KR101044955B1 - Hydrogel Contact Lens with High Performance Comprising Vinyl Group Substituted Phophazene - Google Patents

Abstract

The present invention relates to a high performance hydrogel contact lens, comprising: (a) polyphosphazene substituted with a vinyl group, (b) 2-hydroxy ethylmethacrylate, (c) N-vinyl It relates to a high-performance hydrogel contact lens comprising a polymer obtained by copolymerizing -pyrrolidone (N-vinyl-pyrrolidone) and (d) ethylene glycol dimethacrylate.

The high-performance hydrogel contact lens has a high light transmittance and an oxygen transmittance, and thus has excellent utility.

Hydrogel contact lens, polyphosphazine, copolymerization, light transmittance, oxygen transmittance

Description

Hydrogel Contact Lens with High Performance Comprising Vinyl Group Substituted Phophazene}

The present invention relates to a high performance hydrogel contact lens having a high light transmittance and high oxygen transmittance.

Contact lenses have moderate mechanical strength, biocompatibility, toxicity, optical transparency of materials, refractive index, surface wettability, and water content suitable for cornea. content, swelling, oxygen transmissibility, flexibility, etc. must be met. In particular, considering the ophthalmic problems and side effects caused in the long-term wear of contact lenses, the requirement of oxygen transmissibility is very important. Accordingly, research and development of materials having excellent oxygen permeability have been actively conducted in order to improve oxygen permeability of contact lenses, an example of which is a prepolymer containing silicon. Although hydrogel contact lenses made using the prepolymer have been developed, not only problems with lens deposits and wettability, but also oxygen transmission rates are often lower than corneal oxygen demand.

The present invention for solving the above problems is to provide a high performance hydrogel contact lens excellent in oxygen transmittance and light transmittance.

The present invention for achieving the above object is (a) polyphosphazene substituted with a vinyl group (polyphosphazene), (b) 2-hydroxy ethylmethacrylate (HEMA), (c) N-vinyl It provides a high-performance hydrogel contact lens comprising a polymer obtained by copolymerizing -pyrrolidone (N-vinyl-pyrrolidone, NVP) and (d) ethylene glycol dimethacrylate (EGDMA).

The high-performance hydrogel contact lens of the present invention has good light transmittance and oxygen transmittance, so that it is possible to reduce dryness and redness of eyes, and thus it is suitable for long time wearing.

The present invention relates to a high-performance hydrogel contact lens, (a) polyphosphazene substituted with a vinyl group, (b) 2-hydroxy ethylmethacrylate (HEMA), (c) N It relates to a high-performance hydrogel contact lens comprising a polymer obtained by copolymerizing -vinyl-pyrrolidone (NVP) and (d) ethylene glycol dimethacrylate (EGDMA).

Preferably, the polymer comprises (a) 1 to 20% by weight of polyphosphazine substituted by vinyl group, (b) 59 to 93% by weight of 2-hydroxyethyl methacrylate (HEMA), (c) N-vinyl-pi It is characterized by copolymerizing 4 to 20% by weight of ralidone (NVP) and 0.1 to 0.5% by weight of (d) ethylene glycol dimethacrylate (EGDMA).

Hereinafter, with reference to the preferred production examples, experimental examples of the present invention will be described in detail. The following preparation examples and experimental examples are only presented to understand the contents of the present invention, and those skilled in the art will be capable of many modifications within the technical spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited to these preparation examples, experimental examples.

Preparation Example 1 Polyphosphazine Substituted with a Vinyl Group and 2-Hydroxyethyl Methacrylate

(a) 10 g (0.086 mol) of polyphosphazine substituted with vinyl group and 100 mL of DMSO were placed in a 250 mL Schlenk flask to completely dissolve the polyphosphazine substituted with (a) vinyl group. Then, as shown in FIG. 1, 30 mL of hydrogel type (b) 2-hydroxyethyl methacrylate (HEMA) was slowly added to the Schlenk flask in a low temperature and argon atmosphere using a drop funnel. Dropwise and stirred for one day. When the reaction is carried out in a low temperature atmosphere as described above, since the reaction proceeds slowly, the yield of the product can be increased, and the reactivity of the product with the reaction by-product HCl can be reduced.

Next, the solution obtained from the reaction was removed using impurities with a filter, and the solution was lyophilized under reduced pressure and concentrated to about 10 mL. The concentrated solution was then polymer extracted using 400 mL of acetone. Thereafter, the resultant was dried with a vacuum filter to obtain a polyphosphazine substituted with a vinyl group and 2-hydroxyethyl methacrylate. In order to confirm the chemical structure of the polyphosphazine substituted with 2-hydroxyethyl methacrylate, the ¹ H-NMR spectrum was measured using a Bruker AC-300 MHz spectrometer, which is shown in FIG. 2.

The process for preparing polyphosphazine substituted with vinyl group and 2-hydroxyethyl methacrylate using (a) polyphosphazine substituted with vinyl group and (b) 2-hydroxy ethyl methacrylate (HEMA) It is represented by Reaction Scheme 1 below.

<Scheme 1>

<Manufacture example 2>: High-performance hydrogel contact lens

The high performance hydrogel contact lens of the present invention was prepared by cast molding using a vinyl group obtained from Preparation Example 1 and polyphosphazine substituted with 2-hydroxyethyl methacrylate.

First, (c) N-vinyl-pyrrolidone (NVP) and (d) ethylene glycol dimethacrylate (EGDMA) were mixed with a polyphosphazine substituted with a vinyl group and 2-hydroxyethyl methacrylate. And hold at 70 ° C. for 40 minutes. Thereafter, the hydrogel contact lens was completed through a copolymerization step of heating at 80 ° C. for 40 minutes and performing heat treatment at 100 ° C. for 40 minutes.

Except that (a) polyphosphazine substituted with a vinyl group, (b) 2-hydroxyethyl methacrylate (HEMA), (c) N-vinyl-pyrrolidone (NVP) and (d) ethylene glycol dimetha Four hydrogel contact lenses (P1, P2, P3, and P4) were prepared by varying the composition ratio of acrylate (EGDMA), and the composition ratios are shown in Table 1 below.

TABLE 1

Polyphosphazine substituted with vinyl group HEMA  NVP EGDMA P1 1.96 wt% 92.65 wt% 4.90 wt% 0.49 wt% P2 4.76 wt% 90.00 wt% 4.76 wt% 0.48 wt% P3 6.54 wt% 88.32 wt% 4.67% by weight 0.47 wt% P4 9.09 wt% 85.91% by weight 4.55 wt% 0.45 wt%

Experimental Example 1 Effect of High Performance Hydrogel Contact Lens

In order to confirm the effects of the high-performance hydrogel contact lenses of P1, P2, P3, and P4 of Preparation Example 2, water content, optical transmittence, and oxygen transmittance were measured.

The measurement of the water content (%) was performed in a high-performance hydrogel contact lens of P1, P2, P3, P4 of Preparation Example 2 in 0.9% sodium chloride (NaCl) physiological saline for 24 hours, followed by gravimetric method of ISO 18369-4. Was measured. The light transmittance (%) was measured using the TM-2 of TOPCON in the visible light region (380 ~ 720 nm). The oxygen transmission rate (Dk / t) was measured by O ₂ permeometer 201T of Rdhder development company. In order to increase the accuracy of the measurement, the measurement was repeated three times, and the average of the measured values is shown in Table 2 below.

TABLE 2

Moisture content (%) Light transmittance (%) Oxygen transmittance (Dk / t) P1 35.45 89 52 P2 32.21 89 79 P3 30.89 88 90 P4 28.00 89 101

From the results of Table 2, it can be seen that the high-performance hydrogel contact lens of the present invention is excellent as a contact lens because it has an oxygen transmittance and a water content of about 30%. In addition, the high-performance hydrogel contact lens of the present invention has good light transmittance and oxygen transmittance, so that it is possible to reduce dryness and redness of eyes, which is suitable for wearing for a long time.

The present invention has been described above in connection with specific embodiments of the present invention, but this is only an example and the present invention is not limited thereto. Those skilled in the art can change or modify the described embodiments without departing from the scope of the invention, and such changes or modifications are within the scope of the invention. In addition, the materials of each component described herein can be readily selected and substituted for various materials known to those skilled in the art. Those skilled in the art will also appreciate that some of the components described herein can be omitted without degrading performance or adding components to improve performance. In addition, those skilled in the art may change the order of the method steps described herein depending on the process environment or equipment. Therefore, the scope of the present invention should be determined not by the embodiments described, but by the claims and their equivalents.

1 shows the experimental apparatus used in Preparation Example 1 to prepare polyphosphazine substituted with a vinyl group and 2-hydroxyethyl methacrylate.

Figure 2 shows the 1H-NMR spectrum of polyphosphazine substituted with 2-hydroxyethyl methacrylate of Preparation Example 1.

Claims (2)

delete 1-20 wt% of polyphosphazene substituted by vinyl group, 59-93 wt% of 2-hydroxy ethylmethacrylate, N-vinyl-pyrrolidone 4 to 20% by weight, ethylene glycol dimethacrylate (ethylene glycol dimethacrylate) is a high-performance hydrogel contact lens, characterized in that copolymerized.

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