KR20200089843A - Hydrogel Contact Lens with MPC - Google Patents

Hydrogel Contact Lens with MPC Download PDF

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KR20200089843A
KR20200089843A KR1020190006584A KR20190006584A KR20200089843A KR 20200089843 A KR20200089843 A KR 20200089843A KR 1020190006584 A KR1020190006584 A KR 1020190006584A KR 20190006584 A KR20190006584 A KR 20190006584A KR 20200089843 A KR20200089843 A KR 20200089843A
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contact lens
biocompatible material
mpc
weight
hydrogel contact
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KR1020190006584A
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Korean (ko)
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천성철
주지웅
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뉴바이오 (주)
천성철
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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/26Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/28Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F226/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F226/06Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
    • C08F226/10N-Vinyl-pyrrolidone
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F230/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
    • C08F230/04Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
    • C08F230/08Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/49Phosphorus-containing compounds
    • C08K5/51Phosphorus bound to oxygen
    • C08K5/52Phosphorus bound to oxygen only
    • C08K5/521Esters of phosphoric acids, e.g. of H3PO4
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041Lenses
    • G02B1/043Contact lenses
    • GPHYSICS
    • G02OPTICS
    • G02CSPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C7/00Optical parts
    • G02C7/02Lenses; Lens systems ; Methods of designing lenses
    • G02C7/04Contact lenses for the eyes

Abstract

The present invention relates to a silicone hydrogel contact lens composition which includes a hydrophilic terpolymer and a biocompatible material and shows an improved oxygen transmission rate and wettability and increased bio-affinity. The silicone hydrogel contact lens composition includes 70-90 wt% of 2-hydroxyethyl methacrylate (HEMA), 0.1-10 wt% of N-vinylpyrrolidone, 0.1-5 wt% of ethylene glycol dimethacrylate (EGDMA), 0.1-20 wt% of a biocompatible material (methacryloyloxyethyl phosphoryl choline, MPC), and 5-20 wt% of silicon monomer.

Description

생체적합소재를 포함하는 실리콘 하이드로겔 콘택트렌즈 조성물{Hydrogel Contact Lens with MPC}Silicone hydrogel contact lens composition containing biocompatible material {Hydrogel Contact Lens with MPC}

본 발명은 친수성 터폴리머와 생체적합소재가 포함되게 조성되어 산소투과율 및 습윤성을 향상시킴은 물론 생체친화성을 높여줄 수 있는 생체적합소재를 포함하는 실리콘 하이드로겔 콘택트렌즈 조성물에 관한 것이다.The present invention relates to a silicone hydrogel contact lens composition comprising a biocompatible material capable of improving the oxygen permeability and wettability, as well as improving the oxygen permeability and wettability by being formed to include a hydrophilic terpolymer and a biocompatible material.

일반적으로 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 충족하여야 한다.In general, contact lenses have suitable mechanical strength, bio compatibility, nontoxicity, optical transparency, refractive index, surface wettability, and moisture content suitable for the cornea. Requirements such as (water content), swelling, oxygen transmissibility, and flexibility must be satisfied.

특히, 콘택트렌즈의 장기착용에서 유발되는 안과적 질환의 문제점과 부작용을 고려하면, 상기 산소투과성(oxygen transmissibility)의 요건은 매우 중요하다.In particular, considering the problems and side effects of ophthalmic diseases caused by long-term wearing of contact lenses, the requirement of oxygen transmissibility is very important.

따라서, 콘택트렌즈의 산소투과성의 향상을 위하여 산소투과성이 우수한 재질의 연구 및 개발이 활발하게 진행되고 있으며, 그 일례가 실리콘이 포함된 프리폴리머(prepolymer)이다.Therefore, in order to improve the oxygen permeability of the contact lens, research and development of materials having excellent oxygen permeability have been actively conducted, and an example thereof is a prepolymer containing silicon.

상기 프리폴리머(prepolymer)를 응용하여 제조된 렌즈와 관련된 기술로서, 한국 등록특허 제10-0901806호에 "광학렌즈 성형용 폴리우레탄 수지 조성물 및 내충격성 합성수지 렌즈"가 개시되어 있다.As a technology related to a lens manufactured by applying the prepolymer, Korean Patent Registration No. 10-0901806 discloses a “polyurethane resin composition for forming an optical lens and an impact resistant synthetic resin lens”.

상기 특허는 2이상의 이소시아네이트기를 가진 치환족 폴리이소시아네이트와 2이상의 수산기를 가진 폴리올을 반응시켜 얻어진 프리폴리머, 내부 이형제, 및 Gardner 색수 2 이하로 정제된 4,4'-메틸렌비스(2-클로로아닐린)을 필수성분으로 포함하는 것이다.The patent discloses a prepolymer obtained by reacting a substituted polyisocyanate having two or more isocyanate groups with a polyol having two or more hydroxyl groups, an internal release agent, and 4,4'-methylenebis (2-chloroaniline) purified to a Gardner color number of 2 or less. It is included as an essential ingredient.

하지만, 이러한 플리폴리머(prepolymer)를 응용하여 만든 렌즈는, 렌지 침착물과 습윤성(濕潤性)의 문제점이 있을 뿐만 아니라, 산소투과율이 각막 산소 요구율에 미치지 못하여 사용자에게 불편함을 초래하는 문제점이 있었다.However, a lens made by applying such a prepolymer has a problem in that it not only has a problem of stove deposits and wettability, but also has an oxygen permeability that does not reach the corneal oxygen demand, causing inconvenience to the user. .

한편, 생체적합소재는 생체에 넣어 두어도 부작용을 일으키지 않는 인공장기의 재료이며, 그 중 MPC(2-Methacryloyloxyethyl Phosphoryl Choline)는 세포막과 비슷한 분자구조를 갖는 물질로서 생체조직에 접촉할 경우에도 거부반응이 없고 보습기능도 뛰어나 인공관절 등의 의료용 소재와 화장품 기능개선을 위한 첨가제로 사용되고 있다.On the other hand, biocompatible materials are materials for artificial organs that do not cause side effects even when placed in a living body. Among them, MPC (2-Methacryloyloxyethyl Phosphoryl Choline) is a substance having a molecular structure similar to a cell membrane, and rejects reactions even when it comes into contact with living tissue. It has no moisturizing function and is used as an additive for improving the functional properties of cosmetics and medical materials such as artificial joints.

이러한 생체적합소재는 의료용 소재나 화장품 첨가제에 주로 사용되고 있으나, 본 발명의 콘택트렌즈 분야에는 적용되어 사용된 바가 없다.These biocompatible materials are mainly used for medical materials or cosmetic additives, but have not been applied and used in the contact lens field of the present invention.

대한민국 등록특허공보 제10-1863823호(2018. 5. 28., 공중합된 친수성 터폴리머와 실리콘을 포함한 하이드로겔 콘택트렌즈 조성물)Republic of Korea Patent Registration No. 10-1863823 (May 28, 2018, hydrogel contact lens composition containing a copolymerized hydrophilic terpolymer and silicone) 대한민국 공개특허공보 제10-2010-0111149호(2010. 10. 14., 비닐기로 치환된 포스파진을 포함한 고기능 하이드로젤 콘택트렌즈)Republic of Korea Patent Publication No. 10-2010-0111149 (2010. 10. 14., high-performance hydrogel contact lenses containing phosphazine substituted with vinyl groups) 대한민국 등록특허공보 제10-1123644호(2012. 2. 28., 이산화티타늄을 포함하는 콘택트렌즈 및 이의 제조방법)Republic of Korea Registered Patent Publication No. 10-1123644 (February 28, 2012, contact lenses containing titanium dioxide and manufacturing method thereof) 대한민국 등록특허공보 제10-0346485호(2002. 7. 16., 초임계유체를이용한콘택트렌즈의처리방법)Republic of Korea Patent Registration No. 10-0346485 (July 16, 2002, treatment method of contact lenses using supercritical fluid)

본 발명은 상기한 문제점을 해결하기 위한 것으로, 본 발명의 목적은 친수성 터폴리머와 생체적합소재를 포함시켜 조성함으로써 산소투과율과 습윤성이 우수한 실리콘 하이드로겔 콘택트렌즈 조성물을 제공함에 있다.The present invention is to solve the above problems, the object of the present invention is to provide a silicone hydrogel contact lens composition excellent in oxygen permeability and wettability by incorporating a hydrophilic terpolymer and a biocompatible material.

상기의 목적을 달성하기 위한 생체적합소재를 포함하는 실리콘 하이드로겔 콘택트렌즈 조성물은, 2-하이드록시에틸메타크릴레이트(HEMA: 2-hydroxyethylmethacrylate) 70 ~ 90중량%, N-비닐 피로리돈(NVP: N-vinylpyrrolidone) 0.1 ~ 10중량%, 에틸렌글리콜 디메타크릴레이트(EGDMA: ethylene glycol dimethylacrylate) 0.1 ~ 5중량%, 생체적합소재(MPC: methacryloyloxyethyl phosphoryl choline) 0.1 ~ 20중량%, 실리콘 단량체 5 ~ 20중량%로 조성된다.Silicone hydrogel contact lens composition comprising a biocompatible material for achieving the above object, 2-hydroxyethyl methacrylate (HEMA: 2-hydroxyethylmethacrylate) 70 ~ 90% by weight, N-vinyl pyridone (NVP: N-vinylpyrrolidone) 0.1 ~ 10% by weight, ethylene glycol dimethylacrylate (EGDMA) 0.1 ~ 5% by weight, biocompatible material (MPC: methacryloyloxyethyl phosphoryl choline) 0.1 ~ 20% by weight, silicone monomer 5 ~ 20 It is composed of weight percent.

이때, 상기 실리콘 단량체는 아래의 [화학식1]로 이루어진다.At this time, the silicone monomer is composed of [Formula 1] below.

[화학식 1][Formula 1]

Figure pat00001
Figure pat00001

상기와 같은 구성으로 이루어진 생체적합소재를 포함하는 실리콘 하이드로겔 콘택트렌즈 조성물에 따르면, 산소투과율과 습윤성이 우수하여 착용감이 좋음은 물론 눈의 건조감을 줄일 수 있어 안구질환 감소효과 및 장시간 착용이 가능하게 되고, 생체적합성 소재(MPC)를 사용함에 따라 단백질 흡착을 방지함은 물론 생체친화력의 향상으로 안구질환 예방 등 인체 부작용을 최소화하여 사용시 안정성을 높여줄 수 있는 효과가 있다.According to the composition of the silicone hydrogel contact lens comprising a biocompatible material having the above-described configuration, the oxygen permeability and wettability are excellent, so that it is comfortable to wear as well as to reduce the dryness of the eye, so that it can reduce eye diseases and wear for a long time. In addition, the use of biocompatible materials (MPC) prevents protein adsorption and improves biocompatibility, thereby minimizing human side effects such as prevention of eye diseases, thereby improving stability when used.

도 1은 본 발명에 따른 생체적합소재의 첨가량에 따른 함수율 그래프,
도 2는 본 발명에 따른 생체적합소재의 첨가량에 따른 마찰계수(MIU) 그래프,
도 3은 본 발명에 따른 생체적합소재의 첨가량에 따른 마찰계수 평균값(MMD) 그래프,
도 4는 본 발명에 따른 생체적합소재의 첨가량에 따른 습윤각 그래프,
도 5는 본 발명에 따른 생체적합소재의 첨가량에 따른 단백질 흡착량 그래프.
1 is a graph of water content according to the amount of the biocompatible material according to the present invention,
2 is a friction coefficient (MIU) graph according to the amount of the biocompatible material according to the present invention,
Figure 3 is a friction coefficient average value (MMD) graph according to the amount of the biocompatible material according to the present invention,
Figure 4 is a wetting angle graph according to the amount of the biocompatible material according to the present invention,
5 is a graph of the amount of protein adsorption according to the amount of the biocompatible material according to the present invention.

이하, 첨부된 도면을 참조하여 본 발명의 생체적합소재를 포함하는 실리콘 하이드로겔 콘택트렌즈 조성물에 대하여 상세히 설명하기로 한다.Hereinafter, a silicone hydrogel contact lens composition including the biocompatible material of the present invention will be described in detail with reference to the accompanying drawings.

본 발명의 생체적합소재를 포함하는 실리콘 하이드로겔 콘택트렌즈 조성물은 2-하이드록시에틸메타크릴레이트(HEMA: 2-hydroxyethylmethacrylate) 70 ~ 90중량%, N-비닐 피로리돈(NVP: N-vinylpyrrolidone) 0.1 ~ 10중량%, 에틸렌글리콜 디메타크릴레이트(EGDMA: ethylene glycol dimethylacrylate) 0.1 ~ 5중량%, 생체적합소재(MPC: methacryloyloxyethyl phosphoryl choline) 0.1 ~ 20중량%, 실리콘 단량체 5 ~ 20중량%로 조성된다.The silicone hydrogel contact lens composition comprising the biocompatible material of the present invention is 2-hydroxyethylmethacrylate (HEMA) 70 to 90% by weight, N-vinyl pyridone (NVP: N-vinylpyrrolidone) 0.1 ~ 10% by weight, ethylene glycol dimethacrylate (EGDMA: ethylene glycol dimethylacrylate) 0.1 ~ 5% by weight, biocompatible material (MPC: methacryloyloxyethyl phosphoryl choline) 0.1 ~ 20% by weight, silicone monomer 5 ~ 20% by weight .

상기 2-하이드록시에틸 메타크릴레이트(HEMA: 2-hydroxyethyl methacrylate)는 친수성 아크릴계 단량체이며, 입체규칙성을 갖는 고분자의 일종으로 단량체 기반의 가교 결합을 한다.The 2-hydroxyethyl methacrylate (HEMA) is a hydrophilic acrylic monomer and is a type of polymer having stereoregularity, and is crosslinked based on monomers.

상기 N-비닐 피로리돈(NVP: N-vinyl pyrrolidone)은 보통 'NVP'라고 명명하는 것으로 친수성 단량체로서의 기질을 띤다.The N-vinyl pyrrolidone (NVP) is commonly referred to as'NVP' and has a substrate as a hydrophilic monomer.

상기 N-비닐 피로리돈은 분자구조가 생체와 유사하고, 부분적으로 양전하를 띠기 때문에 물과 결합하려는 성질이 있어 친수성이며, 소프트콘택트렌즈의 함수율을 증가시키거나 경성렌즈의 습윤성을 증가시키는 목적으로 사용된다.The N-vinyl pyridone is hydrophilic because it has a molecular structure similar to that of a living body and is partially positively charged, so it is hydrophilic and used for the purpose of increasing the moisture content of soft contact lenses or increasing the wettability of hard lenses. do.

여기서, 상기 NVP는 총 조성물의 함량 중 0.1중량% 내지 20중량%가 함유될 수 있는데, 20중량% 이하에서는 투과도가 90% 이상의 투명한 렌즈를 얻을 수 있고 50% 이상의 함수율 특성을 보이나, 20중량%를 초과할 경우에는 불투명한 렌즈가 얻어지게 되고 더 많이 첨가된 경우에는 렌즈의 형상을 유지하지 못하고 물에 녹게 된다.Here, the NVP may contain from 0.1% to 20% by weight of the total composition content. Below 20% by weight, a transparent lens having a transmittance of 90% or more can be obtained, and water content of 50% or more is exhibited, but 20% by weight When it exceeds, an opaque lens is obtained, and when added more, the shape of the lens is not maintained and is dissolved in water.

상기 에틸렌글리콜 디메타크릴레이트(EGDMA: ethylene glycol dimethylacrylate)는 각 성분을 합성하는 가교제로 사용되는 것이며, 중합체의 안정과 강도를 향상시키고 함수율을 낮추는 역할을 한다.The ethylene glycol dimethacrylate (EGDMA: ethylene glycol dimethylacrylate) is used as a crosslinking agent to synthesize each component, and improves the stability and strength of the polymer and lowers the water content.

구체적으로 상기 소재는 사슬 모양 고분자 사슬 사이에서 가교 역할을 하게 되며, 수지에 경도나 탄력성 등 기계적 강도와 화학적 안정성을 부여한다.Specifically, the material acts as a bridge between chain-shaped polymer chains and imparts mechanical strength and chemical stability, such as hardness or elasticity, to the resin.

상기 EGDMA는 총 조성물의 함량 중 0.1 ~ 5중량%가 함유될 수 있다. 상기 EGDMA의 함량이 낮을수록 높은 투과성의 렌즈를 제조할 수 있게 되며, 5중량%를 초과할 경우에는 고분자의 합성이 과도하게 일어나 단량체가 경직될 수 있으며 불투명화된다.The EGDMA may contain 0.1 to 5% by weight of the total composition content. The lower the content of the EGDMA, the higher the permeability of the lens can be produced, and if it exceeds 5% by weight, the synthesis of the polymer may occur excessively, resulting in stiffening of the monomer and opacity.

따라서, 상기 NVP의 함량을 높여주면서 EGDMA의 함량을 줄여주도록 조성함이 바람직할 것이다.Therefore, it would be desirable to increase the content of NVP while reducing the content of EGDMA.

한편, 본 발명에서는 콘택트렌즈 조성물에 생체적합소재가 더 혼합되어 조성된다.Meanwhile, in the present invention, a biocompatible material is further mixed into the contact lens composition.

생체적합소재로서 MPC(methacryloyloxyethyl Phosphoryl Choline)가 사용된다.As a biocompatible material, MPC (methacryloyloxyethyl phosphoryl choline) is used.

상기 MPC는 인체의 세포막을 구성하고 있는 인지질(Phospholipid)의 포스포릴콜린 (phosphorylcholine)과 동일한 구조를 가지고 있으며, 메타크릴(methacrylate) 작용기를 가지고 있어 고분자로의 반응이 가능한 생체친화성 단량체 물질이다.The MPC has a structure identical to that of phosphorylcholine of phospholipids constituting the cell membrane of the human body, and is a biocompatible monomer material capable of reacting with a polymer because it has a methacrylate functional group.

상기 MPC는 혈전 생성 억제 효과가 있으며, 단백질 흡착 억제 및 탁월한 세포 흡착 성능이 있다. 그리고 우수한 보습효과는 물론 인체 부작용을 최소화하는 효과가 있다.The MPC has an effect of inhibiting thrombus production, and has protein adsorption inhibition and excellent cell adsorption performance. And it has the effect of minimizing human side effects as well as excellent moisturizing effect.

인지질(Phospholipid) 분자는 단백질보다는 MPC 고분자 표면에 우선적으로 흡착되어 표면을 완전히 덮게 되며, 표면상의 인지질 분자는 자기 조립 특성에 의해 생체막과 같은 조직화된 구조를 형성하고, 표면에서의 단백질 흡착 및 전개를 방지하게 된다.Phospholipid molecules preferentially adsorb on the surface of the MPC polymer rather than proteins to completely cover the surface, and phospholipid molecules on the surface form a structured structure such as a biomembrane by self-assembly properties, and adsorb and develop proteins on the surface. Will be prevented.

상기 실리콘 단량체는 친수성 실리콘 단량체를 사용하였다.As the silicone monomer, a hydrophilic silicone monomer was used.

실리콘 단량체는 총 조성물의 함량 중 5 ~ 20중량%가 혼합되어 지는 것으로, 20중량%를 초과하게 되면 상분리가 쉽게 일어나 산란으로 인해 렌즈의 투과도가 감소되어 불투명한 렌즈를 얻게 된다.The silicone monomer is a mixture of 5 to 20% by weight of the total composition content, and when it exceeds 20% by weight, phase separation easily occurs and the transmittance of the lens is reduced due to scattering, thereby obtaining an opaque lens.

본 발명의 실리콘 단량체는 히드록실기를 함유하여 친수성을 높여준 단량체로서, 화학적 구조식은 아래와 같다.The silicone monomer of the present invention is a monomer containing a hydroxyl group to increase hydrophilicity, and the chemical structural formula is as follows.

Figure pat00002
Figure pat00002

아래에서는 상기 MPC의 혼합량에 따라 제조된 콘택트렌즈의 함수율, 마찰계수(MIU), 마찰계수 평균값(MMD), 습윤각, 단백질 흡착량에 대해 살펴본다.Below, the moisture content, friction coefficient (MIU), friction coefficient average value (MMD), wetting angle, and protein adsorption amount of the contact lens prepared according to the mixing amount of the MPC will be described.

제조된 콘택트 렌즈를 수용액에서 1~12시간 침지하여 불순물을 제거한 수 테스트를 진행하였다. The prepared contact lens was immersed in an aqueous solution for 1 to 12 hours to test the number of impurities removed.

하이드로겔 필름(콘택트렌즈)는 100℃에서 4시간 건조하고, 건조된 실리카겔이 있는 데시케이터에서 실온으로 냉각하고, 무게를 측정하였다(W1). 그리고 건조된 하이드로겔 필름을 이온수에 12시간 침지하여 함습된 하이드로겔 필름을 준비하였다. 표면에 남아있는 물기를 깨끗한 티슈를 이용하여 제거하고, 무게를 측정하였다.(W2)The hydrogel film (contact lens) was dried at 100°C for 4 hours, cooled to room temperature in a desiccator with dried silica gel, and weighed (W1). Then, the dried hydrogel film was immersed in ionic water for 12 hours to prepare a wet hydrogel film. Water remaining on the surface was removed using a clean tissue and weighed. (W2)

함수율 (% )= (W2-W1) / W1 X 100 Water content (% )= (W2-W1) / W1 X 100

도 1은 콘택트렌즈의 함수율을 보여준 그래프로서, MPC의 함량이 증가할수록 콘택트렌즈로 사용되는 하이드로겔 필름의 함수율이 증가됨을 확인할 수 있었다. 1 is a graph showing the moisture content of the contact lens, it was confirmed that as the content of MPC increases, the water content of the hydrogel film used as the contact lens increases.

다음 콘택트렌즈의 착용시 발생되는 마찰력에 대해 테스트를 진행하였다.Next, the friction force generated when the contact lens was worn was tested.

건조된 하이드로겔 필름을 이온수에 12시간 침지하여 습윤시켰다. 습윤된 하이드로겔 표면에 남아있는 물기를 제거하고, 마찰력측정기(KES-SE, Kato Tech. Japan)를 이용하여 마찰계수(MIU) 와 마찰계수 평균값( MMD)을 측정하였다.The dried hydrogel film was immersed in ionic water for 12 hours to wet it. The moisture remaining on the wet hydrogel surface was removed, and the friction coefficient (MIU) and the average friction coefficient (MMD) were measured using a friction force meter (KES-SE, Kato Tech. Japan).

측정결과는 도 2와 도 3에 각각 도시되어 있다. 도시된 그래프에서와 같이 MPC의 함량이 증가할수록 마찰계수(MIU)와 마찰계수 평균값(MMD)이 감소하여 표면마찰력이 감소함을 확인할 수 있었다.The measurement results are shown in FIGS. 2 and 3, respectively. As shown in the graph, as the content of MPC increases, the friction coefficient (MIU) and the average value of the friction coefficient (MMD) decrease, and it can be seen that the surface friction force decreases.

따라서, 콘택트 렌즈로의 형성시 착용감 증진효과를 예측할 수 있다.Therefore, it is possible to predict the effect of enhancing the wearing feeling when forming into a contact lens.

다음 습윤각을 측정하였다.Next wetting angle was measured.

0.1 ~ 20중량%의MPC를 함유한 콘택트렌즈를 100℃에서 구부러짐에 주의하면서 3시간 건조하였다.The contact lens containing 0.1 to 20% by weight of MPC was dried for 3 hours, paying attention to bending at 100°C.

건조된 콘택트렌즈를 평평한 표면에 양면테이프를 이용하여 부착하고, 50㎕의 물방울을 가하고, 10분, 20분 후에 각각의 습윤각을 측정하였으며, 측정결과는 도 4와 같다.The dried contact lens was attached to a flat surface using double-sided tape, 50 μl of water was added, and each wetting angle was measured after 10 minutes and 20 minutes, and the measurement results are shown in FIG. 4.

도 5는 본 발명에 따른 생체적합소재의 첨가량에 따른 단백질 흡착량을 보여주는 그래프이다.5 is a graph showing the amount of protein adsorption according to the amount of the biocompatible material according to the present invention.

시험방법은 소재 배합에 따른 콘택트렌즈를 제조하여 그 표면에 Bovine serum albumin을 흡착시키고, Micro BCA Protein Assay Kit 과 Plate reader를 이용하여 렌즈 표면에 흡착된 단백질을 정량하였다. As a test method, a contact lens according to the material formulation was prepared to adsorb Bovine serum albumin on the surface, and the protein adsorbed on the lens surface was quantified using a Micro BCA Protein Assay Kit and a plate reader.

도 5에서와 같이, MPC의 함량에 따른 단백질 흡착량을 보면 MPC의 함량이 증가할수록 콘택트렌즈 표면의 단백질 흡착량이 감소한 것으로 나타났으며, 이는 콘택트렌즈 표면의 단백질 비흡착성이 증가하였음을 알 수 있다.As shown in FIG. 5, when looking at the amount of protein adsorption according to the content of MPC, it was found that the amount of protein adsorption on the surface of the contact lens decreased as the content of MPC increased. .

상기와 같이 조성된 본 발명의 콘택트렌즈 조성물로 제조된 콘택트렌즈는 우수한 산소투과율로 인해 콘택트렌즈의 착용시 눈의 건조감 및 충혈을 줄여줄 수 있게 되는 것이고, 앞서 설명한 바와 같이 생체적합소재가 혼합됨에 따라 생체친화력의 향상으로 부작용을 최소화하면서도 안구질환 등 질병발생을 방지할 수 있는 효과를 기대할 수 있다.Since the contact lens made of the contact lens composition of the present invention composed as described above can reduce dryness and redness of the eyes when wearing the contact lens due to excellent oxygen permeability, and the biocompatible material is mixed as described above Accordingly, it is possible to expect an effect of preventing diseases such as ocular diseases while minimizing side effects by improving biocompatibility.

Claims (2)

2-하이드록시에틸메타크릴레이트(HEMA: 2-hydroxyethylmethacrylate) 70 ~ 90중량%, N-비닐 피로리돈(NVP: N-vinylpyrrolidone) 0.1 ~ 10중량%, 에틸렌글리콜 디메타크릴레이트(EGDMA: ethylene glycol dimethylacrylate) 0.1 ~ 5중량%, 생체적합소재(MPC: methacryloyloxyethyl phosphoryl choline) 0.1 ~ 20중량%, 실리콘 단량체 5 ~ 20중량%로 조성된 것을 특징으로 하는 생체적합소재를 포함하는 실리콘 하이드로겔 콘택트렌즈 조성물.
2-hydroxyethylmethacrylate (HEMA) 70 to 90% by weight, N-vinylpyrrolidone (NVP) 0.1 to 10% by weight, ethylene glycol dimethacrylate (EGDMA: ethylene glycol dimethylacrylate) 0.1 to 5% by weight, biocompatible material (MPC: methacryloyloxyethyl phosphoryl choline) 0.1 to 20% by weight, silicone monomer 5 to 20% by weight of a silicone hydrogel contact lens composition comprising a biocompatible material .
제1항에 있어서,
상기 실리콘 단량체는 아래의 [화학식1]로 이루어진 것을 특징으로 하는 생체적합소재를 포함하는 실리콘 하이드로겔 콘택트렌즈 조성물.
[화학식 1]
Figure pat00003

According to claim 1,
The silicone monomer is a silicone hydrogel contact lens composition comprising a biocompatible material, characterized in that consisting of the following [Formula 1].
[Formula 1]
Figure pat00003

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100346485B1 (en) 1994-01-31 2002-11-30 바슈 앤드 롬 인코포레이티드 Treatment Method of Contact Lens Using Supercritical Fluid
KR20100111149A (en) 2009-04-06 2010-10-14 성아영 Hydrogel contact lens with high performance comprising vinyl group substituted phophazene
KR101123644B1 (en) 2010-01-13 2012-03-20 뉴바이오 (주) Contact lens comprising titanium dioxide and preparation method thereof
KR101863823B1 (en) 2016-12-29 2018-06-01 뉴바이오(주) Hydrogel contact lenses composition, including copolymerized hydrophilic terpolymers and silicones

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100346485B1 (en) 1994-01-31 2002-11-30 바슈 앤드 롬 인코포레이티드 Treatment Method of Contact Lens Using Supercritical Fluid
KR20100111149A (en) 2009-04-06 2010-10-14 성아영 Hydrogel contact lens with high performance comprising vinyl group substituted phophazene
KR101123644B1 (en) 2010-01-13 2012-03-20 뉴바이오 (주) Contact lens comprising titanium dioxide and preparation method thereof
KR101863823B1 (en) 2016-12-29 2018-06-01 뉴바이오(주) Hydrogel contact lenses composition, including copolymerized hydrophilic terpolymers and silicones

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