Flame-retardant vanillin-derived cross-linkers

Abstract

A flame-retardant vanillin-derived cross-linker, a process for forming a flame-retardant polymer, and an article of manufacture comprising a material that contains the flame-retardant vanillin-derived cross-linker are disclosed. The flame-retardant vanillin-derived cross-linker can be synthesized from vanillin obtained from a bio-based source, and can have at least one phosphoryl or phosphonyl moiety with phenyl, allyl, epoxide, propylene carbonate, or thioether substituents. The process for forming the flame-retardant polymer can include reacting a diol vanillin derivative and a flame-retardant phosphorus-based molecule to form the flame-retardant vanillin-derived cross-linker, and binding the flame-retardant vanillin-derived cross-linker to a polymer. The material in the article of manufacture can be flame-retardant, and contain flame-retardant vanillin-derived cross-linkers. Examples of materials that can be in the article of manufacture can include resins, plastics, adhesives, polymers, etc.

1 . A flame-retardant vanillin-derived cross-linker with a formula of: 
       
         
           
           
               
               
           
         
         wherein FR is a first phosphorus-based moiety with a formula selected from a group consisting of moieties with formulas of: 
       
       
         
           
           
               
               
           
         
         wherein R is a first substituent selected from a group consisting of an allyl substituent, an epoxide substituent, a propylene carbonate substituent, and a thioether substituent selected from a group consisting of a hydroxyl-functionalized thioether substituent, an amino-functionalized thioether substituent, and a carboxylic acid-functionalized thioether substituent; 
         wherein M is a flame-retardant substituent selected from a group consisting of substituents with formulas of: 
       
       
         
           
           
               
               
           
         
         
           wherein R is a second substituent selected from the group consisting of the allyl substituent, the epoxide substituent, the propylene carbonate substituent, and the thioether substituent, and wherein the selection of R depends upon the selection of the first R substituent, and wherein FR is a second phosphorus-based moiety selected from the group consisting of moieties with formulas of: 
         
       
       
         
           
           
               
               
           
         
       
       and
 wherein the flame-retardant vanillin-derived cross-linker participates in a process of forming a flame-retardant polymer, the process comprising:
 forming a diol vanillin derivative synthesized from vanillin obtained from a biological source, wherein the diol vanillin derivative is selected from a group consisting of vanillin derivatives with formulas of: 
 
 
       
         
           
           
               
               
           
         
         
           forming a phosphorus-based flame-retardant molecule selected from a group consisting of phosphorus-based flame-retardant molecules with formulas of: 
         
       
       
         
           
           
               
               
           
         
       
       wherein R is a substituent selected from a group consisting of an epoxide substituent and an allyl substituent;
   chemically reacting the diol vanillin derivative with the phosphorus-based flame-retardant molecule to form the flame-retardant vanillin-derived cross-linker; and   binding the flame-retardant vanillin-derived cross-linker to a polymer selected from a group consisting of polyurethane, an epoxy polymer, a polyhydroxyurethane, a polycarbonate, a polyester, a polyacrylate, a polyimide, a polyamide, a polyurea, and a poly(vinyl-ester).