Abstract:
The present invention is directed to a series of vinyl ether based silicone polymers and their use in personal care applications. They are prepared by the hydrosilylation reaction of a vinyl ether and a silanic hydrogen compound. The compounds find use in personal care applications.

Description:
GOVERNMENT SPONSORSHIP 
       [0001]    None 
       FIELD OF THE INVENTION 
       [0002]    The present invention is directed to a series of vinyl ether based silicone polymers and their use in personal care applications. 
       BACKGROUND OF THE INVENTION 
       [0003]    Dimethicone compounds conform to the following structure: 
         [0000]    
       
                 
         
             
             
         
       
     
         [0004]    Silicone fluids, also called silicone oils, or simple silicone are sold by their viscosity and range from 0.65 cst to 1,000,000 cst. If blending two different viscosity fluids does not make the product the viscosity is related to molecular weight. The viscosity allows for an approximate calculation of the value of “n”. The data is shown below. 
         [0000]    
       
         
               
               
               
               
             
               
               
               
               
             
           
               
                   
               
               
                 Viscosity 25 C. 
                 Approximate 
                 Approximate 
                   
               
               
                 (Centistokes) 
                 Molecular Weight 
                 “n” Value 
                 Compound 
               
               
                   
               
             
             
               
                   
               
             
          
           
               
                 5 
                 800 
                 9 
                 MD 9 M 
               
               
                 50 
                 3,780 
                 53 
                 MD 53 M 
               
               
                 100 
                 6,000 
                 85 
                 MD 85 M 
               
               
                 200 
                 9,430 
                 127 
                 MD 127 M 
               
               
                 350 
                 13,650 
                 185 
                 MD 185 M 
               
               
                 500 
                 17,350 
                 230 
                 MD 230 M 
               
               
                 1,000 
                 28,000 
                 375 
                 MD 375 M 
               
               
                 10,000 
                 67,700 
                 910 
                 MD 910 M 
               
               
                 60,000 
                 116,500 
                 1,570 
                 MD 1570 M 
               
               
                 100,000 
                 139,050 
                 1,875 
                 MD 1875 M 
               
               
                   
               
             
          
         
       
     
         [0005]    One difficulty that is encountered is that these materials are insoluble in oils, water and in fluoro compounds. 
         [0006]    This complication has resulted in difficulty in getting the properties of silicone, including spreadability and feel into systems that contain water or oil. 
         [0007]    Molecules that contain water soluble, oil soluble and silicone soluble groups contain in one molecule three mutually insoluble groups. The concept of “hydrophilic and “hydrophobic” is related to water soluble, and in systems containing silicone needs to be expanded to include silicone compounds. 
         [0000]    
       
         
               
               
               
             
           
               
                   
                   
               
             
             
               
                   
                 Hydrophilic (water loving) 
                 Hydrophobic (water hating) 
               
               
                   
                 Oleophilic (oil loving) 
                 Oleophobic (oil hating) 
               
               
                   
                 Siliphilic (silicone loving 
                 Siliphobic (silicone hating) 
               
               
                   
                   
               
             
          
         
       
     
         [0008]    The way to improve solubility of silicone compounds in other types of solvents is to make molecules that contain silicone groups and groups soluble in the other solvent. Such molecules are amphilic, and have desirable properties. 
         [0009]    To make a molecule soluble in oils, an oil soluble alkyl group is reacted onto the silicone backbone. A typical structure is shown: 
         [0000]    
       
                 
         
             
             
         
       
     
         [0000]    wherein:
   R is —(CH 2 ) m —CH 3 ;   m is an integer ranging from 7 to 44.   
 
         [0012]    Some of the undesirable attributes of these products include: 
         [0013]    1. They are based upon alpha olefin, CH 2 ═CH—(CH 2 ) m-2 —CH 3 , an impure substance and can contain up to 20% unreactive alkane CH 3 —(CH 2 ) m-1 —CH 3 . 
         [0014]    2. The alkyl group contains no polar groups making them of limited application is solubilizing organic materials that have polarity. 
         [0015]    The present invention overcomes these problems and offers unique cosmetic aesthetics by replacing the alkyl group with an alkyl ether group. The raw material used to make the compounds of the present invention are vinyl ethers. They are pure materials (contain no alkane) and have a polar oxygen atom present in the backbone. They satisfy a long felt need n the industry for a chemically pure, polar oil soluble product. 
         [0016]    The vinyl ethers useful as raw materials for the synthesis of the compounds of the present invention conform to the following structure: 
         [0000]      CH 2 ═CH—O—(CH 2 ) z CH 3  
 
         [0017]    These compounds are made by the reaction of the alcohol (which is natural, derived from triglycerides) with acetylene. The chemistry is referred to as Reppe chemistry and is the topic of U.S. Pat. No. 2,017,335 issued to Reppe Dec. 8, 1934, incorporated herein by reference. 
         [0018]    The reaction is applicable to both aliphatic and aromatic alcohols, primary and secondary alcohols, and phenols. Potassium hydroxide is employed as the catalyst. Ethers and esters and secondary amines also react with acetylene under pressure. For example, the reaction between methyl alcohol and acetylene goes very smoothly at about 200° C. to give methyl vinyl ether in the presence of KOH: 
         [0000]    
       
                 
         
             
             
         
       
     
         [0019]    Additional patents related to this chemistry to Reppe include
   U.S. Pat. No. 1,941,108 entitled Production of Vinyl Ethers;   U.S. Pat. No. 1,959,927 entitled Production of Vinyl Ethers;   U.S. Pat. No. 2,021,869 entitled Production of Vinyl Ether;   U.S. Pat. No. 2,066,076 entitled Producing Vinyl Ethers, all incorporated herein by reference.   
 
         [0024]    These materials have been heretofore not attached to silicone to make the polymers of the present invention addressing the long felt need in the personal care market and providing the desirable unexpected benefits described above. 
       THE INVENTION 
     OBJECTIVE OF THE INVENTION 
       [0025]    The object of the present invention is to provide a series of alkyl ether based silicone polymers. 
         [0026]    Another object of the present invention is to provide a process for treating hair and skin with a series of alkyl ether based silicone polymers. 
         [0027]    Other objects of the present invention will become apparent as one reads the disclosure. 
       SUMMARY OF THE INVENTION 
       [0028]    The present invention is directed to a series of alkyl ether based silicone polymers. These materials are made by the hydrosilylation of vinyl ethers, reacted with silanic hydrogen containing polymers. 
     
    
     DETAILED DESCRIPTION OF THE INVENTION 
       [0029]    The present invention is directed to a ether alkyl silicone conforming to the following structure; 
         [0000]    
       
                 
         
             
             
         
       
     
         [0000]    wherein:
   R is —(CH 2 ) 2 —O—(CH 2 ) z —CH 3 ;   z is an integer ranging from 0 to 44;   a is an integer ranging from 0 to 2,000;   b is an integer ranging from 1 to 50.   
 
         [0034]    The present invention is also directed to a ether alkyl silicone conforming to the following structure; 
         [0000]    
       
                 
         
             
             
         
       
     
         [0000]    wherein:
   R′ is —(CH 2 ) 2 —O—(CH 2 ) z —CH 3 ;   z is an integer ranging from 0 to 44;   c is an integer ranging from 0 to 2,000.   
 
         [0038]    The present invention is also directed to a process for conditioning hair and skin, which comprises contacting the hair or skin with an effective conditioning concentration of to a ether alkyl silicone conforming to the following structure; 
         [0000]    
       
                 
         
             
             
         
       
     
         [0000]    wherein:
   R is —(CH 2 ) 2 —O—(CH 2 ) z —CH 3 ;   z is an integer ranging from 0 to 44;   a is an integer ranging from 0 to 2,000;   b is an integer ranging from 1 to 50;
 
said effective conditioning concentration ranging from 0.1 to 20% by weight
   
 
         [0043]    The present invention is also directed to a process for conditioning hair and skin, which comprises contacting the hair or skin with an effective conditioning concentration of an ether alkyl silicone conforming to the following structure; 
         [0000]    
       
                 
         
             
             
         
       
     
         [0000]    wherein:
   R′ is —(CH 2 ) 2 —O—(CH 2 ) z —CH 3 ;   z is an integer ranging from 0 to 44;   c is an integer ranging from 0 to 2,000;
 
said effective conditioning concentration ranging from 0.1 to 20% by weight.
   
 
       Preferred Embodiments 
       [0047]    In a preferred embodiment a ranges from 1 to 50. 
         [0048]    In a preferred embodiment a ranges from 50 to 100. 
         [0049]    In a preferred embodiment z is 18. 
         [0050]    In a preferred embodiment z is 31. 
         [0051]    In a preferred embodiment c ranges from 1 to 50. 
         [0052]    In a preferred embodiment c ranges from 50 to 100. 
       EXAMPLES 
       [0053]    Silicone Polymers 
         [0054]    The silicone polymers useful as raw materials for the preparation of the compounds of the present invention are items of commerce and are commercially available from a variety of sources including Siltech LLC Dacula, Ga. 
         [0055]    Group 1—Internal Silanic Hydrogen Compounds 
         [0056]    The compounds of this group conform to the following structure: 
         [0000]    
       
                 
         
             
             
         
       
     
         [0000]    wherein:
   a is an integer ranging from 0 to 2,000;   b is an integer ranging from 1 to 50.   
 
       Examples 1-7 
       [0059]      
         [0000]    
       
         
               
               
               
             
               
               
               
             
           
               
                   
               
               
                 Example 
                 a 
                 b 
               
               
                   
               
             
             
               
                   
               
             
          
           
               
                 1 
                 0 
                 1 
               
               
                 2 
                 10 
                 10 
               
               
                 3 
                 20 
                 5 
               
               
                 4 
                 50 
                 10 
               
               
                 5 
                 100 
                 20 
               
               
                 6 
                 1000 
                 30 
               
               
                 7 
                 2000 
                 50 
               
               
                   
               
             
          
         
       
     
         [0060]    Group 2—Terminal Silanic Hydrogen Compounds 
         [0061]    The compounds of this group conform to the following structure: 
         [0000]    
       
                 
         
             
             
         
       
     
         [0000]    wherein:
   c is an integer ranging from 0 to 2,000.   
 
       Examples 8-15 
       [0063]      
         [0000]    
       
         
               
               
               
             
               
               
               
             
           
               
                   
                   
               
               
                   
                 Example 
                 c 
               
               
                   
                   
               
             
             
               
                   
               
             
          
           
               
                   
                 8 
                 0 
               
               
                   
                 9 
                 2 
               
               
                   
                 10 
                 5 
               
               
                   
                 11 
                 20 
               
               
                   
                 12 
                 50 
               
               
                   
                 13 
                 100 
               
               
                   
                 14 
                 1000 
               
               
                   
                 15 
                 2000 
               
               
                   
                   
               
             
          
         
       
     
         [0064]    Vinyl Ethers 
         [0065]    Vinyl Ethers are items of commerce commercially available from BASF and ISP and conform to the following structure: 
         [0000]      CH 2 ═CH—O—(CH 2 ) z —CH 3 ;
 
         [0000]    wherein;
   z is an integer ranging from 0 to 44;   
 
       Examples 16-20 
       [0067]      
         [0000]    
       
         
               
               
               
             
               
               
               
             
           
               
                   
                   
               
               
                   
                 Example 
                 z 
               
               
                   
                   
               
             
             
               
                   
               
             
          
           
               
                   
                 16 
                 0 
               
               
                   
                 17 
                 3 
               
               
                   
                 18 
                 11 
               
               
                   
                 19 
                 18 
               
               
                   
                 20 
                 44 
               
               
                   
                   
               
             
          
         
       
     
         [0068]    Hydrosilylation 
         [0069]    Hydrosilylation is a process that reacts terminal vinyl compounds with silanic hydrogen to obtain a Si—C bond. References to this reaction, incorporated herein by reference, include: 
         [0070]    U.S. Pat. Nos. 3,715,334 and 3,775,452 to Karstedt, shows the use of Pt(O) complex with vinylsilicon siloxane ligands as an active hydrosilylation catalyst. 
         [0071]    Additional platinum complexes, such as complexes with platinum halides are shown by, U.S. Pat. No. 3,159,601 Ashby and, U.S. Pat. No. 3,220,972, to Lamoreaux. 
         [0072]    Another hydrosilylation catalyst is shown by Fish, U.S. Pat. No. 3,576,027. Fish prepares a platinum(IV) catalyst by reacting crystalline platinum(IV) chloroplatinic acid and organic silane or siloxane to form a stable reactive platinum hydrosilylation catalyst. 
         [0073]    General Procedure 
         [0074]    To a suitable flask equipped with heating, cooling and agitation is added the specified number of grams of the silanic hydrogen compound (Examples 1-15). The mass is mixed well. To that mixture is added the specified number of grams of the vinyl compound (Example 16-20). The reaction mass is mixed well until homogeneous. To that mixture is added 0.1% Karstedt catalyst, which is commercially available from Geleste. The agitation is stopped and the reaction begins. An exotherm is noted and the temperature is increased to 120° C. and held for 4 hours. Once the concentration of silanic hydrogen is below 0.5% is considered complete. The product is used without additional purification. 
         [0000]    
       
         
               
               
               
               
               
             
               
               
               
               
               
             
               
               
               
               
               
             
           
               
                   
                   
               
               
                   
                 Silanic Hydrogen 
                   
                   
                   
               
               
                   
                 Compound 
                   
                 Vinyl Ether 
               
             
          
           
               
                 Example 
                 Example 
                 Grams 
                 Example 
                 Grams 
               
               
                   
               
             
          
           
               
                 22 
                 1 
                 224 
                 16 
                 70 
               
               
                 23 
                 2 
                 150 
                 17 
                 120 
               
               
                 24 
                 3 
                 389 
                 18 
                 256 
               
               
                 25 
                 4 
                 446 
                 19 
                 372 
               
               
                 26 
                 5 
                 7420 
                 20 
                 809 
               
               
                 27 
                 6 
                 2532 
                 20 
                 809 
               
               
                 28 
                 7 
                 214 
                 19 
                 372 
               
               
                 29 
                 8 
                 68 
                 18 
                 256 
               
               
                 30 
                 9 
                 142 
                 17 
                 120 
               
               
                 31 
                 10 
                 253 
                 16 
                 70 
               
               
                 32 
                 11 
                 808 
                 16 
                 75 
               
               
                 33 
                 12 
                 1918 
                 17 
                 125 
               
               
                 34 
                 13 
                 4727 
                 18 
                 268 
               
               
                 35 
                 14 
                 37068 
                 19 
                 388 
               
               
                 36 
                 15 
                 74081 
                 20 
                 815 
               
               
                   
               
             
          
         
       
     
         [0075]    Applications 
         [0076]    The compounds of the resent invention have improved oil solubility and can be added to formulated products like lipsticks and pigmented products to minimize syneresis. 
         [0077]    The compounds of the present invention can be added to oils to make serums. They enhance the spread and provide unique cosmetic aesthetic, since they are not as hard as the same material made with alkyl groups. 
         [0078]    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.