Polymer resin and preparation method therefor, optical lens and smart glasses
The polymer resin prepared by reacting thiocyanate and amino compounds solves the problems of complex synthesis and poor stability of hydroxyl-modified polyphenylene sulfide, and achieves improved high refractive index, light transmittance and mechanical properties, as well as improved antioxidant properties and stability.
Patent Information
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- ZHUHAI MOJIE TECH CO LTD
- Filing Date
- 2025-06-19
- Publication Date
- 2026-07-02
AI Technical Summary
Existing technologies for increasing the refractive index of polymer resins involve complex synthesis processes for hydroxyl-modified polyphenylene sulfide, which is prone to oxidation of the benzene ring, leading to resin yellowing, poor solubility, poor oxidation resistance and stability, and difficulty in processing.
A polymeric resin containing thioamide and aromatic groups was prepared by reacting thiocyanate and amino compounds under catalyst-free conditions. The hydrogen bond acceptor and donor were embedded in the main chain structure, which simplified the synthesis process and improved the molecular weight and stability.
It achieves high refractive index, good light transmittance, mechanical properties and heat resistance, while enhancing oxidation resistance and stability, and reducing production costs and process difficulty.
Smart Images
Figure CN2025102061_02072026_PF_FP_ABST
Abstract
Description
Polymer resins and their preparation methods, optical lenses and smart glasses
[0001] Cross-reference of related applications
[0002] This application is based on Chinese Patent Application No. 2024119508300, filed on December 26, 2024, entitled "Polymer Resin and Preparation Method Thereof, Optical Lens and Smart Glasses", and claims priority to the aforementioned Chinese Patent Application, the entire contents of which are incorporated herein by reference. Technical Field
[0003] This application relates to the field of resin materials technology, and in particular to a polymer resin and its preparation method, optical lenses, and smart glasses. Background Technology
[0004] Optical materials are mainly divided into two categories: glass and resin, and are widely used in displays, lenses, sensors, and many other fields. Among them, optical resin materials are receiving increasing attention in the field of optical materials due to their advantages such as low specific gravity, high impact toughness, rich structural design, and ease of processing. Refractive index is one of the most important indicators reflecting the properties of optical resin materials. A higher refractive index can effectively improve light efficiency, reduce lens thickness, lower costs, and achieve a better wearing experience.
[0005] Related technologies generally use the introduction of hydroxyl groups into the benzene ring of polyphenylene sulfide to improve the refractive index of the polymer resin. However, the synthesis process of hydroxyl-modified polyphenylene sulfide is complex, and the benzene ring is prone to oxidation, which leads to yellowing, decreased solubility and lower molecular weight of the polymer resin. Consequently, the polymer resin has poor oxidation resistance and stability and is difficult to process. Summary of the Invention
[0006] Based on this, this application provides a polymer resin and its preparation method, an optical lens and smart glasses, which can improve the antioxidant properties and stability of the polymer resin while also having high refractive index properties.
[0007] In a first aspect, this application provides a polymeric resin having the following general structural formula:
[0008] In the formula, at least one of R1 and R2 is an aromatic group, and n is a positive integer from 1 to 10000.
[0009] Secondly, this application provides a polymeric resin, which is prepared from the following raw materials: thiocyanate, amino compound and solvent.
[0010] Thirdly, this application provides a method for preparing a polymeric resin, the method comprising:
[0011] Provides thiocyanates, amino compounds, and solvents;
[0012] The thiocyanate, the amino compound, and the solvent are stirred evenly and reacted to obtain a polymeric resin.
[0013] Fourthly, this application provides an optical lens made of a polymeric resin as described above, or a polymeric resin prepared by the method described above.
[0014] Fifthly, this application provides smart glasses, which include the optical lenses described above.
[0015] This application provides a polymeric resin and its preparation method, an optical lens, and smart glasses. The polymeric resin comprises two structures: a thioamide group and an aromatic group, exhibiting high refractive index, good light transmittance, and excellent mechanical properties, heat resistance, and low shrinkage. Furthermore, the hydrogen bond acceptor and hydrogen bond donor of the polymeric resin provided in this application are both located within the main chain structure of the resin, eliminating the need for additional modification steps during introduction and simplifying the synthesis process. Moreover, the raw materials provided in this application are readily available, highly reactive, and can react without the use of any catalyst, resulting in simple reaction conditions and reduced process difficulty and production costs. In addition, by directly embedding the hydrogen bond acceptor and hydrogen bond donor into the main chain, its solubility can be optimized, the molecular weight of the polymeric resin can be increased, and its thermal stability and processing performance can be improved. Moreover, since the hydrogen bond acceptor and hydrogen bond donor are directly embedded in the main chain structure of the polymeric resin, active sites can be significantly reduced or eliminated, thereby improving the antioxidant properties and stability of the polymeric resin and reducing the probability of yellowing. Attached Figure Description
[0016] To more clearly illustrate the technical solutions of the embodiments of this application, the drawings used in the description of the embodiments will be briefly introduced below. Obviously, the drawings described below are some embodiments of this application. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.
[0017] Figure 1 is a schematic flowchart of a method for preparing a polymeric resin according to an embodiment of this application. Detailed Implementation
[0018] The technical solutions of the embodiments of this application will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some embodiments of this application, and not all embodiments. Based on the embodiments of this application, all other embodiments obtained by those of ordinary skill in the art without creative effort are within the scope of protection of this application.
[0019] The flowchart shown in the attached diagram is for illustrative purposes only and does not necessarily include all content and operations / steps, nor does it necessarily have to be performed in the order described. For example, some operations / steps can be broken down, combined, or partially merged, so the actual execution order may change depending on the actual situation.
[0020] In the following description, the use of suffixes such as "module," "part," or "unit" to denote elements is solely for the purpose of illustration and has no inherent meaning. Therefore, "module," "part," or "unit" may be used interchangeably.
[0021] Related technologies generally use the introduction of hydroxyl groups into the benzene ring of polyphenylene sulfide to improve the refractive index of the polymer resin. However, the synthesis process of hydroxyl-modified polyphenylene sulfide is complicated, and the hydroxyl groups on the benzene ring may become active sites for oxidation reactions, which makes the resin prone to oxidation reactions under light, high temperature or oxygen, thus causing yellowing. It also reduces the solubility of the resin and lowers the molecular weight, resulting in poor oxidation resistance and stability of the polymer resin and making it difficult to process.
[0022] To address the aforementioned challenges, this application provides a polymeric resin and its preparation method, an optical lens, and smart glasses. This polymeric resin possesses a high refractive index, good light transmittance, excellent mechanical properties, heat resistance, and low shrinkage. Furthermore, the raw materials are readily available and highly reactive, requiring no catalyst for reaction. The reaction conditions are simple, the synthesis process is straightforward, the process is easy to implement, and the production cost is low. Moreover, this polymeric resin exhibits good oxidation resistance and stability.
[0023] The embodiments of this application will now be described in detail with reference to the accompanying drawings.
[0024] This application provides a polymeric resin having the following general structural formula:
[0025] In the formula, at least one of R1 and R2 is an aromatic group, and n is a positive integer from 1 to 10000.
[0026] The polymeric resin includes thioamide groups and aromatic groups, and the structural formula of the thioamide groups is as follows:
[0027] The thioamide group comprises a sulfur atom and an NH bond. The sulfur atom in the thioamide group is a high molar refractive index group, which slows down the propagation speed of light, thereby increasing the refractive index. The nitrogen atom in the NH bond can act as a hydrogen bond acceptor, which facilitates the formation of hydrogen bonds, thereby enhancing the intermolecular forces of the resin and achieving a dense atomic packing effect, thus increasing the refractive index. The thioamide group provided in this application has two NH bonds, which can further enhance the intermolecular forces of the resin, thereby further increasing the refractive index.
[0028] For example, R1 can be an aromatic group, and R2 can be any group other than an aromatic group; R2 can be an aromatic group, and R1 can be any group other than an aromatic group; R1 and R2 can both be aromatic groups. n represents an integer from 1 to 10000, for example, n can take values of 1, 60, 120, 700, 3000, 6000, and 10000, etc.
[0029] The polymeric resin provided in this application has an ultra-high refractive index. This is due to two main factors. First, the high degree of unsaturation in the structure of the polymeric resin, such as the six-membered aromatic ring in the aromatic group. The presence of unsaturated double bonds in the aromatic group allows the resin to form a more compact network structure during curing, thereby increasing the refractive index of the polymeric resin. In addition, the thioamide group has a high sulfur atom ratio. Sulfur itself is a group with a high molar refractive index, which slows down the propagation speed of light when it passes through, thus increasing the refractive index. Second, it benefits from the abundance of hydrogen bond acceptors and hydrogen bond donors. Hydrogen bond acceptors can include nitrogen and sulfur atoms in the thioamide group and nitrogen atoms with lone pairs of electrons in the aromatic ring. Hydrogen bond donors can include thioamide groups and NH bonds in the aromatic ring. Since the polymeric resin contains atoms with strong electronegativity (such as oxygen, nitrogen, or sulfur), these atoms easily form hydrogen bonds, and hydrogen bonds can also be formed between groups. Therefore, under the action of multiple hydrogen bonds with varying strengths, the intermolecular forces of the resin can be enhanced, thereby achieving the effect of dense atomic packing, which can further increase the refractive index, making the refractive index of the polymeric resin reach 1.8 or higher.
[0030] Secondly, the polymeric resin provided in this application also has good light transmittance. On the one hand, due to the large atomic radius of sulfur atoms, it is difficult for groups / atoms and groups / groups to form conjugated structures, resulting in weak light absorption; on the other hand, the diverse and varying strengths of hydrogen bonds in the polymeric resin can effectively prevent the formation of ordered crystalline structures between resin molecules, instead forming an amorphous stacked structure, thereby effectively preventing light scattering and enhancing light transmittance.
[0031] Furthermore, the polymeric resin provided in this application also possesses excellent mechanical properties, heat resistance, and low shrinkage. This is because the rigid structure of the aromatic groups and the low chain freedom of the polymer molecules significantly improve the mechanical properties and heat resistance of the polymeric resin, while also effectively reducing its shrinkage.
[0032] Because the polymeric resin provided in this application includes both thioamide and aromatic groups, it possesses high refractive index, good light transmittance, excellent mechanical properties, heat resistance, and low shrinkage. Furthermore, the hydrogen bond acceptors and donors of the polymeric resin provided in this application are located within the main chain structure, eliminating the need for additional modification steps and simplifying the synthesis process. The raw materials provided in this application are readily available, highly reactive, and can react without any catalyst, simplifying the reaction conditions and reducing process complexity and production costs. Moreover, by directly embedding the hydrogen bond acceptors and donors into the main chain, the strong hydrogen bond forces and molecular polarity enhance the solubility of the polymeric resin in polar solvents, thus optimizing its solubility and increasing its molecular weight. Increased molecular weight improves its thermal stability and processing performance. In addition, since the hydrogen bond acceptors and donors are directly embedded in the main chain structure of the polymeric resin, active sites can be significantly reduced or eliminated, thereby improving the antioxidant properties and stability of the polymeric resin and reducing the probability of yellowing.
[0033] In some embodiments, R1 and R2 are both aromatic groups.
[0034] When both R1 and R2 are aromatic groups, the degree of unsaturation of the polymer resin can be increased. The presence of unsaturated double bonds in the aromatic groups allows the resin to form a more compact network structure during the curing process, thereby improving the refractive index, light transmittance, mechanical properties and heat resistance of the polymer resin, and reducing the shrinkage rate of the polymer resin.
[0035] In some embodiments, the aromatic group may be selected from one or more of the following: benzene ring, naphthyl ring, fluorene, carbazole, furan, thiophene, pyrrole, thiazole, imidazole, pyridine, pyrazine, pyrimidine, and pyridazine.
[0036] In some embodiments, the polymeric resin provided in this application is selected from any one of the structural formulas P1-P5.
[0037] in:
[0038] P1:
[0039] P2:
[0040] P3:
[0041] P4:
[0042] P5:
[0043] The following describes the general structural formula provided in this application: The composition of raw materials for the preparation of polymer resin.
[0044] The polymer resin is made from the following raw materials: thiocyanate, amino compound and solvent.
[0045] In the embodiments of this application, a polymeric resin comprising thioamide groups and aromatic groups can be prepared by reacting raw materials such as thiocyanate, amino compounds, and solvents. This results in a polymeric resin with high refractive index, good light transmittance, good mechanical properties, heat resistance, and low shrinkage. Furthermore, the raw materials provided in this application are readily available and highly reactive, and the reaction conditions are simple. The polymeric resin can be prepared without the use of any catalyst, and both hydrogen bond acceptors and hydrogen bond donors are located in the main chain structure of the polymeric resin. The introduction process requires no additional modification steps, thus simplifying the synthesis process and reducing the difficulty and production cost. Moreover, since this preparation method can directly embed hydrogen bond acceptors and hydrogen bond donors into the main chain, the strong hydrogen bond forces and high molecular polarity increase the solubility of the polymeric resin in polar solvents, thereby optimizing its solubility and increasing the molecular weight of the polymeric resin. Increased molecular weight improves its thermal stability and processing performance. Furthermore, since hydrogen bond acceptors and hydrogen bond donors are directly embedded in the main chain structure of polymer resins, active sites can be significantly reduced or eliminated, thereby improving the antioxidant properties and stability of polymer resins and reducing the probability of yellowing.
[0046] In some embodiments, the molar ratio of thiocyanate, amino compound and solvent is (257-350):300:(22000-26000).
[0047] For example, the molar ratio of thiocyanate, amino compound and solvent can be 257:300:22114.
[0048] For example, the molar ratio of thiocyanate, amino compound and solvent can be 330:300:24000.
[0049] For example, the molar ratio of thiocyanate, amino compound and solvent can be 340:300:23800.
[0050] For example, the molar ratio of thiocyanate, amino compound and solvent can be 350:300:23600.
[0051] For example, the molar ratio of thiocyanate, amino compound and solvent can be 350:300:25800.
[0052] In some embodiments, the molar ratio of thiocyanate, amino compound and solvent is (300-305):300:(23300-23350).
[0053] For example, the molar ratio of thiocyanate, amino compound and solvent can be 300:300:23300.
[0054] For example, the molar ratio of thiocyanate, amino compound and solvent can be 305:300:23350.
[0055] For example, the molar ratio of thiocyanate, amino compound and solvent can be 303:300:23320.
[0056] For example, the molar ratio of thiocyanate, amino compound and solvent can be 300:300:23350.
[0057] For example, the molar ratio of thiocyanate, amino compound and solvent can be 301:300:23325.
[0058] For example, the molar ratio of thiocyanate, amino compound and solvent can be 302:300:23340.
[0059] It is understandable that by reasonably controlling the molar ratio of each component, this application can achieve full synergy among the components, and prevent the performance of the final polymer resin from deteriorating due to an excess or deficiency of a certain component, thus ensuring that the final polymer resin has better overall performance.
[0060] The following explanation is based on a molar amount of 300 for amino compounds.
[0061] For example, by controlling the molar amount of thiocyanate to 257–350, thiocyanate can react with amino compounds to form a polymeric resin with thioamide groups and aromatic groups, and the hydrogen bond acceptor and hydrogen bond donor of the polymeric resin are both located in the main chain structure of the polymeric resin.
[0062] For example, by controlling the molar amount of solvent between 22,000 and 26,000, the solvent can fully wet other components and make the components miscible, forming a relatively homogeneous mixed system, which facilitates the preparation of polymer resins.
[0063] In some embodiments, the thiocyanate may be selected from one or more of phenyl diisothiocyanate, terephthalic diisothiocyanate, terephthalic dimethyl dithiocyanate, and pyridine diisothiocyanate.
[0064] In some embodiments, the amino compound may be selected from one or more of 4,4-diaminodiphenyl sulfide, 4,4-thioether-bis(1,3,5-triazine-2-amine), 4,4-(1,4-phenylene di(sulfide))diphenylamine, 9,9-bis(4-aminophenyl)fluorene, 6,6'-thioether-bis(2-aminopyridine), 1,4-bis(3-aminophenoxy)benzene, 1,3-bis(4-aminophenyl)adamantane, and bis[4-(4-aminophenoxy)phenyl]sulfone.
[0065] In some embodiments, the solvent may be one or more of N,N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), and N-methyl-2-pyrrolidone (NMP).
[0066] The following describes a method for preparing the polymeric resin comprising the aforementioned components.
[0067] As shown in Figure 1, this application embodiment also provides a method for preparing a polymeric resin, including the following steps:
[0068] S101 provides thiocyanates, amino compounds, and solvents;
[0069] S102. Thiocyanate, amino compound and solvent are stirred evenly and reacted to obtain polymer resin.
[0070] It should be noted that specific examples of thiocyanate, amino compounds and solvents can be found in the examples above, and will not be repeated here.
[0071] In this embodiment, raw materials such as thiocyanate, amino compounds, and solvents are stirred evenly for reaction to obtain a polymeric resin containing thioamide groups and aromatic groups. This results in a polymeric resin with high refractive index, good light transmittance, good mechanical properties, heat resistance, and low shrinkage. Furthermore, the raw materials provided in this application are readily available and highly reactive, and the reaction conditions are simple. The polymeric resin can be prepared without the use of any catalyst, and both hydrogen bond acceptors and hydrogen bond donors are located in the main chain structure of the polymeric resin. The introduction process requires no additional modification steps, thus simplifying the synthesis process and reducing the difficulty and production cost. Moreover, since this preparation method can directly embed hydrogen bond acceptors and hydrogen bond donors into the main chain, its solubility can be optimized, the molecular weight of the polymeric resin can be increased, and its thermal stability and processing performance can be improved. In addition, because the hydrogen bond acceptors and hydrogen bond donors are directly embedded in the main chain structure of the polymeric resin, active sites can be significantly reduced or eliminated, thereby improving the antioxidant properties and stability of the polymeric resin and reducing the probability of yellowing.
[0072] In some embodiments, in step S102, thiocyanate, amino compound and solvent are stirred evenly to carry out the reaction, the reaction temperature is 22°C to 24°C, the reaction time is 23.5 hours to 24.5 hours, and the reaction environment is a nitrogen atmosphere.
[0073] By controlling the reaction temperature of the above raw materials to 22℃~24℃, the reaction time to 23.5 hours~24.5 hours, and the reaction environment to be a nitrogen atmosphere, the thiocyanate and amino compound can fully react. The thiocyanate and amino compound have high activity and can react without a catalyst. As a result, the prepared polymer resin has a high refractive index, good antioxidant properties, stability, light transmittance, good mechanical properties, heat resistance, and low shrinkage.
[0074] In some specific embodiments, the reaction temperature is 23°C and the reaction time is 24 hours.
[0075] For example, after stirring the thiocyanate, amino compound and solvent evenly to react, the reaction solution is filtered through a filter to remove solid insoluble matter, and the filtrate is added dropwise to methanol to precipitate. The precipitate is filtered and washed with methanol, and then dried under vacuum at 40°C to obtain the polymer resin.
[0076] This application also provides an optical lens, in which a diffractive waveguide structure is assembled. The substrate of the diffractive waveguide structure is made of the polymeric resin described in any of the above embodiments, or of the polymeric resin prepared by the method described in any of the above embodiments.
[0077] This application also provides a smart glasses, which includes the optical lenses described in any of the above embodiments.
[0078] The embodiments of this application will be described below through specific examples.
[0079] Example 1:
[0080] Under nitrogen atmosphere, terephthalic diisothiocyanate (576.8 mg, 3 mmol) and 4,4'-diaminodiphenyl sulfide (648.9 mg, 3 mmol) were added to a 100 mL three-necked reaction flask equipped with a magnetic stir bar. Then, 18 mL of DMF was injected using a syringe to dissolve the raw materials. The mixture was stirred continuously at room temperature (23°C) for 24 hours. The resulting solution was filtered to remove solid insoluble matter, and the filtrate was added dropwise to 250 mL of methanol for precipitation. The precipitate was filtered, washed three times with methanol, and then dried under vacuum at 40°C to obtain polymer resin P1. In this embodiment, the molar ratio of terephthalic diisothiocyanate, 4,4'-diaminodiphenyl sulfide, and DMF was 300:300:23300.
[0081] In this embodiment, the raw material composition is detailed in Table 1.
[0082] Table 1
[0083] In this embodiment, the structural formula of the polymeric resin P1 is:
[0084] Example 2:
[0085] Under nitrogen atmosphere, 480.7 mg (2.5 mmol) of p-phenylene diisothiocyanate and 555.5 mg (2.5 mmol) of 4,4'-thioether-bis(1,3,5-triazine-2-amine) were added to a 100 mL three-necked reaction flask equipped with a magnetic stir bar. Then, 15 mL of DMF was injected using a syringe to dissolve the raw materials. The mixture was stirred continuously at room temperature (23°C) for 24 hours. The resulting solution was filtered to remove solid insoluble matter, and the filtrate was added dropwise to 250 mL of methanol for precipitation. The precipitate was filtered, washed three times with methanol, and then dried under vacuum at 40°C to obtain polymer resin P2. In this embodiment, the molar ratio of p-phenylene diisothiocyanate, 4,4'-thioether-bis(1,3,5-triazine-2-amine), and DMF was 300:300:23280.
[0086] In this embodiment, the raw material composition is detailed in Table 2.
[0087] Table 2
[0088] In this embodiment, the structural formula of the polymeric resin P2 is:
[0089] Example 3:
[0090] Under nitrogen atmosphere, terephthalic diisothiocyanate (672.9 mg, 3.5 mmol) and 4,4'-(1,4-phenylene di(thio))diphenylamine (973.8 mg, 3 mmol) were added to a 100 mL three-necked reaction flask equipped with a magnetic stir bar. Then, 20 mL of DMF was injected using a syringe to dissolve the raw materials. The mixture was stirred continuously at room temperature (23°C) for 24 hours. The resulting solution was filtered to remove solid insoluble matter, and the filtrate was added dropwise to 250 mL of methanol for precipitation. The precipitate was filtered, washed three times with methanol, and then dried under vacuum at 40°C to obtain polymer resin P3. In this embodiment, the molar ratio of terephthalic diisothiocyanate, 4,4'-(1,4-phenylene di(thio))diphenylamine, and DMF was 350:300:25800.
[0091] In this embodiment, the raw material composition is detailed in Table 3.
[0092] Table 3
[0093] In this embodiment, the structural formula of the polymeric resin P3 is:
[0094] Example 4:
[0095] Under nitrogen atmosphere, terephthalic diisothiocyanate (576.8 mg, 3 mmol) and 9,9-bis(4-aminophenyl)fluorene (1219.5 mg, 3.5 mmol) were added to a 100 mL three-necked reaction flask equipped with a magnetic stir bar. Then, 20 mL of DMF was injected using a syringe to dissolve the raw materials. The mixture was stirred continuously at room temperature (23°C) for 24 hours. The resulting solution was filtered to remove solid insoluble matter, and the filtrate was added dropwise to 250 mL of methanol for precipitation. The precipitate was filtered, washed three times with methanol, and then dried under vacuum at 40°C to obtain polymeric resin P4. In this embodiment, the molar ratio of terephthalic diisothiocyanate, 9,9-bis(4-aminophenyl)fluorene, and DMF was 257:300:22114.
[0096] In this embodiment, the raw material composition is detailed in Table 4.
[0097] Table 4
[0098] In this embodiment, the structural formula of the polymeric resin P4 is:
[0099] Example 5:
[0100] Under nitrogen atmosphere, terephthalic diisothiocyanate (538.3 mg, 2.8 mmol) and 6,6'-thioether-bis(2-aminopyridine) (545.5 mg, 2.5 mmol) were added to a 100 mL three-necked reaction flask equipped with a magnetic stir bar. Then, 15 mL of DMF was injected using a syringe to dissolve the raw materials. The mixture was stirred continuously at room temperature (23°C) for 24 hours. The resulting solution was filtered to remove solid insoluble matter, and the filtrate was added dropwise to 250 mL of methanol for precipitation. The precipitate was filtered, washed three times with methanol, and then dried under vacuum at 40°C to obtain polymer resin P5. In this embodiment, the molar ratio of terephthalic diisothiocyanate, 6,6'-thioether-bis(2-aminopyridine), and DMF was 336:300:23280.
[0101] In this embodiment, the raw material composition is detailed in Table 5.
[0102] Table 5
[0103] In this embodiment, the structural formula of the polymeric resin P5 is:
[0104] Comparative example:
[0105] Polymer resin P6 was prepared by introducing hydroxyl groups into the benzene ring of polyphenylene sulfide.
[0106] Experimental example:
[0107] The resin performance parameters of polymeric resins P1-P5 prepared in Examples 1-5 and polymeric resin P6 provided in the comparative example were tested, including refractive index, Abbe number, water absorption, light transmittance, glass transition temperature (Tg) and yellowness index. The results are shown in Table 6.
[0108] The compounds (i.e., polymeric resins P1-P6) obtained in Examples 1 to 5 and the comparative examples were subjected to the following tests:
[0109] 1. Refractive Index Test. The purified resin was dispersed in a polar solvent, such as tetrachloroethane, and then spin-coated onto a silicon wafer. After baking, the refractive index was measured using an ellipsometer. The refractive indices of the compounds prepared in Examples 1 to 5 and the comparative examples are shown in Table 6.
[0110] 2. Abbe number test. The Abbe number is calculated using the refractive index at wavelengths of 486 nm, 587.6 nm, and 656.3 nm. The calculation formula is as follows: Vd=(nD-1) / (nF-nC)
[0111] The Abbe numbers obtained by testing the compounds prepared in Examples 1 to 5 and the comparative examples are shown in Table 6.
[0112] 3. Water Absorption Test. The water absorption rate of 2mm thick sheet-like molded sheets obtained by injection molding from the compounds prepared in Examples 1 to 5 and the comparative example was measured according to ISO 62 after immersion at 23°C for 24 hours. The water absorption rates of the compounds prepared in Examples 1 to 5 and the comparative example are shown in Table 6.
[0113] 4. Transmittance Test. The purified resin was dispersed in a polar solvent, such as tetrachloroethane, and then spin-coated onto the surface of a glass substrate. After baking, the transmittance was tested using a haze meter. The transmittance of the compounds prepared in Examples 1 to 5 and the comparative examples is shown in Table 6.
[0114] 5. Glass transition temperature (Tg) test. A TA Instruments Japan 2910 differential scanning calorimeter was used for the test, with a heating rate of 10 °C / min. The glass transition temperatures (Tg) of the compounds prepared in Examples 1 to 5 and the comparative examples are shown in Table 6.
[0115] 6. Yellowness Index Test. Place the UV-treated polymer resin on a colorimeter, measure according to the instrument's operating instructions, and record the measured yellowness index value.
[0116] The Yellowness Index (YI) is a numerical value that quantifies the yellowness of a sample. It is measured and analyzed using a colorimeter, colorimeter, or spectrophotometer to measure and analyze the color characteristics of an object. The calculation formula is: YI = 100(CxX - CzZ) / Y, where X, Y, and Z represent the tristimulus values, and the values of Cx and Cz can be found in relevant ASTM standards. The Yellowness Index can be positive or negative; a higher Yellowness Index indicates a more yellow sample.
[0117] Table 6
[0118] Therefore, it can be seen that the refractive indices of the polymeric resins P1-P5 prepared in Examples 1-5 are all above 1.819, indicating that the polymeric resins provided in this application have ultra-high refractive indices; the Abbe numbers of polymeric resins P1-P5 are all above 18, indicating that the optical lenses made from the polymeric resins provided in this application have low dispersion and clear imaging; the water absorption rates of polymeric resins P1-P5 are all above 0.1%, meaning that the polymeric resins swell into hydrogels after absorbing water. In this state, even under pressure, it is difficult to separate the water, thus maintaining the stability and integrity of the resin and helping to prevent performance degradation due to water loss during use. This extends the service life of the polymer resins; the light transmittance of polymer resins P1-P5 is all above 84%; the Tg of polymer resins P1-P5 is all above 150℃, indicating that the polymer resins provided in this application have good thermal stability; the yellowness index of polymer resins P1-P5 is all below 1.90, while that of the comparative polymer resin P6 reaches 1.92. Therefore, the antioxidant capacity of polymer resins P1-P5 provided in this application is higher than that of the comparative polymer resin P6. That is, the polymer resins provided in this application have a higher refractive index, good light transmittance, good mechanical properties, heat resistance and low shrinkage, and the polymer resin has excellent antioxidant properties and stability.
[0119] It should be understood that the terminology used in this application specification is for the purpose of describing particular embodiments only and is not intended to limit the application.
[0120] It should also be understood that the term “and / or” as used in this application specification and the appended claims means any combination of one or more of the associated listed items and all possible combinations, and includes such combinations.
[0121] The above description is merely a specific embodiment of this application, but the scope of protection of this application is not limited thereto. Any person skilled in the art can easily conceive of various equivalent modifications or substitutions within the technical scope disclosed in this application, and such modifications or substitutions should all be covered within the scope of protection of this application. Therefore, the scope of protection of this application should be determined by the scope of the claims.
Claims
1. A polymeric resin, wherein, The polymeric resin has the following general structural formula: In the formula, at least one of R1 and R2 is an aromatic group, and n is a positive integer from 1 to 10000.
2. The polymeric resin according to claim 1, wherein, Both R1 and R2 are aromatic groups.
3. The polymeric resin according to claim 1, wherein, The aromatic group is at least one of benzene ring, naphthyl ring, fluorene, carbazole, furan, thiophene, pyrrole, thiazole, imidazole, pyridine, pyrazine, pyrimidine, and pyridazine.
4. The polymeric resin of claim 1, wherein, The polymeric resin is selected from the following structural formula: or, or, or, or, Any one of the compounds in it.
5. The polymeric resin according to claim 1, wherein, The refractive index of the polymeric resin is 1.819 to 1.
828.
6. A polymeric resin, wherein, The polymeric resin is prepared from the following raw materials: thiocyanate, amino compound and solvent.
7. The polymeric resin according to claim 6, wherein, The molar ratio of the thiocyanate, the amino compound, and the solvent is (257–350): 300: (22000–26000).
8. The polymeric resin according to claim 6, wherein, The thiocyanate is at least one of phenyl diisothiocyanate, terephthalic diisothiocyanate, terephthalic dimethyl dithiocyanate, and pyridine diisothiocyanate.
9. The polymeric resin according to claim 6, wherein, The amino compound is at least one of 4,4-diaminodiphenyl sulfide, 4,4-thioether-bis(1,3,5-triazine-2-amine), 4,4-(1,4-phenylene di(sulfide))diphenylamine, 9,9-bis(4-aminophenyl)fluorene, 6,6'-thioether-bis(2-aminopyridine), 1,4-bis(3-aminophenoxy)benzene, 1,3-bis(4-aminophenyl)adamantane, and bis[4-(4-aminophenoxy)phenyl]sulfone.
10. The polymeric resin according to claim 6, wherein, The solvent is selected from one or more of N,N-dimethylformamide, dimethyl sulfoxide, and N-methyl-2-pyrrolidone.
11. A method of preparing a polymeric resin, wherein, The method includes: Provides thiocyanates, amino compounds, and solvents; The thiocyanate, the amino compound, and the solvent are stirred evenly and reacted to obtain a polymeric resin.
12. The method of claim 11, wherein, The reaction temperature is 22℃~24℃, the reaction time is 23.5 hours~24.5 hours, and the reaction environment is a nitrogen atmosphere.
13. The method of claim 11, wherein, The molar ratio of the thiocyanate, the amino compound, and the solvent is (257–350): 300: (22000–26000).
14. The method of claim 13, wherein, The molar ratio of the thiocyanate, the amino compound, and the solvent is (300-350): 300: (23300-25800).
15. The method of claim 11, wherein, The thiocyanate is selected from at least one of phenyl diisothiocyanate, terephthalic diisothiocyanate, terephthalic dimethyl dithiocyanate, and pyridine diisothiocyanate; The amino compound is at least one of 4,4-diaminodiphenyl sulfide, 4,4-thioether-bis(1,3,5-triazine-2-amine), 4,4-(1,4-phenylene di(sulfide))diphenylamine, 9,9-bis(4-aminophenyl)fluorene, 6,6'-thioether-bis(2-aminopyridine), 1,4-bis(3-aminophenoxy)benzene, 1,3-bis(4-aminophenyl)adamantane, and bis[4-(4-aminophenoxy)phenyl]sulfone; The solvent is selected from one or more of N,N-dimethylformamide, dimethyl sulfoxide, and N-methyl-2-pyrrolidone.
16. The method of claim 11, wherein, The molar ratio of the thiocyanate, the amino compound, and the solvent is 350:300:25800. The thiocyanate is terephthalic diisothiocyanate, the amino compound is 4,4'-(1,4-phenylene di(thio))diphenylamine, and the solvent is N,N-dimethylformamide.
17. The method of claim 11, wherein, The molar ratio of the thiocyanate, the amino compound, and the solvent is 300:300:23300, the thiocyanate is terephthalic diisothiocyanate, the amino compound is 4,4'-diaminodiphenyl sulfide, and the solvent is N,N-dimethylformamide.
18. The method of claim 11, wherein, The step of reacting the thiocyanate, the amino compound, and the solvent to obtain the polymeric resin comprises: The thiocyanate, the amino compound, and the solvent are stirred evenly in a molar ratio of (257-350):300:(22000-26000) to carry out the reaction. The solution after the reaction was completed was filtered to remove insoluble matter to obtain a filtrate. Methanol was added dropwise to the filtrate to precipitate the precipitate. The precipitate was filtered and washed with methanol, and then dried in a vacuum environment to obtain a polymer resin.
19. An optical lens, wherein, The optical lens is made of the polymeric resin as described in any one of claims 1 to 10, or of the polymeric resin prepared by the method described in any one of claims 11 to 18.
20. A smart eyewear, wherein, The smart glasses include the optical lenses as described in claim 19.