CN117666168A - Contact lens with anti-fouling coating and preparation method thereof - Google Patents

Contact lens with anti-fouling coating and preparation method thereof Download PDF

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Publication number
CN117666168A
CN117666168A CN202311685223.1A CN202311685223A CN117666168A CN 117666168 A CN117666168 A CN 117666168A CN 202311685223 A CN202311685223 A CN 202311685223A CN 117666168 A CN117666168 A CN 117666168A
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China
Prior art keywords
contact lens
phosphorylcholine
group
glycerol
small molecular
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CN202311685223.1A
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Chinese (zh)
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张弢
程远
徐世伟
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Xishan Institute Of Applied Biotechnology Nanjing University Wuxi
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Xishan Institute Of Applied Biotechnology Nanjing University Wuxi
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Priority to CN202311685223.1A priority Critical patent/CN117666168A/en
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/12—Chemical modification
    • C08J7/16—Chemical modification with polymerisable compounds
    • C08J7/18—Chemical modification with polymerisable compounds using wave energy or particle radiation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/12—Chemical modification
    • C08J7/14—Chemical modification with acids, their salts or anhydrides
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
    • G02B1/18—Coatings for keeping optical surfaces clean, e.g. hydrophobic or photo-catalytic films
    • 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
    • G02C7/049—Contact lenses having special fitting or structural features achieved by special materials or material structures
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
    • C08J2333/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
    • C08J2333/14—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Optics & Photonics (AREA)
  • Ophthalmology & Optometry (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Eyeglasses (AREA)

Abstract

The invention discloses a contact lens with an anti-fouling coating, which is characterized in that a small molecular monomer containing a phosphorylcholine group is grafted on the surface of the contact lens through an unsaturated acid ester group. Its preparing process is also disclosed. The invention carries out surface treatment on the contact lens, and covalent grafts the molecule with phosphorylcholine structure through chemical reaction, so that the contact lens has the properties of anti-pollution, anti-protein, anti-bacterial adhesion and the like, reduces the uncomfortable feeling caused by protein or bacterial adhesion in the use process, prevents ophthalmic diseases and improves the application safety.

Description

Contact lens with anti-fouling coating and preparation method thereof
Technical Field
The invention relates to a contact lens with an anti-fouling coating and a preparation method thereof, belonging to the technical field of medical appliances.
Background
Contact lenses, also known as soft lenses, contact lenses, refer to lenses that are worn on the cornea of an eyeball to correct vision or protect the eye, and also include products such as pupils. The contact lens not only brings great improvement to patients with ametropia such as myopia, hyperopia, astigmatism and the like in aspects of appearance and convenience, but also plays a special role in controlling the development of teenagers' myopia and astigmatism, treating special eye diseases and the like. Among these, wettability and oxygen permeability are two important indicators of contact lenses. Wettability is understood to mean the degree of surface hydrophilicity to which a contact lens corrects vision to a normal level by wrapping air between the eyeball and the cornea to isolate external stimuli. The wettability of the surface of the contact lens is large, and the formed tear film is uniform and stable. Uniform and stable tear film is a necessary condition for comfortable wear, ideal vision and prevention of deposit formation. However, due to the isolating effect of the contact lens, the cornea is unable to obtain a normal oxygen supply, making it vulnerable to hypoxia. Oxygen permeability in maintaining normal physiological activities of the cornea, the permeability of oxygen molecules and some other ions, molecules, is critical. Oxygen permeability is one of the most important properties of contact lens materials. The cornea is avascular to provide the oxygen required for normal metabolism, and therefore the cornea must obtain a large portion of the required oxygen from the tear film. Of the oxygen required for the cornea, 80% comes from air, 15% from limbal vascular network, 5% from aqueous humor. Depending on the condition of corneal hypoxia, it may cause various manifestations such as corneal edema, vision deterioration, nerve ending sensation deterioration, limbal vascular proliferation, and corneal epithelial and endothelial function deterioration. Long-term corneal hypoxia can lead to problems such as corneal surface cell death, corneal congestion, vision deterioration, etc.
On the other hand, the tear fluid of the human body contains a lot of proteins and the like, and when the contact lens is worn, the tear protein secretion in the tear fluid increases, and the tear protein easily adheres to the surface of the lens to block the ventilation holes in the lens, thereby reducing the oxygen content of the lens. In addition, prolonged contact lens wear is also prone to eye infections. This is mainly because contact lenses come into contact with the eyes during wear, which in turn leads to the proliferation of pathogenic bacteria. Although modern contact lenses are made of materials that have some antimicrobial properties, the risk of infection is increased by prolonged wear or poor personal hygiene practices. Symptoms of eye infection include redness of the eye, pain of the eye, increased secretions, etc., and in severe cases may cause corneal inflammation and even permanent vision impairment. Aiming at the surface antibacterial scheme of the contact lens, various products such as nano silver-containing contact lens care solution of MIOTTICA company in Korea are available on the market, and the effect of inhibiting bacteria is achieved through the effect of nano silver directly entering thalli and oxidative metabolism enzyme and the effect of glycoprotein on bacterial cell walls and DNA in cells. Because the nano silver has super-strong permeability, the nano silver can quickly permeate into the skin for sterilization by 2mm, and high requirements are put on the safety of the product and technology. In addition, the multifunctional care solution (Menicare Plus) of Menicon corporation (Menicon) contains hypromellose component, which can improve the wettability of contact lens, and the polyurethane biguanide component can provide antibacterial function. The above-mentioned technology all need to soak the contact lens in the nursing liquid, it is difficult to provide the long-acting antibacterial protection in the course of wearing the contact lens. Based on this, there is a great deal of interest in antimicrobial anti-adhesion coatings for contact lenses.
Chinese patent No. CN105622741a discloses a method for preparing a composition for antimicrobial coating on the surface of a contact lens, which comprises preparing hyaluronic acid modified by antimicrobial peptide by chemical coupling, and then chemically crosslinking 1, 4-butanediol diglycidyl ether with the contact lens to obtain a contact lens with a firm antimicrobial coating on the surface; chinese patent No. CN110453193a discloses a method for preparing a film on a contact lens by using a plasma-assisted chemical vapor deposition method, wherein the surface of a substrate of the contact lens is subjected to plasma modification treatment to form a functional group with a hydrophilic function on the surface of the substrate, and then the contact lens with a polyethylene glycol methacrylate and an N-vinyl-2-pyrrolidone film on the surface is obtained by using a plasma-assisted chemical vapor deposition method based on a corresponding monomer, so that the contact lens has better hydrophilic and anti-fouling capabilities; similarly, chinese patent No. CN111055520a discloses a method for coating hydrophilic surface of contact lens, wherein polyvinyl alcohol, polyvinylpyrrolidone, polyethylene glycol and their compositions are coated on the surface of contact lens by two-step hydration procedure to obtain contact lens with hydrophilic and protein and lipid resistant coating; the Chinese patent No. 110655817A discloses a multifunctional coating with enhanced stability and long-acting antibacterial property, and preparation and application thereof, wherein the multifunctional coating is formed by coordination chelation of phenolic hydroxyl groups and inorganic metal ions on poly (carboxylic betaine-dopamine) copolymer in water, and the sterilization property, antibacterial property and protein adhesion property of betaine components are utilized to improve the performances of eye medical devices such as contact lenses, intraocular lenses and the like; similarly, chinese patent No. 101735096a discloses a betaine ester derivative, an organosilicon material, and a preparation method and use thereof, wherein the material contains a copolymer of the betaine ester derivative and a vinyl-containing organosilicon monomer, and has good oxygen permeability, light permeability, hydrophilicity and anti-fouling capability; chinese patent No. 111566517a discloses a contact lens having a lubricating coating thereon, the hydrophilic copolymer of which comprises repeating units containing an aryl boronate group each having a boric acid group, covalently linked to the hydrogel lens body through a cyclic borate bond, resulting in a contact lens having surface lubricity. None of the above patents relate to the phosphorylcholine structure.
Chinese patent No. 111295601a discloses a method of manufacturing a coated contact lens comprising a first coating polymer containing acid groups and a second coating layer bonded by covalent bonds between nitrogen atoms of second amine groups on the first coating polymer and amine reactive groups of the second coating polymer. The second coating polymer may comprise 2-Methacryloxyethyl Phosphorylcholine (MPC), betaine, and the like. Resulting in coated contact lenses exhibiting reduced adhesion, increased wettability, increased lubricity, and/or increased lipid resistance; the Chinese patent No. 109796616B discloses a bionic polymer and a method for preparing a durable double bionic polymer coating and application thereof, wherein the bionic polymer with side groups containing zwitterionic groups (including phosphorylcholine, betaine and the like), amino hydrochloride and quaternary ammonium cationic groups is prepared into a polymer-dopamine weak alkaline aqueous solution, and different base materials are placed in the polymer-dopamine weak alkaline aqueous solution, and the durable double bionic polymer coating is obtained through leaching and airing. The obtained coating has high light transmittance, good hydrophilicity, strong base material universality, excellent coating stability and good biomolecule adhesion resistance and antibacterial property; chinese patent No. CN112074266a discloses a class of lipid-based coating compositions and objects with lipid-based coatings, which relate to the use of lipid vesicles of phospholipids with phosphatidylcholine groups and pegylated phospholipid compositions in coating devices such as contact lenses, catheters or medical implants; chinese patent No. 106526889B discloses a contact lens formed with a multi-coating layer composed of hydrophilic hydroxyethyl methacrylate and wettable phosphorylcholine and a method for manufacturing the same, in which a biocompatible multi-coating layer composed of hydrophilic hydroxyethyl methacrylate and wettable phosphorylcholine is formed on the front and rear surfaces of a printing layer, providing comfortable and moist wear feeling for 12 hours or more, and preventing proteins and foreign substances by a moisture film formed on the surface of the lens. In the above patents, the phosphorylcholine groups are copolymers or mixtures with other components, and are not formed by covalent grafting of small molecule monomers such as 2-Methacryloyloxyethyl Phosphorylcholine (MPC) or the like directly through chemical modification on the surface of the contact lens.
Disclosure of Invention
The object of the present invention is to obtain contact lenses with a phosphorylcholine coating.
The aim of the invention is achieved by the following technical scheme:
a contact lens with an anti-fouling coating is characterized in that a small molecular monomer containing a phosphorylcholine group is grafted on the surface of the contact lens through an unsaturated acid ester group.
Preferably, the small molecular monomer containing phosphorylcholine groups refers to a compound with one end group of phosphatidylcholine and an unsaturated carbon-carbon double bond structure in the molecule.
Preferably, the small molecular monomer containing a phosphorylcholine group means 2-methacryloyloxyethyl phosphorylcholine, 1, 2-dilauroyl-glycerol-3-phosphorylcholine, 1, 2-dimyristoyl-glycerol-3-phosphorylcholine, 1, 2-dipalmitoyl-glycerol-3-phosphorylcholine, 1, 2-dioleoyl-glycerol 3-phosphorylcholine, 1-palmitoyl-2-oleoyl-3-phosphorylcholine, 1, 2-sinapis-glycerol-3-phosphorylcholine, 1, 2-bis (10, 12-ditridecyl) -3-phosphorylcholine or 1-palmitoyl-2- (10, 12-ditridecyl) -glycerol-3-phosphorylcholine.
Preferably, the unsaturated acid ester group is derived from acrylic anhydride or methacrylic anhydride.
The invention also discloses a preparation method of the contact lens, which comprises the following steps:
(1) Immersing the contact lens in an aqueous suspension of a reagent containing unsaturated anhydride groups, adding an alkaline pH regulator to regulate the pH, and performing a grafting reaction to obtain the contact lens with unsaturated anhydride on the surface;
(2) Immersing the contact lens obtained in the step (1) in an aqueous solution of a small molecular monomer containing a phosphorylcholine group, and carrying out grafting reaction under the irradiation of an ultraviolet lamp to obtain the contact lens with the surface covalently modified with the phosphorylcholine group.
Preferably, the volume ratio of the reagent containing unsaturated anhydride groups to water in the aqueous suspension of the reagent containing unsaturated anhydride groups in the step (1) is 1:100-1:10.
Preferably, sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate is added in the step (1) as a pH regulator, and the addition concentration of the pH regulator is 0.1-5 wt%.
Preferably, the reaction temperature in the step (1) is 4-60 ℃ and the reaction time is 8-24 h.
Preferably, in the step (2), the wavelength of the ultraviolet lamp is 200-400 nm, the distance between the contact lens and the liquid level is 0.1-2 cm, the height between the ultraviolet light source and the liquid level is 0.5-2 cm, and the illumination power is 1-60W; the reaction temperature is 4-60 ℃ and the reaction time is 1-5 min.
Preferably, the concentration of the small molecular monomer containing the phosphorylcholine group in the aqueous solution of the small molecular monomer containing the phosphorylcholine group is 2-20wt%.
The invention provides a simple and efficient method for modifying an anti-fouling coating of a contact lens. Specifically, the unsaturated anhydride of the contact lens is modified to obtain the contact lens with the surface containing carbon-carbon double bond groups. The small molecular monomer containing carbon-carbon double bond and phosphorylcholine group is subjected to covalent reaction with the carbon-carbon double bond group modified on the surface of the contact lens under ultraviolet light to obtain the contact lens with the surface grafted with the phosphorylcholine group, so that the contact lens has the performances of surface hydrophilicity, dirt resistance, protein resistance, bacterial adhesion resistance and the like, discomfort caused by tear protein or bacterial adhesion in the use process is reduced, ophthalmic diseases are prevented, and wearing comfort and the use effect of products are improved.
Drawings
FIG. 1 is a chemical structure diagram of 2-Methacryloyloxyethyl Phosphorylcholine (MPC).
Fig. 2 is a photograph of a typical hand-held ultraviolet lamp.
Fig. 3 is a schematic illustration of a phosphorylcholine coating process for contact lenses.
FIG. 4 is a schematic view of the structure of a contact lens prepared in example 1.
The specific implementation method comprises the following steps:
the present invention is further illustrated by the following examples, which are not intended to limit the scope of the invention in any way.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs, and the terms used herein in this description of this invention are for the purpose of describing particular embodiments only and are not intended to be limiting of this invention.
The materials or instruments used in the following examples, if not specifically described, were available from conventional commercial sources.
Example 1
Taking a complete contact lens, wherein the contact lens is made of a silicon-containing methyl methacrylate and hydroxyethyl methacrylate copolymer, repeatedly ultrasonically cleaning the contact lens by deionized water for three times, and then soaking the contact lens in pure water overnight (40 ℃ for 12 h); the contact lens was taken out and immersed in 10mL of an aqueous suspension of methacrylic anhydride (volume concentration: 10%), an aqueous solution of sodium hydroxide was added dropwise as a pH adjuster (1 wt%), the dropping speed was 0.3mL/min, and the grafting reaction was carried out by treating at 30 ℃ for 8 hours, followed by taking out the contact lens and repeatedly rinsing with pure water 3 times. The contact lens is placed in 10wt% aqueous solution of 2-methacryloyloxyethyl phosphorylcholine (MPC, structure shown in FIG. 1) and reacted at room temperature for 5min under irradiation of ultraviolet light (preferably with a wavelength of 256nm, a power of 30W, and an appearance shown in FIG. 2). The contact lens was then removed and rinsed 3 times with pure water to finally obtain a contact lens with a phosphorylcholine coating, the surface of which, as measured by the static water contact angle, had a water contact angle of less than 90 °, and which showed hydrophilicity. The reaction process is shown in FIG. 3, and the structure of the contact lens is shown in FIG. 4.
When the contact lens with the phosphorylcholine coating is used outside the cornea of a human body, the phosphorylcholine structure modified on the surface of the contact lens is contacted with tear or body fluid, so that the contact lens can play roles in resisting protein and bacterial adhesion, and further has good anti-fouling and moisturizing effects. Meanwhile, the phosphorylcholine structure is modified on the surface of the contact lens in a covalent bond mode, and in the long-term service process, the effects of resisting protein and bacterial adhesion can be continuously exerted, the protein and bacterial adhesion and pollution in the use process are reduced, and the wettability and the comfort of the product are correspondingly improved.
The above embodiments are only for illustrating the technical concept and features of the present invention, and are intended to enable those skilled in the art to understand the present invention and to implement the same, but are not intended to limit the scope of the present invention, and all equivalent changes or modifications made according to the spirit of the present invention should be included in the scope of the present invention.

Claims (10)

1. A contact lens with an anti-fouling coating is characterized in that a small molecular monomer containing a phosphorylcholine group is grafted on the surface of the contact lens through an unsaturated acid ester group.
2. The contact lens of claim 1, wherein the small molecular monomer containing phosphorylcholine group is a compound having a phosphatidylcholine group as one end group and an unsaturated carbon-carbon double bond structure in a molecule.
3. The contact lens of claim 1, wherein the small molecular monomer containing a phosphorylcholine group is 2-methacryloxyethyl phosphorylcholine, 1, 2-dilauroyl-glycerol-3-phosphorylcholine, 1, 2-dimyristoyl-glycerol-3-phosphorylcholine, 1, 2-dipalmitoyl-glycerol-3-phosphorylcholine, 1, 2-dioleoyl-glycerol-3-phosphorylcholine, 1-palmitoyl-2-oleoyl-3-phosphorylcholine, 1, 2-sinapis noyl-glycerol-3-phosphorylcholine, 1, 2-bis (10, 12-ditridecanoyl) -3-phosphorylcholine, or 1-palmitoyl-2- (10, 12-ditridecanoyl) -glycerol-3-phosphorylcholine.
4. The contact lens of claim 1, wherein the unsaturated acid ester group is derived from acrylic anhydride or methacrylic anhydride.
5. A method for producing a contact lens according to any one of claims 1 to 4, characterized in that the steps thereof comprise:
(1) Immersing the contact lens in an aqueous suspension of a reagent containing unsaturated anhydride groups, adjusting the pH to 7.5-8.5, and performing grafting reaction to obtain the contact lens with unsaturated anhydride on the surface;
(2) Immersing the contact lens obtained in the step (1) in an aqueous solution of a small molecular monomer containing a phosphorylcholine group, and carrying out grafting reaction under the irradiation of an ultraviolet lamp to obtain the contact lens with the surface covalently modified with the phosphorylcholine group.
6. The process according to claim 5, wherein the volume ratio of the unsaturated acid anhydride group-containing agent to water in the aqueous suspension of the unsaturated acid anhydride group-containing agent in the step (1) is 1:100 to 1:10.
7. The preparation method according to claim 5, wherein the step (1) comprises adding sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate as a pH adjustor to adjust pH, and the concentration of the pH adjustor is 0.1 to 5wt%.
8. The process according to claim 5, wherein the reaction temperature in the step (1) is 4 to 60℃and the reaction time is 8 to 24 hours.
9. The preparation method according to claim 5, wherein in the step (2), the wavelength of the ultraviolet lamp is 200-400 nm, the distance between the contact lens and the liquid surface is 0.1-2 cm, the height between the ultraviolet light source and the liquid surface is 0.5-2 cm, and the illumination power is 1-60W; the reaction temperature is 4-60 ℃ and the reaction time is 1-5 min.
10. The method according to claim 5, wherein the concentration of the small molecular monomer containing a phosphorylcholine group in the aqueous solution of the small molecular monomer containing a phosphorylcholine group is 2 to 20wt%.
CN202311685223.1A 2023-12-11 2023-12-11 Contact lens with anti-fouling coating and preparation method thereof Pending CN117666168A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202311685223.1A CN117666168A (en) 2023-12-11 2023-12-11 Contact lens with anti-fouling coating and preparation method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202311685223.1A CN117666168A (en) 2023-12-11 2023-12-11 Contact lens with anti-fouling coating and preparation method thereof

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CN117666168A true CN117666168A (en) 2024-03-08

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