Photopolymerizable thermosetting resin compositions

Photosensitive thermosetting liquid composition comprising

• (A) an oligomer or polymer containing at least one carboxylic acid group in the molecule;
• (B) at least one compound of the formula I, II, III, IV, V or VI
• wherein R1 is phenyl which is unsubstituted or substituted by one or more C1-C6alkyl, phenyl, halogen, OR8, SR9 or NR10R11, or R1 is C1-C20alkyl, C2-C20alkenyl, C2-C20alkynyl or C2-C20alkyl optionally be interrupted by one or more —O— and/or optionally substituted by one or more hydroxyl groups, or R1 is C2-C20alkanoyl or benzoyl which is unsubstituted or substituted by one or more C1-C6alkyl, phenyl, OR8, SR9 or NR10R11, or R1 is C2-C12alkoxycarbonyl optionally interrupted by one or more —O— and/or optionally substituted by one or more hydroxyl groups, or R1 is phenoxycarbonyl which is unsubstituted or substituted by C1-C6alkyl, halogen, phenyl, OR8 or NR10R11, or R1 is —CONR10R11, CN, NO2, C1-C4haloalkyl, S(O)mC1-C6alkyl, unsubstituted or C1-C12alkyl-substituted S(O)m—C6-C12aryl, SO2O—C1-C6alkyl, SO2O—C6-C10aryl, or diphenyl-phosphinoyl, or R1 together with R3 or R1 together with R7 may form 5 or 6 membered rings including one or more CO— and/or oxime-groups;
• m is 1 or 2;
• R2 is C2-C12alkanoyl which is unsubstituted or substituted by one or more halogen or CN, or R2 is C3-C12alkenoyl, or benzoyl which is unsubstituted or substituted by one or more C1-C6alkyl, phenyl, halogen CN, OR8, SR9 or NR10R11, or R2 is C2-C12alkoxycarbonyl or phenoxycarbonyl which is unsubstituted or substituted by C1-C6alkyl or halogen;
• R3, R4, R5, R6 and R7 independently of one another are hydrogen, halogen, C1-C12alkyl, cyclopentyl, cyclohexyl or phenyl which is unsubstituted or substituted by one or more OR8, SR9 or NR10R11, or R3, R4, R5, R6 and R7 are benzyl, benzoyl, C2-C12alkanoyl, C2-C12alkoxycarbonyl optionally interrupted by one or more —O— and/or optionally substituted by one or more hydroxyl groups or R3, R4, R5, R6 and R7 are phenoxycarbonyl or a group OR8, SR9, SOR9, SO2R9, NO2, CN, CONR10R11, or NR10R11, wherein the substituents OR8, SR9 and NR10R11 may form 5- or 6-membered rings via the radicals R8, R9, R10 and/or R11 with further substituents on the phenyl ring or with one of the carbon atoms of the phenyl ring;
• R8 is hydrogen, C1-C12alkyl or C2-C6alkyl which is substituted by —OH, —SH, —CN, C1-C4alkoxy, C3-C6alkenoxy, —OCH2CH2CN, —OCH2CH2COO(C1—C4alkyl), —OCO—C1-C4alkyl, —OCO-phenyl, COOH or COO(C1-C4alkyl), or R8 is C2-C6alkyl which is interrupted by one or more —O—, or R8 is —(CH2CH2O)nH, C2-C8alkanoyl, C2-C12alkenyl, C3-C6alkenoyl, cyclohexyl or phenyl which is unsubstituted or substituted by halogen, C1-C12alkyl or C1-C4alkoxy, or R8 is phenyl-C1-C3alkyl or Si(C1-C8alkyl)r(phenyl)3−r or R8 is a group
• n is 1-20;
• r is 1, 2 or 3;
• R9 is hydrogen, C1-C12alkyl, C2-C12alkenyl, cyclohexyl, C2-C6alkyl which is substituted by —OH, —SH, —CN, C1-C4alkoxy, C3-C6alkenoxy, —OCH2CH2CN, —OCH2CH2COO(C1-C4alkyl), —OCO—C1-C4alkyl, —OCO-phenyl, COOH or COO(C1-C4alkyl) or R9 is C2-C12alkyl which is interrupted by one or more —O— or —S— or R9 is phenyl which is unsubstituted or substituted by halogen, C1-C12alkyl or C1-C4alkoxy, or R9 is phenyl-C1-C3alkyl or a group
• R10 and R11 independently of each other are hydrogen, C1-C12alkyl, C2-C4hydroxyalkyl, C2-C10alkoxyalkyl, C2-C5alkenyl, C5-C12cycloalkyl, phenyl-C1-C3alkyl, phenyl which is unsubstituted or substituted by C1-C12alkyl or C1-C4alkoxy, or R10 and R11 are C2-C3alkanoyl, C3-C6alkenoyl or benzoyl, or R10 and R11 together are C2-C6alkylene optionally interrupted by —O— or —NR8—, or R10 and R11 together are C2-C6alkylene which can be substituted by hydroxyl, C1-C4alkoxy, C2-C4alkanoyloxy or benzoyloxy, or, when R10 is hydrogen, R11 may be a group
• R12, R13, R14, R15, R16, R17, R18 and R19 independently of one another are hydrogen, halogen, C1-C12alkyl, cyclopentyl, cyclohexyl or phenyl which is unsubstituted or substituted by one or more OR8, SR9 or NR10R11, or R12, R13, R14, R15, R16, R17, R18 and R19 are benzyl, benzoyl, C2-C12alkanoyl,
• C2-C12alkoxycarbonyl optionally interrupted by one or more —O— and/or optionally substituted by one or more hydroxyl groups or R12, R13, R14, R15, R16, R17, R18 and R19 are phenoxycarbonyl or a group OR8, SR9, SOR9, SO2R9, NO2, CN, CONR10R11, or NR10R11, wherein the substituents OR8, SR9 and NR10R11 may form 5- or 6-membered rings via the radicals R8, R9, R10 and/or R11 with further substituents on the phenyl ring or with one of the carbon atoms of the phenyl ring or, when M4 is a direct bond, R15 and R16 together are ethylene or ethynylene;
• t is 0 or 1;
• M is C1-C12alkylene, cyclohexylene, phenylene, —COO—(C2-C12alkylene)—OOC—, —COO—(CH2CH2O)n—OC— or —CO—(C2-C12-alkylene)—CO—;
• M1 is a direct bond or C1-C12alkylenoxy, optionally interrupted by 1 to 5 —O—, —S— and/or —NR10—;
• M2 is a direct bond or C1-C12-alkylene-S—, optionally interrupted by 1 to 5 —O—, —S— and/or —NR10—;
• M3 is a direct bond, a piperazino group, or C1-C12alkylene-NR10—, optionally interrupted by 1 to 5 —O—, —S— and/or —NR10—;
• M4 is a direct bond, —O—, —S—, —SO—, —SO2—, —CO—, —CH2—, —NR10—, or a group
• Ar is a 5- or 6-membered aromatic heterocyclic ring, which is unsubstituted or substituted by one or more C1-C6alkyl, phenyl, halogen, OR8, SR9, NR10R11, CN, C2-C6alkanoyl or benzoyl;
• wherein 1-phenyl-1,2-propanedione-2-o-benzoyl oxime and 1-phenyl-1,2-propanedione-2-o-ethoxycarbonyl oxime are excluded;
• (C) a photopolymerizable reactive or unreactive diluent;
• and
• (D) as a thermosetting component an epoxy compound containing at least two epoxy groups in one molecule.