Radiation imagery chemistry: process – composition – or product th – Diazo reproduction – process – composition – or product – Composition or product which contains radiation sensitive...
Reexamination Certificate
1999-02-26
2001-02-20
Chu, John S. (Department: 1752)
Radiation imagery chemistry: process, composition, or product th
Diazo reproduction, process, composition, or product
Composition or product which contains radiation sensitive...
C430S171000, C430S176000, C430S281100
Reexamination Certificate
active
06190824
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a photosensitive composition having a good storage stability and a high sensitivity.
2. Description of the Related Art
Heretofore, various image forming methods have been known in diazo-process photography. Examples of these methods include: dye-imaging, which utilizes photodecomposition of an aromatic diazo compound, such as a diazonium salt, a diazo sulfonate, or a diazo compound, for example, an iminoquinone diazide, a naphthoquinone diazide, or the like, together with a coupling agent according to need; preparation of printing plates, proofs, mask films, and the like by utilizing a hardening reaction or a solubilization phenomenon; and foam imaging.
As to photopolymerization, in the field of preparation of materials for printing plates, proofs, mask films, photoresists, and the like, there have been known various image forming methods which utilize changes in properties, such as solubility, tackiness, adhesion, and the like due to a photochemical hardening reaction.
In the diazo-process photography, the amount of energy required for photodecomposition of a photodecomposable aromatic diazo compound to be used is generally very large and sensitive wavelengths extend into a visible blue light region. Consequently, the scope in which diazo-process photography can be used is limited to materials that have a low sensitivity and are printed by ultraviolet light. In order to solve this problem, intense studies have been conducted regarding spectral sensitization of photodecomposable aromatic diazo compounds in a visible light region. As a result, some specific dyes, such as riboflavin, porphyrin, chlorophyll, and the like, are now known to act as spectral sensitizers for diazonium salts and diazo sulfonates. As another example of the sensitization method, Japanese Patent Application Publication (JP-B) No. 50-21,247 discloses a photosensitive material for diazo-process photography wherein the photosensitive composition comprises an aromatic diazo compound together with at least one compound selected from the group consisting of a sulfinic acid and a salt of sulfinic acid in combination with a sensitizing dye.
However, none of these methods of prior art have been put to practice, because these methods are associated with drawbacks, for example, poor stability and restricted scope of selectivity in spectral wavelength regions. Further, these systems have little or no effect in the spectral sensitization for the photodecomposition of diazo compounds such as naphthoquinone diazides.
Despite continuous development of new spectrally sensitizing technologies for photopolymerization, the region of spectral wavelengths that can be used in prior art is still up to 500 nm, and therefore a system, that can be spectrally sensitized in a wavelength region ranging from 500 nm to infrared light and has a high sensitivity and good stability has not been put to practical use.
As a candidate that may overcome the above-mentioned drawbacks, Japanese Patent Application Laid-Open (JP-A) No. 62-143,044 discloses a photopolymerization initiator comprising a cationic dye/borate anion complex. This system can be spectrally sensitized freely in a region ranging from blue light to infrared light, has good stability, and exhibits a high level of sensitivity. However, since the sensitivity is several mJ/cm
2
, the sensitivity needs to be upgraded before the system is put to practical use.
As stated above, a truly satisfactory system, which has a good storage stability and a high sensitivity, has not been proposed in either diazo-process photography or photopolymerization.
SUMMARY OF THE INVENTION
It is, accordingly, an object of the present invention to overcome problems in the prior art by providing a photosensitive composition having a high sensitivity and good stability over time in both diazo-process photography and photopolymerization.
In particular, the object of the present invention is to provide a novel photosensitive composition in which even an aromatic diazo compound such as a photodecomposable naphthoquinone, i.e., a compound traditionally regarded as one incapable of being spectrally sensitized by photodecomposition, is spectrally sensitized in an efficient way.
The photosensitive composition of the present invention comprising a polymerizable monomer, a photopolymerization initiator, and a diazonium salt compound containing an anion portion represented by the general formula (I-1), (I-2), or (II) given below:
wherein, in the general formulas (I-1) and (I-2), R
1
and R
2
each independently represent a phenyl group, an aromatic hydrocarbyl group that may contain a heteroatom and is a group other than the phenyl group, an alkyl group that has 1 to 20 carbon atoms and is substituted by —Si(R
9
)(R
10
)(R
11
), or a group represented by the formulae (ii), (iia), or (iib) given below, and the phenyl group and the aromatic hydrocarbyl group may each be substituted by a group selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an alkyl group having 2 to 20 carbon atoms and containing O, S(O)
p
or NR
5
, OR
6
, R
6
S(O)
p
, R
6
SO
3
, N(R
7
)(R
8
), R
6
OCO, CON(R
7
)(R
8
), COR
9
, Si(R
9
)(R
10
)(R
11
), Sn(R
9
)(R
10
)(R
11
), B(R
12
)(R
13
), a halogen atom, (R
9
)(R
10
)P(O)
q
, and CN, so that at least one ortho position of the phenyl group and the aromatic hydrocarbyl group is substituted by a substituent group; and
R
2a
represents a phenylene group or another divalent aromatic hydrocarbyl group that may contain a heteroatom, wherein the aromatic hydrocarbyl group may be substituted by a group selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an alkyl group having 2 to 20 carbon atoms and containing O, S(O)
p
or NR
5
, OR
6
, R
6
S(O)
p
, R
6
SO
3
, N(R
7
)(R
8
), R
6
OCO, CON(R
7
)(R
8
) COR
9
, Si(R
9
)(R
10
)(R
11
), Sn(R
9
)(R
10
)(R
11
), B(R
12
)(R
13
), a halogen atom, (R
9
)(R
10
)P(O)
q
, CN, and a group represented by the formula (a) given below:
wherein, in the formula (a), R
a
represents an alkylene group, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or a substituted alkylene group bearing a substituent selected from the group consisting of R
6
OCO, CN, and a halogen atom; and
in the formulae (ii), (iia), and (iib), the aromatic ring may be substituted by a group selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an alkyl group having 2 to 20 carbon atoms and containing O, S(O)
p
or NR
5
, OR
6
, R
6
S(O)
9
, R
6
SO
3
, N(R
7
)(R
8
), R
6
OCO, CON(R
7
)(R
8
), COR
9
, Si(R
9
)(R
10
)(R
11
), Sn(R
9
)(R
10
)(R
11
), B(R
12
)(R
13
), a halogen atom, (R
9
)(R
10
)P(O)
q
, and CN; and Y represents (CH
2
)
n
, CH═CH, CO, NR
5
, O, S(O)
p
, or a group represented by the formula given below:
wherein, R
3
represents an alkyl group that has 1 to 20 carbon atoms and is substituted by —Si(R
9
)(R
10
)(R
11
), a phenyl group, or an aromatic hydrocarbyl group that is other than the phenyl group and may contain a heteroatom, and the phenyl group and the aromatic hydrocarbyl group may be substituted by a group selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an alkyl group having 2 to 20 carbon atoms and containing O, S(O)
p
or NR
5
, OR
6
, R
6
S(O)
p
, R
6
SO
3
, N(R
7
)(R
8
), R
6
OCO, CON(R
7
)(R
8
), COR
9
, Si(R
9
)(R
10
)(R
11
), Sn(R
9
)(R
10
)(R
11
), B(R
12
)(R
13
), a halogen atom, (R
9
)(R
10
)P(O)
q
, and CN; and
R
4
represents a group selected from the group consisting of a phenyl group, an aromatic hydrocarbyl group that is other than the phenyl group and may contain a heteroatom, an alkyl group having 1 to 20 carbon atoms, an alkyl group having 2 to 20 carbon atoms and containing O, S(O)
p
or NR
5
, a cycloalkyl group having 3 to 12 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, and a group represented by the formula (a) or (b) given below:
wherein, in the formulas (a) and (b), R
a
and R
b
each inde
Fukushige Yuuichi
Takashima Masanobu
Chu John S.
Fuji Photo Film Co. , Ltd.
Sughrue Mion Zinn Macpeak & Seas, PLLC
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