CN112851853A - Preparation method of silicone hydrogel contact lens - Google Patents

Preparation method of silicone hydrogel contact lens Download PDF

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Publication number
CN112851853A
CN112851853A CN202110215444.7A CN202110215444A CN112851853A CN 112851853 A CN112851853 A CN 112851853A CN 202110215444 A CN202110215444 A CN 202110215444A CN 112851853 A CN112851853 A CN 112851853A
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Prior art keywords
contact lens
hydrogel contact
silicone hydrogel
making
photoinitiator
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张爱军
何蛟
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Aishenghua Suzhou Optical Co ltd
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Aishenghua Suzhou Optical Co ltd
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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers 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
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/20Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00Processes of polymerisation
    • C08F2/46Polymerisation initiated by wave energy or particle radiation
    • C08F2/48Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • GPHYSICS
    • G02OPTICS
    • G02CSPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C7/00Optical parts
    • G02C7/02Lenses; Lens systems ; Methods of designing lenses
    • G02C7/04Contact lenses for the eyes
    • G02C7/049Contact lenses having special fitting or structural features achieved by special materials or material structures

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

Abstract

The present application relates to a method of making a silicone hydrogel contact lens, comprising: s1, mixing and stirring the photoinitiator and the silicon hydrogel material until the photoinitiator and the silicon hydrogel material are dissolved to obtain a mixed solution; s2, filtering the mixed solution to obtain filtrate, injecting the filtrate into a contact lens mold, and pressing and fixing the contact lens mold; s3, placing the contact lens mold in a UV illumination box for illumination polymerization for 5-30min to obtain a molded silicon hydrogel contact lens; s4, mechanically parting to take out the formed silicon hydrogel contact lens, sequentially washing with alcohol, washing with water and soaking and sterilizing with saline buffer solution to obtain the silicon hydrogel contact lens, and preparing the silicon hydrogel contact lens by using a photoinitiator and a silicon hydrogel material through illumination.

Description

Preparation method of silicone hydrogel contact lens
Technical Field
The invention relates to a preparation method of a silicon hydrogel contact lens, belonging to the technical field of contact lenses.
Background
The silicone hydrogel contact lens has good softness and extremely high oxygen permeability, and the wearing comfort of a user is remarkably improved. However, currently, the method of curing to produce silicone hydrogel contact lenses is heat curing, but the method of heat curing takes a long time, at least several hours, even tens of hours. In the prior art, photopolymerization is mentioned, but generally, azodiisobutyronitrile is adopted as an initiator, and a thermal initiator is adopted as an initiator for photocuring, so that good results cannot be obtained in terms of curing time and effect.
Disclosure of Invention
The invention aims to provide a preparation method of a silicone hydrogel contact lens, which has strong continuity and greatly shortens the curing time.
In order to achieve the purpose, the invention provides the following technical scheme: a method of making a silicone hydrogel contact lens, the method comprising:
s1, mixing and stirring the photoinitiator and the silicon hydrogel material until the photoinitiator and the silicon hydrogel material are dissolved to obtain a mixed solution;
s2, filtering the mixed solution to obtain filtrate, injecting the filtrate into a contact lens mould, and pressing and fixing the contact lens mould;
s3, placing the contact lens mold in a UV illumination box for illumination polymerization for 5-30min to obtain a molded silicon hydrogel contact lens;
and S4, mechanically separating the mold, taking out the formed silicon hydrogel contact lens, and sequentially performing alcohol washing, water washing and salt-containing buffer solution soaking sterilization to obtain the silicon hydrogel contact lens.
Further, the photoinitiator is any one or more of 819, 184, 1713 and 796 special for the LED, and the weight percentage of the photoinitiator is 0.3-1.5%.
Further, the light source of the UV illumination box is an LED or a mercury lamp, and the illumination distance of the light source is 100-200 mm.
Furthermore, the wavelength of the light source is 320-420nm, and the light intensity is 100%.
Further, the mixed liquor is filtered using a 0.22um filter element.
Further, the silicone hydrogel material comprises:
(1) a HEMA substrate;
(2) at least one siloxane polymerizing monomer of formula I:
Figure BDA0002953545190000021
wherein: r1Is H or CH3;R2Is C2-3 alkyl or alkyl containing 1-OH substituent group; r3、R4And R5Can be all
Figure BDA0002953545190000022
Or up to two groups are methyl;
(3) at least two hydrophilic monomers;
(4) at least one cross-linking agent.
Further, the hydrophilic monomer includes N-methyl-N-vinylacetamide, N-vinylpyrrolidone, N-dimethylacrylamide.
Further, the crosslinking agent is ethylene glycol dimethacrylate, and the weight percentage of the crosslinking agent is 0.1-0.5%.
Further, the silicone hydrogel material also includes an ultraviolet absorber.
Further, the ultraviolet absorbent is 2- (2 '-hydroxy-5' -methacryloyloxyethyl phenyl) -2H-benzotriazole, and the weight percentage of the ultraviolet absorbent is 0.5-1.8%.
The invention has the beneficial effects that: according to the preparation method of the silicon hydrogel contact lens, the photoinitiator and the silicon hydrogel material are used for preparing the silicon hydrogel contact lens through illumination, the preparation method greatly shortens the polymerization and curing time of the contact lens, the curing of the lens can be completed in tens of minutes or even several minutes, meanwhile, the continuity of the preparation process is improved and promoted, and the yield and the productivity of equipment can be greatly improved when the preparation method is applied to the current production of the contact lens.
The foregoing is a summary of the present invention, and in order to provide a clear understanding of the technical means of the present invention and to be implemented in accordance with the present specification, the following is a detailed description of the preferred embodiments of the present invention.
Detailed Description
The technical solutions of the present invention will be described clearly and completely below, and it should be apparent that the described embodiments are some, but not all, embodiments of the present invention. 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.
In addition, the technical features involved in the different embodiments of the present invention described below may be combined with each other as long as they do not conflict with each other.
The preparation method of the silicone hydrogel contact lens disclosed by the embodiment of the invention comprises the following steps:
s1, mixing and stirring the photoinitiator and the silicon hydrogel material until the photoinitiator and the silicon hydrogel material are dissolved to obtain a mixed solution;
s2, filtering the mixed solution to obtain filtrate, injecting the filtrate into a contact lens mold, and pressing and fixing the contact lens mold;
s3, placing the contact lens mold in a UV illumination box for illumination polymerization for 5-30min to obtain a molded silicon hydrogel contact lens;
and S4, mechanically parting the mold, taking out the formed silicon hydrogel contact lens, and sequentially carrying out alcohol washing, water washing and salt-containing buffer solution soaking sterilization to obtain the silicon hydrogel contact lens.
The photoinitiator may be any one or more of 819, 184, 1713, and 796 specific to LEDs, and the selection of the photoinitiator is not limited thereto, and may be others, which are not listed here. 0.3-1.5% of photoinitiator by weight percent, wherein the photoinitiator can absorb energy with certain wavelength in an ultraviolet region (250-420nm) or a visible light region (400-800nm) to generate free radicals, cations and the like, thereby initiating the polymerization, crosslinking and curing of the monomer and further polymerizing and curing the contact lens.
The light source of the UV illumination box is an LED or a mercury lamp, and the illumination distance of the light source is 100-200 mm. The light wavelength of the light source is 320-420nm, and the light intensity is 100%. When the light source is an LED, the wavelength is preferably 395 nm; when the light source is a mercury lamp, the wavelength is preferably 365 nm.
The mixed liquid is filtered by using a 0.22um filter element, so as to obtain the required filtrate, and the specific filter element used can be selected according to actual needs and is not specifically limited herein.
When the formed silicon hydrogel contact lens is cleaned by using ethanol, the specific operation is to soak the formed silicon hydrogel contact lens for 1 to 2 hours by using 10 percent ethanol solution. The buffer containing salt may be PBS buffer or the like.
The silicone hydrogel material comprises:
(1) a HEMA substrate;
(2) at least one siloxane polymerizing monomer of formula I:
Figure BDA0002953545190000041
wherein: r1Is H or CH3;R2Is C2-3 alkyl or alkyl containing 1-OH substituent group; r3、R4And R5Can be all
Figure BDA0002953545190000042
Or up to two groups are methyl;
(3) at least two hydrophilic monomers;
(4) at least one cross-linking agent.
Wherein the hydrophilic monomer comprises N-methyl-N-vinyl acetamide, N-vinyl pyrrolidone and N, N-dimethylacrylamide. The cross-linking agent is ethylene glycol dimethacrylate, and the weight percentage of the cross-linking agent is 0.1-0.5%.
To render the resulting contact lens uv resistant, the silicone hydrogel material may also include a uv absorber. The ultraviolet absorbent is 2- (2 '-hydroxy-5' -methacryloyloxyethyl phenyl) -2H-benzotriazole, and the weight percentage of the ultraviolet absorbent is 0.5-1.8%.
The hydrophilic monomer, the crosslinking agent and the ultraviolet absorber may also be other materials having corresponding functions, and are not particularly limited herein.
The method can also be used for preparing contact lenses by curing other materials, and the preparation efficiency of the contact lenses is improved.
With respect to the method of making silicone hydrogel contact lenses, the following specific examples are set forth:
the first embodiment is as follows:
taking a HEMA substrate: 30 parts, siloxane polymerization monomer: 25 parts, hydrophilic monomer: 45 parts, ultraviolet absorber: 0.5 part, crosslinking agent: 0.5 part, photoinitiator: 0.3 part of the raw materials are mixed and stirred for 10min to obtain a mixed solution, a 0.22um filter element is used for filtering to obtain a filtrate, and the filtrate is injected into a contact lens mold and is pressed and fixed; and (3) placing the combined mould into an ultraviolet lamp box, irradiating for 30min under a 395nm LED light source, mechanically separating the mould, taking out the formed silicon hydrogel contact lens, and sequentially performing alcohol washing, water washing and salt-containing buffer solution soaking sterilization to obtain the silicon hydrogel contact lens.
Example two:
taking a HEMA substrate: 30 parts, siloxane polymerization monomer: 25 parts, hydrophilic monomer: 45 parts, ultraviolet absorber: 1.5 parts, cross-linking agent: 2 parts, photoinitiator: 3 parts, mixing and stirring for 10min to obtain a mixed solution, filtering by using a 0.22um filter element to obtain a filtrate, injecting the filtrate into a contact lens mold, and pressing and fixing; and (3) placing the combined mould into an ultraviolet lamp box, irradiating for 5min under a 395nm LED light source, mechanically separating the mould, taking out the formed silicon hydrogel contact lens, and sequentially performing alcohol washing, water washing and salt-containing buffer solution soaking sterilization to obtain the silicon hydrogel contact lens.
In conclusion, the preparation method of the silicon hydrogel contact lens disclosed by the invention prepares the silicon hydrogel contact lens by the photoinitiator and the silicon hydrogel material through illumination, the preparation method greatly shortens the polymerization curing time of the contact lens, only dozens of minutes or even minutes are needed to complete the curing of the lens, meanwhile, the continuity of the preparation process is improved and promoted, and the yield and the productivity of equipment can be greatly improved when the preparation method is applied to the current contact lens production.
The technical features of the embodiments described above may be arbitrarily combined, and for the sake of brevity, all possible combinations of the technical features in the embodiments described above are not described, but should be considered as being within the scope of the present specification as long as there is no contradiction between the combinations of the technical features.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.

Claims (10)

1. A method of making a silicone hydrogel contact lens, the method comprising:
s1, mixing and stirring the photoinitiator and the silicon hydrogel material until the photoinitiator and the silicon hydrogel material are dissolved to obtain a mixed solution;
s2, filtering the mixed solution to obtain filtrate, injecting the filtrate into a contact lens mould, and pressing and fixing the contact lens mould;
s3, placing the contact lens mold in a UV illumination box for illumination polymerization for 5-30min to obtain a molded silicon hydrogel contact lens;
and S4, mechanically separating the mold, taking out the formed silicon hydrogel contact lens, and sequentially performing alcohol washing, water washing and salt-containing buffer solution soaking sterilization to obtain the silicon hydrogel contact lens.
2. The method of making a silicone hydrogel contact lens of claim 1, wherein the photoinitiator is any one or more of 819, 184, 1713, 796 specific to LEDs, and is present in an amount of 0.3 to 1.5% by weight of the photoinitiator.
3. The method of claim 1, wherein the light source of the UV light box is an LED or a mercury lamp, and the light distance of the light source is 100-200 mm.
4. The method as claimed in claim 3, wherein the light source has a wavelength of 320-420nm and a light intensity of 100%.
5. The method of making a silicone hydrogel contact lens of claim 1, wherein the mixed liquor is filtered using a 0.22um filter cartridge.
6. The method of making a silicone hydrogel contact lens of claim 1, wherein the silicone hydrogel material comprises:
(1) a HEMA substrate;
(2) at least one siloxane polymerizing monomer of formula I:
Figure FDA0002953545180000011
wherein: r1Is H or CH3;R2Is C2-3 alkyl or alkyl containing 1-OH substituent group; r3、R4And R5Can be all
Figure FDA0002953545180000012
Or up to two groups are methyl;
(3) at least two hydrophilic monomers;
(4) at least one cross-linking agent.
7. The method of making a silicone hydrogel contact lens of claim 6, wherein the hydrophilic monomer comprises N-methyl-N-vinyl acetamide, N-vinyl pyrrolidone, N-dimethylacrylamide.
8. The method of making a silicone hydrogel contact lens of claim 6, wherein the cross-linking agent is ethylene glycol dimethacrylate and is present in an amount of 0.1 to 0.5 weight percent.
9. The method of making a silicone hydrogel contact lens of claim 6, wherein the silicone hydrogel material further comprises an ultraviolet absorber.
10. The method of making a silicone hydrogel contact lens of claim 9, wherein the uv absorber is 2- (2 '-hydroxy-5' -methacryloyloxyethylphenyl) -2H-benzotriazole and the uv absorber is present in an amount of 0.5 to 1.8% by weight.
CN202110215444.7A 2021-02-26 2021-02-26 Preparation method of silicone hydrogel contact lens Pending CN112851853A (en)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130158150A1 (en) * 2011-12-14 2013-06-20 Semprus Biosciences Corp. Multistep uv process to create surface modified contact lenses
CN104114610A (en) * 2011-12-23 2014-10-22 庄臣及庄臣视力保护公司 Silicone hydrogels having a structure formed via controlled reaction kinetics
CN105061674A (en) * 2015-08-10 2015-11-18 爱生华(苏州)光学有限公司 Novel fluorosilicone-containing silicone hydrogel contact lens formula selection and new process
CN108070044A (en) * 2018-02-05 2018-05-25 中国科学院长春应用化学研究所 A kind of gel rubber material and preparation method thereof
CN111253533A (en) * 2018-11-30 2020-06-09 晶硕光学股份有限公司 Silicone hydrogel composition, silicone hydrogel lens, and method for manufacturing silicone hydrogel lens
CN112094387A (en) * 2020-09-07 2020-12-18 华诺森(武汉)生物医药技术有限公司 Novel silica hydrogel contact lens

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130158150A1 (en) * 2011-12-14 2013-06-20 Semprus Biosciences Corp. Multistep uv process to create surface modified contact lenses
CN104114610A (en) * 2011-12-23 2014-10-22 庄臣及庄臣视力保护公司 Silicone hydrogels having a structure formed via controlled reaction kinetics
CN105061674A (en) * 2015-08-10 2015-11-18 爱生华(苏州)光学有限公司 Novel fluorosilicone-containing silicone hydrogel contact lens formula selection and new process
CN108070044A (en) * 2018-02-05 2018-05-25 中国科学院长春应用化学研究所 A kind of gel rubber material and preparation method thereof
CN111253533A (en) * 2018-11-30 2020-06-09 晶硕光学股份有限公司 Silicone hydrogel composition, silicone hydrogel lens, and method for manufacturing silicone hydrogel lens
CN112094387A (en) * 2020-09-07 2020-12-18 华诺森(武汉)生物医药技术有限公司 Novel silica hydrogel contact lens

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Application publication date: 20210528