CN115558102A - Long-chain nylon elastomer and ester amide exchange preparation method - Google Patents
Long-chain nylon elastomer and ester amide exchange preparation method Download PDFInfo
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- CN115558102A CN115558102A CN202211324735.0A CN202211324735A CN115558102A CN 115558102 A CN115558102 A CN 115558102A CN 202211324735 A CN202211324735 A CN 202211324735A CN 115558102 A CN115558102 A CN 115558102A
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- 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
- C08G69/40—Polyamides containing oxygen in the form of ether groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/06—Polyamides derived from polyamines and polycarboxylic acids
Abstract
The invention discloses a long-chain nylon elastomer and an acyl ester exchange preparation method, and belongs to the technical field of material synthesis. The method comprises the following steps: putting the double-end ester group long-chain nylon hard segment and the polyetheramine into a reaction kettle, adding water, a catalyst and an antioxidant, and replacing air in a system with nitrogen; mixing and stirring for 0-2 h at 80 ℃, and then mixing and stirring for 0-2 h at 150-200 ℃; then slowly discharging the micromolecule product in the system, keeping the pressure below 1kPa and the temperature at 200-250 ℃ for reacting for 1-4 h, and finishing polymerization; and discharging, cooling in water, granulating and drying to obtain the nylon elastomer slice. The nylon elastomer of the invention improves the accuracy of the molar ratio of materials through ester-amide exchange reaction, can complete block copolymerization without salifying in advance, and has the elongation at break of over 500 percent, low processing temperature and hardness range of 40D-70D.
Description
Technical Field
The invention relates to the technical field of synthesis and preparation of high polymer materials, in particular to a long-chain nylon elastomer and an ester amide exchange preparation method.
Background
Nylon, as an engineering plastic with the largest use amount, has become a plastic variety with characteristics of multiple varieties, multiple functions, specialization, serialization and the like, and can realize the characteristics of super toughness, high strength, flame retardance, low temperature resistance, heat resistance, even rubber-like elastomers and the like. The nylon elastomer is a thermoplastic elastomer with nylon molecular chains as hard segments and polyether or polyester as soft segments.
By adjusting the molecular weight of the soft segment and the soft segment, the types of the monomers, the relative proportion and the block mode, a series of thermoplastic elastomers with different properties can be obtained. The nylon chain is folded and crystallized at normal temperature to form physical cross-linking points, and the crystal is broken at high temperature to release the cross-linking points, so that the thermoplastic processing can be carried out. The type of hard segment determines the final mechanical properties of the elastomer, such as strength, modulus, etc., as well as the physical properties of melting point, hardness, density, chemical stability, etc. The type of soft segment determines the low temperature resistance, hydrophilicity, etc. of the elastomer.
The conventional polyether ester type nylon elastomer occupies a mainstream market, is almost monopolized by foreign enterprises such as Acoma, yinhua and Yushu, has high market price, mostly takes PA11 or PA12 as a hard segment, and has complex synthesis process and more working procedures. In the polymerization process of the polyether ester nylon elastomer, the polymerization constants of polyester and polyamide are different, and the synthesis of a polyamide hard segment can be completed firstly during copolymerization by controlling the process, and then polyether ester soft segments and the polyamide hard segments are subjected to alternate copolymerization, so that the nylon elastomer with good performance is obtained. However, the process is complex in process control, high in operation difficulty, and dangerous because raw materials need to be supplemented midway.
At present, a lot of researches on nylon elastomers exist, but most of China only has a few products on short-chain nylon elastomers, the hardness is higher, and elastomers with low hardness and good low-temperature resistance in practical application dominate. Secondly, most elastomer polymerization processes need to be carried out in multiple steps, even feeding materials in the middle of high-temperature reaction, and the process is complex. The breakthrough of nylon elastomer polymerization mode is needed, thereby breaking monopoly and occupying market.
Disclosure of Invention
In order to solve the problems in the prior art, the invention discloses a long-chain nylon elastomer and an ester-amide exchange preparation method, which realize the alternate block copolymerization of the long-chain nylon elastomer to obtain a nylon elastomer material with good performance, large elongation at break and low processing temperature, and the hardness is between 40D and 70D.
In order to solve the technical problems, the invention provides the following technical scheme:
on one hand, the invention provides an acyl ester exchange preparation method of a long-chain nylon elastomer, which comprises the steps of preparing a double-end ester group long-chain nylon hard segment with low molecular weight through pre-polymerization end capping, and then carrying out block copolymerization on the nylon hard segment and a polyether amine soft segment through an ester amide exchange method to prepare the long-chain nylon elastomer with good performance. Specifically, the feed is prepared from the following raw materials in parts by weight:
the molar ratio of the double-end ester group long-chain nylon hard segment to the polyether amine is 1:1;
the method specifically comprises the following steps:
putting the double-end ester group long-chain nylon hard segment and the polyetheramine into a reaction kettle, adding water, a catalyst and an antioxidant, and replacing air in a system with nitrogen; mixing and stirring for 0-2 h at 80 ℃, and then mixing and stirring for 0-2 h at 150-200 ℃; then slowly discharging the micromolecule product in the system, keeping the pressure below 1kPa and the temperature at 200-250 ℃ for reacting for 1-4 h, and finishing polymerization; and discharging, cooling in water, granulating and drying to obtain the nylon elastomer slice.
Further, the hard segment structural formula of the double-end ester group long-chain nylon is as follows:
wherein the R' group is C0-C8 alkyl, R 1 Is methyl or ethyl; x is 10 to 13, y is 8 to 11, and n is 2 to 8.
Further, the hard segment of the double-end ester-group long-chain nylon is prepared by the following method:
weighing 30 to 50 weight parts of chain diacid, 42 to 50 weight parts of long-chain diamine, 5 to 25 weight parts of end-capping reagent, 0.1 to 0.5 weight part of second catalyst and 0 to 20 weight parts of water; adding long-chain dibasic acid, long-chain diamine and a blocking agent into a reaction kettle, adding water and a second catalyst, and uniformly mixing; heating to 150-200 ℃, maintaining the pressure for reaction for 2 hours, and then releasing the pressure to obtain the double-end ester group long-chain nylon.
Preferably, the long-chain dibasic acid is selected from sebacic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid; the long-chain diamine is selected from decamethylene diamine, undecane diamine, dodecane diamine and tridecane diamine;
the structural formula of the end capping agent is as follows:
wherein the R' group is C0-C8 alkyl, R 1 Is methyl or ethyl.
Preferably, the second catalyst is one or more of sodium hypophosphite, pyrophosphoric acid and phosphoric acid.
Further, the polyetheramine has the following structural formula:
wherein R is 1 The radical being methyl or ethyl, R 2 The radical is hydrogen or methyl, the radical R is methylene, ethyl, propyl or butyl, and the sum of x, y and z is 33-41.
Preferably, the catalyst is one or more of sodium hypophosphite, pyrophosphoric acid and phosphoric acid;
the antioxidant is a compound system of an antioxidant 1010 and an antioxidant 1098; the weight ratio of the antioxidant 1010 to the antioxidant 1098 is 1.
On the other hand, the invention also provides a long-chain nylon elastomer which is prepared by the acyl ester exchange preparation method of the long-chain nylon elastomer and is used for plastics, antistatic agents and elastic fibers. The elastomer of 40D-55D can be used as skis, snow boots, flexible injection molding parts, silent gears, TPU processing aids and antistatic agents, and the elastomer of 55D-70D can be used as nylon 6, nylon 66 encapsulating materials, explosion-resistant hoses, flexible films, high-grade door and window sealing materials and the like.
Compared with the prior art, the invention has the following beneficial effects:
1) The invention synthesizes the low molecular nylon hard segment in advance, protects the end group by ester group, ensures that the functional group is not damaged by high temperature, and can carry out regular block copolymerization;
2) The end capping agent adopted by the invention has the same chain structure as nylon, and the final characteristics cannot be influenced;
3) The nylon elastomer prepared by the method provided by the invention almost has no terminal carboxyl, does not generate ionized acid under a long-time humid condition, and has better hydrolysis resistance.
The invention utilizes the native advantages of biological fermentation of long-chain diamine and long-chain diacid monomers, and takes the monomers as the elastomer hard segment to prepare the long nylon elastomer, and has the characteristics of wide raw material source, good low-temperature impact property, excellent processing performance and the like.
Detailed Description
In order to make the technical problems, technical solutions and advantages to be solved by the present invention clearer, the following detailed description is given with reference to specific embodiments.
In the present invention, the materials and reagents used are not specifically described, and are commercially available.
The invention provides a long-chain nylon elastomer and an ester-amide exchange preparation method, and specific embodiments are as follows.
Example 1
A method for preparing long-chain nylon elastomer by ester-amide exchange comprises the following steps:
adding 50 parts of dodecanediamine, 30 parts of sebacic acid, 20 parts of an end-capping reagent, 0.25 part of phosphoric acid and 20 parts of water into a reaction kettle, replacing air in the system with nitrogen, heating to 200 ℃, keeping the temperature and stirring for 2 hours, releasing pressure, and discharging to obtain the double-end ester group long-chain nylon hard segment, wherein the number of the repeating units is 2.
The structural formula of the blocking agent is as follows:
adding 37.5 parts of nylon hard segment and 62.5 parts of polyether amine soft segment into a reaction kettle, and adding 10 parts of water, 0.3 part of sodium hypophosphite, 0.25 part of antioxidant 1010 and 0.25 part of antioxidant 1098. After replacing the air in the system with nitrogen, heating to 80 ℃ and uniformly mixing all the materials. Heating to 180 ℃ within 2h, and gradually releasing small molecules such as water vapor and ethanol. Keeping the vacuum degree of the system below 1kPa, reacting for 2h at the temperature of 220 ℃, then filling nitrogen into the system, discharging from a lower discharging port and cooling to obtain the long-chain nylon elastomer 1.
The structure of the polyether amine is as follows:
wherein R is 1 The radical being methyl, R 2 The radical is hydrogen, the sum of x, y is 33, z is 0.
Example 2
A method for preparing long-chain nylon elastomer by ester amide exchange comprises the following steps:
adding 45 parts of decamethylenediamine, 42 parts of sebacic acid, 13 parts of end-capping reagent, 0.5 part of phosphoric acid and 10 parts of water into a reaction kettle, replacing air in the system with nitrogen, heating to 200 ℃, keeping the temperature and stirring for 2 hours, releasing pressure, and discharging to obtain the double-end ester group long-chain nylon hard segment, wherein the number of the repeating units is 4.
Adding 49 parts of nylon hard segment and 51 parts of polyether amine soft segment into a reaction kettle, and adding 20 parts of water, 0.5 part of sodium hypophosphite, 0.5 part of antioxidant 1010 and 0.25 part of antioxidant 1098. After replacing the air in the system with nitrogen, heating to 80 ℃ and uniformly mixing all the materials. Heating to 180 ℃ within 2h, and gradually releasing small molecules such as water vapor and ethanol. Keeping the vacuum degree of the system below 1kPa, reacting for 2h at 220 ℃, then filling nitrogen into the system, discharging from a lower discharging port and cooling to obtain the long-chain nylon elastomer 2.
The end-capping reagent and polyetheramine are as in example 1.
Example 3
A method for preparing long-chain nylon elastomer by ester-amide exchange comprises the following steps:
adding 42 parts of decamethylenediamine, 48 parts of dodecanedioic acid, 10 parts of end-capping reagent, 0.3 part of phosphoric acid and 15 parts of water into a reaction kettle, replacing air in the system with nitrogen, heating to 200 ℃, keeping the temperature and stirring for 2 hours, releasing pressure, and discharging to obtain the double-end ester group long-chain nylon hard segment, wherein the number of the repeating units is 5.
Adding 55 parts of nylon hard segment and 45 parts of polyether amine soft segment into a reaction kettle, and adding 10 parts of water, 0.3 part of sodium hypophosphite, 0.5 part of antioxidant 1010 and 0.25 part of antioxidant 1098. After replacing the air in the system with nitrogen, heating to 80 ℃ and uniformly mixing all the materials. Heating to 180 ℃ within 2h, and gradually releasing small molecules such as water vapor and ethanol. Keeping the vacuum degree of the system below 1kPa, reacting for 2h at the temperature of 220 ℃, then filling nitrogen into the system, discharging from a lower discharging port and cooling to obtain the long-chain nylon elastomer 3.
The end-capping reagent and polyetheramine are as in example 1.
Example 4
A method for preparing long-chain nylon elastomer by ester amide exchange comprises the following steps:
adding 49 parts of dodecanediamine, 41 parts of sebacic acid, 10 parts of an end-capping agent, 0.25 part of phosphoric acid and 20 parts of water into a reaction kettle, replacing air in the system with nitrogen, heating to 200 ℃, keeping the temperature and stirring for 2 hours, releasing pressure, and discharging to obtain the double-end ester group long-chain nylon hard segment, wherein the number of the repeating units is 5.
The structural formula of the blocking agent is as follows:
adding 62 parts of nylon hard segment and 38 parts of polyetheramine soft segment into a reaction kettle, and adding 10 parts of water, 0.3 part of sodium hypophosphite, 0.2 part of antioxidant 1010 and 0.4 part of antioxidant 1098. After replacing the air in the system with nitrogen, heating to 80 ℃ and uniformly mixing all the materials. Heating to 180 ℃ within 2h, and gradually releasing small molecules such as water vapor and ethanol. Keeping the vacuum degree of the system below 1kPa, reacting for 2h at the temperature of 220 ℃, then filling nitrogen into the system, discharging from a lower discharging port and cooling to obtain the long-chain nylon elastomer 4.
The structure of the polyether amine is as follows:
wherein R is 1 The radical being methyl, R 2 The radical is hydrogen, the R radical is methylene, the sum of x and y is 6, z is 35.
Example 5
A method for preparing long-chain nylon elastomer by ester-amide exchange comprises the following steps:
adding 48 parts of dodecanediamine, 45.5 parts of undecanedioic acid, 6.5 parts of end-capping reagent, 0.25 part of phosphoric acid and 20 parts of water into a reaction kettle, replacing air in the system with nitrogen, heating to 200 ℃, keeping the temperature, stirring for 2 hours, discharging after pressure release to obtain the double-end ester group long-chain nylon hard segment, wherein the number of the repeating units is 7.
Adding 69 parts of nylon hard segment and 31 parts of polyether amine soft segment into a reaction kettle, and adding 10 parts of water, 0.3 part of sodium hypophosphite, 0.3 part of antioxidant 1010 and 0.2 part of antioxidant 1098. After replacing the air in the system with nitrogen, heating to 80 ℃ and uniformly mixing all the materials. Heating to 180 ℃ within 2h, and gradually releasing small molecules such as water vapor and ethanol. Keeping the vacuum degree of the system below 1kPa, reacting for 2h at 220 ℃, then filling nitrogen into the system, discharging from a lower discharging port and cooling to obtain the long-chain nylon elastomer 5.
The end-capping reagent and polyetheramine are as in example 4.
Example 6
A method for preparing long-chain nylon elastomer by ester-amide exchange comprises the following steps:
adding 45 parts of dodecanediamine, 50 parts of sebacic acid, 5 parts of an end-capping reagent, 0.25 part of phosphoric acid and 20 parts of water into a reaction kettle, replacing air in the system with nitrogen, heating to 200 ℃, keeping the temperature and stirring for 2 hours, releasing pressure, and discharging to obtain the double-end ester group long-chain nylon hard segment, wherein the number of the repeating units is 9.
Adding 75 parts of nylon hard segment and 25 parts of polyetheramine soft segment into a reaction kettle, and adding 10 parts of water, 0.3 part of sodium hypophosphite, 0.2 part of antioxidant 1010 and 0.3 part of antioxidant 1098. After replacing the air in the system with nitrogen, heating to 80 ℃ and uniformly mixing all the materials. Heating to 180 ℃ within 2h, and gradually releasing small molecules such as water vapor and ethanol. Keeping the vacuum degree of the system below 1kPa, reacting for 2h at the temperature of 220 ℃, then filling nitrogen into the system, discharging from a lower discharging port and cooling to obtain the long-chain nylon elastomer 6.
The end-capping reagent and polyetheramine are as in example 4.
Comparative example 1
Adding 36 parts of hexamethylenediamine, 53 parts of dodecanedioic acid, 10 parts of an end-capping agent, 0.3 part of phosphoric acid and 15 parts of water into a reaction kettle to prepare the long-chain nylon hard segment.
Adding 56 parts of nylon hard segment and 44 parts of polyether amine soft segment into a reaction kettle, and adding 10 parts of water, 0.3 part of sodium hypophosphite, 0.5 part of antioxidant 1010 and 0.25 part of antioxidant 1098. The remaining conditions were the same as in example 3, and this was designated as elastomer D1.
Comparative example 2
Adding 56 parts of dodecanediamine, 34 parts of adipic acid, 10 parts of an end capping agent, 0.3 part of phosphoric acid and 15 parts of water into a reaction kettle to prepare the long-chain nylon hard segment.
Adding 59 parts of nylon hard segment and 41 parts of polyether amine soft segment into a reaction kettle, and adding 10 parts of water, 0.3 part of sodium hypophosphite, 0.5 part of antioxidant 1010 and 0.25 part of antioxidant 1098. The remaining conditions were the same as in example 3 and the elastomer D2 was used.
The elastomers prepared in the examples and comparative examples of the present invention were subjected to performance tests, specifically:
tensile property: referring to the measurement of the tensile property of the GB/T1040.1-2018 plastics, the test is carried out on 1BA type sample bars at the speed of 50mm/min, at least 5 sample bars are tested, and the results are averaged.
Hardness: according to the standard of measuring the indentation hardness (Shore hardness) by using a hardness tester according to GB/T2411-2008 plastic and hard rubber, the Shore hardness D/1s of a wafer sample with the thickness of 6mm is measured, at least five points are taken for testing, and the results are averaged.
The results of the performance tests on the long chain nylon elastomers prepared in examples 1-6 are shown in Table 1. The results of the performance tests on the elastomers prepared in comparative examples 1-2 are shown in Table 2.
TABLE 1
| Numbering | Hardness D | Elongation at break% |
| Long chain Nylon elastomer 1 | 40 | 600 |
| Long chain Nylon elastomer 2 | 50 | 600 |
| Long chain Nylon elastomer 3 | 55 | 600 |
| Long chain nylon elastomer 4 | 60 | 500 |
| Long chain Nylon elastomer 5 | 65 | 500 |
| Long chain Nylon elastomer 6 | 70 | 500 |
As can be seen from Table 1, the long-chain nylon elastomer prepared by the invention has larger elongation at break, and the Shore hardness of the low-hardness mark of the elasticity of the prepared long-chain nylon is 40D-70D.
The invention synthesizes the low molecular nylon hard segment in advance, protects the end group by ester group, ensures that the functional group is not damaged by high temperature, and can carry out regular block copolymerization; and the adopted end-capping reagent has the same chain structure as nylon, so that the final performance is not influenced.
TABLE 2
| Numbering | Hardness D | Elongation at break% |
| Elastomer D1 | 55 | 250 |
| Elastomer D2 | 58 | 250 |
As can be seen from Table 2, the elongation at break is significantly higher and the hardness is not much different in the present invention than in the comparative examples, compared to the elastomers prepared with different diamines (comparative example 1) and diacids (comparative example 2).
In conclusion, the nylon elastomer improves the accuracy of the molar ratio of materials through ester-amide exchange reaction, can complete block copolymerization without salifying in advance, and can prepare a long-chain nylon elastomer material with good performance, wherein the elongation at break of the prepared elastomer is more than 500%, the processing temperature is low, and the hardness range is 40D-70D.
The foregoing is a preferred embodiment of the present invention, and it will be apparent to those skilled in the art that various modifications and adaptations can be made without departing from the principles of the invention and are intended to be within the scope of the invention.
Claims (9)
1. The acyl ester exchange preparation method of the long-chain nylon elastomer is characterized by comprising the following raw materials in parts by weight:
the molar ratio of the double-end ester group long-chain nylon hard segment to the polyether amine is 1:1;
the preparation method of the long-chain nylon elastomer and the acyl ester exchange comprises the following steps:
putting the double-end ester group long-chain nylon hard segment and the polyether amine into a reaction kettle, adding water, a catalyst and an antioxidant, and replacing air in a system with nitrogen; mixing and stirring for 0-2 h at 80 ℃, and then mixing and stirring for 0-2 h at 150-200 ℃; then slowly discharging the micromolecule product in the system, keeping the pressure below 1kPa and the temperature at 200-250 ℃ for reacting for 1-4 h, and finishing polymerization; and discharging, cooling in water, granulating and drying to obtain the nylon elastomer slice.
2. The method for preparing the long-chain nylon elastomer by acyl ester interchange according to claim 1, wherein the hard segment of the double-end ester-group long-chain nylon has the following structural formula:
wherein the R' group is C0-C8 alkyl, R 1 Is methyl or ethyl; x is 10-13, y is 8-11, n is 2-8.
3. An acyl ester exchange preparation method of the long-chain nylon elastomer as claimed in claim 2, characterized in that the double-end ester group long-chain nylon hard segment is prepared by the following method:
weighing 30-50 parts by weight of long-chain dicarboxylic acid, 42-50 parts by weight of long-chain diamine, 5-25 parts by weight of end capping agent, 0.1-0.5 part by weight of second catalyst and 0-20 parts by weight of water; adding long-chain dibasic acid, long-chain diamine and a blocking agent into a reaction kettle, adding water and a second catalyst, and uniformly mixing; heating to 150-200 ℃, maintaining the pressure for reaction for 2 hours, and then releasing the pressure to obtain the double-end ester group long-chain nylon.
4. The method of claim 3, wherein the long-chain dicarboxylic acid is sebacic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid; the long-chain diamine is decamethylene diamine, undecane diamine, dodecane diamine, tridecane diamine;
the structural formula of the end capping agent is as follows:
wherein the R' group is C0-C8 alkyl, R 1 Is methyl or ethyl.
5. The method for preparing long-chain nylon elastomer through acyl ester exchange according to claim 4, wherein the second catalyst is one or more of sodium hypophosphite, pyrophosphoric acid and phosphoric acid.
6. The method for preparing the long-chain nylon elastomer by acyl ester exchange as claimed in claim 2, wherein the structural formula of the polyether amine is as follows:
wherein R is 1 The radicals being methyl orEthyl radical, R 2 The radical is hydrogen or methyl, the radical R is methylene, ethyl, propyl or butyl, and the sum of x, y and z is 33-41.
7. The method for preparing the long-chain nylon elastomer through acyl ester exchange according to claim 1, wherein the catalyst is one or more of sodium hypophosphite, pyrophosphoric acid and phosphoric acid;
the antioxidant is a compound system of an antioxidant 1010 and an antioxidant 1098; the weight ratio of the antioxidant 1010 to the antioxidant 1098 is 1.
8. A long-chain nylon elastomer obtained by the process for producing a long-chain nylon elastomer according to any one of claims 1 to 7 by transesterification.
9. The long-chain nylon elastomer according to claim 8, which has a Shore hardness of 40D to 70D and is used for plastics, antistatic agents or elastic fibers.
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| CN113527668A (en) * | 2021-07-30 | 2021-10-22 | 会通新材料(上海)有限公司 | Long-chain polyamide and preparation method and application thereof |
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| CN104910377A (en) * | 2014-03-10 | 2015-09-16 | 湖南师范大学 | PA6 type polyamide thermoplastic elastomer preparation method |
| CN108299639A (en) * | 2018-02-01 | 2018-07-20 | 沧州旭阳科技有限公司 | A kind of transparent polyamide thermoplastic elastomer (TPE) and preparation method thereof |
| CN110655646A (en) * | 2019-09-16 | 2020-01-07 | 北京化工大学 | Preparation method of long carbon chain nylon elastomer |
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| CN113527668A (en) * | 2021-07-30 | 2021-10-22 | 会通新材料(上海)有限公司 | Long-chain polyamide and preparation method and application thereof |
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