:

Ingredients (% by weight)

Cyclomethicone 41.70

Isodecane 10.00

Red pigment according to Example 1 8.00

Synthetic wax 6.00

Isostearyltrimethylpropane siloxysilicate 5.00

Cetyl stearate / acetylated lanolin, 90:10 5.00

Ceresin 4.00

Paraffin 3.00

Titanium dioxide 2.00

Methyl paraben 0.30

Propylparaben 0.10

Example 11: A waterproof eyeshadow cream with excellent properties has the following composition:

Ingredients (% by weight)

Acrylic acid / butyl acrylate methyl methacrylate

Copolymer, 30% emulsion 10.00

Red pigment according to Example 1 10.00

Mineral oil 8.50 Glycerin 5.50

Microcrystalline wax 3.00

Stearic acid 3.00

Ultramarine blue 2.00

Sorbitan monostearate 1.50

TEA 1.50

Lanolin 1.00

Methyl hydroxypropyl cellulose 0.50

Preservative qs

Example 12: A waterproof eyeshadow gel with excellent usage properties has the following composition:

Ingredients (% by weight)

Propylene glycol 5.00

Sucrose distearate 3.00

Isopropyl palmitate 3.00

Mineral oil 3.00

Lanolin oil 2.00

Synthetic hectorite 2.00

Di-Na EDTA 0.02

Red pigment according to Example 1 1.00

Cl Pigment Blue 15 0.50

Preservative qs

Water to 100

Example 13: A water-in-oil mascara with excellent performance properties has the following composition:

Ingredients (% by weight)

Polyisobutylene 57.60

Microcrystalline wax 20.00 Red pigment according to Example 1 10.00

Carnauba wax 7.00

Bentonite 3.00

Beeswax 2.00

Lanolin 0.40

Example 14: A make-up stick with excellent usage properties has the following

Composition on:

Ingredients (% by weight)

Mineral oil and lanolin alcohol 22.50

Laneth-5 3pm

Titanium dioxide 11.00

Cetyl alcohol 5.00

Carnauba wax 4.50

Red pigment according to Example 1 4.00

Yellow iron oxide 4.00

Candilla wax 0.50

Perfume and preservative qs

Oleyl alcohol to 100

Example 15: A blush (powder) with excellent performance properties has the following

Composition on:

Ingredients (Ge

Talc 58

Zinc stearate 15

Rice starch 15

Red pigment according to Example 1 12

Perfume qs Example 16: A foundation cream with excellent usage properties has the following composition:

Ingredients (% by weight)

Titanium dioxide 12.79

Oleyl alcohol 4.57

Glycerol stearate 3.65

Propylene glycol 3.65

Stearic acid 1.83

Magnesium aluminum silicate 0.91

Triethanolamine 99% 0.91

Cl Iron Oxide Yellow 0.64

Red pigment according to Example 1 0.42

Cl Pigment Brown 6 0.37

Carboxymethyl cellulose 0.10

Water to 100

Example 17: A hair mascara of the following composition is prepared analogously to Example 5:

Ingredients (% by weight)

Red pigment according to Example 1 12.00

White beeswax 6.50

Propylene glycol 6.00

Carnauba wax 4.25

Cetearyl alcohol and dicetyl phosphate and ceteth-10 phosphate (Crodafos CES) 4.00

PVP / hydrolyzed wheat protein copolymer 4.00

Steareth-10 1.00

Stearyl alcohol 1.00

PVP 1.00

Steareth-2 0.50 Laneth-5 0.50

Potassium hydroxide 0.24

Hydroxyethyl cellulose 0.10

Di-Na-EDTA 0.10

Preservative qs

Water to 100

Examples 18 to 25: Instead of the pigments used in Examples 1 to 17, equivalent amounts of the following pigments can also be used in the cosmetic preparations described in these examples.

Example pigment

18 3,6-diphenyl-1,4-diketo-2,5-dihydro-pyrrolo- [3,4-c] pyrrole,

19 3,6-di (4-chlorophenyl) -1,4-diketo-2,5-dihydro-pyrrolo- [3,4-c] pyrrole,

20 3,6-di (4-tert-butylphenyl) -1,4-diketo-2,5-dihydro-pyrrolo- [3,4-c] pyrrole,

21 3,6-di (3-cyanophenyl) -1,4-diketo-2,5-dihydro-pyrrolo- [3,4-c] pyrrole,

22 3,6-di (4-cyanophenyl) -1,4-diketo-2,5-dihydro-pyrrolo- [3,4-c] pyrrole,

23 3,6-di (biphenyl-1-yl) -1,4-diketo-2,5-dihydro-pyrrolo- [3,4-c] -pyrrole,

24 3,6-di (4-methylphenyl) -1,4-diketo-2,5-dihydro-pyrrolo- [3,4-c] pyrrole,

25 3,6-di (3,4-dichlorophenyl) -1,4-diketo-2,5-dihydro-pyrrolo [3,4-c] pyrrole,

Claims

claims

1. Cosmetic preparations or preparations containing, based on the total weight, a) 0.0001-20% of a red pigment from the class of the pyrrolo- [3,4-c] -pyrroles, which is not in the form of the in EP-A -0 408 498 platelets described, and b) 80-99.99% of a cosmetically suitable carrier material.

2. Cosmetic preparations or preparations according to claim 1, characterized in that they are a pigment of formula (I) or (II)

contain, wherein A and B each independently of one another a group of the formula

mean where

R _t and R ₂ are each independently hydrogen, halogen, dC ₅ alkyl, -OdC ₅ alkyl,

-SdC ₅ alkyl, -N ^ Jd-dalkyl, -CF ₃ , -CN or a group of the formula

R ₄

R _{3 is} hydrogen or d-Csalkyl and R ₄ and R ₅ each independently represent hydrogen, halogen, dC ₅ alkyl, -O-Cι-C ₅ alkyl, -SC C ₅ alkyl or -CN.

3. Cosmetic preparations or preparations according to claim 2, in which the two substituents A are identical and a group of the formula

mean, wherein Ri is hydrogen, chlorine, bromine, cyan, methyl, ethyl, tert-butyl or phenyl and R _{2 is} hydrogen, chlorine, methyl, or cyan.

4. Cosmetic preparations or preparations according to Claim 3, characterized in that they contain 3,6-diphenyl-, 3,6-di (4-chlorophenyl) -, 3,6-di (4-tert-butyl- phenyl) -, 3,6-di (3-cyanophenyl) -, 3,6-di (4-cyanophenyl) -, 3,6-di (biphenyl-1 -yl) -, 3,6- Di (4-methylphenyl) - or 3,6-di (3,4-dichlorophenyl) -

1, 4-diketo-2,5-dihydro-pyrrolo- [3,4-c] pyrrole included.

5. Cosmetic preparations or preparations according to Claim 4, characterized in that they contain 3,6-di (4-chlorophenyl) - or 3,6-di (biphenyl-1 -yl) - 1,4-diketo- as pigment. Contain 2,5-dihydro-pyrrolo [3,4-c] pyrrole.

6. Cosmetic preparations or preparations according to one of claims 1 to 5, characterized in that the pigment is present in an amount between 0.005 and 20% by weight, based on the total weight of the preparation.

7. Cosmetic preparations or preparations according to one of claims 1 to 6, characterized in that they are in the form of a stick which contains up to 99.9999% by weight of fat bodies.

8. Cosmetic preparations or preparations according to one of claims 1 to 6, characterized in that they are in the form of an anhydrous or aqueous ointment or cream.

9. Cosmetic preparations or preparations according to any one of claims 1 to 6, characterized in that they are in the form of a water-in-oil emulsion or in the form of an oil-in-water emulsion which 1 to 98.8% by weight Fat phase, 1 to 98.8% by weight of the aqueous phase and 0.2 to 30% by weight of an emulsifier, in each case based on the total weight.

10. Cosmetic preparations or preparations according to one of claims 1 to 6, characterized in that they are in the form of a powder and contain an inorganic or organic filler, such as talc, kaolin, starch, polyethylene powder or polyamide powder, and auxiliaries such as binders or dyes.

11. Cosmetic preparations or preparations according to one of claims 1 to 6, characterized in that they are in the form of a nail polish and contain 0.1 to 5% by weight of the pigment in a lacquer base.

12. Cosmetic preparations or preparations according to one of claims 1 to 6, characterized in that they are in the form of a shampoo, a cream or a gel for dyeing hair, which are composed of the basic materials customary in the cosmetics industry and a pigment of the formula (I) or (II) included.

13. Cosmetic preparations or preparations according to any one of claims 1 to 11, characterized in that they additionally contain conventional cosmetic ingredients, such as fragrances, antioxidants, preservatives and UV filters.