CN110903477A - Mixed diamine modified long carbon chain nylon and preparation method thereof - Google Patents
Mixed diamine modified long carbon chain nylon and preparation method thereof Download PDFInfo
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- CN110903477A CN110903477A CN201911329942.3A CN201911329942A CN110903477A CN 110903477 A CN110903477 A CN 110903477A CN 201911329942 A CN201911329942 A CN 201911329942A CN 110903477 A CN110903477 A CN 110903477A
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- Prior art keywords
- carbon chain
- chain nylon
- long carbon
- diamine
- modified long
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- Pending
Links
- 229920001778 nylon Polymers 0.000 title claims abstract description 48
- 239000004677 Nylon Substances 0.000 title claims abstract description 47
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 150000004985 diamines Chemical class 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000012266 salt solution Substances 0.000 claims abstract description 15
- -1 aryl diamine Chemical class 0.000 claims abstract description 12
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000004327 boric acid Substances 0.000 claims abstract description 8
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 4
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 3
- 230000018044 dehydration Effects 0.000 claims abstract 3
- 230000003197 catalytic effect Effects 0.000 claims abstract 2
- 238000001035 drying Methods 0.000 claims abstract 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical group C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims 1
- 239000003431 cross linking reagent Substances 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 239000012153 distilled water Substances 0.000 abstract description 7
- 239000000463 material Substances 0.000 abstract description 4
- 239000000243 solution Substances 0.000 abstract description 4
- 230000008901 benefit Effects 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 238000011056 performance test Methods 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 238000011031 large-scale manufacturing process Methods 0.000 abstract description 2
- 239000002861 polymer material Substances 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000007599 discharging Methods 0.000 description 7
- 238000005452 bending Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- 239000004952 Polyamide Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- MXAOILAHPVJWBS-UHFFFAOYSA-N 10-(azepan-1-yl)-10-oxodecanamide Chemical compound NC(=O)CCCCCCCCC(=O)N1CCCCCC1 MXAOILAHPVJWBS-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 230000001427 coherent effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- 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
- C08G69/265—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from at least two different diamines or at least two different dicarboxylic acids
-
- 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
- C08G69/28—Preparatory processes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
Abstract
The invention discloses mixed diamine modified long carbon chain nylon and a preparation method thereof, belonging to the technical field of high polymer materials. The method comprises the following steps: adding sebacic acid, distilled water, hexamethylene diamine and aryl diamine into a mixture until the pH value of a reaction solution is 7.0-7.5 to obtain a long-carbon-chain nylon salt solution; and then adding catalytic amount of inorganic boric acid, heating to 220-250 ℃/pressure of 1.5-2.0Mp for dehydration polymerization, relieving pressure and then drying in vacuum to obtain the mixed diamine modified long carbon chain nylon. The method has the advantages of simple operation, simple synthesis process, low cost, short production period and high efficiency, and is suitable for large-scale production. The material of the invention is superior to the existing long carbon chain nylon material through performance tests.
Description
Technical Field
The invention relates to mixed diamine modified long carbon chain nylon and a preparation method thereof, belonging to the technical field of high polymer polymerization.
Background
Long carbon chain nylon, polyamide, PA for short, is a large class of high molecular compounds containing amide groups NH CO on the main molecular chain, wherein the length of the carbon chain in the long carbon chain nylon is more than 10, and the long carbon chain nylon has a plurality of general properties of common polyamide, and also has the characteristics of small relative density, low water absorption rate, good dimensional stability, excellent chemical resistance, good electrical property, corrosion resistance, wear resistance, hard texture, fatigue resistance, low temperature resistance and the like. And the long carbon chain nylon is one of organic polymer materials with the best comprehensive performance.
In order to further improve the performance of the existing materials, the existing materials are modified by adopting mixed diamine, and the research is not sufficient.
Disclosure of Invention
In order to overcome the technical defects, the invention aims to provide the mixed diamine modified long-carbon-chain nylon and a synthesis process thereof. Sebacic acid, hexamethylene diamine and aryl diamine are used as raw materials, and the modified long-carbon-chain nylon is obtained through salifying and dehydrating. The synthesis process is simple, the production cost is low, and the obtained long carbon chain nylon has excellent performance.
A mixed diamine modified long carbon chain nylon comprises the following components: 0.95 to 0.97 equivalents of hexamethylene sebacamide polymer and 0.03 to 0.05 equivalents of sebacic acid aryl diamine mixture.
The invention relates to a preparation method of mixed diamine modified long carbon chain nylon, which comprises the following steps:
salt-forming reaction
Mixing sebacic acid, water, hexamethylenediamine and aryl diamine, and reacting at 90-98 ℃ until the pH value is 7.0-7.5 to obtain a long-carbon-chain nylon salt solution;
dehydration reaction
And (3) putting the salt solution of the long carbon chain nylon into an autoclave, heating to the temperature of 220 ℃ and 250 ℃, controlling the pressure in the autoclave to reach 1.5-2MPa, opening an evacuation valve to release pressure after the reaction is finished, reacting for 1-3 hours under micro vacuum after the pressure reaches normal pressure, and discharging.
Further, in the above technical solution, the aryl diamine is selected from the group consisting of 4,4 ' -diaminodiphenyl ether, 4 ' -diaminodiphenylmethane, and 4,4 ' -diaminobiphenyl.
Further, in the above technical solution, the water is preferably distilled water, and the addition amount is 1.5 to 2.0 equivalents of sebacic acid.
Further, in the technical scheme, the mole ratio of the sebacic acid, the hexamethylene diamine and the aryl diamine is 1:0.95-0.97: 0.03-0.05.
Further, in the above technical scheme, in the salt forming reaction, the reaction termination condition is pH 7.0-7.5. Wherein pH control is a key factor of the reaction.
Further, in the above technical scheme, the micro vacuum is 5-10 mm of water column, and the discharging needs to pass through a die.
Advantageous effects of the invention
Compared with the prior art, the modified long carbon chain nylon is obtained by reacting sebacic acid with hexamethylene diamine and aryl diamine mixed diamine to form salt and then dehydrating at high temperature and high pressure in the presence of inorganic boric acid. The operation method has the advantages of simple and convenient operation, coherent preparation, short production period, low price of raw materials, benefit improvement and suitability for large-scale production.
DETAILED DESCRIPTION OF EMBODIMENT (S) OF INVENTION
Example 1
202g (1mol) of sebacic acid, 318.5g of distilled water, 112.7g (0.97mol) of hexamethylene diamine and 6g (0.03mol) of 4, 4' -diaminodiphenyl ether are added into a reaction bottle, after the addition is finished, the reaction is carried out at 90-98 ℃ for 2 hours, then the pH is detected until the pH is 7.0-7.5, the reaction is finished, and the temperature is reduced to the room temperature, so that a salt solution of the long-carbon-chain nylon is obtained. Putting the prepared long carbon chain nylon salt solution and inorganic boric acid (1.1g) into a stainless steel autoclave, vacuumizing the system, replacing the system with nitrogen for 3 times, heating to 250 ℃ and reacting at the pressure of 1.5-2.0MPa for 10 hours, opening an exhaust valve, and releasing the pressure to the normal pressure. And keeping the temperature for 1-3 hours under micro vacuum (5-10 mm water column), and discharging through a die to obtain the mixed diamine modified long carbon chain nylon. The performance test was as follows: the melting point is 190-200 ℃; tensile strength is 55 MPa; elongation at break 178%; the bending strength is 56MPa.
Example 2
202g (1mol) of sebacic acid, 318.5g of distilled water, 110.4g (0.95mol) of hexamethylene diamine and 10g (0.05mol) of 4, 4' -diaminodiphenyl ether are added into a reaction bottle, after the addition is finished, the reaction is carried out at 90-98 ℃ for 2 hours, then the pH is detected until the pH is 7.0-7.5, the reaction is finished, and the temperature is reduced to the room temperature, so that the salt solution of the long-carbon-chain nylon is obtained. Putting the prepared long carbon chain nylon salt solution and inorganic boric acid (1.1g) into a stainless steel autoclave, vacuumizing the system, replacing the system with nitrogen for 3 times, heating to 250 ℃ and reacting at the pressure of 1.5-2.0MPa for 10 hours, opening an exhaust valve, and releasing the pressure to the normal pressure. And keeping the temperature for 1-3 hours under micro vacuum (5-10 mm water column), and discharging through a die to obtain the mixed diamine modified long carbon chain nylon. The melting point is 190-201 ℃; tensile strength is 55 MPa; elongation at break 179%; the bending strength is 55MPa.
Example 3
Adding 202g (1mol) of sebacic acid and 36g of distilled water into a reaction bottle, heating the reaction bottle in an oil bath to 90 ℃, controlling the reaction temperature to be 90-98 ℃, slowly adding 111.6g (0.97mol) of hot-melt hexamethylene diamine and 7.4g (0.04mol) of 4, 4' -diaminodiphenyl, after the addition is finished, reacting at 90-98 ℃ for 2 hours, detecting the pH until the pH is 7.0-7.5, finishing the reaction, and cooling to room temperature to obtain the salt solution of the long-carbon-chain nylon. Putting the prepared long carbon chain nylon salt solution and inorganic boric acid (1.1g) into a stainless steel autoclave, vacuumizing the system, replacing the system with nitrogen for 3 times, heating to 230 ℃ and 1.5-2.0MPa for reaction for 10 hours, opening an exhaust valve, and releasing the pressure to the normal pressure. And keeping the temperature for 1-3 hours under micro vacuum (5-10 mm water column), and discharging through a die to obtain the mixed diamine modified long carbon chain nylon. Melting point is 191-200 ℃; tensile strength is 55 MPa; elongation at break of 180%; the bending strength is 56MPa.
Example 4
202kg (1kmol) of sebacic acid, 318.5kg of distilled water, 112.7kg (0.97kmol) of hexamethylene diamine and 6kg (0.03kmol) of 4, 4' -diaminodiphenyl ether are added into a reaction kettle, after the addition is finished, the reaction is carried out at 90-98 ℃ for 2 hours, the pH is detected until the pH is 7.0-7.5, the reaction is finished, and the temperature is reduced to the room temperature, so that the salt solution of the long-carbon-chain nylon is obtained. Putting the prepared long carbon chain nylon salt solution and inorganic boric acid (110g) into a stainless steel autoclave, vacuumizing the system, replacing the system with nitrogen for 3 times, heating to the temperature of 220-250 ℃ and the pressure of 1.5-2.0MPa for reaction for 10 hours, opening an exhaust valve, and releasing the pressure to the normal pressure. And keeping the temperature for 1-3 hours under micro vacuum (5-10 mm water column), and discharging through a die to obtain the mixed diamine modified long carbon chain nylon. The melting point is 190-200 ℃; tensile strength is 55 MPa; elongation at break 179%; the bending strength is 56MPa.
Comparative example:
after 202.3g (1mol) of sebacic acid, 318.5g of distilled water and 116.2g (0.97mol) of hexamethylenediamine are added into a reaction bottle, the mixture is reacted at 90-98 ℃ for 2 hours, and then the pH is detected until the pH is 7.0-7.5, and the reaction is finished, and then the temperature is reduced to room temperature, so that a salt solution of the long-carbon-chain nylon is obtained. Putting the prepared long carbon chain nylon salt solution and inorganic boric acid (1.1g) into a stainless steel autoclave, vacuumizing the system, replacing the system with nitrogen for 3 times, heating to 250 ℃ and reacting at the pressure of 1.5-2.0MPa for 10 hours, opening an exhaust valve, and releasing the pressure to the normal pressure. And keeping the temperature for 1-3 hours under micro vacuum (5-10 mm water column), and discharging through a die to obtain the mixed diamine modified long carbon chain nylon. The performance test was as follows: melting point is 208-218 ℃; tensile strength 50.5 MPa; elongation at break 108%; the bending strength was 51MPa.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be able to cover the technical solutions and the inventive concepts of the present invention within the technical scope of the present invention.
Claims (10)
1. The mixed diamine modified long carbon chain nylon is characterized by comprising hexamethylene sebacate diamine polymer and sebacic acid aryl diamine mixture.
2. The hybrid diamine-modified long carbon chain nylon of claim 1, wherein: in the long carbon chain nylon, the mole ratio of the sebacic acid acyl hexamethylene diamine polymer to the sebacic acid aryl diamine is 0.95-0.97: 0.03-0.05.
3. A preparation method for synthesizing the mixed diamine modified long carbon chain nylon of claim 1 is characterized by comprising the following steps:
a: salt-forming reaction
Mixing sebacic acid, water, hexamethylenediamine and aryl diamine, and reacting at 90-98 ℃ until the pH value is 7.0-7.5 to obtain a long-carbon-chain nylon salt solution;
b: dehydration reaction
Adding catalytic amount of inorganic boric acid into the long carbon chain nylon salt solution, heating to 250 ℃ at 220 ℃, controlling the pressure to be 1.5-2.0Mp for dehydration polymerization, relieving the pressure, and drying in micro vacuum to obtain the long carbon chain nylon polymer.
4. The method for preparing the mixed diamine modified long carbon chain nylon according to claim 3, wherein the method comprises the following steps: in the salt forming reaction, the aryl diamine is selected from 4,4 ' -diaminodiphenyl ether, 4 ' -diaminodiphenylmethane and 4,4 ' -diaminobiphenyl.
5. The method for preparing the mixed diamine modified long carbon chain nylon according to claim 3, wherein the method comprises the following steps: in the salt-forming reaction, water is 1.5-2.0 equivalent of sebacic acid.
6. The method for preparing the mixed diamine modified long carbon chain nylon according to claim 3, wherein the method comprises the following steps: in the salt forming reaction, the molar ratio of the sebacic acid to the hexamethylene diamine to the cross-linking agent is 1:0.95-0.97: 0.03-0.05.
7. The method for preparing the mixed diamine modified long carbon chain nylon according to claim 3, wherein the method comprises the following steps: in the salt-forming reaction, the reaction termination condition is that the pH is 7.0-7.5.
8. The method for preparing the mixed diamine modified long carbon chain nylon according to claim 3, wherein the method comprises the following steps: in the dehydration reaction, the dehydration process is carried out by firstly carrying out high pressure and then carrying out pressure relief.
9. The method for preparing the mixed diamine modified long carbon chain nylon according to claim 3, wherein the method comprises the following steps: in the dehydration reaction, the micro vacuum is 5-10 mm water column.
10. The method for preparing the mixed diamine modified long carbon chain nylon according to claim 3, wherein the method comprises the following steps: in the dehydration reaction, the discharge needs to pass through a die.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911329942.3A CN110903477A (en) | 2019-12-20 | 2019-12-20 | Mixed diamine modified long carbon chain nylon and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911329942.3A CN110903477A (en) | 2019-12-20 | 2019-12-20 | Mixed diamine modified long carbon chain nylon and preparation method thereof |
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| Publication Number | Publication Date |
|---|---|
| CN110903477A true CN110903477A (en) | 2020-03-24 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911329942.3A Pending CN110903477A (en) | 2019-12-20 | 2019-12-20 | Mixed diamine modified long carbon chain nylon and preparation method thereof |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN118852609A (en) * | 2024-09-24 | 2024-10-29 | 安徽协合新材料有限公司 | A production process of water-based polyamide wax rheological additive |
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|---|---|---|---|---|
| GB1390557A (en) * | 1971-04-23 | 1975-04-16 | Bayer Ag | High molecular weight linear copolyamides |
| CN101426833A (en) * | 2006-02-16 | 2009-05-06 | 阿克马法国公司 | Copolymers comprising polyamide blocks and polyether blocks and having improved optical properties |
| CN102702510A (en) * | 2012-05-23 | 2012-10-03 | 上海臻威复合材料有限公司 | Alcohol-soluble nylon and preparation method thereof |
| CN106243347A (en) * | 2016-08-24 | 2016-12-21 | 江门市德众泰工程塑胶科技有限公司 | A kind of preparation method of environmental protection polyamide |
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| CN109880081A (en) * | 2019-02-15 | 2019-06-14 | 美瑞新材料股份有限公司 | A kind of preparation method of the polyester polyol containing polyamide segment |
-
2019
- 2019-12-20 CN CN201911329942.3A patent/CN110903477A/en active Pending
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| Title |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN118852609A (en) * | 2024-09-24 | 2024-10-29 | 安徽协合新材料有限公司 | A production process of water-based polyamide wax rheological additive |
| CN118852609B (en) * | 2024-09-24 | 2024-12-27 | 安徽协合新材料有限公司 | A production process of water-based polyamide wax rheological additive |
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