Heteroatom containing cyclic dimers

Abstract

The present invention provides cyclic dimers of alpha acids and polymers derived therefrom. Also provided are processes for preparing and methods of using the cyclic dimers and the polymers derived from the cyclic dimers.

What is claimed is: 
     
         1 . A process for forming a polymer comprising repeat units of Formula (XX), the process comprising heating a plurality of monomers of Formula (II) to a temperature from about 100° C. to about 200° C. such that the monomers form the polymer comprising repeat units of Formula (XX): 
       
         
           
           
               
               
           
         
         wherein:
 R 1 , R 2 , R 3 , R 4 , and R 5  are independently hydrogen, hydrocarbyl, or substituted hydrocarbyl; 
 R 6  is hydrogen, hydrocarbyl, or substituted hydrocarbyl; 
 R 7  is not present; 
 Z is sulfur, sulfone, sulfoxide, or selenium; and 
 n is an integer ≧1. 
 
       
     
     
         2 . The process of  claim 1 , wherein R 1  is hydrogen, alkyl, or substituted alkyl, R 2 , R 3 , R 4 , and R 5  are hydrogen; R 6  is C 1 -C 6  alkyl; and n is from 1 to 10. 
     
     
         3 . The process of  claim 1 , wherein the plurality of monomers have Formula (IIa) and the polymer comprises repeat units of Formula (XXa): 
       
         
           
           
               
               
           
         
         wherein:
 R 2 , R 3 , R 4 , R 5 , R 6 , R 8 , R 9 , and R 10  are independently hydrogen, alkyl, or substituted alkyl; 
 R 7  and R 11  are not present; 
 Y and Z are independently sulfur, sulfone, sulfoxide, or selenium; and 
 n and m are integers ≧1. 
 
       
     
     
         4 . The process of  claim 3 , wherein R 2 , R 3 , R 4 , R 5 , R 8  and R 9  are hydrogen; R 6  and R 10  are C 1 -C 6  alkyl; and each of n and m is from 1 to 10. 
     
     
         5 . The process of  claim 4 , wherein R 6  and R 10  are methyl; Y and Z are sulfur, and each of n and m is 2. 
     
     
         6 . The process of  claim 1 , wherein the polymer comprising repeat units of Formula (XX) has a number average molecular weight of at least about 2,000 Da, at least about 10,000 Da, at least about 100,000 Da, or at least about 1,000,000 Da. 
     
     
         7 . The process of  claim 1 , wherein the polymer comprising repeat units of Formula (XX) contains less than about 5% by weight of free monomer. 
     
     
         8 . The process of  claim 1 , wherein the reaction is conducted in the absence or presence of a catalyst. 
     
     
         9 . The process of  claim 1 , wherein the temperature is from about 120° C. to about 180° C. 
     
     
         10 . The process of  claim 1 , wherein the heating occurs in an extruder, the extruder being a twin screw extruder, a single screw extruder, or an extruder thermoforming machine. 
     
     
         11 . An extrudate prepared by the process of  claim 10 . 
     
     
         12 . The process of  claim 1 , wherein the process further comprises heating in the presence of a plurality of additional monomers to form a copolymer. 
     
     
         13 . The process of  claim 12 , wherein the plurality of additional monomers is chosen from acrylates, aminoacrylates, alkylene succinates, alkylene oxalates, amides, amino acids, anhydrides, arylates, carbonates, celluloses, caprolactones, caprolactams, cyanoacrylates, cyclic ethers, dihydropyrans, dioxanes, dioxanones, ether ether ketones, ethylene glycols, fumarates, hydroxy alkanoates, hydroxy esters, imides, ketals, lactides, lactones, lactams, methacrylates, methyl olefins, orthoesters, phosphazines, styrenes, terephthalates, tetrafurans, trimethylene carbonates, urethanes, vinyl acetates, vinyl ketones, or vinyl halides. 
     
     
         14 . The process of  claim 13 , wherein the additional monomers are lactides, lactones, lactams, hydroxy alkanoates, or hydroxy esters. 
     
     
         15 . The process of  claim 12 , wherein the reaction is conducted in the absence or presence of a catalyst. 
     
     
         16 . The process of  claim 12 , wherein the temperature is from about 120° C. to about 180° C. 
     
     
         17 . The process of  claim 12 , wherein the heating occurs in an extruder, the extruder being a twin screw extruder, a single screw extruder, or an extruder thermoforming machine. 
     
     
         18 . An extrudate prepared by the process of  claim 17 . 
     
     
         19 . The process of  claim 1  further comprising heating in the presence of a polymer comprising at least one hydroxyl or amine group. 
     
     
         20 . The process of  claim 19 , wherein the polymer is a polylactide, polylactone, polylactam, polyolefin, polymethacrylate, polyhydroxyalkanoate, poly hydroxy ester, cellulose, or starch. 
     
     
         21 . The process of  claim 19 , wherein the reaction is conducted in the absence or presence of a catalyst. 
     
     
         22 . The process of  claim 19 , wherein the temperature is from about 120° C. to about 180° C. 
     
     
         23 . The process of  claim 19 , wherein the heating occurs in an extrude, the extruder being a twin screw extruder, a single screw extruder, or an extruder thermoforming machine. 
     
     
         24 . An extrudate prepared by the process of  claim 23 .