Abstract:
The present invention relates to novel compositions and, more particularly, to a class of compounds having specific quaternized amine based upon a phosphate ester. The use of a phosphate ester based upon a fatty alcohol or fatty alcohol alkoxylate as the material used to prepare a phospholipid results in heretofore-unknown compounds. The products are very good wetting agents, have improved hydrolytic stability, are extremely substantitive to human skin and are well tolerated by human tissue making them suitable for use preparation of barrier products for personal care applications. In short they are ideal surfactants for use in many personal care applications.

Description:
FIELD OF THE INVENTION 
     The present invention relates to novel compositions and, more particularly, to a class of compounds having specific quaternized amine based upon a phosphate ester. The use of a phosphate ester based upon a fatty alcohol or fatty alcohol alkoxylate as the material used to prepare a phospholipid results in heretofore-unknown compounds. The products are very good wetting agents, have improved hydrolytic stability, are extremely substantitive to human skin and are well tolerated by human tissue making them suitable for use preparation of barrier products for personal care applications. In short they are ideal surfactants for use in many personal care applications. 
     BACKGROUND OF THE INVENTION 
     Phosphate ester and quaternary amine compounds are well known and have been widely used for many years More recently, various betaine-type derivatives having, in general, quaternized alkyl amine groups and at least one phosphorous-containing anion in the molecule referred to hereinafter as “synthetic phospholipids”, have been disclosed The in U.S. Pat. Nos. are U.S. Pat. Nos. 3,856,893 and 3,928,509 to Diery et al. Diery discloses that the phosphonate compounds of his invention are active anti-microbial compounds. Later amido amine and imidazoline derivatives were disclosed for example, in U.S. Pat. Nos. 4,215,064; 4,233,192 and 4,380,637 to Lindemann et al., U.S. Pat. Nos. 4,209,449; 4,336,385 and 4,503,002 to Mayhew et al., and U.S. Pat. Nos. 4,243,602; 4,283,542 and 4,336,386 to O&#39;Lenick et al. These synthetic phospholipids are suggested as exhibiting an outstanding combination of surfactant characteristics as well as being well tolerated by human tissue, i.e., they exhibit exceptionally low ocular irritation and oral toxicity. While these known phospholipids have been found useful as surfactants in a variety of personal care, they have not exhibited an ability to protect the skin from irritation or provide barrier properties to the skin, protecting it from the negative effects of chemicals and environmental effects. 
     It is very desirable to provide a material from aqueous solution that have a combination of surfactant properties, including foaming, detergency and wetting. The compounds of the present invention provide a wide range of surfactant properties in a single molecule and consequently are referred to as biominimetric-multi-functional surface-active agents. They can be formulated into a plethora of personal care products ranging from baby wipes to body washes and other skin products. In addition the structure of the compounds provides for outstanding substantivity and the phospholipid nature of the molecule allow for very mild natural like materials that can be used in products where low irritation is important. 
     SUMMARY OF THE INVENTION 
     Objective of the Invention 
     It is the objective of the invention to provide a novel phospholipid that contains in the same molecule a phosphated fatty alcohol or fatty alcohol alkoxylate and a process of its use which comprises contacting the hair with an effective surface active concentration of the novel phospholipid. The effective conditioning concentration ranges from between 0.1 and 25% by weight. 
     In accordance with the present invention we have now been discovered novel phospholipid compound, which conform to the following structure: A phospholipid, which conforms to the following structure;                           
     wherein; 
     R 1  is R 5 —(OCH 2 CH 2 O) a —(CH 2 CH(CH 3 )O) b —(OCH 2 CH 2 O) c — 
     a, b and c are independently integers ranging from 0 to 20; 
     x, and z are integers independently ranging from 1 to 2; 
     y is 0 or 1, with the proviso that x+y+z=3; 
     R 2  is selected from the group consisting of; 
     
       
         CH 3 —(CH 2 ) d — 
       
     
     
       
         CH 3 —(CH 2 ) e —C(O)—N(H)—(CH 2 ) 3 — 
       
     
     
       
         CH 3 (CH 2 ) f CH═CH—(CH 2 ) g — 
       
     
      and 
     
       
         CH 3 (CH 2 ) h CH═CH—(CH 2 ) i -C(O)—N(H)—(CH 2 ) 3 — 
       
     
     R 3  is selected from the group consisting of —CH 3 , —CH 2 CH 3 , and —(CH 2 CH 2 O) j —(CH 2 CH(CH 3 )O) k —(OCH 2 CH 2 O) m —H 
     R 4  is selected from the group consisting of —CH 3 , —CH 2 CH 3 , and —(CH 2 CH 2 O) j —(CH 2 CH(CH 3 )O) k —(OCH 2 CH 2 O) m —H 
     R 5  is selected from the group consisting of 
     
       
         CH 3 —(CH 2 ) r — 
       
     
     
       
         CH 3 (CH 2 ) s CH═CH—(CH 2 ) t — 
       
     
      and 
     
       
         CH 3 (CH 2 ) u —C 6 H 5 —O— 
       
     
     d is an integer ranging from 7 to 21; 
     e is an integer ranging from 6 to 20; 
     f and g are independently integers ranging from 2 to 20; 
     h and i are independently integers ranging from 2 to 20; 
     j, k and m are independently integers ranging from 0 to 20, with the proviso that j+k+m be greater than or equal to 1; 
     r is an integer ranging from 6 to 21; 
     s and t are integers ranging from 2 to 20 
     u is an integer ranging from 7 to 21. 
     The invention is also directed to a process for cleaning and conditioning hair, which comprises contacting the hair with an effective conditioning amount of a phospholipid, which conforms to the following structure;                           
     wherein; 
     R 1  is R 5 —(OCH 2 CH 2 O) a —(CH 2 CH(CH 3 )O) b —(OCH 2 CH 2 O) c — 
     a, b and c are independently integers ranging from 0 to 20; 
     x, and z are integers independently ranging from 1 to 2; 
     y is 0 or 1, with the proviso that x+y+y=3; 
     R 2  is selected from the group consisting of; 
     
       
         CH 3 —(CH 2 ) d — 
       
     
     
       
         CH 3 —(CH 2 ) e —C(O)—N(H)—(CH 2 ) 3 — 
       
     
     
       
         CH 3 (CH 2 ) f CH═CH—(CH 2 ) g — 
       
     
      and 
     
       
         CH 3 (CH 2 ) h CH═CH—(CH 2 ) i —C(O)—N(H)—(CH 2 ) 3 — 
       
     
     R 3  is selected from the group consisting of —CH 3 , —CH 2 CH 3 , —(CH 2 CH 2 O) j —(CH 2 CH(CH 3 )O) k —(OCH 2 CH 2 O) m —H 
     R 4  is selected from the group consisting of —CH 3 , —CH 2 CH 3 , —(CH 2 CH 2 O) n —(CH 2 CH(CH 3 )O) p —(OCH 2 CH 2 O) q —H 
     R 5  is selected from the group consisting of 
      CH 3 —(CH 2 ) r — 
     
       
         CH 3 (CH 2 ) s CH═CH—(CH 2 ) t — 
       
     
      and 
     
       
         CH 3 (CH 2 ) u —C 6 H 5 —O— 
       
     
     d is an integer ranging from 7 to 21; 
     e is an integer ranging from 6 to 20; 
     f and g are independently integers ranging from 2 to 20; 
     h and i are independently integers ranging from 2 to 20; 
     j, k and m are independently integers ranging from 0 to 20, with the proviso that j+k+m be greater than or equal to 1. 
     r is an integer ranging from 6 to 21; 
     s and t are integers ranging from 2 to 20; 
     u is an integer ranging from 7 to 21. 
     Preferred Embodiments 
     In a preferred embodiment, R 2  is CH 3 —(CH 2 ) d —. 
     In a preferred embodiment, R 2  is CH 3 —(CH 2 ) e —C(O)—N(H)—(CH 2 ) 3 —. 
     In a preferred embodiment, R 2  is CH 3 (CH 2 ) f CH═CH—(CH 2 ) g —. 
     In a preferred embodiment, R 2  is 
     
       
         CH 3 (CH 2 ) h CH═CH—(CH 2 ) i -C(O)—N(H)—(CH 2 ) 3 —. 
       
     
     In a preferred embodiment, R 3  is —CH 3 . 
     In a preferred embodiment, R 3  is —CH 2 CH 3 , 
     In a preferred embodiment, R 3  is 
     
       
         —(CH 2 CH 2 O) j —(CH 2 CH(CH 3 )O) k —(OCH 2 CH 2 O) m —H. 
       
     
     In a preferred embodiment, R 4 is —CH 3 . 
     In a preferred embodiment, R 4 is —CH 2 CH 3 . 
     In a preferred embodiment, R 4  is 
     
       
         —(CH 2 CH 2 O) n —(CH 2 CH(CH 3 )O) p —(OCH 2 CH 2 O) q —H. 
       
     
     In a preferred embodiment, R 3  and R 4  are both —CH 3    
     In a preferred embodiment, R 3  and R 4  are both 
     
       
         —(CH 2 CH 2 O) n —(CH 2 CH(CH 3 )O) p —(OCH 2 CH 2 O) q —H. 
       
     
     In a preferred embodiment, R 3  and R 4  are both —CH 2 CH 3 . 
     In a preferred embodiment the effective conditioning concentration ranges from 0.1 to 25% by weight. 
     DETAILED DESCRIPTION OF THE INVENTION 
     The present invention is directed to novel phospholipid compounds, which conform to the following structure: In accordance with the present invention we have now been discovered novel phospholipid compound, which conform to the following structure:                           
     wherein; 
     R 1  is R 5 —(OCH 2 CH 2 O) a —(CH 2 CH(CH 3 )O) b —(OCH 2 CH 2 O) c — 
     a, b and c are independently integers ranging from 0 to 20; 
     x, and z are integers independently ranging from 1 to 2; 
     y is 0 or 1, with the proviso that x+y+z=3; 
     R 2  is selected from the group consisting of; 
     
       
         CH 3 —(CH 2 ) d — 
       
     
     
       
         CH 3 —(CH 2 ) e —C(O)—N(H)—(CH 2 ) 3 — 
       
     
     
       
         CH 3  (CH 2 ) f CH═CH—(CH 2 ) g — 
       
     
      and 
     
       
         CH 3  (CH 2 ) h CH═CH—(CH 2 ) i -C(O)—N(H)—(CH 2 ) 3 — 
       
     
     R 3  is selected from the group consisting of —CH 3 , —CH 2 CH 3 , and —(CH 2 CH 2 O) j —(CH 2 CH(CH 3 )O) k —(OCH 2 CH 2 O) m —H 
     R 4  is selected from the group consisting of —CH 3 , —CH 2 CH 3 , and —(CH 2 CH 2 O) j —(CH 2 CH(CH 3 )O) k —(OCH 2 CH 2 O) m —H 
     R 5  is selected from the group consisting of 
     
       
         CH 3 —(CH 2 ) r — 
       
     
     
       
         CH 3  (CH 2 ) s CH═CH—(CH 2 ) t — 
       
     
      and 
      CH 3 (CH 2 ) u —C 6 H 5 —O— 
     d is an integer ranging from 7 to 21; 
     e is an integer ranging from 6 to 20; 
     f and g are independently integers ranging from 2 to 20; 
     h and i are independently integers ranging from 2 to 20; 
     j, k and m are independently integers ranging from 0 to 20, with the proviso that j+k+m be greater than or equal to 1; 
     r is an integer ranging from 6 to 21; 
     s and t are integers ranging from 2 to 20 
     u is an integer ranging from 7 to 21. 
     Phosphate Ester Chemistry 
     Phosphate esters are part of a class of anionic surface-active agents. The commercial products are complex mixtures including monoester and diester. 
     The type or types of starting alcohol used determine the functionality of the phosphate ester. Modification of this group is a major factor in the functionality of a phosphate ester. 
     There are generally two different phosphating agents used commercially. They are polyphosphoric acid (PPA) and phosphorous pentoxide (P 2 O 5 ). The selection of phosphating reagent has an effect upon the ratio of the components and upon the functional properties of the resulting phosphate ester. 
     Reaction 
     The reaction used to make phosphate esters is referred to as phosphation. It is conducted with either polyphosphoric acid or phosphorus pentoxide and results in a product that is a mixture of mono and diester.                           
     Phosphate esters are marketed at 100% activity in their free acid form or can be neutralized to any desired pH with alkali metals, such as sodium or potassium hydroxide; ammonia and other bases. Additionally, several products are available as partially neutralized forms. 
     Most phosphate esters are pale yellow to amber, sweet smelling, viscous liquids or pastes, and combine many important properties including (a) stability to extremes of acidity and alkalinity, (b) excellent heat stability (c) high electrolytic tolerance (d) good solubility in alkali, (e) outstanding coupling ability, and (f) outstanding wetting. 
     Phospholipids 
     Phospholipids are well known materials and are the topic of a number of patents including U.S. Pat. Nos. 4,215,064; 4,233,192 and 4,380,637 to Lindemann et al., U.S. Pat. Nos. 4,209,449; 4,336,385 and 4,503,002 to Mayhew et al., and U.S. Pat. Nos. 4,243,602; 4,283,542 and 4,336,386 to O&#39;Lenick et al. Until the compounds of the present invention phospholipids were prepared by the reaction of a phosphate salt, like disodium hydrogen phosphate with epichlorohydrin to give a chlorohydroxypropyl intermediate that was subsequently reacted with a tertiary amine to give a phospholipid compound.                           
     Phosphate Ester Derived Phospholipids 
     The products of the present invention use the phosphate esters as the source of the phosphate, thereby incorporating an additional highly functional group into the molecule. It is by the incorporation of this group into the molecule that enhanced surfactant properties are obtained.                           
     The second reaction is as follows:                           
     If a diester phosphate is used a compound with no ionizable phosphate group results.                           
     In the diester case, the second reaction is as follows:                           
     The resulting product has two phosphate ester groups present and no ionizable phosphate group, resulting in a cationic quaternary compound. 
     The phosphate monoester compounds are very efficient wetting agents. This attribute makes them very desirable for their ability to wet out fiber like hair and substrates like skin to give uniform deposition of the phospholipid. 
     The phosphate diester product is an outstanding oil emulsifier. This attribute makes the molecule a better detergent and cleaning agent. The improved detergency makes these compounds more desirable and more functional than the phospholipids made from sodium phosphate. 
     The fact that the compounds of the present invention are made from phosphate esters, which are commonly mixtures of mono and diester, results in a multifunctional product that provides wide range of properties in the formulation. The mixed products are a preferred embodiment of the invention, truly giving a multi-functional surfactant. Phosphate esters made with polyphosphoric acid result in products having 90%+ monoester. Products made with P 2 O 5  typically result in products having roughly equal amounts of mono and diester. The resulting phospholipids made from phosphate esters are unique products, due in part to the raw materials used to make them. 
    
    
     EXAMPLES 
     Phosphate Esters 
     Phosphate Esters useful in the preparation of the compounds of the present invention are commercially available from a variety of sources including Siltech Corporation, Toronto Ontario Canada. 
     
       
         R 1 —P(O)—(OH) 2  Monoester 
       
     
     
       
         (R 1 ) 2 —P(O)—OH Diester 
       
     
     R 1  is R 5 —(OCH 2 CH 2 O) a —(CH 2 CH(CH 3 )O) b —(OCH 2 CH 2 O) c — 
     a, b and c are independently integers ranging from 0 to 20. 
     Alkyl Phosphate Esters 
     Compounds of this class are commercially available from a variety of manufacturers including Siltech Corporation of Toronto Ontario Canada. They conform to the following structure; 
     
       
         [CH 3 —(CH 2 ) r —(OCH 2 CH 2 O) a —(CH 2 CH(CH 3 )O) b —(OCH 2 CH 2 O) c —] x —P(O)—[OH] z   
       
     
     wherein 
     r is an integer ranging from 6 to 21; 
     a, b and c are independently integers ranging from 0 to 20. 
     Products made with polyphosphoric acid are on average 90% monoester, 10% diester. This means on average the “x” value is 0.9 and the average z value is 2.1 to equal three substituents. 
     
       
         
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
             
           
               
                   
               
               
                   
                 a 
                   
                 c 
                   
                 x 
                   
                   
               
               
                 Example 
                 value 
                 b value 
                 value 
                 r value 
                 value 
                 z value 
                 monoester 
               
               
                   
               
             
             
               
                   
               
             
          
           
               
                 1 
                 0 
                 0 
                 0 
                 6 
                 0.9 
                 2.1 
                 90% 
               
               
                 2 
                 0 
                 0 
                 0 
                 7 
                 0.9 
                 2.1 
                 90% 
               
               
                 3 
                 0 
                 1 
                 1 
                 9 
                 0.9 
                 2.1 
                 90% 
               
               
                 4 
                 5 
                 5 
                 5 
                 13 
                 0.9 
                 2.1 
                 90% 
               
               
                 5 
                 0 
                 2 
                 0 
                 15 
                 0.9 
                 2.1 
                 90% 
               
               
                 6 
                 5 
                 1 
                 3 
                 17 
                 0.9 
                 2.1 
                 90% 
               
               
                 7 
                 10 
                 10 
                 5 
                 19 
                 0.9 
                 2.1 
                 90% 
               
               
                 8 
                 20 
                 20 
                 20 
                 21 
                 0.9 
                 2.1 
                 90% 
               
               
                   
               
             
          
         
       
     
     Products made with P 2 O 5  are on average 50% monoester, 50% diester. This means on average the “x” value is 1.5 and the average z value is 1.5 to equal three substituents. 
     
       
         
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
             
           
               
                   
               
               
                   
                 a 
                   
                 c 
                   
                 x 
                   
                   
               
               
                 Example 
                 value 
                 b value 
                 value 
                 r value 
                 value 
                 z value 
                 monoester 
               
               
                   
               
             
             
               
                   
               
             
          
           
               
                 9 
                 0 
                 0 
                 0 
                 6 
                 1.5 
                 1.5 
                 50% 
               
               
                 10 
                 0 
                 2 
                 5 
                 7 
                 1.5 
                 1.5 
                 50% 
               
               
                 11 
                 10 
                 10 
                 10 
                 9 
                 1.5 
                 1.5 
                 50% 
               
               
                 12 
                 20 
                 20 
                 20 
                 13 
                 1.5 
                 1.5 
                 50% 
               
               
                 13 
                 2 
                 2 
                 2 
                 15 
                 1.5 
                 1.5 
                 50% 
               
               
                 14 
                 5 
                 2 
                 10 
                 17 
                 1.5 
                 1.5 
                 50% 
               
               
                 15 
                 10 
                 5 
                 3 
                 19 
                 1.5 
                 1.5 
                 50% 
               
               
                 16 
                 10 
                 1 
                 5 
                 21 
                 1.5 
                 1.5 
                 50% 
               
               
                   
               
             
          
         
       
     
     Alkylene Phosphate Esters 
     Compounds of this class are commercially available from a variety of manufacturers including Siltech Corporation of Toronto Ontario Canada. They conform to the following structure; 
     
       
         [CH 3 (CH 2 ) s CH═CH—(CH 2 ) t —(OCH 2 CH 2 O) a —(CH 2 CH(CH 3 )O) b —(OCH 2 CH 2 O) c —] x P(O)—(OH) z   
       
     
     wherein s and t are integers ranging from 2 to 20; 
     The unsaturated alcohols of interest for the preparation of the compounds of the current invention include; 
      CH 3 (CH 2 ) s CH═CH—(CH 2 ) t —OH 
     
       
         
               
               
               
               
               
             
           
               
                   
               
               
                 Designation 
                 Name 
                 Formula 
                 s 
                 t 
               
               
                   
               
             
             
               
                 C12:1 
                 Lauroleyl alcohol 
                 C 12 H 22 O 
                 2 
                 8 
               
               
                 C14:1 
                 Myristoleyl alcohol 
                 C 14 H 26 O 
                 4 
                 8 
               
               
                 C16:1 
                 Palmitoleyl alcohol 
                 C 16 H 30 O 
                 5 
                 8 
               
               
                 C18:1 
                 Oleyl alcohol 
                 C 18 H 34 O 
                 8 
                 8 
               
               
                 C20:1 
                 Gadoleyl alcohol 
                 C 20 H 38 O 
                 10  
                 8 
               
               
                 C22:1 
                 Erucyl alcohol 
                 C 22 H 42 O 
                 10  
                 10  
               
               
                   
               
             
          
         
       
     
     Products made with polyphosphoric acid are on average 90% monoester, 10% diester. This means on average the “x” value is 0.9 and the average z value is 2.1 to equal three substituents. 
     
       
         
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
             
           
               
                   
               
               
                   
                 a 
                 b 
                 c 
                 s 
                 t 
                 x 
                 z 
                   
               
               
                 Example 
                 Value 
                 Value 
                 value 
                 value 
                 value 
                 value 
                 value 
                 monoester 
               
               
                   
               
             
             
               
                   
               
             
          
           
               
                 17 
                 0 
                 0 
                 0 
                 2 
                 8 
                 0.9 
                 2.1 
                 90% 
               
               
                 18 
                 5 
                 5 
                 5 
                 4 
                 8 
                 0.9 
                 2.1 
                 90% 
               
               
                 19 
                 0 
                 0 
                 10 
                 5 
                 8 
                 0.9 
                 2.1 
                 90% 
               
               
                 20 
                 20 
                 20 
                 20 
                 8 
                 8 
                 0.9 
                 2.1 
                 90% 
               
               
                 21 
                 5 
                 2 
                 10 
                 10 
                 8 
                 0.9 
                 2.1 
                 90% 
               
               
                 22 
                 10 
                 5 
                 5 
                 10 
                 10 
                 0.9 
                 2.1 
                 90% 
               
               
                   
               
             
          
         
       
     
     Products made with P 2 O 5  are on average 50% monoester,. 50% diester. This means on average the “x” value is 1.5 and the average z value is 1.5 to equal three substituents. 
     
       
         
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
             
           
               
                   
               
               
                   
                 a 
                 b 
                 c 
                 s 
                 t 
                 x 
                 z 
                   
               
               
                 Example 
                 Value 
                 Value 
                 value 
                 value 
                 value 
                 value 
                 value 
                 monoester 
               
               
                   
               
             
             
               
                   
               
             
          
           
               
                 23 
                 0 
                 0 
                 0 
                 2 
                 8 
                 1.5 
                 1.5 
                 50% 
               
               
                 24 
                 5 
                 5 
                 5 
                 4 
                 8 
                 1.5 
                 1.5 
                 50% 
               
               
                 25 
                 0 
                 0 
                 10 
                 5 
                 8 
                 1.5 
                 1.5 
                 50% 
               
               
                 26 
                 20 
                 20 
                 20 
                 8 
                 8 
                 1.5 
                 1.5 
                 50% 
               
               
                 27 
                 5 
                 2 
                 10 
                 10 
                 8 
                 1.5 
                 1.5 
                 50% 
               
               
                 28 
                 10 
                 5 
                 5 
                 10 
                 10 
                 1.5 
                 1.5 
                 50% 
               
               
                   
               
             
          
         
       
     
     Alkyl Aryl Phosphate Esters 
     Compounds of this class are commercially available from a variety of manufacturers including Siltech Corporation of Toronto Ontario Canada. They conform to the following structure; 
     
       
         [CH 3 (CH 2 ) u —C 6 H 5 —O—(OCH 2 CH 2 O) a —(CH 2 CH(CH 3 )O) b —(OCH 2 CH 2 O) c —] x P(O)—(OH) z   
       
     
     wherein u is an integer ranging from 7 to 21. 
     Products made with polyphosphoric acid are on average 90% monoester, 10% diester. This means on average the “x” value is 0.9 and the average z value is 2.1 to equal three substituents. 
     
       
         
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
             
           
               
                   
               
               
                   
                 a 
                   
                 c 
                   
                 x 
                   
                   
               
               
                 Example 
                 value 
                 b value 
                 value 
                 u value 
                 value 
                 z value 
                 monoester 
               
               
                   
               
             
             
               
                   
               
             
          
           
               
                 29 
                 0 
                 0 
                 0 
                 7 
                 0.9 
                 2.1 
                 90% 
               
               
                 30 
                 5 
                 1 
                 15 
                 19 
                 0.9 
                 2.1 
                 90% 
               
               
                 31 
                 20 
                 5 
                 10 
                 21 
                 0.9 
                 2.1 
                 90% 
               
               
                   
               
             
          
         
       
     
     Products made with P 2 O 5  are on average 50% monoester,. 50% diester. This means on average the “x” value is 1.5 and the average z value is 1.5 to equal three substituents. 
     
       
         
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
             
           
               
                   
               
               
                   
                 a 
                   
                 c 
                   
                 x 
                   
                   
               
               
                 Example 
                 value 
                 b value 
                 value 
                 u value 
                 value 
                 z value 
                 monoester 
               
               
                   
               
             
             
               
                   
               
             
          
           
               
                 32 
                 0 
                 0 
                 0 
                 7 
                 1.5 
                 1.5 
                 50% 
               
               
                 31 
                 20 
                 5 
                 10 
                 21 
                 1.5 
                 1.5 
                 50% 
               
               
                   
               
             
          
         
       
     
     Preparation of 3-chloro-2-hydroxypropyl Phosphate Ester Intermediate 
     General Reaction 
     To a suitable reaction vessel equipped with reflux condenser, thermometer and agitation is added the specified number of grams of the specified phosphate ester (examples 1 to 33), the specified number of grams of water, under good agitation. The pH is then adjusted with the specified 45% aqueous base to a pH of 7.5. Mix well until a solution is obtained. Next add 141.0 grams of Epichlorohydrin under agitation. Apply heat to 90 C., refluxing back into the vessel any distillate. As the temperature increases to 95-100 C. the contents will clear. Hold at this temperature for 3-4 hours. The resulting product is a 40% aqueous solution of; 
     
       
         
               
               
               
               
               
             
               
               
               
               
               
               
             
               
               
               
               
               
               
             
           
               
                   
                   
               
               
                   
                   
                 Phosphate Ester 
                 Water 
                 Base 
               
             
          
           
               
                   
                 Example 
                 Example 
                 Grams 
                 Grams 
                 Type 
               
               
                   
                   
               
             
          
           
               
                   
                 34 
                  1 
                 179.0 
                 642.0 
                 NaOH 
               
               
                   
                 35 
                  2 
                 184.0 
                 650.0 
                 KOH 
               
               
                   
                 36 
                  3 
                 315.0 
                 912.0 
                 NaOH 
               
               
                   
                 37 
                  4 
                 1003.0 
                 2288.0 
                 NaOH 
               
               
                   
                 38 
                  5 
                 397.0 
                 976.0 
                 KOH 
               
               
                   
                 39 
                  6 
                 735.0 
                 1752.0 
                 NaOH 
               
               
                   
                 40 
                  7 
                 1612.0 
                 3504.0 
                 KOH 
               
               
                   
                 41 
                  8 
                 2268.0 
                 4818.0 
                 NaOH 
               
               
                   
                 42 
                  9 
                 171.5 
                 625.0 
                 NaOH 
               
               
                   
                 43 
                 10 
                 786.0 
                 1854.0 
                 NaOH 
               
               
                   
                 44 
                 11 
                 2459.0 
                 5200.0 
                 KOH 
               
               
                   
                 45 
                 12 
                 3575.0 
                 7432.0 
                 NaOH 
               
               
                   
                 46 
                 13 
                 821.0 
                 1924.0 
                 NaOH 
               
               
                   
                 47 
                 14 
                 1606.0 
                 3494.0 
                 KOH 
               
               
                   
                 48 
                 15 
                 1780.0 
                 3842.0 
                 KOH 
               
               
                   
                 49 
                 16 
                 985.0 
                 2252.2 
                 NaOH 
               
               
                   
                 50 
                 17 
                 288.0 
                 738.0 
                 NaOH 
               
               
                   
                 51 
                 18 
                 1129.0 
                 2540.0 
                 KOH 
               
               
                   
                 52 
                 19 
                 1108.0 
                 2500.0 
                 KOH 
               
               
                   
                 53 
                 20 
                 3614.0 
                 7510.0 
                 NaOH 
               
               
                   
                 54 
                 21 
                 1267.0 
                 2816.0 
                 NaOH 
               
               
                   
                 55 
                 22 
                 1492.0 
                 3266.0 
                 KOH 
               
               
                   
                 56 
                 23 
                 432.0 
                 1152.0 
                 KOH 
               
               
                   
                 57 
                 24 
                 1693.0 
                 3668.0 
                 NaOH 
               
               
                   
                 58 
                 25 
                 1662.0 
                 3606.0 
                 KOH 
               
               
                   
                 59 
                 26 
                 5421.0 
                 11124.0 
                 NaOH 
               
               
                   
                 60 
                 27 
                 1900.0 
                 4082.0 
                 KOH 
               
               
                   
                 61 
                 28 
                 2238.0 
                 4758.0 
                 NaOH 
               
               
                   
                 62 
                 29 
                 316.0 
                 914.0 
                 NaOH 
               
               
                   
                 63 
                 30 
                 1533.0 
                 3348.0 
                 KOH 
               
               
                   
                 64 
                 31 
                 2083.0 
                 4448.0 
                 NaOH 
               
               
                   
                 65 
                 32 
                 430.0 
                 1142.0 
                 NaOH 
               
               
                   
                 66 
                 33 
                 2841.0 
                 5964.0 
                 KOH 
               
               
                   
                   
               
             
          
         
       
     
     Tertiary Amines 
     There are a wide number of tertiary amines that can be used in the preparation of the compounds of the present invention. All are commercially available. 
     Alkyl Tertiary Amines 
     This class of compounds is available from a variety of commercial sources, including Kao Chemical, High Point N.C. They conform to the following structure: 
     
       
         CH 3 —(CH 2 ) d —N—(CH 3 ) 2   
       
     
     wherein d is an integer ranging from 7 to 21; 
     
       
         
               
               
               
             
           
               
                   
                   
               
               
                   
                 Example 
                 d Value 
               
               
                   
                   
               
             
             
               
                   
                 67 
                  7 
               
               
                   
                 68 
                  9 
               
               
                   
                 69 
                 11 
               
               
                   
                 70 
                 13 
               
               
                   
                 71 
                 15 
               
               
                   
                 72 
                 17 
               
               
                   
                 73 
                 19 
               
               
                   
                 74 
                 21 
               
               
                   
                   
               
             
          
         
       
     
     Alkylene Tertiary Amines 
     This class of compounds is available from a variety of commercial sources, including Kao Chemical, High Point N.C. They conform to the following struture: 
     
       
         CH 3 (CH 2 ) f CH═CH—(CH 2 ) g —N—(CH 3 ) 2   
       
     
     wherein f and g are independently integers ranging from 2 to 20. 
     
       
         
               
               
               
             
           
               
                   
               
               
                 Example 
                 f value 
                 g value 
               
               
                   
               
             
             
               
                 75 
                 2 
                 8 
               
               
                 76 
                 4 
                 8 
               
               
                 77 
                 5 
                 8 
               
               
                 78 
                 8 
                 8 
               
               
                 79 
                 10  
                 8 
               
               
                 80 
                 10  
                 10  
               
               
                   
               
             
          
         
       
     
     Alkyl Amido Tertiary Amines 
     This class of compounds is available from a variety of commercial sources, including Siltech Corporation Toronto Ontario Canada. They conform to the following structure: 
     
       
         CH 3 —(CH 2 ) e —C(O)—N(H)—(CH 2 ) 3 —N—(CH 3 ) 2   
       
     
     wherein e is an integer ranging from 6 to 20; 
     
       
         
               
               
               
             
           
               
                   
                   
               
               
                   
                 Example 
                 e Value 
               
               
                   
                   
               
             
             
               
                   
                 81 
                  6 
               
               
                   
                 82 
                  8 
               
               
                   
                 83 
                 10 
               
               
                   
                 84 
                 12 
               
               
                   
                 85 
                 14 
               
               
                   
                 86 
                 18 
               
               
                   
                 87 
                 20 
               
               
                   
                   
               
             
          
         
       
     
     Alkyl Amido Alkylene Tertiary Amines 
     This class of compounds is available from a variety of commercial sources, including Siltech Corporation Toronto Ontario Canada. They conform to the following struture: 
     
       
         CH 3 (CH 2 ) h CH═CH—(CH 2 ) i —C(O)—N(H)—(CH 2 ) 3 — 
       
     
     wherein h and i are independently integers ranging from 2 to 20. 
     
       
         
               
               
               
             
           
               
                   
               
               
                 Example 
                 h Value 
                 i Value 
               
               
                   
               
             
             
               
                 88 
                 2 
                 7 
               
               
                 89 
                 4 
                 7 
               
               
                 90 
                 5 
                 7 
               
               
                 91 
                 8 
                 7 
               
               
                 92 
                 10  
                 7 
               
               
                 93 
                 10  
                 9 
               
               
                   
               
             
          
         
       
     
     Alkoxy Alkyl Tertiary Amines 
     This class of compounds is available from a variety of commercial sources, including Siltech Corporation Toronto Ontario Canada. They conform to the following structure:                           
     wherein d is an integer ranging from 7 to 21 and j, k and m are independently integers ranging from 0 to 20, with the proviso that j+k+m be greater than or equal to 1. 
     
       
         
               
               
               
               
               
             
           
               
                   
               
               
                 Example 
                 d value 
                 i value 
                 k value 
                 m value 
               
               
                   
               
             
             
               
                 94 
                  7 
                 1 
                 0 
                  0 
               
               
                 95 
                 11 
                 2 
                 1 
                  5 
               
               
                 96 
                 16 
                 0 
                 10  
                 10 
               
               
                 97 
                 19 
                 20  
                 20  
                 20 
               
               
                 98 
                 21 
                 10  
                 2 
                 10 
               
               
                   
               
             
          
         
       
     
     Preparation of the Phospholipid of the Present Invention 
     Into a suitable reaction flask is charged the specified number of grams of de-ionized water and the various 3-chloro-2-hydroxypropyl phosphate ester intermediates (Examples 34-66) is next added into the reaction vessel. Heat is applied to 90.degree. C. Next, the specified number of grams of the specified tertiary amine (examples 67-98 ) are charged into the reaction vessel under good agitation. The temperature is maintained at between 90.degree. C. and 95.degree. C., until the percentage of free tertiary amine is 0.5% maximum. During the reaction time the pH is kept at between 7 and 8 with NaOH as required, The reaction mass will clear when the product is at 90 C. for about 1 hour. The reaction time is approximately 6 to 9 hours. The % NaCl is monitored and the reaction is deemed complete when the % of theoretical NaCl reaches 98%. 
     
       
         
               
               
               
               
               
             
               
               
               
               
               
             
           
               
                   
               
               
                   
                 Chloro Phosphate 
                 Water 
                 Tertiary amine 
                   
               
             
          
           
               
                 Example 
                 Example 
                 Grams 
                 Example 
                 Grams 
               
               
                   
               
               
                  99 
                 34 
                 314.0 
                 67 
                 157.0 
               
               
                 100 
                 35 
                 370.0 
                 68 
                 185.0 
               
               
                 101 
                 36 
                 426.0 
                 69 
                 213.0 
               
               
                 102 
                 37 
                 482.0 
                 70 
                 241.0 
               
               
                 103 
                 38 
                 536.0 
                 71 
                 268.0 
               
               
                 104 
                 39 
                 594.0 
                 72 
                 297.0 
               
               
                 105 
                 40 
                 650.0 
                 73 
                 325.0 
               
               
                 106 
                 41 
                 706.0 
                 74 
                 353.0 
               
               
                 107 
                 42 
                 422.0 
                 75 
                 211.0 
               
               
                 108 
                 43 
                 476.0 
                 76 
                 238.0 
               
               
                 109 
                 44 
                 504.0 
                 77 
                 252.0 
               
               
                 110 
                 45 
                 608.0 
                 78 
                 304.0 
               
               
                 111 
                 46 
                 644.0 
                 79 
                 322.0 
               
               
                 112 
                 47 
                 700.0 
                 80 
                 350.0 
               
               
                 113 
                 48 
                 426.0 
                 81 
                 213.0 
               
               
                 114 
                 49 
                 510.0 
                 82 
                 255.0 
               
               
                 115 
                 50 
                 538.0 
                 83 
                 269.0 
               
               
                 116 
                 51 
                 594.0 
                 84 
                 297.0 
               
               
                 117 
                 52 
                 650.0 
                 85 
                 325.0 
               
               
                 118 
                 53 
                 762.0 
                 86 
                 381.0 
               
               
                 119 
                 54 
                 818.0 
                 87 
                 409.0 
               
               
                 120 
                 55 
                 510.0 
                 88 
                 255.0 
               
               
                 121 
                 56 
                 566.0 
                 89 
                 283.0 
               
               
                 122 
                 57 
                 594.0 
                 90 
                 297.0 
               
               
                 123 
                 58 
                 678.0 
                 91 
                 339.0 
               
               
                 124 
                 59 
                 734.0 
                 92 
                 367.0 
               
               
                 125 
                 60 
                 790.0 
                 93 
                 395.0 
               
               
                 126 
                 61 
                 430.0 
                 94 
                 215.0 
               
               
                 127 
                 62 
                 1854.0  
                 95 
                 927.0 
               
               
                 128 
                 63 
                 916.0 
                 96 
                 459.0 
               
               
                 129 
                 64 
                 12350.0  
                 97 
                 6175.0  
               
               
                 130 
                 65 
                 4638.0  
                 98 
                 2319.0  
               
               
                   
               
             
          
         
       
     
     APPLICATIONS EXAMPLES 
     The compounds above examples 99-130 are aqueous solutions of the phospholipids of the current invention. They are used without additional purification. 
     The compounds are multi functional surfactants. That is they exhibit wetting properties, foam properties and are subatantive to hair and skin. They provide good cleansing properties and are very mild to skin and eyes. 
     These products can be used in personal care applications, like shampoos, bubble bath products, body wash and as a wetting agent and detergent for use in wipes designed for babies. 
     While the illustrative embodiments of the invention have been described with particularity, it will be understood that various other modifications will be apparent to and can be readily made by those skilled in the art without departing from the spirit and scope of the invention. Accordingly, it is not intended that the scope of the claims appended hereto be limited to the examples and descriptions set forth hereinabove but rather that the claims be construed as encompassing all the features of patentable novelty which reside in the present invention, including all features which would be treated as equivalents thereof by those skilled in the art to which the invention pertains.