Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Polymers from only ethylenic monomers or processes of...
Reexamination Certificate
2002-03-14
2004-09-07
Pezzuto, Helen L. (Department: 1713)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Polymers from only ethylenic monomers or processes of...
C526S259000, C526S266000, C526S287000, C526S288000, C526S298000, C526S305000, C526S333000
Reexamination Certificate
active
06787622
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a novel radical polymerizable compound, more specifically to a radical polymerizable compound capable of utilizing for image forming materials, for example, stereolithography, holography, lithographic printing plate precursors, color proofs, photoresists and color filters, and photosetting resin materials, for example, ink, paint and adhesives. In particular, it relates to a radical polymerizable compound for use in a photopolymerizable composition suitable for the preparation of a lithographic printing plate precursor that is capable of being subjected to a so-called direct plate-making, in which the plate-making is directly conducted based on digital signals, for example, from a computer using various kinds of lasers.
BACKGROUND OF THE INVENTION
A solid laser, semiconductor laser and gas laser having a large output and a small size, which radiate an ultraviolet ray, visible light or infrared ray having a wavelength of from 300 to 1,200 nm, have become easily available, and these lasers are very useful for a recording light source used in the direct plate-making based on digital signals, for example, from a computer.
Various investigations on recording materials sensitive to such laser beams have been made. Typical examples thereof include recording materials capable of being recorded with a infrared laser having a wavelength of not less than 760 nm, for example, positive-working recording materials as described in U.S. Pat. No. 4,708,925 and acid catalyst crosslinking type negative-working recording materials described in JP-A-8-276558 (the term “JP-A” as used herein means an “unexamined published Japanese patent application”), and recording materials responsive to an ultraviolet ray or visible light laser having a wavelength of from 300 to 700 nm, for example, radical polymerization type negative-working recording materials as described in U.S. Pat. No. 2,850,445 and JP-B-44-20189 (the term “JP-B” as used herein means an “examined Japanese patent publication”).
On the other hand, recording materials responsive to short wavelength light of not more than 300 nm are especially important for photoresist materials. In recent years, in integrated circuits, the degree of integration is more and more increased and in the production of a semiconductor substrate of VLSI, etc., fabrication of super-fine patterns composed of line width of finer than half micron has been required. In order to fulfill such requirements, the wavelength of light source used in an exposure apparatus in photolithography is more and more shortened and the use of a far ultraviolet ray or an excimer laser (e.g., XeCl, KrF or ArF) has been investigated. Further, the formation of super-fine patterns by an electron beam has been started to investigate. Particularly, the electron beam is regarded as a promising light source for pattern forming technique to lead the next generation.
A subject common to all of these image recording materials is that how an ON-OFF of the images can be enlarged. In other words, how high sensitivity and preservation stability of the image recording material can be stood together.
Photo radical polymerization systems are ordinarily highly sensitive but their sensitivities severely decrease on polymerization inhibition due to oxygen in the air. Thus, measures of providing a layer for interrupting oxygen on an image forming layer are taken. However, the formation of such a layer for interrupting oxygen may cause fog due to polymerization in the dark, resulting in degradation of preservation stability. It is difficult for the high sensitivity to consist with the preservation stability and satisfactory results have not been obtained in the prior art. Therefore, novel techniques to solve these problems have been desired.
SUMMARY OF THE INVENTION
Therefore, an object of the present invention is to provide a radical polymerizable compound for use in a photo-radical polymerization composition satisfying both high sensitivity and excellent preservation stability, which is promising in image forming techniques due to the highest sensitivity.
Another object of the present invention is to provide a radical polymerizable compound for use in a photopolymerizable composition suitable for a lithographic printing plate precursor capable of performing direct plate-making based on digital data, for example, from a computer by recording using a solid laser or semiconductor laser radiating an ultraviolet ray, visible light or infrared ray.
Other objects of the present invention will become apparent from the following description.
As a result of the earnest investigations, it has been found that the above-described objects of the invention can be achieved by using a compound having a specific polymerizable group in a photopolymerizable composition.
Specifically, the radical polymerizable compound of the present invention has a structure represented by the following formula (I), (II) or (III):
wherein X
3
represents a heterocyclic group that is connected through a hetero atom included therein; Q
1
represents a group represented by CN or COX
2
; X
2
represents a hydroxy group, a substituted oxy group, a substituted thio group, an amino group, a substituted amino group, a heterocyclic group that is connected through a hetero atom included therein or a halogen atom; X
1
represents a substituted oxy group, a substituted amino group, a heterocyclic group that is connected through a hetero atom included therein or a halogen atom; Z
1
and Z
2
each represents a n-valent connecting group having at least 6 carbon atoms, in which the n's connecting parts are all hetero atoms; R
a
and R
b
, which may be the same or different, each represents a hydrogen atom, a halogen atom, a cyano group or an organic residue; or R
a
and R
b
, X
1
and R
a
or R
b
X
3
and R
a
or R
b
, or Q
1
and R
a
or R
b
may combine with each other to form a cyclic structure; and n represents an integer of from 2 to 6.
DETAILED DESCRIPTION OF THE INVENTION
Monomers, oligomers and polymers containing a group having a high polymerization activity, for example, an acrylic ester group, an acrylamido group, a methacrylic ester group or a methacrylamido group have hitherto been employed as most common radical polymerizable compounds. However, since these compounds suffer the polymerization inhibition due to oxygen, when they are used in photopolymerizable compositions, the subject of securing both sensitivity and preservation stability cannot be achieved.
On the other hand, compounds (monomers) having an &agr;-hetero-substituted methylacryl group or an &agr;-halogen-substituted methylacryl group as a group having polymerizability comparing favorably with the acrylic groups are known for polymer constituting components. It is said that the polymerizability of such a compound for polymer constituting component increases owing to the electronic effect and steric effect of hetero atom or halogen atom substituted in the &agr;-position different from groups having low polymerizability, for example, an itaconic acid group having a substituent in the &agr;-position or an &agr;-alkylacryl group.
It has been found that the difficulty which resides in conventional radical polymerizable compounds, specifically the effect of polymerization inhibition due to oxygen can be remarkably reduced by using a compound having a structure including a polymerizable group substituted with a hetero atom or a halogen atom in its &agr;-position together with a photopolymerization initiator in a photopolymerizable composition, and that the subject of securing both high sensitivity and excellent preservation stability, which is an inherent problem in the photopolymerizable composition, can be achieved.
Although the mechanism of reducing the influence of polymerization inhibition due to oxygen is not certain, it is believed that the compound containing a structure represented by formula (I), (II) or (III) according to the present invention has an extremely small termination rate constant due to the effect of substi
Fuji Photo Film Co. , Ltd.
Pezzuto Helen L.
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