CN105623239A - Photochromic composition and use thereof - Google Patents
Photochromic composition and use thereof Download PDFInfo
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- CN105623239A CN105623239A CN201410599321.8A CN201410599321A CN105623239A CN 105623239 A CN105623239 A CN 105623239A CN 201410599321 A CN201410599321 A CN 201410599321A CN 105623239 A CN105623239 A CN 105623239A
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Abstract
The invention relates to an organic photochromic material and concretely relates to a photochromic composition and a use thereof. The photochromic composition comprises one or more photochromic compounds and one or more polymers. The one or more photochromic compounds are selected from indolinespironaphthooxazine photochromic compounds. A use ratio of the one or more photochromic compounds to the one or more polymers is 0.1-10% by dry weight. The photochromic composition has excellent photochromic performances and has high photochromic sensitivity under visible light or UV irradiation. Compared with the existing photochromic composition, the photochromic composition provided through the invention substantially improves light fastness and reduces a cost.
Description
Technical Field
The invention relates to an organic photochromic material, in particular to a photochromic composition and application thereof.
Background
Organic photochromic materials have attracted wide attention because of their reversible photochromic properties under the action of sunlight or ultraviolet light, and have been applied to substrates such as plastics and glass to prepare optical lenses, sunglasses, anti-counterfeiting inks, textiles, building exterior wall coatings, interior decoration materials, films, artware, toys, optical disks and the like.
Although the organic photochromic substance has various applications as described above, it has been found through practical use and patent reports to have many problems in industrial applications.
There are two factors that limit the wide use of organic photochromic substances. One is that such materials have insufficient light fastness, most of which is due to the fact that the photochromic dye is decomposed and deteriorated too fast by light, so that the average service life of the photochromic material is short and difficult to be found in commercial products, which is determined by the reversible color change mechanism of the photochromic dye itself. For example: the existing photochromic anti-counterfeiting product cannot meet the anti-counterfeiting commercialization requirement due to short service life. Secondly, the cost of the photochromic dye is high, which limits the application of the substance in many fields. Therefore, there is a need for stable organic photochromic substances and reduced commercialization costs.
In order to prepare photochromic substances having better light fastness, several methods have been proposed in the prior art.
One method is a chemical copolymerization or grafting method, which refers to that photochromic structural units are connected to the main chain or branched chain of a polymer through chemical copolymerization or grafting reaction to achieve the function of changing color, so as to realize the photochromic performance of the polymer material. For example, EP0195898A teaches the addition of photochromic compounds to the polymerizable matrix of hindered amine light stabilizers; for example, KR2000-0067988 discloses a substrate, which can connect a hindered amine light stabilizer to the main chain of a polymer to form a graft structure, wherein the substrate has a certain effect of prolonging the service life of a spirooxazine photochromic compound.
Another method is to obtain a material with photochromic properties by physically blending a photochromic substance with a polymer. The method can be divided into a polymer film forming method, a microencapsulation or microsphere method, a method for preparing fibers by a spinning technology and the like. KR1995-0009349, for example, describes the preparation of encapsulated photochromic compositions by adding additives, oils and gelatin to a spiro photochromic compound; CN1594732A and CN102382232A disclose methods for preparing photochromic resin microspheres and photochromic water-soluble microspheres, respectively. Although the method of encapsulating the photochromic substance can improve the stability of the photochromic material, there is a problem in that it is difficult to commercialize in mass production due to the complicated process. For example, JP63234084A discloses a photochromic composition with good light fastness, which is prepared by taking indoline spirooxazine photochromic compound as a base material, polyvinyl butyral as a matrix, and adding additives such as light absorber and antioxidant, and has good light fastness after film formation. The light fastness of the composition reaches that of the composition which still has obvious photochromic performance after being irradiated by a xenon lamp for 40 hours. Wherein, the polymer component is 1.8g, the dye is used in an amount of 0.3g, and the mass accounts for 16.7 percent of the dry weight of the polymer material.
However, the photochromic dye in the photochromic composition is used in a large amount, so that the cost is high, and a large amount of organic solvent is used, so that the environment is not utilized, and the commercialization requirement is difficult to meet. Therefore, it is required to develop an environmentally friendly photochromic material having better light resistance, while having low cost and being easily applied to a wide range of industries.
Disclosure of Invention
The invention provides a photochromic composition and application thereof, aiming at overcoming the defects of poor light fastness and high cost in the existing photochromic composition.
In order to achieve the purpose, the invention adopts the technical scheme that:
a photochromic composition is composed of photochromic compound and polymer; wherein the photochromic compound is one or more of indoline spirooxazine photochromic compounds; the addition amount of the photochromic compound accounts for 0.1-10% of the dry weight of the polymer.
The composition may also contain additives, wherein the additives are one or more of dye, antioxidant, solvent, thickener, light stabilizer, heat stabilizer, ultraviolet absorbent, ultraviolet screening agent, ultraviolet inhibitor, free radical scavenger, gel, and adhesion promoter; the addition amount of the additive accounts for 0-50% of the dry weight of the polymer.
The structure of the indoline spirooxazine photochromic compound is shown as a formula I:
wherein,
R1selected from hydrogen, chlorine, bromine, methyl, methoxy or hydroxy;
R2is selected from C1-C18Alkyl, aryl, C substituted by heteroaryl1-C8Alkyl or C3-C8The heterocycloalkyl group of (a);
R3selected from hydrogen, chlorine, bromine, nitro, 5-10 membered nitrogen-containing heterocycle, di (C)1-C3) Alkylamino or para-di (C)1-C3) An alkylaminophenyl group.
The above-mentioned 5-to 10-membered nitrogen-containing heterocyclic ring may be a monocyclic ring or a condensed ring.
Preferred of said formula I are:
R1selected from hydrogen, chlorine, methyl or methoxy;
R2is selected from C1-C6Alkyl, aryl, C substituted by heteroaryl1-C3Alkyl or C3-C5The heterocycloalkyl group of (a);
r3 is selected from hydrogen, chlorine,-N(C2H5)2Or
Further preferred of said formula i are:
R1selected from hydrogen, chlorine or methyl;
R2is selected from C1-C6An alkyl group;
r3 is selected from hydrogen, chlorine,or-N (C)2H5)2。
The polymer is selected from one or more of waterborne polyurethane.
The waterborne polyurethane is selected from one or more of anionic waterborne polyurethane, cationic waterborne polyurethane and nonionic waterborne polyurethane.
Wherein, the definition of the anionic waterborne polyurethane, the cationic waterborne polyurethane or the nonionic waterborne polyurethane is reported in the document waterborne polyurethane material (Schgolvin et al waterborne polyurethane material [ M ]. Beijing: chemical industry Press, 2006.). The aqueous polyurethane can also be selected from polycarbonate aqueous polyurethane, and the polycarbonate aqueous polyurethane comprises aliphatic polycarbonate aqueous polyurethane and aromatic polycarbonate aqueous polyurethane. The aliphatic polycarbonate-based aqueous polyurethane and the aromatic polycarbonate-based aqueous polyurethane respectively include anionic, cationic or nonionic aqueous bases. The waterborne polyurethane is selected from one or a mixture of more of the above.
The waterborne polyurethane can be obtained commercially or synthesized by a conventional mature self-emulsification method. Firstly, polyol and diisocyanate are reacted to prepare a high-viscosity prepolymer with NCO as a terminal group, a low-boiling point solvent such as acetone is added to reduce the viscosity, then a hydrophilic monomer is used for chain extension, water is added under high-speed stirring, and the acetone is removed by reduced pressure distillation after dispersion. The waterborne polyurethane used in the composition of the invention prepared by the method has strong matching property with photochromic compounds, and the specific photochromic compounds and corresponding polymers have the effect of remarkably improving light fastness. The selected polymer has soft long chain structure and low glass transition temperature (T)g) The material has better flexibility and mechanical strength. Photochromic molecules are orderly arranged in a certain space by forming a film with a high molecular polymer. In addition, the photochromic compound can be protected by preferential breakage of unsaturated bonds on the polymer chain after illumination; the specific polymer also provides enough space for the photochromic molecules to perform reversible molecular structure change, so that the chromogen structure of the photochromic molecules is more stable. And in a particular matrix (polymer), one photochromic molecular morphology tends to be more stable than the other morphological molecules, the polymer structure influencing the photochromic balance. The composition may further comprise one or more of the following additives: the additives in the composition are dyes, antioxidants, solvents, thickeners, light stabilizers, ultraviolet absorbers, ultraviolet screening agents, ultraviolet inhibitors, free radical scavengers, gelling agents and adhesion promoters. The dye in the additive serves to modulate the desired substrate color. The functions of the antioxidant, the light stabilizer, the ultraviolet absorber, the ultraviolet screening agent and the free radical eliminator are to enhance the stability of the system. The gelling agent has the functions of increasing the viscosity of the system and changing the rheological property of the system. Wherein saidThe dye can be selected from pigments, direct dyes, acid dyes, basic dyes, disperse dyes, reactive dyes, vat dyes; the antioxidant is selected from phenolic compounds; the light stabilizer is selected from hindered amine light stabilizers; the ultraviolet absorbent is selected from salicylate compounds, metal ion chelates, benzophenone compounds, benzotriazole compounds, and reactive ultraviolet absorbent; the ultraviolet screening agent is selected from ceramic powder or metal oxide fine powder or superfine powder; the free radical scavenger is selected from non-enzymatic scavengers and enzymatic scavengers. The gelling agent is selected from conventional gelling agents.
The preferable additive is a thickening agent and an ultraviolet screening agent, and the thickening agent and the ultraviolet screening agent are both selected from metal oxides, preferably magnesium oxide, zinc oxide, aluminum oxide and silicon oxide.
In the composition, the mass of the photochromic compound accounts for 0.1-10% of the dry weight of the waterborne polyurethane, and the mass of other additives accounts for 0-50% of the dry weight of the waterborne polyurethane, preferably 0.01-30%. The preferable dosage of each component in the composition is 0.1-5% of the weight of the spirooxazine photochromic dye based on the dry weight of the polymer material.
The composition can be applied to the fields of anti-counterfeiting ink, optical lenses, indoor/outdoor decorative materials, paint, coating, artware or toys and the like.
It is still another object of the present invention to provide a photochromic article comprising the above photochromic composition, the photochromic article comprising a substrate, a primer coating, a photochromic coating and a protective coating. The coating is coated on the surface of the base material by the conventional method in the field, and the coating method is knife coating, printing, roll coating and spray coating. The substrate is formed of an organic material, an inorganic material, or a combination thereof. The photochromic coating layer can be formed by coating the photochromic composition into different thicknesses according to different requirements, and the thickness of the photochromic coating layer is generally 2-300 mu m, and preferably 50 mu m. The primer coating and the protective coating are both selected from polyurethanes, and may be applied to a desired thickness as needed, typically to a film thickness of 2 μm to 300 μm, preferably 50 μm. The substrate is preferably filter paper.
The photochromic product is applied to the fields of anti-counterfeiting ink, optical lenses, indoor/outdoor decorative materials, paint, coating, artware or toys.
The photochromic composition disclosed by the invention has the advantages of high light fastness, low cost and the like. The concrete aspects are as follows:
1. the composition of the invention still has obvious photochromism after long-time irradiation of xenon light. Compared with the prior art, the illumination method has better light fastness. According to the method of ISO105-B02, the photochromic material still has obvious photochromic property after being irradiated for 50 hours by a xenon lamp.
2. The composition has low cost, less usage of photochromic dye, adoption of water-based polymer, environmental protection and suitability for commercial production.
Detailed Description
The following specific examples are intended to further illustrate the invention, but the invention is by no means limited to these examples. Various modifications are possible within the scope defined by the claims. The indoline spirooxazine photochromic compounds of the examples can be obtained commercially or prepared according to the methods reported in patents JP07233174A, JP08027155A, US 4980089. The aqueous polyurethane, aqueous acrylic acid and other additives are commercially available. The coating method follows the conventional method in the field, such as: knife coating, printing, and the like.
Preparation examples
Example 1
Preparation of photochromic composition 1: photochromic compound A0.03g and anionic aliphatic waterborne polyurethane WPU-1.3.4 g are uniformly mixed to obtain the photochromic polyurethane.
Synthesizing waterborne polyurethane WPU-1:
the dehydrated polycarbonate diol (molecular weight 1000, hydroxyl value KOH110mg/g, industrial grade, Qingdao Denqing chemical industry) and hexamethylene diisocyanate (reagent grade, Shanghai Ziyi reagent factory) are added into a four-neck flask provided with an electric stirrer, a thermometer and a reflux condenser, the temperature is gradually increased to 60-65 ℃, and the reaction lasts for about 2 hours. Adding hydrophilic chain extender DMPA (2, 2-dimethylolbutyric acid), heating to about 80 ℃, and adding acetone for dilution. And then cooling to 30-40 ℃, and slowly adding deionized water for emulsification under high-speed stirring. Vacuum decompression is carried out to remove acetone to obtain the polyester anionic emulsion WPU-1 with the solid content of 35 percent.
Preparation of photochromic article 1:
primer coating: a coating having a thickness of 100 μm was printed on filter paper using the aqueous polyurethane dispersion described above and dried at 50 ℃ for 10 minutes.
Photochromic coating: on the surface of the primer coating after drying, a coating having a film thickness of 100 μm was coated with the photochromic composition 1 and dried at 50 ℃ for 10 minutes.
Protective coating: on the surface of the dried photochromic coating layer, a coating layer having a thickness of 100 μm was printed with the polymer, and dried at 50 ℃ for 10 minutes.
Example 2
Preparation of photochromic composition 2: 0.04g of photochromic compound B0.04g, 2g of waterborne polyester anionic emulsion WPU-2 and 0.2g of zinc oxide are uniformly mixed to obtain the photochromic emulsion.
Synthesizing waterborne polyurethane WPU-2:
the dehydrated polycaprolactone polyol (molecular weight 1000, hydroxyl value KOH 330-350 mg/g, industrial grade, Japan xylonite chemical) and hydrogenated xylylene diisocyanate (Takenate600, Bayer corporation) are added into a four-neck flask provided with an electric stirrer, a thermometer and a reflux condenser, and the temperature is gradually increased to 60-65 ℃ for reaction for about 2.0 hours. Adding chain extender 1, 4-butanediol, heating to about 80 ℃, and adding acetone for dilution. And then cooling to 30-40 ℃, and slowly adding deionized water for emulsification under high-speed stirring. Vacuum decompression is carried out to remove acetone to obtain the polyester anionic emulsion WPU-2 with the solid content of 38 percent.
Preparation of photochromic article 2:
primer coating: on filter paper, a coating having a thickness of 50 μm was printed with the above aqueous polyurethane dispersion and dried at 50 ℃ for 10 minutes.
Photochromic coating: on the surface of the primer coating after drying, a coating having a film thickness of 50 μm was coated with the photochromic composition 1 and dried at 50 ℃ for 10 minutes.
Protective coating: on the surface of the dried photochromic coating layer, a coating layer having a thickness of 50 μm was printed with the aqueous adhesive b, and dried at 50 ℃ for 10 minutes to obtain a photochromic article 2.
Example 3
Preparation of photochromic composition 3: 0.001g of photochromic compound, 2.6g of nonionic waterborne polyurethane WPU-3, 0.01g of 1,2, 3-benzotriazole and 0.4g of magnesium oxide, and the photochromic compound, the 1,2, 3-benzotriazole and the magnesium oxide are uniformly mixed to obtain the photochromic polyurethane.
Synthesizing waterborne polyurethane WPU-3:
adding dehydrated polyether glycol (N-210, industrial grade, third petrochemical plant of Tianjin petrochemical company) into a four-neck flask provided with an electric stirrer, a thermometer and a reflux condenser, adding a certain amount of acetone, introducing dry nitrogen, starting stirring, gradually heating to 70 ℃, dropwise adding isophorone diisocyanate (IPDI, industrial grade, Shanghai Jinle practical Co., Ltd.), adding dibutyltin dilaurate and ethylene glycol, and reacting for about 3 hours; adding polyethylene glycol monomethyl ether, and reacting for about 0.5 hour; cooling to below 15 deg.c, and slowly adding deionized water while stirring at high speed for emulsification. And removing acetone under vacuum reduced pressure to obtain the non-ionic waterborne polyurethane dispersion WPU-3 with the solid content of 40%.
Preparation of photochromic article 3:
primer coating: on filter paper, a coating having a thickness of 300 μm was printed with the above aqueous polyurethane dispersion and dried at 50 ℃ for 10 minutes.
Photochromic coating: on the surface of the primer coating after drying, a coating having a film thickness of 300 μm was coated with the photochromic composition 1 and dried at 50 ℃ for 10 minutes.
Protective coating: on the surface of the dried photochromic coating layer, a coating layer having a thickness of 300 μm was printed with the polymer, and dried at 50 ℃ for 10 minutes to obtain a photochromic article 3.
Example 4
Preparation of photochromic composition 4: 0.006g of photochromic compound D0.006g, 0.006g of photochromic compound E0.006g, 2.7g of cationic waterborne polyurethane WPU-4 and 0.8g of silicon oxide, and the photochromic polyurethane is obtained after being uniformly mixed.
Synthesizing waterborne polyurethane WPU-4:
adding dehydrated polyester triol (molecular weight 900, hydroxyl value KOH183mg/g, industrial grade, Jining HuaKai resin Co., Ltd.) into a four-neck flask provided with an electric stirrer, a thermometer and a reflux condenser, heating to 60 ℃, adding 4, 4' -dicyclohexylmethane diisocyanate (hydrogenated MDI, DESMODURW, Bayer Co., Ltd.) and trimethylolpropane, reacting for 2 hours at 80-85 ℃, then cooling to about 40 ℃, adding N-methyldiethanolamine, diluting with acetone, and reacting for 20 minutes at 45-50 ℃; slowly adding the reaction product into prepared deionized water added with formic acid under high-speed stirring, and distilling out acetone under reduced pressure to obtain the cationic waterborne polyurethane WPU-4 with the solid content of 40%.
Preparation of photochromic article 4:
primer coating: on the filter paper, a coating having a thickness of 200 μm was printed with the above-mentioned polymer and dried at 50 ℃ for 10 minutes.
Photochromic coating: on the surface of the primer coating after drying, a coating having a thickness of 200 μm was coated with the photochromic composition 4 and dried at 50 ℃ for 10 minutes.
Protective coating: on the surface of the dried photochromic coating layer, a coating layer having a thickness of 200 μm was printed with the above polymer, and dried at 50 ℃ for 10 minutes to obtain a photochromic article 4.
Example 5
Preparation of photochromic composition 5: photochromic compound E0.08g, anionic aliphatic waterborne polyurethane WPU-5, nonionic waterborne polyurethane WPU-6, aluminum oxide 1.0g and tert-butyl hydroquinone 0.02g, and the photochromic compound is obtained after being uniformly mixed.
Synthesizing waterborne polyurethane WPU-5:
polyethylene glycol adipate (Aldrich) and isophorone diisocyanate (IPDI, industrial grade, Shanghai Jinle Kogyo Co., Ltd.) were added into a four-necked flask equipped with an electric stirrer, a thermometer and a reflux condenser, and the temperature was gradually raised to 60 to 65 ℃ for reaction for about 2.0 hours. Adding chain extender glycerol, heating to about 80 ℃, and adding acetone for dilution. And then cooling to 30-40 ℃, and slowly adding deionized water for emulsification under high-speed stirring. Vacuum decompression is carried out to remove acetone to obtain the polyester anionic emulsion WPU-5 with the solid content of 40 percent.
Synthesizing waterborne polyurethane WPU-6:
adding dehydrated polyester triol (molecular weight 900, hydroxyl value KOH183mg/g, industrial grade, Jining Huakai resin Co., Ltd.) into a four-neck flask provided with an electric stirrer, a thermometer and a reflux condenser, adding a certain amount of acetone, introducing dry nitrogen, starting stirring, gradually heating to 70 ℃, dropwise adding 4, 4' -dicyclohexylmethane diisocyanate (hydrogenated MDI, DESMODURW, Bayer Co.), adding dibutyltin dilaurate and ethylene glycol, and reacting for about 3 hours; adding hydroquinone dihydroxyethyl ether, and reacting for about 0.5 hour; cooling to below 15 deg.c, and slowly adding deionized water while stirring at high speed for emulsification. And removing acetone under vacuum reduced pressure to obtain the non-ionic waterborne polyurethane dispersion WPU-6 with the solid content of 40%.
Preparation of photochromic article 5:
primer coating: on filter paper, a coating having a thickness of 2 μm was printed with the above aqueous polyurethane dispersion and dried at 50 ℃ for 10 minutes.
Photochromic coating: on the surface of the primer coating after drying, a coating having a thickness of 2 μm was coated with the photochromic composition 1 and dried at 50 ℃ for 10 minutes.
Protective coating: on the surface of the dried photochromic coating layer, a coating layer having a thickness of 2 μm was printed with the above polymer, and dried at 50 ℃ for 10 minutes to obtain a photochromic article 5.
Comparative example
Comparative example 1
According to example 2 in japanese patent JP 63234084A: 0.3g of photochromic compound with the structure shown in the formula II, 2g of polyvinyl butyral, 0.9g of dicarboxylic ester of triethylene glycol as a plasticizer, 0.015g of light stabilizer with the structure shown in the formula III and 47g of mixed solvent (ethanol, toluene and n-butyl alcohol are 50: 45: 5) are uniformly mixed to obtain the photochromic compound.
Preparation of the article of comparative example 1: on the filter paper, a coating having a thickness of 100 μm was printed and dried at 120 ℃ for 30 minutes.
Comparative example 2
Photochromic compound A0.03g, polyvinyl butyral 2g, light stabilizer with the structure of formula III 0.015g and mixed solvent 47g (ethanol: toluene: n-butanol: 50: 45: 5) are mixed uniformly to obtain the photochromic compound.
Preparation of the article of comparative example 2: the same as in example 1.
Comparative example 3
The photochromic compound is obtained by uniformly mixing 0.1g of photochromic compound with the structure shown in formula II and 3.4g of anionic waterborne polyurethane WPU-1 with the solid content of 35 (w)%.
Preparation of the article of comparative example 3: the same as in example 1.
Examples of Performance
Examples 1 to 5 and comparative examples 1 and 2: photochromic articles 1-5 and comparative examples 1 and 2 were continuously irradiated under a xenon lamp for 50 hours according to ISO 105-B02.
The photochromic articles 1 to 5 before and after irradiation and the comparative examples 1 and 2 were respectively tested for L, A, B (before irradiation) and L ', A ', B ' (after irradiation) values under excitation of ultraviolet light (wavelength 254nm, 365nm) with a colorimeter, and the hue difference value Δ E was calculated as shown in Table 1. The difference value delta E represents the difference of colors, and the calculation formula is delta E ═ L '-L')2+(A－A’)2+(B－B’)2]1/2。
As can be seen from Table 1, the photochromic articles 1-5 prepared from the photochromic composition of the invention still have obvious photochromic property and small color difference value after long-time irradiation by a xenon lamp. Comparative examples 1,2 photochromic articles lost photochromic performance after xenon lamp irradiation.
The photochromic compound accounts for 0.1-10% of the polymer by mass, while the photochromic compound accounts for 15% of the comparative example, so that the photochromic compound obviously reduces the using amount of the compound, saves the cost of the product and has higher light fastness.
TABLE 1 color difference and Properties before and after 50 hours of xenon lamp irradiation for photochromic articles 1-5 and comparative examples 1-2
Claims (9)
1. A photochromic composition characterized by: the composition is a photochromic compound and a polymer; wherein the photochromic compound is one or more of indoline spirooxazine photochromic compounds; the addition amount of the photochromic compound accounts for 0.1-10% of the dry weight of the polymer.
2. The photochromic composition of claim 1 wherein: the composition is added with additives, wherein the additives are one or more of dyes, antioxidants, solvents, thickeners, light stabilizers, heat stabilizers, ultraviolet absorbers, ultraviolet screening agents, ultraviolet inhibitors, free radical scavengers, gelling agents and adhesion promoters; the addition amount of the additive accounts for 0-50% of the dry weight of the polymer.
3. The photochromic composition of claim 1 wherein:
the structure of the indoline spirooxazine photochromic compound is shown as a formula I:
wherein,
R1selected from hydrogen, chlorine, bromine, methyl, methoxy or hydroxy;
R2is selected from C1-C18Alkyl, aryl, C substituted by heteroaryl1-C8Alkyl or C3-C8The heterocycloalkyl group of (a);
R3selected from hydrogen, chlorine, bromine, 5-10 membered nitrogen-containing heterocycles, di (C)1-C3) Alkylamino or para-di (C)1-C3) An alkylaminophenyl group.
4. The photochromic composition of claim 3 wherein: in the formula I, the compound has the following structure,
R1selected from hydrogen, chlorine, methyl or methoxy;
R2is selected from C1-C6Alkyl, aryl, C substituted by heteroaryl1-C3Alkyl or not C3-C5The heterocycloalkyl group of (a);
r3 is selected from hydrogen, chlorine,-N(C2H5)2Or
5. The photochromic composition of claim 1 wherein: the polymer is selected from one or more of waterborne polyurethane.
6. The photochromic composition of claim 5 wherein: the waterborne polyurethane is selected from one or more of anionic waterborne polyurethane, cationic waterborne polyurethane and nonionic waterborne polyurethane.
7. Use of a photochromic composition according to claim 1 wherein: the composition is used as a photochromic substance in anti-counterfeiting ink, optical lenses, indoor/outdoor decorative materials, paint, coating, artware or toys.
8. A photochromic article comprising a substrate, a primer coating, a photochromic coating, and a protective coating, wherein: the photochromic coating is a photochromic composition, wherein the thickness of the photochromic coating is 2-300 μm.
9. Use of a photochromic article according to claim 8 wherein: the photochromic product is applied to the fields of anti-counterfeiting ink, optical lenses, indoor/outdoor decorative materials, paint, coating, artware or toys as a photochromic object.
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| CN113912775A (en) * | 2021-11-03 | 2022-01-11 | 江苏海伦隐形眼镜有限公司 | Indicator material and preparation method and application thereof |
| CN114479555A (en) * | 2022-01-24 | 2022-05-13 | 福州大学 | Photochromic wear-resistant waterborne polyurethane ink |
| CN116891675A (en) * | 2023-06-05 | 2023-10-17 | 江苏励杰光电科技有限公司 | Aqueous photochromic composition and use thereof |
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