CN111057538B - Luminescent material containing rare earth europium complex and preparation method thereof - Google Patents
Luminescent material containing rare earth europium complex and preparation method thereof Download PDFInfo
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- CN111057538B CN111057538B CN201911401893.XA CN201911401893A CN111057538B CN 111057538 B CN111057538 B CN 111057538B CN 201911401893 A CN201911401893 A CN 201911401893A CN 111057538 B CN111057538 B CN 111057538B
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/182—Metal complexes of the rare earth metals, i.e. Sc, Y or lanthanide
Abstract
The invention relates to the technical field of luminescent material preparation, and particularly discloses a luminescent material containing a rare earth europium complex and a preparation method thereof. The luminescent material containing the rare earth europium complex comprises the following components in parts by weight; 80-100 parts of polylactic acid; 10-20 parts of ABS plastic; 1-3 parts of rare earth europium complex; 2-4 parts of a compatilizer; 1-3 parts of a dispersing agent; the rare earth europium complex is a ternary complex based on rare earth europium-DPPD-phenanthroline. According to the invention, the rare earth europium-DPPD-phenanthroline-based ternary complex with excellent luminescence property is added into the polylactic acid composite material for the first time, so that the lactic acid composite material with excellent luminescence property is prepared.
Description
Technical Field
The invention relates to the technical field of luminescent material preparation, in particular to a luminescent material containing a rare earth europium complex and a preparation method thereof.
Background
The rare earth europium-DPPD-phenanthroline-based ternary complex is a rare earth europium complex with good luminescence property synthesized by the inventor at the earlier stage, and is disclosed in the patent of China 201910690772.5 (see the structure shown in formula II). The Chinese patent No. 201910690772.5 also discloses that the ternary complex based on rare earth europium-DPPD-phenanthroline is compatible with polypropylene, and provides a luminescent material of polypropylene, and the luminescent material of polypropylene can be used as a 3D printing material.
In order to provide more luminescent materials, the inventor of the present invention tried to use the rare earth europium-DPPD-phenanthroline-based ternary complex disclosed in the chinese 201910690772.5 patent for other materials. However, due to different properties of different materials, the europium-DPPD-phenanthroline-based ternary complex cannot be well dispersed and compatible with other materials when used in other materials, so that the performance of other materials is reduced.
The polylactic acid is an environment-friendly high polymer material and is also a common material for 3D printing; however, polylactic acid has a low glass transition temperature, and thus is inferior in heat resistance and is easily deformed. In order to increase the glass transition temperature of polylactic acid, other plastics, such as common composite plastics with ABS as polylactic acid, are generally required to be compounded. The inventor finds that when the ternary complex based on the rare earth europium-DPPD-phenanthroline is used in the polylactic acid composite material, the ternary complex based on the rare earth europium-DPPD-phenanthroline cannot be well dispersed in the polylactic acid and ABS materials, and the most direct reaction cannot effectively improve the glass transition temperature of the polylactic acid due to poor dispersibility of the complex and poor compatibility among the components. In order to solve the problem of the dispersibility of the rare earth europium-DPPD-phenanthroline ternary complex in polylactic acid and ABS materials, the inventor also adds a compatilizer and a dispersing agent, and the effect is not good although the effect is certain. The reason is that the rare earth europium-DPPD-phenanthroline ternary complex is a brand new synthetic component, and the existing conventional dispersing agent cannot well disperse the rare earth europium-DPPD-phenanthroline ternary complex in polylactic acid and ABS materials.
Disclosure of Invention
The invention aims to solve the technical problem of providing a luminescent material containing a rare earth europium complex. The luminescent material has excellent luminescent performance by adding the rare earth europium-DPPD-phenanthroline ternary complex.
The technical problem to be solved by the invention is realized by the following technical scheme:
a luminescent material containing rare earth europium complex comprises the following components in parts by weight;
80-100 parts of polylactic acid; 10-20 parts of ABS plastic; 1-3 parts of rare earth europium complex; 2-4 parts of a compatilizer; 1-3 parts of a dispersing agent.
Preferably, the luminescent material containing the rare earth europium complex comprises the following components in parts by weight;
80-90 parts of polylactic acid; 15-20 parts of ABS plastic; 1-2 parts of rare earth europium complex; 3-4 parts of a compatilizer; 1-2 parts of a dispersing agent.
Most preferably, the luminescent material containing the rare earth europium complex comprises the following components in parts by weight;
85 parts of polylactic acid; 15 parts of ABS plastic; 1.5 parts of rare earth europium complex; 3 parts of a compatilizer; and 2 parts of a dispersing agent.
Preferably, the rare earth europium complex is a ternary complex based on rare earth europium-DPPD-phenanthroline.
Preferably, the compatibilizer is selected from maleic anhydride grafted compatibilizers;
most preferably, the maleic anhydride grafted compatibilizer is maleic anhydride grafted ABS.
Preferably, the dispersant is prepared by the following method:
(1) dissolving 3-phenyl glutaric acid in an organic solvent, then adding thionyl chloride, reacting for 3-5 hours at 70-80 ℃, cooling, concentrating and removing the organic solvent to obtain 3-phenyl glutaryl chloride;
(2) dissolving hexadecanol and cyclohexanol in an organic solvent, then adding 3-phenyl glutaryl chloride, reacting for 6-10 h at 40-50 ℃, cooling, concentrating and removing the organic solvent to obtain the dispersing agent.
Preferably, the mass ratio of the 3-phenyl glutaric acid to the thionyl chloride in the step (1) is as follows: 1: 1-1.5; the dosage ratio of the 3-phenyl glutaric acid to the organic solvent is 1g: 5-10 mL;
the dosage ratio of the hexadecanol, the cyclohexanol and the 3-phenyl glutaryl chloride in the step (2) is as follows: 2-3: 0.8-1.2: 1.5-2.5; the ratio of the total weight of the hexadecanol and the cyclohexanol to the amount of the organic solvent is 1g: 5-10 mL;
most preferably, the mass ratio of the 3-phenyl glutaric acid to the thionyl chloride in the step (1) is as follows: 1: 1.2; the dosage ratio of the 3-phenyl glutaric acid to the organic solvent is 1g:8 mL;
the dosage ratio of the hexadecanol, the cyclohexanol and the 3-phenyl glutaryl chloride in the step (2) is as follows: 2.5:1: 2; the ratio of the total weight of the hexadecanol and the cyclohexanol to the amount of the organic solvent is 1g:8 mL.
The preparation method of the luminescent material containing the rare earth europium complex comprises the following steps:
uniformly mixing polylactic acid, ABS plastic, a rare earth europium complex, a compatilizer and a dispersing agent, and banburying in an internal mixer at 180-200 ℃ for 10-20 min to obtain the luminescent material containing the rare earth europium complex.
Has the advantages that: (1) according to the invention, the rare earth europium-DPPD-phenanthroline-based ternary complex with excellent luminescence property is added into the polylactic acid composite material for the first time, so that the lactic acid composite material with the luminescence property is prepared. (2) The invention further aims to solve the technical problems that the europium-DPPD-phenanthroline ternary complex cannot be well dispersed in polylactic acid and ABS materials, so that the compatibility among the components is poor, and the glass transition temperature of the polylactic acid cannot be effectively improved; compared with the conventional dispersant, the novel dispersant can effectively disperse the ternary complex based on the rare earth europium-DPPD-phenanthroline in the polylactic acid and ABS materials, further promotes the compatibility among the components, and most directly promotes the improvement of the glass transition temperature of the polylactic acid.
Detailed Description
The present invention will be described in further detail with reference to specific examples, but the present invention is not limited to these examples in any way.
Polylactic acid in the following examples was purchased from NatureWorks, USA under the designation 6204D; ABS plastic resin is purchased from the Korean LG company and has the brand number of GP-2300;
EXAMPLE 1 preparation of a luminescent Material containing a rare earth europium Complex
85 parts of polylactic acid; 15 parts of ABS plastic; 1.5 parts of rare earth europium-DPPD-phenanthroline-based ternary complex; 3 parts of maleic anhydride grafted ABS; and 2 parts of a dispersing agent.
The dispersant is prepared by the following method:
(1) dissolving 3-phenyl glutaric acid in an organic solvent (benzene), adding thionyl chloride, reacting for 4 hours at 80 ℃, cooling, concentrating and removing the organic solvent to obtain 3-phenyl glutaryl chloride;
(2) dissolving hexadecanol and cyclohexanol in an organic solvent (benzene), then adding 3-phenyl glutaryl chloride, reacting for 8 hours at 40 ℃, cooling, concentrating and removing the organic solvent to obtain the dispersing agent;
the mass ratio of the 3-phenyl glutaric acid to the thionyl chloride in the step (1) is as follows: 1: 1.2; the dosage ratio of the 3-phenyl glutaric acid to the organic solvent is 1g:8 mL;
the dosage ratio of the hexadecanol, the cyclohexanol and the 3-phenyl glutaryl chloride in the step (2) is as follows: 2.5:1: 2; the ratio of the total weight of the hexadecanol and the cyclohexanol to the amount of the organic solvent is 1g:8 mL;
the preparation method comprises the following steps: uniformly mixing polylactic acid, ABS plastic, a ternary complex based on rare earth europium-DPPD-phenanthroline, maleic anhydride grafted ABS and a dispersing agent, and banburying in an internal mixer at 190 ℃ for 15min to obtain the luminescent material containing the rare earth europium complex.
The luminescent material containing the rare earth europium complex prepared by the embodiment has excellent luminescent performance; in the embodiment, the dispersant prepared by a brand new method is added, and the dispersant can well disperse the ternary complex based on the rare earth europium-DPPD-phenanthroline into the polylactic acid and ABS plastic, so that the compatibility among the ternary complex based on the rare earth europium-DPPD-phenanthroline, the polylactic acid and the ABS plastic is further promoted; so that the luminescent material containing the rare earth europium complex has higher glass transition temperature; through detection, the glass transition temperature of the luminescent material containing the rare earth europium complex prepared in the embodiment is 85.8 ℃ (detected by a DSC method).
EXAMPLE 2 preparation of a luminescent Material containing a rare earth europium Complex
80 parts of polylactic acid; 20 parts of ABS plastic; 1 part of rare earth europium-DPPD-phenanthroline-based ternary complex; 2 parts of maleic anhydride grafted ABS; 1 part of a dispersant.
The dispersant is prepared by the following method:
(1) dissolving 3-phenyl glutaric acid in an organic solvent (benzene), adding thionyl chloride, reacting for 5 hours at 70 ℃, cooling, concentrating and removing the organic solvent to obtain 3-phenyl glutaryl chloride;
(2) dissolving hexadecanol and cyclohexanol in an organic solvent (benzene), then adding 3-phenyl glutaryl chloride, reacting for 6 hours at 50 ℃, cooling, concentrating and removing the organic solvent to obtain the dispersing agent;
the mass ratio of the 3-phenyl glutaric acid to the thionyl chloride in the step (1) is as follows: 1: 1.2; the dosage ratio of the 3-phenyl glutaric acid to the organic solvent is 1g:8 mL;
the dosage ratio of the hexadecanol, the cyclohexanol and the 3-phenyl glutaryl chloride in the step (2) is as follows: 2.5:1: 2; the ratio of the total weight of the hexadecanol and the cyclohexanol to the amount of the organic solvent is 1g:8 mL;
the preparation method comprises the following steps: uniformly mixing polylactic acid, ABS plastic, a ternary complex based on rare earth europium-DPPD-phenanthroline, maleic anhydride grafted ABS and a dispersing agent, and banburying in an internal mixer at 190 ℃ for 15min to obtain the luminescent material containing the rare earth europium complex.
The glass transition temperature of the luminescent material containing the rare earth europium complex prepared in the embodiment is 84.1 ℃ through detection by a DSC method.
EXAMPLE 3 preparation of a luminescent Material containing a rare earth europium Complex
100 parts of polylactic acid; 10 parts of ABS plastic; 3 parts of a ternary complex based on rare earth europium-DPPD-phenanthroline; 4 parts of maleic anhydride grafted ABS; 3 parts of a dispersing agent.
The dispersant is prepared by the following method:
(1) dissolving 3-phenyl glutaric acid in an organic solvent (benzene), adding thionyl chloride, reacting for 4 hours at 75 ℃, cooling, concentrating and removing the organic solvent to obtain 3-phenyl glutaryl chloride;
(2) dissolving hexadecanol and cyclohexanol in an organic solvent (benzene), then adding 3-phenyl glutaryl chloride, reacting for 10 hours at 45 ℃, cooling, concentrating and removing the organic solvent to obtain the dispersing agent;
the mass ratio of the 3-phenyl glutaric acid to the thionyl chloride in the step (1) is as follows: 1: 1.2; the dosage ratio of the 3-phenyl glutaric acid to the organic solvent is 1g:8 mL;
the dosage ratio of the hexadecanol, the cyclohexanol and the 3-phenyl glutaryl chloride in the step (2) is as follows: 2.5:1: 2; the ratio of the total weight of the hexadecanol and the cyclohexanol to the amount of the organic solvent is 1g:8 mL;
the preparation method comprises the following steps: uniformly mixing polylactic acid, ABS plastic, a ternary complex based on rare earth europium-DPPD-phenanthroline, maleic anhydride grafted ABS and a dispersing agent, and banburying in an internal mixer at 190 ℃ for 15min to obtain the luminescent material containing the rare earth europium complex.
Through detection, the glass transition temperature of the luminescent material containing the rare earth europium complex prepared in the embodiment is 80.3 ℃ (detected by a DSC method).
Comparative example 1 preparation of luminescent Material containing rare-earth europium Complex
85 parts of polylactic acid; 15 parts of ABS plastic; 1.5 parts of rare earth europium-DPPD-phenanthroline-based ternary complex; 3 parts of maleic anhydride grafted ABS; and 2 parts of a dispersing agent.
The dispersing agent is ethylene bis stearamide;
the preparation method comprises the following steps: uniformly mixing polylactic acid, ABS plastic, a ternary complex based on rare earth europium-DPPD-phenanthroline, maleic anhydride grafted ABS and a dispersing agent, and banburying in an internal mixer at 190 ℃ for 15min to obtain the luminescent material containing the rare earth europium complex.
Through detection, the glass transition temperature of the luminescent material containing the rare earth europium complex prepared by the comparative example is 64.4 ℃ (DSC method detection); is much lower than that of example 1; the dispersant plays an important role in the glass transition temperature of the luminescent material, and the glass transition temperature of the polylactic acid luminescent material containing the rare earth europium-DPPD-phenanthroline ternary complex cannot be greatly improved only by selecting the conventional dispersant.
Comparative example 2 preparation of luminescent Material containing rare-earth europium Complex
85 parts of polylactic acid; 15 parts of ABS plastic; 1.5 parts of rare earth europium-DPPD-phenanthroline-based ternary complex; 3 parts of maleic anhydride grafted ABS; and 2 parts of a dispersing agent.
The dispersant is prepared by the following method:
(1) dissolving 3-phenyl glutaric acid in an organic solvent (benzene), adding thionyl chloride, reacting for 4 hours at 80 ℃, cooling, concentrating and removing the organic solvent to obtain 3-phenyl glutaryl chloride;
(2) dissolving hexadecanol in an organic solvent (benzene), adding 3-phenyl glutaryl chloride, reacting for 8 hours at 40 ℃, cooling, concentrating and removing the organic solvent to obtain the dispersing agent;
the mass ratio of the 3-phenyl glutaric acid to the thionyl chloride in the step (1) is as follows: 1: 1.2; the dosage ratio of the 3-phenyl glutaric acid to the organic solvent is 1g:8 mL;
the dosage ratio of the hexadecanol to the 3-phenyl glutaryl chloride in the step (2) is as follows: 3.5: 2; the dosage ratio of the hexadecanol and the organic solvent is 1g:8 mL;
the preparation method comprises the following steps: uniformly mixing polylactic acid, ABS plastic, a ternary complex based on rare earth europium-DPPD-phenanthroline, maleic anhydride grafted ABS and a dispersing agent, and banburying in an internal mixer at 190 ℃ for 15min to obtain the luminescent material containing the rare earth europium complex.
This comparative example differs from example 1 in that the dispersant was prepared solely from hexadecanol reacted with 3-phenyl glutaryl chloride.
Through detection, the glass transition temperature of the luminescent material containing the rare earth europium complex prepared by the comparative example is 68.2 ℃ (DSC method detection); is much lower than that of example 1; the preparation method of the dispersing agent plays an important role in influencing the glass transition temperature of the luminescent material, and the dispersing agent prepared by the reaction of hexadecanol, cyclohexanol and 3-phenyl glutaryl chloride must be added to greatly improve the glass transition temperature of the polylactic acid luminescent material containing the rare earth europium-DPPD-phenanthroline ternary complex.
Comparative example 3 preparation of luminescent Material containing rare-earth europium Complex
85 parts of polylactic acid; 15 parts of ABS plastic; 1.5 parts of rare earth europium-DPPD-phenanthroline-based ternary complex; 3 parts of maleic anhydride grafted ABS; and 2 parts of a dispersing agent.
The dispersant is prepared by the following method:
(1) dissolving 3-phenyl glutaric acid in an organic solvent (benzene), adding thionyl chloride, reacting for 4 hours at 80 ℃, cooling, concentrating and removing the organic solvent to obtain 3-phenyl glutaryl chloride;
(2) dissolving cyclohexanol in organic solvent (benzene), adding 3-phenyl glutaryl chloride, reacting at 40 deg.C for 8 hr, cooling, concentrating to remove organic solvent to obtain the dispersant;
the mass ratio of the 3-phenyl glutaric acid to the thionyl chloride in the step (1) is as follows: 1: 1.2; the dosage ratio of the 3-phenyl glutaric acid to the organic solvent is 1g:8 mL;
the dosage ratio of cyclohexanol to 3-phenyl glutaryl chloride in the step (2) is as follows: 3.5: 2; the dosage ratio of cyclohexanol to organic solvent is 1g:8 mL;
the preparation method comprises the following steps: uniformly mixing polylactic acid, ABS plastic, a ternary complex based on rare earth europium-DPPD-phenanthroline, maleic anhydride grafted ABS and a dispersing agent, and banburying in an internal mixer at 190 ℃ for 15min to obtain the luminescent material containing the rare earth europium complex.
This comparative example differs from example 1 in that the dispersant was prepared solely by reacting cyclohexanol with 3-phenyl glutaryl chloride.
Through detection, the glass transition temperature of the luminescent material containing the rare earth europium complex prepared by the comparative example is 66.9 ℃ (DSC method detection); is much lower than that of example 1; the preparation method of the dispersing agent plays an important role in influencing the glass transition temperature of the luminescent material, and the dispersing agent prepared by the reaction of hexadecanol, cyclohexanol and 3-phenyl glutaryl chloride must be added to greatly improve the glass transition temperature of the polylactic acid luminescent material containing the rare earth europium-DPPD-phenanthroline ternary complex.
Claims (9)
1. A luminescent material containing rare earth europium complex is characterized by comprising the following components in parts by weight;
80-100 parts of polylactic acid; 10-20 parts of ABS plastic; 1-3 parts of rare earth europium complex; 2-4 parts of a compatilizer; 1-3 parts of a dispersing agent;
the dispersant is prepared by the following method:
(1) dissolving 3-phenyl glutaric acid in an organic solvent, then adding thionyl chloride, reacting for 3-5 hours at 70-80 ℃, cooling, concentrating and removing the organic solvent to obtain 3-phenyl glutaryl chloride;
(2) dissolving hexadecanol and cyclohexanol in an organic solvent, then adding 3-phenyl glutaryl chloride, reacting for 6-10 h at 40-50 ℃, cooling, concentrating and removing the organic solvent to obtain the dispersing agent.
2. The rare earth europium complex-containing luminescent material according to claim 1, which comprises the following components in parts by weight;
80-90 parts of polylactic acid; 15-20 parts of ABS plastic; 1-2 parts of rare earth europium complex; 3-4 parts of a compatilizer; 1-2 parts of a dispersing agent.
3. The rare earth europium complex-containing luminescent material according to claim 2, which comprises the following components in parts by weight;
85 parts of polylactic acid; 15 parts of ABS plastic; 1.5 parts of rare earth europium complex; 3 parts of a compatilizer; and 2 parts of a dispersing agent.
4. The rare earth europium complex-containing luminescent material of claim 1, wherein the rare earth europium complex is a ternary complex based on rare earth europium-DPPD-phenanthroline.
5. The rare earth europium complex-containing luminescent material of claim 1, wherein the compatibilizer is selected from maleic anhydride grafted compatibilizers.
6. The rare earth europium complex-containing luminescent material of claim 5, wherein the maleic anhydride grafted compatibilizer is maleic anhydride grafted ABS.
7. The rare earth europium complex-containing luminescent material of claim 1,
the mass ratio of the 3-phenyl glutaric acid to the thionyl chloride in the step (1) is as follows: 1: 1-1.5; the dosage ratio of the 3-phenyl glutaric acid to the organic solvent is 1g: 5-10 mL;
the dosage ratio of the hexadecanol, the cyclohexanol and the 3-phenyl glutaryl chloride in the step (2) is as follows: 2-3: 0.8-1.2: 1.5-2.5; the ratio of the total weight of the hexadecanol and the cyclohexanol to the amount of the organic solvent is 1g: 5-10 mL.
8. The rare earth europium complex-containing luminescent material of claim 7,
the mass ratio of the 3-phenyl glutaric acid to the thionyl chloride in the step (1) is as follows: 1: 1.2; the dosage ratio of the 3-phenyl glutaric acid to the organic solvent is 1g:8 mL;
the dosage ratio of the hexadecanol, the cyclohexanol and the 3-phenyl glutaryl chloride in the step (2) is as follows: 2.5:1: 2; the ratio of the total weight of the hexadecanol and the cyclohexanol to the amount of the organic solvent is 1g:8 mL.
9. The method for preparing a luminescent material comprising a rare earth europium complex according to any one of claims 1 to 8, which comprises the following steps:
uniformly mixing polylactic acid, ABS plastic, a rare earth europium complex, a compatilizer and a dispersing agent, and banburying in an internal mixer at 180-200 ℃ for 10-20 min to obtain the luminescent material containing the rare earth europium complex.
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