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
2000-04-21
2001-08-28
Ashton, Rosemary E. (Department: 1756)
Radiation imagery chemistry: process, composition, or product th
Imaging affecting physical property of radiation sensitive...
Radiation sensitive composition or product or process of making
C430S287100, C430S907000, C430S915000, C430S922000, C430S923000, C430S924000, C522S110000, C522S114000
Reexamination Certificate
active
06280905
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to a photosensitive resin composition which can be developed by using water. In more particular, it relates to a photosensitive resin composition which has a low hardness, and high resilience and is useful as a material for a photosensitive printing plate, and the like.
Photosensitive resin compositions have hitherto been widely used for photoresist, ink, printing plates, etc. However, many of such photoresist and printing plates require the use of organic solvents at the time of developing. In recent years, however, in addition to the problems of safety and health in process operations, the adverse influence of organic solvents on environment has become a serious problem, so that photosensitive resin composition which can be developed more safely by using water are eagerly desired. To meet such needs, photosensitive resin compositions have been proposed which use as a base material water-soluble polymers, e.g., poly(vinyl alcohol), gelatin and casein.
However, previous water-developable photosensitive resin compositions have a strongly polar hydroxyl group, amide group, or the like, so that photo-cured products resulting from the compositions have a high hardness and a low resilience. Accordingly these compositions are not suited for such uses as, for example, printing on the surface of a flexible packaging material.
SUMMARY OF THE INVENTION
In view of the situations, the object of the present invention is to provide a photosensitive resin composition which can be developed with water, has a low hardness and high resilience and is excellent in balance of properties.
According to the present invention, there is provided a photosensitive resin composition which comprises
(1) a particulate copolymer comprising, as the repeating units in the copolymer, 10-99.8% by mole of the unit of (i) an aliphatic conjugated diene monomer, 0.1-30% by mole of the unit of (ii) a monomer having a polymerizable unsaturated group and an amino group, 0.1-20% by mole of the unit of (iii) a monomer having at least two polymerizable unsaturated groups and 0-40% by mole of the unit of a copolymerizable other monomer having one polymerizable unsaturated group, the total of the units of the monomers (i), (ii), (iii) and (iv) being 100% by mole,
(2) a photopolymerizable unsaturated monomer, and
(3) at least one photopolymerization initiator selected from the group of the compounds represented by the following formulas (I) and (II),
wherein X and Y are each independently a hydrogen atom, halogen atom, carboxyl group, monovalent hydrocarbon group having 1-20 carbon atoms or alkoxyl group having 1-20 carbon atoms and Z is an oxygen atom or sulfur atom.
DETAILED DESCRIPTION OF THE INVENTION
The present invention is described in detail below.
(1) Particulate Copolymer
The particulate copolymer, one of the constituents of the photosensitive resin composition of the present invention, may be prepared by emulsion-polymerizing or suspension-polymerizing a monomer mixture which comprises, as the essential components, (i) an aliphatic conjugated diene monomer (hereinafter referred to as “monomer (i)”), (ii) a monomer having one polymerizable unsaturated group and an amino group (hereinafter referred to as “monomer (ii)”) and (iii) a monomer having at least two polymerizable unsaturated groups (hereinafter referred to as “monomer(iii)”) and, if necessary, additionally (iv) a copolymerizable other monomer having one polymerizable unsaturated group (hereinafter referred to as “monomer(iv)”).
Examples of the monomer (i) include 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadeine and chloroprene, 1,3-butadiene and isoprene being preferred. These monomers (i) may be used each alone or in a combination of two or mere thereof.
In the repeating units in the particulate copolymer, the content of the monomer (i) unit is 10-99.8% by mole, preferably 30-90% by mole. When the content of the monomer (i) unit is less than 10% by mole, the resulting composition tends to have a decreased strength after photo-curing; when the content is higher than 99.8% by mole, the resulting composition tends to be poor in water-developability.
The monomer (ii) is preferably a monomer having a tertiary amino group, examples of which include N,N′-dialkylaminoalkyl acrylates or methacrylates, such as N,N′-dimethylaminomethyl acrylate and methacrylate, N,N′-diethylaminomethyl acrylate and methacrylate, N,N′-2-dimethylaminoethyl acrylate and methacrylate,N,N′-2-diethylaminoethyl acrylate and methacrylate,N,N′-2-(di-n-propylamino) ethyl acrylate and methacrylate N,N′-2-dimethylaminopropyl acrylate and methacrylate, N,N′-2-diethylaminopropyl acrylate and methacrylate, N,N′-2-(di-n-propylamino)-propyl acrylate and methacrylate, N,N′-3-dimethylamino-propyl acrylate and methacrylate, N,N′-3-diethylamino-propyl acrylate and methacrylate, and N,N′-3-(di-n-propylamino) propyl acrylate and methacrylate; N,N′-dialkylamino-alkyl group-containing unsaturated amides, such as N,N′-dimethylaminomethyl acrylamide and methacrylamide, N,N′-diethylaminomethyl acrylamide and methacrylamide, N,N′-(2-dimethylaminoethyl)acrylamide and methacrylamide, N,N′-(2-diethylaminoethyl)acrylamide and methacrylamide, N,N′-(2-dimethylaminopropyl)acrylamide and methacrylamide, N,N′-(2-diethylaminopropyl)acrylamide and methacrylamide, N,N′-(3-dimethylaminopropyl)acrylamide and methacrylamide, and N,N′-(3-diethylaminopropyl)acrylamide and methacrylamide; and vinylaromatic compounds having a tertiary amino group, such as N,N′-dimethyl-p-aminostyrene, N,N′-diethyl-p-aminostyrene and vinylpyridine; preferred of these being N,N′-dimethylaminoethyl methacrylate and N,N′-diethylaminoethyl methacrylate. These monomers having a tertiary amino group may be used each alone or in a combination of two or more thereof.
In the repeating units in the particulate copolymer the content of the monomer (ii) unit is 0.1-30% by mole, preferably 0.5-20% by mole. When the content of the monomer (ii) unit is less than 0.1% by mole, the resulting composition tends to be poor in water-developability; when the content is higher than 30% by mole, the resulting composition tends to be hard and brittle.
Examples of the monomer (iii) include ethylene glycol diacrylate and dimethacrylate, propylene glycol diacrylate and dimethacrylate, 1,4-butanediol diacrylate and dimethacrylate, 1,6-hexanediol diacrylate and dimethacrylate, trimethylolpropane diacrylate and dimethacrylate, trimethylolpropane triacrylate and trimethacrylate, pentaerythritol triacrylate and trimethacrylate, pentaerythritol tetraacrylate and tetramethacrylate, divinylbenzene, diisopropenylbenzene and trivinylbenzene; preferred of these being ethylene glycol diacrylate and dimethacrylate, and divinylbenzene.
These monomers (iii) may be used each alone or in a combination of two or more thereof.
In the repeating units in the particulate copolymer, the content of the monomer (iii) unit is 0.1-20% by mole, preferably 0.5-10% by mole. When the content of the monomer (iii) unit is less than 0.1% by mole, the resulting composition tends to be poor in water-developability; when the content is higher than 20% by mole, the particulate copolymer tends to be poorly compatible with the photopolymerizable unsaturated monomer (2), resulting in poor processability of the composition, and the composition tends to have a greatly decreased strength after photo-curing.
The monomer (iv) is not particularly limited so long as it is a copolymerizable compound having one polymerizable unsaturated group. Example thereof include styrene, &agr;-methylstyrene, o-vinyltoluene, m-vinyltoluene, p-vinyltoluene, acrylonitrile, methacrylonitrile, vinylidene cyanide, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, maleimide, methyl acrylate and methacrylate, ethyl acrylate and methacrylate, n-propyl acrylate and methacrylate, i-propyl acrylate and methacrylate, n
Koshimura Katsuo
Nishioka Takashi
Tanaka Tadaaki
Toyoshima Tsukasa
Ashton Rosemary E.
JSR Corporation
Oblon & Spivak, McClelland, Maier & Neustadt P.C.
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