CN105061674B - A kind of formulation selection and new process of the silicone hydrogel contact lens of novel fluorine siloxanes - Google Patents
A kind of formulation selection and new process of the silicone hydrogel contact lens of novel fluorine siloxanes Download PDFInfo
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- 239000000017 hydrogel Substances 0.000 title claims abstract description 41
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 32
- -1 fluorine siloxanes Chemical class 0.000 title claims abstract description 18
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 16
- 239000011737 fluorine Substances 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title abstract description 16
- 239000000203 mixture Substances 0.000 title abstract description 7
- 238000009472 formulation Methods 0.000 title abstract description 6
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- 238000005498 polishing Methods 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
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- 239000003431 cross linking reagent Substances 0.000 claims abstract description 5
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- 238000006116 polymerization reaction Methods 0.000 claims abstract description 5
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000007710 freezing Methods 0.000 claims description 6
- 230000008014 freezing Effects 0.000 claims description 6
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
- 239000002504 physiological saline solution Substances 0.000 claims description 4
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- FMQPBWHSNCRVQJ-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-methylprop-2-enoate Chemical group CC(=C)C(=O)OC(C(F)(F)F)C(F)(F)F FMQPBWHSNCRVQJ-UHFFFAOYSA-N 0.000 claims description 2
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 claims description 2
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical group FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 2
- RINWGRJHXCCLOV-UHFFFAOYSA-N BPO Chemical compound BPO RINWGRJHXCCLOV-UHFFFAOYSA-N 0.000 claims description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 2
- 239000004006 olive oil Substances 0.000 claims description 2
- 235000008390 olive oil Nutrition 0.000 claims description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims 1
- 239000002245 particle Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 13
- 102100026735 Coagulation factor VIII Human genes 0.000 abstract description 7
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 abstract description 7
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 abstract description 7
- 238000005516 engineering process Methods 0.000 abstract description 7
- 239000007924 injection Substances 0.000 abstract description 2
- 238000002347 injection Methods 0.000 abstract description 2
- 238000000465 moulding Methods 0.000 abstract description 2
- 230000001954 sterilising effect Effects 0.000 abstract description 2
- 210000004556 brain Anatomy 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000011159 matrix material Substances 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 229920001707 polybutylene terephthalate Polymers 0.000 description 3
- 238000012805 post-processing Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
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- 238000011161 development Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical class CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- XJKVPKYVPCWHFO-UHFFFAOYSA-N silicon;hydrate Chemical compound O.[Si] XJKVPKYVPCWHFO-UHFFFAOYSA-N 0.000 description 1
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical compound [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Abstract
The present invention relates to a kind of formulation selection and new process of the silicone hydrogel contact lens of novel fluorine siloxanes.The technological process is：(1) preferable fluorosilicone and silicone compositions, hydrophilic monomer, non-hydrophilic monomers, crosslinking agent, ultraviolet absorber, initiator etc. are uniformly mixed.(2) injection mold is used, carries out hot polymerization or poly-reaction, curing molding.(3) matrix band is placed in 10~50 DEG C of liquid nitrogen frozen casees 5 30 minutes, takes out turning, polishing.(4) it is positioned over again in 10~40 DEG C of liquid nitrogen frozen casees after polishing, freezes 10 20 minutes, eyeglass separation is carried out with ingot stripper.(5) wash, extract, to obtain contact lenses in blocks for sterilizing.Silicone hydrogel contact lens production technology provided by the present invention, it can make existing conventional contact lenses producer original hydrogel (HEMA) contact lenses production equipment, produce new silicone hydrogel contact lens, save expensive special equipment investment, and substantial amounts of time, manpower and brain tactic.
Description
Technical field：
The present invention relates to a kind of formulation selection and new process of the silicone hydrogel contact lens of novel fluorine siloxanes.This hair
The production technology of bright provided silicone hydrogel contact lens, can make existing conventional contact lenses producer, use original water-setting
Glue (HEMA) contact lenses production equipment, produces new silicone hydrogel contact lens.This formulation selection and technique, are saved expensive
Novel production device investment, save the input cost of related substantial amounts of time, manpower and the special equipment talent.
Background technology：
Silicone hydrogel contact lens provide more preferably because of its good pliability and the oxygen permeability significantly improved to consumer
Comfort and the general level of the health, be current world's contact lenses industry development inevitable direction.
Due to the flexible nature of silicone-hydrogel material, turnery processing cannot be generally carried out.Produce silicon water-setting in the world at present
Glue contact lenses are using the method for injection molding.Full set molding production equipment is related to high-precision numerical control machine, die sleeve mould
Sophisticated design, detection and production.Required equipment investment is big, it is desirable to possesses and cultivates specialized personnel；Installation and debugging technical requirements height,
Time-consuming.Therefore general medium-sized and small enterprises are difficult to bear.More fear opinion silicone hydrogel contact lens formula technique and the height of technology
Threshold.
Since the country develops slowly in terms of silicone hydrogel lenses, each producer is main or produces methyl-prop with turning process
The hydrogel lenses of olefin(e) acid hydroxyl ethyl ester (HEMA) material.In recent years, domestic contact lenses company is also constantly attempting silicon water
The research and development of gel.But the Change cost of equipment is prohibitively expensive, the contact lenses company of many is set to have to continue production by gradually
Superseded HEMA eyeglasses.
The major reason that silicone hydrogel lenses are not suitable for turning process preparation is its material softness.In addition, silica gel material with
Strong adhesive force between polybutylene terephthalate (PBT) (PBT) mould, makes the demoulding difficult, or breakage rate is high.So one kind can car
Cut, can polish, eyeglass and the easy silicone hydrogel lenses production and processing technique of mold separation are domestic contact lenses industry institutes
Need.Such technique can use existing equipment, produce the silicone hydrogel lenses of high oxygen flow, of a high price without carrying out
Equipment and the talent renewal and investment.
Found through overtesting, freezing can increase the case hardness of silica gel eyeglass, so that silica gel eyeglass utilizes existing life
Produce equipment and carry out turning preparation.But refrigerating process must control, temperature is too low and overlong time, eyeglass can be caused to become fragile and collapse
Split.In demoulding link, decline by the bondability between the mould and eyeglass of freezing processing so that silica gel eyeglass can picture
HEMA materials eyeglass equally carries out mechanical stripping, significantly facilitates the progress of post processing.
The content of the invention：
1. technical problems to be solved
It is an object of the invention to research and develop a kind of formulation selection and aftertreatment technology, in order to utilize domestic production HEMA materials
The commonly used equipment of eyeglass, carries out the production and post processing of new silicone hydrogel contact lens.
2. technical solution
To achieve these goals, the present invention provides a kind of formula of the silicone hydrogel contact lens of novel fluorine siloxanes
Selection and new process, its feature include herein below：
Formula is characterized in that using the compound representated by (I) and similar structures compound as fluorosilicone materials：
Wherein：R1~R3 can be H or be F；R4 is for the alkyl of C2~4 or containing-F, the alkyl of-OH substituted radicals, R5
For the alkyl of C2~4.It includes the hydrophilic monomer that at least two are not limited to following material combination：N-vinyl pyrrolidone,
N- vinyl acetamides, N- methyl-Nvinylacetamides, N, N- dimethylvinylsiloxy acid amides, methacrylic acid, methacrylic acid
Glycidol；Also comprising one or two kinds of non-hydrophilic monomers, preferably hexafluoro isopropyl methacrylate；Also comprising a kind of crosslinking
Agent, preferably ethylene glycol dimethacrylate；Include a kind of thermal initiator, preferably azodiisobutyronitrile；Include a kind of ultraviolet suction
Receive agent preferred 2- [3- (2H- benzotriazole -2- bases) -4- hydroxy phenyls] Ethyl-2-Methyl acrylate.The weight of initiator is
The 0.3-1.2% of total amount, is preferably in a proportion of 0.7%, initiator including but not limited to：Thermal initiator AIBN, BPO, ADVN, may be used also
To use photoinitiator 1173,184,651, the preferred AIBN of hot polymerization, light gathers preferably 1173.
Silicone hydrogel lenses after gained polymerization, are positioned in -10~-50 DEG C of liquid nitrogen frozen casees 5-30 minutes (preferably -20
DEG C, freeze 15 minutes), then turning is carried out, polish.Eyeglass antiscuffing paste is preferred：Alpha-aluminium oxide: edible olive oil=1: 3 ratio tune
Match somebody with somebody.Gained silicone hydrogel lenses continue to be positioned over -10~-40 DEG C and freeze 10-20 minute after polishing, use ingot stripper progress eyeglass
Separation (preferably -30 DEG C, freeze 15 minutes), the eyeglass after the demoulding is cleaned by ultrasonic using weak lye, preferably 0.5% sodium bicarbonate water
Solution.
Eyeglass extracting process is：Washing complete rear lens with 50% ethanol vibration 1 it is small when, maintenance 20~25 degree of temperature；Again
With 30% ethanol vibration 2 it is small when, maintain 20~25 degree of temperature, then replaced with physiological saline, balance 24 it is small when more than.
3. beneficial effect
It is an object of the invention to research and develop a kind of existing equipment that HEMA material eyeglasses are produced using domestic mainstream, directly
For the production and post processing of silicone hydrogel contact lens, so as to reduce upper huge equipment investment during equipment production, save big
Amount fund, equipment, professional and time cost.
Embodiment：
Following embodiments are used to illustrate the present invention, but are not limited to the scope of application of the present invention.
Embodiment 1：
(1) 10L round-bottomed flasks are chosen, sequentially add 40 parts of fluorosilicone monomer (I), 45 parts of hydroaropic substance, non-hydrophilic
10 parts of material of property, 4 parts of crosslinking agent, ultraviolet absorber 0.5%, initiator 0.5%, are sufficiently mixed, mould fluid injection, polymerization forming,
The dry plate of mould must be attached to.
(2) mould and dry plate are placed in -10 DEG C of environment 30 minutes, take out turning, from freezing state to turning complete when
Between control in less than 8 minutes, 10 minutes, complete the polishing of die blade polishing machine.
(3) die blade has been polished to be placed in -20 DEG C of environment 20 minutes, has carried out mold separation with ingot stripper, obtain eyeglass and do
Piece.
(4) in 20~25 DEG C of environment, dry plate is added into 0.5% sodium bicarbonate aqueous solution, is cleaned by ultrasonic 30 minutes, then
With clear water rinsing twice, eyeglass is separated from water, and is put into 50% ethanol, when gently vibration 1 is small, then it is small with the vibration 2 of 30% ethanol
When, finally replaced 2 times with physiological saline, when standing balance 24 is small in physiological saline, steam sterilizing, obtains final eyeglass.
Embodiment 1~7, formula rate, aftertreatment technology condition are varied from, and basic operation is same as Example 1, formula
Ratio is shown in Table one, and aftertreatment technology and testing result are shown in Table two.
Table one：Embodiment 1~7 matches
Table two：1~7 post-treatment condition of embodiment and result
Table one, table two the results show that 60% and the silicone hydrogel lenses of following fluorosilicone content can be obtained with this technique
Preferable shape, and the preferably eyeglass of surface quality.But when fluorosilicone reaches 70%, the turning effect after freezing is also not bery
It is preferable.
Claims (11)
1. a kind of silicone hydrogel contact lens of novel fluorine siloxanes, it is characterised in that formed including following polymerization
Silicone-hydrogel piece：
(1) with (I) representated by compound：
Wherein：R1~R3 can be H or be F；R4 is for the alkyl of C2~4 or containing-F, the alkyl of-OH substituted radicals, R5 C2
~4 alkyl；
(2) at least two hydrophilic monomers, it includes the combination of following material：N-vinyl pyrrolidone, N- vinylacetyls
Amine, N- methyl-Nvinylacetamides, N, N- dimethylvinylsiloxy acid amides, methacrylic acid, methyl propenoic acid glycidyl；Also
Include a kind of non-hydrophilic monomer, a kind of crosslinking agent, a kind of ultraviolet absorber and a kind of initiator.
2. the silicone hydrogel contact lens of novel fluorine siloxanes according to claim 1, it is characterised in that：Non-hydrophilic
Monomer is hexafluoro isopropyl methacrylate, crosslinking agent is ethylene glycol dimethacrylate, initiator be azodiisobutyronitrile,
Ultraviolet absorber is 2- [3- (2H- benzotriazole -2- bases) -4- hydroxy phenyls] Ethyl-2-Methyl acrylate.
3. the silicone hydrogel contact lens of novel fluorine siloxanes according to claim 1, it is characterised in that initiator
Weight is the 0.3-1.2% of total amount, and initiator is the one or more in thermal initiator AIBN, BPO, ADVN, or photoinitiator
1173rd, the one or more in 184,651.
4. the silicone hydrogel contact lens of novel fluorine siloxanes according to claim 1, it is characterised in that gained polymerize
Silicone-hydrogel piece afterwards, is placed in -10~-50 DEG C of liquid nitrogen frozen casees and carries out turning again after 5-30 minutes, polishing.
5. the silicone hydrogel contact lens of novel fluorine siloxanes according to claim 4, it is characterised in that liquid nitrogen frozen
Box temperature degree is -20 DEG C, and cooling time is 15 minutes.
6. the silicone hydrogel contact lens of novel fluorine siloxanes according to claim 4, it is characterised in that silicone-hydrogel
When piece polishes, antiscuffing paste by 5 μm of particle diameter alpha-aluminium oxide: edible olive oil=1: the allotment of 3 ratios forms.
7. the silicone hydrogel contact lens of novel fluorine siloxanes according to claim 4, it is characterised in that after polishing
Silicone-hydrogel piece is positioned at a temperature of -10~-40 DEG C again, after freezing 10-20 minutes, uses ingot stripper to carry out mould, eyeglass
Separation.
8. the silicone hydrogel contact lens of novel fluorine siloxanes according to claim 7, it is characterised in that after polishing
Silicone-hydrogel piece is placed at a temperature of -30 DEG C, after freezing 15 minutes, uses ingot stripper to carry out mould, eyeglass separation.
9. the silicone hydrogel contact lens of novel fluorine siloxanes according to claim 7, it is characterised in that after the demoulding
Silicone-hydrogel piece is cleaned by ultrasonic using weak base aqueous solution.
10. the silicone hydrogel contact lens of novel fluorine siloxanes according to claim 9, it is characterised in that week-base water
Solution is the sodium bicarbonate aqueous solution of mass fraction 0.5%.
11. the silicone hydrogel contact lens of novel fluorine siloxanes according to claim 9, it is characterised in that washed
Into rear silicone-hydrogel piece with 50% ethanol vibration 1 it is small when, maintain 20~25 DEG C of temperature；Again with 30% ethanol vibration 2 it is small when, maintain
20~25 DEG C of temperature；Replaced again with physiological saline, balance 24 it is small when more than.
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| CN201510487090.6A CN105061674B (en) | 2015-08-10 | 2015-08-10 | A kind of formulation selection and new process of the silicone hydrogel contact lens of novel fluorine siloxanes |
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| CN201510487090.6A CN105061674B (en) | 2015-08-10 | 2015-08-10 | A kind of formulation selection and new process of the silicone hydrogel contact lens of novel fluorine siloxanes |
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| CN106950717B (en) * | 2016-01-06 | 2019-10-22 | 吉林化工学院 | A kind of preparation method of fluorine-containing siloxane interpenetrating network hydrogel |
| CN109796556B (en) * | 2019-01-11 | 2021-06-11 | 华诺森（武汉）生物医药技术有限公司 | Preparation method of mechanically demouldable silicone hydrogel contact lens |
| CN113103697B (en) * | 2021-02-22 | 2022-08-09 | 苏州瑞尔康科技有限公司 | Fluorine-silicon hydrogel colored contact lens and preparation process thereof |
| CN112851853A (en) * | 2021-02-26 | 2021-05-28 | 爱生华(苏州)光学有限公司 | Preparation method of silicone hydrogel contact lens |
| CN114853955A (en) * | 2022-05-31 | 2022-08-05 | 爱生华(苏州)光学有限公司 | Preparation method of high oxygen permeability super-soft silicone hydrogel daily-throwing-through tablet |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4327203A (en) * | 1981-02-26 | 1982-04-27 | Bausch & Lomb Incorporated | Polysiloxane with cycloalkyl modifier composition and biomedical devices |
| US4355147A (en) * | 1981-02-26 | 1982-10-19 | Bausch & Lomb Incorporated | Polysiloxane with polycyclic modifier composition and biomedical devices |
| US5321108A (en) * | 1993-02-12 | 1994-06-14 | Bausch & Lomb Incorporated | Fluorosilicone hydrogels |
| AU713509B2 (en) * | 1995-12-07 | 1999-12-02 | Bausch & Lomb Incorporated | Monomeric units useful for reducing the modulus of silicone hydrogels |
| US20040054026A1 (en) * | 2002-09-18 | 2004-03-18 | Kunzler Jay F. | Elastomeric, expandable hydrogel compositions |
| CN102675561B (en) * | 2011-03-07 | 2014-10-22 | 远东新世纪股份有限公司 | silicone hydrogel with high water content |
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