COATING AGENT

Abstract

A coating agent that may form a base film having excellent adhesiveness to a substrate of a plastic such as a cycloolefin resin and having transparency and a high refractive index. A coating agent including a polymer consisting of only a repeating unit derived from a monomer represented by formula (I) (wherein Ar represents a C6 to C10 aryl group optionally having a substituent and Ar is the same or different; X represents an oxygen atom or NR; R represents a hydrogen atom or a C1 to C6 alkyl group; and Y represents a polymerizable functional group.)

##STR00001##

Claims

1. A coating agent comprising a polymer consisting of only a repeating unit derived from a monomer represented by formula (I): ##STR00007## (wherein Ar represents a C6 to C10 aryl group optionally having a substituent and Ar is the same or different; X represents an oxygen atom or NR; R represents a hydrogen atom or a C1 to C6 alkyl group; and Y represents a polymerizable functional group.)

2. A coating agent comprising a homopolymer having a repeating unit derived from a monomer represented by formula (I): ##STR00008## (wherein Ar represents a C6 to C10 aryl group optionally having a substituent and Ar is the same or different; X represents an oxygen atom or NR; R represents a hydrogen atom or a C1 to C6 alkyl group; and Y represents a polymerizable functional group.)

3. The coating agent according to claim 1, wherein in formula (I), Y is an acryloyl group or a methacryloyl group.

4. The coating agent according to claim 1, wherein the coating agent is a coating agent onto a plastic substrate.

5. The coating agent according to claim 4, wherein the plastic substrate is a polyolefin resin substrate.

6. The coating agent according to claim 2, wherein in formula (I), Y is an acryloyl group or a methacryloyl group.

7. The coating agent according to claim 2, wherein the coating agent is a coating agent onto a plastic substrate.

8. The coating agent according to claim 3, wherein the coating agent is a coating agent onto a plastic substrate.

9. The coating agent according to claim 6, wherein the coating agent is a coating agent onto a plastic substrate.

10. The coating agent according to claim 7, wherein the plastic substrate is a polyolefin resin substrate.

11. The coating agent according to claim 8, wherein the plastic substrate is a polyolefin resin substrate.

12. The coating agent according to claim 9, wherein the plastic substrate is a polyolefin resin substrate.

Description

EXAMPLES

Example 1

1. Synthesis of Trityl Methacrylate

[0090] Trityl chloride (20.00 g, 0.072 mol), triethylamine (12.34 g, 0.122 mol), and super-dehydrated tetrahydrofuran (168.89 g) were added to a 300 mL four-necked flask purged with nitrogen. The reaction solution was cooled to 10 C. or less in an ice bath, and methacrylic acid chloride (9.88 g, 0.115 mol) was slowly dropped. Further, the temperature of the reaction solution was increased to room temperature, and the reaction was performed for 24 hours. After the completion of the reaction, the reaction solution was water-washed with saturated sodium bicarbonate water, and the THF in the organic layer was distilled off by an evaporator. Then, the residue was recrystallized with hexane to obtain 19.34 g (yield 82%) of trityl methacrylate.

[0091] The NMR data of the obtained trityl methacrylate are shown below:

[0092] .sup.1H NMR (acetone-d.sub.6, 500 MH, 300 K, TMS): 7.2-7.5, 6.2, 5.7, 1.9-2.0 ppm

2. Making of Poly(Trityl Methacrylate)

[0093] The polymer was made by a radical polymerization reaction using azobisisobutyronitrile (AIBN) as an initiator.

[0094] The trityl methacrylate (2.00 g, 0.006 mol) synthesized in Example 1 and AIBN (20 mg, 0.12 mmol) were added to a 50 mL Schlenk tube. A stirring bar was placed, and the Schlenk tube was sealed with a three-way cock, and then a gas sampling bag containing nitrogen was placed. The system was degassed by a vacuum pump, and then purged with nitrogen. Then, deoxygenated toluene (8.00 mL) was added, and the mixture was heated in an oil bath at 65 C. for 24 hours for a radical polymerization reaction. After the completion of the reaction, the reaction liquid was added to methanol for reprecipitation. The precipitate was fractionated with a benzene/hexane mixed solvent to remove the oligomer to obtain the polymer as insoluble matter.

[0095] From GPC, the number average molecular weight (Mn) of the polymer was 39631 Da.

3. Preparation of Coating Agent

[0096] Poly(trityl methacrylate) (0.1 g) was dissolved in THF/cyclohexanone=5/5 (v/v) (9.9 g) by heating to obtain a coating agent (A-1) having a solid concentration of 1 wt %.

4. Formation of Coating Film

[0097] A cycloolefin polymer (COP) film having a thickness of 188 m (product name ZEONOR Film ZF-16, manufactured by ZEON Corporation) was cut to 50 mm50 mm, and a film of the coating agent (A-1) was formed by bar coating. The coated film was dried (120 C. for 3 minutes) in an oven to obtain a compact (A-2).

Example 2

1. Synthesis of Tris(4-methylphenyl)methyl Methacrylate

[0098] Chlorotris(4-methylphenyl)methane (2.00 g, 0.006 mol), triethylamine (1.07 g, 0.011 mol), and super-dehydrated tetrahydrofuran (15.74 g) were added to a 100 mL four-necked flask purged with nitrogen. The reaction solution was cooled to 10 C. or less in an ice bath, and methacrylic acid chloride (0.86 g, 0.010 mol) was slowly dropped. Further, the temperature of the reaction liquid was increased to room temperature, and the reaction was performed for 24 hours. After the completion of the reaction, the reaction solution was water-washed with saturated sodium bicarbonate water, and the THF in the organic layer was distilled off by an evaporator. Then, the residue was recrystallized with hexane to obtain tris(4-methylphenyl)methyl methacrylate (1.805 g, yield 78%).

[0099] The NMR data of the obtained tris(4-methylphenyl)methyl methacrylate are shown below:

[0100] .sup.1H NMR (acetone-d.sub.6, 500 MH, 300 K, TMS): 7.2-7.3, 7.1-7.15, 6.15-6.2, 5.6-5.7, 2.3, 1.9-2.0 ppm.

2. Making of Poly{tris(4-methylphenyl)methyl methacrylate}

[0101] The polymer was made by the same method as Example 1 except that tris(4-methylphenyl)methyl methacrylate (2.00 g, 0.005 mol) and AIBN (5.9 mg, 0.04 mmol) were used.

[0102] From GPC, the number average molecular weight (Mn) of the polymer was 42301 Da.

3. Preparation of Coating Agent

[0103] Poly{tris(4-methylphenyl)methyl methacrylate} (0.1 g) was dissolved in THF/cyclohexanone=5/5 (v/v) (9.9 g) by heating to obtain a coating agent (B-1) having a solid concentration of 1 wt %.

4. Formation of Coating Film

[0104] Except that (B-1) was used for the coating agent, the same operation as Example 1 was performed to obtain a compact (B-2).

Example 3

1. Synthesis of Tris(4-chlorophenyl)methyl Methacrylate

[0105] Chlorotris(4-chlorophenyl)methane (5.00 g, 0.013 mol), triethylamine (2.26 g, 0.022 mol), and super-dehydrated tetrahydrofuran (36.30 g) were added to a 100 mL four-necked flask purged with nitrogen. The reaction solution was cooled to 10 C. or less in an ice bath, and methacrylic acid chloride (1.81 g, 0.021 mol) was slowly dropped. Further, the temperature of the reaction liquid was increased to room temperature, and the reaction was performed for 24 hours. After the completion of the reaction, the reaction solution was water-washed with saturated sodium bicarbonate water, and the THF in the organic layer was distilled off by an evaporator. Then, the residue was recrystallized with hexane to obtain tris(4-chlorophenyl)methyl methacrylate (4.58 g, yield 81%).

[0106] The NMR data of the obtained tris(4-chlorophenyl)methyl methacrylate are shown below:

[0107] .sup.1H NMR (acetone-d.sub.6, 500 MH, 300 K, TMS): 7.25-7.4, 6.08, 5.61, 1.90 ppm.

2. Preparation of Poly{tris(4-chlorophenyl)methyl methacrylate}

[0108] The polymer was made by the same method as Example 1 except that tris(4-chlorophenyl)methyl methacrylate (2.00 g, 0.005 mol) and AIBN (5.1 mg, 0.03 mmol) were used.

[0109] From GPC, the number average molecular weight (Mn) of the polymer was 47011 Da.

3. Making of Coating Agent

[0110] Poly{tris(4-chlorophenyl)methyl methacrylate} (0.1 g) was dissolved in THF/cyclohexanone=5/5 (v/v) (9.9 g) by heating to obtain a coating agent (C-1) having a solid concentration of 1 wt %.

4. Formation of Coating Film

[0111] Except that (C-1) was used for the coating agent, the same operation as Example 1 was performed to obtain a compact (C-2).

Example 4

1. Synthesis of Tris(3,5-dimethylphenyl)methyl Methacrylate

[0112] Chlorotris(3,5-dimethylphenyl)methane (5.00 g, 0.01381 mol), triethylamine (2.37 g, 0.02347 mol), and super-dehydrated tetrahydrofuran (37.11 g) were added to a 100 mL four-necked flask purged with nitrogen. The reaction solution was cooled to 10 C. or less in an ice bath, and methacrylic acid chloride (1.90 g, 0.02209 mol) was slowly dropped. Further, the temperature of the reaction liquid was increased to room temperature, and the reaction was performed for 24 hours. After the completion of the reaction, the reaction solution was water-washed with saturated sodium bicarbonate water, and the THF in the organic layer was distilled off by an evaporator. Then, the residue was recrystallized with hexane to obtain tris(3,5-dimethylphenyl)methyl methacrylate (4.50 g, yield 79%).

[0113] The NMR data of the obtained tris(3,5-dimethylphenyl)methyl methacrylate are shown below:

[0114] .sup.1H NMR (acetone-d.sub.6, 500 MH, 300 K, TMS): 7.03, 6.75, 6.0, 5.6, 2.2, 1.9 ppm.

2. Making of Poly{tris(3,5-dimethylphenyl)methyl methacrylate}

[0115] The polymer was made by the same method as Example 1 except that tris(3,5-dimethylphenyl)methyl methacrylate (2.00 g, 0.00485 mol) and AIBN (4.0 mg, 0.024 mmol) were used. From GPC, the number average molecular weight (Mn) of the polymer was 48231 Da.

3. Preparation of Coating Agent

[0116] 0.1 g of poly{tris(3,5-dimethylphenyl)methyl methacrylate} was dissolved in THF/cyclohexanone=5/5 (v/v) (9.9 g) by heating to obtain a coating agent (D-1) having a solid concentration of 1 wt %.

4. Formation of Coating Film

[0117] Except that (D-1) was used for the coating agent, the same operation as Example 1 was performed to obtain a compact (D-2).

(Evaluation of Adhesiveness)

[0118] For the compacts (A-2), (B-2), and (C-2) and the compact (D-2) obtained in the above Examples, a cross-cut peeling test was performed according to the cross-cut tape peeling test method described in JIS K-5400 (1999).

[0119] The coating film on each compact was cross-cut in the form of a grid of 1 mm1 mm squares, and a peeling test was performed using transparent adhesive tape. The results are shown in Table 1.

[0120] For all coating films, no peeling from the COP film was seen.

TABLE-US-00001 TABLE 1 A-2 B-2 C-2 D-2 Test result 100/100 100/100 100/100 100/100