Radiation imagery chemistry: process – composition – or product th – Imaging affecting physical property of radiation sensitive... – Radiation sensitive composition or product or process of making
Reexamination Certificate
2000-09-19
2003-05-06
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
C430S914000, C552S003000, C570S101000
Reexamination Certificate
active
06558871
ABSTRACT:
FIELD OF THE INVENTION
The present invention is related to a photopolymerization initiator comprising an iodonium salt compound and to a photocurable composition containing the said photopolymerization initiator. More particularly, the present invention is directed to a cationically photocurable composition which is cured in a short time upon irradiation with actinic energy rays, such as light, electron rays and X-rays. Since the cured article of the photocurable composition has the excellent material properties, it can be suitably used for coating materials, adhesives, photoresists, inks, silicon release, etc.
The present invention is also directed to a photocurable composition and more particularly to a cationically photocurable composition having an excellent photocurable property and/or a sensitized cationically photocurable composition. The photocurable composition of the present invention is able to be cured upon irradiation with actinic energy rays, such as light, electron rays and X-rays, and it can be suitably used for coating materials, adhesives, inks, photoresists and photosensitive resins for photomolding because it has an excellent long wavelength sensitizing property. Further, the present invention is also directed to a photocuring process for a photocurable composition containing a pigment, a novel compound to be used for the photocurable composition described above having a group functioning as a cationic photopolymerization initiator and a cationically polymerizable group in the molecule, a novel compound having a group functioning as a cationic photopolymerization initiator, a sensitizing group accelerating photoinitiated cationic reaction and a cationically polymerizable initiator, and a process for preparing such compounds.
BACKGROUND ART
In Japanese Patent laid-open gazettes with No. Sho 50-151996, No. Sho 60-47028, etc., iodonium salt compounds similar to the iodonium salt compound specified in the present invention are disclosed, and wherein it is described that these iodonium salt compounds can be used as a catalyst for curing cationically polymerizable compounds, such as epoxy compounds, upon irradiation with light, electron rays and radiation such as X-rays.
In general, iodonium salt compounds have problems such as low solubility to monomers and high toxicity. As a means to solve such problems, it is preferable to introduce a functional group thereinto to enable various modification. However, in case of synthesizing compounds described in the Japanese Patent laid-open gazettes, No. Sho 50-151996 and No. 60-47029 mentioned above, there are many groups, such as alkyl, alkoxy and carbonyl, which are hard to be chemically modified in those compounds, and coloring to those compounds during the synthesis may be caused in many cases. On the other hand, the yield for an iodonium salt compound wherein a chemically-modifiable functioning group such as carboxyl is directly introduced is known as low as much as 20% more or less.
It is known that the photocurable property of an iodonium salt compound is remarkably decreased when the counter anion thereof is hexafluorophosphonate, tetrafluoroborate or the like, except hexafluoroantimonate and tetraperfluorophenylborate. Therefore, the iodonium salt compounds having such counter anion are not suitable for photocuring clear system compositions and pigment-containing compositions. Whereas, some dyestuff derivatives and thioxanthone derivatives are known as an effective sensitizer for those iodonium salt compounds, however, none of sensitizers usable for the clear system compositions and the ones that are usable for pigment-containing compositions, cheap, giving less color and very effective have been known.
An object of the present invention is to provide a photocurable composition containing an iodonium salt compound, being synthesized easily at a high yield, highly sensitive to actinic energy rays, such as light, electron rays and X-rays, having high solubility in a monomer, less colored, less toxic, able to cure irrespective of clear system compositions or pigment-containing compositions in a short time even its counter anion is hexafluorophosphate, tetrafluoroborate or the like, and the cured articles thereof has the excellent material properties.
DISCLOSURE OF THE INVENTION
The inventors of the present invention had worked for finding an iodonium salt compound capable of solving the problems as described above and had found that the less toxic iodonium salt compound giving less color can be easily synthesized at a high yield by using a specific substrate as the starting material. Further, the inventors had found that a photocurable composition having the excellent material properties and being curable in a short time upon irradiation with actinic energy rays, such as light, electron ray and X-ray, particularly a pigment-containing photocurable composition, is obtainable by using the iodonium salt compound and a sensitizer in combination. Furthermore, the inventors had also found that a photocurable composition using a compound in which a group functioning as a cationic photopolymerization initiator, a sensitizing group accelerating the photoinitiated cationic reaction and a cationically polymerizable group, or, a compound in which a group functioning as a cationic photopolymerization initiator, particularly an onium salt compound, and a cationically polymerizable group, are contained in the molecule can be cured with high sensitivity in a short time upon irradiation with actinic rays, such as light, electron ray or X-ray, and the cured article of the photocurable composition shows to have excellent material properties.
The present invention is directed to a photopolymerization initiator characterized in that the photopolymerization initiator comprises at least one of diaryliodonium salt compounds represented by a general formula (I);
wherein R
1
and R
2
represent each independently hydrogen, optionally-substituted alkyl, optionally-substituted cycloalkyl, optionally-substituted alkoxy, or carboxyl or its ester, a and b represent each independently an integer selected from 1 to 4, provided, when a and/or b are 2 or more, the corresponding 2 or more substituents, R
1
and/or R
2
may be the same or different group, and Y- represents non-nucleophilic anion residue, A represents any one group selected from a substituent group represented by the following formulas,
B represents optionally-substituted alkylene or optionally-substituted phenylene, i, j and k represent each independently 0 or 1, provided, all of i, j and k never be 0 at the same time, and i, j and k cannot be 1, 0 and 1 simultaneously, R
3
, R
4
, R
5
, R
8
, R
19
and R
29
represent each independently hydrogen, halogeno, optionally-substituted alkyl, optionally-substituted cycloalkyl, optionally-substituted phenyl, optionally-substituted alkoxy, optionally-substituted cycloalkoxy, optionally-substituted phenoxy, or carboxyl or its ester, R
6
, R
7
, R
9
, R
10
, R
12
, R
13
, R
15
, R
16
, R
17
and R
18
represent each independently hydrogen, optionally-substituted alkyl, optionally-substituted cycloalkyl or optionally-substituted phenyl, c, d, e, f, g and h represent each independently an integer selected from 1 to 5, provided, when c, d, e, f, g and/or h are 2 or more, the corresponding 2 or more substituents, R
3
, R
4
, R
5
, R
8
, R
19
and R
29
, may be the same or different group, n, m, p, q, r, s, t and u represent each independently an integer selected from 1 to 8, provided, when n, m, p, q, r, s, t and/or u are 2 or more, the corresponding 2 or more substituents, R
6
, R
7
, R
9
, R
10
, R
12
, R
13
, R
15
, R
16
, R
17
, R
18
, R
20
, R
21
, R
23
, R
24
, R
26
and R
27
, may be the same or different group, R
11
, R
14
, R
25
and R
28
represent each independently hydrogen, optionally-substituted alkyl, optionally-substituted cycloalkyl, or optionally-substituted phenyl, R
22
represents hydrogen, optionally-substituted alkyl, optionally-substituted cycloalkyl, optionally-substituted phenyl or optionally-substituted alkoxy, v and w r
Kimizuka Shinichi
Shirai Akihiro
Takahashi Eiji
Takahashi Hiroshi
Ashton Rosemary
LaPointe Dennis G.
Nippon Soda Co. Ltd.
LandOfFree
Photocurable composition containing iodonium salt compound does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Photocurable composition containing iodonium salt compound, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Photocurable composition containing iodonium salt compound will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3003917