WO2004014334A1

WO2004014334A1 - Hair detergent compositions

Info

Publication number: WO2004014334A1
Application number: PCT/JP2003/010140
Authority: WO
Inventors: Eiji Terada
Original assignee: Kao Corporation
Priority date: 2002-08-09
Filing date: 2003-08-08
Publication date: 2004-02-19
Also published as: JP2004067640A; EP1531789A1; CN100594875C; CN1671355A; EP1531789B1; AU2003256073A1; TWI338580B; TW200404571A; DE60316954T2; US20060051308A1; JP4147068B2; DE60316954D1

Abstract

AbstractProvided is a hair detergent composition comprising the following components (a), (b) and (c): (a) an anionic surfactant, (b) a monoalkyl glyceryl ether or monoalkenyl glyceryl ether having a C4-12 alkyl or alkenyl group, and (c) a silicone derivative having a group containing both a hydroxy group and a nitrogen atom as a side chain thereof bonded to a silicon atom. The hair detergent composition provides good foaming during washing and at the same time and is capable of giving excellent conditioning effects to the hair.11

Description

Hair Detergent Compositions

Field of the Invention The present invention relates to silicone containing hair detergent compositions which provide benefits including rich foaming upon washing the hair and give excellent conditioning effects to the hair.

Background of the Invention

Although conditioning ingredients such as silicones are usually added to hair detergents for the purpose of giving conditioning effects to the hair, their effects are not always sufficient. Another problem is that they disturb foaming of the detergents.

Summary of the Invention

In the present invention, there is thus provided a hair detergent composition comprising the following components (a) , (b) and (c) :

(a) an anionic surfactant,

(b) a monoalkyl glyceryl ether or monoalkenyl glyceryl ether having a C₄_ι₂ alkyl or alkenyl group, including mixtures thereof, and (c) a silicone derivative having a group containing both a hydroxy group and a nitrogen atom as a side chain thereof bonded to a silicon atom.

Detailed Description of the Invention All references cited are hereby incorporated by reference.

The present invention relates to hair detergent compositions providing rich foaming upon shampooing and is capable of giving excellent conditioning effects to the hair.

The present inventors have found that hair detergent compositions satisfying the above-described demand are obtainable by using, in combination, an anionic surfactant, a specific glyceryl ether, and a silicone derivative having a side chain containing both a hydroxy group and a nitrogen atom.

As the anionic surfactant of Component (a) , sulfate-, sulfonate- and carboxylate-type surfactants are preferred. Specific examples include alkyl sulfates, polyoxyalkylene alkyl ether sulfates, polyoxyalkylene alkenyl ether sulfates, alkyl sulfosuccinates, polyoxyalkylene alkyl sulfosuccinates, polyoxyalkylene alkylphenyl ether sulfates, and higher fatty acid salts. Among these, polyoxyalkylene alkyl ether sulfates and alkyl sulfates are preferred, with those represented by the following formula (al) or (a2) being particularly preferred.

RO(CH₂CH₂O)_nSO₃M (a1) ROSO₃M (a2) wherein, R represents a C₁₀-₁₈ alkyl or alkenyl group, R' represents a C10-18 alkyl group, M represents an alkali metal, alkaline earth metal, ammonium, alkanolamine or basic amino acid, and n stands for a number of from 1 to 5 on weight average.

As Component (a) , two or more of these anionic surfactants may be used in combination. The content of Component (a) in the hair detergent composition of the invention preferably ranges from 0.5 to 60 wt.%, more preferably from 1 to 30 wt.%, especially preferably from 8 to 20 wt.%, from the viewpoints of foaming performance, liquid state during use and detergency.

The alkyl or alkenyl group of the monoalkyl glyceryl ether or monoalkenyl glyceryl ether as Component (b) is preferably a linear or branched C₄-ι₀, especially Cs-io_/* alkyl group. Specific examples include n-butyl, isobutyl, n-pentyl, 2-methylbutyl, isopentyl, n-hexyl, isohexyl, n- heptyl, n-octyl, 2-ethylhexyl, n-decyl and isodecyl groups, of which 2-ethylhexyl and isodecyl groups are especially preferred.

As Component (b) , two or more of the above-described compounds may be used in combination. The content of Component (b) in the hair detergent composition of the invention ranges preferably from 0.1 to 30 wt.%, more preferably from 0.5 to 15 wt.%, especially preferably from 1 to 10 wt.%, from the viewpoints of attaining sufficient foaming power without impairing a feeling upon use and conditioning effects.

The silicone derivative as Component (c) has, as a side chain thereof bonded to a silicon atom, a group containing both a hydroxy group and a nitrogen atom. Preferred specific examples include those represented by the following average formula (1):

wherein, R¹ each independently represents a monovalent hydrocarbon group, a hydroxy group or an alkoxy group, R² each independently represents a monovalent hydrocarbon group,

R³ each independently represents a divalent Cι_ιo hydrocarbon group,

R⁴ each independently represents a group represented by the following formula (2) or (3) :

(3)

wherein, Y each independently represents a hydrogen atom or a group: -CH₂CH (OH) -R³-OH (R³ has the same meaning as described above) , R⁵ each independently represents a hydrogen atom or a group -R³NY₂ (Y and R³ have the same meanings as described above) , with the proviso that all the Ys do not represent a hydrogen atom simultaneously, a stands for a number of from 25 to 1,000, and b stands for a number of from 1 to 200. Examples of the monovalent hydrocarbon group as R¹ include alkyl groups and aryl groups. As R¹, Cι_₃ alkyl groups (particularly, methyl group) and Cι_₁₅, especially Cιo-₁₅ alkoxy groups are preferred.

Examples of the monovalent hydrocarbon group as R² include Cι-6 alkyl groups such as methyl, ethyl, propyl, butyl, pentyl and hexyl, C₆-ιo aryl groups such as phenyl, tolyl and xylyl, and C₆-ι₀ aralkyl groups such as benzyl and phenethyl . Among these, an alkyl group, particularly a methyl group, is preferred. Examples of the divalent Cι_₁₀ hydrocarbon group as R³ include methylene group, alkylene groups such as ethylene, trimethylene, propylene, tetramethylene, methyltrimethylene, ethylethylene and dimethylethylene groups, and alkylene- arylene groups such as a group represented by the formula: - (CH₂) ₂-C₆H₄-. Among these, C₂_₄ alkylene groups are preferred. When Y represents a group: -CH₂CH (OH) -R³-OH, it is preferably a 2, 3-dihydroxypropyl group. As R⁴, groups represented by the formula (3) are preferred, while as R⁵, N- (2, 3-dihydroxypropyl) aminoethyl and N,N-bis(2,3- dihydroxypropyl) aminoethyl groups are preferred. It is preferred that a stands for a number of from 75 to 400 and b stands for a number of from 1 to 20.

The silicone derivative serving as Component (c) can be synthesized, for example, by reacting an amino-modified silicone with an epoxy functional compound such as glycidol as described in EP-0399706A2. Examples of the silicone derivative as Component (c) include compounds represented by the below-described formula, while those of commercially available products include "8500 Conditioning Agent" (CAS

No. 237753-63-8; product of Dow Corning Corp).

R: C*|₃H₂₇ to Ci_δH₃ι

X: 75% of -CH₂CH(OH)CH₂OH and 25% of hydrogen atom As Component (c) , two or more of the above-described derivatives may be used in combination. From the viewpoints of smoothness and softness of the hair during the period of time from shampooing to rinsing, and smoothness of the hair after drying, the content of

Component (c) in the detergent composition of the invention ranges preferably from 0.05 to 4 wt.%, more preferably from 0.07 to 2 wt.%, especially preferably from 0.1 to 1.5 wt.%. To the detergent composition of the invention, a nonionic surfactant or amphoteric surfactant may be added in order to improve foaming performance.

Examples of the nonionic surfactant include polyoxyalkylene sorbitan fatty acid esters, polyoxyalkylene sorbit fatty acid esters, polyoxyalkylene glycerin fatty acid esters, polyoxyalkylene fatty acid esters, polyoxyalkylene alkyl ethers, polyoxyalkylene alkyl phenyl ethers, polyoxyalkylene (hydrogenated) castor oils, sucrose fatty acid esters, polyglycerin alkyl ethers, polyglycerin fatty acid esters, fatty acid alkanolamides and alkyl glycosides. Among these, alkyl glycosides, polyoxyalkylene alkyl ethers, polyoxyalkylene (Cs to C₂₀) fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene hydrogenated castor oils, and fatty acid alkanolamides are preferred. As fatty acid alkanolamides, those having a C₈- ₁₈, especially Cio-iε, acyl group are preferred. The fatty acid alkanolamides may be either monoalkanolamides or dialkanolamides, and those having a C₂-₃ hydroxyalkyl group are preferred. Examples include oleic diethanolamide, palm kernel fatty acid diethanolamide, coconut fatty acid diethanolamide, lauric diethanolamide, polyoxyethylene coconut fatty acid monoethanolamide, coconut fatty acid monoethanolamide, lauric isopropanolamide and lauric monoethanolamide .

• As the amphoteric surfactant, betaine surfactants are usable. Among these, alkyldimethylaminoacetic betaines and fatty acid amidopropyl betaines are more preferred, with fatty acid amidopropyl betaines being particularly preferred. The fatty acid amidopropyl betaines preferably have a C₈_ι₈, especially Cι₀-i₆, acyl group. Among these, lauramidopropyl betaine, palm kernel amidopropyl betaine and cocamidopropyl betaine are especially preferred.

To the detergent composition of the present invention, a conditioning component selected from cationic polymers, cationic surfactants, silicones other than Component (c) and oils can be added in order to improve the finish after drying.

Examples of the cationic polymer include cationized cellulose derivatives, cationic starch, cationized guar gum derivatives, homopolymers of diallyl quaternary ammonium salts, diallyl quaternary ammonium salt/acrylamide copolymers, quaternized polyvinylpyrrolidone derivatives, polyglycol polyamine condensates, vinylimidazolium trichloride/vinylpyrrolidone copolymers, hydroxyethyl cellulose/dimethyldiallylammonium chloride copolymers, vinylpyrrolidone/quaternized dimethylaminoethyl methacrylate copolymers, polyvinylpyrrolidone/alkylamino acrylate copolymers, polyvinylpyrrolidone/alkylamino acrylate/vinylcaprolactam copolymers, vinylpyrrolidone/methacrylamidopropyl trimethylammonium chloride copolymers, alkylacrylamide/acrylate/alkylaminoa1kylacrylamide/polyethy lene glycol methacrylate copolymers, an adipic acid/dimethylaminohydroxypropyl ethylenetriamine copolymer ("Cartaretin", product of Sandoz/USA) , and cationic polymers as described in Japanese Patent Laid-Open Nos. 139734/1978 and 36407/1985. Among these, cationized cellulose derivatives and cationized guar gum derivatives are particularly preferred.

Examples of the cationic surfactant include lauryl trimethyl ammonium chloride, cetyl trimethyl ammonium chloride, cetyl trimethyl ammonium bromide, stearyl trimethyl ammonium chloride, stearyl trimethyl ammonium bromide, lauryl trimethyl ammonium bromide, behenyl trimethyl ammonium chloride, dialkyl dimethyl ammonium chloride, dicetyl dimethyl ammonium chloride, distearyl dimethyl ammonium chloride, dicocoyl dimethyl ammonium chloride, myristyl dimethyl benzyl ammonium chloride, stearyl dimethyl benzyl ammonium chloride, lanolin fatty acid amidopropyl ethyldimethyl ammonium ethyl sulfate, lanolin fatty acid amidoethyl triethyl ammonium ethyl sulfate, stearyl amidopropyl dimethylamine (and salts thereof) , stearyl amidoethyl diethylamine (and salts thereof) , stearoxy propyl dimethylamine (and salts thereof) , stearoxy propyl trimethyl ammonium chloride, lanolin fatty acid amidopropyl triethyl ammonium ethyl sulfate, lanolin fatty acid amidoethyl trimethyl ammonium methyl sulfate, lanolin fatty acid amidopropyl ethyldimethyl ammonium methyl sulfate, isoalkanoic acid (Cι₄_₂o) amidopropyl ethyldimethyl ammonium ethyl sulfate, isoalkanoic acid (Cι₈- ₂₂) amidopropyl ethyldimethyl ammonium ethyl sulfate, isostearic acid amidopropyl ethyldimethyl ammonium ethyl sulfate, isononanoic acid amidopropyl ethyldimethyl ammonium ethyl sulfate and alkyl trimethyl ammonium saccharine . As the silicones other than Component (c) , the following compounds can be given as examples. ( Silicones-1) Dimethylpolysiloxane

Examples include compounds represented by the following formula: (Me)₃SiO-[(Me)₂SiO]_d-Si(Me)₃ wherein, Me represents a methyl group and d stands for a number of from 3 to 2,000. (Sililcones-2) Amino-modified silicone

Various amino-modified silicones are usable, but those having an average molecular weight of from about 3,000 to 100,000 and described under the name of Amodimethicone in the CTFA Dictionary (Cosmetic Ingredient Dictionary, USA) , third edition are particularly preferred. This amino-modified silicone is preferably employed in the form of an aqueous emulsion and "SM 8704C" (product of Dow Corning Toray Silicone) , "DC 929" (product of Dow Corning) , etc. are the commercially available products of the aqueous emulsion. (Silicones-3) The other silicones In addition to the above-described silicones, usable are polyether-modified silicones, methylphenyl polysiloxane, fatty acid-modified silicones, alcohol-modified silicones, alkoxy-modified silicones, epoxy-modified silicones, fluorine-modified silicones, cyclic silicones, and alkyl- modified silicones.

The term "oils" to be used herein as the conditioning component means an oily substance other than silicones and examples include hydrocarbons such as squalene, squalane, liquid paraffin, liquid isoparaffin and cycloparaffin; glycerides such as castor oil, cacao oil, mink oil, avocado i

oil and olive oil; waxes such as beeswax, spermaceti, lanolin and carnauba wax; alcohols such as cetyl alcohol, oleyl alcohol, stearyl alcohol, isostearyl alcohol, 2- octyldodecanol and glycerin; esters such as isopropyl palmitate, isopropyl myristate, octyldodecyl myristate, hexyl laurate, cetyl lactate, propylene glycol monostearate, oleyl oleate, hexadecyl 2-ethylhexanoate, isononyl isononanoate, and tridecyl isononanoate; higher fatty acids such as capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, coconut fatty acid, isostearic acid and isopalmitic acid; and isostearyl glyceryl ether and polyoxypropylene butyl ether. Among these, esters, particularly hexadecyl 2-ethylhexanoate, isononyl isononanoate and isopropyl palmitate, are particularly preferred.

As the conditioning component, two or more of these compounds may be used in combination. Its content in the hair detergent composition of the invention ranges preferably from 0.05 to 10 wt.%, more preferably from 0.07 to 5 wt.%, especially preferably from 0.1 to 2 wt.% from the viewpoints of lubrication of foams, and smoothness during the period of time from shampooing to rinsing.

In addition to the above-described components, components conventionally used for a hair detergent can be incorporated in the hair detergent composition of the present invention, depending on the purpose. Such optional components include antidandruff, vitamins, bactericides, anti-inflammatory agents, antiseptics, chelating agents, humectants such as sorbitol and pantenol, colorants such as dyes and pigments, viscosity regulators such as hydroxyethyl cellulose, methyl cellulose, polyethylene glycol and clay minerals; pH regulators such as citric acid and potassium hydroxide; vegetable extracts; pearling agents; perfumes; coloring matters; ultraviolet absorbers; antioxidants; and the other components as described in the ENCYCLOPEDIA OF SHAMPOO INGREDIENTS (MICELLE PRESS) . Although the form of the hair detergent of the invention can be selected as needed from liquid, powder, gel and granule, a liquid type using water or a lower alcohol, especially water, as a solvent is preferred.

The hair detergent of the invention is preferably used as a shampoo composition.

The hair detergent of the invention preferably has a pH of from 3 to 10, especially preferably from 3 to 7 when diluted to 20 times the weight with water.

-Examples-

The following examples further describe and demonstrate embodiments of the present invention. The examples are given solely for the purpose of illustration and are not to be construed as limitations of the present invention.

Example 1 and Comparative Examples 1 to 3

Shampoo compositions as shown in Table 1 were prepared and they were organoleptically evaluated. (Hair washing method)

After the hair was moistened sufficiently, 5 g or 10 g (5 g for medium-length hair and 10 g for long hair) of the shampoo composition was applied to the hair and the hair was washed therewith. The hair was then rinsed well with water, followed by sufficient drying with hot air from a dryer.

(Organoleptic Evaluation)

The shampoo compositions were evaluated by a panel of 10 experts based on the criteria described below and ranked based on the average score. Evaluation criteria

(1) Foaming performance

4 : Excellent foaming 3 : Good foaming

2 : Average foaming

1: Little foaming

0 : No foaming

(2) Softness of the hair during foaming 4: Very soft 3 : Soft

2 : Slightly soft

1 : Not so soft

0: Rigid (3) Smoothness of the hair during rinsing and after drying

4 : Very smooth

3 : Smooth

2: Slightly smooth

1: Not so smooth 0 : Not smooth

Rank

A: an average score of not less than 3.5

B: an average score of not less than 2.5 but less than 3.5 C: an average score of not less than 1.5 but less than 2.5

D: an average score less than 1.5

Table 1

*silicone derivative:

H₂2CH₂2N, CH₂2C, HCH₂2OH X OH

X: 75% of -CH CH(OH)CH₂OH and 25% of hydrogen atom

Example 2 : Conditioning shampoo

(wt.%)

Sodium polyoxyethylene (2) lauryl ether sulfate 11.0 Isodecyl glyceryl ether 1.5 Silicone derivative 1.0 Cocamidopropyl betaine 3.0 Ethylene glycol distearyl ester 1.0 Cationized guar gum

("Jaguar C-13S", product of RHODIA) 0.4

Sodium chloride 1.0

Polypropylene glycol (Mw=400) 1.0 Malic acid 1.0

Perfume trace

Aqueous solution of sodium hydroxide q.s.

Purified water Balance

*1: sold from Dow Corning under the name of "8500 CONDITIONING AGENT". It contains, as an effective ingredient, 60 wt.% of a silicone derivative (CAS No. 237753-63-8) having a group containing both a hydroxy group and a nitrogen atom as a side chain.

It has been found that the shampoo thus obtained (having pH 3.7 when diluted to 20 times the weight) had excellent foaming performance and at the same time had high hair conditioning effects.

Example 3: Conditioning shampoo

(wt.%) Sodium polyoxyethylene (2) lauryl ether sulfate 8.0

Sodium lauryl sulfate 5.0

Isodecyl glyceryl ether 1.5

Silicone derivative 0.5

Dimethyl polysiloxane (viscosity: 100,000 mPa-s) 0.3 Cocamide MEA 1.0

Myristyl alcohol 1.0

Cetanol 0.5

Glycerin 1.0 Ethylene glycol distearyl ester 1.0

Cationized cellulose ("UCare Polymer JR-30M", product of Amerchol) 0.5

Sodium chloride 0.5

Benzyloxy ethanol 1.0 Lactic acid 1.0

Perfume trace

Aqueous solution of sodium hydroxide q.s.

Purified water Balance

It has been found that the shampoo thus obtained (having a pH of 3.9 when diluted to 20 times the weight) had an excellent foaming performance, and at the same time had high hair conditioning effects.

Claims

1. A hair detergent composition comprising the following components (a) , (b) and (c) :

(a) an anionic surfactant, (b) a monoalkyl glyceryl ether having a C₄_ι₂ alkyl group, a monoalkenyl glyceryl ether having a C₄.-₁₂ alkenyl group, or mixtures thereof and

(c) a silicone derivative having a group containing both a hydroxy group and a nitrogen atom as a side chain thereof bonded to a silicon atom.

2. The hair detergent composition of Claim 1, wherein the anionic surfactant as Component (a) is selected from the group consisting of sulfate-, sulfonate-, carboxylate-type, and mixtures thereof.

3. The hair detergent composition of Claim 1, wherein the anionic surfactant as Component (a) is selected from the group consisting of RO(CH₂CH₂O)_nSO₃M, R'OSO₃M, and mixtures thereof wherein, R represents a C10-18 alkyl or alkenyl group, R' represents a Cι₀-ι₈ alkyl group, M represents an alkali metal, alkaline earth metal, ammonium, alkanolamine or basic amino acid, and n stands for a number of from 1 to 5 on weight average.

4. The hair detergent composition of Claim 1, wherein component (b) is a mono alkyl glyceryl ether having a linear C₄-₁₀ alkyl group, a mono alkyl glyceryl ether having a branched C₄_₁₀ alkyl group, or mixtures thereof.

5. The hair detergent composition of Claim 4, wherein alkyl group is selected from the group consisting of n-butyl, isobutyl, n-pentyl, 2-methylbutyl, isopentyl, n-hexyl, isohexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-decyl and isodecyl groups.

6. The hair detergent composition of Claim 1, wherein the silicone derivative as component (c) is represented by the average formula (1) below

(1)

R³ each independently represents a divalent Cι-₁₀ hydrocarbon group,

(2) (3)

wherein, Y each independently represents a hydrogen atom or a group: -CH₂CH (OH) -R³-OH (R³ has the same meaning as described above) , R⁵ each independently represents a hydrogen atom or a group -R³NY₂ (Y and R³ have the same meanings as described above) , wherein all the Ys do not represent a hydrogen atom simultaneously, a stands for a number of from 25 to 1,000, and b stands for a number of from 1 to 200.

7. The hair detergent composition comprising the following components (a) , (b) , and (c) :

(a) from 0.5% to 60 wt.% of an anionic surfactant,

(b) from 0.1% to 30 wt.% of a monoalkyl glyceryl ether or monoalkenyl glyceral ether having a C₄_i₂ alkyl or alkenyl group, including mixtures thereof, and

(c) from 0.05% to 4 wt.% of a silicone derivative having a group containing both a hydroxy group and a nitrogen atom as a side chain thereof bonded to a silicon atom.

8. The hair detergent composition of Claim 7, wherein the silicone derivative as Component (c) is represented by the average formula (1) below

R³ each independently represents a divalent Cι-ιo hydrocarbon group, R⁴ each independently represents a group represented by the following formula (2) or (3) :

(2) (3) wherein, Y each independently represents a hydrogen atom or a group: -CH₂CH (OH) -R³-0H (R³ has the same meaning as described above) , R⁵ each independently represents a hydrogen atom or a group -R³NY₂ (Y and R³ have the same meanings as described above) , wherein all the Ys do not represent a hydrogen atom simultaneously, a stands for a number of from 25 to 1,000, and b stands for a number of from 1 to 200.