Polymers made from bis(2-hydroxyethyl)isosorbide and enduses thereof

Abstract

This invention provides a new, biomass-derived glycol, bis(2-hydroxyethyl)isosorbide, which is found to be a valuable monomer for a wide variety of polymeric materials

What is claimed is:  
     
         1 . Bis(2-hydroxyethyl)isosorbide.  
     
     
         2 . A polymer composition comprising a polymer and bis(2-hydroxyethyl)isosorbide comonomer.  
     
     
         3 . The polymer composition of  claim 2  wherein the polymer is selected from the group consisting of polyester, polyamide ester, polyurethane, polycarbonate, polycarbonate ester, polyether sulfone, polyether ketone, and polyether ether ketone.  
     
     
         4 . The polymer composition of  claim 2  further comprising a dicarboxylic acid.  
     
     
         5 . The polymer composition of  claim 4  further comprising at least a second glycol.  
     
     
         6 . The polymer composition of  claim 2  or  claim 4  further comprising at least one polyfunctional branching agent.  
     
     
         7 . A polyester comprising: 
 (a) 45.0 to 50.0 mole percent of a dicarboxylic acid,    (b) 0.1 to 50.0 mole percent of bis(2-hydroxyethyl)isosorbide,    (c) 0 to 49.9 mole percent of at least one additional glycol, and    (d) 0 to 5.0 mole percent of at least one polyfunctional branching agent.    
     
     
         8 . The polymer composition of  claim 4 , wherein said dicarboxylic acid is selected from the group consisting of unsubstituted and substituted aromatic, aliphatic, unsaturated, and acyclic dicarboxylic acids; and the lower alkyl esters of aromatic, aliphatic, unsaturated, and acyclic dicarboxylic acids having from 8 carbons to 36 carbons.  
     
     
         9 . The polymer composition of  claim 4  wherein said dicarboxylic acid is selected from the group consisting of terephthalic acid, dimethyl terephthalate, isophthalic acid, dimethyl isophthalate, 2,6-naphthalene dicarboxylic acid, dimethyl-2,6-naphthalate, metal salts of 5-sulfo-dimethylisophthalate, oxalic acid, dimethyl oxalate, malonic acid, dimethyl malonate, succinic acid, dimethyl succinate, methylsuccinic acid, glutaric acid, dimethyl glutarate, 2-methylglutaric acid, 3-methylglutaric acid, adipic acid, dimethyl adipate, 3-methyladipic acid, 2,2,5,5-tetramethylhexanedioic acid, pimelic acid, suberic acid, azelaic acid, dimethyl azelate, sebacic acid, 1,11-undecanedicarboxylic acid, 1,10-decanedicarboxylic acid, undecanedioic acid, 1,12-dodecanedicarboxylic acid, hexadecanedioic acid, docosanedioic acid, tetracosanedioic acid, dimer acid, 1,4-cyclohexanedicarboxylic acid, dimethyl-1,4-cyclohexanedicarboxylate, 1,3-cyclohexanedicarboxylic acid, dimethyl-1,3-cyclohexanedicarboxylate, 1,1-cyclohexanediacetic acid, fumaric acid, maleic anhydride, maleic acid, hexahydrophthalic acid, phthalic acid, and combinations thereof.  
     
     
         10 . The polymer composition of  claim 5  wherein said glycol is selected from the group consisting of unsubstituted, substituted, straight chain, branched, cyclic aliphatic, aliphatic-aromatic and aromatic diols having from 2 carbon atoms to 36 carbon atoms; and poly(alkylene ether) glycols with molecular weights between about 250 to 4,000.  
     
     
         11 . The polymer composition of  claim 5  wherein said glycol is selected from the group consisting ethylene glycol, 1,3-propanediol, 1,2-propanediol,1,2-butanediol, 1,3-butanediol, 1,3-2-methylpropanediol, neopentyl glycol, 1,4-butanediol, 1,3-hexanediol, 1,6-hexanediol, 2-ethyl-2-methyl-1,3-propanediol, 1,8-octanediol, 1,10-decanediol, 1,12-dodecanediol, 1,14-tetradecanediol, 1,16-hexadecanediol, dimer diol, 4,8-bis(hydroxymethyl)-tricyclo[5.2.1.0/2.6]decane, 1,4-cyclohexanedimethanol, di(ethylene glycol), tri(ethylene glycol), poly(ethylene ether) glycols, poly(butylene ether) glycols and combinations thereof.  
     
     
         12 . A process for producing bis(2-hydroxyethyl)isosorbide comprising the steps of: 
 (a) contacting isosorbide with a stoichiometric excess of ethylene carbonate in the presence of a catalyst,    (b) heating the product of step (a) gradually, with mixing, at a temperature sufficient to substantially evolve carbon dioxide from said product, and    (c) cooling the product of step (b) to ambient temperature.    
     
     
         13 . The process of  claim 12  wherein the temperature is from 50° C. to 300° C.  
     
     
         14 . The process of  claim 12  wherein the temperature is from 75° C. to 200° C.  
     
     
         15 . The polymer composition of  claim 3  wherein said polyester is biodegradable.  
     
     
         16 . A polyurethane comprising: 
 (a) 45.0 to 50.0 mole percent of polyisocyanate,    (b) 0.1 to 50.0 mole percent of bis(2-hydroxyethyl)isosorbide,    (c) 0 to 49.9 mole percent of at least one additional glycol, and    (d) 0 to 5.0 mole percent at least one polyester polyol.    
     
     
         17 . The polymer composition of  claim 16 , wherein the polyisocyanate is selected from unblocked polyisocyanates and blocked isocyanates.  
     
     
         18 . The polymer composition of  claim 17  wherein the blocked isocyanate is chemically blocked with a compound selected from the group consisting of methanol, oximes, lactams, imidazole, and phenols.  
     
     
         19 . The polymer composition of  claim 17  wherein the polyisocyanate is selected from the group consisting of diphenylmethane diisocyanate, toluene diisocyanate, xylene diisocyanate, phenylene diisocyanate, naphthalene diisocyanate, 4,4′-methylene-bis-(cyclohexyl isocyanate), isophorone diisocyanate, 1,6-hexamethylene diisocyanate, a biuret from 1,6-hexamethylene diisocyanate, 1,12-dodecane diisocyanate, mixtures thereof.  
     
     
         20 . The polymer composition of  claim 2  in the form of a shaped article.  
     
     
         21 . The shaped article of  claim 20  in the form of a film, sheet, fiber, container or foamed article.