RU2810339C2 - Deposition system for hair - Google Patents

Abstract

FIELD: hair care.

SUBSTANCE: hair care composition contains the following: a) a conditioning base containing a cationic conditioning surfactant containing from 16 to 32 carbon atoms; a fatty alcohol containing from 8 to 22 carbon atoms; b) from 0.1 to 10 wt.% of conditioning silicone; (c) from 0.1 to 5 wt.% of a quaternary ammonium diester which is bis(isostearoyl/oleoylisopropyl) dimonium methosulfate, the weight ratio of b) to c) being from 1:1 to 1:0.1. Also the following is disclosed: a hair care method and the use of a quaternary ammonium diester to deposit silicone onto the hair.

EFFECT: group of inventions provides improved deposition of silicone onto hair.

6 cl, 2 tbl, 2 ex

Description

Field of technology to which the invention relates

The present invention relates to hair care compositions containing a quaternary ammonium diester and the use of these compositions to deposit silicone on hair surfaces.

Prior Art

US 2016081907 (Evonik) discloses hair compositions containing liquid quaternary ammonium esters and/or imidazolinium salts that are stable over a long period of time due to the addition of carbomers or other polymers. US 2016083333 discloses cosmetic compositions containing mixed quaternary esters of quaternary ammonium compounds for the cosmetic treatment of keratin fibers.

DE 102015223028 (Henkel) discloses a cosmetic composition for treating keratin fibers, containing in a cosmetic carrier a) at least one said quaternary ammonium ester in an amount of 0.01-20.0% by weight based on the weight of the total composition, and b ) at least an additional, different from a) cationic and/or cationizable compound in an amount of 0.01-20.0 wt.%.

The combination of certain quaternary ammonium esters with a silicone-containing hair care base has been found to provide improved deposition of silicone onto the hair.

The essence of the invention

In a first aspect, the present invention provides a hair care composition comprising:

a) conditioning base containing:

i) a cationic conditioning surfactant containing from 16 to 32 carbon atoms;

ii) a fatty alcohol containing from 8 to 22 carbon atoms; And

b) from 0.1 to 10 wt.% conditioning silicone;

the composition additionally contains:

(c) from 0.1 to 5% by weight of a quaternary ammonium diester selected from a quaternary ammonium diester that contains branched, saturated chains, a quaternary ammonium diester that contains straight, unsaturated chains, and mixtures thereof;

and where the mass ratio of b) to c) is from 1:1 to 1:0.1.

In a second aspect, the invention provides a method of hair care, comprising the step of applying to the hair a composition according to the first aspect of the invention.

In a third aspect, the invention provides the use of a quaternary ammonium diester selected from a quaternary ammonium diester that contains branched, saturated chains, a quaternary ammonium diester that contains straight, unsaturated chains, and mixtures thereof for deposition of silicone onto hair.

General Description of the Invention

Cationic conditioning surfactant

Conditioner compositions contain a cationic conditioning surfactant that is cosmetically acceptable and suitable for topical application to the hair.

Preferably, the cationic conditioning surfactants have the formula N ⁺ (R ¹ )(R ² )(R ³ )(R ⁴ ), wherein R ¹ , R ² , R ³ and R ⁴ are independently (C ₁ -C ₃₀ ) alkyl or benzyl.

Preferably, one, two or three of R ¹ , R ² , R ³ and R ⁴ are independently (C ₄ -C ₃₀ ) alkyl and the other group or groups R ¹ , R ² , R ³ and R ⁴ are ( C ₁ -C ₆ ) alkyl or benzyl.

More preferably, one or two of R ¹ , R ² , R ³ and R ⁴ are independently (C ₆ -C ₃₀ ) alkyl and the other groups R ¹ , R ² , R ³ and R ⁴ are (C ₁ - C ₆ ) alkyl or benzyl groups. Optionally, alkyl groups may contain one or more ester (-OCO- or -COO-) and/or ether (-O-) linkages within the alkyl chain. Alkyl groups may optionally be replaced by one or more hydroxyl groups. Alkyl groups can be straight or branched, and for alkyl groups containing 3 or more carbon atoms, cyclic. Alkyl groups may be saturated or may contain one or more carbon-carbon double bonds (eg oleyl). Alkyl groups are optionally ethoxylated on the alkyl chain by one or more ethyleneoxy groups.

Suitable cationic conditioning surfactants for use in conditioner compositions in accordance with the present invention include cetyltrimethylammonium chloride (CTAC), behenyltrimethylammonium chloride (BTAC), behenyltrimethylammonium methosulfate (BTMS), cetylpyridinium chloride, tetramethylammonium chloride, tetraethylammonium chloride, octyltrimethylammonium chloride, dodecyltrimethylammonium chloride , hexadecyltrimethylammonium chloride, octyldimethylbenzylammonium chloride, decyldimethylbenzylammonium chloride, stearyldimethylbenzylammonium chloride, didodecyldimethylammonium chloride, dioctadecyldimethylammonium chloride, tallothrimethylammonium chloride, dihydrogenated thallodymethylammonium chloride (for example, Arquad 2HT/75 from Akzo Nobel), coco trimethylammonium chloride, PEG-2-oleammonium chloride and their corresponding hydroxides . Additional suitable cationic surfactants include those materials designated Quaternium-5, Quaternium-31 and Quaternium-18 by the CTFA. Mixtures of any of the above materials may also be suitable. A particularly useful cationic surfactant for use in conditioners according to the invention is cetyltrimethylammonium chloride, commercially available, for example, as GENAMIN CTAC from Hoechst Celanese. Another particularly useful cationic surfactant for use in the conditioners of the invention is behenyl trimethyl ammonium chloride, commercially available, for example, as GENAMIN KDMP from Clariant. Preferably, the cationic surfactant is selected from cetyltrimethylammonium chloride and behenyltrimethylammonium chloride, most preferably behenyltrimethylammonium chloride.

Another example of a class of suitable cationic surfactants for use in the invention, alone or together with one or more other cationic surfactants, is the following combination of (i) and (ii):

(i) amidoamine corresponding to the general formula (II):

R ¹ CONH(CH ₂ )mN(R ² )R ³ , (II)

in which R ¹ represents a non-cyclic hydrocarbon chain of varying degrees of saturation (hydrocarbyl chain) having 10 or more carbon atoms, R ² and R ³ are independently selected from non-cyclic hydrocarbon chains of varying degrees of saturation (hydrocarbyl chains) having from 1 to 10 carbon atoms , and m is an integer from 1 to about 10; And

(ii) acid.

As used herein, the term “non-cyclic hydrocarbon chain of varying degrees of saturation” (hydrocarbyl chain) means an alkyl or alkenyl chain.

Preferred amidoamine compounds are those corresponding to formula (I), in which

R ¹ is a non-cyclic hydrocarbon residue of varying degrees of saturation, preferably a residue having from about 11 to about 24 carbon atoms,

R ² and R ³ are each independently non-cyclic hydrocarbon moieties of varying degrees of saturation, preferably alkyl groups having from 1 to about 4 carbon atoms, and m is an integer from 1 to about 4.

Preferably R ² and R ³ represent methyl or ethyl groups.

Preferably m is 2 or 3, i.e. ethylene or propylene group.

Preferred amidoamines used herein include stearamido-propyldimethylamine, stearamidopropyldiethylamine, stearamidoethyldiethylamine, stearamidoethyldimethylamine, palmitamidopropyldimethylamine, palmitamidopropyldiethylamine, palmitamidoethyldiethylamine, palmitamidoethyldimethylamine, behenamidopropyldimethylamine, behen amidopropyldiethylamine, behenamidoethyldiethylamine, behenamidoethyldimethylamine, arachidamidopropyldimethylamine, arachidamidopropyldiethylamine, arachidamidoethyldiethylamine, arachidamidoethyldimethylamine and mixtures thereof. Particularly preferred amidoamines as used herein are stearamidopropyldimethylamine, stearamidoethyldiethylamine, and mixtures thereof.

Commercially available amidoamines useful herein are: stearamidopropyldimethylamine under the trade names LEXAMINE S-13, which can be obtained from Inolex (Philadelphia Pennsylvania, USA) and AMIDOAMINE MSP, which can be obtained from Nikko (Tokyo, Japan), stearamidoethyldiethylamine under brand AMIDOAMINE S, available from Nikko, behenamidopropyldimethylamine, brand INCROMINE BB, available from Croda (North Humberside, England), and various amidoamines available from SCHERCODINE series, available from Scher (Clifton New Jersey, USA).

The acid may be any organic or mineral acid that is capable of protonating the amidoamine in the conditioner composition. Suitable acids used herein include hydrochloric acid, acetic acid, tartaric acid, fumaric acid, lactic acid, malic acid, succinic acid, and mixtures thereof. Preferably, the acid is selected from the group consisting of acetic acid, tartaric acid, hydrochloric acid, fumaric acid, lactic acid and mixtures thereof.

The primary role of the acid is to protonate the amidoamine in the hair care composition, thereby forming a tertiary amine salt (TAS) in situ in the hair care composition. TAS is essentially an unstable cationic surfactant containing quaternary ammonium or pseudo-quaternary ammonium.

Accordingly, the acid is present in an amount sufficient to protonate more than 95 mol% (293 K) of the amidoamine present. In conditioners for use in the invention, the level of cationic conditioning surfactant will typically range from 0.01 to 10%, more preferably from 0.05 to 7.5%, most preferably from 0.1 to 5 % of the total weight of the cationic conditioning surfactant, based on the total weight of the composition.

Fatty alcohol

The compositions of the present invention contain a fatty alcohol having a carbon-carbon chain length from C ₈ to C ₂₂ .

The combined use of fatty alcohols and cationic surfactants in conditioning compositions is preferred because it results in the formation of a lamellar phase in which the cationic surfactant is dispersed.

The fatty alcohol contains from 8 to 22 carbon atoms, preferably from 16 to 22, most preferably from C16 to C18. Fatty alcohols are generally compounds containing straight chain alkyl groups. Preferably the alkyl groups are saturated. Examples of preferred fatty alcohols are cetyl alcohol, stearyl alcohol, and mixtures thereof. The use of these substances also has the advantage that they contribute to the overall conditioning properties of the compositions to be used in the invention.

The level of fatty alcohol in conditioners for use in the invention is typically from 0.01 to 10%, preferably from 0.1 to 8%, more preferably from 0.2 to 7%, most preferably from 0.3 to 6 % by weight of the composition.

The weight ratio of cationic surfactant to fatty alcohol is from 1:1 to 1:10, preferably from 1:1.5 to 1:8, optimally from 1:2 to 1:5. If the weight ratio of cationic surfactant to fatty alcohol is too high, eye irritation from the composition may result. If it is too low, then this makes the hair, according to some buyers, squeaky to the touch.

Silicone

The compositions of the invention may contain emulsified droplets of a silicone conditioning agent to improve conditioning properties. Suitable silicones include polydiorganosiloxanes, in particular polydimethylsiloxanes, which are designated CTFA dimethicone. Also suitable for use in the compositions of the invention (particularly shampoos and conditioners) are hydroxyl-terminated polydimethylsiloxanes, which are designated CTFA dimethiconol. Also suitable for use in the compositions of the invention are silicone gums having a low degree of cross-linking, as described, for example, in WO 96/31188. Preferably, the silicone is selected from the group consisting of dimethicone, dimethiconol, amodimethicone and mixtures thereof. Also preferred are mixtures of amino-functionalized silicones with dimethicones.

The viscosity of the emulsified silicone itself (not the emulsion or final hair conditioning composition) is typically at least 10,000 cSt at 25°C, the viscosity of the silicone itself is preferably at least 60,000 cSt, most preferably at least 500,000 cSt, ideally at least 1000000 cst. Preferably the viscosity does not exceed 10 ⁹ cSt for ease of formulation.

Emulsified silicones for use in the shampoo compositions of the invention typically have a droplet size D90 of the silicone in the composition that is less than 30, preferably less than 20, more preferably less than 10 microns, ideally 0.01 to 1 micron. Silicone emulsions having an average droplet size (D50) of silicone of 0.15 microns are generally called microemulsions.

Silicone particle size can be measured using a laser light scattering technique, such as the 2600D Particle Sizer from Malvern Instruments. Examples of suitable preformulated emulsions include Xiameter MEM 1785 and microemulsion DC2-1865, which are available from Dow Corning. These are emulsions/microemulsions of dimethiconol. Crosslinked silicone gums are also available in pre-emulsified form, which is advantageous due to ease of formulation.

Another preferred class of silicones for inclusion in the shampoos and conditioners of the invention are amino functional silicones. By "amino-functional silicone" is meant a silicone containing at least one primary, secondary or tertiary amino group, or quaternary ammonium group. Examples of suitable amino-functional silicones include: polysiloxanes having the CTFA designation "amodimethicone". A preferred amodimethicone is commercially available from Dow Corning as DC 7134. Specific examples of amino functional silicones suitable for use in the invention include the amino silicone oils DC2-8220, DC2-8166 and DC2-8566 (all from Dow Corning).

Suitable quaternary silicone polymers are described in EP-A-0530974. The preferred quaternary silicone polymer is K3474 from Goldschmidt.

Also suitable are emulsions of amino-functional silicone oils with a nonionic and/or cationic surfactant.

Preformulated amino-functional silicone emulsions are also available from silicone oil suppliers such as Dow Corning and General Electric. Specific examples include cationic emulsion DC939 and nonionic emulsions DC2-7224, DC2-8467, DC2-8177 and DC2-8154 (all from Dow Corning).

The total amount of silicone is preferably from 0.1 wt% to 10 wt% of the total composition, more preferably from 0.1 wt% to 5 wt%, most preferably a suitable level is 0.5-3 wt%. .

Quaternary ammonium diester

As ingredient iv), the compositions of the invention contain at least one quaternary ammonium ester selected from a quaternary ammonium diester which contains branched, saturated chains, a quaternary ammonium diester which contains straight, unsaturated chains, and mixtures thereof .

The quaternary ammonium diester has a carbon chain length of C16-C18.

Preferably, the quaternary ammonium diester is selected from bis-isostearoylisopropyldimonium methosulfate, bisoleoylisopropyldimonium methosulfate, and mixtures thereof.

The most preferred compound is called bis(isostearoyl/oleoylisopropyl)dimonium methosulfate and is referred to in INCI nomenclature as Quaternium-98; it is a mixture of bis-isostearoylisopropyldimonium methosulfate and bis-oleoylisopropyldimonium methosulfate, and is commercially available under the trade name Varisoft® EQ 100 from Evonik.

Quaternary ammonium diesters are present in the compositions of the invention in amounts of 0.1 to 5 wt.%, preferably 0.1-2, more preferably 0.5-1.5, even more preferably 0.5-1.2, most preferably 0.6-1 wt.% based on the total weight of the composition.

The weight ratio of silicone (b) to diester of quaternary ammonium compound (c) is from 1:1 to 1:0.1, preferably from 1:0.2 to 1:0.4, most preferably from 1:0.25 to 1:0.4.

Additional Ingredients

The composition in accordance with the invention may contain any of a number of ingredients that are common to conditioning compositions.

Other ingredients may include viscosity modifiers, preservatives, coloring agents, polyols such as glycerin and polypropylene glycol, chelating agents such as EDTA, antioxidants such as vitamin E acetate, fragrances, antimicrobials and sunscreens. Each of these ingredients will be present in an amount effective to achieve its purpose. Typically, these optional ingredients are included individually at levels up to about 5% by weight of the total composition.

Preferably, the compositions of the present invention also contain adjuvants suitable for hair care. Typically, such ingredients are individually included at a level of up to 2%, preferably up to 1%, by weight of the total composition.

Suitable hair care adjuvants include:

(i) natural nutrients for hair roots such as amino acids and sugars. Examples of suitable amino acids include arginine, cysteine, glutamine, glutamic acid, isoleucine, leucine, methionine, serine and valine and/or their precursors and derivatives. Amino acids can be added individually, in mixtures or in the form of peptides, such as di- and tripeptides. Amino acids can also be added in the form of a protein hydrolysate, such as keratin or collagen hydrolysate. Suitable sugars are glucose, dextrose and fructose. They can be added individually or in the form of, for example, fruit extracts.

(ii) agents beneficial to hair fibers. Examples are:

- ceramides to moisturize the fiber and maintain the integrity of the cuticle. Ceramides are obtained by extraction from natural sources or as synthetic ceramides and pseudoceramides. The preferred ceramide is Ceramide II from Quest. Ceramide mixtures such as Ceramides LS from Laboratoires Serobiologiques may also be suitable.

- free fatty acids to restore the cuticle and prevent damage. Examples are branched chain fatty acids such as 18-methylleucosanic acid and other homologs of this series, straight chain fatty acids such as stearic, myristic and palmitic acids, and unsaturated fatty acids such as oleic acid, linoleic acid, linolenic acid and arachidonic acid. The preferred fatty acid is oleic acid. Fatty acids can be added individually, as mixtures, or as mixtures derived from extracts, such as lanolin.

Mixtures of any of the above active ingredients may also be used.

In a second aspect, a method of making a conditioning composition in accordance with the first aspect is provided. The method includes forming a conditioning gel phase that contains a cationic surfactant and a fatty substance, and separately forming a solution of a hydrophobically modified polymer, optionally with a cationic surfactant, which, if present, is first added to water.

The two mixtures are then added to each other before adding the remaining ingredients to form the conditioning composition.

Preferably, additional ingredients include flavoring agents, thickening agents and preservatives.

The invention will now be illustrated by the following non-limiting examples:

Examples

The invention will now be illustrated by the following non-limiting examples:

Example 1: Hair Care Compositions Prior to Silicone Deposition Analysis

Three hair conditioner formulations were used to condition the hair before silicone deposition analysis. Composition B corresponds to the present invention, while compositions A and C are comparative compositions. The compositions are shown in Table 1.

Table 1. Compositions of air conditioners A, B and C

Ingredient Active substance content A B C Bis(isostearoyl/oleoylisopropyl) dimonium methosulfate (Varisoft EQ100) 100 0 0.8 0 Distearoylethyl dimonium chloride (Varisoft EQ65) 65 0 0 1.23 Behentrimonium chloride 70 2.29 1.14 1.14 Cetearyl alcohol 100 3.2 3.2 3.2 Dimethicone 600K and amodimethicone 2000 nm 70 3.57 3.57 3.57 Fragrance 100 0.6 0.6 0.6 Preservatives 100 0.5 0.5 0.5 Water 100 up to 100 up to 100 up to 100

The formulations were prepared by adding cationic surfactants to the fatty alcohol and stirring at 85°C. Gradually this mixture was added to water, usually at 55°C so that the temperature of the mixture was 60°C. This temperature was maintained for 30 minutes with stirring. The mixture was then cooled to ambient temperature by adding more water and other ambient temperature ingredients and using external cooling if necessary, and mixed.

Example 2 Treatment of hair with compositions A, B and C, and silicone deposition measurements according to the invention

The hair used was dark brown European hair in strands weighing 5 g and 6 inches long.

The hair was treated with compositions A, B and C as follows:

First, the hair was treated with a clarifying shampoo using the following method:

The hair fibers were kept under running water for 30 seconds, shampoo was applied at the rate of 0.1 ml of shampoo per 1 g of hair and rubbed into the hair for 30 seconds. Excess foam was removed by holding under running water for 30 seconds and the hair shampooing step was repeated. Hair was rinsed under running water for 30 seconds.

Wet hair was then treated with conditioner A or B or C using the following method:

The conditioner was applied to damp hair at the rate of 0.2 g of conditioner per 1 g of hair and rubbed into the hair for 1 minute. The hair was rinsed under running water for 1 minute and excess water was removed. The hair was dried overnight at room temperature.

For each conditioner, 5 replicate hair strands were prepared. The hair was then trimmed and secured to 40mm plastic rings, silicone deposition onto the hair was measured by Intertec Manchester using an X-ray fluorescence spectrometer (XRF) and calibrated using appropriate standards.

Silicone deposition measured on hair strands treated with conditioners A, B and C is shown in Table 2.

Table 2. Silicone deposition data for hair treated with conditioners A, B and C

Air conditioner Average silicone deposition (ppm) Standard deviation A 2154.96 202.93 B 5506.87 373.54 C 3293.09 689.37

Silicone deposition can be seen for hair treated with conditioners A, B and C. Conditioner B has higher silicone deposition which is associated with the quaternary ammonium diester (Varisoft EQ100) in the formulation of the invention. Conditioners A and C do not deposit as much silicone.

Claims (12)

1. A hair care composition containing: a) conditioning base containing: i) a cationic conditioning surfactant containing from 16 to 32 carbon atoms; ii) a fatty alcohol containing from 8 to 22 carbon atoms; And b) from 0.1 to 10 wt.% conditioning silicone; characterized in that the composition additionally contains: (c) from 0.1 to 5% by weight of a quaternary ammonium diester which is bis(isostearoyl/oleoylisopropyl) dimonium methosulfate, wherein the mass ratio of b) to c) is from 1:1 to 1:0.1. 2. Composition according to claim 1, where the ratio of b) to c) is from 1:0.25 to 1:0.4. 3. The composition according to any one of the preceding claims, wherein the diester of the quaternary ammonium compound is present in an amount of from 0.5 to 1.2 wt.% based on the total weight of the composition. 4. The composition according to any of the preceding claims, wherein the silicone is selected from the group consisting of dimethicone, dimethiconol, amodimethicone and mixtures thereof. 5. A method of hair care, including the stage of applying a composition according to any one of claims to the hair. 1-4. 6. The use of a diester of a quaternary ammonium compound, which is bis(isostearoyl/oleoylisopropyl) dimonium methosulfate, in the composition according to any one of paragraphs. 1-4 to deposit silicone on the hair.