Fluorosilicone hydrogel contact lens and preparation method thereof

Abstract

The invention belongs to the technical field of contact lenses, and provides a fluorosilicone hydrogel contact lens, which comprises 20-50 parts of a fluorosilicone prepolymer, 20-45 parts of a hydrophilic monomer, 1-3 parts of a cross-linking agent, 0.5-1 part of an initiator, 30-60 parts of a solvent, 2-4 parts of a diluent, 0.05-0.15 part of a functional auxiliary agent, and 2-3 parts of water. The introduction of fluorine and silicon can improve the high oxygen permeability of the lens and reduce the deposition of protein on the surface of the lens; the use of the hydrophilic monomer improves the hydrophilicity of the lens and reduces the discomfort of wearing. As a mucopolysaccharide substance, sodium hyaluronate has good moisture retention and lubricity, and uncomfortable symptoms such as eye dryness and foreign body sensation are relieved; taurine has an anti-inflammatory effect and can relieve eyewear fatigue and discomfort; the chamomile extract has an anti-inflammatory effect and can relieve eye fatigue. The contact lens provided by the invention has very good biocompatibility and mechanical properties, and the wearing comfort of the lens is enhanced.

Description

Technical Field

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

[0002] A contact lens is a kind of corneal contact lens, which has advantages such as beauty and convenience compared with ordinary glasses, so it is welcomed by more and more consumers. However, it is found during wearing that since the contact lens directly contacts the eyeball, oxygen cannot penetrate through the contact lens, which brings a great burden to the eyeball. The most intuitive phenomena are symptoms such as dry eye syndrome and eye redness. And during the process of taking off and putting on the contact lens, it will inevitably come into contact with the external environment, and bacteria or proteins will directly cause pollution of the contact lens, leading to diseases such as inflammation, conjunctivitis, and keratitis. Therefore, how to solve various symptoms caused during wearing has become a new direction in the research of contact lens products. Summary of the Invention

[0003] The purpose of the present invention is to overcome the defects in the prior art and provide a fluorosilicone hydrogel contact lens and a preparation method thereof.

[0004] In order to achieve the above-mentioned invention purpose, the present invention provides the following technical solutions:

[0005] The present invention provides a fluorosilicone hydrogel contact lens, which is prepared from raw materials comprising the following parts by mass:

[0006] 20 - 50 parts of fluorosiloxane prepolymer, 20 - 45 parts of hydrophilic monomer, 1 - 3 parts of crosslinking agent, 0.5 - 1 part of initiator, 30 - 60 parts of solvent, 2 - 4 parts of diluent, 0.05 - 0.15 part of functional auxiliary agent, and 2 - 3 parts of water.

[0007] Preferably, the fluorosiloxane prepolymer is ethyl 2-methylpropyl-2-ethylcarbamate bis(trifluoromethylsiloxysilyl)propylcarbamate and / or ethyl 2-methylpropyl-2-ethylcarbamate 3-hydroxy-3-[3-tris(trifluoromethylsiloxysilyl)propylamino]propyl;

[0008] The hydrophilic monomer is one or more of 2-hydroxyethyl methacrylate, N-vinylpyrrolidone, and methyl methacrylate.

[0009] Preferably, the crosslinking agent is ethylene glycol dimethacrylate and / or N-[2-(2-methylprop-2-enylamino)ethyl]ethylcarbamate;

[0010] The initiator is one or more of photoinitiator 1173, photoinitiator 184, and photoinitiator 651.

[0011] Preferably, the solvent is n-butanol or n-hexanol;

[0012] The diluent is ethylene glycol monoethyl ether.

[0013] Preferably, the functional adjuvant contains sodium hyaluronate, taurine and chamomile extract;

[0014] The mass ratio of the sodium hyaluronate, taurine and chamomile extract is 1:1-2:5-8.

[0015] The present invention also provides a method for preparing the fluorosilicone hydrogel contact lens, comprising the following steps:

[0016] (1) Mix a fluorosiloxane prepolymer, a hydrophilic monomer, a crosslinking agent, an initiator, a solvent and a diluent to obtain a homogeneous solution;

[0017] (2) Mix the functional adjuvant and water and then add them to the homogeneous solution to obtain a mixture;

[0018] (3) Place the mixture in a mold and sequentially carry out rotational molding and photocuring to obtain a semi-finished product;

[0019] (4) Wash and sterilize the semi-finished product to obtain the fluorosilicone hydrogel contact lens.

[0020] Preferably, in step (1), the rotation speed of the mixing is 400-500 rpm and the time is 20-30 min.

[0021] Preferably, in step (2), the rotation speed of the mixing is 200-300 rpm and the time is 5-10 min.

[0022] Preferably, in step (3), the rotational molding is sequentially carried out with high-speed molding and low-speed shaping;

[0023] The rotation speed of the high-speed molding is 3000-5000 rpm and the time is 20-30 s;

[0024] The rotation speed of the low-speed shaping is 1000-1500 rpm and the time is 10-15 s;

[0025] In step (3), the illumination distance of the photocuring is 100-200 mm, the illumination wavelength is 320-420 nm, and the illumination intensity is 3-6 mW / cm 2 , and the time is 80-100 s.

[0026] Preferably, in step (4), the washing is alkali washing and alcohol washing;

[0027] The solution for alkaline washing is an aqueous solution of sodium bicarbonate, and the concentration of the aqueous sodium bicarbonate solution is 0.1 - 0.5%; the ultrasonic frequency for alkaline washing is 25 - 40 kHz, and the time is 20 - 30 min;

[0028] The reagent for alcohol washing is an aqueous ethanol solution, and the concentration of the aqueous ethanol solution is 50 - 60%; the time for alcohol washing is 3 - 6 h, and the rotation speed is 50 - 100 rpm;

[0029] In step (4), the temperature for sterilization is 60 - 70 °C, and the time is 2 - 5 min.

[0030] The present invention provides a fluorosilicone hydrogel contact lens, which is prepared from raw materials comprising the following parts by mass: 20 - 50 parts of fluorosilicone prepolymer, 20 - 45 parts of hydrophilic monomer, 1 - 3 parts of crosslinking agent, 0.5 - 1 part of initiator, 30 - 60 parts of solvent, 2 - 4 parts of diluent, 0.05 - 0.15 part of functional auxiliary agent, and 2 - 3 parts of water. The present invention uses a fluorosilicone prepolymer. The introduction of fluorine and silicon can improve the high oxygen permeability of the lens, reduce the deposition of proteins on the lens surface, and prevent external contamination; the use of hydrophilic monomers enhances the hydrophilicity of the lens and reduces the discomfort during wearing. The functional auxiliary agent includes sodium hyaluronate, taurine, and chamomile extract. As a mucopolysaccharide substance, sodium hyaluronate has good moisturizing and lubricating properties, and can relieve discomfort symptoms such as dryness and foreign body sensation in the eyes; taurine has an anti-inflammatory effect, can reduce eye fatigue and discomfort, and improve vision; chamomile extract has an anti-inflammatory effect, can relieve eye fatigue, and this extract has a sweet herbal fragrance, making the contact lens have a fragrant smell and making people feel physically and mentally comfortable. The contact lens provided by the present invention has good biocompatibility and mechanical properties, effectively enhancing the comfort during lens wearing. Detailed embodiments

[0031] The present invention provides a fluorosilicone hydrogel contact lens, which is prepared from raw materials comprising the following parts by mass:

[0032] 20 - 50 parts of fluorosilicone prepolymer, 20 - 45 parts of hydrophilic monomer, 1 - 3 parts of crosslinking agent, 0.5 - 1 part of initiator, 30 - 60 parts of solvent, 2 - 4 parts of diluent, 0.05 - 0.15 part of functional auxiliary agent, and 2 - 3 parts of water.

[0033] In the present invention, the mass fraction of the fluorosilicone prepolymer is preferably 25 - 45 parts, more preferably 30 - 40 parts, and still more preferably 34 - 38 parts.

[0034] In the present invention, the mass fraction of the hydrophilic monomer is preferably 25 - 40 parts, more preferably 30 - 35 parts, and still more preferably 32 - 33 parts.

[0035] In the present invention, the mass parts of the crosslinking agent are preferably 1.5 to 2.5 parts, more preferably 1.6 to 2.4 parts, and still more preferably 1.8 to 2.2 parts.

[0036] In the present invention, the mass parts of the initiator are preferably 0.6 to 0.9 parts, more preferably 0.7 to 0.8 parts, and still more preferably 0.74 to 0.75 parts.

[0037] In the present invention, the mass parts of the solvent are preferably 35 to 55 parts, more preferably 40 to 50 parts, and still more preferably 45 to 48 parts.

[0038] In the present invention, the mass parts of the diluent are preferably 2.5 to 3.5 parts, more preferably 2.6 to 3.4 parts, and still more preferably 2.8 to 3.2 parts.

[0039] In the present invention, the mass parts of the functional auxiliary agent are preferably 0.06 to 0.14 parts, more preferably 0.08 to 0.12 parts, and still more preferably 0.09 to 0.10 parts.

[0040] In the present invention, the mass parts of the water are preferably 2.1 to 2.9 parts, more preferably 2.2 to 2.8 parts, and still more preferably 2.4 to 2.5 parts.

[0041] In the present invention, the fluorosiloxane prepolymer is ethyl 2-methylpropyl-2-methylacrylate bis(trifluoromethylsiloxysilyl)propylcarbamate and / or ethyl 2-methylpropyl-2-methylacrylate hydroxy-3-[3-tris(trifluoromethylsiloxy)silanylpropylamino]propyl.

[0042] In the present invention, the hydrophilic monomer is one or more of 2-hydroxyethyl methacrylate, N-vinylpyrrolidone, and methyl methacrylate.

[0043] In the present invention, the crosslinking agent is ethylene glycol dimethacrylate and / or ethyl N-[2-(2-methylprop-2-enylamino)ethyl]carbamate.

[0044] In the present invention, the initiator is one or more of photoinitiator 1173, photoinitiator 184, and photoinitiator 651.

[0045] In the present invention, the solvent is n-butanol or n-hexanol.

[0046] In the present invention, the diluent is ethylene glycol monoethyl ether.

[0047] In the present invention, the functional auxiliary agent includes sodium hyaluronate, taurine, and chamomile extract.

[0048] In the present invention, the mass ratio of sodium hyaluronate, taurine and chamomile extract is preferably 1:1-2:5-8, more preferably 1:1.2-1.8:5.5-7.5, and even more preferably 1:1.4-1.6:6-7.

[0049] The present invention also provides a method for preparing the fluorosilicone hydrogel contact lens, comprising the following steps:

[0050] (1) Mix a fluorosiloxane prepolymer, a hydrophilic monomer, a crosslinking agent, an initiator, a solvent and a diluent to obtain a homogeneous solution;

[0051] (2) Mix a functional auxiliary agent and water and then add them to the homogeneous solution to obtain a mixture;

[0052] (3) Place the mixture in a mold and sequentially carry out rotational molding and photocuring to obtain a semi-finished product;

[0053] (4) Wash and sterilize the semi-finished product to obtain the fluorosilicone hydrogel contact lens.

[0054] In the present invention, in step (1), the rotation speed of the mixing is preferably 400-500 rpm, more preferably 420-480 rpm, and even more preferably 440-460 rpm; the time is preferably 20-30 min, more preferably 22-28 min, and even more preferably 24-26 min.

[0055] In the present invention, in step (2), the rotation speed of the mixing is preferably 200-300 rpm, more preferably 220-280 rpm, and even more preferably 240-260 rpm; the time is preferably 5-10 min, more preferably 6-9 min, and even more preferably 7-8 min.

[0056] In the present invention, in step (3), the rotational molding is high-speed molding and low-speed shaping carried out sequentially.

[0057] In the present invention, the rotation speed of the high-speed molding is preferably 3000-5000 rpm, more preferably 3500-4500 rpm, and even more preferably 3800-4200 rpm; the time is preferably 20-30 s, more preferably 22-28 s, and even more preferably 24-26 s.

[0058] In the present invention, the rotation speed of the low-speed shaping is preferably 1000-1500 rpm, more preferably 1100-1400 rpm, and even more preferably 1200-1300 rpm; the time is preferably 10-15 s, more preferably 11-14 s, and even more preferably 12-13 s.

[0059] In the present invention, the illumination distance for photocuring in step (3) is preferably 100 - 200 mm, more preferably 120 - 180 mm, and even more preferably 140 - 160 mm; the illumination wavelength is preferably 320 - 420 nm, more preferably 340 - 400 nm, and even more preferably 360 - 380 nm; the illumination intensity is preferably 3 - 6 mW / cm 2 , more preferably 4 - 5 mW / cm 2 , and even more preferably 4.4 - 4.8 mW / cm 2 ; the time is preferably 80 - 100 s, more preferably 85 - 95 s, and even more preferably 88 - 92 s.

[0060] In the present invention, the cleaning in step (4) is alkali cleaning and alcohol cleaning.

[0061] In the present invention, the solution for alkali cleaning is an aqueous sodium bicarbonate solution, and the concentration of the aqueous sodium bicarbonate solution is preferably 0.1 - 0.5%, more preferably 0.2 - 0.4%, and even more preferably 0.25 - 0.3%; the ultrasonic frequency for alkali cleaning is preferably 25 - 40 kHz, more preferably 30 - 35 kHz, and even more preferably 32 - 33 kHz; the time is preferably 20 - 30 min, more preferably 22 - 28 min, and even more preferably 24 - 26 min.

[0062] In the present invention, the reagent for alcohol cleaning is an aqueous ethanol solution, and the concentration of the aqueous ethanol solution is preferably 50 - 60%, more preferably 52 - 58%, and even more preferably 54 - 56%; the time for alcohol cleaning is preferably 3 - 6 h, more preferably 3.5 - 5.5 h, and even more preferably 4 - 5 h; the rotation speed is preferably 50 - 100 rpm, more preferably 60 - 90 rpm, and even more preferably 70 - 80 rpm.

[0063] In the present invention, the temperature for sterilization in step (4) is preferably 60 - 70 °C, more preferably 62 - 68 °C, and even more preferably 64 - 66 °C; the time is preferably 2 - 5 min, more preferably 2.5 - 4.5 min, and even more preferably 3 - 4 min.

[0064] The technical solutions provided by the present invention will be described in detail below in conjunction with the embodiments, but they should not be construed as limiting the protection scope of the present invention.

[0065] Example 1

[0066] Prepare the following raw materials: 35 parts of ethyl 2-methylpropenoate with [[(methylbis(trifluoromethylsiloxysilyl)propylcarbamoyloxy]2-methylpropyl]], 26 parts of 2-hydroxyethyl methacrylate, 2 parts of ethylene glycol dimethacrylate, 0.5 part of photoinitiator 1173, 55 parts of n-butanol, 3 parts of ethylene glycol monoethyl ether, 0.08 part of functional additive, and 2.5 parts of water; the mass ratio of sodium hyaluronate, taurine, and chamomile extract in the functional additive is 1:1.5:6.

[0067] Mix the raw materials except for the functional additive and water, and stir for 25 min at 450 rpm to obtain a homogeneous solution; stir the functional additive and water at 250 rpm for 6 min, then add them to the homogeneous solution and stir evenly to obtain a mixture; place the mixture in a mold, first mold it at 4000 rpm for 25 s, and then shape it at 1200 rpm for 12 s; after shaping, control the light distance to be 150 mm, the light wavelength to be 360 nm, and the light intensity to be 5 mW / cm 2 , and cure for 90 s to obtain a semi-finished product; ultrasonically treat the semi-finished product in a 0.3% aqueous sodium bicarbonate solution at 30 kHz for 25 min, then wash it in a 55% aqueous ethanol solution at 80 rpm for 5 h, and finally sterilize it at 65 °C for 2 min to obtain a fluorosilicone hydrogel contact lens.

[0068] Example 2

[0069] Prepare the following raw materials: 40 parts of ethyl 2-methylpropenoate with [[hydroxy-3-[3-tris(trifluoromethylsiloxysilyl)propylamino]propyl]], 43 parts of N-vinylpyrrolidone, 1 part of ethyl N-[2-(2-methylprop-2-enylamino)ethyl]carbamate, 0.7 part of photoinitiator 184, 50 parts of n-hexanol, 4 parts of ethylene glycol monoethyl ether, 0.1 part of functional additive, and 3 parts of water; the mass ratio of sodium hyaluronate, taurine, and chamomile extract in the functional additive is 1:1:5.

[0070] Mix the raw materials except for the functional additive and water, and stir for 30 min at 400 rpm to obtain a homogeneous solution; stir the functional additive and water at 300 rpm for 5 min, then add them to the homogeneous solution and stir evenly to obtain a mixture; place the mixture in a mold, first mold it at 3500 rpm for 30 s, and then shape it at 1400 rpm for 11 s; after shaping, control the light distance to be 180 mm, the light wavelength to be 410 nm, and the light intensity to be 4 mW / cm 2 , and cure for 80 s to obtain a semi-finished product; ultrasonically treat the semi-finished product in a 0.4% aqueous sodium bicarbonate solution at 25 kHz for 30 min, then wash it in a 60% aqueous ethanol solution at 100 rpm for 4 h, and finally sterilize it at 60 °C for 3 min to obtain a fluorosilicone hydrogel contact lens.

[0071] Example 3

[0072] Configure the following raw materials: 44 parts of ethyl 2-methylpropyl-2-enecarboxylate with hydroxy-3-[3-tris(trifluoromethylsiloxy)silanylpropylamino]propyl, 45 parts of methyl methacrylate, 3 parts of ethylene glycol dimethacrylate, 1 part of photoinitiator 651, 55 parts of n-hexanol, 3 parts of ethylene glycol monoethyl ether, 0.09 part of functional additive, 2.5 parts of water; the mass ratio of sodium hyaluronate, taurine and chamomile extract in the functional additive is 1:2:7.

[0073] Mix the raw materials except the functional additive and water, and stir for 25 min at 460 rpm to obtain a homogeneous solution; stir the functional additive and water at 260 rpm for 10 min, then add them to the homogeneous solution and stir evenly to obtain a mixture; place the mixture in a mold, first mold at 4500 rpm for 30 s, and then shape at 1500 rpm for 14 s; after shaping, control the light distance to be 120 mm, the light wavelength to be 360 nm, and the light intensity to be 3 mW / cm 2 , cure for 90 s to obtain a semi-finished product; ultrasonically treat the semi-finished product in a 0.5% aqueous sodium bicarbonate solution at 40 kHz for 23 min, then wash in a 50% aqueous ethanol solution at 80 rpm for 6 h, and finally sterilize at 65 °C for 2 min to obtain a fluorosilicone hydrogel contact lens.

[0074] Example 4

[0075] Configure the following raw materials: 37 parts of ethyl 2-methylpropyl-2-enecarboxylate with methylbis(trifluoromethylsiloxysilyl)propylcarbamoyloxy, 35 parts of methyl methacrylate, 2.5 parts of ethylene glycol dimethacrylate, 0.7 part of photoinitiator 1173, 44 parts of n-butanol, 2.5 parts of ethylene glycol monoethyl ether, 0.06 part of functional additive, 3 parts of water; the mass ratio of sodium hyaluronate, taurine and chamomile extract in the functional additive is 1:1.8:6.

[0076] Mix the raw materials except the functional additive and water, and stir for 30 min at 500 rpm to obtain a homogeneous solution; stir the functional additive and water at 200 rpm for 5 min, then add them to the homogeneous solution and stir evenly to obtain a mixture; place the mixture in a mold, first mold at 3600 rpm for 25 s, and then shape at 1400 rpm for 11 s; after shaping, control the light distance to be 180 mm, the light wavelength to be 410 nm, and the light intensity to be 5 mW / cm 2, it was cured for 80 s to obtain a semi-finished product; the semi-finished product was ultrasonically treated in a 0.3% aqueous sodium bicarbonate solution at 32 kHz for 30 min, then washed in a 60% aqueous ethanol solution at 80 rpm for 3 h, and finally sterilized at 60 °C for 2 min to obtain a fluorosilicone hydrogel contact lens.

[0077] The contact lenses prepared in Examples 1 to 4 were subjected to performance tests, and the results were recorded in Table 1.

[0078] Table 1 Performance test results

[0079]

[0080]

[0081] As can be seen from the above examples, the present invention provides a fluorosilicone hydrogel contact lens. The introduction of fluorine and silicon can improve the high oxygen permeability of the lens, reduce the deposition of proteins on the lens surface, and prevent external contamination; the use of hydrophilic monomers enhances the hydrophilicity of the lens and reduces the discomfort during wearing. The contact lens provided by the present invention has good biocompatibility and mechanical properties, effectively enhancing the comfort of the lens during wearing.

[0082] The above are only the preferred embodiments of the present invention. It should be noted that for those of ordinary skill in the art, without departing from the principle of the present invention, several improvements and modifications can be made, and these improvements and modifications should also be regarded as the protection scope of the present invention.

Claims

1. A fluorosilicone hydrogel contact lens, characterized in that, It is prepared from raw materials containing the following parts by mass: 20-50 parts of fluorosiloxane prepolymer, 20-45 parts of hydrophilic monomer, 1-3 parts of crosslinking agent, 0.5-1 part of initiator, 30-60 parts of solvent, 2-4 parts of diluent, 0.05-0.15 part of functional additive, and 2-3 parts of water.

2. The fluorosilicone hydrogel contact lens according to claim 1, wherein The fluorosiloxane prepolymer is ethyl 2-methylpropyl-2-methylacrylate methylbis(trifluoromethylsiloxysilyl)propylcarbamoyloxy] and / or ethyl 2-methylpropyl-2-methylacrylate hydroxy-3-[3-tris(trifluoromethylsiloxysilyl)propylamino]propyl]; The hydrophilic monomer is one or more of 2-hydroxyethyl methacrylate, N-vinylpyrrolidone, and methyl methacrylate.

3. The fluorosilicone hydrogel contact lens according to claim 2, wherein The crosslinking agent is ethylene glycol dimethacrylate and / or ethyl N-[2-(2-methylprop-2-enylamino)ethyl]carbamate; The initiator is one or more of photoinitiator 1173, photoinitiator 184, and photoinitiator 651.

4. The fluorosilicone hydrogel contact lens according to claim 3, wherein, The solvent is n-butanol or n-hexanol; The diluent is ethylene glycol monoethyl ether.

5. The fluorosilicone hydrogel contact lens according to claim 4, wherein The functional additive contains sodium hyaluronate, taurine, and chamomile extract; The mass ratio of sodium hyaluronate, taurine, and chamomile extract is 1:1-2:5-8.

6. The preparation method of the fluorosilicone hydrogel contact lens according to any one of claims 1 to 5, characterized in that, It includes the following steps: (1) Mix the fluorosiloxane prepolymer, hydrophilic monomer, crosslinking agent, initiator, solvent, and diluent to obtain a homogeneous solution; (2) Mix the functional additive and water and then add them to the homogeneous solution to obtain a mixture; (3) Place the mixture in a mold and sequentially perform rotational molding and photocuring to obtain a semi-finished product; (4) Wash and sterilize the semi-finished product to obtain the fluorosilicone hydrogel contact lens.

7. The preparation method of the fluorosilicone hydrogel contact lens according to claim 6, wherein, In step (1), the rotation speed of the mixing is 400-500 rpm, and the time is 20-30 min.

8. The preparation method of the fluorosilicone hydrogel contact lens according to claim 7, characterized in that, In step (2), the rotation speed of the mixing is 200-300 rpm, and the time is 5-10 min.

9. The preparation method of the fluorosilicone hydrogel contact lens according to claim 8, characterized in that, In step (3), the rotational molding is high-speed molding and low-speed shaping performed sequentially; The rotation speed of the high-speed molding is 3000-5000 rpm, and the time is 20-30 s; The rotation speed of the low-speed shaping is 1000-1500 rpm, and the time is 10-15 s; In step (3), the light curing is carried out at a light irradiation distance of 100-200 mm, a light wavelength of 320-420 nm, a light intensity of 3-6 mW / cm 2 , and a time of 80-100 s.

10. The preparation method of the fluorosilicone hydrogel contact lens according to claim 9, characterized in that, In step (4), the washing is alkali washing and alcohol washing; The solution for alkali washing is an aqueous sodium bicarbonate solution, and the concentration of the aqueous sodium bicarbonate solution is 0.1-0.5%; the ultrasonic frequency for alkali washing is 25-40 kHz, and the time is 20-30 min; The reagent for alcohol washing is an aqueous ethanol solution, and the concentration of the aqueous ethanol solution is 50-60%; the time for alcohol washing is 3-6 h, and the rotation speed is 50-100 rpm; In step (4), the temperature for sterilization is 60-70 °C, and the time is 2-5 min.

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