Silica hydrogel contact lens and preparation method thereof

Abstract

The invention provides a silicone hydrogel contact lens and a preparation method thereof, and belongs to the technical field of contact lenses. The siloxane monomer is utilized to improve the high light transmittance and oxygen permeability of the contact lens, and the hydrophilic monomer endows the hydrogel with hydrophilicity and softness, so that the comfort level of the contact lens is improved; the polyethylene glycol diacrylate is used for reducing the crosslinking density and improving the surface wettability, so that the mechanical property and the surface wettability of the organic silicon hydrogel are favorably improved; the monomethyl itaconate enables the silicone hydrogel contact lens to have good hydrophilicity and high lubrication degree. By means of the monomers, the hydrophilicity and air permeability of the organic silicon hydrogel are improved, the contact lenses have high light transmittance, oxygen permeability and comfortable wearing feeling (hydrophilicity and high lubrication degree), and the high requirements of modern contact lenses for material performance are met.

Description

Technical Field

[0001] The present invention relates to the technical field of contact lenses, and in particular to a silicone hydrogel contact lens and a preparation method thereof. Background Art

[0002] With the development of plastic materials, especially the application of polymethyl methacrylate (PMMA), the design and materials of contact lenses have been significantly improved. The application of this material makes contact lenses lighter and more comfortable, thus opening a new chapter in the popularization of contact lenses. In the 1950s, Czechoslovak polymer scientist Otto Wichterle contributed to the development of a new type of polymer PHEMA (polyhydroxyethyl methacrylate), which has the characteristics of high oxygen permeability, ion permeability, water permeability, etc., and is highly compatible with the eye environment, greatly improving the comfort and durability of soft lenses.

[0003] The development of contact lenses has not only improved the way of vision correction, but also provided more aesthetic choices. The transition from hard lenses to soft lenses has not only improved the comfort of users, but also made contact lenses more widely used to correct myopia, hyperopia, astigmatism and other vision problems. In addition, contact lenses have also played an important role in controlling the development of myopia and astigmatism in adolescents and treating certain eye diseases.

[0004] However, the hydrophilicity and lubricity of existing contact lenses still need to be further improved. Summary of the invention

[0005] The object of the present invention is to provide a silicone hydrogel contact lens and a preparation method thereof. The prepared silicone hydrogel contact lens has high hydrophilicity and lubricity.

[0006] In order to achieve the above-mentioned object of the invention, the present invention provides the following technical solutions:

[0007] The present invention provides a method for preparing a silicone hydrogel contact lens, comprising the following steps:

[0008] Mixing the silicone hydrogel raw material and the photoinitiator, filtering, and obtaining a mixed solution;

[0009] The mixed solution is injected into a contact lens mold, and after a polymerization reaction is carried out under light conditions, the obtained molded silicone hydrogel contact lens is demolded to obtain a silicone hydrogel contact lens;

[0010] The silicone hydrogel raw material comprises 30-60% of organic siloxane monomer, 35-65% of hydrophilic monomer, 1-2% of crosslinking agent, 1-2% of polyethylene glycol diacrylate and 0.5-1.5% of monomethyl itaconate.

[0011] Preferably, the organosiloxane monomer includes one or more of methacryloxymethyltriethoxysilane, methacryloxymethyltrimethylsilane, methacryloxypropyltri(trimethylsiloxy)silane and methylvinyldiethoxysilane.

[0012] Preferably, the hydrophilic monomer includes one or more of hydroxyethyl methacrylate, polyethylene glycol, methacrylic acid, acrylic acid and N-vinylacetamide.

[0013] Preferably, the photoinitiator includes one or more of diphenylacetone, 1-hydroxycyclohexylphenylketone, 2-isopropylthioxanthone, 2-hydroxy-2-methyl-1-phenylpropanone, 2-methyl-2-(4-morpholinyl)-1-[4-(methylthio)phenyl]-1-propanone and (2,4,6-trimethylbenzoyl)diphenylphosphine oxide.

[0014] Preferably, the mass of the photoinitiator is 0.5-2.0% of the mass of the silicone hydrogel raw material.

[0015] Preferably, the crosslinking agent comprises ethylene glycol dimethacrylate and / or triethylene glycol dimethacrylate.

[0016] Preferably, the wavelength of the light is 320-400 nm.

[0017] Preferably, the polymerization reaction time is 20 to 40 minutes.

[0018] The present invention provides a silicone hydrogel contact lens prepared by the preparation method described in the above technical solution.

[0019] The present invention provides a method for preparing a silicone hydrogel contact lens, wherein the siloxane monomer can improve the high light transmittance and oxygen permeability of the contact lens, the hydrophilic monomer gives the hydrogel hydrophilicity and softness, thereby improving the comfort of the contact lens; polyethylene glycol diacrylate is used to reduce the crosslinking density and improve the surface wettability, which helps to improve the mechanical properties and surface wettability of the silicone hydrogel; monomethyl itaconate can make the silicone hydrogel contact lens have good hydrophilicity and high lubricity. The present invention not only improves the hydrophilicity and air permeability of the silicone hydrogel through the above monomers, but also makes the contact lens have high light transmittance, oxygen permeability and comfortable wearing feeling (hydrophilicity and high lubricity), meeting the high requirements of modern contact lenses for material properties.

[0020] The present invention prepares silicone hydrogel contact lenses under light conditions, shortens the polymerization and curing time, and the method is simple and easy to implement. DETAILED DESCRIPTION

[0021] In the present invention, unless otherwise specified, the raw materials or reagents used are commercially available products well known in the art.

[0022] The present invention provides a method for preparing a silicone hydrogel contact lens, comprising the following steps:

[0023] Mixing the silicone hydrogel raw material and the photoinitiator, filtering, and obtaining a mixed solution;

[0024] The mixed solution is injected into a contact lens mold, and after a polymerization reaction is carried out under light conditions, the obtained molded silicone hydrogel contact lens is demolded to obtain a silicone hydrogel contact lens;

[0025] The silicone hydrogel raw material comprises 30-60% of organic siloxane monomer, 35-65% of hydrophilic monomer, 1-2% of crosslinking agent, 1-2% of polyethylene glycol diacrylate and 0.5-1.5% of monomethyl itaconate.

[0026] In the present invention, the silicone hydrogel raw material includes 30-60% of an organic siloxane monomer, preferably 35-55%, and more preferably 40-50%. In the present invention, the organic siloxane monomer includes one or more of methacryloxymethyltriethoxysilane, methacryloxymethyltrimethylsilane, methacryloxypropyltri(trimethylsiloxane)silane, and methylvinyldiethoxysilane; when the organic siloxane monomer is two or more of the above, the present invention has no special restrictions on the ratio of different types of organic siloxane monomers, and any ratio is acceptable.

[0027] In the present invention, the silicone hydrogel raw material includes 35-65% of hydrophilic monomers, preferably 40-60%, and more preferably 45-55%. In the present invention, the hydrophilic monomers preferably include one or more of hydroxyethyl methacrylate, polyethylene glycol, methacrylic acid, acrylic acid, and N-vinylacetamide. When the hydrophilic monomers are two or more of the above, the present invention has no special restrictions on the ratio of different types of hydrophilic monomers, and any ratio is acceptable.

[0028] In the present invention, the silicone hydrogel raw material includes 1-2% of a crosslinking agent, preferably 1.2-1.8%, and more preferably 1.5-1.6%. In the present invention, the crosslinking agent preferably includes ethylene glycol dimethacrylate and / or triethylene glycol dimethacrylate; when the crosslinking agent is the above two, the present invention has no special limitation on the ratio of the two, and any ratio is acceptable.

[0029] In the present invention, the silicone hydrogel raw material includes 1-2% polyethylene glycol diacrylate, preferably 1.2-1.8%, and more preferably 1.5-1.6%.

[0030] In the present invention, the silicone hydrogel raw material includes 0.5-1.5% monomethyl itaconate, preferably 0.6-1.2%, more preferably 1.8-1.0%.

[0031] In the present invention, the photoinitiator preferably includes one or more of diphenylacetone, 1-hydroxycyclohexylphenylketone, 2-isopropylthioxanthone, 2-hydroxy-2-methyl-1-phenylpropanone, 2-methyl-2-(4-morpholinyl)-1-[4-(methylthio)phenyl]-1-propanone and (2,4,6-trimethylbenzoyl)diphenylphosphine oxide. When the photoinitiator is two or more of the above, the present invention has no special restrictions on the ratio of different types of photoinitiators, and any ratio is acceptable.

[0032] In the present invention, the mass of the photoinitiator is preferably 0.5-2.0% of the mass of the silicone hydrogel raw material, preferably 0.6-1.8%, more preferably 0.8-1.5%, and further preferably 1.0-1.2.

[0033] In the present invention, the silicone hydrogel raw material and the photoinitiator are preferably stirred and mixed, and then filtered using a 0.22 μm filter element to obtain a mixed solution.

[0034] The present invention has no particular limitation on the contact lens mold, and any corresponding mold known in the art may be used.

[0035] In the present invention, the wavelength of the light wave of the illumination is preferably 320-400 nm; the light source used for the illumination is preferably an LED lamp, and the illumination distance of the light source is preferably 100 mm.

[0036] In the present invention, the polymerization reaction time is preferably 20 to 40 minutes, more preferably 30 minutes.

[0037] The present invention has no special limitation on the mold splitting, and the mold splitting can be performed in a manner well known in the art.

[0038] After the mold separation, the present invention preferably sequentially performs alcohol washing, water washing and sterilization on the obtained contact lens to obtain a silicone hydrogel contact lens. The present invention has no special limitation on the alcohol washing, water washing and sterilization, and they can be performed in a manner well known in the art; in an embodiment of the present invention, the alcohol washing is specifically ethanol washing.

[0039] The present invention provides a silicone hydrogel contact lens prepared by the preparation method described in the above technical solution.

[0040] The technical solutions provided by the present invention are described in detail below in conjunction with the embodiments, but they should not be construed as limiting the protection scope of the present invention.

[0041] Example 1

[0042] The components of the silicone hydrogel contact lens in this embodiment are:

[0043] Silicone hydrogel raw materials: 45% organosiloxane monomer, 50% hydrophilic monomer, 2.0% crosslinking agent, 1.5% polyethylene glycol diacrylate, 1.5% monomethyl itaconate;

[0044] The mass of the photoinitiator is 1.0% of the mass of the silicone hydrogel raw material;

[0045] The organosiloxane monomer: methacryloxymethyltriethoxysilane and methacryloxymethyltrimethylsilane in a mass ratio of 1:1;

[0046] Hydrophilic monomer: hydroxyethyl methacrylate, polyethylene glycol and methacrylic acid in a mass ratio of 1:1:1;

[0047] Crosslinker: triethylene glycol dimethacrylate;

[0048] Photoinitiator: 2-methyl-2-(4-morpholinyl)-1-[4-(methylthio)phenyl]-1-propanone and (2,4,6-trimethylbenzoyl)diphenylphosphine oxide in a mass ratio of 1:1;

[0049] The above-mentioned silicone hydrogel raw material and photoinitiator are mixed and stirred for 10 minutes, filtered through a 0.22μm filter element to obtain a mixed solution, injected into a contact lens mold, pressed and fixed, and then irradiated under an LED light with a wavelength of 395nm for 30 minutes. The illumination distance of the light source is 100mm. The molded silicone hydrogel contact lens is taken out by mechanical demolding, and washed with ethanol, water and sterilized in sequence to obtain a silicone hydrogel contact lens.

[0050] Example 2

[0051] The components of the silicone hydrogel contact lens in this embodiment are:

[0052] Silicone hydrogel raw materials: organic siloxane monomer 60%, hydrophilic monomer 35%, cross-linking agent 2%, polyethylene glycol diacrylate 2%, monomethyl itaconate 1.0%;

[0053] The mass of the photoinitiator is 0.5% of the mass of the silicone hydrogel raw material;

[0054] The organosiloxane monomer: methacryloxymethyltrimethylsilane and methylvinyldiethoxysilane in a mass ratio of 1:1;

[0055] Hydrophilic monomer: N-vinyl acetamide and methacrylic acid in a mass ratio of 1:1;

[0056] Crosslinker: ethylene glycol dimethacrylate;

[0057] Photoinitiator: diphenyl acetone and 1-hydroxycyclohexyl phenyl ketone in a mass ratio of 1:1;

[0058] The above-mentioned silicone hydrogel raw material and photoinitiator are mixed and stirred for 10 minutes, filtered through a 0.22μm filter element to obtain a mixed solution, injected into a contact lens mold, pressed and fixed, and then irradiated under an LED light with a wavelength of 395nm for 30 minutes. The illumination distance of the light source is 100mm. The molded silicone hydrogel contact lens is taken out by mechanical demolding, and washed with ethanol, water and sterilized in sequence to obtain a silicone hydrogel contact lens.

[0059] Example 3

[0060] The components of the silicone hydrogel contact lens in this embodiment are:

[0061] Silicone hydrogel raw materials: 40% organosiloxane monomer, 55% hydrophilic monomer, 1.5% crosslinking agent, 2% polyethylene glycol diacrylate, 1.5% monomethyl itaconate;

[0062] The mass of the photoinitiator is 1.5% of the mass of the silicone hydrogel raw material;

[0063] The organosiloxane monomer: methacryloxypropyl tris(trimethylsiloxy)silane and methylvinyldiethoxysilane in a mass ratio of 1:1;

[0064] Hydrophilic monomers: polyethylene glycol, methacrylic acid and N-vinylacetamide in a mass ratio of 1:1:1;

[0065] Cross-linking agent: ethylene glycol dimethacrylate and triethylene glycol dimethacrylate in a mass ratio of 1:1;

[0066] Photoinitiator: 2-isopropylthioxanthone and 2-hydroxy-2-methyl-1-phenylpropanone in a mass ratio of 1:1;

[0067] The above-mentioned silicone hydrogel raw material and photoinitiator are mixed and stirred for 10 minutes, filtered through a 0.22μm filter element to obtain a mixed solution, injected into a contact lens mold, pressed and fixed, and then irradiated under an LED light with a wavelength of 395nm for 30 minutes. The illumination distance of the light source is 100mm. The molded silicone hydrogel contact lens is taken out by mechanical demolding, and washed with ethanol, water and sterilized in sequence to obtain a silicone hydrogel contact lens.

[0068] Example 4

[0069] The components of the silicone hydrogel contact lens in this embodiment are:

[0070] Silicone hydrogel raw materials: 35% organosiloxane monomer, 60% hydrophilic monomer, 1.5% crosslinking agent, 2% polyethylene glycol diacrylate, 1.5% monomethyl itaconate;

[0071] The mass of the photoinitiator is 1.0% of the mass of the silicone hydrogel raw material;

[0072] The organosiloxane monomer: methacryloxymethyltriethoxysilane and methylvinyldiethoxysilane in a mass ratio of 1:1;

[0073] Hydrophilic monomer: hydroxyethyl methacrylate, polyethylene glycol, methacrylic acid and acrylic acid in a mass ratio of 1:1:1:1;

[0074] Crosslinker: ethylene glycol dimethacrylate;

[0075] Photoinitiator: 2-hydroxy-2-methyl-1-phenylacetone and (2,4,6-trimethylbenzoyl) diphenylphosphine oxide in a mass ratio of 1:1;

[0076] The above-mentioned silicone hydrogel raw material and photoinitiator are mixed and stirred for 10 minutes, filtered through a 0.22μm filter element to obtain a mixed solution, injected into a contact lens mold, pressed and fixed, and then irradiated under an LED light with a wavelength of 395nm for 30 minutes. The illumination distance of the light source is 100mm. The molded silicone hydrogel contact lens is taken out by mechanical demolding, and washed with ethanol, water and sterilized in sequence to obtain a silicone hydrogel contact lens.

[0077] Example 5

[0078] The components of the silicone hydrogel contact lens in this embodiment are:

[0079] Silicone hydrogel raw materials: 50% organosiloxane monomer, 45% hydrophilic monomer, 2% cross-linking agent, 1.5% polyethylene glycol diacrylate, 1.5% monomethyl itaconate;

[0080] The mass of the photoinitiator is 2.0% of the mass of the silicone hydrogel raw material;

[0081] The organosiloxane monomer: methacryloxypropyl tris(trimethylsiloxy)silane and methylvinyldiethoxysilane in a mass ratio of 1:1;

[0082] Hydrophilic monomer: methacrylic acid and N-vinyl acetamide in a mass ratio of 1:1;

[0083] Cross-linking agent: ethylene glycol dimethacrylate and triethylene glycol dimethacrylate in a mass ratio of 1:1;

[0084] Photoinitiator: 2-isopropylthioxanthone, 2-hydroxy-2-methyl-1-phenylpropanone and (2,4,6-trimethylbenzoyl)diphenylphosphine oxide in a mass ratio of 1:1:1.

[0085] The above-mentioned silicone hydrogel raw material and photoinitiator are mixed and stirred for 10 minutes, filtered through a 0.22μm filter element to obtain a mixed solution, injected into a contact lens mold, pressed and fixed, and then irradiated under an LED light with a wavelength of 395nm for 30 minutes. The illumination distance of the light source is 100mm. The molded silicone hydrogel contact lens is taken out by mechanical demolding, and washed with ethanol, water and sterilized in sequence to obtain a silicone hydrogel contact lens.

[0086] Performance Testing

[0087] 1. Measure the oxygen permeability of contact lenses: Use an oxygen permeability tester to analyze the oxygen permeability of contact lenses.

[0088] 2. Measure the water content of contact lenses, which represents the lubricity of contact lenses.

[0089] 3. Measure the contact angle of contact lenses to evaluate their hydrophilicity and lubricity.

[0090] The test results of the contact lenses of Examples 1 to 5 are shown in Table 1.

[0091] Table 1 Performance parameters of contact lenses prepared in Examples 1 to 5

[0092] Example Oxygen permeability (DK / t) Water content (%) Contact angle (°) Example 1 24.6 58 20 Example 2 24.5 59 18 Example 3 24.2 58 17 Example 4 23 58 19 Example 5 23.5 57 16

[0093] As can be seen from Table 1, the silicone hydrogel contact lens prepared by the present invention has high oxygen permeability, high water content and small contact angle, which indicates that the silicone hydrogel contact lens prepared by the present invention has high hydrophilicity and high lubricity.

[0094] The above is only a preferred embodiment of the present invention. It should be pointed out that for ordinary technicians in this technical field, several improvements and modifications can be made without departing from the principle of the present invention. These improvements and modifications should also be regarded as the scope of protection of the present invention.

Claims

1. A method for preparing a silicone hydrogel contact lens, characterized in that: The following steps are involved: Mixing the silicone hydrogel raw material and the photoinitiator, filtering, and obtaining a mixed solution; The mixed solution is injected into a contact lens mold, and after a polymerization reaction is carried out under light conditions, the obtained molded silicone hydrogel contact lens is demolded to obtain a silicone hydrogel contact lens; The silicone hydrogel raw material comprises 30-60% of organic siloxane monomer, 35-65% of hydrophilic monomer, 1-2% of cross-linking agent, 1-2% of polyethylene glycol diacrylate and 0.5-1.5% of monomethyl itaconate.

2. The preparation method according to claim 1, characterized in that: The organic siloxane monomer includes one or more of methacryloxymethyltriethoxysilane, methacryloxymethyltrimethylsilane, methacryloxypropyltri(trimethylsiloxy)silane and methylvinyldiethoxysilane.

3. The preparation method according to claim 1, characterized in that: The hydrophilic monomer includes one or more of hydroxyethyl methacrylate, polyethylene glycol, methacrylic acid, acrylic acid and N-vinylacetamide.

4. The preparation method according to claim 1, characterized in that: The photoinitiator includes one or more of diphenylacetone, 1-hydroxycyclohexylphenylketone, 2-isopropylthioxanthone, 2-hydroxy-2-methyl-1-phenylpropanone, 2-methyl-2-(4-morpholinyl)-1-[4-(methylthio)phenyl]-1-propanone and (2,4,6-trimethylbenzoyl)diphenylphosphine oxide.

5. The preparation method according to claim 4, characterized in that: The mass of the photoinitiator is 0.5-2.0% of the mass of the silicone hydrogel raw material.

6. The preparation method according to claim 1, characterized in that: The crosslinking agent includes ethylene glycol dimethacrylate and / or triethylene glycol dimethacrylate.

7. The preparation method according to claim 1, characterized in that: The wavelength of the light wave of the illumination is 320-400nm.

8. The preparation method according to claim 1 or 7, characterized in that: The polymerization reaction time is 20 to 40 minutes.

9. The silicone hydrogel contact lens prepared by the preparation method according to any one of claims 1 to 8.