Photopolymerizable thermosetting resin compositions

Details Photopolymerizable thermosetting resin compositions Photopolymerizable thermosetting resin compositions

2000-12-22

2002-11-26

Ashton, Rosemary (Department: 1752)

Radiation imagery chemistry: process, composition, or product th

Imaging affecting physical property of radiation sensitive...

Radiation sensitive composition or product or process of making

C430S325000, C430S330000, C430S280100, C522S100000

Reexamination Certificate

active

06485885

ABSTRACT:

The invention pertains to compositions comprising O-acyloxime photoinitiators and the use of these compositions especially in imaging technique.
From U.S. Pat. Nos. 3,558,309, 4,202,697, 4,255,513, 4,590,145 it is known that oxime ester derivatives are photoinitiators. In JP Kokai Hei 8-272095 solder resist ink compositions comprising inter alia 1-phenyl-1,2-propanedione-2-O-benzoyl oxime and 1-phenyl-1,2-propanedione-2-O-ethoxycarbonyl oxime as photoinitiators are disclosed. In JP Kokai Hei 8-339081 in a similar composition 1-phenyl-1,2-propanedione-2-O-ethoxycarbonyl oxime is employed.
In photopolymerization technology there still exists a need for compositions suitable in particular as imaging formulations which are reactive, alkaline developable, easy to handle, exhibit good resolution properties and meet the high requirements of the industry regarding properties like, for example, thermal stability and storage stability.
Surprisingly it was found, that photosensitive thermosetting liquid compositions 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 R
1
is phenyl which is unsubstituted or substituted by one or more C
1
-C
6
alkyl, phenyl, halogen, OR
8
, SR
9
or NR
10
R
11
, or R
1
is C
1
-C
20
alkyl, C
2
-C
20
alkenyl, C
2
-C
20
alkynyl or C
2
-C
20
-alkyl optionally interrupted by one or more —O— and/or optionally substituted by one or more hydroxyl groups, or R
1
is C
2
-C
20
alkanoyl or benzoyl which is unsubstituted or substituted by one or more C
1
-C
6
alkyl, phenyl, OR
8
, SR
9
or NR
10
R
11
, or R
1
is C
2
-C
12
alkoxycarbonyl optionally interrupted by one or more —O— and/or optionally substituted by one or more hydroxyl groups, or R
1
is phenoxycarbonyl which is unsubstituted or substituted by C
1
-C
6
alkyl, halogen, phenyl, OR
8
or NR
10
R
11
, or R
1
is —CONR
10
R
11
, CN, NO
2
, C
1
-C
4
-haloalkyl, S(O)
m
C
1
-C
6
alkyl, unsubstituted or C
1
-C
12
alkyl-substituted S(O)
m
—C
6
-C
12
aryl, SO
2
O—C
1
-C
6
alkyl, SO
2
O—C
6
-C
10
aryl, or diphenyl-phosphinoyl, or R
1
together with R
3
or R
1
together with R
7
may form 5 or 6 membered rings including one or more CO— and/or oxime-groups;
m is 1 or 2;
R
2
is C
2
-C
12
alkanoyl which is unsubstituted or substituted by one or more halogen or CN, or R
2
is C
3
-C
12
alkenoyl, or benzoyl which is unsubstituted or substituted by one or more C
1
-C
6
alkyl, phenyl, halogen CN, OR
8
, SR
9
or NR
10
R
11
, or R
2
is C
2
-C
12
alkoxycarbonyl or phenoxycarbonyl which is unsubstituted or substituted by C
1
-C
6
alkyl or halogen;
R
3
, R
4
, R
5
, R
6
and R
7
independently of one another are hydrogen, halogen, C
1
-C
12
alkyl, cyclopentyl, cyclohexyl or phenyl which is unsubstituted or substituted by one or more OR
8
, SR
9
or NR
10
R
11
, or R
3
, R
4
, R
5
, R
6
and R
7
are benzyl, benzoyl, C
2
-C
12
alkanoyl, C
2
-C
12
alkoxycarbonyl optionally interrupted by one or more —O— and/or optionally substituted by one or more hydroxyl groups or R
3
, R
4
, R
5
, R
6
and R
7
are phenoxycarbonyl or a group OR
8
, SR
9
, SOR
9
, SO
2
R
9
, NO
2
, CN, CONR
10
R
11
, or NR
10
R
11
, wherein the substituents OR
8
, SR
9
and NR
10
R
11
may form 5- or 6-membered rings via the radicals R
8
, R
9
, R
10
and/or R
11
with further substituents on the phenyl ring or with one of the carbon atoms of the phenyl ring;
R
8
is hydrogen, C
1
-C
12
alkyl or C
2
-C
6
alkyl which is substituted by —OH, —SH, —CN, C
1
-C
4
alkoxy, C
3
-C
6
alkenoxy, —OCH
2
CH
2
CN, —OCH
2
CH
2
COO(C
1
-C
4
alkyl), —OCO—C
1
-C
4
alkyl, —OCO-phenyl, COOH or COO(C
1
-C
4
alkyl), or R
8
is C
2
-C
6
alkyl which is interrupted by one or more —O—, or R
8
is —(CH
2
CH
2
O)
n
H, C
2
-C
8
alkanoyl, C
2
-C
12
alkenyl, C
3
-C
6
alkenoyl, cyclohexl or phenyl which is unsubstituted or substituted by halogen, C
1
-C
12
alkyl or C
1
-C
4
alkoxy, or R
8
is phenyl-C
1
-C
3
alkyl or Si(C
1
-C
8
alkyl)
r
(phenyl)
3−r
or R
8
is a group
n is 1-20;
r is 1, 2 or 3;
R
9
is hydrogen, C
1
-C
12
alkyl, C
2
-C
12
alkenyl, cyclohexyl, C
2
-C
6
alkyl which is substituted by —OH, —SH, —CN, C
1
-C
4
alkoxy, C
3
-C
6
alkenoxy, —OCH
2
CH
2
CN, —OCH
2
CH
2
COO(C
1
-C
4
alkyl), —OCO—C
1
-C
4
alkyl, —OCO-phenyl, COOH or COO(C
1
-C
4
alkyl) or R
9
is C
2
-C
12
alkyl which is interrupted by one or more —O— or —S— or R
9
is phenyl which is unsubstituted or substituted by halogen, C
1
-C
12
alkyl or C
1
-C
4
alkoxy, or R
9
is phenyl-C
1
-C
3
alkyl or a group
R
10
and R
11
independently of each other are hydrogen, C
1
-C
12
alkyl, C
2
-C
4
hydroxyalkyl, C
2
-C
10
alkoxyalkyl, C
2
-C
5
alkenyl, C
5
-C
12
cycloalkyl, phenyl-C
1
-C
3
alkyl, phenyl which is unsubstituted or substituted by C
1
-C
12
alkyl or C
1
-C
4
alkoxy, or R
10
and R
11
are C
2
-C
3
alkanoyl, C
3
-C
6
alkenoyl or benzoyl, or R
10
and R
11
together are C
2
-C
6
alkylene optionally interrupted by —O— or —NR
8
—, or R
10
and R
11
together are C
2
-C
6
alkylene which can be substituted by hydroxyl, C
1
-C
4
alkoxy, C
2
-C
4
alkanoyloxy or benzoyloxy, or, when R
10
is hydrogen, R
11
may be a group
R
12
, R
13
, R
14
, R
15
, R
16
, R
17
, R
18
and R
19
independently of one another are hydrogen, halogen, C
1
-C
12
alkyl, cyclopentyl, cyclohexyl or phenyl which is unsubstituted or substituted by one or more OR
8
, SR
9
or NR
10
R
11
, or R
12
, R
13
, R
14
, R
15
, R
16
, R
17
, R
18
and R
19
are benzyl benzoyl, C
2
-C
12
alkanoyl, C
2
-C
12
alkoxycarbonyl optionally interrupted by one or more —O— and/or optionally substituted by one or more hydroxyl groups or R
12
, R
13
, R
14
, R
15
, R
16
, R
17
, R
18
and R
19
are phenoxycarbonyl or a group OR
8
, SR
9
, SOR
9
, SO
2
R
9
, NO
2
, CN, CONR
10
R
11
, or NR
10
R
11
, wherein the substituents OR
8
, SR
9
and NR
10
R
11
may form 5- or 6-membered rings via the radicals R
8
, R
9
, R
10
and/or R
11
with further substituents on the phenyl ring or with one of the carbon atoms of the phenyl ring or, when M
4
is a direct bond, R
15
and R
16
together are ethylene or ethynylene;
t is 0 or 1;
M is C
1
-C
12
alkylene, cyclohexylene, phenylene, —COO—(C
2
-C
12
alkylene)—OOC—, —COO—(CH
2
CH
2
O)
n
—OC— or —CO—(C
2
-C
12
-alkylene)—CO—;
M
1
is a direct bond or C
1
-C
12
alkylenoxy, optionally interrupted by 1 to 5 —O—, —S— and/or —NR
10
—;
M
2
is a direct bond or C
1
-C
12
alkylene-S—, optionally interrupted by 1 to 5 —O—, —S— and/or —NR
10
—;
M
3
is a direct bond, a piperazino group, or C
1
-C
12
alkylene-NR
10
—, optionally interrupted by 1 to 5—O—, —S— and/or —NR
10
—;
M
4
is a direct bond, —O—, —S—, —SO—, —SO
2
—, —CO—, —CH
2
—, —NR
10
—, or a group
Ar is a 5- or 6-membered aromatic heterocyclic ring, which is unsubstituted or substituted by one or more C
1
-C
6
alkyl, phenyl, halogen, OR
8
, SR
9
, NR
10
R
11
, CN, C
2
-C
6
alkanoyl 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; exhibit an unexpectedly good performance.
Substituted radicals phenyl are substituted one to four times, for example one, two or three times, especially two or three times. Substituents on the phenyl ring are preferably in positions 4 or in 3,4-, 3,4,5-, 2,6-, 2,4- or 2,4,6-configuration on the phenyl ring, in particular in 4- or 3,4-configuration.
C
1
-C
20
alkyl is linear or branched and is, for example, C
1
-C
18
-, C
1
-C14-, C
1
-C
12
-, C
1
-C
8
-, C
1
-C
6
- or C
1
-C
4
alkyl or C
4
-C
12
-, C
4
-C
8
alkyl or, in particular, R
1
is C
6
-C
20
alkyl or C
6
-C
12
alkyl. Examples are methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, 2,4,4-trimethylpentyl, 2-ethylhexyl, octyl, nonyl, decyl, dodecyl, tetradecyl, pentadecyl, hexadecyl, octadecyl and icosyl.
C
1
-C
12
alkyl, C
2
-C
12
alkyl, C
1
-C
8
alkyl, C
1
-C
6
alkyl, C
2
-C
6
alkyl and

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