KR101231181B1 - Silicone-hydrogel compound for soft contact lens and soft contact lens produced using the compound - Google Patents
Silicone-hydrogel compound for soft contact lens and soft contact lens produced using the compound Download PDFInfo
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- KR101231181B1 KR101231181B1 KR1020070061970A KR20070061970A KR101231181B1 KR 101231181 B1 KR101231181 B1 KR 101231181B1 KR 1020070061970 A KR1020070061970 A KR 1020070061970A KR 20070061970 A KR20070061970 A KR 20070061970A KR 101231181 B1 KR101231181 B1 KR 101231181B1
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- South Korea
- Prior art keywords
- acrylamide
- bis
- trimethylsilyl
- vinyl
- pyrrolidone
- Prior art date
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- 239000000017 hydrogel Substances 0.000 title claims abstract description 25
- 150000001875 compounds Chemical class 0.000 title 2
- PWRKXMFQXZHKFF-UHFFFAOYSA-N n-trimethylsilylprop-2-enamide Chemical compound C[Si](C)(C)NC(=O)C=C PWRKXMFQXZHKFF-UHFFFAOYSA-N 0.000 claims abstract description 118
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims abstract description 54
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims abstract description 52
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims abstract description 52
- 239000000203 mixture Substances 0.000 claims abstract description 37
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 30
- 239000000178 monomer Substances 0.000 claims abstract description 27
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 30
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 10
- VKJWJILXLWFQEU-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene Chemical compound C=CC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C VKJWJILXLWFQEU-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 60
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 abstract description 39
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 abstract description 29
- 239000003431 cross linking reagent Substances 0.000 abstract description 26
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 21
- 229910052760 oxygen Inorganic materials 0.000 abstract description 21
- 239000001301 oxygen Substances 0.000 abstract description 21
- 230000035699 permeability Effects 0.000 abstract description 15
- 238000002834 transmittance Methods 0.000 abstract description 5
- WHNPOQXWAMXPTA-UHFFFAOYSA-N 3-methylbut-2-enamide Chemical compound CC(C)=CC(N)=O WHNPOQXWAMXPTA-UHFFFAOYSA-N 0.000 abstract description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 abstract description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 abstract description 2
- 229920000642 polymer Polymers 0.000 description 42
- 238000006116 polymerization reaction Methods 0.000 description 34
- 239000000463 material Substances 0.000 description 22
- 239000003999 initiator Substances 0.000 description 21
- 239000011259 mixed solution Substances 0.000 description 16
- 238000010521 absorption reaction Methods 0.000 description 11
- 230000036571 hydration Effects 0.000 description 11
- 238000006703 hydration reaction Methods 0.000 description 11
- -1 (2-ethylhexanoyl peroxy) hexane (2,5-Dimethyl-2,5-di (2-ethylhexanoyl peroxy) hexane) Chemical compound 0.000 description 9
- LLLWMXQKXWIRDZ-UHFFFAOYSA-N 1-ethenylpyrrolidin-2-one Chemical compound C=CN1CCCC1=O.C=CN1CCCC1=O LLLWMXQKXWIRDZ-UHFFFAOYSA-N 0.000 description 9
- 230000000704 physical effect Effects 0.000 description 9
- 239000004971 Cross linker Substances 0.000 description 8
- ZBGFFOJGTVCHFT-UHFFFAOYSA-N N,N-dimethylprop-2-enamide Chemical compound CN(C(C=C)=O)C.CN(C(C=C)=O)C ZBGFFOJGTVCHFT-UHFFFAOYSA-N 0.000 description 8
- JUIBLDFFVYKUAC-UHFFFAOYSA-N [5-(2-ethylhexanoylperoxy)-2,5-dimethylhexan-2-yl] 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)CCC(C)(C)OOC(=O)C(CC)CCCC JUIBLDFFVYKUAC-UHFFFAOYSA-N 0.000 description 8
- CMJUYECYIWEOKC-UHFFFAOYSA-N CC(C)(CCC(C)(OOC(C(CCCC)CC)=O)C)OOC(C(CCCC)CC)=O.CC(C)(CCC(C)(OOC(C(CCCC)CC)=O)C)OOC(C(CCCC)CC)=O Chemical compound CC(C)(CCC(C)(OOC(C(CCCC)CC)=O)C)OOC(C(CCCC)CC)=O.CC(C)(CCC(C)(OOC(C(CCCC)CC)=O)C)OOC(C(CCCC)CC)=O CMJUYECYIWEOKC-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 210000004087 cornea Anatomy 0.000 description 6
- OAGHFLPWSOJXTL-UHFFFAOYSA-N n,n-bis(trimethylsilyl)prop-2-enamide Chemical compound C[Si](C)(C)N([Si](C)(C)C)C(=O)C=C OAGHFLPWSOJXTL-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000003313 weakening effect Effects 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 2
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 2
- 206010011033 Corneal oedema Diseases 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 235000009120 camo Nutrition 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 235000005607 chanvre indien Nutrition 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 201000004778 corneal edema Diseases 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000011487 hemp Substances 0.000 description 2
- QFOJTGAPBXCVOK-UHFFFAOYSA-N hexyl 2-ethylhexaneperoxoate Chemical compound CCCCCCOOC(=O)C(CC)CCCC QFOJTGAPBXCVOK-UHFFFAOYSA-N 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- 238000012719 thermal polymerization Methods 0.000 description 2
- OKOGWGFTCLWOHO-UHFFFAOYSA-N 1-(2-ethylhexanoylperoxy)hexyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(CCCCC)OOC(=O)C(CC)CCCC OKOGWGFTCLWOHO-UHFFFAOYSA-N 0.000 description 1
- WHUWPAUXKLUBOZ-UHFFFAOYSA-N 5-(2-ethylhexanoylperoxy)hexan-2-yl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)CCC(C)OOC(=O)C(CC)CCCC WHUWPAUXKLUBOZ-UHFFFAOYSA-N 0.000 description 1
- BLFRPUQPAVVGIZ-UHFFFAOYSA-N C(=C)N1C(CCC1)=O.C(=C)N1C(CCC1)=O.C(C=C)(=O)N[Si](C)(C)C Chemical compound C(=C)N1C(CCC1)=O.C(=C)N1C(CCC1)=O.C(C=C)(=O)N[Si](C)(C)C BLFRPUQPAVVGIZ-UHFFFAOYSA-N 0.000 description 1
- SABRKHPEGGYSNE-UHFFFAOYSA-N C(=C)N1C(CCC1)=O.CN(C(C=C)=O)C.C(=C)N1C(CCC1)=O Chemical compound C(=C)N1C(CCC1)=O.CN(C(C=C)=O)C.C(=C)N1C(CCC1)=O SABRKHPEGGYSNE-UHFFFAOYSA-N 0.000 description 1
- 206010020675 Hypermetropia Diseases 0.000 description 1
- KMVUEUAVYMTSBS-UHFFFAOYSA-N N,N-dimethylprop-2-enamide 3-methylbut-2-enamide Chemical compound CC(=CC(=O)N)C.C(C=C)(=O)N(C)C KMVUEUAVYMTSBS-UHFFFAOYSA-N 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 201000009310 astigmatism Diseases 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- IPWIJFBCDPYBIF-UHFFFAOYSA-N ethene;2-(2-methylprop-2-enoyloxy)ethyl 2-methylprop-2-enoate Chemical compound C=C.CC(=C)C(=O)OCCOC(=O)C(C)=C IPWIJFBCDPYBIF-UHFFFAOYSA-N 0.000 description 1
- APWPAIPBHUQYOV-UHFFFAOYSA-N ethenylcarbamic acid 1-silylbutan-1-ol Chemical compound CCCC(O)[SiH3].OC(=O)NC=C.OC(=O)NC=C APWPAIPBHUQYOV-UHFFFAOYSA-N 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229920001600 hydrophobic polymer Polymers 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000004305 hyperopia Effects 0.000 description 1
- 201000006318 hyperopia Diseases 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 208000001491 myopia Diseases 0.000 description 1
- 230000004379 myopia Effects 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000004304 visual acuity Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
- A61F2/00—Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
- A61F2/02—Prostheses implantable into the body
- A61F2/14—Eye parts, e.g. lenses or corneal implants; Artificial eyes
- A61F2/16—Intraocular lenses
-
- 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
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
- G02B1/043—Contact lenses
-
- 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
- C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Ophthalmology & Optometry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Transplantation (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Oral & Maxillofacial Surgery (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Optics & Photonics (AREA)
- Vascular Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Eyeglasses (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
본 발명은 연질 콘텍트렌즈용 실리콘 하이드로겔 조성물 및 그 조성에 의해 제조된 연질 콘텍트렌즈에 관한 것으로, 하기 화학식 1로 표시되는 실리콘계 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide) 단량체와 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate)을 기본으로 하여, 친수성을 향상시키기 위하여 수용성 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone) 혹은 N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide) 단량체를 첨가하고, 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate) 혹은 디비닐 벤젠(Divinyl benzen) 단량체와 같은 가교제를 사용하여, 친수성, 고함수력, 높은 산소투과율, 좋은 탄성력 및 우수한 광 투과도를 지닌 연질 콘텍트렌즈용 실리콘 하이드로겔 조성물 및 그 조성에 의해 제조된 연질 콘텍트렌즈에 관한 것이다.The present invention relates to a silicone hydrogel composition for a soft contact lens and a soft contact lens manufactured by the composition, wherein the silicone N, O-bis (trimethylsilyl) acrylamide (N, O-Bis ( Based on trimethylsilyl) acrylamide monomer and 2-Hydroxyethyl methacrylate, water-soluble N-Vinyl-2-pyrrolidone or N is used to improve hydrophilicity. Hydrophilicity, high water content, by adding a N, dimethyl acrylamide monomer, and using a crosslinking agent such as ethylene glycol dimethacrylate or divinyl benzen monomer The present invention relates to a silicone hydrogel composition for a soft contact lens having high oxygen transmittance, good elasticity and good light transmittance, and a soft contact lens produced by the composition.
[화학식 1]
실리콘, 콘텍트렌즈, N,O-비스(트리메틸실릴)아크릴아마이드, 산소투과도, 친수성 Silicone, Contact Lens, N, O-Bis (trimethylsilyl) acrylamide, Oxygen Permeability, Hydrophilicity
Description
본 발명은 실리콘 하이드로겔 (Silicone-Hydrogel)재질의 연질 콘택트렌즈로서, 보다 상세하게는 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate), 실리콘계 단량체인 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide)를 포함한 연질 콘텍트렌즈용 실리콘 하이드로겔 조성물 및 그 조성에 의해 제조된 연질 콘텍트렌즈에 관한 것이다.The present invention is a soft contact lens made of silicone hydrogel (Silicone-Hydrogel), more specifically 2-hydroxy methacrylate (2-Hydroxyethyl methacrylate), a silicone monomer N, O-bis (trimethylsilyl) acrylamide The present invention relates to a silicone hydrogel composition for a soft contact lens including (N, O-Bis (trimethylsilyl) acrylamide) and a soft contact lens manufactured by the composition.
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 구분되는데, 산소투과도, 함수율 등 일반 렌즈 특성이 상대적으로 우수한 소프트 렌즈의 사용이 확대되고 있다. 이는 HEMA에는 MMA와 달리 단량체 내에 대표적인 친수성 분자 구조인 히드록시기가 있어 함수율이 높기 때문이다 (Refojo et., J. Appl. Poly. Sci., 9:2425(1965)).Generally, contact lenses are classified into hard lenses based on methyl metharylate (MMA) and soft lenses based on 2-hydroxyethyl methacrylate (HEMA). However, the use of soft lenses, which have relatively good general lens characteristics such as oxygen permeability and moisture content, is being expanded. This is because HEMA, unlike MMA, has a high hydrophobicity due to a hydroxyl group, which is a representative hydrophilic molecular structure in monomers (Refojo et., J. Appl. Poly. Sci., 9: 2425 (1965)).
한편, 하이드로겔은 평형상태에서 다량의 수분을 함유한 가교형 고분자를 의미하는데 콘택트렌즈 의료용 고분자 등 생의학적으로 많은 응용을 갖는 물질이다(참조: 미합중국 특허 제 4300820호). On the other hand, hydrogel refers to a cross-linked polymer containing a large amount of water in the equilibrium state is a material having a large number of biomedical applications, such as contact lens medical polymer (see US Patent No. 4300820).
현재, 렌즈에 사용하는 하이드로겔은 대부분 2-하이드록시 에틸메타크릴레이트(2-Hydroxyethyl methacrylate: HEMA)를 단량체로 하고 소량의 가교제와 혼용한 후 라디칼계의 열중합 반응에 의하여 제조되고 있다. 이와 같은 재료로 제조된 렌즈는 재료 특성상 함수율이 약 40%로서 친수성이고 부드러우므로 각막에 부착되어 착용 시에 이물감이 적고 각막에 대한 압박이 적어 편안한 반면, 기계적 강도가 약하고 산소투과성도 약 10 Dk [10-11(㎠/sec)(㎖ O2 ㎜Hg)]로 한계를 갖고 있어 착용감에 제한이 있고, 장시간 착용시에는 단백질이 부착 등의 문제점이 있다(Wilson et al., Encyclo. of Chem. Tech., 7:192(1976) ; 및 미합중국 특허 제 6096138호).Currently, hydrogels used in lenses are mostly prepared by 2-hydroxy ethyl methacrylate (HEMA) as a monomer and mixed with a small amount of crosslinking agent, followed by radical thermal polymerization. The lens made of such a material has a water content of about 40% and is hydrophilic and soft due to its material properties. Therefore, the lens is attached to the cornea and has a low foreign body feeling when worn, and the pressure on the cornea is comfortable, but the mechanical strength and oxygen permeability are about 10 Dk. [10 -11 ( cm 2 / sec) (ml O 2 mmHg)] has a limit to fit, and there is a problem such as adhesion of protein when worn for a long time (Wilson et al., Encyclo. Of Chem Tech., 7: 192 (1976); and US Pat. No. 6096138).
공지된 바와 같이, 렌즈의 착용감은 함수율과 밀접한 관계가 있으므로 함수율을 높이려는 다양한 개발이 시도되었고 일부는 상용화되어 있는데, N-비닐 피롤리돈(N-Vinyl-2-pyrrolidone: NVP), N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide: DMA)등과 같은 수용성 단량체를 이용하여 함수율이 80%, 산소투과율이 약 40 Dk [10-11(㎠/sec)(㎖ O2 ㎜Hg)]인 개선된 고함수성 제품이 개발되었다. 그러나 고함수성 연질렌즈는 건조감이 강하고 재질이 약해 광학적 교정능력이 떨어질 수 있고 렌즈의 삽입과 제거과정이 불편한 단점이 있어, 일회용 렌즈만 주로 사용되고 장기간 사용에는 적합하지 않다 (Refojo. et al., Cont. & Intracular Lens Med. J., 1:36(1975))As is known, the fit of the lens is closely related to the water content, so various developments have been attempted to increase the water content, and some have been commercialized, such as N-Vinyl-2-pyrrolidone (NVP), N, A water-soluble monomer such as N-dimethylacrylamide (DMA) or the like has a water content of 80% and an oxygen transmission rate of about 40 Dk [10 -11 ( cm 2 / sec) (ml O 2 mmHg)]. Improved high functional products have been developed. However, the high-functional soft lens has a weak feeling of dryness and weak material, which may reduce optical correction ability, and the process of inserting and removing the lens is inconvenient. Only a disposable lens is mainly used and not suitable for long-term use (Refojo. Et al., Cont & Intracular Lens Med. J., 1:36 (1975)).
한편, RGP 콘택트렌즈(Rigid Gas Permeable Contact Lens) 제조에 사용되는 실록산 또는 불소를 포함하는 메타크릴계 고분자는 경질 재료이면서도 착용감이 우수하고 특히 산소투과성이 높아 각막에 영향을 적게 주어 안정성을 주며 종래의 폴리메틸메타크릴레이트(polymethylmethacrylate (PMMA))에 비해 각막부종 같은 부작용이 적게 일어난다. 그러나 실록산 또는 불소계 고분자는 대표적인 소수성 고분자이므로 콘택트렌즈로 적용 시에 눈물이 젖지 않는 단점이 있으며, RGP 콘택트렌즈는 딱딱하여 고유의 형상을 가지고 있기 때문에 각막의 왜곡(distortion)이나 눈물 순환의 장애로 인하여 여러 가지 부작용이나 합병증을 일으킬 수 있으며 강도가 낮아 제조공정에 어려움이 있어 가격 면에서 비싸고 착용시 오염과 흠이 나기 쉬운 단점을 가지고 있다. On the other hand, methacryl-based polymers containing siloxane or fluorine used in the manufacture of RGP Rigid Gas Permeable Contact Lenses are hard materials and have excellent fit, and in particular, high oxygen permeability, which affects the cornea and provides stability. Compared to polymethylmethacrylate (PMMA), fewer side effects such as corneal edema occur. However, since siloxane or fluorine-based polymers are representative hydrophobic polymers, tears do not get wet when applied as contact lenses, and RGP contact lenses are hard and have a unique shape, resulting in distortion of the cornea or impairment of tear circulation. It can cause various side effects or complications, and it is difficult in the manufacturing process due to its low strength, which is expensive in terms of cost, and it is easy to be contaminated and scratched when worn.
따라서 현재 널리 사용되고 있는 콘택트렌즈의 문제점을 해결하기 위하여, 실리콘계를 함유하여 산소투과성이 우수한 하이드로겔을 소재로 한 연질렌즈(실리콘 하이드로겔 연질렌즈)를 개발하기 시작하였다. 1998년에 처음으로 제품화하였으며 이 실리콘 하이드로겔 연질렌즈는 시장 점유율이 급격히 증가하여 2003년에 약 150백만불에 이르렀다. (Optician 2005)Therefore, in order to solve the problem of the contact lens which is widely used at present, it has begun to develop a soft lens (silicone hydrogel soft lens) made of a hydrogel containing silicon-based excellent oxygen permeability. First commercialized in 1998, the silicone hydrogel soft lens market share grew rapidly to $ 150 million in 2003. (Optician 2005)
실리콘 하이드로겔은 HEMA 등과 같은 친수성 단량체와 실리콘 함유 단량체의 공중합으로 제조되는데, 일반적인 실리콘 단량체들은 소수성이 극히 높아 HEMA와 같은 친수성 단량체와 공중합 할 때 상의 분리 현상으로 인해 선명도를 유지하는데 어려움이 있다. 따라서 이를 극복하기 위해 친수성과 소수성의 상용성을 향상시키기 위한 상용화제를 개발하여 사용하여야 한다. 상용화제로는 PBVC (poly[dimethysiloxy] di [silylbutanol] bis[vinyl carbamate]), silicon macromer가 사용되는데 개발비용이 많이 들며 분자량이 커서 점도가 높아 렌즈 제조 시에 불편한 문제점이 있다. The silicone hydrogel is prepared by copolymerization of a hydrophilic monomer such as HEMA and a silicone-containing monomer, and general silicone monomers have extremely high hydrophobicity, which makes it difficult to maintain clarity due to phase separation when copolymerizing with a hydrophilic monomer such as HEMA. Therefore, in order to overcome this problem, a compatibilizer for improving the compatibility of hydrophilicity and hydrophobicity should be developed and used. As a compatibilizer, PBVC (poly [dimethysiloxy] di [silylbutanol] bis [vinyl carbamate]) and silicon macromers are used. However, the development cost is high and the molecular weight is large, which causes inconveniences in the manufacture of lenses.
일반적으로 실리콘계 수지는 소수성으로 하이드로겔 형태의 렌즈에는 오히려 함수율을 낮추기 때문에 사용이 제한되고 있으며, 렌즈표면이 소수성이므로 후가공을 통하여 표면을 산소 플라즈마 처리하여 친수화 시켜야 렌즈 착용성에 문제를 일으키지 않으며, 렌즈표면에 단백질 흡착되는 문제점이 있다.In general, silicone-based resins are hydrophobic and are limited in use because they lower water content in hydrogel-type lenses. Since the surface of the lens is hydrophobic, the surface of the lens must be hydrophilized by oxygen plasma treatment through post-processing. There is a problem of protein adsorption on the surface.
또한 실리콘 하이드로겔은 재질의 특성상 탄성율이 낮아 콘택트렌즈의 형태 복원력이 낮고, 실리콘 함유에 따른 렌즈표면의 소수성 증가로 인하여 RGP 렌즈의 단점인 각막의 상피조직과 렌즈 간에 서로 양립되는 특성이 있으며, 렌즈가 각막에 붙는 현상이 발생된다. In addition, silicone hydrogels have low elastic modulus due to the material's properties, resulting in low form resilience of contact lenses. Sticks to the cornea.
본 발명은 상기와 같은 문제점을 해결하기 위한 것으로, 소수성인 실리콘계 단량체를 친수화시키기 위해 친수성을 가진 단량체로 중합시켜 렌즈의 산소투과도를 향상시키는데 그 목적이 있다.The present invention is to solve the above problems, the purpose is to improve the oxygen permeability of the lens by polymerization with a hydrophilic monomer to hydrophilize the hydrophobic silicone-based monomer.
본 발명의 다른 목적은 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone (NVP >99%: Aldrich社)) 혹은 N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide (DMA: Aldrich社))를 추가하여 물을 적절히 함유하도록 함으로써, 상용화제를 사용하지 않고도 광투과성을 우수하게 할 수 있으며, 별도의 표면처리를 하지 않아도 착용에 문제가 발생되지 않는 연질 콘텍트렌즈용 실리콘 하이드로겔 조성물 및 그 조성에 의해 제조된 연질 콘텍트렌즈를 제공하는 것이다.Another object of the present invention is N-vinyl-2-pyrrolidone (N-Vinyl-2-pyrrolidone (NVP> 99%: Aldrich)) or N, N-dimethylacrylamide (N, N-Dimethylacrylamide (DMA: By adding Aldrich)) to properly contain water, it is possible to make excellent light transmittance without using a compatibilizer, and silicone hydrogel for soft contact lens that does not cause a problem of wearing without a separate surface treatment. It is to provide a composition and a soft contact lens produced by the composition.
상기의 목적을 달성하기 위한 본 발명 연질 콘텍트렌즈용 실리콘 하이드로겔 조성물은, 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate) 및 하기의 화학식 1로 표시되는 실리콘계 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide) 단량체를 포함하는 것을 특징으로 한다.Silicone hydrogel composition for a soft contact lens of the present invention for achieving the above object, 2-hydroxy methacrylate (2-Hydroxyethyl methacrylate) and silicone-based N, O-bis (trimethylsilyl) represented by the formula (1) It is characterized in that it contains acrylamide (N, O-Bis (trimethylsilyl) acrylamide) monomer.
또한, 상기 조성물 중 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide)의 함량은 10 중량%이하인 것을 특징으로 한다.In addition, the content of N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) in the composition is characterized in that less than 10% by weight.
또한, 상기 조성물은 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate)를 포함하는 것을 특징으로 한다.In addition, the composition is characterized in that it comprises ethylene glycol dimethacrylate (Ethylene glycol dimethacrylate).
또한, 상기 조성물 중 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide)의 함량은 10 중량%이하이며, 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate)의 함량은 0.5 중량%이하인 것을 특징으로 한다.In addition, the content of N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) in the composition is less than 10% by weight, the content of ethylene glycol dimethacrylate (Ethylene glycol dimethacrylate) is It is characterized by less than 0.5% by weight.
또한, 상기 조성물은 디비닐 벤젠(Divinyl benzen)을 포함하는 것을 특징으로 한다.In addition, the composition is characterized in that it comprises divinyl benzene (Divinyl benzen).
또한, 상기 조성물 중 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide)의 함량은 10 중량%이하이며, 디비닐 벤젠(Divinyl benzen)의 함량은 0.4 중량%이하인 것을 특징으로 한다.In addition, the content of N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) in the composition is less than 10% by weight, the content of divinyl benzen is less than 0.4% by weight It is characterized by.
또한, 상기 조성물은 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone)을 포함하는 것을 특징으로 한다.In addition, the composition is characterized in that it comprises N-vinyl-2-pyrrolidone (N-Vinyl-2-pyrrolidone).
또한, 상기 조성물 중 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide)의 함량은 5 중량%이하이며, 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate)의 함량은 0.4~0.7 중량%이하이며, N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone)의 함량은 45 중량%이하인 것을 특징으로 한다.In addition, the content of N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) in the composition is less than 5% by weight, the content of ethylene glycol dimethacrylate (Ethylene glycol dimethacrylate) is 0.4 to 0.7% by weight or less, the content of N-vinyl-2-pyrrolidone (N-Vinyl-2-pyrrolidone) is characterized in that 45% by weight or less.
또한, 상기 조성물은 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone)을 포함하는 것을 특징으로 한다.In addition, the composition is characterized in that it comprises N-vinyl-2-pyrrolidone (N-Vinyl-2-pyrrolidone).
또한, 상기 조성물은 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide)의 함량은 5 중량%이하이며, 디비닐 벤젠(Divinyl benzen)의 함량은 0.3~0.5 중량%이하이며, N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone)의 함량은 35 중량%이하인 것을 특징으로 한다.In addition, the composition of the content of N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) is less than 5% by weight, the content of divinyl benzen is 0.3 to 0.5% by weight % Or less, the content of N-vinyl-2-pyrrolidone (N-Vinyl-2-pyrrolidone) is characterized in that less than 35% by weight.
또한, 상기 조성물은 N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide)을 포함하는 것을 특징으로 한다.In addition, the composition is characterized in that it comprises N, N-dimethylacrylamide (N, N-Dimethylacrylamide).
또한, 상기 조성물은 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide)의 함량은 5 중량%이하이며, 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate)의 함량은 0.4 중량%이하이며, N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide)의 함량은 40 중량%이하인 것을 특징으로 한다.In addition, the composition of N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) is less than 5% by weight, the content of ethylene glycol dimethacrylate (Ethylene glycol dimethacrylate) is 0.4 wt% or less, and the content of N, N-dimethylacrylamide (N, N-Dimethylacrylamide) is characterized in that 40 wt% or less.
또한, 상기 조성물은 N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide)을 포함하는 것을 특징으로 한다.In addition, the composition is characterized in that it comprises N, N-dimethylacrylamide (N, N-Dimethylacrylamide).
또한, 상기 조성물은 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide)의 함량은 5 중량%이하이며, 디비닐 벤젠(Divinyl benzen)의 함량은 0.4 중량%이하이며, N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide)의 함량은 30 중량%이상인 것을 특징으로 한다.In addition, the composition has a content of N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) is less than 5% by weight, the content of divinyl benzen is less than 0.4% by weight The content of N, N-dimethylacrylamide (N, N-Dimethylacrylamide) is characterized in that more than 30% by weight.
또한, 본 발명은 상기의 목적을 달성하기 위하여 상기의 조성물에 의해 제조된 연질 콘텍트렌즈를 제공한다.In addition, the present invention provides a soft contact lens produced by the composition to achieve the above object.
이하, 본 발명을 보다 상세히 설명한다.Hereinafter, the present invention will be described in more detail.
본 발명은 주원료인 친수성 단량체 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate (BISOMER HEMA ULTRA: Cognis社)), 산소투과도를 향상시키기 위한 실리콘계 단량체인 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide ,자체합성), 친수성을 높이기 위한 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone (NVP >99%: Aldrich社)) 혹은 N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide (DMA: Aldrich社)) 수용성 단량체와 소량의 가교제 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate (EGDMA >98%: Aldrich社)) 혹은 디비닐 벤젠(Divinyl benzen (DVB >80%: Aldrich社)) 단량체를 혼용한 후 라디칼계 개시제 2,5-디메틸-2,5-디(2-에틸헥사노일 퍼록시)헥산(2,5-Dimethyl-2,5-di(2-ethylhexanoyl peroxy)hexane)의 열중합 반응에 의하여 제조되는 공중합체이다. 공중합체는 단량체라 부르는 작은 단위가 반복적으로 연결된 아주 긴 분자 구조로 이들 단량체의 화학적 연결형태(3차원 구조)로 되어있다. The present invention is the main raw material of the hydrophilic monomer 2-hydroxy methacrylate (2-Hydroxyethyl methacrylate (BISOMER HEMA ULTRA: Cognis, Inc.)), N, O-bis (trimethylsilyl) acrylamide which is a silicone monomer for improving oxygen permeability ( N, O-Bis (trimethylsilyl) acrylamide (Synthesis), N-Vinyl-2-pyrrolidone (NVP> 99%: Aldrich) or N, N- to increase hydrophilicity Dimethylylamide (N, N-Dimethylacrylamide (DMA: Aldrich)) Water-soluble monomer and a small amount of crosslinker Ethylene glycol dimethacrylate (EGDMA> 98%: Aldrich) or Divinyl benzen ( DVB> 80%: Aldrich Co.)) monomers are used and then the radical initiator 2,5-dimethyl-2,5-di (2-ethylhexanoyl peroxy) hexane (2,5-Dimethyl-2,5-di (2-ethylhexanoyl peroxy) hexane) is a copolymer prepared by the thermal polymerization reaction. Copolymers are very long molecular structures in which small units, called monomers, are repeatedly connected, forming chemical linkages (three-dimensional structures) of these monomers.
함수율이 40 ~ 70%로 친수성이 매우 좋아 특별한 표면처리를 하지 않았으며, 상용화제를 사용하지도 않았다. 높은 함수율임에도 불구하고 재질이 약하지 않아 1회용 렌즈가 아니며 2주에서 한달간 착용할 수 있는 렌즈이다.The water content was 40 to 70%, so the hydrophilic property was very good. No special surface treatment was used, and no compatibilizer was used. Despite its high water content, its material is not weak, so it is not a disposable lens and can be worn for two weeks to a month.
산소투과도는 50~ 100Dk [10-11(㎠/sec)(㎖ O2 ㎜Hg)]로 높은 수치가 나왔으며 많은 임상테스트를 통해 부작용이 없고 눈에 편안하며 장시간 착용에도 문제가 발생되지 않는다.The oxygen transmission rate is 50 ~ 100Dk [10 -11 (㎠ / sec) (㎖ O 2 ㎜Hg)] and has a high value there is no side effect through a number of clinical tests comfortable to the eye and is not a problem in wearing for a long time.
보통 실리콘 하이드로겔 콘택트렌즈가 가진 취약한 재질의 물성을 개선하였 으며 그 수치는 다음과 같다.The physical properties of the weak materials of ordinary silicone hydrogel contact lenses have been improved.
탄성율(Elongation) 200 ~ 400%, 영률(Young Modulus) 50 ~65 g/㎟, 인장 강도(Tensile strength) 80 ~ 110 g/㎟, 인성(Toughness) 120_~145 g/㎟ 로 콘택트렌즈로서 매우 좋은 물성을 지니고 있다.Elongation 200 ~ 400%, Young Modulus 50 ~ 65 g / mm2, Tensile strength 80 ~ 110 g / mm2, Toughness 120_ ~ 145 g / mm2 It has physical properties.
이하 실시예를 통하여 본 발명을 더욱 상세히 설명하고자 한다. 이들 실시예는 오로지 발명을 보다 구체적으로 설명하기 위한 것으로서, 본 발명의 요지에 따라 본 발명의 범위가 이들 실시예에 의해 제한되지는 않는다는 것은 본 발명이 속하는 기술분야에서 통상의 지식을 가진 자에게 자명할 것이다.Through the following examples will be described the present invention in more detail. These examples are only to explain the invention in more detail, it is to those skilled in the art that the scope of the present invention is not limited by these examples in accordance with the gist of the present invention. Will be self explanatory.
실시예 1Example 1
:N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide), 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate)의 중합Polymerization of N, O-Bis (trimethylsilyl) acrylamide, 2-Hydroxyethyl methacrylate
N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide)의 양을 10 g에서 90 g까지 10 g 단위로 증가시키고, 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate)의 양을 90 g에서 10 g까지 10 g의 단위로 감소시키면서 혼합 용액을 만든 다음, 개시제 2,5-Dimethyl 2,5-di(2-ethylhexanoyl peroxy)hexane 0.1 g ~ 1 g을 용해시켜 110℃에서 30분 동안 중합시킨다.Increase the amount of N, O-Bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) from 10 g to 90 g in 10 g increments, and 2-hydroxy methacrylate (2-Hydroxyethyl methacrylate). To reduce the amount of c) from 90 g to 10 g in 10 g units, and then dissolve 0.1 g to 1 g of initiator 2,5-Dimethyl 2,5-di (2-ethylhexanoyl peroxy) hexane and dissolve 110 g. Polymerize for 30 minutes at < RTI ID = 0.0 >
그 결과 0.2 g (0.2 wt%)이상의 개시제 사용시 그 양에는 관계없이 중합되지 만 투명도(상용성)에는 관여하지 않았다. 10 g (10 wt%)이상의 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide)에서 경화되지만 상용성이 떨어져 투명하지 않고 불투명한 우유빛이 된다.N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide)의 사용량이 증가될수록 경화성은 떨어져 중합물은 부드럽게 되었다.As a result, 0.2 g (0.2 wt%) or more of the initiator was polymerized regardless of the amount, but was not involved in the transparency (compatibility). Cured from more than 10 g (10 wt%) of N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide), but it is not compatible and becomes transparent and opaque milky. As the amount of bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) was increased, the curability decreased and the polymer was softened.
본 중합에서는 0.2 g(0.2 wt%)의 개시제 사용이 바람직하며, N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide)이 높은 가교도를 가져 가교제 없이도 경화가 일어나며, 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate)와 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide) 단량체 10 g(10 wt%)이하에서는 상용성(투명도)이 좋다는 것을 알 수 있다.In the polymerization, 0.2 g (0.2 wt%) of initiator is preferred, and N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) has a high degree of crosslinking and curing occurs without a crosslinking agent. Compatibility under 10 g (10 wt%) of 2-Hydroxyethyl methacrylate and N, O-bis (trimethylsilyl) acrylamide monomer ) Is good.
실시예 2Example 2
: N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide), N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone)의 중합: Polymerization of N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) and N-vinyl-2-pyrrolidone
N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide)의 양을 10 g에서 90 g까지 10 g 단위로 증가시키고, N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone)의 양을 90 g에서 10 g까지 10 g의 단위로 감소시키면서 혼합 용액을 만든 다음, 개시제 2,5-디메틸-2,5-디(2-에틸헥사노일 퍼록시)헥산(2,5- Dimethyl-2,5-di(2-ethylhexanoyl peroxy)hexane) 0.1 g ~ 1 g을 용해시켜 110℃에서 30분 동안 중합 시킨다.Increase the amount of N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) from 10 g to 90 g in 10 g increments and add N-vinyl-2-pyrrolidone (N- A mixed solution was prepared while reducing the amount of vinyl-2-pyrrolidone) from 90 g to 10 g in 10 g units, and then the initiator 2,5-dimethyl-2,5-di (2-ethylhexanoyl peroxy) hexane 0.1 g to 1 g of (2,5-Dimethyl-2,5-di (2-ethylhexanoyl peroxy) hexane) is dissolved and polymerized at 110 ° C. for 30 minutes.
그 결과 개시제 사용량에 관계없이 경화되지 않으며, N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide)의 함량이 증가할수록 경화성이 떨어지며 중합하여도 경화되지 않고 접착제와 같이 끈적거린다.As a result, it does not cure regardless of the amount of initiator used, and as the content of N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) increases, the curability decreases. Sticky
본 중합에서는 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide)과 수용성 단량체 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone)을 중합하여도 경화되지 않아 렌즈로 적용이 불가하며, 경화되기 위해 가교제가 필요함을 알 수 있다.In this polymerization, N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) and the water-soluble monomer N-Vinyl-2-pyrrolidone may be polymerized. It cannot be applied to the lens because it is not cured, and it can be seen that a crosslinking agent is required to be cured.
실시예 3Example 3
: N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide), 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate) 및 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate)의 중합: N, O-Bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide), 2-hydroxy methacrylate (2-Hydroxyethyl methacrylate) and ethylene glycol dimethacrylate (Ethylene glycol dimethacrylate) polymerization
N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide)의 양을 10 g에서 90 g까지 5 g 단위로 증가시키고, 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate)의 양을 90 g에서 10 g까지 5 g의 단위로 감소시키면서 0.1 g ~ 1 g의 가교제 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate) 혼합 용액을 만든 다음, 개시제 2,5-디메틸-2,5-디(2-에틸헥사노 일 퍼록시)헥산(2,5-Dimethyl-2,5-di(2-ethylhexanoyl peroxy)hexane) 0.2 g 을 용해시켜 110℃에서 30분 동안 중합시킨다.Increase the amount of N, O-Bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) from 10 g to 90 g in 5 g increments, and 2-hydroxy methacrylate (2-Hydroxyethyl methacrylate). 0.1 g to 1 g of a crosslinking agent ethylene glycol dimethacrylate mixed solution was prepared while reducing the amount of c) from 90 g to 10 g in 5 g units, followed by initiator 2,5-dimethyl-2, 0.2 g of 5-di (2-ethylhexanoyl peroxy) hexane (2,5-Dimethyl-2,5-di (2-ethylhexanoyl peroxy) hexane) is dissolved and polymerized at 110 DEG C for 30 minutes.
그 결과 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate) 사용량 증가는 투명성(상용성), 경화성을 좋게 하지만 탄성력을 약화시켰으며, 0.5 g(0.5 wt%)이하 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate)에서 렌즈에 적용할 수 있을 정도의 중합물이 나왔다. 20 wt%이하의 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide)에서 경화되어 투명하게 되지만, 10 wt% ~20 wt%이하에서는 수화 후 물의 흡수정도가 좋지 않았다. 10 wt%이하에서 수화상태가 양호하였다. 20 wt%이상에서는 투명하게 경화되지만 수화 후 불투명하게 변했으며 쉽게 끊어지는 현상이 나왔다. As a result, increased use of ethylene glycol dimethacrylate improved transparency (compatibility) and curability, but weakened elasticity, and less than 0.5 g (0.5 wt%) of ethylene glycol dimethacrylate. ), The polymer is enough to apply to the lens. Harden at 20 wt% or less of N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) to become transparent, but below 10 wt% to 20 wt%, water absorption after hydration is good. Did. Hydration was good below 10 wt%. At 20 wt% or more it was cured transparently, but became opaque after hydration and easily broken.
본 중합에서는 가교제 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate)의 사용은 가교도를 높여 투명성(상용성)을 향상시키고 중합물의 경화성을 높여 강도를 강하게 하며, 0.5 wt%이하 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate) 사용이 렌즈 적용에 적당함을 알 수 있다. In this polymerization, the use of the crosslinking agent ethylene glycol dimethacrylate increases the crosslinking degree to improve transparency (compatibility) and to increase the hardenability of the polymer to increase the strength, and 0.5 wt% or less of ethylene glycol dimethacrylate ( Ethylene glycol dimethacrylate) is suitable for lens application.
10 wt%이하 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide), 90 wt%이상 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate) 및 0.5 wt%이하 가교제 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate)의 중합시 상용성이 좋아 투명한 경화 상태를 보이며 수화 상태도 좋은 중합물로 어느 정도 탄력성을 지닌 렌즈에 적용할 수 있음을 알 수 있다.10 wt% or less N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide), 90 wt% or more 2-hydroxy methacrylate and 0.5 wt% or less crosslinking agent Ethylene glycol dimethacrylate (Ethylene glycol dimethacrylate) has good compatibility in the polymerization of the transparent curing state and good hydrated state of the polymer can be applied to the lens with a certain degree of elasticity.
실시예 4Example 4
: N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide), 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate) 및 디비닐 벤젠(Divinyl benzen)의 중합: Polymerization of N, O-Bis (trimethylsilyl) acrylamide, 2-Hydroxyethyl methacrylate and Divinyl benzen
N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide)의 양을 10 g에서 90 g까지 5 g 단위로 증가시키고, 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate)의 양을 90 g에서 5 g까지 5 g의 단위로 감소시키면서 0.1 g ~ 1 g의 가교제 디비닐 벤젠(Divinyl benzen) 혼합 용액을 만든 다음, 개시제 2,5-디메틸-2,5-디(2-에틸헥사노일 퍼록시)헥산(2,5-Dimethyl-2,5-di(2-ethylhexanoyl peroxy)hexane) 0.2 g 을 용해시켜 110℃에서 30분 동안 중합시킨다.Increase the amount of N, O-Bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) from 10 g to 90 g in 5 g increments, and 2-hydroxy methacrylate (2-Hydroxyethyl methacrylate). ) From 0.1 g to 1 g of a crosslinking agent, divinyl benzen mixed solution, while reducing the amount of) from 90 g to 5 g in 5 g units, followed by initiator 2,5-dimethyl-2,5-di ( 0.2 g of 2-ethylhexanoyl peroxy) hexane (2,5-Dimethyl-2,5-di (2-ethylhexanoyl peroxy) hexane) is dissolved and polymerized at 110 DEG C for 30 minutes.
그 결과 디비닐 벤젠(Divinyl benzen) 사용량 증가는 투명성(상용성), 경화성을 좋게 하지만 탄성력을 약화시켰으며, 0.4 g(0.4 wt%)이하 디비닐 벤젠(Divinyl benzen)에서 렌즈에 적용할 수 있을 정도의 중합물이 나왔다. 20 wt% 이하의 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide)에서 경화되어 투명하게 되지만, 10 wt% ~20 wt%이하에서는 수화 후 물의 흡수정도가 좋지 않았다. 10 wt%이하에서 수화상태가 양호 하였다. 20 wt%이상에서는 투명하게 경화되지만 수화 후 불투명하게 변했으며 쉽게 끊어지는 현상이 나왔다. As a result, increased use of divinyl benzen improves transparency (compatibility) and curability but weakens the elasticity, and it can be applied to lenses in divinyl benzen below 0.4 g (0.4 wt%). A degree of polymerization came out. It hardens in 20 wt% or less of N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) and becomes transparent, but water absorption after hydration is less than 10 wt% ~ 20 wt%. Did. Hydration was good at less than 10 wt%. At 20 wt% or more it was cured transparently, but became opaque after hydration and easily broken.
본 중합에서는 가교제 디비닐 벤젠(Divinyl benzen)의 사용은 가교도를 높여 투명성(상용성)을 향상시키고 중합물의 경화성을 높여 강도를 강하게 한다. 0.4 wt%이하 디비닐 벤젠(Divinyl benzen) 사용이 렌즈 적용에 적당함을 알 수 있다.In the present polymerization, the use of the crosslinking agent, divinyl benzen, increases the degree of crosslinking, thereby improving transparency (compatibility) and increasing the curability of the polymer, thereby increasing strength. It can be seen that the use of divinyl benzen below 0.4 wt% is suitable for lens application.
10 wt%이하 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide), 90 wt%이상 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate) 및 0.4 wt%이하 가교제 디비닐 벤젠(Divinyl benzen)이 중합 시에 상용성이 좋아 투명도 및 물흡수도가 좋고 탄력이 있는 중합물을 만들 수 있음을 알 수 있다.10 wt% or less N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide), 90 wt% or more 2-hydroxy methacrylate, and 0.4 wt% or less crosslinking agent Divinyl benzene (divinyl benzen) is good in the compatibility at the time of polymerization can be seen that it can make a polymer with good transparency and water absorption good elasticity.
실시예 3 과 비교하면 디비닐 벤젠(Divinyl benzen)의 사용이 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate)보다 상용성(투명도)에 더 좋다는 것을 알 수 있다.Compared with Example 3, it can be seen that the use of divinyl benzen is more compatible (transparency) than ethylene glycol dimethacrylate (Ethylene glycol dimethacrylate).
실시예 5Example 5
: N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide), 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate), N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone) 및 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate)의 중합: N, O-Bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide), 2-hydroxy methacrylate, N-vinyl-2-pyrrolidone (N- Polymerization of Vinyl-2-pyrrolidone) and Ethylene Glycol Dimethacrylate
실시예 3에서 중합물의 함수율 조정하여 친수성을 향상하고, 물질간의 중합 정도를 확인하기 위해 수용성 단량체인 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone)을 첨가하여 실시한다.In Example 3, the hydrophilicity is improved by adjusting the water content of the polymer, and in order to confirm the degree of polymerization between the substances, N-vinyl-2-pyrrolidone, which is a water-soluble monomer, is added thereto.
N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide)을 5 wt% ~ 50 wt%까지 5 wt% 단위로 증가시키고, 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate)를 90 wt%에서 5 wt% 단위로 감소시키고, N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone)을 5 wt%에서 5 wt% 단위로 증가시키면서 0.1 wt% ~ 1 wt%의 가교제 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate) 혼합 용액을 만든 다음, 개시제 2,5-디메틸-2,5-디(2-에틸헥사노일 퍼록시)헥산(2,5-Dimethyl-2,5-di(2-ethylhexanoyl peroxy)hexane) 0.2 wt%을 용해시켜 110℃에서 30분 동안 중합시킨다.N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) is increased in 5 wt% increments from 5 wt% to 50 wt% and 2-hydroxy methacrylate (2-Hydroxyethyl methacrylate) from 90 wt% to 5 wt% and from 0.1 wt% to 1 with increasing N-Vinyl-2-pyrrolidone from 5 wt% to 5 wt%. A wt% crosslinker was prepared with a mixed solution of ethylene glycol dimethacrylate, and then initiator 2,5-dimethyl-2,5-di (2-ethylhexanoyl peroxy) hexane (2,5-Dimethyl- 0.2 wt% of 2,5-di (2-ethylhexanoyl peroxy) hexane) is dissolved and polymerized at 110 ° C. for 30 minutes.
그 결과 가교제 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate) 1 wt%에서는 5 wt% ~ 10 wt% N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide), 50 wt%이하의 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate), 40 wt%이상의 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone) 중합에서 투명하게 경화가 된다. 하지만 중합물은 쉽게 깨어지며, 수화 후 탄력이 없고 쉽게 찢어졌다. 가교제 0.4 wt% ~ 0.9 wt%에서는 5 wt%이하 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide), 5 wt% ~ 90 wt%이하의 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate), 5 wt% ~ 40 wt%이하의 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone) 중합에서 투명하게 경화가 된다. 특히, 0.4 wt% ~ 0.7 wt% 가교제 사용 중합물은 수화 후 물의 흡수 및 탄력성이 좋았다. As a result, 5 wt% to 10 wt% N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) at 50 wt% of the crosslinking agent ethylene glycol dimethacrylate Less than 2% 2-hydroxy methacrylate, more than 40 wt% of N-Vinyl-2-pyrrolidone polymerization is cured transparently. However, the polymer broke easily, was not elastic and easily torn after hydration. N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) at 5 wt% or less 2-hydroxy meta at 0.4 wt% to 0.9 wt% crosslinking agent 2-Hydroxyethyl methacrylate, cured transparently in N-Vinyl-2-pyrrolidone polymerization of 5 wt% to 40 wt% or less. In particular, the polymer using 0.4 wt% to 0.7 wt% crosslinking agent had good water absorption and elasticity after hydration.
N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone) 사용량 증가는 함수율을 증가시 키고 물질간의 상용화를 향상시켜 투명도를 좋게 했다. 45 wt%이하의 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone)에서 상용성이 좋아 경화되어 투명한 중합물이 나왔으며 함수율은 38 % ~ 55 % 측정값이 나왔다. 45 wt%이상의 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone)에서는 55%이상의 높은 함수율을 가진 중합물이 나왔다. Increasing the amount of N-vinyl-2-pyrrolidone used increased the water content and improved the compatibility between materials to improve transparency. N-Vinyl-2-pyrrolidone (45 wt% or less) was cured with good compatibility, resulting in a transparent polymer, with a water content ranging from 38% to 55%. More than 45 wt% of N-vinyl-2-pyrrolidone resulted in a polymer having a high water content of more than 55%.
본 중합에서는 5%이하의 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide) 사용이 투명성, 탄성력 및 물 흡수력이 좋은 중합물로 렌즈 적용에 적합함을 알 수 있다.In this polymerization, the use of N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) of 5% or less is suitable for lens application as a polymer having good transparency, elasticity and water absorption. .
가교제 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate)의 사용은 가교도를 높여 투명성(상용성)을 향상시키고 중합물의 경화성을 높여 강도를 강하게 하며, 수화 후 렌즈의 탄성력을 약화시킨다. 0.4 wt% ~ 0.7 wt% 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate) 사용이 렌즈 적용에 적합함을 알 수 있다.The use of a crosslinking agent, ethylene glycol dimethacrylate, improves transparency (compatibility) by increasing the degree of crosslinking, strengthens the strength by increasing the curability of the polymer, and weakens the elastic force of the lens after hydration. It can be seen that the use of 0.4 wt% to 0.7 wt% ethylene glycol dimethacrylate is suitable for lens application.
N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone)의 사용량 증가는 물질간의 상용화를 향상시켜 투명성을 좋게 하지만 함수율의 증가를 가져와 중합물의 탄성력 및 인장강도의 약화를 가져왔다. 45 wt%이하 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone)의 사용이 38 % ~55 %의 함수율을 가진 중합물로 탄력성이 좋고 젖음성이 좋아 렌즈 적용에 있어 적합함을 알 수 있다. Increasing the amount of N-vinyl-2-pyrrolidone used improves the compatibility between materials to improve transparency, but increases the water content, resulting in a weakening of the elasticity and tensile strength of the polymer. The use of N-Vinyl-2-pyrrolidone below 45 wt% is a polymer with a water content of 38% to 55%. It has good elasticity and wettability and is suitable for lens application. Can be.
실시예 6Example 6
: N,O-비스(트리메틸실릴)아크릴아마이드(N,O- Bis(trimethylsilyl)acrylamide), 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate), N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone) 및 디비닐 벤젠(Divinyl benzen)의 중합: N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide), 2-hydroxy methacrylate (2-Hydroxyethyl methacrylate), N-vinyl-2-pyrrolidone (N- Polymerization of Vinyl-2-pyrrolidone) and Divinyl benzen
실시예 4에서 중합물의 함수율 조정하여 친수성을 향상하고, 물질간의 중합 정도를 확인하기 위해 수용성 단량체인 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone)을 첨가하고, 실시예 5의 가교제 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate)와 비교하기 위해 디비닐 벤젠(Divinyl benzen)을 사용하여 실시한다.In Example 4, the water content of the polymer was adjusted to improve hydrophilicity, and N-vinyl-2-pyrrolidone, which is a water-soluble monomer, was added to confirm the degree of polymerization between the materials, and Example 5 In order to compare with the crosslinking agent of ethylene glycol dimethacrylate (Ethylene glycol dimethacrylate) is carried out using divinyl benzene (Divinyl benzen).
N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide)를 5 wt% ~ 50 wt%까지 5 wt% 단위로 증가시키고, 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate)를 90 wt%에서 5 wt% 단위로 감소시키고, N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone)을 5 wt%에서 5 wt% 단위로 증가시키면서 0.1 wt% ~ 1 wt%의 가교제 디비닐 벤젠(Divinyl benzen) 혼합 용액을 만든 다음, 개시제 2,5-디메틸-2,5-디(2-에틸헥사노일 퍼록시)헥산(2,5-Dimethyl-2,5-di(2-ethylhexanoyl peroxy)hexane) 0.2 wt%을 용해시켜 110℃에서 30분 동안 중합시킨다.N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) is increased in 5 wt% increments from 5 wt% to 50 wt%, 2-hydroxy methacrylate (2-Hydroxyethyl methacrylate) from 90 wt% to 5 wt% and from 0.1 wt% to 1 with increasing N-Vinyl-2-pyrrolidone from 5 wt% to 5 wt%. A wt% crosslinker divinyl benzen mixed solution was prepared, followed by initiator 2,5-dimethyl-2,5-di (2-ethylhexanoyl peroxy) hexane (2,5-Dimethyl-2,5- 0.2 wt% of di (2-ethylhexanoyl peroxy) hexane) is dissolved and polymerized at 110 ° C. for 30 minutes.
그 결과 가교제 디비닐 벤젠(Divinyl benzen) 1 wt%에서는 5 wt% - 10 wt% N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide), 50wt% ~ 90 wt%이하의 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate), 10 wt%이상의 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone) 중합에서 투명하게 경화가 된다. 하지만 중합물은 쉽게 깨어지며, 수화 후 탄력이 없고 쉽게 찢어졌다. 가교제 0.4 wt% ~ 0.9 wt%에서는 5 wt%이하 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide), 5 wt% ~ 90 wt%이하의 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate), 5 wt% ~ 40 wt%이하의 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone) 중합에서 투명하게 경화가 된다. 특히, 0.4 wt% ~ 0.7 wt% 가교제 사용 중합물은 수화 후 물의 흡수 및 탄력성이 좋았다. As a result, 5 wt%-10 wt% N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) at 50 wt% to 90 wt% In the following 2-hydroxy methacrylate (N-Vinyl-2-pyrrolidone) polymerization of more than 10 wt%, the curing is transparent. However, the polymer broke easily, was not elastic and easily torn after hydration. N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) at 5 wt% or less 2-hydroxy meta at 0.4 wt% to 0.9 wt% crosslinking agent 2-Hydroxyethyl methacrylate, cured transparently in N-Vinyl-2-pyrrolidone polymerization of 5 wt% to 40 wt% or less. In particular, the polymer using 0.4 wt% to 0.7 wt% crosslinking agent had good water absorption and elasticity after hydration.
N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone) 사용량 증가는 함수율을 증가시키고 물질간의 상용화를 향상시켜 투명도를 좋게 했다. 35 wt%이하의 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone)에서 상용성 좋아 경화되어 투명한 중합물이 나왔으며 함수율은 38 % ~ 55 % 측정값이 나왔다. 35 wt%이상의 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone)에서는 55%이상의 높은 함수율을 가진 중합물이 나왔다. Increasing the amount of N-vinyl-2-pyrrolidone used increased the water content and improved the compatibility between materials to improve transparency. N-vinyl-2-pyrrolidone (35 wt% or less) was cured with good compatibility, resulting in a transparent polymer with a water content ranging from 38% to 55%. N-Vinyl-2-pyrrolidone of more than 35 wt% resulted in a polymer having a high water content of more than 55%.
본 중합에서는 5%이하의 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide) 사용이 투명성, 탄성력 및 물 흡수력이 좋은 중합물로 렌즈 적용에 적합함을 알 수 있다.In this polymerization, the use of N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) of 5% or less is suitable for lens application as a polymer having good transparency, elasticity and water absorption. .
가교제 디비닐 벤젠(Divinyl benzen)의 사용은 실시예 5의 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate)보다 높은 가교도로 투명성(상용성)을 더 향상시키고 중합물의 경화성을 높여 강도를 강하게 하며, 수화 후 렌즈의 탄성력을 약화시키며 크기에서는 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate)의 사용보다 더 작게 나왔다. 0.3 wt% ~ 0.5 wt% 디비닐 벤젠(Divinyl benzen) 사용이 투명성도 좋고 탄성력이 좋아 렌즈 적용에 적합함을 알 수 있다. The use of the crosslinker Divinyl benzen improves the transparency (compatibility) with a higher crosslinking degree than the ethylene glycol dimethacrylate of Example 5, increases the curability of the polymer, and strengthens the strength. Afterwards, the elastic force of the lens was weakened, and the size was smaller than that of ethylene glycol dimethacrylate. It can be seen that the use of 0.3 wt% to 0.5 wt% divinyl benzen is suitable for lens application due to its good transparency and elasticity.
N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone)의 사용량 증가는 물질간의 상용화를 향상시켜 투명성을 좋게 하지만 함수율의 증가를 가져와 중합물의 탄성력 및 인장강도의 약화를 가져왔다. 35 wt%이하 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone)의 사용이 38 % ~ 55 %의 함수율을 가진 중합물로 투명성이 좋고 탄성력이 좋아 렌즈 적용에 있어 적합하다Increasing the amount of N-vinyl-2-pyrrolidone used improves the compatibility between materials to improve transparency, but increases the water content, resulting in a weakening of the elasticity and tensile strength of the polymer. Less than 35 wt% N-Vinyl-2-pyrrolidone is a polymer with a water content of 38% to 55%. Its transparency and elasticity make it suitable for lens applications.
실시예 7Example 7
: N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide), 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate), N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide) 및 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate)의 중합: N, O-Bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide), 2-Hydroxyethyl methacrylate, N, N-dimethylacrylamide (N, N- Dimethylacrylamide) and Polymerization of Ethylene Glycol Dimethacrylate
실시예 3에서 중합물의 함수율을 조정하여 친수성을 향상하고, 물질간의 중합 정도를 확인하기 위해 또 다른 수용성 단량체 N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide)을 첨가하여 실시한다.In Example 3, the water content of the polymer was adjusted to improve hydrophilicity, and another water-soluble monomer N, N-dimethylacrylamide was added to confirm the degree of polymerization between the materials.
실시예 5에서 얻은 결과를 통해 5 wt% 이하의 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide) 와 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate)를 90 wt%에서 5 wt% 단위로 감소시키고 N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide)을 5 wt%에서 5 wt% 단위로 증가시키면서 0.4 wt%의 가교제 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate) 혼합 용액을 만든 다음, 개시제 2,5-디메틸-2,5-디(2-에틸헥사노 일 퍼록시)헥산(2,5-Dimethyl-2,5-di(2-ethylhexanoyl peroxy)hexane) 0.2 wt%을 용해시켜 110℃에서 30분 동안 중합시킨다.Based on the results obtained in Example 5, N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) and 2-hydroxyl methacrylate (2-Hydroxyethyl methacrylate) were added. 0.4 wt% of crosslinker ethylene glycol dimethacrylate (Ethylene) while decreasing from 90 wt% to 5 wt% and increasing N, N-dimethylacrylamide from 5 wt% to 5 wt% glycol dimethacrylate) solution was prepared, followed by initiator 2,5-dimethyl-2,5-di (2-ethylhexanoyl peroxy) hexane (2,5-Dimethyl-2,5-di (2-ethylhexanoyl peroxy) hexane) 0.2 wt% is dissolved and polymerized at 110 ° C. for 30 minutes.
그 결과 5 wt%의 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide)에서 40 wt%이상의 N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide)가 상용성이 좋아 경화되어 투명한 중합물이 나왔으며 함수율은 55 %이상으로 팽창률이 매우 컸다. N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide) 사용량 증가는 함수율을 증가시켜 팽창률을 크게 하고 물질간의 상용화를 향상시켜 투명도를 좋게 했다.As a result, more than 40 wt% of N, N-dimethylacrylamide is compatible with 5 wt% of N, O-bis (trimethylsilyl) acrylamide. It was cured to a good quality, and a transparent polymer was obtained. The water content was 55% and the expansion rate was very large. Increasing the amount of N, N-dimethylacrylamide increased the water content, increased the expansion rate, and improved commercialization between materials, resulting in better transparency.
본 중합에서는 5%이하의 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide) 사용이 투명성, 탄성력 및 물 흡수력이 좋은 중합물로 렌즈 적용에 적합함을 알 수 있다.In this polymerization, the use of N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) of 5% or less is suitable for lens application as a polymer having good transparency, elasticity and water absorption. .
N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide)의 사용량 증가는 물질간의 상용화를 향상시켜 투명성을 좋게 하지만 함수율의 증가로 인해 매우 큰 팽창률을 가져와 중합물의 탄성력 및 인장강도의 약화를 가져왔다. 40 wt%이상 70wt% 이하 N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide)의 사용의 중합물에서 투명성과 물흡수도가 좋고 탄력성이 좋아 렌즈로 적용이 가능함을 알 수 있다.Increasing the amount of N, N-dimethylacrylamide improves the compatibility between materials to improve transparency, but has a very large expansion rate due to the increase in water content, resulting in a weakening of the elasticity and tensile strength of the polymer. 40 wt% or more and 70wt% or less In the polymerized product of N, N-dimethylacrylamide, transparency and water absorption are good and the elasticity is good.
실시예 8Example 8
: N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide), 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate), N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide) 및 디비닐 벤젠(Divinyl benzen)의 중합: N, O-Bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide), 2-Hydroxyethyl methacrylate, N, N-dimethylacrylamide (N, N- Polymerization of Dimethylacrylamide and Divinyl Benzen
실시예 4에서 중합물의 함수율 조정하여 친수성을 향상하고, 물질간의 중합 적합성 확인 및 실시예 7의 가교제 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate)와 비교하기 위해 실시한다.The hydrophilicity is improved by adjusting the water content of the polymer in Example 4, and the polymerization is performed to confirm the compatibility between the materials and to compare with the crosslinking agent ethylene glycol dimethacrylate of Example 7.
실시예 5에서 얻은 결과를 통해 5 wt% 이하의 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide) 와 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate)를 90 wt%에서 5 wt% 단위로 감소시키고, N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide)을 5 wt%에서 5 wt% 단위로 증가시키면서, 0.4 wt%의 가교제 디비닐 벤젠(Divinyl benzen) 혼합 용액을 만든 다음, 개시제 2,5-디메틸-2,5-디(2-에틸헥사노일 퍼록시)헥산(2,5-Dimethyl-2,5-di(2-ethylhexanoyl peroxy)hexane) 0.2 wt%을 용해시켜 110℃에서 30분 동안 중합시킨다.Based on the results obtained in Example 5, N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) and 2-hydroxyl methacrylate (2-Hydroxyethyl methacrylate) were added. 0.4 wt% of divinyl benzen, while decreasing from 90 wt% to 5 wt% and increasing N, N-dimethylacrylamide from 5 wt% to 5 wt%. ) Mixed solution, and then the initiator 2,5-dimethyl-2,5-di (2-ethylhexanoyl peroxy) hexane (2,5-Dimethyl-2,5-di (2-ethylhexanoyl peroxy) hexane) 0.2 The wt% is dissolved and polymerized at 110 ° C. for 30 minutes.
그 결과 5 wt%의 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide)에서 30 wt%이상의 N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide)가 상용성이 좋아 경화되어 투명한 중합물이 나왔으며 함수율은 55 %이상으로 팽창률이 매우 컸다. N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide) 사용량 증가는 함수율을 증가시켜 팽창률을 크게 하고 물질간의 상용화를 향상시켜 투명도를 좋게 했다.As a result, more than 30 wt% of N, N-dimethylacrylamide (N, N-Dimethylacrylamide) is compatible with 5 wt% of N, O-bis (trimethylsilyl) acrylamide. It was cured to a good quality, and a transparent polymer was obtained. The water content was 55% and the expansion rate was very large. Increasing the amount of N, N-dimethylacrylamide increased the water content, increased the expansion rate, and improved commercialization between materials, resulting in better transparency.
본 중합에서는 5%이하의 N,O-비스(트리메틸실릴)아크릴아마이드(N,O- Bis(trimethylsilyl)acrylamide) 사용이 투명성, 탄성력 및 물 흡수력이 좋은 중합물로 렌즈 적용에 적합함을 알 수 있다.In this polymerization, the use of N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) of 5% or less is suitable for lens application as a polymer having good transparency, elasticity and water absorption. .
N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide)의 사용량 증가는 물질간의 상용화를 향상시켜 투명성을 좋게 하지만 함수율의 증가로 인해 매우 큰 팽창률을 가져와 중합물의 탄성력 및 인장강도의 약화를 가져왔다. 30 wt%이상 70 wt%이하 N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide)의 사용의 중합물에서 투명성과 물흡수도가 좋고 탄력성이 좋아 렌즈로 적용이 가능함을 알 수 있다. Increasing the amount of N, N-dimethylacrylamide improves the compatibility between materials to improve transparency, but has a very large expansion rate due to the increase in water content, resulting in a weakening of the elasticity and tensile strength of the polymer. 30 wt% or more and 70 wt% or less N, N-dimethylacrylamide (N, N-Dimethylacrylamide) in the polymer of the use of the transparency and water absorption good elasticity can be seen that it can be applied to the lens.
실시예 7과 비교해보면 가교제 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate)보다 디비닐 벤젠(Divinyl benzen)의 사용이 상용성(투명도)을 더 향상시키지만 탄력성면에서는 다소 떨어졌고 지름(diameter)을 작게 함을 알 수 있다. Compared with Example 7, the use of divinyl benzen more than the crosslinker ethylene glycol dimethacrylate improves the compatibility (transparency), but is slightly lower in terms of elasticity and smaller in diameter. It can be seen.
실시예 9Example 9
: N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide), 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate), N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide), N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone) 및 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate)의 중합: N, O-Bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide), 2-Hydroxyethyl methacrylate, N, N-dimethylacrylamide (N, N- Dimethylacrylamide), Polymerization of N-Vinyl-2-pyrrolidone and Ethylene glycol Dimethacrylate
실시예 4에서 중합물의 함수율 조정하여 친수성을 향상하고, 수용성 단량체인 N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide), N-비닐-2-피롤리돈(N- Vinyl-2-pyrrolidone) 이 두단량체의 물질간의 중합 적합성 확인 위해 실시한다.In Example 4, the hydrophilicity was improved by adjusting the water content of the polymer, and N, N-dimethylacrylamide and N-vinyl-2-pyrrolidone, which are water-soluble monomers, were improved. This is carried out to confirm the polymerization suitability between the materials of this monomer.
실시예 7에서 얻은 결과를 통해 5 wt% 이하의 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide), 60 wt% 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate), N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide)와 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone)의 양을 40 wt% 이내에서 적당히 서로의 양을 변화시키면서, 0.4 wt%의 가교제 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate) 혼합 용액을 만든 다음, 개시제 2,5-디메틸-2,5-디(2-에틸헥사노일 퍼록시)헥산(2,5-Dimethyl-2,5-di(2-ethylhexanoyl peroxy)hexane) 0.2 wt%을 용해시켜 110℃에서 30분 동안 중합시킨다.5 wt% or less of N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide), 60 wt% 2-hydroxy methacrylate (2-Hydroxyethyl from the results obtained in Example 7 methacrylate), N, N-dimethylacrylamide and N-vinyl-2-pyrrolidone in an amount of 40 wt%, varying the amount of each other appropriately. 0.4 wt% of crosslinker ethylene glycol dimethacrylate mixed solution was prepared, followed by initiator 2,5-dimethyl-2,5-di (2-ethylhexanoyl peroxy) hexane (2,5 0.2 wt% of -Dimethyl-2,5-di (2-ethylhexanoyl peroxy) hexane) is dissolved and polymerized at 110 ° C. for 30 minutes.
그 결과 N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide)와 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone)의 변화에 관계없이 경화상태에서는 상용성이 좋아 투명한 중합물이 생성되었으나, 물을 흡수하면서 중합물은 뿌연 우유빛으로 변화 되었다.As a result, regardless of the changes of N, N-dimethylacrylamide and N-vinyl-2-pyrrolidone, the compatibility is good in the curing state. Although produced, the polymer turned cloudy milky when it absorbed water.
본 중합에서는 N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide)와 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone)의 변화에 관계없이 경화상태에서는 상용성이 좋아 투명한 중합물을 만들 수는 있지만, 수화되면서 뿌연 우유빛으로 변화되기 때문에 렌즈에 적용함에 있어 사용될 수 없으며 렌즈에 적용하기 위해서는 N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide)와 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone) 중에 한 가지를 선택하여 사용하여야 함을 알 수 있다.In this polymerization, transparent polymers have good compatibility in the curing state regardless of the changes of N, N-dimethylacrylamide and N-vinyl-2-pyrrolidone. It can be used, but it cannot be used to apply to lens because it turns into milky milky color as it is hydrated.N, N-Dimethylacrylamide and N-vinyl-2-P can be applied to lens. It can be seen that one of the N-Vinyl-2-pyrrolidone should be selected and used.
실시예 10Example 10
: N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide), 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate), N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone), N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide) 및 디비닐 벤젠(Divinyl benzen)의 중합: N, O-Bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide), 2-hydroxy methacrylate, N-vinyl-2-pyrrolidone (N- Polymerization of Vinyl-2-pyrrolidone), N, N-dimethylacrylamide and Divinyl benzen
실시예 5에서 중합물의 함수율 조정 및 N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide), N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone) 물질간의 중합 적합성 확인 및 실시예 9와 비교하기 위해 실시한다.Adjusting the water content of the polymer in Example 5 and the confirmation of the polymerization suitability between the N, N- dimethyl acrylamide, N-vinyl-2-pyrrolidone (N-Vinyl-2-pyrrolidone) material To compare with 9.
실시예 8에서 얻은 결과를 통해 5 wt% 이하의 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide), 60 wt% 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate), N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide)와 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone)의 양을 40 wt% 이내에서 적당히 서로의 양을 변화시키면서 0.4 wt%의 가교제 디비닐 벤젠(Divinyl benzen) 혼합 용액을 만든 다음, 개시제 2,5-디메틸-2,5-디(2-에틸헥사노일 퍼록시)헥산(2,5-Dimethyl-2,5-di(2-ethylhexanoyl peroxy)hexane) 0.2 wt%을 용해시켜 110℃에서 30분 동안 중합시킨다.5 wt% or less of N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide), 60 wt% 2-hydroxy methacrylate (2-Hydroxyethyl from the results obtained in Example 8 methacrylate), N, N-dimethylacrylamide and N-vinyl-2-pyrrolidone in an amount of 40 wt%, varying the amount of each other appropriately. 0.4 wt% of a crosslinker divinyl benzen mixed solution was prepared, followed by initiator 2,5-dimethyl-2,5-di (2-ethylhexanoyl peroxy) hexane (2,5-Dimethyl-2, 0.2 wt% of 5-di (2-ethylhexanoyl peroxy) hexane) is dissolved and polymerized at 110 ° C. for 30 minutes.
그 결과 N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide)와 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone)의 변화에 관계없이 경화상태에서는 상용성이 좋아 투명한 중합물이 생성되었으나, 물을 흡수하면서 중합물은 뿌연 우유빛으로 변화 되었다.As a result, regardless of the changes of N, N-dimethylacrylamide and N-vinyl-2-pyrrolidone, the compatibility is good in the curing state. Although produced, the polymer turned cloudy milky when it absorbed water.
본 중합에서는 실시예 9와 비교하여도 같은 결과 얻을 수 있음을 알 수 있다. N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide)와 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone)의 변화에 관계없이 경화상태에서는 상용성이 좋아 투명한 중합물을 만들 수는 있지만, 수화되면서 뿌연 우유빛으로 변화되기 때문에 렌즈에 적용함에 있어 사용될 수 없으며 렌즈에 적용하기 위해서는 N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide)와 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone) 중에 한가지를 선택하여 사용하여야 함을 제공한다. In this polymerization, it can be seen that the same result can be obtained in comparison with Example 9. Regardless of the change of N, N-dimethylacrylamide and N-vinyl-2-pyrrolidone, it is compatible in hardening state to make transparent polymer. However, it cannot be used for lens application because it changes to cloudy milky color as it is hydrated.N, N-Dimethylacrylamide and N-vinyl-2-pyrrolidone (N, N-dimethylacrylamide) N-Vinyl-2-pyrrolidone) should be selected and used.
실시예 9와 비교하여도 같은 결과 얻을 수 있음을 제공한다.Compared with Example 9, the same result can be obtained.
실시예 11~16 및 비교예 1Examples 11-16 and Comparative Example 1
상기의 실시예의 결과를 토대로 하여, 실시예 11~16에서는 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate), N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide), 및 디비닐 벤젠(Divinyl benzen) (혹은 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate))에 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone) 또는 N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide)을 첨가하여 콘텍트 렌즈를 제조하였고, 비교예로서 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate) 및 가교제로 디비닐 벤젠(Divinyl benzen)의 혼합 용액에 개시제 2,5-디메틸-2,5-디(2-에틸헥사노일 퍼록시)헥산(2,5-Dimethyl-2,5-di(2-ethylhexanoyl peroxy)hexane)을 사용하여 콘텍트 렌즈를 제조하여 함수율, 탄성율, 인장강도 및 산소투과도 등의 물성을 비교해 보았다.Based on the results of the above examples, in Examples 11 to 16, 2-hydroxy methacrylate, N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide ), And N-Vinyl-2-pyrrolidone or N, N-dimethylacrylic acid in Divinyl benzen (or Ethylene glycol dimethacrylate). A contact lens was prepared by adding amide (N, N-Dimethylacrylamide), and as a comparative example, 2-hydroxy methacrylate and 2-vinyl benzen were used as a crosslinking agent in a mixed solution of divinyl benzen. Contact lens was prepared using 5-dimethyl-2,5-di (2-ethylhexanoyl peroxy) hexane (2,5-Dimethyl-2,5-di (2-ethylhexanoyl peroxy) hexane) to obtain moisture and elastic modulus. And physical properties such as tensile strength and oxygen permeability.
산소투과도는 조건하에서 단위 두께의 콘택트렌즈 재료의 단위 면적을 단위 압력 변화에 따라 투과하는 산소유속으로. 그 측정방법은 다음과 같다.Oxygen permeability is the oxygen flow rate that permeates the unit area of the contact lens material of unit thickness under the unit pressure change under conditions. The measuring method is as follows.
가. 측정하고자 하는 시편과 툴을 최대한 건조 시킨다. end. Dry the specimen and tool to be measured as much as possible.
나. 밑부분 툴에 렌즈를 장착하고 오링(o-ring)으로 고정시킨 후 윗부분의 툴을 덮어 4개의 나사로 가스의 누수가 없게 고정시킨다.I. Mount the lens on the bottom tool, fix it with an o-ring, and cover the tool on the top to fix the gas leaks with four screws.
다. 약10%의 비눗물로 지시부에 버블을 만들어 준다. All. Make a bubble in the indicator with about 10% soapy water.
라. 기체통과 각 부분의 라인을 연결 해주고 기체 압력 센서를 가동한다. la. Connect the gas cylinder with the line of each part and start the gas pressure sensor.
마. 약2시간여 측정하고자 하는 기체로 각 부분을 퍼지(purge)한다.hemp. Purge each part with the gas to be measured for about 2 hours.
바. 지시부의 버블이 움직이기 시작한 시간과 그때의 환경적인 요소를 기입하고 시간간격을 정하여 확인하고 기록으로 남긴다. bar. Enter the time when the indicator bubble began to move and the environmental factors at that time, determine the time interval, and record it.
사. 계산식을 이용하여 계산한다.four. Calculate using the formula.
상기 계산식은 다음과 같다.The above formula is as follows.
여기서 P,V,T는 실험이 실시되는 환경의 상태를 말하며 P',T'는 STP상태를 말하며 V'를 STP상태에 맞게 환산한 값이다.Where P, V, and T are the states of the environment where the experiment is conducted, and P 'and T' are the STP states and V 'is converted to STP.
여기서 l은 시편의 평균두께를 말하며 Pressure는 압력센서에서 나타내는 값을 대입한다. ①식의 값을 ②에 대입하여 Permeability(DK)를 구한다.Where l is the average thickness of the specimen and Pressure is the value indicated by the pressure sensor. Permeability (DK) is obtained by substituting the value of the equation into ②.
함수율은 시료의 건조 중량에 대한 수분 중량비를 퍼센트로 표시하는 건시료 중량기준 (Dry-weight-basis)을 통상적으로 사용하고 있으나 수분을 포함한 총 중량에 대한 함유 수분비를 퍼센트로 표시하는 습시료 중량기준(Wet-weight-basis)도 많이 사용하고 있다. 그러나 "포화 함수율에서의 상대 함수율"이나 "주위 공기의 상대습도에 의한 평형 함수율" 등 함수율과 관련된 많은 정의가 생겨나고 있으며, 최근에는 시료의 총체적에 대한 함유 수분 체적비를 퍼센트로 표시하는 체적함수율도 일부 사용되고 있다.The moisture content is a dry sample weight standard (Dry-weight-basis) which expresses the water weight ratio to the dry weight of the sample in percentage, but the wet sample weight which expresses the moisture content ratio in percentage to the total weight including water. Wet-weight-basis is also heavily used. However, there are many definitions related to water content, such as "relative water content at saturated water content" or "equilibrium water content due to relative humidity of ambient air". Recently, the volumetric water content ratio expressed as a percentage of the total water content to the total volume of the sample is also introduced. Some are being used.
콘택트렌즈의 경우 습시료 중량기준을 이용하여 수분함량을 측정한다.In the case of contact lenses, the moisture content is measured using the weight of the wet sample.
측정방법은 다음과 같다.The measurement method is as follows.
가. 충분히 렌즈를 수화 시킨다.(약 24시간이상) end. I hydrate a lens enough. (More than approximately 24 hours)
나. 시료(lens)의 물기를 사슴가죽으로 가볍게 눌러서 제거 후 중량을 측정한다.(M1)I. Lightly remove the sample (lens) with deerskin and remove the weight. (M 1 )
다. 시료를 오븐기에서 최소 20분이상(더이상 무게의 변화가 없는 시점) 건 조하여 한다.All. Dry the sample in the oven for at least 20 minutes (no more weight change).
라. 건조된 시료의 중량을 측정한다.(M2)la. Measure the weight of the dried sample (M 2 )
마. 가에서 라까지 같은 방법으로 최소 10개의 랜즈를 측정하고 평균값을 함수율로 정한다.hemp. Measure at least 10 lenses in the same way from a to d and set the average as the moisture content.
계산식은 다음과 같다.The calculation is as follows.
실시예 11: 콘택트 렌즈의 제조 1Example 11: Preparation of Contact Lenses 1
: 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate), N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide), N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone), 및 디비닐 벤젠(Divinyl benzen) (혹은 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate))2-Hydroxyethyl methacrylate, N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide), N-vinyl-2-pyrrolidone (N- Vinyl-2-pyrrolidone), and divinyl benzen (or ethylene glycol dimethacrylate)
64.3 wt% 이상의 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate), 30 wt% 이하의 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone), 5 wt% 이하의 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide) 및 가교제로는 0.5 wt% 이상 디비닐 벤젠(Divinyl benzen) (혹은 0.6 wt% 이상의 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate))의 혼합 용액에, 개시제 2,5-디메틸-2,5-디(2-에틸헥사노일 퍼록시)헥산(2,5-Dimethyl-2,5-di(2-ethylhexanoyl peroxy)hexane) 0.2 wt%이상을 용해시킨 다음, 폴리프로필렌(Polypropylene)으로 제조된 몰드에 주입하고(Casting Mold법) 110℃에서 30분 동안 중합시켜 경화시켰다. 이어, 몰드에서 렌즈를 분리하여 상용상태(투명도)를 확인한 결과, 투명하게 제조되었으며, 수화시켜 함수율 및 렌즈의 상태를 측정하였다.64.3 wt% or more of 2-Hydroxyethyl methacrylate, 30 wt% or less of N-Vinyl-2-pyrrolidone, 5 wt% or less of N, O Bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) And a crosslinking agent in a mixed solution of 0.5 wt% or more of divinyl benzen (or 0.6 wt% or more of ethylene glycol dimethacrylate) to initiator 2,5-dimethyl-2,5-di. 0.2 wt% or more of (2-ethylhexanoyl peroxy) hexane (2,5-Dimethyl-2,5-di (2-ethylhexanoyl peroxy) hexane) is dissolved, and then injected into a mold made of polypropylene. (Casting Mold method) and polymerized at 110 ℃ for 30 minutes to cure. Subsequently, the lens was removed from the mold to confirm the compatibility state (transparency), and then it was manufactured to be transparent, and hydrated to measure the water content and the state of the lens.
실시예 12: 콘택트 렌즈의 제조 2Example 12 Preparation of Contact Lenses 2
: 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate), N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide) N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone) 및 디비닐 벤젠(Divinyl benzen) (혹은 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate))2-Hydroxyethyl methacrylate, N, O-bis (trimethylsilyl) acrylamide N-Vinyl-2-pyrrolidone (N-Vinyl) -2-pyrrolidone) and divinyl benzen (or ethylene glycol dimethacrylate)
83.5 wt%이상의 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate), 15 wt% 이하의 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone), 1 wt% 이하의 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide) 및 가교제로는 0.3 wt% 이상의 디비닐 벤젠(Divinyl benzen) (혹은 0.4 wt% 이상의 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate))의 혼합 용액에, 개시제 2,5-디메틸-2,5-디(2-에틸헥사노일 퍼록시)헥산(2,5-Dimethyl-2,5-di(2-ethylhexanoyl peroxy)hexane) 0.2 wt% 이상을 사용하여 실시예 11과 동일하게 제조하고 물성을 평가하였다.83.5 wt% or more of 2-Hydroxyethyl methacrylate, 15 wt% or less of N-Vinyl-2-pyrrolidone, 1 wt% or less of N, O Bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) And as a crosslinking agent in a mixed solution of 0.3 wt% or more of divinyl benzen (or 0.4 wt% or more of ethylene glycol dimethacrylate), the initiator 2,5-dimethyl-2,5-di (2-Ethylhexanoyl peroxy) hexane (2,5-Dimethyl-2,5-di (2-ethylhexanoyl peroxy) hexane) 0.2 wt% or more was used in the same manner as in Example 11, and physical properties were evaluated.
실시예 13: 콘택트 렌즈의 제조 3Example 13: Preparation of Contact Lenses 3
: 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate), N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide), N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone) 및 디비닐 벤젠(Divinyl benzen) (혹은 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate))2-Hydroxyethyl methacrylate, N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide), N-vinyl-2-pyrrolidone (N- Vinyl-2-pyrrolidone) and divinyl benzen (or ethylene glycol dimethacrylate)
71.4 wt% 이상의 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate), 25 wt%이하의 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone), 3 wt% 이하의 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide) 및 가교제로는 0.4 wt% 이상의 디비닐 벤젠(Divinyl benzen) (혹은 0.5 wt% 이상의 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate))의 혼합 용액에, 개시제 2,5-디메틸-2,5-디(2-에틸헥사노일 퍼록시)헥산(2,5-Dimethyl-2,5-di(2-ethylhexanoyl peroxy)hexane) 0.2 wt% 이상을 사용하여 실시예 11과 동일하게 제조하고 물성을 평가하였다.71.4 wt% or more of 2-Hydroxyethyl methacrylate, 25 wt% or less of N-Vinyl-2-pyrrolidone, 3 wt% or less of N, O Bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) And a crosslinking agent in a mixed solution of 0.4 wt% or more of divinyl benzen (or 0.5 wt% or more of ethylene glycol dimethacrylate), and initiator 2,5-dimethyl-2,5-di. (2-Ethylhexanoyl peroxy) hexane (2,5-Dimethyl-2,5-di (2-ethylhexanoyl peroxy) hexane) 0.2 wt% or more was used in the same manner as in Example 11, and physical properties were evaluated.
실시예 14: 콘택트 렌즈의 제조 4Example 14 Preparation of Contact Lenses 4
: 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate) ,N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide), N-비닐-2-피롤리 돈(N-Vinyl-2-pyrrolidone) 및 디비닐 벤젠(Divinyl benzen) (혹은 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate)): 2-Hydroxyethyl methacrylate, N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide), N-vinyl-2-pyrrolidone (N- Vinyl-2-pyrrolidone) and divinyl benzen (or ethylene glycol dimethacrylate)
64.3 wt% 이하의 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate), 30 wt% 이상의 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone), 5 wt% 이하의 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide) 및 가교제로는 0.5 wt%이상의 디비닐 벤젠(Divinyl benzen) (혹은 0.6 wt% 이상의 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate))의 혼합 용액에, 개시제 2,5-디메틸-2,5-디(2-에틸헥사노일 퍼록시)헥산(2,5-Dimethyl-2,5-di(2-ethylhexanoyl peroxy)hexane) 0.2 wt% 이상을 사용하여 실시예 11과 동일하게 제조하고 물성을 평가하였다.64.3 wt% or less 2-Hydroxyethyl methacrylate, 30 wt% or more N-Vinyl-2-pyrrolidone, 5 wt% or less N, O 0.5 wt% or more of divinyl benzen (or 0.6 wt% or more of ethylene glycol dimethacrylate as a bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) and a crosslinking agent In the mixed solution of)), initiator 2,5-dimethyl-2,5-di (2-ethylhexanoyl peroxy) hexane (2,5-Dimethyl-2,5-di (2-ethylhexanoyl peroxy) hexane) 0.2 Using wt% or more was prepared in the same manner as in Example 11 and the physical properties were evaluated.
실시예 15: 콘택트 렌즈의 제조 5Example 15 Preparation of Contact Lenses 5
: 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate), N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide), N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone) 및 디비닐 벤젠(Divinyl benzen) (혹은 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate))2-Hydroxyethyl methacrylate, N, O-bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide), N-vinyl-2-pyrrolidone (N- Vinyl-2-pyrrolidone) and divinyl benzen (or ethylene glycol dimethacrylate)
65.4 wt% 이하의 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate), 30 wt% 이상의 N-비닐-2-피롤리돈(N-Vinyl-2-pyrrolidone), 4 wt% 이하의 N,O-비스(트리메틸실릴)아크릴아마이드(N,O- Bis(trimethylsilyl)acrylamide) 및 가교제로는 0.4 wt%이상의 디비닐 벤젠(Divinyl benzen) (혹은 0.5 wt% 이상의 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate))의 혼합 용액에, 개시제 2,5-디메틸-2,5-디(2-에틸헥사노일 퍼록시)헥산(2,5-Dimethyl-2,5-di(2-ethylhexanoyl peroxy)hexane) 0.2 wt% 이상을 사용하여 실시예 11과 동일하게 제조하고 물성을 평가하였다.65.4 wt% or less of 2-Hydroxyethyl methacrylate, 30 wt% or more of N-Vinyl-2-pyrrolidone, 4 wt% or less of N, O 0.4 wt% or more of divinyl benzen (or 0.5 wt% or more of ethylene glycol dimethacrylate) as a bis (trimethylsilyl) acrylamide (N, O-Bis (trimethylsilyl) acrylamide) and a crosslinking agent. In the mixed solution of)), initiator 2,5-dimethyl-2,5-di (2-ethylhexanoyl peroxy) hexane (2,5-Dimethyl-2,5-di (2-ethylhexanoyl peroxy) hexane) 0.2 Using wt% or more was prepared in the same manner as in Example 11 and the physical properties were evaluated.
실시예 16: 콘택트 렌즈의 제조 5Example 16: Fabrication of Contact Lenses 5
: 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate), N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide), N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide) 및 디비닐 벤젠(Divinyl benzen) (혹은 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate))2-Hydroxyethyl methacrylate, N, O-bis (trimethylsilyl) acrylamide, N, N-dimethylacrylamide, N, N-dimethylacrylamide Dimethylacrylamide) and Divinyl benzen (or ethylene glycol dimethacrylate)
66.4 wt% 이하의 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate), 30 wt% 이상의 N,N-디메틸아크릴아마이드(N,N-Dimethylacrylamide), 0.3 g의 N,O-비스(트리메틸실릴)아크릴아마이드(N,O-Bis(trimethylsilyl)acrylamide) 및 가교제로는 0.4 wt% 이상의 디비닐 벤젠(Divinyl benzen) (혹은 0.5 wt% 이상의 에틸렌 글리콜 디메타크릴레이트(Ethylene glycol dimethacrylate))의 혼합 용액에, 개시제 2,5-디메틸-2,5-디(2-에틸헥사노일 퍼록시)헥산(2,5-Dimethyl-2,5-di(2-ethylhexanoyl peroxy)hexane) 0.2 wt%이상을 사용하여 실시예 11과 동일하게 제조하고 물성을 평 가하였다.66.4 wt% or less 2-Hydroxyethyl methacrylate, 30 wt% or more N, N-dimethylacrylamide, 0.3 g N, O-bis (trimethylsilyl) Acrylamide (N, O-Bis (trimethylsilyl) acrylamide) and a crosslinking agent in a mixed solution of 0.4 wt% or more of divinyl benzen (or 0.5 wt% or more of ethylene glycol dimethacrylate) Using 0.2 wt% or more of initiator 2,5-dimethyl-2,5-di (2-ethylhexanoyl peroxy) hexane (2,5-Dimethyl-2,5-di (2-ethylhexanoyl peroxy) hexane) Prepared in the same manner as in Example 11 and evaluated the physical properties.
비교예 1: 콘택트 렌즈의 제조Comparative Example 1: Preparation of Contact Lens
기존에 많이 사용되는 9 g의 2-하이드록실 메타크릴레이트(2-Hydroxyethyl methacrylate) 및 가교제로는 1 g의 디비닐 벤젠(Divinyl benzen)의 혼합 용액에, 개시제 2,5-디메틸-2,5-디(2-에틸헥사노일 퍼록시)헥산(2,5-Dimethyl-2,5-di(2-ethylhexanoyl peroxy)hexane) 0.02 g을 용해시킨 다음, 폴리프로필렌(Polypropylene)으로 제조된 몰드에 주입하고(Casting Mold법) 110℃에서 30분 동안 중합시켜 경화시켰다. 이어, 몰드에서 렌즈를 분리하여 함수율 측정한 결과, 38%의 함수율과 산소투과도 10 ~ 20 Dk [10-11(㎠/sec)(㎖ O2 ㎜Hg)]로 낮게 나타냈다.9 g of 2-Hydroxyethyl methacrylate and a crosslinking agent, which are commonly used, are mixed with 1 g of divinyl benzen in a mixed solution, and initiator 2,5-dimethyl-2,5 -Dissolve 0.02 g of di (2-ethylhexanoyl peroxy) hexane (2,5-Dimethyl-2,5-di (2-ethylhexanoyl peroxy) hexane) and inject into a mold made of polypropylene (Casting Mold method) and polymerized at 110 ℃ for 30 minutes to cure. Subsequently, as a result of measuring the water content by removing the lens from the mold, the water content and oxygen permeability of 38% were 10 to 20 Dk [10 −11 ( cm 2 / sec) (ml O 2 mmHg)].
11Example
11
12Example
12
13Example
13
14Example
14
15Example
15
16Example
16
이상64.2%
More than
이상83.4%
More than
이상71.3%
More than
이상64.2%
More than
이상65.3%
More than
이상69%
More than
이하5%
Below
0.6%이상0.5% or more
0.6% or more
0.4%이상0.3% or more
0.4% or more
0.5%이상0.4% or more
0.5% or more
0.6%이상0.5% or more
0.6% or more
0.5%이상0.4% or more
0.5% or more
0.5%이상0.4% or more
0.5% or more
상기와 같은 실시예 및 비교예의 함량을 가지고 제조된 콘텍트렌즈의 물성은 다음과 같다.The physical properties of the contact lenses manufactured with the contents of Examples and Comparative Examples as described above are as follows.
Moisture content (%)
Modulus (%)
(g/mm3)The tensile strength
(g / mm 3 )
(DK)Oxygen permeability
(DK)
상기 표 2에서 볼 수 있는 바와 같이, 본 발명의 실시예들은 친수성이며, 함수율은 40 ~ 70%, 산소투과성이 50~ 90 Dk [10-11(㎠/sec)(㎖ O2 ㎜Hg)]로서 매우 높으며, 비교예와 비교해보면 함수율과 산소투과도에서 월등히 높은 수치를 보이는 것을 알 수 있다. As can be seen in Table 2, the embodiments of the present invention are hydrophilic, water content is 40 ~ 70%, oxygen permeability 50 ~ 90 Dk [10 -11 ( cm 2 / sec) (ml O 2 mmHg)] It is very high, and compared with the comparative example, it can be seen that the water content and oxygen permeability are much higher.
이상에서 살펴본 바와 같이, 본 발명 연질 콘텍트렌즈용 실리콘 하이드로겔 조성물 및 그 조성에 의해 제조된 연질 콘텍트렌즈에 의하면, 안구에 직접 접촉하여 근시, 원시, 난시 따위의 교정을 위하여 사용되는 시력을 보정할 수 있는 콘택트렌즈로서 40 ~ 70%의 친수성 및 고함수력, 높은 산소투과율 (50~100 Dk), 좋은 탄성력(Elongation 200~400%) 및 우수한 광 투과도로 장시간 콘택트렌즈를 착용하는 착용자에게 눈의 건강함과 이물감, 건조감, 각막의 압박 등을 최소화하여 편안함을 제공하고 각막부종이나 기타 질병에서의 발생율을 감소시킬 수 있는 실리콘 하이드로겔 콘택트 렌즈를 제공할 수 있다.As described above, according to the present invention, the silicone hydrogel composition for the soft contact lens and the soft contact lens manufactured by the composition may be used to directly correct the visual acuity used for the correction of myopia, hyperopia, and astigmatism by direct contact with the eye. Eye contact for wearer who wears contact lenses for a long time with 40 ~ 70% hydrophilicity and high water content, high oxygen transmittance (50 ~ 100 Dk), good elasticity (Elongation 200 ~ 400%) and excellent light transmittance. Silicone hydrogel contact lenses can be provided that minimize comfort, dryness, dryness and pressure on the cornea to provide comfort and reduce the incidence of corneal edema and other diseases.
또한, 본 발명에 따른 실리콘 하이드로겔 연질 콘텍트렌즈는 산소투과성이 우수한 산소투과성 하드렌즈(RGP렌즈)의 장점과 부드러운 착용감의 연질렌즈의 장점을 모두 가지고 있어, 이 렌즈는 약 2주에서 한 달간 연속해서 착용이 가능하여 매일 착용 및 탈부착을 해야 하는 기존렌즈의 불편을 해결할 수 있다.In addition, the silicone hydrogel soft contact lens according to the present invention has both the advantages of the oxygen permeable hard lens (RGP lens) excellent in oxygen permeability and the soft lens of the soft fit, the lens is continuous for about two weeks to one month It can be worn to solve the inconvenience of conventional lenses that must be worn and detached every day.
Claims (7)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020070061970A KR101231181B1 (en) | 2007-06-25 | 2007-06-25 | Silicone-hydrogel compound for soft contact lens and soft contact lens produced using the compound |
| CN2007800535071A CN101688042B (en) | 2007-06-25 | 2007-10-18 | Silicone hydrogel compound for soft contact lens and soft contact lens prepared using the compound |
| RU2009146491/05A RU2434899C2 (en) | 2007-06-25 | 2007-10-18 | Silicone-hydrogel compound for soft contact lenses and soft contact lenses made from said compound |
| AU2007355828A AU2007355828B2 (en) | 2007-06-25 | 2007-10-18 | Silicone-hydrogel compound for soft contact lens and soft contact lens produced using the compound |
| CA2686938A CA2686938C (en) | 2007-06-25 | 2007-10-18 | Silicone-hydrogel compound for soft contact lens and soft contact lens produced using the compound |
| JP2010514580A JP5432133B2 (en) | 2007-06-25 | 2007-10-18 | Monomer composition for silicon hydrogel for soft contact lens and soft contact lens produced by the monomer composition |
| PCT/KR2007/005098 WO2009001987A1 (en) | 2007-06-25 | 2007-10-18 | Silicone-hydrogel compound for soft contact lens and soft contact lens produced using the compound |
| UAA201000666A UA92126C2 (en) | 2007-06-25 | 2007-10-18 | Silicone-hydrogel compound for soft contact lens and soft contact lens produced using the compound |
| EP07833407A EP2170992A4 (en) | 2007-06-25 | 2007-10-18 | Silicone-hydrogel compound for soft contact lens and soft contact lens produced using the compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020070061970A KR101231181B1 (en) | 2007-06-25 | 2007-06-25 | Silicone-hydrogel compound for soft contact lens and soft contact lens produced using the compound |
Publications (2)
| Publication Number | Publication Date |
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| KR20080113467A KR20080113467A (en) | 2008-12-31 |
| KR101231181B1 true KR101231181B1 (en) | 2013-02-07 |
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| KR1020070061970A Active KR101231181B1 (en) | 2007-06-25 | 2007-06-25 | Silicone-hydrogel compound for soft contact lens and soft contact lens produced using the compound |
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| Country | Link |
|---|---|
| EP (1) | EP2170992A4 (en) |
| JP (1) | JP5432133B2 (en) |
| KR (1) | KR101231181B1 (en) |
| CN (1) | CN101688042B (en) |
| AU (1) | AU2007355828B2 (en) |
| CA (1) | CA2686938C (en) |
| RU (1) | RU2434899C2 (en) |
| UA (1) | UA92126C2 (en) |
| WO (1) | WO2009001987A1 (en) |
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| KR20190023448A (en) | 2017-08-29 | 2019-03-08 | 대구가톨릭대학교산학협력단 | Compositions for hydrogel contact lens having high performance |
| KR20190075281A (en) | 2017-12-21 | 2019-07-01 | 주식회사 티씨 싸이언스 | Method for manufacturing silicon-containing soft contact lens and Soft contact lens manufactured by the method and Composition for molding the soft contact lens |
| KR20220160733A (en) | 2021-05-28 | 2022-12-06 | 김영일 | Hydrogel contact lenses with excellent durability, humidity and improved commerciality |
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| JP5896404B2 (en) * | 2008-07-21 | 2016-03-30 | ノバルティス アーゲー | Silicone-containing polymer material having hydrolyzable groups |
| CN103969706B (en) * | 2008-12-18 | 2017-08-25 | 诺华股份有限公司 | Lens forming composition suitable for manufacturing silicone hydrogel contact lens |
| KR101044955B1 (en) * | 2009-04-06 | 2011-06-29 | 성아영 | High performance hydrogel contact lenses with phosphazine substituted with vinyl groups |
| TWI758885B (en) | 2010-07-30 | 2022-03-21 | 瑞士商愛爾康公司 | Hydrated contact lens |
| JP6131243B2 (en) | 2011-04-01 | 2017-05-17 | ノバルティス アーゲー | Composition for forming contact lenses |
| CN102382226B (en) * | 2011-08-12 | 2014-03-19 | 天津博纳艾杰尔科技有限公司 | Preparation method of poly-N-vinylpyrrodidone-divinylbenzene microsphere |
| US8940812B2 (en) * | 2012-01-17 | 2015-01-27 | Johnson & Johnson Vision Care, Inc. | Silicone polymers comprising sulfonic acid groups |
| US9395468B2 (en) | 2012-08-27 | 2016-07-19 | Ocular Dynamics, Llc | Contact lens with a hydrophilic layer |
| CN105917270A (en) | 2013-11-15 | 2016-08-31 | 视觉力学有限责任公司 | Contact lens with a hydrophilic layer |
| US9459377B2 (en) * | 2014-01-15 | 2016-10-04 | Johnson & Johnson Vision Care, Inc. | Polymers comprising sulfonic acid groups |
| AU2015201321A1 (en) * | 2014-03-31 | 2015-10-15 | Johnson & Johnson Vision Care, Inc. | Silicone acrylamide copolymer |
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| TW201617692A (en) * | 2014-07-21 | 2016-05-16 | 視覺動力公司 | Contact lenses and methods of making contact lenses |
| JP6774947B2 (en) | 2014-12-09 | 2020-10-28 | タンジブル サイエンス インコーポレイテッド | Medical device coating with biocompatible layer |
| MY197603A (en) | 2017-06-07 | 2023-06-27 | Alcon Inc | Silicone hydrogel contact lenses |
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| KR101944717B1 (en) * | 2017-11-17 | 2019-02-01 | 주식회사 인터로조 | Soft Contact Lens Having UV Protection function and Manufacturing Method Thereof |
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| KR20070010123A (en) * | 2004-03-05 | 2007-01-22 | 존슨 앤드 존슨 비젼 케어, 인코포레이티드 | Wettable hydrogels comprising acyclic polyamides |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20190023448A (en) | 2017-08-29 | 2019-03-08 | 대구가톨릭대학교산학협력단 | Compositions for hydrogel contact lens having high performance |
| KR20190075281A (en) | 2017-12-21 | 2019-07-01 | 주식회사 티씨 싸이언스 | Method for manufacturing silicon-containing soft contact lens and Soft contact lens manufactured by the method and Composition for molding the soft contact lens |
| KR20220160733A (en) | 2021-05-28 | 2022-12-06 | 김영일 | Hydrogel contact lenses with excellent durability, humidity and improved commerciality |
Also Published As
| Publication number | Publication date |
|---|---|
| RU2009146491A (en) | 2011-07-27 |
| CN101688042B (en) | 2012-01-11 |
| RU2434899C2 (en) | 2011-11-27 |
| AU2007355828A8 (en) | 2010-03-18 |
| JP5432133B2 (en) | 2014-03-05 |
| EP2170992A1 (en) | 2010-04-07 |
| CA2686938C (en) | 2013-04-02 |
| AU2007355828A1 (en) | 2008-12-31 |
| CN101688042A (en) | 2010-03-31 |
| UA92126C2 (en) | 2010-09-27 |
| JP2010531474A (en) | 2010-09-24 |
| CA2686938A1 (en) | 2008-12-31 |
| WO2009001987A1 (en) | 2008-12-31 |
| EP2170992A4 (en) | 2010-08-04 |
| AU2007355828B2 (en) | 2011-03-03 |
| KR20080113467A (en) | 2008-12-31 |
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