JPH0635198A - Photopolymerizable composition - Google Patents

Abstract

(57) [Summary] [Structure] Addition-polymerizable compound having at least one ethylenically unsaturated double bond, sensitizer having specific tetrahydroquinoline skeleton and 1-indanone skeleton in molecule, and sensitizer A photopolymerizable composition containing an activator capable of generating an active radical upon irradiation with light under the coexistence with. [Effect] The photopolymerizable composition of the present invention has extremely high sensitivity to visible light, particularly long-wavelength light.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a photopolymerizable composition. In particular, the present invention relates to a photopolymerizable composition having extremely high sensitivity to light rays in the visible region.

[0002]

2. Description of the Related Art Conventionally, many image forming methods utilizing a photopolymerization system are known. For example, a photopolymerizable composition comprising a compound containing an addition-polymerizable ethylenic double bond, a photopolymerization initiator, and an organic polymer binder optionally used is prepared, and the photopolymerizable composition is supported. A photosensitive material having a layer of the photopolymerizable composition applied on the body is prepared, and the desired image is imagewise exposed to polymerize and cure the exposed portion, and the unexposed portion is dissolved and removed to form a cured relief image. And a layer of a photopolymerizable composition is provided between two supports in which at least one of the above-mentioned light-sensitive materials is transparent, and the transparent support side is imagewise exposed to cause a change in adhesive strength due to light. After that, a method of forming an image by peeling the support, a photosensitive material in which a microcapsule layer is provided by coating the support with microcapsules having a photopolymerizable composition and a color material such as a leuco dye in the contents Create The photosensitive material imagewise exposed to photocuring capsules exposed portion, the capsule in the unexposed portion was destroyed by pressure treatment, or heat treatment, and developed by contact with the color material developer,
There are a method for forming a colored image, and an image forming method utilizing a change in toner adhesion of the photopolymerizable composition layer due to light.

Conventionally, benzoyl, benzoin alkyl ether, benzyl ketal, benzophenone, anthraquinone, benzyl, Michler's ketone, etc. have been used as the photopolymerization initiator of the photopolymerizable composition applied to these methods. However, these photopolymerization initiators are significantly lower in light in the visible light region of 400 nm or more as compared with the photopolymerization initiating ability in the ultraviolet light region of 400 nm or less, and therefore the application of the photopolymerizable composition containing them is The range has been limited.

In recent years, with the development of image forming technology, there has been a strong demand for photopolymers having a high sensitivity to light rays in the visible region. For example, it is a light-sensitive material suitable for non-contact type projection exposure plate making, laser plate making by visible light laser, and the like. Among these techniques, the plate making method using an 488 nm oscillation beam of an argon ion laser is considered to be one of the most promising techniques in the future.

Several proposals have hitherto been made for a photopolymerizable photosensitive material containing a photopolymerization initiation system capable of being sensitive to light rays in the visible light region. For example, a system of hexaarylbiimidazole, a radical generator and a dye (Japanese Patent Publication No.
-37377), a system of hexaarylbiimidazole and (p-dialkylaminobenzylidene) ketone (JP-A-47-2528, JP-A-54-1552).
92), systems of cyclic cis-α-dicarbonyl compounds and dyes (JP-A-48-84183), systems of substituted triazines and merocyanine dyes (JP-A-54-15102).
No. 4), a system of ketocoumarin and an activator (JP-A-52-
112681, JP-A-58-15503,
JP-A-60-88005), systems of substituted triazines and sensitizers (JP-A-58-29803, 4030).
No. 2), biimidazole, styrene derivative, thiol system (JP-A-59-56403), organic peroxide and dye system (JP-A-59-140203, JP-A-59-140203).
89340).

[0006]

However, although these prior arts are certainly effective for visible light, they have the drawback that they are not very sensitive and still inadequate from a practical point of view. It was

[0007]

Means for Solving the Problems As a result of intensive investigations by the present inventors to overcome such difficulties and obtain an excellent photopolymerizable composition, the inventors have found that addition polymerization having at least one ethylenic double bond is possible. By containing at least one compound, a sensitizer having a specific tetrahydroquinoline skeleton and a 1-indanone skeleton in the molecule and an activator capable of generating an active radical upon light irradiation in the coexistence of the sensitizer, The inventors have found that the sensitivity is high and the practicality is high, and have arrived at the present invention.

In other words, an object of the present invention is to provide a photopolymerizable composition which is more sensitive to visible light, especially long wavelength light such as 488 nm. Another object of the present invention is to provide a photopolymerizable composition which enables a higher speed plate making work by using a laser having a lower output, for example, an air-cooled argon laser in the case of laser plate making with an argon ion laser. Especially.

Another object of the present invention is to provide a photopolymerizable composition which enables a plate making operation which is extremely advantageous in terms of cost and time. Therefore, the object of the present invention is to
(A) an addition-polymerizable compound having at least one ethylenically unsaturated double bond, (b) a sensitizer represented by the following general formula [I]

[0010]

[Chemical 2]

(Wherein R ¹ represents a hydrogen atom or an alkyl group, R ² and R ³ represent a hydrogen atom, an alkyl group, an alkoxy group or an alkylthio group, respectively,
R ¹ and R ² may be bonded to each other to form a ring structure, R ^{4 to} R ⁶ each represent an alkoxy group, and m represents 0 or 1. And (c) at least one activator that generates a radical upon irradiation with light in the coexistence with the sensitizer is easily achieved by the photopolymerizable composition.

The present invention will be described in detail below. In the photopolymerizable composition of the present invention, the addition-polymerizable compound having at least one ethylenically unsaturated double bond represented by (a) (hereinafter, abbreviated as “ethylenic compound”) means photopolymerizable When the composition is irradiated with actinic rays, it is a compound having an ethylenically unsaturated double bond that undergoes addition polymerization by the action of a photopolymerization initiation system which is a second essential component, and is cured, for example, Is a monomer having a double bond or a polymer having an ethylenically unsaturated double bond in the side chain or main chain. Incidentally, the meaning of the monomer in the present invention is a concept facing a so-called polymer substance, and therefore includes not only a narrowly defined monomer but also a dimer, a trimer and an oligomer. is there.

Examples of the monomer having an ethylenically unsaturated bond include unsaturated carboxylic acids, esters of aliphatic polyhydroxy compounds with unsaturated carboxylic acids; esters of aromatic polyhydroxy compounds with unsaturated carboxylic acids; Examples thereof include esters obtained by an esterification reaction of a saturated carboxylic acid with a polyvalent carboxylic acid and the above-mentioned aliphatic polyhydroxy compound, polyvalent hydroxy compound such as aromatic polyhydroxy compound, and the like.

The ester of the aliphatic polyhydroxy compound and the unsaturated carboxylic acid is not limited, but specific examples thereof include ethylene glycol diacrylate, triethylene glycol diacrylate, trimethylolpropane triacrylate and trimethylolethane triacrylate. , Pentaerythritol diacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol tetraacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate,
Acrylic esters such as glycerol acrylyl, methacrylic acid esters obtained by replacing acrylates of these exemplified compounds with methacrylates, itaconic acid esters similarly replaced with itaconate, crotonic acid esters replaced with crotonate or maleic acid esters replaced with maleate, etc. is there.

Examples of the ester of an aromatic polyhydroxy compound and an unsaturated carboxylic acid include hydroquinone diacrylate, hydroquinone dimethacrylate, resorcin diacrylate, resorcin dimethacrylate and pyrogallol triacrylate. The ester obtained by the esterification reaction of an unsaturated carboxylic acid with a polyvalent carboxylic acid or a polyvalent hydroxy compound is not necessarily a single substance, but representative specific examples include acrylic acid, phthalic acid and ethylene glycol. Examples thereof include condensates, condensates of acrylic acid, maleic acid and diethylene glycol, condensates of methacrylic acid, terephthalic acid and pentaerythritol, condensates of acrylic acid, adibic acid, butanediol and glycerin.

Other examples of the ethylenic compound used in the present invention include acrylamides such as ethylenebisacrylamide; allyl esters such as diallyl phthalate;
Vinyl group-containing compounds such as divinyl phthalate are useful. The polymer having an ethylenically unsaturated bond in the main chain described above is, for example, a polyester obtained by a polycondensation reaction of an unsaturated divalent carboxylic acid and a dihydroxy compound,
There are polyamides and the like obtained by polycondensation reaction of unsaturated divalent carboxylic acid and diamine.

The polymer having an ethylenically unsaturated bond in the side chain is a condensation polycondensation product of a divalent carboxylic acid having an unsaturated bond in the side chain, such as itaconic acid, propylidene succinic acid, ethylidene malonic acid, and a dihydroxy or diamine compound. There is coalescence. Further, a polymer having a functional group having a reactive activity such as a hydroxy group or a methyl halide group in its side chain, for example, polyvinyl alcohol, poly (2-hydroxyethyl methacrylate), polyepichlorohydrin, etc. and acrylic acid,
Polymers obtained by polymer reaction with unsaturated carboxylic acids such as methacrylic acid and crotonic acid can also be suitably used.

Of the above-mentioned ethylenic compounds, acrylic acid ester or methacrylic acid ester monomers are particularly preferably used. Next, in the present invention (b)
The sensitizer represented by the structural formula [I] described above will be described. It has been found that all of these sensitizers have a tetrahydroquinoline structure in the molecule, which significantly increases the sensitivity to visible light. This effect is particularly remarkable for the compound represented by the general formula [I] described above, and as will be described later in Examples and Comparative Examples, by replacing the N, N-dialkylaniline structure in the molecule with a derivative having a tetrahydroquinoline structure, 488 nm A significant increase in sensitivity was observed with respect to the light rays. The usefulness of this effect indicates that it can be applied to an air-cooled argon laser having a low output in the image forming method by the argon ion laser scanning.

In the above general formula [I], when R ^{1 to} R ³ each represent an alkyl group, or when R ² and R ³ each represent an alkoxy group or an alkylthio group, R ^{4 to} R ⁶ each represent an alkoxy group. When representing, the number of carbon atoms is preferably 1 to 10, and the number of carbon atoms is 1
It is particularly preferable that it is from 5 to 5, and it may have a straight chain or a side chain.

Typical examples of the tetrahydroquinoline sensitizer represented by the general formula [I] are shown below.
The tetrahydroquinoline sensitizer used in the present invention is not limited to these specific examples. Unless stated otherwise in the following examples, m = 0 and R ^{1 to} R ³ all represent hydrogen atoms. When R ¹ and R ² form the following ring structure

[0021]

[Chemical 3]

R ^{1 to} R ² ; represented by julolidine ring.

Examples of compounds

[Table 1] [I-1] R¹~ R²A julolidine ring, R^Four~ R
⁶Methoxy group [I-2] R¹~ R²A julolidine ring, R^Four~ R
⁶Ethoxy group [I-3] R¹Ethyl group, R³Ethoxy group, R
^Four~ R⁶Methoxy group [I-4] R¹Ethyl group, R³Ethoxy group, R
^Four~ R⁶Ethoxy group [I-5] R¹-R²A julolidine ring, R³; D
Toxy group, R^Four~ R⁶Methoxy group [I-6] m = 1, R¹~ R²A julolidine ring,
R^Four~ R⁶Methoxy group [I-7] m = 1, R¹~ R²A julolidine ring,
R^Four~ R⁶Ethoxy group [I-8] m = 1, R¹; Ethyl group, R³; Etoki
Shi group, R^Four~ R⁶Methoxy group [I-9] m = 1, R¹; Ethyl group, R³; Etoki
Shi group, R^Four~ R⁶Ethoxy group [I-10] m = 1, R¹~ R²A julolidine ring,
R³Ethoxy group, R ^Four~ R⁶Methoxy group [I-11]

[0024]

[Chemical 4]

The sensitizers of the present invention exemplified above are not limited, but for example, the corresponding aldehydes of indanone derivatives and tetrahydroquinoline derivatives are subjected to acid or base catalysis as exemplified later in Synthesis Examples 1 and 2. It can be synthesized by dehydration condensation.

The sensitizer used in the photopolymerizable composition of the present invention can be preferably used alone or in combination of two or more kinds. The activator represented by (c) in the present invention, which is capable of generating an active radical when irradiated with light in the presence of the above-mentioned sensitizer, is an active radical which induces some action with the photoexcited sensitizer. Any material can be used as long as it has the property of generating Preferred activators include, for example, hexaarylbiimidazole, halogenated hydrocarbon derivatives, organic thiol compounds, diaryliodonium salts and the like. In particular, the combined use of hexaarylbiimidazole and an organic thiol compound significantly increases the sensitivity.

Specific examples of hexaarylbiimidazole include 2,2'-bis (o-chlorophenyl) -4,
4 ', 5,5'-tetraphenylbiimidazole, 2,
2'-bis (o-chlorophenyl) -4,4 ', 5
5'-tetra (p-carboethoxyphenyl) biimidazole, 2,2'-bis (o-chlorophenyl) -4,
4 ', 5,5'-tetra (p-bromophenyl) biimidazole, 2,2'-bis (o-chlorophenyl)-
4,4 ', 5,5'-tetra (o, p-dichlorophenyl) biimidazole, 2,2'-bis (o-bromophenyl) -4,4', 5,5'-tetraphenylbiimidazole, 2 , 2'-bis (o, p-dichlorophenyl)
-4,4 ', 5,5'-Tetraphenylbiimidazole, 2,2'-bis (o-chlorophenyl) -4,
4 ', 5,5'-tetra (m-methoxyphenyl) biimidazole, 2,2'-bis (o, o'-dichlorophenyl) -4,4', 5,5'-tetraphenylbiimidazole, 2, 2'-bis (o-nitrophenyl) -4,
4 ', 5,5'-tetraphenylbiimidazole, 2,
2'-bis (o-methylphenyl) -4,4 ', 5
5'-tetraphenyl biimidazole etc. are mentioned.

Specific examples of the halogenated hydrocarbon derivative include 2,4,6-tris (trichloromethyl) -s-triazine, 2,4,6-tris (tribromomethyl) -s-triazine, and the like. 2-Methyl-4,6-di (trichloromethyl) -s-triazine, 2- (p-methoxyphenyl) -4,6-di (trichloromethyl)-
s-triazine, 2,2,2-trichloromethylacetophenone, tribromomethylphenyl sulfone, 2-trichloromethyl-5- (p-methoxystyryl) -1,
3,4-oxadiazole and the like can be mentioned.

Examples of the organic thiol compound include 2
-Mercaptobenzthiazole, 2-mercaptobenzoxazole, 2-mercaptobenzimidazole, 2
-Mercapto-4 (3H) -quinazolinone, β-mercaptonaphthalene and the like can be mentioned. Examples of the diaryliodonium salt include diphenyliodonium hexafluorophosphate, diphenyliodonium tosylate, diphenyliodonium fluoroborate, diphenyliodonium hexafluoroarsenate, diphenyliodonium chloride, ditolyliodonium hexafluorophosphate, phenyl (p-anisyl) iodonium hexafluoro. Examples thereof include phosphate and bis (m-nitrophenyl) iodonium hexafluorophosphate.

Other than these, the activator in the present invention is known, for example, ketoxime esters such as 3-benzoyloxyiminobutan-2-one, 3,3 ',
4,4'-Tetra (t-butylperoxycarbonyl)
Organic peroxides such as benzophenone, N-phenylglycine, dimedone and the like can also be used. The activator used in the photopolymerizable composition of the present invention can be preferably used alone or in combination of two or more kinds.

The suitable amount of the sensitizer and the activator constituting the photopolymerization initiation system used in the photopolymerizable composition of the present invention described above is not particularly limited, but 100 parts by weight of the (a) ethylenic compound is used. On the other hand, the (b) sensitizer is preferably 0.05 to 20 parts by weight, more preferably 0.2 to 10 parts by weight, and the (c) activator is preferably 0.5 to 100 parts by weight, more preferably It is suitable to use in a proportion of 1 to 50 parts by weight.

In the photopolymerizable composition of the present invention, in addition to the above-mentioned constituents, it is preferable to further add an organic polymer substance as a binder in order to modify the composition and improve the physical properties after photocuring. . The binder may be appropriately selected depending on the improvement purpose such as compatibility, film forming property, developability, and adhesiveness. Specifically, for example, to improve the water-based developability, acrylic acid copolymer, methacrylic acid copolymer, itaconic acid copolymer, partially esterified maleic acid copolymer, acidic cellulose modified product having a carboxyl group in the side chain, Examples include polyethylene oxide and polyvinylpyrrolidone.

To improve the film strength and adhesiveness, a polyether of epichlorohydrin and bisphenol A; soluble nylon; alkyl polymethacrylate such as polymethylmethacrylate or alkyl polyacrylate; alkyl methacrylate and acrylonitrile, acrylic acid , Copolymers with methacrylic acid, vinyl chloride, vinylidene chloride, styrene, etc .; copolymers of acrylonitrile with vinyl chloride, vinylidene chloride; vinylidene chloride, chlorinated polyolefins, copolymers of vinyl chloride with vinyl acetate; poly Vinyl acetate; Acrylonitrile / styrene copolymer; Acrylonitol / butadiene / styrene copolymer; Polyvinyl alkyl ether; Polyvinyl alkyl ketone;
Polystyrene; polyamide; polyurethane; polyethylene terephthalate isophthalate; acetyl cellulose, polyvinyl butyral and the like.
These binders can be added and mixed in a weight ratio of preferably 500% or less, more preferably 200% or less, based on the ethylenic compound.

The photopolymerizable composition of the present invention may further contain a thermal polymerization inhibitor, a coloring agent, a plasticizer, a surface protective agent, a smoothing agent, if necessary.
Coating aids and other additives can be added. Examples of the thermal polymerization inhibitor include hydroquinone, p-methoxyphenol, pyrogallol, catechol, 2,6-di-
There are t-butyl-p-cresol, β-naphthol, and the like. Examples of the colorant include phthalocyanine pigments, azo pigments, carbon black, pigments such as titanium oxide, ethyl violet, crystal violet, azo dyes, anthraquinone dyes. , There are cyanine dyes. When the binder is used, the thermal polymerization inhibitor and the colorant are added in an amount of 0.01% to 3% of the thermal polymerization inhibitor and 0.1% of the colorant with respect to the total weight of the ethylenic compound and the binder.
1% to 20% is preferred.

Examples of the plasticizer include dioctyl phthalate, didodecyl phthalate, triethylene glycol dicaprylate, dimethyl glycol phthalate, tricresyl phosphate, dioctyl adipate, dibutyl sebacate, triacetyl glycerin, and the like. When used, 10% or less of the total weight of the ethylenic compound and the binder can be added.

When using the photopolymerizable composition of the present invention,
The light-sensitive material can be prepared by forming the light-sensitive material without a solvent or dissolving it in a suitable solvent to form a solution, which is applied on a support and dried. Examples of the solvent include methyl ethyl ketone, cyclohexanone, butyl acetate, amyl acetate, ethyl propionate, toluene, xylene, monochlorobenzene, carbon tetrachloride, trichloroethylene,
There are trichloroethane, dimethylformamide, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, bentoxone and the like, and one kind or a combination of two or more kinds can be used.

The support applied when preparing a light-sensitive material using the photopolymerizable composition of the present invention may be any of those usually used. For example, a sheet of metal such as aluminum, magnesium, copper, zinc, chromium, nickel, iron or an alloy containing them as a main component; high-quality paper, art paper,
Papers such as release paper; inorganic sheets such as glass and ceramics; polyethylene terephthalate, polyethylene, polymethylmethacrylate, polyvinyl chloride, vinyl chloride-
Polymer sheets such as vinylidene chloride copolymer, polystyrene, 6-nylon, cellulose triacetate, and cellulose acetate butyrate are available.

Further, the photopolymerizable composition of the present invention is further provided with a known technique for preventing adverse effects such as sensitivity deterioration and storage stability deterioration due to oxygen, for example, providing a peelable transparent cover sheet on the photosensitive layer. Wax-like substance with low oxygen permeability,
An undercoat layer made of a water-soluble polymer or the like can be provided.
The exposure light source that can be applied to the composition of the present invention is not particularly limited, but includes carbon arc, high pressure mercury lamp, xenon lamp, metal halide lamp, fluorescent lamp, tungsten lamp, helium cadmium laser, argon ion laser, etc. visible light of 400 nm or more. A general-purpose light source can be used more suitably.

[0039]

EXAMPLES The present invention will be described in more detail below with reference to synthesis examples, examples and comparative examples, but the present invention is not limited to these examples unless it exceeds the gist.

Synthesis Example 1 (4,6,7-trimethoxy-
Preparation of 1-indanone) 20 g of 2,4,5-trimethoxybenzaldehyde and 20 g of malonic acid were reacted in a solvent of 100 ml of pyridine using piperidine as a catalyst at 80 ° C. for 5 hours. 5 in the reaction solution
00 ml of water was added, and the precipitated 2,4,5-trimethoxycinnamic acid (19 g) was filtered and extracted. Obtained 2,
10 g of 4,5-trimethoxycinnamic acid was reduced with hydrogen using a palladium-carbon catalyst to obtain 9 g of 2,4,5-trimethoxyphenylpropionic acid.

5 g of this 2,4,5-trimethoxyphenylpropionic acid was reacted in 100 g of polyphosphoric acid at 80 ° C. for 4 hours, after the reaction, 500 ml of water was added, and further,
Neutralize with sodium hydroxide aqueous solution and precipitate 4,6,7
3 g of -trimethoxy-1-indanone was extracted by filtration.
The obtained product was identified by thin layer chromatography, nuclear magnetic resonance spectrum and infrared absorption spectrum.

Synthetic Example 2 (Preparation of sensitizer [I-1]) Julolidine-9-carbaldehyde, 4.1 g, 4, 6 synthesized by using dimethylformamide and phosphorus oxychloride according to a conventional method using julolidine as a raw material. , 7-trimethoxy-1-indanone (5 g) and potassium hydroxide (0.5 g) were reacted in an ethanol solvent at 80 ° C. for 10 hours under a nitrogen atmosphere. The reaction product was a silica gel column (Wakogel C-200, using a mixed solvent of ethyl acetate and hexane (1: 9)).
Separated and purified by Wako Pure Chemical Industries, Ltd. [I-1]
1 g was obtained. [I-1] was identified by thin layer chromatography, nuclear magnetic resonance spectrum, and infrared absorption spectrum.

Examples 1 to 9 and Comparative Examples 1 to 6 On a grained and anodized aluminum sheet, using a whirler, a photosensitive composition coating solution having the following composition was applied to a dry film thickness of 2 μm. Then, a polyvinyl alcohol aqueous solution was applied on the surface so that the dry film thickness was 3 μm to prepare a photosensitive material sample.

Next, a step tablet (manufactured by Kodak Co., Ltd.) in which the light amount is attenuated by 1 / √2 each time it is increased by one step is brought into close contact with this photosensitive material sample, and 1 m to 1 kW xenon lamp (USHIO INC. ) OSB-1001A / 2)
Glass filter (Toshiba Glass Co., Ltd., Y-47 and K)
The light of 480 to 490 nm obtained through L-49) was irradiated for 10 seconds. The exposed sample was developed with an aqueous solution containing 2% by weight of butyl cellosolve and 1% by weight of sodium silicate, and the minimum exposure amount necessary for image formation was calculated from the step number of the obtained step-cured image,
The sensitivity of the photosensitive composition was used. The results are shown in Table-1.

[Photosensitive composition coating liquid]

Table 2 Methyl methacrylate / methacrylic acid copolymer 50 parts (weight average molecular weight 45,000, copolymerization ratio 85/15) trimethylolpropane triacrylate 50 parts Victoria Pure Blue BOH 0.1 part Methyl Secosolve 800 parts Tetrahydrofuran 50 parts Sensitizer (listed in Table-1) Activator (listed in Table-1)

[0046]

[Table 3]

In Table 1, sensitizers [S-1] to [S-3].
Are each

[0048]

[Chemical 5]

Represents In addition, in Table 1, the active agent [B-
1] to [B-7] are respectively [B-1]

[0050]

[Chemical 6]

[B-2]

[0052]

[Chemical 7]

[0053]

[B-3] 2,4,6-Trichloromethyl-s-triazine [B-4] Diphenyliodonium hexafluorophosphate [B-5] 2-Mercaptobenzthiazole [B-6] 2-Mercaptobenz Oxazole [B-7] Represents 2-mercaptobenzimidazole.

[0054]

The photopolymerizable composition of the present invention is
In particular, it is extremely sensitive to long-wavelength light. Therefore, the composition is useful in a wide range of application fields, for example, for producing a printing plate such as a flat plate, an intaglio, a letterpress, a printed wiring and
Photoresist for making C, dry film, image formation such as relief image and image duplication, photocurable ink,
Since it can be used for paints, adhesives, etc., it is extremely useful industrially.

Claims (1)

[Claims] 1. At least (a) an addition-polymerizable compound having at least one ethylenically unsaturated double bond, (b) a sensitizer represented by the following general formula [I]: (In the formula, R ¹ represents a hydrogen atom or an alkyl group, and R ^1
2 and R ³ each represent a hydrogen atom, an alkyl group, an alkoxy group or an alkylthio group, or R ¹ and R ² may be bonded to each other to form a ring structure,
R ^{4 to} R ⁶ each represent an alkoxy group, and m represents 0 or 1. And (c) at least one activator which generates an active radical upon irradiation with light in the coexistence with the sensitizer.