Modified textiles and other materials and methods for their preparation

Abstract

Provided are compounds and methods for modifying a material to change properties of the material, as well as a variety of products obtained using the methods. In one embodiment, a material comprising one or more modifiable functional groups is reacted with an activated hydrophobic acyl group in the presence of a hindered base, thereby to covalently attach the hydrophobic acyl group to the modifiable functional groups on the material. The material which is modified may be, for example, a carbohydrate, and the modifiable functional groups on the material may be hydroxyls. For,example, materials such as cellulose may be modified by reacting it with an acid chloride or acid anhydride including a hydrophobic acyl group, in the presence of a hindered base, such as tripentylamine, to attach the hydrophobic acyl groups to the hydroxyls on the cellulose, thereby to increase the hydrophobicity of the cellulose. The methods and compounds disclosed herein may be used to modify materials to improve properties such as resistance, grease repellency, soil resistance and permanent press properties.

What is claimed is:  
     
         1 . A method of modifying a material to increase its hydrophobicity, the method comprising: 
 reacting a material comprising one or more modifiable functional groups with an activated hydrophobic acyl group in the presence of a hindered base, thereby to covalently attach the hydrophobic acyl group to the modifiable functional groups on the material.    
     
     
         2 . The method of  claim 1 , wherein the material comprises a carbohydrate, and the modifiable functional groups on the material are hydroxyls.  
     
     
         3 . The method of  claim 1 , wherein the material comprises cellulose.  
     
     
         4 . The method of  claim 3 , wherein the activated acyl group is an acid chloride or acid anhydride, and wherein the method comprises covalently attaching the acyl group of the acid chloride or acid anhydride to hydroxyls on the cellulose, thereby to increase the hydrophobicity of the cellulose.  
     
     
         5 . The method of  claim 4 , wherein the hindered base is tripentylamine.  
     
     
         6 . The method of  claim 4 , wherein the method comprises reacting the cellulose with an activated acyl group consisting of an acid chloride, RCOCl or anhydride (RCO) 2 O, wherein R is a straight chain C10-20 saturated hydrocarbon.  
     
     
         7 . The method of  claim 4 , wherein the activated acyl group is an acid chloride selected from the group consisting of hexadecanoyl chloride and polyethylene acid chloride.  
     
     
         8 . The method of  claim 4 , wherein the method comprises reacting the cellulose with an activated acyl group comprising an acid chloride, R(CH 2 ) 2 COCl or anhydride, (R(CH 2 ) 2 CO) 2 O, wherein R is CF 3 (CF 2 ) n —wherein n is 0 to 10.  
     
     
         9 . The method of  claim 6 , wherein the hindered base is tripentylamine.  
     
     
         10 . The method of  claim 6 , wherein the method further comprises reacting the cellulose with acetyl chloride to acylate unreacted hydroxyls on the cellulose.  
     
     
         11 . The method of  claim 9 , wherein the cellulose is a cotton material.  
     
     
         12 . The method of  claim 11 , wherein the cotton material is dyed prior to reacting the material.  
     
     
         13 . The method of  claim 11 , further comprising processing the cotton material into clothing or upholstery.  
     
     
         14 . The method of  claim 4  wherein the activated acyl group is an acid chloride selected from the group consisting of  
       
         
           
           
               
               
           
         
       
       wherein in Formula 1, 2 and 3 m, n, o and p are independently 100-10,000.  
     
     
         15 . The method of  claim 1 , wherein the material is a proteinaceous material.  
     
     
         16 . A hydrophobic material comprising cotton obtained by the method of  claim 12 .  
     
     
         17 . The hydrophobic material of  claim 16 , wherein the cotton material comprises cloth, and wherein the hydrophobic groups on the cotton render the cotton water resistant.  
     
     
         18 . A method of modifying a textile material comprising reacting the material with an alkyl silane, thereby to covalently attach the alkyl silane to the material.  
     
     
         19 . The method of  claim 18 , wherein the alkyl silane has the formula RSiX 1 X 2 X 3 , where R is a hydrocarbon or fluorocarbon, and one or more of X 1 , X 2 , and X 3  are independently a halo or alkoxy group, and the remainder of X 1 , X 2 , and X 3  are independently alkyl.  
     
     
         20 . The method of  claim 19 , wherein X 1 , X 2 , and X 3  are independently chloro, ethoxy and methoxy, and the remainder of X 1 , X 2 , and X 3  are methyl.  
     
     
         21 . The method of  claim 18 , wherein the material is a cellulose or wool containing material.  
     
     
         22 . A method of modifying a textile material to increase the hydrophobicity of the material, the method comprising: crosslinking the material with hydrophobically modified dimethyloldihydroxyethyleneurea.  
     
     
         23 . The method of  claim 22 , wherein the textile material is a carbohydrate containing material and the dimethyloldihydroxyethyleneurea comprises a covalently attached hydrocarbon or fluorocarbon group.  
     
     
         24 . A method of modifying a cellulosic material, the method comprising crosslinking the material with a functionalized glucose molecule comprising a reactive group selected from the group consisting of an isothiocyanate, isocyanate, acyl azide, sulfonyl chloride, aldehyde, glyoxal, oxirane, carbonated imidoester, carbodiimide,, succinimide ester, epoxide, alkyl halide, anhydride, acid chloride, and an activated ester.  
     
     
         25 . A method of modifying cellulosic material, the method comprising exposing the material to fluorine gas in an effective amount to fluorinate at least a portion of the material.  
     
     
         26 . A modified material produced by reacting a material with an activated hydrophobic acyl group in the presence of a hindered base, thereby to attach the hydrophobic acyl group to the material.  
     
     
         27 . The modified material of  claim 26 , wherein the material comprises cellulose.  
     
     
         28 . A material produced by the method of  claim 21 .  
     
     
         29 . A material produced by the method of  claim 23 .  
     
     
         30 . A material produced by the method of claim  24 .