CN117626685A - Method for dyeing functional contact lens - Google Patents

Method for dyeing functional contact lens Download PDF

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Publication number
CN117626685A
CN117626685A CN202310986012.5A CN202310986012A CN117626685A CN 117626685 A CN117626685 A CN 117626685A CN 202310986012 A CN202310986012 A CN 202310986012A CN 117626685 A CN117626685 A CN 117626685A
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China
Prior art keywords
lens
lens body
layer
body dry
weight percent
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CN202310986012.5A
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Chinese (zh)
Inventor
林文卿
李静芳
陈季晴
林晓君
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Vizionfocus Inc
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Vizionfocus Inc
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/52—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
    • D06P1/5264—Macromolecular compounds obtained otherwise than by reactions involving only unsaturated carbon-to-carbon bonds
    • D06P1/5285—Polyurethanes; Polyurea; Polyguanides
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/02—After-treatment
    • G—PHYSICS
    • G02—OPTICS
    • G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C7/00—Optical parts
    • G02C7/02—Lenses; Lens systems ; Methods of designing lenses
    • G02C7/04—Contact lenses for the eyes

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Ophthalmology & Optometry (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Eyeglasses (AREA)
  • Coloring (AREA)
  • Surface Treatment Of Optical Elements (AREA)

Abstract

A method of staining a functional contact lens comprising the steps of: a lens body dry sheet is provided comprising a hydrogel having a moisture content of 0-90%, a silicone hydrogel having a moisture content of 0-90%, or a combination thereof. A dual-sided polymethylether prepolymer is prepared and combined with a hydrophilic monomer to form a masking ring material, which is attached to the inner surface of the lens body dry piece to form a masking ring layer. And (3) dripping the coloring agent onto the inner surface, and heating and fixing the coloring agent after ultraviolet irradiation to form a coloring layer on the inner surface by using the shielding ring layer to surround the coloring agent. The lens body dry sheet is put into water for hydration, and the shielding ring layer is removed, so that the lens body wet sheet is obtained.

Description

Method for dyeing functional contact lens
Technical Field
The invention relates to a method for dyeing a contact lens, in particular to a method for precisely dyeing a functional contact lens.
Background
Since the early 1950 s of the invention, the contact lens was commercialized for 60 years so far, and the initial contact lens was made of hard materials (such as PMMA (Poly (methyl methacrylate), polymethyl methacrylate)), and the contact lens has a short wearable time and generates obvious foreign body discomfort due to the hard materials and poor oxygen permeability and hydrophilicity of the contact lens body. The invention of soft contact lenses in the 70 s can be an advanced innovation, which is made of a hydrogel material mainly comprising HEMA (2-Hydroxylethyl methacrylate, 2-hydroxyethyl methacrylate). Because the material has high water absorbability, forms soft and high water content after hydration, greatly improves wearing comfort, but has low oxygen permeability, can be worn for only 8 to 12 hours per day, and often has pathological changes of corneal hypoxic edema and neovascular hyperplasia after long-term wearing. The Taiwan ground small person is thick, the living space is relatively narrow, and the heavy rising pressure is added, so that the population with abnormal eyesight is rapidly increased, and the abnormal eyesight can be corrected by wearing glasses, but the inconvenience of daily life is caused by wearing the glasses, so that people can frequently utilize the contact lenses to correct the eyesight. The contact lens is worn directly on the cornea and the near edge area or scleral area of the eye, and is used for correcting vision or as a cornea shaping device; the development of products is gradually going from the earliest hard materials such as glass and PMMA to hydrophilic HEMA materials, and the development trend in the future is toward Silicon Hydrogel (Silicon Hydrogel) materials which can be worn for a long time.
The technology development is very advanced, and especially, blue light is released from 3C products such as LED lamps, tablet computers, televisions, smartphones and the like. When using the 3C product, the eyes will look directly at the blue light emitted by the screen. Blue light is the part of the visible light closest to ultraviolet light waves with stronger energy, the wavelength is between 380nm and 530nm, and the shorter wavelength can be focused in front of retina in advance, so that scattering is easy to cause, the eyes need to focus more forcefully and cannot relax, and the eye vision object image contrast and definition reduction are easy to cause for a long time, so that eye fatigue is increased. Furthermore, blue light is not absorbed by the cornea and the lens when entering the eye, and can penetrate the cornea and the lens to penetrate into the macula. If the eyes absorb too much blue light, symptoms such as stinging, photophobia and the like will occur in the early stage, the macula part will be inflamed and edematous for a long time, hidden knots may be formed in the center of the macula part, and once the hidden knots are broken to cause bleeding, central vision defect will be caused, and the eyes cannot see things clearly. Thus, with the change of modern life and the long-term stimulation of blue light, maculopathy, which is well developed in the elderly, tends to be decreased in the age group. Blue light resistance has become an important issue.
The commonly known blue-ray-resistant contact lens between workshops is a blue-ray-resistant and UV-resistant contact lens disclosed in taiwan patent No. M487455, which is composed of an upper layer lens, a middle layer lens and a lower layer lens, and the blue-ray-resistant coating agent in the upper layer lens is used for reducing the effect of penetrating blue rays into the contact lens to directly irradiate the eyes, wherein the blue-ray-resistant coating agent is not legally added in the safety permitted range of the American FDA of the contact lens at present, and has the doubt of damaging the eyes, and the efficiency of mass production is not limited except time consumption, labor consumption and cost consumption.
Ultraviolet light with a wavelength of 380-390nm is short and carried energy is high in summer, and long-time exposure of eyes to the sun can cause injuries such as maculopathy, cataract, retinopathy, keratitis (photodamage) and the like. Thus, selecting a suitable pair of sports sunglasses is one of the very important pieces of equipment for summer sports. The sunglasses are beneficial in that the sunglasses can prevent the excessive irritation of sunlight to eyes, filter ultraviolet rays and infrared rays, avoid injuring optic nerves, and are beneficial to improving visual contrast sensitivity, reducing reflected glare and increasing color contrast. For patients with photophobia of the eyes, or dry eye, early cataracts, and keratoconjunctival inflammation, sunglasses can help improve. Taiwan patent No. I554803 discloses a method for manufacturing a blue light-resistant contact lens with blue light resistance and ultraviolet resistance, which simplifies the manufacturing process and consistently produces the contact lens. One or more dyes of yellow, orange, red, green and the like are adjusted according to the color of the dye and the addition proportion, or a blue light absorber is added into hydrogel or a silicone monomer of the contact lens, then processes such as die casting molding or rotary die molding are carried out, after a dry piece is solidified and molded, the dry piece is thrown into a hydration tank for color fixation and hydration extraction, and the finished product of the blue light resistant contact lens is completed. However, this invention is not suitable for high concentrations of dye, since it also blocks the UV-visible light initiation reaction (wavelength 380-400 nm) from polymerization to form lenses.
The company previously invented (taiwan patent No. I697707) therefore proposes the following dyeing method and the contact lens prepared thereby. The special contact lens for sports adopts a unique light filtering technology, can block 90% of dazzling blue light and 95% of ultraviolet rays with different wavelengths, can effectively reduce the dazzling feeling of light, has the effects of reducing the deformation degree of objects and highlighting key objects (such as rapid sports balls) in sports, and can obtain clearer and brighter visual fields from any angle when people exercise. Compared with the traditional frame-type sports goggles, the contact lens special for sports is more comfortable and convenient to wear and safer, and people do not need to worry about blurred vision caused by sweating or accidental injury to eyes caused by violent collision during sports. The bright sun resumes vision faster than the transparent lens. Furthermore, the subject is able to obtain better visual recognition in bright sunlight than a transparent lens. The lens allows the subject to focus more quickly in bright and shadows than a transparent lens. From the foregoing, it is important that the dye/absorber be properly selected and the dyeing process be such that blue light resistant or sports sun contact lenses are produced.
However, after wearing the sports-specific contact lens, the iris of the eye is covered by the dyed dark-colored lens, and the eye color is changed to affect the appearance, so that partial persons repel the lens, but the invention really only plays the role in the whole pupil range, so that the masking ring design can be used for producing the optical zone (pupil zone) precisely dyed lens, and the dyeing process is fast, convenient and stable.
Disclosure of Invention
The invention provides a dyeing method of a functional contact lens, which can fix reactive dye on the surface part of a lens body, and is beneficial to improving the color uniformity of the appearance of the lens without affecting the color of the iris when a user wears the lens. In addition, the dyeing method of the functional contact lens can accurately control the dyeing range, the shape and the thickness of the dyeing layer.
The dyeing method of the functional contact lens provided by the invention comprises the following steps: a lens body dry sheet is provided comprising a hydrogel having a moisture content of 0-90%, a silicone hydrogel having a moisture content of 0-90%, or a combination thereof. A dual-sided polymethylether prepolymer is prepared and combined with a hydrophilic monomer to form a masking ring material, which is attached to the inner surface of the lens body dry piece to form a masking ring layer. And (3) dripping the coloring agent onto the inner surface, and heating and fixing the coloring agent after ultraviolet irradiation to form a coloring layer on the inner surface by using the shielding ring layer to surround the coloring agent. The lens body dry sheet is put into water for hydration, and the shielding ring layer is removed, so that the lens body wet sheet is obtained.
In an embodiment of the invention, the method for attaching the shielding ring material to the inner surface of the lens body dry plate to form the shielding ring layer includes attaching the shielding ring material to the inner surface of the lens body dry plate in a pad printing manner and photo-polymerization curing manner.
In an embodiment of the invention, the method for dyeing a functional contact lens further includes placing the wet lens body in a buffer solution and performing a sterilization step.
In an embodiment of the invention, the method for providing a dry lens body includes uv curing a hydrogel having a water content of 0-90%, a silicone hydrogel having a water content of 0-90%, or a combination thereof.
In an embodiment of the invention, the composition of the shielding ring material includes: about 30 to about 70 weight percent of a polymethylether prepolymer having a molecular weight of about 7,000 to about 20,000; about 30 to about 70 weight percent hydrophilic monomer hydrogel; and 0.1-2 weight percent of ultraviolet initiator.
In an embodiment of the invention, the above-mentioned coloring agent includes: 0.01-5 weight percent of one or more dyes; about 30 to 45 weight percent of a polymethylether prepolymer having a molecular weight of about 7,000 to 20,000;1-5 weight percent of one or more alkaline solutions; and 0.1-2 weight percent of ultraviolet initiator.
In one embodiment of the present invention, the method for forming the dyeing layer on the inner surface by heating and fixing the dyeing agent after ultraviolet irradiation comprises heating at 60-70 ℃ and fixing for 20-60 minutes.
In an embodiment of the invention, the method for hydrating the dry lens body in water includes immersing the dry lens body in an aqueous solution at 60-90 ℃ for 30-60 minutes.
In an embodiment of the invention, no crosslinking reaction occurs between the shielding ring layer and the lens body dry sheet.
In an embodiment of the invention, the region corresponding to the inner surface of the shielding ring layer is a part of a region corresponding to the iris of the user's eye, and the dyeing layer corresponds to the optical region of the pupil of the user's eye.
In the method for dyeing the functional contact lens, the shading ring material is attached to the inner surface of the lens body dry plate to form the shading ring layer. And then the coloring agent is dripped on the inner surface, the shielding ring layer surrounds the coloring agent, and the coloring agent is heated and fixed to form a coloring layer. Finally, the lens body dry sheet is hydrated in water, the shielding ring layer is removed, the dyeing range, the shape and the thickness of the dyeing layer can be accurately controlled by the shielding ring layer, and the color uniformity of the appearance of the lens can be improved without affecting the color of the iris when the user wears the lens.
The foregoing description is only an overview of the present invention, and is intended to be implemented in accordance with the teachings of the present invention, as well as the preferred embodiments thereof, together with the following detailed description of the invention, given by way of illustration only, together with the accompanying drawings.
Drawings
Fig. 1 is a flow chart of a method for staining a functional contact lens according to an embodiment of the invention.
Fig. 2A and 2B are schematic diagrams of a functional contact lens according to an embodiment of the present invention.
Detailed Description
Fig. 1 is a flow chart of a method for staining a functional contact lens according to an embodiment of the invention. Referring to fig. 1, the method for dyeing a functional contact lens of the present embodiment includes the following steps. Step S101: a lens body dry sheet is provided comprising a hydrogel having a moisture content of 0-90%, a silicone hydrogel having a moisture content of 0-90%, or a combination thereof. Step S102: a dual-sided polymethylether prepolymer is prepared and combined with a hydrophilic monomer to form a masking ring material, which is attached to the inner surface of the lens body dry piece to form a masking ring layer. Step S103: and (3) dripping the coloring agent onto the inner surface, and heating and fixing the coloring agent after ultraviolet irradiation to form a coloring layer on the inner surface by using the shielding ring layer to surround the coloring agent. Step S104: the lens body dry sheet is put into water for hydration, and the shielding ring layer is removed, so that the lens body wet sheet is obtained. Optionally, step S105 may be performed again: placing the wet lens of the lens body in the buffer solution, and sterilizing.
Preparation of the Material
Synthesis of polysiloxane prepolymers
The embodiment provides a preparation method of a dual-property silicon-containing prepolymer, which is obtained by using polydimethylsiloxane compound as a raw material to carry out isocyanic acid reaction and then using hydroxyl monomer to carry out end capping, and comprises the following steps: isocyanate reaction: taking a dihydroxy polydimethylsiloxane compound and an isocyanic acid compound as raw materials, and then adding a diluent to react in a medium-temperature environment to obtain a first product; adding a hydrophilic chain extender (chain extender) to the first product, and sequentially carrying out terminal hydroxylation reaction and then chain extension reaction to obtain a second product: the second product and the acrylic ester compound are continuously reacted for at least 12 hours at normal temperature to obtain the amphoteric silicon-containing prepolymer as a third product. Wherein the hydrophilic chain extender is mainly a polyhydric alcohol series, and comprises ethylene glycol, propylene glycol, 1, 4-butanediol, polyethylene glycol, polypropylene glycol diglycidyl ether and the like.
The detailed examples are described below: 50g of dimethylpolysiloxane containing a terminal hydroxyl group (trade name: KF-6001, commercially available from Yue chemical Co., ltd.) was taken, 10g of isophorone diisocyanate and 0.02g of dibutyltin dilaurate were added under nitrogen at room temperature, and after reacting for 12 hours, 30g of polyethylene glycol (weight average molecular weight: 600), 100g of tetrahydrofuran and 0.02g of dibutyltin dilaurate were added, and further reacting was carried out for 24 hours, and disappearance of the-NCO characteristic peak of about 2250cm-1 was confirmed by infrared absorption spectrum to complete the reaction. Then adding 10g of isophorone diisocyanate and 0.02g of dibutyltin dilaurate under the nitrogen environment at room temperature for reaction for 24 hours, then adding 12g of 2-methyl-2-acrylic acid-2, 3-dihydroxypropyl ester and 0.02g of dibutyltin dilaurate for reaction for 24 hours at 60 ℃, and confirming that the characteristic peak of-NCO about 2250cm < -1 > disappears by infrared absorption spectrum to finish the reaction, thereby obtaining polysiloxane prepolymer taking dimethylpolysiloxane as a main structure, wherein the weight average molecular weight is 11,000-13,000 (identified by gel permeation chromatography GPC).
Polymethyl ether prepolymer synthesis
The embodiment provides a preparation method of a bipolar polymethyl ether prepolymer, which is obtained by using polytetramethylene ether glycol PTMEG 1000 (Polytetramethylene Ether Glycol) as a raw material to carry out an isocyanic acid reaction and then using a hydroxy monomer to carry out end capping, and comprises the following steps: isocyanate reaction: taking a dihydroxy polydimethylsiloxane compound and an isocyanic acid compound as raw materials, and then adding a diluent to react in a medium-temperature environment to obtain a first product; adding a hydrophilic chain extender (chain extender) to the first product, and sequentially carrying out terminal hydroxylation reaction and then chain extension reaction to obtain a second product: the second product and the acrylic ester compound are continuously reacted for at least 12 hours at normal temperature to obtain the amphoteric polymethyl ether prepolymer as a third product. Wherein the hydrophilic chain extender is mainly a polyhydric alcohol series, and comprises ethylene glycol, propylene glycol, 1, 4-butanediol, polyethylene glycol, polypropylene glycol diglycidyl ether and the like.
The detailed examples are described below: 50g of polytetramethylene ether glycol PTMEG 1000 (Polytetramethylene Ether Glycol) is taken as a raw material, 10g of isophorone diisocyanate and 0.02g of dibutyltin dilaurate are added under the condition of nitrogen at room temperature, after 24 hours of reaction, 30g of polyethylene glycol (weight average molecular weight is 600), 100g of tetrahydrofuran and 0.02g of dibutyltin dilaurate are added, and after 24 hours of reaction, the disappearance of the-NCO characteristic peak of about 2250cm < -1 > is confirmed by infrared absorption spectrum, and the reaction is completed. Then, 10g of isophorone diisocyanate and 0.02g of dibutyltin dilaurate were added to react for 24 hours under a nitrogen atmosphere at room temperature, then, 12g of 2-methyl-2-acrylic acid-2, 3-dihydroxypropyl ester and 0.02g of dibutyltin dilaurate were added to react for 24 hours at 60 ℃, and the disappearance of the-NCO characteristic peak of about 2250cm-1 was confirmed by infrared absorption spectroscopy to complete the reaction, thereby obtaining a polymethyl ether prepolymer having a weight average molecular weight of about 7,000 to 20,000 (identified by GPC).
In this embodiment, the hydrophilic monomer may be, for example, 2-hydroxyethyl methacrylate (2-hydroxyethyl methacrylate, HEMA); n, N-dimethylacrylamide (N, N-dimethyl acrylamide, DMA), N-diethylacrylamide (N, N-diethyl acrylamide, DEA), N-vinylpyrrolidone (N-vinyl pyrrolidone, NVP), glycerol methacrylate (glycerol methacrylate, GMA), polyethylene glycol methyl methacrylate (polyethylene glycol methacrylate mono methyl ether) of molecular weight 400, or a combination thereof, but not limited thereto.
In this embodiment, the ultraviolet initiator is favorable for UV light curing, and the content of the ultraviolet initiator may be 0.1 to 2 weight percent. The ultraviolet light initiator may be, but is not limited to, trade name1173, abbreviated as I-1173, and trade name +.>819, abbreviated as I-819. In addition, the ultraviolet initiator may be used singly or in combination of two or more kinds(two types are included). The hydrophilic copolymer composition may optionally further comprise other additives to meet practical requirements, and usable additives include, but are not limited to, UV absorbers, leveling agents, and the like.
According to an embodiment of the present invention, the derivative silicon-containing monomer comprises 30 to 80 weight percent of polysiloxane prepolymer and 10 to 50 weight percent of repeating units of hydrophilic monomer based on the total weight, and the ultraviolet light blocking monomer is a monomer having benzotriazole. According to the embodiment of the invention, the ultraviolet light blocking monomer accounts for 0.1-1.5 weight percent of the total weight of the silicone gel composition; in addition, the ultraviolet initiator accounts for 0.1-2 weight percent of the total weight.
The polysiloxane prepolymer is added and stirred for about 0.5 hour to 1.5 hours, and then the hydrophilic monomer/initiator and the ultraviolet light blocking monomer can be added together for continuous stirring for about 0.5 hour to 1.5 hours, so that the silicone gel composition of the invention can be obtained. In one aspect of the present invention, a method for manufacturing the silicone-hydrogel lens is provided. Injecting the silicone gum composition of any of the above embodiments or examples into a mold for producing a lens; and (3) carrying out ultraviolet curing treatment on the silicone gel composition in the mold for 30-60 minutes, and carrying out crosslinking curing reaction on the silicone gel composition to form the silicone gel lens.
The preparation of the hydrogel material can be carried out by adding hydrophilic monomer/initiator and ultraviolet blocking monomer for stirring for 0.5-1.5 hours, wherein the content of the repeating unit of hydrophilic monomer is 95-99 wt%, and the ultraviolet blocking monomer is benzotriazole. According to the embodiment of the invention, the ultraviolet light blocking monomer accounts for 0.1-1.5 weight percent of the total weight of the silicone gel composition; in addition, the ultraviolet initiator accounts for 0.1-2 weight percent of the total weight. The hydrogel composition of the present invention can be obtained.
Preparation of hydrogel lens body dry sheet
In one aspect of the present invention, a method for producing a hydrogel lens is provided. Injecting the hydrogel of any of the above embodiments into a mold for producing a lens; and (3) carrying out ultraviolet curing treatment on the hydrogel composition in the mould for 30-60 minutes, and carrying out crosslinking curing reaction on the hydrogel composition to form the lens body dry sheet. The hydrocolloid, or hydrogel, may comprise any of the known hydrocolloid components such as: hydroxyethyl methacrylate (HEMA), hydroxypropyl methacrylate (Hydroxy propyl methacrylate, HPMA), methyl methacrylate (acrylic monomer) (Methyl methacrylate, MMA), glycerol methacrylate (Glyceryl methacrylate, GMA), N-vinyl pyrrolidone (N-vinyl pyrrolidone, NVP), N '-dimethylaniline (N, N' -dimethylacrylamide, DMA), N '-diethylacrylamide (N, N' -dimethylacrylamide), N-isopropylacrylamide (N-isopropenylacrylamide), 2-hydroxyethyl acrylic acid (2-hydroxyethyl acrylate), vinyl acetate (vinyl acetate), N-acryloylmorpholine (N-acryloymorphholine), 2-dimethylaminoethyl acrylic acid (2-dimethlaminoethyl acrylate), or a combination selected from the group consisting of them, but not limited thereto.
Shadow ring material and application
The shadow ring layer of the present embodiment comprises a shadow ring material for pad printing onto the inner surface of the lens body dry plate, and the "shadow ring layer" is meant to resemble a concentric ring design, leaving the hollow area in the middle for the subsequent dyeing process. Specifically, the region of the inner surface of the masking ring layer corresponds to a portion of the region corresponding to the iris of the user's eye, and the dyed layer corresponds to a hollow region disposed in the middle of the inner surface, which corresponds to the optical zone of the pupil of the user's eye. Wherein the masking ring material comprises about 30 to 70 weight percent of a polymethylether prepolymer having a molecular weight of about 7,000 to 20,000, about 30 to 70 weight percent of a lens material comprising a hydrophilic monomer hydrogel, and 0.1 to 2 weight percent of an ultraviolet initiator, thereby forming a masking ring material composition.
Shadow ring material and process for using the same
In this embodiment, a preferred method of preparing colored lenses is by Pad-print (Pad-print) as follows. First a metal plate is provided, preferably made of steel or more preferably stainless steel, covered with a photoresist material which becomes insoluble in water once cured. The pattern and inner and outer diameters of the shadow ring are selected or designed and then reduced to the desired dimensions using any of a number of techniques (e.g., photographic techniques), placed onto a metal plate, and the photoresist cured. The conditions for performing the pattern etching are known to those skilled in the art. After patterning, the metal plate is then washed with an aqueous solution, and the resulting image is etched onto the metal plate to a suitable depth, e.g., about 10-20 microns, with an inner diameter of 4-8mm and an outer diameter of 6-14mm, so that the shadow ring width is about 2-10mm.
The process comprises depositing a masking ring material onto the filling recesses of the pattern, scraping off the excess material with a doctor blade, extruding the masking ring material with a silica gel head having a suitable geometry and varying hardness (generally about 10Shore A durometer units) to adhere the image on the metal plate, extruding and transferring the masking ring material onto the inner surface of the lens body dry sheet, and polymerizing the transferred masking ring with ultraviolet light to completely cure the masking ring material attached to the inner surface of the lens body dry sheet. It should be understood that the shadow ring layer is attached to the inner surface of the lens body dry sheet, but no cross-linking reaction occurs between the shadow ring layer and the lens body dry sheet. Thus, the masking ring layer may be removed by subsequent additional processing, such as not having a masking ring layer in the final lens body product.
Dye material and application
In this embodiment, the stain comprises one or more dyes, one or more alkaline solutions. The dye is, for example, an organic dye, including but not limited to, reactive dye, xylyl blue dye, xylyl green dye, carbazole violet, vat orange #1, and the like, and combinations thereof. Specifically, the colorant comprises 0.01 to 5 weight percent of one or more dyes, about 30 to 45 weight percent of a polymethylether prepolymer, a molecular weight of about 7,000 to 20,000, 1 to 5 weight percent of one or more alkaline solutions, and 0.1 to 2 weight percent of an ultraviolet initiator. The alkaline solution may be any alkaline compound such as NaOH, KOH, naCO, naHCO3, triethylamine (TEA) or Ethanolamine (ETA) and the like. The dyeing agent is dripped on the inner surface of the lens body dry sheet, and the inner diameter of the shielding ring layer is dripped, after ultraviolet polymerization reaction is carried out for 1-10 minutes, the dyeing agent forms gel state, and then the color is continuously fixed for 20-60 minutes by heating at 60-70 ℃. The Reactive dye is azo Reactive dye, is nontoxic, meets the preparation requirements of contact lenses, and is regulated by the United states Food and Drug Administration (FDA), such as, but not limited to, reactive Blue 21, reactive Blue No 19, reactive Yellow 15, reactive Orange 78, reactive Black 5, C.I. Reactive Yellow 86, C.I. Reactive Red 11, C.I. Reactive Red 180, C.I. Reactive Blue163, and the like. The reactive dye is also a water-soluble dye with active groups on the molecular structure, and can be subjected to covalent bond or hydrogen bond combination with hydroxyl groups, amino groups and carboxyl hydroxyl groups on the contact lens material. In the case of vinyl sulfone reactive dyes, the active groups are vinyl sulfone groups (D-so2ch=ch2) or sulfate esters of β -hydroxyethylsulfonyl groups. During dyeing, beta-hydroxyethyl sulfonyl sulfate is subjected to elimination reaction in an alkaline medium to generate vinyl sulfonyl, and then is subjected to nucleophilic addition reaction with polymer hydroxyl or amino to form covalent bond combination. The reactive dye composition solution may comprise one or more reactive dyes.
The dyed lens body dry sheet is hydrated in water, preferably RO water. Specifically, the dry sheet can fully absorb water and swell after being soaked in aqueous solution at 60-90 ℃ for 30-60 minutes, and the hydrogel or dye residues which do not undergo the crosslinking curing reaction are removed. At this time, since the shielding ring layer is only attached to the surface, the shielding ring layer and the lens body dry sheet do not undergo a crosslinking reaction, and are removed together, so that a functional contact lens wet sheet which is stable and concentrated in the optical zone dyeing can be obtained. Finally, the functional contact lens wet sheet is optionally sterilized at high temperature and high pressure in a buffer solution of phosphoric acid or borate water with pH value of 7.1-7.5.
The reactive dye can form covalent bonds with hydroxyl, amino and carboxyl hydroxyl groups of the lens body to fix the lens body. The alkali-before-dyeing mode is also helpful for improving the fixation rate of the reactive dye and reducing the release of the reactive dye. Reactive dyes bonded to the lens absorb light in a specific wavelength range. Preferably, the specific wavelength range is in the blue wavelength range, so that when visible light is incident on the dyed lens, the light with the specific wavelength is absorbed and shielded by the lens, and the amount of penetrating the lens is reduced.
It should be noted that the portion of the lens body to which the reactive dye is affixed is primarily the surface portion, although the reactive dye enters the lens body from the lens surface. The reactive dye preferably does not penetrate into the interior of the lens body. The tinted layers may have different thicknesses based on the extent to which the reactive dye enters the lens body. The degree of the reactive dye entering the lens body and the thickness of the dyeing layer can be adjusted by the concentration of the ionic salt solution, the osmotic pressure, the concentration of the reactive dye and the alkali concentration. The thickness of the dyed layer may be determined based on the type of reactive dye and the light absorption effect to be achieved.
Fig. 2A and 2B are schematic diagrams of a functional contact lens according to an embodiment of the present invention. Referring to fig. 2A and 2B, a photo taken at 20X magnification under an optical microscope is shown, wherein the colored region is a region of the dye layer, and the region corresponds to an optical region of the pupil of the user's eye. As can be seen from fig. 2A and 2B, the contour between the edge of the dyeing layer and the inner surface of the lens body dry sheet is clear, and there is no edge blurring phenomenon, because in the dyeing method of the functional contact lens according to the embodiment of the present invention, the shielding ring layer (not shown) is formed by attaching the shielding ring material to the inner surface of the lens body dry sheet. And then the coloring agent is dripped on the inner surface, the shielding ring layer surrounds the coloring agent, and the coloring agent is heated and fixed to form a coloring layer. Finally, the lens body dry sheet is hydrated in water, the shielding ring layer is removed, the size (the dyeing layer in fig. 2A is smaller, the dyeing layer in fig. 2B is larger), the shape, the color, the thickness of the dyeing layer and the like of the region of the dyeing layer can be accurately controlled by the shielding ring layer, and the lens body dry sheet is beneficial to improving the color uniformity of the appearance of the lens without affecting the color presented by the iris when a user wears the lens.
In addition, compared with the dyeing method in the prior art, the area size of the dyeing layer is generally difficult to precisely control when the wet piece is dyed, and the whole lens body is easy to dye. The dry-sheet dyeing requires the matching of dies, and when the size, shape, color or thickness of the dyed layer area is to be adjusted, a new die or holder must be replaced to achieve the desired effect, which is too costly and difficult to mass produce. The functional contact lens manufactured by the dyeing method of the functional contact lens provided by the embodiment of the invention can accurately control the size, the shape, the color, the thickness and the like of the area of the dyeing layer by simply adjusting the shielding ring layer, so that the manufacturing process is simple, the cost is saved, and the method can be applied to large-scale mass production.
While the invention has been described with respect to preferred embodiments, it will be understood by those skilled in the art that various changes and modifications may be made without departing from the spirit and scope of the invention, and that any such changes and modifications as described in the above embodiments are intended to be within the scope of the invention.

Claims (10)

1. A method of tinting a functional contact lens comprising:
providing a lens body dry sheet comprising a hydrogel having a moisture content of 0-90%, a silicone hydrogel having a moisture content of 0-90%, or a combination thereof;
preparing a dual-poly methyl ether prepolymer and combining the dual-poly methyl ether prepolymer with a hydrophilic monomer to form a shielding ring material, and attaching the shielding ring material on an inner surface of the lens body dry sheet to form a shielding ring layer;
dropping a coloring agent onto the inner surface, wherein the shielding ring layer surrounds the coloring agent, and the coloring agent is subjected to heating fixation after being irradiated by ultraviolet light so as to form a coloring layer on the inner surface; and
the lens body dry sheet is put into water for hydration, and the shielding ring layer is removed, so that a lens body wet sheet is obtained.
2. The method of claim 1, wherein attaching the masking ring material to the inner surface of the lens body dry sheet to form the masking ring layer comprises pad printing and photo-polymerization curing the masking ring material to the inner surface of the lens body dry sheet.
3. The method of claim 1, further comprising placing the wet lens in a buffer and sterilizing.
4. The method of claim 1, wherein providing the lens body dry sheet comprises uv curing a hydrogel having a moisture content of 0-90%, a silicone hydrogel having a moisture content of 0-90%, or a combination thereof.
5. The method of tinting a functional contact lens of claim 1 wherein the composition of the masking ring material comprises:
30-70 weight percent of a polymethylether prepolymer having a molecular weight of 7,000-20,000;
30-70 weight percent of hydrophilic monomer hydrogel; and
0.1-2 weight percent of ultraviolet initiator.
6. The method of staining a functional contact lens of claim 1, wherein the stain comprises:
0.01-5 weight percent of one or more dyes;
30-45 weight percent of a polymethylether prepolymer having a molecular weight of 7,000-20,000;
1-5 weight percent of one or more alkaline solutions; and
0.1-2 weight percent of ultraviolet initiator.
7. The method of dyeing a functional contact lens according to claim 1, wherein the dyeing agent is heat-fixed after being irradiated with the ultraviolet light to form the dyed layer on the inner surface comprises heating at 60 to 70 ℃ and fixing for 20 to 60 minutes.
8. The method of claim 1, wherein hydrating the lens body dry lens in water comprises immersing the lens body dry lens in an aqueous solution at 60-90 ℃ for 30-60 minutes.
9. The method of claim 1, wherein no cross-linking reaction occurs between the masking ring layer and the lens body dry piece.
10. The method of claim 1, wherein the area of the inner surface of the masking ring layer corresponds to a portion of an area corresponding to an iris of a user's eye, and the layer corresponds to an optical area of a pupil of the user's eye.
CN202310986012.5A 2022-08-29 2023-08-07 Method for dyeing functional contact lens Pending CN117626685A (en)

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US7431454B2 (en) * 2006-03-27 2008-10-07 Johnson & Johnson Vision Care, Inc. Methods for designing tinted contact lenses
CN103483507A (en) * 2013-10-14 2014-01-01 海昌隐形眼镜有限公司 Soft hydrophilic contact lens material and preparation method thereof
US11072137B2 (en) * 2018-10-15 2021-07-27 Argos Vision Inc. Methods of forming contact lenses to reduce the transmittance of light
TWI697707B (en) * 2019-07-09 2020-07-01 望隼科技股份有限公司 Functional contact lens and method for dyeing functional contact lens
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