CN111574708A - Preparation method of aromatic polyamide whisker - Google Patents
Preparation method of aromatic polyamide whisker Download PDFInfo
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- CN111574708A CN111574708A CN202010504777.7A CN202010504777A CN111574708A CN 111574708 A CN111574708 A CN 111574708A CN 202010504777 A CN202010504777 A CN 202010504777A CN 111574708 A CN111574708 A CN 111574708A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/32—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from aromatic diamines and aromatic dicarboxylic acids with both amino and carboxylic groups aromatically bound
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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/46—Post-polymerisation treatment
Abstract
The invention discloses a preparation method of aromatic polyamide whisker, which adopts aromatic diamine as a first reaction monomer, aromatic diacid or acyl halide thereof as a second reaction monomer, wherein the first reaction monomer and the second reaction monomer are subjected to polycondensation reaction in a polymer solution, nano aromatic polyamide is generated in situ after polycondensation, a stabilizer is added, then the solvent of the polymer solution is used for dilution, and the aromatic polyamide whisker is obtained after separation. The aromatic polyamide whisker prepared by the method has the characteristics of high mechanical strength, acid resistance and alkali resistance, and is suitable for being widely applied to the field of composite materials.
Description
Technical Field
The invention relates to a high polymer material technology, in particular to a preparation method of aromatic polyamide whiskers.
Background
Whiskers are micro-nano-sized short fibers grown from high purity single crystals and have mechanical strength equal to that produced by the force between adjacent atoms. The highly oriented structure of the whisker not only enables the whisker to have high strength, high modulus and high elongation, but also has the properties of electricity, light, magnetism, dielectric, electric conduction and super electric conduction.
Whiskers can be classified into two major classes, organic whiskers and inorganic whiskers. At present, the prepared whiskers are generally inorganic materials, such as SiC, potassium titanate, aluminum borate whiskers, aluminum oxide and the like. The metal whiskers are mainly applied to metal matrix composite materials, and the ceramic matrix whiskers and the inorganic salt whiskers can be applied to a plurality of fields such as ceramic composite materials and polymer composite materials. Therefore, when the inorganic material whiskers are used in an organic composite material, an interface treatment is necessary to achieve good combination. However, the existing organic whiskers, such as cellulose whisker, poly (butyl acrylate-styrene) whisker, poly (4-hydroxybenzene methyl ester) whisker (PHB whisker) and the like, have small mechanical strength, acid resistance and alkali resistance, and can not meet the use requirements of composite materials.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a preparation method of an aromatic polyamide whisker, and the aromatic polyamide whisker prepared by the preparation method has excellent mechanical strength, acid resistance and alkali resistance, and meets the application requirements in composite materials.
In order to achieve the purpose, the invention adopts the following technical scheme:
a preparation method of aromatic polyamide whiskers adopts aromatic diamine as a first reaction monomer, aromatic diacid or acyl halide thereof as a second reaction monomer, the first reaction monomer and the second reaction monomer carry out polycondensation reaction in a polymer solution, aromatic polyamide nano whisker suspension is generated in situ after polycondensation, a stabilizer is added, then a solvent of the polymer solution is used for dilution, and the aromatic polyamide whiskers are obtained after separation.
Further, the aromatic diamine is p-phenylenediamine.
Further, the aromatic diacid or the acyl halide thereof comprises one or two of terephthaloyl chloride and terephthalic acid.
Further, the polymer solution comprises one or more of polysulfone solution, polyethersulfone solution, polyethylene solution and polyvinylidene chloride solution.
Further, the solvent of the polymer solution is an organic solvent, and the organic solvent comprises at least one of N, N-dimethylacetamide, dimethyl sulfoxide and N-methylpyrrolidone.
Further, the mass percentage concentration of the polymer in the polymer solution is 15-20%.
Furthermore, the mass percentage concentration of the aromatic polyamide generated in the polycondensation reaction is 4-18%.
Further, 1-5% of stabilizer is added into the system according to the mass percentage concentration, the main purpose is to stabilize the aromatic polyamide whisker generated in the system, so that the whisker does not aggregate or precipitate further, and the stabilizer comprises at least one of span, tween and coco glucoside.
Further, the first reaction monomer is added into the polymer solution, the second reaction monomer is gradually added under the stirring condition after the first reaction monomer is completely dissolved to carry out polycondensation reaction, and then the stabilizer is added.
Compared with the prior art, the invention has the beneficial effects that:
the preparation method of the invention is simple, the prepared poly-p-phenylene terephthamide whisker mainly has rod-shaped straight chain molecule poly-p-phenylene terephthamide parallel aggregation formed micro-nano short fiber, the mechanical strength of the short fiber is equal to the strength generated by adjacent interatomic force, so that the short fiber has the highest theoretical mechanical strength, in addition, as is known, the aromatic polyamide has excellent acid and alkali resistance, and after the aromatic polyamide is used as the nano whisker, the whisker has improved performance, and is more suitable for being used as a reinforcing material and widely applied to the field of composite materials.
Drawings
FIG. 1 is a schematic flow diagram of a method of making one embodiment of the present invention;
FIG. 2 is a transmission electron microscope image of poly-p-phenylene terephthalamide nanowhiskers prepared in example 1 of the present invention;
FIG. 3 is a transmission electron microscope image of poly-p-phenylene terephthalamide nanowhiskers prepared in example 2 of the present invention;
FIG. 4 is a transmission electron microscope image of poly-p-phenylene terephthalamide nanowhiskers prepared in example 3 of the present invention;
FIG. 5 is a transmission electron micrograph of poly (p-phenylene terephthalamide) nanowhiskers prepared according to example 4 of the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be described clearly and completely with reference to the accompanying drawings in 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 obtained by a person skilled in the art without making any inventive step are within the scope of the present invention.
A process for preparing aromatic polyamide whisker includes in-situ polycondensation of two reactive monomers in polymer solution to obtain nano-class aromatic polyamide, adding stabilizer, diluting with the solvent of said polymer solution, and separating.
The first reaction monomer of the two reaction monomers is aromatic diamine, and the second reaction monomer is aromatic diacid or acyl halide thereof. The first reaction monomer is p-phenylenediamine. The second reaction monomer is terephthaloyl chloride or terephthalic acid. The polymer solution is formed by dissolving a polymer in an organic solvent.
The polymer can be one or more of polysulfone, polyethersulfone, polyethylene and polyvinylidene chloride. The organic solvent is one or more than two of N, N-dimethylacetamide, dimethyl sulfoxide and N-methylpyrrolidone. The polymer is dissolved in the organic solvent to form a polymer solution with the mass percentage concentration of 15-20%.
The stabilizer comprises at least one of span, tween, coco glucoside and lauryl glucoside.
In a further preferred embodiment, a stabilizer is added to the polymer solution, and then two reaction monomers are added to carry out in-situ polycondensation reaction.
Referring to fig. 1, the specific preparation process is as follows:
step 1, preparing a polymer solution: adding a polymer formed by mixing one or more than two of polysulfone, polyether sulfone, polyethylene and polyvinylidene chloride into an organic solvent to prepare a polymer solution with the mass percentage concentration of the polymer of 15-20%. The organic solvent is one or more than two of N, N-dimethylacetamide, dimethyl sulfoxide and N-methylpyrrolidone.
Step 3, adding a first reaction monomer: adding a first reaction monomer p-phenylenediamine into the polymer solution at normal temperature, and stirring to obtain a sufficient solution.
And 5, adding a second reaction monomer: and gradually adding the second reaction monomer into the system under the stirring condition to carry out polycondensation reaction. The second reaction monomer is terephthaloyl chloride or terephthalic acid. And adjusting the reaction time and the addition amount of the second reaction monomer to ensure that the mass percentage concentration of the generated aromatic polyamide nanowhiskers in the system is 4-18%. The generated aromatic polyamide nano whisker is poly-p-phenylene terephthamide nano whisker.
Step 6, adding a stabilizer: adding a stabilizer into the system, wherein the stabilizer can be one or a mixture of more than two of span, tween, coco glucoside and lauryl glucoside, and the mass percentage concentration of the stabilizer in the system is controlled to be 1-5%.
And 7, diluting: the organic solution was added to the system.
And 8, separation: filtering or suction filtering to obtain the aromatic polyamide whisker.
And 9, drying. And drying the separated aromatic polyamide whisker to obtain the finished aromatic polyamide whisker product.
Example 1
Preparing 100 parts of N, N-dimethylacetamide solution with polysulfone content of 10% by mass, and then adding p-phenylenediamine to dissolve the solution at room temperature, wherein the mass percentage concentration of the p-phenylenediamine is 1.82%. After complete dissolution, a small amount of terephthaloyl chloride with the mass concentration of 3.42 percent is added for a plurality of times, and the mixture is fully stirred to react for 30 minutes to generate the poly-p-phenylene terephthamide nano whisker with the mass percentage concentration of 4 percent. Adding Tween with the mass percentage concentration of 1% into the solution, and continuing stirring for 20 minutes. Then diluted with N, N-dimethylacetamide in an amount of about 15 times the volume of the system. The poly-p-phenylene terephthamide nano crystal whisker is obtained by suction filtration, separation and drying.
Experiments show that the length-diameter ratio of the prepared poly-p-phenylene terephthamide nano whisker is about 15 times, the tail end of the nano whisker is forked, and the poly-p-phenylene terephthamide nano whisker is not prepared by the existing method.
Example 2
Preparing 100 parts of an N, N-dimethylacetamide solution with the polysulfone mass percentage concentration of 20%, and then adding 1.82% by mass of p-phenylenediamine at room temperature and dissolving. After complete dissolution, a small amount of terephthaloyl chloride with the mass percentage concentration of 3.42 percent is added for a plurality of times, and the mixture is fully stirred to react for 30 minutes to generate the poly-p-phenylene terephthamide nano whisker with the mass percentage concentration of 4 percent. Adding a stabilizing agent Tween with the mass percentage concentration of 2% into the solution, and continuing to stir for 20 minutes. Then diluting with N, N-dimethylacetamide, wherein the dosage of the N, N-dimethylacetamide is 10 times of the volume of the system. The poly-p-phenylene terephthamide nano crystal whisker is obtained by suction filtration, separation and drying.
Experiments show that the length-diameter ratio of the prepared poly-p-phenylene terephthamide nano whisker is about 20 times, and the tail end of the nano whisker is forked.
Example 3
Preparing 100 parts of an N, N-dimethylacetamide solution with the mass percentage concentration of 20% of polyethersulfone, adding 5.45% of p-phenylenediamine at room temperature, and uniformly dissolving. After complete dissolution, a small amount of terephthaloyl chloride with the mass percentage concentration of 10.24 percent is added for a plurality of times, and the mixture is fully stirred and reacts for 30 minutes to generate the poly-p-phenylene terephthamide nano whisker with the mass percentage concentration of 12 percent. Then, lauryl glucoside, a stabilizer at a concentration of 5% by mass, was added to the above solution, and stirring was continued for 20 minutes. Then diluting the system to 20 times by using N, N-dimethylacetamide, and obtaining the poly-p-phenylene terephthamide nano whisker by suction filtration separation and drying.
Experiments show that the length-diameter ratio of the prepared poly-p-phenylene terephthamide nano whisker is about 10 times, and the tail end of the nano whisker is forked.
Example 4
Preparing a dimethyl sulfoxide solution with the mass percentage concentration of polysulfone of 16%, then adding p-phenylenediamine with the mass percentage of 7.26% at room temperature and completely dissolving, then adding p-phthaloyl chloride with the mass percentage of 13.65% a little for a plurality of times, fully stirring and reacting for 30 minutes to generate poly (p-phenylene terephthalamide) whiskers with the mass percentage concentration of 16%. Adding 4% Tween into the solution, and stirring for 20 min. Then diluted by dimethyl sulfoxide, and the dosage of the dimethyl sulfoxide is 20 times of the volume of the system. Finally, obtaining the poly-p-phenylene terephthamide nano crystal whisker by suction filtration separation and drying.
Experiments show that the length-diameter ratio of the prepared poly-p-phenylene terephthamide nano whisker is about 10 times, and the tail end of the nano whisker is forked.
Example 5
Preparing an N-methyl pyrrolidone solution with the polyethylene mass percentage concentration of 10%, then adding p-phenylenediamine with the mass percentage concentration of 8.17% at room temperature and completely dissolving, then adding a small amount of p-phthaloyl chloride with the mass percentage of 15.35% for many times, fully stirring and reacting for 30 minutes to generate a poly (p-phenylene terephthalamide) nano whisker suspension with the mass percentage concentration of 18%. And adding 5% by mass of span serving as a stabilizer into the solution, and continuing stirring for 20 minutes. Then diluting the system by 10 times by using N-methylpyrrolidone, filtering, separating and drying to obtain the poly-p-phenylene terephthamide nano whisker.
Experiments show that the length-diameter ratio of the prepared polyamide nanowhisker is 5 times, and the tail end of the polyamide nanowhisker is forked.
Example 6
Preparing 100 parts of an N, N-dimethylacetamide solution with the mass percentage concentration of 15% of polyethersulfone, adding 3.63% of p-phenylenediamine at room temperature, uniformly dissolving, then adding 6.82% of terephthaloyl chloride in a small amount for multiple times, fully stirring, and reacting for 30 minutes to generate the poly (p-phenylene terephthalamide) nanowhisker with the mass percentage concentration of 8%. Then, cocoglucoside, a stabilizer, was added to the above solution at a mass fraction of 2%, and stirring was continued for 20 minutes. The system was then diluted 10-fold with N, N-dimethylacetamide. The poly-p-phenylene terephthamide nano crystal whisker is obtained by suction filtration, separation and drying.
Experiments show that the length-diameter ratio of the prepared polyamide nanowhisker is 15 times, and the tail end of the polyamide nanowhisker is forked.
Example 7
Preparing a polysulfone/N-methylpyrrolidone solution with the mass fraction of 20%, then adding p-phenylenediamine with the mass fraction of 5.45% at room temperature, uniformly dissolving, then adding p-phthaloyl chloride with the mass fraction of 10.24% in a small amount of times, fully stirring, and reacting for 30 minutes to generate a poly (p-phenylene terephthalamide) nano whisker suspension with the mass percentage concentration of 12%. Cococoglucoside, a stabilizer, was added to the solution at a concentration of 3% by weight, and stirring was continued for 20 minutes. The above system was then diluted 15-fold with N, N-dimethylacetamide. The poly-p-phenylene terephthamide nano crystal whisker is obtained by suction filtration, separation and drying.
Experiments show that the length-diameter ratio of the prepared poly-p-phenylene terephthamide nano whisker is 10 times, and the tail end of the nano whisker is forked.
Example 8
Preparing an N, N-dimethylacetamide solution with the mass percentage concentration of polyvinylidene fluoride of 10%, then adding p-phenylenediamine with the mass percentage concentration of 7.26% at room temperature for dissolution, then adding p-phthaloyl chloride with the mass percentage concentration of 13.65% a little by a plurality of times, fully stirring for reaction for 30 minutes, and then generating poly (p-phenylene terephthalamide) nano whisker suspension with the mass percentage concentration of 16%. Then, lauryl glucoside, a stabilizer with the mass percentage concentration of 4%, is added into the solution, and the stirring is continued for 20 minutes. The system was then diluted 10-fold with N, N-dimethylacetamide. The poly-p-phenylene terephthamide nano crystal whisker is obtained by suction filtration, separation and drying.
Experiments show that the length-diameter ratio of the prepared poly-p-phenylene terephthamide nano whisker is 10 times, and the tail end of the nano whisker is forked.
Example 9
Preparing an N, N-dimethylacetamide solution with the polysulfone mass percentage concentration of 10%, then adding p-phenylenediamine with the mass percentage concentration of 7.26% at room temperature for dissolution, then adding terephthalic acid with the mass percentage concentration of 13.65% a small number of times, fully stirring for reaction for 30 minutes, and then generating poly (p-phenylene terephthalamide) nanowhisker suspension with the mass percentage concentration of 16%. Then, lauryl glucoside, a stabilizer with the mass percentage concentration of 4%, is added into the solution, and the stirring is continued for 20 minutes. The system was then diluted 10-fold with N, N-dimethylacetamide. The poly-p-phenylene terephthamide nano crystal whisker is obtained by suction filtration, separation and drying.
Experiments show that the length-diameter ratio of the prepared poly-p-phenylene terephthamide nano whisker is 10 times, and the tail end of the nano whisker is forked.
Example 10
Preparing an N, N-dimethylacetamide solution with the mass percentage concentration of polyvinylidene fluoride of 15%, then adding p-phenylenediamine with the mass percentage concentration of 3.63% at room temperature for dissolution, then adding terephthalic acid with the mass percentage concentration of 6.82% a little by many times, fully stirring for reaction for 30 minutes, and then generating poly (p-phenylene terephthalamide) nanowhisker suspension with the mass percentage concentration of 8%. Then adding the stabilizer span with the mass percentage concentration of 4% into the solution, and continuing stirring for 20 minutes. The system was then diluted 10-fold with N, N-dimethylacetamide. The poly-p-phenylene terephthamide nano crystal whisker is obtained by suction filtration, separation and drying.
Experiments show that the length-diameter ratio of the prepared poly-p-phenylene terephthamide nano whisker is 15 times, and the tail end of the nano whisker is forked.
Example 11
Preparing an N, N-dimethylacetamide solution with the mass percentage concentration of polyether sulfone of 20%, then adding p-phenylenediamine with the mass percentage concentration of 8.17% at room temperature for dissolution, then adding terephthalic acid with the mass percentage concentration of 15.35% a little by a plurality of times, fully stirring for reaction for 30 minutes, and then generating poly (p-phenylene terephthalamide) nanowhisker suspension with the mass percentage concentration of 18%. Then adding the stabilizing agent Tween with the mass percentage concentration of 5% into the solution, and continuing stirring for 20 minutes. The system was then diluted 10-fold with N, N-dimethylacetamide. The poly-p-phenylene terephthamide nano crystal whisker is obtained by suction filtration, separation and drying.
Experiments show that the length-diameter ratio of the prepared poly-p-phenylene terephthamide nano whisker is about 10 times, and the tail end of the nano whisker is forked.
Example 12
Preparing an N, N-dimethylacetamide solution with the polyethylene mass percentage concentration of 15%, then adding p-phenylenediamine with the mass percentage concentration of 7.26% at room temperature for dissolution, then adding terephthalic acid with the mass percentage concentration of 13.65% a little by many times, fully stirring for reaction for 30 minutes, and then generating poly (p-phenylene terephthalamide) nanowhisker suspension with the mass percentage concentration of 16%. Then, cocoglucoside, a stabilizer, was added to the above solution at a concentration of 5% by mass, and stirring was continued for 20 minutes. The system was then diluted 10-fold with N, N-dimethylacetamide. The poly-p-phenylene terephthamide nano crystal whisker is obtained by suction filtration, separation and drying.
Experiments show that the length-diameter ratio of the prepared poly-p-phenylene terephthamide nano whisker is about 10 times, and the tail end of the nano whisker is forked.
The above description is only for the preferred embodiment of the present invention, but the present invention should not be limited to the embodiment and the disclosure of the drawings, and therefore, all equivalent or modifications that do not depart from the spirit of the present invention are intended to fall within the scope of the present invention.
Claims (10)
1. A preparation method of aromatic polyamide whisker is characterized in that: aromatic diamine is used as a first reaction monomer, aromatic diacid or acyl halide thereof is used as a second reaction monomer, the first reaction monomer and the second reaction monomer carry out polycondensation reaction in a polymer solution, nano aromatic polyamide is generated in situ after polycondensation, a stabilizer is added, then a solvent of the polymer solution is used for dilution, and the aromatic polyamide whisker is obtained after separation.
2. The method of producing the aromatic polyamide whisker according to claim 1, characterized in that: the aromatic diamine is p-phenylenediamine.
3. The method of producing the aromatic polyamide whisker according to claim 1, characterized in that: the aromatic diacid or the acyl halide thereof comprises one or two of terephthaloyl chloride and terephthalic acid.
4. The method of producing the aromatic polyamide whisker according to claim 1, characterized in that: the polymer solution comprises one or more than two of polysulfone solution, polyether sulfone solution, polyethylene solution and polyvinylidene fluoride solution.
5. The method of producing the aromatic polyamide whisker according to claim 1, characterized in that: the solvent of the polymer solution is an organic solvent, and the organic solvent comprises at least one of N, N-dimethylacetamide, dimethyl sulfoxide and N-methylpyrrolidone.
6. The method of producing the aromatic polyamide whisker according to claim 1, characterized in that: the mass percentage concentration of the polymer in the polymer solution is 10-20%.
7. The method of producing the aromatic polyamide whisker according to claim 1, characterized in that: the mass percentage concentration of the aromatic polyamide generated in the polycondensation reaction is 4 to 18 percent.
8. The method of producing the aromatic polyamide whisker according to claim 1, characterized in that: the addition amount of the stabilizer is 1-5% by mass percentage concentration, and the type of the stabilizer comprises at least one of span, tween and coco glucoside.
9. The method of producing the aromatic polyamide whisker according to claim 1, characterized in that: and adding the first reaction monomer into the polymer solution, dissolving completely, and then gradually adding the second reaction monomer under stirring to perform polycondensation reaction.
10. The method of producing the aromatic polyamide whisker according to claim 9, characterized in that: and adding a first reaction monomer, adding a second reaction monomer and then adding a stabilizer into the polymer solution.
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4511623A (en) * | 1982-08-30 | 1985-04-16 | Korea Advanced Institute of Science and Technology, 200-43 | Highly oriented aromatic polyamide short fiber |
US4673724A (en) * | 1984-12-07 | 1987-06-16 | Toyo Boseki Kabushiki Kaisha | Polymeric whisker and production of the same |
JP2009256415A (en) * | 2008-04-14 | 2009-11-05 | Toray Ind Inc | Nano whisker and resin composition |
US20180155853A1 (en) * | 2015-09-25 | 2018-06-07 | Tsinghua University | Preparation method of para-aramid nanofibers |
WO2019225848A1 (en) * | 2018-05-21 | 2019-11-28 | 한국화학연구원 | Method for preparing aramid nanofiber dispersion |
-
2020
- 2020-06-05 CN CN202010504777.7A patent/CN111574708A/en not_active Withdrawn
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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US4511623A (en) * | 1982-08-30 | 1985-04-16 | Korea Advanced Institute of Science and Technology, 200-43 | Highly oriented aromatic polyamide short fiber |
US4673724A (en) * | 1984-12-07 | 1987-06-16 | Toyo Boseki Kabushiki Kaisha | Polymeric whisker and production of the same |
JP2009256415A (en) * | 2008-04-14 | 2009-11-05 | Toray Ind Inc | Nano whisker and resin composition |
US20180155853A1 (en) * | 2015-09-25 | 2018-06-07 | Tsinghua University | Preparation method of para-aramid nanofibers |
WO2019225848A1 (en) * | 2018-05-21 | 2019-11-28 | 한국화학연구원 | Method for preparing aramid nanofiber dispersion |
Non-Patent Citations (1)
Title |
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石强: "PPTA/PSF原位共混膜及其聚胺复合膜的设计与构建", 《中国优秀博硕士学位论文全文数据库(博士)工程科技I辑》 * |
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