CN114736374A - High oxygen permeable silica hydrogel raw material for orthokeratology lens and preparation method thereof - Google Patents
High oxygen permeable silica hydrogel raw material for orthokeratology lens and preparation method thereof Download PDFInfo
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- CN114736374A CN114736374A CN202210365114.0A CN202210365114A CN114736374A CN 114736374 A CN114736374 A CN 114736374A CN 202210365114 A CN202210365114 A CN 202210365114A CN 114736374 A CN114736374 A CN 114736374A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
- G02B1/043—Contact lenses
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Abstract
The invention provides a high oxygen permeability silicon hydrogel raw material for a corneal plastic lens and a preparation method thereof. The end group of the organic silicon macromolecule is unsaturated group, the main chain contains a large number of siloxane structures, and the product prepared from the material has good oxygen transmission, hydrolytic stability, biological stability, light transmittance and higher mechanical property.
Description
Technical Field
The invention relates to the technical field of contact lenses, in particular to a high oxygen permeable silicon hydrogel raw material for a corneal plastic lens and a preparation method thereof
Background art:
the main material used for the production of the cornea plastic mirror (OK mirror) in the early days is polymethyl methacrylate (PMMA), which is hydrogel, and due to the poor oxygen permeability of hydrogel, the cornea cannot absorb enough oxygen for metabolism, and after wearing for a period of time, a series of discomfort symptoms including hyperemia, dryness, foreign body sensation and blurred vision will appear. The silicon hydrogel has two channels of an organic silicon phase and a hydrogel phase for conveying oxygen, has higher oxygen permeability, and can well solve the discomfort symptoms when used for the corneal contact lens. Therefore, highly oxygen permeable orthokeratology lenses based on silicone hydrogels have become a hot spot for numerous large international studies.
The high oxygen permeability silica hydrogel materials have been developed for three generations, the main raw materials for producing orthokeratology lenses at present are monopolized by Gelest and Dowcorning, and the import price is high.
Disclosure of Invention
The invention provides a high oxygen permeability silicon hydrogel raw material for a corneal plastic lens and a preparation method thereof.
The adopted specific technical scheme is as follows: a high oxygen permeable silicone hydrogel raw material for a corneal shaping lens has a structure as shown in formula I:
wherein n is 50-800.
Further, the invention provides a preparation method of the silicon hydrogel raw material for the orthokeratology lens, which comprises the following steps: using dichloromethane as a solvent, mixing micromolecular silane and allyl methacrylate for hydrosilylation reaction at the water bath temperature controlled by 20-40 ℃, reacting for 22-26h to prepare bis (allyl methacrylate) disiloxane, then adding trifluoromethanesulfonic acid, adding octamethylcyclotetrasiloxane or one of 3, 5, 7-tetramethylcyclotetrasiloxane, cooling to below 20 ℃, synthesizing organosilicon macromonomer through anion ring-opening polymerization, reacting for 22-26h, and removing dichloromethane in the solution after the reaction is finished to obtain the high oxygen permeable silica hydrogel raw material.
Dichloromethane is used as a solvent for two times, wherein the first time is to dissolve small-molecule silane and allyl methacrylate in dichloromethane for reaction, the second time is to dissolve octamethylcyclotetrasiloxane or 3, 5, 7-tetramethylcyclotetrasiloxane in dichloromethane for preparation of a solution, and the total mass of dichloromethane used in the whole preparation process is about (3.4-6.3): 1.
further, the small molecule silane monomer has a structure as shown in formula II:
further, the small molecule silane: allyl methacrylate: the mass ratio of octamethylcyclotetrasiloxane or 3, 5, 7-tetramethylcyclotetrasiloxane is 1: (2-3.8): (6.5-10).
The trifluoromethanesulfonic acid is generally added in an amount of about 0.1% of the total mass of allyl methacrylate.
Further, the invention also provides another preparation method of the silicon hydrogel raw material for the orthokeratology lens, which comprises the following steps: using dichloromethane as a solvent, performing hydrosilylation reaction on hydrogen-terminated silicone oil and allyl methacrylate in a water bath at the temperature of 50-70 ℃ to synthesize an organic silicon macromonomer, reacting for 46-50h, and removing dichloromethane in the solution after the reaction is finished to obtain the high oxygen permeable silicone hydrogel raw material.
Further, the terminal hydrogen-containing silicone oil has a structure of formula III:
wherein k is 50-800.
Further, the terminal hydrogen-containing silicone oil: the using ratio of allyl methacrylate is 1: (0.4-0.6).
Dichloromethane is used as solvent, and the total mass of dichloromethane to the total mass of allyl methacrylate is about (4.5-8.5): 1.
further, the invention also provides another preparation method of the silicon hydrogel raw material for the orthokeratology lens, which comprises the following steps: using dichloromethane as a solvent, performing water bath temperature control at 60-70 ℃, reacting hydrogen-terminated silicone oil with allyl alcohol for 22-26h to prepare an intermediate monomer, performing addition reaction polymerization on the intermediate monomer and an addition reagent to obtain an organic silicon macromonomer, and reacting for 22-26h to obtain a high oxygen-permeable silicon hydrogel raw material;
the intermediate monomer has a structure of formula IV:
wherein m is 50-800;
the addition reagent comprises any one of methacryloyl chloride or methyl methacrylate.
Further, the ratio of the hydrogen-terminated silicone oil to the allyl alcohol is 1: (0.3-1).
Dichloromethane as solvent, generally the total mass of dichloromethane to the total mass of allyl alcohol is about (4-5.5): 1.
the invention also provides a silicone hydrogel lens comprising the silicone hydrogel raw material for orthokeratology lens as claimed in claim 1.
The invention has the beneficial effects that:
the synthesized organic silicon macromolecule is a high oxygen permeability silicon hydrogel material, the synthetic raw materials are cheap and easy to purchase, the reaction steps are simple, the reaction time is short, the purity is high, and the production cost of the corneal plastic lens is reduced.
The siloxane prepolymer can endow the lens with high oxygen permeability and certain mechanical strength, and the oxygen permeability of the silicon hydrogel is only related to the content of the silicon-oxygen group and is not related to the structure of the silicon-oxygen group, so that the invention synthesizes the organic silicon macromonomer with an unsaturated end group and a main chain containing a large number of siloxane structures, and the product prepared from the material has good oxygen transmission, hydrolytic stability, biological stability, light transmittance and higher mechanical properties.
Detailed Description
The following specific embodiments are provided to further illustrate the present invention, but the present invention is not limited to only the following embodiments.
The invention provides a silicon hydrogel raw material for a corneal plastic lens and a preparation method thereof, wherein the synthesized organic silicon macromolecule is a high-oxygen-permeability silicon hydrogel material, the synthesized raw material is cheap and easy to purchase, the reaction step is simple, the reaction time is short, the purity is high, and the production cost of the corneal plastic lens is reduced.
The above silicone macromolecule can be prepared by three methods, in which the amount of the platinum catalyst used in a part of the reaction steps is about 0.01 to 1ppm based on the total mass of the substances participating in the reaction step.
The method comprises the following steps: mixing micromolecular silane and allyl methacrylate under the water bath temperature controlled at 20-40 ℃ by taking dichloromethane as a solvent to perform hydrosilylation reaction for 22-26h to prepare bis (allyl methacrylate) disiloxane, then adding one of trifluoromethanesulfonic acid, octamethylcyclotetrasiloxane (D3) or 3, 5, 7-tetramethylcyclotetrasiloxane (D4), cooling to below 20 ℃, synthesizing an organosilicon macromonomer through anion ring-opening polymerization, reacting for 22-26h, and removing dichloromethane in the solution after the reaction is finished to obtain a silicon hydrogel raw material;
the second method comprises the following steps: using dichloromethane as a solvent, performing hydrosilylation reaction on hydrogen-terminated silicone oil and allyl methacrylate in a water bath at the temperature of 50-70 ℃ to synthesize an organic silicon macromonomer, reacting for 46-50h, and removing dichloromethane in the solution after the reaction is finished to obtain a silicon hydrogel raw material;
the third method comprises the following steps: using dichloromethane as a solvent, performing water bath temperature control at 60-70 ℃, reacting hydrogen-terminated silicone oil with allyl alcohol for 22-26h to prepare an intermediate monomer, performing addition reaction polymerization on the intermediate monomer and an addition reagent to obtain an organic silicon macromonomer, and reacting for 22-26h to obtain a silicon hydrogel raw material;
the present invention will be further illustrated with reference to the following specific examples, but the present invention is not limited to the following examples. The experimental methods used in the examples are all conventional methods unless otherwise specified.
Materials, reagents and the like used in the following examples are commercially available unless otherwise specified.
Example 1
Adding 70.8g of dichloromethane into a 500mL four-mouth bottle, stirring, adding 13.43g of weighed 1,1,3, 3-tetramethyldisiloxane, controlling the temperature of a water bath to be 20 ℃, adding 100 mu g of platinum catalyst, placing 27.72g of allyl methacrylate into a constant-pressure dropping funnel, adding into the reaction solution under the temperature control, and continuing to perform heat preservation reaction for 24 hours after the addition is finished; continuously adding 0.027g of trifluoromethanesulfonic acid into the solution, dissolving 89.25g of octamethylcyclotetrasiloxane in 100g of dichloromethane to obtain an octamethylcyclotetrasiloxane solution, cooling the reaction system to below 20 ℃, dropwise adding the octamethylcyclotetrasiloxane solution, continuously preserving the temperature for 22 hours after dropwise adding is completed, washing the reaction solution for multiple times after the reaction is completed, and removing dichloromethane in the solution to obtain the product.
Example 2
Adding 71.3g of dichloromethane into a 500mL four-mouth bottle, stirring, adding 13.58g of weighed 1,1,3, 3-tetramethyldisiloxane, controlling the temperature in a water bath at 40 ℃, adding 100 mu g of platinum catalyst, placing 50g of allyl methacrylate into a constant-pressure dropping funnel, adding into the reaction solution at the controlled temperature, and continuing to perform heat preservation reaction for 24 hours after the addition is finished; continuously adding 0.05g of trifluoromethanesulfonic acid into the solution, dissolving 133.5g of octamethylcyclotetrasiloxane in 100g of dichloromethane to obtain an octamethylcyclotetrasiloxane solution, cooling to below 20 ℃, dropwise adding the octamethylcyclotetrasiloxane solution, continuously carrying out heat preservation reaction for 24 hours after the dropwise adding is finished, washing the reaction solution for multiple times after the reaction is finished, and removing the dichloromethane in the solution to obtain the product.
Example 3
Adding 72.0g of dichloromethane into a 500mL four-mouth bottle, stirring, adding 13.44g of weighed 1,1,3, 3-tetramethyldisiloxane, controlling the temperature in a water bath at 30 ℃, adding 0.4 mu g of platinum catalyst, placing 41.6g of allyl methacrylate into a constant-pressure dropping funnel, adding into the reaction solution under the temperature control, and continuing to perform heat preservation reaction for 24 hours after the addition is finished; continuously adding 0.04g of trifluoromethanesulfonic acid into the solution, dissolving 120.5g of 1,3, 5, 7-tetramethylcyclotetrasiloxane in 100g of dichloromethane to obtain a 1,3, 5, 7-tetramethylcyclotetrasiloxane solution, cooling to below 20 ℃, dropwise adding the 1,3, 5, 7-tetramethylcyclotetrasiloxane solution, continuously preserving the temperature for 26 hours after dropwise adding is finished, washing the reaction solution with water for multiple times after the reaction is finished, and removing dichloromethane from the solution to obtain the product.
Example 4:
adding 123.66g of dichloromethane into a 500mL four-mouth bottle, stirring, adding 35.28g of weighed silicone oil, controlling the temperature of a water bath to 50 ℃, adding a proper amount of platinum catalyst, placing 15.25g of allyl methacrylate into a constant-pressure dropping funnel, adding the mixture into a reaction solution under the controlled temperature, keeping the temperature, stirring and reacting for 46 hours, then adding 50mL of clear water into the reaction solution, carrying out layered organic washing on the reaction solution for multiple times in succession, and removing the dichloromethane in the solution to obtain the final product.
Example 5
Adding 125.73g of dichloromethane into a 500mL four-mouth bottle, stirring, adding 35.19g of weighed silicone oil, controlling the temperature of a water bath at 70 ℃, adding a proper amount of platinum catalyst, placing 25.21g of allyl methacrylate into a constant-pressure dropping funnel, adding the allyl methacrylate into the reaction solution under the controlled temperature, keeping the temperature, stirring and reacting for 48 hours, then adding 50mL of clear water into the reaction solution, carrying out layered organic washing on the reaction solution for multiple times in succession, and removing the dichloromethane from the solution to obtain the final product.
Example 6
Adding 122.03g of dichloromethane into a 500mL four-mouth bottle, stirring, adding 34.87g of weighed silicone oil, controlling the temperature of a water bath to be 60 ℃, adding a proper amount of platinum catalyst, placing 21.63g of allyl methacrylate into a constant-pressure dropping funnel, adding the allyl methacrylate into a reaction solution under the temperature control, keeping the temperature and stirring for reaction for 50 hours, then adding 50mL of clear water into the reaction solution, carrying out layered organic washing on the reaction solution for multiple times in succession, and removing the dichloromethane from the solution to obtain the final product.
Example 7
Adding 100.52g of dichloromethane into a 500mL four-mouth bottle, stirring, adding 34.51g of weighed silicone oil, controlling the temperature in a water bath at 50 ℃, adding a proper amount of platinum catalyst, placing 23.61g of allyl alcohol into a constant-pressure dropping funnel, adding into the reaction liquid under the temperature control, and continuing to perform heat preservation reaction for 22 hours after the addition is finished; and (3) continuously adding 153.7g of methacryloyl chloride into the solution, dropwise adding the methacryloyl chloride, continuously carrying out heat preservation reaction for 24 hours, washing the reaction solution for multiple times after the reaction is finished, and removing dichloromethane in the solution to obtain the product.
Example 8
Adding 118.06g of dichloromethane into a 500mL four-mouth bottle, stirring, adding 38.33g of weighed silicone oil, controlling the temperature of a water bath to be 75 ℃, adding a proper amount of platinum catalyst, placing 23.73g of allyl alcohol into a constant-pressure dropping funnel, adding into the reaction solution under the controlled temperature, and continuing to perform heat preservation reaction for 24 hours after the addition is finished; and continuously adding 97.66g of methyl methacrylate into the solution, dropwise adding the methyl methacrylate, continuously carrying out heat preservation reaction for 22 hours, washing the reaction solution for multiple times after the reaction is finished, and removing dichloromethane in the solution to obtain the product.
Example 9
Adding 132.77g of dichloromethane into a 500mL four-mouth bottle, stirring, adding 36.21g of weighed silicone oil, controlling the temperature in a water bath to be 62 ℃, adding a proper amount of platinum catalyst, placing 26.01g of allyl alcohol into a constant-pressure dropping funnel, adding into the reaction solution under the controlled temperature, and continuing to perform heat preservation reaction for 26 hours after the addition is finished; and continuously adding 100.3g of methyl methacrylate into the solution, dropwise adding the methyl methacrylate, continuously keeping the temperature and reacting for 26 hours, washing the reaction solution for multiple times after the reaction is finished, and removing dichloromethane in the solution to obtain the product.
The products obtained in examples 1 to 9 were used as raw materials of silicone macromonomers to prepare silicone hydrogel lenses, and the specific preparation formula (parts by weight) was as follows:
silicone macromer (material made by the invention): 25 parts of (1);
hydrophilic monomer: 33 parts of hydroxyethyl methacrylate, 22.5 parts of N-vinyl pyrrolidone and 22.5 parts of N-methyl-N-vinyl acetamide;
a crosslinking agent: 0.7 part of ethylene glycol dimethacrylate;
initiator: 0.5 part of azobisisobutyronitrile;
the preparation method of the orthokeratology lens adopts the international popular way: firstly, mixing all monomers, an initiator and a cross-linking agent according to the formula to obtain a polymerization solution, filling the polymerization solution into a plastic mold, introducing nitrogen, heating and curing, cutting a polymer rod obtained after curing into a button shape by using a lathe, and finally cutting the front side and the back side of the material in the button shape to obtain the cornea shaping lens (the preparation processes of the embodiments 1 to 9 are the same).
The lenses obtained were subjected to performance tests, the results of which are shown in table 1:
oxygen permeability coefficient: the test was carried out using the Coulomb method under the national Standard (GBT 11417.3-2012).
Refractive index: the refractive index was measured at 20 ℃ according to ASTM D1218, standard test methods for refractive index and refractive index dispersion of hydrocarbon liquids.
Shore hardness: measurement was carried out using a Shore D durometer.
Modulus: the young's modulus of the water-containing films was measured using an Instron tensile tester.
TABLE 1
Claims (10)
1. A high oxygen permeable silicone hydrogel starting material for use in orthokeratology, having a structure according to formula I:
wherein n is 50-800.
2. The method for preparing the high oxygen permeability silicon hydrogel raw material for the orthokeratology lens as claimed in claim 1, which comprises the following steps: using dichloromethane as a solvent, mixing micromolecular silane and allyl methacrylate for hydrosilylation reaction at the water bath temperature controlled by 20-40 ℃, reacting for 22-26h to prepare bis (allyl methacrylate) disiloxane, then adding trifluoromethanesulfonic acid, adding octamethylcyclotetrasiloxane or one of 1,3, 5, 7-tetramethylcyclotetrasiloxane, cooling to below 20 ℃, synthesizing an organosilicon macromonomer through anion ring-opening polymerization, reacting for 22-26h, and removing dichloromethane in the solution after the reaction is finished to obtain the high oxygen permeable silica hydrogel raw material.
3. The method for preparing the high oxygen permeability silicon hydrogel raw material for the orthokeratology lens as claimed in claim 2, wherein the small molecule silane has a structure as shown in formula II:
4. the preparation method of the high oxygen permeability silicon hydrogel raw material for the orthokeratology lens as claimed in claim 2, characterized in that the small molecule silane: allyl methacrylate: the mass ratio of octamethylcyclotetrasiloxane or 3, 5, 7-tetramethylcyclotetrasiloxane is 1: (2-3.8): (6.5-10).
5. The method for preparing the high oxygen permeability silicon hydrogel raw material for the orthokeratology lens as claimed in claim 1, which comprises the following steps: using dichloromethane as a solvent, carrying out hydrosilylation reaction on hydrogen-terminated silicone oil and allyl methacrylate at the water bath temperature controlled of 50-70 ℃ to synthesize an organic silicon macromonomer, reacting for 46-50h, and removing dichloromethane in the solution after the reaction is finished to obtain the high oxygen permeable silicone hydrogel raw material.
6. The method for preparing the high oxygen permeable silicone hydrogel raw material for orthokeratology lens as claimed in claim 5, wherein the terminal hydrogen-containing silicone oil has a structure of formula III:
wherein k is 50-800.
7. The method for preparing the high oxygen permeability silicone hydrogel raw material for the orthokeratology lens as claimed in claim 5, wherein the terminal hydrogen-containing silicone oil: the mass ratio of allyl methacrylate is 1: (0.4-0.6).
8. The method for preparing the high oxygen permeable silicone hydrogel raw material for the orthokeratology lens as claimed in claim 1, wherein dichloromethane is used as a solvent, water bath temperature is controlled at 60-70 ℃, hydrogen-terminated silicone oil is adopted to react with allyl alcohol for 22-26h to prepare an intermediate monomer, the intermediate monomer and an addition reagent are subjected to addition polymerization to obtain an organic silicone macromonomer, and the reaction is carried out for 22-26h to obtain the high oxygen permeable silicone hydrogel raw material;
the intermediate monomer has a structure shown in formula IV:
wherein m is 50-800;
the addition reagent comprises any one of methacryloyl chloride or methyl methacrylate.
9. The method for preparing the high oxygen permeability silicone hydrogel raw material for orthokeratology lens as claimed in claim 7, wherein the terminal hydrogen-containing silicone oil: the mass ratio of the allyl alcohol is 1: (0.3-1).
10. A silicone hydrogel lens comprising the highly oxygen permeable silicone hydrogel starting material for orthokeratology lens of claim 1.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008268488A (en) * | 2007-04-19 | 2008-11-06 | Seed Co Ltd | Hydrous ophthalmic lens |
| US20180100038A1 (en) * | 2016-10-11 | 2018-04-12 | Novartis Ag | Polymerizable polydimethylsiloxane-polyoxyalkylene block copolymers |
| CN110036057A (en) * | 2016-12-14 | 2019-07-19 | 罗门哈斯公司 | It is used to prepare the non-toxic catalyst of polysiloxanes (methyl) acrylate |
| CN113416310A (en) * | 2021-05-31 | 2021-09-21 | 南京林业大学 | Preparation method of organic silicon modified acrylate |
-
2022
- 2022-04-07 CN CN202210365114.0A patent/CN114736374A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008268488A (en) * | 2007-04-19 | 2008-11-06 | Seed Co Ltd | Hydrous ophthalmic lens |
| US20180100038A1 (en) * | 2016-10-11 | 2018-04-12 | Novartis Ag | Polymerizable polydimethylsiloxane-polyoxyalkylene block copolymers |
| CN110036057A (en) * | 2016-12-14 | 2019-07-19 | 罗门哈斯公司 | It is used to prepare the non-toxic catalyst of polysiloxanes (methyl) acrylate |
| CN113416310A (en) * | 2021-05-31 | 2021-09-21 | 南京林业大学 | Preparation method of organic silicon modified acrylate |
Non-Patent Citations (2)
| Title |
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| BENJAMIN T.CHEESMAN等: ""Linear and star architecture methacrylate-functionalised PDMS"" * |
| THONG-ON, BANDIT等: ""Controlled nanoclustering of magnetic nanoparticles using telechelic polysiloxane and disiloxane"" * |
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