CN106950717A - A kind of preparation method of flucride siloxane interpenetration network hydrogel - Google Patents

A kind of preparation method of flucride siloxane interpenetration network hydrogel Download PDF

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Publication number
CN106950717A
CN106950717A CN201610002566.7A CN201610002566A CN106950717A CN 106950717 A CN106950717 A CN 106950717A CN 201610002566 A CN201610002566 A CN 201610002566A CN 106950717 A CN106950717 A CN 106950717A
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preparation
flucride siloxane
parts
hydrogel
flucride
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CN201610002566.7A
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CN106950717B (en
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董薇
朱智慧
陈杰
金范龙
康正国
王瑾
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Jilin Ruierkang Optical Technology Co.,Ltd.
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Jilin Institute of Chemical Technology
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    • 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
    • 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
    • C08F220/22—Esters containing halogen
    • 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
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • 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
    • C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
    • C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
    • C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
    • 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
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • C08F220/281—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate

Abstract

Specifically it is exactly a kind of method of the linear polymer and hydrophilic polymer crosslinked semi-intercrossing network that are related to flucride siloxane of synthesizing new the invention discloses a kind of flucride siloxane interpenetration network hydrogel preparation method.The first step is to prepare fluorosilicone performed polymer in the case where adding initiator, because forming the prepolymer of straight chain, with regular molecular structure, can improve the oxygen flow and anti-protein deposition of eyeglass；Second step is to add siloxanes performed polymer in hydrophilic monomer to mix, and adds crosslinking agent, thermal initiator, because monomer is well mixed, can improve the isotropism of performed polymer and hydrophilic monomer, improve the transparency and hydrophily；3rd step is press mold, thermal initiation curing molding.The preparation method of the present invention is simple, the ratio of briquetting of eyeglass is high, prepared flucride siloxane hydrogel has good tensile elongation, fatigue resistance, anti-protein adsorptivity, and water content changes some shortcomings of conventional contact lenses up to 45%, so as to improve the wear comfort of contact lenses.

Description

A kind of preparation method of flucride siloxane interpenetration network hydrogel
Technical field
The present invention relates to new with ipn technology prepares that a kind of oxygen flow is good, water content is high and anti-protein is adsorbed Flucride siloxane hydrogel preparation method, improve the biocompatibility and tensile property of material, belong to biological medicine Field of material technology.
Background technology
Contact lenses are also referred to as contact lens, are that one kind is worn on cornea, for correcting defects of vision or protect eyes Eyeglass, according to the soft or hard degree of material can be divided into hard, semi-rigid, soft three kinds.The hard contact lenses of early stage are main With polymethyl methacrylate（PMMA）It is prepared, this hard contact lenses water content is low, oxygen permeability is poor, wears for raw material Foreign body sensation is very strong when wearing, and can also cause a series of disease of cornea.Then soft glued membrane contact lense arises at the historic moment, it main Raw material is methacrylic acid-beta-hydroxy ethyl ester（HEMA）Deng some non-ionic materials, the contact lenses of this material, eyeglass is more soft It is soft, wearing comfort is improved, oxygen permeability has close relation with water content, and usual water content is higher, and oxygen permeability is better, but It is that eyeglass can absorb the moisture in tear, cause eyes dry and astringent because water content is high.Silicone hydrogel contact lenses are due to material There are many small passages in matter matrix, be that gas molecule, ion and hydrone are passed freely through there is provided convenient, improve oxygen flow Property, eyeglass is difficult water shortage, improves the comfortableness worn, but because eyeglass somewhat shows hard when just starting to wear, eyes have Foreign body sensation.In addition this eyeglass has suction-operated to protein, the protein material formation egg that automatic absorbing eyes are secreted White matter is precipitated.Because the protein precipitation of macromolecular volume is adsorbed on the surface of contact lenses, make the oxygen flow of contact lens Coefficient declines, and users cornea's anoxic can be made if wear time is long, so that trigger a series of lesion problems such as cornea redness, Be not suitable for long periods of wear.And fluorine atom has very strong sucting electronic effect in fluorine-containing alkyl monomer, C-F bond energys are very high, fluorine atom There is similar atomic radius with hydrogen atom, the induced polarization rate of fluorocarbons is very low, can effectively reduce the deposition of protein, Therefore a kind of new flucride siloxane hydrogel is by consumer in the urgent need to it can not only increase oxygen permeability coefficient, also can Increase the comfort worn.
Hydrogel interpenetrating network structure is a kind of novel high polymer material grown up 1970s, this material It is mutually to be tangled, interted by two kinds or two or more polymer, and at least contains a kind of strand, they passes through chemical bond Mode be cross-linked to form network structure.This structure does not interfere with its intrinsic characteristic, and can get appropriate performance complement work With.
The characteristics of hydrogel interpenetrating network structure is maximum is to be formed at least in kinetically stable alloy property Material and can be by thermodynamically incompatible mixed with polymers, each polymer is continuous phase in itself, and phase region interval is 10- 100nm, much smaller than the wavelength of visible ray, therefore it is in colorless and transparent.This Phase stracture make it that the vitrifying of polymer turns Become area to shift and broaden, this architectural characteristic determine it not only only have good static mechanical property also have it is good Dynamic mechanical, and also have wider temperature to use scope.Hydrogel interpenetrating network structure is not simply to be blended, be grafted Or polymer architecture formed by block, in performance, it has obvious difference with three above, is mainly reflected in： First, hydrogel interpenetrating network structure can be swelled but can not dissolve in a solvent；Second, formed by hydrogel interpenetrating network Polymerization will not produce creep and flowing.
Value of the invention is that previously prepared flucride siloxane performed polymer can effectively improve the oxygen flow of contact lenses Property and anti-protein precipitation, it formed linear polymer be interspersed in HEMA be main monomer cross-linking polymer system in, entirely Material is isotropic structure, with good translucency, and can be formed in crosslinking agent containing substantial amounts of hydroxyl with hydrone The combination water of intramolecular, reduces the percentage of water loss of eyeglass, and extension is worn, and improves the biocompatibility of hydrogel contact lens, Make to wear more comfortable.
The interpenetrating networks flucride siloxane hydrogel contact lens of the present invention can not only meet the demand that consumer wears, and contain The advantages of water height, good oxygen permeability, tensile elongation and good anti-protein absorption property, and technological process is simplified, contract The short process time, is the condition that factorial praluction is provided convenience.
The content of the invention
It is an object of the invention to provide a kind of new flucride siloxane hydrogel contact lens with its preparation method, this The contact lenses that the method for kind is prepared have water content high, and mechanical performance and tensile property are excellent, and anti-protein is precipitated Function admirable advantage.The present invention prepares the oligomerization of fluorochemical monomer and silicone-containing monomer under catalyst action first The prepolymer of degree, second step adds hydrophilic monomer and crosslinking agent, pressing mold and releasing process is carried out, so as to form the net of IPN The hydrogel contact lens of network structure.
The technical method of the present invention：A kind of new flucride siloxane hydrogel contact lens and preparation method thereof, have Following steps：
A, flucride siloxane hydrogel contact lens performed polymer synthesis：By quality parts ratio trifluoroethyl methacrylate： KH570=1:In 1.5-2.0, the beaker for adding 50ml, 0.2-1% parts of two methyl isobutyrate of initiator azo, side stirring are added Side is heated, and temperature control is at 30-50 DEG C, and then reactant is cooled to room temperature by isothermal reaction 0.5-2h；
B, flucride siloxane hydrogel contact lens mixture preparation：Above-mentioned mixed liquor 1-20 parts, methacrylic acid-β-hydroxyl second HEMA60-98 parts of ester, 0.1-1% parts of crosslinking agent, purge there-necked flask with nitrogen at room temperature, 1-10 are stirred under nitrogen protection small When；
C, a kind of preparation of new flucride siloxane hydrogel contact lens：Above-mentioned mixed liquor is molded entirely, by mould 80-140 DEG C is put into dry baking oven, and solidified forming time is 2-8 hours, carries out the first time demoulding, is put into the hot water of boiling 5-30min, unreacted monomer of going out, is then cooled down with cold water, is carried out second and is stripped, so as to obtain new fluorine-containing silica Alkane interpenetration network hydrogel contact lenses.
A kind of preparation method of above-mentioned new flucride siloxane hydrogel is required according to right 1, it is characterized in that：Step A Described in trifluoroethyl methacrylate and KH570 quality parts ratio be 0.5-3, most preferably 1.0-1.5；The stirring temperature Degree is preferably 30-45 DEG C, most preferably 35-45 DEG C；Mixing time is preferably 0.5-2h, most preferably 0.5-1h；It is described to trigger Agent is preferably 0.2-1%, including azodiisobutyronitrile, the methyl isobutyrate of azo two, benzoyl peroxide, the valeronitrile of azo two, peroxide Change lauroyl, preferably cumene hydroperoxide, the methyl isobutyrate of azo two.
A kind of preparation method of above-mentioned new flucride siloxane hydrogel is required according to right 1, it is characterized in that：Step B Described in the mass fraction of mixed liquor be preferably 2-15 parts, most preferably 2-10 parts；HEMA mass fraction is preferably 70-98 Part, most preferably 80-98 parts；Crosslinking agent is preferably 0.2-0.5%；Described crosslinking agent is ethylene glycol dimethacrylate, three Contracting tetraethylene glycol dimethylacrylate, N are N- methylene-bisacrylamides, trimethylol-propane trimethacrylate, three sweet Alcohol dimethylacrylate, tetramethyl disiloxane are double（Propyl methacrylate）, most preferably tetraethylene-glycol diformazan Base acrylate.
A kind of preparation method of above-mentioned new flucride siloxane interpenetration network hydrogel, its feature are required according to right 1 It is：It is preferably 90-130 DEG C to set temperature described in step C in drying oven, most preferably 100-120 DEG C；Solidified forming time It is optimized for 3-7h, most preferably 4-6h；It is 5-20min, most preferably 5-10min to be put into time-optimized in the hot water of boiling.
Below by embodiment, the present invention is described in further detail, a kind of new flucride siloxane hydrogel and Its preparation method, Bao includes Bu Zhou ﹕ under Yi
A：The synthesis of flucride siloxane hydrogel contact lens performed polymer：By quality parts ratio trifluoroethyl methacrylate： KH570=1:In 1.0-1.5, the beaker for adding 50ml, 0.2-1% parts of two methyl isobutyrate of initiator azo, side stirring are added Side is heated, and temperature control is at 35-45 DEG C, and then reactant is cooled to room temperature by isothermal reaction 0.5-1 hours；
B：The preparation of flucride siloxane hydrogel contact lens mixture：Above-mentioned mixed liquor 2-15 parts, methacrylic acid-β-hydroxyl second HEMA60-98 parts of ester, 0.2-0.5% parts of crosslinking agent tetraethylene-glycol dimethylacrylate, purge three mouthfuls with nitrogen at room temperature Flask, is stirred 1-10 hours under nitrogen protection；
C：A kind of preparation of new flucride siloxane hydrogel contact lens：Above-mentioned mixed liquor is molded entirely, by mould 100-120 DEG C is put into dry baking oven, and solidified forming time is 4-6 hours, carries out the first time demoulding, is put into the hot water of boiling 5-10min, unreacted monomer of going out, is then cooled down with cold water, is carried out second and is stripped, so as to obtain new fluorine-containing silica Alkane interpenetration network hydrogel contact lenses.
Embodiment 1
A, flucride siloxane hydrogel contact lens performed polymer synthesis：By quality parts ratio trifluoroethyl methacrylate： KH570=1:1.5 add in 50ml beaker, add 0.2% part of two methyl isobutyrate of initiator azo, heat while stirring, Temperature control is at 40 DEG C, and then reactant is cooled to room temperature by isothermal reaction 1h；
B, flucride siloxane hydrogel contact lens mixture preparation：Above-mentioned 5 parts of mixed liquor, methacrylic acid-beta-hydroxy ethyl ester 95 parts of HEMA, 0.1% part of crosslinking agent tetraethylene-glycol dimethylacrylate, purge there-necked flask with nitrogen at room temperature, Stirred under nitrogen atmosphere 10 hours；
C, a kind of preparation of new flucride siloxane hydrogel contact lens：Above-mentioned mixed liquor is molded entirely, by mould 120 DEG C are put into dry baking oven, and solidified forming time is 4 hours, carries out the first time demoulding, is put into the hot water 5min of boiling, Go out unreacted monomer, then cooled down with cold water, carry out second and be stripped, so as to obtain new flucride siloxane IPN net Network hydrogel contact lens.
The survey of oxygen permeability coefficient and oxygen permeating amount is carried out according to the method in international ISO 18369.4 to the product in example 1 The measure of the fixed, fatigue resistance of the water content of contact lenses, eyeglass and contact lens other specification.Its experimental result is shown in Table.
Example 2：
In embodiment 1, the trifluoroethyl methacrylate in step A is replaced into Hexafluorobutyl mathacrylate, remaining all phase Together.Its experiment the results are shown in Table 1.
Embodiment 3：
In embodiment 1, the KH570 and the quality parts ratio of trifluoroethyl methacrylate in step A are changed to 1:1.8, its Remaining all identical, its experiment the results are shown in Table 1.
Embodiment 4：
In embodiment 1, the number of the mixed liquor in step B is changed to 10 parts, the number of methacrylic acid-beta-hydroxy ethyl ester is changed to 90 parts, remaining is all identical.Its experiment the results are shown in Table 1.
Embodiment 5：
In embodiment 1, the amount of the methyl isobutyrate of initiator azo two in step A is changed to 0.25% part, remaining is all identical. Its experiment the results are shown in Table 1.
Embodiment 6：
In embodiment 1, the amount of crosslinking agent tetraethylene-glycol dimethylacrylate in step B is changed to 0.3% part, remaining It is all identical.Its experiment the results are shown in Table 1.
Embodiment 7：
In embodiment 1, drying oven solidification temperature temperature in step C is set to 100 DEG C by 120 DEG C, remaining condition all phases Together.Its experiment the results are shown in Table 1.
Embodiment 8：
In embodiment 1, the solidified forming time in step C is had and be changed within 4 hours 6 hours, remaining condition is all identical.It is tested It the results are shown in Table 1.
Comparative example：
In embodiment 1, step A is directly removed, in stepb by quality parts ratio trifluoroethyl methacrylate：KH570 =1:1.5 add in 50ml beaker, add 0.2% part of two methyl isobutyrate of initiator azo, methacrylic acid-beta-hydroxy ethyl ester HEMA95 parts, 0.1% part of crosslinking agent, purge there-necked flask, under nitrogen protection magnetic agitation 10 hours with nitrogen at room temperature.Its Remaining condition is all identical, and its experiment the results are shown in Table 1.
Table 1
Note：Oxygen permeability coefficient unit：×10-11(cm2/S)(mlO2/ml x mmHg)。
It can be seen from table 1：The hydrogel lenses after hydrogel interpenetrating network technology are employed with this technology is not used Compare：Apply the machine that eyeglass is also improved while eyeglass water content, oxygen permeability are improved after hydrogel interpenetrating network technology Tool performance.
The content is only the basic explanation under present inventive concept, and according to technical scheme made it is any etc. Effect conversion, belongs to protection scope of the present invention.

Claims (4)

1. a kind of new flucride siloxane interpenetration network hydrogel contact lenses are comprised the following steps with its preparation method：
A：The synthesis of flucride siloxane hydrogel contact lens performed polymer：By quality parts ratio trifluoroethyl methacrylate： KH570=1:In 1.5-2.0, the beaker for adding 50ml, 0.2-1% parts of two methyl isobutyrate of initiator azo, side stirring are added Side is heated, and temperature control is at 30-50 DEG C, and then reactant is cooled to room temperature by isothermal reaction 0.5-2h；
B：The preparation of flucride siloxane hydrogel contact lens mixture：Above-mentioned mixed liquor 1-20 parts, methacrylic acid-β-hydroxyl second HEMA60-98 parts of ester, 0.1-1% parts of crosslinking agent, purge there-necked flask with nitrogen at room temperature, 1-10 are stirred under nitrogen protection small When；
C：A kind of preparation of new flucride siloxane hydrogel contact lens：Above-mentioned mixed liquor is molded entirely, by mould 80-140 DEG C is put into dry baking oven, and solidified forming time is 2-8 hours, carries out the first time demoulding, is put into the hot water of boiling 5-30min, unreacted monomer of going out, is then cooled down with cold water, is carried out second and is stripped, so as to obtain new fluorine-containing silica Alkane interpenetration network hydrogel contact lenses.
2. a kind of preparation method of above-mentioned new flucride siloxane hydrogel is required according to right 1, it is characterized in that：In step A Described trifluoroethyl methacrylate：：KH570 quality parts ratio is 0.5-3, most preferably 1.0-1.5；The whipping temp Preferably 30-45 DEG C, most preferably 35-45 DEG C；Mixing time is preferably 0.5-2h, most preferably 0.5-1h；Described initiation Agent is azodiisobutyronitrile, the methyl isobutyrate of azo two, benzoyl peroxide, the valeronitrile of azo two, lauroyl peroxide, hydrogen peroxide Change cumene, the preferably methyl isobutyrate of azo two.
3. a kind of preparation method of above-mentioned new flucride siloxane hydrogel is required according to right 1, it is characterized in that：In step B The mass fraction of described mixed liquor is preferably 2-15 parts, most preferably 2-10 parts；HEMA mass fraction is preferably 70-98 Part, most preferably 80-98 parts；Crosslinking agent is preferably 0.2-0.5%；Described crosslinking agent is ethylene glycol dimethacrylate, three Contracting tetraethylene glycol dimethylacrylate, N are N- methylene-bisacrylamides, trimethylol-propane trimethacrylate, three sweet Alcohol dimethylacrylate, tetramethyl disiloxane are double（Propyl methacrylate）, most preferably tetraethylene-glycol diformazan Base acrylate.
4. a kind of preparation method of above-mentioned new flucride siloxane interpenetration network hydrogel is required according to right 1, it is characterized in that： It is preferably 90-130 DEG C to set temperature described in step C in drying oven, most preferably 100-120 DEG C；Solidified forming time is excellent Turn to 3-7h, most preferably 4-6h；It is 5-20min, most preferably 5-10min to be put into time-optimized in the hot water of boiling.
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113103697A (en) * 2021-02-22 2021-07-13 苏州瑞尔康科技有限公司 Fluorosilicone hydrogel colored contact lens and preparation process thereof
CN115068669A (en) * 2022-06-08 2022-09-20 湖南工业大学 Triple-network porous embolism microsphere and preparation method thereof

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CN103941419A (en) * 2014-04-18 2014-07-23 江苏海伦隐形眼镜有限公司 Hydrogel cornea contact lens and preparation method thereof
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
CN105399954A (en) * 2015-12-23 2016-03-16 江苏海伦隐形眼镜有限公司 Hydrophilic siloxane oligomer, silicon hydrogel, corneal contact lens and preparation method

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CN103941419A (en) * 2014-04-18 2014-07-23 江苏海伦隐形眼镜有限公司 Hydrogel cornea contact lens and preparation method thereof
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
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CN113103697A (en) * 2021-02-22 2021-07-13 苏州瑞尔康科技有限公司 Fluorosilicone hydrogel colored contact lens and preparation process thereof
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CN115068669A (en) * 2022-06-08 2022-09-20 湖南工业大学 Triple-network porous embolism microsphere and preparation method thereof

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Address after: No.88 Changchun Street, Yongji Economic Development Zone, Jilin City, Jilin Province

Patentee after: Jilin Ruierkang Optical Technology Co.,Ltd.

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