Method for producing antibacterial polyester and method for producing antibacterial fiber

Abstract

The present invention relates to a method for producing antibacterial polyester, an antibacterial fiber obtained by the method, and the application of the antibacterial fiber in the production of medical and surgical products. The present invention primarily addresses the drawbacks of existing antibacterial polyester fibers, such as poor washability and antibacterial performance. The present invention includes the steps of (i) esterifying a diol with a dibasic acid to obtain ester I, (ii) mixing ester I with a reactive antibacterial component and conducting a pre-polycondensation reaction to obtain a pre-polycondensation product, and (iii) conducting a final polycondensation reaction of the pre-polycondensation product to obtain an antibacterial polyester. The reactive antibacterial component is obtained by esterifying a substance represented by the following formula 3 with a diol. Q is a quaternary ammonium group containing a long-chain hydrocarbon group, the long-chain hydrocarbon group having 6 to 20 carbon atoms, and Ar is an aromatic ring. [Formula 1] JPEG2025538019000015.jpg26170

Description

[Technical Field]

[0001] The present invention relates to a method for producing antibacterial polyester, a method for producing antibacterial polyester and antibacterial fiber obtained by the method, the antibacterial fiber, and the application of the antibacterial fiber in the production of medical and surgical products. [Background technology]

[0002] Polyester fiber is a widely used synthetic fiber in large quantities, widely used in household textiles, clothing, industrial textiles, and more. China's total polyester fiber production is expected to exceed 50 million tons in 2022. Bacterial infection is one of the major threats to human health. The development of polyester fiber with antibacterial properties is highly significant, as it can help prevent the spread of bacteria, reduce the risk of bacterial infection, reduce the use of antibiotics, and improve people's health. Currently, antibacterial polyester fibers are mainly produced by physically incorporating inorganic antibacterial agents such as nanosilver and nanozinc oxide. However, the antibacterial properties of this type of antibacterial polyester fiber are achieved through the diffusion and release of the antibacterial agent, which is lost once release is complete. This is particularly true during daily washing, and the antibacterial properties are not long-term. On the other hand, inorganic antibacterial agents are highly biotoxic and may cause skin allergies when used in textiles that come into contact with the human body, limiting their scope of application. Currently, the most commonly used method for large-scale commercial polyester fiber synthesis is the melt condensation polymerization of dibasic acids and diols, followed by melt spinning. By covalently bonding organic eco-friendly antibacterial agents to the polyester backbone through co-condensation polymerization, it is possible to not only impart long-lasting antibacterial properties to polyester, but also effectively reduce the biotoxicity of the antibacterial agents, which is the development direction of antibacterial polyester fibers. Summary of the Invention [Problem to be solved by the invention]

[0003] One of the technical problems that the present invention aims to solve is the drawback that existing antibacterial polyester fibers have low wash resistance of antibacterial performance. The present invention provides a new method for producing antibacterial polyester, and the antibacterial polyester fiber produced from the antibacterial polyester has the advantages of excellent wash resistance and antibacterial performance. [Means for solving the problem]

[0004] In order to solve the above technical problems, the technical solutions of the present invention are as follows: The method for producing antibacterial polyester includes the following steps. (i) a step of subjecting a diol and a dibasic acid to an esterification reaction to obtain an ester I; (ii) mixing the ester I with a reactive antibacterial component to carry out a pre-condensation polymerization reaction to obtain a pre-condensation polymerization product; (iii) a step of subjecting the preliminary condensation polymerization product to a final condensation polymerization reaction to obtain an antibacterial polyester; The reactive antibacterial component can be obtained by esterification of the substance shown in Formula 3 with a diol.

[0005] [ka] Q is a quaternary ammonium group containing a long-chain hydrocarbon group, the long-chain hydrocarbon group having 6 to 20 carbon atoms, and Ar is an aromatic ring.

[0006] The technical key of the present invention is the use of a reactive antibacterial component in the production of antibacterial polyesters. Once the reactive antibacterial component is disclosed, those skilled in the art can rationally select process conditions to achieve equivalent technical effects without engaging in creative work when using the reactive antibacterial component in the production of antibacterial polyesters. However, compared with the direct co-esterification of the component shown in Formula 3 in step (i) or the esterification of the component after adding the reactive antibacterial component in step (i), the antibacterial polyester obtained by adding the reactive antibacterial component of the present invention in the pre-condensation polymerization reaction stage has been found to have a much better antibacterial effect than the antibacterial polyester obtained by adding the reactive antibacterial component of the present invention in the esterification stage.

[0007] In the above technical solution, Ar is preferably a benzene ring or a naphthalene ring.

[0008] In the above technical solution, the diol in step (i) preferably comprises at least one selected from the group consisting of ethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol and 1,4-cyclohexanedimethanol. For comparison purposes only, ethylene glycol is generally used in the embodiments of the present invention.

[0009] In the above technical solution, in step (i), the dibasic acid preferably comprises at least one selected from the group consisting of terephthalic acid, succinic acid, adipic acid, isophthalic acid and furandicarboxylic acid. For comparison purposes only, terephthalic acid is generally used in the embodiments of the present invention.

[0010] In the above technical solution, in step (i), the molar ratio of diol to dibasic acid is preferably 1.1 to 1.5, for example, the molar ratio of diol to dibasic acid is 1.15, 1.2, 1.25, 1.3, 1.35, 1.4, 1.45, etc., but is not limited thereto.

[0011] In the above technical solution, the esterification rate of the esterification reaction in step (i) is preferably 95% to 99%, for example, but not limited to, 95.5%, 96%, 96.5%, 97%, 97.5%, 98%, 98.5%, etc.

[0012] To achieve the above-mentioned esterification rate, those skilled in the art can reasonably select the esterification temperature and esterification time according to the actual conditions, such as the operating conditions allowed by the reactor. In principle, the higher the esterification temperature and the longer the esterification time, the higher the esterification rate.

[0013] As a non-limiting example, the esterification temperature in step (i) can be selected from 150 to 250°C, and more specific, non-limiting examples include 160°C, 170°C, 180°C, 190°C, 200°C, 210°C, 220°C, 230°C, and 240°C. When water produced by the esterification reaction is continuously separated within this temperature range, even without using a catalyst as in an embodiment of the present invention, the esterification reaction time required to achieve a desired esterification rate is typically 0.5 to 2 hours. Of course, an esterification catalyst can also be used in the esterification reaction, and the use of an esterification catalyst increases the esterification reaction rate.

[0014] The esterification reaction in step (i) may be carried out under the autogenous pressure of the reaction, or may be carried out at a pressure higher than the autogenous pressure by filling the reaction system with an inert gas such as nitrogen. Since the esterification reaction in step (i) is a liquid phase reaction, the pressure does not significantly affect the progress of the esterification reaction.

[0015] In the above technical solution, in step (ii), the mass ratio of the reactive antibacterial component (calculated by the N contained therein) to the esterified product I is calculated based on the dibasic acid required for its preparation, and preferably the mass ratio of the reactive antibacterial component to the esterified product I is t:100, where t is greater than 0 and less than 4. For example, t can be, but is not limited to, 0.01, 0.05, 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1, 1.5, 2, 2.5, 3, 3.5, etc.

[0016] In the above technical solution, in step (ii), the pressure is preferably 400-600 Pa, such as, but not limited to, 410 Pa, 420 Pa, 430 Pa, 440 Pa, 450 Pa, 460 Pa, 470 Pa, 480 Pa, 490 Pa, 500 Pa, 510 Pa, 520 Pa, 530 Pa, 540 Pa, 550 Pa, etc.

[0017] In the above technical solution, in step (ii), the preferred reaction temperature is 255-265°C, such as, but not limited to, 256°C, 257°C, 258°C, 259°C, 260°C, 261°C, 262°C, 263°C, 264°C, etc.

[0018] In the above technical solution, in step (ii), the reaction time is preferably 30-60 minutes, such as, but not limited to, 35 minutes, 40 minutes, 45 minutes, 50 minutes, 55 minutes, etc.

[0019] In the above technical solution, in step (iii), the reaction pressure is preferably less than 100 Pa, for example, but not limited to, 5 Pa, 10 Pa, 20 Pa, 30 Pa, 40 Pa, 50 Pa, 60 Pa, 70 Pa, 80 Pa, 90 Pa, etc.

[0020] In the above technical solution, in step (iii), the reaction temperature is preferably 270-285°C, such as, but not limited to, 271°C, 272°C, 273°C, 274°C, 275°C, 276°C, 277°C, 278°C, 279°C, 280°C, 281°C, 282°C, 283°C, 284°C, etc.

[0021] Those skilled in the art will understand that decreasing the reaction pressure and increasing the reaction temperature in step (iii) are beneficial for accelerating the final condensation polymerization reaction and increasing the intrinsic viscosity of the final condensation polymerization product. When the reaction pressure and reaction temperature in step (iii) are determined, the intrinsic viscosity in step (iii) tends to increase with increasing reaction time. In the above technical solution, step (iii) is preferably carried out until the intrinsic viscosity reaches 0.60 to 0.75 dL / g. For comparison, the intrinsic viscosity in both the working example and the comparative example was 0.68 dL / g.

[0022] In the above technical solution, in step (iii), the reaction time is generally 1.5-3.0 hours under the above reaction temperature and reaction pressure to achieve the required intrinsic viscosity range.

[0023] In the above technical solution, the method for synthesizing the reactive antibacterial component includes the following steps: (1) Compound 1 and compound 2 are subjected to an ion exchange reaction in a solvent to obtain intermediate product 3.

[0024] Compound 1 conforms to the structure shown in Formula 1. [ka]

[0025] Compound 2 conforms to the structure shown in Formula 2. [ka]

[0026] Intermediate product 3 conforms to the structure shown in Formula 3. [ka] X is Cl or Br. M is an alkali metal.

[0027] (2) Intermediate product 3 undergoes an esterification reaction with a diol to obtain a reactive antibacterial component. In the above technical solution, the solvent described in step (1) is preferably water.

[0028] The ion exchange reaction formula in step (1) is expressed as follows:

[0029] [ka] When water is used as the solvent for the ion exchange reaction, the intermediate product 3 precipitates in the reaction system and can be very easily separated from the reaction system.

[0030] Non-limiting examples of Compound 1 include, for example, benzalkonium chloride, hexyltrimethylammonium chloride, octyltrimethylammonium chloride, decyltrimethylammonium chloride, dodecyltrimethylammonium chloride, tetradecyltrimethylammonium chloride, hexadecyltrimethylammonium chloride, octadecyltrimethylammonium chloride, N-hexylpyridinium chloride, N-octylpyridinium chloride, N-decylpyridinium chloride, N-dodecylpyridinium chloride, N-tetradecylpyridinium chloride, N-hexadecylpyridinium chloride, N-octadecylpyridinium chloride, and 1-hexyl-3-methylimidazole bromide. , 1-octyl-3-methylimidazole bromide, 1-decyl-3-methylimidazole bromide, 1-dodecyl-3-methylimidazole bromide, 1-tetradecyl-3-methylimidazole bromide, 1-hexadecyl-3-methylimidazole bromide, 1-octadecyl-3-methylimidazole bromide, bishexyldimethylammonium chloride, bisoctyldimethylammonium chloride, bisdecyldimethylammonium chloride, dodecyldimethylammonium chloride, ditetradecyldimethylammonium chloride, bishexadecyldimethylammonium chloride or dioctadecyldimethylammonium chloride.

[0031] In the above technical solution, any compound 1 conforms to the structure shown in formula 1a.

[0032] [ka] R1 is a long-chain hydrocarbon group, and the number of carbon atoms in R1 is 6 to 20. R2 to R4 are short-chain hydrocarbon groups, and R2 to R4 are each independently preferably a C1 to C2 alkyl group.

[0033] As a non-limiting example, the number of carbon atoms in R1 can be, but is not limited to, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, etc. R1 can be an alkyl group, an alkenyl group, or an aryl group.

[0034] In the above technical solution, compound 2 preferably conforms to the structure shown in formula 2a.

[0035] [ka]

[0036] As an example, compound 2 in an embodiment of the present invention is an alkali metal salt of 5-sulfonic acid isophthalic acid.

[0037] In the above technical solution, the ion exchange reaction is as rapid and complete as the exchange reaction of inorganic ions. Therefore, there are no particular limitations on the specific process conditions for the ion exchange reaction, and process conditions commonly used in the art can be adopted. As an example, compound 1 can be dissolved in an aqueous solution at a weight concentration of 1 to 10% (e.g., 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, etc.) and added to the reaction system. As another example, compound 2 can be dissolved in an aqueous solution at a weight concentration of 1 to 10% (e.g., 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, etc.) and added to the reaction system. There are no special requirements for the reaction temperature, and the reaction proceeds smoothly even at room temperature. Because the ion exchange reaction is fast, there is no particular limitation on the reaction time. However, extending the reaction time (i.e., the apparent reaction time) can be beneficial for obtaining a better precipitate morphology and for easier washing and separation. For example, the apparent reaction time can be 1.5 to 3 hours. Because the ion exchange reaction itself is completed instantaneously, the apparent reaction time is primarily the maturation time of the ion exchange product within the reaction system.

[0038] In the above technical solution, the diol in step (2) preferably comprises at least one selected from the group consisting of 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,4-cyclohexanedimethanol, and diols based on OCH2CH2 units. The diols based on OCH2CH2 units comply with Formula 4:

[0039] [ka]

[0040] Preferably, the number average molecular weight of the diol based on OCH2CH2 units is higher than the molecular weight of ethylene glycol and is 4000 g / mol or less, and m is a value necessary to satisfy the required molecular weight.

[0041] For example, diols based on OCH2CH2 units include, but are not limited to, ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol 300, polyethylene glycol 400, polyethylene glycol 500, polyethylene glycol 600, polyethylene glycol 800, polyethylene glycol 1000, polyethylene glycol 1500, polyethylene glycol 2000, polyethylene glycol 2500, polyethylene glycol 3000, polyethylene glycol 3500, polyethylene glycol 4000, etc. According to the naming convention for polyethylene glycol grades, the number after polyethylene glycol represents the number average molecular weight.

[0042] We found that the different diols used in step (2) have a significant impact on the antibacterial properties of the antibacterial polyester. When the diol used in step (2) is 1,4-cyclohexanedimethanol, the antibacterial performance is significantly better than when the diol used is ethylene glycol, 1,3-propanediol, 1,4-butanediol, or polyethylene glycol.

[0043] Furthermore, when the diol used in step (2) is a mixed alcohol of ethylene glycol and 1,4-cyclohexanedimethanol, it has been found that ethylene glycol and 1,4-cyclohexanedimethanol have a synergistic effect in improving the antibacterial properties of the antibacterial polyester. In this case, the ratio of ethylene glycol to 1,4-cyclohexanedimethanol is not particularly limited, and the same synergistic effect can be obtained. For example, the molar ratio of ethylene glycol to 1,4-cyclohexanedimethanol is 0.1 to 10. More specific, non-limiting examples of molar ratios include 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1, 1.1, 1.2, 1.3, 1.4, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, 5, 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, and 9.5. A molar ratio of 0.2 to 5 is more preferable.

[0044] In the above technical solution, the molar ratio of diol to intermediate product 3 in step (2) is preferably greater than 1 and less than 2, more preferably 1.1-1.5, such as, but not limited to, 1.05, 1.1, 1.15, 1.20, 1.25, 1.3, 1.35, 1.4, 1.45, 1.5, 1.55, 1.6, 1.65, 1.7, 1.75, 1.8, 1.85, 1.9, 1.95, etc.

[0045] In the above technical solution, the esterification reaction in step (2) is preferably carried out until the esterification rate reaches 95% to 99%, for example, but not limited to, 95.5%, 96%, 96.5%, 97%, 97.5%, 98%, 98.5%, etc.

[0046] To achieve the above-mentioned esterification rate, those skilled in the art can reasonably select the esterification temperature and esterification time according to the actual conditions, such as the operating conditions allowed by the reactor. In principle, the higher the esterification temperature and the longer the esterification time, the higher the esterification rate.

[0047] As a non-limiting example, the esterification temperature in step (2) can be selected from 150 to 250°C. More specific, non-limiting examples include 160°C, 170°C, 180°C, 190°C, 200°C, 210°C, 220°C, 230°C, and 240°C. When the water produced by the esterification reaction is continuously separated within this temperature range, even in the case of an embodiment of the present invention where no catalyst is used, the esterification reaction time required to achieve the desired esterification rate is typically 0.5 to 2 hours. Of course, an esterification catalyst can also be used in the esterification reaction, and the use of an esterification catalyst increases the esterification reaction rate.

[0048] The esterification reaction in step (2) can be carried out under the autogenous pressure of the reaction, or can be carried out under a pressure higher than the autogenous pressure by filling the reaction system with an inert gas such as nitrogen. Since the esterification reaction in step (2) is a liquid phase reaction, the pressure does not significantly affect the progress of the esterification reaction.

[0049] Those skilled in the art will understand that both step (2) and step (i) are esterification reactions. Esterification can be easily carried out with or without the addition of a catalyst. However, in the prepolymerization and final polymerization steps (ii) and (iii), the activity of reactive groups becomes limited as the molecular chain length increases, so a polymerization catalyst is usually required. The polymerization catalyst can be added in the esterification step (ii) and / or step (i), and then enter the esterified product into step (ii) and then the polycondensation step (iii). Alternatively, the catalyst can be added during the prepolymerization step (ii) and / or the final polymerization step (iii), achieving the same technical effect without any inventive effort. To promote catalyst dispersion in steps (ii) and (iii) and achieve a more uniform catalytic effect, it is preferable to add the catalyst in the esterification step (ii) and / or step (i). For comparison, all polymerization catalysts in the examples of the present invention are added in step (i).

[0050] The polymerization catalyst may be any of those known to those skilled in the art, such as antimony-based polymerization catalysts (antimony trioxide, antimony acetate, antimony ethylene glycolate, etc.), titanium-based polymerization catalysts, etc., but is not limited thereto, as long as equivalent technical effects can be achieved. For comparative purposes only, all of the polymerization catalysts used in the embodiments are antimony-based catalysts, and the amount of antimony-based catalyst used, expressed as antimony and measured by weight, is 100 to 300 ppmw (e.g., but not limited to, 110 ppmw, 120 ppmw, 130 ppmw, 140 ppmw, 150 ppmw, 160 ppmw, 170 ppmw, 180 ppmw, 190 ppmw, 200 ppmw, 210 ppmw, 220 ppmw, 230 ppmw, 240 ppmw, 250 ppmw, 260 ppmw, 270 ppmw, 280 ppmw, 290 ppmw, etc.) relative to the terephthalic acid added in step (i). For comparative purposes only, all of the antimony-based polymerization catalysts used in the examples are antimony-ethylene glycolate.

[0051] Regarding the concept of the esterification rate in the above steps (2) and (i), it is well known to those skilled in the art that the esterification rate is used to monitor the degree of completion of the esterification reaction and is defined as the ratio of the number of moles of carboxyl groups forming ester groups to the number of moles of carboxyl groups in the feedstock. The esterification rate can be controlled by measuring the amount of water produced and distilled by the esterification reaction. The esterification rate is measured by comparing the weight of water actually produced by the esterification reaction with the weight of water produced assuming that the carboxyl groups in the reaction raw material are completely esterified. The specific calculation is as follows:

[0052] Esterification rate % = (weight of water actually produced by the esterification reaction / weight of water produced assuming that the carboxyl groups in the reaction raw materials are completely esterified) x 100%.

[0053] The second technical problem to be solved by the present invention is to provide an antibacterial polyester. In order to solve the second technical problem above, the technical solution of the present invention is as follows: The antibacterial polyester can be obtained by the manufacturing method described in any of the technical solutions to any of the above technical problems.

[0054] The third technical problem to be solved by the present invention is to provide a method for producing antibacterial fibers. In order to solve the third technical problem above, the technical solution of the present invention is as follows:

[0055] The method for producing antibacterial fibers includes the following steps: (a) mixing spinning-grade PET polyester with the antibacterial polyester described in the technical solution of the second technical problem, and melt-spinning the mixture to obtain primary fibers;

[0056] (b) Hot drawing process of the spun primary fiber.

[0057] The technical key of the present invention lies in the selection of the antibacterial component (which can also be said to be the selection of the antibacterial polyester), and there are no particular limitations on the manufacturing method of the specific antibacterial fiber. Those skilled in the art can make reasonable selections and adjustments among commonly used processes and process conditions to achieve the same technical effect. The processes and process conditions described below are merely non-limiting examples.

[0058] For example, but not by way of limitation, in step (a), the mass ratio of antimicrobial polyester (calculated in terms of the N contained therein) to spinning-grade PET polyester is q:100, where q is greater than 0 and less than 0.2, and more specifically, but not by way of limitation, q is 0.01, 0.02, 0.03, 0.04, 0.05, 0.06, 0.07, 0.08, 0.09, 0.10, 0.11, 0.12, 0.13, 0.14, 0.15, 0.16, 0.17, 0.18, 0.19, etc., and more preferably 0.02 to 0.15. For comparative purposes only, embodiments generally use a value of 0.04 for q.

[0059] For example, but not limited to, the intrinsic viscosity of the spinning-grade PET polyester in step (a) is 0.60-0.70 dL / g. For example, but not limited to, the intrinsic viscosity of the spinning-grade PET polyester is 0.61 dL / g, 0.62 dL / g, 0.63 dL / g, 0.64 dL / g, 0.65 dL / g, 0.66 dL / g, 0.67 dL / g, 0.68 dL / g, 0.69 dL / g, etc. For comparison, the commercially available spinning-grade polyethylene terephthalate (hereinafter referred to as "commercial spinning-grade PET") used in specific embodiments of the present invention is the SB500 type manufactured by Sinopec Yizheng Chemical Fiber Co., Ltd., which has an intrinsic viscosity of 0.67 dL / g, with an actually measured intrinsic viscosity of 0.68 dL / g.

[0060] For example, but not limited to, the melt spinning method described above can be used to produce continuous or staple fibers. Continuous fibers can be FDY, POY, or DTY fibers produced by adding elasticity to POY. Continuous fibers have a diameter of 50-300D (e.g., 50D, 60D, 70D, 80D, 90D, 100D, 110D, 120D, 130D, 140D, 150D, 160D, 170D, 180D, 190D, 200D, etc.). Staple fibers have a length of 38-76mm and a fineness of 0.5-3.0D. Whether continuous or staple fibers are produced is not a key aspect of the present invention, and the same technical effects can be achieved regardless of the above specifications or the manufacturing process used. For comparison purposes only, in a specific embodiment of the present invention, continuous fibers are produced using the FDY process, and the continuous fiber specifications are 150D.

[0061] In the above technical solution, the stretching temperature in step (b) is preferably 120-160°C, such as (but not limited to) 120°C, 125°C, 130°C, 135°C, 140°C, 145°C, 150°C, 155°C, 160°C, etc. For comparison purposes only, the stretching temperature in a specific embodiment of the present invention is 140°C.

[0062] In the above technical solution, the stretching ratio in step (b) is preferably 3.0 to 5.0, such as, but not limited to, 3.1x, 3.2x, 3.3x, 3.4x, 3.x, 3.6x, 3.7x, 3.x, 3.9x, 4.0x, 4.1x, 4.2x, 4.3x, 4.4x, 4.5x, 4.6x, 4.7x, 4.8x, 4.9x, 5.0x, etc. For comparison, the stretching ratio in a specific embodiment of the present invention is 4.0x.

[0063] The fourth technical problem to be solved by the present invention is to provide an antibacterial fiber. In order to solve the above fourth technical problem, the technical solution of the present invention is as follows: The antibacterial fiber is an antibacterial fiber obtained by the manufacturing method described in any of the technical solutions to the third technical problem above.

[0064] The fifth technical problem to be solved by the present invention is to provide applications of antibacterial fibers. In order to solve the above fifth technical problem, the technical solution of the present invention is as follows: The antibacterial fiber described in the technical solution to the fourth technical problem above is applied to the manufacture of medical-surgical products, in particular antibacterial gauze and / or antibacterial bandages.

[0065] It is obvious to those skilled in the art that the antibacterial fiber described above has antibacterial properties and can be used to manufacture medical gauze and bandages. Because the antibacterial fiber is used, the use of gauze and bandages containing the antibacterial fiber can prevent wound infection. When manufacturing gauze and bandages using the antibacterial fiber, those skilled in the art can rationally select a known method for manufacturing gauze and bandages using fibers without any creative effort.

[0066] The intrinsic viscosity of the present invention is measured using Method A in Section 5.1.1 of GB / T14190-2017 (Test Methods for Fiber-Grade Polyester (PET) Specimens), and the solvent used is a 50:50 mixture of phenol and 1,1,2,2-tetrachloroethane by mass.

[0067] Nitrogen content in specific embodiments of the present invention is measured by the Kjeldahl nitrogen method.

[0068] The durability of the antibacterial properties of antibacterial polyester fabrics was evaluated in accordance with "GBT20944.3-2008 Antibacterial Evaluation of Textile Products, Part 3, Vibration Method." Before testing, the textile products were washed 50 times according to method 10.1.2 of the standard. The test bacteria used was Staphylococcus aureus (ATCC6538). The higher the antibacterial rate measured after 50 washes using the above method, the better the textile product's antibacterial properties and the durability of its antibacterial properties. The present invention will be described in detail below with reference to specific embodiments. DETAILED DESCRIPTION OF THE INVENTION

[0069] The antibacterial rate in the examples and comparative examples is the antibacterial rate measured after 50 washes by the above method. In this application, ppmw means 1 / 1000000 parts by weight.

[0070] Example 1 1. Synthesis of reactive antibacterial components 1.1. The compound shown in formula 3 is obtained. While stirring, an aqueous solution of hexadecyltrimethylammonium chloride (weight concentration 5.6%) was added to an equal volume of an aqueous solution of sodium 5-sulfoisophthalate (weight concentration 5.0%), stirred for 2 hours, allowed to stand to separate the layers, filtered, the filter cake was washed three times with water, each time using an equal volume of water to the filter cake, and dried at 80°C for 5 hours to obtain a dry product of the compound represented by Formula 3. The nitrogen content by weight of the product was measured to be 2.64%.

[0071] 1.2. Obtaining reactive antibacterial components Ethylene glycol and the product from step 1.1 were mixed in a molar ratio of 1.3:1 as reaction raw materials, and the esterification reaction was carried out at 180°C. The water produced by the esterification was collected and measured until the esterification rate reached 97%, yielding a reactive antibacterial component. The nitrogen content of the product was determined to be 2.43% by weight.

[0072] 2.Production of antibacterial polyester 2.1.Esterification The reaction raw materials, terephthalic acid, antimony ethylene glycolate, and ethylene glycol (the molar ratio of ethylene glycol to terephthalic acid is 1.2, and the amount of antimony ethylene glycolate used is equivalent to 200 ppmw of the weight of terephthalic acid in terms of antimony), are mixed, and an esterification reaction is carried out at 200°C. The water produced by the esterification is measured and collected until the esterification rate reaches 97%, and esterified product I is obtained.

[0073] 2.2. Pre-condensation polymerization The product of step 1.2 is calculated based on the weight of nitrogen contained therein, and the esterification material I of step 2.1 is calculated based on the weight of terephthalic acid required to prepare it. The product of step 1.2 and the esterification material I of step 2.1 are mixed in a weight ratio of 1.2:100 and subjected to condensation polymerization at an absolute pressure of 500 Pa and 260°C for 45 minutes.

[0074] 2.3. Final condensation polymerization The material obtained in step 2.2 was subjected to a condensation polymerization reaction at 50 Pa absolute pressure and 280°C until the intrinsic viscosity reached 0.68 dL / g, yielding an antibacterial polyester. The nitrogen weight content in the antibacterial polyester was determined to be 0.73%.

[0075] 3. Antibacterial fiber manufacturing 3.1. Melt spinning The antibacterial polyester (calculated by N content) prepared in step 2.3 was mixed with commercial spinning-grade PET at a weight ratio of 0.040:100 and melt-spun at a melt-spinning temperature of 280 °C to obtain primary fibers.

[0076] 3.2. Stretching The spun fiber obtained by melt spinning was heated and drawn to a draw ratio of 4.0 and a drawing temperature of 140°C. Next, FDY fiber was spun. The FDY fiber had a specification of 150D.

[0077] 4. Antibacterial polyester fiber test The test results showed that the antibacterial rate was 89.1%.

[0078] (Comparative Example 1) The main difference from Example 1 is that the compound of Formula 3 is directly added to the esterification step in the preparation of antibacterial polyester, specifically as follows: 1. Obtain the compound shown in formula 3 (same as 1.1 in Example 1) While stirring, an aqueous solution of hexadecyltrimethylammonium chloride (weight concentration 5.6%) was added to an equal volume of an aqueous solution of sodium 5-sulfoisophthalate (weight concentration 5.0%), stirred for 2 hours, allowed to stand to separate the layers, filtered, the filter cake was washed three times with water, each time using an equal volume of water to the filter cake, and dried at 80°C for 5 hours to obtain a dry product of the compound represented by Formula 3. The nitrogen content by weight of the product was measured to be 2.64%.

[0079] 2.Production of antibacterial polyester 2.1.Esterification Terephthalic acid, the product of step 1, antimony ethylene glycolate, and ethylene glycol are mixed (the molar ratio of ethylene glycol to (the total of the product of step 1 and terephthalic acid) is 1.2, the mass ratio of the product of step 1 to terephthalic acid on a nitrogen basis is 1.2:100, and the amount of antimony ethylene glycolate used on an antimony basis corresponds to 200 ppmw of the weight of terephthalic acid), and an esterification reaction is carried out at 200°C. Water produced by the esterification is collected and measured until the esterification rate reaches 97%, thereby obtaining esterified product I.

[0080] 2.2. Pre-condensation polymerization The esterified material I from step 2.1 was subjected to condensation polymerization at 500 Pa absolute pressure and 260° C. for 45 minutes.

[0081] 2.3. Final condensation polymerization The material obtained in step 2.2 was subjected to a condensation polymerization reaction at 280°C under an absolute pressure of 50 Pa until the intrinsic viscosity reached 0.68 dL / g, yielding an antibacterial polyester. The nitrogen weight content in the antibacterial polyester was determined to be 0.73%.

[0082] 3. Antibacterial fiber manufacturing 3.1. Melt spinning The antibacterial polyester (calculated by N content) prepared in step 2.3 was mixed with commercial spinning-grade PET at a weight ratio of 0.040:100 and melt-spun at a melt-spinning temperature of 280 °C to obtain primary fibers.

[0083] 3.2. Stretching The spun fiber obtained by melt spinning was heated and drawn to a draw ratio of 4.0 and a drawing temperature of 140°C. Next, FDY fiber was spun. The FDY fiber had a specification of 150D.

[0084] 4. Antibacterial polyester fiber test The test results showed that the antibacterial rate was 76.8%.

[0085] (Comparative Example 2) 1. Synthesis of reactive antibacterial components Specifically, it is the same as Example 1. 1.1, the compound shown in formula 3 is obtained. While stirring, an aqueous solution of hexadecyltrimethylammonium chloride (weight concentration 5.6%) was added to an equal volume of an aqueous solution of sodium 5-sulfoisophthalate (weight concentration 5.0%), stirred for 2 hours, allowed to stand to separate the layers, filtered, the filter cake was washed three times with water, each time using an equal volume of water to the filter cake, and dried at 80°C for 5 hours to obtain a dry product of the compound represented by Formula 3. The nitrogen content by weight of the product was measured to be 2.64%.

[0086] 1.2. Obtaining reactive antibacterial components Ethylene glycol and the product from step 1.1 were mixed in a molar ratio of 1.3:1 as reaction raw materials, and the esterification reaction was carried out at 180°C until the esterification rate reached 97%. The water produced by the esterification was collected and measured to obtain a reactive antibacterial component. The nitrogen content of the product was determined to be 2.43% by weight.

[0087] 2.Production of antibacterial polyester The main difference from Example 1 is that the product of step 1.2 is added to the esterification step in the production of antibacterial polyester. 2.1.Esterification Terephthalic acid, the product of step 1.2, antimony ethylene glycolate, and ethylene glycol are mixed (the molar ratio of ethylene glycol to terephthalic acid is 1.2, the nitrogen-equivalent mass ratio of the product of step 1.2 to terephthalic acid is 1.2:100, and the amount of antimony ethylene glycolate used in terms of antimony corresponds to 200 ppmw of the weight of terephthalic acid), and an esterification reaction is carried out at 200°C. Water produced by the esterification reaction is collected and measured until the esterification rate reaches 97%, and esterified product I is obtained.

[0088] 2.2. Pre-condensation polymerization The esterified material I from step 2.1 was subjected to condensation polymerization at 500 Pa absolute pressure and 260° C. for 45 minutes.

[0089] 2.3. Final condensation polymerization The material obtained in step 2.2 was subjected to a condensation polymerization reaction at 280°C under an absolute pressure of 50 Pa until the intrinsic viscosity reached 0.68 dL / g, yielding an antibacterial polyester. The nitrogen weight content in the antibacterial polyester was determined to be 0.73%.

[0090] 3. Antibacterial fiber manufacturing 3.1. Melt spinning The antibacterial polyester (calculated by N content) prepared in step 2.3 was mixed with commercial spinning-grade PET at a weight ratio of 0.040:100 and melt-spun at a melt-spinning temperature of 280 °C to obtain primary fibers.

[0091] 3.2. Stretching The spun fiber obtained by melt spinning was heated and drawn to a draw ratio of 4.0 and a drawing temperature of 140°C. Next, FDY fiber was spun. The FDY fiber had a specification of 150D.

[0092] 4. Antibacterial polyester fiber test The test results showed that the antibacterial rate was 82.9%.

[0093] Example 2 1. Synthesis of reactive antibacterial components 1.1. The compound shown in formula 3 is obtained. This is the same as step 1.1 in Example 1, but specifically, it is as follows. While stirring, an aqueous solution of hexadecyltrimethylammonium chloride (weight concentration 5.6%) was added to an equal volume of an aqueous solution of sodium 5-sulfoisophthalate (weight concentration 5.0%), stirred for 2 hours, allowed to stand to separate the layers, filtered, the filter cake was washed three times with water, each time using an equal volume of water to the filter cake, and dried at 80°C for 5 hours to obtain a dry product of the compound represented by Formula 3. The nitrogen content by weight of the product was measured to be 2.64%.

[0094] 1.2. Obtaining reactive antibacterial components The main difference from Step 1.2 of Example 1 is that the diol is 1,4-butanediol.

[0095] The reactive antibacterial component was obtained by mixing 1,4-butanediol and the product from step 1.1 in a molar ratio of 1.3:1, and carrying out an esterification reaction at 180°C. The water produced by the esterification was collected and measured until the esterification rate reached 97%. The nitrogen content of the product was determined to be 2.27% by weight.

[0096] 2.Production of antibacterial polyester 2.1.Esterification The reaction raw materials, terephthalic acid, antimony ethylene glycolate, and ethylene glycol (the molar ratio of ethylene glycol to terephthalic acid is 1.2, and the amount of antimony ethylene glycolate used is equivalent to 200 ppmw of the weight of terephthalic acid in terms of antimony), are mixed, and an esterification reaction is carried out at 200°C. The water produced by the esterification is measured and collected until the esterification rate reaches 97%, and esterified product I is obtained.

[0097] 2.2. Pre-condensation polymerization The product of step 1.2 is calculated based on the weight of nitrogen contained therein, and the esterification material I of step 2.1 is calculated based on the weight of terephthalic acid required to prepare it. The product of step 1.2 and the esterification material I of step 2.1 are mixed in a weight ratio of 1.2:100 and subjected to condensation polymerization at an absolute pressure of 500 Pa and 260°C for 45 minutes.

[0098] 2.3. Final condensation polymerization The material obtained in step 2.2 was subjected to polycondensation at 280°C under an absolute pressure of 50 Pa until the intrinsic viscosity reached 0.68 dL / g, yielding an antibacterial polyester. The nitrogen weight content in the antibacterial polyester was determined to be 0.72%.

[0099] 3. Antibacterial fiber manufacturing 3.1. Melt spinning The antibacterial polyester (calculated by N content) prepared in step 2.3 was mixed with commercial spinning-grade PET at a weight ratio of 0.040:100 and melt-spun at a melt-spinning temperature of 280 °C to obtain primary fibers.

[0100] 3.2. Stretching The spun fiber obtained by melt spinning was heated and drawn to a draw ratio of 4.0 and a drawing temperature of 140°C. Next, FDY fiber was spun. The FDY fiber had a specification of 150D.

[0101] 4. Antibacterial polyester fiber test The test results showed that the antibacterial rate was 87.6%.

[0102] Example 3 1. Synthesis of reactive antibacterial components 1.1. The compound shown in formula 3 is obtained. This is the same as step 1.1 in Example 1, but specifically, it is as follows. While stirring, an aqueous solution of hexadecyltrimethylammonium chloride (weight concentration 5.6%) was added to an equal volume of an aqueous solution of sodium 5-sulfoisophthalate (weight concentration 5.0%), stirred for 2 hours, allowed to stand to separate the layers, filtered, the filter cake was washed three times with water, each time using an equal volume of water to the filter cake, and dried at 80°C for 5 hours to obtain a dry product of the compound represented by Formula 3. The nitrogen content by weight of the product was measured to be 2.64%.

[0103] 1.2. Obtaining reactive antibacterial components The main difference from step 1.2 of Example 1 is that the diol is polyethylene glycol 400. Specifically, The reactive antibacterial component was obtained by mixing polyethylene glycol 400 and the product from step 1.1 in a molar ratio of 1.3:1 and carrying out an esterification reaction at 180°C until the esterification rate reached 97%. The water produced by the esterification was collected and measured, and the nitrogen content of the product was determined to be 1.37% by weight.

[0104] 2.Production of antibacterial polyester 2.1.Esterification The reaction raw materials, terephthalic acid, antimony ethylene glycolate, and ethylene glycol (the molar ratio of ethylene glycol to terephthalic acid is 1.2, and the amount of antimony ethylene glycolate used is equivalent to 200 ppmw of the weight of terephthalic acid in terms of antimony), are mixed, and an esterification reaction is carried out at 200°C. The water produced by the esterification is measured and collected until the esterification rate reaches 97%, and esterified product I is obtained.

[0105] 2.2. Pre-condensation polymerization The product of step 1.2 is calculated based on the weight of nitrogen contained therein, and the esterification material I of step 2.1 is calculated based on the weight of terephthalic acid required to prepare it. The product of step 1.2 and the esterification material I of step 2.1 are mixed in a weight ratio of 1.2:100 and subjected to condensation polymerization at an absolute pressure of 500 Pa and 260°C for 45 minutes.

[0106] 2.3. Final polycondensation The material obtained in step 2.2 was subjected to a polycondensation reaction at 280°C under an absolute pressure of 50 Pa until the intrinsic viscosity reached 0.68 dL / g, yielding an antibacterial polyester. The nitrogen weight content in the antibacterial polyester was determined to be 0.59%.

[0107] 3. Antibacterial fiber manufacturing 3.1. Melt spinning The antibacterial polyester (calculated by N content) prepared in step 2.3 was mixed with commercial spinning-grade PET at a weight ratio of 0.040:100 and melt-spun at a melt-spinning temperature of 280 °C to obtain primary fibers.

[0108] 3.2. Stretching The spun fiber obtained by melt spinning was heated and drawn to a draw ratio of 4.0 and a drawing temperature of 140°C. Next, FDY fiber was spun. The FDY fiber had a specification of 150D.

[0109] 4. Antibacterial polyester fiber test The test results showed that the antibacterial rate was 90.9%.

[0110] Example 4 1. Synthesis of reactive antibacterial components 1.1. The compound shown in formula 3 is obtained. This is the same as step 1.1 in Example 1, but specifically, it is as follows. While stirring, an aqueous solution of hexadecyltrimethylammonium chloride (weight concentration 5.6%) was added to an equal volume of an aqueous solution of sodium 5-sulfoisophthalate (weight concentration 5.0%), stirred for 2 hours, allowed to stand to separate the layers, filtered, the filter cake was washed three times with water, each time using an equal volume of water to the filter cake, and dried at 80°C for 5 hours to obtain a dry product of the compound represented by Formula 3. The nitrogen content by weight of the product was measured to be 2.64%.

[0111] 1.2. Obtaining reactive antibacterial components The main difference from Step 1.2 in Example 1 is that the diol is 1,4-cyclohexanedimethanol. The reactive antibacterial component was obtained by mixing 1,4-cyclohexanedimethanol and the product from step 1.1 in a molar ratio of 1.3:1 at 180°C and conducting an esterification reaction until the esterification rate reached 97%. The water produced by the esterification was collected and measured, and the nitrogen content of the product was determined to be 2.03% by weight.

[0112] 2.Production of antibacterial polyester 2.1.Esterification The reaction raw materials, terephthalic acid, antimony ethylene glycolate, and ethylene glycol (the molar ratio of ethylene glycol to terephthalic acid is 1.2, and the amount of antimony ethylene glycolate used is equivalent to 200 ppmw of the weight of terephthalic acid in terms of antimony), are mixed, and an esterification reaction is carried out at 200°C. The water produced by the esterification is measured and collected until the esterification rate reaches 97%, and esterified product I is obtained.

[0113] 2.2. Pre-condensation polymerization The product of step 1.2 is calculated based on the weight of nitrogen contained therein, and the esterification material I of step 2.1 is calculated based on the weight of terephthalic acid required to prepare it. The product of step 1.2 and the esterification material I of step 2.1 are mixed in a weight ratio of 1.2:100 and subjected to condensation polymerization at an absolute pressure of 500 Pa and 260°C for 45 minutes.

[0114] 2.3. Final condensation polymerization The material obtained in step 2.2 was subjected to a polycondensation reaction at 280°C under an absolute pressure of 50 Pa until the intrinsic viscosity reached 0.68 dL / g, yielding an antibacterial polyester. The nitrogen weight content in the antibacterial polyester was determined to be 0.69%.

[0115] 3. Antibacterial fiber manufacturing 3.1. Melt spinning The antibacterial polyester (calculated by N content) prepared in step 2.3 was mixed with commercial spinning-grade PET at a weight ratio of 0.040:100 and melt-spun at a melt-spinning temperature of 280 °C to obtain primary fibers.

[0116] 3.2. Stretching The spun fiber obtained by melt spinning was heated and drawn to a draw ratio of 4.0 and a drawing temperature of 140°C. Next, FDY fiber was spun. The FDY fiber had a specification of 150D.

[0117] 4. Antibacterial polyester fiber test The test results showed that the antibacterial rate was 95.3%.

[0118] Example 5 1. Synthesis of reactive antibacterial components 1.1. The compound shown in formula 3 is obtained. This is the same as step 1.1 in Example 1, but specifically, it is as follows. While stirring, an aqueous solution of hexadecyltrimethylammonium chloride (weight concentration 5.6%) was added to an equal volume of an aqueous solution of sodium 5-sulfoisophthalate (weight concentration 5.0%), stirred for 2 hours, allowed to stand to separate the layers, filtered, the filter cake was washed three times with water, each time using an equal volume of water to the filter cake, and dried at 80°C for 5 hours to obtain a dry product of the compound represented by Formula 3. The nitrogen content by weight of the product was measured to be 2.64%.

[0119] 1.2. Obtaining reactive antibacterial components The main difference from Step 1.2 in Example 1 is that the diols are ethylene glycol and 1,4-cyclohexanedimethanol. Ethylene glycol, 1,4-cyclohexanedimethanol, and the product from step 1.1 (the molar ratio of ethylene glycol to 1,4-cyclohexanedimethanol is 1:1, and the molar ratio of (the sum of ethylene glycol and 1,4-cyclohexanedimethanol) to the product from step 1.1 is 1.3:1) were mixed as reaction raw materials and subjected to an esterification reaction at 180°C. The reactive antibacterial component was obtained by collecting and measuring the water produced by the esterification reaction until the esterification rate reached 97%. The nitrogen content of the product was determined to be 2.21% by weight.

[0120] 2.Production of antibacterial polyester 2.1.Esterification The reaction raw materials, terephthalic acid, antimony ethylene glycolate, and ethylene glycol (the molar ratio of ethylene glycol to terephthalic acid is 1.2, and the amount of antimony ethylene glycolate used is equivalent to 200 ppmw of the weight of terephthalic acid in terms of antimony), are mixed, and an esterification reaction is carried out at 200°C. The water produced by the esterification is measured and collected until the esterification rate reaches 97%, and esterified product I is obtained.

[0121] 2.2. Pre-condensation polymerization The product of step 1.2 is calculated based on the weight of nitrogen contained therein, and the esterification material I of step 2.1 is calculated based on the weight of terephthalic acid required to prepare it. The product of step 1.2 and the esterification material I of step 2.1 are mixed in a weight ratio of 1.2:100 and polycondensed at an absolute pressure of 500 Pa and 260°C for 45 minutes.

[0122] 2.3. Final condensation polymerization The material obtained in step 2.2 was subjected to a condensation polymerization reaction at 280°C under an absolute pressure of 50 Pa until the intrinsic viscosity reached 0.68 dL / g, yielding an antibacterial polyester. The nitrogen weight content in the antibacterial polyester was determined to be 0.71%.

[0123] 3. Antibacterial fiber manufacturing 3.1. Melt spinning The antibacterial polyester (calculated by N content) prepared in step 2.3 was mixed with commercial spinning-grade PET at a weight ratio of 0.040:100 and melt-spun at a melt-spinning temperature of 280 °C to obtain primary fibers.

[0124] 3.2. Stretching The spun fiber obtained by melt spinning was heated and drawn to a draw ratio of 4.0 and a drawing temperature of 140°C. Next, FDY fiber was spun. The FDY fiber had a specification of 150D.

[0125] 4. Antibacterial polyester fiber test Test results showed that the antibacterial rate was 99.7%.

[0126] Example 6 1. Synthesis of reactive antibacterial components 1.1. The compound shown in formula 3 is obtained. This is the same as step 1.1 in Example 1, but specifically, it is as follows. While stirring, an aqueous solution of hexadecyltrimethylammonium chloride (weight concentration 5.6%) was added to an equal volume of an aqueous solution of sodium 5-sulfoisophthalate (weight concentration 5.0%), stirred for 2 hours, allowed to stand to separate the layers, filtered, the filter cake was washed three times with water, each time using an equal volume of water to the filter cake, and dried at 80°C for 5 hours to obtain a dry product of the compound represented by Formula 3. The nitrogen content by weight of the product was measured to be 2.64%.

[0127] 1.2. Obtaining reactive antibacterial components The main difference from Step 1.2 in Example 1 is that the diols are ethylene glycol and 1,4-cyclohexanedimethanol. Ethylene glycol, 1,4-cyclohexanedimethanol, and the product from step 1.1 (the molar ratio of ethylene glycol to 1,4-cyclohexanedimethanol is 4:1, and the molar ratio of (ethylene glycol and 1,4-cyclohexanedimethanol combined) to the product from step 1.1 is 1.3:1) were mixed as reaction raw materials and subjected to an esterification reaction at 180°C. The reactive antibacterial component was obtained by collecting and measuring the water produced by the esterification reaction until the esterification rate reached 97%. The nitrogen content of the product was determined to be 2.34% by weight.

[0128] 2.Production of antibacterial polyester 2.1.Esterification The reaction raw materials, terephthalic acid, antimony ethylene glycolate, and ethylene glycol (the molar ratio of ethylene glycol to terephthalic acid is 1.2, and the amount of antimony ethylene glycolate used is equivalent to 200 ppmw of the weight of terephthalic acid in terms of antimony), are mixed, and an esterification reaction is carried out at 200°C. The water produced by the esterification is measured and collected until the esterification rate reaches 97%, and esterified product I is obtained.

[0129] 2.2. Pre-condensation polymerization The product of step 1.2 is calculated based on the weight of nitrogen contained therein, and the esterification material I of step 2.1 is calculated based on the weight of terephthalic acid required to prepare it. The product of step 1.2 and the esterification material I of step 2.1 are mixed in a weight ratio of 1.2:100 and subjected to condensation polymerization at an absolute pressure of 500 Pa and 260°C for 45 minutes.

[0130] 2.3. Final condensation polymerization The material obtained in step 2.2 was subjected to a condensation polymerization reaction at 280°C under an absolute pressure of 50 Pa until the intrinsic viscosity reached 0.68 dL / g, yielding an antibacterial polyester. The nitrogen weight content in the antibacterial polyester was determined to be 0.72%.

[0131] 3. Antibacterial fiber manufacturing 3.1. Melt spinning The antibacterial polyester (calculated by N content) prepared in step 2.3 was mixed with commercial spinning-grade PET at a weight ratio of 0.040:100 and melt-spun at a melt-spinning temperature of 280 °C to obtain primary fibers.

[0132] 3.2. Stretching The spun fiber obtained by melt spinning was heated and drawn to a draw ratio of 4.0 and a drawing temperature of 140°C. Next, FDY fiber was spun. The FDY fiber had a specification of 150D.

[0133] 4. Antibacterial polyester fiber test Test results showed that the antibacterial rate was 98.5%.

Claims

1. A method for producing antibacterial polyester, comprising: (i) a step of obtaining an esterified product I by an esterification reaction between a diol and a dibasic acid; (ii) mixing the ester I with a reactive antibacterial component to carry out a pre-condensation polymerization reaction to obtain a pre-condensation polymerization product; (iii) carrying out a final condensation polymerization reaction of the pre-condensation polymerization product to obtain an antibacterial polyester; The reactive antibacterial component is obtained by an esterification reaction of a substance shown in Formula 3 with a diol, 【Chemistry 1】 Q is a quaternary ammonium group containing a long-chain hydrocarbon group, the long-chain hydrocarbon group having 6 to 20 carbon atoms, and Ar is an aromatic ring; The method for producing antibacterial polyester, wherein the diol contains 1,4-cyclohexanedimethanol.

2. 2. The method according to claim 1, wherein the diol is a mixed alcohol of ethylene glycol and 1,4-cyclohexanedimethanol.

3. 3. The method according to claim 2, wherein the molar ratio of ethylene glycol to 1,4-cyclohexanedimethanol is 0.1 to 10.

4. 4. The method according to claim 3, wherein the molar ratio of ethylene glycol to 1,4-cyclohexanedimethanol is 0.2 to 5.

5. 2. The method according to claim 1, wherein Ar is a benzene ring or a naphthalene ring.

6. In the step (i), the diol includes at least one selected from the group consisting of ethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, and 1,4-cyclohexanedimethanol; and / or the dibasic acid includes at least one selected from the group consisting of terephthalic acid, succinic acid, adipic acid, isophthalic acid, and furandicarboxylic acid; and / or the molar ratio of the diol to the diacid is 1.1 to 1.5; and / or the esterification reaction is carried out until the esterification rate reaches 95 to 99%; and / or the reaction temperature is 150 to 250°C.

7. In the step (ii), the reaction pressure is 400 to 600 Pa; and / or the reaction temperature is 255 to 265°C; and / or the reaction time is 30 to 60 minutes.

8. In the step (iii), the reaction pressure is 100 Pa or less, and / or the reaction temperature is 270 to 285°C; and / or the step (iii) is carried out until the intrinsic viscosity reaches 0.60 to 0.75 dL / g.

9. A method for synthesizing the reactive antimicrobial component, comprising: (1) a step of subjecting compound 1 and compound 2 to an ion exchange reaction in a solvent to obtain intermediate product 3; wherein Compound 1 has the structure shown in Formula 1: 【Chemistry 2】 Compound 2 has the structure shown in Formula 2, 【Transformation 3】 The intermediate product 3 has a structure shown in formula 3, X is Cl or Br, and M is an alkali metal; (2) The method according to claim 1, further comprising the step of esterifying the intermediate 3 with a diol to obtain a reactive antibacterial component.

10. 10. The method according to claim 9, wherein the solvent in step (1) is water.

11. Compound 1 has the structure shown in formula 1a, 【Chemistry 4】 R １ is a long chain hydrocarbon group, and R １ The number of carbon atoms in R ２ ~R ４ is a short-chain hydrocarbon group, and / or said compound 2 has the structure shown in formula 2a: 【Transformation 5】 and / or the molar ratio of the diol to the intermediate product 3 in the step (2) is 1 or more and 2 or less; and / or the esterification reaction in the step (2) is carried out until the esterification rate reaches 95 to 99%; and / or the esterification temperature in step (2) is 150 to 250°C.

12. The R ２ ~R ４ are independently a C1-C2 alkyl group, and / or the molar ratio of the diol to the intermediate product 3 in the step (2) is 1.1 to 1.

5.

13. Antibacterial polyester, characterized in that it is obtainable by the preparation method according to any one of claims 1 to 12.

14. A method for producing an antibacterial fiber, comprising: (a) mixing a PET polyester for spinning with the antibacterial polyester of claim 13 and melt-spinning the mixture to obtain a new fiber; (b) A step of hot drawing the spun fiber A method for producing antibacterial fibers.

15. The mass ratio of the antibacterial polyester to the PET polyester for spinning in the step (a) is b:100, calculated based on the N contained therein, and b is greater than 0 and less than 0.2; and / or the stretching temperature in the step (b) is 120 to 160°C; and / or the stretching ratio in the step (b) is 3.0 to 5.

0. The method of claim 14 .

16. An antibacterial fiber obtained by the method according to claim 14 or 15.

17. 17. Use of the antimicrobial fiber according to claim 16 in the manufacture of a medical-surgical product.

18. 17. Use of the antimicrobial fiber according to claim 16 in the manufacture of antimicrobial gauze and / or antimicrobial bandages.

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