CN111303381B - Polyurethane color-changing lens with refractive index of 1.60 and preparation method thereof - Google Patents
Polyurethane color-changing lens with refractive index of 1.60 and preparation method thereof Download PDFInfo
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Abstract
The invention relates to a polyurethane color-changing lens with a refractive index of 1.60 and a preparation method thereof, belonging to the technical field of optical lens preparation. According to the invention, polyether polyol is firstly used as a raw material, mixed with isophorone diisocyanate and added with a catalyst for prepolymerization reaction, tertiary amine compound and acetic acid are added into a prepolymer for ionization reaction, tertiary amine positive electron withdrawing groups are introduced into polyurethane, and finally a silane coupling agent is used for blocking to finally obtain modified polyurethane, and finally the modified polyurethane and spiropyran are mixed, cast and cured to obtain the polyurethane photochromic lens with the refractive index of 1.60.
Description
Technical Field
The invention relates to a polyurethane color-changing lens with a refractive index of 1.60 and a preparation method thereof, belonging to the technical field of optical lens preparation.
Background
At present, a color-changing lens is a lens with a color changing along with the change of external light. The lens can quickly change into dark color under sunlight, the light transmittance of the lens is greatly reduced, and the stronger the light is, the darker the color of the lens is; the weaker the light, the lighter the color of the lens, and when the lens is returned to the room, the color of the lens can quickly fade away and return to the original transparent state. The color-changing lenses on the market at present are divided into two major types according to materials, one type is a relatively traditional glass color-changing lens, and the other type is a novel resin color-changing lens which is put on the market from the last 90 years of the century. Among them, a polyurethane lens is a typical resin lens. There are many kinds of organic photochromic compounds, and the current reports in the literature are mainly divided into two main categories. One is a T-type photochromic compound, which changes color when being irradiated by ultraviolet light or visible light, can automatically recover to the original color after leaving a light source, and mainly comprises several compounds such as spiropyran, spirooxazine, azobenzene, pyrazolone and the like; the other is a P-type photochromic compound, and after the illumination color of the compound is changed, the color can be recovered only by the excitation of light with the other wavelength, mainly including fulgide, diaryl ethylene and the like. These photochromic compounds are dissolved in a resin to produce a lens, and a photochromic lens can be obtained. However, most of the current organic photochromic compounds can only be used in acrylic resin lenses, and if the organic photochromic compounds are mixed with polyurethane lens monomers, the photochromic compounds are either insoluble or have slow fading speed.
In view of the above-mentioned drawbacks, the designer actively makes research and innovation to create a photochromic polyurethane lens with refractive index of 1.60 and a preparation method thereof, so that the photochromic polyurethane lens has industrial application value.
Disclosure of Invention
The invention mainly solves the technical problem that most of the existing organic photochromic compounds can only be used in acrylic resin lenses, and if the photochromic compounds are mixed with polyurethane lens monomers, the photochromic compounds are not dissolved or slowly discolored.
In order to solve the technical problems, the technical scheme adopted by the invention is as follows:
a polyurethane color-changing lens with a refractive index of 1.60 is prepared from modified polyurethane and spiropyran,
the modified polyurethane is prepared from polyether diol N220, polyether triol ZC330, hydroxyalkyl silicone oil, isophorone diisocyanate, dibutyl tin dilaurate acetate, N-methyldiethanolamine, acetic acid and a silane coupling agent;
the silane coupling agent is one of a silane coupling agent KH550 or a silane coupling agent KH 560;
the chemical formula structural formula of the spiropyran is as follows:
wherein R1, R2 and R3 are all selected from H, hydroxyl, phenolic hydroxyl and amino active groups, and R1, R2 and R3 are H when different.
A preparation method of a polyurethane color-changing lens with a refractive index of 1.60 comprises the following specific preparation steps:
(1) preparation of the dehydrated mixture: mixing polyether glycol N220, polyether triol ZC330 and hydroxyalkyl silicone oil, and then performing vacuum dehydration to obtain a dehydrated mixture;
(2) preparation of prepolymer: heating the dehydrated mixture, adding isophorone diisocyanate and dibutyl tin dilaurate acetate, and stirring for prepolymerization reaction to obtain a prepolymer;
(3) preparation of ionized product: reducing the temperature of the reaction kettle, adding N-methyldiethanolamine and acetic acid solution, heating, raising the temperature, and carrying out thermal insulation ionization reaction to obtain an ionized product;
(4) preparing modified polyurethane: reducing the temperature of the reaction kettle, adding a silane coupling agent into the reaction kettle for end sealing, heating, raising the temperature, and carrying out heat preservation reaction to obtain modified polyurethane;
(5)1.60 preparation of polyurethane color-changing lens with refractive index: adding spiropyran into the reaction kettle, continuously reacting, adding triethylamine and acetone into the reaction kettle, stirring and reacting to obtain self-made polyurethane resin, pouring the self-made polyurethane resin into a lens mould, cooling and forming, removing the mould, and removing burrs to obtain the polyurethane photochromic lens with the refractive index of 1.60.
Further, the preparation method comprises the following specific steps:
(1) preparation of the dehydrated mixture: mixing polyether glycol N220, polyether triol ZC330 and hydroxyalkyl silicone oil, putting the mixture into a vacuum dehydration tank, and performing vacuum dehydration to obtain a dehydrated mixture;
(2) preparation of prepolymer: transferring the dehydrated mixture into a reaction kettle, heating to raise the temperature, adding isophorone diisocyanate and dibutyl tin dilaurate acetate into the reaction kettle, and stirring for prepolymerization reaction to obtain a prepolymer;
(3) preparation of ionized product: reducing the temperature of the reaction kettle, adding N-methyldiethanolamine and 1mol/L acetic acid solution for three times within 1min, heating, keeping the temperature, and performing ionization reaction to obtain an ionized product;
(4) preparing modified polyurethane: reducing the temperature of the reaction kettle, adding a silane coupling agent into the reaction kettle within 10min for end capping, heating, raising the temperature, and carrying out heat preservation reaction to obtain modified polyurethane;
(5)1.60 preparation of polyurethane color-changing lens with refractive index: adding spiropyran into the reaction kettle, continuing to react, adding triethylamine and acetone into the reaction kettle, stirring and reacting to obtain self-made polyurethane resin, pouring the self-made polyurethane resin into a lens mold, cooling and forming, removing the mold, and removing burrs to obtain the polyurethane photochromic lens with the refractive index of 1.60.
Further, the preparation method comprises the following specific steps:
(1) preparation of the dehydrated mixture: mixing polyether glycol N220, polyether triol ZC330 and hydroxy hydrocarbon silicone oil according to the mass ratio of 5:5:1, putting the mixture into a vacuum dehydration tank, and performing vacuum dehydration for 1.5-2.0 h under the conditions that the temperature is 110 ℃ and the pressure is-0.01 MPa to obtain a dehydrated mixture;
(2) preparation of prepolymer: transferring the dehydrated mixture into a reaction kettle, heating to 60-70 ℃, adding 50-60% by mass of isophorone diisocyanate and 1-3% by mass of dibutyl tin dilaurate acetate into the reaction kettle, and stirring for prepolymerization for 2-3 h to obtain a prepolymer;
(3) preparation of ionized product: reducing the temperature of the reaction kettle to 40-50 ℃, adding N-methyldiethanolamine with 5% of prepolymer mass and acetic acid solution with 1mol/L concentration with 5% of prepolymer mass into the reaction kettle for three times within 1min, heating to 60-70 ℃, and carrying out heat preservation ionization reaction for 1-2 h to obtain an ionized product;
(4) preparing modified polyurethane: reducing the temperature of the reaction kettle to 40-50 ℃, adding a silane coupling agent with the mass of 3% of that of an ionized product into the reaction kettle within 10min for end capping, heating to 55-65 ℃, and carrying out heat preservation reaction for 0.5-1.0 h to obtain modified polyurethane;
(5)1.60 preparation of polyurethane color-changing lens with refractive index: adding spiropyran accounting for 5% of the mass of the modified polyurethane into the reaction kettle, continuously reacting for 10-12 hours at 60-70 ℃, adding triethylamine accounting for 0.5% of the mass of the modified polyurethane and acetone accounting for 10% of the mass of the modified polyurethane into the reaction kettle, stirring and reacting for 30-40 min to obtain self-made polyurethane resin, pouring the self-made polyurethane resin into a lens mold, cooling and molding the self-made polyurethane resin, disassembling the mold, and removing burrs to obtain the polyurethane photochromic lens with the refractive index of 1.60.
By the scheme, the invention at least has the following advantages:
the invention firstly takes polyether polyol as raw material, mixes the polyether polyol with isophorone diisocyanate and adds catalyst to carry out prepolymerization reaction, then adds tertiary amine compound and acetic acid to carry out ionization reaction to prepolymer, introduces tertiary amine positive electron-withdrawing group to polyurethane, finally carries out end capping by silane coupling agent to obtain modified polyurethane, finally mixes the modified polyurethane and spiropyran, pours and solidifies to process to obtain the 1.60 refractive index polyurethane photochromic lens, the invention modifies polyurethane resin matrix, introduces tertiary amine positive electron-withdrawing group to polyurethane, has strong electron-withdrawing capability, enables the polyurethane to have higher micro-polarizability, can improve the compatibility between the polyurethane matrix and the spiropyran, simultaneously leads the polarity of the whole polyurethane molecule to be increased and the ground state dipole moment of the molecule to be increased, the invention is beneficial to the overturning orientation of the spiropyran chromophore, provides necessary space for the configuration change of spiropyran under ultraviolet light, accelerates the color changing speed of spiropyran molecules, and adds a chemical cross-linking agent triethylamine in the modification process, and heats and polarizes to enable the spiropyran photochromic group to complete the thermal cross-linking reaction in the orientation process, thereby improving the orientation sequence parameter of the chromophore, accelerating the color changing speed of the lens again, and having wide application prospect.
The foregoing is a summary of the present invention, and in order to provide a clear understanding of the technical means of the present invention and to be implemented in accordance with the present specification, the following is a detailed description of the preferred embodiments of the present invention.
Detailed Description
Mixing polyether glycol N220, polyether triol ZC330 and hydroxy hydrocarbon silicone oil according to the mass ratio of 5:5:1, putting the mixture into a vacuum dehydration tank, and performing vacuum dehydration for 1.5-2.0 h under the conditions that the temperature is 110 ℃ and the pressure is-0.01 MPa to obtain a dehydrated mixture; transferring the dehydrated mixture into a reaction kettle, heating to 60-70 ℃, adding 50-60% by mass of isophorone diisocyanate and 1-3% by mass of dibutyl tin dilaurate acetate into the reaction kettle, and stirring for prepolymerization for 2-3 h to obtain a prepolymer; reducing the temperature of the reaction kettle to 40-50 ℃, adding N-methyldiethanolamine with 5% of prepolymer mass and acetic acid solution with 1mol/L concentration with 5% of prepolymer mass into the reaction kettle for three times within 1min, heating to 60-70 ℃, and carrying out heat preservation ionization reaction for 1-2 h to obtain an ionized product; reducing the temperature of the reaction kettle to 40-50 ℃, adding a silane coupling agent with the mass of 3% of that of an ionized product into the reaction kettle within 10min for end sealing, heating to 55-65 ℃, and carrying out heat preservation reaction for 0.5-1.0 h to obtain modified polyurethane; adding 5% of spiropyran by mass of the modified polyurethane into the reaction kettle, continuously reacting for 10-12 h at 60-70 ℃, adding 0.5% of triethylamine by mass of the modified polyurethane and 10% of acetone by mass of the modified polyurethane into the reaction kettle, stirring and reacting for 30-40 min to obtain self-made polyurethane resin, pouring the self-made polyurethane resin into a lens mold, cooling and molding the self-made polyurethane resin, removing the mold, and deburring to obtain the polyurethane photochromic lens with the refractive index of 1.60. The silane coupling agent is one of a silane coupling agent KH550 or a silane coupling agent KH 560;
the chemical formula structural formula of the spiropyran is as follows:
wherein R1, R2 and R3 are all selected from H, hydroxyl, phenolic hydroxyl and amino active groups, and R1, R2 and R3 are not H at the same time.
Example 1
Mixing polyether glycol N220, polyether triol ZC330 and hydroxy hydrocarbon silicone oil according to the mass ratio of 5:5:1, putting the mixture into a vacuum dehydration tank, and performing vacuum dehydration for 1.5h under the conditions that the temperature is 110 ℃ and the pressure is-0.01 MPa to obtain a dehydrated mixture; transferring the dehydrated mixture into a reaction kettle, heating to 60 ℃, adding 50% of isophorone diisocyanate in terms of the mass of the dehydrated mixture and 1-3% of dibutyl tin dilaurate acetate in terms of the mass of the dehydrated mixture into the reaction kettle, and stirring for prepolymerization reaction for 2 hours to obtain a prepolymer; reducing the temperature of the reaction kettle to 40 ℃, adding N-methyldiethanolamine with 5% of prepolymer mass and acetic acid solution with 1mol/L concentration with 5% of prepolymer mass into the reaction kettle for three times within 1min, heating the reaction kettle to 60 ℃, and carrying out heat preservation ionization reaction for 1h to obtain an ionized product; reducing the temperature of the reaction kettle to 40 ℃, adding a silane coupling agent KH550 with the mass of 3% of that of an ionized product into the reaction kettle within 10min for end capping, heating to 55 ℃, and carrying out heat preservation reaction for 0.5h to obtain modified polyurethane; adding 5% of spiropyran by mass of the modified polyurethane into the reaction kettle, continuously reacting for 10 hours at 60 ℃, adding 0.5% of triethylamine by mass of the modified polyurethane and 10% of acetone by mass of the modified polyurethane into the reaction kettle, stirring and reacting for 30min to obtain a self-made polyurethane resin, pouring the self-made polyurethane resin into a lens mold, cooling and forming, removing the mold, and removing burrs to obtain the polyurethane photochromic lens with the refractive index of 1.60.
The chemical formula structural formula of the spiropyran is as follows:
wherein R1, R2 and R3 are all selected from H, hydroxyl, phenolic hydroxyl and amino active groups, and R1, R2 and R3 are not H at the same time.
Example 2
Mixing polyether glycol N220, polyether triol ZC330 and hydroxy hydrocarbon silicone oil according to the mass ratio of 5:5:1, putting the mixture into a vacuum dehydration tank, and performing vacuum dehydration for 1.8h under the conditions that the temperature is 110 ℃ and the pressure is-0.01 MPa to obtain a dehydrated mixture; transferring the dehydrated mixture into a reaction kettle, heating to 65 ℃, adding isophorone diisocyanate accounting for 55% of the mass of the dehydrated mixture and dibutyl tin dilaurate accounting for 2% of the mass of the dehydrated mixture into the reaction kettle, and stirring for prepolymerization reaction for 3 hours to obtain a prepolymer; reducing the temperature of the reaction kettle to 45 ℃, adding N-methyldiethanolamine with 5% of prepolymer mass and acetic acid solution with 1mol/L of 5% of prepolymer mass into the reaction kettle for three times within 1min, heating to 65 ℃, and carrying out heat preservation ionization reaction for 1h to obtain an ionized product; reducing the temperature of the reaction kettle to 45 ℃, adding a silane coupling agent KH550 with the mass of 3% of that of an ionized product into the reaction kettle within 10min for end capping, heating to 60 ℃, and carrying out heat preservation reaction for 0.8h to obtain modified polyurethane; adding 5% of spiropyran by mass of the modified polyurethane into the reaction kettle, continuously reacting for 11h at 65 ℃, adding 0.5% of triethylamine by mass of the modified polyurethane and 10% of acetone by mass of the modified polyurethane into the reaction kettle, stirring and reacting for 35min to obtain self-made polyurethane resin, pouring the self-made polyurethane resin into a lens mold, cooling and molding the self-made polyurethane resin, removing the mold, and removing burrs to obtain the polyurethane photochromic lens with the refractive index of 1.60.
The chemical formula structural formula of the spiropyran is as follows:
wherein R1, R2 and R3 are all selected from H, hydroxyl, phenolic hydroxyl and amino active groups, and R1, R2 and R3 are not H at the same time.
Example 3
Mixing polyether glycol N220, polyether triol ZC330 and hydroxy hydrocarbon silicone oil according to the mass ratio of 5:5:1, putting the mixture into a vacuum dehydration tank, and performing vacuum dehydration for 2.0h under the conditions that the temperature is 110 ℃ and the pressure is-0.01 MPa to obtain a dehydrated mixture; transferring the dehydrated mixture into a reaction kettle, heating to 70 ℃, adding isophorone diisocyanate with the mass of 60% of the dehydrated mixture and dibutyl tin dilaurate with the mass of 3% of the dehydrated mixture into the reaction kettle, and stirring for prepolymerization reaction for 3 hours to obtain a prepolymer; reducing the temperature of the reaction kettle to 50 ℃, adding N-methyldiethanolamine with 5% of prepolymer mass and acetic acid solution with 1mol/L of 5% of prepolymer mass into the reaction kettle three times within 1min, heating the reaction kettle to 70 ℃, and carrying out thermal insulation ionization reaction for 2h to obtain an ionized product; reducing the temperature of the reaction kettle to 50 ℃, adding a silane coupling agent KH560 with the mass of 3% of that of an ionized product into the reaction kettle within 10min for end capping, heating to 65 ℃, and carrying out heat preservation reaction for 1.0h to obtain modified polyurethane; adding 5% of spiropyran by mass of the modified polyurethane into the reaction kettle, continuously reacting for 12 hours at 70 ℃, adding 0.5% of triethylamine by mass of the modified polyurethane and 10% of acetone by mass of the modified polyurethane into the reaction kettle, stirring and reacting for 40min to obtain self-made polyurethane resin, pouring the self-made polyurethane resin into a lens mold, cooling and molding the self-made polyurethane resin, removing the mold, and removing burrs to obtain the polyurethane photochromic lens with the refractive index of 1.60.
The chemical formula structural formula of the spiropyran is as follows:
wherein R1, R2 and R3 are all selected from H, hydroxyl, phenolic hydroxyl and amino active groups, and R1, R2 and R3 are not H at the same time.
Comparative example 1: the preparation was identical to that of inventive example 1, except that the polyurethane was not ionically modified with N-methyldiethanolamine and acetic acid;
comparative example 2: the preparation was the same as in example 1 of the present invention, except that the polyurethane was modified without the addition of the chemical cross-linker triethylamine;
the performance of the photochromic lenses of the present invention and the comparative examples were measured, and the results are shown in table 1:
the detection method comprises the following steps:
the color change speed detection method comprises the following steps: and (3) irradiating the lens to be detected under visible light, recording the time when the lens changes color to a stable state and the time for recovering the color-changing lens after the light source is removed, wherein the shorter the time is, the faster the color-changing speed is.
TABLE 1 Performance test results
After detection, the color-changing lens can complete color change to a stable state within 1 minute under the irradiation of visible light, the visible light transmittance is reduced to 20% -30%, the color-changing lens can fade to 98% before the visible light transmittance reaches color change within 3 minutes after a light source is removed, and then gradually recovers to 100%, while in the comparison example 1, N-methyldiethanolamine and acetic acid are not used for carrying out ionization modification on polyurethane, so the visible light irradiation color-changing time exceeds two minutes, and the recovery time exceeds 4 minutes after the light source is removed, therefore, the ionization modification of the invention really improves the color-changing speed of the lens, in the comparison example 2, because triethylamine serving as a chemical cross-linking agent is not added for modifying the polyurethane, the visible light irradiation color-changing time exceeds one minute, and the recovery time exceeds 3 minutes after the light source is removed, the visible chemical cross-linking agent modification also improves the color changing speed of the lens, and has wide application prospect.
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, it should be noted that, for those skilled in the art, many modifications and variations can be made without departing from the technical principle of the present invention, and these modifications and variations should also be regarded as the protection scope of the present invention.
Claims (4)
1. A polyurethane color-changing lens is prepared from modified polyurethane and spiropyran, and is characterized in that:
the modified polyurethane is prepared from polyether diol N220, polyether triol ZC330, hydroxyalkyl silicone oil, isophorone diisocyanate, dibutyltin diacetate, N-methyldiethanolamine, acetic acid and a silane coupling agent;
the silane coupling agent is one of a silane coupling agent KH550 or a silane coupling agent KH 560;
the chemical formula of the spiropyran is as follows:
in the formula, R1，R2，R3Are all selected from H, hydroxyl, phenolic hydroxyl, amino active groups, and R1，R2，R3Not H at the same time.
2. A preparation method of a polyurethane color-changing lens is characterized by comprising the following specific preparation steps:
(1) preparation of the dehydrated mixture: mixing polyether glycol N220, polyether triol ZC330 and hydroxy silicone oil, and then performing vacuum dehydration to obtain a dehydrated mixture;
(2) preparation of prepolymer: heating the dehydrated mixture, adding isophorone diisocyanate and dibutyltin diacetate, and stirring for prepolymerization reaction to obtain a prepolymer;
(3) preparation of ionized product: reducing the temperature of the reaction kettle, adding N-methyldiethanolamine and acetic acid solution, heating, raising the temperature, and carrying out thermal insulation ionization reaction to obtain an ionized product;
(4) preparing modified polyurethane: reducing the temperature of the reaction kettle, adding a silane coupling agent into the reaction kettle for end sealing, heating, raising the temperature, and carrying out heat preservation reaction to obtain modified polyurethane;
(5) preparing a polyurethane color-changing lens: adding spiropyran into the reaction kettle, continuing to react, adding triethylamine and acetone into the reaction kettle, stirring and reacting to obtain self-made polyurethane resin, pouring the self-made polyurethane resin into a lens mold, cooling and forming, removing the mold, and removing burrs to obtain the polyurethane photochromic lens.
3. The preparation method of the polyurethane photochromic lens according to claim 2 is characterized by comprising the following specific preparation steps:
(1) preparation of the dehydrated mixture: mixing polyether glycol N220, polyether triol ZC330 and hydroxy hydrocarbon silicone oil, putting the mixture into a vacuum dehydration tank, and performing vacuum dehydration to obtain a dehydrated mixture;
(2) preparation of prepolymer: transferring the dehydrated mixture into a reaction kettle, heating, adding isophorone diisocyanate and dibutyltin diacetate into the reaction kettle, and stirring for prepolymerization reaction to obtain a prepolymer;
(3) preparation of ionized product: reducing the temperature of the reaction kettle, adding N-methyldiethanolamine and 1mol/L acetic acid solution for three times within 1min, heating, keeping the temperature, and performing ionization reaction to obtain an ionized product;
(4) preparing modified polyurethane: reducing the temperature of the reaction kettle, adding a silane coupling agent into the reaction kettle within 10min for end capping, heating, raising the temperature, and carrying out heat preservation reaction to obtain modified polyurethane;
(5) preparing a polyurethane color-changing lens: and adding spiropyran into the reaction kettle, continuing to react, adding triethylamine and acetone into the reaction kettle, stirring and reacting to obtain self-made polyurethane resin, pouring the self-made polyurethane resin into a lens mold, cooling and forming, removing the mold, and removing burrs to obtain the polyurethane photochromic lens.
4. The preparation method of the polyurethane photochromic lens according to claim 2 or 3, which is characterized by comprising the following specific preparation steps:
(1) preparation of the dehydrated mixture: mixing polyether glycol N220, polyether triol ZC330 and hydroxy hydrocarbon silicone oil according to the mass ratio of 5:5:1, putting the mixture into a vacuum dehydration tank, and performing vacuum dehydration for 1.5-2.0 h under the conditions that the temperature is 110 ℃ and the pressure is-0.01 MPa to obtain a dehydrated mixture;
(2) preparation of prepolymer: transferring the dehydrated mixture into a reaction kettle, heating to 60-70 ℃, adding 50-60% by mass of isophorone diisocyanate and 1-3% by mass of dibutyltin diacetate into the reaction kettle, and stirring for prepolymerization reaction for 2-3 hours to obtain a prepolymer;
(3) preparation of ionized product: reducing the temperature of the reaction kettle to 40-50 ℃, adding N-methyldiethanolamine with 5% of prepolymer mass and acetic acid solution with 1mol/L concentration with 5% of prepolymer mass into the reaction kettle for three times within 1min, heating to 60-70 ℃, and carrying out heat preservation ionization reaction for 1-2 h to obtain an ionized product;
(4) preparing modified polyurethane: reducing the temperature of the reaction kettle to 40-50 ℃, adding a silane coupling agent with the mass of 3% of that of an ionized product into the reaction kettle within 10min for end capping, heating to 55-65 ℃, and carrying out heat preservation reaction for 0.5-1.0 h to obtain modified polyurethane;
(5) preparing a polyurethane color-changing lens: adding 5% of spiropyran by mass of the modified polyurethane into the reaction kettle, continuously reacting for 10-12 h at 60-70 ℃, adding 0.5% of triethylamine by mass of the modified polyurethane and 10% of acetone by mass of the modified polyurethane into the reaction kettle, stirring and reacting for 30-40 min to obtain a self-made polyurethane resin, pouring the self-made polyurethane resin into a lens mold, cooling and forming, removing the mold, and removing burrs to obtain the polyurethane photochromic lens.
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| WO2001057106A1 (en) * | 2000-02-04 | 2001-08-09 | Ppg Industries Ohio, Inc. | Photochromic coated articles |
| DE10313936A1 (en) * | 2003-03-27 | 2004-10-14 | Consortium für elektrochemische Industrie GmbH | Organopolysiloxane / polyurea / polyurethane block copolymers |
| US20100204428A1 (en) * | 2005-08-04 | 2010-08-12 | Pierino Barbieri | Process and Composition for the Preparation of Transparent Polyurethanes and Polyurethanes Obtained Therefrom |
| KR101850731B1 (en) * | 2016-10-04 | 2018-06-01 | 주식회사 승화 | Polyurethane resin coating solution for photochromic lens |
| CN107778510B (en) * | 2017-11-10 | 2020-10-02 | 南京米兰达视光科学研究院有限公司 | Spiropyran photochromic optical material and preparation method thereof |
| CN107779072B (en) * | 2017-11-10 | 2020-08-25 | 江苏视科新材料股份有限公司 | Photochromic coating liquid and application thereof |
| CN108084327B (en) * | 2017-12-29 | 2020-02-07 | 扬州大学 | Preparation method of impact-resistant fast fading substrate |
| CN108383963B (en) * | 2018-03-22 | 2021-01-26 | 广东工业大学 | Composition, preparation method thereof and application thereof in field of mechanochromic materials |
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