Melamine ring-containing co-polymers; methods of making and using the same

Abstract

The invention provides a melamine-ring containing polymer and methods of preparing the melamine-ring containing structure. The polymer of the invention may be represented by the general structure (I): wherein m is an integer of 1 to 100; R 1 is independently selected from an alkyl group having one to twenty carbon atoms; R 2 is independently selected from the group consisting of an oxygen atom and a sulfur atom; R 3 is independently selected from an alkyl group, an allyl group, an alkynyl group, an aryl group, and a phenyl group, having one to seventy carbon atoms; R 4 is independently selected from —C p H 2p OH; —C p H 2p-1 OH; —C p H 2p-2 OH, wherein p is an integer of one to seven; a hydrogen atom; a carboxyl group, an alkyl group; an allyl group; and an alkynyl group; R 5 is independently selected from the group consisting of an alkyl group, an alkyl group containing at least one ether linkage, and the group represented by the formula (III): and; n is an integer of one to thirty. The invention also includes methods of preparing the polymer of the inventions. The methods include reacting a melamine base resin with a reactant compound that contains a functional group that is a carboxyl group, a hydroxyl group and a thiol group, or a combination of these groups.

1 - 22 . (canceled)  
     
     
         23 . A melamine ring containing co-polymer that is a reaction product of a cashew nut shell liquid and at least one melamine-formaldehyde resin, wherein the cashew nutshell liquid comprises cardanol and cardol, and wherein the cardanol is present in an amount ranging from about 96% to about 98% by weight of the cashew nut shell liquid and the cardol is present in an amount ranging from about 2% to about 4% by weight of the cashew nut shell liquid.  
     
     
         24 . The melamine ring containing co-polymer of  claim 23  wherein the co-polymer has formula (I):  
       
         
           
           
               
               
           
         
         wherein m is an integer of 1 to 100;  
         R 1  is independently selected from an alkyl group having one to twenty carbon atoms;  
         R 2  is independently selected from the group consisting of an oxygen atom and a sulfur atom;  
         R 3  is independently selected from an alkyl group, an allyl group, an alkynyl group, an aryl group, and a phenyl group, having one to seventy carbon atoms;  
         R 4  is independently selected from —C p H 2p OH; —C p H 2p-1 OH; —C p H 2p-2 OH, wherein p is an integer of one to seven; a hydrogen atom; a carboxyl group, an alkyl group; an allyl group; and  
         an alkynyl group;  
         R 5  is independently selected from the group consisting of an alkyl group, an alkyl group containing at least one ether linkage, and the group represented by the formula (III):  
         
           
             
             
                 
                 
             
           
         
         and;  
         n is an integer of one to thirty;  
         wherein the melamine ring-containing co-polymer is the reaction product of at least one melamine base resin and at least one reactant compound, wherein the at least one reactant compound comprises a cashew nut shell liquid and has at least one functional group selected from a carboxyl group, a hydroxyl group, a thiol group and combinations thereof.  
       
     
     
         25 . A compound formed by the process of reacting a melamine base resin and cashew nut shell liquid.  
     
     
         26 . The compound  claim 25 , wherein the process further includes the steps of 
 (a) mixing a melamine base resin and cashew nut shell liquid;    (b) heating the mixture from about 104° C. to about 170° C.; and    (c) reacting the mixture for about 4 to about 6 hours.    
     
     
         27 . The compound  claim 26 , wherein the process yields at least about 87% of the compound.  
     
     
         28 . The compound of  claim 25 , wherein the process of reacting further includes a catalyst selected from the group consisting of a sulfo radical containing catalyst, methanesulfonic acid, phosphoric acid, nitric acid, oxalic acid, maleic acid, hexamic acid, phthalic acid, acrylic acid, para-toluene sulfonic acid, dinonyl naphthalene sulfonic acid, magnesium bromide, zinc nitrate, aluminum nitrate, magnesium nitrate, and combinations thereof.  
     
     
         29 . The compound of  claim 25  wherein the melamine base resin is a modified or unmodified melamine resin, melamine-formaldehyde resin, melamine-urea-formaldehyde resin, or combinations thereof.  
     
     
         30 . The compound of  claim 25  wherein the melamine base resin is a methylated melamine-formaldehyde resin.  
     
     
         31 . The compound of  claim 25  wherein the cashew nut shell liquid comprises cardinal and cardol.  
     
     
         32 . The compound of  claim 31  wherein the cardol concentration is about 15% or less.  
     
     
         33 . A compound formed by the reaction of a methylated melamine-formaldehyde resin and cashew nut shell liquid having cardinal and cardol, wherein the cardol concentration is about 15% or less.  
     
     
         34 . The compound of  claim 33 , wherein R 7  is independently a C 15 -C 30  branched or unbranched, substituted or unsubstituted, alkyl, allyl, or alkynyl group.  
     
     
         35 . A compound having the formula  
       
         
           
           
               
               
           
         
         wherein m is an integer of 1 to 100;  
         R 1  is independently a C 1 -C 20  alkyl group;  
         R 2  is independently an oxygen atom or a sulfur atom;  
         R 3  is independently a C 1 -C 70  alkyl, allyl, alkynyl, aryl, or phenyl group;  
         R 4  is independently selected from the group consisting of an —C p H 2p OH; —C p H 2p-1 OH; —C p H 2p-2 OH, wherein p is an integer of one to seven; a hydrogen atom; a carboxyl group, an alkyl group; an allyl group; and an alkynyl group;  
         R 5  is independently selected from the group consisting of an alkyl group, an alkyl group containing at least one ether linkage, and  
         
           
             
             
                 
                 
             
           
         
         wherein R 7  is independently a C 10 -C 40  branched or unbranched, substituted or unsubstituted alkyl, allyl, or alkynyl group, having the following properties:  
         a dynamic viscosity of about 0.5×10 4  P to about 3×10 4  P,  
         a weight of about 8 to about 9 pounds per gallon, and  
         a Garde-Holt test value no greater than 15.  
       
     
     
         36 . A compound having the formula  
       
         
           
           
               
               
           
         
         wherein m is an integer of 1 to 100;  
         R 1  is independently a C 1 -C 20  alkyl group;  
         R 2  is independently an oxygen atom or a sulfur atom;  
         R 3  is independently a C 1 -C 70  alkyl, allyl, alkynyl, aryl, or phenyl group;  
         R 4  is independently selected from the group consisting of an —C p H 29 OH; —C p H 2p-1 OH; —C p H 2p-2 OH, wherein p is an integer of one to seven; a hydrogen atom; a carboxyl group, an alkyl group; an allyl group; and an alkynyl group;  
         R 5  is independently selected from the group consisting of an alkyl group, an alkyl group containing at least one ether linkage, and  
         
           
             
             
                 
                 
             
           
         
         wherein R 7  is independently a C 10 -C 40  branched or unbranched, substituted or unsubstituted alkyl, allyl, or alkynyl group,  
         wherein the compound has a viscosity that continues to increase upon heating.  
       
     
     
         37 . A method of preparing a melamine ring-containing co-polymer having the formula (I):  
       
         
           
           
               
               
           
         
         wherein m is an integer from 1 to 100;  
         R 1  is independently selected from the group consisting of an alkyl group having one to twenty carbon atoms;  
         R 2  is independently selected from the group consisting of an oxygen atom and a sulfur atom;  
         R 3  is independently selected from the group consisting of an alkyl group, an allyl group, an alkynyl group, an aryl group, and a phenyl group, having one to seventy carbon atoms;  
         R 4  is independently selected from the group consisting of —C p H 2p OH; —C p H 2p-1 OH; —C p H 2p-2 OH, wherein p is an integer of one to seven; a hydrogen atom; a carboxyl group, an alkyl group; an allyl group; and an alkynyl group;  
         R 5  is independently selected from the group consisting of an alkyl group, an alkyl group containing at least one ether linkage, and the group represented by the formula (III):  
         
           
             
             
                 
                 
             
           
         
         wherein R 7  is independently a C 10 -C 40  branched or unbranched, substituted or unsubstituted alkyl, allyl, or alkynyl group, and;  
         n is an integer from one to thirty; comprising the steps of  
         (a) mixing a melamine base resin and cashew nut shell liquid;  
         (b) heating the mixture from about 140° C. to about 170° C.; and  
         (c) reacting the mixture for about 4 to about 6 hours.  
       
     
     
         38 . The method of  claim 37 , wherein the mixing step further comprises the addition of a catalyst selected from the group consisting of a sulfo radical containing catalyst, methanesulfonic acid, phosphoric acid, nitric acid, oxalic acid, maleic acid, hexamic acid, phthalic acid, acrylic acid, para-toluene sulfonic acid, dinonyl naphthalene sulfonic acid, magnesium bromide, zinc nitrate, aluminum nitrate, magnesium nitrate, and combinations thereof.