CN107298873B - Preparation method of melanin - Google Patents
Preparation method of melanin Download PDFInfo
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- CN107298873B CN107298873B CN201610236815.9A CN201610236815A CN107298873B CN 107298873 B CN107298873 B CN 107298873B CN 201610236815 A CN201610236815 A CN 201610236815A CN 107298873 B CN107298873 B CN 107298873B
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- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
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Abstract
The invention discloses a preparation method of melanin. The method comprises the following steps: respectively adding a melanin precursor, a surfactant and an oxidant into a high molecular solution, adjusting the pH value to 7-13, and carrying out an oxidation reaction while stirring to obtain melanin; the molar ratio of the melanin precursor to the oxidant is 1 (0.1-10); the concentration of the water-soluble polymer is 0.01-5%; the concentration of the surfactant is 0.01-2%. The melanin particles prepared by the method have small particle size, and the functional film prepared by the melanin particles has strong ultraviolet shielding capability and high visible light transmittance.
Description
Technical Field
The invention relates to the field of melanin composite materials, and further relates to a preparation method of melanin.
Background
Melanin (Melanin) is a kind of macromolecule whose structural unit contains phenolic hydroxyl group and amino group, widely existing in animals and plants, and is classified into Eumelanin (Eumelanin) and pheomelanin (pheomelanin). The eumelanin can be synthesized from L-3, 4-dihydroxyphenylalanine (3,4-dihydroxy-L-phenylalanine, L-DOPA) or 2- (3-dihydroxyphenyl) ethylamine [2- (3,4-dihydroxyphenyl) ethylamine, dopamine (dopamine) ]. Melanin has many biological functions. It can absorb ultraviolet ray to protect organism from some radiation damage, absorb superoxide radical, and has excellent free radical scavenging capacity, antioxidant and antiaging effects. In addition, melanin also has the characteristics of metal chelation, photosensitization and the like. Therefore, development of a functional composition having ultraviolet shielding properties is expected by utilizing the characteristics of melanin.
Publication No. CN101233196A discloses a functional film containing melanin and a preparation method thereof, because the melanin prepared by the method has larger grain diameter and is unevenly dispersed in a polymer matrix, the obtained functional film has low ultraviolet shielding rate and is opaque. Therefore, how to prepare melanin granules with small particle size remains a critical issue.
The melanin can be extracted from living body, such as by centrifuging squid ink to obtain melanin granules. They are also obtained by oxidative polymerization of melanin precursors, but these methods produce melanin with a large particle size (about 200nm), are not easily dispersed in a polymer matrix, and have low visible light transmittance of the composite.
Disclosure of Invention
In order to solve the problems in the prior art, the invention provides a preparation method of melanin. The melanin particles prepared by the method have small particle size, and the functional film prepared by the melanin particles has strong ultraviolet shielding capability and high visible light transmittance.
The invention aims to provide a preparation method of melanin.
The method comprises the following steps:
respectively adding a melanin precursor, a surfactant and an oxidant into a high molecular solution, adjusting the pH value to 7-13, and carrying out an oxidation reaction while stirring to obtain melanin; the pH can be adjusted by conventional methods, such as the addition of a base, or a buffer solution;
the melanin precursor is one or a combination of a true melanin precursor, a melanoid precursor and an allomelanin precursor;
the surfactant is one or a combination of a cationic surfactant, an anionic surfactant, a nonionic surfactant and an amphoteric surfactant;
the oxidant is one or a combination of oxygen-containing compounds, peroxides, peroxy acids and peroxy acid salts;
the polymer is a water-soluble polymer;
the molar ratio of the melanin precursor to the oxidant is 1 (0.1-10), preferably 1 (5-10);
the concentration of the water-soluble polymer is 0.01-5%, preferably 1-5%;
the concentration of the surfactant is 0.01-2%, preferably 1-2%;
the oxidation reaction temperature is 10-70 ℃, and preferably 50-60 ℃;
the reaction time is 5-24 h, preferably 5-10 h.
The melanin precursor used in the present invention is not particularly limited, and various melanin precursors can be used, and among them, at least one selected from the group consisting of true melanin, melanoid and iso-melanin precursors, which are 3 melanin groups defined by r.a.
More specifically exemplified are the melanin precursors mentioned above: tyrosine, cysteine, catechol, 1, 8-dihydroxynaphthalene, dopamine, dopa, 5, 6-dihydroxyindole-2-carboxylic acid, leuco dopachrome, tryptophan, serotonin, epinephrine, norepinephrine, epinephrine, and the like.
These precursors are preferably reacted in a state capable of being uniformly dissolved, depending on their respective characteristics.
The oxidizing agent used in the present invention is not particularly limited, and any oxidizing agent can be used as long as it is free from side reactions other than oxidation and coordination reactions, and it is preferable to select at least one of an oxygen-containing compound, a peroxide, a peroxy acid, and a peroxy acid salt. More specifically, mention is made of: air, oxygen, ozone, hydrogen peroxide, sodium peroxide, benzoyl peroxide, peracetic acid, perbenzoic acid, potassium persulfate, sodium persulfate, ammonium persulfate, and the like.
The water-soluble polymer used in the present invention is not particularly limited, and any water-soluble polymer can be used as long as it is water-soluble, and examples thereof include polyvinyl alcohol, polyethylene glycol, polyvinylpyrrolidone, hydroxymethyl cellulose, methyl cellulose, ethyl cellulose, carboxymethyl cellulose, polyacrylamide, polyacrylic acid, polymaleic anhydride, polyquaternary ammonium salts, and the like.
The surfactant used in the present invention is not particularly limited as long as it has no side reaction, and for example, one or more of stearic acid, sodium dodecylbenzenesulfonate, quaternary ammonium compound, lecithin, amino acid type, betaine type, fatty acid glyceride, fatty acid sorbitan, and polysorbate can be used.
By adjusting the concentration of the macromolecule, a macromolecule network can be formed in the solution; meanwhile, the surfactant changes the interface state of the melanin particles and the solution, the particle size of the melanin can be controlled between 5nm and 500nm by utilizing the coordination of the polymer and the surfactant, and the average particle size of the melanin can be controlled between 5nm and 200nm according to specific conditions, and is more preferably 5nm to 100 nm.
The melanin pigment particles prepared by the method have small particle size, the average particle size can be less than 100nm, and the minimum particle size can reach 5nm, so that the functional film prepared by the melanin particles prepared by the method has strong ultraviolet shielding capability and high visible light transmittance.
The melanin prepared by the invention is applied to the field of anti-ultraviolet high polymer materials.
The polymer matrix used in the present invention is not particularly limited, and various resins can be used without limitation as long as they are transparent resins. For example, polycarbonate, polymethyl methacrylate, polystyrene, polyethylene terephthalate, a styrene-acrylonitrile copolymer, polyethylene naphthalate, polyarylate, polyether sulfone, or the like can be used. The functional melanin composition has high transparency and strong ultraviolet shielding capability, and is suitable for the fields of ultraviolet shielding high polymer materials such as doors and windows, building curtain walls, ceilings, skylights, aircraft cabin covers and the like.
Drawings
FIG. 1 is a transmission electron microscope image of melanin nanoparticles prepared in example 1 of the present invention;
FIG. 2 is a transmission electron microscope image of melanin nanoparticles prepared in example 2 of the present invention;
FIG. 3 is a transmission electron microscope image of melanin nanoparticles prepared in example 3 of the present invention;
FIG. 4 is a transmission electron micrograph of a melanin nanoparticle prepared according to comparative example 4 of the present invention;
FIG. 5 is a transmission electron microscope image of melanin nanoparticles prepared in comparative example 5 of the present invention.
Detailed Description
The present invention will be further described with reference to the following examples.
Example 1
Weighing 0.18g of dopamine (specification: AR) provided by Shanghai Aladdin Biotechnology Co., Ltd.) and dissolving the dopamine in a solution containing 100g of polyethylene glycol (concentration of 0.01%) (national drug group chemical reagent Co., Ltd.; specification: AR) and stearic acid (concentration of 0.01%), introducing 0.37g of oxygen (molar ratio of dopamine to oxygen of 1:10) to adjust the pH value of the solution to 8.4, stirring the solution for 10 hours, finishing the reaction, and centrifuging the solution to obtain the dopamine-L-dopamine copolymerMelanin 1. The average diameter is about 300 nm.
Example 2
0.2g of catechol (provided by Shanghai Allantin Biochemical technology Co., Ltd., specification: AR) and 2g of sodium persulfate (provided by national drug group chemical reagent Co., Ltd., specification: AR), (the molar ratio of the catechol to the sodium persulfate: 1:5) were weighed and dissolved in a solution (100g) containing 100g of polyethylene glycol (concentration: 1%) (national drug group chemical reagent Co., Ltd., specification: AR) and sodium dodecylbenzenesulfonate (concentration: 1%) (national drug group chemical reagent Co., Ltd., specification: AR), the pH value of the solution was adjusted to 9, 60 ℃, after stirring for 5 hours, the reaction was terminated, and centrifugation was carried out to obtain a solutionMelanin 2. The average diameter is about 150 nm.
Example 3
0.2g of dopa (specification: AR provided by Shanghai Aladdin Biotechnology Ltd.) and 1.4g of sodium persulfate (specification: AR) (molar ratio of dopa to sodium persulfate is 1:6) were weighed and dissolved in a solution containing 100g of polyethylene glycol (concentration: 2%) (national drug group chemical Co., Ltd.; specification: AR) and sodium dodecylbenzenesulfonate (concentration: 1%) (national drug group chemical Co., Ltd.; Limited public Co., Ltd.) (national drug group chemical Co., Ltd.; chemical reagent Limited public Co., Ltd.)Department, specification: AR) solution, adjusting pH value of the solution to 9, 65 ℃, stirring for 8 hours, finishing reaction, and centrifuging to obtain the final productMelanin 3. The average diameter is about 100 nm.
Example 4
Weighing 0.2g of tyrosine (specification: AR) and 1.76g of ammonium persulfate (national drug group chemical reagent limited) (molar ratio of tyrosine to ammonium persulfate is 1:7) provided by Shanghai Aladdin Biochemical technology Co., Ltd.), dissolving in 100g of polyvinylpyrrolidone (concentration is 2%) (national drug group chemical reagent limited, specification: AR) and fatty acid glyceride (concentration is 2%) (national drug group chemical reagent limited, specification: AR) solution, adjusting pH of the solution to 9, 50 ℃, stirring for 5 hours, finishing the reaction, and centrifuging to obtain the final productMelanin 4. The average diameter is about 50 nm.
Example 5
Weighing 0.2g of dopamine (provided by Shanghai Aladdin Biochemical technology Co., Ltd., specification: AR) and 2.47g of potassium persulfate (national drug group chemical reagent Co., Ltd.) (molar ratio of dopamine to potassium persulfate is 1:7), dissolving in a solution containing 100g of polyvinylpyrrolidone (concentration is 5%) (national drug group chemical reagent Co., Ltd., specification: AR) and sodium dodecylbenzenesulfonate (concentration is 2%) (national drug group chemical reagent Co., Ltd., specification: AR), adjusting the pH value of the solution to 9, 50 ℃, stirring for 5 hours, finishing the reaction, and centrifuging to obtain the productMelanin 5. The average diameter was about 5 nm.
Example 6
1000g of polycarbonate (Dow chemical Co., USA, weight average molecular weight about 30000) and 25g of polycarbonate were weighedMelanin 1And 0.5g of antioxidant 4, 4' -thiobis (6-tert-butyl-3-methylphenol) are fully and uniformly mixed in a high-speed mixer, the obtained premix is put into a double-screw extruder, the processing temperature is controlled at 255 ℃, and the polycarbonate composition particles are obtained through melting, plasticizing and granulating. Subsequently, the composition was dried under vacuum at 80 ℃ for 6 hours, and then injection-molded (barrel temperature 250 ℃ C., mold temperature 100 ℃ C.) to obtain a sample piece having a thickness of 3.0 mm.
Comparative example 1
1000g of polycarbonate (Dow chemical company, USA, weight average molecular weight is about 30000) and 0.5g of antioxidant 4, 4' -thiobis (6-tert-butyl-3-methylphenol) are weighed and fully and uniformly mixed in a high-speed mixer, and then the obtained premix is put into a double-screw extruder, the processing temperature is controlled at 255 ℃, and the polycarbonate composition particles are obtained through melting, plasticizing and granulating. Subsequently, the composition was dried under vacuum at 80 ℃ for 6 hours, and then injection-molded (barrel temperature 250 ℃ C., mold temperature 100 ℃ C.) to obtain a sample piece having a thickness of 3.0 mm.
Example 7
Weighing 1000g of polymethyl methacrylate (French Acoma, model HFI-10) and 25gMelanin 2Fully and uniformly mixing in a high-speed mixer, putting the obtained premix into a double-screw extruder, controlling the processing temperature to be 250 ℃, and carrying out melt plasticizing granulation to obtain the polymethyl methacrylate composition particles. Subsequently, the composition was dried under vacuum at 80 ℃ for 6 hours, and then injection-molded (barrel temperature 250 ℃ C., mold temperature 100 ℃ C.) to obtain a sample piece having a thickness of 3.0 mm.
Comparative example 2
1000g of polymethyl methacrylate (French Achima, type HFI-10) is weighed and added into a double screw extruder, the processing temperature is controlled at 250 ℃, and the polymethyl methacrylate composition particles are obtained through melting, plasticizing and granulating. Subsequently, the composition was dried under vacuum at 80 ℃ for 6 hours, and then injection-molded (barrel temperature 250 ℃ C., mold temperature 100 ℃ C.) to obtain a sample piece having a thickness of 3.0 mm.
Example 8
1000g of polystyrene (Taiwan Chimei, type PG-33) and 50g were weighedMelanin 3Fully and uniformly mixing in a high-speed mixer, putting the obtained premix into a double-screw extruder, controlling the processing temperature at 160 ℃, and carrying out melt plasticizing granulation to obtain the polystyrene composition particles. Subsequently, the composition was dried under vacuum at 80 ℃ for 6 hours, and then injection-molded (barrel temperature 250 ℃ C., mold temperature 100 ℃ C.) to obtain a sample piece having a thickness of 3.0 mm.
Comparative example 3
1000g of polystyrene (Taiwan Qimei, model PG-33) is weighed and put into a double-screw extruder, the processing temperature is controlled at 160 ℃, and the polystyrene composition particles are obtained through melting, plasticizing and granulating. Subsequently, the composition was dried under vacuum at 80 ℃ for 6 hours, and then injection-molded (barrel temperature 250 ℃ C., mold temperature 100 ℃ C.) to obtain a sample piece having a thickness of 3.0 mm.
Example 9
1000g of polyethylene terephthalate (Dow chemical Co., USA, model CB-602) and 25g of polyethylene terephthalate were weighedMelanin 4Fully and uniformly mixing in a high-speed mixer, putting the obtained premix into a double-screw extruder, controlling the processing temperature to be 255 ℃, and carrying out melt plasticizing granulation to obtain the polyethylene terephthalate composition particles. Subsequently, the composition was dried under vacuum at 80 ℃ for 6 hours, and then injection-molded (barrel temperature 250 ℃ C., mold temperature 100 ℃ C.) to obtain a sample piece having a thickness of 3.0 mm.
Comparative example 4
1000g of polyethylene terephthalate (model CB-602, Dow chemical company, USA) is weighed and put into a double-screw extruder, the processing temperature is controlled at 255 ℃, and the polyethylene terephthalate composition particles are obtained through melting, plasticizing and granulating. Subsequently, the composition was dried under vacuum at 80 ℃ for 6 hours, and then injection-molded (barrel temperature 250 ℃ C., mold temperature 100 ℃ C.) to obtain a sample piece having a thickness of 3.0 mm.
Example 10
1000g of polyethylene naphthalate (Nippon Tekken, model No. TN8065S) and 20g of polyethylene naphthalate were weighed outMelanin 5Fully and uniformly mixing in a high-speed mixer, putting the obtained premix into a double-screw extruder, controlling the processing temperature at 265 ℃, and carrying out melt plasticizing granulation to obtain the polyethylene naphthalate composition particles. Subsequently, the composition was dried under vacuum at 80 ℃ for 6 hours, and then injection-molded (barrel temperature 250 ℃ C., mold temperature 100 ℃ C.) to obtain a sample piece having a thickness of 3.0 mm.
Comparative example 5
1000g of polyethylene naphthalate (Japan emperor, model No. TN8065S) was weighed and placed in a twin-screw extruder, the processing temperature was controlled at 265 ℃, and melt-plastication granulation was carried out to obtain polyethylene naphthalate composition particles. Subsequently, the composition was dried under vacuum at 80 ℃ for 6 hours, and then injection-molded (barrel temperature 250 ℃ C., mold temperature 100 ℃ C.) to obtain a sample piece having a thickness of 3.0 mm.
Example 11
50g of polyarylate (Japan Eurica, model U-8400H) was dissolved in 900mL of chloroform, and 5g thereof was weighedMelanin 5Adding the mixture into a polyarylate solution, uniformly stirring and mixing, and coating and drying to obtain the polyarylate composition.
Comparative example 6
A polyarylate composition was obtained by dissolving 50g polyarylate (Japan Unica, model U-8400H) in 900mL chloroform, stirring uniformly, and coating and drying.
Testing the ultraviolet shielding performance of the sample by using a double-beam ultraviolet-visible spectrophotometer (TU-1901);
measuring the haze of the sample by using a light transmittance haze meter (WGT-S);
ultraviolet aging test conditions: ultraviolet radiation (0.5W/m)2Wavelength 340nm)1000 h;
and (3) heat-humidity aging conditions: the temperature was 85 ℃ and the humidity was 85% (GT-7005). The evaluation method comprises the following steps of observing the color change of the surface of the sample: the color change is small, and the weather resistance is good; large color change and poor weather resistance.
The optical performance and weather resistance of the samples prepared in examples 6 to 11 and comparative examples 1 to 6 were tested, and the test results are shown in Table 1.
TABLE 1 comparison of test Properties
Transparency is determined according to ISO9050:2003 Standard
According to the examples and comparative examples in table 1, it can be found that the uv-shielding ability and weather resistance of the polymer are significantly improved after the melanin pigment is added, and the polymer composition prepared from the melanin pigment with small particle size has higher transparency and uv-shielding ability.
Claims (6)
1. A method for producing melanin, the method comprising:
respectively adding a melanin precursor, a surfactant and an oxidant into a high molecular solution, adjusting the pH value to 7-13, and carrying out an oxidation reaction while stirring to obtain melanin;
the melanin precursor is one or a combination of tyrosine, cysteine, catechol, 1, 8-dihydroxynaphthalene, dopamine, dopa, 5, 6-dihydroxyindole-2-carboxylic acid, leuco dopamine, tryptophan, serotonin, epinephrine, norepinephrine and epinephrine red;
the surfactant is one or a combination of stearic acid, sodium dodecyl benzene sulfonate and fatty glyceride;
the oxidant is one or a combination of oxygen, ozone, hydrogen peroxide, sodium peroxide, benzoyl peroxide, peracetic acid, perbenzoic acid, potassium persulfate, sodium persulfate and ammonium persulfate;
the polymer is a water-soluble polymer; is one or the combination of polyethylene glycol and polyvinylpyrrolidone;
the molar ratio of the melanin precursor to the oxidant is 1 (0.1-10);
the concentration of the water-soluble polymer is 0.01-5%;
the concentration of the surfactant is 0.01-2%.
2. The method for producing melanin according to claim 1, wherein:
the molar ratio of the melanin precursor to the oxidant is 1 (5-10);
the concentration of the water-soluble polymer is 1-5%;
the concentration of the surfactant is 1-2%.
3. The method for producing melanin according to claim 1, wherein:
the oxidation reaction temperature is 10-70 ℃; the oxidation reaction time is 5-24 h.
4. A method for producing melanin according to claim 3, wherein:
the oxidation reaction temperature is 50-60 ℃; the oxidation reaction time is 5-10 h.
5. A method for producing melanin according to any one of claims 1 to 4, wherein:
the average grain diameter of the prepared melanin is 5-200 nm.
6. A method for producing melanin according to claim 5, wherein:
the average grain diameter of the prepared melanin is 5-100 nm.
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| CN110229326B (en) * | 2018-03-05 | 2020-09-01 | 江南大学 | Preparation method of melanin granules |
| CN110512463A (en) * | 2019-07-12 | 2019-11-29 | 杭州素锐科技有限公司 | A kind of manufacturing process of eyeshield paper |
| CN110888242B (en) * | 2019-10-21 | 2021-05-18 | 湖南波比生物科技有限公司 | Application method of melanin and preparation method of melanin lens |
| CN111378241A (en) * | 2020-05-11 | 2020-07-07 | 江苏可奥熙光学材料科技有限公司 | Blue-light-proof resin composition and preparation method thereof |
| CN111574733A (en) * | 2020-05-29 | 2020-08-25 | 浙江大学 | Preparation method of high-transparency ultraviolet shielding film |
| CN113683771B (en) * | 2021-07-09 | 2022-06-14 | 四川大学 | Preparation of artificial fungus black material and application of ultraviolet protection |
| CN113527660B (en) * | 2021-07-09 | 2022-06-14 | 四川大学 | Preparation of artificial fungus black material and antioxidation application |
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