Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Mixing of two or more solid polymers; mixing of solid...
Reexamination Certificate
2001-02-14
2003-08-26
Lipman, Bernard (Department: 1713)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Mixing of two or more solid polymers; mixing of solid...
C525S344000, C548S183000
Reexamination Certificate
active
06610791
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a novel photosensitive compound and a photosensitive resin and, more particularly, to a photosensitive compound and a photosensitive resin having a wide range of utility including, for example, color cathode-ray tubes and other display tubes, screen printing, immobilized enzymes, PS plates, etching resists, and sandblasting.
2. Background Art
Conventionally, there have been known photosensitive units containing a photosensitive resin obtained through a condensation reaction between non-modified polyvinyl alcohol and a quaternary ammonium salt such as a styrylpyridinium salt or a styrylquinolinium salt (hereafter, resists of this type are referred to as PVA-SbQ-based resists) (see Japanese Patent Publication (kokoku) Nos. 56-5761 and 56-5762, and Japanese Patent Application Laid-Open (kokai) No. 56-11906).
Although these PVA-SbQ-based resists have advantages such as shorter time required for photosensitization, their ionicity is limited to cationic, to thereby limit use and compositions of the resists. In addition, since a mercury lamp (365 nm) and a metal halide light source (400 nm) are used as light sources for exposure, 4-methylquinoline or a similar substance must be used so as to set the photosensitive wavelength of the resists in a longer wavelength range. This is disadvantageous, because of the accompanying increase in cost.
Therefore, in certain uses, such as color cathode-ray tubes, other display tubes, and screen printing, there is still need for resists that exhibit excellent sensitivity at a wavelength as long as 400 nm and that are dissolvable or dispersible in an aqueous solvent. Particularly, in consideration of the excellent characteristics, as a binder polymer, of polyvinyl alcohol (hereinafter abbreviated PVA) for use in the formation of phosphor patterns, demand exists for PVA-based resists of a certain type which have longer photosensitive wavelengths than those possessed by PVA-SbQ-based resists, and in addition, which, with regard to ionicity, permit selection between anionic and nonionic in accordance with use.
Thus, in order to provide a photosensitive resin meeting the aforementioned demand, the present inventors have developed a photosensitive resin produced by introducing an azide compound having a rhodanine skeleton into modified or non-modified poly(vinyl alcohol) through acetalization (hereinafter the resin is referred to as PVA-ARB-based resist) and have filed an application for patent (Japanese Patent Application Laid-Open (kokai) No. 10-310769). The PVA-ARB-based resist proposed in the publication is an excellent photoresist, having high photosensitivity and attaining photosensitivity at a longer wavelength. The steps for synthesizing an azide compound having a rhodanine skeleton and an acetal group—which serves as a photosensitive unit of the PVA-ARB-based resist—include reaction in which an acetal-group-containing amine is transformed to a rhodanine ring.
However, acetal-group-containing amines are comparatively expensive and provide a poor synthesis yield in terms of rhodanine ring formation. Thus, employment of the amines is disadvantageous, due to high production costs. In addition, since the aforementioned photosensitive unit of the PVA-ARB-based resist has poor solubility in water, the amount of the unit to be introduced into a water-soluble polymer is limited. An increase in the amount results in poor developability of unexposed portions of the resist with water and, as a problem in production of photosensitive polymers, a prolonged period of time for dissolving an aqueous solvent during introduction of the unit into a polymer.
SUMMARY OF THE INVENTION
In view of the foregoing, an object of the present invention is to provide a novel photosensitive compound which can be used to prepare a corresponding photosensitive resin. Another object is to provide a photosensitive resin prepared from the photosensitive compound.
The present inventors have conducted extensive studies so as to solve the aforementioned problems, and have found that a novel rhodanine-skeleton-containing azide compound can be produced through condensation of a rhodanine compound and an aldehyde, the rhodanine compound having a variety of substituents such as an acetal group and an amido bonding portion and the aldehyde being an azido-group-containing water-soluble aldehyde or an aldehyde having an azido-group-containing aromatic ring. The present invention has been accomplished on the basis of this finding.
Accordingly, in order to solve the aforementioned problems, the present invention provides a photosensitive compound having a moiety represented by the following formula (I) or (II):
wherein
R
1
represents a hydrogen atom, an alkyl group, an aryl group, or an aralkyl group;
Y is selected from the following formula groups:
wherein each of R
2
and R
3
represents a hydrogen atom, an alkyl group, an aryl group, or an aralkyl group, and l is an integer of 1 to 5; and
Ar is selected from the following formula groups:
wherein X represents lithium, sodium, potassium, ammonium, monoalkylammonium, dialkylammonium, trialkylammonium, or tetraalkylammonium. In R
1
, a C1-C5 alkyl group is preferred as the alkyl group, and examples of aryl groups or aralkyl groups include a phenyl group, a naphthyl group, and a benzyl group. In X, a C1-C5 alkyl group is preferred as the alkyl group in the monoalkyl-, dialkyl-, trialkyl-, and tetraalkylammonium groups.
Particularly, the photosensitive compound of the present invention is represented by any one of the following formulas (III) to (VI):
wherein
R
4
is selected from among C≦6 alkyl groups, and two R
4
's may be joined to each other to form a group —(CH
2
)
m
— (m is 2 or 3);
n is 1, 2, or 3;
R
5
represents a hydrogen atom, an alkyl group, an aryl group, or an aralkyl group; and
each of Y and Ar has the same meaning as described above. In R
5
, a C1-C5 alkyl group is preferred as the alkyl group, and examples of aryl groups or aralkyl groups include a phenyl group, a naphthyl group, and a benzyl group.
The photosensitive resin of the present invention has a moiety represented by the aforementioned formula (I) or (II). Each of R
1
, Y, and Ar has the same meaning as described above.
Particularly, the photosensitive resin of the present invention has a structural unit represented by the following formula (VII) or (VIII):
wherein n is 1, 2, or 3; R
5
represents a hydrogen atom, an alkyl group, an aryl group, or an aralkyl group; and each of Y and Ar has the same meaning as described above. In R
5
, a C1-C5 alkyl group is preferred as the alkyl group, and examples of aryl groups or aralkyl groups include a phenyl group, a naphthyl group, and a benzyl group.
The photosensitive resin composition of the present invention contains a photosensitive resin according to the present invention.
The method of producing an azido-group-containing photosensitive compound or resin according to the present invention comprises a step represented by the following reaction scheme (1) or (2):
wherein Rz is a substituent or a polymer chain and each of R
1
, Y, and Ar has the same meaning as described above. The substituent may contain an acetal group.
In the method of producing a photosensitive resin according to the present invention, the aforementioned Rz may be an acetal-group-containing substituent, and the substituent may further be reacted with a saponified product of poly(vinyl acetate).
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS
The photosensitive compound or resin according to the present invention having a moiety represented by the aforementioned formula (I) or (II) exhibits a photosensitive characteristic of an azide compound, photosensitivity at a long wavelength, and excellent stability. Introduction of such a moiety enables researchers to design a variety of photosensitive compounds or resins with relative ease. The moiety, having an amido portion, exhibits high solubility and developability with water.
Typical examples include the followi
Shibuya Toru
Tada Kentaro
Huntley & Associates
Lipman Bernard
Toyo Gosai Kogyo Co., Ltd.
LandOfFree
Photosensitive compound and photosensitive resin does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Photosensitive compound and photosensitive resin, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Photosensitive compound and photosensitive resin will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3093725