KR102145367B1 - Noble hydrophilic silicone compound, method for preparation thereof and silicone hydrogel contact lens containing the same - Google Patents
Noble hydrophilic silicone compound, method for preparation thereof and silicone hydrogel contact lens containing the same Download PDFInfo
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Abstract
본 발명은 신규한 친수성 실리콘 화합물, 이의 제조방법 및 이를 이용한 실리콘 하이드로겔 콘택트 렌즈에 관한 것으로서, 보다 상세하게는 친수성의 폴리에틸렌 글리콜(polyethyleneglycol; PEG) 사슬을 포함하며, 중합을 위한 이중결합을 가지는 하기 화학식 1로 나타내는 신규한 폴리실록산 구조의 단량체, 이의 제조방법, 및 상기 폴리실록산 단량체를 포함하는 실리콘 하이드로겔 콘택트 렌즈에 관한 것이다.
[화학식 1]
여기서,
n은 1 내지 10의 정수이고,
R은 수소 원자, 또는 하이드록실, 산, 에스테르, 에테르, 티올 및 이들의 조합으로 치환될 수 있는 1 내지 20개의 탄소 원자를 갖는 C1-20 알킬기 또는 아릴기임.The present invention relates to a novel hydrophilic silicone compound, a method for producing the same, and a silicone hydrogel contact lens using the same, and more particularly, to a hydrophilic polyethylene glycol (PEG) chain, and having a double bond for polymerization The present invention relates to a monomer having a novel polysiloxane structure represented by Chemical Formula 1, a method for preparing the same, and a silicone hydrogel contact lens including the polysiloxane monomer.
[Formula 1]
here,
n is an integer from 1 to 10,
R is a hydrogen atom or a C 1-20 alkyl group or aryl group having 1 to 20 carbon atoms which may be substituted with hydroxyl, acid, ester, ether, thiol, and combinations thereof.
Description
본 발명은 신규한 친수성 실리콘 화합물, 이의 제조방법 및 이를 이용한 실리콘 하이드로겔 콘택트 렌즈에 관한 것으로서, 보다 상세하게는 콘택트 렌즈용 하이드로겔 중합체로서 사용하기 위해 친수성의 폴리에틸렌 글리콜( polyethyleneglycol; PEG) 사슬을 포함하며, 중합을 위한 이중결합을 가지는 신규한 폴리실록산 구조의 단량체, 이의 제조방법, 및 상기 폴리실록산 단량체를 포함하는 실리콘 하이드로겔 콘택트 렌즈에 관한 것이다.The present invention relates to a novel hydrophilic silicone compound, a method for producing the same, and a silicone hydrogel contact lens using the same, and more particularly, to a hydrogel polymer for contact lenses, including a hydrophilic polyethylene glycol (PEG) chain And, the present invention relates to a monomer having a novel polysiloxane structure having a double bond for polymerization, a method for preparing the same, and a silicone hydrogel contact lens including the polysiloxane monomer.
콘택트 렌즈 제조용 단량체로서, 다양한 실리콘-포함 단량체들이 개발되어 왔으며, 현재 실리콘 하이드로겔로 만들어진 콘택드 렌즈가 일반적으로 제조되고 있다. As a monomer for manufacturing a contact lens, various silicone-containing monomers have been developed, and a contact lens made of a silicone hydrogel is generally manufactured.
상기 실리콘 하이드로겔은 높은 산소 투과율을 갖는 수팽윤성의 망상 중합체로서, 예를 들면, 3-[트리스(트리메틸실록시)실릴]프로필 메타크릴레이트 등을 콘택트 렌즈 제조용 단량체로써 널리 사용할 수 있다. The silicone hydrogel is a water-swellable network polymer having a high oxygen permeability, and, for example, 3-[tris(trimethylsiloxy)silyl]propyl methacrylate, etc., can be widely used as a contact lens manufacturing monomer.
상기와 같은 콘택트 렌즈용 단량체를 제조하는 종래기술로서, 공개특허공보 제10-2011-0074517호(2011.06.30.)에서는 분지형 연결기를 갖는 폴리에테르를 함유하는 모노-(메트)아크릴레이트 작용화된 친수성 실리콘 단량체에 관해 기재되어 있고, 공개특허공보 제10-2013-0016295호(2013.02.14.)에서는 분자 내에 2개 이상의 -OSi 반복 단위들을 갖는 직쇄 실록사닐기 및 (메트)아크릴아미드기를 포함하는, 실리콘 (메트)아크릴아미드 단량체에 관해 기재되어 있으며, 공개특허공보 제10-2009-0077923호(2009.07.16.)에서는 입체장애적 가수분해-저항성 실리콘 화합물 및 이의 제조방법에 관해 기재되어 있다. As a prior art for preparing the contact lens monomer as described above, Unexamined Patent Publication No. 10-2011-0074517 (2011.06.30.) has a mono-(meth)acrylate functionalization containing a polyether having a branched linking group. The hydrophilic silicone monomer is described, and in Unexamined Patent Publication No. 10-2013-0016295 (2013.02.14.), a straight-chain siloxanyl group and a (meth)acrylamide group having two or more -OSi repeat units in the molecule are included. In the following, a silicone (meth)acrylamide monomer is described, and in Unexamined Patent Publication No. 10-2009-0077923 (2009.07.16), a steric hindrance hydrolysis-resistant silicone compound and a method for producing the same are described. .
그러나 종래 기술에 따른 실리콘 단량체들은 소수성을 띄기 때문에 이들 단량체를 이용하여 제조된 하이드로겔 렌즈의 함수율은 낮았다. 따라서, 2-히드록시에틸 메타아크릴레이트(HEMA, 2-Hydroxyethyl methacrlyate) 등의 친수성 단량체들과 같이 중합에 사용되어 콘택트 렌즈 재료로 사용되고 있다. 하지만, 상기 소수성 실리콘 단량체들은 친수성의 다른 단량체들과 섞이지 않기 때문에 제조된 렌즈가 혼탁해져 광투과율이 낮은 단점을 가졌고, 함수율도 좋지 않았다.However, since silicone monomers according to the prior art exhibit hydrophobicity, the water content of the hydrogel lens manufactured using these monomers was low. Therefore, it is used for polymerization and is used as a contact lens material with hydrophilic monomers such as 2-hydroxyethyl methacrylate (HEMA, 2-Hydroxyethyl methacrlyate). However, since the hydrophobic silicone monomers are not mixed with other hydrophilic monomers, the prepared lens becomes cloudy, resulting in low light transmittance and poor moisture content.
따라서 친수성의 실리콘 단량체를 제조하여 HEMA 등과 혼합하여 하이드로겔 렌즈를 제조하면, 산소 투과성, 광투과율과 습윤성을 동시에 높일 수 있기 때문에, 신규한 실리콘 화합물의 개발에 대한 연구는 지속적으로 요구되고 있다. Therefore, when a hydrogel lens is prepared by preparing a hydrophilic silicone monomer and mixing it with HEMA, etc., oxygen permeability, light transmittance, and wettability can be simultaneously increased, and thus research on the development of a novel silicone compound is continuously required.
최근 산소투과율을 높이기 위해 실리콘 소재를 사용한 고 산소투과율 실리콘 하이드로겔 렌즈(Si-Hy)의 연구가 활발하게 이루어지고 있으며, 특히 산소친화성 실록산(siloxane)에 대한 연구 및 특허가 보고된 바 있다.Recently, in order to increase the oxygen permeability, research on a high oxygen permeability silicone hydrogel lens (Si-Hy) using a silicone material has been actively conducted, and in particular, research and patents on oxygen-affinity siloxane have been reported.
이에, 본 발명자들은 기존 실록산 마크로머(siloxane macromer)의 구조와 다른 새로운 실록산 마크로머(siloxane macromer)를 쉬운 합성방법으로 디자인하여 높은 산소투과율과 함수율을 구현하면서 저렴한 가격에 공급할 수 있음을 밝힘으로써, 본 발명을 완성하였다.Accordingly, the inventors of the present invention revealed that by designing a new siloxane macromer different from the structure of the existing siloxane macromer by an easy synthesis method, it can be supplied at a low price while realizing high oxygen permeability and moisture content, The present invention has been completed.
본 발명의 목적은 상술한 바와 같이 종래 기술에 따른 실리콘 단량체들의 문제점들을 개선하기 위해 발명된 것으로써, 친수성 부분을 포함하며 산소투과성과 습윤성을 높일 수 있는 콘택트 렌즈에 사용될 수 있는 신규한 실리콘 화합물 및 이의 제조방법을 제공하는 것이다.An object of the present invention was invented to improve the problems of silicone monomers according to the prior art as described above, and a novel silicone compound that can be used in a contact lens that includes a hydrophilic portion and can increase oxygen permeability and wettability, and It is to provide a manufacturing method thereof.
본 발명의 또다른 목적은 상기 본 발명에 따른 신규한 실리콘 화합물을 단량체로서 사용하여 중합반응을 통해 얻어지는 콘택트 렌즈용 하이드로겔 조성물을 제공하는 것이다. Another object of the present invention is to provide a hydrogel composition for a contact lens obtained through a polymerization reaction using the novel silicone compound according to the present invention as a monomer.
본 발명의 또다른 목적은 상기 본 발명에 따른 콘택트 렌즈용 하이드로겔 조성물을 포함하는 콘택트 렌즈를 제공하는 것이다. Another object of the present invention is to provide a contact lens comprising the hydrogel composition for a contact lens according to the present invention.
상기 목적을 달성하기 위하여, 본 발명은 하기 화학식 1로 표시되는 실리콘 함유 단량체:In order to achieve the above object, the present invention is a silicone-containing monomer represented by the following formula (1):
[화학식 1][Formula 1]
(여기서,(here,
n은 1 내지 10의 정수이고,n is an integer from 1 to 10,
R은 수소 원자, 또는 하이드록실, 산, 에스테르, 에테르, 티올 및 이들의 조합으로 치환될 수 있는 1 내지 20개의 탄소 원자를 갖는 C1-20 알킬기 또는 아릴기임.)를 제공한다.R is a hydrogen atom or a C 1-20 alkyl group or aryl group having 1 to 20 carbon atoms which may be substituted with hydroxyl, acid, ester, ether, thiol, and combinations thereof.).
또한, 본 발명은 In addition, the present invention
i) H2PDMS(H2Polydimethylsiloxane)와 PEGMA(poly(ethylene glycol) methyl ether methacrylate)를 촉매 존재 하에 반응시켜 PEG-PDMS-PEG를 제조하는 단계;i) preparing PEG-PDMS-PEG by reacting H 2 PDMS (H 2 Polydimethylsiloxane) and PEGMA (poly(ethylene glycol) methyl ether methacrylate) in the presence of a catalyst;
ii) IPDI(Isophorone diisocyanate)와 HEMA(2-hydroxyethyl methacrylate)를 반응시켜 IPDI-HEMA를 제조하는 단계; 및ii) preparing IPDI-HEMA by reacting IPDI (Isophorone diisocyanate) and HEMA (2-hydroxyethyl methacrylate); And
iii) 상기 PEG-PDMS-PEG와 상기 IPDI-HEMA를 촉매 존재 하에 반응시켜 PDMS 말단반응성고분자(macromer)를 제조하는 단계;를 포함하는,iii) preparing a PDMS terminal reactive polymer (macromer) by reacting the PEG-PDMS-PEG and the IPDI-HEMA in the presence of a catalyst; including,
상기 본 발명에 따른 화학식 1로 표시되는 실리콘 함유 단량체의 합성 방법을 제공한다.It provides a method for synthesizing the silicone-containing monomer represented by Chemical Formula 1 according to the present invention.
또한, 본 발명은 상기 본 발명에 화학식 1로 표시되는 실리콘 함유 단량체를 포함하는 중합체를 제공한다.In addition, the present invention provides a polymer containing the silicone-containing monomer represented by Formula 1 in the present invention.
또한, 본 발명은 상기 본 발명에 화학식 1로 표시되는 실리콘 함유 단량체 또는 이의 중합체를 포함하는 콘택트 렌즈를 제공한다.In addition, the present invention provides a contact lens comprising a silicone-containing monomer represented by Formula 1 or a polymer thereof in the present invention.
아울러, 본 발명은 In addition, the present invention
a) 상기 화학식 1로 표시되는 실리콘 함유 단량체 2 내지 80 wt%, pHEMA[poly(2-hydroxyethyl methacrylate)] 15 내지 90 wt%, 친수성 모노머 0.1 내지 60 wt, 가교제 0.05 내지 10 wt% 및 중합개시제 0.05 내지 5 wt%를 혼합하여 교반하는 단계; 및a) 2 to 80 wt% of the silicone-containing monomer represented by Chemical Formula 1, 15 to 90 wt% of pHEMA [poly(2-hydroxyethyl methacrylate)], 0.1 to 60 wt of hydrophilic monomer, 0.05 to 10 wt% of crosslinking agent, and 0.05 of polymerization initiator Mixing and stirring to 5 wt%; And
b) 상기 a)에서 혼합된 혼합물을 모드에 주입한 후 가열하여 중합시키는 단계;를 포함하는 콘택트 렌즈의 제조 방법을 제공한다.b) injecting the mixture mixed in a) into a mode, followed by heating to polymerize it. It provides a method of manufacturing a contact lens comprising.
상기에서 살펴본 바와 같이, 본 발명에 따른 화학식 1로 표시되는 실리콘계 화합물은 친수성 부분에 해당하는 PEG를 양쪽에 포함함으로써, 습윤성을 높일 수 있고, 중합에 의해 얻어지는 하이드로겔 조성물은 산소투과성이 향상되어 콘택트 렌즈에 유용하게 사용될 수 있다. As described above, the silicone-based compound represented by Formula 1 according to the present invention can increase wettability by including PEG corresponding to the hydrophilic moiety on both sides, and the hydrogel composition obtained by polymerization improves oxygen permeability to contact It can be usefully used for lenses.
도 1은 본 발명에 따른 화학식 1로 표시되는 실리콘계 화합물의 합성 과정을 보여주는 그림이다.1 is a diagram showing a synthesis process of a silicone compound represented by Formula 1 according to the present invention.
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
본 발명은 The present invention
하기 화학식 1로 표시되는 실리콘 함유 단량체:Silicone-containing monomer represented by the following formula (1):
(여기서,(here,
n은 1 내지 10의 정수이고,n is an integer from 1 to 10,
R은 수소 원자, 또는 하이드록실, 산, 에스테르, 에테르, 티올 및 이들의 조합으로 치환될 수 있는 1 내지 20개의 탄소 원자를 갖는 C1-20 알킬기 또는 아릴기임.)를 제공한다.R is a hydrogen atom or a C 1-20 alkyl group or aryl group having 1 to 20 carbon atoms which may be substituted with hydroxyl, acid, ester, ether, thiol, and combinations thereof.).
상기 실리콘 함유 단량체는 친수성의 폴리에틸렌 글리콜( polyethyleneglycol; PEG) 사슬을 포함하며, 중합을 위한 이중결합을 가지고 있다.The silicone-containing monomer includes a hydrophilic polyethylene glycol (PEG) chain and has a double bond for polymerization.
상기 실리콘 함유 단량체는 친수성 부분을 포함하며 산소투과성과 습윤성을 높일 수 있는 콘택트 렌즈에 사용될 수 있다.The silicone-containing monomer includes a hydrophilic moiety and can be used in a contact lens capable of enhancing oxygen permeability and wettability.
또한, 본 발명은 In addition, the present invention
i) H2PDMS(H2Polydimethylsiloxane)와 PEGMA(poly(ethylene glycol) methyl ether methacrylate)를 촉매 존재 하에 반응시켜 PEG-PDMS-PEG를 제조하는 단계;i) preparing PEG-PDMS-PEG by reacting H 2 PDMS (H 2 Polydimethylsiloxane) and PEGMA (poly(ethylene glycol) methyl ether methacrylate) in the presence of a catalyst;
ii) IPDI(Isophorone diisocyanate)와 HEMA(2-hydroxyethyl methacrylate)를 반응시켜 IPDI-HEMA를 제조하는 단계; 및ii) preparing IPDI-HEMA by reacting IPDI (Isophorone diisocyanate) and HEMA (2-hydroxyethyl methacrylate); And
iii) 상기 PEG-PDMS-PEG와 상기 IPDI-HEMA를 촉매 존재 하에 반응시켜 PDMS 말단반응성고분자(macromer)를 제조하는 단계;를 포함하는,iii) preparing a PDMS terminal reactive polymer (macromer) by reacting the PEG-PDMS-PEG and the IPDI-HEMA in the presence of a catalyst; including,
상기 본 발명에 따른 화학식 1로 표시되는 실리콘 함유 단량체의 합성 방법을 제공한다.It provides a method for synthesizing the silicone-containing monomer represented by Chemical Formula 1 according to the present invention.
상기 합성 방법은 도 1과 같이 수행되는 것이 바람직하며, 이때 사용되는 촉매의 종류, 반응 시간 및 온도는 당업계에 알려져 있는 방법으로 변경 가능하다.The synthesis method is preferably carried out as shown in FIG. 1, and the type, reaction time, and temperature of the catalyst used at this time can be changed by methods known in the art.
상기 합성 방법은 Hydride terminated-poly(dimethylsiloxane) (H2PDMS)와 poly(ethylene glycol) methacrylate(PEGMA)를 Karstedt′s Catalyst하에 hydrosilylation 반응을 통해 PEG-PDMS-PEG를 합성하는 제1단계; Isophorone diisocyanate (IPDI)와 2-hydroxyethyl methacrylate (HEMA)와의 urethane 반응을 통해, isocyanate기가 적용된 HEMA인 I-HMEA를 합성하는 제2단계; 바로 1/2 당량의 PEG-PDMS-PEG를 넣고, dibutyltin tin dilaurate (DBTDL) 촉매하에 urethane반응을 수행하여, methacrylate기가 양쪽에 연결된 친수성의 PDMS macromer를 합성하는 제3단계를 포함한다.The synthesis method includes a first step of synthesizing PEG-PDMS-PEG through a hydrosilylation reaction of Hydride terminated-poly(dimethylsiloxane) (H2PDMS) and poly(ethylene glycol) methacrylate (PEGMA) under Karstedt's Catalyst; A second step of synthesizing I-HMEA, HEMA to which an isocyanate group is applied, through urethane reaction between isophorone diisocyanate (IPDI) and 2-hydroxyethyl methacrylate (HEMA); It includes a third step of synthesizing a hydrophilic PDMS macromer having a methacrylate group connected to both sides by immediately adding 1/2 equivalent of PEG-PDMS-PEG, and performing urethane reaction under the catalyst of dibutyltin tin dilaurate (DBTDL).
또한, 본 발명은 상기 본 발명에 화학식 1로 표시되는 실리콘 함유 단량체를 포함하는 중합체를 제공한다.In addition, the present invention provides a polymer containing the silicone-containing monomer represented by Formula 1 in the present invention.
또한, 본 발명은 상기 본 발명에 화학식 1로 표시되는 실리콘 함유 단량체 또는 이의 중합체를 포함하는 콘택트 렌즈를 제공한다.In addition, the present invention provides a contact lens comprising a silicone-containing monomer represented by Formula 1 or a polymer thereof in the present invention.
본 발명에 따른 실리콘 하이드로겔 중합체는 습윤성을 높일 수 있고, 또한 중합에 의해 얻어지는 하이드로겔 조성물은 산소투과성이 향상되어 콘택트 렌즈에 유용하게 사용될 수 있다. The silicone hydrogel polymer according to the present invention can improve wettability, and the hydrogel composition obtained by polymerization has improved oxygen permeability and can be usefully used in contact lenses.
본 발명에 따른 실리콘 하이드로겔 중합체에 있어서, 상기 화학식 1로 표시되는 실리콘 함유 단량체의 함량은 1 ~ 98 wt%의 범위로 사용될 수 있고, 바람직하게는 2 ~ 80 wt%의 범위로 사용될 수 있으며, 더욱 바람직하게는 5 ~ 30 wt%의 범위로 사용될 수 있다. In the silicone hydrogel polymer according to the present invention, the content of the silicone-containing monomer represented by Formula 1 may be used in the range of 1 to 98 wt%, preferably in the range of 2 to 80 wt%, More preferably, it may be used in the range of 5 to 30 wt%.
본 발명에 따른 실리콘 하이드로겔 중합체는 상기 화학식 1로 표시되는 실리콘 함유 단량체 외에 추가적인 단량체를 포함할 수 있으며, 상기 추가적인 단량체로서 2-히드록시에틸 메타아크릴레이트(2-Hydroxyethyl methacrlyate, HEMA)가 사용될 수 있다. The silicone hydrogel polymer according to the present invention may include an additional monomer in addition to the silicone-containing monomer represented by Formula 1, and as the additional monomer, 2-hydroxyethyl methacrylate (HEMA) may be used. have.
본 발명에 따른 실리콘 하이드로겔 중합체는 친수성 모노머 및 가교제 중 어느 하나 이상을 추가적으로 포함할 수 있고, 중합반응을 위한 중합개시제를 포함할 수 있다.The silicone hydrogel polymer according to the present invention may additionally include any one or more of a hydrophilic monomer and a crosslinking agent, and may include a polymerization initiator for a polymerization reaction.
본 발명에 따른 실리콘 하이드로겔 중합체는 상기 본 발명에 화학식 1로 표시되는 실리콘계 화합물, 2-히드록시에틸 메타아크릴레이트, 친수성 모노머, 가교제, 중합개시제 등의 추가적으로 포함될 수 있는 성분과 함께 각각의 구성비에 따라 혼합한 후 30분 내지 10시간정도 0℃ 내지 40℃에서 예비적으로 교반한 다음, 메탄올, 에탄올, 물, 아세톤 중에서 선택되는 어느 하나 또는 이들의 혼합액을 용매로 사용하여 혼합한 후, 몰드에 주입한 후 건조용 오븐 등에서 50℃ 내지 150℃ 로 유지하여 중합과정을 통해 제조될 수 있다.The silicone hydrogel polymer according to the present invention is in each composition ratio along with components that may be additionally included, such as a silicone compound represented by Formula 1, 2-hydroxyethyl methacrylate, a hydrophilic monomer, a crosslinking agent, and a polymerization initiator in the present invention. After mixing, the mixture was preliminarily stirred at 0°C to 40°C for about 30 minutes to 10 hours, and then mixed using any one selected from methanol, ethanol, water, and acetone or a mixture thereof as a solvent, and then added to the mold. After injecting, it can be prepared through a polymerization process by maintaining it at 50°C to 150°C in a drying oven.
아울러, 본 발명은 상기 본 발명에 화학식 1로 표시되는 실리콘계 화합물을 단량체로 사용하여 실리콘 하이드로겔 중합체를 제조하는 방법을 제공한다.In addition, the present invention provides a method of preparing a silicone hydrogel polymer using the silicone compound represented by Formula 1 as a monomer in the present invention.
구체적으로,Specifically,
a) 상기 화학식 1로 표시되는 실리콘 함유 단량체 2 내지 80 wt%, pHEMA[poly(2-hydroxyethyl methacrylate)] 15 내지 90 wt%, 친수성 모노머 0.1 내지 60 wt, 가교제 0.05 내지 10 wt% 및 중합개시제 0.05 내지 5 wt%를 혼합하여 교반하는 단계; 및a) 2 to 80 wt% of the silicone-containing monomer represented by Chemical Formula 1, 15 to 90 wt% of pHEMA [poly(2-hydroxyethyl methacrylate)], 0.1 to 60 wt of hydrophilic monomer, 0.05 to 10 wt% of crosslinking agent, and 0.05 of polymerization initiator Mixing and stirring to 5 wt%; And
b) 상기 a)에서 혼합된 혼합물을 모드에 주입한 후 가열하여 중합시키는 단계;를 포함하는 콘택트 렌즈의 제조 방법을 제공한다.b) injecting the mixture mixed in a) into a mode, followed by heating to polymerize it. It provides a method of manufacturing a contact lens comprising.
상기 제조 방법에 있어서, 상기 화학식 1로 표시되는 실리콘계 화합물의 함량은 1 ~ 98 wt%의 범위로 사용할 수 있고, 바람직하게는 2 ~ 80 wt%의 범위를 사용할 수 있다.In the preparation method, the content of the silicone compound represented by Formula 1 may be used in the range of 1 to 98 wt%, and preferably in the range of 2 to 80 wt%.
상기 제조 방법에 있어서, 추가적인 단량체로서, 2-히드록시에틸 메타아크릴레이트(HEMA)는 1 ~ 98 wt%의 범위로 사용할 수 있고, 바람직하게는 2 ~ 90 wt%의 범위를 사용할 수 있다. In the above production method, as an additional monomer, 2-hydroxyethyl methacrylate (HEMA) may be used in the range of 1 to 98 wt%, and preferably in the range of 2 to 90 wt%.
상기 제조 방법에 있어서, 친수성 모노머, 가교제를 추가적으로 포함할 수 있고, 중합반응을 위한 중합개시제에 의해 중합을 진행할 수 있다. In the above production method, a hydrophilic monomer and a crosslinking agent may be additionally included, and polymerization may be performed by a polymerization initiator for a polymerization reaction.
이때, 상기 친수성 모노머로서 N-비닐피롤리돈, N,N-디메틸아크리아마이드, 글리세롤 모노메타아크릴레이트 등과 이들의 혼합물이 사용가능하며, 가교제로서는 에틸렌글리콜 디메타아크릴레이트, 트리에틸렌글리콜 디메타아크릴레이트 등이 사용가능하고, 중합개시제로서는 AIBN이 사용가능하다. At this time, as the hydrophilic monomer, N-vinylpyrrolidone, N,N-dimethylacriamide, glycerol monomethacrylate, and a mixture thereof may be used, and as a crosslinking agent, ethylene glycol dimethacrylate, triethylene glycol dimetha An acrylate or the like can be used, and AIBN can be used as a polymerization initiator.
이때, 상기 친수성 모노머의 함량은 전체 조성물 대비 0.1 내지 60 wt%, 바람직하게는 0.3 내지 50 wt%의 범위일 수 있고, 상기 가교제의 함량은 전체 조성물 대비 0.05 내지 10 wt%, 바람직하게는 0.1 내지 5 wt%일 수 있으며, 상기 중합개시제의 함량은 전체 조성물 대비 0.05 내지 5 wt%, 바람직하게는 0.1 내지 3 wt%의 범위를 가질 수 있다. At this time, the content of the hydrophilic monomer may be in the range of 0.1 to 60 wt%, preferably 0.3 to 50 wt%, based on the total composition, and the content of the crosslinking agent is 0.05 to 10 wt%, preferably 0.1 to It may be 5 wt%, and the content of the polymerization initiator may have a range of 0.05 to 5 wt%, preferably 0.1 to 3 wt% of the total composition.
본 발명의 한가지 실시예로서, 실리콘 하이드로겔 중합체는 상기 화학식 1로 표시되는 실리콘계 화합물 2 내지 80 wt%, 2-히드록시에틸 메타아크릴레이트(HEMA) 15 내지 90 wt%, N-비닐피롤리돈 0.3 내지 20 wt%, 글리세롤 모노메타아크릴레이트 3 내지 30 wt%, 에틸렌글리콜 디메타아크릴레이트 0.1 내지 5 wt%, 중합개시제로서 AIBN 0.1 내지 3 wt%로 이루어지는 조성물의 공중합에 의해 얻어질 수 있다. As an embodiment of the present invention, the silicone hydrogel polymer is 2 to 80 wt% of the silicone compound represented by Formula 1, 2-hydroxyethyl methacrylate (HEMA) 15 to 90 wt%, N-vinylpyrrolidone It can be obtained by copolymerization of a composition comprising 0.3 to 20 wt%, glycerol monomethacrylate 3 to 30 wt%, ethylene glycol dimethacrylate 0.1 to 5 wt%, and AIBN 0.1 to 3 wt% as a polymerization initiator.
상기 제조 방법에 있어서, 공중합을 위한 중합 조건은 25 ~ 150℃에서, 10분 내지 3일 동안 교반하거나 또는 교반을 하지 않은 상태에서 중합할 수 있다. In the above production method, polymerization conditions for the copolymerization may be polymerized at 25 to 150°C, with stirring for 10 minutes to 3 days or without stirring.
이하, 본 발명을 구체적으로 설명하기 위해 실시예를 들어 상세히 설명하기로 한다.Hereinafter, examples will be described in detail in order to describe the present invention in detail.
본 발명은 하기의 실시예에 의하여 보다 더 잘 이해 될 수 있으며, 하기의 실시예는 본 발명의 예시 목적을 위한 것이며, 첨부된 특허청구범위에 의하여 한정되는 보호범위를 제한하고자 하는 것은 아니다.The present invention may be better understood by the following examples, and the following examples are for illustrative purposes of the present invention, and are not intended to limit the scope of protection defined by the appended claims.
<< 실시예Example 1> 모노머 화합물의 제조 1> Preparation of monomer compound
<1-1> PEG-<1-1> PEG- PDMSPDMS -PEG 합성-PEG synthesis
H2PDMS(H2Polydimethylsiloxane) (1.72 mmol, 1 eq.)와 PEGMA(poly(ethylene glycol) methyl ether methacrylate) (3.46 mmol, 2.01 eq.)을 1.5 mL 톨루엔(toluene)에 녹이고, 11 uL의 Pt(dvs)를 첨가한 뒤, 37℃에서 1시간 교반하였다. 반응 종료 후, 톨루엔(toluene)을 증발시키고, 45 mL의 물을 첨가하여 원심분리 12분 (7800 rpm)을 수행하고, 부유물을 제거하였다. 침전물은 THF(TetraHydroFuran) 에 녹이고, MgSO4로 드라이한 후, PEG-PDMS-PEG를 얻었다. H 2 PDMS (H 2 Polydimethylsiloxane) (1.72 mmol, 1 eq.) and PEGMA (poly(ethylene glycol) methyl ether methacrylate) (3.46 mmol, 2.01 eq.) were dissolved in 1.5 mL toluene, and 11 uL of Pt After (dvs) was added, the mixture was stirred at 37°C for 1 hour. After the reaction was completed, toluene was evaporated, 45 mL of water was added, centrifugation was performed for 12 minutes (7800 rpm), and the suspended matter was removed. The precipitate was dissolved in THF (TetraHydroFuran) and dried with MgSO 4 to obtain PEG-PDMS-PEG.
<1-2> <1-2> PDMSPDMS 말단반응성고분자Terminal reactive polymer (( macromermacromer ) 합성) synthesis
IPDI(Isophorone diisocyanate) (0.11 mol)을 250 mL 3-neck 플라스크에 넣고, 기계식 교반기(mechanical stirrer)를 장착하였다. HEMA(2-hydroxyethyl methacrylate) (0.11 mol)을 3시간 동안 천천히 투하(dropping)하며 교반하였다. 상온에서 1시간 더 교반한 다음, 상기 실시예 <1-1>에서 획득한 PEG-PDMS-PEG (0.055 mol)를 천천히 첨가한 후, 75℃로 온도를 증가시키고, 15 uL의 DBTDL(Dibutyltin dilaurate)을 넣고, 5시간 더 교반하였다. 재결정후 PDMS 말단반응성고분자(macromer)를 얻었다. IPDI (Isophorone diisocyanate) (0.11 mol) was placed in a 250 mL 3-neck flask, and a mechanical stirrer was installed. HEMA (2-hydroxyethyl methacrylate) (0.11 mol) was slowly dropped for 3 hours and stirred. After stirring for an additional hour at room temperature, PEG-PDMS-PEG (0.055 mol) obtained in Example <1-1> was slowly added, the temperature was increased to 75°C, and 15 uL of dibutyltin dilaurate (DBTDL) was added. ) And stirred for 5 hours more. After recrystallization, PDMS terminal reactive polymer (macromer) was obtained.
<< 실시예Example 2> 모노머 화합물을 이용한 중합체(실리콘 2> Polymer using monomer compound (silicone 하이드로겔Hydrogel 렌즈)의 제조 Lens)
콘택트렌즈 제조에 사용된 HEMA는 진공 증류하여 불순물과 첨가된 중합방지제인 하이드로퀴논(hydroquinone)를 제거한 후 사용하였다. 상기 메타아크릴기가 도입된 친수성의 실리콘 단량체를 이용하여 얻어지는 하이드로겔 렌즈 제조를 위해 HEMA(poly(2-hydroxyethyl methacrylate))를 기반으로, 상기 <실시예 1>에서 얻어진 화합물, 친수성을 위한 N-비닐피롤리돈(N-Vinyl-2-pyrrolidone, NVP, (99%, Junsei)), 글리세롤 모노메타아크릴레이트(glycerol monomethacrylate, GMMA)가 사용되었고, 또한 가교제로서 에틸렌글리콜 디메타아크릴레이트(Ethylene glycol dimethylacrylate, EGDMA, (98%, Aldrich)), 개시제로서 아조비스 이소부티로니릴(Azobis isobutyronitrile, AIBN(98%, Junsei))를 사용하였다. HEMA used in the manufacture of contact lenses was vacuum-distilled to remove impurities and hydroquinone, an added polymerization inhibitor, before use. Based on HEMA (poly(2-hydroxyethyl methacrylate)) for manufacturing a hydrogel lens obtained using a hydrophilic silicone monomer into which the methacrylic group is introduced, the compound obtained in Example 1, N-vinyl for hydrophilicity Pyrrolidone (N-Vinyl-2-pyrrolidone, NVP, (99%, Junsei)), glycerol monomethacrylate (GMMA) was used, and ethylene glycol dimethylacrylate as a crosslinking agent. , EGDMA, (98%, Aldrich)), azobis isobutyronitrile, AIBN (98%, Junsei)) was used as an initiator.
상기 원료들을 하기 표 1의 실시예 2에 따른 구성비에 따라 혼합한 후, 1시간 동안 상온에서 교반하였다. 혼합된 모노머는 콘택트렌즈 몰드에 주입하고, 건조로(drying oven)(HST-501S, Hanst)에서 90℃, 5시간 동안 중합하였다. The raw materials were mixed according to the composition ratio according to Example 2 in Table 1, and then stirred at room temperature for 1 hour. The mixed monomer was injected into a contact lens mold and polymerized at 90° C. for 5 hours in a drying oven (HST-501S, Hanst).
제조된 렌즈는 증류수에서 3일간 교반하여 불순물을 제거하였다. The prepared lens was stirred in distilled water for 3 days to remove impurities.
<< 실시예Example 3> 다른 구성비에 따른 실리콘 3> Silicon according to different composition ratio 하이드로겔Hydrogel 렌즈의 제조 Manufacture of lenses
상기 <실시예 2>와 동일한 방법으로 헨즈를 제조하되, 하기 표 1의 실시예 3에 따른 구성비에 따라 렌즈를 제조하였다.The hands were manufactured in the same manner as in <Example 2>, but a lens was manufactured according to the composition ratio according to Example 3 in Table 1 below.
(Dk/t)Oxygen permeability
(Dk/t)
(wt%)Moisture content
(wt%)
(실리콘 단량체
5 wt%)Example 2
(Silicone monomer
5 wt%)
12 wt% NVP,
0.5 wt% EGDMA,
0.3 wt% AIBN,
25 wt% GMMA,
5 wt% 실리콘 단량체 화합물57.2 wt% HEMA,
12 wt% NVP,
0.5 wt% EGDMA,
0.3 wt% AIBN,
25 wt% GMMA,
5 wt% silicone monomer compound
(실리콘 단량체
30 wt%)Example 3
(Silicone monomer
30 wt%)
12 wt% NVP,
0.5 wt% EGDMA,
0.3 wt% AIBN,
25 wt% GMMA,
30 wt% 실리콘 단량체 화합물32.2 wt% HEMA,
12 wt% NVP,
0.5 wt% EGDMA,
0.3 wt% AIBN,
25 wt% GMMA,
30 wt% silicone monomer compound
<< 실시예Example 4> 4> 콘택트 렌즈의Contact lens 산소투과도 평가 Oxygen permeability evaluation
상기 <실시예 2> 및 <실시예 3>에서 각각 제조된 콘택트 렌즈의 산소투과도 평가를 진행하였다. 상기 산소투과도는 폴라로그래프(polarographic) 방법으로 산소투과율측정계(K-316 IPI Type Film Oxygen Permeability Meter, Rikaseiki Kogyo Co. Tokyo, Japan)를 이용하여 중심부와 주변부의 산소투과율을 측정하였다.The oxygen permeability of the contact lenses prepared in <Example 2> and <Example 3> was evaluated. The oxygen permeability was measured using an oxygen permeability meter (K-316 IPI Type Film Oxygen Permeability Meter, Rikaseiki Kogyo Co. Tokyo, Japan) by a polarographic method to measure the oxygen permeability of the center and the periphery.
백금판의 직경은 4.5 mm(곡률반경 8.00 mm, 직경 14 mm, 중앙 4.5 mm 직경의 구경을 갖는 PMMA 필터 사용), 습도는 80% 이하, 온도는 35±0.5℃에서 시료당 3회 측정하여 평균값을 얻었고, 산소투과도는 <실시예 2>는 25.3 Dk/t 및 <실시예 3>은 50.7 Dk/t로서 측정되었다. The diameter of the platinum plate is 4.5 mm (using a PMMA filter with a radius of curvature of 8.00 mm, a diameter of 14 mm, and a diameter of 4.5 mm in the center), the humidity is 80% or less, and the temperature is measured three times per sample at 35±0.5°C. Was obtained, and the oxygen permeability was measured as 25.3 Dk/t for <Example 2> and 50.7 Dk/t for <Example 3>.
상기 표 1에 따른 결과를 살펴보면, 콘택트렌즈의 경우, 본 발명에 따른 실리콘 단량체 화합물의 함량이 증가할수록 산소투과도는 높아지는 것을 알 수 있고, 일반적으로 HEMA로만 이루어진 렌즈는 산소투과도 Dk/t가 20정도로 나타나는 것을 감안하는 경우, 본 발명에 따른 콘택트 렌즈의 산소투과도가 매우 우수한 것을 알 수 있다. Looking at the results according to Table 1, in the case of a contact lens, it can be seen that the oxygen permeability increases as the content of the silicone monomer compound according to the present invention increases, and in general, the oxygen permeability Dk/t of a lens made of only HEMA is about 20. In consideration of the appearance, it can be seen that the oxygen permeability of the contact lens according to the present invention is very excellent.
Claims (5)
[화학식 1]
여기서,
n은 1 내지 10의 정수임.
Silicone-containing monomer represented by the following formula (1):
[Formula 1]
here,
n is an integer from 1 to 10.
ii) IPDI(Isophorone diisocyanate)와 HEMA(2-hydroxyethyl methacrylate)를 반응시켜 IPDI-HEMA를 제조하는 단계; 및
iii) 상기 PEG-PDMS-PEG와 상기 IPDI-HEMA를 촉매 존재 하에 반응시켜 PDMS 말단반응성고분자(macromer)를 제조하는 단계;를 포함하는,
상기 화학식 1로 표시되는 실리콘 함유 단량체의 합성 방법.
i) preparing PEG-PDMS-PEG by reacting H 2 PDMS (H 2 Polydimethylsiloxane) and PEGMA (poly(ethylene glycol) methyl ether methacrylate) in the presence of a catalyst;
ii) preparing IPDI-HEMA by reacting IPDI (Isophorone diisocyanate) and HEMA (2-hydroxyethyl methacrylate); And
iii) reacting the PEG-PDMS-PEG with the IPDI-HEMA in the presence of a catalyst to prepare a PDMS terminal reactive polymer (macromer); Containing,
Method for synthesizing the silicone-containing monomer represented by Formula 1.
A polymer comprising the silicone-containing monomer according to claim 1.
A contact lens comprising the silicone-containing monomer of claim 1 or the polymer of claim 3.
b) 상기 a)에서 혼합된 혼합물을 모드에 주입한 후 가열하여 중합시키는 단계;를 포함하는 콘택트 렌즈의 제조 방법.
a) 2 to 80 wt% of the silicone-containing monomer represented by Chemical Formula 1, 15 to 90 wt% of pHEMA [poly(2-hydroxyethyl methacrylate)], 0.1 to 60 wt% of hydrophilic monomer, 0.05 to 10 wt% of crosslinking agent, and polymerization initiator Mixing and stirring 0.05 to 5 wt%; And
b) injecting the mixture mixed in a) into the mode and then heating to polymerize the contact lens.
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