Contact lens material and contact lens

Abstract

The present invention discloses a contact lens material, which comprises: a hydrophilic monomer, a crosslinking agent, an initiator, and a siloxane monomer. Based on the total weight of the contact lens material being 100 parts by weight, a dosage range of the siloxane monomer is between 5 parts by weight and 50 parts by weight. And, a chemical formula of the siloxane monomer is: C a H b O c N d Si e . Wherein, C represents a carbon atom, a is a positive number between 12 and 55; H represents a hydrogen atom, b is a positive number between 29 and 121; O represents an oxygen atom, c is a positive number between 4 and 17; N represents a nitrogen atom, d is a positive number between 0 and 5; Si represents a silicon atom, e is a positive number between 1 and 9. The contact lens material of the present invention can be prepared into a silicone hydrogel contact lens, which has the advantages of low cost, mass production, and simple manufacturing process, etc.

Description

Technical Field

[0001] The present invention relates to a contact lens material, and particularly to a contact lens material and a contact lens lens having high oxygen permeability, water content, and surface wetting properties. Background Art

[0002] Hydrogel contact lenses refer to contact lenses made of hydrogel materials, such as 2-hydroxyethyl methacrylate (p-HEMA), etc. Compounds such as ethylene glycol dimethacrylate (EGDMA) can be added to 2-hydroxyethyl methacrylate to cross-link its polymer chains to increase strength.

[0003] Moreover, since the water content of 2-hydroxyethyl methacrylate is relatively low (only about 35-40%). Therefore, in order to increase the water content, in addition to p-HEMA, one or more hydrophilic monomers are added to the contact lens material to increase the water content of the contact lens, such as N-vinylpyrrolidone (NVP), N,N-dimethylacrylamide (DMA), methacrylic acid (MAA), etc.

[0004] After adding the hydrophilic monomer, the water content of the contact lens can be effectively increased (increased to about 70-80%). However, the higher the water content, the lower the tension and toughness of the contact lens. Therefore, the water content needs to be controlled moderately, usually commonly 45% to 60%. For daily disposable contact lenses, the required oxygen permeability (DK) needs to be between 40-70. However, no matter how the water content of the hydrogel contact lens is increased, its oxygen permeability can only reach between 15-35.

[0005] Relatively, silicone hydrogel contact lenses can effectively improve the oxygen permeability (DK). Silicone hydrogel contact lenses contain hydrophilic silicon-containing polymer materials, and then hydrophilic monomers such as NVP, DMA, MAA, etc. are added to copolymerize to form silicone hydrogel contact lenses. However, the surface of the silicone hydrogel material has hydrophobic properties, which easily leads to bacterial growth and causes problems such as eye inflammation. Therefore, the surface of the polysiloxane hydrogel material usually needs to be modified to improve the wettability of the material surface.

[0006] Therefore, there is an urgent need for a novel silicone hydrogel material to solve the above problems. Summary of the Invention

[0007] The technical problem to be solved by the present invention is to provide a contact lens material and a contact lens lens in view of the deficiencies of the prior art.

[0008] To solve the above technical problems, one of the technical solutions adopted by the present invention is to provide a contact lens material, which comprises: a hydrophilic monomer, a crosslinking agent, an initiator, and a siloxane monomer. Based on the total weight of the contact lens material being 100 parts by weight, the dosage range of the siloxane monomer is between 5 parts by weight and 50 parts by weight. And, a chemical formula of the siloxane monomer is represented by formula (I).

[0009] C a H b O c N d Si e Formula (I).

[0010] Wherein, C represents a carbon atom, a is a positive number between 12 and 55; H represents a hydrogen atom, b is a positive number between 29 and 121; O represents an oxygen atom, c is a positive number between 4 and 17; N represents a nitrogen atom, d is a positive number between 0 and 5; Si represents a silicon atom, e is a positive number between 1 and 9.

[0011] Preferably, the molecular weight range of the siloxane monomer is between 400 and 1,200.

[0012] Preferably, the main chain of the molecular structure of the siloxane monomer has siloxane repeat units or siloxy, and the main chain further has a first hydrophilic segment composed of an amino glycerol (1-aminoglycerol) structural fragment modified by a substituent represented by formula (I-1), and the branched chain of the molecular structure of the siloxane monomer further has a second hydrophilic segment composed of polyethylene glycol (PEG).

[0013]

[0014] Preferably, the molecular structure of the siloxane monomer further has hydrophilic branches grafted on the main chain; wherein, the hydrophilic branch has x carbon atoms and y oxygen atoms, 0 ≤ x + y ≤ 10, and one end of the hydrophilic branch far from the main chain has at least one hydrophilic functional group, which is a hydroxyl functional group (-OH group) or an alkoxy functional group (-Oalkyl group).

[0015] Preferably, a chemical structural bond-line formula of the siloxane monomer is represented by formula (II-1) or formula (II-2 ) Indicates:

[0016]

[0017]

[0018] Preferably, R 1 is H or methyl (-CH3); X 1 is O or NR 8 ; X 2 is CH-OR 9 or absent; R 2 is methyl (-CH3) or absent; R 3 、R 4 、R 7 、R 8 and R 9 are each independently (substituents may be the same or different) H or methyl (-CH3) or R 10 is H or methyl (-CH3); R 5 and R 6 are each independently (substituents may be the same or different) alkyl, aryl, alkoxy, aryloxy or OSiR 11 R 12 R 13 ; R 11 、R 12 and R 13 are each independently (substituents may be the same or different) alkyl, aryl, alkoxy, aryloxy; where a, c and n are each independently (the values may be the same or different), and are positive numbers in the range from 0 to 3; b is a positive number in the range from 0 to 8.

[0019] Preferably, in the bond-line formula of formula (II-1) or formula (II-2 ) , at least one hydroxyl group is a substituent on the main chain, at least one oxygen or nitrogen, or both as backbone atoms, and the siloxane monomer is an ionic or linear or branched monomer.

[0020] Preferably, the hydrophilic monomer is at least one material selected from the following material groups: N-vinylpyrrolidone (NVP), 2-hydroxyethyl methacrylate (HEMA), 2-hydroxyethyl acrylamide (HEAA), glycidyl methacrylate (GMA), monoglycidyl methacrylate (GMMA), methacrylic acid (MAA), acrylic acid (AA), N,N-bis(methacrylamide) (DMA), N,N-bis(methylmethacrylamide), N-vinyl-N-methylacetamide, glycine vinyl carbonate, 2-methacryloyloxyethyl phosphorylcholine, and 2-hydroxy-butyl methacrylate; wherein, based on 100 parts by weight of the total weight of the contact lens material, a dosage range of the hydrophilic monomer is between 40 parts by weight and 90 parts by weight.

[0021] Preferably, the crosslinking agent is at least one material selected from the following material groups: ethylene glycol dimethacrylate (EGDMA), diethylene glycol dimethacrylate (DEGDMA), triethylene glycol dimethacrylate (TEGDMA), tetraethylene glycol dimethacrylate (TTEGDMA), allyl methacrylate (AMA), ethylene glycol diallyl ether (EGDAE), triethylene glycol diallyl ether (TEGDAE), tetraethylene glycol diallyl ether (TTEGDAE), 1,3,5-triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, 1,1,1-tris(hydroxymethyl)propane tri(methacrylate), tris(hydroxymethyl)propane tri(acrylate), pentaerythritol tetra(acrylate), tetraethylene glycol diacrylate, ethylenediacrylamide, 1,4-bis(acrylamide)butene, and poly(ethylene glycol) di(acrylate); wherein, based on 100 parts by weight of the total weight of the contact lens material, a dosage range of the crosslinking agent is between 0.1 part by weight and 5 parts by weight.

[0022] Preferably, the initiator is at least one material selected from the following material groups: bis(1-(2,4-difluorophenyl)-3-pyrrolyl)titanocene, phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, 2-hydroxy-2-methyl-1-phenyl-1-propanone, azodiisooctanenitrile, 2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethyl)valeronitrile, 2,2'-azobis(2-methyl)propanenitrile, 2,2'-azobis(2-methyl)butanenitrile, and benzoyl peroxide; wherein, based on 100 parts by weight of the total weight of the contact lens material, a dosage range of the initiator is between 0.01 part by weight and 2 parts by weight.

[0023] To solve the above technical problems, another technical solution adopted by the present invention is to provide a contact lens, which is prepared from the contact lens material as described above. The contact lens has: a water content between 45 wt% and 80 wt%; an oxygen permeability of not less than 40 barrers; a modulus of elasticity of not more than 1.5 MPa; a dynamic contact angle of not more than 80 degrees; and a lubricity between 5 and 10.

[0024] The beneficial effects of the present invention are as follows. The contact lens material of the present invention can be prepared into a silicone hydrogel contact lens, which has the advantages of low cost, mass production, and simple manufacturing process. Moreover, the surface energy of the contact lens prepared from the contact lens material of the present invention has better surface characteristics (such as hydrophilicity or wettability). Therefore, no additional hydrophilic coating is required on the surface of the contact lens. It is worth mentioning that in the molecular structure of the siloxane monomer, the repeating unit or alkoxysilyl group of the siloxane can improve the oxygen permeability (DK) of the contact lens. Furthermore, the first and second hydrophilic segments in the main chain and the branched chain respectively improve the surface hydrophilicity or wettability of the contact lens.

[0025] To further understand the features and technical content of the present invention, please refer to the following detailed description of the present invention. However, the detailed description provided is only for reference and is not intended to limit the present invention. Detailed Embodiments

[0026] The following are specific embodiments to illustrate the disclosed embodiments of the present invention. Those skilled in the art can understand the advantages and effects of the present invention from the content disclosed in this specification. The present invention can be implemented or applied through other different specific embodiments, and various details in this specification can also be modified and changed based on different viewpoints and applications without departing from the concept of the present invention. The following embodiments will further detail the related technical content of the present invention, but the disclosed content is not intended to limit the protection scope of the present invention.

[0027] It should be understood that although terms such as "first" and "second" may be used herein to describe various components or characteristic compounds, these components or characteristic compounds should not be limited by these terms. These terms are mainly used to distinguish one component from another, or one characteristic compound from another. In addition, the term "or" used herein should, depending on the actual situation, may include any one or a combination of more of the associated listed items.

[0028] In this text, to describe a specific numerical range, the term "a certain value to another value" is adopted, which should be interpreted as covering any value within the numerical range and the smaller numerical ranges defined by any value within the numerical range, as if the arbitrary value and the smaller numerical range were clearly recorded in the specification. Additionally, for the sake of brevity, the structures of each polymer or group are sometimes represented by a skeletal formula in this text, with the carbon atoms, hydrogen atoms, and carbon-hydrogen bonds in the actual structure omitted. However, when specific atoms or atomic groups are clearly depicted in the structural formula, the structural formula shall prevail as depicted.

[0029] [Contact lens material]

[0030] An embodiment of the present invention provides a material for contact lenses. The contact lens material has the property of surface hydrophilicity, and the contact lens material can form a contact lens with a high oxygen permeability and a high water content.

[0031] The contact lens material of the embodiment of the present invention comprises: a silicone monomer, a hydrophilic monomer, a crosslinking agent, and an initiator.

[0032] Based on the total weight of the contact lens material being 100 parts by weight, the dosage range of the silicone monomer is preferably between 5 parts by weight and 50 parts by weight, and particularly preferably between 20 parts by weight and 40 parts by weight, but the present invention is not limited thereto.

[0033] The chemical experimental formula of the silicone monomer is represented by the following formula (I):

[0034] C a H b O c N d Si e Formula (I).

[0035] Among them, C represents a carbon atom, a represents the number of carbon atoms present in the siloxane monomer, and a is preferably a positive number between 12 and 55, and particularly preferably between 17 and 32. H represents a hydrogen atom, b represents the number of hydrogen atoms present in the siloxane monomer, and b is preferably a positive number between 29 and 121, and more preferably between 38 and 71. O represents an oxygen atom, c represents the number of oxygen atoms present in the siloxane monomer, and c is preferably a positive number between 4 and 17, and more preferably between 6 and 14. N represents a nitrogen atom, d represents the number of nitrogen atoms present in the siloxane monomer, and d is preferably a positive number between 0 and 5, and more preferably between 0 and 3. Si represents a silicon atom, e represents the number of silicon atoms present in the siloxane monomer, and e is preferably a positive number between 1 and 9, and more preferably between 3 and 5.

[0036] In some embodiments of the present invention, the molecular weight of the siloxane monomer is preferably between 400 and 1,200, and more preferably between 500 and 700.

[0037] In some embodiments of the present invention, the main chain of the molecular structure of the siloxane monomer has siloxane repeat units or siloxy, and the main chain further has a first hydrophilic segment composed of a 1-aminoglycerol structural fragment modified by a substituent represented by formula (I-1), and the side chain of the molecular structure of the siloxane monomer further has a second hydrophilic segment composed of polyethylene glycol (PEG).

[0038]

[0039] In some embodiments of the present invention, the molecular structure of the siloxane monomer further has a hydrophilic branch grafted on the main chain. Among them, the hydrophilic branch has x carbon atoms and y oxygen atoms, where 0 ≤ x + y ≤ 10, and one end of the hydrophilic branch away from the main chain has at least one hydrophilic functional group, such as a hydroxyl functional group (-OH group) or an alkoxy functional group.

[0040] According to the above configuration, the contact lens material of the embodiments of the present invention can be prepared into a silicone hydrogel contact lens, which has the advantages of low cost, mass production, and simple manufacturing process. Furthermore, the surface energy of the contact lens prepared from the contact lens material of the embodiments of the present invention has better surface characteristics (such as hydrophilicity or wettability). Therefore, the surface of the contact lens does not require any additional hydrophilic coating. It is worth mentioning that in the molecular structure of the siloxane monomer, the repeating unit or alkoxysilyl group of the siloxane can improve the oxygen permeability (DK) of the contact lens. Furthermore, the first and second hydrophilic segments in the main chain and the side chain respectively can improve the surface hydrophilicity or wettability of the contact lens.

[0041] In some embodiments of the present invention, the chemical experimental formula of the siloxane monomer can be represented by the following formulas (I-1), (I-2), and (I-3).

[0042] C 24 H 53 O9NSi3 Formula (I-1).

[0043] C 28 H 61 O 11 NSi3 Formula (I-2).

[0044] C 17 H 38 O6Si3 Formula (I-3).

[0045] Among them, the siloxane monomer represented by the above formula (I-1) has a molecular weight of 583.9354, the siloxane monomer represented by the above formula (I-2) has a molecular weight of 672.0405, and the siloxane monomer represented by the above formula (I-3) has a molecular weight of 422.7365.

[0046] In some embodiments of the present invention, a chemical structural bond line formula (skeletal formula) of the siloxane monomer with a chemical experimental formula as shown in formula (I) is as shown in formula (II-1) or formula (II-2 ) It is shown as:

[0047]

[0048] Among them, R 1 is H or methyl (-CH3); X 1 is O or NR 8 ; X 2 is CH-OR 9 or does not exist; R 2 is methyl (-CH3) or does not exist; R 3 、R 4 、R7 and R 8 and R 9 are each independently (substituents may be the same or different) H, methyl (-CH3), or R 10 is H or methyl (-CH3); R 5 and R 6 are each independently (substituents may be the same or different) alkyl, aryl, alkoxy, aryloxy having 1 to 10 carbon atoms, or OSiR 11 R 12 R 13 ; R 11 and R 12 and R 13 are each independently (substituents may be the same or different) alkyl, aryl, alkoxy, aryloxy having 1 to 10 carbon atoms; wherein a, c, and n are each independently (values may be the same or different) positive numbers ranging from 0 to 3 (preferably ranging from 1 to 3); b is a positive number ranging from 0 to 8 (preferably ranging from 1 to 8).

[0049] In the bond-line formula of the above formula (II-1) or formula (II-2 ) , is a siloxane repeat unit or siloxy.

[0050] Furthermore, the substituent of R 3 or R 7 is the second hydrophilic segment composed of polyethylene glycol (PEG).

[0051] Furthermore, X 1 and X 2 are main chain backbone atoms or groups, or hydrophilic branches.

[0052] Furthermore, at least one hydroxyl group is a substituent on the main chain, at least one oxygen or nitrogen, or both as backbone atoms, and the siloxane monomer may be an ionic or linear or branched monomer.

[0053] In a first specific embodiment of the present invention, the siloxane monomer represented by the chemical experimental formula as in formula (I-1) corresponds to the substituents in formula (II-1) as follows: R 1 ​=CH3; X 1 =O; X 2 =CH-OR 9 ; a = c = 1; b = 0; R 2 = none; n = 2; R 4 = R 7 = R 9 = R 10 = H; R 5 = R 6 = OSiR 11 R 12 R 13 ,R 11 = R 12 = R 13 = CH3。

[0054] In a second specific embodiment of the present invention, the substituents of the siloxane monomer represented by the chemical experimental formula as formula (I-2) corresponding to formula (II-1) are as follows: R 1 = R 5 = R 6 = CH3; X 1 = O; X 2 = CH-OR 9 ; a = c = 1; b = 2; R 2 = none; n = 2; R 4 = R 9 = R 10 = H。

[0055] In a third specific embodiment of the present invention, the substituents of the siloxane monomer represented by the chemical experimental formula as formula (I-3) corresponding to formula (II-1) are as follows: R 1 = CH3; X 1 = O; X 2 = CH-OR 9 ; a = b = 0; c = 1; R 5 = R 6 = OSiR 11 R 12 R 13 ,R 11 = R 12 = R 13 = CH3; R 7 = R 9 = H。

[0056] In some embodiments of the present invention, the hydrophilic monomer is at least one material selected from the following material groups: N-vinyl pyrrolidone (NVP), 2-hydroxyethyl methacrylate (HEMA), 2-hydroxyethyl acrylamide (HEAA), glyceryl methacrylate (GMA), glycerolmono-meth acrylate (GMMA), methacrylic acid (MAA), acrylic acid (AA), N,N-di(methyl acrylamide) (DMA), N,N-di(methyl meth acryl-amide), N-vinyl-N-methyl acetamide, glycine vinyl carbonate, 2-methacryloyloxyethyl phosphorylcholine, and 2-hydroxy-butyl methacrylate.

[0057] Furthermore, based on the total weight of the contact lens material being 100 parts by weight, the dosage range of the hydrophilic monomer is preferably between 40 parts by weight and 90 parts by weight, and particularly preferably between 45 parts by weight and 85 parts by weight, but the present invention is not limited thereto.

[0058] In some embodiments of the present invention, the crosslinking agent is at least one material selected from the following material groups: ethylene glycol di(methacrylate) (EGDMA), di(ethylene glycol)di(methacrylate) (DEGDMA), tri(ethylene glycol)di(methacrylate) (TEGDMA), tetra(ethylene glycol)di(methacrylate) (TTEGDMA), allyl methacrylate (AMA), ethylene glycol di(allyl ether) (EGDAE), tri(ethylene glycol)di(allyl ether) (TEGDAE), tetra(ethylene glycol)di(allyl ether) (TTEGDAE), 1,3,5-triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, 1,1,1-tri(methylolpropane)tri(methacrylate), tri(methylolpropane)tri(acrylate), pentaerythritol tetra(acrylate), tetra(ethylene glycol)di(acrylate), ethylene di(acrylamide), butylene 1,4-di(acrylamide), and poly(ethylene glycol)di(acrylate).

[0059] Further, based on 100 parts by weight of the total weight of the contact lens material, the dosage range of the crosslinking agent is preferably between 0.1 part by weight and 5 parts by weight, and more preferably between 0.1 part by weight and 3 parts by weight, but the present invention is not limited thereto.

[0060] In some embodiments of the present invention, the initiator is a photoinitiator.

[0061] In some embodiments of the present invention, the initiator is at least one material selected from the following material group: bis(1-(2,4-difluorophenyl)-3-pyrrolyl)titanocene, phenylbis-(2,4,6-trimethylbenzoyl)-phosphine oxide, and 2-hydroxy-2-methyl-1-phenyl-1-propanone.

[0062] In some embodiments of the present invention, the initiator is at least one material selected from the following material group: 2,2’-Azodi(2,4-dimethylvaleronitrile) (ADVN), 2,2’-Azobis(2-methylpropionitrile) (AIBN), 2,2’-Azobis(2,4-dimethyl)valeronitrile, 2,2’-Azobis(2methyl)propionitrile, 2,2’-Azobis(2-methyl)butyronitrile, and benzoyl peroxide, but the present invention is not limited thereto.

[0063] Furthermore, based on 100 parts by weight of the total weight of the contact lens material, the dosage range of the initiator is preferably between 0.01 part by weight and 2 parts by weight, and particularly preferably between 0.05 part by weight and 1 part by weight, but the present invention is not limited thereto.

[0064] In order to enhance the ultraviolet light blocking ability of the contact lens material, in some embodiments of the present invention, the contact lens material further comprises an ultraviolet light blocking monomer, and based on 100 parts by weight of the total weight of the contact lens material, the dosage range of the ultraviolet light blocking monomer is between 0.30 parts by weight and 1.80 parts by weight. Among them, the ultraviolet light blocking monomer is selected from at least one of the material groups consisting of a monomer having benzophenone and a monomer having benzotriazole.

[0065] In order to enhance the solubility of the contact lens material, in some embodiments of the present invention, the contact lens material further comprises a co-solvent, and based on 100 parts by weight of the total weight of the contact lens material, the dosage range of the co-solvent is between 3 parts by weight and 15 parts by weight. Among them, the co-solvent is selected from at least one of the material groups consisting of glycerol, isopropyl alcohol, n-butanol, t-butanol, t-amyl alcohol and n-hexanol.

[0066] In order to endow the contact lens material with a specific color, in multiple embodiments of the present invention, the contact lens material further comprises a dye, and based on 100 parts by weight of the total weight of the contact lens material, the dosage range of the dye is between 0.002 parts by weight and 0.050 parts by weight. Among them, the dye is selected from at least one of the material groups consisting of reactive blue 19 (disodium, 1-amino-9,10-dioxo-4-[3-(2-sulfonatooxyethylsulfonyl)anilino]anthracene-2-sulfonate), Sudan III (1-[4-(Phenylazo)phenylazo]-2-naphthol), Indigo (2,2’-Bis(2,3-dihydro-3-oxoindolylidene)) and quinoline yellow (disodium 2-(1,3-dioxo-2,3-dihydro-1H-inden-2-yl)quinolone-6,8-disul fonate).

[0067] [Method for manufacturing contact lenses]

[0068] Another embodiment of the present invention provides a method for manufacturing contact lenses. The method for manufacturing contact lenses includes: injecting the contact lens material into a mold for manufacturing contact lenses, and performing a curing and forming process on the contact lens material to form a semi-finished dry contact lens. Then, soaking the semi-finished dry contact lens in a buffer solution until the semi-finished dry contact lens swells (hydration process). Next, filling a buffer solution into a packaging container, soaking the contact lens in the buffer solution, and then performing a sealing process and a sterilization process, thus completing the production of contact lens products.

[0069] [Contact lens]

[0070] Another embodiment of the present invention provides a contact lens. The contact lens is formed from the contact lens material of the above embodiment. According to the formulation of the contact lens material in the above embodiment, the contact lens of the embodiment of the present invention can have high oxygen permeability, water content, and surface wetting properties.

[0071] The contact lens prepared from the contact lens material of the present invention can have better physical and chemical properties. More specifically, the contact lens has: (a) a water content between 45 wt% and 80 wt%, and preferably between 65 wt% and 80 wt%; (b) an oxygen permeability of not less than 40 barrers, and preferably between 40 barrers and 60 barrers; (c) an elastic modulus of not more than 1.5 MPa, and preferably between 0.3 MPa and 0.6 MPa; (d) a dynamic contact angle of not more than 80 degrees, preferably not more than 60 degrees, and more preferably not more than 30 degrees; (e) a refractive index between 1.350 and 1.442; and (f) a lubricity between 5 and 10, and preferably between 6 and 9.

[0072] [Experimental data and test results]

[0073] Hereinafter, the content of the present invention will be described in detail with reference to Examples S1 to S11. However, the following examples are only for helping to understand the present invention, and the scope of the present invention is not limited to these examples.

[0074] The preparation methods of Examples S1 to S11 include injecting a contact lens material into a mold for manufacturing contact lenses, and performing a curing and molding process on the contact lens material to form a semi-finished dry contact lens. Then, the semi-finished dry contact lens is soaked in a buffer solution until the semi-finished dry contact lens swells (hydration process). Then, a buffer solution is filled into a packaging container, the contact lens is soaked in the buffer solution, and then, a sealing process (sealing temperature is about 125 °C) and a sterilization process (sterilization time is about 30 minutes) are carried out, thus completing the production of the contact lens product.

[0075] Among them, the contact lens material mainly includes: siloxane monomers, hydrophilic monomers, cross-linking agents, and initiators. The preparation methods of Examples S1 to S11 are generally the same, and the difference lies in that the dosages of the components in the contact lens materials of Examples S1 to S11 are different, and the siloxane monomers used are also different. Among them, Examples S1 to S3 use the siloxane monomer having the above chemical formula (I-1) and corresponding to the first specific embodiment. Examples S4 to S6 use the siloxane monomer having the above chemical formula (I-2) and corresponding to the second specific embodiment. Examples S7 and S8 use the siloxane monomer having the above chemical formula (I-1) and corresponding to the first specific embodiment, and the siloxane monomer having the above chemical formula (I-2) and corresponding to the second specific embodiment. Example S9 uses the siloxane monomer having the above chemical formula (I-1) and corresponding to the first specific embodiment, and the siloxane monomer having the above chemical formula (I-3) and corresponding to the third specific embodiment. Example S10 uses the siloxane monomer having the above chemical formula (I-2) and corresponding to the second specific embodiment, and the siloxane monomer having the above chemical formula (I-3) and corresponding to the third specific embodiment. Example S11 uses the siloxane monomer having the above chemical formula (I-3) and corresponding to the third specific embodiment. The formulation compositions of Examples S1 to S11 are shown in Table 1 below.

[0076] The siloxane monomers used in Examples S1 to S11 also have carbon atoms (C), hydrogen atoms (H), oxygen atoms (O), and silicon atoms (Si) in their chemical structures, but the content of nitrogen atoms (N) is different. The siloxane monomer having the above chemical formula (I-3) and corresponding to the third specific embodiment does not have nitrogen atoms, and it can be used as an experimental control group for different compositions of nitrogen, oxygen, and silicon in the contact lens material of the embodiments of the present invention.

[0077] The silicone monomers used in Examples S1 to S11 can all give good performance to the following physical and chemical properties of the contact lenses, which include: the water content (wt%) of the lens body, the oxygen permeability (DK) of the lens body, the elastic modulus (MPa) of the lens body, the dynamic contact angle of the lens surface, and the lubricity of the lens surface. The test methods for the physical and chemical properties of the contact lenses are described below, and the test results are shown in Table 5 below.

[0078] Water content (wt%) of the lens body: The method for measuring the equilibrium water content is to weigh the lens after moving water on the lens surface to obtain the hydrated lens weight, dry the lens in an oven, and weigh the lens in the dry state. Subtract the dry weight from the hydrated weight to get the weight difference. Equilibrium water content (wt%) = (weight difference / hydrated weight) × 100.

[0079] Oxygen permeability (DK) of the lens body: The measurement of oxygen permeability is carried out using the polarographic method described in ISO 9913-1, using an O2 permeameter instrument. The sample is immersed in pure water for at least 12 hours for equilibration and then the oxygen permeability is measured in phosphate buffered saline at 35 °C using an O2 permeameter model 201T (purchased from Rheder Development). The oxygen permeability is recorded in Barrer units.

[0080] Elastic modulus (MPa) of the lens body: The elastic modulus is measured using a tensile testing machine Zwick Z0.5. The lens sample is cut to a width of 2 mm. The thickness of the sample is measured using a micrometer before the start of the test. At the start of the test, the moving speed of the extension part of the sample, the length of the sample, and the distance between the jaws are kept constant. Each sample is placed in buffered saline during the measurement. The modulus is recorded in MPa units.

[0081] Dynamic contact angle (degrees) of the lens surface: The measurement of the dynamic contact angle is carried out using the captive bubble method. According to this method, the silicone hydrogel contact lens is properly clamped between two hard plastics to make the central part of the lens relatively flat, and then the lens is immersed in a small jar containing a borate buffered saline solution. Then a bubble is properly introduced onto the lens surface and stays on the surface. Then a digital camera is used to take a photo, and then a calculator program is used to obtain the left and right contact angles from the drawing, and the average of the left and right contact angles is recorded.

[0082] Lubricity of the lens surface: The lubricity of the lens is blindly scored by 10 people (from 1 to 10). The higher the score, the better the lubricity of the lens surface.

[0083] [Table 1] Formulations of contact lens materials for Examples S1 to S11. Among them, the total weight of the contact lens materials is 100 parts by weight.

[0084]

[0085]

[0086]

[0087] [Table 2] Test results of the physical and chemical properties of the contact lenses of Examples S1 to S11.

[0088]

[0089]

[0090] [Discussion of experimental results]

[0091] Table 2 shows the lens surface properties of Examples S1 to S11, such as the dynamic contact angle and lubricity. Among them, the lower the value of the dynamic contact angle, the better the hydrophilicity of the lens surface. On many highly hydrophilic surfaces, the contact angle ranges from 0 degrees to 30 degrees. The lubricity of the lens surface was blindly scored by 10 people (from 1 to 10), and the higher the score, the better the lubricity of the lens surface. The test results of the dynamic contact angle and lubricity are shown in Table 2 respectively.

[0092] The siloxane monomers used in Examples S1 to S11 can all make the following physical and chemical properties of the contact lenses have good performance, among which Examples S1 to S8 have better performance in terms of hydrophilicity or wettability on the lens surface. Further, in the chemical structures of the siloxane monomers of Examples S1 to S8, oxygen atoms can bond with water molecules through hydrogen bonds to enhance the surface hydrophilicity of the contact lens material. Nitrogen atoms are easily bonded with water molecules through hydrogen bonds in the ionic state.

[0093] In addition, generally speaking, the more the content of silicon atoms, the more hydrophobic the lens surface will be. However, the chemical structures of the siloxane monomers of Examples S1 to S8 have more oxygen atoms and nitrogen atoms, so they can maintain good hydrophilicity and lubricity on the lens surface of the contact lenses. Therefore, the lens surfaces of the contact lenses made from the formulations of Examples S1 to S8 do not need to be coated with any hydrophilic coatings.

[0094] [Advantages of the examples]

[0095] One of the beneficial effects of the present invention is that the contact lens material of the embodiments of the present invention can be prepared into a silicone hydrogel contact lens, which has the advantages of low cost, mass production, and simple manufacturing process. Furthermore, the surface energy of the contact lens prepared from the contact lens material of the embodiments of the present invention has better surface characteristics (such as hydrophilicity or wettability). Therefore, no additional hydrophilic coating is required on the surface of the contact lens. It is worth mentioning that in the molecular structure of the siloxane monomer, the repeating unit or alkoxysilyl group of the siloxane can improve the oxygen permeability (DK) of the contact lens. Furthermore, the first and second hydrophilic segments in the main chain and the side chain respectively can improve the surface hydrophilicity or wettability of the contact lens.

[0096] The content disclosed above is only the preferred feasible embodiment of the present invention, and does not limit the scope of the patent application of the present invention. Therefore, all equivalent technical changes made by using the content of the specification of the present invention are included in the scope of the patent application of the present invention.

Claims

1. A contact lens material, characterized in that, The contact lens material includes: a hydrophilic monomer, a crosslinking agent, an initiator, and a siloxane monomer; Wherein, based on the total weight of the contact lens material being 100 parts by weight, the dosage range of the siloxane monomer is between 5 parts by weight and 50 parts by weight; Wherein, the chemical structural bond-line formula of the siloxane monomer is represented by Formula (II-1) or Formula (II-2): Among them, R 1 is H or methyl; X 1 is O or NR 8 ; X 2 is CH-OR 9 or does not exist; R 2 is methyl or does not exist; R 3 is R 4 、R 7 、R 8 and R 9 are each independently H or methyl or R 10 is H or methyl; R 5 and R 6 are each independently an alkyl group, an aromatic group, an alkoxy group, an aryloxy group or OSiR 11 R 12 R 13 ; R 11 、R 12 and R 13 are each independently an alkyl group, an aromatic group, an alkoxy group, an aryloxy group with the carbon number ranging from 1 to 10; among them, a is a positive number ranging from 1 to 3, c is a positive number ranging from 0 to 3, b is a positive number ranging from 0 to 8, and n is a positive number ranging from 1 to 3.

2. The contact lens material according to claim 1, wherein The molecular weight of the siloxane monomer is between 400 and 1,200.

3. The contact lens material according to claim 1, wherein In the bond-line formula of Formula (II-1) or Formula (II-2), at least one hydroxyl group is a substituent on the main chain, at least one oxygen or nitrogen, or both are skeletal atoms, and the siloxane monomer is an ionic or branched monomer.

4. The contact lens material according to claim 1, characterized in that, The hydrophilic monomer is at least one material selected from the following material groups: N-vinylpyrrolidone, 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylamide, glycerol methacrylate, monoglycerol methacrylate, methacrylic acid, acrylic acid, N,N-dimethylacrylamide, N-vinyl-N-methylacetamide, glycine vinyl carbonate, 2-methacryloyloxyethyl phosphorylcholine, and 2-hydroxy-butyl methacrylate; wherein, based on the total weight of the contact lens material being 100 parts by weight, the dosage range of the hydrophilic monomer is between 40 parts by weight and 90 parts by weight.

5. The contact lens material according to claim 1, characterized in that, The crosslinking agent is at least one material selected from the following material groups: ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, allyl methacrylate, ethylene glycol diallyl ether, triethylene glycol diallyl ether, tetraethylene glycol diallyl ether, 1,3,5-triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, 1,1,1-tris(hydroxymethyl)propane tri(methacrylate), tris(hydroxymethyl)propane tri(acrylate), pentaerythritol tetra(acrylate), tetraethylene glycol diacrylate, ethylenediacrylamide, and poly(ethylene glycol) di(acrylate); wherein, based on the total weight of the contact lens material being 100 parts by weight, the dosage range of the crosslinking agent is between 0.1 parts by weight and 5 parts by weight.

6. The contact lens material according to claim 1, characterized in that, The initiator is at least one material selected from the following material groups: bis(1-(2,4-difluorophenyl)-3-pyrrolyl)titanocene, phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, 2-hydroxy-2-methyl-1-phenyl-1-propanone, azobisisoheptonitrile, 2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethyl)valeronitrile, 2,2'-azobis(2-methyl)propionitrile, 2,2'-azobis(2-methyl)butyronitrile, and benzoyl peroxide; wherein, based on the total weight of the contact lens material being 100 parts by weight, the dosage range of the initiator is between 0.01 parts by weight and 2 parts by weight.

7. A contact lens, which is prepared from the contact lens material described in any one of claims 1 to 6, characterized in that, The contact lens has: a water content between 45 wt% and 80 wt%; an oxygen permeability of not less than 40 barrers; a modulus of elasticity of not more than 1.5 MPa; a dynamic contact angle of not more than 80 degrees; and a lubricity between 5 and 10.

Images