US2015056554A1PendingUtilityA1
Oxime Ester Photoinitiators
Est. expiryMay 11, 2027(~0.8 yrs left)· nominal 20-yr term from priority
G03F 7/30G02B 5/20C07D 409/14G03F 7/027C07D 209/86C07D 403/10G03F 7/2002G03F 7/2037G03F 7/2039C07D 209/80C07D 209/88C07D 409/06G03F 7/004G03F 7/0045C07D 209/82
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Claims
Abstract
Compounds of formula (I), (II), and (III), wherein R 1 , R 2 , R′ 2 and R′″ 2 for example are C 1 -C 20 alkyl, provided that at least one of R 1 , R 2 , R′ 2 and R′″ 2 carries a specified substituent; R 3 , R 4 , and R 5 for example independently of one another are hydrogen or a defined substituent provided that at least one of R 3 , R 4 or R 5 is other than hydrogen or C 1 -C 20 alkyl; R 6 , R 7 , R 8 , R′ 7 , RV, R′ 8 , R″ 6 , R″ 7 , R′″ 6 and R′″ 7 for example independently of one another have one of the meanings as given for R 3 , R 4 , and R 5 ; and R 9 for example is C 1 -C 20 alkyl; exhibit an unexpectedly good performance in photopolymerization reactions.
Claims
exact text as granted — not AI-modified1 . A compound of the formula I
wherein
R 1 is hydrogen, (CO)R″ 2 , C 1 -C 20 alkoxycarbonyl, phenyl-C 1 -C 4 alkyl, C 1 -C 20 alkyl which optionally is substituted by one or more halogen, COOR 11 or CONR 12 R 13 ;
or R 1 is C 2 -C 20 alkyl which is interrupted by O, CO or NR 14 ; or is C 2 -C 12 alkenyl which optionally is interrupted by O, CO or NR 14 , or is C 4 -C 8 cycloalkenyl or C 2 -C 12 alkinyl;
or R 1 is benzoyl, naphthoyl, phenyloxycarbonyl or naphtyloxycarbonyl; or is benzoyl, naphthoyl, phenyloxycarbonyl or naphtyloxycarbonyl each of which is substituted by one or more C 1 -C 20 alkyl, C 1 -C 4 haloalkyl, SR 10 , OR 11 , NR 12 R 13 , halogen, phenyl, COOR 11 , CONR 12 R 13 , CN, NO 2 or by C 3 -C 10 cycloalkyl which optionally is interrupted by O, CO or NR 14 ;
or R 1 is C 3 -C 10 cycloalkyl which optionally is interrupted by O, CO or NR 14 , or is C 3 -C 10 cycloalkylcarbonyl which optionally is interrupted by O, CO or NR 14 , or is C 3 -C 10 cycloalkyloxycarbonyl which optionally is interrupted by O, CO or NR 14 ;
or R 1 is unsubstituted phenyl or naphthyl, or is phenyl or naphthyl which is substituted by one or more C 1 -C 20 alkyl, C 1 -C 4 haloalkyl, SR 10 , OR 11 , NR 12 R 13 , halogen, phenyl, COOR 11 , CONR 12 R 13 , CN, NO 2 , or by C 3 -C 10 cycloalkyl which optionally is interrupted by O, CO or NR 14 ;
R 2 and R′ 2 independently of each other are hydrogen, C 1 -C 20 alkyl which C 1 -C 20 alkyl optionally contains one or more C—C multiple bonds;
C 3 -C 10 cycloalkyl which optionally is interrupted by O, CO or NR 14 and which uninterrupted or interrupted C 3 -C 10 cycloalkyl optionally contains one or more C—C multiple bonds;
or R 2 and R′ 2 are C 1 -C 20 alkyl which is substituted by one or more halogen, OR 11 , COOR 11 , NR 12 R 13 , C 1 -C 20 heteroaryl, C 1 -C 20 heteroaryl-(CO)O, C 1 -C 20 heteroaryl-S, CONR 12 R 13 ,
phenyl or by phenyl which is substituted by SR 10 , OR 11 or NR 12 R 13 , which substituted C 1 -C 20 alkyl optionally contains one or more C—C multiple bonds;
or R 2 and R′ 2 are C 2 -C 20 alkyl which is interrupted by one or more O and/or optionally is substituted by one or more halogen, OR 11 , COOR 11 , NR 12 R 13 , C 1 -C 20 heteroaryl, C 1 -C 20 heteroaryl-(CO)O, C 1 -C 20 heteroaryl-S, CONR 12 R 13 ,
phenyl or by phenyl which is substituted by SR 10 , OR 11 , or NR 12 R 13 , which interrupted C 2 -C 20 alkyl optionally contains C—C multiple bonds;
or R 2 and R′ 2 are unsubstituted phenyl, naphthyl or C 1 -C 20 heteroaryl; or are phenyl, naphthyl or C 1 -C 20 heteroaryl which is substituted by one or more C 1 -C 12 alkyl, C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, phenyl, halogen, CN, NO 2 , SR 10 , OR 11 , NR 12 R 13 or by C 3 -C 10 cycloalkyl which optionally is interrupted by O, CO or NR 14 ;
or R 2 and R′ 2 are C 2 -C 20 alkanoyl, or benzoyl which is unsubstituted or substituted by one or more C 1 -C 6 alkyl, phenyl, SR 10 , OR 11 or NR 12 R 13 ;
or R 2 and R′ 2 are C 2 -C 12 alkoxycarbonyl which optionally is interrupted by one or more O and/or optionally is substituted by one or more OH;
or R 2 and R′ 2 are phenoxycarbonyl which is unsubstituted or substituted by one or more C 1 -C 6 alkyl, halogen, phenyl, SR 10 , OR 11 or NR 12 R 13 ;
or R 2 and R′ 2 are NR 12 R 13 or
or R 2 and R′ 2 form a ring with one of the C-atoms of the phenyl or naphthyl ring to which the group
or (CO)R′ 2 is attached, wherein said formed ring is unsubstituted or substituted;
R″ 2 has one of the meanings given for R 2 and R′ 2 or is
R′″ 2 has one of the meanings given for R 2 and R′ 2 or is
R 3 , R 4 , and R 5 independently of one another are hydrogen, halogen,
C 1 -C 20 alkyl, C 2 -C 20 alkyl which is interrupted by O, CO or NR 14 , or are C 2 -C 12 alkenyl which optionally is interrupted by O, CO or NR 14 , or are C 4 -C 8 cycloalkenyl, C 2 -C 12 alkinyl, phenyl-C 1 -C 4 alkyl, CN, NO 2 or C 3 -C 10 cycloalkyl which optionally is interrupted by O, CO or NR 14 ;
or R 3 , R 4 , and R 5 are phenyl which is unsubstituted or substituted by one or more C 1 -C 20 alkyl, halogen, CN, SR 10 , OR 11 or NR 12 R 13 ;
or R 3 , R 4 , and R 5 are (CO)R′ 2 , SR 10 , OR 11 , SOR 10 , SO 2 R 10 or NR 12 R 13 , wherein the substituents (CO)R′ 2 , OR 11 , SR 10 and NR 12 R 13 optionally form 5- or 6-membered rings via the radicals R 10 , R 11 , R 12 R 13 , 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 R 3 , R 4 or R 5 is other than hydrogen or C 1 -C 20 alkyl; and that
(ii) if one of R 3 , R 4 or R 5 in the para position of the phenyl ring is SR 10 then R 10 is not unsubstituted phenyl; and
(iii) if one of R 3 , R 4 or R 5 in the para position of the phenyl ring is NR 12 R 13 , then R 12 and R 13 are not both C 1 -C 20 alkyl; and
(iv) if one of R 3 , R 4 or R 5 in the para position of the phenyl ring is NR 12 R 13 and R 12 and R 13 together with the N-atom to which they are attached form a ring, said ring is not a morpholino ring; and
(v) if R 3 is hydrogen, R 4 is hydrogen or C 1 -C 20 alkyl in the ortho-position of the phenyl ring and R 5 is OR 11 in the para-position of the phenyl ring, then R 11 is not C 3 -C 10 cycloalkyl or C 3 -C 10 cycloalkyl which is interrupted by O;
R 6 , R 7 , R′ 6 , and R′ 7 , independently of one another have one of the meanings as given for R 3 , R 4 and R 5 ;
R 9 is hydrogen, C 3 -C 8 cycloalkyl, C 2 -C 5 alkenyl, C 1 -C 20 alkoxy, unsubstituted C 1 -C 20 alkyl or C 1 -C 20 alkyl which is substituted by one or more halogen, phenyl, C 1 -C 20 alkylphenyl and/or CN;
or R 9 is phenyl or naphthyl, both of which are unsubstituted or substituted by one or more C 1 -C 6 alkyl, halogen, CN, OR 11 , SR 10 and/or NR 12 R 13 ;
or R 9 is benzyloxy or phenoxy both of which are unsubstituted or substituted by one or more C 1 -C 6 alkyl and/or halogen;
R 10 is hydrogen, C 1 -C 20 alkyl, C 3 -C 12 alkenyl, C 3 -C 10 cycloalkyl which optionally is interrupted by O, CO or NR 14 , or R 10 is phenyl-C 1 -C 4 alkyl or is C 1 -C 20 alkyl which is substituted by OH, SH, CN, C 3 -C 6 alkenoxy, C 1 -C 20 heteroaryl, C 1 -C 20 heteroaryl-(CO)O, C 1 -C 20 heteroaryl-S,
—OCH 2 CH 2 (CO)O(C 1 -C 4 alkyl), —O(CO)—(C 1 -C 4 alkyl), —O(CO)-phenyl, —(CO)OH or —(CO)O(C 1 -C 4 alkyl);
or R 10 is C 2 -C 20 alkyl which is interrupted by one or more O or S;
or R 10 is —(CH 2 CH 2 O) n H, —(CH 2 CH 2 O) n (CO)—(C 1 -C 8 alkyl), C 2 -C 8 alkanoyl, benzoyl, C 3 -C 12 alkenyl or C 3 -C 6 alkenoyl;
or R 10 is phenyl, naphthyl or C 1 -C 20 heteroaryl, each of which is unsubstituted or substituted by one or more halogen, C 1 -C 12 alkyl, C 1 -C 12 alkoxy, phenyl-C 1 -C 3 alkyloxy, phenoxy, C 1 -C 12 alkylsulfanyl, phenylsulfanyl, —N(C 1 -C 12 alkyl) 2 , diphenylamino, —(CO)O(C 1 -C 8 alkyl) or by (CO)N(C 1 -C 8 alkyl) 2 ;
or R 10 is phenyl, naphtyl or C 1 -C 20 heteroaryl which forms a 5- or 6-membered ring with the phenyl ring to which the SR 10 is attached via a direct bond, C 1 -C 4 alkylene, O, S, NR 14 or CO, wherein said phenyl or naphthyl is unsubstituted or substituted by one or more C 1 -C 20 alkyl, C 2 -C 20 alkyl which is interrupted by O, CO or NR 14 , or is substituted by C 3 -C 10 cycloalkyl which is optionally interrupted by O, CO or NR 14 , or is substituted by halogen, C 1 -C 20 alkoxy, C 1 -C 20 alkylcarbonyl or phenylcarbonyl;
n is an integer from 1-12;
R 11 is hydrogen, C 1 -C 20 alkyl which optionally is substituted by one or more halogen; or R 11 is —(CH 2 CH 2 O) n H, —(CH 2 CH 2 O) n (CO)—(C 1 -C 8 alkyl), C 1 -C 8 alkanoyl, C 3 -C 12 alkenyl, C 3 -C 6 alkenoyl, phenyl-C 1 -C 4 alkyl or is C 2 -C 20 alkyl which is interrupted by one or more O; or is C 3 -C 10 cycloalkyl which optionally is interrupted by O, CO or NR 14 ;
or R 11 is C 1 -C 20 alkyl which is substituted by OH, SH, CN, C 3 -C 6 alkenoxy, C 1 -C 20 heteroaryl, C 1 -C 20 heteroaryl-(CO)O, C 1 -C 20 heteroaryl-S, —OCH 2 CH 2 CN, —OCH 2 CH 2 (CO)O(C 1 -C 4 alkyl),
—O(CO)—(C 1 -C 4 alkyl), —O(CO)-phenyl, —(CO)OH or —(CO)O(C 1 -C 4 alkyl);
or R 11 is benzoyl which is unsubstituted or substituted by one or more C 1 -C 6 alkyl, halogen, OH or C 1 -C 4 alkoxy;
or R 11 is phenyl, naphthyl or C 1 -C 20 heteroaryl each of which is unsubstituted or substituted by one or more halogen, OH, C 1 -C 12 alkyl, C 3 -C 10 cycloalkyl or C 1 -C 12 alkoxy;
R 12 and R 13 independently of one another are hydrogen, C 1 -C 20 alkyl, C 2 -C 20 alkyl which is interrupted by O, CO or NR 14 , or are C 2 -C 4 hydroxyalkyl, C 1 -C 12 alkoxy, phenyl-C 1 -C 4 alkyl, (CO)R 15 , C 2 -C 10 alkoxyalkyl, C 3 -C 5 alkenyl or C 3 -C 10 cycloalkyl which optionally is interrupted by O, CO or NR 14 ;
or R 12 and R 13 are phenyl or naphthyl, each of which is unsubstituted or substituted by one or more C 1 -C 20 alkoxy, (CO)R 15 , phenyl, NR 16 R 17 , SR 10 , OR 11 , C 1 -C 20 alkyl, by C 2 -C 20 alkyl which is interrupted by O, CO or NR 14 or are substituted by C 3 -C 10 cycloalkyl which optionally is interrupted by O, CO or NR 14 ;
or R 12 and R 13 independently of each other are C 2 -C 5 alkylene or C 2 -C 5 alkenylene which is attached to one of the C-atoms of the phenyl or naphthyl ring to which the NR 12 R 13 is attached, wherein said C 2 -C 5 alkylene or C 2 -C 5 alkenylene optionally is interrupted by O, CO or NR 14 ; or
R 12 and R 13 independently of one another are phenyl which is attached via a direct bond to the phenyl ring on which the NR 12 R 13 is positioned; or
R 12 and R 13 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 NR 14 , and which ring is unsubstituted or substituted by one or more C 1 -C 20 alkyl, C 1 -C 20 alkoxy, ═O, SR 10 , OR 11 , NR 16 R 17 , (CO)R 15 , NO 2 , CN, phenyl or by C 3 -C 10 cycloalkyl which optionally is interrupted by O, CO or NR 14 ; or
R 12 and R 13 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 C 1 -C 20 alkyl, C 1 -C 20 alkoxy, ═O, SR 10 , OR 11 , NR 16 R 17 , (CO)R 15 , NO 2 , CN, phenyl or by C 3 -C 10 cycloalkyl which optionally is interrupted by O, CO or NR 14 ;
R 14 is hydrogen, C 1 -C 20 alkyl, C 3 -C 8 cycloalkyl, phenyl or (CO)R 15 ;
R 15 is hydrogen, OH, C 1 -C 20 alkyl, C 1 -C 4 haloalkyl, C 2 -C 20 alkyl which is interrupted by O, CO or NR 14 , or is C 3 -C 10 cycloalkyl which optionally is interrupted by O, CO or NR 14 , or is phenyl-C 1 -C 4 alkyl, SR 10 , OR 11 or NR 12 R 13 ;
or R 15 is phenyl, naphthyl or C 1 -C 20 heteroaryl all of which are unsubstituted or substituted by one or more SR 10 , OR 11 , NR 12 R 13 ,
CN, NO 2 , halogen, C 1 -C 20 alkyl, C 1 -C 4 haloalkyl, by C 2 -C 20 alkyl which is interrupted by O, CO or NR 14 or are substituted by C 3 -C 10 cycloalkyl which optionally is interrupted by O, CO or NR 14 ;
R 16 and R 17 independently of each other are hydrogen, C 1 -C 20 alkyl, C 3 -C 10 cycloalkyl or phenyl; or
R 16 and R 17 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 NR 14 ;
or R 16 and R 17 independently of one another are C 2 -C 5 alkylene or C 2 -C 5 alkenylene which is attached to one of the C-atoms of the phenyl or naphthyl ring to which the NR 16 R 17 is attached, wherein said C 2 -C 5 alkylene or C 2 -C 5 alkenylene optionally is interrupted by O, CO or NR 15 , and to which C 2 -C 5 alkylene or C 2 -C 5 alkenylene optionally a benzene ring is condensed;
R 18 , R 19 , R 20 , R′ 18 , R′ 19 , and R′ 20 independently of one another are hydrogen, halogen,
C 1 -C 20 alkyl, C 2 -C 20 alkyl which is interrupted by O, CO or NR 14 , or are C 2 -C 12 alkenyl which optionally is interrupted by O, CO or NR 14 , or are C 4 -C 8 cycloalkenyl, C 2 -C 12 alkinyl, phenyl-C 1 -C 4 alkyl, CN, NO 2 or C 3 -C 10 cycloalkyl which optionally is interrupted by O, CO or NR 14 ;
or R 18 , R 19 , R 20 , R′ 18 , R′ 19 , and R′ 20 are phenyl which is unsubstituted or substituted by one or more C 1 -C 20 alkyl, halogen, CN, SR 10 , OR 11 or NR 12 R 13 ;
or R 18 , R 19 , R 20 , R′ 18 , R′ 19 , and R′ 20 are (CO)R′ 2 , SR 10 , OR 11 , SOR 10 , SO 2 R 10 or NR 12 R 13 , wherein the substituents (CO)R′ 2 , OR 11 , SR 10 and NR 12 R 13 optionally form 5- or 6-membered rings via the radicals R 10 , R 11 , R 12 R 13 , and/or R′ 2 with further substituents on the phenyl ring or with one of the carbon atoms of the phenyl ring;
R″ 18 and R″ 19 independently of each other have one of the meanings as given for for R 3 , R 4 and R 5 ,
or R″ 18 and R″ 19 together are C 1 -C 6 alkylene or C 2 -C 6 alkenylene 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 C 1 -C 20 alkyl, or by C 2 -C 20 alkyl which is interrupted by O, CO or NR 14 , or said bicyclic ring optionally is substituted by C 1 -C 4 haloalkyl, SR 10 , OR 11 , NR 12 R 13 , halogen, phenyl, COOR 11 , CONR 12 R 13 , CN, NO 2 , or C 3 -C 10 cycloalkyl which optionally is interrupted by O, CO or NR 14 ; provided that the group
is attached to either ring; and
R′″ 18 and R′″ 19 independently of each another have one of the meanings as given for for R 3 , R 4 and R 5 ,
or R′″ 18 and R′″ 19 together are C 2 -C 6 alkylene or C 2 -C 6 alkenylene 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 C 1 -C 20 alkyl, by C 2 -C 20 alkyl which is interrupted by O, CO or NR 14 , or said bicyclic ring optionally is substituted by C 1 -C 4 haloalkyl, SR 10 , OR 11 , NR 12 R 13 , halogen, phenyl, COOR 11 , CONR 12 R 13 , CN, NO 2 , or by C 3 -C 10 cycloalkyl which optionally is interrupted by O, CO or NR 14 ;
provided that one or more groups (CO)R′″ 2 are attached to either ring;
R 21 is COOR 11 , CONR 12 R 13 or (CO)R 9 ; or R 21 has one of the meanings as given for R 15 ;
R 22 is COOR 11 , CONR 12 R 13 or (CO)R 9 ; or R 22 has one of the meanings as given for R 12 and R 13 ;
X is O, S, SO or SO 2 ;
X 2 is a direct bond, C 1 -C 20 alkylene which optionally is interrupted by O, CO or NR 14 , and which uninterrupted or interrupted C 1 -C 20 alkylene is unsubstituted or substituted by one or more halogen, OR 11 , COOR 11 , NR 12 R 13 , C 1 -C 20 heteroaryl, C 1 -C 20 heteroaryl(CO)O, C 1 -C 20 heteroaryl-S, CONR 12 R 13 ,
phenyl or by phenyl which is substituted by halogen, C 1 -C 20 alkyl, C 1 -C 4 haloalkyl, SR 10 , OR 11 , or NR 12 R 13 , and which unsubstituted or substituted, interrupted or non-interrupted C 1 -C 20 alkylene optionally contains one or more C—C multiple bonds;
m is an integer 1 or 2;
R 23 has one of the meanings as given for R 9 ;
R 24 is hydrogen, C 1 -C 20 alkyl; C 2 -C 20 alkenyl; C 3 -C 10 cycloalkyl which optionally is interrupted by O, CO or NR 14 , or R 24 is C 3 -C 10 cycloalkenyl; C 1 -C 20 alkyl which is substituted by one or more halogen, OR 11 , COOR 11 , NR 12 R 13 , C 1 -C 20 heteroaryl, C 1 -C 20 heteroaryl(CO)O, C 1 -C 20 heteroaryl-S, CONR 12 R 13 ,
or by phenyl;
or R 24 is C 2 -C 20 alkyl which is interrupted by one or more O and/or optionally is substituted by one or more halogen, OR 11 , COOR 11 , NR 12 R 13 , C 1 -C 20 heteroaryl, C 1 -C 20 heteroaryl-(CO)O, C 1 -C 20 heteroaryl-S, CONR 12 R 13 ,
or by phenyl;
or R 24 is phenyl, naphthyl or C 1 -C 20 heteroaryl, all of which optionally are substituted by one or more C 1 -C 12 alkyl, phenyl, halogen, C 1 -C 4 haloalkyl, CN, NO 2 , SR 10 , OR 11 , NR 12 R 13 or by C 3 -C 10 cycloalkyl which optionally is interrupted by O, CO or NR 14 ;
or R 24 is C 2 -C 20 alkanoyl, or benzoyl which is unsubstituted or substituted by one or more C 1 -C 6 alkyl, halogen, phenyl, SR 10 , OR 11 or NR 12 R 13 ;
or R 24 is C 2 -C 12 alkoxycarbonyl which optionally is interrupted by one or more O and/or optionally is substituted by one or more OH;
or R 24 is phenoxycarbonyl which is unsubstituted or substituted by one or more C 1 -C 6 alkyl, C 1 -C 4 haloalkyl, halogen, phenyl, SR 10 , OR 11 or NR 12 R 13 ;
or R 24 is NR 12 R 13 ;
or R 24 forms a ring with one of the C-atoms of the phenyl or naphthyl ring to which the group
is attached, wherein said formed ring is unsubstituted or substituted; or R 24 is
provided that
(a) at least one of
R 2 in formula I,
R′ 2 in the group (CO)R′ 2
in the definition of R 3 , R 4 , R 5 , R 6 , R 7 , R′ 6 or R′ 7 in formula I or
or
in the definition of R 18 , R 19 , R 20 , R′ 18 , R′ 19 , R′ 20 in the group
for R 24 in formula I via the radicals R 2 or R′ 2 ; or
R″ 2
in the group (CO)R″ 2 in R 1 of formula I or in the group
in R 15 in formula I via the radicals R 1 or R 14
is NR 12 R 13 or
or
(b) at least one of
R 2 in formula I,
R′ 2 in the group (CO)R′ 2
in the definition of R 3 , R 4 , R 5 , R 6 , R 7 , R′ 6 or R′ 7 in formula I or
in the definition of R 18 , R 19 , R 20 , R′ 18 , R′ 19 , R′ 20 in the group
for R 24 in formula I via the radicals R 2 or R′ 2 ; or
R″ 2
in the group (CO)R″ 2 in R 1 of formula I or
in the group
in R 15 in formula I via the radicals R 1 or R 14
forms a ring with one of the C-atoms of the phenyl or naphthyl ring to which the corresponding group
(CO)R′ 2 or (CO)R′″ 2 is attached; or
(c) at least one of
R 2 in formula I,
R′ 2 in the group (CO)R′ 2
in the definition of R 3 , R 4 , R 5 , R 6 , R 7 , R′ 6 or R′ 7 in formula I or
in the definition of R 18 , R 19 , R 20 , R′ 18 , R′ 19 , R′ 20 in the group
for R 24 in formula I via the radicals R 2 or R′ 2 ;
R″ 2
in the group (CO)R″ 2 in R 1 of formula I or
in the group
in R 15 in formula I via the radicals R 1 or R 14 or
contains one or more C—C multiple bonds; or
(d) at least one of
R 2 in formula I,
R′ 2 in the group (CO)R′ 2
in the definition of R 3 , R 4 , R 5 , R 6 , R 7 , R′ 6 or R′ 7 in formula I or
in the definition of R 18 , R 19 , R 20 , R′ 18 , R′ 19 , R′ 20 in the group
for R 24 in formula I via the radicals R 2 or R′ 2 ;
R″ 2
in the group (CO)R″ 2 in R 1 of formula I or
in the group
in R 15 in formula I via the radicals R 1 or R 14
or
R 10 or R 11 occurring in the groups SR 10 , OR 11 or COOR 11 as a substituent in formula I
is C 1 -C 20 alkyl which is substituted by one or more C 1 -C 20 heteroaryl, C 1 -C 20 heteroaryl-(CO)O, C 1 -C 20 heteroaryl-S or
or
(e) at least one of
R 10 or R 11 occurring in the groups SR 10 , OR 11 or COOR 11 as a substituent in formula I
is an unsubstituted or substituted C 1 -C 20 heteroaryl.
2 . A compound of the formula I according to claim 1 , wherein
R 1 is C 1 -C 20 alkyl; R 2 and R′ 2 independently of each other are C 1 -C 20 alkyl which C 1 -C 20 alkyl optionally contains one or more C—C multiple bonds; or R 2 and R′ 2 are C 1 -C 20 alkyl which is substituted by one or more COOR 11 , C 1 -C 20 heteroaryl-S or
or R 2 and R′ 2 are unsubstituted phenyl or C 1 -C 20 heteroaryl; or are phenyl which is substituted by one or more C 1 -C 12 alkyl or SR 10 ;
or R 2 and R′ 2 are
or R 2 and R′ 2 form a ring with one of the C-atoms of the phenyl or naphthyl ring to which the group
or (CO)R′ 2 is attached, wherein said formed ring is unsubstituted or substituted;
R″ 2 has one of the meanings given for R 2 and R′ 2 ;
R′″ 2 has one of the meanings given for R 2 and R′ 2 or is
R 3 , R 4 , and R 5 independently of one another are hydrogen,
or R 3 , R 4 , and R 5 are (CO)R′ 2 , or NR 12 R 13 ,
R 6 , R 7 , R′ 6 , and R′ 7 , independently of one another have one of the meanings as given for R 3 , R 4 and R 5 ;
R 9 is C 1 -C 20 alkyl;
R 10 is C 1 -C 20 heteroaryl;
R 11 is C 1 -C 20 alkyl;
R 12 and R 13 together with the N-atom to which they are attached form a heteroaromatic ring system;
R 18 , R 10 , R 20 , R′ 18 , R′ 19 , and R′ 20 are hydrogen,
or R 18 , R 19 , R 20 , R′ 18 , R′ 19 , and R′ 20 are phenyl which is unsubstituted or substituted by one or more C 1 -C 20 alkyl;
R 21 is (CO)R 9 ;
R 22 is, (CO)R 9 ;
X is O;
X 2 is a direct bond;
m is an integer 1;
R 23 has one of the meanings as given for R 9 ; and
R 24 is C 1 -C 20 alkyl.
3 . A photopolymerizable composition comprising
(a) at least one ethylenically unsaturated photopolymerizable compound and (b) as photoinitiator, at least one compound of the formula I according to claim 1 .
4 . A photopolymerizable composition according to claim 3 comprising in addition to the photoinitiator (b) at least one further photoinitiator (c) and/or other additives (d).
5 . A photopolymerizable composition according to claim 4 comprising as further additive (d) a photosensitizer.
6 . A photopolymerizable composition according to claim 3 , wherein the component (a) is a resin obtained by the reaction of a saturated or unsaturated polybasic acid anhydride with a product of the reaction of an epoxy resin and an unsaturated monocarboxylic acid.
7 . A photopolymerizable composition according to claim 3 additionally comprising a binder polymer (e).
8 . A photopolymerizable composition according to claim 4 comprising as further additive (d) a pigment or a mixture of pigments.
9 . A photopolymerizable composition according to claim 4 comprising as further additive (d) a dispersant or a mixture of dispersants.
10 . A photopolymerizable composition according to claim 4 , comprising 0.005 to 25% by weight of the photoinitiator (b), or the photoinitiators (b) and (c), based on the composition.
11 . A process for the photopolymerization of compounds containing ethylenically unsaturated double bonds, which comprises irradiating a composition according to claim 3 with electromagnetic radiation in the range from 150 to 600 nm, or with electron beam or with X-rays.
12 . A process for the preparation of a compound of the formula I as defined in claim 1 by reacting an oxime compound of formula Ia
wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R′ 6 , R 7 , and R′ 7 , are as defined in claim 1 ,
with an acyl halide or an anhydride of formula V or VI
wherein Hal denotes a halogen atom and R 9 is as defined in claim 1 , in the presence of a base or a mixture of bases.
13 . The composition according to claim 3 for producing pigmented and nonpigmented paints and varnishes, powder coatings, printing inks, printing plates, adhesives, pressure sensitive adhesives, dental compositions, gel coats, photoresists for electronics, electroplating resists, etch resists, both liquid and dry films, solder resists, resists to manufacture color filters for a variety of display applications, resists to generate structures in the manufacturing processes of plasma-display panels, electroluminescence displays and LCD, spacers for LCD, for holographic data storage (HDS), as composition for encapsulating electrical and electronic components, for producing magnetic recording materials, micromechanical parts, waveguides, optical switches, plating masks, etch masks, colour proofing systems, glass fibre cable coatings, screen printing stencils, for producing three-dimensional objects by means of stereolithography, as image recording material, for holographic recordings, microelectronic circuits, decolorizing materials, decolorizing materials for image recording materials, for image recording materials using microcapsules, as a photoresist material for a UV and visible laser direct imaging system, as a photoresist material used for forming dielectric layers in a sequential build-up layer of a printed circuit board.
14 . A process according to claim 11 for producing pigmented and nonpigmented paints and varnishes, powder coatings, printing inks, printing plates, adhesives, pressure sensitive adhesives, dental compositions, gel coats, photoresists for electronics, electroplating resists, etch resists, both liquid and dry films, solder resists, resists to manufacture color filters for a variety of display applications, resists to generate structures in the manufacturing processes of plasma-display panels, electroluminescence displays and LCD, spacers for LCD, for holographic data storage (HDS), as composition for encapsulating electrical and electronic components, for producing magnetic recording materials, micromechanical parts, waveguides, optical switches, plating masks, etch masks, colour proofing systems, glass fibre cable coatings, screen printing stencils, for producing three-dimensional objects by means of stereolithography, as image recording material, for holographic recordings, microelectronic circuits, decolorizing materials, decolorizing materials for image recording materials, for image recording materials using microcapsules, as a photoresist material for a UV and visible laser direct imaging system, as a photoresist material used for forming dielectric layers in a sequential build-up layer of a printed circuit board.
15 . A coated substrate which is coated on at least one surface with a composition according to claim 3 .
16 . A process for the photographic production of relief images, in which a coated substrate according to claim 15 is subjected to imagewise exposure and then the unexposed portions are removed with a developer.
17 . A color filter prepared by providing red, green and blue picture elements and a black matrix, all comprising a photosensitive resin according to claim 3 and a pigment on a transparent substrate and providing a transparent electrode either on the surface of the substrate or on the surface of the color filter layer, wherein said photosensitive resin comprises a polyfunctional acrylate monomer, an organic polymer binder and a photopolymerization initiator of formula I.
18 . A compound of the formula Ia
wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R′ 6 , R 7 , and R′ 7 are as defined in claim 1 .
19 . A photopolymerizable composition according to claim 5 wherein the photosensitizer is selected from the group consisting of benzophenones, thioxanthones, anthraquinones, and coumarin and its derivatives.
20 . A photopolymerizable composition according to claim 7 wherein the binder polymer is a copolymer of methacrylate and methacrylic acid.Join the waitlist — get patent alerts
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