Bathochromic mono-and bis-acylphosphine oxides and sulfides and their use as photoinitiators
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C07F-009/02
C07F-009/00
출원번호
US-0485836
(2002-08-13)
우선권정보
CH-1542/01(2001-08-21)
국제출원번호
PCT/EP02/009045
(2002-08-13)
§371/§102 date
20040204
(20040204)
국제공개번호
WO03/019295
(2003-03-06)
발명자
/ 주소
Wolf,Jean Pierre
Hug,Gebhard
출원인 / 주소
Ciba Specialty Chemicals Corporation
인용정보
피인용 횟수 :
12인용 특허 :
6
초록▼
Compounds of formula (I), wherein A is S or O; x is 0 or 1; a is SR10 or N(R11)(R12); R1 and R 2 are C1-C24alkyl, OR10, CF3 or halogen; R3, R4 and R5 are hydrogen, C 1-C24alkyl, OR10 or halogen; or two of the radicals R11 R21 R31 R4 and/or R9 together form C1-C2oalkylene uninterrupted or interrupted
Compounds of formula (I), wherein A is S or O; x is 0 or 1; a is SR10 or N(R11)(R12); R1 and R 2 are C1-C24alkyl, OR10, CF3 or halogen; R3, R4 and R5 are hydrogen, C 1-C24alkyl, OR10 or halogen; or two of the radicals R11 R21 R31 R4 and/or R9 together form C1-C2oalkylene uninterrupted or interrupted by O, S or NR13; R6, R11 R8 and R9 are hydrogen, C1-C24alkyl; C 2-C24alkyl which is interrupted one or more times by non-consecutive O atoms and unsubstituted or substituted by OH and/or SH, or R6, R7, R8 and Rg are OR10; halogen; or phenyl unsubstituted or substituted one or more times by C-Calkyl; R10, R11 and R12 are e.g. hydrogen; X is e.g. (II), and R2; have one of the meanings given for R1 and R2; and R3', R4' and Rs' have one of the meanings given for R3, R4 and R5; are suitable as photoinitiators, especially for irradiation with light of relatively long wavelengths
대표청구항▼
What is claimed is: 1. A compound of formula I wherein A is S or O; x is 0 or 1; Q is SR10 or N(R11)(R12); R1 and R2 are each independently of the other C1-C24alkyl, OR10, CF3 or halogen; R3, R4 and R5 are each independently of the others hydrogen, C1-C24alkyl, OR10 or halogen; or two of the rad
What is claimed is: 1. A compound of formula I wherein A is S or O; x is 0 or 1; Q is SR10 or N(R11)(R12); R1 and R2 are each independently of the other C1-C24alkyl, OR10, CF3 or halogen; R3, R4 and R5 are each independently of the others hydrogen, C1-C24alkyl, OR10 or halogen; or two of the radicals R1, R2, R3, R4 and/or R5 together form C1-C20alkylene which is uninterrupted or interrupted by O, S or NR13; R6, R7, R8 and R9 are each independently of the others hydrogen, C1-C24alkyl; C2-C24alkyl which is interrupted one or more times by non-consecutive O atoms and which is unsubstituted or substituted by OH and/or SH; or R6, R7, R8 and R9 are OR10; halogen; or phenyl unsubstituted or substituted one or more times by C1-C4alkyl; R10, R11 and R12 are each independently of the others hydrogen, C1-C24alkyl, C 2-C24alkenyl, C3-C8cycloalkyl, phenyl, benzyl, or C2-C20alkyl which is interrupted one or more times by non-consecutive O atoms and which is unsubstituted or substituted by OH and/or SH; or R11 and R12 together with the N atom to which they are bonded form a 5-or 6-membered ring, which may also contain O or S atoms or an NR13 group; R13 is hydrogen, phenyl, C1-C12 alkoxy, C1-C12alkyl, or C2-C12alkyl which is interrupted one or more times by O or S and which is unsubstituted or substituted by OH and/or SH; or OR10 or X is C1-C24alkyl which is unsubstituted or substituted one or more times by OR15, SR 15, N(R16)(R17), phenyl, halogen, CN,--N═ C═A, or X is C2-C24alkyl which is interrupted one or more times by O, S or NR13 and which is unsubstituted or substituted by OR15, SR15, N(R16)(R17) , phenyl, halogen, or X is C1-C24alkoxy which is uninterrupted or interrupted one or more times by O, S or NR13 and which is unsubstituted or substituted one or more times by OR 15, SR15, N(R16)(R17), phenyl, CN,--N═C═A, or X is C3-C24cycloalkyl unsubstituted or substituted by C1-C20alkyl, OR10, CF3 or by halogen; or C2-C24alkenyl unsubstituted or substituted by C6-C14aryl, CN, (CO)OR15 or by (CO)N(R18)(R19); or X is C3-C24cycloalkenyl or is one of the radicals C1-C24alkylthio wherein the alkyl radical is uninterrupted or interrupted one or more times by non-consecutive O or S and unsubstituted or substituted by OR15, SR15 and/or halogen; A1 is O, S or NR21; R14 has one of the meanings given for R6, R7, R8 and R9; R1' and R2' each independently of the other has one of the meanings given for R1 and R2; R3', R4' and R5' each independently of the others has one of the meanings given for R3, R4 and R5; R15, R16 and R17 each independently of the others has one of the meanings given for R10 or is a radical R18 and R19 are each independently of the other hydrogen, C1-C24alkyl, C2-C12 alkenyl, C3-C8cycloalkyl, phenyl, benzyl; or C2-C20alkyl which is interrupted one or more times by O or S and which is unsubstituted or substituted by OH; R20 is C1-C20alkyl which is substituted one or more times by OR15 or halogen; or is C 2-C20alkyl which is interrupted one or more times by non-consecutive O atoms and which is unsubstituted or substituted one or more times by OR15 or halogen; or R20 is C2-C 20alkenyl or C2-C12alkynyl; or R20 is C3-C12cycloalkenyl which is substituted one or more times by halogen, NO2, C1-C6alkyl, OR10 or by C(O)OR18; or is C7-C16arylalkyl or C8-C16arylcycloalkyl; R21 and R22 are each independently of the other hydrogen; C1-C20alkyl which is substituted one or more times by OR15, halogen, styryl, methylstyryl or by--N═ C═A; or C2-C20alkyl which is interrupted one or more times by non-consecutive O atoms and which is unsubstituted or substituted one or more times by OR15, halogen, styryl or by methylstyryl; or R21 and R22 are each independently of the other C2-C12alkenyl; C5-C12 cycloalkyl which is substituted by--N═C═A or--CH2--N═C═A and may additionally be substituted by one or more C 1-C4alkyl substituents; or R21 and R22 are each independently of the other C6-C14aryl unsubstituted or substituted one or more times by halogen, NO2, C1-C6alkyl, C2-C4alkenyl, OR 10,--N═C═A,--CH2--N═C═A or by C(O) OR18; or R21 and R22 are C7-C 16arylalkyl; or R21 and R22 together are C 8-C16arylcycloalkyl; or R21 and R22 are each independently of the other Y1 is O, S, SO, SO2, CH2, C(CH 3)2, CHCH3, C(CF3)2, (CO) or a direct bond; R23, R24, R25, R26 and R27 have one of the meanings given for R6 or are NO 2, CN, SO2R28, OSO2R24, CF 3, CCl3 or halogen; R28 is C1-C12alkyl, halo-substituted C1-C12alkyl, phenyl, or phenyl substituted by OR15 and/or SR15; X1 is CH2, CHCH3 or C(CH3) 2; X3 is C1-C24alkylene; C2-C24alkylene interrupted one or more times by O, S or NR 13; C2-C24alkenylene; C2-C24 alkenylene interrupted one or more times by O, S or NR13; C3-C24cycloalkylene; C3-C 24cycloalkylene interrupted one or more times by O, S or NR 13; C3-C24cycloalkenylene; or C3-C 24cycloalkenylene interrupted one or more times by O, S or NR 13; the radicals C1-C24alkylene, C2-C24alkylene, C2-C24alkenylene, C3-C24cycloalkylene and C3-C24cycloalkenylene being unsubstituted or substituted by OR10, SR10, N(R11)(R12) and/or by halogen; or X3 is one of the radicals phenylene, those radicals being unsubstituted or substituted on the aromatic ring by C1-C20alkyl; C2-C20 alkyl which is interrupted one or more times by non-consecutive O atoms and which is unsubstituted or substituted by OH and/or SH; OR10, SR10, N(R11)(R12), phenyl, halogen, NO 2, CN, (CO)--OR18, (CO)--R18, (CO)--N(R18) (R19), SO2R28, OSO2R28, CF3 and/or by CCl3; or X3 is a group X4 is S, O, CH2, CHCH3, C(CH 3)2, C(CF3)2, CO, SO or SO2; X5 and X6 are each independently of the other CH2, CHCH3 or C(CH3)2; r is 0, 1 or 2; s is a number from 1 to 12; q is a number from 0 to 50; t and p are each a number from 0 to 20; and E, G, G1 and G2 are each independently of the others unsubstituted or halo-substituted C1-C12 alkyl, or phenyl unsubstituted or substituted by one or more C1-C4alkyl substituents. 2. A compound of formula I according to claim 1, wherein A is O; x is 1; Q is SR10 or N(R11)(R12); R1 and R2 are each independently of the other C1-C12alkyl, OR10, CF3 or halogen; R3, R4 and R5 are each independently of the others hydrogen, C1-C12alkyl, OR10 or halogen; R6, R7, R8 and R9 are each independently of the others hydrogen, C1-C12alkyl, OR10, halogen, or phenyl unsubstituted or substituted one or more times by C1-C4alkyl; R10, R11 and R12 are each independently of the others hydrogen, C1-C12alkyl, C 3-C8cycloalkyl, C2-C12alkenyl, phenyl, benzyl, or C2-C20alkyl which is interrupted one or more times by non-consecutive O atoms and which is unsubstituted or substituted by OH and/or SH; or R11 and R12 together with the N atom to which they are bonded form a 5-or 6-membered ring, which may also contain O atoms or a NR13 group; R13 is hydrogen or C1-C12alkyl; or OR10 or X is C1-C24alkyl which is unsubstituted or substituted one or more times by OR15, SR 15, N(R16)(R17), phenyl, halogen, CN, or X is C2-C24alkyl which is interrupted one or more times by O, S or NR13 and which is unsubstituted or substituted by OR15, SR15, N(R16)(R17) , phenyl, halogen, or X is C1-C24alkoxy which is uninterrupted or interrupted one or more times by O, S or NR13 and which is unsubstituted or substituted one or more times by OR 15, SR15, N(R16)(R17), phenyl, CN, or X is C2-C24alkenyl unsubstituted or substituted by C6-C14aryl, CN, (CO)OR15 or by (CO)N(R18)(R19); R1' and R2' each independently of the other has one of the meanings given for R1 and R2; and R3', R4' and R5' each independently of the others has one of the meanings given for R3, R4 and R5; R14 has one of the meanings given for R6, R7, R8 and R9; R15, R16 and R17 each independently of the others has one of the meanings given for R10 ; R18 and R19 are each independently of the other hydrogen, C1-C24alkyl, C2-C12 alkenyl, C3-C8cycloalkyl, phenyl, benzyl; or C2-C20alkyl which is interrupted one or more times by O or S; R20 is C1-C20alkyl which is substituted one or more times by OR15 or halogen; or C2-C20alkyl which is interrupted one or more times by non-consecutive O atoms and which is unsubstituted or substituted one or more times by OR15 or halogen; or R20 is C2-C 20alkenyl; and R21 and R22 are each independently of the other hydrogen; C1-C20alkyl which is substituted one or more times by OR15, halogen, styryl, methylstyryl or by--N═ C═A; or C2-C20alkyl which is interrupted one or more times by non-consecutive O atoms and which is unsubstituted or substituted one or more times by OR15, halogen, styryl or by methylstyryl. 3. A compound of formula I according to claim 1, wherein A is O; x is 0 or 1; Q is SR10 or N(R11)(R12); R1 and R2 are each independently of the other C1-C4alkyl; R3, R4 and R5 are each independently of the others hydrogen or C1-C4alkyl; R6, R7, R8 and R9 are hydrogen; R10, R11 and R12 are each independently of the others C1-C4alkyl, C2-C4alkenyl, or C2-C4alkyl which is interrupted by non-consecutive O atoms; or R11 and R12 together with the N atom to which they are bonded form a 5-or 6-membered ring, which may also contain O atoms; or OR10 or X is C1-C12alkyl which is unsubstituted or substituted one or more times by OR15, phenyl, or X is C2-C12alkyl which is interrupted one or more times by O and which is unsubstituted or substituted by OR 15, phenyl, or X is C2-C12alkenyl unsubstituted or substituted by C6-C10aryl, CN or by (CO)OR15; R1' and R2' each independently of the other has one of the meanings given for R1 and R2; R3', R4' and R5' each independently of the others has one of the meanings given for R3, R4 and R5; R15, R16 and R17 each independently of the others has one of the meanings given for R10 ; R18 and R19 are each independently of the other hydrogen, C1-C4alkyl, phenyl, benzyl; or C 2-C6alkyl which is interrupted one or more times by O; R20 is C1-C6alkyl which is substituted one or more times by OR15; or C2-C6 alkyl which is interrupted one or more times by non-consecutive O atoms and which is unsubstituted or substituted one or more times by OR 15; or R20 is C2-C4alkenyl; and R21 and R22 are each independently of the other hydrogen or C1-C20alkyl. 4. A compound of formula I according to claim 1 wherein A is O; x is 0 or 1; Q is SR10 or N(R11)(R12); R1 and R2 are each independently of the other C1-C4alkyl; R3, R4 and R5 are each independently of the others hydrogen or C1-C4alkyl; R6, R7, R8 and R9 are hydrogen; R10, R11 and R12 are each independently of the others C1-C4alkyl, or C2-C4alkyl which is interrupted by non-consecutive O atoms; or R11 and R12 together with the N atom to which they are bonded form a 5-or 6-membered ring, which may also contain O atoms; or C1-C4alkyl which is substituted by phenyl; R1' and R2' each independently of the other has one of the meanings given for R1 and R2; R3', R4' and R5' each independently of the others has one of the meanings given for R3, R4 and R5. 5. A photocurable composition comprising (a) at least one ethylenically unsaturated photopolymerisable compound and (b) at least one compound of formula I according to claim 1 as photoinitiator. 6. A photocurable composition according to claim 5, comprising in addition to components (a) and (b) further photoinitiators (c) and/or further additives (d). 7. A photocurable composition according to claim 6, comprising as further photoinitiator (c) at least one compound of formula III, IV, V, VI wherein R30 is hydrogen, C1-C18alkyl, C 1-C18alkoxy,--OCH2CH2--OR47, morpholino, SCH3, a group or a group n has a value of from 2 to 10; G3 and G4 are each independently of the other terminal groups of the polymeric unit, hydrogen or CH3; R31 is hydroxy, C1-C16alkoxy, morpholino, dimethylamino or--O(CH2CH2O)m--C1-C16alkyl; R32 and R33 are each independently of the other hydrogen, C1-C6alkyl, phenyl, benzyl, C1-C16alkoxy or--O(CH2CH2O)m--C 1-C16alkyl, or R32 and R33 together with the carbon atom to which they are bonded form a cyclohexyl ring; m is a number from 1 to 20; wherein R31, R32 and R33 are not all simultaneously C1-C16alkoxy or--O(CH2 CH2O)m--C1-C16alkyl; R47 is hydrogen, R34, R36, R37 and R38 are each independently of the others hydrogen or methyl; R35 and R39 are hydrogen, methyl or phenylthio, the phenyl ring of the phenylthio radical being unsubstituted or substituted in the 4-, 2-, 2,4-or 2,4,6-position by C1-C 4alkyl; R40 and R41 are each independently of the other C1-C20alkyl, cyclohexyl, cyclopentyl, phenyl, naphthyl or biphenylyl, those radicals being unsubstituted or substituted by halogen, C1-C12alkyl and/or C1-C12 alkoxy, or R40 and R41 have a S-or N-containing 5-or 6-membered heterocyclic ring or--(CO)R42; R42 is cyclohexyl, cyclopentyl, phenyl, naphthyl or biphenylyl, those radicals being unsubstituted or substituted by halogen, C1-C4alkyl and/or C1-C4alkoxy, or R42 is a S-or N-containing 5-or 6-membered heterocyclic ring; R43 and R44 are each independently of the other cyclopentadienyl unsubstituted or mono-, di-or tri-substituted by C1-C18alkyl, C1-C18alkoxy, cyclopentyl, cyclohexyl or halogen; R45 and R46 are each independently of the other phenyl which is substituted by fluorine atoms or CF3 in at least one of the two positions ortho to the titanium-carbon bond and may contain, as further substituents at the aromatic ring, polyoxaalkyl or pyrrolinyl unsubstituted or substituted by one or two C1-C 12alkyl, di(C1-C12alkyl)aminomethyl, morpholinomethyl, C2-C4alkenyl, methoxymethyl, ethoxymethyl, trimethylsilyl, formyl, methoxy or phenyl substituents, or R45 and R46 are R48, R49 and R50 are each independently of the others hydrogen, halogen, C2-C12 alkenyl, C1-C12alkoxy, C2-C12alkoxy interrupted by from one to four O atoms, cyclohexyloxy, cyclopentyloxy, phenoxy, benzyloxy, or phenyl or biphenylyl each unsubstituted or substituted by C1-C4alkoxy, halogen, phenylthio or by C1-C4alkylthio, wherein R48 and R50 are not both simultaneously hydrogen and in the radical at least one radical R48 or R50 is C 1-C12alkoxy, C2-C12alkoxy interrupted by from one to four O atoms, cyclohexyloxy, cyclopentyloxy, phenoxy or benzyloxy; G5 is O, S or NR51; and R51 is C1-C8alkyl, phenyl or cyclohexyl. 8. A composition according to claim 5 which is a pigmented or non-pigmented surface coating, printing ink, screen-printing ink, offset printing ink, flexographic printing ink, powder coating, printing plate, adhesive, dental compound, bonding compound, glass fiber cable coating, screen-printing stencil, resist material, gel coat or encapsulants for electrical and electronic components.
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