KR20100111149A - Hydrogel contact lens with high performance comprising vinyl group substituted phophazene - Google Patents
Hydrogel contact lens with high performance comprising vinyl group substituted phophazene Download PDFInfo
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- KR20100111149A KR20100111149A KR1020090029567A KR20090029567A KR20100111149A KR 20100111149 A KR20100111149 A KR 20100111149A KR 1020090029567 A KR1020090029567 A KR 1020090029567A KR 20090029567 A KR20090029567 A KR 20090029567A KR 20100111149 A KR20100111149 A KR 20100111149A
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- G—PHYSICS
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- G02C7/00—Optical parts
- G02C7/02—Lenses; Lens systems ; Methods of designing lenses
- G02C7/04—Contact lenses for the eyes
- G02C7/049—Contact lenses having special fitting or structural features achieved by special materials or material structures
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- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C7/00—Optical parts
- G02C7/02—Lenses; Lens systems ; Methods of designing lenses
- G02C7/04—Contact lenses for the eyes
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Abstract
Description
본원발명은 광투과율 및 산소투과율이 높은 고기능 하이드로젤 콘택트렌즈에 관한 것이다.The present invention relates to a high performance hydrogel contact lens having a high light transmittance and high oxygen transmittance.
콘택트렌즈는 적당한 기계적 강도 (tensile strength), 생체적합성 (bio compatibility), 무독성(toxicity), 재료의 투명도(optical transparent), 굴절률(refractive index), 표면 친수성(surface wettability), 각막에 적합한 함수율(water content), 팽윤비(swelling), 산소투과성(oxygen transmissibility), 유연성(flexibility) 등의 요구조건을 충족시켜야 한다. 특히, 콘택트렌즈의 장기착용에서 유발되는 안과적 문제점과 부작용을 고려하면, 상기 산소투과성(oxygen transmissibility)의 요건은 매우 중요하다. 따라서, 콘택트렌즈의 산소투과성의 향상을 위하여 산소투과성이 우수한 재질의 연구 및 개발이 활발하게 진행되고 있 으며, 그 일례가 실리콘이 포함된 프리폴리머(prepolymer)이다. 상기 프리폴리머를 사용하여 만든 하이드로젤 콘택트렌즈(hydrogel contact lens)가 개발되었으나, 렌즈 침착물과 습윤성의 문제점이 있을 뿐만 아니라, 산소투과율이 각막 산소 요구율에 미치지 못하는 경우도 많다.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.
상기의 문제점을 해결하기 위한 본원발명은 산소투과율 및 광투과율이 우수한 고기능 하이드로젤 콘택트렌즈를 제공하고자 한다.The present invention for solving the above problems is to provide a high performance hydrogel contact lens excellent in oxygen transmittance and light transmittance.
상기의 목적을 달성하기 위한 본원발명은 (a) 비닐기로 치환된 폴리포스파진(polyphosphazene), (b) 2-하이드록시에틸메타크릴레이트(2-hydroxy ethylmethacrylate, HEMA), (c) N-비닐-피롤리돈(N-vinyl-pyrrolidone, NVP) 및 (d) 에틸렌 글리콜 디메타크릴레이트(ethylene glycol dimethacrylate, EGDMA)를 공중합하여 얻은 중합체를 포함하는 고기능 하이드로젤 콘택트렌즈를 제공한다.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).
본원발명의 고기능 하이드로젤 콘택트렌즈는 광투과율 및 산소투과율이 좋기 때문에 눈의 건조감 및 충혈을 줄여줄 수 있어서 장시간동안 착용하기에 적합하다.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.
본원발명은 고기능 하이드로젤 콘택트렌즈에 관한 것으로서, (a) 비닐기로 치환된 폴리포스파진(polyphosphazene), (b) 2-하이드록시에틸메타크릴레이트(2-hydroxy ethylmethacrylate, HEMA), (c) N-비닐-피롤리돈(N-vinyl-pyrrolidone, NVP) 및 (d) 에틸렌 글리콜 디메타크릴레이트(ethylene glycol dimethacrylate, EGDMA)를 공중합하여 얻은 중합체를 포함하는 고기능 하이드로젤 콘택트렌즈에 관한 것이다.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).
바람직하게, 상기 중합체는 (a) 비닐기로 치환된 폴리포스파진 1 ~ 20 중량%, (b) 2-하이드록시에틸메타크릴레이트(HEMA) 59 ~ 93 중량%, (c) N-비닐-피롤리돈(NVP) 4 ~ 20 중량%, (d) 에틸렌 글리콜 디메타크릴레이트(EGDMA) 0.1 ~ 0.5 중량%를 공중합한 것을 특징으로 한다.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).
이하에서, 본원발명의 바람직한 제조예, 실험예를 참조하여 상세히 설명한다. 아래의 제조예, 실험예는 본원발명의 내용을 이해하기 위해 제시된 것일 뿐이며 당해 분야에서 통상의 지식을 가진 자라면 본원발명의 기술적 사상 내에서 많은 변형이 가능할 것이다. 따라서 본원발명의 권리범위가 이러한 제조예, 실험예에 한정되는 것으로 해석되어서는 안 된다.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.
<제조예 1> : 비닐기 및 2-히드록시에틸 메타크릴레이트로 치환된 폴리포스파진Preparation Example 1 Polyphosphazine Substituted with a Vinyl Group and 2-Hydroxyethyl Methacrylate
(a) 비닐기로 치환된 폴리포스파진 10 g(0.086 mol) 및 DMSO 100 mL를 250 mL 슈렝크 플라스크에 넣고 상기 (a) 비닐기로 치환된 폴리포스파진를 완전히 용해시켰다. 그 후, 도 1에 나타낸 바와 같이, 하이드로젤 타입의 (b) 2-하이드록시에틸메타크릴레이트(HEMA) 30 mL를 깔때기(drop funnel)를 이용하여 저온 및 아르곤 분위기에서 상기 슈렝크 플라스크에 천천히 드롭와이즈(dropwise)하고 하루동안 교반시켰다. 이와 같이 저온 분위기에서 반응을 시키면 반응이 천천히 진행되므로 생성물의 수득률을 증가시킬 수 있고, 반응 부산물인 HCl 과 생성물의 반응성을 줄일 수 있다.(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.
다음으로, 상기 반응으로부터 얻은 용액을 필터를 사용하여 불순물을 제거하고 감압 하에 상기 용액을 동결건조하여 10 mL 정도로 농축하였다. 그 후, 아세톤 400 mL를 이용하여 상기 농축된 용액을 고분자 추출(extraction)하였다. 그 후 감압여과기로 건조하여 비닐기 및 2-히드록시에틸 메타크릴레이트로 치환된 폴리포스파진을 얻었다. 상기 2-히드록시에틸 메타크릴레이트로 치환된 폴리포스파진의 화학적 구조를 확인하기 위하여 브루커 AC-300 MHz 스펙트로미터를 이용하여 1H- NMR spectrum을 측정하였고, 이는 도 2에 나타냈다.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.
(a) 비닐기로 치환된 폴리포스파진 및 (b) 2-히드록시 에틸 메타크릴레이트(HEMA)를 이용하여 비닐기 및 2-히드록시에틸 메타크릴레이트로 치환된 폴리포스파진을 제조하는 과정은 하기의 반응식 1로 나타냈다.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.
<반응식 1> 
<제조예 2> : 고기능 하이드로젤 콘택트렌즈<Manufacture example 2>: High-performance hydrogel contact lens
상기 제조예 1로부터 얻은 비닐기 및 2-히드록시에틸 메타크릴레이트로 치환된 폴리포스파진을 이용하여 캐스트 몰드법(cast mould)에 의해 본원발명의 고기능 하이드로젤 콘택트렌즈를 제조하였다.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.
우선, 비닐기 및 2-히드록시에틸 메타크릴레이트로 치환된 폴리포스파진 에 (c) N-비닐-피롤리돈(NVP) 및 (d) 에틸렌 글리콜 디메타크릴레이트(EGDMA)를 혼합하여 몰드에 주입시키고 70 ℃에서 40분 동안 유지한다. 그 후, 80 ℃에서 40분 동안 가열하고, 100 ℃에서 40분 동안 열처리하는 공중합 하는 단계를 거쳐서 하이드로겔 콘택트렌즈를 완성하였다.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.
다만, (a) 비닐기로 치환된 폴리포스파진, (b) 2-하이드록시에틸메타크릴레 이트(HEMA), (c) N-비닐-피롤리돈(NVP) 및 (d) 에틸렌 글리콜 디메타크릴레이트(EGDMA)의 조성비를 달리하여 4개의 하이드로겔 콘택트렌즈(P1, P2, P3, P4)를 제조하였고, 그 조성비는 하기의 표 1에 나타냈다.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.
[표 1]TABLE 1
<실험예 1> : 고기능 하이드로젤 콘택트렌즈의 효과Experimental Example 1 Effect of High Performance Hydrogel Contact Lens
상기 제조예 2의 P1, P2, P3, P4 의 고기능 하이드로젤 콘택트렌즈의 효과를 확인하기 위하여 함수율(Water content), 광투과율(Optical transmittence) 및 산소투과율(Oxygen transmittance)을 측정하였다.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.
상기 함수율의 측정(%)은 제조예 2의 P1, P2, P3, P4 의 고기능 하이드로젤 콘택트렌즈는 0.9% 염화나트륨(NaCl) 생리 식염수에 24시간동안 함수시킨 후, ISO 18369-4의 gravimetric method 에 의해 측정하였다. 상기 광투과율(%)은 가시광선 영역(380 ~ 720 nm)에서 TOPCON의 TM-2를 이용하여 측정하였다. 상기 산소투과율(Dk/t)은 Rdhder development company의 O2 permeometer 201T 로 측정하였다. 측정의 정확도를 높이기 위하여 각각 3번씩 반복측정하고, 측정한 값의 평균을 하기의 표 2에 나타냈다.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.
[표 2]TABLE 2
상기의 표 2의 결과로부터, 본원발명의 고기능 하이드로젤 콘택트렌즈는 산소투과율이 뛰어나면서 약 30% 정도의 함수율을 가지기 때문에 콘택트렌즈로서 우수하다는 것을 알 수 알 수 있다. 또한, 본원발명의 고기능 하이드로젤 콘택트렌즈는 광투과율 및 산소투과율이 좋기 때문에 눈의 건조감 및 충혈을 줄여줄 수 있어서 장시간동안 착용하기에 적합하다.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.
이상 본원발명의 구체적 실시형태와 관련하여 본원발명을 설명하였으나 이는 예시에 불과하며 본원발명은 이에 제한되지 않는다. 당업자는 본원발명의 범위를 벗어나지 않고 설명된 실시형태를 변경 또는 변형할 수 있으며, 이러한 변경 또는 변형도 본원발명의 범위에 속한다. 또한, 본 명세서에서 설명한 각 구성요소의 물질은 당업자가 공지된 다양한 물질로부터 용이하게 선택하여 대체할 수 있다. 또한 당업자는 본 명세서에서 설명된 구성요소 중 일부를 성능의 열화 없이 생략하거나 성능을 개선하기 위해 구성요소를 추가할 수 있다. 뿐만 아니라, 당업자는 공정 환경이나 장비에 따라 본 명세서에서 설명한 방법 단계의 순서를 변경할 수도 있다. 따라서 본원발명의 범위는 설명된 실시형태가 아니라 특허청구범위 및 그 균등물에 의해 결정되어야 한다.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.
도 1은 비닐기 및 2-히드록시에틸 메타크릴레이트로 치환된 폴리포스파진을 제조하기 위하여 제조예 1에서 사용한 실험기구를 나타낸다.1 shows the experimental apparatus used in Preparation Example 1 to prepare polyphosphazine substituted with a vinyl group and 2-hydroxyethyl methacrylate.
도 2는 제조예 1의 2-히드록시에틸 메타크릴레이트로 치환된 폴리포스파진의 1H- NMR spectrum 을 나타낸다.Figure 2 shows the 1H-NMR spectrum of polyphosphazine substituted with 2-hydroxyethyl methacrylate of Preparation Example 1.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020090029567A KR101044955B1 (en) | 2009-04-06 | 2009-04-06 | Hydrogel Contact Lens with High Performance Comprising Vinyl Group Substituted Phophazene |
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| KR1020090029567A KR101044955B1 (en) | 2009-04-06 | 2009-04-06 | Hydrogel Contact Lens with High Performance Comprising Vinyl Group Substituted Phophazene |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101237489B1 (en) * | 2010-12-20 | 2013-02-26 | 뉴바이오 (주) | Contact lens comprising vinylphenylboronic acid and manufacturing method thereof |
| KR20200089843A (en) | 2019-01-18 | 2020-07-28 | 뉴바이오 (주) | Hydrogel Contact Lens with MPC |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3715309B1 (en) * | 2004-05-24 | 2005-11-09 | 株式会社資生堂 | Ophthalmic lens material and manufacturing method thereof |
| US7300464B2 (en) * | 2004-09-30 | 2007-11-27 | Alcon, Inc. | Intraocular lens |
| KR100741611B1 (en) * | 2006-06-21 | 2007-07-23 | 성아영 | Urethane contact lens containing silicone and method thereof |
| KR101231181B1 (en) * | 2007-06-25 | 2013-02-07 | 남택인 | Silicone-hydrogel compound for soft contact lens and soft contact lens produced using the compound |
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2009
- 2009-04-06 KR KR1020090029567A patent/KR101044955B1/en active IP Right Grant
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101237489B1 (en) * | 2010-12-20 | 2013-02-26 | 뉴바이오 (주) | Contact lens comprising vinylphenylboronic acid and manufacturing method thereof |
| KR20200089843A (en) | 2019-01-18 | 2020-07-28 | 뉴바이오 (주) | Hydrogel Contact Lens with MPC |
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| Publication number | Publication date |
|---|---|
| KR101044955B1 (en) | 2011-06-29 |
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