WO2013188942A2

WO2013188942A2 - Cleansing compositions

Info

Publication number: WO2013188942A2
Application number: PCT/BR2013/000225
Authority: WO
Inventors: Alvaro Luis GOMES; Gustavo Vandromel RODRIGUES
Original assignee: Dow Corning Do Brasil Limitada
Priority date: 2012-06-21
Filing date: 2013-06-21
Publication date: 2013-12-27
Also published as: WO2013188942A3; BR102012017200A2

Abstract

The invention relates to skin and hair cleansing compositions comprising an organopolysiloxane film former (A), a cooling agent (B) and a cleansing agent (C).

Description

CLEANSING COMPOSITIONS

CROSS-REFERENCE TO RELATED APPLICATIONS

None .

BACKGROUND OF THE INVENTION

Disclosed herein are skin and hair cleansing compositions comprising

(A) an organopolysiloxane film former

(B) a cooling agent and

(C) a cleansing agent.

Skin and hair cleansing compositions are usually used to cleanse. Additional benefits may however be conferred by the compositions such as moisturizing, conditioning, smoothing, exfoliating, depending on the ingredients present in the compositions in addition to the cleansing base .

Organopolysiloxanes are used in skin and hair cleansing compositions to confer a variety of benefits, such as improving foam lathering, improving feel of skin and hair, or improving detangling of hair. Cooling agents are used in cleansing compositions to impart a cooling sensation to the user upon cleansing.

In certain geographies where weather is humid and hot, the effect of cleansing skin and hair may be quickly worn off by the temperature and humidity.

It is an object of the invention to prolong the clean sensation by providing for a skin and hair composition comprising an organopolysiloxane film former and a cooling agent .

BRIEF SUMMARY OF THE INVENTION

Disclosed herein are skin and hair cleansing compositions comprising (A) an organopolysiloxane film former

(B) a cooling agent and

(C) a cleansing agent.

Also disclosed is a soap bar composition comprising an organopolysiloxane film former (A) , a cooling agent (B) and a cleansing agent (C) .

Further disclosed is a method to cleanse skin and hair comprising applying to it the skin and hair cleansing composition .

DETAILED DESCRIPTION OF THE INVENTION

The skin and hair compositions include those systems which cleanse skin or hair, such as shower gel, shampoo, soap bars, synthetic bars (syndet) . The compositions may be in the form of a liquid, a foam or a solid.

The skin and hair cleansing composition may be a soap bar. The term "soap bar" encompasses cleansing bars comprising saponified oils, surfactants and mixtures thereof.

Organopolysiloxane film formers include those polymers that form a film upon drying in themselves. The film may be macroscopically continuous and adherent to keratin materials, and optionally cohesive. In some instances, the film may have cohesion and mechanical properties such that it is possible for said film to be isolated and to be handled in isolation, for example when said film is produced by pouring onto a non-stick surface such as a Teflon-coated or silicone-coated surface. The film may be characterized by various parameters such as tackiness, softness, presence of cracks.

Organopolysiloxane film formers include, but are not limited to, organopolysiloxane resins, vinyl polymers grafted with a carbosiloxane dendrimer (silicone acrylate copolymers), saccharide-siloxane polymer.

The organopolysiloxane resin comprises various siloxy units such as (i) (R3Si0_1/2)a , (ii) (R₂Si0₂/₂)b , (iii) (RSi0_3/2)_c, or (iv) (SiC> 4 /₂ ) _d units which are commonly known in the art, and also used herein, as M, D, T, and Q units respectively. The amount of each siloxy unit present in the organopolysiloxane resin can be expressed as a mole fraction of the total number of moles of all siloxy units present in the organopolysiloxane resin. Thus, the organopolysiloxane resins useful in the present invention comprise the units:

(i) (R₃Si0_1/2)_a

(iii) (RSi0_3/2)c , and

wherein R is a monovalent organic group, a = 0 to 0.8, b = 0 to 0.4, c = 0 to 1.0, d = 0 to 0.8, with the provisos that the value of either c or d > 0, and the value of a + b + c + d = 1. When c = 0, d > 0, and when d = 0, c > 0.

Monovalent organic groups include hydrocarbons such as alkyl groups (methyl, ethyl, propyl, isopropyl, butyl, octyl, nonyl, tetradecyl, octadecyl); cycloalkyl groups (cyclohexyl, cycloheptyl) ; alkenyl groups (vinyl, hexenyl) ; aryl groups (phenyl, diphenyl, naphthyl); alkaryl groups (tolyl, xylyl, ethylphenyl ) ; aralkyl groups (benzyl, phenylethyl) .

The monovalent organic group may contain substituents other than carbon and hydrogen atoms, such as halogen atoms (chlorine, fluorine, bromine, iodine) ; halogen atom containing groups such as haloalkyl groups ( chloromethyl , perfluorobutyl, trifluoroethyl, and nonafluorohexyl ) and haloaryl groups (monochlorophenyl , dibromophenyl , tetrachlorophenyl , monofluorophenyl ) ; oxygen atoms; oxygen atom containing groups such as hydroxy, carboxyl, carbinol, ester, ether, acrylic groups and polyoxyalkylene groups ( polyoxyethylene, polyoxypropylene , polyoxybutylene ) ; nitrogen atoms; nitrogen atom containing groups such as nitrile, amino, amido, cyano, cyanoalkyl and urethane groups; sulphur atoms; sulphur atom containing groups such as sulphide, sulphone, sulphate, sulphonate and mercapto groups; phosphorus atoms; phosphorus atom containing groups such as phosphate, phosphate and phosphonate groups.

The organopolysiloxane resin may be a trimethylsilylsilicate (MQ resin) comprising ≥ 80 mole % of siloxy units selected from (R¹ ₃SiOi/2) _a and (Si0_4/2)d units, where R¹ is an alkyl group having from 1 to 8 carbon atoms, an aryl group, a carbinol group, or an amino group, with the proviso that ≥ 95 mole % of the R¹ groups are alkyl groups, a and d > 0, and the ratio of a/d = 0.5 to 1.5.

MQ resins may contain D and T units, providing that ≥ 80 mole %, alternatively ≥ 90 mole % of the total siloxane units are M and Q units. The MQ resins may also contain hydroxy groups. Typically, the MQ resins have a total weight % hydroxy content of 2 to 10 weight %, alternatively 2 to 5 weight %. The MQ resins can also be further "capped" wherein residual hydroxy groups are reacted further with M groups.

The organopolysiloxane resin may be a silsesquioxane resins (T resin) comprising ≥ 30 mole % of R¹Si0₃/2 units, where R¹ is as defined above. When ≥ 40 mole % of the R¹ groups are propyl, the T resin may be named a propyl silsesquioxane resin.

T resins may contain M, D, and Q units, providing that ≥ 30 mole %, alternatively ≥ 80 mole %, alternatively ≥ 90 mole % of the total siloxane units are T units. The T resins may also contain hydroxy and/or alkoxy groups. Typically, the T resins have a total weight % hydroxy content of 2 to 10 weight % and a total weight % alkoxy content ≤ 20 weight %; alternatively 6 to 8 weight % hydroxy content and ≤ 10 weight % alkoxy content.

The MQ and T organopolysiloxane resins may be used alone or combined together. When used in combination, they may be mixed prior to the addition to the other ingredients of the skin and hair cleansing composition, in presence or absence of a solvent, in a batch, semi-continuous, or continuous process. They may also be mixed at the same time as the addition of the other ingredients of the skin and hair cleansing composition.

The organopolysiloxane resin may be a MQ-T resin having the formula (R² ₃SiOi/₂)a ( ³2SiO 2/2) (R⁴Si0_3/2) _c (S1O4/2) a with R², R³ and R⁴ independently represent an alkyl group containing from 1 to 8 carbon atoms, an aryl group, a carbinol group or an amino group, where 0.05 ≤ a ≤ 0.5; 0 ≤ b ≤ 0.3; c > 0; 0.05 < d < 0.6, and a+b+c+d=l, with the proviso that ≥ 40 mole % of the R⁴ groups in the siloxane resin are propyl. Representatives of such MQ-T resins are taught in WO2005/075542, incorporated herein by reference.

The organopolysiloxane resin may be a silsesquioxane resin wax comprising at least 40 mole % of siloxy units having the formula (R^R' Si0_1/2) _x (R"Si0_3/2) _y, where x and y have a value of 0.05 to 0.95, R¹ is as described above, R' is a monovalent hydrocarbon having 9 - 40 carbon atoms, and R" is a monovalent hydrocarbon group having 1 to 8 carbon atoms or an aryl group. R' and the ratio of y/x are selected such that the silsesquioxane resin wax has a melting point of ≥ about 30°C. Representatives of such silsesquioxane resin waxes are taught in US7482419, incorporated herein by reference.

The organopolysiloxane film former may be a vinyl polymer grafted with a carbosiloxane dendrimer. The vinyl polymer grafted with a carbosiloxane dendrimer is the reaction product of a vinyl polymer with at least one carbosiloxane dendrimer-based unit. The term "carbosiloxane dendrimer structure" designates a structure with branched groups of high molecular masses with high regularity in the radial direction starting from the simple backbone. Such carbosiloxane dendrimer structures are described in the form of a highly branched siloxane-silalkylene copolymer in the laid-open Japanese patent application Kokai 9-171 154. Other vinyl polymers grafted with a carbosiloxane dendrimer are known by the skilled in the art, and described in EP0963751 incorporated herein by reference.

The organopolysiloxane film former may be a saccharide- siloxane polymer. The saccharide-siloxane polymer is the reaction product of a functionalized organosiloxane polymer and at least one hydroxy-functional saccharide component comprising 5 to 12 carbon atoms, in such a way that the organosiloxane component is covalently linked via a linking group to the saccharide component. Saccharide-siloxane polymer may be linear or branched. Saccharide-siloxane polymers are known by the skilled in the art, and described in US 20080199417, US20100105582, WO2012027073, WO2012027143 incorporated herein by reference.

The organopolysiloxane film former may be dispersed in a siloxane or organic solvent. Siloxane solvents include cyclic polysiloxanes , linear polysiloxanes , or mixtures thereof.

Examples of cyclic polysiloxanes include hexamethylcyclotrisiloxane, octamethyIcyclotetrasiloxane, decamethylcyclopentasiloxane, and dodecamethylcyclohexasiloxane .

Examples of linear polysiloxanes include hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, tetradecamethylhexasiloxane, and hexadecamethylheptasiloxane .

Examples of organic solvents include alcohols such as methanol, ethanol, isopropanol, butanol, or n-propanol; ketones such as acetone, methylethyl ketone, or methyl isobutyl ketone; aromatic hydrocarbons such as benzene, toluene, or xylene; aliphatic hydrocarbons such as heptane, hexane, octane, or isododecane; glycol ethers such as propylene glycol methyl ether, dipropylene glycol methyl ether, propylene glycol n-butyl ether, propylene glycol n- propyl ether, or ethylene glycol n-butyl ether; halogenated hydrocarbons such as dichloromethane, 1 , 1 , 1-trichloroethane or methylene chloride, chloroform, dimethyl sulfoxide, dimethyl formamide, acetonitrile, tetrahydrofuran, white spirits, mineral spirits, or naphtha, or esters.

If the organopolysiloxane film former is in the form of a solid, it may be heated to a molten state prior to being added to the other ingredients of the skin and hair cleansing composition. The organopolysiloxane film former (A) may be selected from the group consisting of organopolysiloxane resin, vinyl polymer grafted with a carbosiloxane dendrimer, saccharide-siloxane polymer.

Alternatively, the organopolysiloxane film former (A) may be an organopolysiloxane resin, selected from the group consisting of trimethylsiloxysilicate (MQ) resin, silsesquioxane (T) resin, MQ-T resin, silsesquioxane resin wax, or a mixture thereof.

Alternatively, the organopolysiloxane film former (A) is a trimethylsiloxysilicate (MQ) resin.

The organopolysiloxane film former (A) is present in the skin and hair cleansing composition at a level of from 0.1 to 20%, alternatively of from 0.5 to 10%wt, based on the total weight of the skin and hair cleansing composition .

The cooling agent (B) is meant to impart a refreshing feeling to the skin of the user upon contact with the skin or scalp. The refreshing feeling may also be referred to as cooling sensation, or freshness.

The cooling agent may be selected from the group consisting of menthol; ( - ) -isopulegol ; p-Menthane-3 , 8- diol; carvomenthol ; 1-menthone; 1,8-cineol; 1-carvone; mint oil; peppermint oil; spearmint oil; camphor; thymol; menthyl lactate; menthone glycerine; menthone glycerin acetal; N-ethyl-5-methyl-2- ( 1-methylethyl ) -cyclo- hexanecarboxarnide ; N-ethyl-p-menthane-3-carboxamide ; 4- methyl-3- (1-pyrrolidinyl) -2 [ 5H] -furanone ; N, 2, 3-trimethyl- 2-isopropylbutanamide (also known as 2-isopropyl-N, 2 , 3- trimethylbutyramide) ; monomenthyl esters of di- and polycarboxylic acids such as monomenthyl succinate and monomenthyl glutarate; 3- ( 1- enthoxy) -1 , 2-propanediol ; 1- Menthoxy-2-methyl-l, 2-propanediol ; menthol ethylene glycol carbonate; menthol propylene glycol carbonate; menthoxypropanediol ; methanediol; vanillyl butyl ether; icilin; and mixtures thereof.

Typical cooling agents (B) are menthol, mint oil, peppermint oil, spearmint oil, or a mixture thereof.

The cooling agent (B) is present in the skin and hair cleansing composition at a level of from 0.01 to 20%, alternatively of from 0.1 to 10%wt, alternatively of from 0.5 to 8%wt, based on the total weight of the skin and hair cleansing composition.

The cleansing agent (C) is selected from the group consisting of surfactants and soaps. The soap is typically obtained by saponification of a soap oil with sodium hydroxide .

Examples of surfactants include sodium laureth sulfate, ammonium laureth sulfate, cocamidopropyl betaine, cocoamphodiacetate, sodium dodecylbenzinesulfonate, sodium isethionate, sodium cocoyl isethionate, polyethylene glycols such as PEG-6 methyl ether or PEG-7 glyceryl cocoate, sodium stearate, fatty acid sulphoalkyl amide and ester .

Examples of soap oils include tallow oil, coconut oil, palm oil, palm kernel oil, olive oil, sweet almond oil, rapeseed oil.

Other ingredients in the skin and hair cleansing composition are those generally used in such compositions and include emollients, humectants, thickeners, pH adjusters, opacifiers, exfoliants, preservatives, antioxidants, chelatants, antimicrobials, dyes, essential oils, solvents, soap bar additives. Further ingredients include fragrances.

Examples of emollients include cyclomethicone, dimethicone, caprylyl methicone, hydrocarbyl functional organopolysiloxane, phenyl trimethicone, apricot kernel oil, honey, calendula, shea butter, cocoa butter, hemp oil, aloe vera, mineral oil, sesame oil.

Examples of humectants include glycerin, sorbitol, propylene glycol.

Examples of thickeners include beeswax, stearic acid, cetyl alcohol, cetearyl alcohol, xanthan gum, carbomer, hydroxyethylcellulose .

Examples of pH adjusters include citric acid, sodium hydroxide .

Examples of opacifiers include titanium dioxide, ethylene glycol distearate.

Examples of exfoliants include oat meal, wheat bran, wheat germ.

Examples of preservatives include dimethyloldimethylhydantoin, parabens (methyl, ethyl, propyl, butyl, isobutyl) , phenoxyethanol .

Examples of antioxidants include tocopheryl acetate, butylated hydroxytoluene.

Examples of chelatants include pentasodium pentetate, tetrasodium etidronate, tetrasodium EDTA.

Examples of antimicrobials include triclosan, triclocarban .

Examples of dyes include spices, iron oxides, ultramarines . Examples of essential oils include those extracted from rosewood, cedarwood, lavender, rose, peppermint, lemon, lime, pink grapefruit, litsea, bergamot.

Examples of solvents include ethanol.

Examples of soap bar additives include lanolin derivatives such as hydroxylated lanolin, PEG-75 lanolin; methyl glucosides such as methyl gluceth-20 sesquistearate, PPG-10 methyl glucose ether, methyl gluceth-20. These may be used to reduce bar cracking, to boost foam or to improve skin feel.

The skin and hair cleansing compositions may be prepared by any known or otherwise effective technique, suitable for making and formulating the desired product form. Shower gels and shampoos are usually made by dispersing the various ingredients in water, with or without heating. Soap bars are usually prepared by saponifying the soap oils with sodium hydroxide under cold or hot process. Additional ingredients may be added at the same time or after saponification is resumed, with or without heating.

Soap or surfactant bases may be used, which are melted and where to additional ingredients are added (melt and pour, soapcasting) . When using a soap base, the organopolysiloxane (A) and the cooling agent (B) may be independently added to the soap base or premixed together, with or without heating. Mixing means are those generally used and include rotors, roll mills. Soap bars and syndets may subsequently be molded in the desired shape.

The skin and hair cleansing compositions are applied topically to the desired area of the skin or hair in an amount sufficient to provide a satisfactory cleansing of the skin or hair. The compositions may be diluted with water prior to, during, or after topical application, and then subsequently rinsed or wiped off of the applied surface, for example rinsed off of the applied surface using water or a water-insoluble substrate in combination with water.

The present invention is therefore directed to a method to cleanse skin and hair by applying to it a skin and hair cleansing composition comprising an organopolysiloxane film former (A) and a cooling agent (B) , and subsequently rinsing.

An alternative method to cleanse skin and hair may be by applying to it a skin and hair cleansing composition comprising an organopolysiloxane resin and menthol, and subsequently rinsing.

EXAMPLES

The following examples are included to demonstrate embodiments of the invention. It should be appreciated by those of skill in the art that the techniques disclosed in the examples which follow represent techniques discovered by the inventor to function well in the practice of the invention, and thus can be considered to constitute preferred modes for its practice. However, those of skill in the art should, in light of the present disclosure, appreciate that many changes can be made in the specific embodiments which are disclosed and still obtain a like or similar result without departing from the spirit and scope of the invention. All percentages are in wt . %.

Comparative example 1: a soap bar based on tallow oil, free of organopolysiloxane film former and cooling agent. The soap bar of Comparative Example 1 is prepared by melting and molding a soap base based on tallow oil.

Comparative example 2: a soap bar based on tallow oil, free of organopolysiloxane film former, containing 1.4% of a mixture 1:1 of ethanol/menthol . The soap bar of

Comparative Example 2 is prepared by melting a soap base based on tallow oil, premixing the ethanol and menthol (synthetic crystals from Anhui BBCA, China), subsequently adding the mixture to the soap base and molding.

Example 1: a soap bar based on tallow oil, containing

1.4% of a mixture 1:1:2 of Q resin/cyclopentasiloxane/menthol . The soap bar of Example 1 is prepared by melting a soap base based on tallow oil, premixing the MQ resin and cyclopentasiloxane and menthol (synthetic crystals from Anhui BBCA, China) , subsequently adding the mixture to the soap base and molding.

A sensory evaluation with 12 panelists was performed to assess the following parameters:

• during wash: foam quantity, foam creaminess;

· straight after rinsing and drying : freshness, cleanliness sensation, skin smoothness

• 15 minutes after drying: cleanliness sensation, freshness, skin smoothness.

The procedure for the test was as follows:

· Wash both hands and forearms with detergent under warm water;

• Hold each soap bar in one hand and pass it under the water for one second;

Rub the soap bars against the hands separately for ten times and then set the bars on the side; • Rub left hand against right forearm and vice-versa, for ten times;

• Place the forearms under warm water until almost all the foam is gone; wash hands normally

· Dry both hands and forearms;

• Discharge the sensory on hands, analyzing only the forearms .

Fill the form with the grades of every measured attribute

Example 1 was shown to significantly impart more foam during washing (90% confidence level), more freshness to skin straight after drying and 15 minutes after drying, in addition to imparting smoothness to skin 15 minutes after drying (the latter 3 at 95% confidence level), when compared to Comparative example 1.

Example 1 was shown to significantly impart more freshness to skin 15 minutes after drying ( 90%confidence level), when compared to Comparative example 2, indicating a longer lasting freshness sensation when an organopolysiloxane film former is used with menthol.

Claims

1. A skin and hair cleansing composition characterized by comprising an organopolysiloxane film former (A) , a cooling agent (B) and a cleansing agent (C) .

2. The skin and hair cleansing composition of claim

1 characterized in that (A) is selected from the group consisting of organopolysiloxane resin, vinyl polymer grafted with a carbosiloxane dendrimer, saccharide-siloxane polymer.

3. The skin and hair cleansing composition of claim

2 characterized in that the organopolysiloxane resin is selected from the group consisting of trimethylsiloxysilicate (MQ) resin, silsesquioxane (T) resin, MQ-T resin, silsesquioxane resin wax, and mixtures thereof.

4. The skin and hair cleansing composition of claims 1, 2 or 3 characterized in that (B) is selected from the group consisting of menthol; (-) -isopulegol; p-Menthane- 3,8-diol; carvomenthol ; 1-menthone; 1,8-cineol; 1-carvone; mint oil; peppermint oil; spearmint oil; camphor; thymol; menthyl lactate; menthone glycerine; menthone glycerin acetal; N-ethyl-5-methyl-2- ( 1-methylethyl ) -cyclo- hexanecarboxarnide ; N-ethyl-p-menthane-3-carboxzamide ; 4- methyl-3- ( 1-pyrrolidinyl ) -2 [ 5H] -furanone; N, 2, 3-trimethyl- 2-isopropylbutanamide (also known as 2-isopropyl-N, 2 , 3- trimethylbutyramide) ; monomenthyl esters of di- and polycarboxylic acids such as monomenthyl succinate and monomenthyl glutarate; 3- ( 1-Menthoxy) -1 , 2-propanediol ; 1- enthoxy-2-methyl-l, 2-propanediol ; menthol ethylene glycol carbonate; menthol propylene glycol carbonate; menthoxypropanediol; methanediol ; vanillyl butyl ether; icilin; and mixtures thereof.

5. The skin and hair cleansing composition of claim 4 characterized in that (B) is selected from the group consisting of menthol, mint oil, peppermint oil, spearmint oil, and mixtures thereof.

6. The skin and hair cleansing composition of claims 1, 2, 3, 4 or 5 characterized in that (C) is selected from the group consisting of surfactants and soaps.

7. The skin and hair cleansing composition of claims

1, 2, 3, 4, 5 or 6 characterized in that (A) is present at a level of from 0.1 to 20%.

8. The skin and hair cleansing composition of claims 1, 2, 3, 4, 5, 6 or 7 characterized in that (B) is present at a level of from 0.01 to 20%.

9. A soap bar characterized by comprising an organopolysiloxane film former (A) , a cooling agent (B) and a cleansing agent (C) .

10. The soap bar of claim 9 characterized in that (A) is an organopolysiloxane resin and (B) is menthol.

11. A method to cleanse skin and hair by applying to it a cleansing composition characterized by comprising an organopolysiloxane film former (A) , a cooling agent (B) and a cleansing agent (C) , and subsequently rinsing.

12. The method of claim 11 characterized in that (A) is an organopolysiloxane resin and (B) is menthol.