Patent Publication Number: US-5529712-A

Title: Detergent composition

Description:
TECHNICAL FIELD 
     This invention relates to a detergent composition which comprises an N-acyl glycine salt, an N-acyl alanine salt and/or an N-acyl β-alanine salt, together with a higher fatty acid salt, and to another detergent composition whose use feeling is improved by incorporating further a higher alcohol and/or a polyhydric alcohol. 
     BACKGROUND ART 
     N-Acyl amino acid salts are known as surface active agents generally having high safety, and, particularly, N-acyl glutamic acid salts, N-acyl sarcosine salts, N-acyl β-alanine salts, N-acyl methyl taurine salts and the like are broadly used in detergents. Other N-acyl amino acid salts have also been studied since considerably old times, and N-acyl amino acids were actually synthesized from and examined on natural amino acids and synthetically obtainable amino acids. Especially, there are a number of reports on the results of studies on N-acyl derivatives of natural amino acids. 
     Recently, it was reported that scum formed by the reaction of an N-acyl glycine salt, an N-acyl β-alanine salt or the like with calcium contained in city water was found to have an excellent touch (Japanese Patent Application Laid-Open (Kokai) No. Hei 4-221607). However, the N-acyl amino acid salts disclosed in this report and other natural type N-acyl amino acid salts were not sufficient in their bubble-related performances in terms of bubble retention, creaminess, lathering power and sliminess. 
     The object of the present invention is to provide an excellent detergent composition comprising an N-acyl amino acid salt, which is highly safe and shows quick, effective and creamy lathering and reduced slimy touch to the skin. 
     DISCLOSURE OF THE INVENTION 
     With the aim of achieving the aforementioned object, the inventors of the present invention have conducted intensive studies and found as the result that an excellent detergent composition having the aforementioned properties can be provided by jointly using a salt of a specified N-acyl amino acid and a salt of a specified higher fatty acid, or by blending further them with a specified higher alcohol and/or polyhydric alcohol, and finally accomplished the present invention on the basis of such findings. 
     Accordingly, the present invention relates to a detergent composition which comprises (A) an N-acyl amino acid salt of an amino acid selected from glycine, alanine and β-alanine where the acyl group is a fatty acid residue having 8 to 20 carbon atoms and (B) a higher fatty acid salt having 8 to 20 carbon atoms at a Component (A)/Component (B) weight ratio of 99.5/0.5 to 90/10, and to another detergent composition derived from the above composition, which comprises further a higher alcohol and/or polyhydric alcohol. 
     The present invention will be described in detail as follows. 
     With regard to N-acyl amino acid salts as Component (A) of the detergent composition of the present invention, the N-acyl amino acid moiety is composed of an amino acid selected from glycine, alanine and β-alanine and an acyl group which is a saturated or unsaturated fatty acid residue having 8 to 20 carbon atoms. Examples of such moiety include lauroyl glycine, cocoyl glycine, myristoyl glycine, palmitoyl glycine, stearoyl glycine, oleoyl glycine, lauroyl β-alanine, cocoyl β-alanine, myristoyl β-alanine, palmitoyl β-alanine, stearoyl β-alanine, oleoyl β-alanine, lauroyl alanine, cocoyl alanine, myristoyl alanine, palmitoyl alanine, stearoyl alanine and the like. These N-acyl amino acids may be of either optically active form or racemic form. On the other hand, examples of the base moiety include alkali metals such as sodium, potassium and the like, organic amines such as triethanolamine, diethanolamine, monoethanolamine and the like alkanol amines and basic amino acids such as lysine, ornithine, arginine and the like. These base moieties may be used as a combination of two or more, because such a combination may further improve lathering and bubble retention. 
     With regard to higher fatty acid salts as Component (B), examples of the higher fatty acid moiety include straight- or branched chain, saturated or unsaturated ones each having 8 to 20 carbon atoms, particularly lauric acid, myristic acid, palmitic acid, stearic acid, coconut oil fatty acids, hardened tallow fatty acids and oleic acid, while the base moiety may be selected from the aforementioned base moieties of the Component (A) N-acyl amino acid salts. 
     As a matter of course, the aforementioned N-acyl amino acid salts may be used alone or as a mixture of two or more. The aforementioned higher fatty acid salts can also be used in the same manner. 
     With regard to the ratio (by weight) of Components (A) and (B) to be comprised in the detergent composition of the present invention, bubble quality is rough, bubble retention is poor and bubble volume is insufficient when Component (A)/Component (B)=100/0. The bubble volume-increasing effect of Component (B) becomes significant and the bubble retention, creaminess of bubble quality, non-sliminess and bubble-breaking capacity become appropriate when the ratio is adjusted to the Component (A)/Component (B)=99.5/0.5, the bubble retention becomes relatively good when the Component (A)/Component (B)=98/2, and almost constant effects are obtained when the Component (A)/Component (B)=97/3. The ratio if exceeding the Component (A)/Component (B)=90/10 would cause rapid increase in the generation of unusual smells and jarring touch, thus spoiling feeling of the detergent composition when used. 
     Jarring touch does not occur and refreshed feeling is improved when a specified higher alcohol is jointly used in addition to the active ingredients composed of the specified N-acyl amino acid salt and the specified higher fatty acid salt. 
     Such higher alcohols can be straight- or branched-chain, saturated or unsaturated alcohols having 8 to 24 carbon atoms. Examples of such higher alcohols include, especially, lauryl alcohol, myristyl alcohol, stearyl alcohol, cetanol, cetostearyl alcohol and the like. As a matter of course, these higher alcohols can be used alone or jointly as a mixture of two or more, and the joint use will exert the effect in smaller amounts. 
     With regard to the amount of the higher alcohol (total amount when used as a mixture), 0.5 to 20% by weight based on the total amount of Components (A) and (B) may be effective, and amounts outside this range will not bear refreshed feeling. 
     In addition, hardening and dry-and-rough feeling of the skin and hair and stiffness of the skin can be prevented when a polyhydric alcohol is jointly used in addition to the active principle composed of the specified N-acyl amino acid salt and the specified higher fatty acid salt. 
     Such polyhydric alcohol to be used herein can be those alcohols which have 2 or more hydroxyl groups in one molecule. Examples include glycerol, 1,3-butylene glycol, octanediol, ethylene glycol, diethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, isoprene glycol, maltitol, sorbitol, pentaerythritol and the like. Of these, glycerol, 1,3-butylene glycol and propylene glycol are preferred from the view point of the use feeling and bubble volume. 
     Amounts of the polyhydric alcohol to be blended may be in the range of from 3 to 30% by weight, preferably from 5 to 20% by weight, of the total composition. The amount if smaller than 3% would bear no effect of its blending, and if larger than 30% would result in poor bubble quality and inferior use feeling. 
     With regard to the pH value of the detergent composition of the present invention, a pH value of from 6 to 10 to be provided at the time of the use of the composition is preferable from the safety point of view, and a pH value of from 6.5 to 9 is more desirable in view of the use feeling and lathering property. In consequence, the detergent composition of the present invention may be used as such if the pH value upon dissolution in water is within the above range, though it varies depending on the type of the base moiety of the N-acyl amino acid salt, but, when the value is outside the above range, a pH adjusting agent such as citric acid, carbonate or the like should have preferably been blended in advance so that the pH value is set within the range when it is used. 
     The detergent composition of the present invention may be made into appropriate preparation forms as detergents with no particular limitation, such as liquids, pastes, solids, powders and the like. 
     Also, as a matter of course, the detergent composition of the present invention can comprises such additives as commonly used in cosmetics and detergents, such as drugs, bactericides, perfumes, pigments and the like, corresponding to each application purpose, and within such a range that they do not spoil the characteristics of the present invention. 
     The detergent composition of the present invention shows a significant synergistic effect in terms of the bubble performance when used jointly with other anionic, nonionic and amphoteric surface active agents. 
    
    
     BRIEF DESCRIPTION OF THE DRAWINGS 
     FIG. 1 shows a graph showing the results of Test Example 1. 
    
    
     BEST MODE OF CARRYING OUT THE INVENTION 
     The following examples are provided to further illustrate the present invention. 
     Test Example 1 
     N-Lauroyl glycine was synthesized in accordance with the well known Schotten-Baumann reaction, and the unreacted fatty acid and other impurities were removed from the reaction product by recrystallization to obtain highly purified N-lauroyl glycine (purity, 99.95% or more), which was subsequently neutralized with potassium hydroxide to obtain the potassium salt of N-lauroyl glycine. 
     Using the thus obtained potassium salt of N-lauryl glycine (Component (A)) and potassium myristate (Component (B)) in varied amounts, several aqueous solutions (pH 8.2), each containing the components in a total concentration (surfactant concentration) of 0.5% by weight, were prepared. A 50 g portion of each aqueous solution was taken and stirred in a domestic mixer &#34;Milcer&#34; (manufactured by Iwatani Sangyo) to examine retention of bubbles. The retention is defined based on the formula, (bubble volume (ml) 10 minutes after stirring)/(bubble volume (ml), just after stirring)×100. 
     Another test was carried out on the retention of bubbles completely in the same manner except that potassium laurate was used instead of potassium myristate. 
     The results are shown in FIG. 1. As is evident from the figure, N-acyl amino acid salt alone cannot show sufficient retention of bubbles, while the bubble retention is improved when a very small amount of a higher fatty acid salt is added to the N-acyl amino acid salt (reaching almost the maximum level by the addition of about 2% of the higher fatty acid salt). 
     In order to evaluate creaminess, bubbles collected just after lathering at Points P and Q in FIG. 1 were placed on a slide glass, covered with cover glasses and then observed under a fiber scope microscope &#34;Scopeman&#34; (manufactured by Moritex), simultaneously taking photographs. As the result, it was found that the bubbles collected at Point P where a small amount of the fatty acid salt had been added were excellent in creaminess, while the bubbles collected at Point Q where the fatty acid salt had not been added were confirmed to be unstable, because they united during the microscopic observation. 
     Inventive Examples 1 to 10 and Comparative Examples 1 to 7 
     Various types of N-acyl amino acid salts were prepared in the same manner as described in Test Example 1. 
     Using the thus prepared N-acyl amino acid salts and higher fatty acid salts and higher alcohols in such varied amounts as shown in Table 3, a number of aqueous solutions, each containing these components in a total concentration (surfactant concentration) of 0.5% by weight, were prepared. The pH value of each solution was found to be 7 to 8. Each of the thus prepared solutions was stirred using the domestic mixer used in Test Example 1 to examine the test items shown in Table 1. 
     
                       TABLE 1                                                     
______________________________________                                    
Test item Description                                                     
______________________________________                                    
Bubble volume                                                             
          bubble volume (ml), 5 seconds after stirring                    
Lathering rate                                                            
          ⊚ : very quick, ◯ : quick, Δ:  
          usual, x: not                                                   
          sufficient                                                      
Creaminess of                                                             
          ⊚ : very creamy, ◯ : creamy,         
          Δ: usual, x: not                                          
bubbles   sufficient                                                      
Retention of                                                              
          retention (%) = (bubble volume (ml), 10                         
bubbles   minutes after stirring)/bubble volume (ml),                     
          5 seconds after stirring) × 100                           
______________________________________                                    
 
    
     The compositions of the present invention were evaluated as head hair and body detergents by organoleptic tests by 20 expert panelists composed of 10 females and 10 males, concerning the touch of bubbles, jarring feeling, refreshed feeling and sliminess after washing, and the smells at the time of washing as the sense of touch and feeling. The organoleptic hand-washing and hair-washing tests were carried out using test solutions prepared by diluting each of the compositions having varied blending ratios shown in Table 3 with distilled water to a surfactant concentration of 30% or 15%. 
     The criteria for evaluation of each test item is shown in Table 2. 
     
                       TABLE 2                                                     
______________________________________                                    
Test item  Description                                                    
______________________________________                                    
Touch of bubbles                                                          
           ⊚ : very good, ◯ : good, Δ:   
           usual, and x:                                                  
           bad.                                                           
Jarring feeling                                                           
           ⊚ : very smooth, ◯ : smooth,        
           Δ: jarring, and                                          
(hands)    x: extremely jarring.                                          
Jarring feeling                                                           
           ⊚ : very smooth, ◯ : smooth,        
           Δ: jarring, and                                          
(hair)     x: extremely jarring.                                          
Refreshed  ⊚ : very refreshed, ◯ : refreshed,  
           Δ: usual,                                                
feeling    and x: slimy.                                                  
Sliminess  ◯ : not slimy, and x: slimy.                       
Smells     ⊚ : not feel at all, ◯ : hardly     
           feel, Δ:                                                 
           usual, and x: unpleasant smells.                               
______________________________________                                    
 
    
     The results are shown in Table 3. 
     
                                           TABLE 3                                 
__________________________________________________________________________
                  Inventive Examples                                      
                  1    2  3    4  5                                       
__________________________________________________________________________
Acyl                                                                      
    Lauroyl glycine TEA                                                   
                   95                                                     
amino                                                                     
    Lauroyl glycine sodium                                                
                        92                                                
acid                                                                      
    Myristoyl glycine potassium                                           
                           90                                             
salt                                                                      
    Lauroyl alanine TEA         90                                        
    Lauroyl β-alanine potassium                                      
                                   90                                     
Higher                                                                    
    Sodium laurate              10                                        
fatty                                                                     
    Potassium laurate   8                                                 
acid                                                                      
    Coconut oil fatty acid TEA                                            
                   5       10                                             
salt                                                                      
    Potassium myristate            10                                     
Higher                                                                    
    Cetanol                                                               
alcohol                                                                   
    Lauryl alcohol                                                        
Results                                                                   
    Bubble volume (ml)                                                    
                  300  310                                                
                          320  315                                        
                                  300                                     
    Lathering rate                                                        
                  ⊚                                        
                       ⊚                                   
                          ⊚                                
                               ⊚                           
                                  ⊚                        
    Creaminess of bubbles                                                 
                  ⊚                                        
                       ⊚                                   
                          ⊚                                
                               ⊚                           
                                  ⊚                        
    Retention of bubbles                                                  
                   98   95                                                
                           99   97                                        
                                  100                                     
    Touch of bubbles                                                      
                  ◯                                           
                       ◯                                      
                          ⊚                                
                               ⊚                           
                                  ⊚                        
    Sliminess     ◯                                           
                       ◯                                      
                          ◯                                   
                               ◯                              
                                  ◯                           
    Jarring feeling (hands)                                               
                  ⊚                                        
                       ⊚                                   
                          ⊚                                
                               ⊚                           
                                  ⊚                        
    Jarring feeling (hair)                                                
                  ⊚                                        
                       ⊚                                   
                          ⊚                                
                               ⊚                           
                                  ⊚                        
    Refreshed feeling                                                     
                  ◯                                           
                       ◯                                      
                          ◯                                   
                               ◯                              
                                  ◯                           
    Smells        ⊚                                        
                       ⊚                                   
                          ⊚                                
                               ⊚                           
                                  ⊚                        
__________________________________________________________________________
                  Inventive Examples                                      
                  6    7  8    9  10                                      
__________________________________________________________________________
Acyl                                                                      
    Lauroyl glycine TEA                                                   
                   90                                                     
amino                                                                     
    Lauroyl glycine sodium                                                
                        92                                                
acid                                                                      
    Myristoyl glycine potassium                                           
                           90                                             
salt                                                                      
    Lauroyl alanine TEA         90                                        
    Lauroyl β-alanine potassium                                      
                                   90                                     
Higher                                                                    
    Sodium laurate              7                                         
fatty                                                                     
    Potassium laurate   5                                                 
acid                                                                      
    Coconut oil fatty acid TEA                                            
                   5       7                                              
salt                                                                      
    Potassium myristate            2                                      
Higher                                                                    
    Cetanol        5    3       3                                         
alcohol                                                                   
    Lauryl alcohol         3       8                                      
Results                                                                   
    Bubble volume (ml)                                                    
                  300  270                                                
                          270  300                                        
                                  300                                     
    Lathering rate                                                        
                  ⊚                                        
                       ⊚                                   
                          ⊚                                
                               ⊚                           
                                  ⊚                        
    Creaminess of bubbles                                                 
                  ⊚                                        
                       ⊚                                   
                          ⊚                                
                               ⊚                           
                                  ⊚                        
    Retention of bubbles                                                  
                  100  100                                                
                          100   99                                        
                                   95                                     
    Touch of bubbles                                                      
                  ⊚                                        
                       ⊚                                   
                          ⊚                                
                               ⊚                           
                                  ⊚                        
    Sliminess     ◯                                           
                       ◯                                      
                          ◯                                   
                               ◯                              
                                  ◯                           
    Jarring feeling (hands)                                               
                  ⊚                                        
                       ⊚                                   
                          ⊚                                
                               ⊚                           
                                  ⊚                        
    Jarring feeling (hair)                                                
                  ⊚                                        
                       ⊚                                   
                          ⊚                                
                               ⊚                           
                                  ⊚                        
    Refreshed feeling                                                     
                  ⊚                                        
                       ⊚                                   
                          ⊚                                
                               ⊚                           
                                  ⊚                        
    Smells        ⊚                                        
                       ⊚                                   
                          ⊚                                
                               ⊚                           
                                  ⊚                        
__________________________________________________________________________
                  Comparative Examples                                    
                  1  2  3  4  5  6  7                                     
__________________________________________________________________________
Acyl                                                                      
    Lauroyl glycine TEA                                                   
                  100                                                     
amino                                                                     
    Lauroyl glycine sodium                                                
                     100                                                  
acid                                                                      
    Myristoyl glycine potassium                                           
                        100       86                                      
salt                                                                      
    Lauroyl alanine TEA    100                                            
    Lauroyl β-alanine potassium                                      
                              100                                         
Higher                                                                    
    Sodium laurate                  100                                   
fatty                                                                     
    Potassium laurate             14                                      
acid                                                                      
    Coconut oil fatty acid TEA                                            
salt                                                                      
    Potassium myristate                                                   
Higher                                                                    
    Cetanol                                                               
alcohol                                                                   
    Lauryl alcohol                                                        
Results                                                                   
    Bubble volume (ml)                                                    
                  270                                                     
                     270                                                  
                        270                                               
                           240                                            
                              270                                         
                                 270                                      
                                    270                                   
    Lathering rate                                                        
                  x  x  x  x  x  ⊚                         
                                    ⊚                      
    Creaminess of bubbles                                                 
                  x  x  Δ                                           
                           x  x  ⊚                         
                                    ⊚                      
    Retention of bubbles (%)                                              
                   60                                                     
                      68                                                  
                         74                                               
                            75                                            
                               65                                         
                                  95                                      
                                     60                                   
    Touch of bubbles                                                      
                  Δ                                                 
                     Δ                                              
                        Δ                                           
                           Δ                                        
                              Δ                                     
                                 ⊚                         
                                    ⊚                      
    Sliminess     x  x  x  x  x  ◯                            
                                    ◯                         
    Jarring feeling (hands)                                               
                  ⊚                                        
                     ⊚                                     
                        ⊚                                  
                           ⊚                               
                              ⊚                            
                                 Δ                                  
                                    x                                     
    Jarring feeling (hair)                                                
                  ⊚                                        
                     ⊚                                     
                        ⊚                                  
                           ⊚                               
                              ⊚                            
                                 Δ                                  
                                    x                                     
    Refreshed feeling                                                     
                  Δ                                                 
                     Δ                                              
                        Δ                                           
                           Δ                                        
                              Δ                                     
                                 ◯                            
                                    ⊚                      
    Smells        ◯                                           
                     ◯                                        
                        ◯                                     
                           ◯                                  
                              ◯                               
                                 x  x                                     
__________________________________________________________________________
 *TEA = triethanolamine                                                   
 
    
     Inventive Examples 11 to 21 and Comparative Examples 8 to 18 
     In order to examine the effects of the joint use of the detergent composition of the present invention with other surface active agents, physical property measurement and organoleptic tests were carried out in the same manner as described in the preceding inventive examples. In this case, each aqueous solution was prepared by weighing the respective surface active agents in the amount (g) shown in Table 4 and adding purified water to the weighed agents in such an amount that the total weight was adjusted to 100 g. The pH value of each solution was found to be 7 to 8. 
     The results are shown in Table 4. 
     
                                           TABLE 4                                 
__________________________________________________________________________
                    Inventive Examples                                    
                    11 12 13 14 15 16                                     
__________________________________________________________________________
Acyl Cocoyl glycine TEA                                                   
                    5  10 10       20                                     
amino                                                                     
     Cocoyl glycine potassium                                             
                             20 20                                        
acid Cocoyl glycine sodium                                                
salt Lauroyl glycine sodium                                               
     Cocoyl alanine TEA                                                   
     Cocoyl β-alanine TEA                                            
Higher                                                                    
     Coconut oil fatty acid                                               
                       0.5                                                
                          0.5                                             
fatty                                                                     
     potassium                                                            
acid Soap base                                                            
salt Coconut oil fatty acid TEA                                           
                    0.5      0.5                                          
                                1  2.5                                    
     Potassium myristate                                                  
Higher                                                                    
     Cetanol                 0.5   3                                      
alcohol                                                                   
     Lauryl alcohol             0.5                                       
Anionic                                                                   
     Lauroyl methyltaurine                                                
                    5                                                     
surface                                                                   
     sodium                                                               
active                                                                    
     Monolauryl phosphate TEA                                             
                             2     5                                      
agent                                                                     
     Sodium cocoyl isethionate                                            
Ampho-                                                                    
     Lauryl dimethylaminoacetic                                           
                    8           10                                        
teric                                                                     
     acid betaine                                                         
surface                                                                   
     2-Lauryl-N-carboxymethyl-N-                                          
                       3                                                  
active                                                                    
     hydroxyethylimidazolinium                                            
agent                                                                     
     betaine                                                              
     Coconut oil fatty acid                                               
                          3                                               
     amide propyldimethylamino                                            
     acetic acid betaine                                                  
     Lauryl dimethylamino-2- 5                                            
     hydroxypropyl sulfobetaine                                           
Nonionic                                                                  
     Coconut oil fatty acid                                               
                    2  2  2        3                                      
surface                                                                   
     diethanolamide                                                       
active                                                                    
     Lauryl polyglycoside    1                                            
agent                                                                     
Results                                                                   
     Bubble volume (ml)                                                   
                    295                                                   
                       290                                                
                          290                                             
                             298                                          
                                280                                       
                                   310                                    
     Lathering rate ⊚                                      
                       ⊚                                   
                          ⊚                                
                             ◯                                
                                ⊚                          
                                   ⊚                       
     Creaminess of bubbles                                                
                    ⊚                                      
                       ⊚                                   
                          ⊚                                
                             ⊚                             
                                ⊚                          
                                   ⊚                       
     Retention of bubbles (%)                                             
                    88 99 99 99 97 99                                     
     Touch of bubbles                                                     
                    ◯                                         
                       ⊚                                   
                          ⊚                                
                             ⊚                             
                                ⊚                          
                                   ⊚                       
     Jarring feeling (hands)                                              
                    ⊚                                      
                       ⊚                                   
                          ⊚                                
                             ⊚                             
                                ⊚                          
                                   ⊚                       
     Jarring feeling (hair)                                               
                    ⊚                                      
                       ⊚                                   
                          ⊚                                
                             ⊚                             
                                ⊚                          
                                   ⊚                       
     Sliminess      ◯                                         
                       ◯                                      
                          ◯                                   
                             ◯                                
                                ◯                             
                                   ◯                          
     Refreshed feeling                                                    
                    ◯                                         
                       ◯                                      
                          ◯                                   
                             ⊚                             
                                ⊚                          
                                   ⊚                       
     Smells         ◯                                         
                       ◯                                      
                          ◯                                   
                             ⊚                             
                                ◯                             
                                   ◯                          
__________________________________________________________________________
                    Inventive Examples                                    
                    17  18 19  20 21                                      
__________________________________________________________________________
Acyl Cocoyl glycine TEA                                                   
amino                                                                     
     Cocoyl glycine potassium                                             
acid Cocoyl glycine sodium                                                
salt Lauroyl glycine sodium                                               
                    20  20                                                
     Cocoyl alanine TEA    25                                             
     Cocoyl β-alanine TEA 25 20                                      
Higher                                                                    
     Coconut oil fatty acid                                               
fatty                                                                     
     potassium                                                            
acid Soap base      1                                                     
salt Coconut oil fatty acid TEA                                           
                               2.5                                        
     Potassium myristate                                                  
                        1  2.5    2                                       
Higher                                                                    
     Cetanol                                                              
alcohol                                                                   
     Lauryl alcohol            3                                          
Anionic                                                                   
     Lauroyl methyltaurine                                                
surface                                                                   
     sodium                                                               
active                                                                    
     Monolauryl phosphate TEA                                             
agent                                                                     
     Sodium cocoyl isethionate                                            
                    5                                                     
Ampho-                                                                    
     Lauryl dimethylaminoacetic                                           
teric                                                                     
     acid betaine                                                         
surface                                                                   
     2-Lauryl-N-carboxymethyl-N-  10                                      
active                                                                    
     hydroxyethylimidazolinium                                            
agent                                                                     
     betaine                                                              
     Coconut oil fatty acid                                               
     amide propyldimethylamino                                            
     acetic acid betaine                                                  
     Lauryl dimethylamino-2-                                              
     hydroxypropyl sulfobetaine                                           
Nonionic                                                                  
     Coconut oil fatty acid                                               
                           5      5                                       
surface                                                                   
     diethanolamide                                                       
active                                                                    
     Lauryl polyglycoside                                                 
                        10     2.5                                        
agent                                                                     
Results                                                                   
     Bubble volume (ml)                                                   
                    300 270                                               
                           270 300                                        
                                  290                                     
     Lathering rate ⊚                                      
                        ⊚                                  
                           ⊚                               
                               ⊚                           
                                  ⊚                        
     Creaminess of bubbles                                                
                    ⊚                                      
                        ⊚                                  
                           ⊚                               
                               ⊚                           
                                  ⊚                        
     Retention of bubbles (%)                                             
                    100 100                                               
                           100 99 95                                      
     Touch of bubbles                                                     
                    ⊚                                      
                        ⊚                                  
                           ⊚                               
                               ⊚                           
                                  ⊚                        
     Jarring feeling (hands)                                              
                    ⊚                                      
                        ⊚                                  
                           ⊚                               
                               ⊚                           
                                  ⊚                        
     Jarring feeling (hair)                                               
                    ⊚                                      
                        ⊚                                  
                           ⊚                               
                               ⊚                           
                                  ⊚                        
     Sliminess      ◯                                         
                        ◯                                     
                           ◯                                  
                               ◯                              
                                  ◯                           
     Refreshed feeling                                                    
                    ◯                                         
                        ◯                                     
                           ⊚                               
                               ◯                              
                                  ◯                           
     Smells         ◯                                         
                        ◯                                     
                           ◯                                  
                               ◯                              
                                  ◯                           
__________________________________________________________________________
                    Comparative Examples                                  
                    8  9  10 11 12 13                                     
__________________________________________________________________________
Acyl Cocoyl glycine TEA                                                   
                    5                                                     
amino                                                                     
     Cocoyl glycine potassium                                             
acid Cocoyl glycine sodium                                                
salt Lauroyl glycine sodium                                               
                          20 20 20                                        
     Cocoyl alanine TEA                                                   
                       7           25                                     
     Cocoyl β-alanine TEA                                            
Higher                                                                    
     Coconut oil fatty acid                                               
fatty                                                                     
     potassium                                                            
acid Soap base                                                            
salt Coconut oil fatty acid TEA                                           
     Potassium myristate                                                  
Higher                                                                    
     Cetanol           0.5                                                
alcohol                                                                   
     Lauryl alcohol                                                       
Anionic                                                                   
     Lauroyl methyltaurine                                                
                    5                                                     
surface                                                                   
     sodium                                                               
active                                                                    
     Monolauryl phosphate TEA                                             
                       2                                                  
agent                                                                     
     Sodium cocoyl isethionate                                            
                             5                                            
Ampho-                                                                    
     Lauryl dimethylaminoacetic                                           
                    8                                                     
teric                                                                     
     acid betaine                                                         
surface                                                                   
     2-Lauryl-N-carboxymethyl-N-                                          
active                                                                    
     hydroxyethylimidazolinium                                            
agent                                                                     
     betaine                                                              
     Coconut oil fatty acid                                               
     amide propyldimethylamino                                            
     acetic acid betaine                                                  
     Lauryl dimethylamino-2-                                              
                       5                                                  
     hydroxypropyl sulfobetaine                                           
Nonionic                                                                  
     Coconut oil fatty acid                                               
                    2              5                                      
surface                                                                   
     diethanolamide                                                       
active                                                                    
     Lauryl polyglycoside                                                 
                       1  10    10                                        
agent                                                                     
Results                                                                   
     Bubble volume (ml)                                                   
                    270                                                   
                       240                                                
                          230                                             
                             240                                          
                                250                                       
                                   235                                    
     Lathering rate ⊚                                      
                       Δ                                            
                          Δ                                         
                             Δ                                      
                                Δ                                   
                                   Δ                                
     Creaminess of bubbles                                                
                    x  x  x  x  x  x                                      
     Retention of bubbles (%)                                             
                    60 64 63 67 68 64                                     
     Touch of bubbles                                                     
                    Δ                                               
                       Δ                                            
                          Δ                                         
                             Δ                                      
                                Δ                                   
                                   Δ                                
     Jarring feeling (hands)                                              
                    ◯                                         
                       x  ⊚                                
                             ⊚                             
                                ⊚                          
                                   ⊚                       
     Jarring feeling (hair)                                               
                    ⊚                                      
                       ⊚                                   
                          x  Δ                                      
                                Δ                                   
                                   ◯                          
     Sliminess      x  x  x  x  x  x                                      
     Refreshed feeling                                                    
                    x  x  x  x  x  x                                      
     Smells         ◯                                         
                       ◯                                      
                          ◯                                   
                             ◯                                
                                ◯                             
                                   ◯                          
__________________________________________________________________________
                    Comparative Examples                                  
                    14  15 16  17 181                                     
__________________________________________________________________________
Acyl Cocoyl glycine TEA     85                                            
amino                                                                     
     Cocoyl glycine potassium   80                                        
acid Cocoyl glycine sodium         85                                     
salt Lauroyl glycine sodium                                               
     Cocoyl alanine TEA                                                   
     Cocoyl β-alanine TEA                                            
                     25  20                                               
Higher                                                                    
     Coconut oil fatty acid     20                                        
fatty                                                                     
     potassium                                                            
acid Soap base                                                            
salt Coconut oil fatty acid TEA                                           
                            15                                            
     Potassium myristate           13                                     
Higher                                                                    
     Cetanol                                                              
alcohol                                                                   
     Lauryl alcohol                                                       
Anionic                                                                   
     Lauroyl methyltaurine                                                
surface                                                                   
     sodium                                                               
active                                                                    
     Monolauryl phosphate TEA                                             
agent                                                                     
     Sodium cocoyl isethionate                                            
Ampho-                                                                    
     Lauryl dimethylaminoacetic                                           
teric                                                                     
     acid betaine                                                         
surface                                                                   
     2-Lauryl-N-carboxymethyl-N-                                          
                         10                                               
active                                                                    
     hydroxyethylimidazolinium                                            
agent                                                                     
     betaine                                                              
     Coconut oil fatty acid                                               
     amide propyldimethylamino                                            
     acetic acid betaine                                                  
     Lauryl dimethylamino-2-                                              
     hydroxypropyl sulfobetaine                                           
Nonionic                                                                  
     Coconut oil fatty acid                                               
                         5                                                
surface                                                                   
     diethanolamide                                                       
active                                                                    
     Lauryl polyglycoside                                                 
                     5      5                                             
agent                                                                     
Results                                                                   
     Bubble volume (ml)                                                   
                    260 230                                               
                           300 300                                        
                                  300                                     
     Lathering rate Δ                                               
                        Δ                                           
                           ⊚                               
                               ⊚                           
                                  ⊚                        
     Creaminess of bubbles                                                
                    x   x  ⊚                               
                               ⊚                           
                                  ⊚                        
     Retention of bubbles (%)                                             
                     68  63                                               
                            99  98                                        
                                   97                                     
     Touch of bubbles                                                     
                    Δ                                               
                        Δ                                           
                           ⊚                               
                               ⊚                           
                                  ⊚                        
     Jarring feeling (hands)                                              
                    ⊚                                      
                        ⊚                                  
                           x   x  x                                       
     Jarring feeling (hair)                                               
                    ⊚                                      
                        ◯                                     
                           x   x  x                                       
     Sliminess      x   x  ◯                                  
                               ◯                              
                                  ◯                           
     Refreshed feeling                                                    
                    x   x  ⊚                               
                               ⊚                           
                                  ⊚                        
     Smells         ◯                                         
                        ◯                                     
                           x   x  x                                       
__________________________________________________________________________
 
    
     Inventive Examples 22 and 23 and Comparative Example 19 
     In order to examine the effects of pH on the detergent composition of the present invention, detergent compositions of the compositions shown in Table 5 were prepared and their bubble volumes and used feelings were evaluated. The pH value of each detergent composition was adjusted with potassium hydroxide or citric acid. 
     
                       TABLE 5                                                     
______________________________________                                    
              Comparative                                                 
                       Inventive                                          
              Example  Examples                                           
              19       22       23                                        
______________________________________                                    
Potassium lauroyl glycinate                                               
                25         25       25                                    
Potassium laurate                                                         
                1.5        1.5      1.5                                   
Water           balance    balance  balance                               
pH              5.5        6.5      9.0                                   
Bubble volume (ml)                                                        
                180        280      320                                   
Stiffness       x          ◯                                  
                                    ◯                         
Retention of bubbles                                                      
                x          ◯                                  
                                    ◯                         
______________________________________                                    
 
    
     Used feelings, namely stiffness and bubble retention when the side of the forearm was washed with a nylon towel using each of the above compositions, were evaluated based on the following criteria by 20 expert panelists consisting of 10 females and 10 males. 
     Stiffness ⊚: completely no stiffness, ◯: no stiffness, Δ: usual, and ×: stiffen. 
     Bubble retention ⊚: very good, ◯: good, Δ: usual, and ×: not enough. 
     Inventive Examples 24 to 26 
     In order to examine the effects of the addition of polyhydric alcohols to the detergent composition of the present invention, detergent compositions of the compositions shown in Table 6 were prepared and their bubble volumes and used feelings were evaluated. 
     
                       TABLE 6                                                     
______________________________________                                    
              Inventive Examples                                          
              24      25       26                                         
______________________________________                                    
Potassium lauroyl glycinate                                               
                25        25       25                                     
Potassium laurate                                                         
                1.5       1.5      1.5                                    
Glycerol        5         25       5                                      
Propylene glycol                   10                                     
1,3-Butylene glycol                5                                      
Water           balance   balance  balance                                
pH              8.2       8.2      8.2                                    
Bubble volume (ml)                                                        
                310       305      305                                    
Stiffness       ⊚                                          
                          ⊚                                
                                   ⊚                       
Retention of bubbles                                                      
                ◯                                             
                          ◯                                   
                                   ◯                          
______________________________________                                    
 
    
     Inventive Examples 27 to 31 
     In order to examine the effects of N-acyl amino acid salts on the detergent composition of the present invention, detergent compositions of the compositions shown in Table 7 were prepared and their bubble volumes and used feelings were evaluated. The pH value of each of the detergent compositions was adjusted with 25% aqueous solutions of the respective bases mixed at the mixing ratios shown in the table. 
     
                       TABLE 7                                                     
______________________________________                                    
Inventive Examples                                                        
27           28       29       30     31                                  
______________________________________                                    
Lauroyl 25       25       25     25     25                                
glycine                                                                   
Lauric acid                                                               
        1.5      1.5      1.5    1.5    1.5                               
Base                                                                      
KOH     90       10              10     90                                
NaOH    10       90       25                                              
TEA                       75     90     10                                
Glycerol                         5      10                                
Propylene                               10                                
glycol                                                                    
1,3-                             2                                        
Butylene                                                                  
glycol                                                                    
Water   balance  balance  balance                                         
                                 balance                                  
                                        balance                           
pH      8.5      7.8      7.1    6.8    8.0                               
Bubble  315      310      300    305    310                               
volume                                                                    
(ml)                                                                      
Stiffness                                                                 
        ◯                                                     
                 ◯                                            
                          ◯                                   
                                 ⊚                         
                                        ⊚                  
Bubble  ⊚                                                  
                 ⊚                                         
                          ⊚                                
                                 ⊚                         
                                        ⊚                  
retention                                                                 
______________________________________                                    
 
    
     Inventive Example 32 
     Detergent compositions shown in the following Tables 8 to 16 were prepared in the usual way based on various formulations of materials shown in the tables. 
     
                       TABLE 8                                                     
______________________________________                                    
Body shampoo                                                              
______________________________________                                    
N-Coconut oil fatty acid acyl glycine potassium salt                      
                             20 g                                         
Coconut oil fatty acid sodium salt                                        
                             2                                            
Coconut oil fatty acid diethanolamide                                     
                             5                                            
Cetanol                      1                                            
Sodium chloride              2                                            
Methylparaben                0.2                                          
Sodium benzoate              0.2                                          
Sodium citrate               0.5                                          
Purified water              balance                                       
Total                       100 g                                         
pH 8.2                                                                    
______________________________________                                    
 
    
     
                       TABLE 9                                                     
______________________________________                                    
Cleansing foam                                                            
______________________________________                                    
N-Coconut oil fatty acid acyl DL-alanine sodium salt                      
                             20 g                                         
Potassium myristate          2                                            
Propylene glycol             4                                            
Cetostearyl alcohol          3                                            
Coconut oil fatty acid diethanolamide                                     
                             6                                            
Sodium chloride              2                                            
Sodium sulfate               4                                            
Methylparaben                0.2                                          
Sodium benzoate              0.2                                          
Sodium citrate               0.5                                          
Purified water              balance                                       
Total                       100 g                                         
pH 8.7                                                                    
______________________________________                                    
 
    
     
                       TABLE 10                                                    
______________________________________                                    
Hair shampoo                                                              
______________________________________                                    
Lauroyl glycine sodium salt                                               
                           5 g                                            
Sodium laurate             0.4                                            
Sodium polyoxyethylene lauryl sulfate                                     
                           6                                              
1,3-Butylene glycol        4                                              
Coconut oil fatty acid diethanolamide                                     
                           7                                              
Sodium chloride            2                                              
Sodium edetate             0.1                                            
Purified water            balance                                         
Total                     100 g                                           
pH 7.5                                                                    
______________________________________                                    
 
    
     
                       TABLE 11                                                    
______________________________________                                    
Hair shampoo                                                              
______________________________________                                    
Lauryl dimethylaminoacetic acid betaine                                   
                           10 g                                           
Myristoyl glycine TEA      10                                             
Myristoyl glycine lysine   7                                              
Palmitic acid TEA          0.7                                            
Glycerol                   2.5                                            
1,3-Butylene glycol        2                                              
Coconut oil fatty acid diethanolamide                                     
                           7                                              
Sodium chloride            2                                              
Sodium edetate             0.1                                            
Purified water            balance                                         
Total                     100 g                                           
pH 7.2                                                                    
______________________________________                                    
 
    
     
                       TABLE 12                                                    
______________________________________                                    
Hair shampoo                                                              
______________________________________                                    
Coconut oil fatty acid amidopropyl dimethylamino                          
                            10 g                                          
acetic acid betaine                                                       
Palm kernel oil fatty acid glycine TEA                                    
                            5                                             
Stearic acid lysine salt    0.2                                           
Lauric acid diethanolamide  4                                             
Myristyl alcohol            1                                             
Sodium chloride             2                                             
1-Menthol                   0.1                                           
Purified water             balance                                        
Total                      100 g                                          
pH 7.4                                                                    
______________________________________                                    
 
    
     
                       TABLE 13                                                    
______________________________________                                    
Hair shampoo                                                              
______________________________________                                    
Lauryl dimethylamino-2-hydroxypropyl sulfobetaine                         
                             12 g                                         
Myristoyl-β-alanine TEA                                              
                             6                                            
Myristic acid lysine salt    0.1                                          
Glycerol                     5                                            
Lauric acid diethanolamide   4                                            
Sodium chloride              2                                            
Herb extract                 0.1                                          
Purified water              balance                                       
Total                       100 g                                         
pH 7.0                                                                    
______________________________________                                    
 
    
     
                       TABLE 14                                                    
______________________________________                                    
Syndet bar                                                                
______________________________________                                    
Coconut oil isethionic acid sodium salt                                   
                             60 g                                         
N-Palm kernel oil fatty acid acyl β-alanine                          
                             25 g                                         
potassium salt                                                            
Coconut oil fatty acid lysine salt                                        
                             2                                            
Isoprene glycol              5                                            
Lauryl glycoside             4                                            
Cationized cellulose         0.2                                          
Trimethylaminoacetic acid betaine                                         
                             2                                            
Sodium sulfite               0.05                                         
Sodium thiosulfate           0.1                                          
1-Hydroxyethylidene-1,1-diphosphonic acid Na salt                         
                             0.1                                          
Purified water              balance                                       
Total                       100 g                                         
pH 7.9                                                                    
______________________________________                                    
 
    
     
                       TABLE 15                                                    
______________________________________                                    
Cleansing liquid                                                          
______________________________________                                    
Palm kernel oil fatty acid glycine lysine salt                            
                           15 g                                           
Palm kernel oil fatty acid                                                
                           1                                              
Sodium laurylsulfate       5                                              
Trehalose                  5                                              
Sodium polyacrylate        2                                              
PCA soda                   0.1                                            
Purified water            balance                                         
Total                     100 g                                           
pH 7.2                                                                    
______________________________________                                    
 
    
     
                       TABLE 16                                                    
______________________________________                                    
Aerosol detergent                                                         
______________________________________                                    
Coconut oil glycine arginine salt                                         
                          20 g                                            
Coconut oil fatty acid arginine salt                                      
                          1.5                                             
Lauric acid TEA           0.5                                             
Glycerol                  4.5                                             
Sodium polyglutamate      0.1                                             
Coconut oil fatty acid ethanolamide                                       
                          3                                               
Sodium chloride           2                                               
Butylparaben              0.2                                             
Sodium benzoate           0.2                                             
Sodium citrate            0.5                                             
Propellant                10                                              
Purified water           balance                                          
Total                    100 g                                            
pH 7.6                                                                    
______________________________________                                    
 
    
     Industrial Applicability 
     The considerable improvement of the properties of N-acyl amino acid salts as detergents thus achieved by the present invention has rendered possible easy provision of excellent detergent compositions.