JPS628411B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention provides cosmetics containing zinc pyrithione,
More specifically, the present invention relates to a hair cosmetic having excellent dispersion stabilization performance of zinc pyrithione. Traditionally, zinc pyrithione, that is, [bis-(1
-hydroxy-2(1-hydro)-pyridinethionate) zinc], anionic polymers (acrylic acid type, carboxylic acid type, etc.), nonionic polymers (cellulose type, pyrrolidone type etc.), and amphoteric polymers (acrylic acid, etc.)
etc. are used. However, these polymers are insufficient to stabilize the dispersion of zinc pyrithione unless they are blended in an amount of 1 to 2% or more, and due to the film properties of these polymers, if these polymers remain in the hair, the hair may become stiff or stiff. At present, combing causes flaking, making it difficult to obtain favorable results in terms of performance. In particular, when the cosmetic is a hair rinse, hair treatment, etc., there is a problem in that a large amount of anionic polymers and nonionic polymers remain in the hair because the hair is lightly rinsed. As mentioned above, conventional dispersion stabilizers for zinc pyrithione stabilize zinc pyrithione through the thickening effect associated with gelation, but no dispersion stabilizer for zinc pyrithione with satisfactory performance has yet been found. Not yet. As a result of repeated research to obtain a stabilizer with excellent dispersion stability for zinc pyrithione without using the conventional polymers mentioned above, the present inventors found that an ester having at least one pyrrolidone carboxylic acid residue in the molecule The present inventors have discovered that a chemical reaction product meets the above objectives and have completed the present invention. That is, the cosmetic of the present invention contains zinc pyrithione and one or more compounds represented by the following general formulas (), (), and () as a dispersion stabilizer for zinc pyrithione in an amount ranging from 0.5 to about 0.5 to about 0.5 to about 0.5 to about 0.5 to about
It is characterized by containing 3.3 times the amount. General formula (): General formula (): General formula (): (However, in the above general formulas (), (), (), at least one of X is a pyrrolidone carboxylic acid residue, the rest are hydrogen atoms, higher fatty acid residues, or higher hydroxy fatty acid groups, and a ₁ , a ₂ , a ₃ are each 0 to 20, and b ₁ , b ₂ , b ₃ are each 0
~20, and a ₁ + a ₂ + a ₃ + b ₁ + b ₂ + b ₃ = 3
-70 preferably 5-50, and m ₁ , m ₂ ,
m ₃ , m ₄ , m ₅ , m ₆ are each from 0 to 10,
n ₁ , n ₂ , n ₃ , n ₄ , n ₅ , and n ₆ are each from 0 to 10, and m ₁ +m ₂ +m ₃ +m ₄ +m ₅ +m ₆ +n ₁ +n ₂ +n ₃
+n ₄ +n ₅ +n ₆ =3 to 100, preferably 10 to 70. ) The above general formula ( ) which is an essential component of the present invention
The compounds represented by () and () can usually be obtained by the method shown below. That is, a predetermined amount of ethylene oxide or/and propylene oxide is added to glycerin, hydrogenated castor oil, or sorbitol under an alkali catalyst to form a polyether polyol, to which pyrrolidone carboxylic acid or/and other fatty acids are respectively added. They can be obtained singly or in a mixture of two or more and subjected to an esterification reaction in the absence of a catalyst or in the presence of a catalyst at normal pressure or reduced pressure according to a conventional method. In the compounds represented by the general formulas (), (), () of the present invention, if the sum of a ₁ + a ₂ + a ₃ + b ₁ + b ₂ + b ₃ is less than 3, the hydrophilicity is poor and the interaction with zinc pyrithione is weak. It cannot exhibit a dispersion stabilizing effect, and if it exceeds 70, the hydrophilicity increases and interactions in the solution do not work. Also, n ₁ + n ₂ + n ₃ + n ₄ + n ₅ +
When the sum of n ₆ + m ₁ + m ₂ + m ₃ + m ₄ + m ₅ + m ₆ is less than 3, the hydrophilicity is poor and the interaction with zinc pyrithione is weak, whereas when it exceeds 100, the hydrophilicity increases and the interaction with zinc pyrithione is weak. weak. In addition, at least one of X is a pyrrolidone carboxylic acid residue, and the rest are hydrogen atoms, higher fatty acid residues, or higher hydroxy fatty acid residues. Specific examples of higher fatty acids and higher hydroxy fatty acids that supply the above-mentioned higher fatty acid residues and higher hydroxy fatty acid residues are lauric acid, myristic acid, palmitic acid,
Higher linear saturated fatty acids such as stearic acid, aragic acid, behenic acid, and cerotic acid; Higher linear unsaturated fatty acids such as zomarinic acid, petroselic acid, oleic acid, erucic acid, linoleic acid, and linolenic acid; Higher side chain saturated fatty acids such as isostearic acid; higher hydroxy saturated fatty acids such as 1,2-hydroxystearic acid; higher hydroxy unsaturated fatty acids such as ricinoleic acid. Specific examples of the compound represented by the general formula () are as follows. Monopyroglutamic acid monoisostearate polyoxyethylene glycerin (25EO), monopyroglutamic acid monooleic acid polyoxyethylene glycerin (30EO), dipyroglutamic acid monostearate polyoxyethylene polyoxypropylene glycerin (25EO; 10PO), monopyroglutamic acid Monolinoleic acid polyoxyethylene glycerin (25EO), monopyroglutamic acid monolinolenic acid polyoxyethylene polyoxypropylene glycerin (15EO; 15PO), monopyroglutamic acid monoricinoleic acid polyoxyethylene glycerin (30EO), monopyroglutamic acid monoerucic acid polyoxyethylene glycerin Oxyethylene glycerin (35EO),
Tripyroglutamic acid polyoxyethylene polyoxypropylene glycerin (15EO; 5PO), monopyroglutamic acid monobehenic acid polyoxyethylene polyoxypropylene glycerin (10EO;
20PO). Specific examples of the compound represented by the general formula () are as follows. Monopyroglutamic acid monoisostearate polyoxyethylene hydrogenated castor oil (40EO), monopyroglutamic acid monooleic acid polyoxyethylene hydrogenated castor oil (30EO), monopyroglutamic acid monoerucic acid polyoxyethylene hydrogenated castor oil (45EO), monopyroglutamic acid Monolinoleic acid polyoxyethylene hydrogenated castor oil (35EO), monopyroglutamic acid monoricinoleic acid polyoxyethylene hydrogenated castor oil (50EO), dipyroglutamic acid monopalmitic acid polyoxyethylene polyoxypropylene hydrogenated castor oil (35EO, 5PO), Dipyroglutamic acid Monobehenic acid Polyoxyethylene Polyoxypropylene Hydrogenated castor oil (15EO, 15PO), Tripyroic acid Polyoxyethylene Polyoxypropylene Hydrogenated castor oil (10EO,
25PO), tripyroglutamic acid polyoxyethylene hydrogenated castor oil (50EO), dipyroglutamic acid monopalmitic acid polyoxyethylene polyoxypropylene hydrogenated castor oil (35EO, 5PO). Specific examples of the compound represented by the general formula () are as follows. Polyoxyethylene sorbitol monopyroglutamic acid triisostearate (50EO), polyoxyethylene sorbitol monopyroglutamic acid trioleate (60EO), polyoxyethylene sorbitol monopyroglutamic acid monooleate (70EO), polyoxyethylene sorbitol monopyroglutamic acid monostearate (70EO) Oxyethylene sorbitol (55EO), monopyroglutamate dilinoleate polyoxyethylene sorbitol (60EO), monopyroglutamate monoricinoleate polyoxyethylene sorbitol (45EO), dipyroglutamate dioleate polyoxyethylene polyoxypropylene sorbitol (40EO, 10PO) ), polyoxyethylene polyoxypropylene sorbitol dipyroglutamic acid diisostearate (35EO, 20PO), polyoxyethyl polyoxypropylene sorbitol dipyroglutamic acid monoricinoleate (40EO, 10PO), polyoxyethylene sorbitol tripyroglutamic acid monoisostearate ( 50EO), polyoxyethylene polyoxypropylene sorbitol tripyroglutamate monooleate (50EO, 5PO), polyoxyethylene sorbitol tetrapyroglutamate (60EO), polyoxyethylene polyoxypropylene sorbitol tetrapyroglutamate (40EO, 20PO). In addition, in the specific examples of compounds represented by the general formulas (), (), and () above, EO in parentheses represents ethylene oxide, PO represents propylene oxide,
The numbers indicate the average number of moles. Also,
As can be seen from the experimental examples described below, the compounds represented by the general formulas (), (), and () need to be blended in an amount of 0.5 to about 3.3 times the weight of zinc pyrithione. In addition to the above-mentioned essential ingredients, the cosmetic of the present invention may contain the following optional ingredients within a range that does not affect the effects of the present invention. That is, optional components include hydrocarbons such as liquid paraffin, vaseline, solid paraffin, squalane and olefin oligomer; isopropyl myristate, isopropyl palmitate, stearyl stearate, octyldodecyl myristate, octyldodecyl oleate, and 2-ethylhexane. Esters such as acid triglycerides; Emulsifiers such as polyoxyethylene cetyl ether, polyoxyethylene stearate, and polyoxyethylene sorbitan monolaurate; benzalkonium chloride, cetyltrimethylammonium chloride, cetostearyltrimethylammonium chloride, stearyltrimethylammonium chloride , behenyltrimethylammonium chloride,
Cationic surfactants such as distearyldimethylammonium chloride; N-(2-hydroxyethyl)-
Ampholytic surfactants such as N-[bis(2-carboxyethyl)aminoethyl]laurylamide disodium salt, 2-cocoyl-N-carboxymethyl-N-hydroxyethylimidazolium betaine; higher alcohol sulfate, alcohol ether sulfate ate, anionic surfactants such as α-olefin sulfonate; lauryl alcohol, cetyl alcohol, stearyl alcohol,
Higher alcohols such as behenyl alcohol; higher fatty acids such as palmitic acid, stearic acid, and behenic acid; humectants such as ethylene glycol, propylene glycol, 1,3-butylene glycol, glycerin, and sorbitol; and other solvents, preservatives, fragrances, etc. It is a minor component. The present invention will be explained in more detail based on the following experimental examples. First, the tests and evaluation methods adopted in the experimental examples are as follows. Place the sample in a beaker and evaluate by visual judgment for large particles of zinc pyrithione. In addition, if it cannot be determined visually, microscopic observation (400 magnification) is performed.
If particles of 10μ or more are present, it is determined that zinc pyrithione is aggregated. Evaluation Criteria ◎: Particle size is 5 μm or less ○: Particle size is 5 to 10 μm Δ: Particle size is 10 to 30 μm ×: Particle size is 30 μm or more In each experimental example, the blending amount is expressed in weight %. Test Example 1 Eighteen types of cosmetics having the compositions shown in Table 1 below were prepared and their performance was tested. The results are shown in the same table. In Table 1, zinc pyrithione, ie, bis-[1-hydroxy 2-(1hydro)-pyridinethionate] zinc, indicated by * has the following structural formula.

【table】

[Table] As is clear from Table 1, the cosmetic composition of the present invention containing the zinc pyrithione dispersion stabilizer satisfies the evaluation criteria. Test Example 2 A hair rinse agent composition shown in Table 2 below was prepared and its performance was evaluated. The effect of the composition of the present invention on the comparative composition not containing the zinc pyrithione dispersion stabilizer is clear.

[Table] Test Example 3 Hair treatment compositions shown in Table 3 below were prepared and their performance was evaluated. The results are shown in the same table.

【table】

Claims (1)

[Scope of Claims] 1. Contains zinc pyrithione and one or more compounds represented by the following general formulas (), (), () as a dispersion stabilizer for zinc pyrithione in an amount of 0.5 to about 3.3 times the weight of zinc pyrithione. Cosmetics featuring: General formula (): General formula (): General formula (): (However, in the above general formulas (), (), (), at least one of X is a pyrrolidone carboxylic acid residue, the rest are hydrogen atoms, higher fatty acid residues, or higher hydroxy fatty acid residues, and a ₁ ，
a ₂ and a ₃ are each from 0 to 20, b ₁ , b ₂ , and b ₃ are each from 0 to 20, and a ₁ + a ₂ + a ₃ + b ₁ + b ₂ +
b ₃ = 3 to 70, and m ₁ , m ₂ , m ₃ , m ₄ , m ₅ ,
m ₆ is 0 to 10, respectively, n ₁ , n ₂ , n ₃ , n ₄ ,
n ₅ and n ₆ are each from 0 to 10, and m ₁ + m ₂ +
m ₃ +m ₄ +m ₅ +m ₆ +n ₁ +n ₂ +n ₃ +n ₄ +n ₅ +n ₆ =3
~100. )