Process for manufacturing a hydroxyester derivative intermediate and epoxy resins prepared therefrom

Abstract

A process for manufacturing an α-halohydrin intermediate and an epoxy resin prepared therefrom including epoxidizing an α-halohydrin intermediate produced from an in situ halide substitution-deesterification of an α-hydroxy ester derivative which has been obtained by the coupling reaction of a phenol or a mixture of phenols and a glycidyl ester optionally in the presence of a catalyst.

What is claimed is:  
     
         1 . An epoxy resin product made by epoxidizing an α-halohydrin intermediate of at least one or more phenols formed by reacting (a) an α-hydroxy ester derivative of at least one or more phenols with (b) a hydrogen halide.  
     
     
         2 . An epoxy resin product made by epoxidizing an α-halohydrin intermediate formed by: 
 (a) preparing an α-hydroxy ester derivative of at least one or more phenols by reacting at least one or more phenols with a glycidyl ester or substituted glycidyl ester; and  
 (b) reacting the α-hydroxy ester derivative of at least one or more phenols with a hydrogen halide to form the α-halohydrin intermediate.  
 
     
     
         3 . An epoxy resin product made by the steps of: 
 (a) preparing an α-hydroxy ester derivative of at least one or more phenols by reacting at least one or more phenols with a glycidyl ester of substituted glycidyl ester;    (b) preparing an α-halohydrin intermediate by reacting the α-hydroxy ester derivative of Step (a) with a hydrogen halide; and    (c) epoxidizing the α-halohydrin intermediate of Step (b).    
     
     
         4 . The epoxy resin of  claim 3  wherein the glycidyl ester of substituted glycidyl ester is prepared by esterifying glycidol or a substituted glycidol with a carboxylic acid or a carboxylic acid halide.  
     
     
         5 . The epoxy resin of  claim 4  wherein the glycidyl ester of substituted glycidyl ester is prepared by epoxidation of an allyl ester or a substituted allyl ester of a carboxylic acid.  
     
     
         6 . An epoxy resin product made by the steps of: 
 (a) providing a glycidyl ester or substituted glycidyl ester of a carboxylic acid;    (b) preparing an α-hydroxy ester derivative of at least one or more phenols by reacting at least one or more phenols with the glycidyl ester or a substituted glycidyl ester of Step (a);    (c) preparing an α-halohydrin intermediate by reacting the α-hydroxy ester derivative of Step (b) with a hydrogen halide; and    (d) epoxidizing the α-halohydrin intermediate of Step (c).    
     
     
         7 . An epoxy resin product made by the steps of: 
 (a) providing an allyl ester or a substituted allyl ester of a carboxylic acid;    (b) preparing a glycidyl ester or a substituted glycidyl ester by epoxidizing the allyl ester or a substituted allyl ester of Step (a) with an oxidant;    (c) preparing an α-hydroxy ester derivative of at least one or more phenols by reacting at least one or more phenols with the glycidyl ester or a substituted glycidyl ester of Step (b);    (d) preparing an α-halohydrin intermediate by reacting the α-hydroxy ester derivative of Step (c) with a hydrogen halide; and    (e) epoxidizing the α-halohydrin intermediate of Step (d) to form an epoxy resin product.    
     
     
         8 . An epoxy resin product made by the steps of: 
 (a) providing allyl acetate;    (b) preparing glycidyl acetate by epoxidizing the allyl acetate of Step (a) with an oxidant;    (c) preparing a bis(α-hydroxy acetoxy) derivative of bisphenol A by reacting bisphenol A with the glycidyl acetate of Step (b);    (d) preparing a bis(α-chlorohydrin) intermediate of bisphenol A by reacting the bis(α-hydroxy acetoxy) derivative of bisphenol A of Step (c) with hydrogen chloride; and    (e) epoxidizing the bis(α-chlorohydrin) intermediate of bisphenol A of Step (d) to form an epoxy resin product.    
     
     
         9 . The epoxy resin product of any one of  claims 1  to  8  comprising a structure represented by the following Formula XVIII:  
       Formula XVIII  
       (R 2 ) y Ar(OR 1 ) z    
       wherein y is from 0 to 750; z is from 1 to 150; Ar is an aromatic-containing moiety; R 1 ″ is a glycidyl-containing moiety; and R 2  is a group substituted for a hydrogen atom on the Ar moiety.  
     
     
         10 . The epoxy resin of  claim 9  wherein R 1 ″ is a glycidyl-containing moiety selected from:  
       
         
           
           
               
               
           
         
       
       where R 3  is hydrogen, an alkyl group having from 1 to 20 carbon atoms, a cycloaliphatic group having from 3 to 20 carbon atoms, an aromatic group having from 6 to 20 carbon atoms, or any combination thereof.  
     
     
         11 . The epoxy resin of  claim 10  wherein R 1 ″ is selected from:  
       
         
           
           
               
               
           
         
       
     
     
         12 . The epoxy resin of  claim 9  represented by any one of the following Formulas XIX-XXII:  
       
         
           
           
               
               
           
         
       
       wherein y is 0 to 5; z is 1 to 4; R 1 ″ is a glycidyl-containing moiety; and R 2  is a group substituted for a hydrogen atom on the Ar moiety;  
       
         
           
           
               
               
           
         
       
       wherein y is 0 to 4, and each y can be the same or different; z is 1 to 3, and each z can be the same or different; R 1 ″ is a glycidyl-containing moiety; R 2  is a group substituted for a hydrogen atom on the aromatic ring; and Z is (i) nil, (ii) a heteroatom with or without substituents thereon to complete its necessary bonding valence, (iii) —C(O)—, (iv) —S(O 2 )—, (v) —C(O)NH—, (vi) —P(O)Ar—, (vii) an organic aliphatic or cycloaliphatic moiety, saturated or unsaturated, with or without heteroatoms, or (viii) a partially or fully fluorinated organic aliphatic or cycloaliphatic moiety;  
       
         
           
           
               
               
           
         
       
       wherein y is 0 to 4, and each y can be the same or different; z is 1 to 3, and each z can be the same or different; R 1 ″ is a glycidyl-containing moiety; R 2  is a group substituted for a hydrogen atom on the aromatic ring; Z is (i) nil, (ii) a heteroatom with or without substituents thereon to complete its necessary bonding valence (iii), —C(O)—, (iv) —S(O 2 )—, (v) —C(O)NH—, (vi) —P(O)Ar—, (vii) an organic aliphatic or cycloaliphatic moiety, saturated or unsaturated, with or without heteroatoms, or (viii) a partially or fully fluorinated organic aliphatic or cycloaliphatic moiety; and m is from 0.001 to 10; or  
       
         
           
           
               
               
           
         
       
       wherein y is 0 to 4, and each y can be the same or different; z is 1 to 3, and each z can be the same or different; R 1 ″, is a glycidyl-containing moiety; R 2  is a group substituted for a hydrogen atom on the aromatic ring; Z′ is (i) an organic aliphatic moiety, saturated or unsaturated, with or without heteroatoms, wherein the aliphatic moiety has from 1 to 20 carbon atoms, (ii) a cycloaliphatic moiety, saturated or unsaturated, with or without heteroatoms, having from 3 to 20 carbon atoms, (iii) an aromatic moiety, with or without heteroatoms, having 6 to 20 carbon atoms, a partially or fully fluorinated organic aliphatic, cycloaliphatic or aromatic moiety, (v) or any combination thereof; and m′ is 3 or 4.  
     
     
         13 . The epoxy resin of  claim 12  selected from the group comprising aryl glycidyl ethers and aryl methylglycidyl ethers.  
     
     
         14 . The epoxy resin of  claim 12  selected from the group comprising 1,3-dihydroxybenzene diglycidyl ether; 1,3-dihydroxybenzene dimethylglycidyl ether; 1,4-dihydroxybenzene diglycidyl ether; 1,4-dihydroxybenzene dimethylglycidyl ether; 1,5-naphthalene diglycidyl ether; 1,5-naphthalene dimethylglycidyl ether; 2,6-naphthalene diglycidyl ether; 2,6-naphthalene dimethylglycidyl ether; 4,4′-dihydroxybiphenyl diglycidyl ether; 4,4′-dihydroxybiphenyl dimethylglycidyl ether; 3,3′,5,5′-tetramethyl-4,4′-dihydroxybiphenyl diglycidyl ether; 3,3′,5,5′-tetramethyl-4,4′-dihydroxybiphenyl dimethylglycidyl ether; 3,3′,5,5′-tetramethyl-2,2′,6,6′-tetrabromo-4,4′-dihydroxybiphenyl diglycidyl ether; 3,3′,5,5′-tetramethyl-2,2′,6,6′-tetrabromo-4,4′-dihydroxybiphenyl dimethylglycidyl ether; bis(4-hydroxyphenyl)methane diglycidyl ether; bis(4-hydroxyphenyl)methane dimethylglycidyl ether; 2,2-bis(4-hydroxyphenyl)isopropylidene diglycidyl ether; 2,2-bis(4-hydroxyphenyl)isopropylidene dimethylglycidyl ether; phenol-formaldehyde novolac glycidyl ether (functionality greater than 2); phenol-formaldehyde novolac methylglycidyl ether (functionality greater than 2); o-cresol-formaldehyde novolac glycidyl ether (functionality greater than 2); o-cresol-formaldehyde novolac methylglycidyl ether (functionality greater than 2); phenol-dicyclopentadienyl novolac glycidyl ether (functionality greater than 2); phenol-dicyclopentadienyl novolac methylglycidyl ether (functionality greater than 2); naphthol-formaldehyde novolac glycidyl ether (functionality greater than 2); naphthol-formaldehyde novolac methylglycidyl ether (functionality greater than 2); 1,1,1-tris(4-hydroxyphenyl)methane triglycidyl ether, 1,1,1-tris(4-hydroxyphenyl)methane trimethylglycidyl ether; 1,1,2,2-tetrakis(4-hydroxyphenyl)ethane tetraglycidyl ether; 1,1,2,2-tetrakis(4-hydroxyphenyl)ethane tetramethylglycidyl ether; and mixtures thereof.  
     
     
         15 . The epoxy resin of  claim 14  wherein the epoxy resin is 2,2-bis(4-hydroxyphenyl)isopropylidene diglycidyl ether.  
     
     
         16 . The epoxy resin of any one of  claims 1  to  8  wherein the α-hydroxy ester derivative of at least one or more phenols is represented by the following Formula VI:  
       Formula VI  
       (R 2 )yAr(O R 1 ) z    
       wherein y is from 0 to 750; z is from 1 to 150; Ar is an aromatic-containing moiety; R 1″  is an α-hydroxy ester propyl-containing moiety; and R 2  is a group substituted for a hydrogen atom on the Ar moiety.  
     
     
         17 . The epoxy resin of  claim 16  wherein the α-hydroxy ester derivative of at least one or more phenols, comprises a structure represented by any one or more of Formulas VII-X as follows:  
       
         
           
           
               
               
           
         
       
       wherein y is 0 to 5; z is 1 to 4; R 1′  is an α-hydroxy ester propyl-containing moiety; and R 2  is a group substituted for a hydrogen atom on the aromatic ring;  
       
         
           
           
               
               
           
         
       
       wherein y is 0 to 4, and each y can be the same or different; z is 1 to 3, and each z can be the same or different; R 1  is an α-hydroxy ester propyl-containing moiety; R 2  is a group substituted for a hydrogen atom on the aromatic ring; and Z is (i) nil, (ii) a heteroatom with or without substituents thereon to complete its necessary bonding valence, (iii) —C(O)—, (iv) —S(O 2 )—, (v) —C(O)NH—, (vi) —P(O)Ar′, (vii) an organic aliphatic or cycloaliphatic moiety, saturated or unsaturated, with or without heteroatoms, or (viii) a partially or fully fluorinated organic aliphatic or cycloaliphatic moiety;  
       
         
           
           
               
               
           
         
       
       wherein y is 0 to 4, and each y can be the same or different; z is 1 to 3, and each z can be the same or different; R 1′  is an α-hydroxy ester propyl-containing moiety; R 2  is a group substituted for a hydrogen atom on the aromatic ring; Z is (i) nil, (ii) a heteroatom with or without substituents thereon to complete its necessary bonding valence, (iii) —C(O)—, (iv) —S(O 2 )—, (v) —C(O)NH—, (vi) —P(O)Ar—, (vii) an organic aliphatic or cycloaliphatic moiety, saturated or unsaturated, with or without heteroatoms, or (viii) a partially or fully fluorinated organic aliphatic or cycloaliphatic moiety; and m is from 0.001 to 10; or  
       
         
           
           
               
               
           
         
       
       wherein y is 0 to 4, and each y can be the same or different; z is 1 to 3, and each z can be the same or different; R 1′  is an α-hydroxy ester propyl-containing moiety; R 2  is a group substituted for a hydrogen atom on the aromatic ring; Z′ is (i) an organic aliphatic moiety, saturated or unsaturated, with or without heteroatoms, wherein the aliphatic moiety has from 1 to 20 carbon atoms, (ii) a cycloaliphatic moiety, saturated or unsaturated, with or without heteroatoms, having from 3 to 20 carbon atoms, (iii) an aromatic moiety, with or without heteroatoms, having 6 to 20 carbon atoms, (iv) a partially or fully fluorinated organic aliphatic, cycloaliphatic or aromatic moiety, or (v) any combination thereof; and m′ is 3 or 4.  
     
     
         18 . The epoxy resin of  claim 17  wherein the α-hydroxy ester propyl-containing moiety is selected from:  
       
         
           
           
               
               
           
         
       
       wherein X′ and Y′ may be a hydroxyl group or a carboxylic acid ester moiety, with the proviso that when X′ is a hydroxyl group Y′ must be a carboxylic acid ester moiety and when Y′ is a hydroxyl group X′ must be a carboxylic acid ester moiety; and R 3  is hydrogen, an alkyl group having from 1 to 20 carbon atoms, a cycloaliphatic group having from 3 to 20 carbon atoms, an aromatic group having from 6 to 20 carbon atoms or any combination thereof.  
     
     
         19 . The epoxy resin of  claim 18  wherein R 1′  is selected from:  
       
         
           
           
               
               
           
         
       
       wherein X′ and Y′ may be a hydroxyl group or a carboxylic acid ester moiety, with the proviso that when X′ is a hydroxyl group Y′ must be a carboxylic acid ester moiety and when Y′ is a hydroxyl group X′ must be a carboxylic acid ester moiety.  
     
     
         20 . The epoxy resin of  claim 19  wherein the carboxylic acid ester moiety has the following general structure:  
       
         
           
           
               
               
           
         
       
       wherein R 4  is hydrogen; an alkyl group having from 1 to 20 carbon atoms; an alkenyl group having from 2 to 20 carbon atoms; a cycloaliphatic group having from 3 to 20 carbon atoms; or an aromatic group having from 6 to 20 carbon atoms.  
     
     
         21 . The epoxy resin of  claim 20  wherein R 4  is a methyl group.  
     
     
         22 . The epoxy resin of  claim 17  wherein the α-hydroxy ester derivative of phenols or mixtures of phenols is selected from the group comprising 1,3-dihydroxybenzene bis(3-acetoxy-2-hydroxypropyl) ether; 1,4-dihydroxybenzene bis(3-acetoxy-2-hydroxypropyl) ether; 1,5-dihydroxynaphthalene bis(3-acetoxy-2-hydroxypropyl) ether; 2,6-dihydroxynaphthalene bis(3-acetoxy-2-hydroxypropyl) ether; 4,4′-dihydroxybiphenyl bis(3-acetoxy-2-hydroxypropyl) ether; 3,3′,5,5′-tetramethyl-4,4′-dihydroxybiphenyl bis(3-acetoxy-2-hydroxypropyl) ether; 3,3′,5,5′-tetramethyl-2,2′,6,6′-tetrabromo-4,4′-dihydroxybiphenyl bis(3-acetoxy-2-hydroxypropyl) ether; bis(4-hydroxyphenyl)methane bis(3-acetoxy-2-hydroxypropyl) ether; 2,2-bis(4-hydroxyphenyl) isopropylidene bis(3-acetoxy-2-hydroxypropyl) ether; phenol-formaldehyde novolac (3-acetoxy-2-hydroxypropyl) ether (functionality greater than 2); o-cresol-formaldehyde novolac (3-acetoxy-2-hydroxypropyl) ether (functionality greater than 2); phenol-dicyclopentadienyl novolac (3-acetoxy-2-hydroxypropyl) ether (functionality greater than 2); naphthol-formaldehyde novolac (3-acetoxy-2-hydroxypropyl) ether (functionality greater than 2); 1,1,1-tris(4-hydroxyphenyl)methane tris(3-acetoxy-2-hydroxypropyl) ether; 1,1,2,2-tetrakis(4-hydroxyphenyl)ethane tetrakis(3-acetoxy-2-hydroxypropyl) ether; 1,3-dihydroxybenzene bis(2-acetoxy-3-hydroxypropyl) ether; 1,4-dihydroxybenzene bis(2-acetoxy-3-hydroxypropyl) ether; 1,5-dihydroxynaphthalene bis(2-acetoxy-3-hydroxypropyl) ether; 2,6-dihydroxynaphthalene bis(2-acetoxy-3-hydroxypropyl) ether; 4,4′-dihydroxybiphenyl bis(2-acetoxy-3-hydroxypropyl) ether; 3,3′,5,5′-tetramethyl-4,4′-dihydroxybiphenyl bis(2-acetoxy-3-hydroxypropyl) ether; 3,3′,5,5′-tetramethyl-2,2′,6,6′-tetrabromo-4,4′-dihydroxybiphenyl bis(2-acetoxy-3-hydroxypropyl) ether; bis(4-hydroxyphenyl)methane di(2-acetoxy-3-hydroxypropyl) ether; 2,2-bis(4-hydroxyphenyl) isopropylidene di(2-acetoxy-3-hydroxypropyl) ether; phenol-formaldehyde novolac (2-acetoxy-3-hydroxypropyl) ether (functionality greater than 2); o-cresol-formaldehyde novolac (2-acetoxy-3-hydroxypropyl) ether (functionality greater than 2); phenol-dicyclopentadienyl novolac (2-acetoxy-3-hydroxypropyl) ether (functionality greater than 2); naphthol-formaldehyde novolac (2-acetoxy-3-hydroxypropyl) ether (functionality greater than 2); 1,1,1-tris(4-hydroxyphenyl)methane tris(2-acetoxy-3-hydroxypropyl) ether; 1,1,2,2-tetrakis(4-hydroxyphenyl)ethane tetrakis (2-acetoxy-3-hydroxypropyl) ether; and mixtures thereof.  
     
     
         23 . The epoxy resin of  claim 22  wherein the α-hydroxy ester derivative of phenols or mixtures of phenols is selected from the group comprising 2,2-bis(4-hydroxyphenyl)isopropylidene bis(3-acetoxy-2-hydroxypropyl) ether; 2,2-bis(4-hydroxyphenyl) isopropylidene bis(2-acetoxy-3-hydroxypropyl) ether; and mixtures thereof.  
     
     
         24 . The epoxy resin of  claim 17  wherein the α-hydroxy ester derivative of at least one or more phenols, (Component (A)), is a single component represented by any one of Formulas VI-X or a mixture of two or more components wherein at least one of the components is represented by any one of Formulas VI to X.  
     
     
         25 . The epoxy resin of  claim 24  wherein Component (A), the α-hydroxy ester derivative of at least one or more phenols, is a mixture comprising (i) a component having an α-hydroxy ester moiety wherein X′ and Y′ may be a hydroxyl group or a carboxylic acid ester moiety, with the proviso that when X′ is a hydroxyl group Y′ must be a carboxylic acid ester moiety and when Y′ is a hydroxyl group X′ must be a carboxylic acid ester moiety, (ii) a component having an α-diester moiety wherein X′ and Y′ are both carboxylic acid ester moieties, and (iii) a component having an α-glycol moiety wherein X′ and Y′ are both hydroxyl.  
     
     
         26 . The epoxy resin of  claim 25  wherein the percentages of α-hydroxy ester moieties, α-diester moieties and α-glycol moieties in Component (A) are 5 to 100 percent, 0 to 95 percent and 0 to 95 percent, respectively.  
     
     
         27 . The epoxy resin of  claim 26  wherein the percentages of α-hydroxy ester moieties, α-diester moieties and α-glycol moieties in Component (A) are 15 to 100 percent, 0 to 85 percent and 0 to 85 percent, respectively.  
     
     
         28 . The epoxy resin of  claim 27  wherein the percentages of α-hydroxy ester moieties, α-diester moieties and α-glycol moieties in Component (A) are 30 to 100 percent, 0 to 70 percent and 0 to 70 percent, respectively.  
     
     
         29 . The epoxy resin of  claim 16  wherein the α-hydroxy ester derivative of at least one or more phenols is formed by reacting (1) at least one or more phenols with (2) a glycidyl ester or a substituted glycidyl ester.  
     
     
         30 . The epoxy resin of  claim 29  wherein Component (1), the one or more phenols, comprises a structure represented by the following Formula XI:  
       Formula XI  
       (R 2 ) y Ar(OH) z    
       wherein y is 0 to 750; z is 1 to 150; Ar is an aromatic-containing moiety; and R 2  is a group substituted for a hydrogen atom on the Ar moiety.  
     
     
         31 . The epoxy resin of  claim 30  wherein Component (1), the one or more phenols, comprises a structure represented by any one or more of Formulas XII-XV as follows:  
       
         
           
           
               
               
           
         
       
       wherein y is 0 to 5, and each y can be the same or different; z is 1 to 4, and each z can be the same or different; and R 2  is a group substituted for a hydrogen atom on the aromatic ring;  
       
         
           
           
               
               
           
         
       
       wherein y is 0 to 4, and each y can be he same or different; z is 1 to 3, and each z can be the same or different; R 2  is a group substituted for a hydrogen atom on the aromatic ring; and Z is (i) nil, (ii) a heteroatom with or without substituents thereon to complete its necessary bonding valence, (iii) —C(O)—, (iv) —S(O 2 )—, (v) —C(O)NH—, (vi) —P(O)Ar′, (vii) an organic aliphatic or cycloaliphatic moiety, saturated or unsaturated, with or without heteroatoms, or (viii) a partially or fully fluorinated organic aliphatic or cycloaliphatic moiety;  
       
         
           
           
               
               
           
         
       
       wherein y is 0 to 4, and each y can be the same or different; z is 1 to 3, and each z can be the same or different; R 2  is a group substituted for a hydrogen atom on the aromatic ring; Z is (i) nil, (ii) a heteroatom with or without substituents thereon to complete its necessary bonding valence, (iii) —C(O)—,(iv) —S(O 2 )—, (v) —C(O)NH—, (vi) —P(O)Ar—, (vii) an organic aliphatic or cycloaliphatic moiety, saturated or unsaturated, with or without heteroatoms, or (viii) a partially or fully fluorinated organic aliphatic moiety; and m is from 0.001 to 10; or  
       
         
           
           
               
               
           
         
       
       wherein y is 0 to 4, and each y can be the same or different; z is 1 to 3, and each z can be the same or different; R 2  is a group substituted for a hydrogen atom on the aromatic ring; Z′ (i) is an organic aliphatic moiety, saturated or unsaturated, with or without heteroatoms, wherein the aliphatic moiety has from 1 to 20 carbon atoms, (ii) a cycloaliphatic moiety, saturated or unsaturated, with or without heteroatoms, having from 3 to 20 carbon atoms, (iii) an aromatic moiety, with or without heteroatoms, having 6 to 20 carbon atoms, (iv) a partially or fully fluorinated organic aliphatic, cycloaliphatic or aromatic moiety, or (v) any combination thereof; and m′ is 3 or 4.  
     
     
         32 . The epoxy resin of  claim 29  wherein Component (2), the glycidyl ester or substituted glycidyl ester, comprises a structure represented by the following Formula XVI:  
       
         
           
           
               
               
           
         
       
       wherein R 4  is hydrogen, an alkyl group having from 1 to 20 carbon atoms, an alkenyl group having from 2 to 20 carbon atoms, a cycloaliphatic group having from 3 to 20 carbon atoms, or an aromatic group having from 6 to 20 carbon atoms; and R 5  is a glycidyl moiety.  
     
     
         33 . The epoxy resin of  claim 32  wherein R 5  is selected from:  
       
         
           
           
               
               
           
         
       
       wherein R 3  is hydrogen, an alkyl group having from 1 to 20 carbon atoms, a cycloaliphatic group having from 3 to 20 carbon atoms, an aromatic group having from 6 to 20 carbon atoms, or any combination thereof.  
     
     
         34 . The epoxy resin of  claim 33  wherein R 5  is selected from:  
       
         
           
           
               
               
           
         
       
     
     
         35 . The epoxy resin of  claim 34  wherein Component (2), the glycidyl ester or substituted glycidyl ester, is selected from glycidyl formate, glycidyl acetate, methylglycidyl formate and methylglycidyl acetate.  
     
     
         36 . The epoxy resin of  claim 35  wherein Component (2), the glycidyl ester, is glycidyl acetate.  
     
     
         37 . The epoxy resin of  claim 29  wherein the amount of glycidyl ester or substituted glycidyl ester reacted with at least one or more phenols is from about 0.5 equivalents to about 50 equivalents of glycidyl ester or substituted glycidyl ester per one equivalent of phenolic hydroxyl.  
     
     
         38 . The epoxy resin of  claim 29  wherein the reaction of preparing the α-hydroxy ester derivative is carried out in the presence of a solvent.  
     
     
         39 . The epoxy resin of  claim 29  wherein the reaction of preparing the α-hydroxy ester derivative is carried out in the presence of a catalyst.  
     
     
         40 . The epoxy resin of  claim 39  wherein the catalyst is a phase transfer catalyst.  
     
     
         41 . The epoxy resin of  claim 40  wherein the catalyst is an organopnicogen-containing catalyst.  
     
     
         42 . The epoxy resin of  claim 41  wherein the catalyst is homogeneous or heterogeneous.  
     
     
         43 . The epoxy resin of  claim 42  wherein the catalyst is from about 0.001 percent to about 1000 percent by weight based on the amount of the phenol or mixture of phenols used in the reaction.  
     
     
         44 . The epoxy resin of  claim 29  wherein the reaction of preparing the α-hydroxy ester derivative is carried out at a temperature of from about 10° C. to about 160° C.  
     
     
         45 . The epoxy resin of  claim 16  wherein the α-halohydrin intermediate of at least one or more phenols comprises a structure represented by the following Formula I:  
       Formula I  
       (R 2 ) y Ar(OR 1 ) z    
       wherein y is from 0 to 750; z is from 1 to 150; Ar is an aromatic-containing moiety; R 1  is an α-halohydrin propyl-containing moiety; and R 2  is a group substituted for a hydrogen atom on the Ar moiety.  
     
     
         46 . The epoxy resin of  claim 45  wherein the α-halohydrin intermediate of at least one or more phenols comprises a structure represented by any one or more of the following Formulas II-V:  
       
         
           
           
               
               
           
         
       
       wherein y is 0 to 5; z is 1 to 4; R 1  is an α-halohydrin propyl-containing moiety; and R 2  is a group substituted for a hydrogen atom on the Ar moiety;  
       
         
           
           
               
               
           
         
       
       wherein y is 0 to 4, and each y can be the same or different; z is 1 to 3, and each z can be the same or different; R 1  is an α-halohydrin propyl-containing moiety; R 2  is a group substituted for a hydrogen atom on the aromatic ring; and z is (i) nil, (ii) a heteroatom with or without substituents thereon to complete its necessary bonding valence, (iii) —C(O)—,(iv) —S(O 2 )—, (v) —C(O)NH—, (vi) —P(O)Ar—, (vii) an organic aliphatic or cycloaliphatic moiety, saturated or unsaturated, with or without heteroatoms, or (viii) a partially or fully fluorinated organic aliphatic or cycloaliphatic moiety;  
       
         
           
           
               
               
           
         
       
       wherein y is 0 to 4, and each y can be the same or different; z is 1 to 3, and each z can be the same or different; R 1  is an α-halohydrin propyl-containing moiety; R 2  is a group substituted for a hydrogen atom on the aromatic ring, Z is (i) nil, (ii) a heteroatom with or without substituents thereon to complete its necessary bonding valence, (iii) —C(O)—, (iv) —S(O 2 )—, (v) —C(O)NH—, (vi) —P(O)Ar—, (vii) an organic aliphatic or cycloaliphatic moiety, saturated or unsaturated, with or without heteroatoms, or (viii) a partially or fully fluorinated organic aliphatic or cycloaliphatic moiety; and m is from 0.001 to 10; or  
       
         
           
           
               
               
           
         
       
       wherein y is 0 to 4, and each y can be the same or different; z is 1 to 3, and each z can be the same or different; R 1  is an α-halohydrin propyl-containing moiety; R 2  is a group substituted for a hydrogen atom on the aromatic ring; Z′ is (i) an organic aliphatic moiety, saturated or unsaturated, with or without heteroatoms, wherein the aliphatic moiety has from 1 to 20 carbon atoms, (ii) a cycloaliphatic moiety, saturated or unsaturated, with or without heteroatoms, having from 3 to 20 carbon atoms, (iii) an aromatic moiety, with or without heteroatoms, having 6 to 20 carbon atoms, (iv) a partially or fully fluorinated organic aliphatic, cycloaliphatic or aromatic moiety, or (v) any combination thereof; and m′ is 3 or 4.  
     
     
         47 . The epoxy resin of  claim 46  wherein R 1  is selected from:  
       
         
           
           
               
               
           
         
       
       wherein X and Y may be a halogen atom or hydroxyl group with the proviso that when X is a halogen Y must be a hydroxyl and when Y is a halogen X must be a hydroxyl; and R 3  is hydrogen, an alkyl group having from 1 to 20 carbon atoms, a cycloaliphatic group having from 3 to 20 carbon atoms, an aromatic group having from 6 to 20 carbon atoms, or any combination thereof.  
     
     
         48 . The epoxy resin of  claim 47  wherein R 1  is selected from:  
       
         
           
           
               
               
           
         
       
       wherein X and Y may be a halogen atom or hydroxyl group with the proviso that when X is a halogen Y must be a hydroxyl and when Y is a halogen X must be a hydroxyl.  
     
     
         49 . The epoxy resin of  claim 46  wherein the α-chlorohydrin intermediate of at least one or more phenols is selected from the group comprising 1,3-dihydroxybenzene bis(3-chloro-2-hydroxypropyl) ether; 1,4-dihydroxybenzene bis(3-chloro-2-hydroxypropyl) ether; 1,5-dihydroxynaphthalene bis(3-chloro-2-hydroxypropyl) ether; 2,6-dihydroxynaphthalene bis(3-chloro-2-hydroxypropyl) ether; 4,4′-dihydroxybiphenyl-bis(3-chloro-2-hydroxypropyl) ether; 3,3′,5,5′-tetramethyl-4,4′-dihydroxybiphenyl bis(3-chloro-2-hydroxypropyl) ether; 3,3′,5,5′-tetramethyl-2,2′,6,6′-tetrabromo-4,4′-dihydroxybiphenyl bis(3-chloro-2-hydroxypropyl) ether; bis(4-hydroxyphenyl)methane-bis(3-chloro-2-hydroxypropyl) ether; 2,2-bis(4-hydroxyphenyl)isopropylidene bis(3-chloro-2-hydroxypropyl) ether; phenol-formaldehyde novolac (3-chloro-2-hydroxypropyl) ether (functionality greater than 2); o-cresol-formaldehyde novolac (3-chloro-2-hydroxypropyl) ether (functionality greater than 2); phenol-dicyclopentadienyl novolac (3-chloro-2-hydroxypropyl) ether (functionality greater than 2); naphthol-formaldehyde novolac (3-chloro-2-hydroxypropyl) ether (functionality greater than 2); 1,1,1-tris(4-hydroxyphenyl)methane tris(3-chloro-2-hydroxypropyl) ether; 1,1,2,2-tetrakis(4-hydroxyphenyl)ethane tetrakis(3-chloro-2-hydroxypropyl) ether; 1,3-dihydroxybenzene bis(2-chloro-3-hydroxypropyl) ether; 1,4-dihydroxybenzene bis(2-chloro-3-hydroxypropyl) ether; 1,5-dihydroxynaphthalene bis(2-chloro-3-hydroxypropyl) ether; 2,6-dihydroxynaphthalene bis(2-chloro-3-hydroxypropyl) ether; 4,4′-dihydroxybiphenyl bis(2-chloro-3-hydroxypropyl) ether; 3,3′,5,5′-tetramethyl-4,4′-dihydroxybiphenyl bis(2-chloro-3-hydroxypropyl) ether; 3,3′,5,5′-tetramethyl-2,2′,6,6′-tetrabromo-4,4′-dihydroxybiphenyl bis(2-chloro-3-hydroxypropyl) ether; bis(4-hydroxyphenyl)methane bis(2-chloro-3-hydroxypropyl) ether; 2,2-bis(4-hydroxyphenyl)isopropylidene bis(2-chloro-3-hydroxypropyl) ether; phenol-formaldehyde novolac (2-chloro-3-hydroxypropyl) ether (functionality greater than 2); o-cresol-formaldehyde novolac (2-chloro-3-hydroxypropyl) ether (functionality greater than 2); phenol-dicyclopentadienyl novolac (2-chloro-3-hydroxypropyl) ether (functionality greater than 2); naphthol-formaldehyde novolac (2-chloro-3-hydroxypropyl) ether (functionality greater than 2); 1,1,1-tris(4-hydroxyphenyl)methane tris(2-chloro-3-hydroxypropyl) ether; 1,1,2,2-tetrakis(4-hydroxyphenyl)ethane tetrakis(2-chloro-3-hydroxypropyl) ether; and mixtures thereof.  
     
     
         50 . The epoxy resin of  claim 49  wherein the α-chlorohydrin intermediate of at least one or more phenols is selected from the group comprising 2,2-bis(4-hydroxyphenyl)isopropylidene bis(3-chloro-2-hydroxypropyl) ether; 2,2-bis(4-hydroxyphenyl)isopropylidene bis(2-chloro-3-hydroxypropyl) ether; and mixtures thereof.  
     
     
         51 . The epoxy resin of  claim 45  wherein the α-halohydrin intermediate of at least one or more phenols comprising a structure represented by Formula I is present in an amount of from about 10 to less than about 100 percent by weight.  
     
     
         52 . The epoxy resin of  claim 51  wherein the α-halohydrin intermediate of at least one or more phenols comprising a structure represented by Formula I is present in an amount of from about 25 to less than about 100 percent by weight.  
     
     
         53 . The epoxy resin of  claim 52  wherein the α-halohydrin intermediate of at least one or more phenols comprising a structure represented by Formula I is present in an amount of from about 50 to about 100 percent by weight.  
     
     
         54 . The epoxy resin of  claim 9  comprising at least two or more components wherein at least one of the components is an epoxy resin product as claimed in  claim 9 .  
     
     
         55 . The epoxy resin of  claim 54  wherein the epoxy resin product comprising a structure represented by Formula XVIII is present in an amount of from about 10 to about 100 percent by weight.  
     
     
         56 . The epoxy resin of  claim 55  wherein the epoxy resin product comprising a structure represented by Formula XVIII is present in an amount of from about 25 to about 100 percent by weight.  
     
     
         57 . The epoxy resin of  claim 56  wherein the epoxy resin product comprising a structure represented by Formula XVIII is present in an amount of from about 50 to about 100 percent by weight.