The thickness of the cured film is not particularly limited, but is preferably 0.05 μm to 500 μm, more preferably 0.1 μm to 100 μm, and still more preferably 1 μm to 50 μm.

The cured film is preferably an antithrombotic film.

Since the cured film formed on the medical device according to the embodiment of the present invention suppresses the adhesion of platelets, the adhesion of proteins, and the adhesion of cells, blood clots are difficult to be formed.

EXAMPLES
Example 1
Production of Evaluation Sample

An evaluation sample (hereinafter, sometimes referred to as a “sample 1”) was produced by the method described below.

1. Synthesis of Compound (1-1)

N-methyldiethanolamine (10 g, 83.9 mmol) and tetrahydrofuran (50 mL) were mixed. A solution obtained by diluting 2-isocyanatoethyl methacrylate (27.34 g, 1,176 mmol) with tetrahydrofuran (50 mL) was added dropwise to the mixed solution. Further, a solution obtained by diluting Neostann U600 (538 mg; manufactured by NITTO KASEI CO., LTD.) with tetrahydrofuran (10 mL) was added dropwise to the mixed solution while paying attention to heat generation, and the solution thus obtained is stirred at a room temperature for 12 hours. The formula for the reaction is as shown below. The reaction solution was concentrated under reduced pressure and the obtained crude product was purified by being subjected to silica gel column chromatography (eluent:ethyl acetate to ethyl acetate:methanol=4:1), so that a compound represented by Formula (1-1) [compound (1-1)] was obtained (30 g, yield 83%). With nuclear magnetic resonance (′H NMR), it was confirmed that the obtained compound was a target product.

¹H NMR (methanol-d₄, 400 MHz) δ: 1.93 (6H, s), 2.35 (3H, s), 2.71 (4H, t), 3.39 (4H, t), 4.10-4.19 (8H, m), 5.62 (2H, s), 6.12 (2H, s).

[Image Omitted]

As a synthesis method of the compound (1-1), the following conditions can also be used to carry out the same synthesis as in the method described above.

N-methyldiethanolamine (7 g, 58.7 mmol), tetrahydrofuran (100 mL), and 2-isocyanatoethyl methacrylate (19.6 g, 126 mmol) were mixed and stirred at a room temperature for 24 hours. The reaction solution was concentrated under reduced pressure and the obtained crude product was purified by being subjected to silica gel column chromatography (eluent:ethyl acetate to ethyl acetate:methanol=9:1), so that a compound represented by Formula (1-1) (in the present specification, referred to as a “compound (1-1)”) was obtained (21 g, yield 85%).

2. Preparation of Cured Film-Forming Composition

The synthesized compound (1-1) (containing 30 ppm of 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl (4OH-TEMPO) as a polymerization inhibitor), a polymerization initiator, and a solvent were blended in the blending amount shown in Table 1, and a cured film-forming composition (hereinafter, sometimes referred to as a “cured film-forming composition 1”) was prepared.

[Image Omitted]

3. Production of Cured Film

The prepared cured film-forming composition 1 was applied onto the polyethylene terephthalate (PET) film (Cosmo shine A4300, manufactured by TOYOBO CO., LTD.; double-sided easy-adhesion treated PET film) while adjusting clearance by using a bar coater such that the thickness after drying was 3 μm, and then dried to form a cured film precursor film.

After that, the cured film precursor film was exposed at the exposure amount of 2 J/cm²by using an ultraviolet exposure machine (ECS-401G, manufactured by EYEGRAPHICS Co., Ltd.; light source was a high-pressure mercury lamp), so that a cured film was produced on the PET film.

1. Platelet Adhesiveness

A platelet adhesion experiment was conducted by using the produced evaluation sample (sample 1) and a PET film (DIAFOIL T100E125, manufactured by Mitsubishi Chemical Corporation) as a control sample. Platelet-rich plasma and platelet-poor plasma were recovered by centrifugation from human whole blood anticoagulated with sodium citrate, and platelet-rich plasma was diluted with platelet-poor plasma, thereby preparing a platelet suspension of 4×10⁷cells/mL. Subsequently, each sample surface came into contact with the platelet suspension at 37° C. for 60 minutes, and then was rinsed twice with a phosphate buffer solution. Then, the platelets which have adhered to each sample surface were fixed with a 1% glutaraldehyde solution. Each sample subjected to fixing treatment was washed by being immersed in a phosphate buffer solution for 10 minutes, a 1:1 mixed solution of a phosphate buffer solution and water for 8 minutes, water for 8 minutes, and water again for 8 minutes, and dried with air at a room temperature. After that, the number of the platelets which have adhered to each sample surface of 1×10⁴μm²was observed with an electron microscope, and the number of platelets which have adhered was measured.

In a case where the total number of platelets which have adhered to the PET film (control sample) was set to 100%, the relative number of platelets in the sample 1 was calculated, and the platelet adhesiveness was evaluated according to the following criteria.

- A: 3% or less
- B: more than 3% and 5% or less
- C: more than 5% and 20% or less
- D: more than 20%
  
  2. Fibroblast Adhesiveness

A fibroblast adhesion test was conducted by using, as evaluation substrates, the produced cell adhesion sheet (sample 1) and a PET film (DIAFOIL T100E125, manufactured by Mitsubishi Chemical Corporation) as a control sample. After the surface of each substrate was washed with phosphate buffered saline, each substrate was immersed at 37° C. for 60 minutes in a 1:1 mixed medium of Dulbecco's Modified Eagle's Medium and Ham's F-12 medium (DMEM/F12 medium) prepared by adding fetal bovine serum by 10%, thereby acclimating the substrate. After that, normal human dermal fibroblasts (NHDF) suspended in the above medium were seeded into each sample at a density of 1×10⁴per 1 cm², thereby bringing the suspension and each sample into contact with each other at 37° C. for 60 minutes. Subsequently, the substrates were rinsed twice with a phosphate buffer solution, and the cells which have adhered to each substrate were fixed with a 4% paraformaldehyde solution. The cell nucleus was stained with 4′,6-diamidino-2-phenylindole (DAPI) and the actin skeleton was stained with phalloidin antibody, and the number of cells which have adhered was measured using a fluorescence microscope.

In a case where the total number of fibroblasts which have adhered to the PET film (control sample) was set to 100%, the relative number of fibroblasts in the sample 1 was calculated, and the fibroblast adhesiveness was evaluated according to the following criteria.