KR102232954B1 - Manufacturing method of high wettablility and antimicrobial contact lens using carrageenan - Google Patents
Manufacturing method of high wettablility and antimicrobial contact lens using carrageenan Download PDFInfo
- Publication number
- KR102232954B1 KR102232954B1 KR1020200010310A KR20200010310A KR102232954B1 KR 102232954 B1 KR102232954 B1 KR 102232954B1 KR 1020200010310 A KR1020200010310 A KR 1020200010310A KR 20200010310 A KR20200010310 A KR 20200010310A KR 102232954 B1 KR102232954 B1 KR 102232954B1
- Authority
- KR
- South Korea
- Prior art keywords
- carrageenan
- contact lens
- weight
- ipn
- polymer
- Prior art date
Links
Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D11/00—Producing optical elements, e.g. lenses or prisms
- B29D11/00009—Production of simple or compound lenses
- B29D11/00038—Production of contact lenses
- B29D11/00067—Hydrating contact lenses
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D11/00—Producing optical elements, e.g. lenses or prisms
- B29D11/00009—Production of simple or compound lenses
- B29D11/00038—Production of contact lenses
- B29D11/00125—Auxiliary operations, e.g. removing oxygen from the mould, conveying moulds from a storage to the production line in an inert atmosphere
- B29D11/0025—Removing impurities from contact lenses, e.g. leaching
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers 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
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—Copolymers 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
- C08F226/06—Copolymers 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
- C08F226/10—N-Vinyl-pyrrolidone
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers 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
- C08F230/02—Copolymers 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 phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29L—INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES
- B29L2011/00—Optical elements, e.g. lenses, prisms
- B29L2011/0016—Lenses
- B29L2011/0041—Contact lenses
Abstract
Description
본 발명은 해조다당류인 카라기난을 상호침투고분자네트워크(Interpenetrating polymer network, IPN) 방법으로 하이드로겔 콘택트렌즈에 네트워크시키는 제조방법에 관한 것으로, 카라기난의 결합으로 고습윤성, 단백질 저부착, 그리고 항균성을 가지는 콘택트렌즈 제조방법에 관한 것이다.The present invention relates to a manufacturing method in which carrageenan, a seaweed polysaccharide, is networked to a hydrogel contact lens by an interpenetrating polymer network (IPN) method, and a contact having high wettability, low protein adhesion, and antimicrobial properties due to the binding of carrageenan It relates to a method of manufacturing a lens.
최근 들어 여러 환경적인 요인으로 안구건조증을 가진 사람이 많이 증가되고 있다. 안구건조증은 눈의 불편함, 시각장애, 눈물막 불안정, 그리고 안구표면의 염증 및 손상을 유발한다. 종래의 콘택트렌즈는 착용감을 향상시키기 위하여 고함수율을 지향하고 있으나 고함수율 콘택트렌즈는 안구건조인에게는 오히려 증상을 악화시키기 때문에 고함수율의 콘택트렌즈보다 고습윤성 콘택트렌즈가 눈 건강에 더 좋다. 그리고 콘택트렌즈는 착용과 세척 등의 관리소홀로 각막염 등 안질환을 유발할 수 있다. 단백질과 같은 침전물의 침착으로 인해 거대 유두 각막증과 같은 안질환을 유발하여 문제가 제기되었다. 습윤성이 좋은 콘택트렌즈는 단백질 침착이 적으며 착용감과 건조함과 같은 문제점들을 감소시켜준다.Recently, the number of people with dry eye syndrome is increasing due to various environmental factors. Dry eye syndrome causes eye discomfort, visual impairment, tear film instability, and inflammation and damage to the ocular surface. Conventional contact lenses aim for a high moisture content in order to improve the fit, but a high moisture content contact lens rather worsens the symptoms for the dry eye, so a high wettability contact lens is better for eye health than a high moisture content contact lens. In addition, contact lenses can cause eye diseases such as keratitis due to negligence of wearing and washing. The problem has been raised by causing eye diseases such as giant papillary keratosis due to the deposition of protein-like deposits. Contact lenses with good wettability have less protein deposition and reduce problems such as fit and dryness.
눈 건강을 지키면서 콘택트렌즈를 착용하기 위해서는 습윤성, 산소투과성이 좋으며 단백질 등의 침착물이 적은 콘택트렌즈가 필요하다. 특히 오늘날과 같은 미세먼지 및 환경오염물이 많은 대기로부터 눈을 보호하기 위한 생체적합한 항균 기능이 겸비된 고기능성 콘택트렌즈의 필요성이 대두된다. 안구가 건조한 경우, 눈물 속의 단백질이 콘택트렌즈에 많이 부착되어 이차적인 문제를 야기시키기도 한다.In order to wear contact lenses while maintaining eye health, contact lenses with good wettability and oxygen permeability and less deposits such as proteins are required. In particular, there is a need for high-functional contact lenses with biocompatible antibacterial functions to protect eyes from today's atmosphere with a lot of fine dust and environmental pollutants. When the eyeballs are dry, the protein in the tears adheres a lot to the contact lenses, causing secondary problems.
따라서 일례로서 종래기술인 등록특허공보 등록번호 10-1994668호에는 히알루론산나트륨을 알칼리로 전처리하고 초음파로 분쇄한 다음 양이온교환수지를 통과시켜서 얻어진 생성물을 하이드록실에틸메타아크릴레이트 용액에 희석시켜서 제조되고 히알루론산이 0.01-5.0 중량% 함유된 히알루론산-하이드록시에틸메타아크릴레이트(HA-HEMA) 50.0중량%-99.6중량%와, 글리세롤모노메타아크릴레이트(GMMA) 0.1-40중량%, N-비닐피롤리돈(NVP) 0.1-30 중량%, 가교제로 에틸렌 글리콜 다이 메타크릴레이트 0.1-1.0중량% 및 개시제로 2,2-아조비스(2,4-다이메칠바레로니트릴) 0.1-1.0 중량%를 포함하는 하이드로겔 콘택트렌즈 제조용 조성물로 이루어지고, 상기 조성물의 가교중합으로 생성된 IPN (Interpenetrating Polymer Network) 내부구조를 가지며, 인장강도가 3.0-13.0 kg/㎠이고, 함수율 38-65%이며, 습윤각이 15∼40°인 물성을 가진 것을 특징으로 하는 습윤성 하이드로겔 콘택트렌즈가 공개되어 있다.Therefore, as an example, in the prior art Registration No. 10-1994668, the product obtained by pretreating sodium hyaluronate with alkali, pulverizing with ultrasonic waves, and passing through a cation exchange resin, is prepared by diluting the product in a hydroxylethyl methacrylate solution. Hyaluronic acid-hydroxyethyl methacrylate (HA-HEMA) 50.0 wt%-99.6 wt% containing 0.01-5.0 wt% of uronic acid, glycerol monomethacrylate (GMMA) 0.1-40 wt%, N-vinyl pi 0.1-30% by weight of rolidone (NVP), 0.1-1.0% by weight of ethylene glycol dimethacrylate as a crosslinking agent, and 0.1-1.0% by weight of 2,2-azobis (2,4-dimethylvareronitrile) as an initiator It consists of a composition for manufacturing a hydrogel contact lens containing, has an IPN (Interpenetrating Polymer Network) internal structure produced by crosslinking polymerization of the composition, has a tensile strength of 3.0-13.0 kg/㎠, a moisture content of 38-65%, and wetness A wettable hydrogel contact lens, characterized in that it has physical properties with an angle of 15 to 40°, has been disclosed.
또한, 등록특허공보 등록번호 10-1677960호에는 습윤성 포스파릴콜린(PC ; phosphorylcholine) 중합체로 형성되는 포스파릴콜린 제1코팅층과; 상기 포스파릴콜린 제1코팅층 표면에 하이드록시에틸메타크릴레이트(HEMA ; 2-hydroxyethyl methacrylate) 중합체로 형성되는 HEMA코팅층과; 상기 HEMA코팅층 표면에 인쇄되는 인쇄층과; 상기 인쇄층 표면에 형성되는 하이드록시에틸메타크릴레이트(HEMA ; 2-hydroxyethyl methacrylate) 중합체로 형성되는 렌즈성형층;을 포함하여 이루어지는 것을 특징으로 하는 친수성 하이드록시에틸메타크릴레이트와 습윤성 포스파릴콜린(HEMA-PC)으로 구성된 다층코팅층이 형성된 콘택트렌즈가 공개되어 있다.In addition, Patent Publication No. 10-1677960 discloses a phosphorylcholine first coating layer formed of a wett phosphorylcholine (PC) polymer; A HEMA coating layer formed of a hydroxyethyl methacrylate (HEMA) polymer on the surface of the phosphorylcholine first coating layer; A printing layer printed on the surface of the HEMA coating layer; A lens forming layer formed of a hydroxyethyl methacrylate (HEMA; 2-hydroxyethyl methacrylate) polymer formed on the surface of the printing layer; hydrophilic hydroxyethyl methacrylate and wettable phospharylcholine ( HEMA-PC) is a contact lens in which a multi-layered coating layer is formed.
그러나 상기 종래기술들은 산소투과도성, 착용감, 습윤성이 낮고 단백질 부착저하성도 충분하지 않은 문제점이 여전히 남아 있었다.However, the prior art still has a problem in that the oxygen permeability, the fit, the wettability are low, and the protein adhesion deterioration is not sufficient.
따라서 본 발명은 상기와 같은 문제점을 해결하고자 안출된 것으로, 안구건조증을 가진 사람들에게 가장 필요한 콘택트렌즈의 기능인 고습윤성, 항균성, 그리고 단백질 부착저하 문제를 해결하기 위하여 해조류인 카라기난을 렌즈중합체에 포함시키는 것을 특징으로 한다.Therefore, the present invention was conceived to solve the above problems, and in order to solve the problems of high wettability, antibacterial properties, and protein adhesion, which are the functions of contact lenses most necessary for people with dry eye syndrome, carrageenan, a seaweed, is included in the lens polymer. It is characterized by that.
콘택트렌즈 제작은 하이드로겔의 주 재료인 2-Hydroxyethyl methacrylate(HEMA)와 함수율과 습윤성을 높이기 위해 2-Methacryloyloxyethyl phosphorylcholine(MPC), N-vinylpyrrolidone(NVP)을 사용하며, 개시제인 Azobisisobutyronitrile(AIBN)와 교차결합제 Ethylene glycol dimethacrylate(EGDMA)를 첨가하여 혼합한 후 캐스팅 몰드법으로 100℃에서 1시간 동안 열중합한다. 일차적으로 중합된 콘택트렌즈에 semi-IPN과 full-IPN 방법으로 카라기난 용액을 제조하여 사용한다. 카라기난을 이용한 semi-IPN 방법은 개시제인 APS를 사용하였으며 full-IPN은 개시제 Ammonium persulfate(APS)와 가교제인 N,N'-Methylenebisacrylamide(MBAA)를 첨가하여 제작한다. IPN을 실시한 시간은 37℃에서 1일에서 28일까지 진행 가능하다.Contact lenses are manufactured using 2-Hydroxyethyl methacrylate (HEMA), which is the main material of hydrogel, and 2-Methacryloyloxyethyl phosphorylcholine (MPC), and N-vinylpyrrolidone (NVP) to increase moisture content and wettability. After mixing by adding the binder Ethylene glycol dimethacrylate (EGDMA), thermal polymerization is performed at 100°C for 1 hour using a casting mold method. A carrageenan solution is prepared and used by the semi-IPN and full-IPN methods in the firstly polymerized contact lens. The semi-IPN method using carrageenan used APS, an initiator, and full-IPN was prepared by adding the initiator Ammonium persulfate (APS) and the crosslinking agent N,N'-Methylenebisacrylamide (MBAA). IPN can be performed from 1 to 28 days at 37°C.
카라기난은 황산기의 수와 치환된 위치에 따라 k-카라기난, ι-카라기난, λ-카라기난으로 3종류가 존재하며 본 발명에 사용되는 카라기난은 3종 모두 사용 가능하다. 콘택트렌즈에 적용하는 카라기난은 황산기가 가장 적고 젤성이 가장 높은 k-카라기난이 가장 좋은 성능을 가진다.There are three types of carrageenan, k-carrageenan, ι-carrageenan, and λ-carrageenan, depending on the number of sulfuric acid groups and the substituted position, and all three types of carrageenan used in the present invention can be used. In carrageenan applied to contact lenses, k-carrageenan, which has the least sulfuric acid group and the highest gelability, has the best performance.
따라서 본 발명에 의해 제조된 콘택트렌즈은 하이드로겔 콘택트렌즈에 카라기난을 이용한 IPN으로 카라기난콘택트렌즈를 제조하여 고습윤성, 고산소투과성, 단백질부착저하, 그리고 고항균성을 가지는 현저한 효과가 있다.Therefore, the contact lens manufactured according to the present invention has a remarkable effect having high wettability, high oxygen permeability, protein adhesion reduction, and high antibacterial properties by preparing a carrageenan contact lens with IPN using carrageenan in a hydrogel contact lens.
도 1은 본 발명인 하이드로겔 콘택트렌즈에 카라기난을 첨가하기 위한 IPN 방법과 시간에 따른 접촉각을 나타낸 그래프
도 2은 본 발명인 하이드로겔 콘택트렌즈에 카라기난을 첨가하기 위한 IPN 방법과 시간에 따른 산소투과도를 나타낸 그래프
도 3은 본 발명인 하이드로겔 콘택트렌즈에 카라기난을 첨가하기 위한 IPN 방법과 시간에 따른 단백질 흡착양을 나타낸 그래프
도 4은 본 발명인 하이드로겔 콘택트렌즈에 카라기난을 첨가하여 대조군과 비교한 항균성 그래프1 is a graph showing a contact angle over time and an IPN method for adding carrageenan to a hydrogel contact lens of the present invention
Figure 2 is a graph showing the oxygen permeability over time and the IPN method for adding carrageenan to the hydrogel contact lens of the present invention
Figure 3 is a graph showing the amount of protein adsorption over time and the IPN method for adding carrageenan to the hydrogel contact lens of the present invention
Figure 4 is a graph of antimicrobial activity compared with a control group by adding carrageenan to a hydrogel contact lens of the present invention
본발명은 카라기난을 이용한 고 습윤성 및 항균성 콘택트렌즈 제조방법에 관한 것으로, 용기에 기본시료를 혼합하여 균질화한 다음 캐스트 몰드(cast mold)에 주입하여 열중합하는 1단계;The present invention relates to a method for manufacturing a high wettability and antimicrobial contact lens using carrageenan, comprising: a first step of mixing and homogenizing a basic sample in a container and then injecting it into a cast mold for thermal polymerization;
중합체를 캐스트 몰드에서 꺼내어 초순수로 미반응된 물질을 제거하며 수화시키는 2단계;A second step of removing the polymer from the cast mold, removing unreacted material with ultrapure water, and hydrating;
상기 중합체를 카라기난이 포함된 IPN 용액에 침지시키는 3단계;3 step of immersing the polymer in an IPN solution containing carrageenan;
렌즈 표면에 붙은 미반응 물질을 증류수로 세척하여 콘택트렌즈를 제조하는 5단계;를 포함하는 것을 특징으로 한다.It characterized in that it comprises a; 5 step of manufacturing a contact lens by washing the unreacted material attached to the surface of the lens with distilled water.
또한, 상기 기본시료는 2-hydroxyethyl methacrylate(HEMA), 2-Methacryloyloxyethyl phosphorylcholine(MPC), N-Vinyl-2-pyrrolidone(NVP) 등의 친수성 단량체에 교차결합제 N,N'-Methylenebisacrylamide(MBAA), Ethylene glycol dimethacrylate(EGDMA) 그리고 개시제 Azobisisobutyronitrile(AIBN), Ammonium persulfate(APS)를 포함하는 것을 특징으로 한다.In addition, the basic sample is a crosslinking agent N,N'-Methylenebisacrylamide (MBAA), Ethylene in hydrophilic monomers such as 2-hydroxyethyl methacrylate (HEMA), 2-Methacryloyloxyethyl phosphorylcholine (MPC), and N-Vinyl-2-pyrrolidone (NVP). It is characterized by including glycol dimethacrylate (EGDMA) and the initiator Azobisisobutyronitrile (AIBN), Ammonium persulfate (APS).
또한, 상기 열중합 시간은 1시간인 것을 특징으로 한다.In addition, the thermal polymerization time is characterized in that 1 hour.
본 발명을 첨부도면에 의해 상세히 설명하면 다음과 같다.The present invention will be described in detail with reference to the accompanying drawings as follows.
도 1은 본 발명인 하이드로겔 콘택트렌즈에 카라기난을 첨가하기 위한 IPN 방법과 시간에 따른 접촉각을 나타낸 그래프, 도 2은 본 발명인 하이드로겔 콘택트렌즈에 카라기난을 첨가하기 위한 IPN 방법과 시간에 따른 산소투과도를 나타낸 그래프, 도 3은 본 발명인 하이드로겔 콘택트렌즈에 카라기난을 첨가하기 위한 IPN 방법과 시간에 따른 단백질 흡착양을 나타낸 그래프, 도 4은 본 발명인 하이드로겔 콘택트렌즈에 카라기난을 첨가하여 대조군과 비교한 항균성 그래프이다.1 is a graph showing an IPN method for adding carrageenan to a hydrogel contact lens of the present invention and a contact angle over time. FIG. 2 is a graph showing an IPN method for adding carrageenan to a hydrogel contact lens of the present invention and oxygen permeability over time. The graph shown, Figure 3 is a graph showing the amount of protein adsorption over time and the IPN method for adding carrageenan to the hydrogel contact lens of the present invention, and Figure 4 is antimicrobial activity compared with the control group by adding carrageenan to the hydrogel contact lens of the present invention. It is a graph.
카라기난(carrageenan)은 적색 해조류에서 추출한 다당류이며 수용성으로 겔을 형성하고 항균성과 보습성이 우수한 생체적합성 황산화 폴리갈락탄이다. 카라기난은 고분자물질로서 콘택트렌즈 단량체와의 섞임성이 낮아서 콘택트렌즈 제조를 위해서는 상호침투고분자네트워크 방법을 사용하여야 한다.Carrageenan is a polysaccharide extracted from red seaweed and is a biocompatible sulfated polygalactan that is water-soluble and forms a gel and has excellent antibacterial properties and moisturizing properties. Since carrageenan is a high molecular substance and has low miscibility with contact lens monomers, an interpenetrating polymer network method must be used to manufacture contact lenses.
상호침투 고분자 네트워크(IPN)은 고분자를 혼합하는 고분자 블렌드의 한 형태로써 2개 이상의 네트워크를 포함하는 중합체로 하나의 네트워크 구조에 속한 고분자 사슬이 물리적으로 다른 네트워크와 서로 얽혀 있어 각 네트워크 구조의 분리가 어려운 고분자 혼합구조이다. IPN은 고분자의 새로운 물리화학적 특성을 보여주며 네트워크 특성은 중합체의 유형 및 농도, 가교결합방법 및 이들의 제조에 사용된 전체 절차에 따라 달라질 수 있다. IPN과정에 교차결합제와 개시제를 넣어주는 full-IPN과 개시제만 넣어주는 semi-IPN으로 구분되며, 교차결합 반응에 따라 순차적 IPN과 동시적 IPN으로 구분되기도 한다.Interpenetrating polymer network (IPN) is a type of polymer blend that mixes polymers. It is a polymer containing two or more networks. The polymer chains in one network structure are physically entangled with other networks, so that each network structure can be separated. It is a difficult polymer mixed structure. IPN reveals new physicochemical properties of polymers, and network properties can vary depending on the type and concentration of the polymer, the crosslinking method, and the overall procedure used to prepare them. The IPN process is divided into full-IPN, which puts a cross-linking agent and an initiator, and semi-IPN, which puts only the initiator, and may be divided into sequential IPNs and simultaneous IPNs according to the cross-linking reaction.
본 발명은 카라기난을 이용하여 semi-IPN과 full-IPN 두 가지 방법이 가능하며 IPN 시간은 1일부터 28일까지 가능하다.In the present invention, two methods of semi-IPN and full-IPN are possible using carrageenan, and the IPN time is available from 1 day to 28 days.
카라기난(carrageenan)은 적색 해조류에서 추출한 다당류이며 수용성으로 겔을 형성하고 생체적합성을 가지며 15~40%의 ester sulfate 함량과 100kDa 이상의 평균 분자량을 갖는 황산화 폴리갈락탄이다. 이의 중합체 사슬은 a-1,3- 및 
본 발명은 카라기난을 이용한 고습윤성 및 항균성 콘택트렌즈 제조방법에 관한 것으로, 하이드로겔 콘택트렌즈를 제조하기 위하여 2-hydroxyethyl methacrylate(HEMA), 2-Methacryloyloxyethyl phosphorylcholine(MPC), N-Vinyl-2-pyrrolidone(NVP) 등의 친수성 단량체에 교차결합제 N,N'-Methylenebisacrylamide(MBAA), Ethylene glycol dimethacrylate(EGDMA) 그리고 개시제 Azobisisobutyronitrile(AIBN), Ammonium persulfate(APS) 등을 사용하여 하이드로겔 콘택트렌즈를 제조하고 카라기난을 이용한다.The present invention relates to a method for manufacturing a highly wettable and antibacterial contact lens using carrageenan, and in order to manufacture a hydrogel contact lens, 2-hydroxyethyl methacrylate (HEMA), 2-Methacryloyloxyethyl phosphorylcholine (MPC), N-Vinyl-2-pyrrolidone ( NVP), a crosslinking agent N,N'-Methylenebisacrylamide (MBAA), Ethylene glycol dimethacrylate (EGDMA), an initiator Azobisisobutyronitrile (AIBN), Ammonium persulfate (APS), etc., to prepare a hydrogel contact lens, and carrageenan. Use.
제조방법은 용기에 기본시료를 혼합하여 균질화한 다음 캐스트 몰드(cast mold)에 주입하여 80 ~ 115℃에서 1시간 열중합한다. 최적온도는 100℃이다. 중합체를 캐스트 몰드에서 꺼내어 초순수로 미반응된 물질을 제거하며 수화시킨다. 상기 중합체를 카라기난이 포함된 IPN 용액에 37도에서 침지시킨다. 렌즈 표면에 붙은 미반응 물질을 증류수로 세척하여 콘택트렌즈를 제조하는 것이다.The manufacturing method is to mix a basic sample in a container, homogenize it, inject it into a cast mold, and heat cure at 80 ~ 115℃ for 1 hour. The optimum temperature is 100°C. The polymer is removed from the cast mold and hydrated with ultrapure water to remove unreacted material. The polymer was immersed in an IPN solution containing carrageenan at 37 degrees. A contact lens is manufactured by washing the unreacted material attached to the surface of the lens with distilled water.
실시 예:Example:
본 발명에 사용되는 카라기난이 첨가된 하이드로겔 콘택트렌즈 제조에 사용된 모노머와 비율은 다음과 같다.The monomers and ratios used in manufacturing the hydrogel contact lens to which carrageenan used in the present invention is added are as follows.
본 발명의 혼합비는 중량비로 HEMA 80중량부에 대하여, MPC 2 ~ 20중량부, NVP 2 ~ 20 중량부, EGDMA 0.1 ~ 3중량부, AIBN 0.05 ~ 1중량부의 비율로 만들어진다. 또한 카라기난이 포함된 IPN용액은 증류수 86 ~ 99.35중량%, 카라기난 0.5중량%, MBAA 0.1중량%, APS 0.05 중량%의 비율이다.The mixing ratio of the present invention is made in a ratio of 2 to 20 parts by weight of MPC, 2 to 20 parts by weight of NVP, 0.1 to 3 parts by weight of EGDMA, and 0.05 to 1 parts by weight of AIBN, based on 80 parts by weight of HEMA by weight. In addition, the IPN solution containing carrageenan is a ratio of 86 to 99.35% by weight of distilled water, 0.5% by weight of carrageenan, 0.1% by weight of MBAA, and 0.05% by weight of APS.
카라기난은 젤성이 강하기 때문에 고농도로 취급이 어려우며 콘택트렌즈에 적용 가능한 범위는 0.5중량% ~ 2중량% 범위이다.Since carrageenan has strong gel properties, it is difficult to handle at a high concentration, and the range applicable to contact lenses is in the range of 0.5% by weight to 2% by weight.
IPN 방법은 semi-IPN과 full-IPN 둘 다 사용 가능하며 IPN시간은 1일에서 28일까지 가능하다. IPN방법과 시간에 따라 콘택트렌즈의 성능에 차이가 발생한다.The IPN method can be used for both semi-IPN and full-IPN, and the IPN time is available from 1 day to 28 days. Depending on the IPN method and time, there is a difference in the performance of the contact lens.
본 발명은 카라기난으로 IPN 시간이 경과될수록 렌즈의 습윤성(도 1), 산소투과성(도 2)이 향상되고, 단백질 흡착량(도 3)이 저하되어 콘택트렌즈의 성능이 향상된다. 습윤성은 접촉각으로 확인 가능하며 접촉각의 값이 낮을수록 습윤성이 좋다.In the present invention, as the IPN time elapses with carrageenan, the wettability of the lens (FIG. 1) and oxygen permeability (FIG. 2) improve, and the amount of protein adsorption (FIG. 3) decreases, thereby improving the performance of the contact lens. The wettability can be checked by the contact angle, and the lower the value of the contact angle, the better the wettability.
상기 중합체는 IPN방법에 따른 성능차이를 나타낸다. 즉, 습윤성은 full-IPN(점선)이 semi-IPN(실선)보다 향상성이 좋아지며 산소투과율은 초반에는 방법에 따른 차이가 거의 없다가 7일 이후에는 semi-IPN 하였을 때에 향상성이 더 좋아진다.The polymer shows a difference in performance according to the IPN method. That is, the wettability of full-IPN (dotted line) improves better than semi-IPN (solid line), and the oxygen permeability has little difference depending on the method at the beginning, but the improvement is better when semi-IPN is used after 7 days. Lose.
본 발명 카라기난 콘택트렌즈의 항균성은 IPN 실시 1일 경과 후에 대장균을 이용하여 24시간 배양하여 시험한 것으로 대조군에 비해 현저한 항균효과가 있다.The antimicrobial properties of the carrageenan contact lenses of the present invention were tested by culturing for 24 hours using E. coli 1 day after the IPN implementation, and had a remarkable antibacterial effect compared to the control group.
Claims (3)
중합체를 캐스트 몰드에서 꺼내어 초순수로 미반응된 물질을 제거하며 수화시키는 2단계;
상기 중합체를 카라기난이 포함된 IPN 용액에 침지시키는 3단계;
렌즈 표면에 붙은 미반응 물질을 증류수로 세척하여 콘택트렌즈를 제조하는 5단계;를 포함하는 카라기난을 이용한 고 습윤성 및 항균성 콘택트렌즈 제조방법에 있어서,
상기 용기에 기본시료를 혼합하여 균질화한 다음 캐스트 몰드(cast mold)에 주입하여 80 ~ 115℃에서 1시간 열중합한 후, 중합체를 캐스트 몰드에서 꺼내어 초순수로 미반응된 물질을 제거하며 수화시킨 후, 상기 중합체를 카라기난이 포함된 IPN 용액에 37℃에서 침지시킨 후, 렌즈 표면에 붙은 미반응 물질을 증류수로 세척하여 콘택트렌즈를 제조하는 것으로,
콘택트렌즈 원료혼합비는 중량비로 HEMA 80중량부에 대하여, MPC 2 ~ 20중량부, NVP 2 ~ 20 중량부, EGDMA 0.1 ~ 3중량부, AIBN 0.05 ~ 1중량부의 비율로 만들어지되, 카라기난이 포함된 IPN용액은 증류수 86 ~ 99.35중량%, 카라기난 0.5중량%, MBAA 0.1중량%, APS 0.05중량%의 비율이며, IPN시간은 1일에서 28일까지인 것을 특징으로 하는 카라기난을 이용한 고 습윤성 및 항균성 콘택트렌즈 제조방법A first step of mixing and homogenizing a basic sample in a container and then injecting it into a cast mold for thermal polymerization;
A second step of removing the polymer from the cast mold, removing unreacted material with ultrapure water, and hydrating;
3 step of immersing the polymer in an IPN solution containing carrageenan;
In the method for manufacturing a contact lens with high wettability and antimicrobial properties using carrageenan comprising;
After mixing and homogenizing the basic sample in the container, it is injected into a cast mold and thermally polymerized at 80 to 115°C for 1 hour, and then the polymer is taken out of the cast mold to remove unreacted substances with ultrapure water and hydrated. After immersing the polymer in an IPN solution containing carrageenan at 37°C, the unreacted material adhering to the lens surface is washed with distilled water to prepare a contact lens,
The contact lens raw material mixing ratio is made in a ratio of 2 to 20 parts by weight of MPC, 2 to 20 parts by weight of NVP, 0.1 to 3 parts by weight of EGDMA, 0.05 to 1 part by weight of AIBN, based on 80 parts by weight of HEMA in weight ratio, but contains carrageenan. IPN solution is a ratio of 86 to 99.35% by weight of distilled water, 0.5% by weight of carrageenan, 0.1% by weight of MBAA, and 0.05% by weight of APS, and the IPN time is from 1 day to 28 days. Lens manufacturing method
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020200010310A KR102232954B1 (en) | 2020-01-29 | 2020-01-29 | Manufacturing method of high wettablility and antimicrobial contact lens using carrageenan |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020200010310A KR102232954B1 (en) | 2020-01-29 | 2020-01-29 | Manufacturing method of high wettablility and antimicrobial contact lens using carrageenan |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR102232954B1 true KR102232954B1 (en) | 2021-03-25 |
Family
ID=75222652
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020200010310A KR102232954B1 (en) | 2020-01-29 | 2020-01-29 | Manufacturing method of high wettablility and antimicrobial contact lens using carrageenan |
Country Status (1)
| Country | Link |
|---|---|
| KR (1) | KR102232954B1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20220158112A (en) * | 2021-05-20 | 2022-11-30 | 대구가톨릭대학교산학협력단 | Manufacturing method of antioxidant contact lens using quercetin with natural polysaccharides |
| WO2023216066A1 (en) * | 2022-05-09 | 2023-11-16 | 台北科技大学 | Polysaccharide composition and method for reducing protein adsorption |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10160854B1 (en) * | 2015-08-03 | 2018-12-25 | Gl Chemtec Vision Inc. | Hydrogel materials |
| KR101989247B1 (en) * | 2017-12-05 | 2019-06-13 | 대구가톨릭대학교산학협력단 | Manufacturing method of hydrogel contact lens using blowing agent |
-
2020
- 2020-01-29 KR KR1020200010310A patent/KR102232954B1/en active IP Right Grant
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10160854B1 (en) * | 2015-08-03 | 2018-12-25 | Gl Chemtec Vision Inc. | Hydrogel materials |
| KR101989247B1 (en) * | 2017-12-05 | 2019-06-13 | 대구가톨릭대학교산학협력단 | Manufacturing method of hydrogel contact lens using blowing agent |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20220158112A (en) * | 2021-05-20 | 2022-11-30 | 대구가톨릭대학교산학협력단 | Manufacturing method of antioxidant contact lens using quercetin with natural polysaccharides |
| KR102505084B1 (en) * | 2021-05-20 | 2023-03-02 | 대구가톨릭대학교산학협력단 | Manufacturing method of antioxidant contact lens using quercetin with natural polysaccharides |
| WO2023216066A1 (en) * | 2022-05-09 | 2023-11-16 | 台北科技大学 | Polysaccharide composition and method for reducing protein adsorption |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR102232954B1 (en) | Manufacturing method of high wettablility and antimicrobial contact lens using carrageenan | |
| Hyon et al. | Poly (vinyl alcohol) hydrogels as soft contact lens material | |
| KR100994747B1 (en) | Hydrogel contact lenses having improved wettability | |
| CN103467652B (en) | A kind of hydrogel contact glass and preparation method thereof | |
| CA2588880C (en) | Ophthalmic compositions comprising polyether substituted polymers | |
| DE60316315T2 (en) | LBL COATED CONTACT LENSES AND METHOD FOR THE PRODUCTION THEREOF | |
| US10371965B2 (en) | Hydrogel contact lens having wet surface, and manufacturing method therefor | |
| JPH07508063A (en) | Surface wettable silicone hydrogel | |
| JPS6330820A (en) | Polymer material for transparent hydrogel contact lens and optically transparent hydrophilic contact lens comprising the same | |
| KR20150023485A (en) | Polymers and nanogel materials and methods for making and using the same | |
| KR20100015771A (en) | Silicone-containing prepolymers with dangling hydrophilic polymeric chains | |
| SG188917A1 (en) | Coating process for ophthalmic lenses | |
| HUE027812T2 (en) | Silicone hydrogel lenses with nano-textured surfaces | |
| MX2013001188A (en) | A silicone hydrogel lens with a crosslinked hydrophilic coating. | |
| DE1065621B (en) | Process for the production of hydrophilic, swollen or strongly swellable molded structures | |
| CN102617787A (en) | Hydrogel contact lens material and preparation method thereof | |
| Eldin et al. | Wound dressing membranes based on chitosan: Preparation, characterization and biomedical evaluation | |
| Ko et al. | Study on characteristic changes of contact lenses according to interpenetrating polymer network time and method using seaweed polysaccharide | |
| Ko et al. | Effect of ionic natural polysaccharides on the functional enhancement of porous hydrogel contact lenses | |
| Ng et al. | Polymers in contact lens applications VI. The ‘dissolved’oxygen permeability of hydrogels and the design of materials for use in continuous‐wear lenses | |
| Lai et al. | Control of properties in silicone hydrogels by using a pair of hydrophilic monomers | |
| KR102232953B1 (en) | Manufacturing method of porous silicon hydrogel contact lens containing agiate | |
| KR102149837B1 (en) | Method for manufacturing contact lens with improved fit | |
| KR20180010565A (en) | Hydrogel with improved modulus and medical uses thereof | |
| KR101994668B1 (en) | Wettable hydrogel contact lens |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E701 | Decision to grant or registration of patent right | ||
| GRNT | Written decision to grant |