Patent Publication Number: US-3969087-A

Title: Gels of nonpolar liquids with N-acyl amino acids and derivatives thereof as gelling agents

Description:
BACKGROUND OF THE INVENTION 
     1. Field of the Invention 
     The present invention relates to the gellation or solidification of non-polar organic liquids, and to products obtained therefrom. 
     2. Description of the Prior Art 
     Non-polar organic liquids are used for various purposes in fuels, motor oils, paints, cosmetics, edible oils and the like. 
     In the practical use of non-polar organic liquids, it is often desirable to render them solid. If a container is damaged or broken open, the organic liquids stored therein flow out and spread over a wide area, and recovery of the spilled liquid is difficult. If the spilled organic liquids are inflammable, they burn once ignited. For example, fire and smoke inhalation cause many deaths in otherwise survivable aircraft accidents. The fires usually are caused when the highly volatile fuel spills from damaged tanks and splatters over a wide area. Fuel vaporizes and is easily ignited by hot engine parts or sparks from metal impact. On the contrary, when fuels are gelled, the degree of vaporization and the extent to which the fuel is scattered upon impact are decreased, and so the danger of rapidly spreading fire or explosion is substantially reduced. Thus, gelled fuels are a significant safety factor in jet aircraft. Also, gelled fuels may be handled like fluid liquids under certain stress. Moreover, gelling agents for organic liquids are useful for facilitating the removal or recovery of spilled non-polar organic liquids or other aggregates of non-polar organic liquids, and for preventing the leakage or spillage of such non-polar organic liquids from leaking tanks or holes. 
     A need continues to exist for methods of gelling non-polar organic liquids to avoid the many problems when such liquids are spilled. 
     SUMMARY OF THE INVENTION 
     Accordingly, one object of the present invention is to provide a method of gelling non-polar organic liquids with N-acylamino acids and derivatives thereof. 
     Another object of the present invention is to provide a method of gelling flammable non-polar organic liquids with an N-acylamino acid or derivative thereof to increase the safety factor when handling such liquids. 
     Briefly, these objects and other objects of the present invention as hereinafter will become more readily apparent can be attained by a process of homogeneously admixing a non-polar organic liquid with a small amount of an N-acylamino acid or derivative thereof, and allowing the mixed solution to stand so that the gel might form. 
     DESCRIPTION OF THE PREFERRED EMBODIMENTS 
     According to the present invention, gels may be prepared by homogeneously admixing non-polar organic liquids with effectively small proportions of at least one of an N-acylamino acid related compound having the general formula: ##EQU1## wherein RCO is selected from the group consisting of C 2  to C 30  aliphatic acyl radicals and aralkyl acyl radicals, z is selected from the group of hydroxy, -NH 2 , -OR 1 , -NHR 2 , ##EQU2## and --0 -  R 5  NH 3   +   (where R 1 , R 2 , R 3 , R 4 , and R 5  are selected from C 1  to C 30  aliphatic hydrocarbon radicals and aralkyl radicals), X is hydrogen or methyl, and Y can be ##EQU3## (where R 6  is a C 1  to C 4  aliphatic hydrocarbon radical, benzyl, phenyl, --CH 2  OH, ##EQU4## --CH 2  SH, --CH 2  CH 2  S--CH 3 , or --(CH 2 ) p  --COZ(and p is a positive integer of 1 or 2, and Z is the same as above), --(CH 2 ) m  NHCOR (where m is a positive integer of 3 or 4 and COR is the same as above) or --(CH 2 ) n  -- (where n is a positive integer of 1 to 6), with the proviso that when Z is --OR 1 , ##EQU5## and R 6  is --(CH 2 ) m  NHCOR and that at least one of R, R 1 , R 2 , R 3 , R 4  or R 5  is a C 5  to C 30  aliphatic hydrocarbon radical to form a gel. 
     In the above general formula, the RCO radical is an aliphatic acyl radical derived from a saturated or unsaturated fatty acid having 2 to 30 carbon atoms such as, for example, acetic, acid, propionic acid, butyric acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, elaidic acid, 5 the naturally occurring mixed fatty acids, such as coconut oil fatty acid, tallow oil fatty acid or hydrogenated tallow oil fatty acid and synthetic fatty acids or an aralkyl acyl radical such as phenylacetyl, α-naphthaleneacetyl or hydrocinnamoyl. The R 1 , R 2 , R 3 , R 4  and R 5  groups are C 1  to C 30  alkyl or alkenyl hydrocarbon radicals such as methyl, ethyl, propyl, butyl, amyl, hexyl, cyclohexyl, octyl, nonyl, decyl, dodecyl, undecylenyl, hendecyl, tridecyl, tetradecyl, cetyl, pentadecyl, heptadecyl, hexadecyl, hexadecenyl, octadecyl, octadecenyl, octadecadienyl, oleyl, elaidyl or mixtures thereof, or aralkyl radicals such as benzyl and hydrocinnamyl. 
     The amino acid moiety of the gelling agent having the above formula (I), i.e., the radical with the formula: ##EQU6## 
     is preferably derived from acidic amino acids, neutral amino acids, sulfur containing amino acids, hydroxy amino acids, N-methyl derivatives of α-amino acids, ω-amides of acidic amino acids, basic amino acids, β-amino acids and ω-amino acids. Most preferably, the moiety expressed by formula (II) is derived from the group consisting of aspartic acid, glutamic acid, glutamine, glycine, sarcosine, α-alanine, β-alanine, α-aminobutyric acid, valine, norvaline, leucine, isoleucine, norleucine, phenylglycine, phenylalanine, serine, threonine, cysteine, methionine, N.sup.δ-acylornithine, N.sup.ε-acyllysine, γ-aminovaleric acid and ω-aminocaproic acid. 
     In the gelling agents of the present invention, at least one of the C 5  to C 30  higher aliphatic hydrocarbon radicals must be present either in the N-acyl moiety or in the other radical of the formula, i.e., the ester, amide or amine salt, or both moieties may contain a higher aliphatic hydrocarbon radical. 
     The following is a list of the number of gelling agents characterized by the above formula (I). The list of compounds is exemplary and presented for the purpose of illustration only and is not meant to be limiting in any manner. 
     1. Examples of the N-acyl amino acids include N-lauroyl-α-alanine, N.sup.α ,N.sup.δ-dicaproyl-, N.sup.α ,N.sup.δ-dicapryloyl-, N.sup.α ,N.sup.δ-didecanonoyl-, N.sup.α ,N.sup.δ-dilauroyl and N.sup.α ,N.sup.δ-dicocoyl orithine (cocoyl means the acyl radical of coconut oil fatty acid), N.sup.α ,N.sup.ε-dicaproyl-, N.sup.α ,N.sup.ε-dicapryloyllysine, N-lauroyl valine and N-lauroyl glutamic acid. 
     2. Examples of the N-acyl amino acid esters include N.sup.α, N.sup.δ-dicaprylylornithine octyl, decyl, lauryl and stearyl esters, N.sup.α ,N.sup.ε-dicapryloyllysine octyl, decyl and lauryl esters, N.sup.α ,N.sup.ε-dilauroyllysine hexyl, octyl, decyl and lauryl esters, N.sup.α ,N.sup.ε-dicocoyllysine hexyl, octyl, decyl and lauryl esters, N.sup.α ,N.sup.ε-di(tallowyl) and N.sup.α ,N.sup.ε-di(hydrogenated tallowyl) lysine hexyl, octyl, decyl and lauryl esters (tallowyl refers to the acyl radical of tallow oil fatty acid). 
     3. Examples of the N-acylamino acid amides include N-acetyl glutamic acid- α ,γ-dilauryl and -α ,γ-distearyl amides; N-caproyl glutamic acid-α ,γ-diamide,α-γ, -dibutyl, -α ,γ-dihexyl,-α ,γ-dioctyl, -α ,γ-dilauryl and -α ,γ-distearyl amides; N-lauroyl glutamic acid -α ,γ-diamide, -α ,γ-dibutyl, -α ,γ-dihexyl, -α ,γ-dioctyl, -α ,γ-dilauryl and -α ,γ-distearyl amides; N-cocoyl glutamic acid -α ,γ-diamide, -α ,γ-dibutyl, -α ,γ-dioctyl, -α ,γ-dilauryl and -α ,γ-distearyl amides; N-hydrogenated tallowyl glutamic acid -α ,γ-diamide, -α ,γ-dibutyl, -α ,γ-dhexyl, -α ,γ-dioctyl, -α ,γ-dilauryl and -α ,γ-distearyl amides; N.sup.α ,N.sup.ε-diacetyllysine octyl, lauryl and stearyl amides; N.sup.α,N.sup.ε-dicaproyllysine amide butyl, hexyl, octyl, lauryl and stearyl amides; N.sup.α ,N.sup.ε-dicapryloyllysine amide, butyl, dibutyl, hexyl, octyl, lauryl and stearyl amides; N.sup.α,N.sup.ε-dilauroyllysine amide, butyl, dibutyl, hexyl, octyl, lauryl and stearyl amides; N.sup.α,N.sup.ε-dicocoyllysine amide, butyl, dibutyl, hexyl, octyl, lauryl, stearyl amides; N.sup.α,N.sup.ε-di(hydrogenated tallowyl) lysine amide, butyl, dibutyl, hexyl, octyl, lauryl and stearyl amides; N-lauroylvaline amide, butyl, hexyl, octyl and lauryl amides; N-lauroylphenylalanine amide, butyl, hexyl, octyl and lauryl amides; N-capryloyl leucine amide, butyl, hexyl, octyl and lauryl amides; and N-palmitoylmethionine amide, butyl, hexyl and octyl amides. 
     4. Examples of the N-acyl amino acid amine salts include N.sup.α,N.sup.δ-dicaproyllysine butyl, octyl, lauryl and stearyl amine salts; N.sup.α,N.sup.δ-dilauroyllysine butyl, octyl, lauryl and stearyl amine salts; N.sup.α,N.sup.δ-dicocoyllysine butyl, octyl, lauryl and stearyl amine salts; N.sup.α,N.sup.ε-di(hydrogenated tallowyl) lysine butyl, octyl, lauryl and stearyl amine salts; and N-lauroylphenylalanine octyl, lauryl, and stearyl amine salts. 
     The gelling agents which may be employed in this invention can agglomerate to form a coherent structure and trap the non-polar organic liquid within the gel matrix. On the other hand, the highly oil soluble derivatives of N-acyl amino acids such as N-acylglutamic acid diesters and N-acyl neutral amino acid esters cannot agglomerate to form a coherent structure and so cannot form a gel network. 
     Among the four kinds of gelling agents which may be employed in this invention, the N-acyl amino acids may be easily prepared by acylating the amino acid with acyl chloride in an aqueous media in the presence of a base such as sodium hydroxide. The ester or amide of the N-acylamino acid may be obtained by reacting an N-acyl amino acid with an alcohol or an amine (inclusive of ammonia) in the presence or absence of an acidic catalyst while heating. The amine salt of the N-acyl amino acid may be obtained by neutralizing the N-acyl amino acid with an amine. 
     The gels of this invention may be prepared simply by homogeneously admixing a gelling agent having the above formula (I) with non-polar organic liquids and then allowing the mixture to stand until gel formation occurs. Homogeneous mixture of the reactants may be conducted at temperatures ranging from room temperature to the boiling point of the non-polar organic liquid. The gelling agent may be added in the form of very fine powdered particles or as solutions dissolved in a suitable solvent such as acetone, methanol or ethanol, or in a small amount of the hot non-polar organic liquids to be gelled. The gel of the present invention may be formed by dissolving the gelling agent in a non-polar organic liquid at elevated temperatures, and thereafter cooling the resulting solution to a low temperature whereby gel formation occurs while standing. In all cases gel formation occurs as long as a mixture of a gelling agent and the non-polar organic liquid is sufficiently homogenized. 
     According to the present invention, the gelling agent may be employed generally in the range of 0.05% to 20% by weight based upon the amount of non-polar organic liquid to be gelled. The firmness of the resulting gel may be optionally varied depending on the kind and amount of gelling agent added. However, the addition of more than 10% by weight of the gelling agent causes no appreciable increase in the shear strength of the resultant gel. The preferred amount of the gelling agent is 0.1 to 10% by weight based upon the non-polar organic liquid. A suitable amount of gelling agent may be determined experimentally and it will vary with the desired physical properties of the gel and other components therein. 
     The non-polar organic liquids which can be gelled by the process of the present invention are generally almost any of those which have a dielectric constant of less than about 20 which have a solubility less than 10% by weight in water. Suitable examples of such non-polar organic liquids include petroleum hydrocarbons such as gasoline, naphthas, kerosine, gas oil, heavy oil and crude oil; lubricating oils such as spindle oil and turbine oil; liquid paraffin, pure hydrocarbons such as benzene, xylene, toluene, hexane, heptane, octane, and cyclohexane; esters such as butyl acetate, amyl acetate, diethyl phthalate, dibutyl phthalate, dioctyl phthalate, diethyl sebacate and dioctyl sebacate; ketones such as methyl isobutyl ketone and diisobutyl ketone; aldehyde such as anisaldehyde; chlorinated hydrocarbons such as carbon tetrachloride, tetrachloroethylene and chlorobenzene; phosphoric esters such as tributyl phosphate and tricresyl phosphate; normally liquid polyoxyalkylene monoalkyl ethers such as polyoxyethylenemonolauryl ether containing 4 to 6 oxyethylene units, polyoxypropylene mono C 4  to C 12  alkyl ether containing 10 to 50 oxypropylene units such as polyoxypropylene mono butyl ether, polyoxypropylene mono lauryl ether; normally liquid polyoxypropylene mono lauryl ether; normally liquid polyoxyalkylene glycol fatty acid esters, such as polyoxyethylene glycol lauric or oleic acid ester containing 4 to 6 oxyethylene units; fatty oils such as corn oil, soybean oil, olive oil, rape seed oil, cotton seed oil, sardine oil, herring oil and whale oil; silicone oil, mixtures thereof and liquids containing predominantly these non-polar organic liquids. On the other hand, organic liquids having a dielectric constant greater than about 20, such as acetone and ethanol, and having a solubility more than 10% by weight in water such as acetic acid and butyric acid do not gel satisfactorily. 
     The non-polar organic liquids may contain other ingredients as may be desired to achieve special effects. An emulsion or suspension of the non-polar organic liquid with water may be gelled. In the case of a system which forms a water in oil type emulsion or suspension wherein the water content is below 50%, the entire system may be gelled. And, in the case of a system which forms an oil in water type emulsion or suspension, the non-polar organic component may be gelled as an aggregate. 
     The gelling agent of the present invention is useful for the gelation of fuel oil and the recovery of drained oil. Furthermore, a wide variety of other materials can be prepared as for example, gelling or thixotropic agents for paints or inks, gelling agents for greases, solidifying agents for margarine comprising liquid oils, gelling agents or binders for liquid oil type cosmetics, binders or carriers for medicaments and gelling agents for napalm type incendiaries. 
     By the process of the present invention, gelled non-polar organic liquid are easily prepared with no involved procedures and the present gelling agents are capable of gelling non-polar organic liquid in only small amounts. Moreover, when the gelling agents of the present invention are employed for fuel oils, the fuels are gelled and the safety factor increases. Furthermore, the gelling agents themselves are flammable and they do not disturb the flammability of the fuel. 
     Having generally described the invention, a further understanding can be obtained by reference to certain specific examples which are provided herein for purposes of illustration only are not intended to be limiting unless otherwise specified. 
    
    
     EXAMPLE 1 
     One gram of each of the derivatives of N-acylamino acids shown in the table below was dissolved in 100 grams of kerosine with stirring at a temperature of 120°C. The resulting solutions were cooled to room temperature. After standing for 2 hours, gelled kerosine was prepared. Gelled olive oil was obtained similarly. The shear strength of these gels was measured with a rheo meter, RUD-J (a product of Fuji Rika Kogyo Co.). The results are tabulated below. 
     
         Derivatives of N-acylamino acids                                          
                      Shear strength of gel                               
                      Kerosine                                            
                            Olive Oil                                     
                      g/cm.sup.2                                          
                            g/cm.sup.2                                    
__________________________________________________________________________
N.sup.α,N.sup.ε-dicaproyllysine lauryl ester                
                      36    122                                           
N.sup.α,N.sup.ε-distearoyllysine n-hexyl ester              
                      14    63                                            
N.sup.α,N.sup.ε-dilauroyllysine benzyl ester                
                      9.3   7.6                                           
N.sup.α,N.sup.ε-di(2-ethyl-hexanoyl)lysine lauryl           
ester                 15    16                                            
N.sup.α,N.sup.δ-dicapryloylornithine lauryl                   
                      13ter 36                                            
N-lauroylglutamic acid-α,γ-diamide                            
                      28    29                                            
N-lauroylglutamic acid-α,γ-di-n-                              
butylamide            223   235                                           
N-lauroylglutamic acid-α,γ-distearyl-                         
amide                 41    26                                            
N-acetylglutamic acid-α,γ-dilaurylamide                       
                      13    25                                            
N-phenacetylglutamic acid-α,γ-                                
dilaurylamide         11    10                                            
N-lauroylglutamic acid-α,γ-di(2-ethyl                         
hexylamide)           35    28                                            
N-stearoyl aspartic acid-α,β-di-n-                             
butylamide            12    13                                            
N-lauroyl valine n-butylamide                                             
                      3.0   19                                            
N-lauroyl sarcosine n-butylamide                                          
                      0.9   1.4                                           
N-palmitoyl-ε-amino caproic acid                                  
n-butylamide          3.0   4.0                                           
N.sup.α,N.sup.ε-dicapryloyllysine laurylamide               
                      153   89                                            
N.sup.α,N.sup.ε-dicapryloyllysine benzylamide               
                      12    13                                            
Laurylamine N-lauroyl valinate                                            
                      3.2   4.1                                           
Stearylamine N-lauroylalaninate                                           
                      3.1   4.2                                           
Laurylamine N-lauroylphenylalaninate                                      
                      4.0   74                                            
Stearlamine N.sup.α,N.sup.ε-dicapryloyllysinate             
                      17    61                                            
n-Butylamine N.sup.α,N.sup.ε-dilauroyllysinate              
                      20    25                                            
N.sup.α,N.sup.δ-dicapryloylornithine di-n-butyl               
amide                 1.9   2.9                                           
__________________________________________________________________________
 
    
     In addition to the gelled kerosines in the table above, gelled kerosines having a shear strength more than 15 g/cm 2  were obtained using the following acid derivatives. 
     N.sup.α,N.sup.δ-dicaproyl-, N.sup.α,N.sup.δ-dilauroyl-, N.sup.α,N.sup.δ-dicocoylornithine; N.sup.α,N.sup.ε-dicaproyl-, N.sup.α,N.sup.ε-dicapryloyl-, N.sup.α,N.sup.ε-dilauroyl-, N.sup.α,N.sup.ε-dicocoyllysine; N.sup.α,N.sup.δ-dicapryloyl ornithine n-octyl, 2-ethylhexyl, decyl esters; N.sup.α,N.sup.δ-dilauroylornithine n-hexyl, n-octyl, 2-ethylhexyl, decyl, lauryl esters; N.sup.α,N.sup.δ-dicocoylornithine n-hexyl, n-octyl, 2-ethylhexyl, decyl, lauryl esters; N.sup.α,N.sup.δ-distearoylornithine n-hexyl, n-octyl, 2-ethylhexyl, decyl, lauryl ester; N.sup.α,N.sup.δ-ditallowylornithine n-hexyl, n-octyl, 2-ethylhexyl, decyl, lauryl ester;N.sup.α,N.sup.ε-dicapryloyllysine n-hexyl, n-octyl, 2-ethylhexyl, decyl esters; N.sup.α,N.sup.ε-dilauroyllysine n-hexyl, n-octyl, laruyl, 2-ethylhexyl, decylesters;N.sup.α,N.sup.ε-dicocoyllysine n-hexyl, n-octyl, lauryl, 2-ethylhexyl, decyl esters; N.sup.α,N.sup.ε-distearoyllysine n-octyl, lauryl, n-ethylhexyl, decyl esters; N.sup.α,N.sup.εditallowyllysine n-hexyl, n-octyl, lauryl, 2-ethylhexyl, decyl esters; N-acetylglutamic acid-α,γ-distearylamide; N-capryloylglutamic acid-α,γ-diamide, di-n-butyl, di-isobutyl, di-n-octyl, di-2-ethylhexyl, dilauryl, distearylamide; N-cocoylglutamic acid-α,γ-diamide, di-n-butyl, diisobutyl, di-n-octyl, di-2-ethylhexyl, dilauryl, distearylamide; N-stearoylglutamic acid-α,γ-diamide, di-n-butyl, diisobutyl, di-n-octyl, di-2-ethylhexyl, dilauryl, distearylamide; N-tallowylglutamic acid-α,γ-diamide, di-n-butyl, diisobutyl, di-n-octyl, di-2-ethylhexyl, dilauryl, distearylamide; N-lauroylglutamic acid-α, γ-diisobutyl, dilaurylamide; N.sup.α,N.sup.ε-diacetyllysine lauryl, stearylamide; N.sup.α,N.sup.ε-dicapryloyllysine amide, n-butyl, isobutyl, n-octyl, 2-ethylhexyl, stearylamide; N.sup.α,N.sup.ε-dilauroyllysine amide, n-butyl, isobutyl, n-octyl, 2-ethylhexyl, lauryl, stearyl amide; N.sup.α,N.sup.ε-dicocoyllysine amide, n-butyl, isobutyl, n-octyl, 2-ethylhexyl, lauryl, stearylamide; N.sup.α,N.sup.ε-distearoyllysine amide, n-butyl, isobutyl, n-octyl, 2-ethylhexyl, lauryl, stearylamide; N.sup.α,N.sup.ε-ditallowyllysine amide, n-butyl, isobutyl, n-octyl, 2-ethylhexyl, lauryl, stearylamide; N.sup.α,N.sup.ε-dicapryloyllysine n-octyl-, 2-ethylhexyl-, lauryl-amine salt; N.sup.α,N.sup.ε-dilauroyllysine n-octyl-, 2-ethylhexyl-, lauryl-stearyl amine salt; N.sup.α,N.sup.ε-dicocoyllysine n-butyl-, isobutyl-, n-octyl-, 2-ethylhexyl-, lauryl-, stearyl amine salt; N.sup.α,N.sup.ε-distearoyllysine n-butyl-, isobutyl-, n-octyl-, 2-ethylhexyl-, lauryl-, stearyl amine salt; N.sup.α,N.sup.ε-ditallowyllysine n-butyl, isobutyl-, n-octyl-, 2-ethylhexyl-, lauryl-, stearyl amine salt; N.sup.α,N.sup.δ-dicapryloylornithine n-octyl-, 2-ethylhexyl-, lauryl-, stearyl amine salt; N.sup.α,N.sup.δ-dilauroylornithine n-butyl-, isobutyl-, n-octyl-, 2-ethylhexyl-, lauryl-, stearyl amine salt N.sup.α,N.sup.δ-dicocoylornithine n-butyl-, isobutyl-, n-octyl-, 2-ethylhexyl-, lauryl-, stearyl amine salt; N.sup.α,N.sup.δ-distearoylornithine n-butyl-, isobutyl-, n-octyl-, 2-ethylhexyl-, lauryl, stearyl amine salt; N.sup.α,N.sup.δ-ditallowylornithine n-butyl-, isobutyl-, n-octyl-, 2-ethylhexyl-, lauryl-, stearyl amine salt. 
     EXAMPLE 2 
     Gelled non-polar organic liquids containing 1 wt% of N.sup.α,N.sup.δ-dicapryloylornithine, N-lauroylglutamic acid-α, γ-di-n-butylamide or stearylamine N.sup.α,N.sup.ε-dilauroyllysinate were prepared by the procedure of Example 1 with the exception that the amino acid derivatives were dissolved in the nonpolar organic liquids at a temperature of 75° - 120°C. The results are tabulated below. 
     
                      Shear Strength of Gel                                        
Non-polar    N.sup.α,N.sup.γ-dicap-                           
                      N-lauroyl-                                          
                             Stearylamine                                 
organic      ryloylornithine                                              
                      glutamic                                            
                             N.sup.α,N.sup.ε-di-            
liquid                acid-α-γ-                               
                             lauroylly-                                   
                      di-n-butyl-                                         
                             sinate                                       
                      amide                                               
             (g/cm.sup.2)                                                 
                      (g/cm.sup.2)                                        
                             (g/cm.sup.2)                                 
__________________________________________________________________________
Benzene      30       131    12                                           
Cyclohexane  14       75     18                                           
Heavy Oil *1 11       202    19                                           
Spindle Oil *2                                                            
             17       345    30                                           
Turbine Oil *3                                                            
             21       177    32                                           
Carbon tetrachloride                                                      
             102      10     12                                           
Dioctyl sebacate                                                          
             25       264    45                                           
n-Butyl acetate                                                           
             11       13     12                                           
Dioctyl phthalate                                                         
             15       87     33                                           
Methyl isobutyl ketone                                                    
             2.5      26     3.8                                          
Liquid paraffin                                                           
             16       398    57                                           
Polyoxypropylene *4                                                       
glycol monobutyl ether                                                    
             22       173    80                                           
Polyoxyethylene *5                                                        
glycol monooleate                                                         
             23       168    75                                           
Corn oil     10       125    89                                           
Rapeseed oil 12       189    108                                          
Soybean oil  13       353    122                                          
Tricresyl phosphate                                                       
             2.1      217    15                                           
Gasoline     12       162    16                                           
Gas oil      15       211    19                                           
Xylene       24       85     13                                           
Toluene      16       62     9                                            
Cotton seed oil                                                           
             11       174    103                                          
Diisobutylketone                                                          
             3.0      35     4.5                                          
Diethyl phthalate                                                         
             15       83     28                                           
Octane       8.0      63     15                                           
__________________________________________________________________________
 *1 Viscosity of 2.1 C.P. (50°C)                                   
 *2 Viscosity of 4.0 cst (50° C) and a pour point below -5°C
 *3 Viscosity of 17.5-22.5 cst (50°C) and a pour point below       
 -5°C                                                              
 *4 Containing 40 oxypropylene units                                      
 *5 Containing 5 oxyethylene units                                        
 
    
     EXAMPLE 3 
     A series of gelled kerosine samples containing from 0.1 to 5 wt% of N-lauroylglutamic acid-α,γ-di-n-octylamide was prepared in the manner described in Example 1. The results are tabulated below. 
     
         ______________________________________                                    
N-laurylglutamic acid-                                                    
                 Shear strength of kerosine                               
α,γ-di-n-octylamide (wt%)                                     
                 gel (g/cm.sup.2)                                         
______________________________________                                    
0.1              6                                                        
0.5              56                                                       
1.0              130                                                      
2.0              387                                                      
5.0              475                                                      
______________________________________                                    
 
    
     EXAMPLE 4 
     Three grams each of the powdered derivatives of the N-acylamino acids shown in the table below were admixed in 100 grams of a non-polar organic liquid. Each mixture was vigorously shaken for 10 minutes and allowed to stand overnight. Each mixture gelled and the results are tabulated below. 
     
         ______________________________________                                    
                               Shear                                      
Derivative of N-acylamino acid                                            
                   Non-polar   strength                                   
                   organic     of gel                                     
                   liquid      (g/cm.sup.2)                               
______________________________________                                    
N.sup.α,N.sup.δ-dicapryloylornithine                          
                   Benzene     45                                         
&#34;                  Carbon tetra-                                          
                   chloride    140                                        
&#34;                  Kerosine    23                                         
N-lauroylglutamic acid-α,γ-                                   
di-n-octylamide    Benzene     85                                         
N-lauroylglutamic acid-α,γ-                                   
di-n-stearylamide  Benzene     4.5                                        
______________________________________                                    
 
    
     EXAMPLE 5 
     A series of experiments were conducted using N-lauroyl-glutamic acid-α,γ-di-n-butylamide. One gram of N-lauroyl-glutamic acid-α ,γ-di-n-butylamide was dissolved in 5 ml of stirred ethyl acetate at a temperature of 60°C. The solution obtained was added to 100 grams of the stirred non-polar organic liquid. After standing for one hour, each solution gelled. The results are tabulated below. 
     
         ______________________________________                                    
Non-polar organic liquid                                                  
                  Shear strength of gel                                   
                  (g/cm.sup.2)                                            
______________________________________                                    
Ligroin           89                                                      
Kerosine          185                                                     
Gasoline          83                                                      
Heavy Oil         145                                                     
Liquid paraffin   298                                                     
Olive Oil         176                                                     
Soybean Oil       212                                                     
Rapeseed Oil      153                                                     
Corn Oil          97                                                      
______________________________________                                    
 
    
     EXAMPLE 6 
     Gels of non-polar organic liquids were prepared containing 1 wt% of N.sup.α,N.sup.ε-dicapryloyllysine laurylester in the manner described in Example 5. The results are tabulated below. 
     
         ______________________________________                                    
Non-polar organic liquid                                                  
                  Shear strength of gel                                   
                  (g/cm.sup.2)                                            
______________________________________                                    
Kerosine          18                                                      
Cyclohexane       13                                                      
Heavy Oil         25                                                      
Liquid paraffin   31                                                      
Dioctyl phthalate 16                                                      
Polyoxypropylene-                                                         
glycol monobutylether *1                                                  
                  52                                                      
Olive Oil         59                                                      
______________________________________                                    
 *1 Contains 40 oxypropylene units                                        
 
    
     EXAMPLE 7 
     A series of experiments were conducted using N-lauroylglutamic acid. Four grams of N-lauroylglutamic acid were dissolved in 10 ml of acetone at a temperature of 55°C. The solution was added to 100 grams of a stirred non-polar organic liquid. After standing overnight, the mixture gelled, and the results are tabulated below. 
     
         ______________________________________                                    
Non-polar organic liquid                                                  
                  Shear strength of gel                                   
                  (g/cm.sup.2)                                            
______________________________________                                    
Benzene           3.0                                                     
Spindle Oil       4.5                                                     
Olive Oil         3.8                                                     
______________________________________                                    
 
    
     EXAMPLE 8 
     A series of experiments were conducted using N-lauroylalanine in the same manner as in Example 7. The results are tabulated below. 
     
         ______________________________________                                    
Non-polar organic liquid                                                  
                  Shear strength of gel                                   
                  (g/cm.sup.2)                                            
______________________________________                                    
Kerosine          28                                                      
Heavy Oil         17                                                      
Spindle Oil       29                                                      
Turbine Oil       32                                                      
______________________________________                                    
 
    
     EXAMPLE 9 
     One gram each of the derivatives of the N-acylamino acids shown in the table below was admixed in 90 grams of a non-polar organic liquid, and each mixture was heated at a temperature of 80°C for 10 minutes. To each solution, 10 grams of water were added and each solution was vigorously shaken at a temperature of 80°C. After cooling to room temperature, each suspension had gelled. The results are tabulated below. 
     
         __________________________________________________________________________
Derivative of N-acylamino acid                                            
                 Non-polar Shear Strength                                 
                 organic   of gel                                         
                 liquid    (g/cm.sup.2)                                   
__________________________________________________________________________
N-lauroylglutamic acid-α,γ-                                   
distearylamide   Kerosine  15                                             
&#34;                Heavy Oil 21                                             
&#34;                Liquid Paraffin                                          
                           109                                            
&#34;                Polyoxypropylene                                         
&#34;                glycol mono-                                             
                 butyl ether *1                                           
                           20                                             
&#34;                Olive Oil 91                                             
N-lauroylvaline laurylamide                                               
                 Liquid Paraffin                                          
                           3.5                                            
N.sup.α,N.sup.ε-dicapryloyllysine                           
lauryl ester       &#34;       15                                             
Stearylamine N.sup.α,N.sup.ε-di-                            
capryloyl lysinate                                                        
                 Polyoxypropylene                                         
                 glycol mono-                                             
                 butyl ether *1                                           
                           31                                             
N-capryloylleucine laurylamide                                            
                 Liquid paraffin                                          
                           8.3                                            
Laurylamine N-lauroylphenyl-                                              
alaninate        Olive Oil 62                                             
__________________________________________________________________________
 *1 Contains 40 oxypropylene units                                        
 
    
     EXAMPLE 10 
     One gram of N-lauroylglutamic acid-α ,γ -di-n-butylamide was dissolved in 5 ml of methanol at a temperature of 50°C. The solution was added slowly to the mixture of 70 grams of olive oil and 30 grams of water with vigorous stirring. After standing for 20 minutes, the mixture had gelled. The shear strength of the gel was 189 g/cm 2 . 
     EXAMPLE 11 
     One-half gram of N-lauroylglutamic acid- α ,γ -di-n-octylamide was dissolved in 5 ml of benzene at a temperature of 50°C. This solution was added to 1 liter of sea water having suspended therein 25 grams of heavy oil, and was stirred for 30 seconds. After standing for 20 minutes, the heavy oil solidified and floated on the surface of the sea water. The mixture was filtered through wire gauze (20 mesh) and 31 grams of solidified heavy oil was collected which contained benzene and a small amount of water. The content of the heavy oil in the mother liquor was below 75 ppm, as determined by measurements according to the procedure of Japanese Industrial Standards (JIS) K-0102. A similar experiment was conducted in which crude oil (Iranian heavy) was substituted for the heavy oil. Thirty grams of crude oil were collected and the content of the crude oil in the mother liquor was below 100 ppm. 
     EXAMPLE 12 
     One half ml or 0.1 ml of ethanol containing 10 wt/vol% of a derivative of an N-acylamino acid was added to 5 liters of water containing from 0.5 to 2.5 grams of a suspended non-polar organic liquid. The mixture was stirred vigorously for 10 minutes and then allowed to stand for 1 hour. The non-polar organic liquid solidified and floated. The solidified substance was removed by filtration. The residual amount of non-polar organic liquid in the mother liquor was measured by the methods of JIS K-0102 and the results are tabulated below. 
     
         Derivative of N-                                                          
            Admixed       Oil content                                     
acylamino acid                                                            
            volume of     In the                                          
                               In the                                     
            ethanol       original                                        
                               mother                                     
            solution      water                                           
                               liquor                                     
            (ml)          (ppm)                                           
                               (ppm)                                      
__________________________________________________________________________
N-lauroylglutamic                                                         
acid-α,γ-di-n-                                                
butyl amide 0.5   Heavy Oil                                               
                          100  0.57                                       
N-caproylglutamic                                                         
acid-α,γ-di-                                                  
stearylamide                                                              
            &#34;     &#34;       &#34;    0.71                                       
N-lauroyl valine                                                          
laurylamide &#34;     &#34;       &#34;    0.63                                       
N-palmitoylmethionine                                                     
n-butyl amide                                                             
            &#34;     &#34;       &#34;    3.95                                       
N-stearoylleucine                                                         
benzyl amide                                                              
            &#34;     &#34;       &#34;    3.55                                       
N-lauroylphenylalanine                                                    
lauryl amide                                                              
            &#34;     &#34;       &#34;    3.50                                       
N-capryloylglycine                                                        
stearyl amide                                                             
            &#34;     &#34;       &#34;    4.36                                       
N-stearoylserine                                                          
2-ethyl hexylamide                                                        
            &#34;     &#34;       &#34;    5.93                                       
N.sup.α,N.sup.ε-dicapryloyl                                 
lysine lauryl ester                                                       
            &#34;     &#34;       &#34;    0.59                                       
N-lauroyl-ε-amino                                                 
caproic acid lauryl                                                       
amide       &#34;     &#34;       &#34;    3.83                                       
Stearylamine N.sup.α,N.sup.ε-                               
dicapryloyllysinate                                                       
            &#34;     &#34;       &#34;    0.90                                       
N-lauroylglutamic                                                         
acid-α,γ-di-n-                                                
butyl amide &#34;     Soybean Oil                                             
                          &#34;    0.36                                       
  &#34;         &#34;     Turbine Oil                                             
                          &#34;    0.42                                       
N-lauroylglutamic                                                         
acid-α,γ-di-                                                  
stearylamide                                                              
            0.1   Heavy Oil                                               
                          &#34;    3.1                                        
  &#34;         0.5   &#34;       500  2.9                                        
  &#34;         0.1   Soybean Oil                                             
                          100  2.6                                        
  &#34;         0.5   &#34;       500  3.9                                        
__________________________________________________________________________
 
    
     EXAMPLE 13 
     A series of experiments were conducted in the same manner described in Example 12 using water in which the non-polar organic liquid was emulsified with surfactants. The results are tabulated below. 
     
         ______________________________________                                    
                         Oil and surfact-                                 
          Admixed        ant content                                      
          volume of      In the  In the                                   
          ethanol        original                                         
                                 mother                                   
          solution       water   liquor                                   
          (ml)           (ppm)   (ppm)                                    
______________________________________                                    
N-lauroylglutamic                                                         
acid-ε,γ-di-n-                                              
butyl amide 0.5       Soybean Oil                                         
                                 100   1.5                                
                      Sodium do-                                          
                      decylsul-                                           
                      fate (SDS) 100                                      
  &#34;         &#34;         Heavy Oil  100   3.8                                
                      SDS        100                                      
N-lauroylglutamic                                                         
acid-α,γ-di-                                                  
stearylamide                                                              
            &#34;         &#34;          100   2.5                                
                      &#34;          100                                      
  &#34;         &#34;         Turbine oil                                         
                                 100   2.1                                
                      SDS        100                                      
______________________________________                                    
 
    
     EXAMPLE 14 (Cosmetics) 
     One gram of N-lauroylglutamic acid-α ,.sub.≳ -di-n-butylamide was dissolved in 45 grams of stirred liquid paraffin at a temperature of 120°C. To the stirred solution, 48.8 grams of olive oil, 5 grams of white vaseline, 0.2 grams of rose essence and a very small quantity of coloring matter were added at a temperature of 80°C. The resulting solution was cooled to room temperature. After standing for one hour, a gelled and clear hair conditioner was prepared. 
     EXAMPLE 15 (Cosmetics) 
     One gram of N.sup.α ,N.sup.ε -dicapryloyl lysine lauryl ester was dissolved at a temperature of 90°C in 68.8 grams of a solution which consisted of 54.1 grams of liquid paraffin, 4 grams of squalene, 4 grams of isopropylmyristate, 2 grams of bees wax, 4.5 grams of polyoxyethylene stearyl ether and 0.2 grams of methyl benzoate. To the solution, 27 grams of water and 3 grams of polyethylene glycol were added and the obtained suspension was shaken vigorously and an emulsion was formed at a temperature of 80°C. Then, the emulsion was cooled to a temperature of 60°C and 0.3 grams of rose essence were added thereto with stirring. The resulting emulsion was cooled to room temperature and allowed to stand overnight and then gelled. The gel obtained was a cleansing-jelly which spread well and adapted well on the skin. 
     EXAMPLE 16 (Paint) 
     Forty-five grams of chlorinated rubber (20% solution in toluene; viscosity of 10 centipoise), 18 grams of chlorinated paraffin, 58 grams of titanium dioxide, 70 grams of toluene, 4 grams of xylene and 4 grams of butyl acetate were mixed sufficiently in a ball mill. To the paint, 6 grams of a hot toluene solution containing 1 gram of N-lauroylglutamic acid-α ,γ -di-n-butylamide was added with stirring. The solution was allowed to stand overnight, and the mixture gelled. The thixotropic properties of the paint (1) and a similar paint (2) containing no N-lauroylglutamic acid-α ,γ -di-n-butylamide as a control were measured with a viscosimeter type B. The results are tabulated below. 
     
         ______________________________________                                    
(A)      Viscosity at                                                     
                     (B)    Viscosity at                                  
                                      Ratio                               
         6 rpm (cp)         60 rpm (cp)                                   
                                      A/B                                 
______________________________________                                    
(1)      8400           2400        3.5                                   
(2)       550            540        1.0                                   
______________________________________                                    
 
    
     Having now fully described this invention, it will be apparent to one of ordinary skill in the art that many changes and modifications can be made thereto without departing from the spirit or scope of the invention as set forth herein.