JP7774256B2 - Oxygen inhibition reducer, polymerizable composition, cured product, and method for producing the cured product - Google Patents

Description

The present invention relates to an oxygen inhibition reducer, a polymerizable composition, a cured product, and a method for producing the cured product.

When photocuring a photocurable resin composition, curing is inhibited by oxygen diffusing from the coating surface into the coating and by oxygen dissolved within the coating. The coating surface, which comes into direct contact with air, is particularly susceptible to oxygen inhibition, resulting in poor curing of the surface, resulting in abnormal appearance and reduced surface properties. Therefore, there is a need for the development of a photocuring system that can effectively reduce curing inhibition caused by oxygen.

Oxygen inhibition is generally known to occur through the following mechanism: When a photocurable resin composition is irradiated with light, active radical species are generated from the photopolymerization initiator, which then attack the unsaturated bonds in the monomer, generating growing radical species and causing curing to proceed. If oxygen is present, the growing radical species are trapped by the oxygen, generating peroxy radical species. Since peroxy radical species do not react with the monomer, curing is inhibited.

One way to reduce oxygen inhibition is to increase the proportion of photopolymerization initiator added to the entire photocurable resin composition. However, increasing the number of photopolymerization initiators added can lead to problems such as a deterioration in the physical properties of the coating film and bleeding of the photopolymerization initiator onto the coating film surface.

Patent Document 1 also discloses a method of using an amine compound as an oxygen inhibition reducer to reduce oxygen inhibition. Amine compounds undergo hydrogen abstraction from peroxy radical species, turning themselves into active radical species and having the effect of restarting curing that has been stopped by oxygen. However, the effect of amine compounds in reducing oxygen inhibition is insufficient, and the cured product turns yellow, limiting the conditions under which they can be used. For these reasons, further improvements are desired.

Non-Patent Document 1 also discloses a method for efficiently sensitized decomposition of organic peroxides by irradiating light on ketone compounds contained in polymer chains. Sensitized decomposition by ketone compounds of organic peroxides generated by recombination or hydrogen abstraction of peroxy radical species is thought to be able to efficiently reduce cure inhibition by oxygen with a small amount of addition, because the ketone compounds act catalytically and can regenerate two active radical species from one peroxide bond.

Japanese Patent Application Laid-Open No. 2000-158594

macromolecules, 1978, 11, 937-942.

The present invention provides an oxygen inhibition reducer that can effectively reduce cure inhibition caused by oxygen without causing yellowing of the cured product.

Furthermore, the present invention provides a polymerizable composition, a cured product thereof, and a method for producing the cured product.

That is, the present invention relates to an oxygen inhibition reducer containing a compound represented by the following general formula (1):
(In formula (1), -X- may or may not be present. When present, X represents an oxygen atom or a sulfur atom. A represents an alkylene group which may contain an ether bond, a thioether bond, an ester bond, or an amide bond. Y represents a fluoroalkyl group having 1 to 18 carbon atoms.)

The present invention also relates to a polymerizable composition containing the oxygen inhibition reducer and a radically polymerizable compound, a cured product formed from the polymerizable composition, and a method for producing the cured product.

The compound of the present invention represented by the above general formula (1) has an aryl ketone structure, which sensitizes the decomposition of compounds containing peroxy radical species generated by oxygen inhibition during photocuring, effectively reducing curing inhibition caused by oxygen and preventing yellowing of the cured product. Furthermore, the presence of a fluoroalkyl group causes segregation at the coating film surface, thereby improving poor curing on the coating film surface, which is most susceptible to the effects of oxygen inhibition.

<Oxygen inhibition reducer>
The oxygen inhibition reducer of the present invention includes a compound represented by the following general formula (1):
(In formula (1), -X- may or may not be present. When present, X represents an oxygen atom or a sulfur atom. A represents an alkylene group which may contain an ether bond, a thioether bond, an ester bond, or an amide bond. Y represents a fluoroalkyl group having 1 to 18 carbon atoms.)

In the general formula (1), X is preferably an oxygen atom or a sulfur atom, from the viewpoints of increasing sensitivity to lamp light and increasing the efficiency of sensitized decomposition.

In the general formula (1), A is preferably an alkylene group having 0 to 6 carbon atoms. The alkylene group may be linear or branched. Among these, from the viewpoint of ease of synthesis, A preferably contains an ether bond, an ester bond, or an amide bond, and particularly preferably contains an ether bond or an amide bond.

In the general formula (1), the fluoroalkyl group may be linear or branched. It preferably has 1 to 18 carbon atoms, and particularly preferably 2 to 7.

A wide variety of known techniques can be used to produce the compound represented by general formula (1), including, for example, a step of reacting a hydroxy-substituted aryl ketone derivative with a fluoroalkyl halide compound in the presence of a base, a step of reacting a carboxy-substituted aryl ketone derivative with a hydroxyfluoroalkyl compound under reflux, or a step of reacting a carboxy-substituted aryl ketone derivative with an aminofluoroalkyl compound in the presence of a condensing agent. After the reaction, the process may include a step of distilling off (removing) excess raw materials under reduced pressure, or a purification step.

<Polymerizable composition>
The polymerizable composition of the present invention contains a compound represented by the general formula (1) and a radically polymerizable compound. Furthermore, the polymerizable composition can be imparted with developability by containing an alkali-soluble resin. Furthermore, the polymerizable composition can contain other components in appropriate combination.

<Radical polymerizable compound>
As the radical polymerizable compound of the present invention, a compound having an ethylenically unsaturated group can be preferably used. Examples of the radical polymerizable compound include (meth)acrylic acid esters, styrenes, maleic acid esters, fumaric acid esters, itaconic acid esters, cinnamic acid esters, crotonic acid esters, vinyl ethers, vinyl esters, vinyl ketones, allyl ethers, allyl esters, N-substituted maleimides, N-vinyl compounds, unsaturated nitriles, and olefins. Among these, it is preferable to use (meth)acrylic acid esters, which have high reactivity. The radical polymerizable compound may be used alone or in combination of two or more types.

The (meth)acrylic acid esters may be monofunctional or polyfunctional compounds. Examples of monofunctional compounds include alkyl (meth)acrylates such as methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, lauryl (meth)acrylate, and stearyl (meth)acrylate; ester compounds of (meth)acrylic acid and alicyclic alcohols such as cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, and 2-ethyl-2-adamantyl (meth)acrylate; aryl (meth)acrylates such as phenyl (meth)acrylate and benzyl (meth)acrylate; 2- Monomers having a hydroxy group, such as hydroxyethyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, 3-hydroxy-1-adamantyl (meth)acrylate, polyethylene glycol mono(meth)acrylate, and polypropylene glycol mono(meth)acrylate; methoxyethyl (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, phenoxypolyethylene glycol (meth)acrylate, 2-phenylphenoxyethyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, (2-methyl-2-ethyl-1,3-dioxolan-4-yl)methyl (meth)acrylate, and (3-ethyloxetan-3-yl)methyl Monomers having a chain or cyclic ether bond, such as (meth)acrylate and cyclic trimethylolpropane formal (meth)acrylate; monomers having a nitrogen atom, such as N,N-dimethylaminoethyl (meth)acrylate, N,N-dimethyl(meth)acrylamide, N-methylol(meth)acrylamide, N-isopropyl(meth)acrylamide, N,N-dimethylaminopropyl(meth)acrylamide, diacetone(meth)acrylamide, (meth)acryloylmorpholine, and N-(meth)acryloyloxyethylhexahydrophthalimide; monomers having an isocyanate group, such as 2-(meth)acryloyloxyethyl isocyanate; glycidyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate glycidyl ether monomers having an epoxy group such as 2-((meth)acryloyloxy)ethyl phosphate; monomers having a phosphorus atom such as 2-((meth)acryloxypropyltrimethoxysilane; monomers having a silicon atom such as 3-(meth)acryloxypropyltrimethoxysilane; monomers having a fluorine atom such as 2,2,2-trifluoroethyl (meth)acrylate, 2,2,3,3,3-pentafluoropropyl (meth)acrylate, and 2-(perfluorohexyl)ethyl (meth)acrylate; and monomers having a carboxyl group such as (meth)acrylic acid, mono(2-(meth)acryloyloxyethyl) succinate, mono(2-(meth)acryloyloxyethyl) phthalate, mono(2-(meth)acryloyloxyethyl) maleate, and ω-carboxy-polycaprolactone mono(meth)acrylate.

Examples of the polyfunctional compounds include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, glycerin di(meth)acrylate, glycerin tri(meth)acrylate, glycerin propoxy tri(meth)acrylate, trimethylolethane tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, pentaerythritol di(meth)acrylate monostearate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, and hydroxypivalic acid neopentyl. Polyhydric alcohols such as diglycol di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, 2,2-bis(4-(meth)acryloxyethoxyphenyl)propane, 2,2-bis(4-(meth)acryloxypolyethoxyphenyl)propane, 9,9-bis(4-(2-(meth)acryloyloxyethoxy)phenyl)fluorene, and 9,9-bis(4-(2-(2-(meth)acryloyloxyethoxy)ethoxy)phenyl)fluorene. and (meth)acrylic acid ester compounds; examples include bis(4-(meth)acryloxyphenyl)sulfide, bis(4-(meth)acryloylthiophenyl)sulfide, tris(2-(meth)acryloyloxyethyl)isocyanurate, ethylenebis(meth)acrylamide, zinc (meth)acrylate, zirconium (meth)acrylate, aliphatic urethane acrylate, aromatic urethane acrylate, epoxy acrylate, and polyester acrylate.

From the viewpoints of improving the sensitivity of the polymerizable composition, reducing oxygen inhibition, and improving the mechanical strength, hardness, heat resistance, durability, and chemical resistance of the cured coating film, the (meth)acrylic acid esters are preferably ester compounds of the polyhydric alcohols and (meth)acrylic acid, and particularly preferred are trimethylolethane triacrylate, trimethylolpropane triacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol pentaacrylate, and dipentaerythritol hexaacrylate.

The content of the compound represented by general formula (1) is preferably 0.1 to 40 parts by mass, more preferably 0.5 to 20 parts by mass, and even more preferably 1 to 15 parts by mass, relative to 100 parts by mass of the radical polymerizable compound.

<Alkali-soluble resin>
The polymerizable composition can be suitably used as a negative resist by further blending an alkali-soluble resin. The alkali-soluble resin can be any resin commonly used in negative resists, and is not particularly limited as long as it is soluble in an alkaline aqueous solution, but is preferably a resin containing a carboxyl group. The alkali-soluble resin may be used alone or in combination of two or more types.

A polymerization initiator can be added to the polymerizable composition to promote curing or improve the physical properties of the cured product. The polymerization initiator decomposes when exposed to active energy rays, and the active species generated have the function of initiating the polymerization (curing) of the radically polymerizable compound. The polymerization initiator may be used alone or in combination of two or more types.

The polymerization initiator may be any known initiator, such as α-hydroxyacetophenone derivatives such as 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-propiophenone, 4'-(2-hydroxyethoxy)-2-hydroxy-2-methylpropiophenone, and 2-hydroxy-1-(4-(4-(2-hydroxy-2-methylpropionyl)benzyl)phenyl)-2-methylpropan-1-one; 2-methyl-4'-methylthio-2-morpholinopropiophenone, and 2-benzyl-2-(N,N-dimethylamino)-1-(4-morpholinophenyl)butane. α-aminoacetophenone derivatives such as 2-(dimethylamino)-2-(4-methylbenzyl)-1-(4-morpholinophenyl)butan-1-one; acylphosphine oxide derivatives such as diphenyl-2,4,6-trimethylbenzoylphosphine oxide, phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, and ethyl(mesitylcarbonyl)phenylphosphinate; 1-[4-(phenylthio)phenyl]octane-1,2-dione-2-(O-benzoyloxime), 1-[({1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazo oxime ester derivatives such as 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine, 2-(3,4-dimethoxystyryl)-4,6-bis(trichloromethyl)-1,3,5-triazine, and 2-(4-ethoxynaphthyl)-4,6-bis(trichloromethyl)-1,3,5-triazine; benzyl ketal derivatives such as 2,2-dimethoxy-2-phenylacetophenone; thioxanthone derivatives such as isopropylthioxanthone, 4-(4-methylphenylthio)-1,3,5-triazine, and 4-(4-methylphenylthio)-1,3,5-triazine; e) Benzophenone derivatives such as benzophenone; coumarin derivatives such as 3-benzoyl-7-diethylaminocoumarin and 3,3'-carbonylbis(7-diethylaminocoumarin); imidazole derivatives such as 2-(2-chlorophenyl)-1-[2-(2-chlorophenyl)-4,5-diphenyl-1,3-diazol-2-yl]-4,5-diphenylimidazole; organic peroxides such as 3,3',4,4'-tetrakis(tert-butylperoxycarbonyl)benzophenone and dibenzoyl peroxide; azo compounds such as azobisisobutyronitrile; camphorquinone, etc.

The content of the polymerization initiator is preferably 0.1 to 40 parts by mass, more preferably 0.5 to 20 parts by mass, and even more preferably 1 to 15 parts by mass, per 100 parts by mass of the radically polymerizable compound.

A solvent can also be added to the polymerizable composition to improve viscosity, coatability, and the smoothness of the cured film. There are no particular restrictions on the solvent, as long as it can dissolve or disperse the radically polymerizable compound and the like and volatilizes at the drying temperature.

Examples of the solvent include water, alcohol solvents, carbitol solvents, ester solvents, ketone solvents, ether solvents, lactone solvents, unsaturated hydrocarbon solvents, cellosolve acetate solvents, carbitol acetate solvents, propylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether, etc. The solvents may be used alone or in combination of two or more.

The amount of the solvent used is preferably 10 to 1,000 parts by mass, and more preferably 20 to 500 parts by mass, per 100 parts by mass of the solids content of the polymerizable composition.

<Method for preparing polymerizable composition>
When preparing the polymerizable composition, the oxygen inhibition reducer, the radical polymerizable compound, and, if necessary, the alkali-soluble resin and other components are placed in a container, and dissolved or dispersed according to a conventional method using a paint shaker, a bead mill, a sand grind mill, a ball mill, an attritor mill, a two-roll mill, a three-roll mill, etc. Furthermore, if necessary, the mixture may be filtered through a mesh or membrane filter, etc.

In preparing the polymerizable composition, the oxygen inhibition reducer and polymerization initiator may be added to the polymerizable composition from the beginning. However, if the polymerizable composition is to be stored for a relatively long period of time, it is preferable to dissolve or disperse the oxygen inhibition reducer and polymerization initiator in a composition containing a radically polymerizable compound immediately before use.

<Method of producing cured product>
The cured product of the present invention is formed from the polymerizable composition. Examples of a method for producing the cured product include a production method including a step of applying the polymerizable composition onto a substrate and then irradiating the polymerizable composition with active energy rays.

Examples of the coating method include spin coating, bar coating, spray coating, dip coating, flow coating, slit coating, doctor blade coating, gravure coating, screen printing, offset printing, inkjet printing, and dispenser printing. The substrate may be, for example, a film or sheet made of glass, silicon wafer, metal, plastic, or the like, or a three-dimensional molded product; the shape of the substrate is not limited.

The step of irradiating the polymerizable composition with active energy rays, such as electron beams, ultraviolet rays, visible light, or radiation, polymerizes the radically polymerizable compound to obtain a cured product.

The active energy rays are preferably light with a wavelength of 250 to 450 nm, and from the viewpoint of rapid curing, light with a wavelength of 350 to 410 nm is more preferable.

The light source for the light irradiation can be a low-pressure mercury lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, a metal halide lamp, an ultraviolet electrodeless lamp, an LED lamp, a xenon arc lamp, a carbon arc lamp, sunlight, a solid-state laser such as a YAG laser, a semiconductor laser, or a gas laser such as an argon laser. If necessary, curing can be achieved by using a sensitizer that absorbs the light as the additive.

The exposure dose of the actinic energy ray should be appropriately set depending on the wavelength and intensity of the actinic energy ray and the composition of the polymerizable composition. For example, the exposure dose in the UV-A region is preferably 10 to 5,000 mJ/ ^cm2 , and more preferably 30 to 1,000 mJ/ ^cm2 .

Furthermore, when the polymerizable composition contains the solvent, the method for producing the cured product may include a drying step.

In the drying step, methods for drying the solvent include, for example, heat drying, forced-air heat drying, and reduced-pressure drying. The heat drying method is not particularly limited, but examples include an oven, a hot plate, infrared radiation, and electromagnetic wave radiation. Furthermore, an example of a forced-air heat drying method is a blower drying oven.

In addition, during the drying process, the temperature of the polymerizable composition is lower than the set drying temperature due to the latent heat of vaporization of the solvent, ensuring a longer time until the polymerizable composition gels. Because the time until gelation is affected by factors such as the drying method and film thickness, the drying temperature and time should be set appropriately, including the selection of solvent. For example, the drying temperature is preferably 20 to 120°C, and more preferably 40 to 100°C. The drying time is preferably 1 to 60 minutes, and more preferably 1 to 30 minutes.

The dry film thickness of the polymerizable composition (film thickness of the cured product) is set appropriately depending on the application, but is preferably 0.05 to 500 μm, and more preferably 0.1 to 100 μm.

<Pattern Forming Method>
When the polymerizable composition contains an alkali-soluble resin, a pattern can be formed by photolithography. The polymerizable composition is applied to a substrate in the same manner as described above, and, if necessary, dried to form a dry film. The dried film is then irradiated with active energy rays through a mask, whereby the radically polymerizable compound in the exposed areas polymerizes to form a cured film. Alternatively, a highly accurate pattern shape can also be produced by direct drawing using a laser without using a mask.

After the above exposure, the unexposed areas are developed and removed using an alkaline developer such as a 0.3 to 3% by weight aqueous solution of sodium carbonate, yielding a patterned cured film. Furthermore, to enhance adhesion between the cured film and the substrate, post-baking is performed at 180 to 250°C for 20 to 90 minutes as post-drying. In this way, the desired pattern based on the cured film is formed.

The polymerizable composition of the present invention can be used in a wide variety of applications, including paints and coatings such as hard coating agents, optical disk coating agents, optical fiber coating agents, mobile terminal coating agents, home appliance coating agents, cosmetic container coating agents, woodworking coating agents, internal anti-reflection coating agents for optical elements, high and low refractive index coating agents, heat-shielding coating agents, heat-dissipating coating agents, and anti-fogging agents; offset printing inks, gravure printing inks, screen printing inks, inkjet printing inks, conductive inks, insulating inks, and inks for light guide plates; photosensitive printing plates; nanoimprint materials; resins for 3D printers; holographic recording materials; dental materials; waveguide materials; black stripes for lens sheets; and coatings for optical elements. They can be used for a variety of applications, including green sheets and electrode materials for capacitors; adhesives and sealants for FPDs, HDDs, optical pickup adhesives, image sensor adhesives, organic EL sealants, OCA for touch panels, OCR for touch panels, etc.; resists for FPDs such as color resists, black resists, protective films for color filters, photospacers, black column spacers, frame resists, photoresists for TFT wiring, and interlayer insulating films; resists for printed circuit boards such as liquid solder resists and dry film resists; semiconductor resists, buffer coat films, and other semiconductor materials, and there are no particular restrictions on their applications.

The present invention will be explained in more detail below using examples, but the present invention is not limited to these examples.

Example 1
[Synthesis of Compound 1]
[Synthesis Example 1: Synthesis of Compound 1]
A 200 mL two-neck flask was charged with 0.40 g (1.5 mmol) of 2-(9-oxoxanthen-2-yl)propionic acid, 0.32 g (2.0 mmol) of 1,1'-carbonyldiimidazole, and 30 mL of dehydrated acetone and stirred at room temperature for 7 hours. 0.67 g (4.5 mmol) of 2,2,3,3,3-pentafluoropropylamine was gradually added, and the mixture was stirred at 80°C for 6 hours. After adding 30 mL of ethyl acetate and 30 mL of water, the aqueous phase was removed by separation. The aqueous phase was further extracted twice with 30 mL of ethyl acetate. The combined oil phase was concentrated under reduced pressure to obtain a crude product. The crude product was recrystallized in toluene to obtain 0.07 g (12% yield) of Compound 1. The results of ¹ H-NMR and ¹⁹ F-NMR analyses of the resulting Compound 1 are shown in Table 1.

Example 2
[Synthesis of Compound 2]
[Synthesis Example 2: Synthesis of Compound 2]
A 200 mL two-neck flask was charged with 1.1 g (5.0 mmol) of 4-benzoylbenzoic acid, 0.9 g (5.5 mmol) of 1,1'-carbonyldiimidazole, and 30 mL of anhydrous tetrahydrofuran, and the mixture was stirred at room temperature for 6 hours. 2.2 g (15 mmol) of 2,2,3,3,3-pentafluoropropylamine was gradually added, and the mixture was stirred at room temperature for 4 hours. After adding 50 mL of ethyl acetate and 50 mL of water, the aqueous phase was removed by separation. The aqueous phase was further extracted twice with 50 mL of ethyl acetate. The combined oil phase was concentrated under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography (n-hexane/ethyl acetate = 3/1) to obtain 1.3 g (74% yield) of compound 2. ^{The 1} H-NMR and ¹⁹ F-NMR analysis results for the resulting compound 2 are shown in Table 2.

Example 3
[Synthesis of Compound 3]
[Synthesis Example 3: Synthesis of Compound 3]
A 200 mL two-neck flask was charged with 0.40 g (1.5 mmol) of 4-benzoylbenzoic acid, 0.34 g (2.0 mmol) of 1,1'-carbonyldiimidazole, and 30 mL of anhydrous tetrahydrofuran, and the mixture was stirred at room temperature for 7 hours. 2.0 g (4.5 mmol) of 1H,1H-heptafluorobutylamine was gradually added, and the mixture was stirred at 80°C for 6 hours. 30 mL of ethyl acetate and 30 mL of water were added, and the aqueous phase was removed by separation. The aqueous phase was further extracted twice with 30 mL of ethyl acetate. The combined oil phase was concentrated under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography (n-hexane/ethyl acetate = 2/1) to obtain 1.2 g (yield 57%) of compound 3. ^{The 1} H-NMR and ¹⁹ F-NMR analysis results for the resulting compound 3 are shown in Table 3.

<Preparation of polymerizable composition (A)>
The radical polymerizable compound and solvent in the amounts shown in Table 4 were mixed and stirred, and the oxygen inhibition reducer and polymerization initiator were added and stirred thoroughly to prepare polymerizable compositions (A) of Example 4 and Comparative Example 1.

In Table 4 above, BAPO represents phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide (manufactured by IGM);
TMPTA is trimethylolpropane triacrylate (Tokyo Chemical Industry Reagents);
THF refers to tetrahydrofuran (Tokyo Chemical Industry Co., Ltd. reagent);

<Evaluation of cure inhibition by oxygen>
The polymerizable composition (A) prepared above was applied to a glass substrate using a spin coater. After application, the glass substrate was dried in a clean oven at 60°C for 3 minutes to remove the solvent, producing a coating film. Next, using an exposure device with a UV-LED lamp as the light source, the substrate was irradiated with light of 365 nm wavelength at an exposure dose of 150,000 mJ/ ^cm2 . The residual acrylate percentage (%) of the cured film was measured using attenuated total reflection infrared spectroscopy (ATR-IR). The residual acrylate percentage was calculated using the peak areas of the absorption spectrum of the out-of-plane bending vibration of the double bond group (809 cm ^-1 ) and the absorption spectrum of the carbonyl group (1728 cm ^-1 ), which remained unchanged before and after exposure, based on the following formula. The cured film was also visually inspected for yellowing. The results are shown in Table 5.

<Preparation of polymerizable composition (B)>
The radical polymerizable compound and solvent in the amounts shown in Table 6 were mixed and stirred, and the oxygen inhibition reducer and polymerization initiator were added and stirred thoroughly to prepare polymerizable compositions (B) of Example 5 and Comparative Example 2.

<Evaluation of cure inhibition by oxygen>
The polymerizable composition (B) prepared above was applied to a glass substrate using a spin coater. After application, the glass substrate was dried in a clean oven at 60°C for 3 minutes to remove the solvent, producing a coating film. Next, using a proximity exposure device with a low-pressure mercury lamp as the light source, the substrate was irradiated with light of 254 nm wavelength at an exposure dose of 6000 mJ/ ^cm2 . The cured film was measured for residual acrylate content (%) using attenuated total reflection infrared spectroscopy (ATR-IR). The residual acrylate content was calculated using the absorption spectrum (1634 cm ^-1 ) of the out-of-plane bending vibration of the double bond group and the peak area of the standard peak (2970 cm ^-1 ) that remained unchanged before and after exposure, based on the following formula. The cured film was also visually inspected for yellowing. The results are shown in Table 7.

Claims (4)

An oxygen inhibition reducer comprising a compound represented by the following general formula (1):
(In formula (1) , X represents an oxygen atom . A represents an alkylene group which may contain an ether bond, a thioether bond, an ester bond, or an amide bond. Y represents a fluoroalkyl group having 1 to 18 carbon atoms.) A polymerizable composition comprising the oxygen inhibition reducer according to claim 1 and a radical polymerizable compound. A cured product formed from the polymerizable composition of claim 2. A method for producing a cured product, comprising the step of irradiating the polymerizable composition according to claim 2 with active energy rays.