A soft hydrophilic contact lens material, a soft hydrophilic contact lens, and a preparation method and application thereof

Abstract

The present invention provides a soft hydrophilic contact lens material, a soft hydrophilic contact lens, and a preparation method and application thereof. The soft hydrophilic contact lens material comprises the following components in percentage by weight: 70% - 99% of a hydrophilic monomer, 0.1% - 10% of an antioxidant monomer, 0.05% - 6% of a crosslinking agent, 0.005% - 5% of an initiator, and 0.5% - 15% of a diluent. In the present invention, the use of the hydrophilic monomer and the antioxidant monomer endows the material with high softness, improves the wearing comfort, and the antioxidant monomer improves the antioxidant performance of the soft hydrophilic contact lens material, reduces free radicals during the wearing process of the contact lens, thereby reducing the possibility of inflammatory reactions and the possibility of contact lens dry eye. At the same time, the antioxidant monomer has an ultraviolet absorption function, which can bring the effect of ultraviolet protection for cells. Moreover, due to the good biosecurity of both the hydrophilic monomer and the antioxidant monomer, the safety of the material is improved.

Description

[0001] This application claims the priority of the patent application with the application number 2024108111010. The filing date of the prior application is June 21, 2024, and the invention title is a soft hydrophilic contact lens material, a soft hydrophilic contact lens, and its preparation method and application. Technical Field

[0002] The present invention belongs to the technical field of hydrogel contact lenses, and relates to a soft hydrophilic contact lens material, a soft hydrophilic contact lens, and its preparation method and application. Background Art

[0003] Ocular surface dry eye is a common ophthalmic disease with a complex pathogenesis, involving tear film stability, ocular surface inflammatory response, and the balance of the ocular surface microenvironment. Wearing soft contact lenses can affect the stability of the ocular surface tear fluid environment, thereby causing discomfort and even complications. Surveys show that wearing soft contact lenses can increase the risk of dry eye by 1.93 - 2.96 times, and clinical studies also show that about 30% - 50% of soft contact lens wearers have dry eye symptoms. Soft contact lenses may increase the osmotic pressure of tears by inducing tear evaporation and electrolyte concentration changes. Hyperosmolarity can cause morphological changes such as cell dehydration, and at the same time activate a series of signal transduction pathways, generate oxidative free radicals, induce inflammatory reactions and apoptosis, causing and exacerbating dry eye. Currently, dry eye is treated with eye drops or eye drops, but patient compliance is not high, and the bioavailability is not high (that is, most of them will be metabolized by tears), and if over-dropped, there will be biological toxicity. Therefore, reducing the levels of oxidative free radicals and tear inflammatory factors at the source is very important for reducing dry eye symptoms during wearing.

[0004] However, currently in China, except for optometric applications such as myopia correction, there are no other functional designs for contact lenses. Therefore, in this field, there is a desire to develop a hydrogel contact lens that can effectively reduce the concentration of free radicals in tears, reduce the inflammatory response, and thus improve the dry eye feeling during wearing. Summary of the Invention

[0005] Aiming at the deficiencies of the prior art, the purpose of the present invention is to provide a soft hydrophilic contact lens material, a soft hydrophilic contact lens, and its preparation method and application.

[0006] To achieve the purpose of this invention, the following technical solutions are adopted:

[0007] On the one hand, the present invention provides a soft hydrophilic contact lens material, and the soft hydrophilic contact lens material comprises the following components in weight percentages:

[0008] Hydrophilic monomer 70% - 99%, antioxidant monomer 0.1% - 10%, crosslinking agent 0.05% - 6%, initiator 0.005% - 5%, diluent 0.5% - 15%.

[0009] In the present invention, hydrophilic monomers and antioxidant monomers are used, enabling the material to form a network structure through the copolymerization of monomers under the action of a crosslinking agent and an initiator during the preparation of soft hydrophilic contact lenses. The antioxidant monomers are stably distributed in the copolymerized network structure. The hydrophilic monomers ensure that the material has high softness and improves the wearing comfort. The antioxidant monomers enhance the antioxidant performance of the soft hydrophilic contact lens material, reduce free radicals during the wearing of the contact lens, thereby reducing the possibility of inflammatory reactions and the possibility of contact lens dry eye. At the same time, the antioxidant monomers have an ultraviolet absorption function, which can bring the effect of ultraviolet protection for cells. Moreover, due to the good biosecurity of both the hydrophilic monomers and the antioxidant monomers, the safety of the material is improved.

[0010] Preferably, the hydrophilic monomer is selected from at least one of 2-hydroxyethyl methacrylate (HEMA), methacrylic acid (MAA), N-vinylpyrrolidone (NVP), N,N-dimethylacrylamide, acrylic acid, 2-hydroxyethyl acrylate, 2-hydroxybutyl methacrylate, 2-hydroxybutyl acrylate, N-vinylacetamide (NVA), or N-vinyl-N-methylacetamide.

[0011] Preferably, the hydrophilic monomer is a combination of 2-hydroxyethyl methacrylate and methacrylic acid.

[0012] Preferably, in the combination of 2-hydroxyethyl methacrylate and methacrylic acid, the weight ratio of 2-hydroxyethyl methacrylate to methacrylic acid is 50:1 to 80:1, such as 50:1, 53:1, 55:1, 58:1, 60:1, 63:1, 66:1, 68:1, 70:1, 73:1, 75:1, 78:1, or 80:1.

[0013] In the soft hydrophilic contact lens material of the present invention, the weight percentage content of the hydrophilic monomer is 70% to 99%, for example, it can be 70%, 73%, 75%, 78%, 80%, 83%, 85%, 88%, 90%, 93%, 95%, 98%, or 99%. In the present invention, if the weight percentage content of the hydrophilic monomer is lower than 70%, the water content of the soft hydrophilic contact lens material will be too low, and the wearing comfort of the contact lens will be reduced. If the weight percentage content of the hydrophilic monomer is higher than 99%, the content of additives such as crosslinking agents and initiators will be too low, and the moldability of the contact lens will be reduced.

[0014] Preferably, the antioxidant monomer is an antioxidant monomer containing a carbon-carbon unsaturated bond.

[0015] Preferably, the antioxidant monomer is at least one of Biginelli-type monomers or Hantzsch-type monomers.

[0016] Preferably, the antioxidant monomer is a combination of at least one of the following compounds:

[0017]

[0018]

[0019] In the soft hydrophilic contact lens material of the present invention, the weight percentage content of the antioxidant monomer is 0.1% to 10%, such as 0.1%, 0.3%, 0.5%, 0.8%, 1%, 1.5%, 1.8%, 2%, 2.5%, 2.8%, 3%, 3.5%, 4%, 4.5%, 5%, 5.5%, 6%, 6.5%, 7%, 7.5%, 8%, 8.5%, 9%, 9.5% or 10%. In the present invention, if the content of the antioxidant monomer is less than 0.1%, the free radical scavenging effect of the soft hydrophilic contact lens material is low, and the effect of improving dry eye is not obvious. If the content of the antioxidant monomer is higher than 10%, the moisture retention of the soft hydrophilic contact lens material is low, the water evaporation rate is too fast, and there is a certain degree of eye irritation after wearing.

[0020] Preferably, the crosslinking agent is selected from ethylene glycol dimethacrylate (EGDMA) and / or allyl methacrylate.

[0021] In the soft hydrophilic contact lens material of the present invention, the weight percentage content of the crosslinking agent is 0.05% to 6%, such as 0.05%, 0.08%, 0.1%, 0.5%, 0.8%, 1%, 1.5%, 2%, 2.5%, 3%, 3.5%, 4%, 4.5%, 5%, 5.5% or 6%.

[0022] Preferably, the initiator is selected from at least one of Irgacure 819, azobisisoheptonitrile, benzoin methyl ether, 2-hydroxy-2-methyl-1-phenylpropanone, and 2,2-diethoxyacetophenone.

[0023] In the soft hydrophilic contact lens material of the present invention, the weight percentage content of the initiator is 0.005% to 5%, such as 0.005%, 0.008%, 0.01%, 0.05%, 0.08%, 0.1%, 0.5%, 0.8%, 1%, 1.3%, 1.5%, 1.8%, 2%, 2.5%, 2.8%, 3%, 3.5%, 3.8%, 4%, 4.3%, 4.5%, 4.8% or 5%.

[0024] Preferably, the diluent is selected from glycerol.

[0025] In the soft hydrophilic contact lens material of the present invention, the weight percentage content of the diluent is 0.5% to 15%, such as 0.5%, 0.8%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14% or 15%.

[0026] Preferably, the soft hydrophilic contact lens material further comprises a colorant.

[0027] Preferably, the colorant is selected from at least one of pigment violet, phthalocyanine green, titanium dioxide, cobalt chromium blue, chromium sesquioxide, iron oxide red, phthalocyanine blue, reactive blue, reactive yellow, reactive green, and vitamin B12.

[0028] Preferably, the weight percentage content of the colorant in the soft hydrophilic contact lens material is 0.1% to 1%, such as 0.1%, 0.3%, 0.5%, 0.8% or 1%.

[0029] In the present invention, the preparation method of the soft hydrophilic contact lens material comprises the following steps:

[0030] Mix the hydrophilic monomer, antioxidant monomer, crosslinking agent, initiator, diluent and optionally the colorant evenly to obtain the soft hydrophilic contact lens material.

[0031] Preferably, the mixing is carried out under stirring at room temperature.

[0032] On the other hand, the present invention provides a soft hydrophilic contact lens, which is prepared from the soft hydrophilic contact lens material as described above.

[0033] On the other hand, the present invention provides a preparation method of the soft hydrophilic contact lens as described above, and the preparation method comprises the following steps:

[0034] (1) Inject the soft hydrophilic contact lens material into the female mold of the mold, then press the male mold into the female mold for mold closing, and put the closed mold into a curing machine to carry out monomer polymerization under ultraviolet irradiation;

[0035] (2) After the polymerization is completed, separate the male and female molds, leave the lens in the female mold, take out the dry sheet of the soft hydrophilic contact lens, carry out hydration extraction, and perform surface inspection during this period;

[0036] (3) Sterilize the soft hydrophilic contact lens after the hydration extraction is completed and the surface inspection is qualified to obtain the soft hydrophilic contact lens.

[0037] Preferably, the mold in step (1) is a plastic male mold and a plastic female mold that are injection-molded by an injection molding machine according to the design for molding a soft hydrophilic contact lens, and the mold that has passed the R value detection.

[0038] In the present invention, the R value refers to the radius of curvature of the mold surface.

[0039] Preferably, the master mold in step (1) is a master mold with its surface treated by Plasma to ensure its surface wetting degree and ensure that the subsequent lenses can adhere to the master mold. The judgment basis for the qualified master mold treatment is to test the surface treatment degree of the master mold with a Dynabeads pen. If the wetting degree exceeds 5 seconds, it is judged as qualified.

[0040] In the present invention, the Plasma-treated master mold is placed on the lens-making disc, and the base material liquid of the soft hydrophilic contact lens is injected into the master mold through an injector, and then the male mold is pressed into the master mold for mold closing.

[0041] Preferably, the ultraviolet irradiation in step (1) is carried out using an ultraviolet lamp.

[0042] Preferably, the wavelength of the ultraviolet irradiation is controlled within 405 - 410 nm.

[0043] Preferably, the energy value of the ultraviolet irradiation is controlled within 10 - 150 mw / cm 2 , such as 10 mw / cm 2 , 11 mw / cm 2 , 12 mw / cm 2 , 13 mw / cm 2 , 14 mw / cm 2 or 15 mw / cm 2 .

[0044] Preferably, the polymerization time in step (1) is controlled within 10 - 60 min, such as 10 min, 15 min, 18 min, 20 min, 23 min, 25 min, 28 min, 30 min, 35 min, 40 min, 45 min, 50 min, 55 min or 60 min.

[0045] Preferably, the hydration extraction temperature in step (2) is controlled within 25 - 80 °C, such as 25 °C, 28 °C, 30 °C, 35 °C, 38 °C, 40 °C, 45 °C, 50 °C, 55 °C, 60 °C, 65 °C, 70 °C, 75 °C or 80 °C, and the hydration extraction time is controlled within 60 - 180 min, such as 60 min, 65 min, 70 min, 75 min, 80 min, 90 min, 100 min, 120 min, 140 min, 150 min, 160 min, 170 min or 180 min.

[0046] Preferably, the sterilization in step (3) is to load the soft hydrophilic contact lenses that have completed hydration extraction and passed surface inspection into a container of a PP cup, inject the preservation solution, and seal it with a lid; then perform high-temperature and humid heat sterilization treatment.

[0047] Preferably, the sterilization temperature is 100 - 130°C, such as 100°C, 105°C, 110°C, 115°C, 120°C, 125°C or 130°C, and the sterilization time is 10 - 45 min, such as 10 min, 13 min, 15 min, 20 min, 25 min, 28 min, 30 min, 35 min, 38 min, 40 min, 43 min or 45 min.

[0048] On the other hand, the present invention provides a drug - releasing material, and the drug - releasing material comprises the soft hydrophilic contact lens material as described above.

[0049] On the other hand, the present invention provides a bandage lens, and the preparation raw materials of the bandage lens comprise the soft hydrophilic contact lens material as described above.

[0050] On the other hand, the present invention provides a wound dressing, and the wound dressing comprises the soft hydrophilic contact lens material as described above.

[0051] Compared with the prior art, the present invention has the following beneficial effects:

[0052] The present invention prepares a soft hydrophilic contact lens material by using a hydrophilic monomer, an antioxidant monomer, a cross - linker, an initiator and a diluent. A soft hydrophilic contact lens is prepared therefrom. Under the action of the cross - linker and the initiator, monomers copolymerize to form a network structure, so that the antioxidant monomer is stably distributed in the copolymerized network structure, making the soft hydrophilic contact lens material have good antioxidant performance, reducing free radicals during the wearing process of the contact lens, thereby reducing the possibility of inflammatory reaction and the possibility of contact lens - induced dry eye. At the same time, the antioxidant monomer has an ultraviolet absorption function, which can bring the effect of ultraviolet protection for cells and has good biosafety.

[0053] The soft hydrophilic contact lens material of the present invention can be applied to contact lenses, drug - releasing materials, bandage lenses, wound dressings, etc., and has broad application prospects. Specific Embodiments

[0054] The technical solution of the present invention will be further described below through specific embodiments. Those skilled in the art should understand that the embodiments are only for helping to understand the present invention and should not be regarded as specific limitations to the present invention.

[0055] Example 1

[0056] In this example, a soft hydrophilic contact lens material is provided, and the soft hydrophilic contact lens material comprises the following components in weight percentage:

[0057] 86.5% hydrophilic monomer, 0.5% antioxidant monomer, 2% crosslinking agent, 1% initiator, 10% diluent.

[0058] The hydrophilic monomer is HEMA and MAA, and the weight ratio of the two is 66:1. The antioxidant monomer is M1: The crosslinking agent is EGDMA, the initiator is Irgacure 819, and the diluent is glycerol.

[0059] Mix the hydrophilic monomer, antioxidant monomer, crosslinking agent, initiator and diluent evenly under stirring at room temperature to obtain the soft hydrophilic contact lens material.

[0060] Example 2

[0061] The difference from Example 1 is only that the soft hydrophilic contact lens material comprises the following components in weight percentages:

[0062] 86% hydrophilic monomer, 1% antioxidant monomer, 2% crosslinking agent, 1% initiator, 10% diluent.

[0063] Example 3

[0064] The difference from Example 1 is only that the soft hydrophilic contact lens material comprises the following components in weight percentages:

[0065] 85.5% hydrophilic monomer, 1.5% antioxidant monomer, 2% crosslinking agent, 1% initiator, 10% diluent.

[0066] Example 4

[0067] The difference from Example 1 is only that the soft hydrophilic contact lens material comprises the following components in weight percentages:

[0068] 85% hydrophilic monomer, 2% antioxidant monomer, 2% crosslinking agent, 1% initiator, 10% diluent.

[0069] Example 5

[0070] The difference from Example 1 is only that the soft hydrophilic contact lens material comprises the following components in weight percentages:

[0071] 84.5% hydrophilic monomer, 2.5% antioxidant monomer, 2% crosslinking agent, 1% initiator, 10% diluent.

[0072] Example 6

[0073] The difference from Example 1 is only that the soft hydrophilic contact lens material comprises the following components in weight percentages:

[0074] 84% hydrophilic monomer, 3% antioxidant monomer, 2% crosslinking agent, 1% initiator, 10% diluent.

[0075] Example 7

[0076] The difference from Example 1 is only that the soft hydrophilic contact lens material comprises the following components in weight percentages:

[0077] 81% hydrophilic monomer, 6% antioxidant monomer, 6% crosslinking agent, 2% initiator, 5% diluent.

[0078] Example 8

[0079] The difference from Example 1 is only that the soft hydrophilic contact lens material comprises the following components in weight percentages:

[0080] 73.5% hydrophilic monomer, 10% antioxidant monomer, 1% crosslinking agent, 0.5% initiator, 15% diluent.

[0081] Example 9

[0082] The difference from Example 1 is only that antioxidant monomer M1 in Example 1 is replaced with the following antioxidant monomer M2:

[0083]

[0084] Example 10

[0085] The difference from Example 2 is only that antioxidant monomer M1 in Example 2 is replaced with the following antioxidant monomer M2:

[0086]

[0087] Example 11

[0088] The difference from Example 3 is only that antioxidant monomer M1 in Example 3 is replaced with the following antioxidant monomer M2:

[0089]

[0090] Example 12

[0091] The difference from Example 4 is only that antioxidant monomer M1 in Example 4 is replaced with the following antioxidant monomer M2:

[0092]

[0093] Example 13

[0094] The difference from Example 5 is only that antioxidant monomer M1 in Example 5 is replaced with the following antioxidant monomer M2:

[0095]

[0096] Example 14

[0097] It is only different from Example 6 in that the antioxidant monomer M1 in Example 6 is replaced with the following antioxidant monomer M2:

[0098]

[0099] Example 15

[0100] It is only different from Example 14 in that the soft hydrophilic contact lens material comprises the following components by weight percentage: hydrophilic monomer 83.5%, antioxidant monomer 3.5%, crosslinking agent 2%, initiator 1%, diluent 10%.

[0101] Example 16

[0102] It is only different from Example 14 in that the soft hydrophilic contact lens material comprises the following components by weight percentage: hydrophilic monomer 83%, antioxidant monomer 4%, crosslinking agent 2%, initiator 1%, diluent 10%.

[0103] Example 17

[0104] It is only different from Example 7 in that the antioxidant monomer M1 in Example 7 is replaced with the following antioxidant monomer M2:

[0105]

[0106] Example 18

[0107] It is only different from Example 8 in that the antioxidant monomer M1 in Example 8 is replaced with the following antioxidant monomer M2:

[0108]

[0109] Example 19

[0110] It is only different from Example 1 in that the antioxidant monomer M1 in Example 1 is replaced with the following antioxidant monomer M3:

[0111]

[0112] Example 20

[0113] It is only different from Example 2 in that the antioxidant monomer M1 in Example 2 is replaced with the following antioxidant monomer M3:

[0114]

[0115] Example 21

[0116] It is only different from Example 3 in that the antioxidant monomer M1 in Example 3 is replaced with the following antioxidant monomer M3:

[0117]

[0118] Example 22

[0119] It is only different from Example 3 in that the antioxidant monomer M1 in Example 3 is replaced with the following antioxidant monomer M4:

[0120]

[0121] Example 23

[0122] It is only different from Example 6 in that the antioxidant monomer M1 in Example 6 is replaced with the following antioxidant monomer M4:

[0123]

[0124] Example 24

[0125] It is only different from Example 1 in that the antioxidant monomer M1 in Example 1 is replaced with the following antioxidant monomer M5: (Prepared with reference to paragraphs 0062 - 0064 of the specification in CN109942760A).

[0126] Example 25

[0127] It is only different from Example 4 in that the antioxidant monomer M1 in Example 4 is replaced with the following antioxidant monomer M5:

[0128]

[0129] Example 26

[0130] It is only different from Example 7 in that the antioxidant monomer M1 in Example 7 is replaced with the following antioxidant monomer M5:

[0131]

[0132] Example 27

[0133] It is only different from Example 1 in that the antioxidant monomer M1 in Example 1 is replaced with the following antioxidant monomer M6: (Its preparation is carried out with reference to step (1) in Example 1 of CN111004359A).

[0134] Example 28

[0135] The difference from Example 4 is only that the antioxidant monomer M1 in Example 4 is replaced with the following antioxidant monomer M6:

[0136]

[0137] Example 29

[0138] The difference from Example 7 is only that the antioxidant monomer M1 in Example 7 is replaced with the following antioxidant monomer M6:

[0139]

[0140] Example 30

[0141] The difference from Example 1 is only that the antioxidant monomer M1 in Example 1 is replaced with the following antioxidant monomer M7: (Its preparation is carried out with reference to step (1) in Example 1 of CN111004359A, where 4-hydroxybenzaldehyde is replaced with 4-hydroxy-3-methoxybenzaldehyde).

[0142] Example 31

[0143] The difference from Example 4 is only that the antioxidant monomer M1 in Example 4 is replaced with the following antioxidant monomer M7:

[0144]

[0145] Example 32

[0146] The difference from Example 7 is only that the antioxidant monomer M1 in Example 7 is replaced with the following antioxidant monomer M7:

[0147]

[0148] Example 33

[0149] The difference from Example 1 is only that the antioxidant monomer M1 in Example 1 is replaced with the following antioxidant monomer M8:

[0150]

[0151] Example 34

[0152] The difference from Example 4 is only that the antioxidant monomer M1 in Example 4 is replaced with the following antioxidant monomer M8:

[0153]

[0154] Example 35

[0155] The difference from Example 7 is only that the antioxidant monomer M1 in Example 7 is replaced with the following antioxidant monomer M8:

[0156]

[0157] Example 36

[0158] The difference from Example 1 is only that the antioxidant monomer M1 in Example 1 is replaced with the following antioxidant monomer M8: And the amounts of each component in the soft hydrophilic contact lens material are as follows:

[0159] Hydrophilic monomer 99%, antioxidant monomer 0.1%, crosslinking agent 0.35%, initiator 0.05%, diluent 0.5%.

[0160] Example 37

[0161] The difference from Example 1 is only that the weight ratio of HEMA and MAA is 50:1.

[0162] Example 38

[0163] The difference from Example 1 is only that the weight ratio of HEMA and MAA is 80:1.

[0164] Example 39

[0165] The difference from Example 1 is only that the hydrophilic monomer is only HEMA and its content is 86.5%.

[0166] Example 40

[0167] The difference from Example 1 is only that the hydrophilic monomer is only MAA and its content is 86.5%.

[0168] Example 41

[0169] The difference from Example 5 is only that the antioxidant monomer is a combination of M1 and M3, and their amounts are 1.5% and 1% respectively.

[0170] Example 42

[0171] The difference from Example 6 is only that the antioxidant monomer is a combination of M1 and M4, and their amounts are 1% and 2% respectively.

[0172] Example 43

[0173] The difference from Example 2 is only that the antioxidant monomer is a combination of M1 and M2, and their amounts are 0.5% and 0.5% respectively.

[0174] Example 44

[0175] The difference from Example 4 is only that the antioxidant monomer is a combination of M5 and M6, and their dosages are 1% and 1% respectively.

[0176] Example 45

[0177] The difference from Example 4 is only that the antioxidant monomer is a combination of M6 and M8, and their dosages are 1% and 1% respectively.

[0178] Comparative Example 1

[0179] The difference from Example 1 is only that the antioxidant monomer used is curcumin (CAS: 458-37-7)

[0180] Comparative Example 2

[0181] The difference from Example 1 is only that the antioxidant monomer used is silymarin, and the structure is as follows:

[0182]

[0183] Comparative Example 3

[0184] The difference from Example 1 is only that poly(ethylene glycol) methacrylate is used to replace the antioxidant monomer in Example 1.

[0185] Comparative Example 4

[0186] The difference from Example 1 is only that the soft hydrophilic contact lens material comprises the following components in weight percentages:

[0187] Hydrophilic monomer 87%, crosslinking agent 2%, initiator 1%, diluent 10%.

[0188] Comparative Example 5

[0189] The difference from Example 8 is only that the soft hydrophilic contact lens material comprises the following components in weight percentages:

[0190] Hydrophilic monomer 70.5%, antioxidant monomer 13%, crosslinking agent 1%, initiator 0.5%, diluent 15%.

[0191] Comparative Example 6

[0192] The difference from Example 1 is only that the soft hydrophilic contact lens material comprises the following components in weight percentages:

[0193] Hydrophilic monomer 86.95%, antioxidant monomer 0.05%, crosslinking agent 2%, initiator 1%, diluent 10%.

[0194] Comparative Example 7

[0195] The difference from Example 8 is only that the soft hydrophilic contact lens material comprises the following components in percentage by weight:

[0196] Hydrophilic monomer 68%, antioxidant monomer 10%, crosslinking agent 6%, initiator 1%, diluent 15%.

[0197] Comparative Example 8

[0198] The difference from Example 1 is only that the soft hydrophilic contact lens material comprises the following components in percentage by weight:

[0199] Hydrophilic monomer 99.3%, antioxidant monomer 0.1%, crosslinking agent 0.05%, initiator 0.05%, diluent 0.5%.

[0200] Application Example 1

[0201] The soft hydrophilic contact lens material of Example 1 is used to prepare a soft hydrophilic contact lens, and the preparation method comprises the following steps:

[0202] 1) Prepare the mold: Use an injection molding machine to inject a plastic male mold and a plastic female mold for molding the soft hydrophilic contact lens according to the design, and after passing the R value test, reserve them for use;

[0203] 2) Treat the female mold: Treat the surface of the injected female mold with Plasma. The judgment basis for qualified treatment is to test the surface treatment degree of the female mold with a dyne pen. If the wetting degree exceeds 5 seconds, it is judged as qualified to ensure its surface wetting degree and ensure that the subsequent lens can remain in the female mold;

[0204] 3) Inject materials and close the mold: Place the treated female mold on the lens-making plate, inject the soft hydrophilic contact lens material liquid prepared in Example 1 into the female mold through a liquid injection machine, and then press the male mold into the female mold to close the mold;

[0205] 4) Polymerize and cure: Place the male and female molds after injecting materials and closing the mold into a curing machine, and carry out monomer polymerization under the action of a UV lamp to obtain a cured dry sheet of the soft hydrophilic contact lens; The irradiation wavelength of the UV lamp is controlled at 410 nm, and the energy value of the UV lamp is controlled at 100 mw / cm 2 , and the polymerization time is 40 min;

[0206] 6) Hydration extraction: After polymerization and curing are completed, the male and female molds are separated, and the lens remains in the female mold. The dry soft hydrophilic contact lens is taken out by a mold splitting machine and placed in a hydration extraction tray for hydration extraction, during which surface inspection is carried out. The temperature of hydration extraction is controlled at 50 °C, and the time of hydration extraction is controlled at 120 min. The specific operation of the surface inspection is as follows: The dry soft hydrophilic contact lens is observed with the naked eye when magnified 7 - 10 times in the buffer solution for hydration extraction. The standard is that the lens has no inclusions that affect normal use, such as spots, residual debris, or dendritic bubbles, etc.; nor any defects, such as cracks or broken edges on the surface; and the shape around the lens edge is uniform.

[0207] 7) Sterilization: The soft hydrophilic contact lens after surface inspection is placed in a container of a PP cup, preservation liquid is injected, and an aluminum foil is covered and sealed by a hot pressing method to achieve complete sealing; then it is placed in a sterilization box and put into a sterilizer for high-temperature and high-humidity sterilization treatment. The sterilization parameters are: temperature 120 °C, time 30 min.

[0208] Application Example 2 - 45 and Comparative Application Example 1 - 8

[0209] The difference from Application Example 1 is only that the soft hydrophilic contact lens materials prepared in Example 1 are respectively replaced with the soft hydrophilic contact lens materials prepared in Example 2 - 45 or Comparative Application Example 1 - 8.

[0210] The diameter, base curve, central thickness, visible light transmittance, ultraviolet transmittance, water content, and free radical scavenging rate of the soft hydrophilic contact lenses prepared in the application examples are tested. The test methods are as follows:

[0211] (1) The diameter, base curve, and central thickness are tested according to the mechanical property test method of GB / T11417.6 - 2012.

[0212] (2) The visible light transmittance and ultraviolet transmittance are tested according to the light transmittance test method in GB / T11417.5 - 2012.

[0213] (3) The water content is tested according to the test method in GB / T11417.7 - 2012.

[0214] (4) Free radical scavenging efficiency: I. Preparation of ABTS working solution: Weigh 76.8 mg of ABTS (2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)) and make up the volume to 20 mL with water; weigh 13.2 mg of potassium persulfate and make up the volume to 20 mL with water. Mix the two evenly and let it stand for more than 14 hours to obtain the ABTS working solution, with a shelf life of 2 weeks. II. Take 1.5 mL of the ABTS working solution and add it to 40 mL (31.57 g) of ethanol to prepare the ABTS detection solution, which should be prepared and used on the same day. III. In each well of a 12-well plate, add 1 mL of the ABTS detection solution and at the same time add the lens; let it stand for 1 h; add 3 mL of ethanol for dilution, take 3 mL of the diluted solution and measure the transmittance at 734 nm. Measurement mode: Select the wavelength range of 680 - 740 nm, for soft lenses, record the reading at 734 nm. Use the absorbance of the pure ABTS detection solution as a control. For each group, the sample addition and measurement are spaced 3 minutes apart for parallel test characterization. Free radical scavenging rate = (1 - (1 - transmittance of the experimental group) / (1 - transmittance of the control group)) × 100%.

[0215] (5) Moisture retention test. The test method is as follows: Immerse the edge area of the contact lens in standard saline and expose the central area to air. Then, after removing the surface solution of the contact lens according to the test method in GB / T 11417.7 - 2012, measure the water content at the 4-hour time point and the 8-hour time point (the better the moisture retention, the higher the water content after a certain period of exposure to air).

[0216] The test results are shown in Table 1 - 5 (the sample numbers in the table represent the samples for parallel testing, and the multiple values under one item in one example in the table represent the values obtained from the parallel sample tests respectively).

[0217] Table 1

[0218]

[0219]

[0220]

[0221]

[0222]

[0223] Table 2

[0224]

[0225]

[0226]

[0227]

[0228] Table 3

[0229]

[0230]

[0231] Table 4

[0232]

[0233]

[0234] Table 5

[0235]

[0236]

[0237]

[0238]

[0239] Tests show that the soft hydrophilic contact lenses of the present invention have good antioxidant properties, ultraviolet absorption properties, and moisturizing properties, and have good biosecurity. It is easy to prepare soft hydrophilic contact lenses meeting national standards through traditional preparation processes such as photocuring.

[0240] In Comparative Application Example 1, the solubility of curcumin in the raw materials is low, resulting in low radical scavenging ability of the contact lenses and insignificant improvement in dry eye effect.

[0241] In Comparative Application Example 2, the solubility of silymarin in the raw materials is low, resulting in low radical scavenging ability of the contact lenses and insignificant improvement in dry eye effect.

[0242] In Comparative Application Example 3, poly(ethylene glycol) methacrylate itself does not have antioxidant ability, resulting in the contact lenses having basically no radical scavenging ability and basically no improvement in dry eye effect.

[0243] In Comparative Application Example 4, no antioxidant monomer is added, resulting in the contact lenses having basically no radical scavenging ability and basically no improvement in dry eye effect.

[0244] In Comparative Application Example 5, the proportion of the antioxidant monomer is higher than 10%, and the contact lenses have low moisture retention, and the excessive water evaporation rate causes certain eye irritation after wearing.

[0245] In Comparative Application Example 6, the proportion of the antioxidant monomer is lower than 0.1%, and the radical scavenging ability of the contact lenses is reduced, and the improvement in dry eye effect is not obvious.

[0246] If the proportion of the hydrophilic monomer in Comparative Application Example 7 is less than 70%, the water content of the contact lens is too low, and the comfort of the contact lens is reduced.

[0247] If the proportion of the hydrophilic monomer in Comparative Application Example 8 is higher than 99%, the contents of auxiliaries such as crosslinking agents and initiators are too low, the moldability of the contact lens is poor, a formed contact lens product cannot be produced, and the parameters cannot be obtained.

[0248] The applicant declares that the present invention uses the above embodiments to illustrate the soft hydrophilic contact lens material, the soft hydrophilic contact lens, and their preparation methods and applications of the present invention. However, the present invention is not limited to the above embodiments, that is, it does not mean that the present invention must rely on the above embodiments to be implemented. Those skilled in the art should understand that any improvement to the present invention, the equivalent substitution of each raw material of the product of the present invention, the addition of auxiliary components, and the selection of specific methods, etc., all fall within the protection scope and the disclosure scope of the present invention.

Claims

1. A soft hydrophilic contact lens material, characterized in that: The soft hydrophilic contact lens material comprises the following components in weight percentage: Hydrophilic monomer 70% to 99%, antioxidant monomer 0.1% to 10%, cross-linking agent 0.05% to 6%, initiator 0.005% to 5%, diluent 0.5% to 15%; in: The hydrophilic monomer is selected from at least one of hydroxyethyl methacrylate, methacrylic acid, N-vinyl pyrrolidone, N,N-dimethylacrylamide, acrylic acid, hydroxyethyl acrylate, hydroxybutyl methacrylate, hydroxybutyl acrylate, N-vinyl acetamide or N-vinyl-N-methylacetamide; The antioxidant monomer is an antioxidant monomer containing a carbon-carbon unsaturated bond, and the antioxidant monomer is specifically at least one of a Biginelli type monomer or a Hantzsch type monomer; The cross-linking agent is selected from ethylene glycol dimethacrylate and / or allyl methacrylate; The initiator is selected from at least one of Irgacure 819, azobisisoheptanenitrile, benzoin methyl ether, 2-hydroxy-2-methyl-1-phenylpropanone or 2,2-diethoxyacetophenone.

2. The soft hydrophilic contact lens material according to claim 1, characterized in that: The hydrophilic monomer is a combination of hydroxyethyl methacrylate and methacrylic acid; The weight ratio of hydroxyethyl methacrylate to methacrylic acid in the combination of hydroxyethyl methacrylate and methacrylic acid is 50:1 to 80:

1.

3. The soft hydrophilic contact lens material according to claim 1, characterized in that: The antioxidant monomer is any one or a combination of at least two of the following compounds:

4. The soft hydrophilic contact lens material according to claim 1, characterized in that: The diluent is selected from glycerol; The soft hydrophilic contact lens material also includes a colorant; The colorant is selected from at least one of pigment violet, phthalocyanine green, titanium dioxide, cobalt chrome blue, chromium trioxide, red iron oxide, phthalocyanine blue, reactive blue, reactive yellow, reactive green or vitamin B12; The weight percentage content of the colorant in the soft hydrophilic contact lens material is 0.1% to 1%.

5. The method for preparing a soft hydrophilic contact lens material according to any one of claims 1 to 4, characterized in that: The preparation method comprises the following steps: The hydrophilic monomer, the antioxidant monomer, the cross-linking agent, the initiator, the diluent and the optional colorant are uniformly mixed to obtain the soft hydrophilic contact lens material; The mixing was performed under stirring at room temperature.

6. A soft hydrophilic contact lens, characterized in that: The soft hydrophilic contact lens is prepared from the soft hydrophilic contact lens material according to any one of claims 1 to 4.

7. The method for preparing a soft hydrophilic contact lens according to claim 6, characterized in that: The preparation method comprises the following steps: (1) injecting a soft hydrophilic contact lens material into a female mold of a mold, then pressing the male mold into the female mold for mold closing, placing the mold after mold closing into a curing machine, and polymerizing the monomer under ultraviolet irradiation; (2) After the polymerization is completed, the male and female molds are separated, and the lens is kept in the female mold. The soft hydrophilic contact lens dry sheet is taken out and hydrated and extracted, and surface inspection is performed during the process; (3) sterilizing the soft hydrophilic contact lens that has been hydrated and extracted and passed the surface inspection to obtain the soft hydrophilic contact lens; The mold in step (1) is a plastic male mold and a plastic female mold for molding a soft hydrophilic contact lens, which are injected by an injection molding machine according to the design and are qualified by R value detection; The master mold in step (1) is a master mold that is surface treated with plasma, and the basis for judging whether the master mold is qualified is: the degree of surface treatment of the master mold is tested by a dyne pen, and if the wetting degree exceeds 5 seconds, it is judged to be qualified; The ultraviolet irradiation in step (1) is performed using an ultraviolet lamp; The wavelength of the ultraviolet irradiation is controlled at 405-410 nm; The energy value of the ultraviolet irradiation is controlled at 10-150 mw / cm 2 ; The polymerization time of step (1) is controlled within 10 to 60 minutes; The hydration extraction temperature in step (2) is controlled at 25 to 80° C., and the hydration extraction time is controlled at 60 to 180 min. The sterilization in step (3) is to place the soft hydrophilic contact lens that has completed the hydration extraction and passed the surface inspection into a PP cup container, inject a preservation solution, and seal it with a cover; then perform a high temperature wet heat sterilization treatment; The sterilization temperature is 100-130° C., and the sterilization time is 10-45 minutes.

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