CN110200743B - Self-fixing tracing punctal plug and preparation method thereof - Google Patents
Self-fixing tracing punctal plug and preparation method thereof Download PDFInfo
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- CN110200743B CN110200743B CN201910452379.2A CN201910452379A CN110200743B CN 110200743 B CN110200743 B CN 110200743B CN 201910452379 A CN201910452379 A CN 201910452379A CN 110200743 B CN110200743 B CN 110200743B
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
- A61F9/00—Methods or devices for treatment of the eyes; Devices for putting-in contact lenses; Devices to correct squinting; Apparatus to guide the blind; Protective devices for the eyes, carried on the body or in the hand
- A61F9/0008—Introducing ophthalmic products into the ocular cavity or retaining products therein
- A61F9/0017—Introducing ophthalmic products into the ocular cavity or retaining products therein implantable in, or in contact with, the eye, e.g. ocular inserts
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
- A61F9/00—Methods or devices for treatment of the eyes; Devices for putting-in contact lenses; Devices to correct squinting; Apparatus to guide the blind; Protective devices for the eyes, carried on the body or in the hand
- A61F9/007—Methods or devices for eye surgery
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F120/00—Homopolymers 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 a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F120/10—Esters
- C08F120/20—Esters of polyhydric alcohols or polyhydric phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
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Abstract
The invention provides a self-fixing tracing punctal plug and a preparation method thereof, wherein the preparation method comprises the following steps: fully mixing a monomer, a cross-linking agent, an initiator and water to obtain a mixed solution A; injecting the mixed solution A into a mold, carrying out polymerization forming through thermal initiation or catalyst initiation or light initiation, and obtaining hollow hydrogel after demolding; soaking and cleaning the hollow hydrogel and then drying; putting the nickel-titanium wires in the center of the dry hollow hydrogel, putting the nickel-titanium wires and the dry hollow hydrogel into an original-size mold, and then putting the whole mold into the mixed solution A to initiate polymerization molding; taking out the mold when the solution starts to polymerize to have certain viscosity; and (5) after the viscous solution in the mould is completely formed, demoulding and cutting to obtain the tracing punctum plug. The punctal plug can be expanded by water absorption and can be fixed in the lacrimal canaliculus after being implanted; contains nickel-titanium wires, and can display the position of the punctum plug in the lacrimal canaliculus through X-ray computed tomography, thereby ensuring the accuracy of the implantation position and the clinical observation after implantation.
Description
Technical Field
The invention relates to the field of medical equipment, in particular to a self-fixing tracing punctal plug and a preparation method thereof.
Background
Dry eye has become a global epidemic with an increasing trend in prevalence. The pathogenesis of the dry eye is very complex, cornea, conjunctiva, lacrimal gland, meibomian gland and nerve pathways connected among the corneal gland, the conjunctiva, the lacrimal gland and the meibomian gland play a role in regulating and controlling the formation of a tear film and the secretion of tears, and the normal structure and the function of the ocular surface are maintained and protected, wherein the abnormality of any link can damage the normal repair and prevention mechanism of the ocular surface, and the dry eye is caused. The lacrimal passage is blocked by the punctum plug, so that the stability of the lacrimal film can be well maintained, and the dry eye symptom can be relieved. Wherein, the embolism mainly comprises a silica gel embolism and a hydrogel embolism. Hydrogel punctal plugs are typically placed in the lacrimal canaliculus without contact with the cornea for greater comfort. However, the hydrogel punctal plugs implanted into the body for a long time are hidden in lacrimal canaliculi, and the dynamic conditions of displacement, deformation, cracking, shedding, loss of work and the like are difficult to be verified by common observation or X-ray image examination. The hydrogel is compounded with high-density matters such as metal wires, so that the prepared hydrogel can be displayed under an X-ray image. In the preparation of the developing hydrogel, the metal wires are required to be completely wrapped in the hydrogel so as to ensure that the metal wires cannot be separated from the hydrogel in a dry state and a wet state. However, in the preparation process, because the density of the metal wires is high, the metal wires are put in before polymerization and sink to the bottom of the container, and the hydrogel cannot completely wrap the metal wires. When placed after polymerization has begun, the formed hydrogel has structural defects, and the wires are also easily detached or exposed.
Disclosure of Invention
In order to solve the technical problems in the prior art, the invention provides a preparation method of a self-fixing tracing punctal plug, which comprises the following steps:
(1) fully mixing a monomer, a cross-linking agent, an initiator and water to obtain a mixed solution A;
selecting any one or more of ammonium persulfate, potassium persulfate, water-soluble azo initiators and water-soluble photoinitiators as an initiator;
(2) when the initiator contains ammonium persulfate or potassium persulfate, adding the mixed solution A into a catalyst, injecting the catalyst into a mold, and inserting a metal rod with a corresponding size into a specified position;
when the initiator is a water-soluble azo initiator and/or a water-soluble photoinitiator, directly injecting the mixed solution A into a mold, and inserting a metal rod with a corresponding size into a specified position;
(3) and (3) carrying out polymerization forming by thermal initiation or catalyst initiation or light initiation, and demoulding to obtain the hollow hydrogel.
(4) Soaking and cleaning the demolded hollow hydrogel in deionized water for a period of time, and drying in a drying oven at a certain temperature;
(5) putting a nickel-titanium wire in the center of the dry hollow hydrogel, putting the nickel-titanium wire and the dry hollow hydrogel into a mould with the original size, putting the whole mould into the mixed solution A to initiate polymerization, and taking out the mould when the polymerization solution has certain viscosity;
(6) and (3) after the viscous solution in the mould is completely formed, demoulding, cutting and soaking in deionized water to obtain the tracing punctum plug.
Preferably, the first and second electrodes are formed of a metal,
further comprising the step of (7) drying the punctal plugs, and packaging and sterilizing the same.
Preferably, the first and second electrodes are formed of a metal,
the monomer is selected from one or more of hydroxyethyl methacrylate, vinyl pyrrolidone, sulfobetaine, 2-methacryloyloxyethyl and carboxyl betaine;
the cross-linking agent is any one or more of ethylene glycol diacetate, polyethylene glycol diacrylate and N, N' -methylene bisacrylamide;
the water-soluble azo initiator is argon diisobutyl amidine hydrochloride and/or azodiisopropyl imidazoline hydrochloride;
the water-soluble photoinitiator is Irgacure 2959 and/or alpha-ketoglutaric acid.
Preferably, the catalyst is tetramethylethylenediamine.
Preferably, the concentration of the monomer is 0.05-6 mol/L.
Preferably, the concentration of the cross-linking agent is 0.01-0.2 mol/L.
Preferably, the concentration of the initiator is 0.001-0.1 mol/L.
Preferably, the diameter of the metal rod is 0.1-0.5 mm.
Preferably, the diameter of the nickel-titanium wire is 0.05-0.5 mm, and the length of the nickel-titanium wire is 0.5-1.5 mm.
The invention also provides the punctal plug obtained by the preparation method of the self-fixing tracing punctal plug, the middle of the punctal plug contains nickel-titanium wires, and the length L of the wet punctal plug is11.5-3.5mm, and wet outer diameter phi1Is 0.7 to 13mm, dry length L21.0-2.0mm, dry outer diameter phi20.3-0.8 mm.
Compared with the prior art, the invention has the beneficial effects that:
(1) the punctal plug prepared by the method contains nickel-titanium wires, and is convenient for clinical observation of doctors through X-ray computed tomography.
(2) Through two times of polymerization, the outer layer and the inner layer of the punctal plug are connected through an interpenetrating network, the combination is firm, and the metal wire in the punctal plug can not fall off or be exposed from the punctal plug in the process of mutually converting the wet state and the dry state of the punctal plug.
(3) The punctal plug prepared by the method is made of hydrogel materials, can be directly implanted into lacrimal canaliculus without contacting with cornea, reduces foreign body sensation, has better comfort degree than a silica gel plug, is a hard straight short rod before implantation, absorbs water to swell and soften after implantation, and achieves the fixing effect.
Drawings
Fig. 1 is a schematic structural view of a self-anchoring tracer punctal plug of the invention, wherein fig. 1(a) is a schematic view in an aqueous state and fig. 1(b) is a schematic view in a dry state.
Detailed Description
The invention provides a preparation method of a self-fixing tracing punctal plug, which selects hydrogel materials and can be implanted into lacrimal canaliculus by using ophthalmological forceps. After implantation, punctal plugs absorb water in a larger volume, thereby accommodating the lacrimal canaliculus size. The punctal plug contains nickel-titanium wires, and can display the position of the punctal plug through X-ray computed tomography, and the dynamic conditions of displacement, deformation, cracking, falling, power loss and the like of the punctal plug can be verified through the examination of X-ray images.
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example one
The invention provides a preparation method of a self-fixing tracing punctal plug, which comprises the following steps:
(1) fully mixing a monomer, a cross-linking agent, an initiator and water to obtain a mixed solution A;
selecting hydroxyethyl methacrylate with the concentration of 2 mol/L;
selecting glycol diacetate with the concentration of 0.025 mol/L;
selecting an initiator ammonium persulfate with the concentration of 0.025 mol/L.
(2) Taking 1mL of mixed solution, adding 10 mu L of catalyst tetramethylethylenediamine, fully mixing, injecting into a punctum plug mould with the inner diameter of 1mm within five minutes, inserting a metal rod with the diameter of 0.5mm within ten minutes, and demoulding after one hour to obtain a hollow hydrogel tube;
(3) soaking and cleaning the demolded hollow hydrogel tube in deionized water for 24 hours, and drying the hollow hydrogel tube in a 50-degree oven to obtain a dry hollow hydrogel tube;
(4) putting a nickel-titanium wire with the length of 1.0mm and the diameter of 0.2mm in the center of the dry hollow hydrogel, putting the nickel-titanium wire and the dry hollow hydrogel into a mould with the original size, putting the whole mould into a mixed solution A added with a catalyst tetramethyl ethylenediamine, and taking out the mould when the solution starts to polymerize for 3 minutes and the solution in a mould tube has certain viscosity and cannot flow out, and horizontally putting the mould on a clean bench for continuous polymerization;
(5) and (3) after the viscous solution in the mould is completely formed, demoulding, cutting and soaking in deionized water to obtain the tracing punctum plug.
(6) Drying the punctum plugs, packaging and sterilizing for use.
The punctal plugs with the outer diameter of 1mm and containing the nickel-titanium wires with the outer diameter of 0.2mm are prepared by the method. After implantation, punctal plugs absorb large volumes, adapting to the lacrimal canaliculus size. The punctal plug can obviously display the nickel-titanium wire through X-ray computed tomography, and doctors can perform clinical observation through the nickel-titanium wire.
Example two
The invention provides a preparation method of a self-fixing tracing punctal plug, which comprises the following steps:
(1) fully mixing a monomer, a cross-linking agent, an initiator and water to obtain a mixed solution A;
selecting vinyl pyrrolidone with the concentration of 0.5 mol/L;
selecting hydroxyethyl methacrylate with the concentration of 1.5 mol/L;
selecting glycol diacetate with the concentration of 0.05 mol/L;
the photoinitiator Irgacure 2959 was chosen, the concentration of which was 0.025 mol/L.
(2) The mixed solution was poured into a punctal plug mold having an inner diameter of 0.8mm, and a metal rod having a diameter of 0.3mm was inserted, and after irradiation with a 365nm ultraviolet lamp for 20 minutes, the hollow hydrogel tube was obtained by demolding.
(3) Soaking and cleaning the demolded hollow hydrogel tube in deionized water for 24 hours, and drying the tube in a 50-DEG oven;
(4) putting a nickel-titanium wire with the length of 1.0mm and the diameter of 0.1mm in the center of a dry hollow hydrogel tube, putting the nickel-titanium wire and the dry hollow hydrogel tube into a mould with the original size, putting the whole mould into a mixed solution A, irradiating for 10 minutes by using a 365nm ultraviolet lamp, taking out the mould when the solution in the mould tube has certain viscosity and cannot flow out, horizontally putting the mould on a clean bench, and continuously irradiating for 10 minutes by using the 365nm ultraviolet lamp;
(5) and (3) after the viscous solution in the mould is completely formed, demoulding, cutting and soaking in deionized water to obtain the tracing punctum plug.
(6) Drying the punctum plugs, packaging and sterilizing for use.
The punctal plug which is prepared by the method and contains the nickel-titanium wire with the outer diameter of 0.1mm and the outer diameter of 0.8 mm. After implantation, punctal plugs absorb large volumes, adapting to the lacrimal canaliculus size. The punctal plug can display nickel-titanium wires through X-ray computed tomography, and is convenient for doctors to carry out clinical observation.
EXAMPLE III
The invention provides a preparation method of a self-fixing tracing punctal plug, which comprises the following steps:
(1) fully mixing a monomer, a cross-linking agent, an initiator and a salt solution to obtain a mixed solution;
selecting hydroxyethyl methacrylate with the concentration of 1 mol/L;
selecting carboxyl betaine with the concentration of 0.5 mol/L;
selecting glycol diacetate with the concentration of 0.1 mol/L;
selecting water-soluble azo initiator azobisisobutylimidazoline hydrochloride, wherein the concentration of the azo initiator azobisisobutylimidazoline hydrochloride is 0.025 mol/L.
(2) And (3) injecting the mixed solution into a punctal plug mold with the inner diameter of 0.6mm, inserting a metal rod with the diameter of 0.2mm, putting the punctal plug into an oven at 60 ℃ for 24 hours, and demolding to obtain the punctal plug.
(3) Soaking and cleaning the demolded hollow hydrogel in deionized water for 24 hours, and drying in a 50-degree oven;
(4) putting a nickel-titanium wire with the length of 1.0mm and the diameter of 0.1mm in the center of the dry hollow hydrogel, putting the nickel-titanium wire and the dry hollow hydrogel into a mould with the original size, putting the whole mould into an oven with the temperature of 60 ℃ for 5 minutes, taking out the mould when the solution in the mould tube has certain viscosity and cannot flow out, and putting the mould into the oven with the temperature of 60 ℃ again for 24 hours;
(5) and (3) after the viscous solution in the mould is completely formed, demoulding, cutting and soaking in deionized water to obtain the tracing punctum plug.
(6) Drying the punctum plugs, packaging and sterilizing for use.
The punctal plug which is prepared by the method and contains the nickel-titanium wire with the outer diameter of 0.1mm and the outer diameter of 0.6 mm. After implantation, punctal plugs absorb large volumes, adapting to the lacrimal canaliculus size. The punctal plug can display nickel-titanium wires through X-ray computed tomography, and is convenient for doctors to carry out clinical observation.
The above examples are only intended to illustrate the technical solution of the present invention, but not to limit it; although the present invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some technical features may be equivalently replaced; and such modifications or substitutions do not depart from the spirit and scope of the corresponding technical solutions of the embodiments of the present invention.
Claims (7)
1. A method of making a self-fixating tracer punctal plug comprising the steps of:
(1) fully mixing a monomer, a cross-linking agent, an initiator and water to obtain a mixed solution A;
selecting any one or more of ammonium persulfate, potassium persulfate, water-soluble azo initiators and water-soluble photoinitiators as an initiator;
(2) when the initiator contains ammonium persulfate or potassium persulfate, adding the mixed solution A into a catalyst, injecting the catalyst into a mold, and inserting a metal rod with a corresponding size into a specified position;
when the initiator is a water-soluble azo initiator and/or a water-soluble photoinitiator, directly injecting the mixed solution A into a mold, and inserting a metal rod with a corresponding size into a specified position;
(3) carrying out polymerization forming by thermal initiation or catalyst initiation or photo initiation, and obtaining hollow hydrogel after demolding;
(4) soaking and cleaning the demolded hollow hydrogel in deionized water for a period of time, and drying in a drying oven at a certain temperature;
(5) putting the nickel-titanium wires in the center of the dry hollow hydrogel, putting the nickel-titanium wires and the dry hollow hydrogel into a mould with the original size, then putting the whole mould into the mixed solution A, initiating polymerization molding, and taking out the mould when the solution starts to polymerize to have certain viscosity;
(6) after the viscous solution in the mold is completely formed, demolding, cutting and soaking in deionized water to obtain the tracing punctum plug;
the monomer is selected from one or more of hydroxyethyl methacrylate, vinyl pyrrolidone, sulfobetaine, 2-methacryloyloxyethyl and carboxyl betaine; the cross-linking agent is any one or more of ethylene glycol diacetate, polyethylene glycol diacrylate and N, N' -methylene bisacrylamide; the water-soluble azo initiator is argon diisobutyl amidine hydrochloride and/or azodiisopropyl imidazoline hydrochloride; the water-soluble photoinitiator is Irgacure 2959 and/or alpha-ketoglutaric acid.
2. The method of claim 1, further comprising the step of (7) drying the punctal plug, packaging and sterilizing.
3. The method of claim 1, wherein the catalyst is tetramethylethylenediamine.
4. The method of claim 1, wherein the monomer is present at a concentration of 0.05 to 6 mol/L; the concentration of the cross-linking agent is 0.01-0.2 mol/L; the concentration of the initiator is 0.001-0.1 mol/L.
5. The method of claim 1, wherein the metal rod has a diameter of 0.1mm to 0.5 mm.
6. The method of claim 1, wherein the nickel titanium wire has a diameter of 0.05 to 0.5mm and a length of 0.5 to 1.5 mm.
7. The punctal plug of any one of claims 1 to 6, which is obtained by the method of preparing a self-fixating tracer punctal plug, wherein the punctal plug comprises nickel titanium wires in the middle, and wherein the length L1 of the punctal plug in a wet state is 1.5 to 3.5mm, the outer diameter Φ 1 in a wet state is 0.7 to 1.3 mm, the length L2 in a dry state is 1.0 to 2.0mm, and the outer diameter Φ 2 in a dry state is 0.3 to 0.8 mm.
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| US5283063A (en) * | 1992-01-31 | 1994-02-01 | Eagle Vision | Punctum plug method and apparatus |
| CN2429148Y (en) * | 2000-06-14 | 2001-05-09 | 施立红 | Lacrimal duct recovery instrument |
| CN2518483Y (en) * | 2001-06-02 | 2002-10-30 | 李秀山 | Lacrimal implantation tube |
| WO2003015891A1 (en) * | 2001-08-13 | 2003-02-27 | The Board Of Trustees Of The Leland Stanford Junior University | Bonded phase photopolymerized sol-gel column and associated methods |
| CN2790427Y (en) * | 2005-05-23 | 2006-06-28 | 张德玉 | Lacrimal tract stent |
| CN101270173A (en) * | 2007-11-27 | 2008-09-24 | 中国科学院长春应用化学研究所 | High-gel strength, salt resistant amphoteric ion type nano-composite hydrogel and preparing method |
| CN103059215A (en) * | 2012-12-20 | 2013-04-24 | 华南理工大学 | Glycine betaine ester intelligent hydrogel relatively controllable in structure and preparation method and application |
| EP3324902A1 (en) * | 2015-07-22 | 2018-05-30 | Incept, LLC | Coated punctal plug |
| CN106344257B (en) * | 2016-08-31 | 2018-07-10 | 李志强 | A kind of lacrimal passage bolt of body scalable |
| CN107617126A (en) * | 2017-08-11 | 2018-01-23 | 天津大学 | A kind of surface modification method of porous material and application |
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