JPH08231340A - Cosmetic formulation - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a cosmetic preparation containing an alkyl and/or alkenyl oligoglucoside sulphate and a silicone compound and improved in foaming property and conditioning property. SOLUTION: This cosmetic preparation contains 0.5-25 wt.% alkyl and/or alkenyloligoglycoside sulphate and 0.01-10 wt.% silicone compound (e.g. dimethylpolysiloxane) as active ingredients and further contains 1-50 wt.% of a cationic polymer, a surfactant, a thickener, an emulsifier, superfat agent, a substance derived from organisms, a film-forming agent, a preservative, a pigment, a perfume, etc. The cosmetic preparation can be formulated in the form of skin care preparation such as cream or lotion, hair care preparation such as hair shampoo or hair lotion, foaming bathing agent, etc.

Description

Detailed Description of the Invention

[0001]

This invention relates to cosmetic formulations containing alkyl and / or alkenyl oligoglycoside sulphates and silicone compounds.

[0002]

Alkyl and / or alkenyl oligoglycoside sulphates, in particular alkyl oligoglucoside sulphates, are known sugar-based anionic surfactants and are highly effervescent, cleansing and skin-compatible.
However, in cosmetic preparations, especially hair care preparations, the alkyl oligoglucoside sulphate is not always satisfactory in effervescence. On the one hand, foaming
On the other hand, foam stability is not sufficient, especially in hard water.
It is also a problem that, after rinsing, amides often leave an undesired feel on the hair and also tend to have a detrimental effect on combing.

[0003]

The object of the present invention is to provide a cosmetic preparation containing alkyl and / or alkenyl oligoglycoside sulphates which does not have the disadvantages mentioned above.

[0004]

The present invention relates to cosmetic formulations containing (a) alkyl and / or alkenyl oligoglycoside sulphates and (b) silicone compounds. Surprisingly, it has been found that the foaming properties of alkyl and / or alkenyl oligoglycoside sulphates, especially alkyl oligoglucoside sulphates, are significantly improved by the addition of silicone compounds. According to the invention, the foam properties and hair conditioning properties are also improved at the same time.

Alkyl and / or alkenyl oligos
Glycoside sulphate alkyl and / or alkenyl oligoglycoside sulphates are known anionic sugar surfactants,
Formula (I):

Embedded image R ¹ O— [G] _p (I) [wherein, R ¹ is an alkyl and / or alkenyl group having 4 to 22 carbon atoms, and G is a sugar unit having 5 or 6 carbon atoms. Yes, p is a number from 1 to 10. ] And the alkyl and / or alkenyl oligoglycoside shown by these,
It is obtained by reacting with a sulfating agent and then neutralizing the reaction product with aqueous base.

To prepare alkyl and / or alkenyl oligoglycoside sulphates, the glycoside starting material is preferably dissolved in an inert solvent and then sulfur trioxide or a sulfur trioxide complex (eg SO ₃ / pyridine complex). React with. Such a method is, for example,
European Patent Application EP-A0186242 [Procter & Gamble] and E
P-A0363601 [Huels], as well as U.S. Patent US-PS 4609478 [Olin]. Instead of an inert solvent such as methylene chloride or dimethylformamide, a solvent that is not chemically inert such as a fatty alcohol may be used. In that case, not only the hydroxyl groups of the sugar but also the hydroxyl groups of the solvent are sulfated. Furthermore, it is also possible to obtain mixtures of sulfonates and sulphates by reaction of alkenyl glycosides with SO ₃ [German Patent Application DE-A 3918135 (Henke
l))].

The alkyl and / or alkenyl oligoglycoside sulphates can be derived from aldoses or ketoses (preferably glucose) having 5 or 6 carbon atoms. Preferred alkyl and / or alkenyl oligoglycoside sulphates are alkyl and / or alkenyl oligoglucoside sulphates.

The index p in formula (I) is the degree of oligomerization (DP
Degree), i.e. the distribution of mono- and oligoglucosides and is a number from 1 to 10. The p for individual compounds is always an integer, in particular it can be a value from 1 to 6, but the value p as an alkyl oligoglucoside sulphate is an analytically determined value and is usually not an integer. Preference is given to using alkyl and / or alkenyl oligoglycoside sulphates having an average degree of oligomerization p of 1.1 to 3.0. Alkyl and / or alkenyl oligoglycoside sulphates having a degree of oligomerization of less than 1.7, in particular 1.2 to 1.4, are preferred from the application point of view.

The alkyl or alkenyl radical R ¹ can be derived from primary alcohols having 4 to 11 carbon atoms, preferably 8 to 10 carbon atoms. Examples of such alcohols are butanol, capron alcohol, capryl alcohol, caprin alcohol and undecyl alcohol, and industrial mixtures thereof [for example by hydrogenating technical fatty acid methyl esters or by the use of rhylene (Ro
elen) is obtained by hydrogenating an aldehyde derived from the oxo synthesis]. Obtained as the first distillate in distillation of an industrial C _8-18 coconut oil fatty alcohol, the content of C ₁₂ alcohol as an impurity derived from possible alcohol less than 6 wt%, the chain length C ₈ -C ₁₀ Alkyl oligoglucoside sulfates (DP = 1 to 3), as well as alkyl oligoglucoside sulfates (DP = 1 to 3) derived from industrial C ₉ / C ₁₁ oxo alcohols are preferred.

Further, an alkyl or alkenyl group R
¹ may be derived from a primary alcohol having 12 to 22 carbon atoms, preferably 12 to 14 carbon atoms. Examples of such alcohols are lauryl alcohol, myristyl alcohol, cetyl alcohol, palmitoleyl alcohol,
Stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, aralkyl alcohol, gadreyl alcohol, behenyl alcohol, erucyl alcohol, and industrial mixtures thereof (obtained as above).
Is. Alkyl oligoglucoside sulphates with a DP of 1 to 3 derived from hydrogenated C ₁₂ / C ₁₄ coconut oil fatty alcohol are preferred.

The alkyl and / or alkenyl oligoglycoside sulphates can be used in the form of alkali metal and / or alkaline earth metal salts, ammonium, alkylammonium, alkanolammonium or glucanmonium salts. Preference is given to using sodium salts and / or magnesium salts.

Silicone Compounds Examples of suitable silicone compounds are given below. Formula (II):

Embedded image (CH ₃ ) ₃ SiO [(CH ₃ ) ₂ SiO] _n1 Si (CH ₃ ) ₃ (II) [wherein n1 is a number from 3 to 600]. ] The dimethyl polysiloxane shown by these.

(2) Formula (III):

Embedded image (CH ₃ ) ₃ SiO [(CH ₃ ) ₂ SiO] _a [(CH ₃ ) ₂ SiO] _b [(C ₆ H ₅ ) ₂ SiO] _c Si (CH ₃ ) ₃ (III) [formula Among them, the sum of (a + b + c) is 1 to 600, and at least two of a, b and c are not 0. ] The methylphenyl polysiloxane shown by these.

(3) Formula (IV):

Embedded image (R _d A _(3-d) ) Si [OSi (A) ₂ ] _p − [OSi (A _e R _(2-e) )] _q −OSi (R _d A _(3-d) ) (IV) [In the formula, R is hydrogen, a phenyl group, an OH group, or an alkyl group having 1 to 8 carbon atoms, d is 0 or a number of 1 to 3, e is 0 or 1, p is 0 or 1-1.
Is a number of 999, q is a number of 1-2, the sum of (p + q) is 1-2, A is a group C _f H _2f L, and f is 2-8.
And L is the formula (IVa) to (IVf):

Embedded image —NH—CH ₂ CH ₂ —N (R *) ₂ (IVa)

Embedded image —N (R *) ₂ (IVb)

Embedded image —OCH ₂ CH (OH) —CH ₂ —N (R *) ₂ (IVc)

Embedded image _{-OCH 2 CH (OH) -CH 2} -N + (R *) 3 B - (IVd)

[Of 10] _{^{-N + (R *) 3 B}} - (IVe)

Embedded image —N—CH ₂ CH ₂ —N ⁺ (R *) ₃ B ^— (IVf) (In the formulas IVa to IVf, R * is hydrogen, phenyl, benzyl, and / or alkyl having 1 to 20 carbon atoms. And B ^- is a group represented by any of the following ^: Fluoride, chloride or iodide. ] The amino modified silicone shown by these.

Equation (4) (V):

[Chemical 12] [In the formula, R′CO is an acyl group having 6 to 22 carbon atoms, g, h and i are each a number of 1 to 350, and j is 0 or a number of 1 to 10. ] The fatty acid modified silicone shown by.

(5) Formulas (VIa) and (VIb):

[Chemical 13]

Embedded image [Wherein, k and l are each 1 to 500, preferably 1
To 200, and B is an alkylene group having 1 to 4 carbon atoms, which optionally has a hydroxy substituent. ]
Alcohol-modified silicone represented by.

Equation (6) (VII):

[Chemical 15] [Wherein R "is an alkyl group having 6 to 22 carbon atoms, m1, m2 and m3 are numbers from 1 to 300, and m4 is 0 or a number from 4 to 22]. Alcohol-modified silicone.

Formula (7) (VIIIa)

Embedded image [In the formula, Ra represents an alkyl group having 1 to 6 carbon atoms, and P
O is a group OCH ₂ CH (CH ₃ ), EO is a group OCH ₂ C
H ₂ and p 1 and p 2 are each 0 or 1 to 50
And p3 is 0 or a number from 1 to 400. ] And / or formula (VIIIb):

[Chemical 17] [Wherein q1 is a number of 2 to 100, preferably 20 to 80, q2 is a number of 1 to 50, preferably 3 to 30, EO is a group OCH ₂ CH ₂ and PO is a group OCH. ₂ C
H (CH ₃ ), q3 and q4 are 0 or 1 to 50,
It is preferably a number of 5 to 25, and ^Ra is a carbon atom number of 1 to
6 is an alkyl group. ] The polyether modified silicone shown by these.

Equation (8) (IX):

Embedded image [In the formula, r1 is a number of 1 to 500, preferably 1 to 250, r2 is a number of 1 to 50, preferably 1 to 30, and D is an alkylene group having 1 to 3 carbon atoms. ] The epoxy modified silicone shown by these.

Expression (X):

[Chemical 19] [In the formula, s1 is a number of 1 to 400, preferably 1 to 250. ] Fluorine modified silicone shown by.

Expression (XI):

Embedded image [In the formula, Rb is an alkyl group having 1 to 3 carbon atoms, and t
1 is a number from 3 to 8. ] The cyclic silicone shown by these.

Formula (11) (XIIa):

[Chemical 21] [Wherein R ^c is an alkyl group having 2 to 18 carbon atoms,
E is an alkylene group having 1 to 4 carbon atoms, and u1 and u2 are each 1 to 500, preferably 1 to 200. ] And / or formula (XIIb):

[Chemical formula 22] [In the formula, R ^d is an alkyl group having 10 to 16 carbon atoms, and v 1 and v 2 are each 1 to 500, preferably 1
~ 200. ] The alkyl modified silicone shown by these.

With regard to the desired properties of the surface-active preparation, it is particularly advantageous to combine the surfactant with a particular silicone compound. For example, methyl polysiloxane (1),
Methylphenyl polysiloxane (2), amino modified silicone (3), polyether modified silicone (7), and / or
Alternatively, particularly fine creamy foams are obtained with cyclic silicones (10).

In the present invention, the silicone compound is 1
Also specifically included are surface active silicone compounds having a structure derived from polydimethylsiloxane in which one or more methyl groups are replaced with hydrophilic nonionic or ionic groups. An overview of suitable materials is given, for example, by B. Gruening and G. Kellner.
oerner), Tens Surf Deto (Tens. Surf. De)
t. ), 26, 312 (1989); P. Hamyer
(P. Hameyer) and T. Gould,
Manufact Chem., 20,
January 1990; and B. Gruening and H. Leidreiter, Seiffen-
Eile-Fette-Vakuze (Seifen-Oele-Fette
Wachse), 118, 117 (1992). The detergent mixture of the present invention comprises the silicone compound in an amount of 0.01 to 10% by weight, preferably 0.1 to 5% by weight, more preferably 0.5 to 2.5% by weight, based on the solid content of the mixture. Can be included.

Cosmetic formulation The cosmetic formulation of the present invention is preferably a skin care formulation and a hair care formulation. The formulations of the present invention may contain minor amounts of additional surfactants that are compatible with the other ingredients. Examples of such surfactants are fatty alcohol polyglycol ether sulphates, monoglyceride sulphates, ether carboxylic acids, mono- and / or dialkyl sulphosuccinates, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, alkyls and / or It is an alkenyl oligoglucoside, a fatty acid-N-alkylglucamide, an alkylamidobetaine, and / or a protein hydrolyzate, or a condensate of a protein and a fatty acid (of animal or preferably plant origin).

Skin care formulations, such as creams, lotions and the like, are usually in addition to the above-mentioned surfactants, oils, emulsifiers, fats and waxes, stabilizers, fats, thickeners, substances of biological origin, film formers, preservatives. Contains agents, pigments and fragrances. Hair care formulations, such as hair shampoos, hair lotions, effervescent bath agents and the like, in addition to the surfactant,
Emulsifiers, superfatting agents, thickeners, biogenic substances, film formers, preservatives, dyes and fragrances can be contained as further auxiliaries and additives.

Suitable oils are, for example, Guerbet alcohols consisting of C _6-18 , preferably C _8-10 fatty alcohols, esters of linear C _6-20 fatty acids with linear C _6-20 fatty alcohols, Ester of branched C _6-13 carboxylic acid and linear C _16-18 fatty alcohol, ester of linear C _10-18 fatty acid and branched alcohol (particularly 2-ethylhexanol), linear And / or esters of branched fatty acids with dihydric alcohols and / or Guerbet alcohols, C
_6-10 fatty acid triglycerides, vegetable oils, branched primary alcohols, substituted cyclohexanes, gelbe carbonates,
And / or dialkyl ether.

Suitable emulsifiers are the known w / o and o / w emulsifiers, such as hydrogenated and ethoxylated castor oil, glycerol fatty acid esters, or polyglycerol polyricinolates. An example of fat is glyceride. Suitable waxes are inter alia beeswax, paraffin wax or microwax, optionally in combination with a hydrophilic wax (eg cetostearyl alcohol).

Suitable stabilizers are metal salts of fatty acids, for example magnesium, aluminum and / or zinc salts of stearic acid. Superfatting agents may be selected from substances such as, for example, polyethoxylated lanolin derivatives, lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides. The fatty acid alkanolamides also act as foam stabilizers.

Suitable thickeners are, for example, polysaccharides, especially xanthan gum, guar, agar, alginates, methylcellulose, carboxymethylcellulose and hydroxyethylcellulose, relatively high molecular weight fatty acid polyethylene glycol monoesters and diesters, polyacrylates, polyvinyl alcohols and Polyvinylpyrrolidone, surfactants (eg narrow range fatty alcohol ethoxylates or alkyl oligoglucosides), and electrolytes (eg sodium chloride and ammonium chloride). The biological substance is, for example, a plant extract and a vitamin complex. Film formers are typically, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone / vinyl acetate copolymers, acrylic acid-based polymers, quaternary cellulose derivatives, and similar compounds.

Suitable cationic polymers are, for example, cationic cellulose derivatives, cationic starches, diallylammonium salts / acrylamide copolymers, quaternized polyvinylpyrrolidone derivatives, quaternized vinylpyrrolidone / vinylimidazole polymers, polyglycols / Amine condensation products, quaternized collagen polypeptides, polyethyleneimines, cationic silicone polymers, adipic acid / dimethylaminohydroxypropyldiethylenetriamine copolymers, polyaminopolyamides, cationic chitin derivatives, cationic guar gum and / or quaternized ammonium It is a salt polymer.
Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid. Suitable pearlescent agents are, for example, glycol distearates such as ethylene glycol distearate, and fatty acid monoglycol esters.

The dye is, for example, "Kosmetische Faerbemittel", Farbstoffkommission Shaft (Farbstoffkommission).
der Deutschen Forschungsgemeinschaft), Verlag Chemie, Weinheim, 1984, pp. 81-106 and may be selected from cosmetically suitable and approved substances. Dye is typically 0.001 based on the total mixture
Used at a concentration of ~ 0.1% by weight.

The total amount of auxiliaries and additives may be 1 to 50% by weight, preferably 5 to 40% by weight, based on the formulation,
The content of non-aqueous component (“active substance”) is 20 to 8 based on the formulation.
It is 0% by weight, preferably 30 to 70% by weight. The formulations may be prepared in a known manner, for example by hot, cold, hot-hot / cold or PIT emulsification. This preparation is merely mechanical and involves no chemical reactions.

[0034]

Industrial Application Mixtures of alkyl and / or alkenyl oligoglycoside sulphates with silicone compounds are mild and have improved foaming and hair conditioning properties. Thus, such inventive mixtures are suitable for the production of cosmetic formulations, especially hair care formulations, such as shampoos, rinses and tonics.

[0035]

【Example】

Ia. Using the surfactant A1) C ₁₂ / C ₁₆ coconut oil alkyl oligoglucoside sulfates · Na salt (DP = 1.5) A2) C 8 / C 16 alkyl oligoglucoside sulfates · Mg salt (DP = 1.3 ) B1) C ₁₂ / C ₁₄ coconut oil alcohol 3.6EO (ethylene oxide) sulfate · Na salt B2) C ₈ / C ₁₀ alkylpolyglucoside (DP = 1.5) B3) soy protein coconut oil fatty acid condensates B4) coconut Betaine derived from oil fatty acid

Ib. Silicone compound used S1) Dimethylpolysiloxane [Th.Goldschmidt AG] S2) Methylphenylpolysiloxane (KF56, Shin-Etsu Chemical Co., Ltd.) S3) Amino-modified siloxane (SF8517, Toray) S4) Aminoalkylpolysiloxane Siloxane (SM8702,
Toray)

Ic. Additive Z1) 2-octyldodecanol Z2) Dioctylcyclohexane Z3) Almond oil Z4) Di-n-octyl ether Z5) Cetyl / stearyl (50:50) alcohol

II. Preparations Preparations F1 to F4 are the preparations of the present invention, and preparations F5 to F8
Is a comparative formulation. The composition of the formulation is shown in Table 1. The numerical values in Table 1 are% by weight. Formulation is 100% by weight with water added
And

[Table 1]

III. Effervescence The effervescence of the formulations in hard water (16 ° d) was measured at 23 ° C according to DIN 53902 / Part 2. Foaming, foam volume after 5 minutes, foam quality, and when the formulation was used as a shampoo, the feel of the hair after rinsing was evaluated. Table 2 shows the results.

[0040]

[Table 2] Legend: BF = foaming FC = collapse of foam (volume of foam after 5 minutes) FP = quality of foam (++: rich creamy foam; +: coarse foam) HF = feel of hair after rinsing ( ++: Smooth and good combing; ++: Poor feel, but good combing; +:
(Both feel and combing are bad)

IV. Dry and wet combing test a) Dry combing Dry combing with charging was tested. Relative humidity was 20%. The adjustment time was 12 hours at 30 ° C. One comb
After passing through 0 times, the measurement was performed with the charge tap of the double Faraday box. The measurement error averaged 2.5% and the statistical certainty was at least 99.9%. The results of this combing test are shown in Table 3. b) Wet combing Wet combing of brown hair [Alkinco # 6634, hair length 12 cm, hair weight 1 g] was tested. After zero measurement, the hair tresses were dipped in the preparations F1 to F8 (100 ml). 5
After the contact time of 1 minute, the hair tresses are rinsed with running water (1 l / min, 38 ° C)
Rinse for a minute. The hair tresses were remeasured and compared to zero measurements. The measurement error averaged 2% and the statistical certainty was at least 99%. The results are also shown in Table 3.

[0042]

[Table 3]

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI Technical indication location A61K 7/08 A61K 7/08 (72) Inventor Jörg Kale 40789 Monheim, Grazer, Germany Strasse 48 (72) Inventor Bernd Fabry 41352 Korschenbroich, Danziger Strasse 31

Claims (7)

[Claims] 1. A cosmetic preparation containing (a) an alkyl and / or alkenyl oligoglycoside sulfate and (b) a silicone compound. 2. Formula (I): embedded image R ¹ O— [G] _p (I) [wherein R ¹ is an alkyl and / or alkenyl group having 4 to 22 carbon atoms, and G is It is a sugar unit having 5 or 6 carbon atoms, and p is a number from 1 to 10. ] And the alkyl and / or alkenyl oligoglycoside shown by these,
The cosmetic preparation according to claim 1, which contains an alkyl and / or alkenyl oligoglycoside sulfate obtained by reacting with a sulfating agent and then neutralizing with an aqueous base. 3. The cosmetic preparation according to claim 1, which contains an alkyl oligoglucoside sulfate as the alkyl and / or alkenyl oligoglycoside sulfate. 4. Alkyl and / or alkenyl oligoglycoside sulphate in an amount of 0.5-2 based on the formulation.
The cosmetic preparation according to claim 1 or 2, which is contained in an amount of 5% by weight. 5. Dimethylpolysiloxane, methylphenylpolysiloxane, amino-modified silicone, fatty acid-modified silicone, alcohol-modified silicone, fatty acid / alcohol-modified silicone, polyether-modified silicone,
5. A silicone compound selected from the group consisting of epoxy modified silicone, fluorine modified silicone, cyclic silicone, and alkyl modified silicone.
The cosmetic preparation according to any one of 1. 6. The cosmetic preparation according to claim 1, which contains the silicone compound in an amount of 0.01 to 10% by weight. 7. The cosmetic preparation according to claim 1, further comprising a cationic polymer.