Phosphorus Containing Compounds Useful for Making Halogen-Free, Ignition-Resistant Polymer

Abstract

Phosphorus-containing compounds are disclosed which are obtainable by reacting: (A) at least one organophosphorus compound having a group selected from the group H—P═O; the group P—H and the group P—OH; and (B) at least one compound having the following Formula (I): [R′(Y) m′ ] m (X—O—R″) n   Formula (I) wherein R′ is an organic group; Y is a functional group selected from hydroxy, carboxylic acid, carboxylate, acid anhydride, and amine; —SH, —SO 3 H, —CONH 2 , —NHCOOR, phosphite and phosphinate groups X is a hydrocarbylene group; R″ is hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms, R is alkyl or aryl group having from 1 to 12 carbon atoms; m′, m and n are, independently, numbers equal to or greater than 1. These compounds are useful for making flame retardant epoxy and polyurethane resins and ignition resistant thermoplastic resins, each of which is useful for a variety of end uses requiring flame retardancy or ignition resistance. Flame retardant epoxy resins may be used to make electrical laminates. Flame retardant polyurethane is useful for making rigid polyurethane foam used in construction and flexible polyurethane foam used to make vehicle upholstery. Ignition resistant thermoplastic resins are useful for making television cabinets, computer monitors, printer housings, automotive parts, and housings and parts for appliances. This invention is particularly useful in end use applications in which a low bromine or low halogen content is required or desired.

1 . A process for making a phosphorus-containing compound comprising reacting: 
 (A) at least one organophosphorus compound having a group selected from the group H—P═O, the group P—H and the group P—OH; and    (B) at least one compound having the following Formula (I):      [R′(Y) m′ ] m (X—O—R″) n    Formula (I)  wherein    R′ is an organic group;      Y is a functional group selected from hydroxy, carboxylic acid, carboxylate, acid anhydride, amine, —SH, —SO 3 H, —CONH 2 , —NHCOOR phosphinate and phosphate; 
 X is a hydrocarbylene group;  
 R″ is a hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms, R is alkyl or aryl group having from 1 to 12 carbon atoms; and  
 m′, m and n are, independently, numbers equal to or greater than 1.  
   
     
     
         2 . The process according to  claim 1 , wherein R′ of Formula (I) comprises at least one arylene group and n is at least 2.  
     
     
         3 . The process of  claim 1 , wherein R′ of Formula (I) comprises at least two arylene groups linked to each other by one or more hydrocarbylene or hydrocarbylene ether groups and m is at least 2.  
     
     
         4 . The process of  claim 2 , wherein the arylene groups are phenyl groups, each hydrocarbylene is a methylene group, and each hydrocarbylene ether is a methylene oxy group.  
     
     
         5 . The process of  claim 1 , wherein Y is hydroxy; and wherein R″ is a hydrogen, methyl, ethyl, propyl, or butyl group.  
     
     
         6 . The process of  claim 1 , wherein the compound of Formula (I), Component (B), is represented by the following Formula (II) or Formula (III):  
         [Ar(Y) m′ —X′][Ar(Y) m′ —X] b (X—O—R″)n   Formula (II)  (R″—O—X) c [Ar(Y) m′ —X—O—X] a [Ar(Y) m′ —X] b [Ar(Y) m′ ] b′ (X—O—R″) d    Formula (III)  
       wherein each “Ar” independently represents an aromatic group optionally substituted with one or more alkyl groups having 1 to 4 carbon atoms; 
 Y is a functional group selected from hydroxy, carboxylic acid, carboxylate, acid anhydride, amine, —SH, —SO 3 H, —CONH 2 , —NHCOOR, phosphinate and phosphate;  
 X is a hydrocarbylene group;  
 R″ is hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms, R is alkyl or aryl group having from 1 to 12 carbon atoms; and 
 each R″—O—X— is bonded directly to an Ar group; subscripts a, b, b′, c and d each independently represent a number equal to or greater than zero; and each unit with the subscripts a, b, b′, c and d is bonded directly to an Ar group of another unit in Formula (II) or Formula (III), which has the same or different unit formula; and m′, m, n are, independently, a number equal to or greater than 1.  
 
 
     
     
         7 . The process of  claim 1  wherein the compound of Formula (I), Component (B), is represented by the following Formula (IV): 
 Formula (IV)                          wherein each Ar independently represents an aromatic group optionally substituted with one or more alkyl groups having 1 to 4 carbon atoms;    Y is a functional group selected from hydroxy, carboxylic acid, carboxylate, acid anhydride, amine, —SH, —SO 3 H, —CONH 2 , —NHCOOR, phosphinate and phosphate;    X is a hydrocarbylene group;    R″ is hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms, R is alkyl or aryl group having from 1 to 12 carbon atoms; and    each R″—O—X— is bonded directly to an Ar group; e is an integer from 0 to 4, f is 1 or greater and m′ is 1 or greater; and a, b, c and d each, independently, represent a number equal to or greater than zero.    
     
     
         8 . The process of  claim 1  wherein the compound of Formula (I), Component (B), is represented by the following Formula (V) or Formula (VI):  
       
         
           
           
               
               
           
         
         wherein R1 each independently is hydrogen or an alkyl group having from 1 to 10 carbon atoms;  
         Y is a functional group selected from hydroxy, carboxylic acid, carboxylate, acid anhydride, amine, —SH, —SO 3 H, —CONH 2 , —NHCOOR, phosphinate and phosphate;  
         X is a hydrocarbylene group;  
         R″ is a hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms;  
         R is alkyl or aryl group having from 1 to 12 carbon atoms  
         p each independently represents a number from zero to 4; and  
         a and b each independently represent a number equal to or greater than zero.  
       
     
     
         9 . The process of  claim 1 , wherein the compound of Formula (I), Component (B), is a compound having the following chemical Formula (VII):  
       
         
           
           
               
               
           
         
         wherein R2 each independently is hydrogen, an alkyl group having from 1 to 10 carbon atoms, CH 2 OH, or CH2OR″;  
         R1 each independently is hydrogen or an alkyl group having from 1 to 10 carbon atoms;  
         R″ is a hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms; and  
         b represents a number equal to or greater than zero; or wherein the compound of Formula (I), Component (B), is a compound having the following chemical Formula (VIII) or Formula (VIIIa):  
         
           
             
             
                 
                 
             
           
         
         wherein R2 each independently is hydrogen, an alkyl group having from 1 to 10 carbon atoms, CH 2 OH, or CH 2 OR″;  
         R1 each independently is hydrogen or an alkyl group having from 1 to 10 carbon atoms;  
         R″ is a hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms; and  
         a represents a number equal to or greater than zero; or wherein the compound of Formula (I), Component (B), is a compound having the following chemical Formula (IX) or Formula (IXa):  
         
           
             
             
                 
                 
             
           
         
         wherein R″ is a hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms;  
         c represents a number equal to or greater than zero; and  
         p represents a number equal to or greater than zero.  
       
     
     
         10 . The process of  claim 1 , wherein the compound of Formula (I), Component (B), is a ethyl, propyl, butyl or methyl etherified phenol formaldehyde condensation product, a ethyl, propyl, butyl or methyl etherified cresol formaldehyde, a ethyl, propyl, butoxy or methoxy methylated phenol novolac or a resole compound.  
     
     
         11 . The process of  claim 1 , wherein the organophosphorus compound, Component (A), is a compound represented by one of following Formulas (X) through (XXII):  
       
         
           
           
               
               
           
         
         wherein in Formulae (X) to (XIII), R A  and R B  may be the same or different and are selected from substituted or unsubstituted aryl or aryloxy groups and hydroxyl groups provided that not more than one of R A  and R B  is a hydroxyl group, and R C  and R D  may be the same or different and are selected from hydrocarbylene and hydrocarbenylene; or  
         
           
             
                   
                   
                   
                 
                       
                       
                   
                       
                       
                   
                       
                     Formula (XIV) 
                     R A PH 2   
                   
                       
                     Formula (XV) 
                     (R A O) 2 P(O)H 
                   
                       
                     Formula (XVI) 
                     R A P(O)(OH)H 
                   
                       
                     Formula (XVII) 
                     R A P(O)(OH) 2   
                   
                       
                     Formula (XVIII) 
                     R A R B P(O)OH 
                   
                       
                     Formula (XIX) 
                     (R A O) 2 P(O)H 
                   
                       
                     Formula (XXI) 
                     (R A ) 2 P(O)H 
                   
                       
                     Formula (XXII) 
                     R A P(O)(OH)H 
                   
                       
                     Formula (XXI) 
                     R A P(O)(OH) 2   
                   
                       
                       
                   
                       
                       
                   
               
                  
                  
                 
                 
                  
                  
                  
                  
                  
                  
                  
                  
                  
                  
                  
                 
              
             
           
         
         wherein in Formulae (XIV) to (XXI), R A  and R B  may be the same or different and are selected from substituted or unsubstituted aryl or aryloxy groups.  
       
     
     
         12 . The process according to  claim 11 , wherein R C  and R D  of Formula (XI) are each an arylene group.  
     
     
         13 . The process of  claim 1 , wherein the organophosphorus compound, Component (A), is phenylphosphine, diphenyl phosphate, diethyl phosphate, dimethylphosphite, phenylphosphinic acid, phenylphosphonic acid, dimethylphosphinic acid, or mixtures thereof.  
     
     
         14 . The process according to  claim 1 , wherein the organophosphorus compound is 9,10-dihydro-9-oxa-10-phosphananthrene 10-oxide.  
     
     
         15 . A process for making a curable phosphorus-containing composition comprising blending: 
 (I) a phosphorus-containing compound comprising the reaction product of: 
 (A) at least one organophosphorus compound having a group selected from the group H—P═O, the group P—H and the group P—OH; and  
 (B) at least one compound having the following Formula (I):  
   [R(Y) m′ ] m (X—O—R″) n    Formula (I)  
 wherein  
 R 1  is an organic group;  
 Y is a functional group selected from hydroxy, carboxylic acid, carboxylate, acid anhydride, amine, —SH, —SO 3 H, —CONH 2 , —NHCOOR, phosphinate and phosphate;  
 X is a hydrocarbylene group;  
 R″ is hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms, R is alkyl or aryl group having from 1 to 12 carbon atoms; and  
 m′, m and n are, independently, numbers equal to or greater than 1; and  
   (II) a thermosetting composition.    
     
     
         16 . The process of  claim 15  wherein the thermosetting composition, Component (II), contains an epoxy resin; a polyisocyanate resin; a polymerizable unsaturated compound; a benzoxazine-containing compound or a polybenzoxazine-containing compound; bismaleimide, triazines, or a blend of bismaleimide and triazine compounds; or an epoxy and at least one co-curing agent.  
     
     
         17 . The process of  claim 16  wherein the polymerizable unsaturated compounds are selected from the group consisting of vinylesters, acrylates, cyanate esters, and cyanamides.  
     
     
         18 . The process of  claim 16  wherein the co-curing agent is a compound which reacts with an epoxy group.  
     
     
         19 . The process of  claim 18  wherein the co-curing agent is a hydroxyl, an acid, an acid anhydride, a phenolic compound, a nitrogen-containing compound, a compound which generates a reactive group at an elevated temperature, or mixture thereof.  
     
     
         20 . The process of  claim 19  wherein the phenolic compound is a phenol novolac, a cresol novolac, a bisphenol A novolac, a phenol novolac of dicyclopentadiene, a polybenzoxazine generated from a benzoxazine ring-containing compound or mixtures thereof.  
     
     
         21 . The process of  claim 19  wherein the acid anhydride is a maleic acid anhydride, a phthalic acid anhydride, methylhexahydrophthalic acid anhydride, a styrene-maleic acid anhydride copolymer, or mixtures thereof.  
     
     
         22 . The process of  claim 19  wherein the nitrogen-containing curing agent is a mono or polyamine; a polyamide; dicyandiamide; sulfanilamide; a primary, a secondary or a tertiary amine; imidazoles; 2-methylimidaole; 2-ethyl, 4-methyl imidazole; 2-phenylimidazole; benziimidazole; diaminodiphenylmethane; diaminodiphenylsulfone; or mixtures thereof.  
     
     
         23 . A process for making a phosphorus-containing composition comprising blending: 
 (I) a phosphorus-containing compound comprising the reaction product of: 
 (A) at least one organophosphorus compound having a group selected from the group H—P═O, the group P—H and the group P—OH; and  
 (B) at least one compound having the following Formula (I):  
   [R′(Y) m′ ] m (X—O—R″) n    Formula (I)  
 wherein  
 R′ is an organic group;  
 Y is a functional group selected from hydroxy, carboxylic acid, carboxylate, acid anhydride, amine, —SH, —SO 3 H, —CONH 2 , —NHCOOR, phospinate and phosphate;  
 X is a hydrocarbylene group;  
 R″ is hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms, R is alkyl or aryl group having from 1 to 12 carbon atoms; and  
 m′, m and n are, independently, numbers equal to or greater than 1; and  
   (III) a thermoplastic.    
     
     
         24 . The process of  claim 23  wherein the thermoplastic, Component (III), is selected from the group consisting of polycarbonate, polystyrene, polypropylene, polyethylene, polyphenylene oxide resins or a mixture thereof.  
     
     
         25 . A process for making a curable phosphorus-containing composition comprising blending: 
 (I) a phosphorus-containing compound comprising the reaction product of: 
 (A) at least one organophosphorus compound having a group selected from the group H—P═O, the group P—H and the group P—OH; and  
 (B) at least one compound having the following Formula (I):  
   [R′(Y) m′ ] m (X—O—R″) n    Formula (V)  
 wherein  
 R′ is an organic group;  
 Y is a functional group selected from hydroxy, carboxylic acid, carboxylate, acid anhydride, amine, —SH, —SO 3 H, —CONH 2 , —NHCOOR, phospinate and phosphate;  
 X is a hydrocarbylene group;  
 R″ is hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms, R is alkyl or aryl group having from 1 to 12 carbon atoms; and  
 m′, m and n are, independently, numbers equal to or greater than 1;  
   (II) a thermosetting composition; and    (III) a thermoplastic.    
     
     
         26 . A process for making a phosphorus-containing epoxy resin compound comprising reacting: 
 (I) a phosphorus-containing compound comprising the reaction product of: 
 (A) at least one organophosphorus compound having a group selected from the group H—P═O, the group P—H, and the group P—OH; and  
 (B) at least one compound having the following Formula (I):  
   [R′(Y) m′ ] m (X—O—R″) n    Formula (I)  
 wherein  
 R′ is an organic group;  
 Y is a functional group selected from hydroxy, carboxylic acid, carboxylate, acid anhydride, amine, —SH, —SO 3 H, —CONH 2 , —NHCOOR, phospinate and phosphite  
 X is a hydrocarbylene group;  
 R″ is hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms, R is alkyl or aryl group having from 1 to 12 carbon atoms; and  
 m′, m and n are, independently, numbers equal to or greater than 1; and  
   (IV) at least one epoxy resin.    
     
     
         27 . A process for making a curable phosphorus-containing epoxy resin composition comprising blending: 
 (C) an epoxy resin compound comprising the reaction product of: 
 (I) a phosphorus-containing compound comprising the reaction product of: 
 (A) at least one organophosphorus compound having a group selected from the group H—P═O, the group P—H, and the group P—OH; and  
 (B) at least one compound having the following Formula (I):  
   [R′(Y) m′ ] m (X—O—R″) n    Formula (I)  
 wherein  
 R′ is an organic group;  
 Y is a functional group selected from hydroxy, carboxylic acid, carboxylate, acid anhydride, amine, —SH, —SO 3 H, —CONH 2 , —NHCOOR, phosphinate and phosphite;  
 X is a hydrocarbylene group;  
 R″ is hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms, R is alkyl or aryl group having from 1 to 12 carbon atoms; and  
 m′, m and n are, independently, numbers equal to or greater than 1; and  
 
 (IV) at least one epoxy resin; and  
   (D) at least one curing agent.    
     
     
         28 . The process of  claim 27  including an additional epoxy resin other than the epoxy compound of Component (C).  
     
     
         29 . A process for making a curable phosphorus-containing epoxy resin composition comprising blending: 
 (I) a phosphorus-containing compound comprising the reaction product of: 
 (A) at least one organophosphorus compound having a group selected from the group H—P═O, the group P—H, and the group P—OH; and  
 (B) at least one compound having the following Formula (I):  
   [R′(Y) m′ ] m (X—O—R) n    Formula (I)  
 wherein  
 R′ is an organic group;  
 Y is a functional group selected from hydroxy, carboxylic acid, carboxylate, acid anhydride, amine, —SH, —SO 3 H, —CONH 2 , —NHCOOR, phosphinate and phosphate;  
 X is a hydrocarbylene group;  
 R″ is hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms, R is alkyl or aryl group having from 1 to 12 carbon atoms; and  
 m′, m and n are, independently, numbers equal to or greater than 1; and  
   (IV) at least one epoxy resin.    
     
     
         30 . A process for making a phosphorus-containing, benzoxazine ring-containing compound comprising reacting: 
 (I) a phosphorus-containing compound comprising the reaction product of: 
 (A) at least one organophosphorus compound having a group selected from the group H—P═O, the group P—H, and the group P—OH; and  
 (B) at least one compound having the following Formula (V):  
   [R′(Y) m′ ] m (X—O—R″) n    Formula (I)  
 wherein  
 R′ is an organic group;  
 Y is a hydroxy functional group or an amine functional group;  
 X is a hydrocarbylene group;  
 R″ is hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms, R is alkyl or aryl group having from 1 to 12 carbon atoms; and  
 m′, m and n are, independently, numbers equal to or greater than 1;  
   (V) at least one amine compound when the Y functional group of Component (B) is a hydroxyl or at least one hydroxyl group-containing compound when the Y functional group of Component (B) is an amine; and    (VI) an aldehyde compound.    
     
     
         31 . The process of  claim 30  wherein the aldehyde is formaldehyde, para-formaldehyde or other aldehydes having the general formula RCHO, where R is alkyl or aryl group having from 1 to 12 carbon atoms.  
     
     
         32 . A process for making a curable phosphorus-containing, benzoxazine ring-containing resin composition comprising blending: 
 (E) a benzoxazine ring-containing compound comprising the reaction product of: 
 (I) a phosphorus-containing compound comprising the reaction product of: 
 (A) at least one organophosphorus compound having a group selected from the group H—P═O, the group P—H, and the group P—OH; and  
 (B) at least one compound having the following Formula (I):  
   [R′(Y) m′ ] m (X—O—R″) n    Formula (I)  
 wherein  
 R′ is an organic group;  
 Y is a hydroxy functional group or an amine functional group;  
 X is a hydrocarbylene group;  
 R″ is hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms; and  
 m′, m and n are, independently, numbers equal to or greater than 1; and  
 (V) at least one amine compound when the Y functional group of Component (B) is a hydroxyl or at least one hydroxyl group-containing compound when the Y functional group of Component (B) is an amine; and  
 (VI) an aldehyde compound; and  
 
   (F) a thermosetting composition.    
     
     
         33 . A process for making a curable phosphorus-containing, benzoxazine ring- containing resin composition comprising blending: 
 (E) a benzoxazine ring-containing compound comprising the reaction product of: 
 (I) a phosphorus-containing compound comprising the reaction product of: 
 (A) at least one organophosphorus compound having a group selected from the group H—P═O, the group P—H, and the group P—OH; and  
 (B) at least one compound having the following Formula (I):  
   R′(Y) m′ ] m (X—O—R″) n    Formula (I)  
 wherein  
 R′ is an organic group;  
 Y is a hydroxy functional group or an amine functional group;  
 X is a hydrocarbylene group;  
 R″ is a hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms; and  
 m′, m and n are, independently, numbers equal to or greater than 1; and  
 (V) at least one amine compound when the Y functional group of Component (B) is a hydroxyl or at least one hydroxyl group-containing compound when the Y functional group of Component (B) is an amine; and  
 (VI) an aldehyde compound; and  
 
   (G) a thermoplastic.    
     
     
         34 . A process for making a phosphorus-containing, thermolabile group-containing compound comprising reacting: 
 (I) a phosphorus-containing compound comprising the reaction product of: 
 (A) at least one organophosphorus compound having a group selected from the group H—P═O, the group P—H, and the group P—OH; and  
 (B) at least one compound having the following Formula (I):  
   [R′(Y) m′ ] m (X—O—R″) n    Formula (I)  
 wherein  
 R′ is an organic group;  
 Y is a functional group selected from hydroxy, carboxylic acid, carboxylate, acid anhydride, and amine, —SH, —SO 3 H, —CONH 2 , —NHCOOR;  
 X is a hydrocarbylene group;  
 R″ is hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms, R is alkyl or aryl group having from 1 to 12 carbon atoms; and  
 m′, m and n are, independently, numbers equal to or greater than 1; and  
   (VII) at least one thermolabile group-containing compound.    
     
     
         35 . A process for making a curable phosphorus-containing, thermolabile resin composition comprising reacting: 
 (H) a thermolabile group-containing compound comprising the reaction product of: 
 (I) a phosphorus-containing compound comprising the reaction product of: 
 (A) at least one organophosphorus compound having a group selected from the group H—P═O, the group P—H and the group P—OH; and  
 (B) at least one compound having the following Formula (I):  
   [R′(Y) m′ ] m (X—O—R″) n    Formula (I)  
 wherein  
 R′ is an organic group;  
 Y is a functional group selected from hydroxy, carboxylic acid, carboxylate, acid anhydride, amine, —SH, —SO 3 H, —CONH 2 , —NHCOOR, phospinate and phosphite;  
 X is a hydrocarbylene group;  
 R″ is hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms, R is alkyl or aryl group having from 1 to 12 carbon atoms;  
 m′, m and n are, independently, numbers equal to or greater than 1; and  
 
 (VII) at least one thermolabile group-containing compound; and  
   (J) a thermosetting composition.    
     
     
         36 . The process of  claim 27 ,  claim 29 ,  claim 30 ,  claim 32 ,  claim 33 ,  claim 34  or  claim 35  including at least one epoxy resin; at least one curing agent; at least one catalyst; at least one inhibitor; or a thermoplastic material.  
     
     
         37 . The process of  claim 36  wherein the thermoplastic material is selected from the group consisting of a polycarbonate, a polystyrene, a polypropylene, a polyethylene, a polypropylene and a polyphenylene oxide resin mixture, and mixtures thereof.  
     
     
         38 . Any one of the preceding Claims wherein the epoxy resin is selected from group consisting of a phenol epoxy novolac, a cresol epoxy novolac, a polyoxazolidone ring containing epoxy resin, a bromine free epoxy resin; a brominated epoxy resin, or a phosphorus-containing epoxy resin.  
     
     
         39 . A phosphorus-containing compound comprising the reaction product of: 
 (A) at least one organophosphorus compound having a group selected from the group H—P═O, the group P—H and the group P—OH; and    (B) at least one compound having the following Formula (I):      [R′(Y) m′ ] m (X—O—R″) n    Formula (V)  wherein    R′ is an organic group;    Y is a functional group selected from hydroxy, carboxylic acid, carboxylate, acid anhydride, amine, —SH, —SO 3 H, —CONH 2 , —NHCOOR, phosphinate and phosphate;    X is a hydrocarbylene group;    R″ is hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms; and    m′, m and n are, independently, numbers equal to or greater than 1.      
     
     
         40 . A curable phosphorus-containing composition comprising: 
 (I) a phosphorus-containing compound comprising the reaction product of: 
 (A) at least one organophosphorus compound having a group selected from the group H—P═O, the group P—H and the group P—OH; and  
 (B) at least one compound having the following Formula (I):  
   [R′(Y) m′ ] m (X—O—R″) n    Formula (I)  
 wherein  
 R′ is an organic group;  
 Y is a functional group selected from hydroxy, carboxylic acid, carboxylate, acid anhydride, amine, —SH, —SO 3 H, —CONH 2 , —NHCOOR, phospinate and phosphate;  
 X is a hydrocarbylene group;  
 R″ is hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms, R is alkyl or aryl group having from 1 to 12 carbon atoms; and  
 m′, m and n are, independently, numbers equal to or greater than 1; and  
   (II) a thermosetting composition.    
     
     
         41 . The composition of  claim 40  wherein the thermosetting composition, Component (II), contains an epoxy resin; a polyisocyanate resin; polymerizable unsaturated compounds; a benzoxazine-containing compound or a polybenzoxazine-containing compound wherein the polybenzoxazine-containing compound is obtained from the polymerization of benzoxazine-containing compounds; bismaleimide, triazines, or a blend of bismaleimide and triazine compounds; or an epoxy and at least one co-curing agent.  
     
     
         42 . The composition of  claim 41  wherein the polymerizable unsaturated compound is selected from the group consisting of a double or triple bonds containing compounds.  
     
     
         43 . The composition of  claim 41  wherein the polymerizable unsaturated compound is selected from the group consisting of vinylesters, acrylates, cyanate esters, and cyanamides.  
     
     
         44 . The composition of  claim 41  wherein the co-curing agent is a compound which reacts with an epoxy group.  
     
     
         45 . The composition of  claim 44  wherein the curing agent is a hydroxyl, an acid, an acid anhydride, a phenolic compound, a nitrogen contain compound, or a compound which generates a reactive group at an elevated temperature, or mixtures thereof.  
     
     
         46 . The composition of  claim 45  wherein the phenolic compound is a phenol novolac, a cresol novolac, a bisphenol A novolac, a phenol novolac of dicyclopentadien, a polybenzoxazine generated from benzoxazine ring containing compounds, and mixtures thereof.  
     
     
         47 . The composition of  claim 45  wherein the acid anhydride is a maleic acid anhydride, a phthalic acid anhydride, methylhexahydrophthalic acid anhydride or a styrene-maleic acid anhydride copolymer.  
     
     
         48 . The composition of  claim 45  wherein the nitrogen-containing curing agent is a mono or polyamine; polyamide; dicyandiamide; a sulfanilamide; a primary, a secondary, or a tertial amine amine; imidazoles; 2-methylimidaole; 2-ethyl, 4-methyl imidazole; 2-phenylimidazole; benziimidazole; diaminodiphenylmethane; diaminodiphenylsulfone; or mixtures thereof.  
     
     
         49 . A phosphorus-containing composition comprising: 
 (I) a phosphorus-containing compound comprising the reaction product of: 
 (A) at least one organophosphorus compound having a group selected from the group H—P═O, the group P—H and the group P—OH; and  
 (B) at least one compound having the following Formula (I):  
   [R′(Y) m′ ] m (X—O—R″) n    Formula (I)  
 wherein  
 R′ is an organic group;  
 Y is a functional group selected from hydroxy, carboxylic acid, carboxylate, acid anhydride, amine, —SH, —SO 3 H, —CONH 2 , —NHCOOR, phospinate and phosphate;  
 X is a hydrocarbylene group;  
 R″ is hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms, R is alkyl or aryl group having from 1 to 12 carbon atoms; and  
 m′, m and n are, independently, numbers equal to or greater than 1; and  
   (III) a thermoplastic.    
     
     
         50 . The composition of  claim 49  wherein the thermoplastic, Component (III), is polycarbonate, polystyrene, polypropylene, polyethylene, a polypropylene, and polyphenylene oxide resin mixture or a mixture thereof.  
     
     
         51 . A curable phosphorus-containing composition comprising: 
 (I) a phosphorus-containing compound comprising the reaction product of: 
 (A) at least one organophosphorus compound having a group selected from the group H—P═O, the group P—H and the group P—OH; and  
 (B) at least one compound having the following Formula (I): 
   [R′(Y) m′ ] m (X—O—R″) n    Formula (I) 
 wherein  
 R′ is an organic group;  
 Y is a functional group selected from hydroxy, carboxylic acid, carboxylate, acid anhydride, amine, —SH, —SO 3 H, —CONH 2 , —NHCOOR, phospinate and phosphate;  
 X is a hydrocarbylene group;  
 R″ is hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms, R is alkyl or aryl group having from 1 to 12 carbon atoms; and  
 m′, m and n are, independently, numbers equal to or greater than 1;  
   (II) a thermosetting composition; and    (III) a thermoplastic.    
     
     
         52 . A phosphorus-containing epoxy resin compound comprising the reaction product of: 
 (I) a phosphorus-containing compound comprising the reaction product of: 
 (A) at least one organophosphorus compound having a group selected from the group H—P═O, the group P—H, and the group P—OH; and  
 (B) at least one compound having the following Formula (I):  
   [R′(Y) m′ ] m (X—O—R″) n    Formula (I)  
 wherein  
 R′ is an organic group;  
 Y is a functional group selected from hydroxy, carboxylic acid, carboxylate, acid anhydride, amine, —SH, —SO 3 H, —CONH 2 , —NHCOOR, phospinate and phosphate;  
 X is a hydrocarbylene group;  
 R″ is hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms, R is alkyl or aryl group having from 1 to 12 carbon atoms; and  
 m′, m and n are, independently, numbers equal to or greater than 1; and  
   (IV) at least one epoxy resin.    
     
     
         53 . A curable phosphorus-containing epoxy resin composition comprising: 
 (C) an epoxy resin compound comprising the reaction product of: 
 (I) a phosphorus-containing compound comprising the reaction product of: 
 (A) at least one organophosphorus compound having a group selected from the group H—P═O, the group P—H, and the group P—OH; and  
 (B) at least one compound having the following Formula (I):  
   [R′(Y) m′ ] m (X—O—R″) n    Formula (V)  
 wherein  
 R′ is an organic group;  
 Y is a functional group selected from hydroxy, carboxylic acid, carboxylate, acid anhydride, amine, —SH, —SO 3 H, —CONH 2 , —NHCOOR, phosphinate and phosphite;  
 X is a hydrocarbylene group;  
 R″ is hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms, R is alkyl or aryl group having from 1 to 12 carbon atoms; and  
 m′, m and n are, independently, numbers equal to or greater than 1; and  
 
 (IV) at least one epoxy resin; and  
   (D) at least one curing agent.    
     
     
         54 . The composition of  claim 53  including an additional epoxy resin other than the epoxy compound of Component (C).  
     
     
         55 . A curable phosphorus-containing epoxy resin composition comprising: 
 (I) a phosphorus-containing compound comprising the reaction product of: 
 (A) at least one organophosphorus compound having a group selected from the group H—P═O, the group P—H, and the group P—OH; and  
 (B) at least one compound having the following Formula (I):  
   [R′(Y) m′ ] m (X—O—R″) n    Formula (I)  
 wherein  
 R′ is an organic group;  
 Y is a functional group selected from hydroxy, carboxylic acid, carboxylate, acid anhydride, amine, —SH, —SO 3 H, —CONH 2 , —NHCOOR, phosphinate and phosphate;  
 X is a hydrocarbylene group;  
 R″ is hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms, R is alkyl or aryl group having from 1 to 12 carbon atoms; and  
 m′, m and n are, independently, numbers equal to or greater than 1; and  
   (IV) at least one epoxy resin.    
     
     
         56 . The composition of  claim 55  including a thermoplastic material.  
     
     
         57 . The composition of  claim 56  wherein the thermoplastic material is selected from the group consisting of a polycarbonate, a polystyrene, a polypropylene, a polyethylene, and a mixture of a polypropylene and a polyphenylene oxide resin, and mixtures thereof.  
     
     
         58 . A phosphorus-containing, benzoxazine ring-containing compound comprising the reaction product of: 
 (I) a phosphorus-containing compound comprising the reaction product of: 
 (A) at least one organophosphorus compound having a group selected from the group H—P═O, the group P—H, and the group P—OH; and  
 (B) at least one compound having the following Formula (I):  
   [R′(Y) m′ ] m (X—O—R″) n    Formula (I)  
 wherein  
 R′ is an organic group;  
 Y is a hydroxy functional group or an amine functional group;  
 X is a hydrocarbylene group;  
 R″ is hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms; and  
 m′, m and n are, independently, numbers equal to or greater than 1.  
   (V) at least one amine compound when the Y functional group of Component (B) is a hydroxyl or at least one hydroxyl group-containing compound when the Y functional group of Component (B) is an amine; and    (VI) an aldehyde compound.    
     
     
         59 . A curable phosphorus-containing, benzoxazine ring-containing resin composition comprising: 
 (E) a benzoxazine ring-containing compound comprising the reaction product of: 
 (I) a phosphorus-containing compound comprising the reaction product of: 
 (A) at least one organophosphorus compound having a group selected from the group H—P═O, the group P—H, and the group P—OH; and  
 (B) at least one compound having the following Formula (I):  
   [R′(Y) m′ ] m (X—O—R″) n    Formula (I)  
 wherein  
 R′ is an organic group;  
 Y is a hydroxy functional group or an amine functional group;  
 X is a hydrocarbylene group;  
 R″ is hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms; and  
 m′, m and n are, independently, numbers equal to or greater than 1; and  
 (V) at least one amine compound when the Y functional group of Component  
 (B) is a hydroxyl or at least one hydroxyl group-containing compound when the Y functional group of Component (B) is an amine; and  
 (VI) an aldehyde compound; and  
 
   (F) a thermosetting composition.    
     
     
         60 . A curable phosphorus-containing, benzoxazine ring-containing resin composition comprising: 
 (E) a benzoxazine ring-containing compound comprising the reaction product of: 
 (I) a phosphorus-containing compound comprising the reaction product of: 
 (A) at least one organophosphorus compound having a group selected from the group H—P═O, the group H—P, and the group P—OH; and  
 (B) at least one compound having the following Formula (I):  
   [R′(Y) m′ ] m (X—O—R″) n    Formula (I)  
 wherein  
 R′ is an organic group;  
 Y is a hydroxyl functional group or an amine functional group;  
 X is a hydrocarbylene group;  
 R″ is hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms; and  
 m′, m and n are, independently, numbers equal to or greater than 1; and  
 
 (V) at least one amine compound when the Y functional group of Component (B) is a hydroxyl or at least one hydroxyl group-containing compound when the Y functional group of Component (B) is an amine; and  
 (VI) at least one aldehyde compounds; and  
   (G) a thermoplastic.    
     
     
         61 . A phosphorus-containing, thermolabile group-containing compound comprising the reaction product of: 
 (I) a phosphorus-containing compound comprising the reaction product of: 
 (A) at least one organophosphorus compound having a group selected from the group H—P═O, the group P—H, and the group P—OH; and  
 (B) at least one compound having the following Formula (I):  
   [R′(Y) m′ ] m (X—O—R″) n    Formula (I)  
 wherein  
 R′ is an organic group;  
 Y is a functional group selected from hydroxy, carboxylic acid, carboxylate, acid anhydride, and amine,—SH, —SO 3 H, —CONH 2 , —NHCOOR;  
 X is a hydrocarbylene group;  
 R″ is hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms, R is alkyl or aryl group having from 1 to 12 carbon atoms; and  
 m′, m and n are, independently, numbers equal to or greater than 1; and  
   (VII) at least one thermolabile group-containing compound.    
     
     
         62 . A curable phosphorus-containing, thermolabile resin composition comprising: 
 (H) a thermolabile group containing compound comprising the reaction product of: 
 (I) a phosphorus-containing compound comprising the reaction product of: 
 (A) at least one organophosphorus compound having the a group selected from group H—P═O, the group P—H, and the group P—OH; and  
 (B) at least one compound having the following Formula (1):  
   [R′(Y) m′ ] m (X—O—R″) n    Formula (I)  
 wherein  
 R′ is an organic group;  
 Y is a functional group selected from hydroxy, carboxylic acid, carboxylate, acid anhydride, amine, —SH, —SO 3 H, —CONH 2 , —NHCOOR, phospinate and phosphite;  
 X is a hydrocarbylene group;  
 R″ is hydrogen or a hydrocarbyl group having from 1 to 8 carbon atoms, R is alkyl or aryl group having from 1 to 12 carbon atoms;  
 m′, m and n are, independently, numbers equal to or greater than 1; and  
 
 (VII) at least one thermolabile group-containing compound; and  
   (J) a thermosetting composition.    
     
     
         63 . The composition of  claim 55 ,  claim 57 ,  claim 58 ,  claim 59 ,  claim 60 ,  claim 61 , or  claim 62  including at least one epoxy resin; at least one curing agent; at least one co-curing agent; at least one catalyst; or at least one inhibitor.  
     
     
         64 . Any one of the preceding Claims wherein the epoxy resin is selected from group consisting of a phenol epoxy novolac, a cresol epoxy novolac, a polyoxazolidone ring containing epoxy resin, a bromine free epoxy resin, a brominated epoxy resin, or a phosphorous-containing epoxy resin.  
     
     
         65 . A product obtainable according to the process of  claim 1 , wherein the phosphorous content of the product is at least 4 weight-percent.  
     
     
         66 . The product of  claim 65 , wherein the organophosphorus compound, Component (A), is 9,10-dihydro-9-oxa-10-phosphananthrene 10-oxide.  
     
     
         67 . The product of any one of claims  65 , wherein the compound of Formula (I), Component is an etherified resole.  
     
     
         68 . The product of  claim 65 , wherein the R″ group is methyl, ethyl, propyl or butyl.  
     
     
         69 . An epoxy compound obtainable by reacting at least one product according to  claim 65  with at least one compound having more than one epoxy group per molecule.  
     
     
         70 . A curable flame resistant epoxy resin composition comprising at least one crosslinkable epoxy compound according to  claim 69 , at least one curing agent and, optionally, at least one crosslinkable epoxy resin other than the epoxy compound according to  claim 69 .  
     
     
         71 . An epoxy compound obtainable by epoxidizing the phenolic groups of the compound in  claim 65 .  
     
     
         72 . A curable ignition resistance curing composition comprising at least one crosslinkable epoxy or a mixture of different epoxy resins, a phosphorus-containing compound of  claim 65 , a crosslinker, a catalyst and optionally an inhibitor.  
     
     
         73 . The composition of  claim 72  wherein the inhibitor is a Lewis acid.  
     
     
         74 . The composition of  claim 73  wherein the Lewis acid is boric acid.  
     
     
         75 . A prepreg comprising at least one flame resistant epoxy resin composition according to  claim 72  and at least one reinforcing material.  
     
     
         76 . A laminate comprising at least one prepreg according to  claim 75  and at least one electron-conductive layer.  
     
     
         77 . A circuit board obtainable by curing a laminate according to  claim 76  wherein the electron-conductive layer comprises at least one circuit pattern.  
     
     
         78 . A polyol obtainable by reacting at least one product according to  claim 65  with at least one of ethylene oxide or propylene oxide  
     
     
         79 . A flame resistant polyurethane resin obtainable by reacting at least one polyol according to  claim 78  with at least one compound having more than one isocyanate group per molecule.  
     
     
         80 . An ignition resistant thermoplastic composition obtainable by blending the product according to  claim 65 , or a derivative thereof, with at least one thermoplastic resin or a mixture of thermoplastic resins.  
     
     
         81 . An ignition resistant thermoplastic/thermosetting hybrid composition obtainable by blending the product according to  claim 65  or a derivative thereof, with (i) at least one thermoplastic resin or a mixture of thermoplastic resins; and (ii) at least one thermosetting composition or a mixture of thermosetting compositions.  
     
     
         82 . The composition according to  claim 80 , wherein the thermoplastic resin is selected from one or more of polycarbonate, polystyrene, polypropylene, polyethylene, and polyphenylene oxide resins.  
     
     
         83 . A coating composition comprising an epoxy and the compound of  claim 39  and optionally a co-curing agent and optionally a catalyst.  
     
     
         84 . The coating composition of  claim 83  including a co-curing agent and a catalyst.