CN107092043B - 1.67 polyurethane lens with blue-violet protection performance and manufacturing method thereof - Google Patents
1.67 polyurethane lens with blue-violet protection performance and manufacturing method thereof Download PDFInfo
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- CN107092043B CN107092043B CN201710338793.1A CN201710338793A CN107092043B CN 107092043 B CN107092043 B CN 107092043B CN 201710338793 A CN201710338793 A CN 201710338793A CN 107092043 B CN107092043 B CN 107092043B
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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
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
- C08G18/3876—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing mercapto groups
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Abstract
The invention relates to a 1.67 polyurethane lens with blue and violet light protection performance and a manufacturing method thereof, which is characterized in that: the lens resin formula adopts 4, 8-dimercaptomethyl-1, 11 dimercapto-3, 6, 9-trithioundecane: 5% -50%; 5, 7-dimercaptomethyl-1, 11-dimercapto-3, 6, 9-trithiaundecane: 5% -50%; bis (2,2 mercapto) ethyl tetrasulfide: 5% -50%; m-xylylene isocyanate: 5% -50%; cyclohexane dimethylene diisocyanate: 5 to 50 percent of five resins are compounded, the catalyst adopts an organic tin catalyst, the blue-violet light absorbent adopts benzotriazole and benzophenone, the organic dye adopts red, green and blue dyes, and the dyes are used for toning the substrate. The refractive index of the substrate of the resin lens obtained by polymerizing the resin is 1.67, and the visible light transmittance of the lens obtained by hard coating the substrate is more than or equal to 93 percent; the blue-violet light transmittance is respectively 280nm to 380nm, and the transmittance is less than or equal to 0.5 percent; 380nm-420nm is less than or equal to 20 percent.
Description
[ technical field ] A method for producing a semiconductor device
The invention relates to the technical field of polyurethane lens production, in particular to a 1.67 polyurethane lens with blue-violet light protection performance and a manufacturing method thereof.
[ background of the invention ]
The polyurethane is prepared by the polymerization reaction of an active hydrogen-containing compound and an isocyanate compound, and has two types of thermoplastic type and thermosetting type. In order to destroy the crystallization property of polyurethane, the material has better light transmittance, and crosslinking is necessary, so that the thermosetting type is mainly used. The active hydrogen-containing compounds are mainly alcohols and phenols containing OH, thiols containing SH and thiophenols. In the pursuit of high refractive index, documents have recently reported that SH compounds are almost all. Isocyanate-containing compounds can be further classified into two groups, i.e., ordinary isocyanates containing NCO and isothiocyanates containing NCS. The NCO compound is a precursor of polyurethane products, is convenient to use and has extremely wide application.
International high-grade polyurethane resin lens materials are basically monopolized by the japan mitsui corporation. The high refractive index lens materials were developed by the company Mitsui from the beginning of the 80 s. In 1987, polyurethane lens material of the first product of the Mitsui chemical Co., Ltd was officially released. The refractive index was 1.60 and the commercial lot number MR-6. In 1991, Mitsui chemical corporation developed a polyurethane ophthalmic lens material with a refractive index of 1.67. In 2000, polyurethane materials having a refractive index of 1.74 were also introduced by mitsui chemical ltd. Over 20 years of its development, polyurethane lens materials developed by other companies have not made breakthrough progress.
The research on the manufacturing method of the 1.67 polyurethane lens with the blue-violet light prevention performance, particularly the addition of the blue-violet light prevention agent into the polyurethane lens, is not reported. The blue light prevention lens can effectively filter blue light in a coating and blue-violet light absorbent adding mode. The patent: the blue light level protective resin lens with the refractive index of 1.67 and the application publication number CN 103676201A and the preparation method thereof are characterized In that the blue light level protective resin lens with the refractive index of 1.67 comprises a resin substrate with the refractive index of 1.67, a hard coating layer is coated on the resin substrate In a dip-coating manner, and a first SiO2 film layer, a ZrO2 film layer, a second SiO2 film layer, a Ti2O3 film layer, an In2O3 film layer and a third SiO2 film layer are sequentially deposited on the surface of the hard coating layer. The resin lens has a filtering effect of 45-50% on blue light with a wavelength of 400-500 nm, the blue light is effectively filtered by a film layer reflection method, and the filtering effect on low-energy blue-violet light with a wavelength of 380-420 nm is poor.
Patent of adding blue light absorber through substrate: application publication No. CN 104327237 a, a blue-light-proof resin lens, its characterized in that: the catalytic polymerization reaction is initiated after three types of chemical components A, B, C are mixed, wherein the component A: b: the mass ratio of C is 30-50: 20-50: 0.1-1, wherein the component A is a polyisocyanate compound, the component B is mercaptan, and the component C is an indole or benzotriazole compound. The patent: application publication No. CN 103465418A, a manufacturing method of blue-light-proof resin lens, which is characterized in that: filling ultraviolet absorbent and blue absorbent in thermosetting optical resin monomer, and injecting the thermosetting optical resin monomer into an optical glass mold for thermosetting molding, wherein the thermosetting optical resin monomer specifically comprises the following steps: 1) preparation of blue light absorber: mixing OLP melanin powder with 600 ppm-800 ppm or 60 ppm-90 ppm of the weight of the thermosetting optical resin monomer, a polar organic solvent and a fat-soluble solubilizer, wherein the mixing weight ratio is OLP melanin powder: polar organic solvent: fat-soluble solubilizer 1: (20-50): (0.00001-0.0002), mixing and stirring until the mixture is fully dissolved to form the blue light absorbent; 2) and (2) adding the ultraviolet absorbent into the thermosetting optical resin monomer according to 0.5-2% of the weight of the thermosetting optical resin monomer for mixing, then adding the blue light absorbent obtained in the step (1) for mixing, stirring in vacuum, and injecting into an optical glass mold for thermosetting molding. However, both of these patents are primarily universal blue light filters and do not work well in 1.67 polyurethane lens systems.
[ summary of the invention ]
The invention aims to overcome the defects of the prior art and provides a 1.67 polyurethane lens with blue-violet protection performance and a manufacturing method thereof.
The purpose of the invention is realized by the following technical scheme:
a1.67 polyurethane lens with blue and violet light protection performance comprises a monomer and an auxiliary agent,
the monomer comprises the following components in percentage by mass:
4, 8-dimercaptomethyl-1, 11-dimercapto-3, 6, 9-trithiaundecane: 5 to 50 percent
5, 7-dimercaptomethyl-1, 11-dimercapto-3, 6, 9-trithiaundecane: 5 to 50 percent
Bis (2,2 mercapto) ethyl tetrasulfide: 5 to 50 percent
M-xylylene isocyanate: 5 to 50 percent
Cyclohexane dimethylene diisocyanate: 5 to 50 percent
The auxiliary agent comprises the following components in percentage by mass:
catalyst: 1.0-10.0 ‰
Blue-violet light absorber: 0.1 to 5 percent
Organic dye: 0.1-4 ‰
The blue violet light absorbent is one or more of benzotriazole and benzophenone, including 2 ~ (2 '. about.hydroxy-3'. about.t-butyl-5 '. about.methylphenyl) -5-chlorobenzotriazole or 2 ~ (2'. about.hydroxy-5't-octylphenyl) benzotriazole or 2 ~ (hydroxy-4-methoxybenzophenone or 2, 2'. about.dimethyl-4-methylamino benzophenone, and the dosage is 0.1% -5%.
The catalyst comprises the specific components of an organic tin catalyst;
the organic dye is one or more of red dye, green dye and blue dye;
a method for manufacturing a 1.67 polyurethane lens with blue-violet protection performance comprises the following specific steps:
(1) adding the auxiliary agent into isocyanate, stirring and dissolving, and adding mercapto polyol while stirring after the auxiliary agent is completely dissolved; the ratio of the mercapto-polyol to the polyisocyanate is 0.5: 1-2.0: 1 in terms of the molar ratio of the functional group NCO/SH; pouring the raw materials into a mold after vacuum defoaming, curing and molding the raw materials according to a curing program, then cooling to 60 ℃, and obtaining the substrate of the 1.67 polyurethane lens with the blue-violet performance after demolding and cleaning; the curing procedure was:
25℃～35℃ 2h～5h
35℃～41℃ 5h～10h
41℃～57℃ 3h～5h
57℃～81℃ 3h～5h
81℃～96℃ 3h～5h
96℃～125℃ 2h～4h
125℃～125℃ 2h～4h
125℃～60℃ 2h～4h
60℃～60℃ 0.5h～4h
at 60 ℃, removing the mold to obtain the 1.67 polyurethane lens substrate with the blue and violet light protection performance; the novel manufacturing scheme of the manufacturing method is simple and convenient, and the lens is endowed with excellent performance. The adopted curing program fully considers the heat release and heat absorption problems in the free radical polymerization process, and the designed curing curve can better ensure the molding process of the lens and ensure that the mold-opening phenomenon of the mold-explosion is controlled below 1.5 percent.
(2) The 1.67 polyurethane lens with the blue and violet light protection performance obtained by opening the mould is firstly cleaned and secondarily cured at the temperature of 120 ℃ for 2 hours, and the stress of the substrate in the thermosetting molding process is removed. The lens surface is then physically polished and chemically etched, followed by dipping the lens surface into a layer of organosilane coating. The surface organosilane is dried in the coating equipment and then enters an oven for strengthening. The strengthening temperature is 120 ℃ for 2 hours. The surface hardness of the lens is increased from 1H to 3H. However, the light transmittance of the lens is only 88%, and the reflectivity can reach more than 3%, which easily causes the obvious reflection of the light of the wearerSuch as a mouse. After the lens is hardened, a plurality of layers of coatings are needed to reduce the reflection of the surface of the lens. Sequentially depositing a first SiO layer on the surface of the hard coating layer2Film layer, second layer of ZrO2Film layer, third layer of SiO2Film layer, fourth layer of ZrO2A film layer, a fifth SiO2 film layer, a sixth ITO film layer and a seventh ZrO layer2And (5) film layer. According to the manufacturing method of the 1.67 polyurethane lens with the blue and violet light protection performance obtained by the manufacturing scheme, the visible light transmittance is more than or equal to 93 percent, the blue and violet light transmittance is respectively wave bands of 280nm to 380nm, and the transmittance is less than or equal to 0.5 percent; 380nm-420nm is less than or equal to 20 percent. The impact strength of the lens can reach 60kJ/M2, and the rimless glasses can be assembled.
The refractive index of the substrate of the resin lens obtained by polymerizing the resin is 1.67, and the visible light transmittance of the lens obtained by hard coating the substrate is more than or equal to 93 percent; the blue-violet light transmittance is respectively 280nm to 380nm, and the transmittance is less than or equal to 0.5 percent; 380nm-420nm is less than or equal to 20 percent.
Compared with the prior art, the invention has the following positive effects:
the application relates to a method for manufacturing a 1.67 polyurethane lens with blue-violet protection performance, which is characterized by comprising the following steps: the lens resin formula adopts 4, 8-dimercaptomethyl-1, 11-dimercapto-3, 6, 9-trithioundecane: 5% -50%; 5, 7-dimercaptomethyl-1, 11-dimercapto-3, 6, 9-trithiaundecane: 5% -50%; bis (2,2 mercapto) ethyl tetrasulfide: 5% -50%; m-xylylene isocyanate: 5% -50%; cyclohexane dimethylene diisocyanate: 5 to 50 percent of five resins are compounded, the catalyst adopts an organic tin catalyst, the blue-violet light absorbent adopts benzotriazole and benzophenone, the organic dye adopts red, green and blue dyes, and the dyes are used for toning the substrate. The refractive index of the substrate of the resin lens obtained by polymerizing the resin is 1.67, and the visible light transmittance of the lens obtained by hard coating the substrate is more than or equal to 93 percent; the blue-violet light transmittance is respectively 280nm to 380nm, and the transmittance is less than or equal to 0.5 percent; 380nm-420nm is less than or equal to 20 percent.
[ detailed description ] embodiments
The following provides a specific embodiment of a 1.67 polyurethane lens having blue-violet protection properties and a method for manufacturing the same according to the present invention.
Example 1
4, 8-dimercaptomethyl-1, 11-dimercapto-3, 6, 9-trithiaundecane: 200.0g
5, 7-dimercaptomethyl-1, 11-dimercapto-3, 6, 9-trithiaundecane: 250.0g
Bis (2,2 mercapto) ethyl tetrasulfide: 50.0g
M-xylylene isocyanate: 300.0g
Cyclohexane dimethylene diisocyanate: 200.0g
Dibutyl tin dichloride: 2.0g
2- (2 '-hydroxy-5' -tert-octylphenyl) benzotriazole: 1.2g
Blue and green organic dyes: each 2.5g
The mixture obtained according to the above formulation was filtered through a 0.5 μm filter disc, poured into a glass mold prepared in advance, placed in an oven and subjected to radical polymerization according to the given curing procedure.
25℃-35℃ 3h
35℃-41℃ 6h
41℃-57℃ 4h
57℃-81℃ 4h
81℃-96℃ 4h
96℃-125℃ 3h
125℃-125℃ 2h
125℃-60℃ 2h
60℃-60℃ 0.5h
And (3) at 60 ℃, removing the mold, and then hardening and coating the lens to obtain the acrylic resin lens with the blue and violet light protection performance.
The lenses prepared were made using ISO8980.3-1999 Burr spectacle lens third part: the results of the examination by the methods specified in "method for measuring and testing Transmission Performance" and "QB 2506-2001" ophthalmic lens for optical resin "were as follows:
1 original transmittance: 93.2 percent
2, the blue-violet light transmittance is respectively 280nm to 380nm, and the transmittance is less than or equal to 0.2 percent; 380-420 nm less than or equal to 11 percent
3 impact resistance: as specified by QB 2506.
Example 2
4, 8-dimercaptomethyl-1, 11-dimercapto-3, 6, 9-trithiaundecane: 250.0g
5, 7-dimercaptomethyl-1, 11-dimercapto-3, 6, 9-trithiaundecane: 200.0g
Bis (2,2 mercapto) ethyl tetrasulfide: 50.0g
M-xylylene isocyanate: 350.0g
Cyclohexane dimethylene diisocyanate: 150.0g
Dibutyl tin dichloride: 2.0g
2- (2 '-hydroxy-5' -tert-octylphenyl) benzotriazole: 1.5g
Blue and green organic dyes: each 2.5g
The mixture obtained according to the above formulation was filtered through a 0.5 μm filter disc, poured into a glass mold prepared in advance, placed in an oven and subjected to radical polymerization according to the given curing procedure.
25℃-35℃ 3h
35℃-41℃ 6h
41℃-57℃ 4h
57℃-81℃ 4h
81℃-96℃ 4h
96℃-125℃ 3h
125℃-125℃ 2h
125℃-60℃ 2h
60℃-60℃ 0.5h
And (3) at 60 ℃, removing the mold, and then hardening and coating the lens to obtain the acrylic resin lens with the blue and violet light protection performance.
The lenses prepared were made using ISO8980.3-1999 Burr spectacle lens third part: the results of the examination by the methods specified in "method for measuring and testing Transmission Performance" and "QB 2506-2001" ophthalmic lens for optical resin "were as follows:
1 original transmittance: 93.1 percent
2, the blue-violet light transmittance is respectively 280nm to 380nm, and the transmittance is less than or equal to 0.1 percent; 380-420 nm less than or equal to 9.5 percent
3 impact resistance: as specified by QB 2506.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, several modifications and decorations can be made without departing from the concept of the present invention, and these modifications and decorations should also be regarded as being within the protection scope of the present invention.
Claims (4)
1. A1.67 polyurethane lens with blue and violet light protection performance is characterized by comprising a monomer and an auxiliary agent,
the monomer comprises the following components in percentage by mass:
4, 8-dimercaptomethyl-1, 11-dimercapto-3, 6, 9-trithiaundecane: 5 to 50 percent
5, 7-dimercaptomethyl-1, 11-dimercapto-3, 6, 9-trithiaundecane: 5 to 50 percent
Bis (2,2 mercapto) ethyl tetrasulfide: 5 to 50 percent
M-xylylene isocyanate: 5 to 50 percent
Cyclohexane dimethylene diisocyanate: 5 to 50 percent
The auxiliary agent comprises the following components in percentage by mass:
catalyst: 1.0-10.0 ‰
Blue-violet light absorber: 0.1 to 5 percent
Organic dye: 0.1-4 ‰
The blue-violet light absorber is one or more of 2 ~ (2 '. about.3'. about.t.butyl-5 '. about.methyl phenyl) -5-chlorobenzotriazole, 2 ~ (2'. about.5 '. about.t.octylphenyl) benzotriazole, 2 ~ (hydroxy) -4-methoxybenzophenone and 2, 2'. about.dimethyl-4-methylamino benzophenone;
the manufacturing method of the 1.67 polyurethane lens with the blue-violet light protection performance comprises the following specific steps:
(1) adding the auxiliary agent into isocyanate, stirring and dissolving, and adding mercapto polyol while stirring after the auxiliary agent is completely dissolved; the ratio of the mercapto-polyol to the polyisocyanate is 0.5: 1-2.0: 1 in terms of the molar ratio of the functional group NCO/SH; pouring the raw materials into a mold after vacuum defoaming, curing and molding the raw materials according to a curing program, then cooling to 60 ℃, and obtaining the substrate of the 1.67 polyurethane lens with the blue-violet performance after demolding and cleaning; the curing procedure was:
25℃～35℃ 2h～5h
35℃～41℃ 5h～10h
41℃～57℃ 3h～5h
57℃～81℃ 3h～5h
81℃～96℃ 3h～5h
96℃～125℃ 2h～4h
125℃～125℃ 2h～4h
125℃～60℃ 2h～4h
60℃～60℃ 0.5h～4h
at 60 ℃, removing the mold to obtain the 1.67 polyurethane lens substrate with the blue and violet light protection performance;
(2) carrying out lens cleaning and secondary curing on the 1.67 polyurethane lens with the blue and violet light protection performance obtained by opening the mold, wherein the temperature of the secondary curing is 120 ℃ for 2 hours, and removing the stress of the substrate in the thermosetting molding process; then, the surface of the lens is physically polished and chemically corroded, and then a layer of organic silane coating is immersed on the surface of the lens; surface organosilane is dried in coating equipment and then enters an oven for reinforcement; the strengthening temperature is 120 ℃ for 2 hours; after the lens is hardened, a plurality of layers of coating films are needed, and a first layer of SiO is deposited on the surface of the hardened film layer in sequence2Film layer, second layer of ZrO2Film layer, third layer of SiO2Film layer, fourth layer of ZrO2Film layer, fifth layer of SiO2Film layer, sixth ITO film layer and seventh ZrO layer2A film layer; a1.67 polyurethane lens with blue-violet protection properties was obtained.
2. The 1.67 polyurethane lens with blue-violet protection as claimed in claim 1, wherein the specific component of the catalyst is an organotin catalyst.
3. The 1.67 polyurethane lens for protecting blue-violet according to claim 1, wherein the organic dye is one or more of red dye, green dye and blue dye.
4. The 1.67 polyurethane lens with blue-violet protection of claim 1, wherein the 1.67 polyurethane lens has a visible light transmittance of 93% or more and a blue-violet transmittance of 0.5% or less in a wavelength range of 280nm to 380 nm; the transmittance of blue-violet light with the wave band of 380nm-420nm is less than or equal to 20 percent; the impact strength of the lens is as high as 60kJ/m2And assembling the rimless glasses.
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| CN109504072A (en) * | 2018-07-23 | 2019-03-22 | 广州市辉乐医药科技有限公司 | A kind of eyeglass of high visible light multistage protection laser |
| CN112099123A (en) * | 2019-06-18 | 2020-12-18 | 上海宜酷光学科技有限公司 | Vector substrate absorption type blue light-proof high-transmittance lens and preparation method thereof |
| CN110330784A (en) * | 2019-07-24 | 2019-10-15 | 上海康耐特光学有限公司 | A kind of polyurethane mixture and its preparation method and application includes its modification eyeglass |
| CN112346165B (en) * | 2020-11-06 | 2022-04-29 | 南京工业大学 | A kind of high-strength anti-blue light, anti-ultraviolet PC lens and preparation method thereof |
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| KR101401784B1 (en) * | 2009-11-13 | 2014-05-30 | 미쓰이 가가쿠 가부시키가이샤 | Film and application thereof |
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| EP3135703B1 (en) * | 2014-04-25 | 2019-10-16 | Mitsui Chemicals, Inc. | Polymerizable composition for optical material, optical material, and method for producing optical material |
| CN104327237A (en) * | 2014-10-10 | 2015-02-04 | 浙江海洋学院 | Blue light-proof resin lens and preparation process thereof |
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| CN103676203A (en) * | 2013-12-05 | 2014-03-26 | 上海伟星光学有限公司 | Dark brown resin lens with visible-light color-changing performance and manufacture method thereof |
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