CN113262719A - Application of peptide-like compound, micro-nano metal powder and preparation method thereof - Google Patents

Application of peptide-like compound, micro-nano metal powder and preparation method thereof Download PDF

Info

Publication number
CN113262719A
CN113262719A CN202110549512.3A CN202110549512A CN113262719A CN 113262719 A CN113262719 A CN 113262719A CN 202110549512 A CN202110549512 A CN 202110549512A CN 113262719 A CN113262719 A CN 113262719A
Authority
CN
China
Prior art keywords
micro
metal powder
nano metal
preparation
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN202110549512.3A
Other languages
Chinese (zh)
Inventor
刘成
孙光辉
蔡世昌
曾俊良
牛亮峰
梁玮
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Suzhou Xinghan New Material Technology Co ltd
Original Assignee
Suzhou Xinghan New Material Technology Co ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Suzhou Xinghan New Material Technology Co ltd filed Critical Suzhou Xinghan New Material Technology Co ltd
Priority to CN202110549512.3A priority Critical patent/CN113262719A/en
Publication of CN113262719A publication Critical patent/CN113262719A/en
Pending legal-status Critical Current

Links

Images

Classifications

    • 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
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B22—CASTING; POWDER METALLURGY
    • B22F—WORKING METALLIC POWDER; MANUFACTURE OF ARTICLES FROM METALLIC POWDER; MAKING METALLIC POWDER; APPARATUS OR DEVICES SPECIALLY ADAPTED FOR METALLIC POWDER
    • B22F1/00—Metallic powder; Treatment of metallic powder, e.g. to facilitate working or to improve properties
    • B22F1/05—Metallic powder characterised by the size or surface area of the particles
    • B22F1/054—Nanosized particles
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B22—CASTING; POWDER METALLURGY
    • B22F—WORKING METALLIC POWDER; MANUFACTURE OF ARTICLES FROM METALLIC POWDER; MAKING METALLIC POWDER; APPARATUS OR DEVICES SPECIALLY ADAPTED FOR METALLIC POWDER
    • B22F9/00—Making metallic powder or suspensions thereof
    • B22F9/16—Making metallic powder or suspensions thereof using chemical processes
    • B22F9/18—Making metallic powder or suspensions thereof using chemical processes with reduction of metal compounds
    • B22F9/24—Making metallic powder or suspensions thereof using chemical processes with reduction of metal compounds starting from liquid metal compounds, e.g. solutions
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y40/00—Manufacture or treatment of nanostructures

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nanotechnology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Composite Materials (AREA)
  • Manufacturing & Machinery (AREA)
  • Powder Metallurgy (AREA)
  • Manufacture Of Metal Powder And Suspensions Thereof (AREA)

Abstract

The invention provides application of a peptide-like compound, micro-nano metal powder and a preparation method thereof, wherein the peptide-like compound is used as a dispersing agent in preparation of the micro-nano metal powder; the preparation method of the micro-nano metal powder comprises the following steps: adding a peptoid compound and a metal salt into a solvent, uniformly mixing, adding a reducing agent, stirring for reaction, filtering, and collecting precipitates to obtain the micro-nano metal powder. The peptoid compound is used as a dispersing agent in the preparation of the micro-nano metal powder, so that the agglomeration of the micro-nano metal powder can be inhibited, the prepared micro-nano metal powder is uniformly dispersed, and compared with the conventional preparation process of the micro-nano metal powder, the preparation process of the peptoid compound is more environment-friendly by using a surfactant; the preparation route is simple, the synthesis condition is mild, and the operability is strong.

Description

Application of peptide-like compound, micro-nano metal powder and preparation method thereof
Technical Field
The invention relates to the technical field of nano materials, in particular to application of a peptide-like compound, micro-nano metal powder and a preparation method thereof.
Background
Micro-nano metal powder, especially micro-nano copper powder, has excellent conductivity, so that the micro-nano copper powder is widely applied to the fields of catalysis, electronic paste, microelectronics, solid lubricants and the like. At present, the preparation method of micro-nano metal powder is divided into a physical method and a chemical method, and the physical method has great dependence on equipment and high production cost, so that the preparation method is greatly restricted. At present, a chemical reduction method is usually adopted to prepare micro-nano metal powder, the method is simple and convenient to operate and low in production cost, but in order to prevent phenomena such as oxidation and agglomeration of nano copper in a synthesis process, surfactants such as polyvinylpyrrolidone (PVP), Cetyl Trimethyl Ammonium Bromide (CTAB) and the like are usually required to be added in the production process, and although the surfactants can achieve good dispersion effects, the surfactants have toxicity and can damage the environment particularly in large-scale production, so that further use of the surfactants is greatly limited. Therefore, a technical scheme that the traditional surfactant is not used and the prepared micro-nano metal powder is uniformly dispersed is needed.
Disclosure of Invention
In view of the above, the invention provides an application of a peptide-like compound, micro-nano metal powder and a preparation method thereof, so as to solve or partially solve the technical problems in the prior art.
In a first aspect, the invention provides an application of a peptoid compound, and an application of the peptoid compound as a dispersant in preparation of micro-nano metal powder, wherein the peptoid compound is a beta-hydroxybutyryl-amino acid compound, and a structural formula of the beta-hydroxybutyryl-amino acid is as follows:
Figure BDA0003074664600000011
(R)nis alpha-amino acid substituent or polypeptide chain formed by alpha-amino acid condensation polymerization.
In a second aspect, the invention also provides a preparation method of the micro-nano metal powder, which comprises the following steps:
and adding the peptoid compound and the metal salt into a solvent, uniformly mixing, adding a reducing agent, stirring for reaction, filtering, and collecting precipitates to obtain the micro-nano metal powder.
Preferably, in the preparation method of the micro-nano metal powder, the metal salt is copper salt.
Preferably, in the preparation method of the micro-nano metal powder, the copper salt comprises at least one of copper sulfate, copper chloride and copper nitrate.
Preferably, in the preparation method of the micro-nano metal powder, the reducing agent comprises at least one of ascorbic acid, formic acid, oxalic acid, sodium borohydride and sodium hypophosphite.
Preferably, in the method for preparing the micro-nano metal powder, the solvent includes at least one of water, DMF, DMSO, ethylene glycol, glycerol, and acetone.
Preferably, the preparation method of the micro-nano metal powder comprises the steps of adding the peptoid compound and the metal salt into a solvent, uniformly mixing, adding a reducing agent, adjusting the pH value to 7-10, stirring for reaction, filtering, and collecting precipitates to obtain the micro-nano metal powder.
Preferably, in the preparation method of the micro-nano metal powder, the reaction time is 0.5-1 h in the step of stirring reaction.
Preferably, in the preparation method of the micro-nano metal powder, the mass-volume ratio of the peptoid compound, the metal salt, the reducing agent and the solvent is (0.5-5) g, (0.5-10) g, (1-5) g and (50-500) mL.
In a third aspect, the invention also provides micro-nano metal powder prepared by the preparation method.
Compared with the prior art, the application of the peptide-like compound, the micro-nano metal powder and the preparation method thereof have the following beneficial effects:
(1) the peptoid compound is used as a dispersing agent in the preparation of the micro-nano metal powder, so that the agglomeration of the micro-nano metal powder can be inhibited, the prepared micro-nano metal powder is uniformly dispersed, and compared with the conventional preparation process of the micro-nano metal powder, the preparation process of the peptoid compound is more environment-friendly by using a surfactant;
(2) according to the preparation method of the micro-nano metal powder, the peptoid compound is used as the dispersing agent, and the uniformly dispersed micro-nano metal powder can be prepared;
(3) according to the preparation method of the micro-nano metal powder, the peptide-like compounds with different structural formulas can be used for preparing the micro-nano metal powder with different shapes, particle size distributions and structures, so that the structure and the shape of the micro-nano metal powder can be regulated.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below. It is obvious that the drawings in the following description are only some embodiments of the invention, and that for a person skilled in the art, other drawings can be derived from them without inventive effort.
FIG. 1 is a surface topography of micro-nano copper powder prepared in embodiment 1 of the invention;
FIG. 2 is a surface topography of the micro-nano copper powder prepared in embodiment 2 of the invention;
FIG. 3 is a surface topography of the micro-nano copper powder prepared in embodiment 3 of the invention;
FIG. 4 is a surface topography of the micro-nano copper powder prepared in embodiment 4 of the invention;
FIG. 5 is a surface topography of the micro-nano copper powder prepared in example 5 of the present invention;
FIG. 6 is a surface topography of the micro-nano copper powder prepared in example 6 of the present invention;
FIG. 7 is a surface topography of the micro-nano copper powder prepared in example 7 of the present invention;
FIG. 8 is a surface topography of the micro-nano copper powder prepared in example 8 of the present invention;
FIG. 9 is an XRD (X-ray diffraction) spectrum of the micro-nano copper powder prepared in the embodiment 1 of the invention;
FIG. 10 is a graph showing the variation of the resistivity of the micro-nano copper powder prepared in the embodiment 1 of the present invention with pressure;
fig. 11 is a graph showing the variation of the electrical conductivity of the micro-nano copper powder prepared in embodiment 1 of the present invention with pressure.
Detailed Description
In the following, the technical solutions in the embodiments of the present invention will be clearly and completely described in conjunction with the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be obtained by a person skilled in the art without any inventive step based on the embodiments of the present invention, are within the scope of the present invention.
The embodiment of the application provides application of a peptide-like compound, in particular to application of the peptide-like compound as a dispersing agent in preparation of micro-nano metal powder, wherein the peptide-like compound is a beta-hydroxybutyryl-amino acid compound, and the structural formula of the beta-hydroxybutyryl-amino acid is as follows:
Figure BDA0003074664600000041
(R)nis alpha-amino acid substituent or polypeptide chain formed by alpha-amino acid condensation polymerization.
It should be noted that, in the embodiment of the present application, the peptoid compound is used as a dispersant in the preparation of the micro-nano metal powder, so that the agglomeration of the micro-nano metal powder can be inhibited, and the micro-nano metal powder is uniformly dispersed. In particular, the peptoid compound in the embodiment of the application is a beta-hydroxybutyryl-amino acid compound, the specific structure and the synthesis method thereof adopt the prior art, and the application does not improve the structure and the synthesis method.
Specifically, in some embodiments, the α -amino acid can be alanine, arginine, aspartic acid, cysteine, glutamine, glutamic acid, histidine, isoleucine, glycine, asparagine, leucine, lysine, methionine, phenylalanine, proline, serine, threonine, tryptophan, tyrosine, valine, or the like, and the corresponding (R) n is a polypeptide chain formed by condensation polymerization of the above α -amino acids.
In some embodiments, the β -hydroxybutyryl-amino acid compound includes dipeptide, tripeptide, tetrapeptide, pentapeptide, and like peptoid compounds formed from β -hydroxybutyric acid and various α -amino acids.
In some embodiments, the beta-hydroxybutyryl-amino acid compound is a beta-hydroxybutyryl-isoleucine pseudo-dipeptide having the formula
Figure BDA0003074664600000042
In some embodiments, the beta-hydroxybutyryl-amino acid compound is a beta-hydroxybutyryl-glutamic acid pseudodipeptide having the formula
Figure BDA0003074664600000043
In some embodiments, the beta-hydroxybutyryl-amino acid compound is a pseudo-tripeptide of beta-hydroxybutyryl-alanine-glutamic acid having the formula
Figure BDA0003074664600000051
In some embodiments, the beta-hydroxybutyryl-amino acid compound is a beta-hydroxybutyryl-glycine-methionine pseudo-tripeptide of formula
Figure BDA0003074664600000052
In some embodiments, the beta-hydroxybutyryl-amino acid compound is a beta-hydroxybutyryl-alanine-proline pseudo-tripeptide of formula
Figure BDA0003074664600000053
In some embodiments, the β -hydroxybutyryl-amino acid compound is a β -hydroxybutyryl-leucyl-valyl-glutamic acid pseudotetrapeptide having the structural formula
Figure BDA0003074664600000054
In some embodiments, the β -hydroxybutyryl-amino acid compound is a β -hydroxybutyryl-glycyl-alanyl-methionine pseudotetrapeptide having the formula
Figure BDA0003074664600000055
In some embodiments, the β -hydroxybutyryl-amino acid compound is a β -hydroxybutyryl-alanyl-valyl-isoleucyl-glycine pseudopentapeptide having the structural formula
Figure BDA0003074664600000061
Based on the same invention concept, the invention also provides a preparation method of the micro-nano metal powder, which comprises the following steps:
and adding the peptoid compound and the metal salt into a solvent, uniformly mixing, adding a reducing agent, stirring for reaction, filtering, and collecting precipitates to obtain the micro-nano metal powder.
In this embodiment, specific micro-nano metal powder includes cobalt powder, nickel powder, zinc powder, aluminum powder, copper powder, iron powder, molybdenum powder, and the like, corresponding metal salts are cobalt salt, nickel salt, zinc salt, aluminum salt, copper salt, iron salt, molybdenum salt, and the like, and specific metal salts are sulfate, nitrate, chloride, and the like of corresponding metals. The peptoid compounds with different structural formulas can be used for preparing micro-nano metal powder with different shapes, particle size distributions and structures, so that the structure and the shape of the micro-nano metal powder can be regulated.
In some embodiments, the metal salt is a copper salt.
In some embodiments, the copper salt comprises at least one of copper sulfate, copper chloride, and copper nitrate.
In some embodiments, the reducing agent comprises at least one of ascorbic acid, formic acid, oxalic acid, sodium borohydride, and sodium hypophosphite.
In some embodiments, the solvent comprises at least one of water, DMF, DMSO, ethylene glycol, glycerol, and acetone. Wherein, DMF is N, N-dimethylformamide, and DMSO is dimethyl sulfoxide.
In some embodiments, the peptoid compound and the metal salt are added into a solvent, uniformly mixed, added with a reducing agent, adjusted to have a pH value of 7-10, stirred for reaction, filtered, and collected for precipitation, so as to obtain the micro-nano metal powder.
In some embodiments, the reaction time in the stirring step is 0.5 to 1 hour.
In some embodiments, the mass-to-volume ratio of the peptoid compound, the metal salt, the reducing agent and the solvent is (0.5-5) g, (0.5-10) g, (1-5) g and (50-500) mL.
Based on the same inventive concept, the embodiment of the application also provides the micro-nano metal powder prepared by the preparation method.
The following further describes a preparation method of the micro-nano metal powder according to the present application with specific examples.
Example 1
The embodiment of the application provides a preparation method of micro-nano copper powder, which comprises the following steps:
0.01mol of CuSO4Dissolving 5g of beta-hydroxybutyryl-isoleucine pseudo dipeptide in 0.5L of deionized water, stirring uniformly, adding 0.02mol of ascorbic acid, adding ammonia water to adjust the pH value to 7, stirring to react for 3h, centrifuging to collect precipitate, cleaning with deionized water and ethanol, and drying at 40 ℃ to obtain the micro-nano copper powder.
The synthesis method of the beta-hydroxybutyryl-isoleucine pseudo dipeptide comprises the following steps:
s1, adding 0.02mol of tert-butyl dimethyl silyl ether beta-hydroxybutyric acid, 0.02mol of isoleucine ethyl ester hydrochloride and 0.002mol of 4-dimethylamino pyridine into 100mL of dichloromethane, then adding 0.024mol of triethylamine, and stirring to react for 30 minutes to obtain a reaction solution;
s2, dissolving 0.03mol of N, N' -dicyclohexylcarbodiimide in 40mL of dichloromethane, then dripping the reaction solution into the dichloromethane, stirring and reacting for 3 hours at room temperature after dripping, then carrying out suction filtration, washing the filtrate twice with 80mL of water, washing the filtrate twice with 30mL of 0.1M dilute hydrochloric acid, washing the filtrate once with 30mL of saturated sodium bicarbonate aqueous solution, washing the filtrate once with 30mL of saturated sodium chloride aqueous solution, drying the dichloromethane phase and concentrating;
s3, dissolving the condensed concentrated solution with 90mL of tetrahydrofuran, adding 1 equivalent of tetrabutyl ammonium fluoride, stirring at room temperature for 2h, then adding water to quench the reaction, removing the tetrahydrofuran under reduced pressure, extracting the water phase with 50mL of dichloromethane for 3 times respectively, combining the organic phases, washing with 50mL of saturated sodium chloride once, and concentrating; adding 1-time equivalent of 1M sodium hydroxide aqueous solution into the concentrated solution, keeping the pH value at 7-8, stirring for reacting for 1h, washing the reaction solution with 40mL dichloromethane for three times, concentrating the water phase, and recrystallizing with ethanol/acetone to obtain a white solid, namely the beta-hydroxybutyryl-isoleucine pseudo-dipeptide sodium salt; adding an equivalent hydrogen chloride ethanol solution into the beta-hydroxybutyryl-isoleucine pseudo dipeptide sodium salt, filtering and concentrating to obtain the beta-hydroxybutyryl-isoleucine pseudo dipeptide.
The nuclear magnetic data of the beta-hydroxybutyryl-isoleucine pseudo dipeptide prepared in the above way are as follows:1H NMR(400MHz，D2O)δ4.11(m，1H)，4.02(m，1H)，2.34(m，2H)，1.75(m，1H)，1.32(m，1H)，1.12(d，3H)，1.05(m，1H)，0.80(m，6H).HRMS(ESI+)：Calculated for C10H20NO4[M+H]+：218.1387；Found：218.1395。
example 2
The embodiment of the application provides a preparation method of micro-nano copper powder, which comprises the following steps:
0.01mol of CuSO45g of beta-hydroxybutyl acidDissolving acyl-glutamic acid pseudo dipeptide in 0.5L of deionized water, stirring uniformly, then adding 0.02mol of ascorbic acid, adding ammonia water to adjust the pH value to 7, stirring for reaction for 3 hours, centrifuging, collecting precipitate, washing with deionized water and ethanol, and finally drying at 40 ℃ to obtain the micro-nano copper powder.
The method for synthesizing the beta-hydroxybutyryl-glutamic acid pseudodipeptide can be referred to the method for synthesizing the beta-hydroxybutyryl-isoleucine pseudodipeptide in example 1, and specifically, the beta-hydroxybutyryl-glutamic acid pseudodipeptide is prepared from tert-butyldimethylsiloxane beta-hydroxybutyric acid and glutamic acid ethyl ester hydrochloride. The nuclear magnetic data of the beta-hydroxybutyryl-glutamic acid pseudo dipeptide is as follows:1HNMR(400MHz，D2O)δ4.23(m，1H)，4.15(m，1H)，2.49(m，2H)，2.25(m，2H)，2.09(m，1H)，1.92(m，1H)，1.26(d，3H).HRMS(ESI+)：Calculated for C9H16NO6[M+H]+：234.0972；Found：234.0979。
example 3
The embodiment of the application provides a preparation method of micro-nano copper powder, which comprises the following steps:
0.01mol of CuSO4Dissolving 5g of beta-hydroxybutyryl-alanine-glutamic acid pseudo-tripeptide in 0.5L of deionized water, stirring uniformly, adding 0.02mol of ascorbic acid, adding ammonia water to adjust the pH value to 7, stirring for reaction for 3 hours, centrifuging to collect precipitate, washing with deionized water and ethanol, and finally drying at 40 ℃ to obtain the micro-nano copper powder.
Wherein, the synthesis method of the beta-hydroxybutyryl-alanine-glutamic acid pseudo tripeptide can refer to the beta-hydroxy in the example 1
The synthesis process of butyryl-isoleucine pseudo dipeptide includes the specific steps of preparing tert-butyl dimethyl silyl ether beta-hydroxy butyric acid, alanine ethyl ester hydrochloride and glutamic acid ethyl ester hydrochloride. Nuclear magnetic data for the β -hydroxybutyryl-alanine-glutamic acid pseudo-tripeptide are:1H NMR(400MHz，D2O)δ4.25(m，1H)，4.09(m，1H)，4.00(m，1H)，2.33(m，2H)，2.07(m，2H)，1.95(m，1H)，1.78(m，1H)，1.28(m，3H)，1.11(d，3H).HRMS(ESI+)：Calculated for C12H21N2O7[M+H]+：305.1343；Found：305.1349。
example 4
The embodiment of the application provides a preparation method of micro-nano copper powder, which comprises the following steps:
0.01mol of CuSO4Dissolving 5g of beta-hydroxybutyryl-glycine-methionine pseudo-tripeptide in 0.5L of deionized water, stirring uniformly, adding 0.02mol of ascorbic acid, adding ammonia water to adjust the pH value to 7, stirring for reacting for 3 hours, centrifuging to collect precipitate, washing with deionized water and ethanol, and finally drying at 40 ℃ to obtain the micro-nano copper powder.
Wherein, the synthesis method of the beta-hydroxybutyryl-glycine-methionine pseudo tripeptide can be referred to the beta-hydroxy group in example 1
The butyryl-isoleucine pseudo dipeptide is prepared with tert-butyl dimethyl silyl ether beta-hydroxy butyric acid, glycine ethyl ester hydrochloride and methionine ethyl ester hydrochloride. The nuclear magnetic data of the beta-hydroxybutyryl-glycine-methionine pseudo-tripeptide are as follows:1H NMR(400MHz，D2O)δ4.21(m，1H)，4.07(m，1H)，3.84(m，2H)，2.35(m，4H)，2.00(m，1H)，1.98(s，3H)，1.80(m，1H)，1.13(d，3H).HRMS(ESI+)：Calculated for C11H21N2O5S[M+H]+：293.1166；Found：293.1173。
example 5
The embodiment of the application provides a preparation method of micro-nano copper powder, which comprises the following steps:
0.01mol of CuSO4Dissolving 5g of beta-hydroxybutyryl-alanine-proline pseudo-tripeptide in 0.5L of deionized water, stirring uniformly, adding 0.02mol of ascorbic acid, adding ammonia water to adjust the pH value to 7, stirring for reacting for 3 hours, centrifuging to collect precipitate, washing with deionized water and ethanol, and finally drying at 40 ℃ to obtain the micro-nano copper powder.
Wherein, the synthesis method of the pseudo tripeptide of beta-hydroxybutyryl-alanine-proline can refer to the beta-hydroxy-in example 1
A process for synthesizing butyryl-isoleucine pseudo dipeptide from tert-butyldimethylsiloxane beta-hydroxyButyric acid and alanine ethyl ester hydrochloride, proline ethyl ester hydrochloride. The nuclear magnetic data of the beta-hydroxybutyryl-alanine-proline pseudo tripeptide are as follows:1H NMR(400MHz，D2O)δ4.60(m，1H)，4.16(m，2H)，3.55(m，2H)，2.31(m，2H)，2.01(m，2H)，1.84(m，2H)，1.28(m，3H)，1.12(m，3H).HRMS(ESI+)：Calculated for C12H21N2O5[M+H]+：273.1445；Found：273.1454。
example 6
The embodiment of the application provides a preparation method of micro-nano copper powder, which comprises the following steps:
0.01mol of CuSO4Dissolving 5g of beta-hydroxybutyryl-leucyl-valyl-glutamic acid pseudo-tetrapeptide in 0.5L of deionized water, stirring uniformly, adding 0.02mol of ascorbic acid, adding ammonia water to adjust the pH value to 7, stirring to react for 3 hours, centrifuging to collect precipitates, washing with deionized water and ethanol, and finally drying at 40 ℃ to obtain the micro-nano copper powder.
The method for synthesizing the β -hydroxybutyryl-leucyl-valyl-glutamic acid pseudotetrapeptide can be referred to the method for synthesizing the β -hydroxybutyryl-isoleucine pseudodipeptide in example 1, and specifically, the β -hydroxybutyryl-isoleucine pseudodipeptide is prepared from tert-butyldimethylsiloxane β -hydroxybutyric acid, and leucine ethyl ester hydrochloride, valine ethyl ester hydrochloride, and glutamic acid ethyl ester hydrochloride. The nuclear magnetic data for the β -hydroxybutyryl-leucyl-valyl-glutamic acid pseudotetrapeptide is:1H NMR(400MHz，D2O)δ4.25(m，2H)，4.06(m，1H)，3.94(m，1H)，2.51(m，2H)，2.35(m，2H)，2.11(m，2H)，1.98(m，1H)，1.52(m，3H)，1.11(d，3H)，0.76(m，12H).HRMS(ESI+)：Calculated for C20H36N3O8[M+H]+：446.2497；Found：446.2504。
example 7
The embodiment of the application provides a preparation method of micro-nano copper powder, which comprises the following steps:
0.01mol of CuSO45g of beta-hydroxybutyryl-glycyl-alanyl-methionine pseudotetrapeptide in 0.5L of deionized water with stirringAnd uniformly stirring, adding 0.02mol of ascorbic acid, adding ammonia water to adjust the pH value to 7, stirring to react for 3 hours, centrifuging to collect precipitates, washing with deionized water and ethanol, and finally drying at 40 ℃ to obtain the micro-nano copper powder.
The method for synthesizing the β -hydroxybutyryl-glycyl-alanyl-methionine pseudotetrapeptide can be referred to the method for synthesizing the β -hydroxybutyryl-isoleucine pseudodipeptide in example 1, and specifically, the β -hydroxybutyryl-isoleucine pseudodipeptide is prepared from tert-butyldimethylsiloxane β -hydroxybutyric acid, glycine ethyl ester hydrochloride, alanine ethyl ester hydrochloride, and methionine ethyl ester hydrochloride. The nuclear magnetic data for the β -hydroxybutyryl-glycyl-alanyl-methionine pseudotetrapeptide are:1H NMR(400MHz，D2O)δ4.31(m，1H)，4.22(m，1H)，4.12(m，1H)，3.84(m，2H)，2.57(m，2H)，2.37(m，2H)，2.05(s，3H)，1.95(m，2H)，1.32(d，3H)，1.12(d，3H).HRMS(ESI+)：Calculated for C14H26N3O6S[M+H]+：364.1537；Found：364.1531。
example 8
The embodiment of the application provides a preparation method of micro-nano copper powder, which comprises the following steps:
0.01mol of CuSO4Dissolving 5g of beta-hydroxybutyryl-alanyl-valyl-isoleucyl-glycine pseudo-pentapeptide in 0.5L of deionized water, uniformly stirring, adding 0.02mol of ascorbic acid, adding ammonia water to adjust the pH value to 7, stirring to react for 3 hours, centrifugally collecting precipitates, cleaning with deionized water and ethanol, and finally drying at 40 ℃ to obtain the micro-nano copper powder.
The method for synthesizing β -hydroxybutyryl-alanyl-valyl-isoleucyl-glycine pseudopentapeptide can be referred to the method for synthesizing β -hydroxybutyryl-isoleucine pseudodipeptide in example 1, and specifically, it is prepared from tert-butyldimethylsiloxane β -hydroxybutyric acid and alanine ethyl ester hydrochloride, valine ethyl ester hydrochloride, isoleucine ethyl ester hydrochloride, glycine ethyl ester hydrochloride. The nuclear magnetic data for the β -hydroxybutyryl-alanyl-valyl-isoleucyl-glycine pseudo-pentapeptide is:1H NMR(400MHz，D2O)δ4.21(m，2H)，4.05(m，4H)，2.35(m，2H)，2.00(m，1H)，1.83(m，1H)，1.35(m，4H)，1.09(m，4H)，0.77(m，12H).HRMS(ESI+)：Calculated for C20H37N4O7[M+H]+：445.2657；Found：445.2653。
the results of testing the surface topography of the micro-nano copper powder prepared in the above examples 1 to 8 are shown in fig. 1 to 8, respectively.
As can be seen from fig. 1 to 8, the micro-nano copper powder prepared in different embodiments is uniform in distribution and good in dispersibility, and the micro-nano copper powder prepared in different embodiments has different particle sizes. As can be seen from FIG. 1, the average particle size of the micro-nano copper powder prepared in example 1 is 500-600 nm. As can be seen from FIG. 2, the average particle size of the micro-nano copper powder prepared in example 2 is 600-700 nm. As can be seen from FIG. 3, the average particle size of the micro-nano copper powder prepared in example 3 is 500-600 nm. As can be seen from FIG. 4, the average particle size of the micro-nano copper powder prepared in example 4 is 600-800 nm. As can be seen from fig. 5, the average particle size of the micro-nano copper powder prepared in example 5 is 1 um. As can be seen from FIG. 6, the average particle size of the micro-nano copper powder prepared in example 6 is 1-1.2 um. As can be seen from FIG. 7, the average particle size of the micro-nano copper powder prepared in example 7 is 600-800 nm. As can be seen from FIG. 8, the average particle size of the micro-nano copper powder prepared in example 8 is 500-600 nm.
XRD (X-ray diffraction) patterns of the micro-nano copper powder prepared in the example 1 and the standard copper powder are shown in figure 9. Wherein the Synthesized Copper in fig. 9 is an XRD pattern of the micro-nano Copper powder prepared in example 1 of the present application, and PDF #04-0836Copper is a standard Copper powder XRD pattern. From fig. 9, it can be seen that the prepared micro-nano copper powder map is close to the standard copper powder map, which indicates that the copper powder is synthesized by the method of the present application.
The resistivity and the conductivity of the micro-nano copper powder prepared in example 1 are tested, and the results are shown in fig. 10-11.
The resistivity tests of fig. 10 and 11 were performed using an automated powder resistivity tester model ST2742B, manufactured by suzhou crystal lattice electronics limited, and show data on resistivity and conductivity of the samples to be tested at 2-30 MPa. The test method comprises the following steps: 2g of the sample was taken and placed in a sample cell and an automated powder resistivity tester was started to test the resistivity of the sample at different pressures. And (3) testing temperature: and (4) room temperature.
According to the results shown in fig. 10 and fig. 11, the micro-nano copper powder prepared by using the novel peptide-like compound as the dispersant has low resistivity and high conductivity, and the dispersant can play a good role in oxidation resistance and agglomeration prevention.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.

Claims (10)

1. The application of the peptide-like compound is characterized in that the peptide-like compound is applied to preparation of micro-nano metal powder as a dispersing agent, wherein the peptide-like compound is a beta-hydroxybutyryl-amino acid compound, and the structural formula of the beta-hydroxybutyryl-amino acid is as follows:
Figure FDA0003074664590000011
(R)nis alpha-amino acid substituent or polypeptide chain formed by alpha-amino acid condensation polymerization.
2. A preparation method of micro-nano metal powder is characterized by comprising the following steps: adding the peptoid compound and the metal salt of claim 1 into a solvent, uniformly mixing, adding a reducing agent, stirring for reaction, filtering, and collecting precipitates to obtain the micro-nano metal powder.
3. The method for preparing micro-nano metal powder according to claim 2, wherein the metal salt is copper salt.
4. The method for preparing micro-nano metal powder according to claim 3, wherein the copper salt comprises at least one of copper sulfate, copper chloride and copper nitrate.
5. The method for preparing micro-nano metal powder according to claim 2, wherein the reducing agent comprises at least one of ascorbic acid, formic acid, oxalic acid, sodium borohydride and sodium hypophosphite.
6. The method for preparing micro-nano metal powder according to claim 2, wherein the solvent comprises at least one of water, DMF, DMSO, ethylene glycol, glycerol and acetone.
7. The preparation method of the micro-nano metal powder as claimed in claim 2, wherein the peptoid compound and the metal salt are added into a solvent, uniformly mixed, added with a reducing agent, adjusted to have a pH value of 7-10, stirred for reaction, filtered, and precipitated to obtain the micro-nano metal powder.
8. The method for preparing micro-nano metal powder according to claim 2, wherein in the step of stirring for reaction, the reaction time is 0.5-1 h.
9. The preparation method of the micro-nano metal powder as claimed in claim 2, wherein the mass-to-volume ratio of the peptoid compound, the metal salt, the reducing agent and the solvent is (0.5-5) g, (0.5-10) g, (1-5) g, (50-500) mL.
10. The micro-nano metal powder is characterized by being prepared by the preparation method according to any one of claims 2 to 9.
CN202110549512.3A 2021-05-20 2021-05-20 Application of peptide-like compound, micro-nano metal powder and preparation method thereof Pending CN113262719A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202110549512.3A CN113262719A (en) 2021-05-20 2021-05-20 Application of peptide-like compound, micro-nano metal powder and preparation method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202110549512.3A CN113262719A (en) 2021-05-20 2021-05-20 Application of peptide-like compound, micro-nano metal powder and preparation method thereof

Publications (1)

Publication Number Publication Date
CN113262719A true CN113262719A (en) 2021-08-17

Family

ID=77231978

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202110549512.3A Pending CN113262719A (en) 2021-05-20 2021-05-20 Application of peptide-like compound, micro-nano metal powder and preparation method thereof

Country Status (1)

Country Link
CN (1) CN113262719A (en)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011026572A1 (en) * 2009-09-01 2011-03-10 Eth Zurich Dispersant stabilization of inorganic non-metallic particles
US20110230427A1 (en) * 2010-03-22 2011-09-22 David Bruce Robinson Materials and methods for stabilizing nanoparticles in salt solutions
CN105268991A (en) * 2015-11-09 2016-01-27 上海纳米技术及应用国家工程研究中心有限公司 Method for preparing high-concentration nano silver monomer dispersion liquid
BR102016004486A2 (en) * 2016-02-29 2016-02-29 CISTEINIL SYNTHETIC PEPTIDES AS REDUCING AND STABILIZING AGENTS IN THE GREEN SYNTHESIS OF A STAGE OF METALLIC NANOPARTICLES AND QUANTUM DOTS WITH MORPHOLOGY AND SIZE MODULATED BY THE PH
CN108017555A (en) * 2017-11-28 2018-05-11 郑州海斯威生物技术有限公司 A kind of beta-hydroxy butyryl-amino-acid compound and preparation method and application
CN108394927A (en) * 2018-04-13 2018-08-14 唐山学院 A kind of preparation method of the nano cupric oxide of morphology controllable

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011026572A1 (en) * 2009-09-01 2011-03-10 Eth Zurich Dispersant stabilization of inorganic non-metallic particles
US20110230427A1 (en) * 2010-03-22 2011-09-22 David Bruce Robinson Materials and methods for stabilizing nanoparticles in salt solutions
CN105268991A (en) * 2015-11-09 2016-01-27 上海纳米技术及应用国家工程研究中心有限公司 Method for preparing high-concentration nano silver monomer dispersion liquid
BR102016004486A2 (en) * 2016-02-29 2016-02-29 CISTEINIL SYNTHETIC PEPTIDES AS REDUCING AND STABILIZING AGENTS IN THE GREEN SYNTHESIS OF A STAGE OF METALLIC NANOPARTICLES AND QUANTUM DOTS WITH MORPHOLOGY AND SIZE MODULATED BY THE PH
CN108017555A (en) * 2017-11-28 2018-05-11 郑州海斯威生物技术有限公司 A kind of beta-hydroxy butyryl-amino-acid compound and preparation method and application
CN108394927A (en) * 2018-04-13 2018-08-14 唐山学院 A kind of preparation method of the nano cupric oxide of morphology controllable

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
王爱丽等: "不同有机官能团对室温下纳米银形貌控制合成的影响", 《贵金属》, vol. 27, no. 02, 30 June 2006 (2006-06-30) *
王静等: "单分散的银纳米粒子的制备及表征", 《江苏科技大学学报(自然科学版)》, vol. 24, no. 04, 31 August 2010 (2010-08-31), pages 350 - 352 *

Similar Documents

Publication Publication Date Title
Li et al. Preparation of water-soluble magnetite nanocrystals from hydrated ferric salts in 2-pyrrolidone: mechanism leading to Fe3O4
US20140328737A1 (en) Cobalt extraction method
CN103157803A (en) Method of preparing nano-alloy through solid phase chemical reaction
CN109485085B (en) A kind of preparation method of hollow octahedra cuprous oxide
CN111871400B (en) Preparation method and application of guanidine salt ionic liquid modified magnetic solid phase extraction adsorbent
CN103303980B (en) The method of sulfonated lignin template synthesis nano-sized iron oxide
CN113814408B (en) Preparation and component regulation and control method of CuPd alloy nanocrystalline
CN113262719A (en) Application of peptide-like compound, micro-nano metal powder and preparation method thereof
CN104650358B (en) Porphyrin-based heteronuclear double-metal polymer, and preparation method and applications thereof
CN109569642B (en) Coprecipitation preparation method of copper-manganese-containing bi-component oxide
CN108587569B (en) Oil-soluble ferroferric oxide/modified graphene oxide composite material and preparation method and application thereof
WO2013069563A1 (en) Cobalt extraction method
CN108976148A (en) A kind of preparation method of 1,2- Propane Diamine 5- bromosalicylaldehyde Bis-Schiff Bases corrosion inhibiter
CN1810293A (en) Magnetic resonance imaging contrast medium based on metal fullerene and its prepn process
JP2010077520A (en) Method for producing fine copper particle, and fine copper particle
CN115595591A (en) Glycine derivative corrosion inhibitor and preparation method and application thereof
CN113275584B (en) Micro-nano silver powder and preparation method and application thereof
CN114988478A (en) Method for preparing battery-grade manganese sulfate by synergistic elution crystallization of chelating agent
US8673261B2 (en) Process for preparing magnetite (Fe3O4) and derivatives thereof
CN115069290A (en) Nitrogen-defect-containing porous carbon nitride-loaded monoatomic copper catalyst, preparation method thereof and application thereof in light nitrogen fixation
Voronkova et al. Complexation and flotation of nonferrous metal ions from alkaline solutions with N-acyl-N′-(p-toluenesulfonyl) hydrazines
CN110681875B (en) Isosteviol metal gel and preparation method and application thereof
CN110496603A (en) A kind of synthetic method of copper-based flexibility MOF material
CN110646526A (en) Enrichment analysis method of perfluorinated compounds in food based on magnetic microporous organic network composite material
CN112079761B (en) Bisamide nonionic surfactant and synthesis method and application thereof

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
RJ01 Rejection of invention patent application after publication

Application publication date: 20210817

RJ01 Rejection of invention patent application after publication