Oximesulfonic acid esters and the use thereof as latent sulfonic acids

A compound of formula Ib

• 33
• wherein
• m is 0 or 1 and x is 1 or 2;
• R1″ is phenyl mono- or poly-substituted by C1-C6alkyl, phenyl, OR4, SR4 and/or by NR5R6, it being possible for the substituents OR4, SR4 and NR5R6 to form 5- or 6-membered rings, via the radicals R4, R5 and/or R6, with further substituents or with one of the carbon atoms of the phenyl ring,
• or R1″ is naphthyl, anthracyl or phenanthryl, the radicals naphthyl, anthracyl and phenanthryl being unsubstituted or mono- or poly-substituted by C1-C6alkyl, phenyl, OR4, SR4 and/or by NR5R6, it being possible for the substituents OR4, SR4 and NR5R6 to form 5-or 6-membered rings, via the radicals R4, R5 and/or R6, with further substituents or with one of the carbon atoms of the naphthyl, anthracyl or phenanthryl ring,
• or R1″ is a heteroaryl radical that is unsubstituted or substituted by C1-C6alkyl, phenyl, OR4, SR4 and/or by NR5R6, it being possible for the substituents OR4, SR4 and NR5R6 to form 5- or 6-membered rings, via the radicals R4, R5 and/or R6, with further substituents or with one of the carbon atoms of the heteroaryl ring, with the proviso that R1″ is not unsubstituted thienyl;
• R2 has one of the meanings of R1″ or is unsubstituted phenyl, C1-C6alkanoyl, benzoyl that is unsubstituted or substituted by C1-C6alkyl, phenyl, OR4, SR4 and/or by NR5R6, C2-C6alkoxycarbonyl, phenoxycarbonyl, R5R6N, morpholino, piperidino, CN, C1-C4haloalkyl, S(O)nC1-C6-alkyl, unsubstituted or C1-C12alkyl-substituted S(O)n-C6-C10aryl, SO2O-C1-C6alkyl, SO2O-C6-C10aryl or NHCONH2, wherein n is 1 or 2,
• or R1″ and R2, if appropriate together with the CO group, form a 5- or 6-membered ring that is unsubstituted or substituted by C1-C6alkyl, phenyl, OR4, SR4 or by NR5R6 and that may additionally be interrupted by O, S, NR5 and/or by CO and to which one or more benzo radicals may be fused;
• R3, when x is 1, is C1-C18alkyl, phenyl-C1-C3alkyl, camphoryl, C1-C10haloalkyl, phenyl, naphthyl, anthracyl or phenanthryl, the radicals phenyl, naphthyl, anthracyl and phenanthryl being unsubstituted or mono- or poly-substituted by halogen, C1-C4haloalkyl, CN, NO2, C1-C16alkyl, OR4, COOR7, —OCO-C1-C4alkyl, SO20R7 and/or by R5R6N, with the proviso that when R3 is phenyl, 3-chlorophenyl or 4-methylphenyl, R1 as a methoxy-substituted phenyl ring must contain at least one further substituent on the ring, which substituent is not, however, methoxy or methyl, and with the proviso that no two of the substituents OR4 form a 1,3-dioxolan ring,
• or R3, when x is 2, is C2-C12alkylene, phenylene, naphthylene,
• 34
• diphenylene or oxydiphenylene, the radicals phenylene, naphthylene,
• 35
• diphenylene and oxydiphenylene being unsubstituted or substituted by C1-C12alkyl;
• R4 is hydrogen or C1-C12alkyl that is unsubstituted or substituted by OH, C1-C4alkoxy, C1-C12alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl and/or by C1-C6alkanoyl and that may additionally be interrupted by —O—;
• R5 and R6 are each independently of the other hydrogen or C1-C12alkyl that is unsubstituted or substituted by OH, C1-C4alkoxy, C1-C12alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)-sulfonyl and/or by C1-C6alkanoyl and that may additionally be interrupted by —O—, or R5 and R6 are phenyl, C1-C6alkanoyl, benzoyl, C1-C6alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, naphthylsulfonyl, anthracylsulfonyl or phenanthrylsulfonyl, or R5 and R6, together with the nitrogen atom to which they are bonded, form a 5-, 6- or 7-membered ring that may be interrupted by —O— or by —NR4—;
• and
• R7 is C1-C12alkyl that is unsubstituted or substituted by OH and/or by C1-C4alkoxy and that may additionally be interrupted by —O—.

A process for the photopolymerisation with radiation of wavelengths over 390 nm, wherein as a photosensitive acid donor a compound of the formula Ia

• 36
• wherein
• m is 0 or 1 and x is 1 or 2;
• R1′ is phenyl mono- or poly-substituted by C1-C6alkyl, phenyl, OR4, SR4 and/or by NR5R6, it being possible for the substituents OR4, SR4 and NR5R6 to form 5- or 6-membered rings, via the radicals R4, R5 and/or R6, with further substituents or with one of the carbon atoms of the phenyl ring,
• or R1′ is naphthyl, anthracyl or phenanthryl, the radicals naphthyl, anthracyl and phenanthryl being unsubstituted or mono- or poly-substituted by C1-C6alkyl, phenyl, OR4, SR4 and/or by NR5R6, it being possible for the substituents OR4, SR4 and NR5R6 to form 5- or 6-membered rings, via the radicals R4 or R5, with further substituents or with one of the carbon atoms of the naphthyl, anthracyl or phenanthryl ring,
• or R1′ is a heteroaryl radical that is unsubstituted or substituted by C1-C6alkyl, phenyl, OR4, SR4 and/or by NR5R6, it being possible for the substituents OR4, SR4 and NRSR6 to form 5- or 6-membered rings, via the radicals R4, R5 and/or R6, with further substituents or with one of the carbon atoms of the heteroaryl ring;
• R2 has one of the meanings of R1′ or is unsubstituted phenyl, C1-C6alkanoyl, benzoyl that is unsubstituted or substituted by C1-C6alkyl, phenyl, OR4, SR4 and/or by NR5R6, C2-C6alkoxycarbonyl, phenoxycarbonyl, R5R6N, morpholino, piperidino, CN, C1-C4haloalkyl, S(O)nC1-C6-alkyl, unsubstituted or C1-C12alkyl-substituted S(O)n-C6-C12aryl, SO2O-C1-C6alkyl, SO2O-C6-C10aryl or NHCONH2, wherein n is 1 or 2;
• or R1′ and R2, if appropriate together with the CO group, form a 5- or 6-membered ring that is unsubstituted or substituted by C1-C6alkyl, phenyl, OR4, SR4 or by NR5R6 and that may additionally be interrupted by O, S, CO and/or by NR5 and to which one or more benzo radicals may be fused;
• R3, when x is 1, is C1-C18alkyl, phenyl-C1-C3alkyl, camphoryl, C1-C10haloalkyl, phenyl, naphthyl, anthracyl or phenanthryl, the radicals phenyl, naphthyl, anthracyl and phenanthryl being unsubstituted or mono- or poly-substituted by halogen, C1-C4haloalkyl, CN, NO2, C1-C16alkyl, OR4, COOR7, —OCO-C1-C4alkyl, SO2OR7 and/or by R5R6N,
• or R3, when x is 2, is C2-C12alkylene, phenylene, naphthylene,
• 37
• diphenylene or oxydiphenylene, the radicals phenylene, naphthylene,
• 38
• diphenylene and oxydiphenylene being unsubstituted or substituted by C1-C12alkyl;
• R4 is hydrogen or C1-C12alkyl that is unsubstituted or substituted by OH, C1-C4alkoxy, C1-C12alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl and/or by C1-C6alkanoyl and that may additionally be interrupted by —O—;
• R5 and R6 are each independently of the other hydrogen or C1-C12alkyl that is unsubstituted or substituted by OH, C1-C4alkoxy, C1-C12alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)-sulfonyl and/or by C1-C6alkanoyl and that may additionally be interrupted by —O—,
• or R5 and R6 are phenyl, C1-C6alkanoyl, benzoyl, C1-C6alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, naphthylsulfonyl, anthracylsulfonyl or phenanthrylsulfonyl,
• or R5 and R6, together with the nitrogen atom to which they are bonded, form a 5-, 6- or 7-membered ring that may be interrupted by —O— or by —NR4—;
• and
• R7 is C1-C12alkyl that is unsubstituted or substituted by OH and/or by C1-C4alkoxy and that may additionally be interrupted by —O—,
• is added.