Abstract:
The present invention relates to a series of novel silicone alkoxylated esters which have terminal carboxyl groups that form salt complexes with certain amid containing cationic compounds to form very mild conditioning products suited for personal care applications like shampoos, body wash, hand wash and bath products.

Description:
BACKGROUND OF THE INVENTION 
     1. Field of the Invention 
     The present invention relates to a series of novel silicone alkoxylated esters which have terminal carboxyl groups that form salt complexes with certain amid containing cationic compounds to form very mild conditioning products suited for personal care applications like shampoos, body wash, hand wash and bath products. 
     2. Description of the Related Art 
     There has been a long felt need for a shampoo product that provides conditioning and softening properties when applied to the hair, and is at the same time mild to the hair, skin and eyes. This is most important in the area of baby shampoo, where tearing is an additional concern. 
     The classical way to get conditioning is to incorporate cationic compounds into the shampoo. These products provide acceptable softness and anti-static properties when applied to the hair, and a good after feel when applied to the skin, but are aggressive to the skin and eye, allowing for their use at low levels in general use products, and not at all in baby and sensitive skin products. Included in this group are compounds like stearyl dimethyl benzyl alkonium chloride and cetyl tri-methyl ammonium chloride. There have been few products mild enough to use in sensitive skin products. 
     U.S. Pat. No. 5,296,625, incorporated herein by reference, issued March 1994 to O&#39;Lenick et al describes a class of carboxy substituted silicone compounds useful as raw materials in the practice of the current invention. It is by proper selection of the compounds of the U.S. Pat. No. 5,296,625 and the cationic polymeric compound that the products of the present invention are prepared. 
     U.S. Patent U.S. Pat. No. 3,560,544, issued Feb. 2, 1971, to Haulska et al likewise discloses carboxy substituted silicone polymers. These polymers are also useful as raw materials in the preparation of the compounds of the present invention. 
     THE INVENTION 
     Object of the Invention 
     It is the object of the present invention to provide novel silicone fatty polymeric quat compounds having outstanding conditioning properties at low concentrations and at the same time are very mild to the skin and eye. 
     These compounds are substantive to the surface of hair and have increased solubility in fatty materials including mineral oil, fatty triglycerides and traditional fatty quaternary ammonium compounds. It needs to be clearly understood that with the introduction of silicone into the molecule and with the formation of a complex (a salt) the resulting conditioning complex has unique properties. 
     Traditionally, one would think of a conditioner as having a water-loving (hydrophilic) group and a water-hating (hydrophilic)group. We have learned this approach, while simplistic is not accurate. The water-hating (hydrophobic) group is insoluble in water, but can be either a silicone or oil soluble group, or in a preferred case both. 
     In order to make the compounds of the current invention, we consider the molecule as having a water loving (hydrophilic group) an oil loving (oleophilic group) and silicone loving (siliphilic group) in the molecule. The group opposites then are three, hydrophobic (water hating), oleophobic (oil hating), siliphobic (silicone hating). Consequently, hydrophobic (water hating) materials can be either oleophilic or siliphilic, oleophobic (oil hating) materials may be either hydrophilic or siliphilic. Siliphobic (silicone hating) materials may be either oleophilic or hydrophilic. Only by balancing the product and having a cationic charge on it, can the desired improved conditioning be achieved. 
     SUMMARY OF THE INVENTION 
     Objective of the Invention 
     The present invention relates to complexes of novel silicone alkoxylated esters, which contain carboxyl groups that are combined with specific polymeric quats to form the desired conditioning products. 
     The present invention is also directed toward a process for conditioning hair, which comprises contacting the hair with and effective conditioning amount of the compounds of the present invention. The effective conditioning concentration ranges from 0.01 to 25% by weight of the compound. 
    
    
     DETAILED DESCRIPTION OF THE INVENTION 
     The compounds of the present invention therefore have a pendant group, which is as follows: 
                        
 
wherein;
         Me is methyl;   R and R′ are CH 3  or —(CH 2 ) 3 —O—(EO) a —(PO) b —(EO) c —(O)—R″—C(O)—O − 
                         
   with the proviso that both R and R′ are not CH 3 ;   x is an integer ranging from 1 to 100;   y is an integer ranging from 1 to 100;   R″ is selected from the group consisting of 
                         
   R 1  is selected from the group consisting of lower alkyl CH 3 (CH) n — and phenyl;   n is an integer from 0 to 8;   a, b and c are integers independently ranging from 0 to 20;   EO is an ethylene oxide residue —(CH 2 CH 2 —O)—;   PO is a propylene oxide residue —(CH 2 CH(CH 3 )—O)—;   o is an integer ranging from 1 to 100;   q is an integer ranging from 0 to 500,   R 7  is alkyl having from 1 to 20 carbon atoms.       

     The complexes of the present invention are made by making a salt of the carboxy silicone of O&#39;Lenick&#39;s U.S. Pat. No. 5,296,625, incorporated herein by reference, as follows; 
                        
     wherein;
       Me is methyl;   R and R′ are CH 3  or —(CH 2 ) 3 —O—(EO) a —(PO) b —(EO) c —C(O)—R″—C(O)—OH   with the proviso that both R and R′ are not CH 3 ;   R″ is selected from the group consisting of —CH 2 —CH 2 —; —CH═CH—; —CH 2 —C(R 7 )—H; 
                         
           R 1  is selected from lower alkyl CH 3 (CH) n - or phenyl;   n is an integer from 0 to 8;   a, b and c are integers independently ranging from 0 to 20;   EO is an ethylene oxide residue —(CH 2 CH 2 —O)—;   PO is a propylene oxide residue —(CH 2 CH(CH 3 )O)—;   o is an integer ranging from 1 to 100;   q is an integer ranging from 0 to 500.   R 7  is alkyl having from 1 to 20 carbon atoms.   
           with certain alkyl polymeric cationic compounds conforming to the following structure: 
                         
   wherein;
           x is an integer ranging from 1 to 100;   y is an integer ranging from 1 to 100.   
           
       

     Another aspect of the present invention is a process of treating hair which comprises contacting the hair with an effective conditioning concentration of a compound conforming to the following structure; 
                        
 
wherein;
         Me is methyl;   R and R′ are CH 3  or —(CH 2 ) 3 —O—(EO) a (PO) b —(EO) c —C(O)—R″—C(O)—O − 
                         
   with the proviso that both R and R′ are not CH 3 ;   x is un integer ranging from 1 to 100;   y is an integer ranging from 1 to 100;   R″ is selected from the group consisting of 
                         
   R 1  is selected from the group consisting of lower alkyl CH 3 (CH) n — and phenyl;   n is an integer from 0 to 8;   a, b and c are integers independently ranging from 0 to 20;   EO is an ethylene oxide residue —(CH 2 CH 2 —O)—;   PO is a propylene oxide residue —(CH 2 CH(CH 3 )—O)—;   o is an integer ranging from 1 to 100;   q is an integer ranging from 0 to 500,   R 7  is alkyl having from 1 to 20 carbon atoms.       

     The effective conditioning concentration ranges for 0.01 to 25% by weight of the compound. 
     Preferred Embodiments 
     In a preferred embodiment of the complex R″ is —CH 2 —CH 2 —. 
     In a preferred embodiment of the complex R″ is —CH═CH—. 
     In a referred embodiment of the complex R″ is 
                        
 
     In a preferred embodiment of using the complex R″ is —CH 2 —CH 2 —. 
     In a preferred embodiment of using the complex T″ is —CH═CH—. 
     In a preferred embodiment of using the complex R″ is 
                        
 
     In a preferred embodiment, the effective conditioning concentration ranges from 0.01 to 25% by weight of the compound. 
     EXAMPLES 
     Carboxy Silicone 
     The compounds used in the preparation of the complexes of the present invention are taken from U.S. Pat. No. 5,296,625 issued in 1994 to O&#39;Lenick, incorporated herein by reference. 
     Examples 1-19 
     
       
         
               
               
               
             
               
               
               
             
           
               
                   
                   
               
               
                   
                 Example 
                 O&#39;Lenick Example 
               
               
                   
                   
               
             
             
               
                   
               
             
          
           
               
                   
                 1 
                 14 
               
               
                   
                 2 
                 15 
               
               
                   
                 3 
                 16 
               
               
                   
                 4 
                 17 
               
               
                   
                 5 
                 18 
               
               
                   
                 6 
                 19 
               
               
                   
                 7 
                 20 
               
               
                   
                 8 
                 21 
               
               
                   
                 9 
                 22 
               
               
                   
                 10 
                 23 
               
               
                   
                 11 
                 24 
               
               
                   
                 12 
                 25 
               
               
                   
                 13 
                 26 
               
               
                   
                 14 
                 27 
               
               
                   
                 15 
                 28 
               
               
                   
                 16 
                 29 
               
               
                   
                 17 
                 30 
               
               
                   
                 18 
                 31 
               
               
                   
                 19 
                 32 
               
               
                   
                   
               
             
          
         
       
     
     Examples 20-29 
     Polymeric Cationic Compounds 
     The polymeric cationic compounds of the present invention are commercially available from a variety of sources including National Starch Inc. of New Jersey. 
     They conform to the following structure; 
                        
         x is an integer ranging from 1 to 100;   y is an integer ranging from 1 to 100.       

     EXAMPLES 
     
       
         
               
               
               
             
               
               
               
             
           
               
                   
               
               
                 Example 
                   
                   
               
               
                 Number 
                 x 
                 y 
               
               
                   
               
             
             
               
                   
               
             
          
           
               
                 20 
                 10 
                 90 
               
               
                 21 
                 20 
                 80 
               
               
                 22 
                 30 
                 50 
               
               
                 23 
                 40 
                 30 
               
               
                 24 
                 50 
                 20 
               
               
                 25 
                 60 
                 10 
               
               
                 26 
                 70 
                 50 
               
               
                 27 
                 80 
                 1 
               
               
                 28 
                 90 
                 10 
               
               
                 29 
                 100 
                 100 
               
               
                   
               
             
          
         
       
     
     Preparation of Complexes 
     The complexes of the present invention are made by combining the anionic silicone raw material together with the cationic compound, then neutralizing the resultant mixture with base to pH of 6-7. The resulting complex is a mixed salt of the silicone, and the quat. 
     
       
         
               
               
               
               
             
               
               
               
               
               
               
             
               
               
               
               
               
               
             
           
               
                   
                   
               
               
                   
                   
                 Polymeric 
                   
               
               
                   
                 Carboxy Silicone 
                 Cationic Compound 
                 Water 
               
             
          
           
               
                 Example 
                 Example 
                 Grams 
                 Example 
                 Grams 
                 Grams 
               
               
                   
               
             
          
           
               
                 30 
                 1 
                 1,110 
                 20 
                 378 
                 3,720 
               
               
                 31 
                 2 
                 2,429 
                 21 
                 406 
                 7,088 
               
               
                 32 
                 3 
                 2,147 
                 22 
                 434 
                 6,452 
               
               
                 33 
                 4 
                 5,398 
                 23 
                 462 
                 14,650 
               
               
                 34 
                 5 
                 533 
                 24 
                 490 
                 2,557 
               
               
                 35 
                 6 
                 4,723 
                 25 
                 452 
                 12,938 
               
               
                 36 
                 7 
                 3,083 
                 26 
                 449 
                 8,830 
               
               
                 37 
                 8 
                 3,750 
                 27 
                 508 
                 10,645 
               
               
                 38 
                 9 
                 1,663 
                 28 
                 536 
                 5,500 
               
               
                 39 
                 10 
                 1,288 
                 29 
                 536 
                 4,560 
               
               
                 40 
                 11 
                 6,100 
                 29 
                 508 
                 16,520 
               
               
                 41 
                 12 
                 10,115 
                 28 
                 536 
                 26,627 
               
               
                 42 
                 13 
                 50,269 
                 27 
                 508 
                 126,942 
               
               
                 43 
                 14 
                 86,185 
                 26 
                 449 
                 216,585 
               
               
                 44 
                 15 
                 2,655 
                 25 
                 452 
                 7,767 
               
               
                 45 
                 16 
                 2,370 
                 24 
                 490 
                 7,150 
               
               
                 46 
                 17 
                 5,227 
                 23 
                 462 
                 14,222 
               
               
                 47 
                 18 
                 500 
                 22 
                 436 
                 2,340 
               
               
                 48 
                 19 
                 5,723 
                 21 
                 406 
                 15,323 
               
               
                   
               
             
          
         
       
     
     Applications 
     The compounds of the present invention are very substantive to the skin and hair. They are effective in providing conditioning and softening is body washes, shampoos, hand soap, and hand dish detergents at concentrations of between 0.1 and 2.0% by weight. 
     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.