PHOTOCURABLE RESIN COMPOSITION, INK AND COATING MATERIAL

Abstract

The purpose of the present invention is to provide a photocurable resin composition which exhibits excellent compatibility, drying properties when cured by irradiation with light, scratch resistance and adhesion to a substrate. The present invention is a photocurable resin composition containing a styrene-acrylate copolymer and an ethylenically unsaturated compound. The styrene-acrylate copolymer contains 10-90 mol % of constituent units (A) derived from a styrene-based compound and 10-90 mol % of constituent units (B) derived from an acrylate compound. The constituent units (B) derived from an acrylate compound contain constituent units (b-1) derived from a compound having at least three (meth)acryloyl groups in the molecule.

Claims

1. A photocurable resin composition comprising: a styrene-acrylate copolymer; and an ethylenically unsaturated compound, wherein in the styrene-acrylate copolymer, a proportion of a constituent unit (A) derived from the styrene-based compound is 10 to 90 mol %, a proportion of a constituent unit (B) derived from the acrylate compound is 10 to 90 mol %, and the constituent unit (B) derived from the acrylate compound contains a constituent unit (b-1) derived from a compound having at least three (meth)acryloyl groups in a molecule.

2. A photocurable resin composition comprising: a styrene-acrylate copolymer; a monomer having a radically polymerizable double bond; and a photopolymerization initiator, wherein in the styrene-acrylate copolymer, a proportion of a constituent unit (A) derived from the styrene-based compound is 10 to 90 mol %, a proportion of a constituent unit (B) derived from the acrylate compound is 10 to 90 mol %, and the constituent unit (B) derived from the acrylate compound contains a constituent unit (b-1) derived from a compound having at least three (meth)acryloyl groups in a molecule.

3. A photocurable resin composition comprising: a styrene-acrylate copolymer; a monomer having a radically polymerizable double bond; a photopolymerization initiator; and a sensitizer, wherein in the styrene-acrylate copolymer, a proportion of a constituent unit (A) derived from the styrene-based compound is 10 to 90 mol %, a proportion of a constituent unit (B) derived from the acrylate compound is 10 to 90 mol %, and the constituent unit (B) derived from the acrylate compound contains a constituent unit (b-1) derived from a compound having at least three (meth)acryloyl groups in a molecule.

4. The photocurable resin composition according to claim 1, wherein the compound having at least three (meth)acryloyl groups in the molecule is an acrylate compound having three (meth)acryloyl groups or an acrylate compound having four (meth)acryloyl groups.

5. The photocurable resin composition according to claim 1, wherein the compound having at least three (meth)acryloyl groups in the molecule is at least one selected from the group consisting of trimethylolpropane tri(meth)acrylate, trimethyloloctane tri(meth)acrylate, trimethylolpropane polyethoxy tri(meth)acrylate, trimethylolpropane polypropoxy tri(meth)acrylate, trimethylolpropane polyethoxy polypropoxy tri(meth)acrylate, tris[(meth)acryloyloxyethyl]isocyanurate, pentaerythritol tri(meth)acrylate, pentaerythritol polyethoxy tetra(meth)acrylate, pentaerythritol polypropoxy tetra(meth)acrylate, pentaerythritol tetra(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, and dipentaerythritol tetra(meth)acrylate.

6. The photocurable resin composition according to claim 1, wherein the constituent unit (B) derived from the acrylate compound further contains a constituent unit (b-2) derived from an aromatic acrylate compound and a constituent unit (b-3) derived from an aliphatic acrylate compound.

7. The photocurable resin composition according to claim 1, wherein a molecular weight distribution (mass average molecular weight (Mw)/number average molecular weight (Mn)) of the styrene-acrylate copolymer is in a range of 1 to 50.

8. The photocurable resin composition according to claim 1, wherein an iodine value of the styrene-acrylate copolymer is 1 to 100.

9. An ink comprising the photocurable resin composition according to claim 1.

10. A coating material comprising the photocurable resin composition according to claim 1.

11. The coating material according to claim 10, which is the overprint varnish.

12. The photocurable resin composition according to claim 2, wherein the compound having at least three (meth)acryloyl groups in the molecule is an acrylate compound having three (meth)acryloyl groups or an acrylate compound having four (meth)acryloyl groups.

13. The photocurable resin composition according to claim 2, wherein the compound having at least three (meth)acryloyl groups in the molecule is at least one selected from the group consisting of trimethylolpropane tri(meth)acrylate, trimethyloloctane tri(meth)acrylate, trimethylolpropane polyethoxy tri(meth)acrylate, trimethylolpropane polypropoxy tri(meth)acrylate, trimethylolpropane polyethoxy polypropoxy tri(meth)acrylate, tris[(meth)acryloyloxyethyl]isocyanurate, pentaerythritol tri(meth)acrylate, pentaerythritol polyethoxy tetra(meth)acrylate, pentaerythritol polypropoxy tetra(meth)acrylate, pentaerythritol tetra(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, and dipentaerythritol tetra(meth)acrylate.

14. The photocurable resin composition according to claim 2, wherein the constituent unit (B) derived from the acrylate compound further contains a constituent unit (b-2) derived from an aromatic acrylate compound and a constituent unit (b-3) derived from an aliphatic acrylate compound.

15. The photocurable resin composition according to claim 2, wherein a molecular weight distribution (mass average molecular weight (Mw)/number average molecular weight (Mn)) of the styrene-acrylate copolymer is in a range of 1 to 50.

16. The photocurable resin composition according to claim 2, wherein an iodine value of the styrene-acrylate copolymer is 1 to 100.

17. An ink comprising the photocurable resin composition according to claim 2.

18. A coating material comprising the photocurable resin composition according to claim 2.

19. The coating material according to claim 18, which is the overprint varnish.

20. The photocurable resin composition according to claim 3, wherein the compound having at least three (meth)acryloyl groups in the molecule is an acrylate compound having three (meth)acryloyl groups or an acrylate compound having four (meth)acryloyl groups.

Description

EXAMPLES

[0130] Hereinafter, the first aspect, the second aspect, and the third aspect of the present invention will be described in more detail with reference to Examples, but the following Examples do not limit the scope of rights of the present invention at all. In the present invention, “part” represents “part by mass”, and “%” represents “mass %”.

Method for Measuring Mass Average Molecular Weight (Mw), Number Average Molecular Weight (Mn), and Molecular Weight Distribution (Mw/Mn) of Styrene-Acrylate Copolymer

[0131] The mass average molecular weight (Mw), the number average molecular weight (Mn), and the molecular weight distribution (Mw/Mn) of the styrene-acrylate copolymer were measured using Gel Permeation Chromatography (GPC). Mw and Mn are values of mass average molecular weight and number average molecular weight in terms of standard polystyrene.

[0132] Column: Shodex LF-804×2 columns are connected in series.

[0133] Flow rate: 1.0 mL/min

[0134] Temperature: 40° C.

[0135] Detector: RID-20A

[0136] Sample: 20 mg of a sample was dissolved in 10 mL of tetrahydrofuran to prepare a sample for measurement.

Measurement of Iodine Value

[0137] The iodine value of the styrene-acrylate copolymer used in the production was measured according to the method defined in JIS K6235.

(Synthesis Example 1A) Styrene-Acrylate Copolymer (Copolymer 1A)

[0138] Into a four-necked flask equipped with a stirrer, a reflux condenser, a thermometer, and a dropping funnel, 130 g of mesitylene was added and heated to 160° C. with stirring. A mixture of 16 g of styrene, 12 g of benzyl acrylate, 14 g of 2-ethylhexyl acrylate, 22 g of trimethylolpropane triacrylate, and 5 g of tert-butylperoxybenzoate was added dropwise to the reaction vessel over 6 hours. Thereafter, the styrene-acrylate copolymer was subjected to a polymerization reaction for 30 minutes, and then cooled to room temperature. The obtained polymerization solution was treated with a 10-fold amount of hexane to remove unreacted acrylate, and dried at 80° C. under reduced pressure to obtain copolymer 1A. (Yield: 60%, mass average molecular weight: 27,000, number average molecular weight: 5,500, molecular weight distribution: 4.9, iodine value: 10). Copolymer 1A is a styrene-acrylate copolymer in which the proportion of the constituent unit (A) derived from a styrene-based compound is 10 to 90 mol %, the proportion of the constituent unit (B) derived from an acrylate compound is 10 to 90 mol %, and the constituent unit (B) derived from an acrylate compound contains the structural unit (b-1) derived from a compound having at least three (meth)acryloyl groups in the molecule.

(Synthesis Example 2A) Styrene-Acrylate Copolymer (Copolymer 2A)

[0139] Into a four-necked flask equipped with a stirrer, a reflux condenser, a thermometer, and a dropping funnel, 130 g of mesitylene was added and heated to 160° C. with stirring. A mixture of 16 g of styrene, 13 g of benzyl acrylate, 15 g of 2-ethylhexyl acrylate, 18 g of 1,6-hexanediol diacrylate, and 5 g of tert-butylperoxybenzoate was added dropwise to the reaction vessel over 6 hours. Thereafter, the styrene-acrylate copolymer was subjected to a polymerization reaction for 30 minutes, and then cooled to room temperature. The obtained polymerization solution was treated with a 10-fold amount of hexane to remove unreacted acrylate, and dried at 80° C. under reduced pressure to obtain copolymer 2A. (Yield: 60%, mass average molecular weight: 29,000, number average molecular weight: 11,000, molecular weight distribution: 2.6, iodine value: 5). Copolymer 2A is a styrene-acrylate copolymer in which the proportion of the constituent unit (A) derived from a styrene-based compound is 10 to 90 mol % and the proportion of the constituent unit (B) derived from an acrylate compound is 10 to 90 mol %, but the constituent unit (B) derived from an acrylate compound does not contain the constituent unit (b-1) derived from a compound having at least three (meth)acryloyl groups in the molecule.

EXAMPLES

[0140] A photocurable resin composition having each composition described in the following Table 1A was prepared, and each characteristic was evaluated.

Examples 1A to 10A and Comparative Examples 1A to 7A

1A) Evaluation of Solubility (Compatibility) of Active Energy Ray Curable Composition

[0141] Each component described in Table 1A was heated and mixed at 90° C. for 2 hours to prepare an active energy ray curable composition. Each composition was cooled to room temperature (25° C.), and solubility (compatibility between the styrene-acrylate copolymer and the ethylenically unsaturated compound) was evaluated based on whether the appearance after elapse of one night was transparent. The sample whose appearance was transparent even after cooling was evaluated as ∘, and the sample whose appearance was cloudy was evaluated as x. The evaluation results are shown in Table 1A.

2A) Drying Property Test

[0142] An active energy ray curable composition prepared from each component described in Table 1A was coated on a piece of one-side coated art paper (art paper, manufactured by Oji Paper Co., Ltd.) using an RI tester, and cured with a metal halide lamp (lamp distance: 11 cm, conveyor speed: 100 m/min) having an output of 80 W/cm. As the UV curing apparatus, a conveyor type ultraviolet curing apparatus manufactured by Eye Graphics Co., Ltd. was used. The sample was passed a plurality of times until no fingerprint was left on the surface (tack free) when the coating film was touched with a finger. The case where the number of times of passage was 5 or less was evaluated as ∘, and the case where the number of times of passage was 6 or more was evaluated as x.

3A) Scratch Property Test

[0143] An active energy ray curable composition prepared from each component described in Table 1A was coated on a piece of one-side coated art paper in the same manner as in the drying property test, and cured. The surface of the obtained coating film was rubbed with a nail to confirm the surface state. The case where the coating film exhibited no change or the coating film was scraped while resisting was evaluated as ∘, and the case where the coating film was easily scraped was evaluated as x. The evaluation results are shown in Table 1A.

TABLE-US-00001 TABLE 1A Compar- Compar- Compar- Compar- ative ative ative ative Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- ple 1A ple 2A ple 3A ple 4A ple 1A ple 2A ple 3A ple 5A ple 4A Resin Copolymer 1A 30 30 10 40 30 Copolymer 2A 30 U-2PPA *1 30 30 VS1063 *2 30 Ethylenically DPHA *3 70 unsaturated DTMPTA *4 70 90 60 70 70 70 compound 3EO-TMPTA *5 70 70 3PO-TMPTA *6 TMPTA *7 TPGDA *8 GPTA *9 HDDA *19 Photopolymerization Omnirad 907 *11 5 5 5 5 5 5 5 5 5 initiator Solubility ◯ ◯ ◯ ◯ ◯ ◯ X ◯ ◯ Drying property ◯ ◯ ◯ ◯ X X — ◯ X Scratch property ◯ ◯ ◯ ◯ ◯ ◯ — ◯ ◯ Compar- Compar- Compar- ative ative ative Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- ple 6A ple 7A ple 8A ple 5A ple 9A ple 6A ple 10A ple 7A Resin Copolymer 1A 30 30 30 30 30 Copolymer 2A U-2PPA *1 30 30 30 VS1063 *2 Ethylenically DPHA *3 unsaturated DTMPTA *4 compound 3EO-TMPTA *5 3PO-TMPTA *6 70 TMPTA *7 70 TPGDA *8 70 70 GPTA *9 70 70 HDDA *19 70 70 Photopolymerization Omnirad 907 *11 5 5 5 5 5 5 5 5 initiator Solubility ◯ ◯ ◯ ◯ ◯ ◯ ◯ ◯ Drying property ◯ ◯ ◯ X ◯ X ◯ X Scratch property ◯ ◯ ◯ ◯ ◯ ◯ ◯ ◯

[0144] Components other than copolymers 1A and 2A shown in Table 1A are as follows.

[0145] The composition amounts shown in Table 1A are expressed in parts by mass.

[0146] *1: U-2PPA: urethane acrylate, manufactured by Shin-Nakamura Chemical Co.,

[0147] Ltd.

[0148] *2: VS-1063: polystyrene resin, manufactured by Seiko PMC Corporation.

[0149] *3: DPHA: Aronix M-404 dipentaerythritol hexaacrylate, manufactured by Toagosei Co., Ltd.

[0150] *4: DTMPTA: MIRAMER M410 ditrimethylolpropane tetraacrylate, manufactured by Miwon Specialty Chemical Co., Ltd.

[0151] *5: 3E0-TMPTA: MIRAMER M3130 ethylene oxide-modified trimethylolpropane triacrylate, manufactured by Miwon Specialty Chemical Co., Ltd.

[0152] *6: 3PO-TMPTA: SR492TFN propylene oxide-modified trimethylolpropane triacrylate, manufactured by Sartomer Company Inc.

[0153] *7: TMPTA: MIRAMER M300 trimethylolpropane triacrylate, manufactured by Miwon Specialty Chemical Co., Ltd.

[0154] *8: TPGDA: SR306H tripropylene glycol diacrylate, manufactured by Sartomer Company Inc.

[0155] *9: GPTA: MIRAMER M320 propylene oxide-modified glycerol triacrylate, manufactured by Miwon Specialty Chemical Co., Ltd.

[0156] *10: HDDA: SR238NS 1,6-hexanediol diacrylate, manufactured by Sartomer Company Inc.

[0157] *11: Omnirad 907: 2-methyl-1-[4-(methylthio)phenyl]-2 morpholinopropane-1-one, manufactured by IGM Resins B.V.

[0158] Table 1A shows that the photocurable resin composition containing the styrene-acrylate copolymer of the first aspect is excellent in compatibility, drying property, and scratch resistance even when various acrylates are used.

(Synthesis Example 1B) Styrene-Acrylate Copolymer (Copolymer 1B)

[0159] Into a four-necked flask equipped with a stirrer, a reflux condenser, a thermometer, and a dropping funnel, 130 g of mesitylene was added and heated to 160° C. with stirring. A mixture of 16 g of styrene, 12 g of benzyl acrylate, 14 g of 2-ethylhexyl acrylate, 22 g of trimethylolpropane triacrylate, and 5 g of tert-butylperoxybenzoate was added dropwise to the reaction vessel over 6 hours. Thereafter, the styrene-acrylate copolymer was subjected to a polymerization reaction for 30 minutes, and then cooled to room temperature. The obtained polymerization solution was treated with a 10-fold amount of hexane to remove unreacted acrylate, and dried at 80° C. under reduced pressure to obtain copolymer 1B. (Yield: 60%, weight average molecular weight: 27,000, number average molecular weight: 5,500, molecular weight distribution: 4.9, iodine value: 10)

EXAMPLES

[0160] A photocurable resin composition having each composition described in the following Table 1B was prepared, and each characteristic was evaluated.

Examples 1B to 10B and Comparative Examples 1B to 6B

1B) Drying Property Test

[0161] An active energy ray curable composition prepared from each component described in Table 1B was coated on a piece of one-side coated art paper (art paper, manufactured by Oji Paper Co., Ltd.) using an RI tester, and cured with a metal halide lamp (lamp distance: 11 cm, conveyor speed: 100 m/min) having an output of 80 W/cm. Note that, as the UV curing apparatus, a conveyor type ultraviolet curing apparatus manufactured by Eye Graphics Co., Ltd. was used. The sample was passed a plurality of times until no fingerprint was left on the surface (tack free) when the coating film was touched with a finger. The case where the number of times of passage was 3 or less was evaluated as ⊙, the case where the number of times of passage was 4 or 5 was evaluated as ∘, and the case where the number of times of passage was 6 or more was evaluated as x. The evaluation results are shown in Table 1B.

2B) Scratch Property Test

[0162] An active energy ray curable composition prepared from each component described in Table 1B was coated on a piece of one-side coated art paper in the same manner as in the drying property test, and cured. The surface of the obtained coating film was rubbed with a nail to confirm the surface state. The case where the coating film exhibited no change or the coating film was scraped while resisting was evaluated as ∘, and the case where the coating film was easily scraped was evaluated as x. The evaluation results are shown in Table 1B.

TABLE-US-00002 TABLE 1B Compar- Compar- Compar- Compar- ative ative ative ative Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- ple 1B ple 1B ple 2B ple 2B ple 3B ple 3B ple 4B ple 4B Resin Copolymer 1B 20 20 20 20 U-2PPA *1 20 20 20 20 Monomer DPHA *2 80 80 80 80 80 80 80 80 Photopolymerization Omnirad 907 *3 5 5 initiator Omnirad 379 *4 5 5 Omnirad TPO *5 5 5 Omnirad 184 *6 5 5 Omnirad 651 *7 Omnirad 1173 *8 Drying property ⊙ ◯ ⊙ X ⊙ ◯ ◯ X Scratch property ◯ ◯ ◯ ◯ ◯ ◯ ◯ ◯ Compar- Compar- ative ative Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- ple 5B ple 5B ple 6B ple 6B ple 7B ple 8B ple 9B ple 10B Resin Copolymer 1B 20 20 20 20 20 20 U-2PPA *1 20 20 Monomer DPHA *2 80 80 80 80 80 80 80 80 Photopolymerization Omnirad 907 *3 initiator Omnirad 379 *4 2 10 Omnirad TPO *5 2 10 Omnirad 184 *6 Omnirad 651 *7 5 5 Omnirad 1173 *8 5 5 Drying property ◯ X ◯ X ◯ ⊙ ◯ ⊙ Scratch property ◯ ◯ ◯ ◯ ◯ ◯ ◯ ◯

[0163] Components other than copolymer 1B shown in Table 1B are as follows. The composition amounts shown in Table 1B are expressed in parts by mass.

[0164] *1: U-2PPA: urethane acrylate, manufactured by Shin-Nakamura Chemical Co., Ltd.

[0165] *2: DPHA: Aronix M-404 dipentaerythritol hexaacrylate, manufactured by Toagosei Co., Ltd.

[0166] *3: Omnirad 907: 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropane-1-one, manufactured by IGM Resins B.V.

[0167] *4: Omnirad 379: 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholine-4-yl-phenyl)-butane-1-one, manufactured by IGM Resins B.V.

[0168] *5: Omnirad TPO: 2,4,6-trimethylbenzoyldiphenylphosphine oxide, manufactured by IGM Resins B.V.

[0169] *6: Omnirad 184: 1-hydroxycyclohexyl phenyl ketone, manufactured by IGM Resins B.V.

[0170] *7: Omnirad 651: 2,2-dimethoxy-2-phenylacetophenone, manufactured by IGM Resins B.V.

[0171] *8: Omnirad 1173: 2-hydroxy-2-methyl-1-phenylpropanone, manufactured by IGM Resins B.V.

[0172] Table 1B reveals that the photocurable resin composition containing the styrene-acrylate copolymer of the second aspect and various photopolymerization initiators has excellent drying property and scratch resistance. Among them, a combination of a styrene-acrylate copolymer and Omnirad 907, a combination of a styrene-acrylate copolymer and Omnirad 379, and a combination of a styrene-acrylate copolymer and Omnirad TPO exhibited particularly excellent drying property.

(Synthesis Example 1C) Styrene-Acrylate Copolymer (Copolymer 1C)

[0173] Into a four-necked flask equipped with a stirrer, a reflux condenser, a thermometer, and a dropping funnel, 130 g of mesitylene was added and heated to 160° C. with stirring. A mixture of 16 g of styrene, 12 g of benzyl acrylate, 14 g of 2-ethylhexyl acrylate, 22 g of trimethylolpropane triacrylate, and 5 g of tert-butylperoxybenzoate was added dropwise to the reaction vessel over 6 hours. Thereafter, the styrene-acrylate copolymer was subjected to a polymerization reaction for 30 minutes, and then cooled to room temperature. The obtained polymerization solution was treated with a 10-fold amount of hexane to remove unreacted acrylate, and dried at 80° C. under reduced pressure to obtain copolymer 1C. (Yield: 60%, mass average molecular weight: 27,000, number average molecular weight: 5,500, molecular weight distribution: 4.9, iodine value: 10)

EXAMPLES

[0174] A photocurable resin composition having each composition described in the following Table 1C was prepared, and each characteristic was evaluated.

Examples 1C to 9C and Comparative Examples 1C to 5C

1C) Drying Property Test

[0175] An active energy ray curable composition prepared from each component described in Table 1C was coated on a piece of one-side coated art paper (art paper, manufactured by Oji Paper Co., Ltd.) using an RI tester, and cured with a metal halide lamp (lamp distance: 11 cm, conveyor speed: 100 m/min) having an output of 80 W/cm. Note that, as the UV curing apparatus, a conveyor type ultraviolet curing apparatus manufactured by Eye Graphics Co., Ltd. was used. The sample was passed a plurality of times until no fingerprint was left on the surface (tack free) when the coating film was touched with a finger. The case where the number of times of passage was 3 or less was evaluated as ⊙, the case where the number of times of passage was 4 or 5 was evaluated as ∘, and the case where the number of times of passage was 6 or more was evaluated as x. The evaluation results are shown in Table 1C.

2C) Scratch Property Test

[0176] An active energy ray curable composition prepared from each component described in Table 1C was coated on a piece of one-side coated art paper in the same manner as in the drying property test, and cured. The surface of the obtained coating film was rubbed with a nail to confirm the surface state. The case where the coating film exhibited no change or the coating film was scraped with resisting was evaluated as ∘, and the case where the coating film was easily scraped was evaluated as x. The evaluation results are shown in Table 1C.

TABLE-US-00003 TABLE 1C Compar- Compar- Compar- Compar- ative ative ative ative Exam- Exam- Exam- Exam- Exam- Exam- Exam- ple 1C ple 1C ple 2C ple 3C ple 2C ple 4C ple 3C Resin Copolymer 1C 20 20 20 20 U-2PPA *1 20 20 20 Monomer DPHA *2 80 80 80 80 80 80 80 Photopolymerization Omnirad 369 *3 2.5 2.5 2.5 2.5 2.5 2.5 2.5 initiator Omnirad TPO *4 Omnirad 819 *5 Sensitizer EAB-SS *6 2.5 2.5 KAYACURE DETX-S *7 2.5 2.5 KAYACURE EPA *8 2.5 Drying property ◯ X X X ⊙ X ◯ Scratch property ◯ ◯ ◯ ◯ ◯ ◯ ◯ Compar- ative Exam- Exam- Exam- Exam- Exam- Exam- Exam- ple 5C ple 4C ple 5C ple 6C ple 7C ple 8C ple 9C Resin Copolymer 1C 20 20 20 20 20 20 U-2PPA *1 20 Monomer DPHA *2 80 80 80 80 80 80 80 Photopolymerization Omnirad 369 *3 2.5 initiator Omnirad TPO *4 2.5 2.5 2.5 Omnirad 819 *5 2.5 2.5 2.5 Sensitizer EAB-SS *6 2.5 2.5 KAYACURE DETX-S *7 2.5 2.5 KAYACURE EPA *8 2.5 2.5 2.5 Drying property X ◯ ⊙ ◯ ◯ ◯ ◯ Scratch property ◯ ◯ ◯ ◯ ◯ ◯ ◯

[0177] Components other than copolymer 1C shown in Table 1C are as follows.

[0178] The composition amounts shown in Table 1C are expressed in parts by mass.

[0179] *1: U-2PPA: urethane acrylate, manufactured by Shin-Nakamura Chemical Co., Ltd.

[0180] *2: DPHA: Aronix M-404 dipentaerythritol hexaacrylate, manufactured by Toagosei Co., Ltd.

[0181] *3: Omnirad 369: 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1, manufactured by IGM Resins B.V.

[0182] *4: Omnirad TPO: 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, manufactured by IGM Resins B.V.

[0183] *5: Omnirad 819: bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, manufactured by IGM Resins B.V.

[0184] *6: EAB-SS: 4,4′-bis-(diethylamino)benzophenone, manufactured by Daido Chemical Industry Co., Ltd.

[0185] *7: KAYACURE DETX-S: 2,4-diethylthioxanthone, manufactured by Nippon Kayaku Co., Ltd.

[0186] *8: KAYACURE EPA: p-dimethylaminobenzoic acid ethyl ester, manufactured by Nippon Kayaku Co., Ltd.

[0187] Table 1C reveals that the photocurable resin composition containing the styrene-acrylate copolymer of the third aspect and various sensitizers has excellent drying property and scratch resistance.

INDUSTRIAL APPLICABILITY

[0188] The photocurable resin composition of the first aspect has excellent drying property and scratch resistance with respect to a base material such as paper, and is excellent in each physical property such as compatibility, drying property, adhesion, and scratch resistance even when used as an ink, and thus is useful for various printing inks, coating materials, coating agents, photoresists, and the like.

[0189] Each of the photocurable resin compositions of the second aspect and the third aspect has excellent drying property and scratch resistance with respect to a base material such as paper, and is excellent in each physical property such as drying property, adhesion, and scratch resistance even when used as an ink, and thus is useful for various printing inks, coating materials, coating agents, photoresists, and the like.