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
2000-10-02
2004-05-25
Huff, Mark F. (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
C430S138000, C430S281100, C430S293000, C568S001000, C522S016000
Reexamination Certificate
active
06740466
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a photopolymerizable composition with which recording can be easily carried out not only using ultraviolet light but also using visible to infrared light and can be suitably applied to a wide range of fields including ink, color filter, hologram, proof, sealant, adhesive, planographic printing, resin relief plate, and photoresist, and to a recording material which does not require the use of a developing solution and the like and does not produce unnecessary wastes and can easily form black and white or colored perfectly dry images having excellent clarity and high contrast.
2. Description of the Related Art
Basically, a photopolymerizable composition contains a photopolymerization initiator and an addition-polymerizable compound having two or more ethylenically unsaturated bonds in the molecule (i.e., a polyfunctional monomer) and, when irradiated with light, the photopolymerizable composition hardens, changes its adhesiveness, or becomes insoluble in solvent. Utilizing these properties, a photopolymerizable composition has been widely used in such applications as photography, printing, metal surface processing, and ink.
Recently, the image formation utilizing a photopolymerizable composition has been extensively studied. For example, an image-forming system, which utilizes photosensitive microcapsules enclosing a photopolymerizable composition, has been proposed. In addition, in recent years, there has been an attempt to form digital images by spectrally sensitizing a photopolymerizable composition to a visible light region and using a laser as a light source (e.g., Journal of the Photographic Society of Japan, Vol. 49(1986), No.5, pp.210). Research to apply a photopolymerizable composition to a full-color photosensitive material (e.g., Japanese Patent Application Laid-Open (JP-A) No. 59-189340) has also been carried out. Further, a novel photopolymerizable composition using an organoboron anion salt of an organic cationic dye (e.g., European Patent No. 223,587A1) has been proposed. These photo- and heat-sensitive recording materials utilizing photopolymerizable compositions enable a perfectly dry image-recording system without using a developing solution and the like, and therefore these recording materials are environmentally very advantageous because wastes are not produced.
When images are recorded in a photosensitive recording material, it is advantageous if an inexpensive infrared laser and green to red light can be utilized in addition to UV light and short-wave visible light. However, many of recording materials utilizing photopolymerizable compositions are sensitive to ultraviolet light but are not sensitive to visible to infrared light or, even if sensitive to such light, the sensitivity is insufficient. As a result, since these recording materials are not free from the problems that the images formed are unclear and the contrast between image portions and non-image portions is insufficient, a need exists for further improvement.
SUMMARY OF THE INVENTION
The task of the present invention is to solve the problems of the prior art and to achieve the following objects. That is, an object of the present invention is to provide a photopolymerizable composition which has a high sensitivity to not only ultraviolet light but also to visible to infrared light and can be suitably applied to a wide range of fields including ink, color filter, hologram, proof, sealant, adhesive, planographic printing, resin relief plate, and photoresist. Another object of the present invention is to provide a recording material which enables a perfectly dry image-recording system and which can easily form black and white or colored images having excellent clarity and high contrast by the use of the above-mentioned photosensitive composition. In particular, an object of the present invention is to provide a recording material in which the fogging of the background is reduced.
In order to solve the problems described above, the photosensitive composition according to the first object of the present invention comprises a polymerizable compound having an ethylenically unsaturated bond, a compound represented by the following general formula (1), and an organoboron compound represented by the following general formula (A):
In the general formula (1) Q
1
to Q
3
each independently represents an oxygen atom or a sulfur atom; R
1
and R
2
each independently represents a hydrogen atom, an aliphatic group, an aromatic group, or a heterocyclic group; and Z
1
and Z
2
each independently represents a substituent necessary for the compound represented by the general formula (1) to become a dye;
In the general formula (A), Ra
1
, Ra
2
, and Ra
3
each independently represents an aliphatic group, an aromatic group, a heterocyclic group, or —SiRa
5
Ra
6
Ra
7
where Ra
5
, Ra
6
, and Ra
7
each independently represents an aliphatic group or an aromatic group; Ra
4
represents an aliphatic group; and Y
+
represents a group capable of forming a cation.
In the photopolymerizable composition according to the first object, the compound represented by the general formula (1) is preferably a compound represented by the following general formula (4):
In the general formula (4), L
1
and L
2
each independently represents a methine group which may be substituted; m represent an integer of 0 to 3; and G
1
and G
2
each independently represents an electron-withdrawing group, or G
1
and G
2
join together to form an aromatic ring or a heterocycle.
In order to solve the problems described above, the photosensitive composition according to the second object of the present invention comprises a polymerizable compound having an ethylenically unsaturated bond, a compound represented by the following general formula (2), and a compound capable of interacting with the compound represented by the following general formula (2) to generate a radical:
In the general formula (2), X
1
represents NR
12
, a sulfur atom, a selenium atom, or an oxygen atom; R
4
, R
5
, and R
12
each independently represents a hydrogen atom, an aliphatic group, an aromatic group, or a heterocyclic group; and R
6
, R
7
, R
8
, R
9
, R
10
, and R
11
each independently represents a hydrogen atom or a monovalent substituent, with the proviso that two or more selected from R
6
, R
7
, R
8
, R
9
, R
10
, R
11
, and R
12
may join together to form a ring.
In order to solve the problems described above, the photosensitive composition according to the third object of the present invention comprises a polymerizable compound having an ethylenically unsaturated bond, a compound represented by the following general formula (3), and a compound capable of interacting with the compound represented by the following general formula (3) to generate a radical:
In the general formula (3), R
13
and R
14
each independently represents a hydrogen atom or a monovalent substituent; and Z
3
and Z
4
each independently represents a substituent necessary for the compound represented by the general formula (3) to become a dye.
In the photopolymerizable composition according to the third object, the compound represented by the general formula (3) is preferably a compound represented by the following general formula (5):
In the general formula (5), L
1
and L
2
each independently represents a methine group which may be substituted; m represents an integer of 0 to 3; and G
1
and G
2
each independently represents an electron-withdrawing group, or G
1
and G
2
join together to form an aromatic ring or a heterocycle.
In the photopolymerizable compositions according to the second and third objects, the compound, which can interact with the compound represented by the general formula (2) or the compound represented by the general formula (3) to generate a radical, is preferably an organoboron compound represented by the following general formula (A):
In the general formula (A), R
a
1
, R
a
2
, and R
a
3
each independently represents an aliphatic group, an aromatic group, a heteroc
Kawamura Koichi
Matsumoto Hirotaka
Sorori Tadahiro
Takashima Masanobu
Washizu Shintaro
Fuji Photo Film Co. , Ltd.
Huff Mark F.
Sughrue & Mion, PLLC
Thornton Yvette C.
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