CN112341619A - High-elongation meta-aramid polymer and preparation method thereof - Google Patents
High-elongation meta-aramid polymer and preparation method thereof Download PDFInfo
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- CN112341619A CN112341619A CN202011175357.5A CN202011175357A CN112341619A CN 112341619 A CN112341619 A CN 112341619A CN 202011175357 A CN202011175357 A CN 202011175357A CN 112341619 A CN112341619 A CN 112341619A
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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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- 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
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- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
- D01F6/60—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyamides
- D01F6/605—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyamides from aromatic polyamides
Abstract
The invention discloses a high-elongation meta-aramid polymer and a preparation method thereof, wherein the polymer has the following structural general formula:
Description
Technical Field
The invention belongs to the technical field of aramid fiber polymers, and particularly relates to an aramid fiber polymer and a preparation method thereof.
Background
Aromatic polyamide fibers are classified into para-type and meta-type depending on their molecular structures. The para-type product is generally applied as high-strength high-modulus fiber, and the meta-type product is mainly used as a high-temperature resistant fiber material.
The material prepared from the meta-aramid polymer has excellent characteristics, so that the material is developed and applied in various fields. The most mature development at present is the application of the fiber field, and the prepared aramid fiber is known as one of three high-performance fiber materials in the world at present and has the excellent characteristics of high temperature resistance, intrinsic flame retardance, electrical insulation, radiation resistance, chemical corrosion resistance and the like; the material is widely applied to the fields of military police safety protective clothing, high-temperature environment-friendly filter materials, industrial safety protective clothing, high-end electrical appliance insulating materials, secondary stress parts of airplanes and high-speed trains, industrial textiles and the like, and is an important basic material related to the national civilization.
But the meta-aramid fiber in the current market has generally low elongation, and the prepared fabric has poor comfort and cannot meet the high-end market demand.
Disclosure of Invention
The invention aims to provide a high-elongation meta-aramid polymer and a preparation method thereof, so as to improve the elongation of the meta-aramid polymer and solve the technical problem.
In order to achieve the purpose, the invention adopts the following technical scheme:
a high-elongation meta-aramid polymer has the following structural formula:
wherein n > m, R1Derived from a diphenylalkane compound.
The invention further improves the following steps: the R is1The method specifically comprises the following steps:
A preparation method of a high-elongation meta-aramid polymer comprises the following steps:
s1, preparing a first polar solution and a second polar solution;
the preparation method of the first polar solution comprises the following steps: dissolving m-phenylenediamine in a first polar solvent, and then adding isophthaloyl dichloride for full reaction to obtain the compound;
the preparation method of the first polar solution comprises the following steps: dissolving diamine compounds in a first polar solvent, and then adding isophthaloyl dichloride for full reaction to obtain the compound;
s2, uniformly mixing the first polar solution and the second polar solution in proportion, and adding isophthaloyl dichloride for complete reaction;
s3, neutralizing the reaction product of the step S2 to a pH value of more than 8.0 to obtain the high-elongation meta-aramid polymer.
The invention further improves the following steps: in step S1, the ratio of the amounts of m-phenylenediamine dissolved in the first polar solution to the first polar solvent is (40-44): (320-400); when the first polar solution was prepared, isophthaloyl dichloride was added in an amount of 4/5 of the amount of the substance of m-phenylenediamine.
The invention further improves the following steps: in the step S1, the ratio of the amounts of the diamine compound and the second polar solvent in the second polar solution is (1-1.1): (16-18); when the second polarity solution is prepared, the isophthaloyl dichloride is added in an amount of 4/5 of the amount of the diamine-based compound.
The invention further improves the following steps: the structural general formula of the diamine compound is as follows:
NH2-R1-NH2。
the invention further improves the following steps: in step S1, specifically: dissolving m-phenylenediamine in a first polar solvent, cooling to below 20 ℃, and then adding isophthaloyl dichloride for full reaction;
in step S1, specifically: dissolving diamine compound in the second polar solvent, cooling to below 20 deg.c and adding isophthaloyl dichloride for reaction.
The invention further improves the following steps: amount of the substance of m-phenylenediamine in the first polar solution in step S2: the amount of the diamine compound in the second polar solution is (40-44): (1-1.1).
The invention further improves the following steps: the amount of the substance of isophthaloyl dichloride added in step S2 is 1/5 of the sum of the amount of the substance of m-phenylenediamine in the first polar solution in step S2 and the amount of the substance of the diamine-based compound in the second polar solution in step S2.
The invention further improves the following steps: when the first polar solvent and the second polar solution are prepared in the step S1, the time of full reaction after adding the isophthaloyl dichloride is 1-1.5h, and the reaction temperature is below 20 ℃; in step S2, the reaction temperature is below 40 ℃ and the complete reaction time is 0.6-1.2 h.
The invention further improves the following steps: the viscosity of the prepared high-elongation meta-aramid polymer is 1000-1800 Po.
The invention further improves the following steps: the prepared high-elongation meta-aramid polymer is subjected to solidification molding by a dimethylacetamide aqueous solution containing 2% boric acid, and then is subjected to washing, drafting, drying, heat setting, oiling, curling and cutting to form the meta-aramid high-elongation short fiber.
Compared with the prior art, the invention has the following beneficial effects:
1. the high-elongation meta-aramid polymer is prepared by modifying a molecular structure by introducing a diphenylalkane structure on the basis of the original meta-aramid, simultaneously keeps the characteristics of the meta-aramid and enhances the intermolecular force, so that fibers prepared from the modified meta-aramid polymer have excellent spinnability, better tensile property and higher elongation at break in the production process.
2. The high-elongation meta-aramid polymer provided by the invention adopts a simple and easy-to-operate polymerization mode, has an excellent cost advantage, and is easy to realize industrial production.
Detailed Description
To further illustrate the present invention, the following are specific examples and should not be construed as limiting the invention. The characteristics in the examples and comparative examples were measured in the following manner.
In the present invention, the polymer viscosity [ Po ]: the dynamic viscosity of the polymer solution is tested by BROOKFIELD DV-II + Pro, a rotor No. 4 is selected, and the result is finally converted into the viscosity at standard temperature (25 ℃) for characterization.
Fiber breaking strength [ cN/dtex ] and elongation at break [% ]: the fibers obtained were tested for breaking strength and elongation at break using the company Australin VP500, VN 500.
The invention provides a high-elongation meta-aramid polymer, which has the following structural general formula:
wherein n > m, R1Derived from a diphenylalkane compound; n, m ═ (40-44): (1-1.1); the overall molecular weight range is 32-35 million. The R is1The method specifically comprises the following steps:
The invention also provides a preparation method of the high-elongation meta-aramid polymer, which comprises the following steps:
s1, preparing a first polar solution and a second polar solution;
the preparation method of the first polar solution comprises the following steps: dissolving m-phenylenediamine in a first polar solvent, and then adding isophthaloyl dichloride for full reaction to obtain the compound;
the preparation method of the first polar solution comprises the following steps: dissolving diamine compounds in a first polar solvent, and then adding isophthaloyl dichloride for full reaction to obtain the compound;
s2, uniformly mixing the first polar solution and the second polar solution in proportion, and adding isophthaloyl dichloride for complete reaction;
s3, neutralizing the reaction product of the step S2 to a pH value of more than 8.0 to obtain the high-elongation meta-aramid polymer.
In step S1, the ratio of the amounts of m-phenylenediamine dissolved in the first polar solution to the first polar solvent is (40-44): (320-400); when the first polar solution was prepared, isophthaloyl dichloride was added in an amount of 4/5 of the amount of the substance of m-phenylenediamine.
In the step S1, the ratio of the amounts of the diamine compound and the second polar solvent in the second polar solution is (1-1.1): (16-18); when the second polarity solution is prepared, the isophthaloyl dichloride is added in an amount of 4/5 of the amount of the diamine-based compound.
The invention further improves the following steps: the structural general formula of the diamine compound is as follows:
NH2-R1-NH2。
amount of the substance of m-phenylenediamine in the first polar solution in step S2: the amount of the diamine compound in the second polar solution is (40-44): (1-1.1).
The amount of the substance of isophthaloyl dichloride added in step S2 is 1/5 of the sum of the amount of the substance of m-phenylenediamine in the first polar solution in step S2 and the amount of the substance of the diamine-based compound in the second polar solution in step S2.
The viscosity of the prepared high-elongation meta-aramid polymer is 1000-1800 Po.
The polar solvent involved in the above method may be selected from dimethylformamide, dimethylacetamide or N-methylpyrrolidone, but dimethylacetamide and N-methylpyrrolidone are preferred in the present invention in view of the fact that dimethylacetamide has high thermal stability, hydrolytic stability, and is less corrosive and toxic than dimethylformamide in practical production.
Example 1
Adding 22 parts of m-phenylenediamine to 200 parts of dimethylacetamide by mass, stirring and dissolving, and cooling. Controlling the temperature below 20 ℃, adding 17.6 parts of isophthaloyl dichloride according to the reaction ratio of 1:1 of diamine and acyl chloride, and fully reacting for 1h to obtain solution I.
Adding 0.55 part of 4, 4-diaminodiphenylmethane in parts by mass into 9 parts of dimethylacetamide, stirring for dissolving, and cooling. Controlling the temperature below 20 ℃, adding 0.44 part of isophthaloyl dichloride into the diamine and the acyl chloride according to the reaction ratio of 1:1, and fully reacting for 1 hour to obtain a solution II.
Mixing the first step and the second step uniformly to obtain a solution of m-phenylenediamine and 4, 4-diaminodiphenylmethane with the ratio of 40:1, adding 4.51 parts of isophthaloyl dichloride at the temperature of below 40 ℃, and reacting for 1.0 h. After the reaction is finished, propylamine is added for neutralization, and finally the high-elongation meta-aramid polymer with the viscosity of 1725Po (25 ℃) is obtained.
The polymer is coagulated and formed by a dimethylacetamide aqueous solution containing 2% boric acid, and then the polymer is washed, drafted, dried, heat-set, oiled, curled and cut, and the strength of the obtained short fiber can reach more than 4.0cN/dtex through testing, and the elongation at break is more than 50%.
Example 2
Adding 20 parts of m-phenylenediamine to 180 parts of dimethylacetamide by mass, stirring and dissolving, and cooling. Controlling the temperature below 20 ℃, adding 16 parts of isophthaloyl dichloride according to the reaction ratio of 1:1 of diamine and acyl chloride, and fully reacting for 1h to obtain solution I.
Adding 0.5 part of 4,4' -diaminobibenzyl into 9 parts of dimethylacetamide by mass, stirring and dissolving, and cooling. Controlling the temperature below 20 ℃, adding 0.4 part of isophthaloyl dichloride into the diamine and the acyl chloride according to the reaction ratio of 1:1, and fully reacting for 1 hour to obtain a solution II.
Mixing the first and the second components uniformly to obtain a solution of m-phenylenediamine and 4,4' -diaminobibenzyl in a ratio of 40:1, adding 4.1 parts of isophthaloyl dichloride at a temperature of below 40 ℃, and reacting for 1.0 h. After the reaction is completed, propylamine is added for neutralization, and finally the high-elongation meta-aramid polymer with the viscosity of 1610Po (25 ℃) is obtained.
The polymer is coagulated and formed by a dimethylacetamide aqueous solution containing 2% boric acid, and then the polymer is washed, drafted, dried, heat-set, oiled, curled and cut, and the strength of the obtained short fiber can reach more than 4.0cN/dtex through testing, and the elongation at break is more than 50%.
Example 3
Adding 40 parts of m-phenylenediamine to 350 parts of N-methylpyrrolidone, stirring and dissolving, and cooling. Controlling the temperature below 20 ℃, adding 32 parts of isophthaloyl dichloride according to the reaction ratio of 1:1 of diamine and acyl chloride, and fully reacting for 1.5h to obtain solution I.
Adding 1 part of 4, 4-diaminodiphenylmethane in an amount of 16 parts by mass into N-methylpyrrolidone, stirring and dissolving, and cooling. Controlling the temperature below 20 ℃, adding 0.8 part of isophthaloyl dichloride into the mixture according to the reaction ratio of 1:1 between diamine and acyl chloride, and fully reacting for 1.5 hours to obtain a solution II.
Uniformly mixing the first step and the second step to obtain a solution of m-phenylenediamine and 4, 4-diaminodiphenylmethane with the ratio of 40:1, adding 8.2 parts of isophthaloyl dichloride at the temperature of below 40 ℃, and reacting for 1.0 h. After the reaction is finished, propylamine is added for neutralization, and finally the high-elongation meta-aramid polymer with the viscosity of 1582Po (25 ℃) is obtained.
The polymer is solidified and formed by N-methyl pyrrolidone water solution containing 2 percent of boric acid, and then the polymer is washed, drafted, dried, heat-set, oiled, curled and cut, and the strength of the obtained short fiber can reach more than 4.0cN/dtex through testing, and the elongation at break is more than 50 percent.
Example 4
Adding 20 parts of m-phenylenediamine by mass into 160 parts of N-methylpyrrolidone, stirring and dissolving, and cooling. Controlling the temperature below 20 ℃, adding 16 parts of isophthaloyl dichloride according to the reaction ratio of 1:1 of diamine and acyl chloride, and fully reacting for 1h to obtain solution I.
Adding 0.5 part of 4,4' -diaminobibenzyl calculated by mass into 8 parts of N-methylpyrrolidone, stirring and dissolving, and cooling. Controlling the temperature below 20 ℃, adding 0.4 part of isophthaloyl dichloride into the diamine and the acyl chloride according to the reaction ratio of 1:1, and fully reacting for 1 hour to obtain a solution II.
Mixing the first and the second components uniformly to obtain a solution of m-phenylenediamine and 4,4' -diaminobibenzyl in a ratio of 40:1, adding 4.1 parts of isophthaloyl dichloride at a temperature of below 40 ℃, and reacting for 1.0 h. After the reaction is finished, propylamine is added for neutralization, and finally the high-elongation meta-aramid polymer with the viscosity of 1490Po (25 ℃) is obtained.
The polymer is solidified and formed by N-methyl pyrrolidone water solution containing 2 percent of boric acid, and then the polymer is washed, drafted, dried, heat-set, oiled, curled and cut, and the strength of the obtained short fiber can reach more than 4.0cN/dtex through testing, and the elongation at break is more than 50 percent.
The high-elongation meta-aramid polymer prepared by the invention is subjected to solidification molding by a dimethylacetamide aqueous solution containing 2% boric acid, and then is subjected to washing, drafting, drying, heat setting, oiling, curling and cutting to form the meta-aramid high-elongation short fiber. Sampling for detection, wherein the sample length is as follows: 51 mm; gauge length: 20 mm; testing speed: 20 mm/min; tension force: 150 mg; the performance parameters are shown in table 1:
TABLE 1 short-staple performance test table
The above-mentioned embodiments are merely illustrative of the preferred embodiments of the present invention, and do not limit the scope of the present invention, and various modifications and improvements of the technical solution of the present invention by those skilled in the art should fall within the protection scope defined by the claims of the present invention without departing from the spirit of the present invention.
Claims (10)
1. The high-elongation meta-aramid polymer is characterized by having the following structural general formula:
wherein n > m, R1Derived from a diphenylalkane compound.
2. The method of claim 1The high-elongation meta-aramid polymer is characterized in that R1The method specifically comprises the following steps:
3. A preparation method of a high-elongation meta-aramid polymer is characterized by comprising the following steps:
s1, preparing a first polar solution and a second polar solution;
the preparation method of the first polar solution comprises the following steps: dissolving m-phenylenediamine in a first polar solvent, and then adding isophthaloyl dichloride for full reaction to obtain the compound;
the preparation method of the second polarity solution comprises the following steps: dissolving diamine compounds in a first polar solvent, and then adding isophthaloyl dichloride for full reaction to obtain the compound;
s2, uniformly mixing the first polar solution and the second polar solution in proportion, and adding isophthaloyl dichloride for complete reaction;
s3, neutralizing the reaction product of the step S2 to a pH value of more than 8.0 to obtain the high-elongation meta-aramid polymer.
4. The method of claim 3, wherein the ratio of the amounts of m-phenylenediamine dissolved in the first polar solvent to the first polar solvent in the first polar solution in the step S1 is (40-44): (320-400); when the first polar solution was prepared, isophthaloyl dichloride was added in an amount of 4/5 of the amount of the substance of m-phenylenediamine.
5. The method of claim 3, wherein the amount ratio of the diamine compound to the second polar solvent in the second polar solution in the step S1 is (1-1.1): (16-18); when the second polarity solution is prepared, the isophthaloyl dichloride is added in an amount of 4/5 of the amount of the diamine-based compound.
6. The method for preparing the high-elongation meta-aramid polymer according to claim 3, wherein the diamine compound has a general structural formula as follows:
NH2-R1-NH2。
7. the method for preparing a high-elongation meta-aramid polymer as claimed in claim 3, wherein in the step S1, specifically: dissolving m-phenylenediamine in a first polar solvent, cooling to below 20 ℃, and then adding isophthaloyl dichloride for full reaction;
in step S1, specifically: dissolving diamine compound in the second polar solvent, cooling to below 20 deg.c and adding isophthaloyl dichloride for reaction.
8. The method of claim 3, wherein the amount of the meta-phenylene diamine in the first polar solution in the step S2 is as follows: the amount of the diamine compound in the second polar solution is (40-44): (1-1.1).
9. The method of claim 3, wherein the amount of the isophthaloyl dichloride added in the step S2 is 1/5 of the sum of the amount of the m-phenylenediamine in the first polar solution in the step S2 and the amount of the diamine-based compound in the second polar solution in the step S2.
10. The method for preparing a high-elongation meta-aramid polymer according to claim 3, wherein when the first polar solvent and the second polar solution are prepared in step S1, the sufficient reaction time after adding the isophthaloyl dichloride is 1-1.5h, and the reaction temperature is 20 ℃ or lower;
in step S2, the reaction temperature is below 40 ℃ and the complete reaction time is 0.6-1.2 h.
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| CN202011175357.5A CN112341619A (en) | 2020-10-27 | 2020-10-27 | High-elongation meta-aramid polymer and preparation method thereof |
| PCT/CN2021/112535 WO2022088852A1 (en) | 2020-10-27 | 2021-08-13 | High-elongation meta-aramid polymer and preparation method therefor |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2022088852A1 (en) * | 2020-10-27 | 2022-05-05 | 烟台泰和新材料股份有限公司 | High-elongation meta-aramid polymer and preparation method therefor |
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Application publication date: 20210209 |