CN114921081A - Photo-curing resin lens monomer and preparation method thereof - Google Patents
Photo-curing resin lens monomer and preparation method thereof Download PDFInfo
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- CN114921081A CN114921081A CN202210660330.8A CN202210660330A CN114921081A CN 114921081 A CN114921081 A CN 114921081A CN 202210660330 A CN202210660330 A CN 202210660330A CN 114921081 A CN114921081 A CN 114921081A
- Authority
- CN
- China
- Prior art keywords
- parts
- resin lens
- lens monomer
- monomer
- curing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 239000000178 monomer Substances 0.000 title claims abstract description 47
- 239000011347 resin Substances 0.000 title claims abstract description 44
- 229920005989 resin Polymers 0.000 title claims abstract description 44
- 238000000016 photochemical curing Methods 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title abstract description 10
- 238000001723 curing Methods 0.000 claims abstract description 26
- 239000002994 raw material Substances 0.000 claims abstract description 19
- 239000002904 solvent Substances 0.000 claims abstract description 16
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 11
- 239000004695 Polyether sulfone Substances 0.000 claims abstract description 10
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 10
- 230000002745 absorbent Effects 0.000 claims abstract description 10
- 239000002250 absorbent Substances 0.000 claims abstract description 10
- CPZVJYPXOWWFSW-QXMHVHEDSA-N dibenzyl (z)-but-2-enedioate Chemical compound C=1C=CC=CC=1COC(=O)\C=C/C(=O)OCC1=CC=CC=C1 CPZVJYPXOWWFSW-QXMHVHEDSA-N 0.000 claims abstract description 10
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 10
- 229920006393 polyether sulfone Polymers 0.000 claims abstract description 10
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 10
- 229920002338 polyhydroxyethylmethacrylate Polymers 0.000 claims abstract description 10
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000003756 stirring Methods 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 239000011521 glass Substances 0.000 claims description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical group C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 3
- 239000012965 benzophenone Substances 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000007872 degassing Methods 0.000 claims description 3
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical group C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 claims description 3
- 239000012153 distilled water Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 238000000465 moulding Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000006096 absorbing agent Substances 0.000 claims 1
- 230000004438 eyesight Effects 0.000 abstract description 3
- 230000000379 polymerizing effect Effects 0.000 abstract description 3
- 238000007493 shaping process Methods 0.000 abstract description 3
- 230000002265 prevention Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000003674 animal food additive Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Epoxy Resins (AREA)
Abstract
The invention discloses a photo-curing resin lens monomer which is prepared from the following raw materials in parts by weight: 5-15 parts of dibenzyl maleate, 5-15 parts of polyether sulfone, 30-50 parts of polyethylene glycol epoxy acrylate, 30-40 parts of polyhydroxyethyl methacrylate, 15-20 parts of octabromoether, 20-30 parts of n-butyl titanate, 5-8 parts of ultraviolet absorbent, 5-10 parts of curing agent and 25-30 parts of solvent. The monomer formed by polymerizing the components has higher refractive index and stronger impact resistance and wear resistance. The preparation method provided by the invention has the advantages of simple process, good controllability and repeatability of the process, mild reaction conditions, no pollution, low cost, high refractive index of the prepared product and good impact resistance. Through ultraviolet curing shaping, shorten curing time, guarantee lens product quality simultaneously, improve the comfort of wearing, effectively prevention and control eyesight.
Description
Technical Field
The invention belongs to the technical field of lens processing, and particularly relates to a photo-curing resin lens monomer and a preparation method thereof.
Background
At present, a thermosetting process is generally adopted in a resin lens forming process, the process is that a glass mold filled with optical resin monomers is pre-gelled for a certain time and then sent into curing equipment for heating, so that the optical resin monomers are cured and formed, the curing time is long, the production period is 20-40 hours, the production efficiency of the resin lens is seriously influenced, the production energy consumption is high, and the cost is high. In addition, the blending of the resin monomer also affects the curing efficiency and the surface definition and the optical refractive index of the lens, and a novel and efficient resin lens with better surface performance is lacked.
Disclosure of Invention
In view of this, the present application provides a photo-curable resin lens monomer and a preparation method thereof, which are used to solve the problems of poor quality of the lens monomer due to simple material preparation and low curing efficiency of the conventional resin lens monomer.
In order to solve the technical problem, the application discloses a photo-curing resin lens monomer which is prepared from the following raw materials in parts by weight: 5-15 parts of dibenzyl maleate, 5-15 parts of polyether sulfone, 30-50 parts of polyethylene glycol epoxy acrylate, 30-40 parts of polyhydroxyethyl methacrylate, 15-20 parts of octabromoether, 20-30 parts of n-butyl titanate, 5-8 parts of an ultraviolet absorbent, 5-10 parts of a curing agent and 25-30 parts of a solvent.
According to an embodiment of the present invention, the ultraviolet absorber is benzophenone.
According to an embodiment of the present invention, the curing agent is diaminodiphenylmethane.
According to an embodiment of the present invention, the solvent is methanol or isopropanol.
Further, the feed additive is prepared from the following raw materials in parts by weight: 10 parts of dibenzyl maleate, 10 parts of polyether sulfone, 40 parts of polyethylene glycol epoxy acrylate, 35 parts of polyhydroxyethyl methacrylate, 18 parts of octabromoether, 25 parts of n-butyl titanate, 8 parts of an ultraviolet absorbent, 8 parts of a curing agent and 28 parts of a solvent.
A preparation method of a photo-curing resin lens monomer comprises the following steps:
step 1, providing 5-15 parts of dibenzyl maleate, 5-15 parts of polyether sulfone, 30-50 parts of polyethylene glycol epoxy acrylate and 30-40 parts of polyhydroxyethyl methacrylate, preliminarily mixing to obtain a resin monomer A, and storing in vacuum;
step 2, providing 15-20 parts of octabromoether, 20-30 parts of n-butyl titanate and 25-30 parts of solvent, adding a catalyst, stirring at 60-90 ℃, reacting for 3-5 hours, removing the solvent by reduced pressure distillation after the reaction is finished, washing with distilled water, separating liquid, purifying the product by reduced pressure distillation, and preparing a mixture B;
step 3, stirring the resin monomer A and the mixture B in a vacuum reaction kettle for 1.5-2 hours in vacuum until the resin monomer A and the mixture B are fully dissolved to obtain a resin lens monomer raw material;
step 4, adding 5-8 parts of ultraviolet absorbent into the resin lens monomer raw material obtained in the step 3, stirring for 2-2.5 hours in vacuum, standing and degassing;
step 5, adding 5-10 parts of curing agent into the resin lens monomer raw material obtained in the step 4, and stirring for 20-30 min in vacuum;
step 6, pouring the resin lens monomer raw material obtained in the step 5 into a glass mold, and carrying out ultraviolet curing for 20-25min for molding;
and 7, separating the glass mold by using a mold opening knife to obtain the cured resin lens monomer.
Compared with the prior art, the invention can obtain the following technical effects:
the monomer formed by polymerizing each component has higher refractive index and stronger impact resistance and abrasion resistance. The preparation method provided by the invention has the advantages of simple process, good controllability and repeatability of the process, mild reaction conditions, no pollution, low cost, high refractive index of the prepared product and good impact resistance. Through ultraviolet curing shaping, shorten curing time, guarantee lens product quality simultaneously, improve the comfort of wearing, effectively prevent and control eyesight.
Of course, it is not necessary for any one product in which the invention is practiced to achieve all of the above-described technical effects simultaneously.
Detailed Description
The following embodiments are described in detail with reference to the accompanying drawings, so that the implementation process of the present invention for solving the technical problems and achieving the technical effects by applying technical means can be fully understood and implemented.
A photo-curing resin lens monomer is prepared from the following raw materials in parts by weight: 5-15 parts of dibenzyl maleate, 5-15 parts of polyether sulfone, 30-50 parts of polyethylene glycol epoxy acrylate, 30-40 parts of polyhydroxyethyl methacrylate, 15-20 parts of octabromoether, 20-30 parts of n-butyl titanate, 5-8 parts of ultraviolet absorbent, 5-10 parts of curing agent and 25-30 parts of solvent.
Preferably, the ultraviolet absorber is benzophenone. The curing agent is diaminodiphenylmethane. The solvent is methanol or isopropanol.
Further, the feed additive is prepared from the following raw materials in parts by weight: 10 parts of dibenzyl maleate, 10 parts of polyether sulfone, 40 parts of polyethylene glycol epoxy acrylate, 35 parts of polyhydroxyethyl methacrylate, 18 parts of octabromoether, 25 parts of n-butyl titanate, 8 parts of an ultraviolet absorbent, 8 parts of a curing agent and 28 parts of a solvent.
A preparation method of a photo-curing resin lens monomer comprises the following steps:
step 1, providing 5-15 parts of dibenzyl maleate, 5-15 parts of polyether sulfone, 30-50 parts of polyethylene glycol epoxy acrylate and 30-40 parts of polyhydroxyethyl methacrylate, preliminarily mixing to obtain a resin monomer A, and storing in vacuum;
step 2, providing 15-20 parts of octabromoether, 20-30 parts of n-butyl titanate and 25-30 parts of solvent, adding a catalyst, stirring at 60-90 ℃, reacting for 3-5 hours, removing the solvent by reduced pressure distillation after the reaction is finished, washing with distilled water, separating liquid, purifying the product by reduced pressure distillation, and preparing a mixture B;
step 3, stirring the resin monomer A and the mixture B in a vacuum reaction kettle for 1.5-2 hours in vacuum until the resin monomer A and the mixture B are fully dissolved to obtain a resin lens monomer raw material;
step 4, adding 5-8 parts of ultraviolet absorbent into the resin lens monomer raw material obtained in the step 3, stirring for 2-2.5h in vacuum, standing and degassing;
step 5, adding 5-10 parts of curing agent into the resin lens monomer raw material obtained in the step 4, and stirring for 20-30 min in vacuum;
step 6, pouring the resin lens monomer raw material obtained in the step 5 into a glass mold, and carrying out ultraviolet curing for 20-25min for molding;
and 7, separating the glass mold by using a mold opening knife to obtain the cured resin lens monomer.
The monomer formed by polymerizing the components has higher refractive index and stronger impact resistance and wear resistance. The preparation method provided by the invention has the advantages of simple process, good controllability and repeatability of the process, mild reaction conditions, no pollution, low cost, high refractive index of the prepared product and good impact resistance. Through ultraviolet curing shaping, shorten curing time, guarantee lens product quality simultaneously, improve the comfort of wearing, effectively prevent and control eyesight.
The foregoing description shows and describes several preferred embodiments of the present application, but as aforementioned, it is to be understood that the application is not limited to the forms disclosed herein, and is not to be construed as excluding other embodiments, but rather is capable of use in various other combinations, modifications, and environments and is capable of changes within the scope of the application as expressed herein, commensurate with the above teachings, or the skill or knowledge of the relevant art. And that modifications and variations may be effected by those skilled in the art without departing from the spirit and scope of the application, which is to be protected by the claims appended hereto.
Claims (6)
1. A photo-curing resin lens monomer is characterized by being prepared from the following raw materials in parts by weight: 5-15 parts of dibenzyl maleate, 5-15 parts of polyether sulfone, 30-50 parts of polyethylene glycol epoxy acrylate, 30-40 parts of polyhydroxyethyl methacrylate, 15-20 parts of octabromoether, 20-30 parts of n-butyl titanate, 5-8 parts of an ultraviolet absorbent, 5-10 parts of a curing agent and 25-30 parts of a solvent.
2. The photocurable lens monomer of claim 1, wherein said uv absorber is benzophenone.
3. The photocurable resin lens monomer of claim 1, wherein the curing agent is diaminodiphenylmethane.
4. The photocurable lens monomer of claim 1, wherein the solvent is methanol or isopropanol.
5. The photo-curable resin lens monomer according to claim 1, which is prepared from the following raw materials in parts by weight: 10 parts of dibenzyl maleate, 10 parts of polyether sulfone, 40 parts of polyethylene glycol epoxy acrylate, 35 parts of polyhydroxyethyl methacrylate, 18 parts of octabromoether, 25 parts of n-butyl titanate, 8 parts of ultraviolet absorbent, 8 parts of curing agent and 28 parts of solvent.
6. A method of preparing a photocurable resin lens monomer according to claim 1, comprising the steps of:
step 1, providing 5-15 parts of dibenzyl maleate, 5-15 parts of polyether sulfone, 30-50 parts of polyethylene glycol epoxy acrylate and 30-40 parts of polyhydroxyethyl methacrylate, preliminarily mixing to obtain a resin monomer A, and storing in vacuum;
step 2, providing 15-20 parts of octabromoether, 20-30 parts of n-butyl titanate and 25-30 parts of solvent, adding a catalyst, stirring at 60-90 ℃, reacting for 3-5 hours, removing the solvent by reduced pressure distillation after the reaction is finished, washing with distilled water, separating liquid, purifying the product by reduced pressure distillation, and preparing a mixture B;
step 3, stirring the resin monomer A and the mixture B in a vacuum reaction kettle for 1.5-2 hours in vacuum until the resin monomer A and the mixture B are fully dissolved to obtain a resin lens monomer raw material;
step 4, adding 5-8 parts of ultraviolet absorbent into the resin lens monomer raw material obtained in the step 3, stirring for 2-2.5 hours in vacuum, standing and degassing;
step 5, adding 5-10 parts of curing agent into the resin lens monomer raw material obtained in the step 4, and stirring for 20-30 min in vacuum;
step 6, pouring the resin lens monomer raw material obtained in the step 5 into a glass mold, and carrying out ultraviolet curing for 20-25min for molding;
and 7, separating the glass mold by using a mold opening knife to obtain the cured resin lens monomer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210660330.8A CN114921081A (en) | 2022-06-13 | 2022-06-13 | Photo-curing resin lens monomer and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210660330.8A CN114921081A (en) | 2022-06-13 | 2022-06-13 | Photo-curing resin lens monomer and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN114921081A true CN114921081A (en) | 2022-08-19 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210660330.8A Pending CN114921081A (en) | 2022-06-13 | 2022-06-13 | Photo-curing resin lens monomer and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114921081A (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105175608A (en) * | 2015-09-16 | 2015-12-23 | 寿光市鲁源盐化有限公司 | High-refractivity lens resin monomer |
| CN110720056A (en) * | 2017-05-31 | 2020-01-21 | 株式会社尼康依视路 | Spectacle lens, composition for forming primer layer, and method for producing spectacle lens |
| CN113717321A (en) * | 2021-09-22 | 2021-11-30 | 明月镜片股份有限公司 | Preparation method of light-cured resin lens monomer |
-
2022
- 2022-06-13 CN CN202210660330.8A patent/CN114921081A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105175608A (en) * | 2015-09-16 | 2015-12-23 | 寿光市鲁源盐化有限公司 | High-refractivity lens resin monomer |
| CN110720056A (en) * | 2017-05-31 | 2020-01-21 | 株式会社尼康依视路 | Spectacle lens, composition for forming primer layer, and method for producing spectacle lens |
| CN113717321A (en) * | 2021-09-22 | 2021-11-30 | 明月镜片股份有限公司 | Preparation method of light-cured resin lens monomer |
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Application publication date: 20220819 |