KR20190118790A - A silicone hydrogel lens obtained by copolymerizing a hydrophilic terpolymer and silicon, and a process for producing the same - Google Patents
A silicone hydrogel lens obtained by copolymerizing a hydrophilic terpolymer and silicon, and a process for producing the same Download PDFInfo
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Abstract
Description
본 발명은 높은 산소투과율을 부각시켜 착용감 및 눈건강을 개선시키도록 한 친수성 터폴리머와 실리콘을 공중합한 실리콘 하이드로겔 렌즈 및 그의 제조방법에 관한 것이다.The present invention relates to a silicone hydrogel lens copolymerized with a hydrophilic terpolymer and silicone, which improves wearing comfort and eye health by highlighting a high oxygen permeability and a method of manufacturing the same.
일반적으로, 콘택트렌즈는 적당한 기계적 강도(tensile strength), 생체적합성(biocompatibility), 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 moderate mechanical strength, biocompatibility, toxicity, optical transparency of materials, refractive index, surface wettability, and moisture content suitable for the cornea. requirements such as water content, swelling, oxygen transmissibility, and flexibility should be met.
특히, 콘택트렌즈의 장기착용에서 유발되는 안과적 질환의 문제점과 부작용을 고려하면, 위에서 언급한 산소투과성의 요건은 매우 중요하다 할 것이다.In particular, considering the problems and side effects of ophthalmic diseases caused by long-term wear of contact lenses, the above-mentioned oxygen permeability requirements will be very important.
따라서, 콘택트렌즈의 산소투과성 향상을 위해 산소투과성이 우수한 재질의 연구 및 개발이 활발하게 진행되고 있으며, 그 일례로서 실리콘이 포함된 프리폴리머(prepolymer)를 들 수 있다.Accordingly, research and development of materials having excellent oxygen permeability have been actively conducted to improve oxygen permeability of contact lenses, and examples thereof include prepolymers containing silicon.
프리폴리머를 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 a prepolymer, Korean Patent No. 10-0901806 discloses a polyurethane resin composition and an impact resistant synthetic resin lens for molding an optical lens.
위 기술은, 2 이상의 이소시아네이트(isocyanate)기를 가진 치환족 폴리이소시아네이트(polyisocyanates)와 2 이상의 수산기를 가진 폴리올(polyol)을 반응시켜 얻어진 프리폴리머(prepolymer), 내부 이형제 및 Gardner 색수 2 이하로 정제된 4,4'-메틸렌비스(2-클로로아닐린)을 필수성분으로 포함하는 것이다.The above technique is a prepolymer obtained by reacting a substituted polyisocyanates having two or more isocyanate groups with a polyol having two or more hydroxyl groups, an internal mold release agent, and purified by Gardner color number 2 or less. 4'-methylenebis (2-chloroaniline) is included as an essential component.
하지만, 이러한 프리폴리머를 응용하여 만든 렌즈는 침착물과 습윤성(濕潤性)의 문제가 있을 뿐만 아니라, 산소투과율이 각막 산소 요구율에 미치지 못해 사용자에게 불편을 초래하였다. 또한, 수분과 접하지 않으려는 실리콘 성분의 소수성화로 인해 착용감이 급격히 나빠져 장시간 착용하기에는 무리가 있었다.However, the lens made by applying the prepolymer not only has a problem of deposit and wettability, but also causes inconvenience to the user because the oxygen permeability does not meet the corneal oxygen demand. In addition, due to the hydrophobicization of the silicone component that does not want to come in contact with the moisture, the fit is rapidly worsened, it was unreasonable to wear for a long time.
본 발명은 상기한 바와 같은 문제점을 해결하기 위한 것으로, 본 발명의 목적은 산소투과율(oxygen transmission rate)과 착용감이 우수한 친수성 터폴리머와 실리콘을 공중합한 실리콘 하이드로겔 렌즈 및 그의 제조방법을 제공함에 있다.The present invention is to solve the problems described above, an object of the present invention is to provide a silicone hydrogel lens copolymerized with a hydrophilic terpolymer and silicone excellent in oxygen transmission rate and fit and a manufacturing method thereof. .
본 발명의 과제 해결 수단 구성은, a) 하기 화학식 1의 단량체와 1-vinyl-2-pyrrolidone(NVP)를 30 - 90 : 10 - 70%의 중량비율로 라디칼 중합한 다음, 여기에 N,N-dimethyl acrylamide(DMA) 또는 Ethylene glycol dimethacrylate(EGDMA) 중 단독 또는 이들의 혼합물과, 하기 화학식 2의 Azobisisobutyronitrile(AIBN)으로 Terpolymer를 라디칼 중합하여 콘택트렌즈 제조용 조성물을 제조하며; b) 상기 a)단계의 콘택트렌즈 제조용 조성물을 몰드에 주입하여 전면부 또는 후면부 중 어느 하나의 면이 볼록형상인 렌즈로 사출한 후, 사출된 렌즈의 단부를 유선형의 엣지(edge) 형태로 성형하여 형성되는 것을 특징으로 한다.According to one aspect of the present invention, a) a radical polymerization of a monomer of the following formula (1) and 1-vinyl-2-pyrrolidone (NVP) at a weight ratio of 30-90: 10-70%, followed by N, N preparing a composition for preparing a contact lens by radically polymerizing Terpolymer with -dimethyl acrylamide (DMA) or Ethylene glycol dimethacrylate (EGDMA) alone or a mixture thereof and Azobisisobutyronitrile (AIBN) of Formula 2; b) injecting the composition for manufacturing the contact lens of step a) into a mold and injecting either of the front surface or the rear surface into a convex lens, and molding the end of the injected lens into a streamlined edge shape. It is characterized by being formed.
[화학식 1][Formula 1]
[화학식 2][Formula 2]
또한, 상기 a)단계의 라디칼 중합은 120 - 140℃의 온도에서 40 - 50분 동안 이루어지고, 상기 b)단계의 성형된 렌즈는 전면부가 상단에서 하단으로 갈수록 곡면중심으로부터의 거리가 점차 길어지도록 형성되고, 후면부가 곡면중심으로부터 동일한 반지름을 갖도록 형성될 수 있다.In addition, the radical polymerization of step a) is carried out for 40-50 minutes at a temperature of 120-140 ℃, the molded lens of step b) so that the distance from the center of the curved surface is gradually longer from the top to the bottom It may be formed, and the rear portion may be formed to have the same radius from the curved center.
더불어, 상기 1-vinyl-2-pyrrolidone(NVP)은 라디칼 중합을 위한 비닐기를 가진 구조인 것이 바람직하다.In addition, the 1-vinyl-2-pyrrolidone (NVP) is preferably a structure having a vinyl group for radical polymerization.
상기와 같은 방법으로 제조된 본 발명의 실리콘 하이드로겔 렌즈는, 산소투과율(oxygen transmission rate) 및 광투과율(light transmittance)이 우수하고, 사용자의 눈의 건조함, 충혈 등을 방지하여 착용감이 뛰어난 효과가 있다. 이와 더불어 거시적 경제관점에서 국내에 정체되어 있는 실리콘 하이드로겔 렌즈보다 더욱이 많은 부분에 기술적인 장점을 부각시켜 국내외 시장에 따른 부가가치 창출에도 기여할 수 있다.The silicone hydrogel lens of the present invention manufactured by the above method has excellent oxygen transmission rate and light transmittance, and prevents dryness of the user's eyes, redness, and the like, and is excellent in wearing comfort. There is. In addition, it can contribute to the creation of added value according to domestic and foreign markets by highlighting the technical advantages in many parts than the silicone hydrogel lens stagnant in Korea in the macroeconomic perspective.
도 1은 본 발명의 바람직한 일 실시예에 따른 친수성 터폴리머와 실리콘을 공중합한 실리콘 하이드로겔 렌즈를 나타낸 사진,
도 2는 도 1의 렌즈와 타사제품의 렌즈 단면 엣지(edge) 부위를 비교한 사진.1 is a photo showing a silicone hydrogel lens copolymerized with a hydrophilic terpolymer and silicone according to an embodiment of the present invention,
Figure 2 is a photograph comparing the lens cross-sectional edge portion of the lens of Figure 1 and other companies.
본 발명에서 사용된 렌즈는 개체의 눈과 각막 상에 위치될 수 있는 구조체를 지칭하며, 상처 치유 또는 트랜스퍼슈티컬(Transferceutical)의 전달, 진단 평가 또는 모니터링, 또는 UV 차단 및 가시광 또는 눈부심(glare) 감소, 또는 이들의 조합을 포함하는 교정적, 미용적, 치료적 이점을 제공할 수 있는 인체보조기구로, 렌즈는 소프트 콘택트렌즈, 하드 콘택트렌즈 또는 하이브리드 콘택트렌즈 일 수 있으며, 바람직하게는 유연성과 착용감이 우수한 소프트 콘택트렌즈(soft contact lens) 일 수 있다.Lenses used in the present invention refer to structures that can be located on the eye and cornea of an individual, and can be used for wound healing or transfer of transparent, transfer, diagnostic evaluation or monitoring, or UV blocking and visible or glare. With braces that can provide corrective, cosmetic, and therapeutic benefits, including a reduction, or a combination thereof, the lens may be a soft contact lens, a hard contact lens, or a hybrid contact lens, preferably with flexibility and fit This may be an excellent soft contact lens.
본 발명의 친수성 터폴리머와 실리콘을 공중합한 실리콘 하이드로겔 렌즈는,Silicone hydrogel lens copolymerized with the hydrophilic terpolymer of the present invention, silicone,
a) 하기 화학식 1의 단량체와 1-vinyl-2-pyrrolidone(NVP)를 30 - 90 : 10 - 70%의 중량비율로 라디칼 중합한 다음, 여기에 N,N-dimethyl acrylamide(DMA) 또는 Ethylene glycol dimethacrylate(EGDMA) 중 단독 또는 이들의 혼합물과, 하기 화학식 2의 Azobisisobutyronitrile(AIBN)으로 Terpolymer를 라디칼 중합하여 콘택트렌즈 제조용 조성물을 제조하며;a) radical polymerization of the monomer of Formula 1 with 1-vinyl-2-pyrrolidone (NVP) at a weight ratio of 30-90: 10-70%, and then N, N-dimethyl acrylamide (DMA) or Ethylene glycol preparing a composition for preparing a contact lens by radically polymerizing Terpolymer with dimethacrylate (EGDMA) alone or a mixture thereof and Azobisisobutyronitrile (AIBN) represented by the following Chemical Formula 2;
b) 상기 a)단계의 콘택트렌즈 제조용 조성물을 몰드에 주입하여 전면부 또는 후면부 중 어느 하나의 면이 볼록형상인 렌즈로 사출한 후, 사출된 렌즈의 단부를 유선형의 엣지(edge) 형태로 성형하여 형성된다.b) injecting the composition for manufacturing the contact lens of step a) into a mold and injecting either of the front surface or the rear surface into a convex lens, and molding the end of the injected lens into a streamlined edge shape. Is formed.
[화학식 1][Formula 1]
[화학식 2][Formula 2]
상기 화학식 1로 이루어진 단량체는 산소투과향상을 도모하는 Methacryloxypropyltrimethoxysilane(CAS NO.: 2530-85-0)일 수 있으며, 높은 렌즈 특성(산소투과도 향상 등)을 보이는 특징이 있다.The monomer of Chemical Formula 1 may be Methacryloxypropyltrimethoxysilane (CAS NO .: 2530-85-0) to improve oxygen permeability, and has high lens characteristics (such as improved oxygen permeability).
상기 1-vinyl-2-pyrrolidone(NVP)은 친수성 단량체의 기질을 가진 물질로, 상기 Methacryloxypropyltrimethoxysilane와 1-vinyl-2-pyrrolidone 30 - 90 : 10 - 70%의 중량비율로 라디칼 중합한다. 라디칼 중합을 개시하기 위한 상기 중량비율은 적절한 렌즈의 형상을 유지하면서 대략 40% 이상의 고함수율을 가진 렌즈를 제조하기 위한 최적의 비율이다.The 1-vinyl-2-pyrrolidone (NVP) is a material having a substrate of a hydrophilic monomer, and is radically polymerized at a weight ratio of Methacryloxypropyltrimethoxysilane and 1-vinyl-2-pyrrolidone 30-90: 10-70%. The weight ratio for initiating radical polymerization is an optimal ratio for producing a lens having a high water content of approximately 40% or more while maintaining the proper lens shape.
여기서, 상기 Methacryloxypropyltrimethoxysilane와 1-vinyl-2-pyrrolidone의 라디칼 중합은 120 - 140℃의 온도에서 40 - 50분 동안 이루어지는 것이 바람직하다.Here, the radical polymerization of the Methacryloxypropyltrimethoxysilane and 1-vinyl-2-pyrrolidone is preferably carried out for 40-50 minutes at a temperature of 120-140 ℃.
이때, 상기 라디칼 중합과정에서 대략 100℃ 부근에서 120 내지 140℃에 도달하기 까지 온도를 서서히 상승시키는게 바람직한데, 이는 처음부터 너무 높은 온도에서 라디칼 중합할 경우 렌즈에 기포가 발생하여 불량 제품을 초래할 수 있으므로, 이 같은 현상을 방지하고자 온도를 서서히 상승시키는 것이다.At this time, in the radical polymerization process, it is preferable to gradually increase the temperature until it reaches 120 to 140 ° C. at about 100 ° C., which may cause bubbles in the lens when the radical polymerization is performed at too high a temperature from the beginning, resulting in a defective product. Therefore, the temperature is gradually raised to prevent such a phenomenon.
또한, 라디칼 중합 시간이 40분 미만 또는 50분을 초과할 경우 제조된 렌즈의 인장강도 및 습윤성 저하, 착용감이 열등해지거나, 라디칼 반응이 형성되지 않아 친수성 단량체로서의 기질을 발휘하지 못하므로, Methacryloxypropyltrimethoxysilane와 1-vinyl-2-pyrrolidone의 라디칼 중합 시간은 40 내지 50분이 바람직하다.In addition, when the radical polymerization time is less than 40 minutes or more than 50 minutes, the tensile strength and wettability of the manufactured lens, the wearability is inferior, or the radical reaction is not formed, and thus the substrate as a hydrophilic monomer is not exhibited. The radical polymerization time of 1-vinyl-2-pyrrolidone is preferably 40 to 50 minutes.
본 발명의 다른 실시예로서, 상기 1-vinyl-2-pyrrolidone을 대체하여 친수성 아크릴계 단량체이며, 입체 규칙성을 갖는 고분자의 일종으로 단량체 기반의 가교결합을 하는 Hydroxyethyl methacrylate(HEMA)를 사용할 수도 있다.As another embodiment of the present invention, hydroxyethyl methacrylate (HEMA), which is a hydrophilic acrylic monomer and replaces monomer-based crosslinks, may be used as a hydrophilic acrylic monomer by replacing 1-vinyl-2-pyrrolidone.
상기 단량체들이 중합을 개시하고 나서 중합 기작이 마무리되면, 여기에 N,N-dimethyl acrylamide(DMA) 또는 Ethylene glycol dimethacrylate(EGDMA) 중 단독 또는 이들의 혼합물을 첨가한다.When the polymerization mechanism is finished after the monomers start the polymerization, either alone or a mixture of N, N-dimethyl acrylamide (DMA) or Ethylene glycol dimethacrylate (EGDMA) is added thereto.
상기 N,N-dimethyl acrylamide(DMA)는 아크릴로니트릴(acrylonitrile)을 가수분해(화학반응 중 물분자가 작용하여 일어나는 분해반응)하여 만든 물질로, 물 속에서 중합시키면 임의의 가교도인 중합체(폴리아크릴아마드겔(polyacrylamide gel))를 임의의 형상으로 합성할 수 있다. 또한, 흡착성이 적고 보수성이 양호하며 열, 산알칼리 및 계면활성제에 강한 특성이 있다.The N, N-dimethyl acrylamide (DMA) is a material made by hydrolyzing acrylonitrile (decomposition reaction caused by the action of water molecules during a chemical reaction). Acrylamide gel (polyacrylamide gel) can be synthesized in any shape. In addition, it has a low adsorption property, good water retention, and has strong properties against heat, acid alkali and surfactant.
상기 Ethylene glycol dimethacrylate(EGDMA)는 물질을 합성하는 일종의 가교제 역할을 하는 것으로, 본 발명의 일 실시예에 따르면 상기 N,N-dimethyl acrylamide 또는 Ethylene glycol dimethacrylate 중 어느 하나 또는 이들을 혼합한 혼합물을 사용할 수 있다. 이때, 상기 N,N-dimethyl acrylamide와 Ethylene glycol dimethacrylate를 혼합할 경우 동일비율로 혼합하는게 바람직하다. 이는 어느 한 물질이 많거나 적게 되면 고분자의 합성이 과도하게 일어나 소수성 단량체 및 친수성 반응기로 기능화된 친수성 단량체가 일체화되거나, 각 물질들간의 혼합 내지는 합성이 곤란하기 때문이다.The ethylene glycol dimethacrylate (EGDMA) serves as a kind of crosslinking agent for synthesizing a material, and according to an embodiment of the present invention, any one or a mixture of N, N-dimethyl acrylamide or ethylene glycol dimethacrylate may be used. . In this case, when the N, N-dimethyl acrylamide and Ethylene glycol dimethacrylate is mixed, it is preferable to mix the same ratio. This is because when one material is more or less, the synthesis of the polymer is excessive, so that the hydrophobic monomer and the hydrophilic monomer functionalized by the hydrophilic reactor are integrated, or mixing or synthesis between the materials is difficult.
상기 과정을 거쳐서 Azobisisobutyronitrile(AIBN)으로 Terpolymer를 라디칼 중합하여 콘택트렌즈 제조용 조성물을 제조한다.Through the above process, a terpolymer is polymerized with Azobisisobutyronitrile (AIBN) to prepare a composition for preparing a contact lens.
상기 Azobisisobutyronitrile은 화학식 (CH3)2C(CN)2N2를 갖는 유기 화합물로서, 일반적인 유기 용제에는 용해되지만 물에는 용해되지 않는 특성이 있다. 본 발명에 있어서 상기 Azobisisobutyronitrile은 라디칼 중합을 위한 개시제로서 하기 화학식으로 이루어진다.Azobisisobutyronitrile is an organic compound having the formula (CH 3 ) 2 C (CN) 2 N 2, and is soluble in a general organic solvent but insoluble in water. In the present invention, Azobisisobutyronitrile is composed of the following formula as an initiator for radical polymerization.
이때, 상기 Terpolymer 합성이 진행되는데, 상기 Terpolymer는 공중합체 중 3종류의 단량체로 형성된 것으로 상기한 단량체들과의 기계적 강도를 유지하는데 도움을 주며, 또 단량체들간의 중합 친수성 단량체(아크릴계)와 소수성 단량체(실리콘계)들의 결합이 자연스럽게 이루어지도록 한다.At this time, the terpolymer synthesis is carried out, the terpolymer is formed of three kinds of monomers to help maintain the mechanical strength with the above-mentioned monomers, and polymerized hydrophilic monomer (acrylic) and hydrophobic monomer between the monomers Allow the combination of (silicon-based) to occur naturally.
한편, 상기 과정을 거쳐 제조된 콘택트렌즈 제조용 조성물은 전면부 또는 후면부 중 어느 하나의 면이 볼록형상인 몰드에 주입하여 도 1에 나타낸 바와 같은 렌즈로 사출한다.On the other hand, the composition for manufacturing a contact lens prepared by the above process is injected into the mold as shown in Figure 1 by injecting a surface of any one of the front or rear portion of the convex shape.
일 구현예로서, 도면에는 도시되지 않았지만 상기 몰드는 상부몰드와 하부몰드를 포함할 수 있으며, 상기 하부몰드에는 실린더교정면과 구면교정면을 형성하고, 원기둥 형상의 상부몰드를 결합하여 렌즈를 제조하되, 상기 하부몰드와 상부몰드 사이의 공간부에 콘택트렌즈 제조용 조성물을 주입하여 제조된 렌즈의 전면에는 근시, 원시를 위한 주형 광학부와 난시를 위한 원주형 광학부를 동시에 형성시킬 수 있다.As an embodiment, although not shown in the drawing, the mold may include an upper mold and a lower mold, and the lower mold forms a cylinder calibration surface and a spherical calibration surface, and combines a cylindrical upper mold to manufacture a lens. However, the front surface of the lens prepared by injecting a composition for manufacturing a contact lens into the space between the lower mold and the upper mold may be formed at the same time to the myopia, mold optics for hyperopia and cylindrical optics for astigmatism.
또한, 상기 렌즈는 볼록곡면형상의 전면부와 오목곡면형상의 후면부로 이루어질 수 있으며, 렌즈의 상단에서 하단으로 갈수록 두께가 점차 두꺼워지도록 형성되는 것으로, 렌즈의 후면부는 곡면중심으로부터 동일한 반지름을 가지도록 형성되고, 전면부는 상단에서 하단으로 갈수록 곡면중심으로부터의 거리가 점차 길어지도록 형성됨으로써 종래의 실리콘 렌즈보다 착용감을 더욱 극대화시킬 수 있는 것이다.In addition, the lens may be formed of a convex curved front portion and a concave curved rear portion, and is formed to gradually increase in thickness from the top to the bottom of the lens, so that the rear portion of the lens has the same radius from the curved center. It is formed, the front portion is formed so that the distance from the center of the curved surface is gradually longer from the top to the bottom to be able to maximize the wear more than conventional silicon lenses.
또, 상기 하부몰드에는 실린더교정면 및 구면교정면이 형성되는데, 상기 하부몰드의 오목한 표면은 렌즈의 주형 광학부, 원주형 광학부를 형성하기 위해 오목한 반구홈이 형성된 하부몰드의 수평지름을 기준으로 하여 하반구면에는 실린더 교정면이 형성되고, 상반구면에는 구면교정면이 형성될 수 있다.In addition, the lower mold is formed with a cylinder calibration surface and a spherical surface, the concave surface of the lower mold is based on the horizontal diameter of the lower mold formed with a concave hemisphere groove to form the mold optical portion, the cylindrical optical portion of the lens. Thus, a cylinder calibration surface may be formed on the lower hemisphere, and a spherical calibration surface may be formed on the upper hemisphere.
따라서, 제조된 렌즈의 두께는 상기 구면교정면에 의해 형성된 주형광학부로부터 실린더교정면에 의해 형성된 원주형 광학부로 갈수록 점차 두꺼워지도록 형성되는 것이다.Therefore, the thickness of the manufactured lens is formed to gradually become thicker from the mold optical portion formed by the spherical surface to the cylindrical optical portion formed by the cylinder surface.
사출공정이 완료된 렌즈는 도 2에 나타낸 바와 같이, 단부를 유선형의 엣지(edge) 형태로써 성형한다. 렌즈의 양 끝단을 엣지 처리, 즉 렌즈를 착용하고 눈을 깜박였을 때 렌즈의 아래쪽과 위쪽으로 적절한 눈물 순환을 시켜줄 수 있는 형상을 채택함으로써 종래 실리콘 렌즈에서 부각된 문제점인 단백질 침착의 감소, 감염에 의한 안질환의 위험 감소, 일반렌즈보다 편한 착용감, 연속착용에 대한 부작용의 감소 등을 해결할 수 있다. 다시 말해 끝 단부 부분이 라운드진 형상임에 따라 사용자의 눈에 착용 시 결막과 상안점에 자극을 주지 않아 착용감이 우수해지는 것이다.After the injection process is completed, the lens is molded in the form of a streamlined edge as shown in FIG. 2. Edge treatment at both ends of the lens, that is, a shape that allows proper tear circulation to the bottom and top of the lens when the lens is worn and the eye blinks, reduces protein deposition and infection, which is a problem of conventional silicone lenses. It can reduce the risk of eye diseases, comfortable fit than ordinary lenses, and reduce the side effects of continuous wearing. In other words, as the end portion is rounded shape, it does not irritate the conjunctiva and the eyepiece when worn on the user's eyes, thereby improving the fit.
이하, 실시예 및 실험예를 통하여 본 발명을 더욱 구체적으로 설명하기로 한다.Hereinafter, the present invention will be described in more detail with reference to Examples and Experimental Examples.
[실시예]EXAMPLE
(a) Methacryloxypropyltrimethoxysilane과 1-vinyl-2-pyrrolidone이 공중합된 물질 100g에 N,N-dimethyl acrylamide(DMA)와 Ethylene glycol dimethacrylate(EGDMA)의 혼합물과 Azobisisobutyronitrile(AIBN)으로 Terpolymer를 라디칼 중합하여 콘택트렌즈 제조용 조성물을 제조한 다음 (b) 제조된 콘택트렌즈 제조용 조성물을 몰드에 주입하여 볼록형상인 렌즈로 사출한 후, 사출된 렌즈의 단부는 유선형의 엣지(edge) 형태로 성형하였다.(a) Contact lens production by radical polymerization of terpolymer with a mixture of N, N-dimethyl acrylamide (DMA) and Ethylene glycol dimethacrylate (EGDMA) and Azobisisobutyronitrile (AIBN) in 100 g of methacryloxypropyltrimethoxysilane and 1-vinyl-2-pyrrolidone copolymerized After the composition was prepared, (b) the prepared composition for preparing a contact lens was injected into a mold and injected into a convex lens, and the end of the injected lens was molded into a streamlined edge shape.
라디칼 중합 조건은 130℃로 40분간 가열하였으며, 상기 N,N-dimethyl acrylamide(DMA), Ethylene glycol dimethacrylate(EGDMA) 및 Azobisisobutyronitrile(AIBN)은 조성비를 달리하여 총 4개의 하이드로겔 렌즈(P1, P2, P3, P4)를 제조하였고, 그 조성비는 하기 표 1에 나타내었다.The radical polymerization conditions were heated to 130 ℃ for 40 minutes, the N, N-dimethyl acrylamide (DMA), Ethylene glycol dimethacrylate (EGDMA) and Azobisisobutyronitrile (AIBN) were a total of four hydrogel lenses (P1, P2, P3, P4) were prepared, and the composition ratio thereof is shown in Table 1 below.
(DMA)N, N-dimethyl acrylamide
(DMA)
(AIBN)
Azobisisobutyronitrile
(AIBN)
(EGDMA)Ethylene glycol dimethacrylate
(EGDMA)
[실험예]Experimental Example
상기 실시예의 P1, P2, P3 및 P4의 하이드로겔 렌즈의 효과를 확인하기 위해 함수율(water content), 광투과율(optical transmittence) 및 산소투과율(oxygen transmittance)을 측정하였다.In order to confirm the effect of the hydrogel lens of the P1, P2, P3 and P4 of the above embodiment, the water content, optical transmittence and oxygen transmittance were measured.
상기 함수율의 측정(%)은 실시예의 P1, P2, P3 및 P4의 하이드로겔 렌즈는 0.9% 염화나트륨(NaCl) 생리 식염수에 24시간 동안 침지시킨 후, ISO 18369-4의 gravimetric method에 의해 측정하였다.The water content (%) of the hydrogel lens of P1, P2, P3 and P4 of the Example was immersed in 0.9% sodium chloride (NaCl) saline for 24 hours, and then measured by the gravimetric method of ISO 18369-4.
상기 광투과율(%)은 가시광선 영역(380 - 720㎚)에서 TOPCON의 TM-2를 이용하여 측정하였다.The light transmittance (%) was measured using TOPCON TM-2 in the visible light region (380-720 nm).
상기 산소투과율(Dk/t)은 Rdhder development company사의 O2 permeometer 201T로 측정하였다. The oxygen permeability (Dk / t) was measured by O 2 permeometer 201T of Rdhder development company.
한편, 측정의 정확도를 높이기 위하여 각각 3번씩 반복측정하였고, 측정한 값의 평균을 구해 하기 표 2에 나타내었다.On the other hand, in order to increase the accuracy of the measurement was repeated three times each, and the average of the measured values are shown in Table 2 below.
상기 표 2를 참조하여 설명하면, 본 발명에 따른 하이드로겔 렌즈는 산소투과율이 뛰어나면서 약 40% 정도의 함수율을 가지기 때문에 콘택트렌즈로서 매우 우수하다는 것을 확인할 수 있다.Referring to Table 2, it can be seen that the hydrogel lens according to the present invention is very excellent as a contact lens because the oxygen transmittance is excellent and has a water content of about 40%.
또한, 본 발명에 따른 하이드로겔 렌즈는 광투과율 및 산소투과율이 우수하기 때문에 눈의 건조감 및 충혈을 줄여줄 수 있어 장시간 동안 착용하기에 적합하다는 결론을 도출할 수 있다.In addition, since the hydrogel lens according to the present invention has excellent light transmittance and oxygen transmittance, it is possible to reduce the dryness and redness of the eyes, and thus, it can be concluded that it is suitable for wearing for a long time.
Claims (5)
b) 상기 a)단계의 콘택트렌즈 제조용 조성물을 몰드에 주입하여 전면부 또는 후면부 중 어느 하나의 면이 볼록형상인 렌즈로 사출한 후, 사출된 렌즈의 단부를 유선형의 엣지(edge) 형태로 성형하여 형성되는 것을 특징으로 하는 친수성 터폴리머와 실리콘을 공중합한 실리콘 하이드로겔 렌즈의 제조방법.
[화학식 1]
[화학식 2]
b) injecting the composition for preparing the contact lens of step a) into a mold and injecting the lens into a convex lens on either side of the front part or the rear part, and molding the end of the injected lens into a streamlined edge shape. Method for producing a silicone hydrogel lens copolymerized with a hydrophilic terpolymer and silicone, characterized in that formed.
[Formula 1]
[Formula 2]
상기 a)단계의 라디칼 중합은 120 - 140℃의 온도에서 40 - 50분 동안 이루어지는 것을 특징으로 하는 친수성 터폴리머와 실리콘을 공중합한 실리콘 하이드로겔 렌즈의 제조방법.According to claim 1,
The radical polymerization of step a) is a method for producing a silicone hydrogel lens copolymerized with a hydrophilic terpolymer and silicone, characterized in that for 40 to 50 minutes at a temperature of 120-140 ℃.
상기 b)단계의 성형된 렌즈는 전면부가 상단에서 하단으로 갈수록 곡면중심으로부터의 거리가 점차 길어지도록 형성되고, 후면부가 곡면중심으로부터 동일한 반지름을 갖도록 형성되는 것을 특징으로 하는 친수성 터폴리머와 실리콘을 공중합한 실리콘 하이드로겔 렌즈의 제조방법.According to claim 1,
The molded lens of step b) is formed so that the distance from the center of the curved surface is gradually longer from the upper end to the lower end, and the hydrophilic terpolymer and silicone is characterized in that the rear end is formed to have the same radius from the curved center. Method for producing a silicone hydrogel lens.
상기 1-vinyl-2-pyrrolidone(NVP)은 라디칼 중합을 위한 비닐기를 가진 구조인 것을 특징으로 하는 친수성 터폴리머와 실리콘을 공중합한 실리콘 하이드로겔 렌즈의 제조방법.According to claim 1,
The 1-vinyl-2-pyrrolidone (NVP) is a method of manufacturing a silicone hydrogel lens copolymerized with a hydrophilic terpolymer and silicon, characterized in that the structure having a vinyl group for radical polymerization.
Silicone hydrogel lens copolymerized with a hydrophilic terpolymer and silicone prepared by any one of claims 1 to 4.
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| KR100901806B1 (en) | 2002-04-10 | 2009-06-11 | 탈렉스 옵티칼 컴파니 리미티드 | Polyurethane resin composition for optical lenses and impact strength synthentic resin lenses |
| KR101123644B1 (en) | 2010-01-13 | 2012-03-20 | 뉴바이오 (주) | Contact lens comprising titanium dioxide and preparation method thereof |
| KR101556995B1 (en) * | 2015-03-09 | 2015-10-06 | 주식회사 비에스코퍼레이션 | Manufacturing method of toric lens |
| KR101796910B1 (en) | 2009-12-28 | 2017-11-13 | 존슨 앤드 존슨 비젼 케어, 인코포레이티드 | Macromonomer mixture, terminal-reactive polymer mixture, intermediate for macromonomer and silicone hydrogel |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR100901806B1 (en) | 2002-04-10 | 2009-06-11 | 탈렉스 옵티칼 컴파니 리미티드 | Polyurethane resin composition for optical lenses and impact strength synthentic resin lenses |
| KR101796910B1 (en) | 2009-12-28 | 2017-11-13 | 존슨 앤드 존슨 비젼 케어, 인코포레이티드 | Macromonomer mixture, terminal-reactive polymer mixture, intermediate for macromonomer and silicone hydrogel |
| KR101123644B1 (en) | 2010-01-13 | 2012-03-20 | 뉴바이오 (주) | Contact lens comprising titanium dioxide and preparation method thereof |
| KR101556995B1 (en) * | 2015-03-09 | 2015-10-06 | 주식회사 비에스코퍼레이션 | Manufacturing method of toric lens |
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