US20160327809A1 - Polymerizable composition for coloring contact lenses - Google Patents
Polymerizable composition for coloring contact lenses Download PDFInfo
- Publication number
- US20160327809A1 US20160327809A1 US14/918,561 US201514918561A US2016327809A1 US 20160327809 A1 US20160327809 A1 US 20160327809A1 US 201514918561 A US201514918561 A US 201514918561A US 2016327809 A1 US2016327809 A1 US 2016327809A1
- Authority
- US
- United States
- Prior art keywords
- contact lenses
- polymerizable composition
- colorant
- lenses according
- coloring
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 57
- 238000004040 coloring Methods 0.000 title claims abstract description 27
- 239000003086 colorant Substances 0.000 claims abstract description 48
- 239000002131 composite material Substances 0.000 claims abstract description 28
- -1 (methyl)methacryloxy group Chemical group 0.000 claims abstract description 25
- 239000002243 precursor Substances 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 239000000178 monomer Substances 0.000 claims abstract description 12
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 7
- 150000004706 metal oxides Chemical class 0.000 claims abstract description 7
- 239000012670 alkaline solution Substances 0.000 claims abstract description 6
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 13
- 239000003999 initiator Substances 0.000 claims description 12
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical group C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 7
- 229920002635 polyurethane Polymers 0.000 claims description 7
- 239000004814 polyurethane Substances 0.000 claims description 7
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims description 6
- 239000002270 dispersing agent Substances 0.000 claims description 6
- 239000002562 thickening agent Substances 0.000 claims description 6
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 5
- 239000003431 cross linking reagent Substances 0.000 claims description 5
- 239000004925 Acrylic resin Substances 0.000 claims description 4
- 229920000178 Acrylic resin Polymers 0.000 claims description 4
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims description 4
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 4
- 239000000017 hydrogel Substances 0.000 claims description 4
- 229920001296 polysiloxane Polymers 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 3
- WIYVVIUBKNTNKG-UHFFFAOYSA-N 6,7-dimethoxy-3,4-dihydronaphthalene-2-carboxylic acid Chemical compound C1CC(C(O)=O)=CC2=C1C=C(OC)C(OC)=C2 WIYVVIUBKNTNKG-UHFFFAOYSA-N 0.000 claims description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 3
- RMKZLFMHXZAGTM-UHFFFAOYSA-N [dimethoxy(propyl)silyl]oxymethyl prop-2-enoate Chemical compound CCC[Si](OC)(OC)OCOC(=O)C=C RMKZLFMHXZAGTM-UHFFFAOYSA-N 0.000 claims description 3
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 3
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 3
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 3
- 229920001568 phenolic resin Polymers 0.000 claims description 3
- 239000005011 phenolic resin Substances 0.000 claims description 3
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 claims description 3
- 239000000499 gel Substances 0.000 claims description 2
- 239000007822 coupling agent Substances 0.000 abstract 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000005259 measurement Methods 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 238000002845 discoloration Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 230000035699 permeability Effects 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 238000005562 fading Methods 0.000 description 4
- SZVJSHCCFOBDDC-UHFFFAOYSA-N ferrosoferric oxide Chemical compound O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 4
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical group CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 2
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 2
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000002953 phosphate buffered saline Substances 0.000 description 2
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002352 surface water Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- DGMIADDEEIQHOC-UHFFFAOYSA-N C=C.C=C.C=C.CC(=C)C(=O)OCCOC(=O)C(C)=C Chemical compound C=C.C=C.C=C.CC(=C)C(=O)OCCOC(=O)C(C)=C DGMIADDEEIQHOC-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- UKMBKKFLJMFCSA-UHFFFAOYSA-N [3-hydroxy-2-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)OC(=O)C(C)=C UKMBKKFLJMFCSA-UHFFFAOYSA-N 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- MLCHBQKMVKNBOV-UHFFFAOYSA-M dioxido(phenyl)phosphanium Chemical compound [O-]P(=O)C1=CC=CC=C1 MLCHBQKMVKNBOV-UHFFFAOYSA-M 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- OWYXWJZFFXUBOK-UHFFFAOYSA-N ethene 2-(2-methylprop-2-enoyloxy)ethyl 2-methylprop-2-enoate Chemical compound C=C.C=C.C=C.C=C.CC(=C)C(=O)OCCOC(=O)C(C)=C OWYXWJZFFXUBOK-UHFFFAOYSA-N 0.000 description 1
- FFYWKOUKJFCBAM-UHFFFAOYSA-N ethenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC=C FFYWKOUKJFCBAM-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- WCYDYSJNRRTEID-UHFFFAOYSA-N n,n-dimethylprop-2-enamide;ethane-1,2-diamine Chemical compound NCCN.CN(C)C(=O)C=C WCYDYSJNRRTEID-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C7/00—Optical parts
- G02C7/10—Filters, e.g. for facilitating adaptation of the eyes to the dark; Sunglasses
- G02C7/108—Colouring materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
-
- 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
-
- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C7/00—Optical parts
- G02C7/02—Lenses; Lens systems ; Methods of designing lenses
- G02C7/04—Contact lenses for the eyes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2265—Oxides; Hydroxides of metals of iron
Definitions
- the present disclosure relates to a polymerizable composition for coloring contact lenses. More particularly, the polymerizable composition for coloring contact lenses has good adhesion to the contact lenses so that no discoloration or fading occurred on the colored contact lenses made from hydrogel or silicone hydrogel.
- One of the conventional methods for manufacturing colored contact lens is to mix a colorant and the hydrophilic monomers to form a mixture, and then a colored layer is formed by printing or transferring the mixture on a surface of the contact lens.
- the method is unfavorable because the colored layer lacks the interaction force with the contact lens, so that the colored layer is easily peeling from contact lenses and discoloration or fading occurs.
- Another one of the conventional methods for manufacturing colored contact lenses is first to form a colored layer on the contact lens surface, and than a transparent layer is covered on the colored layer to protect the colored layer from being damaged and discolored. But, this method is so complicated and costly.
- the polymerizable composition of the present disclosure provides good adhesion to contact lenses to avoid discoloration or fading on the colored contact lenses.
- the manufacturing method for coloring contact lenses of the present disclosure is simpler than the conventional manufacturing methods.
- a novel polymerizable composition for coloring contact lenses comprising a composite colorant and at least one hydrophilic monomer.
- the composite colorant is produced by a reaction of a colorant precursor and a (methyl)methacryloxy group-containing silane coupling agent.
- the colorant precursor is produced by a reaction of a metal oxide a siloxane compound under alkaline solution.
- the (methyl)methacryloxy group-containing silane coupling agent for manufacturing the composite colorant is selected from the group consisting of 3-(meth)acryloxypropyltrimethoxysilane, 3-(meth)acryloxypropyltriethoxysilane, 3-(meth)acryloxypropylmethyldiethoxysilane and 3-(meth)acryloxypropylmethyl-dimethoxysilane and a combination thereof.
- the metal oxide for manufacturing the colorant precursor applied for coloring contact lenses is known in the art, for example, such as inorganic colorant and/or inorganic pigment.
- the inorganic colorant and/or inorganic can be, but not limited to, Iron Oxide Black, Iron Oxide Blown, Iron Oxide Yellow, Iron Oxide Red or Titanium Dioxide.
- the siloxane compound for manufacturing the colorant precursor is tetraethoxy silane or tetramethoxy silane.
- the hydrophilic monomer is selected from the group consisting of N-vinylpyrrolidone (NVP), 2-hydroxyethyl methacrylate (HEMA), N,N-dimethylacrylamide (DMA), methyl acrylic acid, acrylic acid, glycidyl methacrylate (OMA), (methyl)acrylamide, 2-(N,N-dimethylamino) ethyl methacrylate (DMAEMA), vinyl acetate, 2-(dimethylamino)ethyl methacrylate, N-acrylolmorpholine and a combination thereof.
- NRP N-vinylpyrrolidone
- HEMA 2-hydroxyethyl methacrylate
- DMA N,N-dimethylacrylamide
- OMA glycidyl methacrylate
- vinyl acetate 2-(dimethylamino)ethyl methacrylate
- N-acrylolmorpholine N-acrylolmorpholine
- the polymerizable composition for coloring contact lenses further includes a thickener which is selected from the group consisting of polyurethane, acrylic resin, phenolic resin, polyvinylpyrrodine and a combination thereof.
- the polymerizable composition for coloring contact lenses further includes a crosslinking agent.
- the polymerizable composition for coloring contact lenses further includes a dispersant.
- the polymerizable composition for coloring contact lenses further includes a photo initiator or a thermal initiator.
- the composite colorant is present at an amount of 10 weight percent to 60 weight percent based on the total amount of the polymerizable composition.
- the polymerizable composition is used for coloring contact lenses made from silicone gel or hydrogel.
- the present disclosure provides a navel polymerizable composition for coloring contact lenses, comprising a composite colorant and at least one hydrophilic monomer.
- the composite colorant is produced by a reaction of a colorant precursor and a (methyl)methacryloxy group-containing silane coupling agent, wherein the colorant precursor is produced by a reaction of a metal oxide and a siloxane compound under alkaline condition.
- the hydrophilic monomers for manufacturing the polymerizable composition can be, but not limited to N-vinylpyrrolidone (NVP), 2-hydroxyethyl methacrylate (HEMA), N,N-dimethylacrylamide (DMA), methyl acrylic acid (MAA), acrylic acid, glycidyl methacrylate (GMA), (methyl)acrylamide, 2-(N,N-dimethylamino) ethyl methacrylate (DMAEMA), vinyl acetate, 2-(Dimethylamino)ethyl methacrylate, N-acrylolmorpholine and a combination thereof.
- NRP N-vinylpyrrolidone
- HEMA 2-hydroxyethyl methacrylate
- DMA N,N-dimethylacrylamide
- MAA methyl acrylic acid
- GMA glycidyl methacrylate
- DMAEMA 2-(N,N-dimethylamino) ethyl methacrylate
- vinyl acetate 2-
- the hydrophilic monomers is present at an amount of 10 weight percent to 30 weight percent based on the total weight of the polymerizable composition.
- the composite colorant is present at an amount of 10 weight percent to 60 weight percent based on the total weight of the polymerizable composition.
- the composite colorant is produced by a reaction of a colorant precursor and a (methyl)methacryloxy group-containing silane coupling agent.
- the (methyl)methacryloxy group-containing silane coupling agent for manufacturing the composite colorant selected from the group consisting of 3-(meth)acryloxypropyltrimethoxysilane, 3-(meth)acryloxypropyltriethoxysilane, 3-(meth)acryloxypropylmethyldiethoxysilane and 3-(meth)acryloxypropylmethyl-dimethoxysilane and a combination thereof.
- reaction condition for the colorant precursor reacted with the (methyl)methacryloxy group-containing silane coupling agent is at 30° C. to 70° C. for 2 hours to 24 hours.
- the colarant precursor is produced by a reaction of a metal oxide and a siloxane compound under alkaline solution.
- the metal oxide for manufacturing the colorant precursor applied for coloring contact lenses is known in the art, for example, such as inorganic colorant and/or inorganic pigment.
- the inorganic colorant and/or inorganic can be, but not limited to, Iron Oxide Black, Iron Oxide Blown, Iron Oxide Yellow, Iron Oxide Red or Titanium Dioxide.
- the siloxane compound for manufacturing the colorant precursor is tetraethoxy silane or tetramethoxy silane.
- the pH value of alkaline solution is in the range of 8 to 10.
- the solvent in the alkaline solution is selected from the group consisting of water, methanol, ethanol and a combination thereof.
- the polymerizable composition further includes a thickener which is selected from the group consisting of polyurethane, acrylic resin, phenolic resin, polyvinylpyrrodine and a combination thereof.
- the thickener is present at an amount of 20 weight percent to 40 weight percent based on the total weight of the polymerizable composition.
- the thickener is the combination of the polyurethane and poly(N-vinylpyrrolidone), wherein the viscosity of the polyurethane at 25° C. is in the range of 50,000 cps to 150,000 cps, preferably in the range of 80,000 cps to 110,000 cps and the poly(N-vinylpyrrolidone) is such as PVP-k series, which can be but not limited to, PVP-k15, PVP-k16, PVP-k17, PVP-k18, VPV-k29, PVP-k30, PVP-k32 or PVP-k90.
- PVP-k series can be but not limited to, PVP-k15, PVP-k16, PVP-k17, PVP-k18, VPV-k29, PVP-k30, PVP-k32 or PVP-k90.
- the polymerizable composition further includes a cross-linking agent.
- the cross-linking agent is such as, for example ethylene glycol dimethacrylate (EGDMA), tetraethylene ethylene glycol dimethacrylate (TrEGOMA), triethylene ethylene glycol dimethacrylate (TEGDMA), Poly(ethylene glycol) dimethacrylate, trimethyloipropane trimethacrylate (TMPTA), vinyl methacrylate, ethylenediamine dimethyl acrylamide, glycerol dimethacrylate, triallyisocyanurate or triallyl cyanurate or the combination thereof.
- the crosslinking agent is present at an amount of 1 to 3 weight percent based on the total weight of the polymerizable composition.
- the polymerizable composition further includes a dispersant.
- the dispersant is selected from the group consisting of phosphoester, acrylic ester monomer and acrylic resin. Further, the dispersant is present at the amount of 2 weight percent to 10 weight percent based on the total v weight of the polymerizable composition.
- the polymerizable composition further includes a photo initiator or a thermal initiator.
- a photo initiator or a thermal initiator can be not limited to, such as, for example, azobisisoheptonitrile, 2,2′-azobis(isobutyronitrile) (AIBN), 2,2′-azobis(2,4-dimethylvaleronitrile), 2,2′-azobis(2-methyl-propanenitrile), 2,2′-azobis(2-methyl-butanenitrile).
- the suitable photoinitiator can be not limited to, such as, for example, 2,4,6-trimethylbenzoyl diphenyl oxide, 2-Hydroxy-2-methylpropiophenone, 2,2-Diethoxyacetophenone or ethyl(2,4,6-trimethylbenzoly)phenylphosphinate.
- the photo initiator or a thermal initiator is present at the amount of 2 weight percent to 5 weight percent based on the total amount of the polymerizable composition.
- the composite colorant is present at the amount of 0.1 weight percent to 0.5 weight percent based on the total amount of the polymerizable composition.
- Iron Oxide Black powder (trade name is Sicovit and is available from BASF, Germany), 150 ml of deionized water, 150 ml of ethanol, 22 ml of aqueous solution of ammonium (the weight percent concentration is 25%) and 5 ml of tetraethoxysilane (available from Acros Organics, US) were mixed uniformly in a flask to form a mixture.
- the mixture was heated to 65° C. for 2 hours, after that, 8 ml of 3-methacryloxypropyltrimethoxysilane (trade name is KBM503 and is valuable from Shin-Etsu Silicone, Japan) was added into the flask and reacted for another 6 hours. Then, the supernatant of the resulting reaction solution was removed by using of centrifugation, after that, the remaining solution was washed with ethanol and deionized water. After the solvent was removed, the composite colorant (I) was obtained.
- Example B The preparation method of Example B was the same as Example A, except that the amount of silane coupling agent.
- the silane coupling used in Example B was 4 ml.
- Example C The preparation method of Example C was the same as Example A, except that the amount of silane coupling agent.
- the silane coupling agent used in Example C was 2 ml.
- Example D The preparation method of Example D was the same as Example A, except that the amount of silane coupling agent.
- the silane coupling agent used in Example C was 1 ml.
- the composite colorant (I), 2-hydroxyethyl methacrylate (HEMA), methacrylic acid (MAA), polyurethane (trade name is AgiSyn 230SM-Z90, and is available from Dsm-AGI Corp., Taiwan), polyvinylpyrrodine (trade name is PVP-k30, the weight average molecular weight is 40,000 and is available from Sigma-Aldrich, US), Disponer 910 (available from Element's Specialties, UK) and a photoinitiator, 2-Hydroxy-2-methylpropiophenone (trade name is Darocur 1173 and is available from Basf, Taiwan) were grinded into a ball mill (RETSCHPM 400) to form a polymerizable composition with a viscosity between 9,000 to 10,000 cps and the average particle size thereof is 1 ⁇ m.
- the detailed composition of polymerizable composition of Example 1 was listed in Table 1 as below.
- the polymerzable composition was injected into a mold of a contact lens made of polypropylene (PP) and conducted a UV irradiating treatment or a thermal irradiating treatment to form a coloring layer thereon.
- PP polypropylene
- siloxane macromer (I) (disclosed in TW. Patent No. 1459071, synthesis of siloxane macromer A), a siloxane macromer (II) (disclosed in TW. Patent No. 1459071, synthesis of siloxane macromer B), 2-hydroxyethyl methacrylate (HEMA), N-vinylpyrrodine (NVP), crass-linking agent, photo initiator, 2-hydroxy-2-methylpropiophenone (trade name is Darocur 1173 and is available from Basf, Taiwan) were mixed at amounts shown in Table 1 to form a contact lens material.
- HEMA 2-hydroxyethyl methacrylate
- NDP N-vinylpyrrodine
- crass-linking agent photo initiator
- 2-hydroxy-2-methylpropiophenone (trade name is Darocur 1173 and is available from Basf, Taiwan) were mixed at amounts shown in Table 1 to form a contact lens material.
- the contact lens material was added by drops on the coloring layer formed on the mold of the contact lens and was cured at 80° C. for 5 hrs, than 135° C. for 2 hrs. After the polymerization was completed, the mold was immersed in alcohol for 1 hour and the resulting molded lens was taken out of the mold. In Final, the resulting lens was conducted a hydration treatment to obtain the colored contact lens.
- the detailed composition of contact lenses material of Example 1 is in Table 2.
- Example 3 The preparation method of Example 3 was the same as Example 1, except the type of composite colorant.
- the composite colorant (III) was used in the Example 3.
- the detailed composition of Example 3 was listed in Table 1 and Table 2.
- Example 4 The preparation method of Example 4 was the same as Example 1, except the composite colorant.
- the composite colorant (IV) was used in Example 4.
- the detailed composition of Example 4 was listed in Table 1 and Table 2.
- Comparative Example 1 The preparation method of Comparative Example 1 was the same as Example 1, except the composite colorant.
- the Iron Oxide Black powder (trade name is Sicovi and is available from BASF, Taiwan) was used in Comparative Example 1.
- the detailed composition of Comparative Example 1 was listed in Table 1 and Table 2.
- the contact lens was immersed in the phosphate buffered saline (PBS) for 24 hours. Then, the contact lens was removed therefrom and taken to remove all surface water. After that, the weight of contact lens was measured. Next, the contact lens was hydrated at 600 W for 5 minutes by microwave and after that the weight of hydrated contact lens was measured.
- the water contact of contact lenses was calculated by the following equation:
- test sample was cut from the middle area of a contact lens into a sample size of 10 mm. Then, the test sample was immersed in a buffer specified in ISO 18369-3 Section 4.7 for 2 hours. After that, the test sample was taken to remove all surface water and be conducted to proceed tensile modulus and tensile strength measurement by using an AI-3000 (available from Gotech Testing Maching Inc.) in a condition of temperature between 20 ⁇ 5° C. and a humidity between 55% ⁇ 10%. The measurement was carried out at a constant loading speed of 10 mm/min. In final, the tensile modulus and tensile strength were determined according to the initial gradient of the strain-stress curve. The unit of the tensile modulus is defined as MPa and the unit of tensile strength is defined as gram.
- the oxygen permeability (Dk) was measured according to ISO standards 18369-4:2006, 4.4.3, by using a oxygen permeability tester (201T).
- the units of oxygen permeability (Dk) is defined as 10 ⁇ 10 (mlO 2 mm)/(cm 2 sec mm Hg).
- the appearance of the contact lens was observed by visual to judge if the deformation occurred or not.
- the contact lens was put on a stage and a cotton swab was used to rub the surface of the contact lens for 40 times. In final, the surface of the cotton swab was observed by visual to judge if any color fading from the contact lenses.
- the water content of the contact lenses prepared according to Example 1 to Example 4 is 46% to 48%
- the tensile modulus thereof is about 0.57 MPa to 0.63 MPa and the tensile strength thereof is about 45 g to 51 g.
- the oxygen permeability thereof is about 100 to 120.
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Abstract
Description
- This application claims the priority benefit of Taiwanese application Ser. No. 104114162, filed on May 4, 2015, which is incorporated herein by reference.
- 1. Technical Field
- The present disclosure relates to a polymerizable composition for coloring contact lenses. More particularly, the polymerizable composition for coloring contact lenses has good adhesion to the contact lenses so that no discoloration or fading occurred on the colored contact lenses made from hydrogel or silicone hydrogel.
- 2. Description of Related Art
- Nowadays, concerning fashion or clothes matching, people begin to wear colored contact lenses capable of altering their natural iris color. However these different colored or patterned contact lenses would fade or discolor so as to make the wearers have ocular allergy.
- One of the conventional methods for manufacturing colored contact lens is to mix a colorant and the hydrophilic monomers to form a mixture, and then a colored layer is formed by printing or transferring the mixture on a surface of the contact lens. However, the method is unfavorable because the colored layer lacks the interaction force with the contact lens, so that the colored layer is easily peeling from contact lenses and discoloration or fading occurs.
- Another one of the conventional methods for manufacturing colored contact lenses is first to form a colored layer on the contact lens surface, and than a transparent layer is covered on the colored layer to protect the colored layer from being damaged and discolored. But, this method is so complicated and costly.
- Therefore, a novel polymerizable composition for coloring contact lenses is highly demanded. The polymerizable composition of the present disclosure provides good adhesion to contact lenses to avoid discoloration or fading on the colored contact lenses. In addition, the manufacturing method for coloring contact lenses of the present disclosure is simpler than the conventional manufacturing methods.
- According to aforementioned reasons, it is an object of the present disclosure to provide a novel polymerizable composition for coloring contact lenses, comprising a composite colorant and at least one hydrophilic monomer. The composite colorant is produced by a reaction of a colorant precursor and a (methyl)methacryloxy group-containing silane coupling agent. The colorant precursor is produced by a reaction of a metal oxide a siloxane compound under alkaline solution.
- In an embodiment of the present disclosure, the (methyl)methacryloxy group-containing silane coupling agent for manufacturing the composite colorant is selected from the group consisting of 3-(meth)acryloxypropyltrimethoxysilane, 3-(meth)acryloxypropyltriethoxysilane, 3-(meth)acryloxypropylmethyldiethoxysilane and 3-(meth)acryloxypropylmethyl-dimethoxysilane and a combination thereof.
- In an embodiment of the present disclosure, the metal oxide for manufacturing the colorant precursor applied for coloring contact lenses is known in the art, for example, such as inorganic colorant and/or inorganic pigment. The inorganic colorant and/or inorganic can be, but not limited to, Iron Oxide Black, Iron Oxide Blown, Iron Oxide Yellow, Iron Oxide Red or Titanium Dioxide.
- In an embodiment of the present disclosure, the siloxane compound for manufacturing the colorant precursor is tetraethoxy silane or tetramethoxy silane.
- In an embodiment of the present disclosure, the hydrophilic monomer is selected from the group consisting of N-vinylpyrrolidone (NVP), 2-hydroxyethyl methacrylate (HEMA), N,N-dimethylacrylamide (DMA), methyl acrylic acid, acrylic acid, glycidyl methacrylate (OMA), (methyl)acrylamide, 2-(N,N-dimethylamino) ethyl methacrylate (DMAEMA), vinyl acetate, 2-(dimethylamino)ethyl methacrylate, N-acrylolmorpholine and a combination thereof.
- In an embodiment of the present disclosure, the polymerizable composition for coloring contact lenses further includes a thickener which is selected from the group consisting of polyurethane, acrylic resin, phenolic resin, polyvinylpyrrodine and a combination thereof.
- In an embodiment of the present disclosure, the polymerizable composition for coloring contact lenses further includes a crosslinking agent.
- In an embodiment of the present disclosure, the polymerizable composition for coloring contact lenses further includes a dispersant.
- In an embodiment of the present disclosure, the polymerizable composition for coloring contact lenses further includes a photo initiator or a thermal initiator.
- In an embodiment of the present disclosure, the composite colorant is present at an amount of 10 weight percent to 60 weight percent based on the total amount of the polymerizable composition.
- In an embodiment of the present disclosure, the polymerizable composition is used for coloring contact lenses made from silicone gel or hydrogel.
- In the following detailed description, for purposes of explanation, numerous specific details are set forth in order to provide a thorough understanding of the disclosed embodiments. It will be apparent, however, that one or more embodiments may be practiced without these specific details.
- According to an aspect of the present disclosure, the present disclosure provides a navel polymerizable composition for coloring contact lenses, comprising a composite colorant and at least one hydrophilic monomer. The composite colorant is produced by a reaction of a colorant precursor and a (methyl)methacryloxy group-containing silane coupling agent, wherein the colorant precursor is produced by a reaction of a metal oxide and a siloxane compound under alkaline condition.
- In an embodiment of the present disclosure, the hydrophilic monomers for manufacturing the polymerizable composition can be, but not limited to N-vinylpyrrolidone (NVP), 2-hydroxyethyl methacrylate (HEMA), N,N-dimethylacrylamide (DMA), methyl acrylic acid (MAA), acrylic acid, glycidyl methacrylate (GMA), (methyl)acrylamide, 2-(N,N-dimethylamino) ethyl methacrylate (DMAEMA), vinyl acetate, 2-(Dimethylamino)ethyl methacrylate, N-acrylolmorpholine and a combination thereof.
- Moreover, for enhancing, the compatibility between the polymerizable composition and the contact lenses, the hydrophilic monomers is present at an amount of 10 weight percent to 30 weight percent based on the total weight of the polymerizable composition.
- In an embodiment of the present disclosure, concerning the performance and optical transmittance of the colored contact lenses, the composite colorant is present at an amount of 10 weight percent to 60 weight percent based on the total weight of the polymerizable composition.
- According to the present disclosure, the composite colorant is produced by a reaction of a colorant precursor and a (methyl)methacryloxy group-containing silane coupling agent.
- In an embodiment of the present disclosure, the (methyl)methacryloxy group-containing silane coupling agent for manufacturing the composite colorant selected from the group consisting of 3-(meth)acryloxypropyltrimethoxysilane, 3-(meth)acryloxypropyltriethoxysilane, 3-(meth)acryloxypropylmethyldiethoxysilane and 3-(meth)acryloxypropylmethyl-dimethoxysilane and a combination thereof.
- In addition, in an embodiment of the present disclosure, the reaction condition for the colorant precursor reacted with the (methyl)methacryloxy group-containing silane coupling agent is at 30° C. to 70° C. for 2 hours to 24 hours.
- According to the present disclosure, the colarant precursor is produced by a reaction of a metal oxide and a siloxane compound under alkaline solution.
- In an embodiment of the present disclosure, the metal oxide for manufacturing the colorant precursor applied for coloring contact lenses is known in the art, for example, such as inorganic colorant and/or inorganic pigment. The inorganic colorant and/or inorganic can be, but not limited to, Iron Oxide Black, Iron Oxide Blown, Iron Oxide Yellow, Iron Oxide Red or Titanium Dioxide.
- In an embodiment of the present disclosure, the siloxane compound for manufacturing the colorant precursor is tetraethoxy silane or tetramethoxy silane.
- In an embodiment of the present disclosure, the pH value of alkaline solution is in the range of 8 to 10. The solvent in the alkaline solution is selected from the group consisting of water, methanol, ethanol and a combination thereof.
- In an embodiment of the present disclosure, the polymerizable composition further includes a thickener which is selected from the group consisting of polyurethane, acrylic resin, phenolic resin, polyvinylpyrrodine and a combination thereof.
- For obtaining the appreciate viscosity of the polymerizable composition, the thickener is present at an amount of 20 weight percent to 40 weight percent based on the total weight of the polymerizable composition.
- In an embodiment of the present disclosure, the thickener is the combination of the polyurethane and poly(N-vinylpyrrolidone), wherein the viscosity of the polyurethane at 25° C. is in the range of 50,000 cps to 150,000 cps, preferably in the range of 80,000 cps to 110,000 cps and the poly(N-vinylpyrrolidone) is such as PVP-k series, which can be but not limited to, PVP-k15, PVP-k16, PVP-k17, PVP-k18, VPV-k29, PVP-k30, PVP-k32 or PVP-k90.
- In an embodiment of the present disclosure, the polymerizable composition further includes a cross-linking agent. The cross-linking agent is such as, for example ethylene glycol dimethacrylate (EGDMA), tetraethylene ethylene glycol dimethacrylate (TrEGOMA), triethylene ethylene glycol dimethacrylate (TEGDMA), Poly(ethylene glycol) dimethacrylate, trimethyloipropane trimethacrylate (TMPTA), vinyl methacrylate, ethylenediamine dimethyl acrylamide, glycerol dimethacrylate, triallyisocyanurate or triallyl cyanurate or the combination thereof. Further, the crosslinking agent is present at an amount of 1 to 3 weight percent based on the total weight of the polymerizable composition.
- In an embodiment of the present disclosure, the polymerizable composition further includes a dispersant. The dispersant is selected from the group consisting of phosphoester, acrylic ester monomer and acrylic resin. Further, the dispersant is present at the amount of 2 weight percent to 10 weight percent based on the total v weight of the polymerizable composition.
- In an embodiment of the present disclosure, the polymerizable composition further includes a photo initiator or a thermal initiator. The suitable thermal initiator, can be not limited to, such as, for example, azobisisoheptonitrile, 2,2′-azobis(isobutyronitrile) (AIBN), 2,2′-azobis(2,4-dimethylvaleronitrile), 2,2′-azobis(2-methyl-propanenitrile), 2,2′-azobis(2-methyl-butanenitrile). The suitable photoinitiator, can be not limited to, such as, for example, 2,4,6-trimethylbenzoyl diphenyl oxide, 2-Hydroxy-2-methylpropiophenone, 2,2-Diethoxyacetophenone or ethyl(2,4,6-trimethylbenzoly)phenylphosphinate. The photo initiator or a thermal initiator is present at the amount of 2 weight percent to 5 weight percent based on the total amount of the polymerizable composition.
- According to different types of the colored contact lenses, the composite colorant is present at the amount of 0.1 weight percent to 0.5 weight percent based on the total amount of the polymerizable composition.
- The present disclosure will be explained in further detail with reference to the examples. However, the present disclosure is not limited to these examples.
- 100 g of Iron Oxide Black powder (trade name is Sicovit and is available from BASF, Germany), 150 ml of deionized water, 150 ml of ethanol, 22 ml of aqueous solution of ammonium (the weight percent concentration is 25%) and 5 ml of tetraethoxysilane (available from Acros Organics, US) were mixed uniformly in a flask to form a mixture. Next, the mixture was heated to 65° C. for 2 hours, after that, 8 ml of 3-methacryloxypropyltrimethoxysilane (trade name is KBM503 and is valuable from Shin-Etsu Silicone, Japan) was added into the flask and reacted for another 6 hours. Then, the supernatant of the resulting reaction solution was removed by using of centrifugation, after that, the remaining solution was washed with ethanol and deionized water. After the solvent was removed, the composite colorant (I) was obtained.
- The preparation method of Example B was the same as Example A, except that the amount of silane coupling agent. The silane coupling used in Example B was 4 ml.
- The preparation method of Example C was the same as Example A, except that the amount of silane coupling agent. The silane coupling agent used in Example C was 2 ml.
- The preparation method of Example D was the same as Example A, except that the amount of silane coupling agent. The silane coupling agent used in Example C was 1 ml.
- The preparation method of colored contact lenses
- First, the composite colorant (I), 2-hydroxyethyl methacrylate (HEMA), methacrylic acid (MAA), polyurethane (trade name is AgiSyn 230SM-Z90, and is available from Dsm-AGI Corp., Taiwan), polyvinylpyrrodine (trade name is PVP-k30, the weight average molecular weight is 40,000 and is available from Sigma-Aldrich, US), Disponer 910 (available from Element's Specialties, UK) and a photoinitiator, 2-Hydroxy-2-methylpropiophenone (trade name is Darocur 1173 and is available from Basf, Taiwan) were grinded into a ball mill (RETSCHPM 400) to form a polymerizable composition with a viscosity between 9,000 to 10,000 cps and the average particle size thereof is 1 μm. The detailed composition of polymerizable composition of Example 1 was listed in Table 1 as below.
- Then, the polymerzable composition was injected into a mold of a contact lens made of polypropylene (PP) and conducted a UV irradiating treatment or a thermal irradiating treatment to form a coloring layer thereon.
- After the polymerization was completed, a siloxane macromer (I) (disclosed in TW. Patent No. 1459071, synthesis of siloxane macromer A), a siloxane macromer (II) (disclosed in TW. Patent No. 1459071, synthesis of siloxane macromer B), 2-hydroxyethyl methacrylate (HEMA), N-vinylpyrrodine (NVP), crass-linking agent, photo initiator, 2-hydroxy-2-methylpropiophenone (trade name is Darocur 1173 and is available from Basf, Taiwan) were mixed at amounts shown in Table 1 to form a contact lens material. Then, the contact lens material was added by drops on the coloring layer formed on the mold of the contact lens and was cured at 80° C. for 5 hrs, than 135° C. for 2 hrs. After the polymerization was completed, the mold was immersed in alcohol for 1 hour and the resulting molded lens was taken out of the mold. In Final, the resulting lens was conducted a hydration treatment to obtain the colored contact lens. The detailed composition of contact lenses material of Example 1 is in Table 2.
- The preparation method of Example 2 was the same as Example 1, except the composite colorant. The composite colorant (II) was used in Example 2. The detailed composition of Example 2 was listed in Table 1 and Table 2.
- The preparation method of Example 3 was the same as Example 1, except the type of composite colorant. The composite colorant (III) was used in the Example 3. The detailed composition of Example 3 was listed in Table 1 and Table 2.
- The preparation method of Example 4 was the same as Example 1, except the composite colorant. The composite colorant (IV) was used in Example 4. The detailed composition of Example 4 was listed in Table 1 and Table 2.
- The preparation method of Comparative Example 1 was the same as Example 1, except the composite colorant. The Iron Oxide Black powder (trade name is Sicovi and is available from BASF, Taiwan) was used in Comparative Example 1. The detailed composition of Comparative Example 1 was listed in Table 1 and Table 2.
- The physical properties of the colored contact lenses prepared from Example 1 to Example 4 and Comparative 1 were measured according to the following measuring method. The resulting data were listed in the Table 3.
- (a) Measurement of the Water Content of Contact Lenses
- The contact lens was immersed in the phosphate buffered saline (PBS) for 24 hours. Then, the contact lens was removed therefrom and taken to remove all surface water. After that, the weight of contact lens was measured. Next, the contact lens was hydrated at 600 W for 5 minutes by microwave and after that the weight of hydrated contact lens was measured. The water contact of contact lenses was calculated by the following equation:
-
(The weight of hydrated contact lenses−The weight of dry contact lenses)/The weight of hydrated contact lenses×100%. - (b) Measurement of Tensile Modulus and Tensile Strength of Contact Lenses
- The test sample was cut from the middle area of a contact lens into a sample size of 10 mm. Then, the test sample was immersed in a buffer specified in ISO 18369-3 Section 4.7 for 2 hours. After that, the test sample was taken to remove all surface water and be conducted to proceed tensile modulus and tensile strength measurement by using an AI-3000 (available from Gotech Testing Maching Inc.) in a condition of temperature between 20±5° C. and a humidity between 55%±10%. The measurement was carried out at a constant loading speed of 10 mm/min. In final, the tensile modulus and tensile strength were determined according to the initial gradient of the strain-stress curve. The unit of the tensile modulus is defined as MPa and the unit of tensile strength is defined as gram.
- (c) Measurement of Oxygen Permeability of Contact Lenses
- The oxygen permeability (Dk) was measured according to ISO standards 18369-4:2006, 4.4.3, by using a oxygen permeability tester (201T). The units of oxygen permeability (Dk) is defined as 10−10 (mlO2mm)/(cm2 sec mm Hg).
- (d) Evaluation of Deformation of Contact Lenses
- The appearance of the contact lens was observed by visual to judge if the deformation occurred or not.
- (d) Evaluation of Discolor of Contact Lenses
- The contact lens was put on a stage and a cotton swab was used to rub the surface of the contact lens for 40 times. In final, the surface of the cotton swab was observed by visual to judge if any color fading from the contact lenses.
- It can be seen from Table 3 that, comparing with Comparative Example 1, the adhesion of the colored contact lens preparing according to Example 1 to Example 4 are so good that no discoloration occurred. Furthermore, the colored contact lens thereof also has no deformation occurrence.
- In addition, the water content of the contact lenses prepared according to Example 1 to Example 4 is 46% to 48%, the tensile modulus thereof is about 0.57 MPa to 0.63 MPa and the tensile strength thereof is about 45 g to 51 g. Besides, the oxygen permeability thereof is about 100 to 120.
- While the disclosure has been described by way of example(s) and in terms of the embodiments, it is to be understood that the disclosure is not limited thereto. On the contrary, it is intended to cover various modifications and similar arrangements and procedures, and the scope of the appended claims therefore should be accorded the broadest interpretation so as to encompass all such modifications and similar arrangements and procedures.
-
TABLE 1 The detailed composition of the polymerizable composition of Example 1 to Example 4 and Comparative Example 1 Compar- ative Example Example (wt %) (wt %) Composition 1 2 3 4 1 Colorant Composite 50 50 50 50 50 colorant Hydrophilic 2-HEAM 12.8 12.8 12.8 12.8 12.8 monomer MAA 3.4 3.4 3.4 3.4 3.4 Base resin Polyurethane 15 15 15 15 15 Thickener PVP 11.5 11.5 11.5 11.5 11.5 Dispersant Disponer910 2.5 2.5 2.5 2.5 2.5 Cross- TMPTA 1.8 1.8 1.8 1.8 1.8 linking agent Initiator UV-1173 3.0 3.0 3.0 3.0 3.0 -
TABLE 2 The detailed composition of contact lenses of Example 1 to Example 4 and Comparative Example 1 Compar- ative Example Example (wt %) (wt %) Composition 1 2 3 4 1 Siloxane Siloxane 41.8 41.8 38.6 20.9 38.6 macromer macromer(I) Siloxane 6.3 6.3 5.8 20.9 5.8 macromer(II) Hydrophilic NVP 44.9 43.9 41.5 51.2 41.5 monomer 2-HEMA 6.3 6.3 13.5 6.3 13.5 Cross- EGDMA 0 1 0 0 0 linking agent Initiator AIBN 0.7 0.7 0.7 0.7 0.7 Solvent Hexane 25.1 25.1 9.7 25.1 25.1 -
TABLE 3 The measurement results of Example 1 to Example 4 and Comparative Example 1 Comparative Example Example Test item 1 2 3 4 1 Water content (%) 46.5 46.4 47.2 46.9 46.4 Tensile modulus 0.63 0.60 0.57 0.58 0.61 (MPa) Tensile Strength (g) 46 49 51 45 41 OxygenX 104 107 120 114 111 (MPa) Thickness (um) 0.077 0.069 0.075 0.071 0.070 Deformation No No No No No Discoloration No No No No Yes
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US11867985B2 (en) | 2017-06-23 | 2024-01-09 | Largan Medical Co., Ltd. | Contact lens and product thereof |
US11300812B2 (en) | 2017-07-07 | 2022-04-12 | Largan Medical Co., Ltd. | Contact lens and product thereof |
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