Method for preparing light-absorbing polymeric compositions

Abstract

The present invention recites a method comprising reacting in a solvent in the presence of a base a) at least one diacidic monomer comprising about 1 to 100 mole % of at least one light-absorbing monomer having a light absorption maximum between about 300 nm and about 1200 nm and 99-0 mole % of a non-light absorbing monomer which does not absorb significant light at wavelengths above 300 nm or has a light absorption maximum below 300 nm, with b) an organic compound of Formula II X—B—X 1 wherein B is a divalent organic radical to form a light absorbing composition comprising a mixture of a polymer having the formula and a cyclic compound having the general formula wherein B is as defined above; n is at least 2, m is 1, 2, 3 or 4 and A comprises the residue of a diacidic monomer comprising about 1 to 100 mole % of at least one light-absorbing monomer having a light absorption maximum between about 300 nm and about 1000 nm and wherein the remaining portion of A comprises the residue of a non-light absorbing monomer which does not absorb significant light at wavelengths above 300 nm or has a light absorption maximum below 300 nm.

1 - 58 . (canceled)  
     
     
         59 . The diacidic anthraquinone compounds having Formulae  
       
         
           
           
               
               
           
         
       
       wherein R 14  is selected from the group consisting of hydrogen, 1-4 groups selected from amino, C 1 -C 10  alkylamino, C 3 -C 8  alkenylamino, C 3 -C 8  alkynylamino, C 3 -C 8  cycloalkylamino, arylamino, halogen, C 1 -C 6  alkoxy, C 1 -C 6  alkylthio, aryl, aroyl, C 1 -C 6  alkanoyl, C 1 -C 6  alkanoyloxy, NHCO C 1 -C 6  alkyl, NHCOaryl, NHCO 2  C 1 -C 6  alkyl, NHSO 2  C 1 -C 6  alkyl, NHSO 2  aryl, C 1 -C 6  alkoxycarbonyl, aryloxy, arylthio, heteroarylthio, cyano, nitro, trifluoromethyl, thiocyano, SO 2 C 1 -C 6  alkyl, SO 2  aryl, —SO 2 NH C 1 -C 6  alkyl, —SO 2 N(C 1 -C 6  alkyl) 2 , —SO 2 N(C 1 -C 6  alkyl) aryl, CONFH C 1 -C 6  alkyl, CON(C 1 -C 6  alkyl) 2 , CON(C 1 -C 6  alkyl) aryl, C 1 -C 6  alkyl, furfurylamino, tetrahydrofurfurylamino, 4-(hydroxymethyl) cyclohexanemethylamino,  
       
         
           
           
               
               
           
         
       
       or hydroxy; Q and Q′ are independently selected from the group consisting of —O—, —N(COR 10 )—, —N(SO 2 R 10 )—, —N(R 10 )—, —S—, —SO 2 —, —CO 2 —, —CON(R 10 )—, SO 2 N (R 10 )—, wherein R 10  is selected from the group consisting of hydrogen, aryl, C 3 -C 8  cycloalkyl, or C 1 -C 10  alkyl; R 16 ′ is selected from hydrogen or one or two groups selected from C 1 -C 6  alkyl, halogen and C 1 -C 6  alkoxy; wherein each C 1 -C 6  alkyl group and [[C 1 -C 6  alkyl group]] C 1 -C 6  alkyoxy group which is a portion of another group may contain at least one substituent selected from the group consisting of hydroxy, cyano, chlorine, fluorine, C 1 -C 6  alkoxy, C 3 -C 8  cycloalkoxy, C 1 -C 6  alkylcyclohexyl, hydroxmethyl cyclohexyl, aryl and heteroaryl; with the provision that two acidic groups containing one acidic proton each or one acidic group containing two acidic hydrogens be present in the compounds of Formula XIV, XIXc, XIXd, XIXe XIXf.  
     
     
         60 . The diacidic anthraquinone compounds having the following structures:  
       
         
           
           
               
               
           
         
       
       wherein Sub is a substituent selected from the group consisting of halogen, trifluoromethyl, aroyl, C 1 -C 6  alkanoyl, C 1 -C 6  alkoxycarbonyl, C 1 -C 6  alkoxy, C 1 -C 6  alkylthio, aryloxy, arylthio, heteroarylthio, cyano, nitro, SO 2 NHC 1 -C 6  alkyl, SO 2 N (C 1 -C 6  alkyl) 2 , SO 2 N (C 1 -C 6  alkyl) aryl, CONH C 1 -C 6  alkyl, CON (C 1 -C 6  alkyl) 2 , CON (C 1 -C 6  alkyl) aryl, C 1 -C 6  alkyl, SO 2  C 1 -C 6  alkylsulfonyl and SO 2  aryl; Sub 1  is a substituent selected from the group consisting of amino, C 1 -C 12  alkylarnino, arylamino and C 3 -C 8  cycloalkylamino. Q′ is selected from the group consisting of —O—, —N(COR 10 )—, —N(SO 2 R 10 )—, —N(R 10 )—, —S—, —SO 2 —, —CO 2 —, —CON(R 10 )—, SO 2 N (R 10 )—, wherein R 10  is selected from the group consisting of hydrogen, aryl, C 3 -C 8  cycloalkyl, or C 1 -C 10  alkyl; and R 16 ′ is selected from hydrogen or one or two groups selected from C 1 -C 6  alkyl, halogen and C 1 -C 6  alkoxy.  
     
     
         61 - 62 . (canceled)  
     
     
         63 . The diacidic anthraquinone compounds having the formulae  
       
         
           
           
               
               
           
         
       
       where R 16 ′ is selected from the group consisting of hydrogen or one or two groups selected from C 1 -C 6  alkyl, halogen and C 1 -C 6  alkoxy; and Sub 3  is a substituent selected from C 1 -C 6  alkylthio, arylthio and heteroarylthio and Sub 2  is a substituent selected from the group consisting of amino, C 1 -C 10  alkylamino, C 3 -C 8  alkenylamino, C 3 -C 8  alkynylamino, C 3 -C 8  cycloalkylamino, arylamino, furfurylamino, tetrahydrofurfurylamino, 4-(hydroxymethyl) cyclohexanemethylamino, NHCO C 1 -C 6  alkyl, NHCO aryl, NHCO 2  C 1 -C 6  alkyl, NHSO 2  C 1 -C 6  alkyl, NHSO 2  aryl and  
       
         
           
           
               
               
           
         
       
     
     
         64 . The diacidic anthraquinone compounds of  claim 59  having the formulae:  
       
         
           
           
               
               
           
         
       
       wherein Sub 2  is a substituent selected from the group consisting of amino, C 1 -C 10  alkylamino, C 3 -C 8  alkenylamino, C 3 -C 8  alkynylamino, C 3 -C 8  cycloalkylamino, arylamino, furfurylamino, tetrahydrofurfurylamino, 4-(hydroxymethyl) cyclohexanemethylamino, NHCO C 1 -C 6  alkyl, NHCO aryl, NHCO 2  C 1 -C 6  alkyl, NHSO 2  C 1 -C 6  alkyl, NHSO 2  aryl and  
       
         
           
           
               
               
           
         
       
       Sub 4  is selected from the group consisting of Sub 2 , NHCO C 1 -C 6  alkyl, NHCO 2  C 1 -C 6  alkyl, NHCO aryl, NHSO 2  C 1 -C 6  alkyl, NHSO 2  aryl, C 1 -C 6  alkylthio, arylthio, heteroarylthio and hydroxy; Q is selected from the group consisting of —O—, S—, —SO 2 —; Q′ selected from the group consisting of —O—, —N(COR 10 )—, —N(SO 2 R 10 )—, —N(R 10 )—, —S—, —SO 2 —, —CO 2 —, —CON(R 10 )—, SO 2 N (R 10 )—, wherein R 10  is selected from the group consisting of hydrogen, aryl, C 3 -C 8  cycloalkyl, or C 1 -C 10  alkyl.  
     
     
         65 . A diacidic anthraquinone compounds having the formula  
       
         
           
           
               
               
           
         
       
       wherein Sub is a substituent selected from the group consisting of halogen, trifluoromethyl, aroyl, C 1 -C 6  alkanoyl, C 1 -C 6  alkoxycarbonyl, C 1 -C 6  alkoxy, C 1 -C 6  alkylthio, aryloxy, arylthio, heteroarylthio, cyano, nitro, SO 2 NHC 1 -C 6  alkyl, SO 2 N (C 1 -C 6  alkyl) 2 , SO 2 N (C 1 -C 6  alkyl) aryl, CONH C 1 -C 6  alkyl, CON (C 1 -C 6  alkyl) 2 , CON (C 1 -C 6  alkyl) aryl, C 1 -C 6  alkyl, SO 2  C 1 -C 6  alkylsulfonyl and SO 2  aryl; Sub 1  is a substituent selected from the group consisting of amino, C 1 -C 12  alkylamino, arylamino and C 3 -C 8  cycloalkylamino, and R 16 ′ is selected from hydrogen or one or two groups selected from C 1 -C 6  alkyl, halogen and C 1 -C 6  alkoxy.  
     
     
         66 . The diacidic anthraquinone compounds having the structures  
       
         
           
           
               
               
           
         
       
       wherein Q is selected from the group consisting of —O—, —S— and —SO 2 —; Q′ is selected from the group consisting of —O—, —N(COR 10 )—, —N(SO 2 R 10 )—, —N(R 10 )—, —S—, —SO 2 —, —CO 2 —, —CON(R 10 )—, SO 2 N (R 10 )—, wherein R 10  is selected from the group consisting of hydrogen, aryl, C 3 -C 8  cycloalkyl, or C 1 -C 10  alkyl; and R 16 ′ is selected from the group consisting of hydrogen or one or two groups selected from C 1 -C 6  alkyl, halogen and C 1 -C 6  alkoxy.  
     
     
         67 . The diacidic anthraquinone compounds having the structures:  
       
         
           
           
               
               
           
         
       
       wherein Sub 1  is a substituent selected from the group consisting of amino, C 1 -C 12  alkylamino, arylamino and C 3 -C 8  cycloalkylamino: Sub 4  is selected from the group consisting of amino, C 1 -C 10  alkylamino, C 3 -C 8  alkenylamino, C 3 -C 8  alkynylamino, C 3 -C 8  cycloalkylamino, arylaamino, furfurylamino, tetrahydrofurfurylamino, 4-(hydroxymethyl) cyclohexanemethylamino, NHCO C 1 -C 6  alkyl, NHCO aryl, NHCO 2 , C 1 -C 6  alkyl, NHSO 2  C 1 -C 6  alkyl, NHSO 2  aryl  
       
         
           
           
               
               
           
         
       
       NHCO C 1 -C 6  alkyl, NHCO 2  C 1 -C 6  alkyl, NHCO aryl, NHSO 2  C 1 -C 6  alkyl, NHSO 2  aryl, C 1 -C 6  alkylthio, arylthio, heteroarylthio and hydroxy: Q is selected from the group consisting of —O—, —S— and —SO 2 —; Q′ is selected from the group consisting of —O—, —N(COR 10 )—, —N(SO 2 R 10 )—, —N(R 10 )—, —S—, —SO 2 —, —CO 2 —, —CON(R 10 )—, SO 2 N (R 10 )—, wherein R 10  is selected from the group consisting of hydrogen, aryl, C 3 -C 8  cycloalkyl, or C 1 -C 10  alkyl; and R 16 ′ is selected from the group consisting of hydrogen or one or two groups selected from C 1 -C 6  alkyl, halogen and C 1 -C 6  alkoxy.  
     
     
         68 . The diacidic anthraquinone compounds having the structures:  
       
         
           
           
               
               
           
         
       
       wherein Q is selected from the group consisting of —O—, —S— and —SO 2 —; Sub 1  is a substitutent selected from the group consisting of amino, C 1 -C 12  alkylamino, arylamino and C 3 -C 8  cycloalkylamino; Q′ is selected from the group consisting of —O—, —N(COR 10 )—, —N(SO 2 R 10 )—, —N(R 10 )—, —S—, —SO 2 —, —CO 2 —, —CON(R 10 )—, SO 2 N (R 10 )—, wherein R 10  is selected from the group consisting of hydrogen, aryl, C 3 -C 8  cycloalkyl, or C 1 -C 10  alkyl; and R 16 ′ is selected from the group consisting of hydrogen or one or two groups selected from C 1 -C 6  alkyl, halogen and C 1 -C 6  alkoxy.  
     
     
         69 - 108 . (canceled)