CN112852411A - Chemiluminescent composition - Google Patents

Chemiluminescent composition Download PDF

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CN112852411A
CN112852411A CN201911186690.3A CN201911186690A CN112852411A CN 112852411 A CN112852411 A CN 112852411A CN 201911186690 A CN201911186690 A CN 201911186690A CN 112852411 A CN112852411 A CN 112852411A
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agent
chemiluminescent composition
luminescent
weight
oxidizing agent
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陈聪玲
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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
    • C09K11/07—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials having chemically interreactive components, e.g. reactive chemiluminescent compositions
    • 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
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B

Abstract

A chemiluminescent composition comprises a luminescent agent and an oxidizing agent, wherein the solvent of the oxidizing agent is glycerol triacetate, the solvent of the luminescent agent is n-tributyl citrate and butyl benzoate, an organic blue fluorescent material is adopted as a fluorescent agent, and the organic blue fluorescent material can enable the fluorescence intensity to be higher and the luminescence duration to be longer.

Description

Chemiluminescent composition
Technical Field
The invention relates to the field of chemiluminescent compositions, in particular to a chemiluminescent composition.
Background
Chemiluminescence refers to visible light emitted in the reaction process of certain chemical substances, and the chemiluminescence technology is mature and widely applied to multiple fields after development and research for forty years since the chemiluminescence principle was discovered in the 70 th 20 th century. In toy art ware, the manufacture of objects that emit light by means of chemical reactions has long been known and is based on the chemiluminescence produced by the mixing of two components, which before emission need to be kept separate and when emission is required are brought into contact, the two components, usually an oxidizing agent and a luminescent agent, are mixed to produce chemiluminescence, requiring that the solvents chosen must be sufficiently miscible.
At present, the chemiluminescent substances on the market use benzoate solvents (DMP and DBP), which may affect human health, wherein phthalic acid esters have potential carcinogenicity, and countries such as Europe and America have strict control on the use of the phthalic acid esters. Related laws and regulations are also made in China, and the use of phthalate esters in food packaging materials, medical appliances, toys for children and the like is gradually eliminated.
The prior green environment-friendly chemiluminescent composition used for food packaging materials, medical appliances and children toys has the problems of insufficient luminous intensity and short luminous time.
Disclosure of Invention
In order to overcome the defects in the prior art, the invention provides the chemiluminescent composition which is green and environment-friendly and has enough luminous intensity and luminous duration.
The technical scheme adopted by the invention is as follows: a chemiluminescent composition comprises a luminescent agent and an oxidizing agent, wherein the oxidizing agent comprises an oxide and a solvent A, the luminescent agent comprises a fluorescent agent and a solvent B, the solvent B is tributyl citrate and dipropylene glycol dimethyl ether, the fluorescent agent is an organic blue fluorescent material, and the solvent A is glyceryl triacetate.
Further, the luminous agent comprises 100 parts by weight of oxalate, 0.01-0.05 part by weight of sodium salicylate and 1-1.5 parts by weight of fluorescent agent, and the oxidant comprises 1-60 parts by weight of tributyl citrate, 1-100 parts by weight of dipropylene glycol dimethyl ether, 2-5 parts by weight of 90% hydrogen peroxide and 0.01-0.05 part by weight of catalyst A.
Furthermore, the organic blue fluorescent material is prepared by performing Suzuki coupling reaction on 9-phenylanthracene-10 borate and 4, 4' -dibromodiphenyl disubstituted methane.
Further, the mass ratio of the luminescent agent to the oxidizing agent is 1: 2-1: 3.
further, the catalyst A is sodium salicylate or tetrabutyl ammonium salicylate.
The invention has the beneficial effects that: the invention provides a green environment-friendly luminescent composition, wherein a benzoate solvent harmful to human bodies is replaced by green environment-friendly solvents of tributyl citrate and dipropylene glycol dimethyl ether, so that the composition is non-toxic and harmless, does not have adverse effect on human health, and obtains the same luminescent effect.
Drawings
The invention is described in further detail below with reference to the following figures and embodiments:
FIG. 1 is a nuclear magnetic spectrum of an organic blue fluorescent material;
FIG. 2 is a mass spectrum of the organic blue fluorescent material.
Detailed Description
Example 1:
the embodiment discloses a chemiluminescent composition, which comprises a luminescent agent and an oxidizing agent, wherein the oxidizing agent comprises an oxide and a solvent A, the luminescent agent comprises a fluorescent agent and a solvent B, the solvent B is tributyl citrate and dipropylene glycol dimethyl ether, the fluorescent agent is an organic blue fluorescent material, and the solvent A is glycerol triacetate.
Further, the luminous agent comprises 100 parts by weight of oxalate, 0.01-0.05 part by weight of sodium salicylate and 1-1.5 parts by weight of fluorescent agent, and the oxidant comprises 1-60 parts by weight of tributyl citrate, 1-100 parts by weight of dipropylene glycol dimethyl ether, 2-5 parts by weight of 90% hydrogen peroxide and 0.01-0.05 part by weight of catalyst A.
Furthermore, the organic blue fluorescent material is prepared by performing Suzuki coupling reaction on 9-phenylanthracene-10 borate and 4, 4' -dibromodiphenyl disubstituted methane.
Further, the mass ratio of the luminescent agent to the oxidizing agent is 1: 2-1: 3.
further, the catalyst A is sodium salicylate or tetrabutyl ammonium salicylate.
Wherein:
synthesis of organic blue fluorescent material:
as shown in the figures 1 and 2, adding 1.5-6 mmol of 9-phenylanthracene-10 borate, 0.5-2 mmol of 4, 4' -dibromodiphenyl disubstituted methane, 0.1-0.4 mmol of palladium tetrakis (triphenyl) phosphine catalyst, 20-80 mL of toluene, 5-20 mL of ethanol and 311-44 mmol of K2CO (solution prepared by 5-20 mL of distilled water) into a reaction bottle, and refluxing for 12-24 h at 100-110 ℃ under the protection of nitrogen to perform Suzuki coupling reaction; and after the reaction is finished, extracting, performing rotary evaporation, performing column chromatography, and recrystallizing to obtain the organic blue fluorescent material.
(1) Preparing a luminescent agent:
dissolving 3.75g of bis (2, 4, 5-trichloro salicylic acid n-amyl) oxalate (CPPO) and 0.075g of organic blue fluorescent material in a mixed solution of tributyl citrate and butyl benzoate, and stirring until the materials are completely dissolved to obtain a luminescent agent; wherein the mass ratio of tributyl citrate to butyl benzoate is 6: 4; the mass percentage concentration of the oxalate component is 15 percent, and the mass percentage concentration of the organic blue fluorescent material is 0.30 percent;
(2) preparing an oxidizing agent:
dissolving 1.5g of hydrogen peroxide and 0.0025g of tetrabutyl amine salicylate in glycerol triacetate, and stirring to obtain an oxidant; wherein, the mass percent concentration of the hydrogen peroxide is 1.5 percent, and the mass percent concentration of the tetrabutyl amine salt is 0.0025 percent.
(3) Chemiluminescent composition and test
And (3) mixing the luminous agent in the step (1) and the oxidizing agent in the step (2) (wherein the volume ratio of the luminous agent to the oxidizing agent is 1:4 to obtain a green environment-friendly chemiluminescent composition, and measuring the green environment-friendly chemiluminescent composition to be 330LUS by using a TES-1330A illumination instrument to be close to the wall of a luminescent test tube until the complete extinguishment duration is about 4 hours.
Example 2:
(1) preparing a luminescent agent:
dissolving 2.5g of bis (2, 4, 5-trichloro salicylic acid n-amyl) oxalate (CPPO) and 0.06g of organic blue fluorescent material in a mixed solution of tributyl citrate and butyl benzoate, and stirring until the materials are completely dissolved to obtain a luminescent agent; wherein the mass ratio of tributyl citrate to butyl benzoate is 6: 4; the mass percentage concentration of the oxalate component is 10 percent, and the mass percentage concentration of the organic blue fluorescent material is 0.24 percent;
(2) preparation of oxidizing agent
Dissolving 2.5g of hydrogen peroxide and 0.01g of tetrabutyl amine salicylate in glycerol triacetate, and stirring to obtain an oxidant; wherein, the mass percent concentration of the hydrogen peroxide is 2.5 percent, and the mass percent concentration of the tetrabutyl ammonium salt is 0.013 percent.
(3) Chemiluminescent composition and test
And (3) mixing the luminous agent in the step (1) and the oxidizing agent in the step (2) (wherein the volume ratio of the luminous agent to the oxidizing agent is 1:1 to obtain a green environment-friendly chemiluminescent composition, and measuring the green environment-friendly chemiluminescent composition to be 310LUS by using a TES-1330A illumination instrument to be close to the wall of a luminescent test tube until the complete extinguishment duration is about 8 hours.
Example 3:
(1) preparing a luminescent agent:
dissolving 6g (2, 4, 5-trichloro salicylic acid n-amyl) oxalate (CPPO) and 0.16g di (phenylethynyl) anthracene in a mixed solution of tributyl citrate and butyl benzoate, and stirring until the materials are completely dissolved to obtain a luminescent agent; wherein the mass ratio of tributyl citrate to butyl benzoate is 7: 2; the mass percentage concentration of the oxalate component is 6 percent, and the mass percentage concentration of the organic blue fluorescent material is 0.16 percent;
(2) preparing an oxidizing agent:
dissolving 0.75g of hydrogen peroxide and 0.04g of tetrabutyl amine salicylate in glycerol triacetate, and stirring to obtain an oxidant; wherein, the mass percent concentration of the hydrogen peroxide is 3.0 percent, and the mass percent concentration of the tetrabutyl amine salicylate is 0.04 percent.
(3) Chemiluminescent composition and test
Mixing the luminescent agent of step (1) and the oxidizing agent of step (2) (wherein the volume ratio of luminescent agent to oxidizing agent is 4: 1 chemiluminescent composition, measured as 300LUS by TES-1330A illumination meter adjacent to the wall of the luminophore, to a complete extinction duration of about 12 hours.
Example 4:
(1) preparing a luminescent agent:
dissolving 3.75g of bis (2, 4, 5-trichloro salicylic acid n-amyl) oxalate (CPPO) and 0.075g of 9,10 (diacetylene) anthracene in a mixed solution of tributyl citrate and butyl benzoate, and stirring until the materials are completely dissolved to obtain a luminescent agent; wherein the mass ratio of tributyl citrate to butyl benzoate is 6: 4; the mass percentage concentration of the oxalate component is 15 percent, and the mass percentage concentration of 9,10 (diacetylene) anthracene is 0.30 percent;
(2) preparation of oxidizing agent
Dissolving 1.5g of hydrogen peroxide and 0.0025g of tetrabutyl amine salicylate in glycerol triacetate, and stirring to obtain an oxidant; wherein, the mass percent concentration of the hydrogen peroxide is 1.5 percent, and the mass percent concentration of the tetrabutyl amine salt is 0.0025 percent.
(3) Chemiluminescent composition and test
And (3) mixing the luminous agent in the step (1) and the oxidizing agent in the step (2) (wherein the volume ratio of the luminous agent to the oxidizing agent is 1:4 to obtain a green environment-friendly chemiluminescent composition, and measuring the green environment-friendly chemiluminescent composition to be 300LUS by using a TES-1330A illumination instrument to be close to the wall of a luminescent test tube until the complete extinguishment duration is about 3 hours.
Example 5:
(1) preparing a luminescent agent:
dissolving 2.5g of bis (2, 4, 5-trichloro salicylic acid n-amyl) oxalate (CPPO) and 0.06g of 9,10 (diacetylene) anthracene in a mixed solution of tributyl citrate and butyl benzoate, and stirring until the materials are completely dissolved to obtain a luminescent agent; wherein the mass ratio of tributyl citrate to butyl benzoate is 6: 4; the mass percentage concentration of the oxalate component is 10 percent, and the mass percentage concentration of 9,10 (diacetylene) anthracene is 0.24 percent;
(2) preparation of oxidizing agent
Dissolving 2.5g of hydrogen peroxide and 0.01g of tetrabutyl amine salicylate in glycerol triacetate, and stirring to obtain an oxidant; wherein, the mass percent concentration of the hydrogen peroxide is 2.5 percent, and the mass percent concentration of the tetrabutyl ammonium salt is 0.013 percent.
(3) Chemiluminescent composition and test
And (3) mixing the luminous agent in the step (1) and the oxidizing agent in the step (2) (wherein the volume ratio of the luminous agent to the oxidizing agent is 1:1 to obtain a green environment-friendly chemiluminescent composition, and measuring the composition to be 280LUS by using a TES-1330A illumination instrument to be close to the wall of a luminescent test tube until the complete extinguishment duration is about 6 hours.
Example 6:
(1) preparing a luminescent agent:
dissolving 6g (2, 4, 5-trichloro salicylic acid n-amyl) oxalate (CPPO) and 0.16g di (phenylethynyl) anthracene in a mixed solution of tributyl citrate and butyl benzoate, and stirring until the materials are completely dissolved to obtain a luminescent agent; wherein the mass ratio of tributyl citrate to butyl benzoate is 7: 2; the mass percent concentration of the oxalate component is 6 percent, and the mass percent concentration of 9,10 (diacetylene) anthracene is 0.16 percent;
(2) preparing an oxidizing agent:
dissolving 0.75g of hydrogen peroxide and 0.04g of tetrabutyl amine salicylate in glycerol triacetate, and stirring to obtain an oxidant; wherein, the mass percent concentration of the hydrogen peroxide is 3.0 percent, and the mass percent concentration of the tetrabutyl amine salicylate is 0.04 percent.
(3) Chemiluminescent composition and test
Mixing the luminescent agent of step (1) and the oxidizing agent of step (2) (wherein the volume ratio of luminescent agent to oxidizing agent is 4: 1 chemiluminescent composition, measured as 250LUS by TES-1330A illumination meter adjacent to the wall of the luminophore, to a complete extinction duration of about 9 hours.
The above examples show that, after the fluorescent agent is replaced by the organic blue fluorescent material from 9,10- (diacetylene) anthracene, the luminous intensity is improved by about 10%, and the luminous time is prolonged by about 30%, and the organic blue fluorescent material has an excellent effect of combining with a green environment-friendly solvent, is a non-toxic green compound, and conforms to a green environment-friendly chemiluminescent composition.
Table one example 1-6 data record table
Figure BDA0002292566450000071

Claims (5)

1. A chemiluminescent composition comprises a luminescent agent and an oxidizing agent, wherein the oxidizing agent comprises an oxide and a solvent A, the luminescent agent comprises a fluorescent agent and a solvent B, and the chemiluminescent composition is characterized in that the solvent B is tributyl citrate and dipropylene glycol dimethyl ether, the fluorescent agent is an organic blue fluorescent material, and the solvent A is glyceryl triacetate.
2. A chemiluminescent composition of claim 1 wherein the organic blue fluorescent material is prepared by Suzuki coupling reaction of 9-benzanthracene-10 borate and 4, 4' -dibromodiphenyl disubstituted methane.
3. The chemiluminescent composition according to claim 1, wherein the luminescent agent comprises 100 parts by weight of oxalate, 0.01-0.05 part by weight of sodium salicylate and 1-1.5 parts by weight of fluorescent agent, and the oxidizing agent comprises 1-60 parts by weight of tributyl citrate, 1-100 parts by weight of dipropylene glycol dimethyl ether, 2-5 parts by volume of 90% hydrogen peroxide and 0.01-0.05 part by weight of catalyst A.
4. A chemiluminescent composition according to claim 1 or claim 3 wherein the ratio of the luminescent agent to the oxidizing agent is 1: 2-1: 3.
5. a chemiluminescent composition according to claim 3 wherein catalyst a is sodium salicylate or ammonium tetrabutyl salicylate.
CN201911186690.3A 2019-11-28 2019-11-28 Chemiluminescent composition Pending CN112852411A (en)

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