KR20150067931A - Acrylic silicone resin composition for contact lens and contact lens produced using thereof - Google Patents
Acrylic silicone resin composition for contact lens and contact lens produced using thereof Download PDFInfo
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Abstract
Description
본 발명은 콘택트렌즈용 아크릴 실리콘 수지 조성물 및 이를 이용한 콘택트렌즈에 관한 것으로, 보다 상세하게는 산소투과성이 우수한 실리콘 중간체를 아크릴레이션(Acrylation)반응 통하여 아크릴 모노머와 혼합하여 산소투과성을 향상시킨 콘택트렌즈용 아크릴 실리콘 수지 조성물 및 이를 이용한 콘택트렌즈에 관한 것이다.The present invention relates to an acrylic silicone resin composition for a contact lens and a contact lens using the acrylic silicone resin composition. More particularly, the present invention relates to an acrylic silicone resin composition for a contact lens which has excellent oxygen permeability by mixing with an acrylic monomer through an acrylation reaction, Acrylic silicone resin composition and a contact lens using the same.
일반적으로 콘택트렌즈는 크게 메틸 메타크릴레이트 (Methyl metharylate : MMA)를 기본 물질로 하는 하드 렌즈와, 2-하이드록시에틸 메타크릴레이트 (2-Hydroxyethyl methacrylate: HEMA)를 기본 물질로 하는 소프트 렌즈로 구분된다. 상기 MMA와 HEMA 재료들은 뛰어난 광투과율과 투명도로 안경을 대체하는 안 의료용기구인 콘택트렌즈 제조에 이용되어 왔으며 생체적합성 또한 우수하여 콘택트렌즈의 대중화를 이끌었다. Generally, the contact lenses are divided into a hard lens made of methyl methacrylate (MMA) as a base material and a soft lens made of 2-hydroxyethyl methacrylate (HEMA) as a base material. do. The MMA and HEMA materials have been used in the manufacture of contact lenses, which are an eye medical instrument replacing eyeglasses with excellent light transmittance and transparency, and are also excellent in biocompatibility, leading to popularization of contact lenses.
하지만 이 재료들을 사용하여 제조한 콘택트렌즈는 대기 중의 산소를 안구에 전달하는 능력이 매우 낮아 신생혈관, 각막부종 등의 안구질환을 유발하였다. 이에 따라 최근에는 산소투과율을 높여 콘택트렌즈 착용으로 인한 산소 전달 부족에 따른 안질환 발생을 예방하기 위하여 실리콘이 포함되어 있는 preppolymer를 사용하여 재조한 실리콘하이드로젤 콘택트렌즈가 연구 출시되고 있다(대한민국 공개특허제10-2008-0113467호;연질 콘텍트렌즈용 실리콘 하이드로겔 조성물 및 그 조성에의해 제조된 연질 콘텍트렌즈, 대한민국 공개특허 제10-2013-0086607호;수분이 풍부한 표면을 갖는 실리콘 히드로겔 렌즈), However, contact lenses manufactured using these materials have a very low ability to transfer oxygen in the air to the eye, resulting in eye diseases such as neovascularization and corneal edema. Recently, a silicone hydrogel contact lens reconditioned using a prepolymer containing silicone has been investigated in order to prevent the occurrence of ocular disease due to lack of oxygen transfer due to wearing of a contact lens by increasing the oxygen transmission rate 10-2008-0113467, Silicone Hydrogel Composition for Soft Contact Lens and Soft Contact Lens Made by the Composition, Korean Patent Laid-Open No. 10-2013-0086607, Silicone Hydrogel Lens Having a Water-Rich Surface)
하지만 실리콘 하이드로젤 콘택트렌즈는 산소투과성이 비교적 우수하나 재질의 특성상 탄성이 낮고 친수화를 위한 후가공이 필요한 단점을 가진다. However, silicone hydrogel contact lenses have relatively good oxygen permeability, but they are low in elasticity due to the nature of the material and require post-processing for hydrophilizing.
뿐만 아니라 실리콘 하이드로젤 콘택트렌즈는 현재까지 외국기업이 대부분의 시장을 점유하고 있으며 국내 기업의 경우 실리콘 하이드로젤 콘택트렌즈 개발이 미미한 수준이어서 국산화가 용이한 제품의 개발이 요청된다. In addition, silicone hydrogel contact lenses are currently dominated by foreign companies in most markets, and Korean companies are required to develop products that are easy to localize because silicone hydrogel contact lenses are not developed at all.
본 발명은 상기와 같은 점을 인식하여 안출된 것으로 본 발명의 목적은 산소투과성이 우수한 실리콘 중간체를 아크릴레이션(Acrylation)반응 통하여 아크릴 모노머와 혼합하여 산소투과성을 향상시킨 콘택트렌즈용 아크릴 실리콘 수지 조성물 및 이를 이용한 콘택트렌즈를 제공하기 위한 것이다.SUMMARY OF THE INVENTION It is an object of the present invention to provide an acrylic silicone resin composition for contact lenses in which an oxygen permeability is improved by mixing a silicon intermediate with an acrylic monomer through an acrylation reaction, And to provide a contact lens using the same.
상기와 같은 목적을 달성하기 위하여 본 발명에 따른 콘택트렌즈용 아크릴 실리콘 수지 조성물은, 하이드록시기를 가지는 폴리디메틸 실리콘 중간체와 하이드록시기를 가지는 아크릴 모노머를 촉매 탈수중합하여 얻는 것을 특징으로 한다.In order to achieve the above object, the acrylic silicone resin composition for a contact lens according to the present invention is characterized in that a polydimethyl silicone intermediate having a hydroxy group and an acrylic monomer having a hydroxy group are obtained by catalytic dehydration condensation.
또한, 본 발명에 따른 콘택트렌즈용 아크릴 실리콘 수지 조성물은, 상기 폴리디메틸 실리콘 중간체는 10~80 중량%이고, 상기 아크릴 모노머는 20 ~ 90 중량%이며, 반응 촉진을 위한 촉매는 1 ~ 5 중량%가 혼합되어 반응되는 것을 특징으로 한다.In the acrylic silicone resin composition for a contact lens according to the present invention, the polydimethyl silicone intermediate is 10 to 80% by weight, the acrylic monomer is 20 to 90% by weight, the catalyst for promoting the reaction is 1 to 5% Are mixed and reacted.
또한, 본 발명에 따른 콘택트렌즈용 아크릴 실리콘 수지 조성물은, 상기 아크릴 모노머는 2-HEMA(2-Hydroxyethylmethacrylate), 2-HEA(2-Hydroxyethylacrylate), HPA(hydroxypropylacrylate), HPMA(hydroxypropylmethacrylate) 중에서 적어도 어느 하나 이상이 선택되어 혼합된 것을 특징으로 한다.In the acrylic silicone resin composition for a contact lens according to the present invention, the acrylic monomer may be at least one of 2-HEMA (2-Hydroxyethylmethacrylate), 2-HEA (2-Hydroxyethylacrylate), HPA (hydroxypropyllacrylate) Or more is selected and mixed.
또한, 본 발명에 따른 콘택트렌즈용 아크릴 실리콘 수지 조성물을 이용한 콘택트 렌즈는, 상기 아크릴 실리콘 수지 조성물을 이용하여 제조된 것을 특징으로 한다.Also, the contact lens using the acrylic silicone resin composition for a contact lens according to the present invention is characterized in that it is manufactured using the acrylic silicone resin composition.
상기와 같은 구성에 의하여 본 발명에 따른 콘택트렌즈용 아크릴 실리콘 수지 조성물 및 이를 이용한 콘택트렌즈는 자유라디칼 중합이 가능하고 다른 아크릴 모노머와 중합 상용성이 뛰어날 뿐 아니라 고 산소 투과성이 우수한 장점을 갖는다.The acrylic silicone resin composition for a contact lens according to the present invention and the contact lens using the acrylic silicone resin composition according to the present invention have the advantage of excellent free radical polymerization, excellent polymerization compatibility with other acrylic monomers, and high oxygen permeability.
도 1 내지 도 3은 본 발명의 일실시예에 따른 콘택트렌즈용 아크릴 실리콘 수지 조성을 이용하여 제조된 콘택트렌즈 폴리머의 산소투과성 측정시 전류 및 온도 변화를 기록한 그래프
도 4는 일반적인 종래 콘택트렌즈 폴리머의 산소투과성 측정시 전류 및 온도 변화를 기록한 그래프1 to 3 are graphs showing changes in current and temperature during the measurement of oxygen permeability of a contact lens polymer prepared using an acrylic silicone resin composition for a contact lens according to an embodiment of the present invention
FIG. 4 is a graph showing changes in current and temperature during measurement of oxygen permeability of a conventional contact lens polymer
본 발명에 따른 콘택트렌즈용 아크릴 실리콘 수지 조성물은 산소 투과성이 우수하고 하이드록시기를 가지는 폴리디메틸 실리콘 중간체와 이를 라디칼 중합이 가능하도록 아크릴레이션을 위한 하이드록시 그룹이 있는 아크릴 모노머 및 반응성 촉매를 포함하며, 보다 상세하게는 하이드록시기를 가지는 폴리디메틸 실리콘 중간체 10~80 중량%, 하이드록시를 가지는 아크릴 모노머 20 ~ 90 중량%, 반응 촉진을 위한 촉매 1 ~ 5 중량%를 포함한다. The acrylic silicone resin composition for a contact lens according to the present invention comprises a polydimethyl silicone intermediate having excellent oxygen permeability and a hydroxyl group, an acrylic monomer having a hydroxy group for acrylation and a reactive catalyst for radical polymerization thereof, More specifically, it comprises 10 to 80% by weight of a polydimethylsilicon intermediate having a hydroxy group, 20 to 90% by weight of an acrylic monomer having hydroxy, and 1 to 5% by weight of a catalyst for promoting the reaction.
상기와 같이 제조된콘택트렌즈용 아크릴 실리콘 수지 조성물을 다른 아크릴 모노머와 중합 개시제와 혼합하여 고 산소 투과성 콘택트 렌즈 폴리머를 제조할 수 있다.The acrylic silicone resin composition for contact lenses prepared as described above may be mixed with other acrylic monomers and a polymerization initiator to prepare a high-oxygen-permeable contact lens polymer.
상기 폴리디메틸 실리콘 중간체는 사슬내에 반응성 하이드록시 그룹이 1개 이상을 포함하며, 중량 평균분자량은 Mw 100 ~ 2,000인 것이 바람직하다. 폴리디메틸 실리콘 중간체의 분자량이 2,000 이상인 경우 아크릴 모노머와 라디칼 중합시 중합물의 외관이 뿌옇게 된다. The polydimethyl silicone intermediate preferably contains at least one reactive hydroxy group in the chain and has a weight average molecular weight of Mw 100 to 2,000. When the polydimethylsilane intermediate has a molecular weight of 2,000 or more, the appearance of the polymer is cloudy with the acrylic monomer and the radical polymerization.
상기 폴리디메틸 실리콘 중간체는 10~80 중량%이 혼합되는 것이 적당하다. 상기 폴리디메틸 실리콘 중간체를 10 중량% 이하 사용할 경우 실리콘 중간체 함량이 작아 산소투과성 특성이 떨어지며, 80 중량% 이상 사용할 경우는 실리콘 중간체 함량이 너무 많아 라디칼 중합시 중합물의 외관이 뿌옇게 된다. The polydimethyl silicone intermediate is suitably mixed in an amount of 10 to 80% by weight. When the polydimethylsilicon intermediate is used in an amount of 10 wt% or less, the silicon intermediate content is low and the oxygen permeability is inferior. When the polydimethylsilicon intermediate is used in an amount of 80 wt% or more, the silicon intermediate content is too high.
폴리디메틸 실리콘 중간체 구조식Structure of polydimethylsilicon intermediate
상기 하이드록시 아크릴 모노머는 2-HEMA(2-Hydroxyethylmethacrylate), 2-HEA(2-Hydroxyethylacrylate), HPA hydroxypropylacrylate, HPMA(hydroxypropylmethacrylate) 중 어느 하나 또는 이들을 혼합하여 사용하며, 실리콘 중간체의 하이드록시 함량에 따라 20 ~ 90중량% 사용한다.
The hydroxyacrylic monomer may be selected from the group consisting of 2-HEMA (2-Hydroxyethylmethacrylate), 2-HEA (2-Hydroxyethylacrylate), HPA hydroxypropylacrylate and HPMA (hydroxypropylmethacrylate) To 90% by weight.
2-HEMA(2-Hydroxyethylmethacrylate) 구조식2-HEMA (2-Hydroxyethylmethacrylate) Structural Formula
2-HEA(2-Hydroxyethylacrylate) 구조식2-HEA (2-Hydroxyethylacrylate) Structural Formula
HPA (Hydroxypropylacrylate) 구조식HPA (Hydroxypropylacrylate) Structure
HPMA(hydroxypropylmethacrylate) 구조식HPMA (hydroxypropylmethacrylate) structural formula
상기 반응성 촉매는 실리콘 중간체의 하이드록시 그룹과 아크릴의 하이드록시 그룹의 반응을 촉진시켜 줄 수 있는 티타늄계(Ti), 틴(Sn)계를 사용하며, 자세하게는 티타늄이소프로폭사이드, 티타늄부톡사이드 사용한다. 상기 반응성 촉매를 1 중량% 이하 사용시 반응 속도가 너무 느리며, 5 중량%이상 사용시 반응속도가 너무 빨라 겔(gel)화될수 있으므로 1 ~ 5 중량% 사용이 적당하다.The reactive catalyst may be a titanium (Ti) or a tin (Sn) system which can promote the reaction between the hydroxy group of the silicon intermediate and the hydroxy group of the acryl. More specifically, titanium isopropoxide, titanium butoxide use. When the reactive catalyst is used in an amount of 1% by weight or less, the reaction rate is too slow. When the reactive catalyst is used in an amount of 5% by weight or more, the reaction rate becomes too fast.
티타늄이소프로폭사이드(Titanium isopropoxide)Titanium isopropoxide < RTI ID = 0.0 >
티타늄부톡사이드(Titanium butoxide)Titanium butoxide
이하에서는 구체적인 실시예 및 비교예를 통하여 본 발명에 따른 콘택트렌즈용 아크릴 실리콘 수지 조성물 및 이를 이용한 콘택트렌즈를 보다 상세하게 설명한다.
Hereinafter, the acrylic silicone resin composition for a contact lens and the contact lens using the same according to the present invention will be described in detail with reference to specific examples and comparative examples.
<실시예1 : 산소투과성이 뛰어난 아크릴 실리콘 수지 조성물 합성>≪ Example 1: Synthesis of acrylic silicone resin composition having excellent oxygen permeability >
교반기, 냉각장치, 가열장치, 수분분리기 그리고 질소가 설치된 플라스크에 하이드록시 폴리디메틸 실리콘 40 중량%, 2-HEA(2-Hydroxyethylacrylate) 55 중량% 및 티타튬이소프록폭사이드 5 중량 % 혼합 후 100℃로 승온하여 탈수반응 한다. 더 이상 탈수가 되지 않을 때까지 가열 반응을 실시한다.
40% by weight of hydroxypolydimethylsilicon, 55% by weight of 2-HEA (2-Hydroxyethylacrylate) and 5% by weight of titanium tetraisopropoxide was added to a flask equipped with a stirrer, a cooling device, a heating device, To conduct dehydration reaction. Heating reaction is carried out until dehydration no longer occurs.
아크릭실리콘 수지 조성물 반응 메카니즘Acrylic silicone resin composition reaction mechanism
상기와 같은 방법으로 합성된 수지는 다른 아크릴 모노머와 혼합하여 라디칼 반응을 하여 산소투과성이 뛰어난 콘택트렌즈 폴리머를 제조하였다.
The resin thus synthesized was mixed with other acrylic monomers and subjected to a radical reaction to produce a contact lens polymer excellent in oxygen permeability.
<실시예2 : 고 산소투과성 콘택트렌즈 폴리머1 제조>Example 2: Production of highly oxygen-permeable
상기 실시예1에서 합성한 아크릴 실리콘 수지 조성물 10 중량%와, MA(methacrylate), HPMA(Hydroxyproply methacrylate), EOEMA(2-Ethoxyethyl methacrylate), EGDMA(Ethylene glycol dimethacrylate), MMA(Mthyl methacrylate) 중에서 적어도 하나 이상이 혼합된 혼합물 모노머 89 중량%, 및 라디칼 중합개시제 AIBN(Azobisisobutyronitrile ) 1 중량%를 혼합한 후 90℃와 100℃ 사이에서 1시간 동안 중합반응 실시한다.
10 wt% of the acrylic silicone resin composition synthesized in Example 1 and at least one of MA (methacrylate), HPMA (Hydroxypropyl methacrylate), EOEMA (2-Ethoxyethyl methacrylate), EGDMA (Ethylene glycol dimethacrylate) and MMA 89% by weight of a mixture monomer having a mixture of the above components and 1% by weight of a radical polymerization initiator AIBN (Azobisisobutyronitrile) are mixed and polymerization reaction is carried out at 90 ° C and 100 ° C for 1 hour.
<실시예3 : 고 산소투과성 콘택트렌즈 폴리머2 제조>Example 3: Production of high-oxygen-permeable
상기 실시예1에서 합성한 아크릴 실리콘 수지 조성물 60 중량%와, MA(methacrylate), HPMA(Hydroxyproply methacrylate), EOEMA(2-Ethoxyethyl methacrylate), EGDMA(Ethylene glycol dimethacrylate), MMA(Mthyl methacrylate)중에서 적어도 하나 이상이 혼합된 혼합물 모노머 39 중량%, 및 라디칼 중합개시제 AIBN(Azobisisobutyronitrile ) 1 중량%를 혼합한 후 90℃와 100℃ 사이에서 1시간 동안 중합반응 실시한다.
60 wt% of the acrylic silicone resin composition synthesized in Example 1 and at least one of MA (methacrylate), HPMA (Hydroxypropyl methacrylate), EOEMA (2-Ethoxyethyl methacrylate), EGDMA (Ethylene glycol dimethacrylate) and MMA , 39% by weight of a mixture of the above mixed monomers and 1% by weight of a radical polymerization initiator AIBN (Azobisisobutyronitrile) are mixed, and polymerization reaction is carried out at 90 ° C and 100 ° C for 1 hour.
<실시예4 : 고 산소투과성 콘택트렌즈 폴리머3 제조>Example 4: Production of high-oxygen-permeable
상기 실시예1에서 합성한 아크릴 실리콘 수지 조성물 80 중량%와, MA(methacrylate), HPMA(Hydroxyproply methacrylate), EOEMA(2-Ethoxyethyl methacrylate), EGDMA(Ethylene glycol dimethacrylate), MMA(Mthyl methacrylate)중에서 적어도 하나 이상이 혼합된 혼합물 모노머 89 중량%, 및 라디칼 중합개시제 AIBN(Azobisisobutyronitrile ) 1 중량%를 혼합한 후 90℃와 100℃ 사이에서 1시간 동안 중합반응 실시한다.
80% by weight of the acrylic silicone resin composition synthesized in Example 1 and at least one of MA (methacrylate), HPMA (Hydroxypropyl methacrylate), EOEMA (2-Ethoxyethyl methacrylate), EGDMA (Ethylene glycol dimethacrylate) and MMA 89% by weight of a mixture monomer having a mixture of the above components and 1% by weight of a radical polymerization initiator AIBN (Azobisisobutyronitrile) are mixed, and polymerization reaction is carried out at 90 ° C and 100 ° C for 1 hour.
<비교예1 : 일반 콘택트렌즈 폴리머>≪ Comparative Example 1: General contact lens polymer >
2-HEMA(2-Hydroxyethylmethacrylate) 94 중량%, MMA(methylmethacrylate) 5 중량% 및 라디칼 중합개시제 AIBN(Azobisisobutyronitrile ) 1 중량%를 혼합 후 90℃와 100℃ 사이에서 1시간 동안 중합반응 실시한다.
94% by weight of 2-HEMA (2-hydroxyethylmethacrylate), 5% by weight of MMA (methylmethacrylate) and 1% by weight of a radical polymerization initiator AIBN (Azobisisobutyronitrile) are mixed and polymerization reaction is carried out at 90 ° C and 100 ° C for 1 hour.
<실시예5 : 산소투과성 아크릴 실리콘수지 물성 평가><Example 5: Evaluation of physical properties of oxygen-permeable acrylic silicone resin>
실시예2 ~ 4 및 비교예1 에서 얻어진 콘택트렌즈 폴리머의 외관과 산소투과성 등의 물성을 측정하였다. 표 1은 상기 콘택트렌즈 폴리머의 물성평가 결과를 정리한 것이다.The appearance of the contact lens polymer obtained in Examples 2 to 4 and Comparative Example 1 and physical properties such as oxygen permeability were measured. Table 1 summarizes the physical property evaluation results of the contact lens polymer.
* 외 관 : 중합물의 투명도 확인* Appearance: Confirmation of transparency of polymer
* 산소투과성(Dk) :측정기기는 Polarograghic (O2 PermeometerTM MODEL 201T)를 사용하였다. 도 1 내지 도 4는 상기 실시예2 내지 4 및 비교예1에서 제조된 콘택트렌즈 폴리머의 산소투과성 측정의 전류 및 온도 변화를 기록한 그래프이다.* Oxygen permeability (Dk): Polarograghic (O 2 Permeometer TM MODEL 201T) was used as the measuring instrument. FIGS. 1 to 4 are graphs showing changes in current and temperature in the measurement of oxygen permeability of the contact lens polymer prepared in Examples 2 to 4 and Comparative Example 1. FIG.
상기 표 1에서 나타난 바와 같이 본 발명에 따른 콘택트렌즈용 아크릴 실리콘 수지 조성물을 다른 아크릴 수지와 개시 중합을 통하여 만든 콘택트렌즈 폴리머는 산소 투과성이 우수하다는 것을 확인할 수 있다.As shown in Table 1, the acrylic resin composition for contact lenses according to the present invention is superior in oxygen permeability to other acrylic resin and contact lens polymer prepared through initiation polymerization.
Claims (5)
상기 폴리디메틸 실리콘 중간체는 10~80 중량%이고,
상기 아크릴 모노머는 20 ~ 90 중량%이며,
반응 촉진을 위한 촉매는 1 ~ 5 중량%가 혼합되어 반응되는 것을 특징으로 하는 콘택트렌즈용 아크릴 실리콘 수지 조성물.The method according to claim 1,
The polydimethylsilicon intermediate is 10 to 80% by weight,
The acrylic monomer is 20 to 90% by weight,
And 1 to 5% by weight of a catalyst for promoting the reaction is mixed and reacted.
상기 아크릴 모노머는 2-HEMA(2-Hydroxyethylmethacrylate), 2-HEA(2-Hydroxyethylacrylate), HPA(hydroxypropylacrylate), HPMA(hydroxypropylmethacrylate) 중에서 적어도 어느 하나 이상이 선택되어 혼합된 것을 특징으로 하는 콘택트렌즈용 아크릴 실리콘 수지 조성물.The method according to claim 1 or 2, wherein
Wherein the acrylic monomer is at least one selected from 2-HEMA (2-Hydroxyethylmethacrylate), 2-HEA (2-Hydroxyethylacrylate), HPA (hydroxypropyllacrylate) and HPMA (hydroxypropylmethacrylate) Resin composition.
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| KR1020130153502A KR20150067931A (en) | 2013-12-10 | 2013-12-10 | Acrylic silicone resin composition for contact lens and contact lens produced using thereof |
| PCT/KR2014/000602 WO2015088099A1 (en) | 2013-12-10 | 2014-01-21 | Acrylic silicone resin composition for contact lens and contact lens using same |
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| US7214809B2 (en) * | 2004-02-11 | 2007-05-08 | Johnson & Johnson Vision Care, Inc. | (Meth)acrylamide monomers containing hydroxy and silicone functionalities |
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