NL8500271A - Cosmetic lipstick compsn. - contains lanolin ester or (1)-docosanoyloxy-(3)-ethylhexyloxy (2)-propanol to prevent colour migration - Google Patents

Abstract

A cosmetic compsn. for lipstick contains essentially (i) >=1 fat soluble polymer contg. vinyl ester moieties; (ii) >=10; of novel 1-docosanoyloxy-3-(2-ethyl hexyloxy)-propanol-2 of formula (II) or a cpd. of formula (I) (where R is the residue of lanolin alcohol; R1 is a radical C10H21 and n is 1.5); (iii) >=1 fat and (iv) >=1 non-toxic colourant. The use of cpds. (ii) prevents colour migration on the lips resulting in a more brilliant film.

Description

1 'H.0. 35000

A method for preparing a cosmetic lip red preparation as well as a method for preparing an isopropanol derivative suitable for use in such a preparation.

The invention relates to a method for preparing a cosmetic lip-red preparation by combining at least one fat-soluble polymer with: vinyl ester units, at least one fat-like substance and at least one non-toxic dye.

French Pat. No. 2,222,351 relates to specific bigsubstituted glycerol derivatives of the formula R 1 -X-CH 1 -OHCOHJ-C 1 -YI 2 wherein X and Y, independently, are an oxygen atom or a carboxyl group, a branched alkyl group of 5-8 carbon atoms with 1-3 carbon atoms in the branch (s) 15 and R2 represent a linear alkyl group of 11-18 carbon atoms as well as the use of these derivatives in the preparation of a variety of cosmetic preparations such as lip red preparations. An indication for the use of these bigsubstituted glycerol derivatives or other similar derivatives with fat-soluble polymers containing vinyl ester units in the preparation of lip red compositions is neither disclosed nor suggested in this patent.

French patent specification 2,232,302 discloses the use of homopolymers obtained by homopolymerization of vinyl esters, acrylates or methacrylates in, for example, lip-red preparations. However, such lip red compositions have been found to have some disadvantages, in particular migration of the clay substances into the corners of the mouth. However, there is no indication in this French patent specification of the use of, for example, both polymers with vinyl ester units and of a high molecular weight 1,3-bigesubstituted isopropanol derivative.

It has been found that in the preamble lip red compositions with excellent utilization properties such as an increased gloss and the absence of a migration of the dyes in the region of the corners of the mouth can be prepared if at least 10 wt.% 35-behenoyloxy- are added therein. 3- (2-ethylhexoxy) -propanol-2 of the formula C21H43 "C00" CH2 "C (0H) H" CH2 ~ "" CH2 ~ G <: G2H5) h "G4H9.

Preferably, 10-30% by weight of 1-behenoyloxy-3- (2-ethylhexoxy) -propanol-2 is used.

40 1-Behenoyloxy-3- (2-ethylhexoxy) -propanol- (2) can be obtained in a manner known per se for analogous compounds of 8500271, for example, by reaction of behenic acid with the 2-ethylhexylglycidyl ther. This conversion is carried out in the presence of a basic catalyst, such as sodium amethoxide or ethanolate, and the reaction mixture is heated at a temperature of about 130 ° C for 2-8 hours. The product is isolated from the reaction mixture by several times with water wash, neutralize with a base, and then dry under reduced pressure. The volatile products are removed at a temperature of about 130 ° C under a pressure of 0.133 Pa, after which the desired product is distilled at a temperature of about 205 ° C under a pressure of 0.133 Pa. The product obtained is a solid at room temperature and has a final melting point of about 35 to 40 ° C.

The latter compound replaces at least a portion of the fatty material, which consists of either a wax or a mixture of a wax and an oil.

According to the invention, the fat-like material is generally present in an amount of from 35 to 75% by weight.

Among the waxes which can be used as a fatty substance, particular mention can be made of: ozokerite, lanolin, lanolin alcohol, hydrogenated lanolin, acetylated lanolin, lanolin wax, beeswax, candellila wax, microcrystalline wax, carnauba wax, cetyl alcohol , stearyl alcohol, spermaceti, cocoa butter, fatty acids of lanolin, petrolatum, vaselines, solid mono-, di- and tri-25 glycerides at a temperature of 25 ° C, solid fatty esters at a temperature of 25 ° C, siloxane waxes, such as methyl octadecanoxypolysiloxane and poly (dimethylsiloxy) -stearoxysiloxane, stearic acid monoethanolamide, rosin and derivatives thereof, such as glycol and glycerol abietates, at a temperature of 25 ° C, solid hydrogenated oils, sucroglycerides and oleates, myristates, 30 lanolates, stearates and dihydroxy stearates calcium, magnesium, zircon and aluminum.

Among the oils which can be used as a fatty substance, the following can be mentioned in particular: paraffin oil, purcellin oil, perhydrosqualene, sweet almond oil, avocado oil, calophyllum oil, castor oil 35, soft horse fat, soft lard, olive oil, mineral oils with a boiling point between 310 and 410 ° C, siloxane oils, such as dimethylpolysiloxanes, linoleic alcohol, linolenic alcohol, oleic alcohol, grain germ oils, such as wheat germ oil, isopropyl alkylate, isopropyl palmitate, iso-propyl myristate, butyl myristate, cetyl methyl stearate, cetyl methyl stearate butyl stearate, octyl hydroxystearate, decyl oleate, 8500271 3

.- A

acetylglycerides, caprylic and caprols, such as glycol and glycerol, castoric acid esters of alcohols and polyols, such as of cetyl alcohol, isostearyl alcohol, isocetylloxide, isopropyl adipate, hexyl dodecanol.

According to the invention, as waxes or oils, derivatives of alkane-1,2-diols, in particular alkane-1,2-diol esters of fatty acids, as described in French patent 2,281,916, or compounds such as described in French Patents 2,222,351 and 2,281,743.

The polymers with vinyl ester units useful in the lip red compositions of the invention must be soluble in fat-like materials, that is, they must have a high affinity for waxes and oils. These polymers, as noted above, are either homopolymers or copolymers and must be present in the composition of the invention at a concentration of 10 to 35% by weight. Of the homopolymers, particular mention can be made of the bomopolymers obtained by polymerization of vinyl polymers. caprolate, vinyl α, α-dimethylvalerate, vinyl caprylate, vinyl esters of cecanoic acid (cecanoic acid is a trade name for a mixture of linear and branched fatty acids having the same number of carbon atoms, namely 8, 9 or 10), vinyl laurate, vinyl stearate and vinyl isostearate.

Of the copolymers, particular mention can be made of the copolymers obtained by copolymerizing vinyl acetate / allyl stearate, vinyl acetate / vinyl laurate, vinyl acetate / vinyl stearate, vinyl acetate / octadecene, vinyl acetate / octadecenyl vinyl ether, vinyl propyl ether, vinyl propyl ether, vinyl propyl ether vinyl stearate / octadecene (l), vinyl acetate / dodecene (l), vinyl stearate / ethyl vinyl ether, vinyl propionate / cetyl vinyl ether, vinyl stearate / allyl acetate, vinyl-e, α-dimethyl caprylate / vinyl laurate, allyl-α, α-dimethyl urate Vinyl dimethyl propionate / vinyl stearate, allyl dimethyl propionate / vinyl stearate, vinyl propionate / vinyl stearate, vinyl dimethyl propionate / vinyl laurate and allyl propionate / allyl stearate.

These copolymers may optionally be cross-linked with a cross-linking agent to increase their molecular weight. Among these cross-linking agents, in particular, tetraallyloxyethane, divinyl benzene, divinyl suberate (= divinyl ester of octanedioic acid), the divinyl ester of dodecanedioic acid and the divinylester of octadecanedioic acid.

These homopolymers and copolymers preferably have a molecular weight between 2000 and 500,000 and in particular between 6000 and 40,000.

850027! 4

These vinyl ester homopolymers and copolymers are described in more detail in French Pat. Nos. 2,232,302 and 2,232,303.

The coloring agents used in the compositions of the invention are, of course, non-toxic dyes, such as the dyes commonly used in lip red compositions.

In general, they are present in an amount of between 2 and 30% by weight, the following being exemplified by the dyes: eosins and other halogenated derivatives of fluorescent cells (bromic acids) and in particular the substances which known under the designations D and C Red no.21, D and C Red no.27, D and C Orange no.5, inorganic pigments, such as iron and chromium oxides, ultramarines (polysulfides of aminosilicates), titanium dioxide, and organic pigments such as D and C Red no.36 and D and C Orange no.17.

The dyes also include the pigment coatings, such as the calcium coatings of D and C Red Nos. 6, 7, 21 and 27, the barium coatings of D and Cellow Nos. 5 and 6 and the zirconia coatings of D and C Red no.21 and D and C Orange no.5.

It will be understood, of course, that these compositions according to the invention may also contain other conventional ingredients, such as iridescent substances in an amount of 2 to 20% by weight, perfumes, anti-sunscreens, antioxidants and preservatives.

Of the iridescent substances, bismuth oxychloride, mica titanium and guanine crystals can be mentioned in particular. Of the antioxidants, particular mention may be made of the phenolic antioxidants, such as propyl, octyl and dodecyl esters of bile acid, butylated hydroxyanisole, butylated hydroxytoluene and nordihydroguaiic acid.

In certain cases it is also necessary to use certain solvents for coloring substances insoluble in the fatty substances. Glycols, tetrahydrofurfuryl esters, polyethylene glycols and monoalkanolamides can be mentioned as examples of these solvents.

The following describes, by way of example, the preparation of 1-management-noyloxy-3- (2-ethylhexoxy) -propanol- (2) as well as the preparation of various cosmetic lip-red preparations according to the invention. Preparation of 1-behenoyloxy-3- (2-ethylhexoxy) -propanol- (2).

To 335 g (1.050 mol) of molten behenic acid (or docosanoic acid) in a flask, 2.9 g (50 meq) of powdered sodium methanolate were added with stirring, after which the mixture was heated to 130 ° C under a nitrogen atmosphere. heated.

8300271 5

Then, 186 g (1 mol) of 2-ethylhexyl-glycidyl ether was added dropwise with stirring, and the mixture was heated at 130 DEG C. under a nitrogen atmosphere for another 6 hours from the end of the feed.

5 The conversion rate was determined on the basis of the remainder

acid number. The conversion was continued until a conversion rate of I.

about 95% had been reached.

The product thus obtained was washed once with 500 ml of boiling water containing the necessary amount of sodium hydroxide to neutralize the residual acidity.

After the water, 200 ml of isopropanol were added to facilitate decantation. Subsequently, washing was carried out twice more with 500 ml of water each at a temperature of 80 ° C.

The resulting product was then dried on a boiling water bath in vacuo and with stirring.

The product was finally purified by molecular distillation: 1) Removal of volatiles at a temperature of 130 ° C under a pressure of 0.133 Pa.

2) Distillation of the product at a temperature of 205 ° C under a pressure of 0.133 Pa.

Yield during distillation: 78%.

Total yield: 67%.

Analysis:

Saponification number: theoretical: 1.98 meq / g; Found: 2.0 meq / g;

Hydroxyl number: theoretical: 1.98 meq / g; found: 1.85 meq / g.

Acid number: 0

End melting point: 35 ° C.

Example I

A lip red preparation according to the invention was prepared by preparing a mixture of the following ingredients: microcrystalline wax 12 g acetylated lanolin 5.9 g 35 lanolin 10 g hydrogenated lanolin 10 g lanolin alcohols 11 g butylated hydroxyanisole 0.1 g 31.3 wt. .% vinyl acetate / 68.7 wt.% 40 allyl stearate copolymer 8 g 8500271 6 vinyl laurate homopolymer 15 g l-behenoyloxy-3- (2-ethylhexoxy) propanol- (2) 15 g

Coloring agents: 5 titanium oxide 1 g

Al-lacquer of D and C Sed No. 27 7.5 g D and C Red No. 36 1 g

Al-lacquer of D and C Yellow No. 6 * 2.5 g perfume 1_g 10 100 g

Example II

A lip red preparation according to the invention was prepared by preparing a mixture of the following ingredients: 15 microcrystalline wax 9 g acetylated lanolin 9 g oleyl alcohol 11 g liquid lanolin 8 g mineral oil 10.9 g 20 butylated hydroxytoluene 0.1 g 31.3 wt. .% vinyl acetate / 68.7 wt.% allyl stearate copolymer 10 g vinyl laurate homopolymer 11 g 1-behenoyloxy-3- (2-thylhexoxy) - 25 propanol- (2) 20 g

Coloring agents: titanium oxide 3.5 g zirconium lacquer of D and C Red No. 21 3.5 g calcium lacquer of D and C Red No. 6 0.2 g 30 D and C Red No. 36 1.5 g

Al-lacquer of D and C Yellow No. 6 1.5 g perfume 0> 8 g 100 g 1 2 3 4 5 6 6 5 0 0 2 7 1

Example III

2

A lip red preparation according to the invention was prepared by preparing a 3 mixture of the following ingredients: 4 ozokerite 15 g 5 lanolin 8 g 6 mineral oil 3 g

a

7 oleyl alcohol 5 g triglycerides 3 g castor oil 8.4 g fautylated hydroxytoluene 0.1 g 5 31.3 wt% vinyl acetate / 68.7 wt% allyl stearate copolymer 10 g vinyl laurate homopolymer 10 g 1-b ehenoyloxy-3- (2 ethylhexoxy) propanol (2) 15 g 10 Coloring agents;

Al-lacquer of D and C Red No. 27 1 g

Ca-lacquer of D and C Red No. 7 1 gj D and C Red No. 36 1 g 5 D and C Red No. 6 5 gj 15 Al-lacquer of D and C Yellow No. 5 1 g micatitane 11 g perfume 1> 5 g 100 g 20 Example IV j

A lip red preparation according to the invention was prepared by preparing a mixture of the following ingredients: microcrystalline wax 8 g liquid lanolin 10 g mineral oil 4 g acetylated lanolin 6.9 g hydrogenated palm oil 6 g compound of the formula R-COO-C ^ "CH-R" where

30 OH

R = * C15H31 R, = ci4 srael range * 55 - 60 ° C 5 g butylated hydroxyanisole 0.1 g 31.3 wt% vinyl acetate / 68.7 wt% allyl-35 stearate copolymer 15 g vinyl laurate homopolymer 10 g l-behenoyloxy- 3- (2-ethylhexoxy) propanol- (2) 15 g

Coloring agents: 40 titanium oxide 3.75 g «3 C ü 2 7 1 8

Al-lacquer of D and C Red No. 27 1.25 g D and C Red No. 30 1 g

Al-lacquer of D and C Yellow No. 6 1 g bismuth oxychloride 12 g 5 perfume 1 g 100 g

Example V

A lip red preparation according to the invention was prepared by preparing a mixture of the following ingredients: ozokerite 4 g microcrystalline wax 6 g acetylated lanolin 10 g castor oil 10 g 15 hydrogenated coconut oil 10 g lanolin alcohols 3.9 g compound of the formula R- COO-CE ^ -CH-R '

OH

20 R »c 15 H 3 i

melting range: 55 - 60 ° C

acid number: 0.2 mq / g 6 g butylated hydroxytoluene 0.1 g 31.3 wt% vinyl acetate / 68.7 wt% allyl-25 stearate copolymer 8 g vinyl laurate homopolymer 16 g l-behenoyloxy-3- (2- ethylhexoxy) -propanol- (2) 15 g

Coloring agents: titanium oxide 6.5 g 30 Ca-lacquer of D and C Red no.7 0.5 g D and C Red no.36 0.5 g iron oxide black 0.4 g

Al-lacquer of D and C Yellow No. 4 2.6 g perfume 0.5 g 35 100 g

Example VI

A lip red preparation according to the invention was prepared by preparing a mixture of the following ingredients: 40 polyvinyl laurate 9.2 g 8 5 9 ö 2 7 1 9 polyethylene fat (molecular weight 1500) 33 g l-behenoyloxy-3- (2-ethylhexoxy) -propanol- (2) 14 g compound of the formula R-COO-C 1 -CH-R 'i

5 OH

R "C 15 H 31

Rf = * 0 ^ 2 ^ 14 melting range * 55 - 60 ° C 4 g lanolin 9.7 g liquid lanolin 10.5 g 10 p-dimethylaminobenzoic acid amyl ester 1 g D-Panthenol 1 g

Calendula oil 8 g polyethylene wax 2 g di-tert-butyl-p-cresol 0.1 g i 15 mineral oil 3 g

Coloring fabrics:

Al-lacquer of D and C Red No. 21 0.2 g D and C Red No. 6 0.5 g iron oxide yellow 0.3 g 20 iron oxide black 0.4 g

Al-lacquer of D and C Yellow No. 5 2.5 g perfume 0> 6 g 100 g

Example VII

A lip red preparation according to the invention was prepared by preparing a mixture of the following ingredients: polyvinyl laurate 28 g 31.3 wt.% Vinyl acetate / 68.7 wt.% Allyl stearate copolymer 4.8 g. 30 polyethylene fat 33 g l- behenoyloxy-3- (2-ethylhexoxy) -propanol- (2) 19.3 g compound of the formula R-C00-CH2-CH-R'i

35 OH

R “G15H31 R '* O ^ / O ^ melting range * 55 - 60 ° C 1 g tert.butyl anisole 0.1 g acetylated lanolin 4.8 g 40 mineral oil 4.8 g 8 5 5 0 2 7 1> * 10

Coloring fabrics:

Al-lacquer of D and C Red No. 21 g D and C Red No. 36 0.3 s

D and C Red No. 30 S

5 D and C Red No. 13 0> 2 g

Al-lacquer of D and C Yellow No. 5 2 g perfume —P.A .. & 100 g ✓ 8 5 0 0 2 7 f

Claims (5)

11 "CONCLUSIONS 1. A method of preparing a cosmetic lip-red composition by using at least one fat-soluble polymer with vinyl ester units. » at least one fatty substance and at least one non-toxic dye to be combined with each other, characterized in that at least 10% by weight of 1-behenoyloxy-3- (2-ethyl-hexoxy) -propanol is also used -2 using the formula -O-CI ^ C ^ H ^. 2. Process according to claim 1, characterized in that 10-30% by weight of 1-behenoyloxy-3- (2-ethylhexoxy) -propanol-2 is used. 3. Process for preparing an isopropanol derivative suitable for use in the process according to claim 1, characterized in that 1-behenoyloxy-3- (2-ethylhexoxy) -propanol-2 is prepared in a manner known per se. 4. Process according to claim 3, characterized in that behenic acid (»docosanoic acid) is reacted with 2-ethylhexyl-glycidyl ether for 2-8 hours at a temperature of about 130 ° C in the presence of a basic catalyst. j Method according to claim 4, characterized in that | That the basic catalyst used is sodium methanolate or ethanolate. *** 8500271