Patent Document

GOVERNMENT SPONSORSHIP 
     None 
     FIELD OF THE INVENTION 
     The present invention is directed to a series of citrate co-polymers film formers that are effective in making uniform films. In addition to being outstanding film formers, these co-polymers provide unique solubilities, liquidity and outstanding feel when applied to the skin, making them highly desirable in the cosmetic field. 
     BACKGROUND OF THE INVENTION 
     Citric acid is a common material of natural origin. The structure is: 
     
       
                 
         
             
             
         
      
     
     CAS Registry Number: 77-92-9 
     CAS Index Name: 1,2,3-Propanetricarboxylic Acid 
     Citric acid is made during the fermentation process; using cultures of  Aspergillus niger  are fed on a sucrose or glucose-containing medium. 
     Citric acid is one of a series of compounds involved in the physiological oxidation of fats, proteins, and carbohydrates to carbon dioxide and water. This series of chemical reactions is central to nearly all metabolic reactions, and is the source of two-thirds of the food-derived energy in higher organisms. Krebs received the 1953 Nobel Prize in physiology or Medicine for the discovery. The series of reactions is known by various names including, citric acid cycle, the Krebs cycle, and the tricarboxylic acid cycle. 
     Citrate esters are also well known. They conform to the following structure: 
                                
These esters are made by the reaction of citric acid with alcohols.
 
     U.S. Pat. No. 4,292,192 issued to Hooper et al. teaches that detergent bars for personal washing are given a deodorant property by including an ester of citric acid. The ester maybe an acetyl derivative. The amount of ester used will be in the range of 0.3% to 3.0%. Examples of the esters are triethyl citrate and acetyl tributyl citrate. 
     An article published in Cosmetic and Toiletries Magazine (Vol. 110 August 1995) by O&#39;Lenick et al addresses Guerbet Citrate Esters. It specifically deals with oil phase emollient esters and breathable non occlusive esters that have fluoro components contained in the ester. Both type of esters are hydrophobic (i.e. oil loving). This article discloses the state of the art of citrate esters, specifically as oil soluble materials that can be applied to skin. The article is posted on http://www.surfatech.com/pdfs/Guerbet%20Citrate%20Ester%20Article.pdf 
     The ability to make compounds having differing solubility in water allows one to make surface active agents, or surfactants. The proper selection of the ratio of water soluble to oil soluble material in the molecule allows for the manufacture of emulsifiers useful over a wide range of formulations. 
     HLB is a methodology that explains this phenomenon. The method was developed by Griffin in 1954 and relates an estimation of surfactant properties to the percentage of water soluble group in a molecule. Specifically, the system addresses polyoxyethylene groups in a non-ionic surfactant/
 
HLB=% PEG in the molecule/5
 
HLB value of 0 corresponds to a completely hydrophobic molecule, and a value of 20 would correspond to a molecule made up completely of hydrophilic components.
 
The HLB value can be used to predict the surfactant properties of a molecule:
 
A value &lt;10: Lipid soluble (water insoluble)
 
A value &gt;10: Water soluble
 
A value from 4 to 8 indicates an anti-foaming agent
 
A value from 7 to 11 indicates a W/O (water in oil) emulsifier
 
A value from 12 to 16 indicates oil in water emulsion
 
A value from 11 to 14 indicates a wetting agent
 
A value from 12 to 15 is typical of detergents
 
A value of 16 to 20 indicates a solubiliser or hydrotrope.
 
     The citrate esters known prior to the compounds of the present invention are oil phases. It was previously unappreciated that by making specific heretofore unknown esters, a series of citrate esters could be developed that are emulsifiers. There has been a long felt need for emulsifiers that provide excellent emulsification and citrate esters have not been available that had any water soluble groups, until this invention. 
     THE INVENTION 
     Object of the Invention 
     The current invention is directed toward a series of citrate ester co-polymers that contain polymeric alkoxylated groups that allow for the preparation of a series of film formers that range in solubilites. 
     SUMMARY OF THE INVENTION 
     The compounds of the present invention are citrate copolymers that have differing amounts of polyoxyethylene groups, fatty alcohols, fatty diols and poly(ethylene glycol) groups on the polymer backbone. 
     There are two necessary requirements to make the compounds of the present invention (1) the polymer must be made with alkoxylated methyl alcohol (thereby blocking one end of the polymer and increasing the polymers polarity.) and (2) the citrate copolymer must have as least one fatty group to promote surface activity. 
     The reaction of PEG (Poly(ethylene glycol)) with a citrate results in a polymer that have limited water solubility. Like wise, the reaction of a citrate with an alkyl diol will promote water in-solubility. 
     
       
         
               
               
               
             
           
               
                   
               
             
             
               
                 H-(OCH 2 CH 2 ) 9 OH 
                 PEG 400 
                 Two Reactive OH groups 
               
               
                 H-(OCH 2 CH 2 ) 9 OCH 3   
                 MePEG 400 
                 One Reactive OH Group 
               
               
                 HO(CH 2 ) 3 OH 
                 1,3 Propane Diol 
                 Two Reactive OH Groups 
               
               
                 HO(CH 2 ) 2 CH 3   
                 1-Propanol 
                 One Reactive OH Group 
               
               
                   
               
             
          
         
       
     
    
    
     DETAILED DESCRIPTION OF THE INVENTION 
     The citrate co-polyesters of the present invention conform to the following structure: 
                                
Wherein;
 
x is an integer ranging from 3 to 15;
 
R 1  is independently selected from groups consisting of —(CH 2 CH 2 O) a CH 3 , linear alkyl having 8 to 26 carbon atoms, and guerbet having 8 to 26 carbons, with the proviso that —(CH 2 CH 2 O) a CH 3  makes up 4-95% of R 1 ;
 
a is an integer ranging from 5 to 25;
 
R 2  is independently selected from groups consisting of —O(CH 2 ) b O—, and —O(CH 2 CH 2 O) c —, with the proviso that —O(CH 2 ) b O— makes up 4-95% of R 2 ;
 
b is an integer ranging from 2 to 12;
 
c is an integer ranging from 5 to 25.
 
     Another aspect of the present invention is a process for conditioning skin, which comprises contacting the skin with an effective conditioning concentration of a citrate co-polyesters of the present invention conform to the following structure: 
                                
wherein;
 
x is an integer ranging from 3 to 15;
 
R 1  is independently selected from groups consisting of —(CH 2 CH 2 O) a CH 3 , linear alkyl having 8 to 26 carbon atoms, and guerbet having 8 to 26 carbons, with the proviso that —(CH 2 CH 2 O) a CH 3  makes up 4-95% of R 1 ;
 
a is an integer ranging from 5 to 25;
 
R 2  is independently selected from groups consisting of —O(CH 2 ) b O—, and —O(CH 2 CH 2 O) c —, with the proviso that —O(CH 2 ) b O— makes up 4-95% of R 2 ;
 
b is an integer ranging from 2 to 12;
 
c is an integer ranging from 5 to 25.
 
     PREFERRED EMBODIMENT 
     In a preferred embodiment said effective conditioning concentration ranges from 0.1 to 20% by weight. 
     In a preferred embodiment a is an integer ranging from 5 to 15. 
     In a preferred embodiment a is an integer ranging from 20 to 25. 
     In a preferred embodiment x is 5. 
     In a preferred embodiment x is 15. 
     In a preferred embodiment x is 25. 
     In a preferred embodiment y is 2. 
     In a preferred embodiment y is 9. 
     EXAMPLES 
     Raw Materials 
     Poly(Ethylene Glycol) Monomethyl Ether 
     Poly(ethylene glycol) monomethyl ether is commercially available from a variety of sources one of which is FCI Technology of Gastonia, N.C. It conforms to the following structure;
 
CH 3 (CH 2 CH 2 O) a —H
 
wherein;
 
a is an integer from 5 to 25;
 
     
       
         
               
               
               
             
               
               
               
             
           
               
                   
               
               
                   
                   
                 Molecular Weight 
               
               
                 Example 
                 a 
                 (g/mol) 
               
               
                   
               
             
             
               
                   
               
             
          
           
               
                 1 
                 5 
                 237 
               
               
                 2 
                 8 
                 367 
               
               
                 3 
                 15 
                 676 
               
               
                 4 
                 23 
                 1027 
               
               
                 5 
                 25 
                 1116 
               
               
                   
               
             
          
         
       
     
     Fatty Alcohols 
     Fatty alcohols are useful in the practice of the present invention are items of commerce they are available as either single components or mixtures. 
     Fatty alcohols are useful as raw materials in the preparation of compounds of the present invention are commercially available from a variety of sources including Procter and Gamble of Cincinnati Ohio. 
     The structures are well known to those skilled in the art.
 
R—OH
 
     
       
         
               
             
               
               
               
               
               
             
               
               
               
               
               
             
           
               
                   
               
               
                 Saturated 
               
             
          
           
               
                   
                 Example 
                 R Formula 
                 Common Name 
                 Molecular Weight 
               
               
                   
                   
               
             
          
           
               
                   
                 6 
                 C 8 H 18   
                 Capryl 
                 130 
               
               
                   
                 7 
                 C 10 H 22   
                 Capric 
                 158 
               
               
                   
                 8 
                 C 12 H 25   
                 Lauryl 
                 186 
               
               
                   
                 9 
                 C 14 H 30   
                 Myristyl 
                 214 
               
               
                   
                 10 
                 C 15 H 32   
                 Pentadecyl 
                 229 
               
               
                   
                 11 
                 C 16 H 34   
                 Cetyl 
                 243 
               
               
                   
                 12 
                 C 18 H 36   
                 Stearyl 
                 269 
               
               
                   
                 13 
                 C 20 H 40   
                 Arachidyl 
                 297 
               
               
                   
                 14 
                 C 22 H 44   
                 Behenyl 
                 325 
               
               
                   
                 15 
                 C 26 H 52   
                 Cetryl 
                 381 
               
               
                   
                 16 
                 C 34 H 68   
                 Geddyl 
                 493 
               
               
                   
                   
               
             
          
         
       
     
     
       
         
               
             
               
               
               
               
               
             
               
               
               
               
               
             
           
               
                   
               
               
                 Unsaturated 
               
             
          
           
               
                   
                 Example 
                 R Formula 
                 Common Name 
                 Molecular Weight 
               
               
                   
                   
               
             
          
           
               
                   
                 17 
                 C 18 H 36   
                 Oleyl 
                 268 
               
               
                   
                 18 
                 C 18 H 34   
                 Linoleyl  
                 266 
               
               
                   
                   
               
             
          
         
       
     
     Guerbet Alcohols 
     Guerbet alcohols useful as raw materials in the preparation of compounds of the present invention are commercially available from a variety of sources including Sasol North America Incorporated of Houston Tex. 
     The structures are well known to those skilled in the art. 
                                
y is an integer ranging from 3-15 and x is an integer ranging from 5-17.
 
     
       
         
               
               
               
             
               
               
               
             
           
               
                   
               
               
                 Example 
                 y 
                 x 
               
               
                   
               
             
             
               
                   
               
             
          
           
               
                 19 
                 15 
                 17 
               
               
                 20 
                 3 
                 5 
               
               
                 21 
                 9 
                 7 
               
               
                   
               
             
          
         
       
     
     Poly(Ethylene Glycol) 
     Poly(ethylene glycol) is an item of commerce available from a variety of sources including FCI Incorporated in. It conforms to the following structure:
 
HO(CH 2 CH 2 O) x H
 
x is an integer ranging from 5 to 25.
 
     
       
         
               
               
               
             
               
               
               
             
           
               
                   
               
               
                 Example 
                 x 
                 MW 
               
               
                   
               
             
             
               
                   
               
             
          
           
               
                 22 
                 5 
                 220 
               
               
                 23 
                 15 
                 660 
               
               
                 24 
                 25 
                 1,100 
               
               
                   
               
             
          
         
       
     
     Alkyl Diols 
     They conform to the following structure:
 
HOCH 2 (CH 2 ) y OH
 
wherein;
 
y is an integer ranging from 2 to 11
 
     
       
         
               
               
               
             
               
               
               
             
           
               
                   
               
               
                 Example 
                 y 
                 MW 
               
               
                   
               
             
             
               
                   
               
             
          
           
               
                 25 
                 2 
                 76 
               
               
                 26 
                 9 
                 174 
               
               
                 27 
                 11 
                 202 
               
               
                   
               
             
          
         
       
     
     Citric Acid 
     Citric acid is an item of commerce available from a variety of sources including Pfizer. It conforms to the following structure: 
     
       
                 
         
             
             
         
      
     
     Citric acid is 2-hydroxypropane-1,2,3-tricarboxylic acid and has a CAS number of 77-92-9. 
     Compounds of the Present Invention 
     Poly(Ethylene Glycol) Mono Methyl Ether, Alkyl Citrate Polymers 
     Citrate polymers were prepared by SurfaTech Corporation, of Lawernceville, Ga. They are made by the esterification reaction of citric acid, methoxy-poly (ethylene glycol), a fatty alcohol and an alkyl diol. Poly (ethylene glycol). They conform to the following structure; 
                                
wherein;
 
R 1  is independently selected from groups consisting of —(CH 2 CH 2 O) a CH 3 , linear alkyl having 8 to 26 carbon atoms, and a Guerbet alkyl having 8 to 26 carbons, with the proviso that —(CH 2 CH 2 O) a CH 3  makes up 4-95% of R 1 ;
 
a is an integer ranging from 5 to 25;
 
R 2  is —O(CH 2 ) b O—;
 
b is an integer ranging from 2 to 12;
 
x is an integer ranging from 3 to 15;
 
     
       
         
               
               
               
               
               
             
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
             
           
               
                   
               
               
                   
                 Outside Alcohol 
                   
                 Repeat Unit 
                 Citric 
               
               
                   
                 R 1   
                   
                 R 2   
                 Acid 
               
             
          
           
               
                 Example 
                 Example 
                 Grams 
                 Example 
                 Grams  
                 Example 
                 Grams 
                 Grams 
               
               
                   
               
             
          
           
               
                 28 
                 2 
                 20.9 
                 20 
                 44.4 
                 25 
                 22.7 
                 68.7 
               
               
                 29 
                 2 
                 112.3 
                 20 
                 14.9 
                 25 
                 30.5 
                 92.4 
               
               
                 30 
                 2 
                 16.0 
                 20 
                 102.3 
                 25 
                 34.8 
                 96.8 
               
               
                 31 
                 2 
                 83.5 
                 20 
                 17.9 
                 25 
                 22.7 
                 126.0 
               
               
                 32 
                 2 
                 28.4 
                 21 
                 97.3 
                 25 
                 30.8 
                 93.4 
               
               
                 33 
                 2 
                 108.3 
                 21 
                 23.2 
                 25 
                 29.4 
                 89.1 
               
               
                 34 
                 2 
                 12.8 
                 21 
                 131.9 
                 25 
                 27.9 
                 89.1 
               
               
                 35 
                 2 
                 83.5 
                 21 
                 17.9 
                 25 
                 22.7 
                 126.0 
               
               
                 36 
                 2 
                 33.3 
                 8 
                 70.8 
                 25 
                 36.2 
                 109.7 
               
               
                 37 
                 2 
                 112.3 
                 8 
                 14.9 
                 25 
                 30.5 
                 92.4 
               
               
                 38 
                 2 
                 16.0 
                 8 
                 102.3 
                 25 
                 34.8 
                 96.8 
               
               
                 39 
                 2 
                 83.5 
                 8 
                 17.9 
                 25 
                 22.7 
                 126.0 
               
               
                 40 
                 2 
                 29.5 
                 12 
                 91.2 
                 25 
                 32.1 
                 97.2 
               
               
                 41 
                 2 
                 109.3 
                 12 
                 21.1 
                 25 
                 29.7 
                 89.9 
               
               
                 42 
                 2 
                 13.5 
                 12 
                 125.3 
                 25 
                 29.4 
                 81.7 
               
               
                 43 
                 2 
                 83.5 
                 12 
                 17.9  
                 25 
                 22.7 
                 126.0 
               
               
                 44 
                 2 
                 27.5 
                 14 
                 102.1 
                 25 
                 29.9 
                 90.5 
               
               
                 45 
                 2 
                 107.5 
                 14 
                 24.9  
                 25 
                 29.2 
                 88.4 
               
               
                 46 
                 2 
                 12.3 
                 14 
                 136.9 
                 25 
                 26.7 
                 74.1 
               
               
                 47 
                 2 
                 83.5 
                 14 
                 17.9  
                 25 
                 22.7 
                 126.0 
               
               
                 48 
                 2 
                 37.1 
                 20 
                 78.9 
                 22 
                 11.7 
                 122.2 
               
               
                 49 
                 2 
                 122.9 
                 20 
                 16.3  
                 22 
                 9.7 
                 101.1 
               
               
                 50 
                 2 
                 17.8 
                 20 
                 113.6 
                 22 
                 11.2 
                 107.4 
               
               
                 51 
                 2 
                 83.5 
                 20 
                 17.9  
                 22 
                 22.7 
                 126.0 
               
               
                 52 
                 2 
                 31.1 
                 21 
                 106.7 
                 22 
                 9.8 
                 102.4 
               
               
                 53 
                 2 
                 118.2 
                 21 
                 25.3  
                 22 
                 9.3 
                 97.2 
               
               
                 54 
                 2 
                 13.9  
                 21 
                 143.3 
                 22 
                 8.8 
                 84.0 
               
               
                 55 
                 2 
                 83.5 
                 21 
                 17.9  
                 22 
                 22.7 
                 126.0 
               
               
                 56 
                 2 
                 37.1  
                 8 
                 78.9  
                 22 
                 11.7 
                 122.2 
               
               
                 57 
                 2 
                 122.9 
                 8 
                 16.3 
                 22 
                 9.7 
                 101.1 
               
               
                 58 
                 2 
                 17.8  
                 8 
                 113.6 
                 22 
                 11.2 
                 107.4 
               
               
                 59 
                 2 
                 83.5  
                 8 
                 17.9  
                 22 
                 22.7 
                 126.0 
               
               
                 60 
                 2 
                 32.5  
                 12 
                 100.3 
                 22 
                 10.2 
                 107.0 
               
               
                 61 
                 2 
                 119.4 
                 12 
                 23.0  
                 22 
                 9.4 
                 98.2 
               
               
                 62 
                 2 
                 14.8  
                 12 
                 136.8 
                 22 
                 9.3 
                 89.2 
               
               
                 63 
                 2 
                 83.5  
                 12 
                 17.9  
                 22 
                 22.7 
                 126.0 
               
               
                 64 
                 2 
                 30.0  
                 14 
                 111.6 
                 22 
                 9.4 
                 98.9 
               
               
                 65 
                 2 
                 117.2 
                 14 
                 27.2  
                 22 
                 9.2 
                 96.4 
               
               
                 66 
                 2 
                 13.3  
                 14 
                 148.1 
                 22 
                 8.4 
                 80.2 
               
               
                 67 
                 2 
                 83.5  
                 14 
                 17.9  
                 22 
                 22.7 
                 126.0 
               
               
                 68 
                 2 
                 15.8  
                 20 
                 33.5  
                 23 
                 148.8 
                 51.9 
               
               
                 69 
                 2 
                 58.0 
                 20 
                 7.7 
                 23 
                 136.6 
                 47.7 
               
               
                 70 
                 2 
                 7.7 
                 20 
                 49.4 
                 23 
                 146.1 
                 46.8 
               
               
                 71 
                 2 
                 83.5 
                 20 
                 17.9 
                 23 
                 22.7 
                 126.0 
               
               
                 72 
                 2 
                 14.6 
                 21 
                 50.0 
                 23 
                 137.5 
                 48.0 
               
               
                 73 
                 2 
                 56.9 
                 21 
                 12.2 
                 23 
                 134.1 
                 46.8 
               
               
                 74 
                 2 
                 6.9 
                 21 
                 71.1  
                 23 
                 130.3 
                 41.7 
               
               
                 75 
                 2 
                 83.5  
                 21 
                 17.9  
                 23 
                 22.7 
                 126.0 
               
               
                 76 
                 2 
                 15.8 
                 8 
                 33.5  
                 23 
                 148.8 
                 51.9 
               
               
                 77 
                 2 
                 58.0 
                 8 
                 7.7 
                 23 
                 136.6 
                 47.7 
               
               
                 78 
                 2 
                 7.7 
                 8 
                 49.4 
                 23 
                 146.1 
                 46.8 
               
               
                 79 
                 2 
                 83.5  
                 8 
                 17.9 
                 23 
                 22.7 
                 126.0 
               
               
                 80 
                 2 
                 14.9  
                 12 
                 45.9  
                 23 
                 140.3 
                 49.0 
               
               
                 81 
                 2 
                 57.2  
                 12 
                 11.0  
                 23 
                 134.8 
                 47.0 
               
               
                 82 
                 2 
                 7.1 
                 12 
                 65.8  
                 23 
                 134.1 
                 42.9 
               
               
                 83 
                 2 
                 83.5 
                 12 
                 17.9  
                 23 
                 22.7 
                 126.0 
               
               
                 84 
                 2 
                 14.3 
                 14 
                 53.3  
                 23 
                 135.2 
                 47.2 
               
               
                 85 
                 2 
                 56.7 
                 14 
                 13.2 
                 23 
                 133.6 
                 46.6 
               
               
                 86 
                 2 
                 6.8 
                 14 
                 75.2  
                 23 
                 127.3 
                 40.7 
               
               
                 87 
                 2 
                 83.5 
                 14 
                 17.9  
                 23 
                 22.7 
                 126.0 
               
               
                 88 
                 2 
                 11.3 
                 20 
                 24.0  
                 24 
                 177.5 
                 37.2 
               
               
                 89 
                 2 
                 42.5 
                 20 
                 5.6 
                 24 
                 166.9 
                 35.0 
               
               
                 90 
                 2 
                 5.6 
                 20 
                 35.6  
                 24 
                 175.2 
                 33.6 
               
               
                 91 
                 2 
                 83.5  
                 20 
                 17.9  
                 24 
                 22.7 
                 126.0 
               
               
                 92 
                 2 
                 10.7  
                 21 
                 36.6  
                 24 
                 167.6 
                 35.1 
               
               
                 93 
                 2 
                 41.9 
                 21 
                 9.0 
                 24 
                 164.6 
                 34.5 
               
               
                 94 
                 2 
                 5.1 
                 21 
                 52.7  
                 24 
                 161.2 
                 30.9 
               
               
                 95 
                 2 
                 83.5  
                 21 
                 17.9  
                 24 
                 22.7 
                 126.0 
               
               
                 96 
                 2 
                 11.3  
                 8 
                 24.0  
                 24 
                 177.5 
                 37.2 
               
               
                 97 
                 2 
                 42.5 
                 8 
                 5.6 
                 24 
                 166.9 
                 35.0 
               
               
                 98 
                 2 
                 5.6 
                 8 
                 35.6  
                 24 
                 175.2 
                 33.6 
               
               
                 99 
                 2 
                 83.5 
                 8 
                 17.9  
                 24 
                 22.7 
                 126.0 
               
               
                 100 
                 2 
                 10.8  
                 12 
                 33.4  
                 24 
                 170.1  
                 35.6 
               
               
                 101 
                 2 
                 42.1  
                 12 
                 8.1 
                 24 
                 165.2  
                 34.6 
               
               
                 102 
                 2 
                 5.2 
                 12 
                 48.5 
                 24 
                 164.7  
                 31.6 
               
               
                 103 
                 2 
                 83.5  
                 12 
                 17.9  
                 24 
                 22.7 
                 126.0 
               
               
                 104 
                 2 
                 10.5  
                 14 
                 39.1  
                 24 
                 165.6  
                 34.7 
               
               
                 105 
                 2 
                 41.8  
                 14 
                 9.7 
                 24 
                 164.1  
                 34.4 
               
               
                 106 
                 2 
                 5.0 
                 14 
                 56.2  
                 24 
                 158.4  
                 30.4 
               
               
                 107 
                 2 
                 83.5  
                 14 
                 17.9  
                 24 
                 22.7 
                 126.0 
               
               
                 108 
                 2 
                 28.1  
                 20 
                 59.7  
                 26 
                 69.8 
                 92.4 
               
               
                 109 
                 2 
                 97.0  
                 20 
                 12.9 
                 26 
                 60.3 
                 79.8 
               
               
                 110 
                 2 
                 13.6  
                 20 
                 86.7  
                 26 
                 67.6 
                 82.1 
               
               
                 111 
                 2 
                 83.5  
                 20 
                 17.9  
                 26 
                 22.7 
                 126.0 
               
               
                 112 
                 2 
                 24.5  
                 21 
                 84.0 
                 26 
                 60.9 
                 80.6 
               
               
                 113 
                 2 
                 94.0  
                 21 
                 20.2 
                 26 
                 58.4 
                 77.4 
               
               
                 114 
                 2 
                 11.2  
                 21 
                 115.4  
                 26 
                 55.8 
                 67.7 
               
               
                 115 
                 2 
                 83.5  
                 21 
                 17.9 
                 26 
                 22.7 
                 126.0 
               
               
                 116 
                 2 
                 28.1 
                 8 
                 59.7  
                 26 
                 69.8 
                 92.4 
               
               
                 117 
                 2 
                 97.0 
                 8 
                 12.9  
                 26 
                 60.3 
                 79.8 
               
               
                 118 
                 2 
                 13.6 
                 8 
                 86.7  
                 26 
                 67.6 
                 82.1 
               
               
                 119 
                 2 
                 83.5 
                 8 
                 17.9 
                 26 
                 22.7 
                 126.0 
               
               
                 120 
                 2 
                 25.3  
                 12 
                 78.2  
                 26 
                 63.0 
                 83.4 
               
               
                 121 
                 2 
                 94.8  
                 12 
                 18.3  
                 26 
                 58.9 
                 78.0 
               
               
                 122 
                 2 
                 11.8  
                 12 
                 108.8  
                 26 
                 58.5 
                 70.9 
               
               
                 123 
                 2 
                 83.5  
                 12 
                 17.9  
                 26 
                 22.7 
                 126.0 
               
               
                 124 
                 2 
                 23.8  
                 14 
                 88.5 
                 26 
                 59.2 
                 78.4 
               
               
                 125 
                 2 
                 93.4  
                 14 
                 21.7  
                 26 
                 58.0 
                 76.9 
               
               
                 126 
                 2 
                 10.8  
                 14 
                 120.3  
                 26 
                 53.7 
                 65.2 
               
               
                 127 
                 2 
                 83.5  
                 14 
                 17.9  
                 26 
                 22.7 
                 126.0 
               
               
                 128 
                 2 
                 26.9  
                 20 
                 57.1 
                 27 
                 77.5 
                 88.5 
               
               
                 129 
                 2 
                 93.4  
                 20 
                 12.4 
                 27 6 
                 7.4 
                 76.8 
               
               
                 130 
                 2 
                 13.0  
                 20 
                 83.1  
                 27 
                 75.2 
                 78.6 
               
               
                 131 
                 2 
                 83.5  
                 20 
                 17.9  
                 27 
                 22.7 
                 126.0 
               
               
                 132 
                 2 
                 23.6  
                 21 
                 80.8  
                 27 
                 68.0 
                 77.6 
               
               
                 133 
                 2 
                 90.6  
                 21 
                 19.4  
                 27 
                 65.4 
                 74.6 
               
               
                 134 
                 2 
                 10.8  
                 21 
                 111.4  
                 27 
                 62.5 
                 65.3 
               
               
                 135 
                 2 
                 83.5  
                 21 
                 17.9  
                 27 
                 22.7 
                 126.0 
               
               
                 136 
                 2 
                 26.9 
                 8 
                 57.1 
                 27 
                 77.5 
                 88.5 
               
               
                 137 
                 2 
                 93.4 
                 8 
                 12.4  
                 27 
                 67.4 
                 76.8 
               
               
                 138 
                 2 
                 13.0 
                 8 
                 83.1 
                 27 
                 75.2 
                 78.6 
               
               
                 139 
                 2 
                 83.5 
                 8 
                 17.9  
                 27 
                 22.7 
                 126.0 
               
               
                 140 
                 2 
                 24.4  
                 12 
                 75.2 
                 27 
                 70.3 
                 80.2 
               
               
                 141 
                 2 
                 91.3  
                 12 
                 17.6  
                 27 
                 65.9 
                 75.2 
               
               
                 142 
                 2 
                 11.3  
                 12 
                 104.9 
                 27 
                 65.4 
                 68.4 
               
               
                 143 
                 2 
                 83.5  
                 12 
                 17.9  
                 27 
                 22.7 
                 126.0 
               
               
                 144 
                 2 
                 23.0  
                 14 
                 85.3  
                 27 
                 66.2 
                 75.6 
               
               
                 145 
                 2 
                 90.0  
                 14 
                 20.9  
                 27 
                 65.0 
                 74.1 
               
               
                 146 
                 2 
                 10.4  
                 14 
                 116.3 
                 27 
                 60.2 
                 63.0 
               
               
                 147 
                 2 
                 83.5  
                 14 
                 17.9  
                 27 
                 22.7 
                 126.0 
               
               
                   
               
             
          
         
       
     
     EXAMPLES 
     Esterification Reactions 
     In addition to the molecular weight of poly(ethylene glycol) monomethyl ether (MePEG), it is very important for the practice of the current invention resulting in a compound of the present, to have the correct ratio of fatty groups to MePEG groups. Also, the length of the alkyl diol and molecular weight of the polymer is of paramount importance. 
     General Procedure 
     To the specified number of grams of citric acid is added to a specified amount of MePEG (Examples 2-5) and the specified number of grams of alcohol (Examples 6-21). The reaction mixture is heated to 160-180° C. The alkyl diol is added when the temperature is reached. Water is removed by vacuum during the reaction process. The reaction is monitored by determination of acid value. The acid value will diminish as the reaction proceeds. The reaction is cooled once the acid value fails to change over an additional two hours at temperature. The product is used without purification. 
     Poly(Ethylene Glycol) Mono Methyl Ether, Di-Alkyl Citrate Co-Polymers 
     Citrate di-alkyl co-polymers were prepared by SurfaTech Corporation, of Lawernceville, Ga. They are made by the esterification reaction of citric acid, methoxy-poly (ethylene glycol), a fatty alcohol and at least two different alkyl diol. 
     
       
         
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
             
           
               
                   
               
               
                   
                 Outside Alcohol 
                   
                 Repeat Unit 
                   
                 Citric 
               
               
                   
                 R 1   
                   
                 R 2   
                   
                 Acid 
               
             
          
           
               
                 Example 
                 Example 
                 Grams 
                 Example 
                 Grams 
                 Example 
                 Grams 
                 Example 
                 Grams 
                 Grams 
               
               
                   
               
             
          
           
               
                 148 
                 2 
                 32.1 
                 20 
                 68.3 
                 25 
                 27.9 
                 26 
                 16.0 
                 105.7 
               
               
                 149 
                 2 
                 108.8 
                 20 
                 14.5 
                 25 
                 23.6 
                 26 
                 13.5 
                 89.6 
               
               
                 150 
                 2 
                 29.0 
                 20 
                 61.6 
                 25 
                 6.3 
                 26 
                 57.7 
                 95.4 
               
               
                 151 
                 2 
                 99.7 
                 20 
                 13.2 
                 25 
                 5.4 
                 26 
                 49.6 
                 82.1 
               
               
                 152 
                 2 
                 27.3 
                 21 
                 93.5 
                 25 
                 23.7 
                 27 
                 15.7 
                 89.8 
               
               
                 153 
                 2 
                 104.2 
                 21 
                 22.3  
                 25 
                 22.6 
                 27 
                 15.0 
                 85.8 
               
               
                 154 
                 2 
                 24.4 
                 21 
                 83.7 
                 25 
                 5.3 
                 27 
                 56.3 
                 80.3 
               
               
                 155 
                 2 
                 93.7 
                 21 
                 20.1 
                 25 
                 5.1 
                 27 
                 54.1 
                 77.1 
               
               
                 156 
                 2 
                 32.1 
                 8 
                 68.3 
                 25 
                 27.9 
                 26 
                 16.0 
                 105.7 
               
               
                 157 
                 2 
                 108.8 
                 8 
                 14.5 
                 25 
                 23.6 
                 26 
                 13.5 
                 89.6 
               
               
                 158 
                 2 
                 29.0 
                 8 
                 61.6 
                 25 
                 6.3 
                 26 
                 57.7 
                 95.4 
               
               
                 159 
                 2 
                 99.7 
                 8 
                 13.2 
                 25 
                 5.4 
                 26 
                 49.6 
                 82.1 
               
               
                 160 
                 2 
                 28.3 
                 12 
                 87.4 
                 25 
                 24.6 
                 27 
                 16.4 
                 93.3 
               
               
                 161 
                 2 
                 105.2 
                 12 
                 20.3 
                 25 
                 22.8 
                 27 
                 15.2 
                 86.5 
               
               
                 162 
                 2 
                 25.2 
                 12 
                 77.9 
                 25 
                 5.5 
                 27 
                 58.3 
                 83.1 
               
               
                 163 
                 2 
                 94.4 
                 12 
                 18.2 
                 25 
                 5.1 
                 27 
                 54.5 
                 77.7 
               
               
                 164 
                 2 
                 23.1 
                 14 
                 85.9 
                 27 
                 53.4 
                 26 
                 11.5 
                 76.1 
               
               
                 165 
                 2 
                 90.7 
                 14 
                 21.1 
                 27 
                 52.3 
                 26 
                 11.3 
                 74.6 
               
               
                 166 
                 2 
                 23.6 
                 14 
                 87.8 
                 27 
                 13.6 
                 26 
                 47.0 
                 77.8 
               
               
                 167 
                 2 
                 92.7 
                 14 
                 21.5 
                 27 
                 13.4  
                 26 
                 46.1 
                 76.3 
               
               
                   
               
             
          
         
       
     
     Poly(Ethylene Glycol) Mono Methyl Ether, Alkyl PEG Citrate Copolymers 
     Alkyl/PEG citrate co-polymers were prepared by SurfaTech Corporation, of Lawernceville, Ga. They are made by the esterification reaction of citric acid, methoxy-poly (ethylene glycol), a fatty alcohol, alkyl diol and poly(ethylene glycol). 
     
       
         
               
               
               
               
               
               
             
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
             
           
               
                   
               
               
                   
                 Outside Alcohol 
                   
                 Repeat Unit 
                   
                 Citric 
               
             
          
           
               
                   
                   
                 R 1   
                   
                 R 2   
                   
                 Acid 
               
             
          
           
               
                 Example 
                 Example 
                 Grams 
                 Example 
                 Grams 
                 Example  
                 Grams  
                 Example  
                 Grams  
                 Grams 
               
               
                   
               
             
          
           
               
                 168 
                 2 
                 21.1 
                 20 
                 44.8 
                 27 
                 48.6 
                 24 
                 66.2 
                 69.3 
               
               
                 169 
                 2 
                 75.3 
                 20 
                 10.0 
                 27 
                 43.5 
                 24 
                 59.2 
                 62.0 
               
               
                 170 
                 2 
                 12.8 
                 20 
                 27.2 
                 27 
                 7.4 
                 24 
                 160.6 
                 42.1 
               
               
                 171 
                 2 
                 47.7 
                 20 
                 6.3 
                 27 
                 6.9 
                 24 
                 149.9 
                 39.2 
               
               
                 172 
                 2 
                 19.0 
                 21 
                 65.1 
                 27 
                 43.8 
                 24 
                 59.7 
                 62.5 
               
               
                 173 
                 2 
                 73.5 
                 21 
                 15.8 
                 27 
                 42.4 
                 24 
                 57.8 
                 60.5 
               
               
                 174 
                 2 
                 12.0 
                 21 
                 41.1 
                 27 
                 6.9 
                 24 
                 150.6 
                 39.4 
               
               
                 175 
                 2 
                 47.0  
                 21 
                 10.1 
                 27 
                 6.8 
                 24 
                 147.6 
                 38.6 
               
               
                 176 
                 2 
                 21.1 
                 8 
                 44.8 
                 27 
                 48.6 
                 24 
                 66.2 
                 69.3 
               
               
                 177 
                 2 
                 75.3 
                 8 
                 10.0 
                 27 
                 43.5 
                 24 
                 59.2 
                 62.0 
               
               
                 178 
                 2 
                 12.8 
                 8 
                 27.2 
                 27 
                 7.4 
                 24 
                 160.6 
                 42.1 
               
               
                 179 
                 2 
                 47.7 
                 8 
                 6.3 
                 27 
                 6.9 
                 24 
                 149.9 
                 39.2 
               
               
                 180 
                 2 
                 19.5 
                 12 
                 60.1 
                 27 
                 45.0 
                 24 
                 61.2 
                 64.1 
               
               
                 181 
                 2 
                 74.0 
                 12 
                 14.3 
                 27 
                 42.7 
                 24 
                 58.1 
                 60.9 
               
               
                 182 
                 2 
                 12.2 
                 12 
                 37.6 
                 27 
                 7.0 
                 24 
                 153.1 
                 40.1 
               
               
                 183 
                 2 
                 47.1 
                 12 
                 9.1 
                 27 
                 6.8 
                 24 
                 148.2 
                 38.8 
               
               
                 184 
                 2 
                 18.6 
                 14 
                 69.0 
                 27 
                 42.9 
                 24 
                 58.4 
                 61.1 
               
               
                 185 
                 2 
                 73.1 
                 14 
                 17.0 
                 27 
                 42.2 
                 24 
                 57.5 
                 60.2 
               
               
                 186 
                 2 
                 11.8 
                 14 
                 43.9 
                 27 
                 6.8 
                 24 
                 148.6 
                 38.9 
               
               
                 187 
                 2 
                 46.8 
                 14 
                 10.9 
                 27 
                 6.8 
                 24 
                 147.1 
                 38.5 
               
               
                 188 
                 2 
                 23.6 
                 20 
                 50.1 
                 27 
                 54.4  
                 23 
                 44.4  
                 77.5 
               
               
                 189 
                 2 
                 83.2 
                 20 
                 11.1 
                 27 
                 48.0  
                 23 
                 39.2 
                 68.5 
               
               
                 190 
                 2 
                 17.2 
                 20 
                 36.6 
                 27 
                 9.9 
                 23 
                 129.7 
                 56.6 
               
               
                 191 
                 2 
                 62.7 
                 20 
                 8.3 
                 27 
                 9.1 
                 23 
                 118.3 
                 51.6 
               
               
                 192 
                 2 
                 21.0 
                 21 
                 71.9 
                 27 
                 48.4  
                 23 
                 39.6 
                 69.1 
               
               
                 193 
                 2 
                 81.0 
                 21 
                 17.4 
                 27 
                 46.8  
                 23 
                 38.2 
                 66.7 
               
               
                 194 
                 2 
                 15.8 
                 21 
                 54.1 
                 27 
                 9.1 
                 23 
                 119.0 
                 51.9 
               
               
                 195 
                 2 
                 61.5 
                 21 
                 13.2 
                 27 
                 8.9 
                 23 
                 115.9 
                 50.6 
               
               
                 196 
                 2 
                 23.6 
                 8 
                 50.1 
                 27 
                 54.4  
                 23 
                 44.4 
                 77.5 
               
               
                 197 
                 2 
                 83.2 
                 8 
                 11.1 
                 27 
                 48.0  
                 23 
                 39.2  
                 68.5 
               
               
                 198 
                 2 
                 17.2 
                 8 
                 36.6 
                 27 
                 9.9 
                 23 
                 129.7 
                 56.6 
               
               
                 199 
                 2 
                 62.7 
                 8 
                 8.3 
                 27 
                 9.1 
                 23 
                 118.3 
                 51.6 
               
               
                 200 
                 2 
                 21.6 
                 12 
                 66.7  
                 27 
                 49.9  
                 23 
                 40.7  
                 71.1 
               
               
                 201 
                 2 
                 81.6 
                 12 
                 15.7  
                 27 
                 47.1 
                 23 
                 38.5 
                 67.1 
               
               
                 202 
                 2 
                 16.1 
                 12 
                 49.8  
                 27 
                 9.3 
                 23 
                 121.7 
                 53.1 
               
               
                 203 
                 2 
                 61.8 
                 12 
                 11.9  
                 27 
                 8.9 
                 23 
                 116.5 
                 50.8 
               
               
                 204 
                 2 
                 20.5 
                 14 
                 76.1 
                 27 
                 47.3  
                 23 
                 38.6  
                 67.4 
               
               
                 205 
                 2 
                 80.6 
                 14 
                 18.7 
                 27 
                 46.5  
                 23 
                 38.0  
                 66.3 
               
               
                 206 
                 2 
                 15.5 
                 14 
                 57.6 
                 27 
                 8.9 
                 23 
                 116.9 
                 51.0 
               
               
                 207 
                 2 
                 61.2 
                 14 
                 14.2 
                 27 
                 8.8 
                 23 
                 115.4 
                 50.4 
               
               
                 208 
                 2 
                 26.7 
                 20 
                 56.8 
                 27 
                 61.7  
                 22 
                 16.8 
                 88.0 
               
               
                 209 
                 2 
                 92.9 
                 20 
                 12.3 
                 27 
                 53.6  
                 22 
                 14.6  
                 76.5 
               
               
                 210 
                 2 
                 26.3 
                 20 
                 55.9 
                 27 
                 15.2  
                 22 
                 66.1 
                 86.5 
               
               
                 211 
                 2 
                 91.6 
                 20 
                 12.2 
                 27 
                 13.2  
                 22 
                 57.6 
                 75.4 
               
               
                 212 
                 2 
                 23.5 
                 21 
                 80.4 
                 27 
                 54.2  
                 22 
                 14.7 
                 77.2 
               
               
                 213 
                 2 
                 90.2 
                 21 
                 19.3 
                 27 
                 52.1  
                 22 
                 14.2 
                 74.2 
               
               
                 214 
                 2 
                 23.1 
                 21 
                 79.3  
                 27 
                 13.3  
                 22 
                 58.1 
                 76.1 
               
               
                 215 
                 2 
                 89.0 
                 21 
                 19.1 
                 27 
                 12.8  
                 22 
                 55.9 
                 73.2 
               
               
                 216 
                 2 
                 26.7 
                 8 
                 56.8 
                 27 
                 61.7  
                 22 
                 16.8  
                 88.0 
               
               
                 217 
                 2 
                 92.9 
                 8 
                 12.3  
                 27 
                 53.6  
                 22 
                 14.6 
                 76.5 
               
               
                 218 
                 2 
                 26.3 
                 8 
                 55.9  
                 27 
                 15.2  
                 22 
                 66.1 
                 86.5 
               
               
                 219 
                 2 
                 91.6 
                 8 
                 12.2 
                 27 
                 13.2 
                 22 
                 57.6 
                 75.4 
               
               
                 220 
                 2 
                 24.2 
                 12 
                 74.8 
                 27 
                 56.0 
                 22 
                 15.2 
                 79.8 
               
               
                 221 
                 2 
                 90.9 
                 12 
                 17.5 
                 27 
                 52.5 
                 22 
                 14.3 
                 74.8 
               
               
                 222 
                 2 
                 23.9 
                 12 
                 73.7 
                 27 
                 13.8 
                 22 
                 60.0 
                 78.6 
               
               
                 223 
                 2 
                 89.7 
                 12 
                 17.3 
                 27 
                 12.9 
                 22 
                 56.4 
                 73.8 
               
               
                 224 
                 2 
                 22.8 
                 14 
                 84.9 
                 27 
                 52.7 
                 22 
                 14.4 
                 75.2 
               
               
                 225 
                 2 
                 89.6 
                 14 
                 20.8 
                 27 
                 51.7 
                 22 
                 14.1 
                 73.8 
               
               
                 226 
                 2 
                 22.5 
                 14 
                 83.7 
                 27 
                 13.0 
                 22 
                 56.6 
                 74.2 
               
               
                 227 
                 2 
                 88.4 
                 14 
                 20.5 
                 27 
                 12.8 
                 22 
                 55.6 
                 72.7 
               
               
                 228 
                 2 
                 22.0 
                 12 
                 67.7 
                 25 
                 19.1 
                 24 
                 60.0 
                 72.3 
               
               
                 229 
                 2 
                 82.8 
                 12 
                 16.0 
                 25 
                 18.0 
                 24 
                 65.1 
                 68.1 
               
               
                 230 
                 2 
                 12.4 
                 12 
                 38.3 
                 25 
                 2.7 
                 24 
                 155.9  
                 40.8 
               
               
                 231 
                 2 
                 48.0 
                 12 
                 9.2 
                 25 
                 2.6 
                 24 
                 150.7  
                 39.5 
               
               
                 232 
                 2 
                 24.0 
                 8 
                 51.0 
                 25 
                 20.8 
                 24 
                 75.3 
                 78.9 
               
               
                 233 
                 2 
                 84.5 
                 8 
                 11.2 
                 25 
                 18.3 
                 24 
                 66.4 
                 69.5 
               
               
                 234 
                 2 
                 13.0 
                 8 
                 27.7 
                 25 
                 2.8 
                 24 
                 163.6  
                 42.8 
               
               
                 235 
                 2 
                 48.5 
                 8 
                 6.4 
                 25 
                 2.6 
                 24 
                 152.5  
                 39.9 
               
               
                 236 
                 2 
                 23.2 
                 14 
                 86.3 
                 25 
                 20.2 
                 23 
                 43.8 
                 76.5 
               
               
                 237 
                 2 
                 91.1 
                 14 
                 21.2 
                 25 
                 19.8 
                 23 
                 43.0 
                 75.0 
               
               
                 238 
                 2 
                 15.9 
                 14 
                 58.9 
                 25 
                 3.4 
                 23 
                 119.6  
                 52.2 
               
               
                 239 
                 2 
                 62.6 
                 14 
                 14.5 
                 25 
                 3.4 
                 23 
                 118.0  
                 51.5 
               
               
                 240 
                 2 
                 23.9 
                 21 
                 81.8 
                 25 
                 20.7 
                 23 
                 45.0 
                 78.6 
               
               
                 241 
                 2 
                 91.7 
                 21 
                 19.7 
                 25 
                 19.9 
                 23 
                 43.2 
                 75.5 
               
               
                 242 
                 2 
                 16.1 
                 21 
                 55.4 
                 25 
                 3.5 
                 23 
                 121.8  
                 53.2 
               
               
                 243 
                 2 
                 62.9 
                 21 
                 13.5 
                 25 
                 3.4 
                 23 
                 118.5  
                 51.7 
               
               
                 244 
                 2 
                 28.2 
                 12 
                 86.9 
                 25 
                 24.5 
                 22 
                 17.7 
                 92.7 
               
               
                 245 
                 2 
                 104.6 
                 12 
                 20.2 
                 25 
                 22.7 
                 22 
                 16.4 
                 86.1 
               
               
                 246 
                 2 
                 24.7 
                 12 
                 76.3 
                 25 
                 5.4 
                 22 
                 62.2 
                 81.4 
               
               
                 247 
                 2 
                 92.6 
                 12 
                 17.9 
                 25 
                 5.0 
                 22 
                 58.2 
                 76.2 
               
               
                 248 
                 2 
                 21.6 
                 8 
                 46.0 
                 26 
                 43.0 
                 24 
                 68.0 
                 71.3 
               
               
                 249 
                 2 
                 77.2 
                 8 
                 10.3 
                 26 
                 38.4 
                 24 
                 60.7 
                 63.5 
               
               
                 250 
                 2 
                 12.8 
                 8 
                 27.3 
                 26 
                 6.4 
                 24 
                 161.3  
                 42.2 
               
               
                 251 
                 2 
                 47.9 
                 8 
                 6.4 
                 26 
                 5.9 
                 24 
                 150.4  
                 39.4 
               
               
                 252 
                 2 
                 24.3 
                 20 
                 51.6 
                 26 
                 48.3 
                 23 
                 45.8 
                 80.0 
               
               
                 253 
                 2 
                 85.5 
                 20 
                 11.4 
                 26 
                 42.5 
                 23 
                 40.3 
                 70.3 
               
               
                 254 
                 2 
                 17.3 
                 20 
                 36.8 
                 26 
                 8.6 
                 23 
                 130.4  
                 56.9 
               
               
                 255 
                 2 
                 63.0 
                 20 
                 8.4 
                 26 
                 7.8 
                 23 
                 118.9  
                 51.9 
               
               
                 256 
                 2 
                 23.5 
                 14 
                 87.4 
                 26 
                 46.8 
                 22 
                 14.8 
                 77.5 
               
               
                 257 
                 2 
                 92.3 
                 14 
                 21.4 
                 26 
                 45.9 
                 22 
                 14.5 
                 75.9 
               
               
                 258 
                 2 
                 22.7 
                 14 
                 84.3 
                 26 
                 11.3 
                 22 
                 57.1 
                 74.7 
               
               
                 259 
                 2 
                 89.0 
                 14 
                 20.7 
                 26 
                 11.1 
                 22 
                 56.0 
                 72.3 
               
               
                 260 
                 2 
                 24.2 
                 21 
                 82.9 
                 26 
                 48.1 
                 22 
                 15.2 
                 79.6 
               
               
                 261 
                 2 
                 92.9 
                 21 
                 19.9 
                 26 
                 46.2 
                 22 
                 14.6 
                 76.4 
               
               
                 262 
                 2 
                 23.3 
                 21 
                 79.9 
                 26 
                 11.6 
                 22 
                 58.6 
                 76.7 
               
               
                 263 
                 2 
                 89.6 
                 21 
                 19.2 
                 26 
                 11.1 
                 22 
                 56.3 
                 73.7 
               
               
                   
               
             
          
         
       
     
     Applications 
     The compounds of the present invention are useful as polymeric emulsifiers and can be used in a wide range of applications, emulsions (oil in water and silicone in water), invert emulsions (water in oil and silicone in water). The variations are made by altering the amount of me-peg in the molecule. 
     Another key advantage of the compounds of the present invention is the ability to provide polymers that are soluble over a wide range of solvents, including but not limited to oil, polar oils like esters, alcohol, hydroalcoholic solutions, and water. Delivered out of these solvents the compounds of the present invention are polymeric emollients and moisturizers. 
     In biochemical applications, partition coefficients is often expressed in terms of an octanol/water coefficient (Ko/w)—the ratio at equilibrium of the concentration of a non-ionized organic compound in an organic solvent (e.g., octanol) versus the concentration of the compound water. Ko/w has been correlated with lipophilicity, the affinity of a compound for a lipophilic environment. Compounds having Ko/w of greater than one are lipophilic; those below one are hydrophilic. Ko/w thus provides an important predictive measure of the ability of a compound to pass through the acid mantle and permeate the lipophilic membranes of cells of the epidermis and dermis. Polar (i.e., hydrophilic) materials extract a different, but also highly-desirable class of compounds from botanical materials. The ability to extract a variety actives (i.e., both lipophilic and hydrophilic) over a wide range of polarities has heretofore been unattainable. 
     Prior to the present invention, extraction technology has been limited by the nature of available solvents (e.g., oil, aqueous, hydroalcohol and glycol). Surprisingly, applicants have discovered that a series of silicone molecules customized to alter their solubilities in oil, water, silicone and hydroalcoholic solvents produces an almost infinite number of extraction solvents that selectively and specifically extract desired active fractions from botanical materials. In addition to improving extraction efficiency, the customized polymer extraction vehicles of the present invention contribute to the aesthetics and functionality of topical formulations—they impart outstanding skin feel and are non-irritating while retaining the actives on the skin for longer periods of time. 
     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.

Technology Category: 8