JPS62151499A - Detergent composition - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

Detailed Description of the Invention The present invention provides products that have excellent foaming power and foam feel, good storage stability against discoloration, and are less irritating to the skin and hair, such as shampoos, kitchen detergents, and cosmetic detergents. It relates to cleaning compositions such as.

In recent years, amino acid acylated products have attracted attention as surfactants that foam well and have low irritation properties, and N-acylglutamate is a typical amino acid-based surfactant. This surfactant can be used in combination with, for example, fatty acid dialkanolamide (Japanese Unexamined Patent Publication No. 47-42809), a fatty acid-based nonionic surfactant (% JP-A-50-22803-120610), etc. It is said that performance can be improved.

However, the present inventors conducted various studies regarding these conclusions and found that these conventional detergent compositions using N-acylamino acid salts are still insufficient in terms of foaming power and foam feel. It turns out that I can't say that. Furthermore, due to the inherent properties of nitrogen-containing compounds, N-acylamino acid salts are almost unable to avoid discoloration or discoloration during storage at high temperatures and under light irradiation.

The present invention has been made to improve the above-mentioned disadvantages, and contains an N-acylamino acid salt, has excellent foaming performance, and has good long-term storage stability under high temperature and light irradiation. The purpose is to provide a hypoallergenic cleaning agent.

In order to achieve this objective, the present inventors have conducted extensive research and found that when urea and 1-hydroxy-2-pyridone compounds are used in combination with N-acylamino acid salts, foaming of cleaning agents The strength is increased, the foam feel is improved, and the storage stability is significantly improved, preventing discoloration even after long-term storage under high temperature and light irradiation, and the gentle effect on skin and hair is impaired. The present invention was completed based on the discovery that this is not the case.

The present invention provides a cleaning composition characterized by containing an N-acylamino acid salt, urea, and a 1-hydroxy-2-pyridone compound represented by the following general formula (1), the composition comprising: In (I), R1 is an alkyl group having 1 to 17 carbon atoms, an alkenyl group having 2 to 17 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, or a cycloalkyl group having 7 to 9 carbon atoms. a bicycloalkyl group having atoms, a cycloalkyl-alkyl group in which the alkyl group has 1 to 4 carbon atoms (the dicycloalkyl residue may be substituted by an alkyl group having 1 to 4 carbon atoms) ), aryl groups, aralkyl groups in which the alkyl group has 1 to 4 carbon atoms, arylalkenyl groups in which the alkenyl group has 2 to 4 carbon atoms, aryl groups in which the alkyl groups each have 1 to 4 carbon atoms an oxyalkyl or arylmercaptoalkyl group, a benzhydryl group, a phenylsulfonylalkyl group in which the alkyl group has 1 to 4 carbon atoms, a furyl group, or a furylalkenyl group in which the alkenyl group has 2 to 4 carbon atoms; The above-mentioned aryl residues may be substituted by an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a nitro group, a cyano group, or a halodane group (R2 is hydrogen) atom or an alkyl group having 1 to 4 carbon atoms, an alkenyl group or alkynyl group having 2 to 4 carbon atoms, a halodane, a phenyl group or a benzyl group; X is an organic base, an alkyl metal ion, an ammonium ion , represents an alkaline earth metal ion or a divalent to tetravalent cation.

The present invention will be explained in more detail below.

The acyl group of the N-acylamino acid salt blended into the liquid detergent of the present invention is a lauroyl group, boristoyl group, nocermitoyl group, etc., and the amino acid is glutamic acid, glycine, beta-alanine, etc. - Salts of acylamino acids include hexasalts such as sodium, lithium, monoethanolamine, jetanolamine, and triethanolamine. Note that N-acyl N-alkyl amino acid salts can also be included in the N-acyl amino acid salts of the present invention. In this case, the alkyl group is a methyl group, an ethyl group,
These include globyl group and inpropyl group.

Preferred N-acylamino acid salts include N-lauroylglutamic acid, N-myristoylglutamic acid, N-
N-acylamino acids such as parbatoylglutamic acid, N-miIJstoylbetaalanine, N-valmitoylbetaalanine, and N-lauroyl N-ethylglycine, N-lauroyl/l/N-inglovirglycine, N
-Lauroylsarcosine, N-myristoyldercosine, N-1J? Lumitoyldercosine, N-lauroyl N
There are six salts of N-acyl N-alkylamino acids such as sodium, lithium, monoethanolamine, jetanolamine, and triethanolamine, such as -methylpetalani/etc.

The amount of N-acylamino acid salt blended is preferably 3 to 30% by weight of the entire cleaning composition, more preferably 5 to 30% by weight.
It is 20% by weight. Within this range, particularly remarkable effects are exhibited.

The amount of urea, which is the second essential component of the cleaning agent of the present invention, is 0.1 to 10% of the cleaning agent from the viewpoint of actual effectiveness.
It is preferable to set it as % by weight, and when it is less than 0.1%, it may be difficult to fully exhibit the effect of improving foam performance and storage stability.

In addition to the above components, the cleaning agent of the present invention further contains a 1-hydroxy-2-pyridone compound represented by the above-mentioned general formula (1) as a third essential component. Specific examples of the compound include organic amine salts of the compounds shown below.

1-hydroxy-2-pyridone, 1-hydroxy-4-
Methyl-2-pyridone, 1-hydroxy-6-methyl-
2-Pyridone, 1-hydro-4,6-cymethyl-2
-pyridone, 1-hydroxy-4-methyl-6-hegutyl-2-giriton, 1-hydroxy-4-methyl-6-
(1-ethylpentyl)-2-pi'Jton, 1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2-pyridone, 1-hydroxy-4-methyl-
6-undecyl-2-pyridone, 1-hydroxy-4-
Methyl-6-propenyl-2-hyliton, 1-hydroxy-4-methyl-6-octeny)v-'l-pyridone, 1-hydroxy-4-methyl-6-(2,2-butyl-vinyA/ )-2-pyridone, 1-hydroxy-4
-Methyl-6-(dichlorohexenylidey-methyl)-2
-pyridone, 1-hydroxy-4-methyl-6-cyclohexyl-2-pyridone, 1-hydroxy-4-methyl-6-(methyl-cyclohexyl)-2-pyridone, 1
-hydroxy-4-methyl-6-(2-bicyclo[2,
2,1]heptyl)-2-pyridone, 1-hydroxy-
4-Methyl-6-(2-(=dimethylcyclohexyl)
-Clopyl]-2-pyrido/, 1-hydroxy-4-methyl-6-(4-methyl-phenyl)-2-pyridone,
1-hydroxy-4-methyl-6-(3-methyl-phenyl)-2-pyridone, 1-hydroxy-4-methyl-
6-(4-tert-butyl-phenyl)-2-pyridone, 1
-Hydroxy-4-methyl-6-(3-methyl-4-chloro-phenyl)-2-pyridone, 1-hydroxy-4
-Methyl-6-(3,5-dichloro-phenyl)-2-
Pyridone, 1-hydroxy-4-methy6-(3-bromo-4-chloro-phenyl)-2-pyridone, 1-hydroxy-4-methyl-6-(4-methoxystyryl)-
2-pyridone, 1-hydroxy-4-methyl-6-(1
-(4-nitrophenoxy)-butyl]-2-pyridone, 1-hydroxy-4-methyl-6-(4-cyanophenoxymethyl)-2-pyridone, 1-hydroxy-4-
Methyl-6-(phenylsulfonylmethyl)-2-pyridone, 1-hydroxy-4-methyl-6-(:1-(4
-Chlorphenylsulfonyl)-butyl)-2-pyridone, 1-hydroxy-4-methyl-6-pentrue-2-
Pyridone, 1-hydroxy-4-methyl-6-(2゜4
-dimethylbenzyl)-2-pyridone, 1-hydroxy-4-methyl-6-(tert-butyl-benzyl)-2-hydone, 1-hydroxy-4-methyl-6-2-chloro-benzyl)- 2-pyrido/, 1-hydroxy-4-
Methyl-6-(4-10lupensol) -2-hi! Jton, 1-hydroxy-4-methyA/-6-(2,5-)
Chlor-pentyl)-2-pyridone, 1-hydroxy 4
-Methyl-6-(4-bromo-benzyl)-2-pyridone, 1-hydroxy-4-methyl-6-(phenoxymethyl)-2-pyridone, 1-hydroxy-4-methyl-
6-(3-methylphenoxy-methyl)-2-pyridone, 1-hydroxy-4-methyl-6-(4-sec-butylphenoxy-methyl)-2-pyridone, 1-hydroxy-4-methyl-6- (2,4,5-trichlorophenoxy-methyl)-2-pyridone, 1-hydroxy-4-methyl-6-(4-!romphenoxymethyl)-2-pyridone, 1-hydroxy-4-methyl-6 -(4-chlorophenylmercapto-methyl)-2-pyridone, 1-
Hydroxy-4-methyl-6-(4-methylphenylmercapto-methyl)-2-pyridone, 1-hydroxy-
4-Methyl-6-(2-naphthyl)-2-pyridone, 1
-Hydroxy-4-methyl-6-penzhydryl-2-
Pyridone, 1-hydroxy-4-methyl-6-furyl-
2-pyridone, 1-hydroxy-4-methyl-6-(furylvinyl)-2-pyridone, 1-hydroxy-4-methyl-6-styryl-2-pyridone, 1-hydroxy-
4-Methyl-6-(phenylbutadienyl)-2-pyridone, 1-hydroxy-4-phenyl-6-methyl-2
-pyridone, 1-hydroxy-4,6-diphenyl-2
- Pyridone et al.

The above-mentioned compounds are used as salts, for example organic amine salts can be used. Specifically, ethanolamine, jetanolamine, N-ethylethanolamine, N-methyl-soethanolamine, triethanolamine, diethylamine-ethanol, 2-amino-2
-Methyl-n-propanol, dimethylamitube C1? /-ru, 2-avano-2-methyl-propanthol, triynepropanolamine, ethylenediamine, hexamethylenediamine, morpholine, piperidine, cyclohexylamine, triglyamine, dobucilabane, N,N-dimethyl-dodecyl Amine, stearylamine, oleylamine, benzylamine, somonolamine, N-ethylbenzylamine, dimethylstearylamine, N-methyl-morpholine, N-methylpyranone, 4-methylcyclohexylamine, N-hydroxyethyl-morpholine. can give.

The 1-hydroxy-2-pyridone compound used in this invention may be an inorganic salt. It is possible to use, for example, alkali metal salts such as sodium or potassium salts, ammonium salts or alkaline earth metal salts such as magnesium or calcium salts. Furthermore, salts with di- to tetravalent cations such as zinc salts, aluminum salts, or zirconium salts can also be used.

The blending amount of the 1-hydroxy-2-pyridone compound is not particularly limited, but the amount of the 1-hydroxy-2-pyridone compound is 0.01~
A content of 2% by weight is preferable from the viewpoint of practical effects.

In addition to the above-mentioned components, the cleaning composition of the present invention may optionally contain components depending on its type, purpose of use, etc. For example, in addition to the N-acyl amino acid salt, other anionic surfactants, nonionic surfactants, amphoteric surfactants, and cationic surfactants can be blended. In addition, low-temperature stabilizers, water-soluble polymer compounds,
Viscosity regulator, -4 regulator, antioxidant, emulsifier, humectant, oil, solubilizer, fragrance, protein derivative, animal and plant extract,
Bactericides, dyes, etc. can be added.

As described above, the cleaning composition of the present invention has foaming power and foam feel by containing N-azila epsilon acid salt, urea, and 1-hydroxy-2-pyridone compound as main ingredients. It has excellent commercial value, has good long-term storage stability under high temperatures and light irradiation, and is mild to the skin and hair, and is suitable for use in shampoos, kitchen detergents, cosmetics, and various other cleaning products. It is prepared and used as an agent.

EXAMPLES The present invention will be specifically explained below with reference to Examples and Comparative Examples. Before describing each side, we will explain the test method.

(1) Foaming power 201 nt of 6% concentration aqueous solution of liquid detergent composition (25°C
) was collected in a 100-liter cylinder, 0.2 y of liquid lanolin was added thereto as an artificial stain, shaken 20 times for 10 seconds, and the foam volume (G) was measured after 1 minute.

(2) Foam feel (sensory evaluation) Hair is divided into two parts, a comparison sample and a test sample of 3 y are applied to each side, and after lathering, the feel of the lather is evaluated and judged by 10 testers according to the following criteria. In addition, as a comparative sample, I-lyoxyethylene alkyl ether sodium sulfate (average number of added moles of EO p = 3, abbreviated as AES-Na)
Alkyl group: C1□/C13=1/1) was used.

++: Foam feel is clearly superior to AES-Na.

+: Slightly better foam feel than AES-Na.

±: The feel of foam is similar to that of AES-Na.

-: Foam feel is inferior to AES-Na.

--: Very poor foam feel compared to AES-Na.

A sample solution was prepared and stored at 60° C. or under xenon lamp irradiation for one month, and color change was visually determined.

[Evaluation criteria for storage at 60°C and storage under xenon irradiation] ○: No discoloration Δ: Slight discoloration ×: Obvious discoloration (4) Skin irritation Two methods (1) and (2) below The evaluation was carried out by

(1) Sensory evaluation Evaluation was conducted by immersion test conducted by 10 testers using a 1% aqueous solution (35° C.) of the liquid cleaning composition. That is, the dipping-drying operation was performed 15 times at intervals of 1 minute, and the degree of rough skin on the hands was visually judged after 24 hours using the following criteria.

○: Almost no skin roughness Δ: Some dry exfoliating changes in the stratum corneum surface layer of the skin ×: Dry exfoliating changes in more than 30% of the skin (2) BSA molecular ellipticity Molecular ellipticity of bovine serum albumin (BSA molecule This is an evaluation using ellipticity) as an indicator.

The method for measuring BSA molecular ellipticity is as follows.

That is, after mixing 100 ppm of bovine serum albumin and a liquid detergent composition, a sodium phosphate buffer was added to give a concentration of 50 mM, and JASCOCD S was added at 25°C.
Circular dichroism is measured using a pectropolarimeter to determine molecular ellipticity (θ). By the way, the molecular ellipticity of undenatured bovine serum albumin is 11.3 x 1
0' deg-cm2/decimal. In addition,
It has been confirmed that those with molecular ellipticity equivalent to that of bovine serum albumin and showing no denaturation cause almost no skin irritation. (The numerical unit in the table is -[θ)XIO'. ) Table 1 (cleaning compositions), Table 2 (cleaning compositions) and Table 3 (shampoo compositions) show the various results obtained in Examples 1 to 9 and Comparative Examples 1 to D. The data are summarized and shown.

In the composition column of Table 6, 1-hydroxy-2-pyrido/
The compounds listed as "based compound materials" and "axe 2" are shown below.

Tatami 1: II2: ■ H, NCH2CH20H Table 3 Experimental results of Shangu composition (Example 9) N-cocoylglutamate triethanolamine
10 Sodium polyoxyethylene alkyl ether sulfate (p=3, alkyl group C1□/C,,=1/1)
5 Coconut oil fatty acid diethanolamide
3 urea
31-Hydroxy-2-pyridone compound 6 1 Fragrance
0.3 Purified water
Residual foaming power
80 foam feel
++Storage stability 60℃
○Xenon lamp
○Skin irritation sensory evaluation
○BSA molecular ellipticity 1
0.3□ゎ ρ1.1-4B Commissioner of the Patent Office Michibe Uga 1, Indication of the case Special Responsibility No. 60-295022 2, Name of the invention Cleaning composition 3, Person who makes i'i'a correction Relationship to the incident Patent amount 1 person (676) Lion Corporation 4 generations 1] 11 people

Claims (1)

[Claims] 1. N-acyl amino acid salt, urea and the following formula (I)
A cleaning composition containing a 1-hydroxy-2-pyridone compound represented by the general formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼... (I) In the formula, R_1 is 1 Alkyl groups with ~17 carbon atoms, alkenyl groups with 2 to 17 carbon atoms, 5
A cycloalkyl group having ~8 carbon atoms, a picycloalkyl group having 7 to 9 carbon atoms, a cycloalkyl-alkyl group in which the alkyl group has 1 to 4 carbon atoms (provided that the cycloalkyl residue is optionally substituted by an alkyl group having 1 to 4 carbon atoms), an aryl group, an aralkyl group in which the alkyl group has 1 to 4 carbon atoms, an alkenyl group having 2 to 4 carbon atoms Arylalkenyl groups, aryloxyalkyl or arylmercaptoalkyl groups in which the alkyl groups each have 1 to 4 carbon atoms, benzhydryl groups, phenylsulfonylalkyl groups in which the alkyl groups each have 1 to 4 carbon atoms, furyl groups or alkenyl groups. The group represents a furylalkenyl group having 2 to 4 carbon atoms, and the above-mentioned aryl residues are alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, nitro groups, Optionally substituted by a cyano group or a halogen; R_2 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, an alkenyl group or an alkynyl group having 2 to 4 carbon atoms, a halogen, a phenyl group or a benzyl group represents a group; X represents an organic base, an alkyl metal ion, an ammonium ion, an alkaline earth metal ion, or a divalent to tetravalent cation.