JPH03255121A - Urethane (meth)acrylate, resin composition and printing ink resin composition containing the same, and cured products thereof - Google Patents

Abstract

PURPOSE:To obtain the title compound which can give a resin composition capable of, in turn, giving a cured product excellent in light and weathering resistances and is suitable especially for a printing ink by reacting a hindered amine compound with an organic polyisocyanate and hydroxylated (meth)acrylic ester. CONSTITUTION:A hindered amine compound having a group of formula I in the molecule (e.g. a compound of formula II or III) is allowed to react with an organic polyisocyanate (e.g. hexamethylene diisocyanate) and a hydroxylated (meth)acrylic ester [e.g. beta-hydroxyethyl (meth)acrylate] to obtain a urethane (meth)acrylate. This compound can give a resin composition which, in turn, can give a cured product of excellent light and weathering resistances and is suitable especially for a printing ink.

Description

DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention is directed to the use of urethane (meth) hindered amine compounds.
The present invention relates to an acrylate, a resin composition using the same, which has excellent light resistance and weather resistance, and is particularly suitable for printing ink, and a cured product thereof.

(Prior art) In recent years, the development of ultraviolet curable printing inks has been actively promoted with the aim of preventing pollution by making printing inks solvent-free, improving productivity by rapid curing, and improving the physical properties of cured films. . Various types of ultraviolet curable printing inks have been proposed so far. For example, there are those described in JP-A-56-93776 and JP-A-56-116764. Industrially, ultraviolet curable printing inks have been used in various inks, such as lithographic printing inks, letterpress printing inks, intaglio printing inks, and screen printing inks.

(Problem to be solved by the invention) Ultraviolet curable printing inks are used in various fields,
Recently, it has come to be used for outdoor purposes as well. When used for outdoor purposes, the cured product must have excellent light and weather resistance, but conventional UV-curable printing inks require a cured product with excellent light and weather resistance. The current situation is that there is very little that can be done.

(Means for Solving Problem 11) As a result of intensive research to improve the above problems, the present inventors have found that the following characteristic printing ink resin composition can improve the above problems. They found this and completed the present invention. That is, the present invention provides a hindered amine compound (a
), an organic polyisocyanate (b) and a hydroxyl group-containing (
Urethane (meth)acrylate (4) obtained by reacting meth)acrylic acid ester (C), (21 above (1)
) A resin composition and a printing ink resin composition characterized by containing the urethane (meth)acrylate matrix and an ethylenically unsaturated group-containing compound other than the matrix component (B+ and a photopolymerization initiator (Q) as an optional component) (3) A cured product of the resin composition or printing ink resin composition according to (21) above.

Urethane (meth)acrylate (4) used in the present invention
can be obtained by reacting a hindered amine compound (a) having these in the molecule, an organic polyisocyanate (b), and a (meth)acrylic acid ester (C) having a hydroxyl group. As a specific example of a hindered amine compound having in the molecule, for example, (Adeka, Argaska Jikki Co., Ltd., MA [LA-57) R1
R4 represents , and both groups coexist.

etc. can be mentioned.

Typical examples of organic polyisocyanate fbl include tolylene diisocyanate, 4゜4-diphenylmethane diisocyanate, inphorone diisocyanate, 4,4-dicyclohexylmethane diisocyanate, hexamethylene diisocyanate, 2,2,4-
Examples include trimer of trimethylhexamethylene diisocyanate, isophorone diisocyanate, and trimer of hexamethylene diisocyanate. The preferred ratio of use of the hindered amine compound (a) and the organic polyisocyanate (b) in the urethanization reaction is as follows: The red ratio is such that the NCO group has a chemical equivalent of 1.1 to 2.0, particularly preferably 1.5 to 2.
The ratio is such that the chemical equivalent is 0.

This urethanization reaction can be carried out in procedures known to those skilled in the art. The reaction temperature of this urethanization reaction is preferably room temperature to 100°C, particularly preferably 50 to 80°C.
It is. The reaction time is preferably 3 to 50 hours, particularly preferably 5 to 15 hours. Then, in the (meth)acrylation reaction, a (meth)acrylic ester having a hydroxyl group is added to one chemical equivalent of the NGO group of the compound having a terminal incyanate group obtained in the urethanization reaction. It is preferable to use the hydroxyl group in an amount of 0.9 to 1.5 chemical equivalents, particularly 1.0 to 1.1 chemical equivalents. The reaction temperature is preferably room temperature to 100°C, particularly preferably 50 to 80°C. The reaction time is preferably 3~
50 hours, particularly preferably 5 to 15 hours. Representative examples of (meth)acrylic esters (C) having a hydroxyl group include β-hydroxyethyl (meth)acrylate,
β-hydroxypropyl (meth)acrylate, 1,4
Examples include -butanediol mono(meth)acrylate, ε-caprolactone-β-hydroxyethyl (meth)acrylate, and pentaerythritol tri(meth)acrylate.

In the present invention, ethylenically unsaturated group-containing compounds other than component (4) are used. (Representative Bl components include, for example, tetrahydrofurfuryl (meth)acrylate, 2-hydroxyethyl (meth)acrylate,
Carpitol (meth)acrylate, phenoxyethyl (meth)acrylate, isobornyl (meth)acrylate, N-vinylpyrrolidone, N-vinylhyridine, acryloylmorpholine, hydrogenated dicyclopentadiene (meth)acrylate (manufactured by Hitachi Chemical ■).

FA-513A, FA-513M, etc.), 1,6-hexanediol di(meth)acrylate, hydroxypivalic acid neobentyl glycol di(meth)acrylate, tricyclodecane dimethyloldi(meth)acrylate, polyethoxy di of bisphenol A (meth)acrylate, polyproboxylic di(meth) of bisphenol A
acrylate, neopentyl glycol di(meth)acrylate, di(meth)acrylate of ε-caprolactone adduct of neopentyl glycol hydroxypivalate, trimethylolpropane tri(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, Dipentaerythritol penta and hexa (meth)
Acrylate, polypentaerythritol poly(meth)
Acrylates, epoxy (meth)acrylates (e.g., reaction products of epoxy resins such as bisphenol A type, bisized polybutadiene, and (meth)acrylic acid), polyester (meth)acrylates (e.g., ethylene glycol, propylene glycol, diethylene glycol) , dipropylene glycol, 1,5-bentanediol, 1
, 6-hexanediol and other diol components and succinic acid,
(meth)acrylates of polyester diols consisting of dibasic acids such as adipic acid, phthalic acid, hexahydrophthalic acid, and tetrahydrophthalic acid; lactone-modified polyester diols consisting of the diol component, dibasic acids, and ε-caprolactone or valerolactone; (meth)acrylate, etc.), polycarbonate (meth)acrylate (for example, (meth)acrylate of polycarbonate diol containing 1,6-hexanediol as the diol component)
, polyurethane (meth)acrylate (for example, a polyol compound, an organic diisocyanate, and a (meth)acrylic ester having a hydroxyl group) in substantially NCO
It can be obtained by reacting the desired groups. Here, typical polyol compounds include ethylene glycol, fluoropylene gelicol, 1,3
- Polyols such as butylene glycol, neopentyl glycol, cyclohexane dimetatool, tricyclodecane dimethylol, 1,4-butanediol, 1,6-hexanediol, trimethylolpropane, polypropylene glycol, polyethylene glycol, polytetra The alcohol component is a polyether polyol such as methylene glycol or propylene-modified polytetramethylene glycol, the above polyol or polyether polyol, or a compound in which ε-canrolactone or valerolactone is added to the above polyol, and on the other hand, adipic acid,
Polyester polyols whose acid components are dibasic acids such as sebacic acid, azelaic acid, dodecane dicarboxylic acid, phthalic acid, tetrahydrophthalic acid, and hexahydrophthalic acid, or their anhydrides, and the aforementioned polyols, polyether polyols, and polyester polyols. Examples include polycarbonate polyols that serve as alcohol components.

Typical organic diisocyanates include tolylene diisocyanate 1-,4,4-diphenylmethane diisocyanate, inphorone diisocyanate, 4,4-dicyclohexylmethane diisocyanate, hexamethylene diisocyanate, 2,2', 4-trimethyl hexa Examples include methylene diisocyanate. The preferable ratio of these used in the urethanization reaction between the polyol compound and the organic diincyanate is such that the NGO group of the organic diisonanate is 1.1 to 2.0 chemical equivalents per 1 chemical equivalent of the OH group of the polyol compound. The ratio is particularly preferably 1.5 to 2.0 chemical equivalents.

This urethanization reaction can be carried out in procedures known to those skilled in the art. The reaction temperature of this urethanization reaction is preferably room temperature to 100°C, particularly preferably 50 to 80°C.
It is. The reaction time is preferably 3 to 50 hours, particularly preferably 5 to 15 hours. Then, in the (meth)acrylation reaction, for one chemical equivalent of the NCO group of the compound having a terminal incyanate group obtained in the urethanization reaction, a (meth)acrylate having a hydroxyl group is
Preferably, the acrylic ester is used in such a manner that its OH group has a chemical equivalent of 0.9 to 1.5, particularly 1.0 to 1.1.

Representative examples of (meth)acrylic acid esters having a hydroxyl group include β-hydroxyethyl (meth)acrylate, β-hydroxypropyl (meth)acrylate, and ε-caprolactone-β-hydroxyethyl (meth)acrylate.
Examples include acrylate, 1,4-butanediol mono(meth)acrylate, and the like. ), etc.

The ethylenically unsaturated group-containing compound FB+ may be used alone or in combination of two or more compounds in any proportion, if necessary. These ethylenically unsaturated group-containing compounds (D) can be easily obtained from the market.

Next, in the present invention, a photopolymerization initiator used as an optional component (0 includes, for example, benzoin, benzyl, benzoin methyl ether).

Pentwinisopropyl ether, acetophenone, 2
．． 2-dimethoxy-2-phenylacetophenone, 2.
2-jethoxy-2-phenylacetophenone, 1,1
-dichloroacetophenone, 1-hydroxycyclohexylphenyl ketone.

2-#f-1-44-(methylthio)phenyl]-2
-morpholino~propan-1-one, N,N-dimethylaminoacetophenone, 2-methylanthraquinone, 2
-ethylanthraquinone, 2-tert-butylanthraquinone, 1-chloroanthraquinone, 2-amylanthraquinone, 2-aminoanthraquine, 2.4-dimethylthioxanthone, 2.4-diethylthioxanthone,
Examples include 2.4-diisopropylthioxanthone, acetophenone dimethyl ketal, benzophenone, methylbenzophenone, 4.4-dichlorobenzophenone, 4.4-bisdiethylaminobenzophenone, and Michler's ketone. These can be used alone or in combination of two or more. Furthermore, such a photopolymerization initiator (0 is a single known photosensitizer such as N,N-dimethylaminobenzoic acid ethyl ester, N,N-dimethylaminobenzoic acid isoamyl ester, triethanolamine, triethylamine) Alternatively, it can be used in combination of two or more types.

Resin composition and printing ink resin composition of the present invention (hereinafter referred to as
Both are collectively referred to as a composition. ), the amount of urethane (meth)acrylate (4) used is preferably 0.01 to 20 parts by weight, particularly preferably 0.5 to 20 parts by weight, when the ethylenically unsaturated group-containing compound pile) is 100 parts by weight. 5 parts by weight.

The amount of photopolymerization initiator (0) used is preferably 0 to 25 parts by weight when the total amount of component (4) + FB + component is 100 parts by weight.
Parts by weight, particularly preferably 2 to 20 parts by weight.

The composition of the present invention may optionally include non-reactive resins [for example, diallyl phthalate resin (Daiso Tsubu, manufactured by Osaka Soda Corporation), cyclic ketone resin (Hilac 780, 110H, manufactured by Hitachi Chemical Corporation), rosin resin. , rosin resin modified phenolic resin, acrylic resin, etc.] can be added.
This makes it possible to improve the performance of the cured film.

In addition, antioxidants, ultraviolet absorbers, polymerization inhibitors, plasticizers,
Coloring components such as fillers, solvents, pigments or dyes, and other auxiliary agents may be used in combination.

Examples of the plasticizer include dibutyl phthalate, butylphthalyl butyl glycolate, tricresyl phosphate chloride paraffin, and the like. Examples of the filler include glass fiber, powdered silica, pallite, and calcium carbonate. As a polymerization inhibitor, f is used to prevent dark reactions and prevent photopolymerization.
, but such compounds include quinone nitrone compounds, sulfur compounds, etc. Specifically, p-benzoquinone, 2,5-di-tert-butyl p-benzoquinone, nitrosobenzene, phenothiazine, Examples include tcrt-butylhydroquinone, hydroquinone monomethyl ether, and hydroquinone. Furthermore, examples of the above pigments include extender pigments such as alumina white, clay talc, barium carbonate, and precipitated barium sulfate, zinc white, lead white, yellow lead, ultramarine blue, navy blue,
Examples include inorganic pigments such as titanium oxide, red iron oxide, and carbon black, and organic pigments such as Brilliant Carmino 6B, Permanentret R1, Benzidine Yellow, Lakelet C, and Phthalocyanine Blue. Other auxiliary agents include antifoaming agents such as silicone, leveling agents, polyoxyethylene glycol alkyl ether, surfactants such as 5')') acid sorter, alkylbenzylammonium chloride, eugenol, and methyl ethyl ketoxime. Anti-skinning agent such as 2゜2'
- UV absorbers such as dihydroxy-4-methoxybenzophenone, antioxidants such as 6-methyl-2,4-tert-butylphenol, organic bentonites,
Thickeners such as aluminum octoate and silica gel, flame retardants such as chlorinated paraffin and diphenyl chloride, polymerization regulators such as dodecyl mercaptan, ethyl mercaptoacetate, pentaerythritol tetrakis (β-mercaptopropionate), triphenyl phosphite,
Mention may be made of storage stabilizers such as diethylhydroxylamine. The composition of the present invention can be obtained by mixing each component. The thus obtained composition of the present invention is coated or printed on a metal plate, glass, plastic plate, film, paper, stone plate, wood board, or other substrate by a conventional method, and then irradiated with ultraviolet rays or an electron beam by a conventional method. It can be cured by irradiation to form a cured product. In some cases, the composition of the present invention may be dispersed in water and cured with peroxides to obtain a finely powdered cured product. When using a photopolymerization initiator, it can be cured by irradiation with ultraviolet light. Examples of light sources that generate such ultraviolet light include carbon arc lamps, mercury vapor lamps, ultraviolet fluorescent lamps, tungsten lamps, incandescent lamps, xenon lamps, and argon glow lamps.

The resin composition of the present invention has excellent curability, and the cured product thereof has excellent adhesion, light resistance, and weather resistance. Therefore, the resin composition of the present invention is useful as a printing ink resin composition.
It can also be used as a paint or coating agent.

(Examples) The present invention will be explained in more detail below using Examples. Parts in Examples indicate parts by weight.

[Examples 1 to 8 of urethane (meth)acrylate (4)
] Example 1 Hindered amine compound having a structural formula (Adeka Argus ■
ARKLS DN-10) 282 parts, hexamethylene diisocyanate 504 parts, methyl ethyl ketone 2
Then, 05 parts of methoquinone and 255 parts of 2-hydroxyethyl acrylate were charged and the reaction was carried out at 80°C for about 15 hours until the residual NCO in the reaction solution became 01% by weight or less. The reaction was carried out, and then methyl ethyl ketone was distilled off to obtain urethane acrylate as a pale yellow transparent solid. Obtained urethane acrylate
and k in methyl ethyl ketone at a concentration of 58.3% by weight.
The viscosity (25°C) was measured to be 32.
00 cps.

Example 2° Structural formula The viscosity (25°C) was measured and found to be 4500 cps.

Example 36 481 parts of hindered amine compound having the structural formula (manufactured by Sankyo ■, Sanol LS-770, inphorone diisocyanate)
444.6 parts of methyl ethyl ketone and 200 parts of methyl ethyl ketone were charged and reacted at 80°C for about 10 hours.
and 255 parts of 2-hydroxyethyl acrylate were charged, and the reaction was carried out at 80°C for about 15 hours until the residual NCO in the reaction solution decreased to 0.1% by weight or less.Then, methyl ethyl ketone was distilled off to form a white solid urethane. Obtained acrylate.

The obtained urethane acrylate was dissolved in methyl ethyl ketone at a concentration of 58.3% by weight as a hindered amine compound (manufactured by Adeka Argus, MAR).
K LA-57) 790 parts, hexamethylene diinocyanate 672 parts and methyl ethyl ketone 300 parts were charged and reacted at 80°C for about 10 hours. Then, 1.0 part of methoquinone and 510 parts of 2-hydroxyethyl acrylate were charged and the mixture was reacted at 80°C. Residual NCO in reaction solution is 0.1% by weight
The reaction was carried out for about 15 hours until the amount of urethane acrylate was reduced to below, and then methyl ethyl ketone was distilled off to obtain urethane acrylate as a light brown solid. The obtained urethane acrylate was dissolved in methyl ethyl ketone at a concentration of 58.3% by weight. The viscosity (at 25°C) was measured to be 7600.
It was cps.

Example 4 168 parts of structural formula diisocyanate and 2 parts of methyl ethyl ketone
00 parts of the reaction solution was charged and reacted at 80°C for about 10 hours, then 03 parts of methoquinone and 127 parts of 2-hydroxyethyl acrylate were added, and the residual NCO in the reaction solution was heated to 80°C until the residual NCO was 0.4 parts.
The reaction was carried out for about 15 hours until the concentration became 1% by weight or less, and then methyl ethyl ketone was distilled off to obtain urethane acrylate as a pale yellow solid. The obtained urethane acrylate was dissolved in methyl ethyl ketone to a concentration of 583% by weight, and the viscosity (at 25°C) was measured to be 2500.
It was cps.

Hindered amine compound (ADEKA AGA Ju
g, MARK LA-68; 1900 parts, 1008 parts of hexamethylene diisocyanate) and 7500 parts of methyl ethyl keto were charged, and reacted at 80'C for about 10 hours.
Next, 1.8 parts of methoquinone and 766 parts of 2-hydroxyethyl acrylate were charged, and the remaining N in the reaction solution was heated at 80°C.
The reaction was carried out for about 15 hours until the GO concentration was 0.01% by weight or less, and then methyl ethyl ketone was removed with () to obtain a light brown solid urethane acrylate. The viscosity (at 25° C.) was determined to be 2100 cps.

Example 6 225 parts of MARK LA-87 manufactured by Gas Corporation, 174 parts of tolylene diincyanate and 2 parts of methyl ethyl ketone
00 parts of the reaction solution was charged, and reacted for about 10 hours in SO'C. Next, 03 parts of methoquinone and 127 parts of 2-hydroxyethyl acrylate were charged, and the reaction solution was heated at 80°C for about 15 hours until the residual NCO in the reaction solution reached 01% by weight or less. Perform a time reaction,
Then, methyl ethyl ketone was distilled off to obtain urethane acrylate as a pale yellow solid. The obtained urethane acrylate was dissolved in methyl ethyl ketone to a concentration of 58.3% by weight, and its viscosity (at 25°C) was measured to be 2300 cps.

Example 7 Hindered amine compound having the structural formula (Hindered amine compound having ADEKA AR (manufactured by Sankyo Co., Ltd., Sanol LS-
770) 481 parts, hexamethylene diisocyanate 3
34 parts and 7200 parts of methyl ethyl keto were charged, and 80
After reacting at °C for about 10 hours, 05 parts of methoquinone and 255 parts of 2-hydroxyethyl acrylate were added, and the reaction was continued at 80'C for about 15 hours until the residual NCO in the reaction solution became 0.1% by weight or less. Then, it was dissolved in methyl ethyl ketone to a concentration of 58.3% by weight, and the viscosity (25°C) was measured: 4500 C1)
It was S.

Example 8 Hindered amine compound having the structural formula (ADEKA ARGUS n
MARK LA-57) 790 parts, hexamethylene diisocyanate 672 parts and methyl ethyl keto 73
00 parts and reacted at 80°C for about 10 hours, then 1.0 part of methoquinone and 572 parts of 2-hydroxyl methyl ester were added, and the remaining NC0I of the reaction solution was charged at 806C.
The reaction was carried out for about 15 hours until the concentration became 1% by weight or less, and then the methyl ethyl ketone was distilled off to obtain a pale brown solid urethane acrylate.The obtained urethane acrylate was dissolved in methyl ethyl ketone in an amount of 58.3% by weight. It dissolved in a reddish color and its viscosity (at 25°C) was measured to be 7500 cps.

[Synthesis Examples 1 and 2 of ethylenically unsaturated group-containing compound (Bl)
Synthesis Example 1 Poly-ε-caprolactone polyol (manufactured by Daicel Chemical, product name Plaxel 205, OH value 213.7
mgKOH/g, number average molecular weight 525.1) 262.
6 parts, also poly-ε-caprolactone type, polyol (manufactured by Daicel Chemical ■, product name Plaxel 208, OHHI
337.8 mgKOH/g, number average molecular weight 814.4
) 407.2 parts, inphoron diisocyanate 1-2
77.9 parts were charged, and after raising the temperature, the reaction was carried out at 80'C for 13 hours.Then, the reaction solution was cooled to 60°C, and 55.3 parts of β-hydroxyacrylate, 0.50 parts of methoquinone, and di-n-butyltin dilaurate were added. Add 0.20 parts and raise the temperature to 8.
The reaction was carried out at 0° C. for about 15 hours to obtain polyurethane acrylate.

Synthesis Example 2 Epoxidized soybean oil (manufactured by Adeka Argus Chemical, ADK
CIZER0-130P, oxirane oxygen content 69
%) 246.7 parts, acrylic acid 53.3 parts, benzyltrimethylammonium chloride 1.1 parts as an esterification catalyst, methoxyphenol 0.15 as a polymerization inhibitor
The reaction temperature was kept at 90'C and the reaction was continued for about 24 hours until the acid value became 3.0 or less. The acid value of the reactant is 2.1 (mgKOH/g), and the viscosity is 1680.
0 CPS (30'C), and the appearance was a brown transparent liquid resin. Next, 300 parts of the epoxidized soybean oil acrylic ester and 14 parts of inphorone diisocyanate were charged and reacted at 70 to 80°C for about 15 hours to obtain a modified epoxidized soybean oil acrylic ester urethane.

Examples 9 to 17, Comparative Examples 1 to 2゜After blending each component according to the composition shown in Table 1,
The printing ink resin composition of the present invention was prepared by kneading with three rolls. Each ink was printed on a polycarbonate plate with a screen so that the ink film was 15μ, and Examples 9 to 1
For 6, the printing plate was heated with a metal halide lamp (output 2
KWt 80 w/cm ) at the lower I Q cm was placed on a conveyor with a line speed of 10 m, and photocured. Further, in Example 17, curing was performed by electron beam irradiation. The initial adhesion of the cured film immediately after curing was evaluated according to the method described below.

Furthermore, using an accelerated exposure tester (Sunshine Carbon Weatherometer: Suga Test Instruments WE-8UN-DC model), the treatment was performed for 100 hours at a rainfall of 12 minutes/60 minutes per cycle and a black panel temperature of 63±3℃. Weather resistance was evaluated by observing adhesion and appearance. These results are shown in Table-1.

[Adhesion]

Cross-cut cellophane tape peeling test on cured film: Cut film cutting lines reaching the base material at 1f1 intervals on the film,
Make 100 squares of 1d each, vertically and horizontally, and paste cello tape on top of it, then peel it off quickly. The cellophane tape peeling test is performed 1 to 3 times on the same location.

◎・・・・・・・・・ Even after 3 tests, there was a lot of peeling ○・
・・・・・・・・・ There was no peeling after the first test, but after the second test there was 8 peeling △・・・・・・・・・ The number of peeling after the first test was 1～
50 pieces×・・・・・・ Number of peeling amount after first test 51
~100 pieces [Appearance] (4) Discoloration or cloudiness◎・・・・・・・・・No discoloration (yellowing, whitening) or cloudiness ○・・・・・・Slight discoloration or cloudiness Occurrence × ・・・・・・・・・ (8) Crashes ◎・・・・・・・・・ ○・・・・・・・・・ △・・・・・・・・・ × ・・・・・・・・・・・ Discoloration or clouding is bright red. Discoloration or clouding is noticeable. There is no peeling of the film. It is almost invisible. There is a little bit of L・ and it is noticeable △・・・・・・・・・■KAYARAD MANDA: Human xypivalic acid neopentyl glycol diacrylate (manufactured by Nippon Kayaku ■, trade name) Photopolymerization initiator, 2-methyl-1-(4-(methylthio)phenyl)-2-morpholino-propan-1-one, manufactured by Kayer.

"■KAYACURE DETX: manufactured by Nippon Kayaku ■, photopolymerization initiator, 2,4.-diethylthioxanthone (effects of the invention) The resin composition of the present invention uses a novel urethane (meth)acrylate, As a result, the cured film has excellent weather resistance and light resistance, and the resin composition of the present invention is suitable as a printing ink for outdoor use.

Claims (1)

[Claims] 1. In the molecule, there are ▲mathematical formulas, chemical formulas, tables, etc.▼Hindered amine compound (a) having a group, organic polyisocyanate (b), and (meth)acrylic acid ester having a hydroxyl group (c) Urethane (meth) obtained by reacting
Acrylate. 2. Urethane (meth)acrylate according to claim 1 (
A resin composition comprising A), an ethylenically unsaturated group-containing compound (B) other than the component (A), and a photopolymerization initiator (C) as an optional component. 3. A printing ink resin composition comprising the resin composition according to claim 2. 4. A cured product of the resin composition according to claim 2 or 3.