Method for preparing light-absorbing polymeric compositions

The diacidic anthraquinone compounds having Formulae

• 583
• wherein R14 is selected from the group consisting of hydrogen, 1-4 groups selected from amino, C1-C10 alkylamino, C3-C8 alkenylamino, C3-C8 alkynylamino, C3-C8 cycloalkylamino, arylamino, halogen, C1-C6 alkoxy, C1-C6 alkylthio, aryl, aroyl, C1-C6 alkanoyl, C1-C6 alkanoyloxy, NHCO C1-C6 alkyl, NHCOaryl, NHCO2 C1-C6 alkyl, NHSO2 C1-C6 alkyl, NHSO2 aryl, C1-C6 alkoxycarbonyl, aryloxy, arylthio, heteroarylthio, cyano, nitro, trifluoromethyl, thiocyano, SO2C1-C6 alkyl, SO2 aryl, —SO2NH C1-C6 alkyl, —SO2N(C1-C6 alkyl)2, —SO2N(C1-C6 alkyl) aryl, CONFH C1-C6 alkyl, CON(C1-C6 alkyl)2, CON(C1-C6 alkyl) aryl, C1-C6 alkyl, furfurylamino, tetrahydrofurfurylamino, 4-(hydroxymethyl) cyclohexanemethylamino,
• 584
• or hydroxy;
• Q and Q′ are independently selected from the group consisting of —O—, —N(COR10)—, —N(SO2R10)—, —N(R10)—, —S—, —SO2—, —CO2—, —CON(R10)—, SO2N (R10)—, wherein R10 is selected from the group consisting of hydrogen, aryl, C3-C8 cycloalkyl, or C1-C10 alkyl;
• R16′ is selected from hydrogen or one or two groups selected from C1-C6 alkyl, halogen and C1-C6 alkoxy;
• wherein each C1-C6 alkyl group and [[C1-C6 alkyl group]] C1-C6 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, C1-C6 alkoxy, C3-C8 cycloalkoxy, C1-C6 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.

The diacidic anthraquinone compounds having the following structures:

• 585
• wherein Sub is a substituent selected from the group consisting of halogen, trifluoromethyl, aroyl, C1-C6 alkanoyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxy, C1-C6 alkylthio, aryloxy, arylthio, heteroarylthio, cyano, nitro, SO2NHC1-C6 alkyl, SO2N (C1-C6 alkyl)2, SO2N (C1-C6 alkyl) aryl, CONH C1-C6 alkyl, CON (C1-C6 alkyl)2, CON (C1-C6 alkyl) aryl, C1-C6 alkyl, SO2 C1-C6 alkylsulfonyl and SO2 aryl;
• Sub1 is a substituent selected from the group consisting of amino, C1-C12 alkylarnino, arylamino and C3-C8 cycloalkylamino. Q′ is selected from the group consisting of —O—, —N(COR10)—, —N(SO2R10)—, —N(R10)—, —S—, —SO2—, —CO2—, —CON(R10)—, SO2N (R10)—, wherein R10 is selected from the group consisting of hydrogen, aryl, C3-C8 cycloalkyl, or C1-C10 alkyl;
• and R16′ is selected from hydrogen or one or two groups selected from C1-C6 alkyl, halogen and C1-C6 alkoxy.

The diacidic anthraquinone compounds having the formulae

• 586
• where R16′ is selected from the group consisting of hydrogen or one or two groups selected from C1-C6 alkyl, halogen and C1-C6 alkoxy;
• and Sub3 is a substituent selected from C1-C6 alkylthio, arylthio and heteroarylthio and Sub2 is a substituent selected from the group consisting of amino, C1-C10 alkylamino, C3-C8 alkenylamino, C3-C8 alkynylamino, C3-C8 cycloalkylamino, arylamino, furfurylamino, tetrahydrofurfurylamino, 4-(hydroxymethyl) cyclohexanemethylamino, NHCO C1-C6 alkyl, NHCO aryl, NHCO2 C1-C6 alkyl, NHSO2 C1-C6 alkyl, NHSO2 aryl and
• 587

The diacidic anthraquinone compounds having the structures

• 591
• wherein Q is selected from the group consisting of —O—, —S— and —SO2—;
• Q′ is selected from the group consisting of —O—, —N(COR10)—, —N(SO2R10)—, —N(R10)—, —S—, —SO2—, —CO2—, —CON(R10)—, SO2N (R10)—, wherein R10 is selected from the group consisting of hydrogen, aryl, C3-C8 cycloalkyl, or C1-C10 alkyl;
• and R16′ is selected from the group consisting of hydrogen or one or two groups selected from C1-C6 alkyl, halogen and C1-C6 alkoxy.

The diacidic anthraquinone compounds having the structures:

• 592
• wherein Sub1 is a substituent selected from the group consisting of amino, C1-C12 alkylamino, arylamino and C3-C8 cycloalkylamino:
• Sub4 is selected from the group consisting of amino, C1-C10 alkylamino, C3-C8 alkenylamino, C3-C8 alkynylamino, C3-C8 cycloalkylamino, arylaamino, furfurylamino, tetrahydrofurfurylamino, 4-(hydroxymethyl) cyclohexanemethylamino, NHCO C1-C6 alkyl, NHCO aryl, NHCO2, C1-C6 alkyl, NHSO2 C1-C6 alkyl, NHSO2 aryl
• 593
• NHCO C1-C6 alkyl, NHCO2 C1-C6 alkyl, NHCO aryl, NHSO2 C1-C6 alkyl, NHSO2 aryl, C1-C6 alkylthio, arylthio, heteroarylthio and hydroxy:
• Q is selected from the group consisting of —O—, —S— and —SO2—;
• Q′ is selected from the group consisting of —O—, —N(COR10)—, —N(SO2R10)—, —N(R10)—, —S—, —SO2—, —CO2—, —CON(R10)—, SO2N (R10)—, wherein R10 is selected from the group consisting of hydrogen, aryl, C3-C8 cycloalkyl, or C1-C10 alkyl;
• and R16′ is selected from the group consisting of hydrogen or one or two groups selected from C1-C6 alkyl, halogen and C1-C6 alkoxy.

The diacidic anthraquinone compounds having the structures:

• 594
• wherein Q is selected from the group consisting of —O—, —S— and —SO2—;
• Sub1 is a substitutent selected from the group consisting of amino, C1-C12 alkylamino, arylamino and C3-C8 cycloalkylamino;
• Q′ is selected from the group consisting of —O—, —N(COR10)—, —N(SO2R10)—, —N(R10)—, —S—, —SO2—, —CO2—, —CON(R10)—, SO2N (R10)—, wherein R10 is selected from the group consisting of hydrogen, aryl, C3-C8 cycloalkyl, or C1-C10 alkyl;
• and R16′ is selected from the group consisting of hydrogen or one or two groups selected from C1-C6 alkyl, halogen and C1-C6 alkoxy.