Photocurable resin composition

Abstract

To provide a photocurable resin composition comprising an N-vinyl amide compound, a polyfunctional (meth)acrylate monomer and a photopolymerization initiator and having excellent adhesion to an optical substrate and free from an appearance defect such as a crack or shrinkage and a laminate having a coat layer obtained by curing the photocurable resin composition.

Claims

1. A photocurable resin composition comprising: (A) an N-vinyl amide compound represented by the following formula (1): ##STR00015## wherein R.sup.1 and R.sup.2 are each independently a hydrogen atom or hydrocarbon group having 1 to 5 carbon atoms, or R.sup.1 and R.sup.2 may be bonded together to form a hydrocarbon group having 2 to 6 carbon atoms; (B) a polyfunctional (meth)acrylate monomer represented by the following formula (2): ##STR00016## wherein R.sup.4 and R.sup.5 are each independently a hydrogen atom or methyl group, R.sup.3 is a trivalent to hexavalent organic residue, a is an integer of 0 to 3, and b is an integer of 3 to 6; (C) a photopolymerization initiator; and (D) a compound having a 2,2,6,6-tetramethyl-4-piperidyl skeleton and represented by the following formula (4) as a radical scavenger; ##STR00017## wherein R.sup.9 and R.sup.10 are each independently a hydrogen atom or methyl group, and e is an integer of 5 to 12.

2. The photocurable resin composition according to claim 1 which comprises 100 to 900 parts by mass of the polyfunctional (meth)acrylate monomer (B) based on 100 parts by mass of the N-vinyl amide compound (A).

3. The photocurable resin composition according to claim 1, wherein the polyfunctional (meth)acrylate monomer (B) comprises a hydroxyl group-containing polyfunctional (meth)acrylate monomer represented by the following formula (3); ##STR00018## wherein R.sup.7 and R.sup.8 are each independently a hydrogen atom or methyl group, R.sup.6 is a tetravalent to hexavalent organic residue, c is an integer of 0 to 3, and d is an integer of 3 to 5.

4. The photocurable resin composition according to claim 3 which comprises 100 to 900 parts by mass of the polyfunctional (meth)acrylate monomer (B) based on 100 parts by mass of the N-vinyl amide compound (A) and 0.001 to 60 parts by mass of the hydroxyl group-containing polyfunctional (meth)acrylate monomer based on 100 parts by mass of the polyfunctional (meth)acrylate monomer (B).

5. The photocurable resin composition according to claim 1 which comprises 0.005 to 10 parts by mass of (D) a radical scavenger comprising the compound having 2,2,6,6-tetramethyl-4-piperidyl skeleton represented by the above formula (4) based on 100 parts by mass of the total of the above (A) an N-vinyl amide compound and the above (B) a polyfunctional (meth)acrylate monomer.

6. A laminate comprising an optical substrate and a cured film of the photocurable resin composition of claim 1 on the surface of the optical substrate.

7. A laminate comprising a primer layer, a coat layer containing a photochromic compound and a hard coat layer in this order on the cured film of the photocurable resin composition of the laminate of claim 6.

8. The photocurable resin composition according to claim 2, wherein the polyfunctional (meth)acrylate monomer (B) comprises a hydroxyl group-containing polyfunctional (meth)acrylate monomer represented by the following formula (3); ##STR00019## wherein R.sup.7 and R.sup.8 are each independently a hydrogen atom or methyl group, R.sup.6 is a tetravalent to hexavalent organic residue, c is an integer of 0 to 3, and d is an integer of 3 to 5.

9. The photocurable resin composition according to claim 2 which comprises 100 to 900 parts by mass of the polyfunctional (meth)acrylate monomer (B) based on 100 parts by mass of the N-vinyl amide compound (A) and 0.001 to 60 parts by mass of the hydroxyl group-containing polyfunctional (meth)acrylate monomer based on 100 parts by mass of the polyfunctional (meth)acrylate monomer (B).

10. The photocurable resin composition according to claim 2 which comprises 0.005 to 10 parts by mass of (D) a radical scavenger comprising the compound having 2,2,6,6-tetramethyl-4-piperidyl skeleton represented by the above formula (4) based on 100 parts by mass of the total of the above (A) an N-vinyl amide compound and the above (B) a polyfunctional (meth)acrylate monomer.

11. The photocurable resin composition according to claim 3 which comprises 0.005 to 10 parts by mass of (D) a radical scavenger comprising the compound having 2,2,6,6-tetramethyl-4-piperidyl skelton represented by the above formula (4) based on 100 parts by mass of the total of the above (A) an N-vinyl amide compound and the above (B) a polyfunctional (meth)acrylate monomer.

12. The photocurable resin composition according to claim 4 which comprises 0.005 to 10 parts by mass of (D) a radical scavenger comprising the compound having 2,2,6,6-tetramethyl-4-piperidyl skelton represented by the above formula (4) based on 100 parts by mass of the total of the above (A) an N-vinyl amide compound and the above (B) a polyfunctional (meth)acrylate monomer.

13. A laminate comprising an optical substrate and a cured film of the photocurable resin composition of claim 2 on the surface of the optical substrate.

14. A laminate comprising an optical substrate and a cured film of the photocurable resin composition of claim 3 on the surface of the optical substrate.

15. A laminate comprising an optical substrate and a cured film of the photocurable resin composition of claim 4 on the surface of the optical substrate.

16. A laminate comprising an optical substrate and a cured film of the photocurable resin composition of claim 5 on the surface of the optical substrate.

17. A laminate comprising a primer layer, a coat layer containing a photochromic compound and a hard coat layer in this order on the cured film of the photocurable resin composition of the laminate of claim 3.

18. A laminate comprising a primer layer, a coat layer containing a photochromic compound and a hard coat layer in this order on the cured film of the photocurable resin composition of the laminate of claim 4.

19. A laminate comprising a primer layer, a coat layer containing a photochromic compound and a hard coat layer in this order on the cured film of the photocurable resin composition of the laminate of claim 5.

Description

EXAMPLES

(1) The following examples are provided for the purpose of further illustrating the present invention but are in no way to be taken as limiting. Components used in the following examples are given below.

(2) Component (A) (N-vinyl amide compound)

(3) A-1: N-vinyl pyrrolidone

(4) A-2: N-vinyl acetamide

(5) Component (B) (polyfunctional (meth)acrylate monomer containing no hydroxyl group which is polyfunctional (meth)acrylate monomer represented by formula (2))

(6) B-1: pentaerythritol tetraacrylate

(7) B-2: trimethylolpropane triacrylate (hydroxy group-containing polyfunctional (meth)acrylate monomer represented by formula (3))

(8) B-3: pentaerythritol triacrylate

(9) B-4: dipentaerythritol pentaacrylate Component (C) (photopolymerization initiator)

(10) C-1: bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide

(11) C-2: 2,4,6-trimethylbenzoyl-diphenylphosphine oxide Component (D); radical scavenger

(12) D-1: bis(1,2,2,6,6-pentamethyl-piperidyl)sebacate

(13) D-2: ethylenebis(oxyethylene)bis[3,5-tert-butyl-4-hydroxy-m-toluyl]propionate

(14) D-3: tris-(2-methyl-4-hydroxy-5-tert-butylphenyl)-butane

(15) D-4: bis(1-octyloxy-2,2,6,6-tetramethyl-4-piperidyl)sebacate

(16) (E) another monomer component

(17) E-1: ethylene glycol diacrylate

(18) Photochromic compound

(19) PC1:

(20) ##STR00012##
PC2:

(21) ##STR00013##
PC3:

(22) ##STR00014##

Example 1

(23) (Preparation of Photocurable Resin Composition)

(24) 7.5 parts by mass of C-1 and 1 part by mass of a surfactant (L-7001 of Dow Corning Toray Co., Ltd.) were added to and dissolved in a mixture of 100 parts by mass of A-1, 313 parts by mass of B-1 and 87 pars by mass of B-3 under agitation. After dissolution was confirmed, the resulting solution was filtered with a 0.45 m membrane filter and deaerated under a reduced pressure of 0.09 Mpa for 10 minutes. The amounts of these components are shown in Table 1 but the amount of the above surfactant is not shown in Table 1.

(25) (Production of Laminate)

(26) A polycarbonate resin plastic lens (refractive index of 1.59) was used as the plastic substrate. This plastic optical substrate was subjected to a supersonic treatment with a 50 C. 5% sodium hydroxide aqueous solution for 5 minutes, rinsed with running water for 5 minutes and then with distilled water for 5 minutes and dried at 150 C. After drying, a spin coater was used to apply the photocurable resin composition to a thickness of 5.5 to 7.2 m. This coating film was irradiated with ultraviolet light by using F3000SQ (of Heraeus Co., Ltd.) having an output of 120 mW/cm.sup.2 and equipped with a D valve to be cured so as to obtain a laminate having the cured body (cured body layer thickness of 5.0 to 6.5 m) (cured film)) of the photocurable resin composition. The following evaluations were made on the obtained laminate. The evaluation results are shown in Table 1.

(27) <Evaluation Methods of Laminate>

(28) 1. Appearance

(29) The laminate was irradiated with light from a high-pressure mercury lamp to project a projection plane on white paper which was observed visually. The evaluation criteria are given below.

(30) : no problem with appearance

(31) : a small appearance defect such as shrinkage can be seen

(32) X: an appearance defect such as a crack or shrinkage can be seen

(33) 2. Adhesion

(34) Adhesion was evaluated by a cross-cut tape test. That is, a cutter knife was used to make cuts in the surface of the laminate having the cured body (cured film) of the photocurable resin composition at intervals of about 1 mm so as to form 100 squares. A cellophane adhesive tape (Cellotape (registered trademark) of Nichiban Co., Ltd.) was strongly attached to the surface and then peeled off from the surface at a stretch in a 90 direction to count the number of squares (out of the 100 squares) left behind of the coating film. The adhesion was evaluated based on the following three criteria.

(35) A: 100/100

(36) B: 99/100 to 95/100

(37) C: less than 95/100

(38) 3. Adhesion after Immersion in Boiling Water

(39) After the laminate was immersed in boiling water for 1 hour, the plastic lens was taken out and water drops were wiped off from the plastic lens to evaluate adhesion in the same manner as the above adhesion evaluation method. After evaluation, this laminate was immersed in boiling water again. This operation was repeated three times to carry out the test until the total boiling time became 3 hours.

(40) 4. Steel Wool Scratch Resistance

(41) The surface of the plastic lens of the laminate having the cured body (cured film) of the photocurable resin composition was rubbed with steel wool (BONSTAR #0000 of Nippon Steel Wool Co., Ltd.) 10 times in both ways to evaluate the degree of scratching visually based on the following four criteria. The evaluation criteria are given below.

(42) A: rarely scratched (less than 5 scratches are seen)

(43) B: slightly scratched (5 or more to less than 10 scratches are seen)

(44) C: scratched (10 or more to less than 20 scratches are seen)

(45) D: markedly scratched (20 or more scratches are seen)

(46) E: peeled off

Examples 2 to 15, Comparative Examples 1 to 2

(47) Laminates having a cured body (cured film) of each of the photocurable resin compositions shown in Table 1 was manufactured and evaluated in the same manner as in Example 1. The evaluation results are shown in Table 1. In the examples and comparative examples, the same amount of the same surfactant as in Example 1 was used and therefore not shown in Table 1.

(48) TABLE-US-00001 TABLE 1 evaluation results of laminate Photocurable resin composition (parts by mass) adhesion after immersion Component Component Component another in boiling water scratch (A) (B) (C) component appearance adhesion (1H) (2H) (3H) resistance Ex. 1 A-1 B-1/B-3 C-1 A A A A A (100) (313/87) (7.5) Ex. 2 A-1 B-1/B-2/B-3 C-1 A A A A A (100) (197/159/45) (7.5) Ex. 3 A-1 B-2/B-3 C-1 A A A A A (100) (168/232) (7.5) Ex. 4 A-1 B-1/B-4 C-1 A A A A A (100) (342/58) (7.5) Ex. 5 A-1 B-1/B-3 C-1 A A A A A (100) (98/135) (5) Ex. 6 A-1 B-1/B-3 C-1 A A A B A (100) (520/280) (13.5) Ex. 7 A-1 B-1/B-3 C-1 A A A A B (100) (65/36) (3) Ex. 8 A-1 B-4 C-1 A A B C A (100) (400) (7.5) Ex. 9 A-1 B-1/B-3 C-1 E-1 A A A A A (100) (313/87) (7.5) (25) Ex. 10 A-1 B-1 C-1 A A A A A (100) (313) (6.2) Ex. 11 A-1 B-1/B-3 C-1 A B B C A (100) (40/360) (7.5) Ex. 12 A-1 B-1/B-3 C-1 A B A A C (100) (28/39) (2.5) Ex. 13 A-1 B-1/B-3 C-1 A B B C A (100) (580/420) (16.5) Ex. 14 A-2 B-1/B-3 C-1 A A A A A (100) (313/87) (7.5) Ex. 15 A-2 B-1/B-4 C-1 A A A A A (100) (342/58) (7.5) C. Ex. 1 B-1 C-1 B B C C A (400) (6) C. Ex. 2 A-1 C-1 x C C C C E (100) (1.5) Ex.: Example C. Ex.: Comparative Example

Example 16

(49) (Preparation of Photochromic Coating Agent)

(50) A photochromic coating agent was obtained by mixing together the following components under agitation at 70 C. for 15 minutes based on the following formulation. trimethylolpropane trimethacrylate: 20 parts by mass ditrimethylolpropane tetramethacrylate: 30 parts by mass 2,2-bis[4-(methacryloxy-polyethoxy)phenyl]propane (average chain length of ethylene glycol chains of 10, average molecular weight of 804): 30 parts by mass polyethylene glycol dimethacrylate (average chain length of ethylene glycol chains of 14, average molecular weight of 736): 20 parts by mass

(51) PC1: 0.3 part by mass

(52) PC2: 1.0 part by mass

(53) PC3: 2.0 parts by mass

(54) bis(1,2,2,6,6-pentamethyl-4-piperidyl)sebacate: 3 parts by mass

(55) ethylenebis(oxyethylene)bis[3-(5-tert-butyl-4-hydroxy-m-tolyl)propionate]: 3 parts by mass

(56) phenylbis(2,4,6-trimethylbenzoyl)-phosphine oxide (polymerization initiator): 0.3 part by mass

(57) L-7001 (of Dow Corning Toray Co., Ltd.): 0.1 part by mass

(58) (Preparation of Hard Coat Agent)

(59) 20.8 parts by mass of -glycidoxypropyl trimethoxysilane and 8.2 part by mass of tetraethoxysilane as organic silicon compounds and 4.9 parts by mass of t-butyl alcohol and 0.1 part by mass of L-7001 (of Dow Corning Toray Co., Ltd.) as organic solvents were mixed together. A mixture of 9.0 parts by mass of water and 18.0 parts by mass of SNOWTEX 0-40 (of Nissan Chemical Industries, Ltd.) was added to the resulting solution under agitation and kept stirred for 20 hours after the end of addition. Then, 3.4 parts by mass of ethylene glycol monoisopropyl ether, 4.5 parts by mass of acetyl acetone, 15.1 parts by mass of t-butyl alcohol, 15.16 parts by mass of methanol and 0.84 part by mass of tris(acetylacetonato)aluminum (III) were mixed with the resulting solution and stirred for 2 hours to prepare a hard coat agent.

(60) (Manufacture of Laminate Having a Primer Layer, a Coat Layer Containing a Photochromic Compound (Photochromic Coat Layer) and a Hard Coat Layer in this Order on the Cured Body (Cured Film) of Photocurable Resin Composition)

(61) A laminate having the cured body (cured film) of the photocurable resin composition prepared in the same manner as in Example 1 was immersed in a 40 C. 20% potassium hydroxide aqueous solution for 30 seconds, rinsed with running water for 5 minutes and then with distilled water for 5 minutes and dried at 150 C. Then, TR-SC-P (manufactured by Tokuyama Corporation; containing a moisture-curable urethane resin as the main component) was used as a primer coating solution to be applied to the surface of the laminate having the cured body (cured film) of the photocurable resin composition by spin coating. After the application of the primer coating solution, it was left at room temperature for 5 minutes to form a primer layer having a thickness of 7 m.

(62) Thereafter, about 1 g of the above photochromic coating agent was spin coated on the surface of the above primer layer to a thickness of 401 m. The coated laminate was irradiated with light by adjusting integrated illuminance on the surface of the laminate to 10 J/cm.sup.2 within 40 seconds with the F3000SQ in a nitrogen gas atmosphere to cure the coating film. Thereafter, the photochromic coat layer was formed by heating in a 90 C. incubator for 1 hour.

(63) The laminate having the photochromic coat layer was subjected to a corona discharge treatment for 30 seconds, immersed in a 50 C. 10% sodium hydroxide aqueous solution and then subjected to alkali etching for 5 minutes by using an ultrasonic cleaner. After alkali etching, the laminate was rinsed with tap water and distilled water sequentially to remove the residual alkali and dried at 150 C. A hard coat agent was dip coated on this laminate to a thickness of 2.5 m. After dip coating, the hard coat agent was precured in a 70 C. oven for 15 minutes and thermally cured at 130 C. for 3 hours to obtain a laminate having a hard coat layer. The appearance of the obtained laminate, and the adhesion and adhesion after immersion in boiling water of the layers formed on the plastic substrate were evaluated by the same methods as described above. The results are shown in Table 2.

Examples 17 to 30, Comparative Examples 3 to 5

(64) Laminates were formed on the laminate having the cured body (cured film) of each of the photocurable resin compositions shown in Table 2 in the same manner as in Example 16 and evaluated in the same manner as in Example 1. The evaluation results are shown in Table 2. Since the same amount of the same surfactant as in Example 1 was used in the photocurable resin compositions of the examples and comparative examples, the amount of the surfactant was not shown in Table 2.

(65) TABLE-US-00002 TABLE 2 evaluation results of laminate Photocurable resin composition (parts by mass) adhesion after immersion Component Component Component another in boiling water (A) (B) (C) component appearance adhesion (1H) (2H) (3H) Ex. 16 A-1 B-1/B-3 C-1 A A A A (100) (313/87) (7.5) Ex. 17 A-1 B-1/B-2/B-3 C-1 A A A A (100) (197/159/45) (7.5) Ex. 18 A-1 B-2/B-3 C-1 A A A A (100) (168/232) (7.5) Ex. 19 A-1 B-1/B-4 C-1 A A A A (100) (342/58) (7.5) Ex. 20 A-1 B-1/B-3 C-1 A A A A (100) (98/135) (5) Ex. 21 A-1 B-1/B-3 C-1 A A B B (100) (520/280) (13.5) Ex. 22 A-1 B-1/B-3 C-1 A A A A (100) (65/36) (3) Ex. 23 A-1 B-4 C-1 A B B C (100) (400) (7.5) Ex. 24 A-1 B-1/B-3 C-1 E-1 A A A A (100) (313/87) (7.5) (25) Ex. 25 A-1 B-1 C-1 A A B C (100) (313) (6.2) Ex. 26 A-1 B-1/B-3 C-1 A B C C (100) (40/360) (7.5) Ex. 27 A-1 B-1/B-3 C-1 A A A B (100) (28/39) (2.5) Ex. 28 A-1 B-1/B-3 C-1 A B C C (100) (580/420) (16.5) Ex. 29 A-2 B-1/B-3 C-1 A A A A (100) (313/87) (7.5) Ex. 30 A-2 B-1/B-4 C-1 A A A A (100) (342/58) (7.5) C. Ex. 3 B-1 C-1 B C C C (400) (6) C. Ex. 4 A-1 C-1 x C C C C (100) (1.5) C. Ex. 5 B-1/B-2 C-1 A C C C (400/100) (7.5) Ex.: Example C. Ex.: Comparative Example

Examples 31 to 36

(66) Photocurable resin compositions shown in Table 3 were prepared. Laminates were manufactured by using the obtained photocurable resin compositions in the same manner as in Example 16, and the physical properties of the laminates right after molding were evaluated in the same manner as in Example 16. The evaluation results are shown in Table 3.

(67) Then, the photocurable resin compositions having the same composition as in Example 16 and Example 19 and the photocurable resin compositions (Examples 31 to 36) shown in Table 3 were kept in an incubator kept at 40 C. for 2 weeks and 1 month. After the elapse of the storage periods, laminates were manufactured by using the photocurable resin compositions taken out from the incubator and evaluated in the same manner as in Example 16. The evaluation results of the photocurable resin compositions after 2 weeks of storage are shown in Table 4. The evaluation results of the photocurable resin compositions after 1 month of storage are shown in Table 5.

(68) Since the same amount of the same surfactant as in Example 1 was used in the photocurable resin compositions of the examples, the amount of the surfactant was not shown in Tables 3, 4 and 5.

(69) TABLE-US-00003 TABLE 3 evaluation results of laminate (initial) Photocurable resin composition (parts by mass) adhesion after immersion Component Component Component another in boiling water (A) (B) (C) component appearance adhesion (1H) (2H) (3H) Ex. 31 A-1 B-1/B-3 C-1 D-1 A A A A (100) (313/87) (7.5) (0.1) Ex. 32 A-1 B-1/B-3 C-1 D-2 A A A A (100) (313/87) (7.5) (0.4) Ex. 33 A-1 B-1/B-3 C-1 D-3 A A A A (100) (313/87) (7.5) (0.5) Ex. 34 A-1 B-1/B-3 C-1 D-4 A A A A (100) (313/87) (7.5) (0.5) Ex. 35 A-1 B-1/B-4 C-1 D-1 A A A A (100) (342/58) (7.5) (1.0) Ex. 36 A-1 B-1/B-3 C-2 D-1 A A A A (100) (313/87) (7.5) (0.1) Ex. 16 A-1 B-1/B-3 C-1 A A A A (100) (313/87) (7.5) Ex. 19 A-1 B-1/B-4 C-1 A A A A (100) (342/58) (7.5) Ex.: Example

(70) TABLE-US-00004 TABLE 4 evaluation results of laminate (2 weeks) Photocurable resin composition (parts by mass) adhesion after immersion Component Component Component another in boiling water (A) (B) (C) component appearance adhesion (1H) (2H) (3H) Ex. 31 A-1 B-1/B-3 C-1 D-1 A A A A (100) (313/87) (7.5) (0.1) Ex. 32 A-1 B-1/B-3 C-1 D-2 A A A A (100) (313/87) (7.5) (0.4) Ex. 33 A-1 B-1/B-3 C-1 D-3 A A A A (100) (313/87) (7.5) (0.5) Ex. 34 A-1 B-1/B-3 C-1 D-4 A A A A (100) (313/87) (7.5) (0.5) Ex. 35 A-1 B-1/B-4 C-1 D-1 A A A A (100) (342/58) (7.5) (1.0) Ex. 36 A-1 B-1/B-3 C-2 D-1 A A A A (100) (313/87) (7.5) (0.1) Ex. 16 A-1 B-1/B-3 C-1 A A A A (100) (313/87) (7.5) Ex. 19 A-1 B-1/B-4 C-1 A A A A (100) (342/58) (7.5) Ex.: Example

(71) TABLE-US-00005 TABLE 5 evaluation results of laminate (1 month) Photocurable resin composition (parts by mass) adhesion after immersion Component Component Component another in boiling water (A) (B) (C) component appearance adhesion (1H) (2H) (3H) Ex. 31 A-1 B-1/B-3 C-1 D-1 A A A A (100) (313/87) (7.5) (0.1) Ex. 32 A-1 B-1/B-3 C-1 D-2 A A A A (100) (313/87) (7.5) (0.4) Ex. 33 A-1 B-1/B-3 C-1 D-3 A A A A (100) (313/87) (7.5) (0.5) Ex. 34 A-1 B-1/B-3 C-1 D-4 A A A A (100) (313/87) (7.5) (0.5) Ex. 35 A-1 B-1/B-4 C-1 D-1 A A A A (100) (342/58) (7.5) (1.0) Ex. 36 A-1 B-1/B-3 C-2 D-1 A A A A (100) (313/87) (7.5) (0.1) Ex. 16 A-1 B-1/B-3 C-1 A C C C (100) (313/87) (7.5) Ex. 19 A-1 B-1/B-4 C-1 A C C C (100) (342/58) (7.5) Ex.: Example

Examples 37 to 42

(72) Photocurable resin composition having the same compositions as in Examples 31 to 36 were used to manufacture laminates in the same manner as in Examples 31 to 36 except that a polyurethane resin plastic lens (trade name: TRIVEX, refractive index of 1.53) was used as the plastic substrate, and the same evaluations were made on the laminates.

(73) The same photocurable resin composition as in Example 31 was used in Example 37, the same photocurable resin composition as in Example 32 was used in Example 38, the same photocurable resin composition as in Example 33 was used in Example 39, the same photocurable resin composition as in Example 34 was used in Example 40, the same photocurable resin composition as in Example 35 was used in Example 41, and the same photocurable resin composition as in Example 36 was used in Example 42. Since the same amount of the same surfactant as in Example 1 was used in the photocurable resin compositions of these examples, the amount of the surfactant was not shown in Tables 6, 7 and 8.

(74) The results are shown in Tables 6, 7 and 8.

(75) TABLE-US-00006 TABLE 6 evaluation results of laminate (initial) Photocurable resin composition (parts by mass) adhesion after immersion Component Component Component another in boiling water (A) (B) (C) component appearance adhesion (1H) (2H) (3H) Ex. 37 A-1 B-1/B-3 C-1 D-1 A A A A (100) (313/87) (7.5) (0.1) Ex. 38 A-1 B-1/B-3 C-1 D-2 A A A A (100) (313/87) (7.5) (0.4) Ex. 39 A-1 B-1/B-3 C-1 D-3 A A A A (100) (313/87) (7.5) (0.5) Ex. 40 A-1 B-1/B-3 C-1 D-4 A A A A (100) (313/87) (7.5) (0.5) Ex. 41 A-1 B-1/B-4 C-1 D-1 A A A A (100) (342/58) (7.5) (1.0) Ex. 42 A-1 B-1/B-3 C-2 D-1 A A A A (100) (313/87) (7.5) (0.1) Ex.: Example

(76) TABLE-US-00007 TABLE 7 evaluation results of laminate (2 weeks) Photocurable resin composition (parts by mass) adhesion after immersion Component Component Component another in boiling water (A) (B) (C) component appearance adhesion (1H) (2H) (3H) Ex. 37 A-1 B-1/B-3 C-1 D-1 A A A A (100) (313/87) (7.5) (0.1) Ex. 38 A-1 B-1/B-3 C-1 D-2 A A A A (100) (313/87) (7.5) (0.4) Ex. 39 A-1 B-1/B-3 C-1 D-3 A A A A (100) (313/87) (7.5) (0.5) Ex. 40 A-1 B-1/B-3 C-1 D-4 A A A A (100) (313/87) (7.5) (0.5) Ex. 41 A-1 B-1/B-4 C-1 D-1 A A A A (100) (342/58) (7.5) (1.0) Ex. 42 A-1 B-1/B-3 C-2 D-1 A A A A (100) (313/87) (7.5) (0.1) Ex.: Example

(77) TABLE-US-00008 TABLE 8 evaluation results of laminate (1 month) Photocurable resin composition (parts by mass) adhesion after immersion Component Component Component another in boiling water (A) (B) (C) component appearance adhesion (1H) (2H) (3H) Ex. 37 A-1 B-1/B-3 C-1 D-1 A A A A (100) (313/87) (7.5) (0.1) Ex. 38 A-1 B-1/B-3 C-1 D-2 A A A A (100) (313/87) (7.5) (0.4) Ex. 39 A-1 B-1/B-3 C-1 D-3 A A A A (100) (313/87) (7.5) (0.5) Ex. 40 A-1 B-1/B-3 C-1 D-4 A A A A (100) (313/87) (7.5) (0.5) Ex. 41 A-1 B-1/B-4 C-1 D-1 A A A A (100) (342/58) (7.5) (1.0) Ex. 42 A-1 B-1/B-3 C-2 D-1 A A A A (100) (313/87) (7.5) (0.1) Ex.: Example

Effect of the Invention

(78) According to the present invention, a cured body (cured film) of a photocurable resin composition free from an appearance defect such as a crack while it has high adhesion to a plastic substrate and a laminate having the cured body can be obtained. It is assumed that the reason that the photocurable resin composition of the present invention has the above effect is that an N-vinyl amide compound contained in the photocurable resin composition of the present invention is dissolved in a part close to the surface of the plastic optical substrate moderately. That is, it is considered that the photocurable resin composition permeates and diffuses into the plastic substrate from the surface and strong mechanical coupling with the plastic substrate is obtained by polymerizing and curing the photocurable resin composition by irradiation in that state. As a result, high adhesion between the cured body (cured film) of the photocurable resin composition and the plastic substrate is obtained.

(79) Further, since the N-vinyl amide compound has a polymerizable group, it seems that volume shrinkage at the time of curing is suppressed, adhesion between the cured body (cured film) of the photocurable resin composition and the plastic substrate is further enhanced, and the production of an appearance defect such as a crack can be suppressed by copolymerizing it with the polyfunctional acrylate monomer which is blended with the N-vinyl amide compound. Since volume shrinkage can be suppressed as described above, the cracking of the cured body (cured film) of the photocurable resin composition can be suppressed as well. Due to this small volume shrinkage, the photocurable resin composition of the present invention is useful as a coating agent for the surface of an optical substrate except for plastic substrates, for example, a substrate made of an inorganic material such as glass.