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Oxime Ester Photoinitiators

  • US 20090087759A1
  • Filed: 11/08/2006
  • Published: 04/02/2009
  • Est. Priority Date: 12/01/2005
  • Status: Active Grant
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First Claim
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1. A compound of the formula I, II, or III whereinR1 is hydrogen, (CO)R″

  • 2, C1-C20alkoxycarbonyl, phenyl-C1-C4alkyl, C1-C20alkyl which optionally is substituted by one or more halogen, COOR11, CONR12R13;

    or R1 is C2-C20alkyl which is interrupted by O, CO or NR14;

    C2-C12alkenyl which optionally is interrupted by O, CO or NR14, or is C4-C8cycloalkenyl or C2-C12alkinyl;

    or R1 is benzoyl, naphthoyl, phenyloxycarbonyl or naphtyloxycarbonyl;

    or is benzoyl, naphthoyl, phenyloxycarbonyl or naphtyloxycarbonyl each of which is optionally substituted by one or more C1-C20alkyl, C1-C4haloalkyl, SR10, OR11, NR12R13, halogen, phenyl, COOR11, CONR12R13, CN, NO2 or C3-C10cycloalkyl which optionally is interrupted by O, CO or NR14;

    or R1 is C3-C10cycloalkyl which optionally is interrupted by O, CO or NR14, C3-C10cycloalkylcarbonyl which optionally is interrupted by O, CO or NR14, C3-C10cycloalkyloxycarbonyl which optionally is interrupted by O, CO or NR14;

    or R1 is unsubstituted phenyl or naphthyl, or is phenyl or naphthyl which is substituted by one or more C1-C20alkyl, C1-C4haloalkyl, SR10, OR11, NR12R13, halogen, phenyl, COOR11, CONR12R13, CN, NO2, or C3-C10cycloalkyl which optionally is interrupted by O, CO or NR14;

    R2 and R′

    2 independently of each other are hydrogen, C1-C20alkyl, C3-C10cycloalkyl which optionally is interrupted by O, CO or NR14 or R2 and R′

    2 are C1-C20alkyl optionally substituted by one or more halogen, OR11, COOR11, CONR12R13, phenyl or phenyl substituted by SR10, OR11, or NR12R13;

    or R2 and R′

    2 are C2-C20alkyl interrupted by one or more O and/or optionally substituted by one or more halogen, OR11, COOR11, CONR12R13, phenyl or phenyl substituted by SR10, OR11, or NR12R13;

    or R2 and R′

    2 are unsubstituted phenyl or naphthyl or are phenyl or naphthyl which is substituted by one or more C1-C12alkyl, phenyl, halogen, CN, NO2, SR10, OR11, NR12R13 or by C3-C10cycloalkyl Which optionally is interrupted by O, CO or NR14;

    or R2 and R′

    2 are C2-C20alkanoyl, or benzoyl which is unsubstituted or substituted by one or more C1-C6alkyl, phenyl, SR10, OR11, NR12R13;

    or R2 and R′

    2 are C2-C12alkoxycarbonyl optionally interrupted by one or more O and/or optionally substituted by one or more OH;

    or R2 and R′

    2 are phenoxycarbonyl which is unsubstituted or substituted by one or more C1-C6alkyl, halogen, phenyl, SR10, OR11 or NR12R13;

    R″

    2 has one of the meanings given for R2 and R′

    2 or is R′

    ″

    2 has one of the meanings given for R2 and R′

    2 or is R3, R4, and R5 independently of one another are hydrogen, halogen, C1-C20alkyl, C2-C20alkyl which is interrupted by O, CO or NR14, C2-C12alkenyl which optionally is interrupted by O, CO or NR14, or are C4-C8cycloalkenyl, C2-C12alkinyl, phenyl-C1-C4alkyl, CN, NO2 or C3-C10cycloalkyl which optionally is interrupted by O, CO or NR14;

    or R3, R4, and R5 are phenyl which is unsubstituted or substituted by one or more SR10, OR11, or NR12R13;

    or R3, R4, and R5 are (CO)R2, SR10, OR11, SOR10,OR11, SO2R10 or NR12R13, wherein the substituents (CO)R12, OR11, SR10 and NR12R13 optionally form 5- or 6-membered rings via the radicals R10, R11, R12 R13, and/or R′

    2 with further substituents on the phenyl ring or with one of the carbon atoms of the phenyl ring;

    provided that (i) at least one of R3, R4 or R5 is other than hydrogen or C1-C20alkyl; and

    that (ii) if one of R3, R4 or R5 in the para position of the phenyl ring is SR10 then R10 is not unsubstituted phenyl; and

    (iii) if one of R3, R4 or R5 in the para position of the phenyl ring is NR12R13, then R12 and R13 are not both C1-C20alkyl; and

    (iv) if one of R3, R4 or R5 in the para position of the phenyl ring is NR12R13 and R12 and R13 together with the N-atom to which they are attached form a ring, said ring is not a morpholino ring; and

    (v) if R3 is hydrogen, R4 is hydrogen or C1-C20alkyl in the ortho-position of the phenyl ring and R5 is OR11 in the para-position of the phenyl ring, then R11 is not C3-C10cycloalkyl or C3-C10cycloalkyl which is interrupted by O;

    R6, R7, R8, R′

    6, R′

    7, R′

    8, R″

    6, R″

    7, R′

    ″

    6 and R′

    ″

    7 independently of one another have one of the meanings as given for R3, R4 and R5;

    or R16 and R17 in formula II together are C1-C6alkylene or C2-C6alkenylene to form a bicyclic ring together with the phenyl to which they are attached, wherein said bicyclic ring optionally is substituted by one or more C1-C20alkyl, C2-C20alkyl which is interrupted by O, CO or NR14, C1-C4haloalkyl, SR10, OR11, NR12R13, halogen, phenyl, COOR11, CONR12R13, CN, NO2, or C3-C10cycloalkyl which optionally is interrupted by O, CO or NR14;

    provided that the group is attached to either ring;

    or R′

    ″

    6 and R′

    ″

    7 in formula IIII together are C2-C6alkylene or C2-C6alkenylene to form a bicyclic ring together with the phenyl to which they are attached, wherein said bicyclic ring optionally is substituted by one or more C1-C20alkyl, C2-C20alkyl which is interrupted by O, CO or NR14, C1-C4haloalkyl, SR10, OR11, NR12R13, halogen, phenyl, COOR11, CONR12R13, CN, NO2, or C3-C10cycloalkyl which optionally is interrupted by O, CO or NR14;

    provided that one or more groups (CO)R′

    ″

    2 are attached to either ring;

    R9 is hydrogen, C3-C8cycloalkyl, C2-C5alkenyl, C1-C20alkoxy, unsubstituted C1-C20alkyl or C1-C20alkyl which is substituted by one or more halogen, phenyl, C1-C20alkylphenyl and/or CN;

    or R9 is phenyl or naphthyl, both of which are unsubstituted or substituted by one or more C1-C6alkyl, halogen, CN, OR11, SR10and/or NR12R13;

    or R9 is benzyloxy or phenoxy both of which are unsubstituted or substituted by one or more C1-C6alkyl and/or halogen;

    R10 is hydrogen, C1-C20alkyl, C3-C12alkenyl, C3-C10cycloalkyl which optionally is interrupted by O, CO or NR14, or R10 is phenyl-C1-C4alkyl;

    C1-C8alkyl which is substituted by OH, SH, CN, C3-C6alkenoxy, —

    OCH2CH2CN, —

    OCH2CH2(CO)O(C1-C4alkyl), —

    O(CO)—

    (C1-C4alkyl), —

    O(CO)-phenyl, —

    (CO)OH or —

    (CO)O(C1-C4alkyl);

    or R10 is C2-C20alkyl which is interrupted by one or more O or S;

    or R10 is —

    (CH2CH2O)nH, —

    (CH2CH2O)n(CO)—

    (C1-C8alkyl), C2-C8alkanoyl, benzoyl, C3-C12alkenyl, C3-C6alkenoyl;

    or R10 is phenyl or naphthyl, each of which is unsubstituted or substituted by one or more halogen, C1-C12alkyl, C1-C12alkoxy, phenyl-C1-C3alkyloxy, phenoxy, C1-C12alkylsulfanyl, phenylsulfanyl, —

    N(C1-C12alkyl)2, diphenylamino, —

    (CO)O(C1-C8alkyl) or (CO)N(C1-C8alkyl)2;

    or R10 is phenyl or naphtyl which forms a 5- or 6-membered ring with the phenyl ring to which the SR10 is attached via a direct bond, C1-C4alkylene, O, S, NR14 or CO, wherein said phenyl or naphthyl is unsubstituted or substituted by one or more C1-C20alkyl, C2-C20alkyl which is interrupted by O, CO or NR14, or is substituted by C3-C10cycloalkyl which is optionally interrupted by O, CO or NR14, or is substituted by halogen, C1-C20alkoxy, C1-C20alkylcarbonyl or phenylcarbonyl;

    n is an integer from 1-12;

    R11, is hydrogen, C1-C20alkyl which optionally is substituted by one or more halogen;

    or is —

    (CH2CH2O)nH, —

    (CH2CH2O)n(CO)—

    (C1-C8alkyl), C1-C8alkanoyl, C3-C12alkenyl, C3-C6alkenoyl, phenyl-C1-C4alkyl;

    C2-C20alkyl which is interrupted by one or more O;

    C3-C10cycloalkyl which optionally is interrupted by O, CO or NR14;

    or R11, is C1-C8alkyl which is substituted by OH, SH, CN, C3-C6alkenoxy, —

    OCH2CH2CN, —

    OCH2CH2(CO)O(C1-C4alkyl), —

    O(CO)—

    (C1-C4alkyl), —

    O(CO)-phenyl, —

    (CO)OH or —

    (CO)O(C1-C4alkyl);

    or R11 is benzoyl which is unsubstituted or substituted by one or more C1-C6alkyl, halogen, OH or C1-C4alkoxy;

    or R11 is phenyl or naphthyl each of which is unsubstituted or substituted by one or more halogen, OH, C1-C12alkyl, C3-C10cycloalkyl or C1-C12alkoxy;

    R12 and R13 independently of one another are hydrogen, C1-C20alkyl, C2-C20alkyl which is interrupted by O, CO or NR14, C2-C4hydroxyalkyl, C1-C12alkoxy, phenyl-C1-C4alkyl, (CO)R15, C2-C10alkoxyalkyl, C3-C5alkenyl, C3-C10cycloalkyl which optionally is interrupted by O, CO or NR14;

    or R12 and R13 are phenyl or naphthyl, each of which is unsubstituted or substituted by one or more C1-C20alkoxy, (CO)R15, phenyl, NR16R17, SR10, OR11, C1-C20alkyl, C2-C20alkyl which is interrupted by O, CO or NR14 or by C3-C10cycloalkyl which optionally is interrupted by O, CO or NR14;

    or R12 and R13 independently of each other are C2-C5alkylene or C2-C5alkenylene which is attached to one of the C-atoms of the phenyl or naphthyl ring to which the NR12R13 is attached, wherein said C2-C5alkylene or C2-C5alkenylene optionally is interrupted by O, CO or NR14;

    orR12 and R13 independently of one another are phenyl which is attached via a direct bond to the phenyl ring on which the NR12R13 is positioned;

    orR12 and R13 together with the N-atom to which they are attached form a 5- or 6-membered saturated or unsaturated ring which optionally is interrupted by O, N or NR14, and which ring is unsubstituted or substituted by one or more C1-C20alkyl, C1-C20alkoxy, ═

    O, SR10, OR11, or NR16R17, (CO)R15, NO2, CN, phenyl or by C3-C10cycloalkyl which optionally is interrupted by O, CO or NR14;

    orR12 and R13 together with the N-atom to which they are attached form a heteroaromatic ring system, which heteroaromatic ring system is unsubstituted or substituted by one or more C1-C20alkyl, C1-C20alkoxy, ═

    O, SR10, OR11, NR16R17, (CO)R15, NO2, CN, phenyl or by C3-C10cycloalkyl which optionally is interrupted by O, CO or NR14;

    R14 is hydrogen, C1-C20alkyl, C3-C8cycloalkyl, phenyl or (CO)R15;

    R15 is OH, C1-C20alkyl, C2-C20alkyl which interrupted by O, CO or NR14, C3-C10cycloalkyl which, optionally is interrupted by O, CO or NR14, or is phenyl-C1-C4alkyl, SR10, OR11, or NR12R13;

    or R15 is phenyl or naphtyl both of which are unsubstituted or substituted by one or more SR10, OR11, NR12R13, CN, NO2, halogen, C1-C20alkyl, C2-C20alkyl which is interrupted by O, CO or NR14 or C3-C10cycloalkyl which optionally is interrupted by O, CO or NR14;

    R16 and R17 independently of each other are hydrogen, C1-C20alkyl, C3-C10cycloalkyl or phenyl;

    orR16 and R17 together with N-atom to which they are attached form a 5- or 6-membered saturated or unsaturated ring, which optionally is interrupted by O, S or NR14;

    or R16 and R17 independently of one another are C2-C5alkylene or C2-C5alkenylene which is attached to one of the C-atoms of the phenyl or naphthyl ring to which the NR16R17 is attached, wherein said C2-C5alkylene or C2-C5alkenylene optionally is interrupted by O, CO or NR15, and to which C2-C5alkylene or C2-C5alkenylene optionally a benzene ring is condensed;

    R18, R19, R20, R′

    18, R′

    19, and R′

    20 independently of one another have one of the meanings as given for R6, R7, R8, R′

    6, R′

    7 and R′

    8;

    R″

    18 and R″

    19 independently of each other have one of the meanings as given for R″

    6 and R″

    7; and

    R′

    ″

    18 and R′

    ″

    19 independently of each another have one of the meanings as given for R′

    ″

    6 and R′

    ″

    7.

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