Hydrophilized fiber substrate and method for hydrophilizing a hydrophobic surface of a fiber substrate

Abstract

A hydrophilized fiber, comprising a fiber having a hydrophobic surface and a phosphinate compound according to formula (I): wherein A is an organic group comprising one or more monomeric units derived from an ethylenically unsaturated monomer or an organic group according to formula (II): A′ is an organic group according to formula (III): B, R 4 , and R 10 are each independently methylene or poly(methylene), which may optionally be substituted on one or more of such methylene units, and which may optionally be interrupted at one or more positions by an oxygen atom, R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 9 , R 11 , R 12 , and R 13 are each independently H, alkyl, alkoxyl, cycloalkyl, alkenyl, aryl, aralkyl, alkaryl or heterocyclyl, m, n, and n′ are each independently 0 or an integer of from 1 to about 100, provided that m cannot be 0 if n′ is 0, q and s are each independently 0 or an integer of from 1 to about 50, and p, r, and r′ are each independently an integer of from 1 to about 20, or a salt thereof, disposed on at least a portion of such hydrophobic surface in an amount effective to increase the hydrophilicity of such portion of such hydrophobic surface is useful as a component of a hydrophilized fabric and a disposable absorbent article.

1 . A hydrophilized fiber, comprising a fiber having a hydrophobic surface and a phosphinate compound according to formula (I):  
     
       
         
         
             
             
         
       
     
     wherein: 
 A is an organic group comprising one or more monomeric units derived from an ethylenically unsaturated monomer or an organic group according to formula (II):  
                     
 A′ is an organic group according to formula (III):  
                     
 B, R 4 , and R 10  are each independently methylene or poly(methylene), which may optionally be substituted on one or more of such methylene units, and which may optionally be interrupted at one or more positions by an oxygen atom,  
 R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 9 , R 11 , R 12 , and R 13  are each independently H, alkyl, alkoxyl, cycloalkyl, alkenyl, aryl, aralkyl, alkaryl, or heterocyclyl,  
 m, n, and n′ are each independently 0 or an integer of from 1 to about 100, provided that m cannot be 0 if n′ is 0,  
 q and s are each independently 0 or an integer of from 1 to about 50, and  
 p, r, and r′ are each independently an integer of from 1 to about 20, or a salt thereof,  
 disposed on at least a portion of such hydrophobic surface in an amount effective to increase the hydrophilicity of such portion of such hydrophobic surface.  
 
   
   
       2 . The hydrophilized fiber of  claim 1 , wherein the fiber is a hydrophobic synthetic polymer fiber.  
   
   
       3 . A hydrophilized fabric, comprising one or more hydrophilized fibers according to  claim 1 .  
   
   
       4 . The hydrophilized fabric of  claim 3 , wherein the fabric is a nonwoven fabric.  
   
   
       5 . The hydrophilized fiber of  claim 1 , wherein n and n′ are each 0 and m is an integer of from 1 to about 100.  
   
   
       6 . The hydrophilized fiber of  claim 1 , wherein m is 0 and n and n′ are each independently an integer of from 1 to about 100.  
   
   
       7 . The hydrophilized fiber of  claim 1 , wherein A is derived from an ethylenically unsaturated monomer.  
   
   
       8 . The hydrophilized fiber of  claim 1 , wherein A is derived from an ethylenically unsaturated monomer and is an organic group according to the formula (IV):  
     
       
         
         
             
             
         
       
       R 20  is H or methyl,  
       D is O or NH,  
       R 21  is H, alkyl or hydroxyalkyl, and  
       t is an integer of from 1 to about 100.  
     
   
   
       9 . The hydrophilized fiber of  claim 1 , wherein A is an organic group according to formula (II).  
   
   
       10 . The hydrophilized fiber of  claim 9 , wherein R 1 , R 2 , R 3 , and R 5  are each independently H or (C 1 -C 6 )alkyl, each R 4  is independently methylene or a poly(methylene) radical comprising from 2 to about 50 methylene units, which may optionally be substituted on one or more of the methylene units, R 6  is H or alkyl, p is an integer of from 1 to about 10, and q is 0 or an integer of from 1 to about 20.  
   
   
       11 . The hydrophilized fiber of  claim 10 , wherein each R 4  is independently a methylene or poly(methylene) radical comprising from 1 to about 50 methylene units that is substituted on one or more of the methylene units with a group according to formula (V):  
     
       
         
         
             
             
         
       
     
     wherein R 22  and each R 23  is independently H, alkyl, hydroxyl, or carboxyl, provided that at least one R 22  or R 23  of such radical is alkyl, hydroxyl, or carboxyl, and wherein v is an integer of from 1 to about 49.  
   
   
       12 . The hydrophilized fiber of  claim 10 , wherein each R 4  is independently a poly(oxyalkylene) radical comprising from 1 to about 50 oxyalkylene units.  
   
   
       13 . The hydrophilized fiber of  claim 1 , wherein A′ is according to formula (III), each r and r′ is independently an integer of from 1 to about 10, s is 0, R 7 , R 8 , R 9 , R 12 , and R 13  are each independently H, alkyl, cycloalkyl, hydroxyalkyl, alkoxyalkyl, alkenyl, aryl, aralkyl, or alkaryl.  
   
   
       14 . The hydrophilized fiber of  claim 1 , wherein each B is independently a methylene or poly(methylene) radical of from 1 to about 50 methylene units, which may be optionally substituted on one or more of the methylene units with hydroxyl, alkyl, or carboxyl, and which may be interrupted at one or more positions by an oxygen atom  
   
   
       15 . The hydrophilized fiber of  claim 1 , wherein: 
 m is 0,    n′ is an integer of from 1 to about 30,    A is a group according to formula (II), wherein R 1 , R 2 , R 3 , R 5 , and R 6  are each H, R 4  is methylene or (C 2 -C 30 )poly(methylene), p is an integer of from 1 to about 20,and q is an integer of from 1 to about 30, and    B is a group according to formula (V), wherein R 22  is hydroxy(C 1 -C 6 )alkyl, R 23  is H, and u is an integer of from 1 to about 10.    
   
   
       16 . The hydrophilized fiber of  claim 1 , wherein: 
 m is 0,    n′ is an integer of from 1 to about 30,    A is a group according to formula (II), wherein R 1 , R 2 , and R 3  are each H, R 6  is (C 2 -C 30 )alkyl, p is an integer of from 1 to about 20, and q is 0, and    B is a group according to formula (V), wherein R 22  is hydroxy(C 1 -C 6 )alkyl, R 23  is H, and u is an integer of from 1 to about 10.    
   
   
       17 . The hydrophilized fiber of  claim 1 , wherein: 
 m is an integer of from 1 to about 30,    n and n′ are each 0,    A is a group according to formula (II), wherein R 1 , R 2 , R 3 , R 5 , and R 6  are each H, R 4  is methylene or (C 2 -C 30 )poly(methylene), p is an integer of from 1 to about 20, and q is an integer of from 1 to about 30, and    A′ is a group according to formula (III), wherein R 7 , R 8 , R 12 , R 13  are each H, R 9  is hydroxy(C 1 -C 6 )alkyl, r and r′ are each independently integers of from 1 to about 20, and s is 0.    
   
   
       18 . The hydrophilized fiber of  claim 1 , wherein: 
 m is an integer of from 1 to about 30,    n and n′ are each 0,    A is a group according to formula (II), wherein R 1 , R 2 , and R 3  are each H, R 6  is (C 2 -C 30 )alkyl, p is an integer of from 1 to about 20, and q is 0, and    A′ is a group according to formula (III), wherein R 7 , R 8 , R 12 , R 13  are each H, R 9  is hydroxy(C 1 -C 6 )alkyl, r and r′ are each independently integers of from 1 to about 20, and s is 0.    
   
   
       19 . The hydrophilized fiber of  claim 1 , wherein: 
 m is an integer of from 1 to about 30,    n and n′ are each 0,    A is a group according to formula (IV), wherein R 20  is H or methyl, R 21  is H or (C 1 -C 6 )alkyl, and t is an integer of from 1 to about 20, and    A′ is a group according to formula (III), wherein R 7 , R 8 , R 9 , R 11 , R 12 , and R 13  are each H, R 10  is methylene or (C 2 -C 30 )poly(methylene), r and r′ are each independently integers of from 1 to about 20, and s is an integer of from 1 to about 20.    
   
   
       20 . The hydrophilized fiber of  claim 1 , wherein the phosphinate compound according to formula (I) exhibits a weight average molecular weight of from about 300 to about 500,000 grams per mole.  
   
   
       21 . An absorbent article, comprising a hydrophilized fabric according to  claim 3 .  
   
   
       22 . The absorbent article of  claim 21 , wherein the absorbent article has a composite laminate structure and comprises at least one layer of a porous hydrophilized fabric, at least one layer of a nonporous water impermeable film, and at least one layer of an adsorbent material, disposed between the layer of porous hydrophilized fabric and the layer of nonporous water impermeable film  
   
   
       23 . The absorbent article of  claim 22 , wherein porous hydrophilized fabric is a porous hydrophilized nonwoven fabric.  
   
   
       24 . The absorbent article of  claim 22 , wherein the absorbent material is a superabsorbent material.  
   
   
       25 . A method for hydrophilizing a fiber having a hydrophobic surface, comprising treating such at least a portion of a hydrophobic surface with a phosphinate compound according to formula (I):  
     
       
         
         
             
             
         
       
     
     wherein: 
 A is an organic group comprising one or more monomeric units derived from an ethylenically unsaturated monomer or an organic group according to formula (II):  
                     
 A′ is an organic group according to formula (III):  
                     
 B, R 4 , and R 10  are each independently methylene or poly(methylene), which may optionally be substituted on one or more of such methylene units, and which may optionally be interrupted at one or more positions by an oxygen atom,  
 R 1 , R 2 , R 3 , R 5 , R 6 , R 7,  R 8 , R 9 , R 11 , R 12 , and R 13  are each independently H, alkyl, alkoxyl, cycloalkyl, alkenyl, aryl, aralkyl, alkaryl, or heterocyclyl,  
 m, n, and n′ are each independently 0 or an integer of from 1 to about 100, provided that m cannot be 0 if n′ is 0,  
 q and s are each independently 0 or an integer of from 1 to about 50, and  
 p, r, and r′ are each independently an integer of from 1 to about 20, or a salt thereof,  
 to deposit a quantity of such compound on such portion of such hydrophobic surface.  
 
   
   
       26 . A hydrophilized fiber, comprising a fiber having a hydrophobic surface and a phosphinate layer, said phosphinate layer comprising the crosslinked reaction product of a reaction between a phosphinate compound and a crosslinking agent for the phosphinate compound, wherein the phosphinate compound is according to formula (I):  
     
       
         
         
             
             
         
       
     
     wherein: 
 A is an organic group comprising one or more monomeric units derived from an ethylenically unsaturated monomer or an organic group according to formula (II):  
                     
 A′ is an organic group according to formula (III):  
                     
 B, R 4 , and R 10  are each independently methylene or poly(methylene), which may optionally be substituted on one or more of such methylene units, and which may optionally be interrupted at one or more positions by an oxygen atom,  
 R 1 , R 2 , R 3 , R 5 , R 6 , R 7,  R 8 , R 9 , R 11 , R 12  and R 13  are each independently H, alkyl, alkoxyl, cycloalkyl, alkenyl, aryl, aralkyl, alkaryl, or heterocyclyl,  
 m, n, and n′ are each independently 0 or an integer of from 1 to about 100, provided that m cannot be 0 if n′ is 0,  
 q and s are each independently 0 or an integer of from 1 to about 50, and  
 p, r, and r′ are each independently an integer of from 1 to about 20, or a salt thereof,  
 disposed on at least a portion of such hydrophobic surface in an amount effective to increase the hydrophilicity of such portion of such hydrophobic surface.  
 
   
   
       27 . The hydrophilized fiber of  claim 26 , wherein the crosslinking agent is a diepoxide.  
   
   
       28 . The hydrophilized fiber of  claim 26 , wherein the phosphinate layer further comprises a phosphinate compound according to formula (I) that is not crosslinked.