Polyethers containing non-bisphenolic cyclic groups

Abstract

Metal food or beverage containers are coated with a polyether polymer containing at least two ether linkages in the polymer backbone. The polymer is substantially free of segments derived from bisphenol A and epoxides thereof, and is a reaction product of, or can be derived from, (i) an aryl- or heteroaryl-group-containing diepoxide that is not derived from a polyhydric phenol or a glycidyl ester and (ii) a polymer backbone extender that has two functional groups reactive with an epoxy group and which following reaction with the diepoxide provides at least one pendant aryl or heteroaryl group on the polymer backbone, or provides at least one divalent aryl or heteroaryl group in the polymer backbone and linked to the backbone via ether linkages.

We claim: 
     
         1 . An article comprising a food or beverage container, or a portion thereof, having a metal substrate and a food-contact coating applied on at least a portion of the metal substrate, wherein the coating is formed from a coating composition that includes a polyether polymer having a polymer backbone, wherein the polymer contains at least two ether linkages in the polymer backbone; is substantially free of segments derived from bisphenol A and epoxides thereof; and is a reaction product of, or can be derived from, reactants including: (i) an aryl- or heteroaryl-group-containing diepoxide that is not derived from a polyhydric phenol or a glycidyl ester and (ii) a polymer backbone extender that has two functional groups reactive with an epoxy group and which following reaction with the diepoxide provides at least one pendant aryl or heteroaryl group on the polymer backbone, or provides at least one divalent aryl or heteroaryl group in the polymer backbone and linked to the backbone via ether linkages. 
     
     
         2 . The article of any preceding claim, wherein the diepoxide provides a pendant aryl or heteroaryl group on the polymer backbone. 
     
     
         3 . The article of any preceding claim, wherein the diepoxide provides an aryl or heteroaryl group in the polymer backbone and linked to it via ether linkages. 
     
     
         4 . The article of any preceding claim, wherein the diepoxide includes a single aryl or heteroaryl group. 
     
     
         5 . The article of any preceding claim, wherein the diepoxide includes a single phenylene group. 
     
     
         6 . The article of any of  claims 1  to  3 , wherein the diepoxide includes a plurality of aryl or heteroaryl groups. 
     
     
         7 . The article of any preceding claim, wherein the aryl or heteroaryl groups are nonphenolic. 
     
     
         8 . The article of any preceding claim, wherein the diepoxide is derived from an aryl- or heteroaryl-group containing diol. 
     
     
         9 . The article of any preceding claim, wherein the diepoxide is derived from a compound having a single phenyl hydroxyl group and a functional group that is not a phenyl hydroxyl group, wherein the functional group is capable of reacting with epichlorohydrin to provide an epoxide group. 
     
     
         10 . The article of  claim 9 , wherein the functional group is an alcohol or acid group. 
     
     
         11 . The article of any preceding claim, wherein the polymer has a number average molecular weight of at least 2,000. 
     
     
         12 . The article of any preceding claim, wherein the polymer has a number average molecular weight of at least 2,500. 
     
     
         13 . The article of any preceding claim, wherein the polymer has a number average molecular weight less than 20,000. 
     
     
         14 . The article of any preceding claim, wherein the polymer has a Tg of at least 30° C. 
     
     
         15 . The article of any preceding claim, wherein the polymer has a Tg of at least 60° C. 
     
     
         16 . The article of any preceding claim, wherein the diepoxide includes a segment of Formula I shown below: 
       
         
           
           
               
               
           
         
       
       wherein:
 each depicted oxygen atom in Formula I is present in an ether linkage; 
 R 1  is a trivalent organic group having from 1 to about 10 carbon atoms; 
 X is a divalent organic group having from 1 up to about 10 carbon atoms, an oxygen atom, a sulfur atom, or a nitrogen-containing group; 
 n is 0 or 1; and 
 Ar 1  is an aryl or heteroaryl group which does not contain a bisphenol monomer segment. 
 
     
     
         17 . The article of  claim 16 , wherein the segment of Formula I is derived from a phenyl aliphatic diol. 
     
     
         18 . The article of  claim 16 , wherein R 1  is an alkyl or cycloalkyl group and does not include an aryl or heteroaryl group. 
     
     
         19 . The article of  claim 16 , wherein n is 0 and R 1  includes from 2 to about 6 carbon atoms. 
     
     
         20 . The article of any of  claims 16  to  19 , wherein the segment of Formula I has an atomic weight less than 500 Daltons. 
     
     
         21 . The article of any preceding claim, wherein the polymer is derived from a diepoxide of Formula II shown below: 
       
         
           
           
               
               
           
         
       
       wherein:
 each depicted oxygen atom in Formula II attached to R 1  is present in an ether linkage; 
 R 1  is a trivalent organic group having from 1 to about 10 carbon atoms; 
 X is a divalent organic group having from 1 up to about 10 carbon atoms, an oxygen atom, a sulfur atom, or a nitrogen-containing group; 
 n is 0 or 1; 
 Ar 1  is an aryl or heteroaryl group which does not contain a bisphenol monomer segment. 
 Y, if present, is a divalent organic group including at least one carbon atom; 
 each t is independently 0 or 1; and 
 each R 2  is a hydrogen atom. 
 
     
     
         22 . The article of any preceding claim, wherein the diepoxide includes a segment of Formula IV shown below:
   —O—R 3 —Ar 2 —R 4 —O—  IV
   
       wherein:
 the terminal oxygen atoms attached to R 3  and R 4  in Formula IV are present in ether linkages; 
 R 3  and R 4  independently are each divalent organic groups having from 1 to about 10 carbon atoms; and 
 Ar 2  is a divalent nonphenolic aryl or heteroaryl group which does not contain a bisphenol monomer segment. 
 
     
     
         23 . The article of  claim 22 , wherein the diepoxide compound does not include ester linkages. 
     
     
         24 . The article of  claim 22  or  claim 23 , wherein the segment of Formula IV has an atomic weight less than 500 Daltons. 
     
     
         25 . The article of any of  claims 22  to  24 , wherein R 3 , R 4  or both R 3  and R 4  do not include an ester linkage directly attached to Ar 2 . 
     
     
         26 . The article of any of  claims 22  to  24 , wherein R 3 , R 4  or both R 3  and R 4  do not include any ester linkages. 
     
     
         27 . The article of any preceding claim, wherein the polymer is derived from a diepoxide of Formula V shown below: 
       
         
           
           
               
               
           
         
       
       wherein:
 the depicted oxygen atoms attached to R 3  and R 4  in Formula V are present in ether linkages; 
 R 3  and R 4  independently are each divalent organic groups having from 1 to about 10 carbon atoms; 
 Ar 2  is a divalent nonphenolic aryl or heteroaryl group which does not contain a bisphenol monomer segment; 
 Y, if present, is a divalent organic group including at least one carbon atom; 
 each t is independently 0 or 1; and 
 each R 2  is a hydrogen atom. 
 
     
     
         28 . The article of any preceding claim, wherein the diepoxide comprises 1-phenyl-1,2-propanediol diglycidyl ether. 
     
     
         29 . The article of any preceding claim, wherein the diepoxide comprises 2-phenyl-1,2-propanediol diglycidyl ether. 
     
     
         30 . The article of any preceding claim, wherein the diepoxide comprises 1-phenyl-1,3-propanediol diglycidyl ether. 
     
     
         31 . The article of any preceding claim, wherein the diepoxide comprises 2-phenyl-1,3-propanediol diglycidyl ether. 
     
     
         32 . The article of any preceding claim, wherein the diepoxide comprises 1-phenyl-1,2-ethanediol diglycidyl ether. 
     
     
         33 . The article of any preceding claim, wherein the diepoxide comprises vanillyl alcohol diglycidyl ether. 
     
     
         34 . The article of any preceding claim, wherein the diepoxide comprises 1,2-, 1,3- or 1,4-benzenedimethanol diglycidyl ether. 
     
     
         35 . The article of any preceding claim, wherein the diepoxide comprises 2,5-furandimethanol diglycidyl ether. 
     
     
         36 . The article of any preceding claim, wherein the extender provides a pendant aryl or heteroaryl group on the polymer backbone. 
     
     
         37 . The article of any preceding claim, wherein the extender provides an aryl or heteroaryl group in the polymer backbone and linked to it via ether linkages. 
     
     
         38 . The article of any preceding claim, wherein the extender includes a segment of Formula I shown below: 
       
         
           
           
               
               
           
         
       
       wherein:
 each depicted oxygen atom in Formula I is present in an ether linkage; 
 R 1  is a trivalent organic group having from 1 to about 10 carbon atoms; 
 X is a divalent organic group having from 1 up to about 10 carbon atoms, an oxygen atom, a sulfur atom, or a nitrogen-containing group; 
 n is 0 or 1; and 
 Ar 1  is an aryl or heteroaryl group which does not contain a bisphenol monomer segment. 
 
     
     
         39 . The article of any preceding claim, wherein the polymer is derived from an extender of Formula III shown below: 
       
         
           
           
               
               
           
         
       
       wherein:
 R 1  is a trivalent organic group having from 1 to about 10 carbon atoms; 
 X is a divalent organic group having from 1 up to about 10 carbon atoms, an oxygen atom, a sulfur atom, or a nitrogen-containing group; 
 n is 0 or 1; 
 Ar 1  is an aryl or heteroaryl group which does not contain a bisphenol monomer segment; and 
 each Z is independently an epoxide-reactive functional group, or both Z moieties may together with R 1  form an acid anhydride. 
 
     
     
         40 . The article of any preceding claim, wherein the extender includes a segment of Formula IV shown below:
   —O—R 3 —Ar 2 —R 4 —O—  IV
   
       wherein:
 the terminal oxygen atoms attached to R 3  and R 4  in Formula IV are present in ether linkages; 
 R 3  and R 4  independently are each divalent organic groups having from 1 to about 10 carbon atoms; and 
 Ar 2  is a divalent nonphenolic aryl or heteroaryl group which does not contain a bisphenol monomer segment. 
 
     
     
         41 . The article of any preceding claim, wherein the polymer is derived from an extender of Formula VI shown below:
   HO—R 3 —Ar 2 —R 4 —OH  VI
   
       wherein:
 the terminal oxygen atoms attached to R 3  and R 4  in Formula IV are present in ether linkages; 
 R 3  and R 4  independently are each divalent organic groups having from 1 to about 10 carbon atoms; and 
 Ar 2  is a divalent nonphenolic aryl or heteroaryl group which does not contain a segment derived from a bisphenol monomer. 
 
     
     
         42 . The article of any preceding claim, wherein the extender is a dihydric phenol. 
     
     
         43 . The article of any preceding claim, wherein the extender is a dihydric phenol having a molecular weight of from about 100 to about 400 Daltons. 
     
     
         44 . The article of any preceding claim, wherein the extender is hydroquinone, catechol, resorcinol, or a substituted variant thereof. 
     
     
         45 . The article of any preceding claim, wherein the polymer includes at least 25 wt. % aryl or heteroaryl groups. 
     
     
         46 . The article of any preceding claim, wherein the polymer includes at least 45 wt. % aryl or heteroaryl groups. 
     
     
         47 . The article of  claim 40  or  claim 41 , wherein the aryl or heteroaryl groups are phenylene groups. 
     
     
         48 . The article of  claim 40  or  claim 41 , wherein the heteroaryl groups are furanylene groups. 
     
     
         49 . The article of any preceding claim, wherein the polyether polymer has a polydispersity index of about 2 to about 5. 
     
     
         50 . The article of any preceding claim, wherein the polyether polymer is substantially free of segments derived from bisphenol monomers or epoxides of bisphenol monomers. 
     
     
         51 . The article of any preceding claim, wherein the polyether polymer is essentially free of bound polyhydric phenols having estrogenic activity greater than or equal to that of bisphenol S, and epoxides thereof. 
     
     
         52 . The article of any preceding claim, wherein the polyether polymer is free of halogen atoms. 
     
     
         53 . The article of any preceding claim, wherein the polyether polymer is free of sulfur atoms. 
     
     
         54 . The article of any preceding claim, wherein the backbone of the polyether polymer is free of ester linkages. 
     
     
         55 . The article of any preceding claim, wherein the coating composition includes a liquid carrier. 
     
     
         56 . The article of any preceding claim, wherein the coating composition is solvent-based and contains at least 20 wt. % non-volatile components, based on total resin solids. 
     
     
         57 . The article of any preceding claim, wherein the coating composition is water-based and contains at least 50 wt. % water. 
     
     
         58 . The article of any preceding claim, wherein the coating composition includes a crosslinker. 
     
     
         59 . The article of any preceding claim, wherein the polymer is derived from ingredients including the diglycidyl ether of vanillyl alcohol. 
     
     
         60 . The article of any preceding claim, wherein the polymer is derived from ingredients including the diglycidyl ether of 2,5-furandimethanol. 
     
     
         61 . The article of any preceding claim, wherein the polymer is derived from ingredients including one or more of the diglycidyl ether of 1,2-benzenedimethanol, the diglycidyl ether of 1,3-benzenedimethanol, the diglycidyl ether of 1,4-benzenedimethanol, the diglycidyl ether of 1,4-benzenediethanol, the diglycidyl ether of 1,3-benzenedipropanol, the diglycidyl ether of 1,4-benzenedipropanol, the diglycidyl ether of 2-(4-hydroxyphenyl)ethanol, the diglycidyl ether of 4,4′-(1,4-phenylene)bis(4-methyl-2-pentanol), the diglycidyl ether of 2-(3-hydroxyphenyl)ethanol, the diglycidyl ether of 2-hydroxyphenethyl alcohol, the diglycidyl ether of 2-hydroxyphenylacetic acid, or the diglycidyl ether of 4-hydroxy-3,5-dimethoxybenzoic acid.