Contact lens material with lasting fragrance and preparation method thereof

Abstract

The invention belongs to the technical field of contact lenses, and discloses a long-lasting fragrance-retaining contact lens material and a preparation method thereof. The invention discloses a light-sensitive adhesive which is prepared from the following raw materials: hydroxyethyl methylacrylate, N-vinyl pyrrolidone, acrylamide, glycidyl methacrylate, methacryloyloxypropyl tri (trimethylsiloxane) silane, a cross-linking agent, a modified essential oil microcapsule and a photoinitiator. According to the modified essential oil microcapsule, gelatin-Arabic gum serves as a capsule wall to wrap the essential oil, fragrance can be continuously released, the capsule wall material is high in hydrophilicity, good in biocompatibility and free of irritation to the cornea, and the wearing comfort is improved. Meanwhile, modification is carried out, through surface functionalization of the silane coupling agent, the essential oil microcapsule can be well connected with a contact lens base material, the compatibility with the base material is good, falling of the essential oil microcapsule is avoided, fragrance can be kept for a long time, and pleasant sensory experience is brought to consumers.

Description

Technical Field

[0001] The present invention relates to the technical field of contact lenses, and particularly to a contact lens material with long-lasting fragrance and a preparation method thereof. Background Art

[0002] Contact lenses, also known as corneal contact lenses or corneal contact glasses, refer to lenses worn on the cornea of the eye to correct vision or protect the eyes. Colored contact lenses are contact lenses. According to the hardness of the material, it includes hard, semi-hard, and soft types. Contact lenses not only bring great improvement to patients with refractive errors such as myopia, hyperopia, and astigmatism in terms of appearance and convenience. Moreover, the field of vision is wide and the vision is vivid. In addition, it also plays a special role in controlling the development of myopia and astigmatism in teenagers and treating special eye diseases.

[0003] The materials of traditional contact lenses are mainly hydrogels or silicone hydrogels, and the functions mainly focus on oxygen permeability, moisture retention, and mechanical properties. With the improvement of the consumption level, consumers have higher and higher requirements for other additional functions of contact lenses, such as color, fragrance, etc. However, there is no existing contact lens material that can achieve long-lasting release of fragrance. Currently, fragrance materials are mostly used in textiles or daily chemical products, but directly applying them to ophthalmic medical devices requires solving problems such as safety (such as the irritation of the essence), stability (such as the fragrance slow-release period), and material compatibility (such as the binding strength between the essence and the hydrogel).

[0004] Therefore, how to provide a contact lens material that can release fragrance persistently is an urgent problem to be solved currently. Summary of the Invention

[0005] The purpose of the present invention is to provide a contact lens material with long-lasting fragrance and a preparation method thereof, to solve the problem that the existing contact lenses do not have the function of long-lasting release of fragrance.

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

[0007] The present invention provides a contact lens material with long-lasting fragrance, comprising the following raw materials in parts by mass:

[0008] 50 - 70 parts of 2-hydroxyethyl methacrylate, 10 - 30 parts of N-vinylpyrrolidone, 1 - 10 parts of acrylamide, 5 - 15 parts of glycidyl methacrylate, 10 - 20 parts of methacryloxypropyl tris(trimethylsiloxy)silane, 5 - 15 parts of cross-linking agent, 3 - 20 parts of modified essential oil microcapsules, 5 - 20 parts of photoinitiator.

[0009] Preferably, the cross-linking agent is ethylene glycol dimethacrylate and / or ethylene glycol diacrylate.

[0010] Preferably, the photoinitiator is one of photoinitiator TPO, photoinitiator 184, and photoinitiator 819.

[0011] Preferably, the preparation method of the modified essential oil microcapsules is as follows:

[0012] Using essential oil as the core material, mix the essential oil, emulsifier, and gelatin aqueous solution to obtain an oil-in-water emulsion; heat the oil-in-water emulsion and then add the gum arabic aqueous solution, and then adjust the pH to 3.5 - 4.5 to obtain the essential oil microcapsule solution;

[0013] Mix the essential oil microcapsule solution and the curing agent, and then adjust the pH to 10 - 11.5 for curing reaction; after the curing reaction, perform water washing and drying to obtain the essential oil microcapsules;

[0014] Mix the essential oil microcapsules, silane coupling agent, and water, and then adjust the pH to 7 - 7.5 for modification reaction to obtain the modified essential oil microcapsules.

[0015] Preferably, the essential oil is one or more of rose essential oil, lavender essential oil, tea tree essential oil, jasmine essential oil, basil essential oil, sandalwood essential oil, and chamomile essential oil.

[0016] Preferably, the dosage ratio of the essential oil, emulsifier, gelatin in the gelatin aqueous solution, and gum arabic in the gum arabic aqueous solution is 1 - 10 mL: 0.01 - 0.1 g: 5 - 20 g: 5 - 20 g; the concentrations of the gelatin aqueous solution and the gum arabic aqueous solution are independently 10 - 40 g / L.

[0017] Preferably, the curing agent is glutaraldehyde; the silane coupling agent is KH-550 and / or KH-570.

[0018] Preferably, the temperature of the modification reaction is 60 - 80 °C; the time of the modification reaction is 1 - 3 h.

[0019] The present invention also provides a preparation method of a long-lasting fragrance-retaining contact lens material, comprising the following steps:

[0020] Mix 2-hydroxyethyl methacrylate, N-vinylpyrrolidone, acrylamide, glycidyl methacrylate, methacryloxypropyl tris(trimethylsiloxy)silane, crosslinking agent, photoinitiator, and modified essential oil microcapsules to obtain a raw material liquid; inject the raw material liquid into a contact lens mold and perform photopolymerization under a protective atmosphere and UV light irradiation to obtain the long-lasting fragrance-retaining contact lens material.

[0021] Preferably, the wavelength of the UV light irradiation is 350 - 400 nm; the time of the photopolymerization is 10 - 90 min.

[0022] As can be seen from the above technical solutions, compared with the prior art, the present invention has the following beneficial effects:

[0023] (1) The present invention uses 2-hydroxyethyl methacrylate monomer as the main matrix, and adds N-vinylpyrrolidone and siloxane monomer to improve the oxygen permeability of the contact lens. The addition of glycidyl methacrylate reduces the shrinkage rate. The contact lens matrix material of the present invention has good hydrophilicity, good light transmittance, oxygen permeability, water content, high biocompatibility, comfortable to wear, and can be worn for a long time.

[0024] (2) The present invention also adds essential oil microcapsules, which are encapsulated with gelatin-arabic gum as the capsule wall, so that the fragrance can be continuously released. And the capsule wall material has high hydrophilicity and good biocompatibility, is non-irritating to the cornea, and improves the wearing comfort. At the same time, the essential oil microcapsules are modified. Through the surface functionalization of the silane coupling agent, the essential oil microcapsules can form a good connection with the contact lens matrix material, have good compatibility with the matrix material, avoid the shedding of the essential oil microcapsules, can leave a lasting fragrance, and bring a pleasant sensory experience to consumers.

[0025] (3) The contact lens material of the present invention uses a photopolymerization method, the preparation process is simple, the polymerization time is greatly shortened, the production efficiency of the contact lens is improved, and it is conducive to large-scale industrial production. Detailed Embodiments

[0026] The present invention provides a contact lens material with a lasting fragrance, comprising the following raw materials in parts by mass:

[0027] 50-70 parts of 2-hydroxyethyl methacrylate, 10-30 parts of N-vinylpyrrolidone, 1-10 parts of acrylamide, 5-15 parts of glycidyl methacrylate, 10-20 parts of methacryloxypropyltris(trimethylsiloxy)silane, 5-15 parts of crosslinking agent, 3-20 parts of modified essential oil microcapsules, 5-20 parts of photoinitiator.

[0028] In the present invention, the crosslinking agent is preferably ethylene glycol dimethacrylate and / or ethylene glycol diacrylate, further preferably ethylene glycol dimethacrylate or ethylene glycol diacrylate, and more preferably ethylene glycol dimethacrylate.

[0029] In the present invention, the photoinitiator is preferably one of photoinitiator TPO, photoinitiator 184, and photoinitiator 819, further preferably photoinitiator 184 or photoinitiator 819, and more preferably photoinitiator 184.

[0030] In the present invention, the preparation method of the modified essential oil microcapsules is:

[0031] Using essential oil as the core material, mix the essential oil, emulsifier and gelatin aqueous solution to obtain an oil-water emulsion; heat the oil-water emulsion and then add the gum arabic aqueous solution, and then adjust the pH to 3.5 - 4.5 to obtain an essential oil microcapsule solution;

[0032] Mix the essential oil microcapsule solution and the curing agent, and then adjust the pH to 10 - 11.5 to carry out a curing reaction; after the curing reaction is completed, carry out water washing and drying to obtain essential oil microcapsules;

[0033] Mix the essential oil microcapsules, silane coupling agent and water, and then adjust the pH to 7 - 7.5 to carry out a modification reaction to obtain modified essential oil microcapsules.

[0034] In the present invention, the essential oil is preferably one or more of rose essential oil, lavender essential oil, tea tree essential oil, jasmine essential oil, basil essential oil, sandalwood essential oil, chamomile essential oil, further preferably one or more of rose essential oil, lavender essential oil, jasmine essential oil, chamomile essential oil, and more preferably lavender essential oil.

[0035] In the present invention, the dosage ratio of the essential oil, emulsifier, gelatin in the gelatin aqueous solution, and gum arabic in the gum arabic aqueous solution is preferably 1 - 10 mL: 0.01 - 0.1 g: 5 - 20 g: 5 - 20 g, further preferably 2 - 8 mL: 0.01 - 0.05 g: 6 - 15 g: 6 - 15 g, and more preferably 5 mL: 0.03 g: 10 g: 10 g; the concentrations of the gelatin aqueous solution and the gum arabic aqueous solution are independently preferably 10 - 40 g / L, further preferably 15 - 30 g / L, and more preferably 20 g / L; the emulsifier is preferably polyvinyl alcohol, and further preferably polyvinyl alcohol with a molecular weight of 120000.

[0036] In the present invention, stirring is also included during the mixing of the essential oil and the gelatin aqueous solution; the rotation speed of the stirring is preferably 1000 - 3000 rpm, further preferably 1200 - 2500 rpm, and more preferably 2000 rpm; the mixing time is preferably 10 - 60 min, further preferably 12 - 40 min, and more preferably 20 min.

[0037] In the present invention, the heating temperature of the oil-water emulsion is preferably 40 - 60 °C, further preferably 50 - 60 °C, and more preferably 60 °C.

[0038] In the present invention, stirring is also included after adjusting the pH to 3.5 - 4.5; the rotation speed of the stirring is preferably 500 - 1000 rpm, further preferably 600 - 900 rpm, and more preferably 800 rpm; the stirring time is preferably 10 - 30 min, further preferably 15 - 25 min, and more preferably 20 min.

[0039] In the present invention, the curing agent is preferably glutaraldehyde; the volume ratio of the gelatin aqueous solution to glutaraldehyde is preferably 1:0.01 - 0.3, more preferably 1:0.07 - 0.2, and still more preferably 1:0.1.

[0040] In the present invention, the temperature of the curing reaction is preferably 0 - 20°C, more preferably 1 - 10°C, and still more preferably 5°C; the time of the curing reaction is preferably 30 - 120 min, more preferably 60 - 100 min, and still more preferably 90 min.

[0041] In the present invention, the silane coupling agent is preferably KH-550 and / or KH-570, more preferably KH-550 or KH-570, and still more preferably KH-570.

[0042] In the present invention, the dosage ratio of the essential oil microcapsules, the silane coupling agent, and water is preferably 1 - 5 g:1 - 10 mL:90 - 100 mL, more preferably 2 - 4 g:5 - 10 mL:95 - 100 mL, and still more preferably 3 g:9 mL:100 mL.

[0043] In the present invention, the temperature of the modification reaction is preferably 60 - 80°C, more preferably 70 - 80°C, and still more preferably 80°C; the time of the modification reaction is preferably 1 - 3 h, more preferably 1 - 2 h, and still more preferably 1 h.

[0044] The present invention also provides a method for preparing a long-lasting fragrance-retaining contact lens material, comprising the following steps:

[0045] Mix hydroxyethyl methacrylate, N-vinylpyrrolidone, acrylamide, glycidyl methacrylate, methacryloxypropyl tris(trimethylsiloxy)silane, a crosslinking agent, a photoinitiator, and modified essential oil microcapsules to obtain a raw material liquid; inject the raw material liquid into a contact lens mold and carry out photopolymerization under a protective atmosphere and UV light irradiation to obtain a long-lasting fragrance-retaining contact lens material.

[0046] In the present invention, the mixing method is stirring; the stirring speed is preferably 100 - 500 rpm, more preferably 150 - 300 rpm, and still more preferably 200 rpm; the mixing time is preferably 10 - 60 min, more preferably 30 - 50 min, and still more preferably 40 min.

[0047] In the present invention, the protective atmosphere is preferably nitrogen.

[0048] In the present invention, the wavelength of the UV light is preferably 350 - 400 nm, more preferably 355 - 380 nm, and even more preferably 365 nm; the time for photopolymerization is preferably 10 - 90 min, more preferably 20 - 60 min, and even more preferably 45 min.

[0049] The technical solutions in the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only a part of the embodiments of the present invention, rather than all the embodiments. All other embodiments obtained by those of ordinary skill in the art based on the embodiments of the present invention without creative efforts shall fall within the protection scope of the present invention.

[0050] Example 1

[0051] This example provides a long-lasting fragrance-retaining contact lens material, comprising the following raw materials in parts by mass:

[0052] 65 parts of 2-hydroxyethyl methacrylate, 20 parts of N-vinylpyrrolidone, 4 parts of acrylamide, 12 parts of glycidyl methacrylate, 14 parts of methacryloxypropyl tris(trimethylsiloxy)silane, 8 parts of ethylene glycol dimethacrylate, 16 parts of modified essential oil microcapsules, and 15 parts of photoinitiator 184.

[0053] The preparation method of the long-lasting fragrance-retaining contact lens material of this example comprises the following steps:

[0054] (1) Using lavender essential oil as the core material, the essential oil, polyvinyl alcohol (molecular weight of 120,000) and 20 g / L gelatin aqueous solution are stirred and mixed at 2000 rpm for 20 min to obtain an oil-water emulsion; the oil-water emulsion is heated to 60 °C, 20 g / L gum arabic aqueous solution is added, and then the pH is adjusted to 4 and stirred at 800 rpm for 20 min to obtain an essential oil microcapsule solution; wherein, the dosage ratio of the essential oil, polyvinyl alcohol, gelatin in the gelatin aqueous solution, and gum arabic in the gum arabic aqueous solution is 5 mL: 0.03 g: 10 g: 10 g;

[0055] The essential oil microcapsule solution and glutaraldehyde are mixed at a volume ratio of 1:0.1, and then the pH is adjusted to 11, and the curing reaction is carried out at 5 °C for 90 min; after the curing reaction is completed, washing and drying are carried out to obtain essential oil microcapsules;

[0056] The essential oil microcapsules, silane coupling agent KH-570, and water are mixed at a dosage ratio of 3 g: 9 mL: 100 mL, then the pH is adjusted to 7, and the modification reaction is carried out at 80 °C for 1 h, and then filtration and drying are carried out to obtain modified essential oil microcapsules;

[0057] (2) Stir and mix hydroxyethyl methacrylate, N-vinylpyrrolidone, acrylamide, glycidyl methacrylate, methacryloxypropyltris(trimethylsiloxy)silane, ethylene glycol dimethacrylate, photoinitiator, and modified essential oil microcapsules at 200 rpm for 40 min to obtain a raw material solution; inject the raw material solution into a contact lens mold, and carry out photopolymerization for 45 min under the conditions of a nitrogen atmosphere and UV light with a wavelength of 365 nm to obtain a contact lens material with long-lasting fragrance retention; soak the contact lens material with long-lasting fragrance retention in deionized water for later use.

[0058] Example 2

[0059] This example provides a contact lens material with long-lasting fragrance retention, which contains the following raw materials in parts by mass:

[0060] 55 parts of hydroxyethyl methacrylate, 10 parts of N-vinylpyrrolidone, 5 parts of acrylamide, 8 parts of glycidyl methacrylate, 20 parts of methacryloxypropyltris(trimethylsiloxy)silane, 5 parts of ethylene glycol dimethacrylate, 5 parts of modified essential oil microcapsules, and 9 parts of photoinitiator TPO.

[0061] The preparation method of the contact lens material with long-lasting fragrance retention in this example is specifically referred to in Example 1. The difference is that in step (1), lavender essential oil is replaced by rose essential oil, and the dosage ratio of essential oil, polyvinyl alcohol, gelatin in the gelatin aqueous solution, and arabic gum in the arabic gum aqueous solution is 2 mL: 0.05 g: 7 g: 7 g. In step (2), the photopolymerization time is 20 min.

[0062] Example 3

[0063] This example provides a contact lens material with long-lasting fragrance retention, which contains the following raw materials in parts by mass:

[0064] 60 parts of hydroxyethyl methacrylate, 20 parts of N-vinylpyrrolidone, 7 parts of acrylamide, 10 parts of glycidyl methacrylate, 15 parts of methacryloxypropyltris(trimethylsiloxy)silane, 6 parts of ethylene glycol dimethacrylate, 10 parts of modified essential oil microcapsules, and 12 parts of photoinitiator 184.

[0065] The preparation method of the contact lens material with long-lasting fragrance retention in this example is specifically referred to in Example 1. The difference is that in step (1), lavender essential oil is replaced by jasmine essential oil, and the dosage ratio of essential oil microcapsules, silane coupling agent KH-570, and water is 2 g: 5 mL: 90 mL. In step (2), the photopolymerization time is 30 min.

[0066] Example 4

[0067] This embodiment provides a contact lens material with long-lasting fragrance retention, comprising the following raw materials in parts by mass:

[0068] 70 parts of 2-hydroxyethyl methacrylate, 30 parts of N-vinylpyrrolidone, 1 part of acrylamide, 15 parts of glycidyl methacrylate, 10 parts of methacryloxypropyltris(trimethylsiloxy)silane, 7 parts of ethylene glycol diacrylate, 13 parts of modified essential oil microcapsules, and 15 parts of photoinitiator 819.

[0069] For the preparation method of the contact lens material with long-lasting fragrance retention in this embodiment, please refer to Example 1 specifically. The difference is that in step (1), lavender essential oil is replaced by chamomile essential oil, and the dosage ratio of essential oil, polyvinyl alcohol, gelatin in the gelatin aqueous solution, and gum arabic in the gum arabic aqueous solution is 2 mL: 0.07 g: 15 g: 15 g. The dosage ratio of essential oil microcapsules, silane coupling agent KH-550, and water is 5 g: 2 mL: 100 mL. In step (2), the photo-polymerization time is 60 min.

[0070] Comparative Example 1

[0071] This comparative example provides a contact lens material. Please refer to Example 1 specifically. The difference is that the essential oil microcapsules are not modified with a silane coupling agent.

[0072] The contact lens materials prepared in Examples 1 to 4 and Comparative Example 1 were tested for light transmittance, oxygen permeability coefficient, and water content according to GB / T 11417.5-2012 and GB / T 11417.7-2012. The results are shown in Table 1.

[0073] Table 1 Test results of light transmittance, oxygen permeability coefficient, and water content of contact lens materials

[0074]

[0075] As can be seen from Table 1, the light transmittance of the contact lenses of the present invention is above 90%, the oxygen permeability coefficient is about 28×10 -11 or so, and the water content reaches about 50%. The performance meets the usage requirements of contact lenses, and the high water content improves the wearing comfort.

[0076] The contact lens materials prepared in Examples 1 to 4 and Comparative Example 1 were immersed in artificial tears ( Sodium hyaluronate eye drops, specification 0.1%). They were taken out after being immersed for 1 day, 7 days, 14 days, 21 days, 30 days, and 60 days respectively, and the fragrance of the contact lenses was subjected to sensory evaluation: 0 points, no detectable odor; 1 point, just detectable odor; 2 points, detectable obvious odor; 3 points, moderately strong odor; 4 points, very strong odor. Each evaluation was carried out by 3 professional personnel simultaneously, and the average value was rounded to an integer. The results are shown in Table 2.

[0077] Table 2 Sensory evaluation results of the fragrance of the contact lenses after soaking

[0078]

[0079] As can be seen from Table 2, the fragrance of the contact lenses of the present invention only began to decline after 14 days of soaking, and there was still a detectable odor even after soaking for 60 days, indicating that the present invention can sustain the fragrance. For Comparative Example 1, the essential oil microcapsules were not modified with a silane coupling agent, and the fragrance retention time of the obtained contact lenses was shorter than that of the present invention. There was no interaction between the essential oil microcapsules and the matrix material, and they were more likely to fall off.

[0080] The above are only the preferred embodiments of the present invention. It should be pointed out that for those of ordinary skill in the art, without departing from the principle of the present invention, several improvements and refinements can be made, and these improvements and refinements should also be regarded as the protection scope of the present invention.

Claims

1. A contact lens material with long-lasting fragrance retention, characterized in that, It contains raw materials in the following parts by mass: 50 - 70 parts of hydroxyethyl methacrylate, 10 - 30 parts of N-vinylpyrrolidone, 1 - 10 parts of acrylamide, 5 - 15 parts of glycidyl methacrylate, 10 - 20 parts of methacryloxypropyl tris(trimethylsiloxy)silane, 5 - 15 parts of crosslinking agent, 3 - 20 parts of modified essential oil microcapsules, 5 - 20 parts of photoinitiator.

2. The persistent fragrance-retaining contact lens material according to claim 1, wherein The crosslinking agent is ethylene glycol dimethacrylate and / or ethylene glycol diacrylate.

3. The persistent fragrance-retaining contact lens material according to claim 2, wherein The photoinitiator is one of photoinitiator TPO, photoinitiator 184, and photoinitiator 819.

4. The persistent fragrance-retaining contact lens material according to claim 3, wherein, The preparation method of the modified essential oil microcapsules is as follows: Using essential oil as the core material, mix the essential oil, emulsifier and gelatin aqueous solution to obtain an oil-water emulsion; heat the oil-water emulsion and then add gum arabic aqueous solution, and then adjust the pH to 3.5 - 4.5 to obtain an essential oil microcapsule solution; Mix the essential oil microcapsule solution and curing agent, and then adjust the pH to 10 - 11.5 for curing reaction; after the curing reaction, wash with water and dry to obtain essential oil microcapsules; Mix the essential oil microcapsules, silane coupling agent and water, and then adjust the pH to 7 - 7.5 for modification reaction to obtain modified essential oil microcapsules.

5. The persistent fragrance-retaining contact lens material according to claim 4, characterized in that, The essential oil is one or more of rose essential oil, lavender essential oil, tea tree essential oil, jasmine essential oil, basil essential oil, sandalwood essential oil, and chamomile essential oil.

6. The persistent fragrance-retaining contact lens material according to claim 4, characterized in that The dosage ratio of the essential oil, emulsifier, gelatin in the gelatin aqueous solution, and gum arabic in the gum arabic aqueous solution is 1 - 10 mL: 0.01 - 0.1 g: 5 - 20 g: 5 - 20 g; the concentrations of the gelatin aqueous solution and the gum arabic aqueous solution are independently 10 - 40 g / L.

7. A persistent fragrance-retaining contact lens material according to claim 4 or 6, characterized in that, The curing agent is glutaraldehyde; the silane coupling agent is KH-550 and / or KH-570.

8. The persistent fragrance-retaining contact lens material according to claim 7, characterized in that, The temperature of the modification reaction is 60 - 80 °C; the time of the modification reaction is 1 - 3 h.

9. A method for preparing a contact lens material with long-lasting fragrance retention according to any one of claims 1 to 8, characterized in that, It includes the following steps: Mix hydroxyethyl methacrylate, N-vinylpyrrolidone, acrylamide, glycidyl methacrylate, methacryloxypropyl tris(trimethylsiloxy)silane, crosslinking agent, photoinitiator, and modified essential oil microcapsules to obtain a raw material liquid; inject the raw material liquid into a contact lens mold and carry out photopolymerization under a protective atmosphere and UV light irradiation to obtain a contact lens material with long-lasting fragrance.

10. The preparation method of a long-lasting fragrance-retaining contact lens material according to claim 9, characterized in that, The wavelength of the UV light irradiation is 350 - 400 nm; the time of the photopolymerization is 10 - 90 min.

Images