JPH1149645A - Hair damage preventing agent - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject damage-preventing agent capable of exhibiting excellent hair damage-preventing effect by using an alkyldiaminoalkane having a specific structure or its specific salt. SOLUTION: This damage-preventing agent contains at least on kind of nitrogen-containing compound selected from a group comprising an alkyldiaminoalkane of the formula (R<1> is an 8-22C alkyl or alkenyl; R<2> , R<4> and R<5> are each H, a 1-4C alkyl or alkenyl; R<3> is a 1-6C alkylene), its acid addition salt and its quaternary ammonium salt. The compound of the formula is obtained by reacting, e.g. the corresponding alkylamine with acrylonitrile to afford cyanoethylamine and subjecting cyanoethylamine to reduction with hydrogen, and the compound includes N-tallow alkyl-1,3-diaminopropane, N- coconut oil alkyl-1,3-diaminopropane, etc. Furthermore, the nitrogen-containing compound is contained, preferably in an amount of 0.01-10 wt.% in the damage- preventing agent.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an agent for preventing damage to hair, which can be effectively applied to hair to prevent troubles such as fluffing and cracks of hair.

2. Description of the Related Art Due to an increase in fashionable consciousness, many adult women have given their hairs a chemical treatment such as perm, hair bleach or hair coloring. In such a case, damage troubles such as loss of luster of hair, rust, split ends and cut hairs have occurred. Since hair is dead tissue, self-repair is impossible, and once damage has started, the progress of the damage is accelerated in daily life such as shampooing, brushing, and using a dryer. Cause serious worries.

Conventionally, as a method for preventing the generation of split ends, the surface of hair is coated with a film-forming substance such as a cationic surfactant, a high molecular compound, or a liquid oil to reduce the frictional force in the cuticle layer. Attempts have been made to suppress peeling damage during brushing and to reinforce hair strength (Japanese Patent Application Laid-Open No. 57-57).
-88111, JP-A-5-85921, JP-A-6-505973). Further, for the purpose of repairing damaged parts, there has been proposed a method of permeating and replenishing degradation products such as collagen and keratin similar to hair components and their derivatives into hair (JP-A-57-88109, Japanese Unexamined Patent Publication (Kokai) No. 2-53712) has not yet obtained a sufficient effect, and there has been a strong demand for the development of a hair damage inhibitor excellent in damage prevention or repair effect. On the other hand, as a method of searching for an agent for preventing hair damage, for example, in the evaluation of split hair generation, a method using an automatic brushing device in accordance with actual behavior has been proposed (Arai et al., Cosmetic Magazine,
29 (2) , 125 (1995)), the development of a simpler and more quantitative evaluation system has been desired, and the present inventors have prepared a new damaged model hair and devised an evaluation method (Japanese Patent Application Hei 8-329232).

[0003]

SUMMARY OF THE INVENTION The present invention has been made to meet the above-mentioned demands, and has as its object to provide a hair damage inhibitor capable of preventing hair troubles such as hair fluffing and cracks. .

According to the present invention, the use of an alkyldiaminoalkane having a specific structure, an acid addition salt thereof or a quaternary ammonium salt thereof provides an excellent hair in an experimental system based on the above-mentioned damaged model hair. This is based on the finding that an effect of preventing damage can be obtained, and in fact, hair fluffing and cracking can be prevented. That is, the present invention is characterized in that it contains at least one nitrogen-containing compound selected from the group consisting of alkyldiaminoalkanes represented by the following general formula [I], acid addition salts thereof and quaternary ammonium salts thereof. And a hair damage preventing agent.

[0004]

Embedded image

Wherein R ¹ is an alkyl or alkenyl group having 8 to 22 carbon atoms, R ² , R ⁴ and R ⁵ are hydrogen or an alkyl or alkenyl group having 1 to 4 carbon atoms, R ³
Is an alkylene group having 1 to 6 carbon atoms. )

BEST MODE FOR CARRYING OUT THE INVENTION The alkyldiaminoalkane used in the present invention is represented by the above general formula [I]. Where:
The alkyl group and the alkenyl group in R ¹ , R ² , R ⁴ and R ⁵ may be in a linear, branched or cyclic state.
R ¹ is preferably an alkyl group having 10 to 20 carbon atoms, and R ² , R ⁴ and R ⁵ are preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ³
Is preferably a group represented by (CH ₂ ) _n [n is 2 to 6].

The acid addition salts of the alkyldiaminoalkane represented by the general formula [I] used in the present invention include salts with inorganic acids such as hydrochloric acid, nitric acid and sulfuric acid, alkyl sulfuric acid, benzenesulfonic acid, toluenesulfonic acid, and the like. Salts with organic acids such as acetic acid and tartaric acid are included. Here, examples of the alkyl sulfuric acid include alkyl sulfuric acids having 1 to 8 carbon atoms. As the quaternary ammonium salt of the alkyldiaminoalkane represented by the general formula [I] used in the present invention, those represented by the following general formula [II] are preferable.

[0007]

Embedded image

[0008] wherein, R ¹ to R ⁵ are the same as in the general formula [I], R ⁶ and R ⁷ are each independently
An alkyl or alkenyl group having 1 to 4 carbon atoms;
^- anion, a and b represent the number of each 0 or 1, a + b is greater than or equal to 1, c is equal to a + b. Here, R ⁶ and R ⁷ are preferably the same substituent, and more preferably, R ² , R ⁴ , R ⁵ , R ⁶ and R ⁷ are the same substituent. Further, a + b is preferably 2. X ^- is the halogen ion, nitric acid, sulfuric acid,
Acid residues such as alkylsulfuric acid, benzenesulfonic acid, toluenesulfonic acid, acetic acid, tartaric acid and the like can be mentioned.

The alkyldiaminoalkane represented by the general formula [I] can be easily obtained by, for example, reacting a corresponding alkylamine with acrylonitrile to obtain cyanoethylamine and then performing hydrogen reduction.
For example, N-tallow alkyl-1,3-diaminopropane (tallow alkylaminopropylamine), N-coconut oil alkyl
-1,3-diaminopropane (coconut oil alkylaminopropylamine) and the like. Alternatively, it can be obtained by reacting an alkyl halide with a corresponding alkyl diamine to separate a 1-mol adduct. As an example, N-stearyl-1,6-diaminohexane (stearylaminohexylamine) can be obtained by reacting stearyl chloride with hexamethylenediamine. These derivatives can also be prepared by a general alkylation reaction. Further, the compound represented by the general formula [I
It is also easy to make a quaternary salt represented by I]. For example, N, N ', N'-trimethyl-N-tallowalkyl-diaminopropane can be obtained by reacting N-tallowalkyl-1,3-diaminopropane with formalin. Further, by reacting this with methyl chloride, N, N, N ', N', N'-pentamethyl-N-tallowalkyl-1,3-propanediammonium dichloride can be obtained.

In the present invention, it is essential to contain the above-mentioned nitrogen-containing compound. In this case, the alkyldiaminoalkane represented by the general formula [I], its acid addition salt and its fourth
Mixtures of two or more quaternary ammonium salts can also be used. The nitrogen-containing compound is contained in the hair damage inhibitor in an amount of 0.
The content is preferably from 0.1 to 10% by weight (hereinafter abbreviated as%), and more preferably from 0.05 to 5%. The balance of the hair damage inhibitor of the present invention is preferably water or aqueous alcohol (particularly, a mixed solvent of lower alcohol and water). In particular, it is preferable to use a mixed solvent of ethanol and water.
The hair damage preventive agent of the present invention may contain, as desired, various additive components commonly used in conventional hair cosmetics, in addition to the nitrogen-containing compound, as long as the object of the present invention is not impaired. it can.

Examples of such additional components include a cationic polymer compound, an amphoteric polymer compound, a nonionic polymer compound, a silicone polymer compound, a cationic surfactant, and a nonionic surfactant. , An amphoteric surfactant,
Organic acids such as citric acid and succinic acid and salts thereof, preservatives, bactericides, thickeners, thickeners, ultraviolet absorbers, antioxidants, physiologically active ingredients such as vitamins, drugs and natural product extracts, high-grade Alcohols, hydrocarbons, ester oils, fatty acids, silicone oils, paraffin oils, oils such as squalane, petrolatum, coloring agents, fragrances, chelating agents, pH adjusters, solubilizing agents such as ethyl carbitol, isoprene glycol, benzyl alcohol, etc. And humectants such as peptides, ethylene glycol, propylene glycol, sorbitol, glycerin and amino acids. More preferably, the hair damage preventing agent of the present invention contains 0.01 to 10% of the nitrogen-containing compound, the balance being a mixed solvent of ethanol and water, and the nitrogen-containing compound dissolved therein. Is preferred. The hair damage inhibitor of the present invention can be widely used in many product forms such as, for example, liquid, foam, spray, gel, and cream. Among these, it is particularly preferable that the hair is contained in a spray container, so that the hair damage preventing agent can be easily applied to the hair.

[0012]

By spraying or applying the hair damage preventive agent of the present invention on hair, it is possible to effectively prevent hair damage troubles such as hair fluffing and cracks. Hereinafter, the present invention will be described specifically with reference to examples, but the present invention is not limited to the following examples.

【Example】

Example 1 Hair was prepared according to the method for searching for a hair damage preventing agent described in Japanese Patent Application No. 8-329232. That is, after a hair of 10 cm from the root of a 27-year-old woman who has not been subjected to chemical treatment is degreased (chloroform: methanol = 2: 1), 1 mL of 25 mM tris-glycine buffer (pH 8.3) is added to 10 mg of hair. In addition, SDS (sodium dodecyl sulfate) was then added to a final concentration of 1%, followed by a further 2.3.
% Dithiothreitol (DTT)
Elution was performed at 37 ° C for 4 hours. Thereafter, the compounds shown in Table 1 were immersed in a hair damage inhibitor dissolved in a 20% ethanol solution, dried at 80 ° C. for 15 minutes, and then freeze-dried to evaluate the frequency of crack generation, fluffiness and hair surface condition. The results are shown in Table 1. In addition, the hair surface condition was visually determined according to the following criteria. Hair surface condition ○: Almost no roughness △: Somewhat rough ×: Very rough

[0013]

[Table 1] Table 1 ──────────────────────────────────── Compound content Crack generation Percentage Fluffing Hair surface (%) (%) Prevention Surface condition control (untreated) 0 100 × ○ 0.1 65 △ ○ 0.5 60 ○ ○ N-stearyl-1,3-diaminopro 1.0 50 ○ ○ Bread 2.0 45 ○ ○ 5.0 40 ○ ○ N-dodecyl-1,3-diaminopro 1.0 60 △ ○ Pan 5.0 45 ○ ○ N-myristyl-1,3-diaminopro 1.0 50 △ ○ Pan 5.0 40 ○ ○ N, N ', N'-trimethyl -N- palmitic 0.5 50 ○ ○ le-1,4-diaminobutane hydrochloride 2.5 35 ○ ○ N, N ', N'-trimethyl-N-steari 0.5 50 ○ ○ ru- 1,3-diaminopropane 2.5 30 ○ ○ N, N, N ', N', N'-pentamethyl dichloride 0.5 40 ○ ○ -N- Stearyl-1,3-propanedi 1.030 ○ ○ Ammonium 2.0 25 ○ ○ Diacetic acid N, N, N ', N ', N'-Pentamethyl 0.5 50 ○ ○ -N- Palmityl-1,6-hexa 1.0 35 ○ ○ diammonium 2.0 30 ○ ○ N-dodecyl-1,3-diaminopropane 0.5 + 25 ○ ○ di chloride N, N, N ', N ', N'- pentamethyl 0.5-N-stearyl - 1,4 -Butandiammonium (comparative example) 1.0 85 × △ N, N, N-trimethyl chloride 2.0 75 × × Tallowalkylammonium 5.0 65 △ ×

From the results shown in Table 1, it can be seen that the hair damage inhibitor of the present invention containing a nitrogen-containing compound significantly suppresses cracking and fluffing during freeze-drying, and does not roughen the surface of the hair. . Example 2 A spray-type hair damage inhibitor having the following composition was prepared. This hair damage inhibitor was evaluated for the frequency of cracks, fluffiness and hair surface condition in the same manner as in Example 1. As a result, the frequency of cracks was 20% and the fluffiness and hair surface condition were good. N-stearyl-1,3-diaminopropane hydrochloride 0.5% Polyvinylpyrrolidone 1.0% Cationic polymer compound * 1) 0.5% Quaternary trimethylammonium-derived polypeptide * 2) 4.0% Glycine 0.5% Polyoxyethylene (30) hydrogenated castor oil 0.5% Oxybenzonesulfonic acid 0.1% Methylparaben 0.1% Dibutylhydroxytoluene 0.05% Fragrance 0.5% Green No. 3 trace amount citric acid (pH Adjusted to 6) Appropriate amount Ethanol 10% Purified water Remainder * 1): Cationized cellulose (Lion Co., Ltd., Leogard GPS) * 2): Quaternary trimethylammonium-introduced keratin hydrolyzate (Seiwa Kasei Co., Ltd.) Promois WK-Q)

Example 3 An aerosol foam type hair damage inhibitor having the following composition was prepared. Example 1 of this hair damage inhibitor
As a result, the frequency of occurrence of cracks, fluffiness and hair surface condition were evaluated in the same manner as described above. As a result, the frequency of crack occurrence was 20%, and the fluffiness and hair surface condition were also good. N, N, N ', N', N'-pentamethyl-N-tallowalkyl-1,3-propanediammonium dichloride 0.5% Amphoteric polymer compound * 3) 0.5% Collagen peptide * 4) 1 0.0% Arginine 0.5% Polyoxyethylene (10) -methylpolysiloxane copolymer 4.0% Polyoxyethylene monooleate (20) sorbitan 0.5% Fragrance 0.3% Liquefied petroleum gas 10% Ethanol 25% purified water balance * 3): N-methacryloyloxyethyl N, N-dimethylammonium-α-N-methylcarboxybetaine / alkyl methacrylate copolymer (Diachemco, Yuka Former AM75 204W) * 4): Collagen water Decomposed product (Seiwa Chemical Co., Ltd., Promois W-42) The numerical value in parentheses in the above compound is ethylene oxide or The average number of moles of the added Ren'okishido (hereinafter the same).

Example 4 A gel type hair damage inhibitor having the following composition was prepared. This hair damage inhibitor was evaluated for the frequency of cracks, fluffiness and hair surface condition in the same manner as in Example 1. As a result, the frequency of cracks was 20% and the fluffiness and hair surface condition were good. N, N ', N'-trimethyl-N-coco oil alkyl-1,6-diaminohexane acetate 0.5% amphoteric polymer compound * 5) 0.5% carboxyvinyl polymer 0.5% polyoxypropylene ( 12) Diglyceryl ether 2.0% Polyoxyethylene (30) hydrogenated castor oil 0.5% Methyl paraben 0.1% Fragrance 0.3% Triethanolamine (pH adjusted to 7) Appropriate amount Ethanol 10% Purified water balance * 5): N-methacryloyloxyethyl N, N-dimethylammonium-α-N-methylcarboxybetaine / alkyl methacrylate copolymer (Diachemco, Yuka Former AM75 301)

Claims (1)

[Claims] 1. It comprises at least one nitrogen-containing compound selected from the group consisting of an alkyldiaminoalkane represented by the following general formula [I], an acid addition salt thereof and a quaternary ammonium salt thereof. Hair damage inhibitor. Embedded image (Wherein, R ¹ is an alkyl group or alkenyl group having 8 to 22 carbon atoms, and R ² , R ⁴ and R ⁵ are hydrogen or 1 carbon atoms.
To 4 alkyl or alkenyl group, R ³ is 1 to carbon atoms
6 alkylene groups. )